Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109036749/gd3304sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109036749/gd3304Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109036749/gd3304IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109036749/gd3304IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109036749/gd3304IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109036749/gd3304Vsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109036749/gd3304VI_100sup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109036749/gd3304VI_300sup8.hkl |
CCDC references: 247117; 701170; 701171; 701172; 701173; 701174; 701175
Compounds (I)–(VI) were synthesized by the methods described by Zaitsev et al. (2008). Single colourless crystals suitable for X-ray diffraction analysis were obtained from toluene solutions upon freezing to 258 K.
In the structures of (I) and (III)–(V), the hydroxyl H atoms were found in difference Fourier syntheses and refined with isotropic displacement parameters. In (II), all H atoms were found in a difference Fourier synthesis and refined isotropically. In (VI), the disordered hydroxyl H atoms were also found in a difference Fourier synthesis and refined with Uiso(H) = 1.5Ueq(O). The occupancies of these hydroxyl H atoms were refined in the last runs of SHELXL97 (Sheldrick, 2008). Their values converged to 0.51 (2):0.49 (2) for both datasets collected at 100 and 300 K from the same crystal. In all compounds, all other (C-bound) H atoms were placed in calculated positions and refined using a riding model, with C—H = 0.95 (aromatic), 0.98 (CH3), 0.99 (CH2) or 1.00 Å (CH), and with Uiso(H) = kUeq(carrier), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and k = 1.2 for all other H atoms. In the noncentrosymmetric structures (I), (II), (IV) and (V), Friedel pairs were merged in the final refinements (MERG 3 instruction in SHELXL97). In (VI), the possibility of a superstructure was checked but was not confirmed.
For all compounds, data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C17H21NO2 | F(000) = 292 |
Mr = 271.35 | Dx = 1.245 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 4308 reflections |
a = 5.8366 (1) Å | θ = 2.5–29.9° |
b = 15.3018 (4) Å | µ = 0.08 mm−1 |
c = 8.1078 (2) Å | T = 120 K |
β = 91.444 (1)° | Block, colourless |
V = 723.88 (3) Å3 | 0.40 × 0.20 × 0.10 mm |
Z = 2 |
Bruker SMART 1K diffractometer | 1677 independent reflections |
Radiation source: fine-focus sealed tube | 1626 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −7→7 |
Tmin = 0.968, Tmax = 0.992 | k = −19→19 |
4958 measured reflections | l = −10→10 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0487P)2 + 0.0768P] where P = (Fo2 + 2Fc2)/3 |
1677 reflections | (Δ/σ)max < 0.001 |
190 parameters | Δρmax = 0.26 e Å−3 |
2 restraints | Δρmin = −0.19 e Å−3 |
C17H21NO2 | V = 723.88 (3) Å3 |
Mr = 271.35 | Z = 2 |
Monoclinic, Pc | Mo Kα radiation |
a = 5.8366 (1) Å | µ = 0.08 mm−1 |
b = 15.3018 (4) Å | T = 120 K |
c = 8.1078 (2) Å | 0.40 × 0.20 × 0.10 mm |
β = 91.444 (1)° |
Bruker SMART 1K diffractometer | 1677 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1626 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.992 | Rint = 0.029 |
4958 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 2 restraints |
wR(F2) = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.26 e Å−3 |
1677 reflections | Δρmin = −0.19 e Å−3 |
190 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.8651 (2) | 0.35398 (9) | 0.27939 (17) | 0.0166 (3) | |
O1 | 0.6689 (2) | 0.52412 (8) | 0.25285 (17) | 0.0253 (3) | |
O2 | 0.9803 (2) | 0.40890 (8) | −0.01196 (15) | 0.0206 (3) | |
C1 | 0.5441 (3) | 0.45589 (11) | 0.3303 (2) | 0.0214 (3) | |
H1A | 0.3781 | 0.4644 | 0.3078 | 0.026* | |
H1B | 0.5714 | 0.4588 | 0.4512 | 0.026* | |
C2 | 0.6157 (3) | 0.36586 (11) | 0.2676 (2) | 0.0188 (3) | |
H2A | 0.5404 | 0.3200 | 0.3332 | 0.023* | |
H2B | 0.5635 | 0.3591 | 0.1511 | 0.023* | |
C3 | 0.9522 (3) | 0.34606 (12) | 0.4504 (2) | 0.0212 (3) | |
H3A | 0.9002 | 0.3962 | 0.5147 | 0.032* | |
H3B | 1.1201 | 0.3448 | 0.4516 | 0.032* | |
H3C | 0.8944 | 0.2919 | 0.4988 | 0.032* | |
C4 | 0.9550 (3) | 0.28428 (10) | 0.17160 (19) | 0.0151 (3) | |
H4 | 1.1226 | 0.2792 | 0.1986 | 0.018* | |
C5 | 0.9338 (3) | 0.31695 (10) | −0.0104 (2) | 0.0163 (3) | |
H5 | 0.7735 | 0.3069 | −0.0525 | 0.020* | |
C11 | 0.8504 (3) | 0.19411 (10) | 0.2025 (2) | 0.0163 (3) | |
C6 | 0.9644 (3) | 0.13769 (11) | 0.3123 (2) | 0.0209 (3) | |
H6 | 1.1094 | 0.1541 | 0.3582 | 0.025* | |
C7 | 0.8684 (3) | 0.05745 (12) | 0.3557 (2) | 0.0265 (4) | |
H7 | 0.9476 | 0.0200 | 0.4313 | 0.032* | |
C8 | 0.6575 (4) | 0.03254 (12) | 0.2885 (2) | 0.0266 (4) | |
H8 | 0.5920 | −0.0220 | 0.3176 | 0.032* | |
C9 | 0.5422 (3) | 0.08783 (12) | 0.1780 (2) | 0.0236 (4) | |
H9 | 0.3981 | 0.0707 | 0.1314 | 0.028* | |
C10 | 0.6368 (3) | 0.16814 (11) | 0.1354 (2) | 0.0190 (3) | |
H10 | 0.5563 | 0.2055 | 0.0605 | 0.023* | |
C12 | 1.0991 (3) | 0.27011 (11) | −0.12307 (19) | 0.0161 (3) | |
C13 | 1.0579 (3) | 0.18331 (11) | −0.1715 (2) | 0.0205 (3) | |
H13 | 0.9265 | 0.1535 | −0.1337 | 0.025* | |
C14 | 1.2093 (3) | 0.14079 (12) | −0.2747 (2) | 0.0243 (4) | |
H14 | 1.1815 | 0.0818 | −0.3055 | 0.029* | |
C15 | 1.4011 (3) | 0.18402 (13) | −0.3333 (2) | 0.0243 (4) | |
H15 | 1.5042 | 0.1548 | −0.4034 | 0.029* | |
C16 | 1.4396 (3) | 0.27083 (12) | −0.2876 (2) | 0.0217 (4) | |
H16 | 1.5683 | 0.3012 | −0.3285 | 0.026* | |
C17 | 1.2906 (3) | 0.31327 (11) | −0.1823 (2) | 0.0185 (3) | |
H17 | 1.3198 | 0.3721 | −0.1508 | 0.022* | |
H1 | 0.770 (5) | 0.5387 (16) | 0.321 (4) | 0.035 (7)* | |
H2 | 0.948 (5) | 0.4278 (18) | 0.081 (4) | 0.042 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0161 (6) | 0.0189 (7) | 0.0149 (7) | 0.0006 (5) | 0.0014 (5) | −0.0018 (5) |
O1 | 0.0322 (7) | 0.0203 (6) | 0.0231 (6) | −0.0007 (5) | −0.0033 (6) | 0.0022 (5) |
O2 | 0.0283 (6) | 0.0155 (6) | 0.0183 (6) | 0.0005 (5) | 0.0050 (5) | 0.0013 (5) |
C1 | 0.0220 (8) | 0.0200 (8) | 0.0223 (8) | 0.0020 (7) | 0.0023 (7) | −0.0022 (7) |
C2 | 0.0160 (7) | 0.0201 (8) | 0.0202 (8) | −0.0001 (6) | 0.0015 (6) | −0.0018 (6) |
C3 | 0.0209 (8) | 0.0266 (9) | 0.0160 (8) | 0.0010 (7) | −0.0003 (6) | −0.0012 (6) |
C4 | 0.0140 (6) | 0.0163 (7) | 0.0151 (7) | 0.0007 (6) | 0.0016 (6) | 0.0002 (6) |
C5 | 0.0163 (7) | 0.0158 (7) | 0.0167 (7) | 0.0008 (6) | 0.0017 (6) | 0.0014 (6) |
C11 | 0.0190 (8) | 0.0154 (7) | 0.0145 (7) | 0.0011 (6) | 0.0039 (6) | −0.0002 (6) |
C6 | 0.0225 (8) | 0.0193 (8) | 0.0208 (8) | 0.0019 (6) | −0.0007 (7) | −0.0003 (6) |
C7 | 0.0377 (10) | 0.0189 (8) | 0.0228 (9) | 0.0027 (8) | 0.0001 (8) | 0.0037 (7) |
C8 | 0.0371 (10) | 0.0181 (8) | 0.0247 (9) | −0.0059 (7) | 0.0057 (8) | −0.0009 (7) |
C9 | 0.0241 (8) | 0.0240 (9) | 0.0228 (8) | −0.0058 (7) | 0.0037 (7) | −0.0039 (7) |
C10 | 0.0185 (7) | 0.0199 (8) | 0.0189 (8) | 0.0006 (6) | 0.0018 (6) | −0.0002 (6) |
C12 | 0.0177 (7) | 0.0186 (8) | 0.0120 (7) | 0.0014 (6) | −0.0001 (6) | 0.0009 (6) |
C13 | 0.0226 (8) | 0.0198 (8) | 0.0193 (8) | −0.0012 (7) | 0.0022 (7) | 0.0002 (6) |
C14 | 0.0294 (10) | 0.0218 (8) | 0.0216 (9) | 0.0037 (7) | 0.0005 (7) | −0.0039 (7) |
C15 | 0.0240 (8) | 0.0319 (10) | 0.0170 (8) | 0.0078 (7) | 0.0018 (7) | −0.0009 (7) |
C16 | 0.0175 (8) | 0.0316 (9) | 0.0162 (8) | −0.0001 (7) | 0.0022 (6) | 0.0023 (7) |
C17 | 0.0194 (7) | 0.0214 (8) | 0.0147 (8) | −0.0015 (6) | −0.0002 (6) | 0.0014 (6) |
N1—C2 | 1.468 (2) | C11—C10 | 1.405 (2) |
N1—C3 | 1.469 (2) | C6—C7 | 1.398 (3) |
N1—C4 | 1.483 (2) | C6—H6 | 0.9500 |
O1—C1 | 1.427 (2) | C7—C8 | 1.387 (3) |
O1—H1 | 0.83 (3) | C7—H7 | 0.9500 |
O2—C5 | 1.4329 (19) | C8—C9 | 1.393 (3) |
O2—H2 | 0.83 (3) | C8—H8 | 0.9500 |
C1—C2 | 1.530 (2) | C9—C10 | 1.394 (2) |
C1—H1A | 0.9900 | C9—H9 | 0.9500 |
C1—H1B | 0.9900 | C10—H10 | 0.9500 |
C2—H2A | 0.9900 | C12—C17 | 1.394 (2) |
C2—H2B | 0.9900 | C12—C13 | 1.404 (2) |
C3—H3A | 0.9800 | C13—C14 | 1.394 (2) |
C3—H3B | 0.9800 | C13—H13 | 0.9500 |
C3—H3C | 0.9800 | C14—C15 | 1.394 (3) |
C4—C11 | 1.532 (2) | C14—H14 | 0.9500 |
C4—C5 | 1.560 (2) | C15—C16 | 1.396 (3) |
C4—H4 | 1.0000 | C15—H15 | 0.9500 |
C5—C12 | 1.524 (2) | C16—C17 | 1.394 (2) |
C5—H5 | 1.0000 | C16—H16 | 0.9500 |
C11—C6 | 1.397 (2) | C17—H17 | 0.9500 |
C2—N1—C3 | 113.00 (13) | C6—C11—C4 | 118.40 (15) |
C2—N1—C4 | 114.56 (13) | C10—C11—C4 | 123.01 (14) |
C3—N1—C4 | 112.18 (13) | C7—C6—C11 | 121.06 (17) |
C1—O1—H1 | 105.5 (19) | C7—C6—H6 | 119.5 |
C5—O2—H2 | 106.7 (19) | C11—C6—H6 | 119.5 |
O1—C1—C2 | 111.44 (14) | C8—C7—C6 | 119.97 (17) |
O1—C1—H1A | 109.3 | C8—C7—H7 | 120.0 |
C2—C1—H1A | 109.3 | C6—C7—H7 | 120.0 |
O1—C1—H1B | 109.3 | C7—C8—C9 | 119.70 (17) |
C2—C1—H1B | 109.3 | C7—C8—H8 | 120.2 |
H1A—C1—H1B | 108.0 | C9—C8—H8 | 120.2 |
N1—C2—C1 | 111.62 (14) | C10—C9—C8 | 120.44 (17) |
N1—C2—H2A | 109.3 | C10—C9—H9 | 119.8 |
C1—C2—H2A | 109.3 | C8—C9—H9 | 119.8 |
N1—C2—H2B | 109.3 | C9—C10—C11 | 120.41 (16) |
C1—C2—H2B | 109.3 | C9—C10—H10 | 119.8 |
H2A—C2—H2B | 108.0 | C11—C10—H10 | 119.8 |
N1—C3—H3A | 109.5 | C17—C12—C13 | 119.00 (15) |
N1—C3—H3B | 109.5 | C17—C12—C5 | 120.59 (14) |
H3A—C3—H3B | 109.5 | C13—C12—C5 | 120.40 (14) |
N1—C3—H3C | 109.5 | C14—C13—C12 | 120.20 (16) |
H3A—C3—H3C | 109.5 | C14—C13—H13 | 119.9 |
H3B—C3—H3C | 109.5 | C12—C13—H13 | 119.9 |
N1—C4—C11 | 113.74 (13) | C15—C14—C13 | 120.65 (16) |
