Koetjapic acid chloro-form hemisolvate.

The asymmetric unit of the title compound, C(30)H(46)O(4)·0.5CHCl(3), consists of one koetjapic acid [systematic name: (3R,4aR,4bS,7S,8S,10bS,12aS)-7-(2-carboxy-ethyl)-3,4b,7,10b,12a-penta-methyl-8-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,7,8,9,10,10b,11,12,12a-hexa-deca-hydro-chrysene-3-carboxylic acid] mol-ecule and one half-mol-ecule of chloro-form solvent, which is disordered about a twofold rotation axis. The symmetry-independent component is further disordered over two sites, with occupancies of 0.30 and 0.20. The koetjapic acid contains a fused four-ring system, A/B/C/D. The A/B, B/C and C/D junctions adopt E/trans/cis configurations, respectively. The conformation of ring A is inter-mediate between envelope and half-chair and ring B adopts an envelope conformation whereas rings C and D adopt chair conformations. A weak intra-molecular C-H⋯O hydrogen bond is observed. The koetjapic acid mol-ecules are linked into dimers by two pairs of inter-molecular O-H⋯O hydrogen bonds. The dimers are stacked along the c axis.

Related literature

For the biological properties of Sandoricum koetjape and koetjapic acid, see: Aisha et al. (2009 ▶); Kaneda et al. (1992 ▶); Sun et al. (1999 ▶); Ismail et al. (2003 ▶); Rasadah et al. (2004 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C30H46O4·0.5CHCl3

M = 530.35

Orthorhombic,

a = 12.8950 (3) Å

b = 33.7309 (8) Å

c = 6.5307 (1) Å

V = 2840.59 (10) Å3

Z = 4

Cu Kα radiation

μ = 1.88 mm−1

T = 100 K

0.34 × 0.28 × 0.11 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.567, T max = 0.827

26063 measured reflections

4654 independent reflections

4467 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.169

S = 1.09

4654 reflections

357 parameters

40 restraints

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.68 e Å−3

Absolute structure: Flack (1983 ▶), 1876 Friedel pairs

Flack parameter: 0.08 (5)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016430/ci5066sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016430/ci5066Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C30H46O4·0.5CHCl3	F(000) = 1148
Mr = 530.35	Dx = 1.240 Mg m−3
Orthorhombic, P21212	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2 2ab	Cell parameters from 9931 reflections
a = 12.8950 (3) Å	θ = 2.6–65.7°
b = 33.7309 (8) Å	µ = 1.88 mm−1
c = 6.5307 (1) Å	T = 100 K
V = 2840.59 (10) Å3	Block, colourless
Z = 4	0.34 × 0.28 × 0.11 mm

Bruker APEXII DUO CCD area-detector diffractometer	4654 independent reflections
Radiation source: fine-focus sealed tube	4467 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 66.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.567, Tmax = 0.827	k = −38→39
26063 measured reflections	l = −5→7

