1-[(1R,2S,4R,7S)-3,3-Dichloro-4,11,11-trimethyl­tricyclo[5.4.0.0^2,4]undecan-7-yl]ethanone

The title compound, C₁₆H₂₄Cl₂O, crystallizes with two independent mol­ecules in the asymmetric unit. Each mol­ecule is built up from two fused six-membered rings, one of which is fused to a three-membered ring. The two mol­ecules differ essentially in the orientation of two of the methyl groups. The dihedral angles between the mean planes through the two six-membered rings are 57.98 (13) and 55.29 (13)°. The mol­ecular conformation is stabilized by intra­molecular C—H...Cl hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.084
• Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT791_ALERT_4_G The Model has Chirality at C1      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C6      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C9      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C10     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C17     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C22     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C23     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C24     (Chiral SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

1-[(1R,2S,4R,7S)-3,3-Dichloro-4,11,11-trimethyl­tricyclo[5.4.0.0^2,4]undecan-7-yl]ethanone

Crystal data

C16H24Cl2O	Dx = 1.250 Mg m^−3
Mr = 303.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 6602 reflections
a = 13.373 (3) Å	θ = 2.1–26.4°
b = 13.996 (3) Å	µ = 0.39 mm^−1
c = 17.219 (4) Å	T = 296 K
V = 3222.9 (12) Å^3	Prismatic, colourless
Z = 8	0.24 × 0.2 × 0.15 mm
F(000) = 1296

Data collection

Bruker X8 APEX diffractometer	6117 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
φ and ω scans	θmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −16→16
Tmin = 0.679, Tmax = 0.747	k = −17→17
42837 measured reflections	l = −21→21
6602 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0451P)^2 + 0.5607P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
6602 reflections	Δρmax = 0.25 e Å^−3
351 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Absolute structure: Flack x determined using 2562 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.003 (11)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.36988 (6)	0.29957 (5)	0.55069 (4)	0.05611 (18)
Cl3	0.95794 (5)	0.53104 (6)	0.79873 (4)	0.0617 (2)
