2,2′-[1,2-Bis(4-chloro­phenyl)­ethane-1,2-diyl]­bis(1-tetralone)

Shi, D.; Rong, L.; Wang, J.; Wang, X.; Hu, H.

doi:10.1107/S1600536803017768

2,2'-[1,2-Bis(4-chlorophenyl)ethane-1,2-diyl]bis(1-tetralone)

D. Shi, L. Rong, J. Wang, X. Wang and H. Hu

The title compound, C₃₄H₂₈Cl₂O₂, was synthesized by the self-coupling reaction of 2-(4-chlorobenzyl)-1-tetralone induced by low-valent titanium reagent (TiCl₄/Zn) in tetrahydrofuran. The X-ray analysis reveals that the two cyclohexenone rings adopt different conformations, viz. envelope and distorted half-chair.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017768/ci6261sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017768/ci6261Isup2.hkl Contains datablock I

CCDC reference: 194441

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Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R factor = 0.037
wR factor = 0.088
Data-to-parameter ratio = 13.6

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No syntax errors found



Alert level A
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing ..          ?

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

In the early seventies, Tyreik & Wolochowicz (1973), Mukaiyama et al. (1973) and McMurry & Fleming (1974) established that low-valent titanium can abstract oxygen from ketones or aldehydes leading to formation of olefins. An increasing interest in the reaction induced by low-valent titanium reagents is observed and a large number of functional groups can be reduced (Shi et al., 1993, 1997, 1998). We report here the crystal structure of the title compound, (I), synthesized by the reaction of 2-(4-chlorobenzyl)-1-tetralone induced by low-valent titanium reagent (TiCl₄/Zn).

The molecular structure of (I) is shown in Fig. 1 and selected bond lengths and angles are listed in Table 1. The C7—C24 linkage resulting from dimerization reaction of 2-(4-chlorobenzyl)-1-tetralone has a length of 1.549 (2) Å. The bond angles around C7 and C24 deviate from the ideal value for a sp³ carbon. One of the cyclohexenone rings (C8–C11/C16/C17) adopts an envelope conformation with C9 deviating by 0.652 (2) Å from the plane determined by the other five atoms. The other cyclohexenone ring (C25–C28/C33/C34) adopts a distorted half-chair conformation, with atoms C25 and C26 deviating from the C27/C28/C33/C34 plane by −0.186 (2) and 0.576 (2) Å, respectively. In addition, the X-ray analysis reveals that the configuration of (I) is threo and its conformation is gauche. Carbonyl atoms O1 and O2 are involved in weak intramolecular C—H···O interactions (Table 2) and the molecular packing in the crystal (Fig. 2) is stabilized by C—H···π interactions involving C30—H30 and phenyl ring (C18–C23) at (x, 1 + y, z).

Experimental top

The title compound, (I), was prepared by the reaction of 2-(4-chlorobenzyl)-1-tetralone induced by low-valent titanium reagent (TiCl₄/Zn); m.p. 491–493 K. Single crystals were obtained by slow evaporation of ethanol solution.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability of displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The molecular packing of (I), viewed down the c axis.

2,2'-[1,2-bis(4-chlorophenyl)ethane-1,2-diyl]bis(1-tetralone) top

Crystal data top

C₃₄H₂₈Cl₂O₂	Z = 2
M_r = 539.46	F(000) = 564
Triclinic, P1	D_x = 1.339 Mg m⁻³
Hall symbol: -P 1	Melting point = 491–493 K
a = 10.411 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.975 (1) Å	Cell parameters from 31 reflections
c = 13.296 (2) Å	θ = 4.4–15.0°
α = 103.54 (1)°	µ = 0.27 mm⁻¹
β = 112.97 (1)°	T = 294 K
γ = 93.89 (1)°	Block, colorless
V = 1338.2 (4) Å³	0.52 × 0.48 × 0.48 mm

Data collection top

Siemens P4 diffractometer	3392 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	R_int = 0.015
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
ω scans	h = 0→12
Absorption correction: ψ scan (XSCANS; Siemens, 1994)	k = −12→12
T_min = 0.865, T_max = 0.877	l = −15→14
5121 measured reflections	3 standard reflections every 97 reflections
4671 independent reflections	intensity decay: 4.3%