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.060	w = 1/[σ2(Fo2) + (0.0958P)2 + 1.9305P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.169	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.53 e Å−3
4654 reflections	Δρmin = −0.68 e Å−3
357 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
40 restraints	Extinction coefficient: 0.0082 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1876 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.08 (5)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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. 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.2093 (2)	0.96882 (8)	0.3593 (5)	0.0439 (8)
H1	0.2417	0.9868	0.4147	0.066*
O2	0.1261 (2)	0.96828 (8)	0.6601 (5)	0.0436 (8)
O3	0.7713 (3)	0.96911 (9)	0.8069 (6)	0.0514 (9)
H3	0.8000	0.9887	0.7590	0.077*
O4	0.6996 (5)	0.96705 (14)	0.4969 (7)	0.106 (2)
C1	0.5175 (3)	0.84482 (11)	0.6074 (6)	0.0304 (8)
C2	0.4878 (3)	0.86704 (12)	0.4167 (6)	0.0329 (9)
H2A	0.5314	0.8577	0.3056	0.039*
H2B	0.5037	0.8949	0.4378	0.039*
C3	0.3751 (3)	0.86394 (12)	0.3479 (6)	0.0328 (9)
H3A	0.3678	0.8412	0.2578	0.039*
H3B	0.3572	0.8875	0.2700	0.039*
C4	0.2988 (3)	0.85964 (10)	0.5262 (6)	0.0262 (8)
C5	0.1868 (3)	0.85387 (10)	0.4384 (6)	0.0264 (8)
H5A	0.1946	0.8317	0.3427	0.032*
C6	0.1433 (3)	0.88781 (10)	0.3023 (6)	0.0292 (8)
H6A	0.2020	0.9006	0.2369	0.035*
H6B	0.1027	0.8755	0.1944	0.035*
C7	0.0758 (3)	0.92092 (11)	0.3973 (7)	0.0339 (9)
C8	0.0003 (3)	0.90414 (12)	0.5567 (7)	0.0391 (10)
H8A	−0.0273	0.9259	0.6374	0.047*
H8B	−0.0574	0.8918	0.4859	0.047*
C9	0.0491 (3)	0.87389 (12)	0.7005 (7)	0.0354 (9)
H9A	−0.0044	0.8636	0.7905	0.042*
H9B	0.1000	0.8873	0.7851	0.042*
C10	0.1020 (3)	0.83885 (11)	0.5927 (6)	0.0300 (9)
C11	0.1466 (3)	0.81017 (12)	0.7559 (6)	0.0356 (9)
H11A	0.1008	0.8107	0.8737	0.043*
H11B	0.1444	0.7835	0.7001	0.043*
C12	0.2567 (3)	0.81809 (12)	0.8308 (6)	0.0325 (9)
H12A	0.2788	0.7966	0.9190	0.039*
H12B	0.2578	0.8424	0.9103	0.039*
C13	0.3322 (3)	0.82188 (10)	0.6488 (5)	0.0252 (8)
C14	0.4463 (3)	0.82387 (10)	0.7164 (5)	0.0254 (8)
C15	0.4753 (3)	0.79887 (11)	0.8945 (6)	0.0303 (8)
H15A	0.4413	0.7734	0.8803	0.036*
H15B	0.4484	0.8113	1.0176	0.036*
C16	0.5911 (3)	0.79172 (12)	0.9237 (6)	0.0346 (9)
H16A	0.6142	0.7710	0.8312	0.042*
H16B	0.6043	0.7830	1.0628	0.042*
C17	0.6514 (3)	0.82981 (11)	0.8812 (6)	0.0304 (8)
