In the title compound, C
24H
23ClO
4, the side chain displays an extended conformation. The main secondary interactions involve a bifurcated hydrogen-bond system (C—H
)
2O to the carbonyl O atom. Each ring is involved in a long C—H
π interaction.
Supporting information
CCDC reference: 270230
Key indicators
- Single-crystal X-ray study
- T = 133 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.116
- Data-to-parameter ratio = 23.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.89 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H27B .. O4 .. 2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H37B .. CL .. 3.00 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C37 .. CL .. 3.98 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
2-[Bis(4-methoxyphenyl)methyl]benzyl chloroacetate
top
Crystal data top
C24H23ClO4 | Z = 2 |
Mr = 410.87 | F(000) = 432 |
Triclinic, P1 | Dx = 1.320 Mg m−3 |
a = 7.6817 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.6398 (6) Å | Cell parameters from 8877 reflections |
c = 13.4992 (8) Å | θ = 2.7–30.5° |
α = 108.529 (4)° | µ = 0.21 mm−1 |
β = 92.712 (4)° | T = 133 K |
γ = 97.109 (4)° | Prism, colourless |
V = 1033.67 (10) Å3 | 0.35 × 0.21 × 0.16 mm |
Data collection top
Bruker SMART 1000 CCD diffractometer | 6274 independent reflections |
Radiation source: fine-focus sealed tube | 4988 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 8.192 pixels mm-1 | θmax = 30.5°, θmin = 1.6° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −14→15 |
Tmin = 0.890, Tmax = 0.967 | l = −19→19 |
22190 measured reflections | |
Refinement top
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) = 0.116 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0613P)2 + 0.2812P] where P = (Fo2 + 2Fc2)/3 |
6274 reflections | (Δ/σ)max = 0.001 |
264 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl | 0.08165 (5) | 0.36901 (3) | 0.78479 (2) | 0.03444 (10) | |
O1 | −0.11035 (12) | 0.20368 (8) | 0.49316 (7) | 0.02504 (18) | |
O2 | −0.08259 (15) | 0.41702 (9) | 0.60003 (7) | 0.0346 (2) | |
O3 | 0.50891 (13) | 0.20767 (9) | 0.64641 (7) | 0.0289 (2) | |
O4 | 0.62835 (13) | 0.32648 (10) | −0.00575 (7) | 0.0321 (2) | |
C1 | 0.14283 (15) | 0.26084 (11) | 0.28743 (8) | 0.0189 (2) | |
H1 | 0.0915 | 0.3463 | 0.3099 | 0.023* | |
C11 | −0.01109 (15) | 0.14686 (11) | 0.24512 (8) | 0.0187 (2) | |
C12 | −0.15431 (15) | 0.13752 (11) | 0.30509 (9) | 0.0199 (2) | |
C13 | −0.28469 (16) | 0.02543 (12) | 0.27056 (9) | 0.0238 (2) | |
H13 | −0.3793 | 0.0185 | 0.3123 | 0.029* | |
