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The asymmetric unit of the title compound, C
30H
28Cl
2O
2, contains a half molecule with the other half generated by the crystallographic twofold symmetry. The hydroxyl groups are in the
trans configuration. The molecular structure is stabilized by O—H
Cl and C—H
O hydrogen bonds, and C—H
π interactions stabilize the crystal packing.
Supporting information
CCDC reference: 270263
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.076
- wR factor = 0.175
- Data-to-parameter ratio = 16.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.54
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.05 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14A .. CG1 .. 2.90 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1998) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 AND PARST (Nardelli, 1995).
1,2-Bis(2-chlorophenyl)-1,2-bis(3,4-dimethylphenyl)ethane-1,2-diol
top
Crystal data top
C30H28Cl2O2 | F(000) = 1032 |
Mr = 491.42 | Dx = 1.312 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2531 reflections |
a = 7.667 (2) Å | θ = 1.8–27.1° |
b = 22.862 (6) Å | µ = 0.29 mm−1 |
c = 14.654 (4) Å | T = 293 K |
β = 104.478 (4)° | Needle, colourless |
V = 2487.0 (11) Å3 | 0.52 × 0.24 × 0.16 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 1904 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.044 |
Graphite monochromator | θmax = 27.1°, θmin = 1.8° |
ω scans | h = −9→9 |
9108 measured reflections | k = −28→28 |
2531 independent reflections | l = −18→18 |
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)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.175 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0773P)2 + 2.2226P] where P = (Fo2 + 2Fc2)/3 |
2531 reflections | (Δ/σ)max < 0.001 |
157 parameters | Δρmax = 0.76 e Å−3 |
0 restraints | Δρmin = −0.22 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 | |
Cl1 | 0.39440 (12) | 0.31179 (4) | −0.02469 (6) | 0.0504 (3) | |
O1 | 0.2961 (3) | 0.33349 (10) | 0.15886 (15) | 0.0428 (6) | |
H1 | 0.2716 | 0.3378 | 0.1015 | 0.064* | |
C1 | 0.4879 (4) | 0.32981 (12) | 0.1947 (2) | 0.0351 (7) | |
C2 | 0.5602 (4) | 0.27432 (13) | 0.1550 (2) | 0.0374 (7) | |
C3 | 0.6721 (4) | 0.23329 (14) | 0.2119 (3) | 0.0488 (8) | |
H3 | 0.7091 | 0.2399 | 0.2765 | 0.059* | |
C4 | 0.7294 (5) | 0.18339 (16) | 0.1754 (3) | 0.0594 (10) | |
H4 | 0.8022 | 0.1567 | 0.2155 | 0.071* | |
C5 | 0.6797 (5) | 0.17278 (15) | 0.0801 (3) | 0.0586 (10) | |
H5 | 0.7163 | 0.1386 | 0.0558 | 0.070* | |
C6 | 0.5765 (5) | 0.21269 (15) | 0.0216 (3) | 0.0501 (9) | |
H6 | 0.5443 | 0.2063 | −0.0431 | 0.060* | |
C7 | 0.5194 (4) | 0.26288 (13) | 0.0590 (2) | 0.0398 (7) | |
C8 | 0.5810 (4) | 0.38387 (13) | 0.1664 (2) | 0.0390 (7) | |
