Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600576717012316/ei5022sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600576717012316/ei5022Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S1600576717012316/ei5022sup3.pdf |
CCDC reference: 1524601
Program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).
C15H15NO | Dx = 1.195 Mg m−3 |
Mr = 225.28 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 1346 reflections |
a = 9.5277 (8) Å | θ = 3.3–18.9° |
b = 11.1555 (11) Å | µ = 0.08 mm−1 |
c = 11.7848 (10) Å | T = 293 K |
V = 1252.6 (2) Å3 | Block, colourless |
Z = 4 | 0.5 × 0.5 × 0.5 mm |
F(000) = 480 |
Xcalibur, Sapphire3 diffractometer | 1322 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.108 |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 29.5°, θmin = 3.3° |
Tmin = 0.713, Tmax = 1.000 | h = −12→11 |
16911 measured reflections | k = −14→14 |
3189 independent reflections | l = −16→16 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.015P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.063 | (Δ/σ)max < 0.001 |
wR(F2) = 0.108 | Δρmax = 0.12 e Å−3 |
S = 0.97 | Δρmin = −0.12 e Å−3 |
3189 reflections | Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
156 parameters | Extinction coefficient: 0.0122 (14) |
1 restraint | Absolute structure: Flack x determined using 401 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −1.9 (10) |
Hydrogen site location: inferred from neighbouring sites |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. olex2_refinement_description 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B) 2.b Aromatic/amide H refined with riding coordinates: C14(H14), N1(H1), C13(H13), C5(H5), C1(H1A), C10(H10), C11(H11), C3(H3), C2(H2), C4(H4) 2.c Idealised Me refined as rotating group: C15(H15A,H15B,H15C) |
x | y | z | Uiso*/Ueq | ||
O1 | −0.0275 (3) | −0.6733 (3) | −0.3283 (3) | 0.0677 (10) | |
C6 | 0.1316 (5) | −0.6668 (4) | −0.1749 (4) | 0.0493 (12) | |
C14 | 0.3313 (5) | −0.7751 (4) | −0.6445 (4) | 0.0600 (13) | |
H14 | 0.314021 | −0.856900 | −0.650694 | 0.072* | |
C9 | 0.2651 (5) | −0.7104 (5) | −0.5608 (4) | 0.0537 (12) | |
N1 | 0.1902 (4) | −0.7411 (4) | −0.3621 (3) | 0.0627 (12) | |
H1 | 0.272632 | −0.752847 | −0.334489 | 0.075* | |
C13 | 0.4235 (5) | −0.7207 (5) | −0.7201 (4) | 0.0645 (15) | |
H13 | 0.466828 | −0.766568 | −0.775959 | 0.077* | |
C7 | 0.0919 (5) | −0.6947 (4) | −0.2950 (4) | 0.0544 (13) | |
C5 | 0.2463 (5) | −0.7184 (4) | −0.1217 (4) | 0.0679 (15) | |
H5 | 0.303957 | −0.770560 | −0.161953 | 0.081* | |
C1 | 0.0506 (5) | −0.5895 (4) | −0.1140 (5) | 0.0654 (14) | |
H1A | −0.026841 | −0.554057 | −0.148366 | 0.079* | |
C8 | 0.1647 (5) | −0.7730 (5) | −0.4807 (4) | 0.0661 (15) | |
H8A | 0.069162 | −0.751564 | −0.500657 | 0.079* | |
H8B | 0.174434 | −0.859003 | −0.489598 | 0.079* | |
C10 | 0.2939 (5) | −0.5903 (5) | −0.5534 (5) | 0.0679 (14) | |
H10 | 0.251583 | −0.544295 | −0.497188 | 0.082* | |
C12 | 0.4511 (5) | −0.6005 (6) | −0.7134 (4) | 0.0666 (15) | |