Cl2	0.17235 (7)	0.21684 (5)	0.54209 (6)	0.0714 (2)
Cl4	0.98018 (6)	0.32934 (6)	0.76753 (6)	0.0755 (3)
O2	0.3205 (2)	0.73129 (15)	0.45534 (15)	0.0799 (7)
C1	0.25547 (17)	0.50152 (15)	0.53392 (11)	0.0317 (4)
H1	0.3249	0.4834	0.5447	0.038*
C22	0.72518 (16)	0.49498 (15)	0.76550 (12)	0.0340 (4)
H22	0.7646	0.5487	0.7853	0.041*
C10	0.19975 (17)	0.41104 (16)	0.51128 (13)	0.0356 (5)
H10	0.1278	0.4117	0.5221	0.043*
C9	0.22970 (19)	0.36088 (17)	0.43609 (14)	0.0400 (5)
C23	0.79869 (17)	0.42024 (16)	0.73703 (13)	0.0370 (5)
H23	0.7747	0.3541	0.7387	0.044*
C17	0.66252 (17)	0.53344 (17)	0.69536 (13)	0.0401 (5)
C15	0.3382 (2)	0.64824 (18)	0.46980 (15)	0.0505 (6)
C24	0.86437 (18)	0.44530 (18)	0.66748 (14)	0.0418 (5)
C25	0.8422 (2)	0.54421 (19)	0.63672 (14)	0.0463 (6)
H25A	0.8789	0.5551	0.5889	0.056*
H25B	0.8627	0.5920	0.6743	0.056*
C21	0.6619 (2)	0.45593 (18)	0.83496 (14)	0.0446 (5)
O1	0.5301 (2)	0.6488 (2)	0.69931 (19)	0.0942 (9)
C6	0.25692 (19)	0.57096 (16)	0.46278 (13)	0.0390 (5)
C2	0.2116 (2)	0.54496 (19)	0.60989 (14)	0.0451 (6)
C26	0.7303 (2)	0.5520 (2)	0.62175 (14)	0.0484 (6)
H26A	0.7122	0.5064	0.5817	0.058*
H26B	0.7160	0.6154	0.6019	0.058*
C8	0.3150 (2)	0.41262 (18)	0.39601 (14)	0.0454 (6)
H8A	0.3280	0.3838	0.3458	0.054*
H8B	0.3752	0.4080	0.4271	0.054*
C11	0.24772 (19)	0.31444 (17)	0.51377 (15)	0.0424 (5)
C7	0.2858 (2)	0.51667 (19)	0.38574 (13)	0.0486 (6)
H7A	0.2295	0.5198	0.3503	0.058*
H7B	0.3412	0.5501	0.3615	0.058*
C18	0.5816 (2)	0.4601 (2)	0.67344 (17)	0.0559 (7)
H18A	0.5374	0.4886	0.6352	0.067*
H18B	0.6136	0.4055	0.6493	0.067*
C28	0.6174 (2)	0.6318 (2)	0.71223 (17)	0.0552 (7)
C5	0.1527 (2)	0.6152 (2)	0.45342 (18)	0.0587 (7)
H5A	0.1558	0.6640	0.4135	0.070*
H5B	0.1070	0.5661	0.4356	0.070*
C30	0.7319 (3)	0.4090 (2)	0.89434 (16)	0.0613 (8)
H30A	0.6937	0.3875	0.9382	0.092*
H30B	0.7809	0.4546	0.9112	0.092*
H30C	0.7649	0.3554	0.8708	0.092*
C27	0.90911 (19)	0.43261 (19)	0.74687 (15)	0.0459 (6)
C16	0.4435 (2)	0.6165 (3)	0.4879 (2)	0.0647 (8)
H16A	0.4900	0.6542	0.4585	0.097*
H16B	0.4511	0.5503	0.4744	0.097*
H16C	0.4563	0.6247	0.5424	0.097*
C3	0.1089 (2)	0.5890 (2)	0.59315 (19)	0.0625 (8)
H3A	0.0620	0.5382	0.5810	0.075*
H3B	0.0851	0.6211	0.6395	0.075*
C20	0.5847 (2)	0.3842 (2)	0.80557 (18)	0.0570 (7)
H20A	0.6191	0.3282	0.7859	0.068*
H20B	0.5428	0.3642	0.8486	0.068*
C31	0.6090 (3)	0.5389 (2)	0.87730 (17)	0.0615 (8)