H17A	0.6197	0.8505	0.9658	0.036*
C18	0.6348 (3)	0.84244 (11)	0.6529 (6)	0.0270 (8)
C19	0.6891 (3)	0.88239 (12)	0.6111 (6)	0.0335 (9)
H19A	0.7628	0.8790	0.6352	0.040*
H19B	0.6803	0.8888	0.4673	0.040*
C20	0.6517 (4)	0.91792 (12)	0.7379 (7)	0.0440 (11)
H20A	0.5779	0.9218	0.7178	0.053*
H20B	0.6640	0.9130	0.8823	0.053*
C21	0.7097 (5)	0.95397 (14)	0.6711 (8)	0.0539 (13)
C22	0.3104 (3)	0.89708 (11)	0.6604 (6)	0.0325 (9)
H22A	0.2509	0.8996	0.7478	0.049*
H22B	0.3157	0.9200	0.5742	0.049*
H22C	0.3718	0.8948	0.7427	0.049*
C23	0.1407 (3)	0.95455 (11)	0.4877 (7)	0.0338 (9)
C24	0.0136 (4)	0.94111 (12)	0.2222 (8)	0.0453 (11)
H24A	0.0608	0.9509	0.1205	0.068*
H24B	−0.0260	0.9627	0.2770	0.068*
H24C	−0.0324	0.9221	0.1610	0.068*
C25	0.0193 (3)	0.81565 (11)	0.4729 (7)	0.0378 (9)
H25A	−0.0317	0.8055	0.5663	0.057*
H25B	0.0515	0.7940	0.4017	0.057*
H25C	−0.0136	0.8329	0.3758	0.057*
C26	0.3264 (3)	0.78339 (11)	0.5175 (6)	0.0326 (9)
H26A	0.3786	0.7842	0.4128	0.049*
H26B	0.2592	0.7815	0.4551	0.049*
H26C	0.3378	0.7607	0.6036	0.049*
C27	0.7649 (3)	0.82688 (13)	0.9473 (6)	0.0357 (9)
C28	0.8203 (3)	0.79269 (13)	0.9245 (7)	0.0440 (11)
H28A	0.8880	0.7912	0.9730	0.066*
H28B	0.7904	0.7709	0.8604	0.066*
C29	0.8118 (3)	0.86138 (13)	1.0484 (6)	0.0407 (10)
H29A	0.8764	0.8538	1.1099	0.061*
H29B	0.7657	0.8711	1.1523	0.061*
H29C	0.8240	0.8818	0.9491	0.061*
C30	0.6836 (3)	0.81256 (12)	0.5030 (6)	0.0361 (9)
H30A	0.6690	0.8205	0.3649	0.054*
H30B	0.6549	0.7867	0.5271	0.054*
H30C	0.7573	0.8118	0.5236	0.054*
C31	0.5335 (9)	0.9947 (3)	0.0839 (17)	0.087 (5)	0.50
H31A	0.6041	0.9856	0.0890	0.104*	0.299 (3)
H31B	0.5871	0.9780	0.1384	0.104*	0.201 (3)
Cl1	0.4660 (3)	0.95921 (9)	0.1615 (9)	0.1061 (18)	0.597 (7)
Cl2	0.5000	1.0000	−0.2013 (6)	0.127 (3)	0.597 (7)
Cl3	0.4269 (6)	0.9672 (3)	−0.0147 (14)	0.153 (4)	0.403 (7)
Cl4	0.4584 (9)	1.0233 (3)	0.2864 (15)	0.107 (4)	0.201 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0454 (17)	0.0302 (14)	0.0561 (18)	−0.0102 (13)	0.0042 (15)	−0.0052 (14)
O2	0.0436 (17)	0.0284 (14)	0.059 (2)	−0.0053 (12)	0.0067 (15)	−0.0103 (14)
O3	0.0545 (19)	0.0332 (15)	0.067 (2)	−0.0172 (14)	−0.0117 (17)	0.0117 (15)
O4	0.166 (5)	0.075 (3)	0.076 (3)	−0.080 (3)	−0.044 (3)	0.034 (2)
C1	0.0276 (19)	0.033 (2)	0.0302 (19)	−0.0056 (16)	−0.0014 (16)	0.0033 (15)
C2	0.030 (2)	0.044 (2)	0.0252 (19)	0.0015 (17)	0.0039 (16)	0.0049 (16)