C9 | 0.7599 (5) | 0.38254 (15) | 0.1626 (2) | 0.0475 (8) | |
H9 | 0.8240 | 0.3476 | 0.1740 | 0.057* | |
C10 | 0.8446 (6) | 0.43270 (18) | 0.1419 (3) | 0.0608 (10) | |
H10 | 0.9639 | 0.4305 | 0.1383 | 0.073* | |
C11 | 0.7568 (6) | 0.48516 (18) | 0.1265 (3) | 0.0632 (11) | |
C12 | 0.5772 (6) | 0.48803 (14) | 0.1296 (2) | 0.0571 (10) | |
C13 | 0.4907 (5) | 0.43672 (14) | 0.1484 (2) | 0.0478 (8) | |
H13 | 0.3696 | 0.4384 | 0.1487 | 0.057* | |
C14 | 0.4775 (7) | 0.54348 (18) | 0.1159 (3) | 0.0800 (13) | |
H14A | 0.4819 | 0.5602 | 0.0564 | 0.120* | |
H14B | 0.5311 | 0.5701 | 0.1657 | 0.120* | |
H14C | 0.3544 | 0.5364 | 0.1165 | 0.120* | |
C15 | 0.8547 (8) | 0.5405 (2) | 0.1075 (4) | 0.1067 (19) | |
H15A | 0.9755 | 0.5308 | 0.1056 | 0.160* | |
H15B | 0.8580 | 0.5684 | 0.1569 | 0.160* | |
H15C | 0.7920 | 0.5571 | 0.0482 | 0.160* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0581 (6) | 0.0568 (5) | 0.0356 (5) | −0.0062 (4) | 0.0104 (4) | −0.0013 (4) |
O1 | 0.0384 (12) | 0.0521 (13) | 0.0365 (12) | 0.0025 (10) | 0.0067 (10) | −0.0017 (10) |
C1 | 0.0345 (17) | 0.0379 (16) | 0.0331 (16) | 0.0006 (12) | 0.0086 (13) | 0.0007 (12) |
C2 | 0.0381 (17) | 0.0383 (16) | 0.0388 (17) | −0.0049 (13) | 0.0156 (14) | −0.0016 (12) |
C3 | 0.051 (2) | 0.0477 (18) | 0.049 (2) | 0.0055 (15) | 0.0159 (17) | 0.0018 (15) |
C4 | 0.062 (2) | 0.048 (2) | 0.072 (3) | 0.0148 (17) | 0.025 (2) | 0.0043 (18) |
C5 | 0.061 (2) | 0.044 (2) | 0.080 (3) | 0.0003 (17) | 0.036 (2) | −0.0118 (18) |
C6 | 0.049 (2) | 0.053 (2) | 0.055 (2) | −0.0101 (17) | 0.0252 (17) | −0.0148 (17) |
C7 | 0.0386 (17) | 0.0394 (16) | 0.0444 (18) | −0.0091 (13) | 0.0162 (14) | −0.0032 (13) |
C8 | 0.050 (2) | 0.0403 (17) | 0.0266 (16) | −0.0044 (14) | 0.0095 (14) | −0.0019 (12) |
C9 | 0.052 (2) | 0.052 (2) | 0.0387 (19) | −0.0075 (16) | 0.0116 (16) | −0.0018 (15) |
C10 | 0.064 (2) | 0.073 (3) | 0.046 (2) | −0.023 (2) | 0.0141 (19) | −0.0006 (18) |
C11 | 0.083 (3) | 0.064 (3) | 0.041 (2) | −0.029 (2) | 0.012 (2) | −0.0006 (17) |
C12 | 0.099 (3) | 0.0392 (18) | 0.0297 (18) | −0.0024 (18) | 0.0093 (19) | 0.0010 (13) |
C13 | 0.065 (2) | 0.0445 (18) | 0.0332 (17) | 0.0006 (16) | 0.0100 (16) | 0.0009 (13) |
C14 | 0.113 (4) | 0.058 (2) | 0.069 (3) | 0.010 (2) | 0.022 (3) | 0.009 (2) |
C15 | 0.139 (5) | 0.085 (3) | 0.094 (4) | −0.057 (3) | 0.026 (4) | 0.015 (3) |
Geometric parameters (Å, º) top
Cl1—C7 | 1.756 (3) | C8—C9 | 1.388 (5) |
O1—C1 | 1.435 (4) | C9—C10 | 1.388 (5) |
O1—H1 | 0.82 | C9—H9 | 0.93 |
C1—C8 | 1.535 (4) | C10—C11 | 1.366 (6) |
C1—C2 | 1.554 (4) | C10—H10 | 0.93 |
C1—C1i | 1.585 (6) | C11—C12 | 1.391 (6) |
C2—C7 | 1.388 (4) | C11—C15 | 1.532 (5) |
C2—C3 | 1.398 (4) | C12—C13 | 1.408 (5) |
C3—C4 | 1.378 (5) | C12—C14 | 1.468 (5) |
C3—H3 | 0.93 | C13—H13 | 0.93 |
C4—C5 | 1.373 (6) | C14—H14A | 0.96 |