H31A	0.5644	0.5706	0.8420	0.092*
H31B	0.6580	0.5836	0.8958	0.092*
H31C	0.5716	0.5142	0.9205	0.092*
C13	0.2015 (3)	0.4657 (3)	0.67104 (15)	0.0666 (9)
H13A	0.2657	0.4371	0.6800	0.100*
H13B	0.1557	0.4180	0.6527	0.100*
H13C	0.1769	0.4926	0.7187	0.100*
C12	0.1507 (2)	0.3210 (2)	0.38231 (18)	0.0618 (8)
H12A	0.1773	0.2671	0.3548	0.093*
H12B	0.1309	0.3693	0.3458	0.093*
H12C	0.0937	0.3013	0.4122	0.093*
C32	0.8843 (2)	0.3703 (2)	0.60542 (17)	0.0616 (8)
H0A	0.9474	0.3832	0.5809	0.092*
H0B	0.8320	0.3722	0.5673	0.092*
H0C	0.8862	0.3081	0.6290	0.092*
C19	0.5189 (2)	0.4252 (3)	0.7417 (2)	0.0694 (9)
H19A	0.4801	0.4780	0.7623	0.083*
H19B	0.4727	0.3765	0.7239	0.083*
C4	0.1105 (3)	0.6595 (2)	0.5268 (2)	0.0705 (9)
H4A	0.1508	0.7143	0.5413	0.085*
H4B	0.0430	0.6818	0.5169	0.085*
C14	0.2817 (3)	0.6214 (2)	0.64349 (17)	0.0617 (8)
H14A	0.2882	0.6730	0.6071	0.093*
H14B	0.3463	0.5939	0.6530	0.093*
H14C	0.2545	0.6452	0.6913	0.093*
C29	0.6857 (3)	0.7112 (2)	0.7387 (2)	0.0675 (8)
H29A	0.6538	0.7717	0.7300	0.101*
H29B	0.7471	0.7086	0.7098	0.101*
H29C	0.6998	0.7038	0.7930	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0571 (4)	0.0460 (3)	0.0652 (4)	0.0108 (3)	−0.0111 (3)	0.0052 (3)
Cl3	0.0468 (4)	0.0750 (5)	0.0635 (4)	−0.0098 (3)	−0.0161 (3)	−0.0089 (4)
Cl2	0.0777 (5)	0.0410 (3)	0.0954 (6)	−0.0158 (3)	0.0135 (4)	0.0114 (4)
Cl4	0.0587 (5)	0.0715 (5)	0.0962 (6)	0.0261 (4)	−0.0045 (4)	0.0146 (4)
O2	0.113 (2)	0.0382 (11)	0.0888 (16)	−0.0112 (12)	−0.0047 (15)	0.0144 (11)
C1	0.0328 (10)	0.0319 (10)	0.0303 (10)	0.0008 (8)	0.0021 (8)	−0.0004 (8)
C22	0.0348 (11)	0.0313 (10)	0.0360 (10)	−0.0029 (9)	−0.0018 (9)	−0.0012 (8)
C10	0.0332 (11)	0.0340 (11)	0.0397 (11)	−0.0009 (9)	0.0043 (9)	−0.0009 (9)
C9	0.0428 (12)	0.0357 (11)	0.0415 (12)	0.0006 (10)	−0.0013 (10)	−0.0064 (9)
C23	0.0362 (11)	0.0341 (11)	0.0408 (12)	−0.0001 (9)	−0.0013 (9)	−0.0010 (9)
C17	0.0354 (11)	0.0423 (12)	0.0425 (11)	−0.0003 (10)	−0.0047 (9)	−0.0001 (10)
C15	0.0699 (18)	0.0381 (13)	0.0435 (13)	−0.0105 (12)	0.0003 (12)	0.0036 (10)
C24	0.0366 (12)	0.0450 (13)	0.0438 (12)	−0.0013 (10)	0.0018 (10)	−0.0038 (10)
C25	0.0473 (14)	0.0528 (14)	0.0387 (12)	−0.0057 (12)	0.0050 (10)	0.0057 (11)
C21	0.0492 (14)	0.0403 (12)	0.0443 (12)	−0.0044 (11)	0.0091 (10)	−0.0006 (10)
O1	0.0635 (15)	0.0844 (18)	0.135 (2)	0.0334 (14)	−0.0193 (16)	−0.0021 (17)