C3	0.033 (2)	0.036 (2)	0.030 (2)	−0.0023 (16)	−0.0003 (16)	0.0074 (16)
C4	0.0269 (18)	0.0229 (17)	0.0287 (18)	−0.0009 (14)	0.0005 (15)	−0.0021 (14)
C5	0.0267 (18)	0.0226 (17)	0.0298 (19)	−0.0008 (14)	−0.0016 (15)	−0.0012 (14)
C6	0.0297 (19)	0.0253 (18)	0.033 (2)	−0.0020 (15)	−0.0062 (16)	−0.0020 (15)
C7	0.0256 (19)	0.0235 (18)	0.053 (2)	0.0005 (15)	−0.0041 (19)	−0.0037 (17)
C8	0.030 (2)	0.0284 (19)	0.059 (3)	−0.0028 (17)	0.0018 (19)	−0.0086 (18)
C9	0.027 (2)	0.036 (2)	0.043 (2)	−0.0044 (16)	0.0065 (17)	−0.0050 (18)
C10	0.0264 (18)	0.0276 (19)	0.036 (2)	−0.0038 (15)	0.0027 (16)	−0.0006 (16)
C11	0.030 (2)	0.036 (2)	0.041 (2)	−0.0039 (17)	0.0063 (18)	0.0087 (17)
C12	0.031 (2)	0.036 (2)	0.031 (2)	0.0012 (16)	0.0034 (16)	0.0055 (17)
C13	0.0256 (18)	0.0250 (17)	0.0250 (17)	−0.0030 (14)	0.0028 (14)	0.0002 (14)
C14	0.031 (2)	0.0205 (17)	0.0246 (17)	−0.0027 (14)	−0.0020 (14)	−0.0041 (14)
C15	0.034 (2)	0.0255 (18)	0.031 (2)	−0.0047 (16)	0.0044 (17)	0.0018 (15)
C16	0.038 (2)	0.033 (2)	0.033 (2)	−0.0072 (18)	−0.0078 (17)	0.0074 (16)
C17	0.0301 (19)	0.0321 (19)	0.0288 (18)	−0.0076 (16)	−0.0003 (16)	0.0018 (15)
C18	0.0269 (19)	0.0263 (18)	0.0277 (18)	−0.0041 (15)	0.0005 (15)	0.0024 (14)
C19	0.030 (2)	0.036 (2)	0.035 (2)	−0.0099 (16)	0.0028 (17)	0.0069 (16)
C20	0.048 (3)	0.032 (2)	0.052 (3)	−0.0112 (19)	0.004 (2)	−0.0015 (19)
C21	0.075 (4)	0.033 (2)	0.054 (3)	−0.014 (2)	−0.013 (3)	0.005 (2)
C22	0.032 (2)	0.0271 (19)	0.038 (2)	−0.0031 (16)	−0.0067 (17)	−0.0032 (16)
C23	0.030 (2)	0.0221 (18)	0.050 (2)	0.0003 (15)	−0.0005 (19)	−0.0031 (18)
C24	0.037 (2)	0.031 (2)	0.067 (3)	0.0004 (18)	−0.012 (2)	0.003 (2)
C25	0.031 (2)	0.028 (2)	0.054 (2)	−0.0047 (17)	−0.0031 (19)	−0.0002 (18)
C26	0.032 (2)	0.0250 (18)	0.041 (2)	−0.0009 (15)	−0.0048 (17)	−0.0022 (16)
C27	0.037 (2)	0.043 (2)	0.0267 (19)	−0.0099 (18)	−0.0052 (16)	0.0083 (17)
C28	0.036 (2)	0.042 (2)	0.054 (3)	−0.0047 (19)	−0.013 (2)	0.009 (2)
C29	0.037 (2)	0.050 (3)	0.035 (2)	−0.0166 (19)	−0.0029 (18)	0.0055 (18)
C30	0.036 (2)	0.040 (2)	0.032 (2)	0.0063 (17)	−0.0022 (17)	−0.0023 (17)
C31	0.066 (8)	0.051 (7)	0.143 (13)	0.020 (6)	−0.016 (8)	−0.002 (8)
Cl1	0.103 (3)	0.0606 (17)	0.154 (4)	−0.0130 (16)	0.036 (3)	0.032 (2)
Cl2	0.245 (7)	0.078 (3)	0.059 (2)	0.095 (4)	0.000	0.000
Cl3	0.154 (6)	0.141 (6)	0.162 (7)	−0.086 (5)	0.055 (5)	−0.070 (6)
Cl4	0.151 (8)	0.077 (5)	0.094 (6)	−0.008 (6)	0.001 (6)	−0.038 (5)