C14 | −0.27877 (17) | −0.07602 (13) | 0.17647 (10) | 0.0273 (3) | |
H14 | −0.3678 | −0.1521 | 0.1543 | 0.033* | |
C15 | −0.14176 (18) | −0.06505 (12) | 0.11534 (10) | 0.0275 (3) | |
H15 | −0.1383 | −0.1326 | 0.0498 | 0.033* | |
C16 | −0.00883 (16) | 0.04513 (12) | 0.14990 (9) | 0.0231 (2) | |
H16 | 0.0853 | 0.0510 | 0.1077 | 0.028* | |
C17 | −0.17387 (17) | 0.24519 (12) | 0.40609 (9) | 0.0238 (2) | |
H17A | −0.1043 | 0.3311 | 0.4085 | 0.029* | |
H17B | −0.2990 | 0.2579 | 0.4112 | 0.029* | |
C18 | −0.06852 (16) | 0.30155 (12) | 0.58486 (9) | 0.0233 (2) | |
C19 | −0.00495 (19) | 0.24264 (13) | 0.66594 (10) | 0.0281 (3) | |
H19A | 0.0872 | 0.1871 | 0.6379 | 0.034* | |
H19B | −0.1043 | 0.1838 | 0.6799 | 0.034* | |
C21 | 0.23792 (15) | 0.24888 (11) | 0.38522 (8) | 0.0187 (2) | |
C22 | 0.25989 (15) | 0.12410 (11) | 0.39381 (9) | 0.0204 (2) | |
H22 | 0.2126 | 0.0450 | 0.3381 | 0.024* | |
C23 | 0.34881 (16) | 0.11304 (11) | 0.48156 (9) | 0.0220 (2) | |
H23 | 0.3609 | 0.0271 | 0.4859 | 0.026* | |
C24 | 0.42067 (15) | 0.22829 (11) | 0.56358 (9) | 0.0211 (2) | |
C25 | 0.39875 (16) | 0.35365 (11) | 0.55750 (9) | 0.0232 (2) | |
H25 | 0.4456 | 0.4326 | 0.6135 | 0.028* | |
C26 | 0.30761 (16) | 0.36249 (11) | 0.46867 (9) | 0.0216 (2) | |
H26 | 0.2928 | 0.4483 | 0.4651 | 0.026* | |
C27 | 0.56593 (18) | 0.32359 (14) | 0.73605 (10) | 0.0315 (3) | |
H27A | 0.6511 | 0.3861 | 0.7165 | 0.038* | |
H27B | 0.6216 | 0.2967 | 0.7915 | 0.038* | |
H27C | 0.4642 | 0.3674 | 0.7616 | 0.038* | |
C31 | 0.27152 (15) | 0.27217 (11) | 0.20694 (8) | 0.0196 (2) | |
C32 | 0.41475 (18) | 0.20277 (14) | 0.19131 (11) | 0.0300 (3) | |
H32 | 0.4306 | 0.1439 | 0.2300 | 0.036* | |
C33 | 0.53624 (18) | 0.21674 (15) | 0.12050 (11) | 0.0309 (3) | |
H33 | 0.6330 | 0.1678 | 0.1112 | 0.037* | |
C34 | 0.51402 (16) | 0.30270 (12) | 0.06400 (9) | 0.0236 (2) | |
C35 | 0.36937 (17) | 0.37120 (12) | 0.07620 (9) | 0.0243 (2) | |
H35 | 0.3523 | 0.4285 | 0.0363 | 0.029* | |
C36 | 0.24988 (16) | 0.35540 (11) | 0.14708 (9) | 0.0214 (2) | |
H36 | 0.1513 | 0.4024 | 0.1549 | 0.026* | |
C37 | 0.7768 (2) | 0.2573 (2) | −0.01895 (15) | 0.0541 (5) | |
H37A | 0.8452 | 0.2790 | 0.0490 | 0.065* | |
H37B | 0.8507 | 0.2848 | −0.0678 | 0.065* | |
H37C | 0.7369 | 0.1606 | −0.0471 | 0.065* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl | 0.0371 (2) | 0.03979 (18) | 0.02513 (15) | 0.01096 (14) | 0.00302 (12) | 0.00685 (13) |
O1 | 0.0350 (5) | 0.0207 (4) | 0.0206 (4) | 0.0060 (3) | 0.0071 (3) | 0.0071 (3) |
O2 | 0.0529 (7) | 0.0231 (4) | 0.0283 (5) | 0.0150 (4) | 0.0050 (4) | 0.0054 (4) |