Refinement top

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0415P)² + 0.0134P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4671 reflections	Δρ_max = 0.16 e Å⁻³
344 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0082 (11)

Crystal data top

C₃₄H₂₈Cl₂O₂	γ = 93.89 (1)°
M_r = 539.46	V = 1338.2 (4) Å³
Triclinic, P1	Z = 2
a = 10.411 (2) Å	Mo Kα radiation
b = 10.975 (1) Å	µ = 0.27 mm⁻¹
c = 13.296 (2) Å	T = 294 K
α = 103.54 (1)°	0.52 × 0.48 × 0.48 mm
β = 112.97 (1)°

Data collection top

Siemens P4 diffractometer	3392 reflections with I > 2σ(I)
Absorption correction: ψ scan (XSCANS; Siemens, 1994)	R_int = 0.015
T_min = 0.865, T_max = 0.877	3 standard reflections every 97 reflections
5121 measured reflections	intensity decay: 4.3%
4671 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.05	Δρ_max = 0.16 e Å⁻³
4671 reflections	Δρ_min = −0.20 e Å⁻³
344 parameters

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	U_iso*/U_eq
Cl1	0.46763 (6)	−0.12191 (5)	0.31639 (5)	0.05752 (17)
Cl2	−0.32745 (6)	0.16497 (6)	0.24082 (5)	0.0678 (2)
O1	0.26254 (14)	0.47766 (13)	0.03461 (11)	0.0540 (4)
O2	0.26291 (16)	0.64897 (12)	0.46526 (11)	0.0571 (4)
C1	0.40741 (19)	0.01511 (16)	0.28585 (16)	0.0390 (4)
C2	0.3391 (2)	0.01562 (17)	0.17461 (16)	0.0465 (5)
H2	0.3218	−0.0575	0.1158	0.056*
C3	0.2964 (2)	0.12577 (17)	0.15090 (15)	0.0429 (5)
H3	0.2492	0.1256	0.0753	0.052*
C4	0.32177 (18)	0.23713 (16)	0.23681 (14)	0.0357 (4)
C5	0.3885 (2)	0.23150 (17)	0.34802 (15)	0.0435 (5)
H5	0.4043	0.3036	0.4074	0.052*
C6	0.4324 (2)	0.12182 (17)	0.37330 (16)	0.0440 (5)
H6	0.4781	0.1206	0.4486	0.053*
C7	0.28695 (18)	0.35986 (16)	0.20678 (14)	0.0359 (4)
H7	0.2124	0.3351	0.1289	0.043*
C8	0.41883 (18)	0.43099 (17)	0.20320 (15)	0.0389 (4)
H8	0.4620	0.3627	0.1739	0.047*
C9	0.53717 (19)	0.50844 (19)	0.31668 (16)	0.0483 (5)
H9A	0.5029	0.5790	0.3516	0.058*
H9B	0.5659	0.4552	0.3677	0.058*
C10	0.6637 (2)	0.5593 (2)	0.29875 (18)	0.0546 (5)
H10A	0.7353	0.6130	0.3709	0.065*
H10B	0.7046	0.4884	0.2725	0.065*
C11	0.62387 (19)	0.63492 (17)	0.21344 (16)	0.0419 (5)
C12	0.7213 (2)	0.7338 (2)	0.22015 (18)	0.0537 (5)
H12	0.8129	0.7524	0.2774	0.064*
C13	0.6836 (2)	0.8039 (2)	0.1434 (2)	0.0613 (6)
H13	0.7494	0.8702	0.1497	0.074*