C6	0.0482 (13)	0.0342 (11)	0.0347 (11)	−0.0002 (10)	−0.0057 (10)	0.0033 (9)
C2	0.0487 (14)	0.0489 (14)	0.0378 (12)	0.0015 (12)	0.0080 (10)	−0.0089 (10)
C26	0.0528 (15)	0.0534 (15)	0.0391 (12)	0.0011 (12)	−0.0055 (11)	0.0060 (11)
C8	0.0536 (15)	0.0492 (14)	0.0334 (11)	−0.0016 (12)	0.0092 (10)	−0.0078 (10)
C11	0.0428 (13)	0.0322 (11)	0.0522 (13)	−0.0041 (10)	0.0033 (10)	0.0036 (10)
C7	0.0649 (16)	0.0484 (14)	0.0325 (11)	−0.0077 (13)	0.0022 (11)	0.0043 (10)
C18	0.0465 (14)	0.0605 (17)	0.0608 (16)	−0.0076 (13)	−0.0138 (12)	−0.0071 (14)
C28	0.0565 (16)	0.0521 (15)	0.0572 (15)	0.0159 (13)	−0.0039 (13)	0.0044 (12)
C5	0.0636 (18)	0.0466 (14)	0.0658 (17)	0.0117 (13)	−0.0223 (14)	0.0047 (13)
C30	0.079 (2)	0.0618 (18)	0.0433 (14)	−0.0028 (16)	0.0049 (14)	0.0144 (12)
C27	0.0382 (12)	0.0465 (14)	0.0530 (14)	0.0041 (11)	−0.0052 (10)	0.0002 (11)
C16	0.0553 (17)	0.0665 (19)	0.0724 (19)	−0.0230 (15)	0.0036 (15)	0.0022 (16)
C3	0.0478 (15)	0.0632 (18)	0.0764 (19)	0.0103 (14)	0.0148 (14)	−0.0240 (15)
C20	0.0551 (16)	0.0506 (15)	0.0652 (17)	−0.0151 (13)	0.0176 (14)	−0.0010 (13)
C31	0.0688 (19)	0.0599 (18)	0.0558 (15)	−0.0006 (15)	0.0206 (14)	−0.0106 (14)
C13	0.086 (2)	0.077 (2)	0.0370 (13)	−0.0027 (18)	0.0186 (14)	−0.0001 (13)
C12	0.0664 (19)	0.0543 (16)	0.0646 (17)	−0.0038 (14)	−0.0169 (15)	−0.0172 (13)
C32	0.0594 (17)	0.0658 (18)	0.0597 (16)	0.0008 (15)	0.0126 (14)	−0.0160 (14)
C19	0.0435 (15)	0.077 (2)	0.087 (2)	−0.0209 (15)	−0.0014 (15)	−0.0084 (18)
C4	0.0552 (18)	0.0583 (18)	0.098 (2)	0.0257 (15)	−0.0131 (17)	−0.0148 (17)
C14	0.0718 (19)	0.0671 (18)	0.0463 (14)	−0.0036 (16)	−0.0012 (14)	−0.0212 (13)
C29	0.092 (2)	0.0382 (13)	0.0719 (19)	0.0098 (15)	−0.0013 (17)	0.0010 (13)

Geometric parameters (Å, º)

Cl1—C11	1.765 (3)	C8—H8A	0.9700
Cl3—C27	1.767 (3)	C8—H8B	0.9700
Cl2—C11	1.766 (2)	C7—H7A	0.9700
Cl4—C27	1.766 (3)	C7—H7B	0.9700
O2—C15	1.212 (3)	C18—C19	1.524 (5)
C1—C10	1.520 (3)	C18—H18A	0.9700
C1—C2	1.557 (3)	C18—H18B	0.9700
C1—C6	1.564 (3)	C28—C29	1.508 (5)
C1—H1	0.9800	C5—C4	1.516 (5)
C22—C23	1.517 (3)	C5—H5A	0.9700
C22—C21	1.564 (3)	C5—H5B	0.9700
C22—C17	1.565 (3)	C30—H30A	0.9600
C22—H22	0.9800	C30—H30B	0.9600
C10—C11	1.497 (3)	C30—H30C	0.9600
C10—C9	1.526 (3)	C16—H16A	0.9600
C10—H10	0.9800	C16—H16B	0.9600
C9—C11	1.507 (3)	C16—H16C	0.9600
C9—C12	1.512 (4)	C3—C4	1.510 (5)
C9—C8	1.517 (4)	C3—H3A	0.9700
C23—C27	1.496 (3)	C3—H3B	0.9700