C4—H4 | 0.93 | C14—H14B | 0.96 |
C5—C6 | 1.362 (5) | C14—H14C | 0.96 |
C5—H5 | 0.93 | C15—H15A | 0.96 |
C6—C7 | 1.388 (4) | C15—H15B | 0.96 |
C6—H6 | 0.93 | C15—H15C | 0.96 |
C8—C13 | 1.385 (4) | | |
| | | |
C1—O1—H1 | 109.5 | C8—C9—C10 | 120.8 (3) |
O1—C1—C8 | 110.9 (2) | C8—C9—H9 | 119.6 |
O1—C1—C2 | 109.8 (2) | C10—C9—H9 | 119.6 |
C8—C1—C2 | 108.8 (2) | C11—C10—C9 | 121.5 (4) |
O1—C1—C1i | 102.8 (3) | C11—C10—H10 | 119.2 |
C8—C1—C1i | 109.4 (2) | C9—C10—H10 | 119.2 |
C2—C1—C1i | 114.91 (19) | C10—C11—C12 | 119.2 (3) |
C7—C2—C3 | 115.3 (3) | C10—C11—C15 | 120.8 (4) |
C7—C2—C1 | 121.5 (3) | C12—C11—C15 | 120.1 (4) |
C3—C2—C1 | 123.2 (3) | C11—C12—C13 | 119.1 (3) |
C4—C3—C2 | 122.1 (3) | C11—C12—C14 | 121.5 (4) |
C4—C3—H3 | 119.0 | C13—C12—C14 | 119.4 (4) |
C2—C3—H3 | 119.0 | C8—C13—C12 | 121.8 (4) |
C5—C4—C3 | 120.5 (4) | C8—C13—H13 | 119.1 |
C5—C4—H4 | 119.8 | C12—C13—H13 | 119.1 |
C3—C4—H4 | 119.8 | C12—C14—H14A | 109.5 |
C6—C5—C4 | 119.4 (3) | C12—C14—H14B | 109.5 |
C6—C5—H5 | 120.3 | H14A—C14—H14B | 109.5 |
C4—C5—H5 | 120.3 | C12—C14—H14C | 109.5 |
C5—C6—C7 | 119.8 (3) | H14A—C14—H14C | 109.5 |
C5—C6—H6 | 120.1 | H14B—C14—H14C | 109.5 |
C7—C6—H6 | 120.1 | C11—C15—H15A | 109.5 |
C2—C7—C6 | 122.8 (3) | C11—C15—H15B | 109.5 |
C2—C7—Cl1 | 122.2 (2) | H15A—C15—H15B | 109.5 |
C6—C7—Cl1 | 115.0 (3) | C11—C15—H15C | 109.5 |
C13—C8—C9 | 117.6 (3) | H15A—C15—H15C | 109.5 |
C13—C8—C1 | 120.7 (3) | H15B—C15—H15C | 109.5 |
C9—C8—C1 | 121.6 (3) | | |
| | | |
O1—C1—C2—C7 | 52.6 (4) | C2—C1—C8—C13 | 147.2 (3) |
C8—C1—C2—C7 | −69.0 (3) | C1i—C1—C8—C13 | −86.5 (4) |
C1i—C1—C2—C7 | 167.8 (3) | O1—C1—C8—C9 | −157.1 (3) |
O1—C1—C2—C3 | −128.7 (3) | C2—C1—C8—C9 | −36.1 (4) |
C8—C1—C2—C3 | 109.7 (3) | C1i—C1—C8—C9 | 90.2 (3) |
C1i—C1—C2—C3 | −13.4 (4) | C13—C8—C9—C10 | 0.3 (5) |
C7—C2—C3—C4 | −3.5 (5) | C1—C8—C9—C10 | −176.5 (3) |
C1—C2—C3—C4 | 177.7 (3) | C8—C9—C10—C11 | 1.4 (5) |
C2—C3—C4—C5 | 1.1 (6) | C9—C10—C11—C12 | −1.5 (6) |
C3—C4—C5—C6 | 1.5 (6) | C9—C10—C11—C15 | 177.6 (4) |
C4—C5—C6—C7 | −1.4 (5) | C10—C11—C12—C13 | −0.1 (5) |
C3—C2—C7—C6 | 3.5 (4) | C15—C11—C12—C13 | −179.2 (4) |
C1—C2—C7—C6 | −177.6 (3) | C10—C11—C12—C14 | 178.5 (4) |
C3—C2—C7—Cl1 | −175.3 (2) | C15—C11—C12—C14 | −0.6 (6) |
C1—C2—C7—Cl1 | 3.5 (4) | C9—C8—C13—C12 | −1.9 (5) |
C5—C6—C7—C2 | −1.2 (5) | C1—C8—C13—C12 | 174.9 (3) |
C5—C6—C7—Cl1 | 177.7 (3) | C11—C12—C13—C8 | 1.8 (5) |
O1—C1—C8—C13 | 26.2 (4) | C14—C12—C13—C8 | −176.8 (3) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Cl1 | 0.82 | 2.35 | 3.010 (2) | 138 |
C13—H13···O1 | 0.93 | 2.48 | 2.817 (4) | 102 |
C3—H3···O1i | 0.93 | 2.34 | 2.943 (4) | 122 |
C14—H14A···Cg1ii | 0.96 | 2.90 | 3.751 (5) | 148 |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x+1/2, y+1/2, z+1. |
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