C14	0.5484 (2)	0.7766 (2)	0.05667 (18)	0.0574 (6)
H14	0.5229	0.8243	0.0048	0.069*
C15	0.4524 (2)	0.67827 (18)	0.04805 (16)	0.0472 (5)
H15	0.3619	0.6586	−0.0110	0.057*
C16	0.48817 (18)	0.60779 (16)	0.12610 (15)	0.0372 (4)
C17	0.37838 (19)	0.50442 (17)	0.11436 (15)	0.0389 (4)
C18	−0.16661 (19)	0.24110 (18)	0.25482 (17)	0.0430 (5)
C19	−0.0730 (2)	0.32180 (18)	0.35748 (17)	0.0472 (5)
H19	−0.0943	0.3361	0.4205	0.057*
C20	0.0544 (2)	0.38200 (17)	0.36625 (16)	0.0418 (5)
H20	0.1183	0.4360	0.4363	0.050*
C21	0.08899 (18)	0.36399 (16)	0.27367 (14)	0.0351 (4)
C22	−0.00811 (19)	0.27985 (18)	0.17199 (15)	0.0456 (5)
H22	0.0127	0.2640	0.1087	0.055*
C23	−0.1347 (2)	0.21895 (19)	0.16212 (16)	0.0485 (5)
H23	−0.1980	0.1631	0.0929	0.058*
C24	0.22459 (18)	0.43878 (16)	0.28373 (14)	0.0349 (4)
H24	0.2945	0.4546	0.3626	0.042*
C25	0.19947 (18)	0.57050 (16)	0.26492 (14)	0.0361 (4)
H25	0.2775	0.6023	0.2489	0.043*
C26	0.06263 (19)	0.57157 (17)	0.16419 (15)	0.0437 (5)
H26A	0.0537	0.5081	0.0962	0.052*
H26B	−0.0184	0.5505	0.1798	0.052*
C27	0.0651 (2)	0.70260 (18)	0.14470 (16)	0.0502 (5)
H27A	0.1381	0.7179	0.1187	0.060*
H27B	−0.0253	0.7045	0.0852	0.060*
C28	0.09294 (18)	0.80685 (17)	0.25047 (16)	0.0416 (5)
C29	0.0560 (2)	0.9253 (2)	0.2449 (2)	0.0553 (6)
H29	0.0134	0.9403	0.1742	0.066*
C30	0.0809 (2)	1.0201 (2)	0.3412 (2)	0.0661 (7)
H30	0.0561	1.0988	0.3353	0.079*
C31	0.1425 (2)	1.0000 (2)	0.4469 (2)	0.0658 (6)
H31	0.1578	1.0643	0.5121	0.079*
C32	0.1811 (2)	0.88434 (19)	0.45544 (18)	0.0529 (5)
H32	0.2233	0.8707	0.5268	0.064*
C33	0.15758 (19)	0.78711 (16)	0.35800 (16)	0.0396 (4)
C34	0.20949 (18)	0.66681 (17)	0.37178 (15)	0.0383 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0692 (4)	0.0426 (3)	0.0719 (4)	0.0213 (3)	0.0355 (3)	0.0227 (3)
Cl2	0.0474 (3)	0.0867 (4)	0.0790 (4)	0.0038 (3)	0.0319 (3)	0.0334 (3)
O1	0.0424 (8)	0.0706 (10)	0.0424 (8)	0.0009 (7)	0.0084 (7)	0.0231 (7)
O2	0.0809 (10)	0.0448 (8)	0.0329 (8)	0.0155 (7)	0.0112 (7)	0.0089 (6)
C1	0.0390 (11)	0.0359 (10)	0.0474 (12)	0.0079 (8)	0.0229 (9)	0.0126 (9)
C2	0.0563 (13)	0.0347 (11)	0.0455 (12)	0.0044 (9)	0.0239 (10)	0.0022 (9)
C3	0.0467 (11)	0.0440 (11)	0.0335 (10)	0.0058 (9)	0.0141 (9)	0.0081 (9)
C4	0.0325 (10)	0.0381 (10)	0.0382 (10)	0.0061 (8)	0.0170 (8)	0.0103 (8)