N1—C4—C5 | 107.83 (12) | C15—C14—H14 | 119.7 |
C11—C4—C5 | 114.90 (13) | C13—C14—H14 | 119.7 |
N1—C4—H4 | 106.6 | C14—C15—C16 | 119.12 (16) |
C11—C4—H4 | 106.6 | C14—C15—H15 | 120.4 |
C5—C4—H4 | 106.6 | C16—C15—H15 | 120.4 |
O2—C5—C12 | 109.50 (13) | C15—C16—C17 | 120.45 (16) |
O2—C5—C4 | 108.20 (13) | C15—C16—H16 | 119.8 |
C12—C5—C4 | 112.32 (13) | C17—C16—H16 | 119.8 |
O2—C5—H5 | 108.9 | C12—C17—C16 | 120.56 (15) |
C12—C5—H5 | 108.9 | C12—C17—H17 | 119.7 |
C4—C5—H5 | 108.9 | C16—C17—H17 | 119.7 |
C6—C11—C10 | 118.42 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.83 (3) | 1.97 (3) | 2.7954 (19) | 170 (3) |
O2—H2···N1 | 0.83 (3) | 2.04 (3) | 2.6111 (18) | 126 (2) |
Symmetry code: (i) x, −y+1, z+1/2. |
C21H27NO2 | F(000) = 704 |
Mr = 325.44 | Dx = 1.206 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 6375 reflections |
a = 8.5024 (4) Å | θ = 2.3–29.9° |
b = 11.9480 (5) Å | µ = 0.08 mm−1 |
c = 17.6485 (7) Å | T = 120 K |
V = 1792.85 (13) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.24 × 0.20 mm |
Bruker SMART 1K diffractometer | 2712 independent reflections |
Radiation source: fine-focus sealed tube | 2398 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ω scans | θmax = 29.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −11→11 |
Tmin = 0.977, Tmax = 0.985 | k = −12→16 |
12996 measured reflections | l = −19→24 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.083 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0452P)2 + 0.2289P] where P = (Fo2 + 2Fc2)/3 |
2712 reflections | (Δ/σ)max < 0.001 |
325 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C21H27NO2 | V = 1792.85 (13) Å3 |
Mr = 325.44 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.5024 (4) Å | µ = 0.08 mm−1 |
b = 11.9480 (5) Å | T = 120 K |
c = 17.6485 (7) Å | 0.30 × 0.24 × 0.20 mm |
Bruker SMART 1K diffractometer | 2712 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2398 reflections with I > 2σ(I) |
Tmin = 0.977, Tmax = 0.985 | Rint = 0.040 |
12996 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.083 | All H-atom parameters refined |
S = 1.03 | Δρmax = 0.21 e Å−3 |
2712 reflections | Δρmin = −0.20 e Å−3 |
325 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.35346 (16) | 0.52971 (12) | 0.27771 (8) | 0.0168 (3) | |
O1 | 0.28678 (14) | 0.74120 (10) | 0.30108 (7) | 0.0189 (2) | |
O2 | 0.66413 (14) | 0.47597 (11) | 0.20799 (7) | 0.0221 (3) | |
C1 | 0.5350 (2) | 0.52078 (14) | 0.16482 (9) | 0.0189 (3) | |
C2 | 0.37558 (19) | 0.48853 (14) | 0.19995 (10) | 0.0184 (3) | |
C3 | 0.5592 (2) | 0.64710 (15) | 0.16528 (11) | 0.0225 (4) | |
C4 | 0.5423 (2) | 0.47535 (18) | 0.08388 (10) | 0.0263 (4) | |
C5 | 0.4226 (2) | 0.45467 (15) | 0.33634 (10) | 0.0227 (4) | |
C6 | 0.2884 (3) | 0.42443 (16) | 0.38944 (11) | 0.0280 (4) | |
C7 | 0.1827 (2) | 0.52712 (16) | 0.38402 (10) | 0.0232 (4) | |
C8 | 0.18740 (19) | 0.55350 (13) | 0.29899 (9) | 0.0167 (3) | |
C9 | 0.14822 (18) | 0.67934 (13) | 0.28141 (9) | 0.0167 (3) | |
C10 | 0.10664 (18) | 0.70077 (14) | 0.19757 (9) | 0.0180 (3) | |
C11 | 0.1615 (2) | 0.79812 (15) | 0.16237 (10) | 0.0228 (4) | |
C12 | 0.1260 (2) | 0.82006 (18) | 0.08651 (11) | 0.0306 (4) | |
C13 | 0.0340 (2) | 0.7466 (2) | 0.04558 (10) | 0.0314 (4) | |
C14 | −0.0230 (2) | 0.65083 (18) | 0.08018 (10) | 0.0279 (4) | |
C15 | 0.0126 (2) | 0.62770 (16) | 0.15586 (10) | 0.0224 (4) | |
C16 | 0.01362 (19) | 0.71839 (13) | 0.33306 (9) | 0.0172 (3) | |
C17 | 0.0390 (2) | 0.79870 (15) | 0.38896 (10) | 0.0218 (3) | |
C18 | −0.0794 (2) | 0.82608 (17) | 0.44028 (10) | 0.0260 (4) | |
C19 | −0.2242 (2) | 0.77320 (16) | 0.43673 (10) | 0.0247 (4) | |
C20 | −0.2520 (2) | 0.69529 (17) | 0.37973 (10) | 0.0251 (4) | |
C21 | −0.1349 (2) | 0.66812 (15) | 0.32815 (10) | 0.0226 (4) | |
H1 | 0.360 (3) | 0.695 (2) | 0.2932 (14) | 0.037 (7)* | |
H2 | 0.673 (3) | 0.406 (2) | 0.2018 (15) | 0.039 (7)* | |
H8 | 0.111 (2) | 0.5054 (17) | 0.2722 (10) | 0.016 (5)* | |
H11 | 0.226 (3) | 0.8489 (19) | 0.1884 (13) | 0.029 (6)* | |
H12 | 0.166 (2) | 0.8904 (19) | 0.0638 (12) | 0.024 (5)* | |
H13 | 0.004 (3) | 0.759 (2) | −0.0051 (15) | 0.040 (6)* | |
H14 | −0.094 (3) | 0.5981 (19) | 0.0528 (11) | 0.026 (5)* | |
H15 | −0.030 (2) | 0.5631 (18) | 0.1773 (11) | 0.021 (5)* | |
H17 | 0.141 (2) | 0.8358 (17) | 0.3923 (11) | 0.019 (5)* | |
H18 | −0.063 (3) | 0.881 (2) | 0.4783 (12) | 0.030 (6)* | |
H19 | −0.306 (3) | 0.7904 (18) | 0.4737 (12) | 0.026 (5)* | |
H20 | −0.358 (3) | 0.6615 (19) | 0.3750 (12) | 0.027 (6)* | |
H21 | −0.158 (2) | 0.6126 (17) | 0.2876 (11) | 0.015 (5)* | |
H22 | 0.294 (2) | 0.5219 (18) | 0.1672 (11) | 0.023 (5)* | |
H23 | 0.368 (2) | 0.4065 (18) | 0.1989 (12) | 0.022 (5)* | |
H31 | 0.650 (3) | 0.6659 (19) | 0.1338 (12) | 0.027 (6)* | |
H32 | 0.467 (3) | 0.6827 (18) | 0.1449 (12) | 0.024 (5)* | |
H33 | 0.573 (2) | 0.6771 (18) | 0.2192 (12) | 0.023 (5)* | |
H41 | 0.535 (3) | 0.393 (2) | 0.0857 (12) | 0.031 (6)* | |
H42 | 0.451 (3) | 0.507 (2) | 0.0521 (13) | 0.040 (7)* | |
H43 | 0.642 (3) | 0.4923 (19) | 0.0583 (13) | 0.028 (6)* | |
H51 | 0.506 (3) | 0.494 (2) | 0.3651 (12) | 0.032 (6)* | |
H52 | 0.473 (3) | 0.3898 (19) | 0.3115 (12) | 0.027 (5)* | |
H61 | 0.327 (3) | 0.409 (2) | 0.4391 (14) | 0.033 (6)* | |
H62 | 0.231 (3) | 0.358 (2) | 0.3697 (12) | 0.027 (6)* | |
H71 | 0.077 (3) | 0.513 (2) | 0.4013 (13) | 0.034 (6)* | |
H72 | 0.229 (3) | 0.589 (2) | 0.4111 (13) | 0.033 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0180 (6) | 0.0155 (6) | 0.0168 (6) | 0.0015 (5) | −0.0003 (5) | 0.0015 (5) |
O1 | 0.0165 (5) | 0.0148 (5) | 0.0255 (6) | −0.0015 (5) | −0.0002 (5) | −0.0021 (5) |
O2 | 0.0193 (5) | 0.0162 (6) | 0.0307 (7) | 0.0028 (5) | −0.0023 (5) | 0.0004 (5) |
C1 | 0.0188 (7) | 0.0168 (7) | 0.0210 (8) | 0.0019 (7) | 0.0002 (7) | 0.0005 (6) |
C2 | 0.0179 (7) | 0.0183 (8) | 0.0191 (8) | −0.0007 (6) | 0.0009 (6) | −0.0022 (6) |
C3 | 0.0237 (8) | 0.0166 (8) | 0.0273 (9) | 0.0012 (7) | 0.0032 (8) | 0.0038 (7) |
C4 | 0.0264 (9) | 0.0294 (10) | 0.0231 (9) | 0.0003 (8) | 0.0033 (7) | −0.0032 (7) |
C5 | 0.0232 (8) | 0.0206 (8) | 0.0244 (8) | 0.0017 (7) | −0.0030 (7) | 0.0052 (7) |
C6 | 0.0342 (10) | 0.0235 (9) | 0.0263 (9) | 0.0058 (9) | 0.0039 (8) | 0.0096 (7) |
C7 | 0.0301 (10) | 0.0207 (8) | 0.0186 (8) | 0.0047 (8) | 0.0035 (7) | 0.0038 (7) |
C8 | 0.0166 (7) | 0.0145 (7) | 0.0190 (7) | −0.0015 (6) | 0.0002 (6) | 0.0005 (6) |
C9 | 0.0181 (7) | 0.0136 (7) | 0.0183 (7) | −0.0014 (6) | −0.0006 (6) | 0.0001 (6) |
C10 | 0.0162 (7) | 0.0203 (7) | 0.0176 (7) | 0.0047 (6) | 0.0018 (6) | 0.0002 (6) |
C11 | 0.0231 (8) | 0.0216 (8) | 0.0236 (9) | 0.0038 (7) | 0.0012 (7) | 0.0039 (7) |
C12 | 0.0335 (10) | 0.0328 (10) | 0.0256 (9) | 0.0081 (9) | 0.0084 (8) | 0.0112 (8) |
C13 | 0.0343 (10) | 0.0428 (11) | 0.0170 (8) | 0.0154 (10) | 0.0022 (8) | 0.0036 (8) |
C14 | 0.0254 (9) | 0.0369 (11) | 0.0216 (9) | 0.0078 (8) | −0.0024 (7) | −0.0043 (7) |
C15 | 0.0216 (8) | 0.0258 (8) | 0.0199 (8) | 0.0018 (7) | 0.0009 (7) | 0.0000 (7) |
C16 | 0.0194 (7) | 0.0156 (7) | 0.0167 (7) | 0.0024 (6) | 0.0000 (6) | 0.0018 (6) |
C17 | 0.0235 (8) | 0.0202 (8) | 0.0218 (8) | −0.0023 (7) | 0.0008 (7) | −0.0029 (7) |
C18 | 0.0297 (9) | 0.0279 (9) | 0.0203 (8) | 0.0021 (8) | 0.0009 (7) | −0.0061 (7) |
C19 | 0.0251 (9) | 0.0278 (9) | 0.0212 (8) | 0.0059 (7) | 0.0045 (7) | 0.0018 (7) |
C20 | 0.0211 (8) | 0.0277 (9) | 0.0266 (9) | −0.0011 (8) | 0.0032 (7) | 0.0013 (7) |
C21 | 0.0221 (8) | 0.0235 (8) | 0.0220 (9) | −0.0020 (7) | −0.0002 (7) | −0.0022 (7) |
N1—C2 | 1.470 (2) | C8—C9 | 1.571 (2) |
N1—C8 | 1.488 (2) | C8—H8 | 0.99 (2) |
N1—C5 | 1.490 (2) | C9—C16 | 1.536 (2) |
O1—C9 | 1.4334 (19) | C9—C10 | 1.543 (2) |
O1—H1 | 0.84 (3) | C10—C15 | 1.394 (2) |
O2—C1 | 1.439 (2) | C10—C11 | 1.399 (2) |
O2—H2 | 0.85 (3) | C11—C12 | 1.397 (3) |
C1—C3 | 1.523 (2) | C11—H11 | 0.94 (2) |
C1—C4 | 1.530 (2) | C12—C13 | 1.380 (3) |
C1—C2 | 1.540 (2) | C12—H12 | 0.99 (2) |
C2—H22 | 0.98 (2) | C13—C14 | 1.385 (3) |
C2—H23 | 0.98 (2) | C13—H13 | 0.94 (3) |
C3—H31 | 0.98 (2) | C14—C15 | 1.397 (3) |
C3—H32 | 0.96 (2) | C14—H14 | 1.00 (2) |
C3—H33 | 1.02 (2) | C15—H15 | 0.93 (2) |
C4—H41 | 0.99 (2) | C16—C17 | 1.393 (2) |
C4—H42 | 1.03 (3) | C16—C21 | 1.401 (2) |
C4—H43 | 0.99 (2) | C17—C18 | 1.393 (3) |
C5—C6 | 1.520 (3) | C17—H17 | 0.98 (2) |
C5—H51 | 0.99 (2) | C18—C19 | 1.386 (3) |
C5—H52 | 0.99 (2) | C18—H18 | 0.95 (2) |
C6—C7 | 1.524 (3) | C19—C20 | 1.391 (3) |
C6—H61 | 0.96 (2) | C19—H19 | 0.98 (2) |
C6—H62 | 0.99 (2) | C20—C21 | 1.388 (2) |
C7—C8 | 1.534 (2) | C20—H20 | 0.99 (2) |
C7—H71 | 0.96 (3) | C21—H21 | 0.99 (2) |
C7—H72 | 0.96 (2) | ||
C2—N1—C8 | 114.89 (13) | N1—C8—C9 | 109.52 (13) |
C2—N1—C5 | 113.36 (14) | C7—C8—C9 | 112.60 (14) |
C8—N1—C5 | 108.29 (13) | N1—C8—H8 | 113.0 (11) |
C9—O1—H1 | 103.1 (17) | C7—C8—H8 | 109.4 (11) |
C1—O2—H2 | 111.3 (17) | C9—C8—H8 | 108.8 (11) |
O2—C1—C3 | 105.26 (14) | O1—C9—C16 | 108.19 (13) |
O2—C1—C4 | 109.37 (14) | O1—C9—C10 | 109.57 (13) |
C3—C1—C4 | 110.56 (15) | C16—C9—C10 | 110.37 (13) |
O2—C1—C2 | 111.43 (13) | O1—C9—C8 | 105.75 (12) |
C3—C1—C2 | 111.37 (14) | C16—C9—C8 | 109.37 (13) |
C4—C1—C2 | 108.83 (14) | C10—C9—C8 | 113.38 (13) |
N1—C2—C1 | 113.88 (14) | C15—C10—C11 | 118.52 (16) |
N1—C2—H22 | 108.9 (12) | C15—C10—C9 | 122.28 (15) |
C1—C2—H22 | 106.2 (12) | C11—C10—C9 | 119.18 (15) |