O3 | 0.0333 (5) | 0.0314 (5) | 0.0209 (4) | −0.0008 (4) | −0.0044 (3) | 0.0101 (3) |
O4 | 0.0278 (5) | 0.0461 (6) | 0.0290 (5) | 0.0038 (4) | 0.0086 (4) | 0.0211 (4) |
C1 | 0.0193 (5) | 0.0182 (5) | 0.0199 (5) | 0.0042 (4) | 0.0038 (4) | 0.0065 (4) |
C11 | 0.0182 (5) | 0.0192 (5) | 0.0197 (5) | 0.0045 (4) | 0.0020 (4) | 0.0070 (4) |
C12 | 0.0196 (5) | 0.0217 (5) | 0.0203 (5) | 0.0064 (4) | 0.0031 (4) | 0.0081 (4) |
C13 | 0.0194 (6) | 0.0288 (6) | 0.0267 (6) | 0.0041 (4) | 0.0041 (4) | 0.0131 (5) |
C14 | 0.0254 (6) | 0.0263 (6) | 0.0284 (6) | −0.0020 (4) | −0.0026 (5) | 0.0092 (5) |
C15 | 0.0299 (7) | 0.0254 (6) | 0.0225 (5) | 0.0012 (5) | 0.0004 (4) | 0.0027 (4) |
C16 | 0.0232 (6) | 0.0241 (5) | 0.0208 (5) | 0.0034 (4) | 0.0045 (4) | 0.0054 (4) |
C17 | 0.0275 (6) | 0.0242 (5) | 0.0228 (5) | 0.0096 (4) | 0.0082 (4) | 0.0091 (4) |
C18 | 0.0245 (6) | 0.0235 (5) | 0.0231 (5) | 0.0068 (4) | 0.0096 (4) | 0.0071 (4) |
C19 | 0.0358 (7) | 0.0263 (6) | 0.0243 (6) | 0.0095 (5) | 0.0075 (5) | 0.0089 (5) |
C21 | 0.0180 (5) | 0.0186 (5) | 0.0195 (5) | 0.0026 (4) | 0.0035 (4) | 0.0058 (4) |
C22 | 0.0228 (6) | 0.0164 (5) | 0.0202 (5) | 0.0018 (4) | 0.0009 (4) | 0.0041 (4) |
C23 | 0.0232 (6) | 0.0194 (5) | 0.0240 (5) | 0.0029 (4) | 0.0017 (4) | 0.0078 (4) |
C24 | 0.0194 (6) | 0.0251 (5) | 0.0189 (5) | 0.0013 (4) | 0.0023 (4) | 0.0081 (4) |
C25 | 0.0255 (6) | 0.0201 (5) | 0.0198 (5) | −0.0013 (4) | 0.0025 (4) | 0.0026 (4) |
C26 | 0.0248 (6) | 0.0163 (5) | 0.0228 (5) | 0.0018 (4) | 0.0038 (4) | 0.0052 (4) |
C27 | 0.0276 (7) | 0.0428 (7) | 0.0194 (5) | −0.0010 (5) | −0.0001 (4) | 0.0059 (5) |
C31 | 0.0199 (5) | 0.0187 (5) | 0.0200 (5) | 0.0018 (4) | 0.0020 (4) | 0.0066 (4) |
C32 | 0.0285 (7) | 0.0399 (7) | 0.0343 (6) | 0.0144 (5) | 0.0116 (5) | 0.0250 (6) |
C33 | 0.0245 (7) | 0.0451 (7) | 0.0341 (7) | 0.0146 (5) | 0.0109 (5) | 0.0234 (6) |
C34 | 0.0211 (6) | 0.0296 (6) | 0.0201 (5) | −0.0010 (4) | 0.0016 (4) | 0.0099 (4) |
C35 | 0.0302 (7) | 0.0225 (5) | 0.0220 (5) | 0.0020 (4) | 0.0012 (4) | 0.0106 (4) |
C36 | 0.0244 (6) | 0.0180 (5) | 0.0214 (5) | 0.0043 (4) | 0.0008 (4) | 0.0059 (4) |
C37 | 0.0299 (8) | 0.1039 (15) | 0.0518 (10) | 0.0221 (9) | 0.0191 (7) | 0.0513 (11) |
Geometric parameters (Å, º) top
Cl—C19 | 1.7695 (13) | C32—C33 | 1.3953 (17) |
O1—C18 | 1.3343 (14) | C33—C34 | 1.3846 (17) |
O1—C17 | 1.4641 (14) | C34—C35 | 1.3908 (18) |
O2—C18 | 1.1991 (15) | C35—C36 | 1.3905 (17) |
O3—C24 | 1.3706 (14) | C1—H1 | 1.0000 |
O3—C27 | 1.4300 (15) | C13—H13 | 0.9500 |
O4—C34 | 1.3772 (14) | C14—H14 | 0.9500 |
O4—C37 | 1.4201 (19) | C15—H15 | 0.9500 |