C5	0.0518 (12)	0.0394 (11)	0.0371 (11)	0.0119 (9)	0.0184 (9)	0.0060 (8)
C6	0.0490 (12)	0.0454 (12)	0.0405 (11)	0.0124 (9)	0.0190 (9)	0.0158 (9)
C7	0.0342 (10)	0.0400 (10)	0.0311 (9)	0.0060 (8)	0.0118 (8)	0.0095 (8)
C8	0.0369 (10)	0.0405 (10)	0.0399 (10)	0.0085 (8)	0.0151 (9)	0.0135 (8)
C9	0.0401 (11)	0.0558 (13)	0.0442 (12)	0.0064 (10)	0.0088 (9)	0.0222 (10)
C10	0.0358 (11)	0.0608 (13)	0.0619 (13)	0.0078 (10)	0.0106 (10)	0.0255 (11)
C11	0.0388 (11)	0.0405 (11)	0.0501 (12)	0.0101 (9)	0.0221 (10)	0.0122 (9)
C12	0.0402 (12)	0.0587 (13)	0.0621 (14)	0.0042 (10)	0.0232 (11)	0.0154 (11)
C13	0.0646 (15)	0.0539 (14)	0.0789 (16)	0.0027 (12)	0.0424 (14)	0.0235 (12)
C14	0.0706 (15)	0.0574 (14)	0.0607 (14)	0.0144 (12)	0.0372 (13)	0.0289 (11)
C15	0.0533 (12)	0.0511 (12)	0.0439 (11)	0.0130 (10)	0.0246 (10)	0.0171 (10)
C16	0.0381 (10)	0.0378 (10)	0.0404 (10)	0.0108 (8)	0.0214 (9)	0.0096 (8)
C17	0.0374 (11)	0.0432 (11)	0.0369 (10)	0.0109 (9)	0.0165 (9)	0.0099 (8)
C18	0.0373 (11)	0.0477 (12)	0.0545 (13)	0.0150 (9)	0.0228 (10)	0.0251 (10)
C19	0.0598 (13)	0.0467 (12)	0.0497 (13)	0.0167 (10)	0.0351 (11)	0.0167 (10)
C20	0.0506 (12)	0.0368 (11)	0.0403 (11)	0.0098 (9)	0.0218 (9)	0.0096 (8)
C21	0.0377 (10)	0.0346 (10)	0.0350 (10)	0.0111 (8)	0.0148 (8)	0.0126 (8)
C22	0.0440 (12)	0.0575 (13)	0.0362 (11)	0.0047 (10)	0.0205 (9)	0.0100 (10)
C23	0.0401 (11)	0.0597 (13)	0.0388 (11)	0.0032 (10)	0.0112 (9)	0.0128 (10)
C24	0.0354 (10)	0.0376 (10)	0.0291 (9)	0.0073 (8)	0.0109 (8)	0.0091 (8)
C25	0.0353 (10)	0.0380 (10)	0.0333 (10)	0.0076 (8)	0.0124 (8)	0.0099 (8)
C26	0.0439 (11)	0.0430 (11)	0.0359 (10)	0.0095 (9)	0.0085 (9)	0.0105 (9)
C27	0.0483 (12)	0.0558 (13)	0.0429 (12)	0.0131 (10)	0.0099 (10)	0.0226 (10)
C28	0.0321 (10)	0.0413 (11)	0.0528 (12)	0.0075 (9)	0.0168 (9)	0.0177 (9)
C29	0.0439 (12)	0.0523 (13)	0.0733 (15)	0.0149 (10)	0.0198 (11)	0.0306 (12)
C30	0.0593 (15)	0.0427 (13)	0.099 (2)	0.0228 (11)	0.0328 (14)	0.0213 (13)
C31	0.0722 (16)	0.0449 (13)	0.0806 (18)	0.0170 (12)	0.0387 (14)	0.0043 (12)
C32	0.0591 (14)	0.0464 (12)	0.0552 (13)	0.0134 (10)	0.0274 (11)	0.0105 (10)
C33	0.0370 (10)	0.0354 (10)	0.0472 (11)	0.0066 (8)	0.0193 (9)	0.0101 (9)
C34	0.0356 (10)	0.0379 (10)	0.0359 (11)	0.0047 (8)	0.0104 (9)	0.0091 (8)