C23—C24	1.526 (3)	C20—C19	1.521 (5)
C23—H23	0.9800	C20—H20A	0.9700
C17—C28	1.531 (4)	C20—H20B	0.9700
C17—C18	1.538 (4)	C31—H31A	0.9600
C17—C26	1.580 (4)	C31—H31B	0.9600
C15—C16	1.508 (5)	C31—H31C	0.9600
C15—C6	1.539 (4)	C13—H13A	0.9600
C24—C27	1.503 (4)	C13—H13B	0.9600
C24—C25	1.512 (4)	C13—H13C	0.9600
C24—C32	1.522 (4)	C12—H12A	0.9600
C25—C26	1.522 (4)	C12—H12B	0.9600
C25—H25A	0.9700	C12—H12C	0.9600
C25—H25B	0.9700	C32—H0A	0.9600
C21—C20	1.526 (4)	C32—H0B	0.9600
C21—C30	1.534 (4)	C32—H0C	0.9600
C21—C31	1.543 (4)	C19—H19A	0.9700
O1—C28	1.213 (4)	C19—H19B	0.9700
C6—C5	1.534 (4)	C4—H4A	0.9700
C6—C7	1.577 (3)	C4—H4B	0.9700
C2—C3	1.533 (4)	C14—H14A	0.9600
C2—C13	1.535 (4)	C14—H14B	0.9600
C2—C14	1.536 (4)	C14—H14C	0.9600
C26—H26A	0.9700	C29—H29A	0.9600
C26—H26B	0.9700	C29—H29B	0.9600
C8—C7	1.518 (4)	C29—H29C	0.9600
C10—C1—C2	110.86 (18)	C19—C18—C17	114.3 (2)
C10—C1—C6	108.84 (17)	C19—C18—H18A	108.7
C2—C1—C6	114.84 (18)	C17—C18—H18A	108.7
C10—C1—H1	107.3	C19—C18—H18B	108.7
C2—C1—H1	107.3	C17—C18—H18B	108.7
C6—C1—H1	107.3	H18A—C18—H18B	107.6
C23—C22—C21	110.91 (18)	O1—C28—C29	119.7 (3)
C23—C22—C17	109.56 (18)	O1—C28—C17	121.4 (3)
C21—C22—C17	114.86 (19)	C29—C28—C17	118.7 (2)
C23—C22—H22	107.0	C4—C5—C6	114.6 (2)
C21—C22—H22	107.0	C4—C5—H5A	108.6
C17—C22—H22	107.0	C6—C5—H5A	108.6
C11—C10—C1	122.34 (19)	C4—C5—H5B	108.6
C11—C10—C9	59.77 (16)	C6—C5—H5B	108.6
C1—C10—C9	118.18 (19)	H5A—C5—H5B	107.6
C11—C10—H10	115.1	C21—C30—H30A	109.5
C1—C10—H10	115.1	C21—C30—H30B	109.5
C9—C10—H10	115.1	H30A—C30—H30B	109.5
C11—C9—C12	119.8 (2)	C21—C30—H30C	109.5
C11—C9—C8	119.3 (2)	H30A—C30—H30C	109.5
C12—C9—C8	115.0 (2)	H30B—C30—H30C	109.5
C11—C9—C10	59.16 (15)	C23—C27—C24	61.17 (16)
C12—C9—C10	120.4 (2)	C23—C27—Cl4	117.33 (19)
C8—C9—C10	111.31 (19)	C24—C27—Cl4	119.62 (19)
C27—C23—C22	121.5 (2)	C23—C27—Cl3	120.81 (19)
C27—C23—C24	59.62 (16)	C24—C27—Cl3	120.98 (19)
C22—C23—C24	117.92 (19)	Cl4—C27—Cl3	109.73 (14)
C27—C23—H23	115.4	C15—C16—H16A	109.5
C22—C23—H23	115.4	C15—C16—H16B	109.5
C24—C23—H23	115.4	H16A—C16—H16B	109.5
C28—C17—C18	111.7 (2)	C15—C16—H16C	109.5
C28—C17—C22	111.9 (2)	H16A—C16—H16C	109.5
C18—C17—C22	109.7 (2)	H16B—C16—H16C	109.5
C28—C17—C26	103.3 (2)	C4—C3—C2	113.1 (3)
C18—C17—C26	108.4 (2)	C4—C3—H3A	109.0
C22—C17—C26	111.60 (18)	C2—C3—H3A	109.0
O2—C15—C16	120.5 (3)	C4—C3—H3B	109.0
O2—C15—C6	121.3 (3)	C2—C3—H3B	109.0