C1—C31 | 1.5257 (15) | C16—H16 | 0.9500 |
C1—C21 | 1.5267 (15) | C17—H17A | 0.9900 |
C1—C11 | 1.5284 (15) | C17—H17B | 0.9900 |
C11—C16 | 1.3952 (15) | C19—H19A | 0.9900 |
C11—C12 | 1.4086 (15) | C19—H19B | 0.9900 |
C12—C13 | 1.3963 (16) | C22—H22 | 0.9500 |
C12—C17 | 1.5043 (15) | C23—H23 | 0.9500 |
C13—C14 | 1.3880 (17) | C25—H25 | 0.9500 |
C14—C15 | 1.3839 (18) | C26—H26 | 0.9500 |
C15—C16 | 1.3949 (17) | C27—H27A | 0.9800 |
C18—C19 | 1.5134 (17) | C27—H27B | 0.9800 |
C21—C26 | 1.3907 (15) | C27—H27C | 0.9800 |
C21—C22 | 1.3986 (15) | C32—H32 | 0.9500 |
C22—C23 | 1.3840 (16) | C33—H33 | 0.9500 |
C23—C24 | 1.3950 (16) | C35—H35 | 0.9500 |
C24—C25 | 1.3922 (16) | C36—H36 | 0.9500 |
C25—C26 | 1.3948 (17) | C37—H37A | 0.9800 |
C31—C32 | 1.3872 (16) | C37—H37B | 0.9800 |
C31—C36 | 1.3941 (15) | C37—H37C | 0.9800 |
| | | |
C18—O1—C17 | 115.63 (9) | C12—C13—H13 | 119.4 |
C24—O3—C27 | 116.41 (10) | C15—C14—H14 | 120.4 |
C34—O4—C37 | 116.74 (11) | C13—C14—H14 | 120.4 |
C31—C1—C21 | 111.18 (9) | C14—C15—H15 | 120.0 |
C31—C1—C11 | 114.30 (9) | C16—C15—H15 | 120.0 |
C21—C1—C11 | 109.87 (9) | C15—C16—H16 | 119.3 |
C16—C11—C12 | 118.21 (10) | C11—C16—H16 | 119.3 |
C16—C11—C1 | 121.28 (10) | O1—C17—H17A | 110.1 |
C12—C11—C1 | 120.38 (9) | C12—C17—H17A | 110.1 |
C13—C12—C11 | 119.70 (10) | O1—C17—H17B | 110.1 |
C13—C12—C17 | 117.93 (10) | C12—C17—H17B | 110.1 |
C11—C12—C17 | 122.37 (10) | H17A—C17—H17B | 108.4 |
C14—C13—C12 | 121.28 (11) | C18—C19—H19A | 109.3 |
C15—C14—C13 | 119.27 (11) | Cl—C19—H19A | 109.3 |
C14—C15—C16 | 120.02 (11) | C18—C19—H19B | 109.3 |
C15—C16—C11 | 121.45 (11) | Cl—C19—H19B | 109.3 |
O1—C17—C12 | 108.15 (9) | H19A—C19—H19B | 107.9 |
O2—C18—O1 | 124.89 (12) | C23—C22—H22 | 119.2 |
O2—C18—C19 | 126.01 (11) | C21—C22—H22 | 119.2 |
O1—C18—C19 | 109.08 (10) | C22—C23—H23 | 120.1 |
C18—C19—Cl | 111.67 (9) | C24—C23—H23 | 120.1 |
C26—C21—C22 | 117.64 (10) | C24—C25—H25 | 120.2 |
C26—C21—C1 | 120.87 (9) | C26—C25—H25 | 120.2 |
C22—C21—C1 | 121.48 (10) | C21—C26—H26 | 119.2 |
C23—C22—C21 | 121.61 (10) | C25—C26—H26 | 119.2 |
C22—C23—C24 | 119.88 (10) | O3—C27—H27A | 109.5 |
O3—C24—C25 | 124.59 (10) | O3—C27—H27B | 109.5 |
O3—C24—C23 | 115.80 (10) | H27A—C27—H27B | 109.5 |
C25—C24—C23 | 119.61 (10) | O3—C27—H27C | 109.5 |
C24—C25—C26 | 119.56 (10) | H27A—C27—H27C | 109.5 |
C21—C26—C25 | 121.68 (10) | H27B—C27—H27C | 109.5 |
C32—C31—C36 | 117.46 (10) | C31—C32—H32 | 118.9 |
C32—C31—C1 | 122.00 (10) | C33—C32—H32 | 118.9 |
C36—C31—C1 | 120.53 (10) | C34—C33—H33 | 120.4 |