N1—C2—H23 | 110.0 (13) | C12—C11—C10 | 120.63 (18) |
C1—C2—H23 | 107.6 (12) | C12—C11—H11 | 118.3 (14) |
H22—C2—H23 | 110.1 (17) | C10—C11—H11 | 121.0 (14) |
C1—C3—H31 | 109.3 (14) | C13—C12—C11 | 120.32 (19) |
C1—C3—H32 | 109.1 (13) | C13—C12—H12 | 121.3 (12) |
H31—C3—H32 | 109.1 (16) | C11—C12—H12 | 118.3 (13) |
C1—C3—H33 | 111.6 (12) | C12—C13—C14 | 119.54 (17) |
H31—C3—H33 | 110.9 (17) | C12—C13—H13 | 123.6 (17) |
H32—C3—H33 | 106.7 (17) | C14—C13—H13 | 116.8 (17) |
C1—C4—H41 | 108.7 (13) | C13—C14—C15 | 120.62 (19) |
C1—C4—H42 | 110.4 (14) | C13—C14—H14 | 121.3 (12) |
H41—C4—H42 | 109.9 (19) | C15—C14—H14 | 118.0 (12) |
C1—C4—H43 | 113.0 (13) | C10—C15—C14 | 120.35 (18) |
H41—C4—H43 | 105.7 (19) | C10—C15—H15 | 121.9 (12) |
H42—C4—H43 | 109.0 (17) | C14—C15—H15 | 117.7 (12) |
N1—C5—C6 | 105.97 (14) | C17—C16—C21 | 118.60 (16) |
N1—C5—H51 | 110.9 (13) | C17—C16—C9 | 120.95 (15) |
C6—C5—H51 | 109.6 (12) | C21—C16—C9 | 120.32 (14) |
N1—C5—H52 | 109.5 (12) | C18—C17—C16 | 120.70 (17) |
C6—C5—H52 | 114.4 (13) | C18—C17—H17 | 119.8 (12) |
H51—C5—H52 | 106.5 (18) | C16—C17—H17 | 119.5 (12) |
C5—C6—C7 | 102.29 (14) | C19—C18—C17 | 120.38 (17) |
C5—C6—H61 | 110.6 (14) | C19—C18—H18 | 118.8 (14) |
C7—C6—H61 | 114.9 (15) | C17—C18—H18 | 120.9 (14) |
C5—C6—H62 | 109.9 (13) | C18—C19—C20 | 119.25 (17) |
C7—C6—H62 | 109.4 (13) | C18—C19—H19 | 120.5 (13) |
H61—C6—H62 | 109 (2) | C20—C19—H19 | 120.3 (13) |
C6—C7—C8 | 102.19 (14) | C21—C20—C19 | 120.63 (17) |
C6—C7—H71 | 113.1 (15) | C21—C20—H20 | 120.0 (13) |
C8—C7—H71 | 111.7 (14) | C19—C20—H20 | 119.3 (13) |
C6—C7—H72 | 110.1 (14) | C20—C21—C16 | 120.39 (16) |
C8—C7—H72 | 108.6 (14) | C20—C21—H21 | 119.3 (11) |
H71—C7—H72 | 111 (2) | C16—C21—H21 | 120.4 (11) |
N1—C8—C7 | 103.45 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.84 (3) | 1.99 (3) | 2.6223 (18) | 131 (2) |
O2—H2···O1i | 0.85 (3) | 1.99 (3) | 2.8404 (17) | 172 (2) |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
C17H21NO2 | F(000) = 584 |
Mr = 271.35 | Dx = 1.210 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4201 reflections |
a = 9.3438 (2) Å | θ = 2.4–30.0° |
b = 15.9896 (4) Å | µ = 0.08 mm−1 |
c = 10.9479 (3) Å | T = 120 K |
β = 114.441 (1)° | Block, colourless |
V = 1489.08 (6) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Bruker SMART 1K diffractometer | 3416 independent reflections |
Radiation source: fine-focus sealed tube | 2508 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −9→12 |
Tmin = 0.977, Tmax = 0.984 | k = −20→17 |
10283 measured reflections | l = −13→14 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0376P)2 + 0.2784P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3416 reflections | Δρmax = 0.26 e Å−3 |
191 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0050 (15) |
C17H21NO2 | V = 1489.08 (6) Å3 |
Mr = 271.35 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.3438 (2) Å | µ = 0.08 mm−1 |
b = 15.9896 (4) Å | T = 120 K |
c = 10.9479 (3) Å | 0.30 × 0.20 × 0.20 mm |
β = 114.441 (1)° |
Bruker SMART 1K diffractometer | 3416 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2508 reflections with I > 2σ(I) |
Tmin = 0.977, Tmax = 0.984 | Rint = 0.039 |
10283 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.26 e Å−3 |
3416 reflections | Δρmin = −0.18 e Å−3 |
191 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.85622 (13) | 0.05759 (7) | 0.74752 (11) | 0.0209 (3) | |
O1 | 1.00400 (13) | −0.06277 (7) | 0.64116 (13) | 0.0371 (3) | |
O2 | 0.80726 (11) | 0.09856 (6) | 0.49626 (10) | 0.0230 (2) | |
C1 | 1.09664 (17) | −0.00902 (9) | 0.74820 (15) | 0.0274 (3) | |
H1A | 1.1236 | 0.0425 | 0.7121 | 0.033* | |
H1B | 1.1956 | −0.0374 | 0.8066 | 0.033* | |
C2 | 1.00289 (17) | 0.01278 (9) | 0.82778 (14) | 0.0263 (3) | |
H2A | 0.9771 | −0.0393 | 0.8633 | 0.032* | |
H2B | 1.0682 | 0.0480 | 0.9052 | 0.032* | |
C3 | 0.74175 (17) | 0.05058 (9) | 0.80697 (15) | 0.0263 (3) | |
H3A | 0.6438 | 0.0786 | 0.7489 | 0.039* | |
H3B | 0.7845 | 0.0771 | 0.8956 | 0.039* | |
H3C | 0.7206 | −0.0086 | 0.8161 | 0.039* | |
C4 | 0.88563 (16) | 0.14520 (8) | 0.72346 (13) | 0.0202 (3) | |
H4A | 0.9992 | 0.1534 | 0.7478 | 0.024* | |
H4B | 0.8545 | 0.1826 | 0.7803 | 0.024* | |
C5 | 0.78997 (15) | 0.16750 (8) | 0.57320 (13) | 0.0183 (3) | |
C6 | 0.61520 (15) | 0.18108 (8) | 0.54241 (13) | 0.0196 (3) | |
C7 | 0.56931 (16) | 0.25041 (9) | 0.59572 (14) | 0.0240 (3) | |
H7 | 0.6460 | 0.2898 | 0.6486 | 0.029* | |
C8 | 0.41220 (17) | 0.26216 (9) | 0.57198 (16) | 0.0291 (3) | |
H8 | 0.3825 | 0.3094 | 0.6088 | 0.035* | |
C9 | 0.29885 (17) | 0.20507 (10) | 0.49461 (15) | 0.0315 (4) | |
H9 | 0.1916 | 0.2133 | 0.4777 | 0.038* | |
C10 | 0.34365 (17) | 0.13601 (10) | 0.44236 (15) | 0.0297 (4) | |
H10 | 0.2668 | 0.0965 | 0.3902 | 0.036* | |
C11 | 0.50079 (16) | 0.12408 (9) | 0.46581 (14) | 0.0251 (3) | |
H11 | 0.5299 | 0.0766 | 0.4291 | 0.030* | |
C12 | 0.85580 (15) | 0.24542 (8) | 0.53429 (13) | 0.0184 (3) | |
C13 | 0.93583 (16) | 0.30651 (8) | 0.62954 (14) | 0.0233 (3) | |
H13 | 0.9503 | 0.2994 | 0.7201 | 0.028* | |
C14 | 0.99440 (17) | 0.37765 (9) | 0.59293 (15) | 0.0259 (3) | |
H14 | 1.0483 | 0.4188 | 0.6584 | 0.031* | |
C15 | 0.97449 (17) | 0.38869 (9) | 0.46163 (16) | 0.0279 (3) | |
H15 | 1.0154 | 0.4371 | 0.4370 | 0.033* | |
C16 | 0.89443 (18) | 0.32875 (9) | 0.36600 (15) | 0.0270 (3) | |
H16 | 0.8799 | 0.3364 | 0.2756 | 0.032* | |
C17 | 0.83539 (16) | 0.25766 (8) | 0.40184 (14) | 0.0219 (3) | |
H17 | 0.7807 | 0.2170 | 0.3356 | 0.026* | |
H1 | 1.060 (2) | −0.0751 (12) | 0.596 (2) | 0.062 (6)* | |
H2 | 0.816 (2) | 0.0551 (12) | 0.547 (2) | 0.053 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0188 (6) | 0.0214 (6) | 0.0233 (6) | 0.0025 (5) | 0.0096 (5) | 0.0037 (5) |
O1 | 0.0323 (6) | 0.0335 (6) | 0.0558 (8) | −0.0081 (5) | 0.0285 (6) | −0.0159 (6) |
O2 | 0.0292 (5) | 0.0184 (5) | 0.0228 (5) | −0.0001 (4) | 0.0124 (4) | −0.0018 (4) |
C1 | 0.0211 (7) | 0.0259 (7) | 0.0338 (8) | 0.0039 (6) | 0.0100 (6) | 0.0018 (6) |
C2 | 0.0254 (8) | 0.0269 (7) | 0.0243 (7) | 0.0061 (6) | 0.0078 (6) | 0.0069 (6) |
C3 | 0.0256 (7) | 0.0293 (7) | 0.0271 (7) | 0.0028 (6) | 0.0142 (6) | 0.0054 (6) |
C4 | 0.0203 (7) | 0.0210 (7) | 0.0187 (7) | 0.0000 (6) | 0.0073 (5) | 0.0002 (5) |
C5 | 0.0211 (7) | 0.0171 (6) | 0.0174 (6) | −0.0018 (5) | 0.0085 (5) | −0.0023 (5) |
C6 | 0.0199 (7) | 0.0222 (7) | 0.0160 (6) | −0.0010 (5) | 0.0066 (5) | 0.0048 (5) |
C7 | 0.0233 (7) | 0.0238 (7) | 0.0245 (7) | −0.0009 (6) | 0.0096 (6) | 0.0028 (6) |
C8 | 0.0274 (8) | 0.0292 (8) | 0.0351 (8) | 0.0069 (6) | 0.0173 (7) | 0.0093 (7) |
C9 | 0.0184 (7) | 0.0433 (9) | 0.0320 (8) | 0.0036 (7) | 0.0097 (6) | 0.0144 (7) |
C10 | 0.0219 (7) | 0.0399 (9) | 0.0231 (7) | −0.0086 (7) | 0.0052 (6) | 0.0041 (7) |
C11 | 0.0258 (7) | 0.0276 (8) | 0.0193 (7) | −0.0037 (6) | 0.0068 (6) | 0.0020 (6) |
C12 | 0.0157 (6) | 0.0193 (7) | 0.0201 (6) | 0.0015 (5) | 0.0074 (5) | 0.0001 (5) |
C13 | 0.0229 (7) | 0.0250 (7) | 0.0221 (7) | −0.0012 (6) | 0.0095 (6) | −0.0009 (6) |
C14 | 0.0246 (7) | 0.0214 (7) | 0.0333 (8) | −0.0046 (6) | 0.0136 (6) | −0.0037 (6) |
C15 | 0.0302 (8) | 0.0197 (7) | 0.0408 (9) | −0.0001 (6) | 0.0219 (7) | 0.0021 (6) |
C16 | 0.0329 (8) | 0.0275 (7) | 0.0256 (8) | 0.0054 (6) | 0.0170 (6) | 0.0057 (6) |
C17 | 0.0236 (7) | 0.0218 (7) | 0.0213 (7) | 0.0023 (6) | 0.0102 (6) | −0.0006 (6) |
N1—C3 | 1.4684 (17) | C6—C7 | 1.4002 (19) |
N1—C4 | 1.4722 (16) | C7—C8 | 1.394 (2) |
N1—C2 | 1.4721 (17) | C7—H7 | 0.9500 |
O1—C1 | 1.4219 (18) | C8—C9 | 1.389 (2) |
O1—H1 | 0.88 (2) | C8—H8 | 0.9500 |
O2—C5 | 1.4364 (15) | C9—C10 | 1.386 (2) |
O2—H2 | 0.87 (2) | C9—H9 | 0.9500 |
C1—C2 | 1.510 (2) | C10—C11 | 1.395 (2) |
C1—H1A | 0.9900 | C10—H10 | 0.9500 |
C1—H1B | 0.9900 | C11—H11 | 0.9500 |
C2—H2A | 0.9900 | C12—C17 | 1.3959 (19) |
C2—H2B | 0.9900 | C12—C13 | 1.3984 (19) |
C3—H3A | 0.9800 | C13—C14 | 1.3913 (19) |
C3—H3B | 0.9800 | C13—H13 | 0.9500 |
C3—H3C | 0.9800 | C14—C15 | 1.382 (2) |
C4—C5 | 1.5541 (18) | C14—H14 | 0.9500 |
C4—H4A | 0.9900 | C15—C16 | 1.388 (2) |
C4—H4B | 0.9900 | C15—H15 | 0.9500 |
C5—C12 | 1.5261 (18) | C16—C17 | 1.3891 (19) |
C5—C6 | 1.5402 (18) | C16—H16 | 0.9500 |
C6—C11 | 1.3909 (19) | C17—H17 | 0.9500 |
C3—N1—C4 | 112.09 (11) | C11—C6—C5 | 121.36 (12) |
C3—N1—C2 | 111.55 (11) | C7—C6—C5 | 120.01 (12) |
C4—N1—C2 | 111.92 (11) | C8—C7—C6 | 120.64 (13) |
C1—O1—H1 | 107.3 (14) | C8—C7—H7 | 119.7 |
C5—O2—H2 | 104.0 (13) | C6—C7—H7 | 119.7 |
O1—C1—C2 | 108.32 (12) | C9—C8—C7 | 120.23 (14) |
O1—C1—H1A | 110.0 | C9—C8—H8 | 119.9 |
C2—C1—H1A | 110.0 | C7—C8—H8 | 119.9 |
O1—C1—H1B | 110.0 | C10—C9—C8 | 119.41 (14) |
C2—C1—H1B | 110.0 | C10—C9—H9 | 120.3 |
H1A—C1—H1B | 108.4 | C8—C9—H9 | 120.3 |
N1—C2—C1 | 112.77 (11) | C9—C10—C11 | 120.51 (14) |
N1—C2—H2A | 109.0 | C9—C10—H10 | 119.7 |
C1—C2—H2A | 109.0 | C11—C10—H10 | 119.7 |
N1—C2—H2B | 109.0 | C6—C11—C10 | 120.61 (14) |
C1—C2—H2B | 109.0 | C6—C11—H11 | 119.7 |
H2A—C2—H2B | 107.8 | C10—C11—H11 | 119.7 |
N1—C3—H3A | 109.5 | C17—C12—C13 | 118.55 (12) |
N1—C3—H3B | 109.5 | C17—C12—C5 | 120.45 (12) |
H3A—C3—H3B | 109.5 | C13—C12—C5 | 121.00 (12) |
N1—C3—H3C | 109.5 | C14—C13—C12 | 120.59 (13) |
H3A—C3—H3C | 109.5 | C14—C13—H13 | 119.7 |
H3B—C3—H3C | 109.5 | C12—C13—H13 | 119.7 |
N1—C4—C5 | 109.85 (10) | C15—C14—C13 | 120.29 (14) |
N1—C4—H4A | 109.7 | C15—C14—H14 | 119.9 |
C5—C4—H4A | 109.7 | C13—C14—H14 | 119.9 |