Geometric parameters (Å, º) top

Cl1—C1	1.7420 (18)	C15—H15	0.93
Cl2—C18	1.7409 (19)	C16—C17	1.490 (2)
O1—C17	1.214 (2)	C18—C19	1.370 (3)
O2—C34	1.217 (2)	C18—C23	1.371 (3)
C1—C6	1.370 (2)	C19—C20	1.390 (3)
C1—C2	1.370 (2)	C19—H19	0.93
C2—C3	1.379 (2)	C20—C21	1.388 (2)
C2—H2	0.93	C20—H20	0.93
C3—C4	1.391 (2)	C21—C22	1.387 (2)
C3—H3	0.93	C21—C24	1.526 (2)
C4—C5	1.386 (2)	C22—C23	1.380 (2)
C4—C7	1.520 (2)	C22—H22	0.93
C5—C6	1.384 (2)	C23—H23	0.93
C5—H5	0.93	C24—C25	1.546 (2)
C6—H6	0.93	C24—H24	0.98
C7—C24	1.549 (2)	C25—C34	1.521 (2)
C7—C8	1.555 (2)	C25—C26	1.531 (2)
C7—H7	0.98	C25—H25	0.98
C8—C9	1.524 (2)	C26—C27	1.520 (2)
C8—C17	1.525 (2)	C26—H26A	0.97
C8—H8	0.98	C26—H26B	0.97
C9—C10	1.521 (3)	C27—C28	1.501 (3)
C9—H9A	0.97	C27—H27A	0.97
C9—H9B	0.97	C27—H27B	0.97
C10—C11	1.506 (3)	C28—C29	1.391 (3)
C10—H10A	0.97	C28—C33	1.399 (2)
C10—H10B	0.97	C29—C30	1.368 (3)
C11—C16	1.391 (2)	C29—H29	0.93
C11—C12	1.396 (3)	C30—C31	1.377 (3)
C12—C13	1.372 (3)	C30—H30	0.93
C12—H12	0.93	C31—C32	1.373 (3)
C13—C14	1.384 (3)	C31—H31	0.93
C13—H13	0.93	C32—C33	1.395 (3)
C14—C15	1.372 (3)	C32—H32	0.93
C14—H14	0.93	C33—C34	1.484 (2)
C15—C16	1.388 (2)

C6—C1—C2	120.94 (17)	C19—C18—C23	120.48 (18)
C6—C1—Cl1	119.56 (15)	C19—C18—Cl2	120.28 (15)
C2—C1—Cl1	119.48 (14)	C23—C18—Cl2	119.24 (16)
C1—C2—C3	119.24 (17)	C18—C19—C20	119.16 (18)
C1—C2—H2	120.4	C18—C19—H19	120.4
C3—C2—H2	120.4	C20—C19—H19	120.4
C2—C3—C4	121.87 (17)	C21—C20—C19	121.97 (18)
C2—C3—H3	119.1	C21—C20—H20	119.0
C4—C3—H3	119.1	C19—C20—H20	119.0
C5—C4—C3	116.90 (17)	C22—C21—C20	116.78 (17)
C5—C4—C7	122.94 (15)	C22—C21—C24	122.41 (16)
C3—C4—C7	119.99 (16)	C20—C21—C24	120.75 (16)
C6—C5—C4	121.94 (17)	C23—C22—C21	121.88 (17)
C6—C5—H5	119.0	C23—C22—H22	119.1
C4—C5—H5	119.0	C21—C22—H22	119.1
C1—C6—C5	119.07 (17)	C18—C23—C22	119.71 (18)
C1—C6—H6	120.5	C18—C23—H23	120.1
C5—C6—H6	120.5	C22—C23—H23	120.1
C4—C7—C24	111.85 (14)	C21—C24—C25	110.19 (14)
C4—C7—C8	108.79 (14)	C21—C24—C7	111.58 (14)
C24—C7—C8	115.78 (14)	C25—C24—C7	114.44 (14)
C4—C7—H7	106.6	C21—C24—H24	106.7
C24—C7—H7	106.6	C25—C24—H24	106.7
C8—C7—H7	106.6	C7—C24—H24	106.7
C9—C8—C17	112.59 (15)	C34—C25—C26	109.18 (14)
C9—C8—C7	117.29 (15)	C34—C25—C24	112.25 (14)
C17—C8—C7	112.40 (14)	C26—C25—C24	116.14 (14)
C9—C8—H8	104.3	C34—C25—H25	106.2
C17—C8—H8	104.3	C26—C25—H25	106.2
C7—C8—H8	104.3	C24—C25—H25	106.2
C10—C9—C8	110.31 (16)	C27—C26—C25	109.78 (15)
C10—C9—H9A	109.6	C27—C26—H26A	109.7
C8—C9—H9A	109.6	C25—C26—H26A	109.7
C10—C9—H9B	109.6	C27—C26—H26B	109.7
C8—C9—H9B	109.6	C25—C26—H26B	109.7
H9A—C9—H9B	108.1	H26A—C26—H26B	108.2
C11—C10—C9	112.25 (15)	C28—C27—C26	112.39 (15)
C11—C10—H10A	109.2	C28—C27—H27A	109.1
C9—C10—H10A	109.2	C26—C27—H27A	109.1
C11—C10—H10B	109.2	C28—C27—H27B	109.1
C9—C10—H10B	109.2	C26—C27—H27B	109.1
H10A—C10—H10B	107.9	H27A—C27—H27B	107.9
C16—C11—C12	118.46 (18)	C29—C28—C33	118.08 (18)
C16—C11—C10	120.44 (17)	C29—C28—C27	121.39 (18)
C12—C11—C10	121.10 (17)	C33—C28—C27	120.52 (16)
C13—C12—C11	120.9 (2)	C30—C29—C28	121.4 (2)
C13—C12—H12	119.6	C30—C29—H29	119.3
C11—C12—H12	119.6	C28—C29—H29	119.3
C12—C13—C14	120.5 (2)	C29—C30—C31	120.5 (2)
C12—C13—H13	119.8	C29—C30—H30	119.8
C14—C13—H13	119.8	C31—C30—H30	119.8
C15—C14—C13	119.2 (2)	C32—C31—C30	119.6 (2)
C15—C14—H14	120.4	C32—C31—H31	120.2
C13—C14—H14	120.4	C30—C31—H31	120.2
C14—C15—C16	120.98 (19)	C31—C32—C33	120.5 (2)
C14—C15—H15	119.5	C31—C32—H32	119.7
C16—C15—H15	119.5	C33—C32—H32	119.7
C15—C16—C11	119.99 (17)	C32—C33—C28	119.88 (17)
C15—C16—C17	118.63 (17)	C32—C33—C34	118.64 (17)
C11—C16—C17	121.38 (16)	C28—C33—C34	121.40 (16)
O1—C17—C16	120.68 (17)	O2—C34—C33	121.16 (16)
O1—C17—C8	121.60 (17)	O2—C34—C25	121.86 (16)
C16—C17—C8	117.68 (15)	C33—C34—C25	116.91 (15)