C31—C32—C33 | 122.11 (11) | C32—C33—H33 | 120.4 |
C34—C33—C32 | 119.21 (12) | C36—C35—H35 | 120.1 |
O4—C34—C33 | 123.94 (11) | C34—C35—H35 | 120.1 |
O4—C34—C35 | 116.09 (11) | C35—C36—H36 | 119.3 |
C33—C34—C35 | 119.97 (11) | C31—C36—H36 | 119.3 |
C36—C35—C34 | 119.74 (11) | O4—C37—H37A | 109.5 |
C35—C36—C31 | 121.48 (11) | O4—C37—H37B | 109.5 |
C31—C1—H1 | 107.0 | H37A—C37—H37B | 109.5 |
C21—C1—H1 | 107.0 | O4—C37—H37C | 109.5 |
C11—C1—H1 | 107.0 | H37A—C37—H37C | 109.5 |
C14—C13—H13 | 119.4 | H37B—C37—H37C | 109.5 |
| | | |
C31—C1—C11—C16 | 14.29 (15) | C27—O3—C24—C25 | 6.43 (17) |
C21—C1—C11—C16 | −111.49 (11) | C27—O3—C24—C23 | −173.14 (10) |
C31—C1—C11—C12 | −169.84 (10) | C22—C23—C24—O3 | −178.93 (11) |
C21—C1—C11—C12 | 64.39 (13) | C22—C23—C24—C25 | 1.47 (17) |
C16—C11—C12—C13 | 2.77 (16) | O3—C24—C25—C26 | 179.41 (11) |
C1—C11—C12—C13 | −173.23 (10) | C23—C24—C25—C26 | −1.03 (17) |
C16—C11—C12—C17 | −176.85 (10) | C22—C21—C26—C25 | 0.95 (17) |
C1—C11—C12—C17 | 7.15 (16) | C1—C21—C26—C25 | −178.36 (10) |
C11—C12—C13—C14 | −1.73 (17) | C24—C25—C26—C21 | −0.20 (18) |
C17—C12—C13—C14 | 177.91 (11) | C21—C1—C31—C32 | 36.38 (15) |
C12—C13—C14—C15 | −0.62 (18) | C11—C1—C31—C32 | −88.70 (14) |
C13—C14—C15—C16 | 1.87 (19) | C21—C1—C31—C36 | −142.65 (10) |
C14—C15—C16—C11 | −0.77 (19) | C11—C1—C31—C36 | 92.27 (12) |
C12—C11—C16—C15 | −1.56 (17) | C36—C31—C32—C33 | 1.5 (2) |
C1—C11—C16—C15 | 174.40 (11) | C1—C31—C32—C33 | −177.60 (12) |
C18—O1—C17—C12 | 160.60 (10) | C31—C32—C33—C34 | 0.2 (2) |
C13—C12—C17—O1 | 81.55 (13) | C37—O4—C34—C33 | 0.0 (2) |
C11—C12—C17—O1 | −98.82 (12) | C37—O4—C34—C35 | 179.94 (14) |
C17—O1—C18—O2 | 1.44 (18) | C32—C33—C34—O4 | 178.28 (12) |
C17—O1—C18—C19 | −179.76 (10) | C32—C33—C34—C35 | −1.7 (2) |
O2—C18—C19—Cl | −9.37 (17) | O4—C34—C35—C36 | −178.41 (10) |
O1—C18—C19—Cl | 171.84 (8) | C33—C34—C35—C36 | 1.54 (18) |
C31—C1—C21—C26 | 88.73 (12) | C34—C35—C36—C31 | 0.12 (18) |
C11—C1—C21—C26 | −143.74 (10) | C32—C31—C36—C35 | −1.58 (17) |
C31—C1—C21—C22 | −90.55 (12) | C1—C31—C36—C35 | 177.49 (10) |
C11—C1—C21—C22 | 36.98 (14) | H1—C1—C11—C12 | −51.5 |
C26—C21—C22—C23 | −0.49 (17) | H1—C1—C21—C26 | −27.9 |
C1—C21—C22—C23 | 178.81 (10) | H1—C1—C31—C36 | −26.1 |
C21—C22—C23—C24 | −0.71 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O2i | 1.00 | 2.43 | 3.3793 (14) | 157 |
C26—H26···O2i | 0.95 | 2.58 | 3.4039 (15) | 145 |
C27—H27B···O4ii | 0.98 | 2.65 | 3.4856 (16) | 143 |
C37—H37B···Cliii | 0.98 | 3.00 | 3.9767 (16) | 179 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z+1; (iii) x+1, y, z−1. |