N1—C4—H4B | 109.7 | C14—C15—C16 | 119.65 (13) |
C5—C4—H4B | 109.7 | C14—C15—H15 | 120.2 |
H4A—C4—H4B | 108.2 | C16—C15—H15 | 120.2 |
O2—C5—C12 | 107.87 (10) | C15—C16—C17 | 120.34 (13) |
O2—C5—C6 | 110.25 (10) | C15—C16—H16 | 119.8 |
C12—C5—C6 | 109.70 (10) | C17—C16—H16 | 119.8 |
O2—C5—C4 | 106.84 (10) | C16—C17—C12 | 120.57 (13) |
C12—C5—C4 | 111.16 (10) | C16—C17—H17 | 119.7 |
C6—C5—C4 | 110.94 (10) | C12—C17—H17 | 119.7 |
C11—C6—C7 | 118.59 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N1 | 0.87 (2) | 2.07 (2) | 2.6765 (15) | 126.0 (16) |
O1—H1···O2i | 0.88 (2) | 1.93 (2) | 2.8101 (15) | 177 (2) |
Symmetry code: (i) −x+2, −y, −z+1. |
C16H27NO2 | F(000) = 584 |
Mr = 265.39 | Dx = 1.092 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4891 reflections |
a = 8.6781 (5) Å | θ = 2.8–28.7° |
b = 12.8084 (7) Å | µ = 0.07 mm−1 |
c = 14.5243 (8) Å | T = 120 K |
V = 1614.41 (16) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Bruker SMART 1K diffractometer | 2428 independent reflections |
Radiation source: fine-focus sealed tube | 1986 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 29.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −11→11 |
Tmin = 0.979, Tmax = 0.986 | k = −7→17 |
11540 measured reflections | l = −19→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0435P)2 + 0.1881P] where P = (Fo2 + 2Fc2)/3 |
2428 reflections | (Δ/σ)max < 0.001 |
185 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C16H27NO2 | V = 1614.41 (16) Å3 |
Mr = 265.39 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.6781 (5) Å | µ = 0.07 mm−1 |
b = 12.8084 (7) Å | T = 120 K |
c = 14.5243 (8) Å | 0.30 × 0.25 × 0.20 mm |
Bruker SMART 1K diffractometer | 2428 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1986 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.986 | Rint = 0.039 |
11540 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.17 e Å−3 |
2428 reflections | Δρmin = −0.18 e Å−3 |
185 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.33183 (16) | 0.03617 (11) | −0.00955 (10) | 0.0249 (3) | |
O1 | 0.10809 (16) | −0.14653 (9) | 0.01479 (9) | 0.0297 (3) | |
O2 | 0.40324 (16) | −0.18861 (9) | −0.03175 (9) | 0.0320 (3) | |
C1 | 0.4068 (2) | 0.14075 (13) | −0.00743 (12) | 0.0296 (4) | |
H1A | 0.5147 | 0.1301 | −0.0296 | 0.036* | |
C2 | 0.3331 (3) | 0.22025 (15) | −0.07315 (14) | 0.0412 (5) | |
H2A | 0.3319 | 0.1917 | −0.1357 | 0.062* | |
H2B | 0.3931 | 0.2851 | −0.0724 | 0.062* | |
H2C | 0.2273 | 0.2348 | −0.0533 | 0.062* | |
C3 | 0.4195 (2) | 0.17997 (15) | 0.09170 (13) | 0.0339 (4) | |
C4 | 0.4949 (3) | 0.11861 (18) | 0.15682 (15) | 0.0454 (5) | |
H4 | 0.5368 | 0.0531 | 0.1390 | 0.055* | |
C5 | 0.5098 (3) | 0.1519 (2) | 0.24784 (17) | 0.0622 (8) | |
H5 | 0.5596 | 0.1085 | 0.2917 | 0.075* | |
C6 | 0.4526 (4) | 0.2473 (2) | 0.27417 (18) | 0.0727 (9) | |
H6 | 0.4637 | 0.2702 | 0.3360 | 0.087* | |
C7 | 0.3794 (4) | 0.3092 (2) | 0.21094 (18) | 0.0697 (9) | |
H7 | 0.3396 | 0.3752 | 0.2292 | 0.084* | |
C8 | 0.3629 (3) | 0.27612 (18) | 0.11993 (15) | 0.0478 (6) | |
H8 | 0.3123 | 0.3200 | 0.0767 | 0.057* | |
C11 | 0.1692 (2) | 0.04041 (13) | 0.01720 (13) | 0.0284 (4) | |
H11A | 0.1059 | 0.0470 | −0.0392 | 0.034* | |
H11B | 0.1523 | 0.1040 | 0.0546 | 0.034* | |
C12 | 0.1122 (2) | −0.05432 (13) | 0.07207 (12) | 0.0296 (4) | |
C13 | 0.2141 (3) | −0.07307 (16) | 0.15569 (12) | 0.0391 (5) | |
H13A | 0.1701 | −0.1292 | 0.1932 | 0.059* | |
H13B | 0.2203 | −0.0090 | 0.1924 | 0.059* | |
H13C | 0.3177 | −0.0931 | 0.1353 | 0.059* | |
C14 | −0.0548 (2) | −0.03491 (17) | 0.09920 (16) | 0.0432 (5) | |
H14A | −0.0951 | −0.0962 | 0.1317 | 0.065* | |
H14B | −0.1164 | −0.0223 | 0.0437 | 0.065* | |
H14C | −0.0605 | 0.0262 | 0.1396 | 0.065* | |
C21 | 0.3589 (2) | −0.01954 (13) | −0.09660 (11) | 0.0293 (4) | |
H21A | 0.3987 | 0.0310 | −0.1423 | 0.035* | |
H21B | 0.2588 | −0.0457 | −0.1197 | 0.035* | |
C22 | 0.4715 (2) | −0.11187 (14) | −0.09130 (13) | 0.0317 (4) | |
C23 | 0.4893 (3) | −0.15751 (18) | −0.18736 (14) | 0.0543 (7) | |
H23A | 0.5557 | −0.2193 | −0.1846 | 0.081* | |
H23B | 0.5358 | −0.1053 | −0.2281 | 0.081* | |
H23C | 0.3878 | −0.1773 | −0.2113 | 0.081* | |
C24 | 0.6267 (2) | −0.07987 (16) | −0.05172 (17) | 0.0453 (5) | |
H24A | 0.6950 | −0.1407 | −0.0496 | 0.068* | |
H24B | 0.6122 | −0.0524 | 0.0107 | 0.068* | |
H24C | 0.6727 | −0.0258 | −0.0907 | 0.068* | |
H1 | 0.196 (4) | −0.163 (2) | 0.0063 (17) | 0.064 (9)* | |
H2 | 0.470 (3) | −0.242 (2) | −0.0305 (17) | 0.063 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0237 (7) | 0.0204 (6) | 0.0307 (7) | −0.0014 (6) | −0.0026 (6) | 0.0011 (6) |
O1 | 0.0305 (7) | 0.0232 (6) | 0.0355 (6) | −0.0047 (5) | 0.0035 (6) | −0.0051 (5) |
O2 | 0.0319 (7) | 0.0239 (6) | 0.0402 (7) | 0.0062 (6) | 0.0054 (6) | 0.0077 (5) |
C1 | 0.0290 (9) | 0.0251 (8) | 0.0348 (9) | −0.0066 (7) | −0.0018 (8) | 0.0035 (7) |
C2 | 0.0545 (13) | 0.0259 (9) | 0.0431 (11) | −0.0026 (9) | −0.0091 (10) | 0.0053 (8) |
C3 | 0.0290 (9) | 0.0352 (10) | 0.0375 (9) | −0.0155 (8) | −0.0017 (8) | −0.0003 (8) |
C4 | 0.0426 (12) | 0.0487 (13) | 0.0449 (11) | −0.0154 (11) | −0.0135 (10) | 0.0026 (10) |
C5 | 0.0657 (16) | 0.0780 (18) | 0.0429 (11) | −0.0374 (15) | −0.0192 (12) | 0.0082 (14) |
C6 | 0.098 (2) | 0.080 (2) | 0.0400 (13) | −0.0490 (18) | −0.0003 (14) | −0.0118 (13) |
C7 | 0.100 (2) | 0.0548 (15) | 0.0544 (15) | −0.0259 (16) | 0.0164 (17) | −0.0199 (13) |
C8 | 0.0574 (14) | 0.0396 (11) | 0.0464 (12) | −0.0132 (11) | 0.0058 (11) | −0.0047 (10) |
C11 | 0.0250 (8) | 0.0229 (8) | 0.0374 (9) | 0.0004 (7) | −0.0047 (8) | −0.0036 (7) |
C12 | 0.0300 (9) | 0.0256 (8) | 0.0331 (9) | −0.0059 (7) | 0.0020 (8) | −0.0070 (7) |
C13 | 0.0471 (12) | 0.0392 (11) | 0.0310 (10) | −0.0110 (10) | 0.0001 (9) | 0.0005 (8) |
C14 | 0.0349 (10) | 0.0374 (10) | 0.0575 (13) | −0.0071 (9) | 0.0110 (10) | −0.0145 (10) |
C21 | 0.0360 (10) | 0.0259 (8) | 0.0259 (8) | 0.0012 (7) | −0.0022 (8) | 0.0042 (7) |
C22 | 0.0365 (10) | 0.0253 (8) | 0.0333 (9) | 0.0046 (8) | 0.0057 (8) | 0.0061 (7) |
C23 | 0.0846 (19) | 0.0402 (13) | 0.0381 (11) | 0.0200 (13) | 0.0136 (12) | 0.0034 (9) |
C24 | 0.0293 (10) | 0.0357 (10) | 0.0709 (14) | 0.0025 (8) | 0.0046 (10) | 0.0069 (10) |
N1—C11 | 1.465 (2) | C8—H8 | 0.9500 |
N1—C21 | 1.471 (2) | C11—C12 | 1.534 (2) |
N1—C1 | 1.489 (2) | C11—H11A | 0.9900 |
O1—C12 | 1.445 (2) | C11—H11B | 0.9900 |
O1—H1 | 0.80 (3) | C12—C13 | 1.522 (3) |
O2—C22 | 1.437 (2) | C12—C14 | 1.523 (3) |
O2—H2 | 0.89 (3) | C13—H13A | 0.9800 |
C1—C3 | 1.529 (2) | C13—H13B | 0.9800 |
C1—C2 | 1.535 (3) | C13—H13C | 0.9800 |
C1—H1A | 1.0000 | C14—H14A | 0.9800 |
C2—H2A | 0.9800 | C14—H14B | 0.9800 |
C2—H2B | 0.9800 | C14—H14C | 0.9800 |
C2—H2C | 0.9800 | C21—C22 | 1.536 (2) |
C3—C8 | 1.388 (3) | C21—H21A | 0.9900 |
C3—C4 | 1.393 (3) | C21—H21B | 0.9900 |
C4—C5 | 1.395 (3) | C22—C23 | 1.521 (3) |
C4—H4 | 0.9500 | C22—C24 | 1.520 (3) |
C5—C6 | 1.372 (4) | C23—H23A | 0.9800 |
C5—H5 | 0.9500 | C23—H23B | 0.9800 |
C6—C7 | 1.370 (4) | C23—H23C | 0.9800 |
C6—H6 | 0.9500 | C24—H24A | 0.9800 |
C7—C8 | 1.396 (3) | C24—H24B | 0.9800 |
C7—H7 | 0.9500 | C24—H24C | 0.9800 |
C11—N1—C21 | 113.58 (14) | O1—C12—C14 | 105.01 (14) |
C11—N1—C1 | 112.45 (13) | C13—C12—C14 | 111.89 (16) |
C21—N1—C1 | 112.60 (13) | O1—C12—C11 | 110.82 (14) |
C12—O1—H1 | 106.5 (19) | C13—C12—C11 | 110.61 (15) |
C22—O2—H2 | 105.7 (17) | C14—C12—C11 | 108.20 (16) |
N1—C1—C3 | 110.28 (14) | C12—C13—H13A | 109.5 |
N1—C1—C2 | 113.69 (15) | C12—C13—H13B | 109.5 |
C3—C1—C2 | 113.44 (16) | H13A—C13—H13B | 109.5 |
N1—C1—H1A | 106.3 | C12—C13—H13C | 109.5 |
C3—C1—H1A | 106.3 | H13A—C13—H13C | 109.5 |
C2—C1—H1A | 106.3 | H13B—C13—H13C | 109.5 |
C1—C2—H2A | 109.5 | C12—C14—H14A | 109.5 |
C1—C2—H2B | 109.5 | C12—C14—H14B | 109.5 |
H2A—C2—H2B | 109.5 | H14A—C14—H14B | 109.5 |
C1—C2—H2C | 109.5 | C12—C14—H14C | 109.5 |
H2A—C2—H2C | 109.5 | H14A—C14—H14C | 109.5 |
H2B—C2—H2C | 109.5 | H14B—C14—H14C | 109.5 |
C8—C3—C4 | 117.8 (2) | N1—C21—C22 | 115.61 (14) |
C8—C3—C1 | 122.96 (18) | N1—C21—H21A | 108.4 |
C4—C3—C1 | 119.22 (18) | C22—C21—H21A | 108.4 |
C3—C4—C5 | 121.0 (2) | N1—C21—H21B | 108.4 |
C3—C4—H4 | 119.5 | C22—C21—H21B | 108.4 |
C5—C4—H4 | 119.5 | H21A—C21—H21B | 107.4 |
C6—C5—C4 | 120.2 (3) | O2—C22—C23 | 109.34 (16) |
C6—C5—H5 | 119.9 | O2—C22—C24 | 108.78 (16) |
C4—C5—H5 | 119.9 | C23—C22—C24 | 111.15 (19) |
C7—C6—C5 | 119.8 (2) | O2—C22—C21 | 107.13 (14) |
C7—C6—H6 | 120.1 | C23—C22—C21 | 108.34 (16) |
C5—C6—H6 | 120.1 | C24—C22—C21 | 112.01 (15) |
C6—C7—C8 | 120.4 (3) | C22—C23—H23A | 109.5 |
C6—C7—H7 | 119.8 | C22—C23—H23B | 109.5 |
C8—C7—H7 | 119.8 | H23A—C23—H23B | 109.5 |
C3—C8—C7 | 120.9 (3) | C22—C23—H23C | 109.5 |
C3—C8—H8 | 119.6 | H23A—C23—H23C | 109.5 |
C7—C8—H8 | 119.6 | H23B—C23—H23C | 109.5 |
N1—C11—C12 | 114.78 (15) | C22—C24—H24A | 109.5 |
N1—C11—H11A | 108.6 | C22—C24—H24B | 109.5 |
C12—C11—H11A | 108.6 | H24A—C24—H24B | 109.5 |
N1—C11—H11B | 108.6 | C22—C24—H24C | 109.5 |
C12—C11—H11B | 108.6 | H24A—C24—H24C | 109.5 |
H11A—C11—H11B | 107.5 | H24B—C24—H24C | 109.5 |
O1—C12—C13 | 110.17 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.80 (3) | 1.91 (3) | 2.703 (2) | 170 (3) |
O2—H2···O1i | 0.89 (3) | 1.88 (3) | 2.7713 (18) | 174 (2) |
Symmetry code: (i) x+1/2, −y−1/2, −z. |
C20H27NO2 | F(000) = 680 |
Mr = 313.43 | Dx = 1.131 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5538 reflections |