C6—C1—C2—C3	0.6 (3)	C18—C19—C20—C21	0.8 (3)
Cl1—C1—C2—C3	−177.59 (14)	C19—C20—C21—C22	−1.8 (3)
C1—C2—C3—C4	0.6 (3)	C19—C20—C21—C24	175.49 (16)
C2—C3—C4—C5	−1.9 (3)	C20—C21—C22—C23	1.5 (3)
C2—C3—C4—C7	173.47 (17)	C24—C21—C22—C23	−175.74 (17)
C3—C4—C5—C6	2.1 (3)	C19—C18—C23—C22	−0.9 (3)
C7—C4—C5—C6	−173.18 (16)	Cl2—C18—C23—C22	179.32 (14)
C2—C1—C6—C5	−0.5 (3)	C21—C22—C23—C18	−0.2 (3)
Cl1—C1—C6—C5	177.73 (14)	C22—C21—C24—C25	92.90 (19)
C4—C5—C6—C1	−0.9 (3)	C20—C21—C24—C25	−84.20 (19)
C5—C4—C7—C24	−43.6 (2)	C22—C21—C24—C7	−35.4 (2)
C3—C4—C7—C24	141.35 (16)	C20—C21—C24—C7	147.53 (16)
C5—C4—C7—C8	85.6 (2)	C4—C7—C24—C21	−59.28 (18)
C3—C4—C7—C8	−89.49 (19)	C8—C7—C24—C21	175.33 (13)
C4—C7—C8—C9	−80.28 (19)	C4—C7—C24—C25	174.74 (14)
C24—C7—C8—C9	46.7 (2)	C8—C7—C24—C25	49.4 (2)
C4—C7—C8—C17	146.85 (15)	C21—C24—C25—C34	81.45 (17)
C24—C7—C8—C17	−86.21 (18)	C7—C24—C25—C34	−151.86 (15)
C17—C8—C9—C10	−53.4 (2)	C21—C24—C25—C26	−45.1 (2)
C7—C8—C9—C10	173.82 (15)	C7—C24—C25—C26	81.5 (2)
C8—C9—C10—C11	55.0 (2)	C34—C25—C26—C27	61.5 (2)
C9—C10—C11—C16	−29.0 (3)	C24—C25—C26—C27	−170.42 (15)
C9—C10—C11—C12	150.73 (18)	C25—C26—C27—C28	−53.8 (2)
C16—C11—C12—C13	0.9 (3)	C26—C27—C28—C29	−159.23 (17)
C10—C11—C12—C13	−178.8 (2)	C26—C27—C28—C33	20.9 (3)
C11—C12—C13—C14	−0.9 (3)	C33—C28—C29—C30	−0.3 (3)
C12—C13—C14—C15	−0.2 (3)	C27—C28—C29—C30	179.80 (19)
C13—C14—C15—C16	1.2 (3)	C28—C29—C30—C31	−0.7 (3)
C14—C15—C16—C11	−1.2 (3)	C29—C30—C31—C32	1.1 (3)
C14—C15—C16—C17	178.37 (17)	C30—C31—C32—C33	−0.4 (3)
C12—C11—C16—C15	0.1 (3)	C31—C32—C33—C28	−0.6 (3)
C10—C11—C16—C15	179.85 (17)	C31—C32—C33—C34	176.08 (18)
C12—C11—C16—C17	−179.43 (16)	C29—C28—C33—C32	1.0 (3)
C10—C11—C16—C17	0.3 (3)	C27—C28—C33—C32	−179.17 (17)
C15—C16—C17—O1	4.0 (3)	C29—C28—C33—C34	−175.60 (16)
C11—C16—C17—O1	−176.42 (17)	C27—C28—C33—C34	4.3 (3)
C15—C16—C17—C8	−178.18 (16)	C32—C33—C34—O2	5.0 (3)
C11—C16—C17—C8	1.4 (2)	C28—C33—C34—O2	−178.41 (17)
C9—C8—C17—O1	−156.51 (17)	C32—C33—C34—C25	−172.04 (17)
C7—C8—C17—O1	−21.4 (2)	C28—C33—C34—C25	4.6 (2)
C9—C8—C17—C16	25.7 (2)	C26—C25—C34—O2	145.95 (18)
C7—C8—C17—C16	160.87 (14)	C24—C25—C34—O2	15.7 (2)
C23—C18—C19—C20	0.6 (3)	C26—C25—C34—C33	−37.1 (2)
Cl2—C18—C19—C20	−179.62 (14)	C24—C25—C34—C33	−167.31 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.98	2.37	2.820 (2)	107
C20—H20···O2	0.93	2.55	3.183 (3)	125
C24—H24···O2	0.98	2.37	2.797 (2)	106
C30—H30···CgPⁱ	0.93	2.72	3.626 (3)	166