C16—C15—C6	117.9 (2)	H3A—C3—H3B	107.8
C27—C24—C25	120.3 (2)	C19—C20—C21	112.5 (2)
C27—C24—C32	119.2 (2)	C19—C20—H20A	109.1
C25—C24—C32	114.9 (2)	C21—C20—H20A	109.1
C27—C24—C23	59.21 (16)	C19—C20—H20B	109.1
C25—C24—C23	111.9 (2)	C21—C20—H20B	109.1
C32—C24—C23	119.6 (2)	H20A—C20—H20B	107.8
C24—C25—C26	108.5 (2)	C21—C31—H31A	109.5
C24—C25—H25A	110.0	C21—C31—H31B	109.5
C26—C25—H25A	110.0	H31A—C31—H31B	109.5
C24—C25—H25B	110.0	C21—C31—H31C	109.5
C26—C25—H25B	110.0	H31A—C31—H31C	109.5
H25A—C25—H25B	108.4	H31B—C31—H31C	109.5
C20—C21—C30	110.6 (2)	C2—C13—H13A	109.5
C20—C21—C31	110.0 (2)	C2—C13—H13B	109.5
C30—C21—C31	106.7 (2)	H13A—C13—H13B	109.5
C20—C21—C22	110.0 (2)	C2—C13—H13C	109.5
C30—C21—C22	109.2 (2)	H13A—C13—H13C	109.5
C31—C21—C22	110.3 (2)	H13B—C13—H13C	109.5
C5—C6—C15	111.5 (2)	C9—C12—H12A	109.5
C5—C6—C1	108.8 (2)	C9—C12—H12B	109.5
C15—C6—C1	112.59 (19)	H12A—C12—H12B	109.5
C5—C6—C7	109.2 (2)	C9—C12—H12C	109.5
C15—C6—C7	103.4 (2)	H12A—C12—H12C	109.5
C1—C6—C7	111.26 (18)	H12B—C12—H12C	109.5
C3—C2—C13	109.9 (2)	C24—C32—H0A	109.5
C3—C2—C14	109.7 (2)	C24—C32—H0B	109.5
C13—C2—C14	107.4 (2)	H0A—C32—H0B	109.5
C3—C2—C1	109.7 (2)	C24—C32—H0C	109.5
C13—C2—C1	109.1 (2)	H0A—C32—H0C	109.5
C14—C2—C1	111.0 (2)	H0B—C32—H0C	109.5
C25—C26—C17	114.6 (2)	C20—C19—C18	111.1 (2)
C25—C26—H26A	108.6	C20—C19—H19A	109.4
C17—C26—H26A	108.6	C18—C19—H19A	109.4
C25—C26—H26B	108.6	C20—C19—H19B	109.4
C17—C26—H26B	108.6	C18—C19—H19B	109.4
H26A—C26—H26B	107.6	H19A—C19—H19B	108.0
C9—C8—C7	108.5 (2)	C3—C4—C5	111.6 (2)
C9—C8—H8A	110.0	C3—C4—H4A	109.3
C7—C8—H8A	110.0	C5—C4—H4A	109.3
C9—C8—H8B	110.0	C3—C4—H4B	109.3
C7—C8—H8B	110.0	C5—C4—H4B	109.3
H8A—C8—H8B	108.4	H4A—C4—H4B	108.0
C10—C11—C9	61.08 (15)	C2—C14—H14A	109.5
C10—C11—Cl1	120.89 (17)	C2—C14—H14B	109.5
C9—C11—Cl1	121.24 (18)	H14A—C14—H14B	109.5
C10—C11—Cl2	117.51 (17)	C2—C14—H14C	109.5
C9—C11—Cl2	119.17 (18)	H14A—C14—H14C	109.5
Cl1—C11—Cl2	109.73 (13)	H14B—C14—H14C	109.5
C8—C7—C6	115.29 (19)	C28—C29—H29A	109.5
C8—C7—H7A	108.5	C28—C29—H29B	109.5
C6—C7—H7A	108.5	H29A—C29—H29B	109.5
C8—C7—H7B	108.5	C28—C29—H29C	109.5
C6—C7—H7B	108.5	H29A—C29—H29C	109.5
H7A—C7—H7B	107.5	H29B—C29—H29C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.98	2.64	3.227 (2)	118
C8—H8B···Cl1	0.97	2.61	3.184 (3)	118
C22—H22···Cl3	0.98	2.61	3.205 (2)	120
C25—H25B···Cl3	0.97	2.63	3.196 (3)	117