a = 8.9681 (8) Å | θ = 2.5–29.4° |
b = 12.5151 (11) Å | µ = 0.07 mm−1 |
c = 16.3960 (14) Å | T = 120 K |
V = 1840.2 (3) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.20 × 0.10 mm |
Bruker SMART 1K diffractometer | 2772 independent reflections |
Radiation source: fine-focus sealed tube | 2376 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ω scans | θmax = 29.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −6→12 |
Tmin = 0.982, Tmax = 0.993 | k = −17→15 |
13036 measured reflections | l = −16→22 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0347P)2 + 0.2857P] where P = (Fo2 + 2Fc2)/3 |
2772 reflections | (Δ/σ)max < 0.001 |
219 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C20H27NO2 | V = 1840.2 (3) Å3 |
Mr = 313.43 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.9681 (8) Å | µ = 0.07 mm−1 |
b = 12.5151 (11) Å | T = 120 K |
c = 16.3960 (14) Å | 0.25 × 0.20 × 0.10 mm |
Bruker SMART 1K diffractometer | 2772 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2376 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.993 | Rint = 0.045 |
13036 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.086 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.25 e Å−3 |
2772 reflections | Δρmin = −0.19 e Å−3 |
219 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.85952 (16) | 0.77498 (11) | 0.19666 (9) | 0.0187 (3) | |
O1 | 1.09159 (15) | 0.79961 (11) | 0.07312 (8) | 0.0242 (3) | |
O2 | 0.82898 (15) | 0.69725 (11) | 0.03022 (8) | 0.0244 (3) | |
C1 | 0.74550 (19) | 0.79181 (14) | 0.26025 (10) | 0.0205 (3) | |
H11 | 0.6548 | 0.7518 | 0.2422 | 0.025* | |
C2 | 0.7875 (2) | 0.74692 (15) | 0.34383 (11) | 0.0283 (4) | |
H2A | 0.8006 | 0.6694 | 0.3398 | 0.042* | |
H2B | 0.7080 | 0.7629 | 0.3830 | 0.042* | |
H2C | 0.8808 | 0.7797 | 0.3623 | 0.042* | |
C3 | 0.70169 (19) | 0.90978 (15) | 0.26258 (11) | 0.0214 (4) | |
C4 | 0.7442 (2) | 0.97833 (15) | 0.32537 (12) | 0.0266 (4) | |
H4 | 0.7999 | 0.9513 | 0.3701 | 0.032* | |
C5 | 0.7059 (2) | 1.08579 (16) | 0.32311 (13) | 0.0302 (4) | |
H5 | 0.7364 | 1.1319 | 0.3660 | 0.036* | |
C6 | 0.6240 (2) | 1.12599 (16) | 0.25894 (14) | 0.0326 (5) | |
H6 | 0.5986 | 1.1997 | 0.2574 | 0.039* | |
C7 | 0.5788 (2) | 1.05855 (15) | 0.19666 (13) | 0.0310 (4) | |
H7 | 0.5214 | 1.0857 | 0.1526 | 0.037* | |
C8 | 0.6173 (2) | 0.95203 (15) | 0.19879 (12) | 0.0256 (4) | |
H8 | 0.5857 | 0.9063 | 0.1559 | 0.031* | |
C11 | 0.8686 (2) | 0.66259 (13) | 0.17157 (10) | 0.0199 (4) | |
H11A | 0.8371 | 0.6167 | 0.2177 | 0.024* | |
H11B | 0.9736 | 0.6450 | 0.1586 | 0.024* | |
C12 | 0.7717 (2) | 0.63768 (13) | 0.09766 (10) | 0.0199 (4) | |
H12 | 0.6668 | 0.6605 | 0.1089 | 0.024* | |
C13 | 0.7751 (2) | 0.51779 (14) | 0.08189 (10) | 0.0208 (4) | |
C14 | 0.6618 (2) | 0.45290 (15) | 0.11208 (12) | 0.0270 (4) | |
H14 | 0.5791 | 0.4841 | 0.1394 | 0.032* | |
C15 | 0.6691 (3) | 0.34255 (16) | 0.10237 (13) | 0.0352 (5) | |
H15 | 0.5915 | 0.2986 | 0.1232 | 0.042* | |
C16 | 0.7885 (3) | 0.29681 (17) | 0.06266 (12) | 0.0371 (5) | |
H16 | 0.7937 | 0.2214 | 0.0567 | 0.044* | |
C17 | 0.9011 (3) | 0.36087 (16) | 0.03131 (12) | 0.0338 (5) | |
H17 | 0.9827 | 0.3294 | 0.0033 | 0.041* | |
C18 | 0.8944 (2) | 0.47086 (16) | 0.04095 (11) | 0.0260 (4) | |
H18 | 0.9717 | 0.5145 | 0.0195 | 0.031* | |
C21 | 1.0045 (2) | 0.82471 (14) | 0.21296 (10) | 0.0194 (3) | |
H21A | 1.0741 | 0.7695 | 0.2334 | 0.023* | |
H21B | 0.9923 | 0.8790 | 0.2564 | 0.023* | |
C22 | 1.0727 (2) | 0.87806 (14) | 0.13747 (10) | 0.0203 (4) | |
C23 | 0.9759 (2) | 0.96925 (16) | 0.10625 (13) | 0.0308 (4) | |
H23A | 1.0221 | 1.0007 | 0.0577 | 0.046* | |
H23B | 0.9666 | 1.0239 | 0.1487 | 0.046* | |
H23C | 0.8768 | 0.9418 | 0.0922 | 0.046* | |
C24 | 1.2299 (2) | 0.91583 (15) | 0.15766 (12) | 0.0258 (4) | |
H24A | 1.2707 | 0.9553 | 0.1111 | 0.039* | |
H24B | 1.2933 | 0.8539 | 0.1693 | 0.039* | |
H24C | 1.2268 | 0.9626 | 0.2056 | 0.039* | |
H2 | 0.753 (3) | 0.701 (2) | −0.0058 (16) | 0.056 (8)* | |
H1 | 1.005 (3) | 0.7799 (18) | 0.0595 (14) | 0.041 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0182 (7) | 0.0190 (7) | 0.0190 (7) | −0.0023 (6) | 0.0016 (6) | −0.0007 (6) |
O1 | 0.0208 (7) | 0.0315 (7) | 0.0203 (6) | −0.0060 (6) | 0.0035 (5) | −0.0054 (5) |
O2 | 0.0262 (7) | 0.0267 (7) | 0.0202 (6) | −0.0055 (6) | −0.0051 (6) | 0.0049 (5) |
C1 | 0.0181 (8) | 0.0214 (8) | 0.0219 (8) | −0.0035 (7) | 0.0028 (7) | −0.0002 (7) |
C2 | 0.0366 (11) | 0.0270 (9) | 0.0213 (9) | 0.0014 (9) | 0.0073 (8) | 0.0024 (8) |
C3 | 0.0158 (8) | 0.0238 (8) | 0.0248 (9) | −0.0023 (7) | 0.0049 (7) | 0.0006 (7) |
C4 | 0.0205 (9) | 0.0289 (10) | 0.0304 (10) | −0.0013 (8) | 0.0009 (8) | −0.0032 (8) |
C5 | 0.0224 (9) | 0.0278 (9) | 0.0405 (11) | −0.0026 (8) | 0.0019 (8) | −0.0083 (9) |
C6 | 0.0231 (9) | 0.0228 (9) | 0.0519 (13) | 0.0018 (8) | 0.0048 (10) | 0.0007 (9) |
C7 | 0.0212 (9) | 0.0315 (11) | 0.0405 (11) | 0.0008 (8) | −0.0010 (9) | 0.0079 (9) |
C8 | 0.0198 (8) | 0.0293 (10) | 0.0277 (9) | −0.0027 (8) | 0.0016 (8) | −0.0017 (8) |
C11 | 0.0208 (8) | 0.0190 (8) | 0.0200 (8) | −0.0007 (7) | −0.0011 (7) | 0.0001 (7) |
C12 | 0.0195 (8) | 0.0193 (8) | 0.0208 (8) | −0.0012 (7) | 0.0000 (7) | 0.0011 (7) |
C13 | 0.0233 (9) | 0.0215 (9) | 0.0176 (8) | −0.0002 (7) | −0.0058 (7) | −0.0008 (7) |
C14 | 0.0288 (10) | 0.0265 (9) | 0.0258 (9) | −0.0032 (8) | −0.0017 (8) | −0.0008 (8) |
C15 | 0.0476 (13) | 0.0250 (10) | 0.0330 (11) | −0.0089 (10) | −0.0061 (10) | 0.0021 (8) |
C16 | 0.0575 (14) | 0.0223 (10) | 0.0313 (11) | 0.0031 (11) | −0.0142 (10) | −0.0036 (8) |
C17 | 0.0416 (12) | 0.0364 (11) | 0.0234 (9) | 0.0130 (10) | −0.0065 (9) | −0.0091 (9) |
C18 | 0.0250 (9) | 0.0321 (10) | 0.0208 (9) | 0.0018 (8) | −0.0027 (8) | −0.0008 (8) |
C21 | 0.0178 (8) | 0.0202 (8) | 0.0203 (8) | −0.0013 (7) | 0.0015 (7) | −0.0011 (7) |
C22 | 0.0200 (8) | 0.0200 (8) | 0.0208 (8) | −0.0025 (7) | 0.0023 (7) | −0.0012 (7) |
C23 | 0.0266 (10) | 0.0312 (10) | 0.0344 (10) | −0.0001 (9) | 0.0055 (9) | 0.0095 (9) |
C24 | 0.0217 (9) | 0.0278 (9) | 0.0280 (9) | −0.0041 (8) | 0.0038 (8) | −0.0048 (8) |
N1—C21 | 1.466 (2) | C11—H11B | 0.9900 |
N1—C11 | 1.468 (2) | C12—C13 | 1.523 (2) |
N1—C1 | 1.475 (2) | C12—H12 | 1.0000 |
O1—C22 | 1.451 (2) | C13—C18 | 1.393 (3) |
O1—H1 | 0.84 (3) | C13—C14 | 1.392 (3) |
O2—C12 | 1.429 (2) | C14—C15 | 1.392 (3) |
O2—H2 | 0.90 (3) | C14—H14 | 0.9500 |
C1—C2 | 1.528 (2) | C15—C16 | 1.378 (3) |
C1—C3 | 1.528 (2) | C15—H15 | 0.9500 |
C1—H11 | 1.0000 | C16—C17 | 1.388 (3) |
C2—H2A | 0.9800 | C16—H16 | 0.9500 |
C2—H2B | 0.9800 | C17—C18 | 1.387 (3) |
C2—H2C | 0.9800 | C17—H17 | 0.9500 |
C3—C4 | 1.393 (3) | C18—H18 | 0.9500 |
C3—C8 | 1.395 (3) | C21—C22 | 1.534 (2) |
C4—C5 | 1.388 (3) | C21—H21A | 0.9900 |
C4—H4 | 0.9500 | C21—H21B | 0.9900 |
C5—C6 | 1.378 (3) | C22—C23 | 1.522 (3) |
C5—H5 | 0.9500 | C22—C24 | 1.523 (3) |
C6—C7 | 1.385 (3) | C23—H23A | 0.9800 |
C6—H6 | 0.9500 | C23—H23B | 0.9800 |
C7—C8 | 1.378 (3) | C23—H23C | 0.9800 |
C7—H7 | 0.9500 | C24—H24A | 0.9800 |
C8—H8 | 0.9500 | C24—H24B | 0.9800 |
C11—C12 | 1.523 (2) | C24—H24C | 0.9800 |
C11—H11A | 0.9900 | ||
C21—N1—C11 | 114.14 (14) | C13—C12—H12 | 109.4 |
C21—N1—C1 | 115.16 (13) | C11—C12—H12 | 109.4 |
C11—N1—C1 | 111.92 (13) | C18—C13—C14 | 119.09 (17) |
C22—O1—H1 | 106.6 (16) | C18—C13—C12 | 120.83 (17) |
C12—O2—H2 | 105.3 (17) | C14—C13—C12 | 120.00 (17) |
N1—C1—C2 | 114.23 (15) | C15—C14—C13 | 120.3 (2) |
N1—C1—C3 | 109.50 (13) | C15—C14—H14 | 119.9 |
C2—C1—C3 | 113.34 (15) | C13—C14—H14 | 119.9 |
N1—C1—H11 | 106.4 | C16—C15—C14 | 120.2 (2) |
C2—C1—H11 | 106.4 | C16—C15—H15 | 119.9 |
C3—C1—H11 | 106.4 | C14—C15—H15 | 119.9 |
C1—C2—H2A | 109.5 | C15—C16—C17 | 120.03 (19) |
C1—C2—H2B | 109.5 | C15—C16—H16 | 120.0 |
H2A—C2—H2B | 109.5 | C17—C16—H16 | 120.0 |
C1—C2—H2C | 109.5 | C18—C17—C16 | 120.0 (2) |
H2A—C2—H2C | 109.5 | C18—C17—H17 | 120.0 |
H2B—C2—H2C | 109.5 | C16—C17—H17 | 120.0 |
C4—C3—C8 | 117.97 (17) | C17—C18—C13 | 120.42 (19) |
C4—C3—C1 | 122.88 (16) | C17—C18—H18 | 119.8 |
C8—C3—C1 | 119.14 (16) | C13—C18—H18 | 119.8 |
C5—C4—C3 | 120.60 (19) | N1—C21—C22 | 113.05 (14) |
C5—C4—H4 | 119.7 | N1—C21—H21A | 109.0 |
C3—C4—H4 | 119.7 | C22—C21—H21A | 109.0 |
C6—C5—C4 | 120.38 (19) | N1—C21—H21B | 109.0 |
C6—C5—H5 | 119.8 | C22—C21—H21B | 109.0 |
C4—C5—H5 | 119.8 | H21A—C21—H21B | 107.8 |
C5—C6—C7 | 119.74 (18) | O1—C22—C23 | 109.22 (15) |
C5—C6—H6 | 120.1 | O1—C22—C24 | 105.07 (14) |
C7—C6—H6 | 120.1 | C23—C22—C24 | 111.58 (15) |
C8—C7—C6 | 119.85 (19) | O1—C22—C21 | 109.81 (13) |
C8—C7—H7 | 120.1 | C23—C22—C21 | 111.73 (15) |
C6—C7—H7 | 120.1 | C24—C22—C21 | 109.21 (15) |
C7—C8—C3 | 121.45 (19) | C22—C23—H23A | 109.5 |
C7—C8—H8 | 119.3 | C22—C23—H23B | 109.5 |
C3—C8—H8 | 119.3 | H23A—C23—H23B | 109.5 |
N1—C11—C12 | 112.80 (14) | C22—C23—H23C | 109.5 |
N1—C11—H11A | 109.0 | H23A—C23—H23C | 109.5 |
C12—C11—H11A | 109.0 | H23B—C23—H23C | 109.5 |
N1—C11—H11B | 109.0 | C22—C24—H24A | 109.5 |
C12—C11—H11B | 109.0 | C22—C24—H24B | 109.5 |
H11A—C11—H11B | 107.8 | H24A—C24—H24B | 109.5 |
O2—C12—C13 | 112.05 (14) | C22—C24—H24C | 109.5 |
O2—C12—C11 | 107.67 (14) | H24A—C24—H24C | 109.5 |
C13—C12—C11 | 108.99 (14) | H24B—C24—H24C | 109.5 |
O2—C12—H12 | 109.4 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.84 (3) | 1.95 (3) | 2.7717 (19) | 165 (2) |