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₃₄H₂₈Cl₂O₂
M_r	539.46
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	10.411 (2), 10.975 (1), 13.296 (2)
α, β, γ (°)	103.54 (1), 112.97 (1), 93.89 (1)
V (Å³)	1338.2 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.52 × 0.48 × 0.48

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	ψ scan (XSCANS; Siemens, 1994)
T_min, T_max	0.865, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	5121, 4671, 3392
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.088, 1.05
No. of reflections	4671
No. of parameters	344
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20

Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXTL (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top

Cl1—C1	1.7420 (18)	C7—C24	1.549 (2)
Cl2—C18	1.7409 (19)	C7—C8	1.555 (2)
O1—C17	1.214 (2)	C21—C24	1.526 (2)
O2—C34	1.217 (2)	C24—C25	1.546 (2)
C4—C7	1.520 (2)

C4—C7—C24	111.85 (14)	C21—C24—C25	110.19 (14)
C4—C7—C8	108.79 (14)	C21—C24—C7	111.58 (14)
C24—C7—C8	115.78 (14)	C25—C24—C7	114.44 (14)
O1—C17—C16	120.68 (17)	O2—C34—C33	121.16 (16)
O1—C17—C8	121.60 (17)	O2—C34—C25	121.86 (16)
C16—C17—C8	117.68 (15)	C33—C34—C25	116.91 (15)

C4—C7—C24—C21	−59.28 (18)	C4—C7—C24—C25	174.74 (14)
C8—C7—C24—C21	175.33 (13)	C8—C7—C24—C25	49.4 (2)