C11 | 0.3858 (6) | −0.5373 (5) | −0.6292 (5) | 0.0767 (17) | |
H11 | 0.403762 | −0.455626 | −0.622637 | 0.092* | |
C3 | 0.1947 (6) | −0.6146 (5) | 0.0502 (5) | 0.0813 (18) | |
H3 | 0.216023 | −0.596478 | 0.125256 | 0.098* | |
C2 | 0.0811 (6) | −0.5627 (5) | −0.0019 (5) | 0.0768 (17) | |
H2 | 0.024611 | −0.509477 | 0.038140 | 0.092* | |
C15 | 0.5490 (6) | −0.5395 (6) | −0.7953 (5) | 0.102 (2) | |
H15A | 0.591896 | −0.598406 | −0.843504 | 0.152* | |
H15B | 0.620461 | −0.497520 | −0.753825 | 0.152* | |
H15C | 0.497103 | −0.483577 | −0.840860 | 0.152* | |
C4 | 0.2758 (6) | −0.6931 (5) | −0.0095 (5) | 0.0846 (19) | |
H4 | 0.351754 | −0.729915 | 0.025656 | 0.102* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0413 (19) | 0.097 (3) | 0.065 (2) | 0.0048 (19) | −0.0082 (18) | 0.012 (2) |
C6 | 0.040 (3) | 0.056 (3) | 0.052 (3) | −0.004 (2) | −0.003 (2) | 0.007 (2) |
C14 | 0.066 (3) | 0.067 (3) | 0.047 (3) | −0.005 (3) | −0.012 (3) | −0.003 (3) |
C9 | 0.045 (3) | 0.073 (3) | 0.043 (3) | 0.002 (2) | −0.008 (2) | −0.003 (3) |
N1 | 0.038 (2) | 0.100 (3) | 0.051 (3) | −0.005 (2) | −0.008 (2) | −0.002 (2) |
C13 | 0.067 (4) | 0.084 (4) | 0.043 (3) | 0.005 (3) | 0.000 (3) | 0.003 (3) |
C7 | 0.043 (3) | 0.069 (4) | 0.052 (3) | −0.009 (3) | −0.002 (3) | 0.010 (3) |
C5 | 0.063 (4) | 0.092 (4) | 0.049 (3) | 0.010 (3) | −0.004 (3) | −0.001 (3) |
C1 | 0.062 (4) | 0.067 (4) | 0.068 (4) | 0.001 (3) | −0.007 (3) | −0.003 (3) |
C8 | 0.058 (4) | 0.096 (4) | 0.044 (3) | −0.007 (3) | 0.000 (3) | −0.008 (3) |
C10 | 0.067 (4) | 0.071 (4) | 0.065 (3) | 0.012 (3) | −0.006 (3) | −0.014 (3) |
C12 | 0.053 (4) | 0.088 (4) | 0.059 (4) | 0.001 (3) | −0.009 (3) | 0.018 (3) |
C11 | 0.076 (4) | 0.069 (4) | 0.085 (4) | −0.005 (3) | 0.003 (4) | 0.013 (4) |
C3 | 0.076 (4) | 0.104 (5) | 0.065 (4) | −0.006 (4) | −0.015 (4) | −0.010 (3) |
C2 | 0.073 (4) | 0.085 (4) | 0.072 (4) | −0.001 (3) | 0.008 (3) | −0.025 (3) |
C15 | 0.080 (5) | 0.134 (5) | 0.090 (5) | −0.015 (4) | −0.007 (4) | 0.039 (4) |
C4 | 0.075 (4) | 0.119 (6) | 0.059 (4) | 0.026 (4) | −0.015 (3) | −0.002 (4) |
O1—C7 | 1.227 (5) | N1—C8 | 1.462 (5) |
C6—C7 | 1.498 (6) | C13—C12 | 1.369 (6) |
C6—C5 | 1.385 (6) | C5—C4 | 1.381 (6) |
C6—C1 | 1.361 (6) | C1—C2 | 1.386 (6) |
C14—C9 | 1.376 (6) | C10—C11 | 1.383 (6) |
C14—C13 | 1.390 (6) | C12—C11 | 1.367 (6) |
C9—C8 | 1.515 (6) | C12—C15 | 1.506 (6) |
C9—C10 | 1.370 (6) | C3—C2 | 1.371 (6) |
N1—C7 | 1.331 (5) | C3—C4 | 1.364 (6) |
C5—C6—C7 | 122.7 (5) | C4—C5—C6 | 120.6 (5) |
C1—C6—C7 | 119.1 (5) | C6—C1—C2 | 121.3 (5) |
C1—C6—C5 | 118.2 (5) | N1—C8—C9 | 112.2 (4) |
C9—C14—C13 | 121.3 (5) | C9—C10—C11 | 120.3 (5) |
C14—C9—C8 | 119.6 (5) | C13—C12—C15 | 121.7 (5) |
C10—C9—C14 | 117.8 (5) | C11—C12—C13 | 117.4 (5) |
C10—C9—C8 | 122.5 (5) | C11—C12—C15 | 120.9 (6) |
C7—N1—C8 | 123.1 (4) | C12—C11—C10 | 122.4 (5) |
C12—C13—C14 | 120.8 (5) | C4—C3—C2 | 119.2 (5) |
O1—C7—C6 | 119.7 (5) | C3—C2—C1 | 120.1 (5) |
O1—C7—N1 | 122.6 (5) | C3—C4—C5 | 120.7 (5) |
N1—C7—C6 | 117.7 (4) |