O2—H2···O1i | 0.90 (3) | 1.82 (3) | 2.7211 (18) | 175 (2) |
Symmetry code: (i) x−1/2, −y+3/2, −z. |
C17H21NO2 | F(000) = 584 |
Mr = 271.35 | Dx = 1.208 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5344 reflections |
a = 9.5577 (9) Å | θ = 2.4–30.4° |
b = 9.9481 (9) Å | µ = 0.08 mm−1 |
c = 15.9403 (15) Å | T = 100 K |
β = 100.136 (2)° | Plate, colourless |
V = 1492.0 (2) Å3 | 0.18 × 0.16 × 0.04 mm |
Z = 4 |
Bruker SMART 1K diffractometer | 2932 independent reflections |
Radiation source: fine-focus sealed tube | 2482 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −9→11 |
Tmin = 0.986, Tmax = 0.997 | k = −12→11 |
7956 measured reflections | l = −19→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0395P)2 + 0.4707P] where P = (Fo2 + 2Fc2)/3 |
2932 reflections | (Δ/σ)max < 0.001 |
195 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C17H21NO2 | V = 1492.0 (2) Å3 |
Mr = 271.35 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.5577 (9) Å | µ = 0.08 mm−1 |
b = 9.9481 (9) Å | T = 100 K |
c = 15.9403 (15) Å | 0.18 × 0.16 × 0.04 mm |
β = 100.136 (2)° |
Bruker SMART 1K diffractometer | 2932 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2482 reflections with I > 2σ(I) |
Tmin = 0.986, Tmax = 0.997 | Rint = 0.022 |
7956 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.24 e Å−3 |
2932 reflections | Δρmin = −0.25 e Å−3 |
195 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.13144 (11) | 0.27954 (10) | 0.52216 (6) | 0.0168 (2) | |
O1 | 0.37764 (12) | 0.44412 (10) | 0.52060 (7) | 0.0256 (2) | |
H1A | 0.296 (5) | 0.473 (4) | 0.501 (2) | 0.038* | 0.490 (18) |
H1B | 0.450 (3) | 0.487 (4) | 0.504 (2) | 0.038* | 0.510 (18) |
O2 | −0.10814 (12) | 0.43810 (9) | 0.53834 (6) | 0.0216 (2) | |
H2A | −0.191 (4) | 0.472 (4) | 0.514 (2) | 0.032* | 0.490 (18) |
H2B | −0.043 (4) | 0.460 (3) | 0.510 (2) | 0.032* | 0.510 (18) |
C1 | 0.38458 (14) | 0.30256 (13) | 0.50782 (8) | 0.0219 (3) | |
H11A | 0.4813 | 0.2698 | 0.5315 | 0.026* | |
H11B | 0.3654 | 0.2827 | 0.4460 | 0.026* | |
C2 | 0.27655 (13) | 0.23023 (13) | 0.55095 (8) | 0.0193 (3) | |
H21A | 0.2799 | 0.1328 | 0.5388 | 0.023* | |
H21B | 0.3023 | 0.2426 | 0.6134 | 0.023* | |
C3 | 0.07927 (14) | 0.24067 (14) | 0.43373 (8) | 0.0233 (3) | |
H3A | 0.1532 | 0.2578 | 0.3995 | 0.035* | |
H3B | −0.0056 | 0.2934 | 0.4111 | 0.035* | |
H3C | 0.0553 | 0.1448 | 0.4313 | 0.035* | |
C4 | 0.03329 (13) | 0.23669 (12) | 0.57829 (8) | 0.0163 (3) | |
H4A | 0.0255 | 0.1365 | 0.5750 | 0.020* | |
C5 | −0.11683 (13) | 0.29630 (12) | 0.54587 (8) | 0.0171 (3) | |
H5 | −0.1530 | 0.2584 | 0.4880 | 0.021* | |
C6 | 0.06569 (14) | 0.18334 (14) | 0.73457 (8) | 0.0214 (3) | |
H6 | 0.0287 | 0.0964 | 0.7191 | 0.026* | |
C7 | 0.10109 (15) | 0.21730 (15) | 0.82022 (8) | 0.0274 (3) | |
H7 | 0.0888 | 0.1541 | 0.8630 | 0.033* | |
C8 | 0.15458 (15) | 0.34431 (15) | 0.84275 (9) | 0.0283 (3) | |
H8 | 0.1770 | 0.3691 | 0.9011 | 0.034* | |
C9 | 0.17529 (14) | 0.43510 (14) | 0.78005 (9) | 0.0251 (3) | |
H9 | 0.2139 | 0.5214 | 0.7958 | 0.030* | |
C10 | 0.14015 (13) | 0.40100 (13) | 0.69453 (8) | 0.0200 (3) | |
H10 | 0.1547 | 0.4638 | 0.6520 | 0.024* | |
C11 | 0.08351 (13) | 0.27458 (13) | 0.67089 (8) | 0.0172 (3) | |
C12 | −0.21970 (13) | 0.25736 (13) | 0.60404 (8) | 0.0169 (3) | |
C13 | −0.26413 (13) | 0.34890 (13) | 0.65996 (8) | 0.0203 (3) | |
H13 | −0.2319 | 0.4393 | 0.6612 | 0.024* | |
C14 | −0.35558 (14) | 0.30825 (14) | 0.71397 (8) | 0.0248 (3) | |
H14 | −0.3861 | 0.3714 | 0.7517 | 0.030* | |
C15 | −0.40267 (14) | 0.17624 (15) | 0.71330 (8) | 0.0248 (3) | |
H15 | −0.4647 | 0.1490 | 0.7506 | 0.030* | |
C16 | −0.35869 (14) | 0.08426 (14) | 0.65787 (8) | 0.0233 (3) | |
H16 | −0.3902 | −0.0064 | 0.6573 | 0.028* | |
C17 | −0.26856 (13) | 0.12498 (13) | 0.60331 (8) | 0.0199 (3) | |
H17 | −0.2397 | 0.0620 | 0.5649 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0166 (5) | 0.0185 (5) | 0.0156 (5) | 0.0007 (4) | 0.0036 (4) | 0.0009 (4) |
O1 | 0.0182 (5) | 0.0206 (5) | 0.0385 (6) | −0.0013 (4) | 0.0070 (4) | 0.0044 (4) |
O2 | 0.0200 (5) | 0.0174 (5) | 0.0280 (5) | 0.0015 (4) | 0.0058 (4) | 0.0074 (4) |
C1 | 0.0197 (7) | 0.0224 (7) | 0.0243 (7) | 0.0035 (5) | 0.0057 (5) | 0.0018 (5) |
C2 | 0.0188 (6) | 0.0188 (6) | 0.0206 (6) | 0.0033 (5) | 0.0042 (5) | 0.0017 (5) |
C3 | 0.0225 (7) | 0.0288 (7) | 0.0190 (6) | 0.0000 (5) | 0.0049 (5) | −0.0014 (5) |
C4 | 0.0183 (6) | 0.0119 (6) | 0.0189 (6) | −0.0002 (5) | 0.0038 (5) | 0.0010 (5) |
C5 | 0.0174 (6) | 0.0156 (6) | 0.0180 (6) | −0.0013 (5) | 0.0018 (5) | 0.0011 (5) |
C6 | 0.0202 (6) | 0.0216 (7) | 0.0230 (7) | 0.0022 (5) | 0.0049 (5) | 0.0035 (5) |
C7 | 0.0258 (7) | 0.0367 (8) | 0.0202 (7) | 0.0092 (6) | 0.0055 (5) | 0.0086 (6) |
C8 | 0.0264 (7) | 0.0396 (9) | 0.0178 (6) | 0.0119 (6) | 0.0003 (5) | −0.0035 (6) |
C9 | 0.0203 (7) | 0.0267 (7) | 0.0265 (7) | 0.0047 (6) | −0.0008 (5) | −0.0070 (6) |
C10 | 0.0179 (6) | 0.0189 (6) | 0.0230 (7) | 0.0020 (5) | 0.0032 (5) | 0.0001 (5) |
C11 | 0.0137 (6) | 0.0191 (6) | 0.0189 (6) | 0.0029 (5) | 0.0034 (5) | 0.0013 (5) |
C12 | 0.0139 (6) | 0.0186 (6) | 0.0171 (6) | −0.0005 (5) | −0.0004 (5) | 0.0027 (5) |
C13 | 0.0210 (6) | 0.0193 (7) | 0.0202 (6) | −0.0027 (5) | 0.0026 (5) | 0.0001 (5) |
C14 | 0.0260 (7) | 0.0283 (7) | 0.0210 (6) | −0.0003 (6) | 0.0065 (5) | −0.0024 (6) |
C15 | 0.0218 (7) | 0.0332 (8) | 0.0203 (6) | −0.0054 (6) | 0.0057 (5) | 0.0055 (6) |
C16 | 0.0212 (7) | 0.0216 (7) | 0.0255 (7) | −0.0055 (5) | 0.0003 (5) | 0.0060 (5) |
C17 | 0.0187 (6) | 0.0180 (6) | 0.0222 (6) | 0.0004 (5) | 0.0012 (5) | 0.0014 (5) |
N1—C3 | 1.4621 (16) | C6—C7 | 1.3892 (19) |
N1—C2 | 1.4666 (16) | C6—C11 | 1.3944 (18) |
N1—C4 | 1.4689 (15) | C6—H6 | 0.9500 |
O1—C1 | 1.4261 (16) | C7—C8 | 1.386 (2) |
O1—H1A | 0.83 (5) | C7—H7 | 0.9500 |
O1—H1B | 0.89 (3) | C8—C9 | 1.387 (2) |
O2—C5 | 1.4194 (15) | C8—H8 | 0.9500 |
O2—H2A | 0.88 (4) | C9—C10 | 1.3874 (18) |
O2—H2B | 0.85 (3) | C9—H9 | 0.9500 |
C1—C2 | 1.5186 (18) | C10—C11 | 1.3947 (18) |
C1—H11A | 0.9900 | C10—H10 | 0.9500 |
C1—H11B | 0.9900 | C12—C13 | 1.3919 (18) |
C2—H21A | 0.9900 | C12—C17 | 1.3967 (18) |
C2—H21B | 0.9900 | C13—C14 | 1.3905 (18) |
C3—H3A | 0.9800 | C13—H13 | 0.9500 |
C3—H3B | 0.9800 | C14—C15 | 1.388 (2) |
C3—H3C | 0.9800 | C14—H14 | 0.9500 |
C4—C11 | 1.5172 (17) | C15—C16 | 1.388 (2) |
C4—C5 | 1.5545 (17) | C15—H15 | 0.9500 |
C4—H4A | 1.0000 | C16—C17 | 1.3879 (19) |
C5—C12 | 1.5156 (17) | C16—H16 | 0.9500 |
C5—H5 | 1.0000 | C17—H17 | 0.9500 |
C3—N1—C2 | 110.88 (10) | C4—C5—H5 | 108.2 |
C3—N1—C4 | 111.38 (10) | C7—C6—C11 | 121.15 (13) |
C2—N1—C4 | 112.49 (9) | C7—C6—H6 | 119.4 |
C1—O1—H1A | 110 (3) | C11—C6—H6 | 119.4 |
C1—O1—H1B | 112 (2) | C8—C7—C6 | 119.42 (13) |
H1A—O1—H1B | 116 (3) | C8—C7—H7 | 120.3 |
C5—O2—H2A | 111 (2) | C6—C7—H7 | 120.3 |
C5—O2—H2B | 111 (2) | C7—C8—C9 | 119.98 (12) |
H2A—O2—H2B | 111 (3) | C7—C8—H8 | 120.0 |
O1—C1—C2 | 110.53 (11) | C9—C8—H8 | 120.0 |
O1—C1—H11A | 109.5 | C8—C9—C10 | 120.54 (13) |
C2—C1—H11A | 109.5 | C8—C9—H9 | 119.7 |
O1—C1—H11B | 109.5 | C10—C9—H9 | 119.7 |
C2—C1—H11B | 109.5 | C9—C10—C11 | 120.09 (12) |
H11A—C1—H11B | 108.1 | C9—C10—H10 | 120.0 |
N1—C2—C1 | 112.38 (10) | C11—C10—H10 | 120.0 |
N1—C2—H21A | 109.1 | C6—C11—C10 | 118.79 (12) |
C1—C2—H21A | 109.1 | C6—C11—C4 | 119.23 (11) |
N1—C2—H21B | 109.1 | C10—C11—C4 | 121.89 (11) |
C1—C2—H21B | 109.1 | C13—C12—C17 | 118.88 (11) |
H21A—C2—H21B | 107.9 | C13—C12—C5 | 121.90 (11) |
N1—C3—H3A | 109.5 | C17—C12—C5 | 119.20 (11) |
N1—C3—H3B | 109.5 | C14—C13—C12 | 120.14 (12) |
H3A—C3—H3B | 109.5 | C14—C13—H13 | 119.9 |
N1—C3—H3C | 109.5 | C12—C13—H13 | 119.9 |
H3A—C3—H3C | 109.5 | C15—C14—C13 | 120.59 (13) |
H3B—C3—H3C | 109.5 | C15—C14—H14 | 119.7 |
N1—C4—C11 | 113.20 (10) | C13—C14—H14 | 119.7 |
N1—C4—C5 | 109.75 (9) | C16—C15—C14 | 119.65 (12) |
C11—C4—C5 | 110.13 (10) | C16—C15—H15 | 120.2 |
N1—C4—H4A | 107.9 | C14—C15—H15 | 120.2 |
C11—C4—H4A | 107.9 | C15—C16—C17 | 119.84 (12) |
C5—C4—H4A | 107.9 | C15—C16—H16 | 120.1 |
O2—C5—C12 | 111.08 (10) | C17—C16—H16 | 120.1 |
O2—C5—C4 | 110.05 (10) | C16—C17—C12 | 120.90 (12) |
C12—C5—C4 | 111.06 (10) | C16—C17—H17 | 119.6 |
O2—C5—H5 | 108.2 | C12—C17—H17 | 119.6 |
C12—C5—H5 | 108.2 | ||
C3—N1—C2—C1 | 69.45 (14) | C9—C10—C11—C4 | 175.32 (11) |
C4—N1—C2—C1 | −165.08 (10) | N1—C4—C11—C6 | −139.83 (11) |
O1—C1—C2—N1 | 55.99 (14) | C5—C4—C11—C6 | 96.90 (13) |
C3—N1—C4—C11 | 179.80 (10) | N1—C4—C11—C10 | 43.69 (16) |
C2—N1—C4—C11 | 54.61 (14) | C5—C4—C11—C10 | −79.58 (14) |
C3—N1—C4—C5 | −56.72 (13) | O2—C5—C12—C13 | −17.12 (16) |
C2—N1—C4—C5 | 178.09 (10) | C4—C5—C12—C13 | 105.71 (13) |
N1—C4—C5—O2 | −54.85 (13) | O2—C5—C12—C17 | 164.63 (11) |
C11—C4—C5—O2 | 70.41 (12) | C4—C5—C12—C17 | −72.53 (14) |
N1—C4—C5—C12 | −178.28 (10) | C17—C12—C13—C14 | 0.03 (18) |
C11—C4—C5—C12 | −53.01 (13) | C5—C12—C13—C14 | −178.22 (12) |
C11—C6—C7—C8 | 0.2 (2) | C12—C13—C14—C15 | 0.5 (2) |
C6—C7—C8—C9 | −1.4 (2) | C13—C14—C15—C16 | −0.4 (2) |
C7—C8—C9—C10 | 1.3 (2) | C14—C15—C16—C17 | −0.3 (2) |
C8—C9—C10—C11 | −0.01 (19) | C15—C16—C17—C12 | 0.82 (19) |
C7—C6—C11—C10 | 1.06 (19) | C13—C12—C17—C16 | −0.69 (18) |
C7—C6—C11—C4 | −175.53 (12) | C5—C12—C17—C16 | 177.61 (11) |
C9—C10—C11—C6 | −1.17 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O1i | 0.89 (3) | 1.89 (3) | 2.771 (2) | 170 (3) |
O1—H1A···O2ii | 0.83 (5) | 2.01 (5) | 2.8353 (16) | 173 (4) |
O2—H2A···O1ii | 0.88 (4) | 1.96 (4) | 2.8353 (16) | 171 (3) |
O2—H2B···O2ii | 0.85 (3) | 2.03 (3) | 2.859 (2) | 164 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |
C17H21NO2 | F(000) = 584 |
Mr = 271.35 | Dx = 1.173 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3073 reflections |
a = 9.5879 (5) Å | θ = 2.4–28.7° |
b = 10.0655 (6) Å | µ = 0.08 mm−1 |
c = 16.1252 (9) Å | T = 300 K |
β = 99.034 (1)° | Plate, colourless |
V = 1536.89 (15) Å3 | 0.18 × 0.16 × 0.04 mm |
Z = 4 |
Bruker SMART 1K diffractometer | 3025 independent reflections |
Radiation source: fine-focus sealed tube | 2099 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −11→9 |
Tmin = 0.986, Tmax = 0.997 | k = −12→11 |
8282 measured reflections | l = −14→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0518P)2 + 0.1373P] where P = (Fo2 + 2Fc2)/3 |
3025 reflections | (Δ/σ)max < 0.001 |
195 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C17H21NO2 | V = 1536.89 (15) Å3 |
Mr = 271.35 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.5879 (5) Å | µ = 0.08 mm−1 |
b = 10.0655 (6) Å | T = 300 K |
c = 16.1252 (9) Å | 0.18 × 0.16 × 0.04 mm |
β = 99.034 (1)° |
Bruker SMART 1K diffractometer | 3025 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2099 reflections with I > 2σ(I) |
Tmin = 0.986, Tmax = 0.997 | Rint = 0.027 |
8282 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.18 e Å−3 |
3025 reflections | Δρmin = −0.16 e Å−3 |
195 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.13034 (12) | 0.28024 (12) | 0.52004 (7) | 0.0410 (3) | |
O1 | 0.37554 (17) | 0.44375 (14) | 0.51848 (10) | 0.0698 (4) | |
H1A | 0.292 (7) | 0.477 (5) | 0.501 (3) | 0.105* | 0.51 (2) |
H1B | 0.461 (6) | 0.502 (6) | 0.513 (4) | 0.105* | 0.49 (2) |
O2 | −0.10849 (16) | 0.43621 (12) | 0.53813 (8) | 0.0543 (3) | |
H2A | −0.190 (6) | 0.475 (5) | 0.518 (3) | 0.081* | 0.51 (2) |
H2B | −0.041 (5) | 0.461 (4) | 0.518 (3) | 0.081* | 0.49 (2) |
C1 | 0.38199 (17) | 0.30547 (19) | 0.50519 (12) | 0.0600 (5) | |
H11A | 0.4759 | 0.2734 | 0.5272 | 0.072* | |
H11B | 0.3642 | 0.2872 | 0.4454 | 0.072* | |
C2 | 0.27463 (16) | 0.23294 (16) | 0.54767 (10) | 0.0501 (4) | |
H21A | 0.2792 | 0.1387 | 0.5357 | 0.060* | |
H21B | 0.2983 | 0.2446 | 0.6080 | 0.060* | |
C3 | 0.08071 (19) | 0.2418 (2) | 0.43275 (10) | 0.0630 (5) | |
H3A | 0.1530 | 0.2603 | 0.3994 | 0.095* | |
H3B | −0.0028 | 0.2914 | 0.4114 | 0.095* | |
H3C | 0.0594 | 0.1486 | 0.4302 | 0.095* | |
C4 | 0.03132 (15) | 0.23746 (14) | 0.57566 (9) | 0.0391 (3) | |
H4A | 0.0234 | 0.1405 | 0.5717 | 0.047* | |
C5 | −0.11738 (15) | 0.29667 (15) | 0.54522 (9) | 0.0421 (4) | |
H5 | −0.1520 | 0.2606 | 0.4893 | 0.051* | |
C6 | 0.06436 (19) | 0.18146 (19) | 0.72902 (11) | 0.0588 (5) | |
H6 | 0.0286 | 0.0975 | 0.7140 | 0.071* | |
C7 | 0.1006 (2) | 0.2136 (3) | 0.81363 (12) | 0.0817 (7) | |
H7 | 0.0891 | 0.1515 | 0.8547 | 0.098* | |
C8 | 0.1530 (2) | 0.3369 (3) | 0.83594 (13) | 0.0860 (7) | |
H8 | 0.1760 | 0.3593 | 0.8924 | 0.103* | |
C9 | 0.1719 (2) | 0.4274 (2) | 0.77537 (12) | 0.0706 (6) | |
H9 | 0.2093 | 0.5107 | 0.7909 | 0.085* | |
C10 | 0.13587 (17) | 0.39601 (17) | 0.69139 (10) | 0.0524 (4) | |
H10 | 0.1488 | 0.4585 | 0.6508 | 0.063* | |
C11 | 0.08071 (15) | 0.27249 (15) | 0.66697 (9) | 0.0410 (4) | |
C12 | −0.22040 (15) | 0.25797 (15) | 0.60285 (9) | 0.0414 (4) | |
C13 | −0.26360 (17) | 0.34606 (17) | 0.65922 (10) | 0.0525 (4) | |
H13 | −0.2307 | 0.4331 | 0.6616 | 0.063* | |
C14 | −0.3560 (2) | 0.3055 (2) | 0.71241 (11) | 0.0685 (5) | |
H14 | −0.3852 | 0.3659 | 0.7498 | 0.082* | |
C15 | −0.4043 (2) | 0.1778 (2) | 0.71042 (12) | 0.0715 (6) | |
H15 | −0.4655 | 0.1513 | 0.7467 | 0.086* | |
C16 | −0.3627 (2) | 0.08911 (19) | 0.65501 (12) | 0.0659 (5) | |
H16 | −0.3949 | 0.0019 | 0.6537 | 0.079* | |
C17 | −0.27270 (17) | 0.12926 (17) | 0.60097 (11) | 0.0532 (4) | |
H17 | −0.2466 | 0.0689 | 0.5625 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0377 (7) | 0.0473 (7) | 0.0389 (6) | 0.0005 (5) | 0.0086 (5) | 0.0019 (5) |
O1 | 0.0403 (8) | 0.0620 (9) | 0.1083 (11) | −0.0016 (6) | 0.0156 (7) | 0.0194 (7) |
O2 | 0.0408 (7) | 0.0498 (7) | 0.0741 (8) | 0.0036 (5) | 0.0144 (6) | 0.0241 (6) |
C1 | 0.0414 (10) | 0.0757 (13) | 0.0658 (11) | 0.0097 (8) | 0.0178 (8) | 0.0088 (9) |
C2 | 0.0440 (9) | 0.0512 (10) | 0.0569 (10) | 0.0098 (7) | 0.0134 (7) | 0.0056 (7) |
C3 | 0.0591 (11) | 0.0854 (13) | 0.0464 (10) | −0.0034 (9) | 0.0139 (8) | −0.0076 (9) |
C4 | 0.0402 (8) | 0.0346 (8) | 0.0430 (8) | −0.0018 (6) | 0.0086 (6) | 0.0021 (6) |
C5 | 0.0368 (8) | 0.0475 (9) | 0.0415 (8) | −0.0046 (6) | 0.0046 (6) | 0.0047 (7) |
C6 | 0.0568 (11) | 0.0676 (12) | 0.0532 (10) | 0.0085 (9) | 0.0125 (8) | 0.0182 (9) |
C7 | 0.0769 (14) | 0.121 (2) | 0.0493 (11) | 0.0318 (14) | 0.0152 (10) | 0.0301 (12) |
C8 | 0.0772 (15) | 0.130 (2) | 0.0462 (11) | 0.0363 (15) | −0.0035 (10) | −0.0117 (13) |
C9 | 0.0571 (11) | 0.0864 (15) | 0.0635 (12) | 0.0110 (10) | −0.0052 (9) | −0.0226 (11) |
C10 | 0.0468 (9) | 0.0577 (11) | 0.0511 (10) | 0.0034 (8) | 0.0029 (7) | −0.0049 (8) |
C11 | 0.0334 (8) | 0.0482 (9) | 0.0416 (8) | 0.0064 (6) | 0.0062 (6) | 0.0061 (7) |
C12 | 0.0332 (8) | 0.0463 (9) | 0.0431 (8) | −0.0031 (6) | 0.0015 (6) | 0.0065 (7) |
C13 | 0.0520 (10) | 0.0550 (10) | 0.0514 (10) | −0.0087 (8) | 0.0112 (8) | −0.0005 (8) |
C14 | 0.0703 (13) | 0.0843 (14) | 0.0555 (11) | −0.0065 (11) | 0.0243 (9) | −0.0044 (9) |
C15 | 0.0634 (12) | 0.0957 (16) | 0.0591 (11) | −0.0186 (11) | 0.0210 (9) | 0.0162 (11) |
C16 | 0.0582 (11) | 0.0608 (12) | 0.0777 (13) | −0.0204 (9) | 0.0075 (10) | 0.0188 (10) |
C17 | 0.0452 (9) | 0.0495 (10) | 0.0646 (10) | −0.0076 (8) | 0.0075 (8) | 0.0034 (8) |
N1—C2 | 1.4647 (19) | C6—C11 | 1.384 (2) |
N1—C3 | 1.4653 (19) | C6—C7 | 1.392 (3) |
N1—C4 | 1.4692 (18) | C6—H6 | 0.9300 |
O1—C1 | 1.411 (2) | C7—C8 | 1.366 (3) |
O1—H1A | 0.87 (7) | C7—H7 | 0.9300 |
O1—H1B | 1.02 (6) | C8—C9 | 1.369 (3) |
O2—C5 | 1.4129 (19) | C8—H8 | 0.9300 |
O2—H2A | 0.89 (6) | C9—C10 | 1.381 (2) |
O2—H2B | 0.81 (5) | C9—H9 | 0.9300 |
C1—C2 | 1.511 (2) | C10—C11 | 1.384 (2) |
C1—H11A | 0.9700 | C10—H10 | 0.9300 |
C1—H11B | 0.9700 | C12—C13 | 1.379 (2) |
C2—H21A | 0.9700 | C12—C17 | 1.388 (2) |
C2—H21B | 0.9700 | C13—C14 | 1.388 (2) |
C3—H3A | 0.9600 | C13—H13 | 0.9300 |
C3—H3B | 0.9600 | C14—C15 | 1.364 (3) |
C3—H3C | 0.9600 | C14—H14 | 0.9300 |
C4—C11 | 1.516 (2) | C15—C16 | 1.367 (3) |
C4—C5 | 1.552 (2) | C15—H15 | 0.9300 |
C4—H4A | 0.9800 | C16—C17 | 1.379 (2) |
C5—C12 | 1.510 (2) | C16—H16 | 0.9300 |
C5—H5 | 0.9800 | C17—H17 | 0.9300 |
C2—N1—C3 | 110.80 (13) | C4—C5—H5 | 108.1 |
C2—N1—C4 | 112.90 (11) | C11—C6—C7 | 121.04 (19) |
C3—N1—C4 | 111.44 (12) | C11—C6—H6 | 119.5 |
C1—O1—H1A | 113 (3) | C7—C6—H6 | 119.5 |
C1—O1—H1B | 120 (3) | C8—C7—C6 | 119.62 (19) |
H1A—O1—H1B | 117 (5) | C8—C7—H7 | 120.2 |
C5—O2—H2A | 114 (3) | C6—C7—H7 | 120.2 |
C5—O2—H2B | 114 (3) | C7—C8—C9 | 120.10 (19) |
H2A—O2—H2B | 115 (4) | C7—C8—H8 | 119.9 |
O1—C1—C2 | 111.01 (14) | C9—C8—H8 | 119.9 |
O1—C1—H11A | 109.4 | C8—C9—C10 | 120.4 (2) |
C2—C1—H11A | 109.4 | C8—C9—H9 | 119.8 |
O1—C1—H11B | 109.4 | C10—C9—H9 | 119.8 |
C2—C1—H11B | 109.4 | C9—C10—C11 | 120.69 (17) |
H11A—C1—H11B | 108.0 | C9—C10—H10 | 119.7 |
N1—C2—C1 | 112.53 (13) | C11—C10—H10 | 119.7 |
N1—C2—H21A | 109.1 | C6—C11—C10 | 118.08 (15) |
C1—C2—H21A | 109.1 | C6—C11—C4 | 119.65 (15) |
N1—C2—H21B | 109.1 | C10—C11—C4 | 122.18 (13) |
C1—C2—H21B | 109.1 | C13—C12—C17 | 118.02 (15) |
H21A—C2—H21B | 107.8 | C13—C12—C5 | 122.21 (14) |
N1—C3—H3A | 109.5 | C17—C12—C5 | 119.76 (14) |
N1—C3—H3B | 109.5 | C12—C13—C14 | 120.33 (16) |
H3A—C3—H3B | 109.5 | C12—C13—H13 | 119.8 |
N1—C3—H3C | 109.5 | C14—C13—H13 | 119.8 |
H3A—C3—H3C | 109.5 | C15—C14—C13 | 120.67 (18) |
H3B—C3—H3C | 109.5 | C15—C14—H14 | 119.7 |
N1—C4—C11 | 113.05 (12) | C13—C14—H14 | 119.7 |
N1—C4—C5 | 110.12 (11) | C14—C15—C16 | 119.84 (17) |
C11—C4—C5 | 110.45 (12) | C14—C15—H15 | 120.1 |
N1—C4—H4A | 107.7 | C16—C15—H15 | 120.1 |
C11—C4—H4A | 107.7 | C15—C16—C17 | 119.84 (17) |
C5—C4—H4A | 107.7 | C15—C16—H16 | 120.1 |
O2—C5—C12 | 111.09 (13) | C17—C16—H16 | 120.1 |
O2—C5—C4 | 110.07 (12) | C16—C17—C12 | 121.29 (17) |
C12—C5—C4 | 111.32 (11) | C16—C17—H17 | 119.4 |
O2—C5—H5 | 108.1 | C12—C17—H17 | 119.4 |
C12—C5—H5 | 108.1 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O1i | 1.02 (6) | 1.81 (6) | 2.789 (3) | 160 (5) |
O1—H1A···O2ii | 0.87 (7) | 1.98 (7) | 2.849 (2) | 177 (5) |
O2—H2A···O1ii | 0.89 (6) | 1.96 (6) | 2.849 (2) | 176 (4) |
O2—H2B···O2ii | 0.81 (5) | 2.09 (4) | 2.880 (3) | 168 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C17H21NO2 | C21H27NO2 | C17H21NO2 | C16H27NO2 |
Mr | 271.35 | 325.44 | 271.35 | 265.39 |
Crystal system, space group | Monoclinic, Pc | Orthorhombic, P212121 | Monoclinic, P21/n | Orthorhombic, P212121 |
Temperature (K) | 120 | 120 | 120 | 120 |
a, b, c (Å) | 5.8366 (1), 15.3018 (4), 8.1078 (2) | 8.5024 (4), 11.9480 (5), 17.6485 (7) | 9.3438 (2), 15.9896 (4), 10.9479 (3) | 8.6781 (5), 12.8084 (7), 14.5243 (8) |
α, β, γ (°) | 90, 91.444 (1), 90 | 90, 90, 90 | 90, 114.441 (1), 90 | 90, 90, 90 |
V (Å3) | 723.88 (3) | 1792.85 (13) | 1489.08 (6) | 1614.41 (16) |
Z | 2 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.08 | 0.08 | 0.08 | 0.07 |
Crystal size (mm) | 0.40 × 0.20 × 0.10 | 0.30 × 0.24 × 0.20 | 0.30 × 0.20 × 0.20 | 0.30 × 0.25 × 0.20 |
Data collection | ||||
Diffractometer | Bruker SMART 1K diffractometer | Bruker SMART 1K diffractometer | Bruker SMART 1K diffractometer | Bruker SMART 1K diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) | Multi-scan (SADABS; Bruker, 2004) | Multi-scan (SADABS; Bruker, 2004) | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.968, 0.992 | 0.977, 0.985 | 0.977, 0.984 | 0.979, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4958, 1677, 1626 | 12996, 2712, 2398 | 10283, 3416, 2508 | 11540, 2428, 1986 |
Rint | 0.029 | 0.040 | 0.039 | 0.039 |
(sin θ/λ)max (Å−1) | 0.649 | 0.682 | 0.650 | 0.682 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.077, 1.06 | 0.035, 0.083, 1.03 | 0.044, 0.097, 1.05 | 0.041, 0.095, 1.06 |
No. of reflections | 1677 | 2712 | 3416 | 2428 |
No. of parameters | 190 | 325 | 191 | 185 |
No. of restraints | 2 | 0 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | All H-atom parameters refined | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.19 | 0.21, −0.20 | 0.26, −0.18 | 0.17, −0.18 |
(V) | (VI_100) | (VI_300) | |
Crystal data | |||
Chemical formula | C20H27NO2 | C17H21NO2 | C17H21NO2 |
Mr | 313.43 | 271.35 | 271.35 |
Crystal system, space group | Orthorhombic, P212121 | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 120 | 100 | 300 |
a, b, c (Å) | 8.9681 (8), 12.5151 (11), 16.3960 (14) | 9.5577 (9), 9.9481 (9), 15.9403 (15) | 9.5879 (5), 10.0655 (6), 16.1252 (9) |
α, β, γ (°) | 90, 90, 90 | 90, 100.136 (2), 90 | 90, 99.034 (1), 90 |
V (Å3) | 1840.2 (3) | 1492.0 (2) | 1536.89 (15) |
Z | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.07 | 0.08 | 0.08 |
Crystal size (mm) | 0.25 × 0.20 × 0.10 | 0.18 × 0.16 × 0.04 | 0.18 × 0.16 × 0.04 |
Data collection | |||
Diffractometer | Bruker SMART 1K diffractometer | Bruker SMART 1K diffractometer | Bruker SMART 1K diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) | Multi-scan (SADABS; Bruker, 2004) | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.982, 0.993 | 0.986, 0.997 | 0.986, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13036, 2772, 2376 | 7956, 2932, 2482 | 8282, 3025, 2099 |
Rint | 0.045 | 0.022 | 0.027 |
(sin θ/λ)max (Å−1) | 0.682 | 0.617 | 0.617 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.086, 1.07 | 0.038, 0.092, 1.07 | 0.044, 0.113, 1.06 |
No. of reflections | 2772 | 2932 | 3025 |
No. of parameters | 219 | 195 | 195 |
No. of restraints | 0 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.19 | 0.24, −0.25 | 0.18, −0.16 |
Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.83 (3) | 1.97 (3) | 2.7954 (19) | 170 (3) |
O2—H2···N1 | 0.83 (3) | 2.04 (3) | 2.6111 (18) | 126 (2) |
Symmetry code: (i) x, −y+1, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.84 (3) | 1.99 (3) | 2.6223 (18) | 131 (2) |
O2—H2···O1i | 0.85 (3) | 1.99 (3) | 2.8404 (17) | 172 (2) |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N1 | 0.87 (2) | 2.07 (2) | 2.6765 (15) | 126.0 (16) |
O1—H1···O2i | 0.88 (2) | 1.93 (2) | 2.8101 (15) | 177 (2) |
Symmetry code: (i) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.80 (3) | 1.91 (3) | 2.703 (2) | 170 (3) |
O2—H2···O1i | 0.89 (3) | 1.88 (3) | 2.7713 (18) | 174 (2) |
Symmetry code: (i) x+1/2, −y−1/2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.84 (3) | 1.95 (3) | 2.7717 (19) | 165 (2) |
O2—H2···O1i | 0.90 (3) | 1.82 (3) | 2.7211 (18) | 175 (2) |
Symmetry code: (i) x−1/2, −y+3/2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O1i | 0.89 (3) | 1.89 (3) | 2.771 (2) | 170 (3) |
O1—H1A···O2ii | 0.83 (5) | 2.01 (5) | 2.8353 (16) | 173 (4) |
O2—H2A···O1ii | 0.88 (4) | 1.96 (4) | 2.8353 (16) | 171 (3) |
O2—H2B···O2ii | 0.85 (3) | 2.03 (3) | 2.859 (2) | 164 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O1i | 1.02 (6) | 1.81 (6) | 2.789 (3) | 160 (5) |
O1—H1A···O2ii | 0.87 (7) | 1.98 (7) | 2.849 (2) | 177 (5) |
O2—H2A···O1ii | 0.89 (6) | 1.96 (6) | 2.849 (2) | 176 (4) |
O2—H2B···O2ii | 0.81 (5) | 2.09 (4) | 2.880 (3) | 168 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |
In the last two decades, polydentate ligand frameworks have been widely used in the synthesis of transition metal complexes which may be applied as catalysts for fine organic reactions or polymerization processes (Odom, 2005; Mountford, 1998; Coates, 2002). Within this field, ligands featuring anionic O donors (alkoxides, aryloxides), and especially alkoxides with an additional intramolecular donor group, have attracted particular attention (Mack & Eisen, 1998; Chmura et al., 2006; Knight et al., 2004). Among these ligands, diethanolamines look highly intriguing, due to the relative ease of manipulating the ligand topology (cyclic or open-chain), steric hindrance, chirality and coordination ability. We reported recently the synthesis of several titanium complexes based on chiral diethanolamines (Zaitsev et al., 2008).
N-Aryldiethanolamines are well known (El-Sayed et al., 2001; Centore & Tuzi, 2003; Luger & Roch, 1983; Chen & Shi, 2006), but in their structures the N atom never normally participates in hydrogen bonding due to significant aryl–N conjugation. Additionally, the structures of N-diethanolamines where the N atom bonds to a Csp3 atom are rare (Skinner et al., 2005; Wu & Rehder, 2005). Here, we report the structures of six N-alkyldiethanolamines, (I)–(VI). In the molecules of (I)–(VI), all bond lengths have normal values and the N atoms adopt pyramidal conformations, with the sums of the bond angles in the range 334.7–341.3°. However, analysis of the hydrogen bonding in these compounds demonstrates four distinct topologies.
In structures (I) and (II), the N atom forms a bent intramolecular hydrogen bond with one of the Oa atoms (A in Scheme 1; Fig. 1, Tables 1 and 2). The Oa—H···N angle varies from 126 (2) to 131 (2)°. The resulting five-membered rings are non-planar, and both `envelope' and `twist' conformations are observed. Atom Oa accepts an intermolecular hydrogen bond from a hydroxyl group Ob—H of an adjacent molecule. Atom Ob, however, serves only as a hydrogen-bond donor for the neighbouring molecule. This motif results in the formation of chains (Fig. 2).
As in the structures of (I) and (II), in compound (III) the N atom forms an intramolecular hydrogen bond with one of the Oa atoms, with an Oa—H···N angle of 126 (2)° (Table 2). However, in contrast with (I) and (II), the molecules of (III) form centrosymmetric S(5)R44(14) dimers (Bernstein et al., 1995) (Fig. 3).
In structures (IV) and (V), the N atom does not participate in hydrogen bonding (B in Scheme 1; Fig. 4). This is probably caused by the steric requirements of the bulky CH(Me)Ph substituent bound to the amine N atoms. The O atoms form an intramolecular Oa—H···Ob hydrogen bond, resulting in an eight-membered cycle closure. Additionally, both O atoms are engaged in intermolecular hydrogen bonds, combining adjacent molecules into chains (Fig. 5). The Oa—H···Ob bond is close to linear. The identical structural motif to that in (IV) was found previously for the related diethanolamine derivative o-(C5NH4)CH2N(CH2CMe2OH)2 (Skinner et al., 2005) and for some aryl-substituted ligands (Seo et al., 2007).
In the structure of (VI), the N atom is not involved in hydrogen bonding and no intramolecular hydrogen bonds were observed. However, both O atoms form intermolecular hydrogen bonds, resulting in chain generation. Interestingly, both hydroxyl H atoms are disordered over two positions with approximately equal occupancies (Fig. 6). Thus, (VI) demonstrates two distinct non-equivalent systems of intermolecular O—H···O bonds (see Scheme 2; Fig. 7). We have previously observed the same type of chains in the structure of 2-(hydroxymethyl)-6-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)phenol (Chukicheva et al., 2006). We made two data collections from the same crystal at different temperatures (100 and 300 K), but found only minimal structural changes.
In the structures of (I), (II) and (IV)–(VI), the chains are organized in such a way as to hide the hydrophilic groups inside, and hence the outer surfaces of the chains are hydrophobic. These chains are combined in two- or three-dimensional networks by T-shaped aromatic C—H···π interactions. No face-to-face intermolecular π=-π interactions were found. In the structure of (III), the dimers are also connected by intermolecular C—H···π interactions.
In all four packing motifs, we observed that the N atoms are not involved in intermolecular hydrogen bonding. However, Wu & Rehder (2005) found another supramolecular aggregation for the structure of allyldiethanolamine, (VII), where the N atom does interact intermolecularly with the hydroxyl groups. In (VII), one of two OH groups serves as both donor and acceptor of hydrogen bonds, while another acts as donor only. The latter results in the formation of hydrophobic chains of the molecules (see Scheme 3).
It is noteworthy that three of the compounds investigated here [(II), (IV) and (V)] were obtained from enantiopure amines (Zaitsev et al., 2008) and crystallize in the Sohncke space group P212121, forming helical chains along 21 screw axes. Therefore, they possess the potential for the effective transfer of chirality to a metal centre which is essential for successful asymmetric metal-based catalysis.