O1—C23	1.310 (5)	C17—C27	1.529 (6)
O1—H1	0.82	C17—C18	1.565 (5)
O2—C23	1.232 (5)	C17—H17A	0.98
O3—C21	1.296 (6)	C18—C30	1.539 (5)
O3—H3	0.82	C18—C19	1.543 (5)
O4—C21	1.227 (6)	C19—C20	1.534 (6)
C1—C14	1.360 (5)	C19—H19A	0.97
C1—C2	1.504 (5)	C19—H19B	0.97
C1—C18	1.544 (5)	C20—C21	1.492 (6)
C2—C3	1.525 (6)	C20—H20A	0.97
C2—H2A	0.97	C20—H20B	0.97
C2—H2B	0.97	C22—H22A	0.96
C3—C4	1.531 (5)	C22—H22B	0.96
C3—H3A	0.97	C22—H22C	0.96
C3—H3B	0.97	C24—H24A	0.96
C4—C22	1.545 (5)	C24—H24B	0.96
C4—C13	1.565 (5)	C24—H24C	0.96
C4—C5	1.565 (5)	C25—H25A	0.96
C5—C6	1.554 (5)	C25—H25B	0.96
C5—C10	1.571 (5)	C25—H25C	0.96
C5—H5A	0.98	C26—H26A	0.96
C6—C7	1.546 (5)	C26—H26B	0.96
C6—H6A	0.97	C26—H26C	0.96
C6—H6B	0.97	C27—C28	1.365 (6)
C7—C23	1.528 (5)	C27—C29	1.468 (6)
C7—C8	1.534 (6)	C28—H28A	0.93
C7—C24	1.554 (6)	C28—H28B	0.93
C8—C9	1.523 (6)	C29—H29A	0.96
C8—H8A	0.97	C29—H29B	0.96
C8—H8B	0.97	C29—H29C	0.96
C9—C10	1.536 (5)	C30—H30A	0.96
C9—H9A	0.97	C30—H30B	0.96
C9—H9B	0.97	C30—H30C	0.96
C10—C25	1.538 (6)	C31—C31i	0.94 (2)
C10—C11	1.550 (5)	C31—Cl4i	1.460 (13)
C11—C12	1.525 (6)	C31—Cl3i	1.526 (10)
C11—H11A	0.97	C31—Cl1	1.564 (9)
C11—H11B	0.97	C31—Cl1i	1.635 (9)
C12—C13	1.543 (5)	C31—Cl3	1.779 (11)
C12—H12A	0.97	C31—Cl4	1.903 (12)
C12—H12B	0.97	C31—Cl2	1.920 (12)
C13—C14	1.538 (5)	C31—H31A	0.96
C13—C26	1.558 (5)	C31—H31B	0.96
C14—C15	1.484 (5)	Cl1—C31i	1.635 (9)
C15—C16	1.525 (6)	Cl1—H31B	1.6921
C15—H15A	0.97	Cl2—C31i	1.920 (12)
C15—H15B	0.97	Cl3—C31i	1.526 (10)
C16—C17	1.527 (5)	Cl4—C31i	1.460 (13)
C16—H16A	0.97	Cl4—Cl4i	1.91 (2)
C16—H16B	0.97
C23—O1—H1	109.5	H16A—C16—H16B	108.2
C21—O3—H3	109.5	C16—C17—C27	112.4 (3)
C14—C1—C2	121.4 (3)	C16—C17—C18	109.4 (3)
C14—C1—C18	122.3 (3)	C27—C17—C18	114.7 (3)
C2—C1—C18	115.8 (3)	C16—C17—H17A	106.6
C1—C2—C3	116.9 (3)	C27—C17—H17A	106.6
C1—C2—H2A	108.1	C18—C17—H17A	106.6
C3—C2—H2A	108.1	C30—C18—C19	105.9 (3)
C1—C2—H2B	108.1	C30—C18—C1	108.2 (3)
C3—C2—H2B	108.1	C19—C18—C1	111.4 (3)
H2A—C2—H2B	107.3	C30—C18—C17	111.8 (3)
C2—C3—C4	113.3 (3)	C19—C18—C17	110.1 (3)
C2—C3—H3A	108.9	C1—C18—C17	109.3 (3)
C4—C3—H3A	108.9	C20—C19—C18	116.4 (3)
C2—C3—H3B	108.9	C20—C19—H19A	108.2
C4—C3—H3B	108.9	C18—C19—H19A	108.2
H3A—C3—H3B	107.7	C20—C19—H19B	108.2
C3—C4—C22	107.0 (3)	C18—C19—H19B	108.2
C3—C4—C13	106.8 (3)	H19A—C19—H19B	107.3
C22—C4—C13	110.4 (3)	C21—C20—C19	108.8 (4)
C3—C4—C5	109.0 (3)	C21—C20—H20A	109.9
C22—C4—C5	113.5 (3)	C19—C20—H20A	109.9
C13—C4—C5	109.9 (3)	C21—C20—H20B	109.9
C6—C5—C4	116.8 (3)	C19—C20—H20B	109.9
C6—C5—C10	110.7 (3)	H20A—C20—H20B	108.3
C4—C5—C10	116.6 (3)	O4—C21—O3	123.9 (5)
C6—C5—H5A	103.5	O4—C21—C20	120.7 (5)
C4—C5—H5A	103.5	O3—C21—C20	115.4 (4)
C10—C5—H5A	103.5	C4—C22—H22A	109.5
C7—C6—C5	120.4 (3)	C4—C22—H22B	109.5
C7—C6—H6A	107.2	H22A—C22—H22B	109.5
C5—C6—H6A	107.2	C4—C22—H22C	109.5
C7—C6—H6B	107.2	H22A—C22—H22C	109.5
C5—C6—H6B	107.2	H22B—C22—H22C	109.5
H6A—C6—H6B	106.9	O2—C23—O1	123.4 (4)
C23—C7—C8	111.1 (4)	O2—C23—C7	123.2 (4)
C23—C7—C6	112.5 (3)	O1—C23—C7	113.3 (4)
C8—C7—C6	111.3 (3)	C7—C24—H24A	109.5
C23—C7—C24	104.0 (3)	C7—C24—H24B	109.5
C8—C7—C24	109.5 (3)	H24A—C24—H24B	109.5
C6—C7—C24	108.2 (4)	C7—C24—H24C	109.5
C9—C8—C7	113.8 (3)	H24A—C24—H24C	109.5
C9—C8—H8A	108.8	H24B—C24—H24C	109.5
C7—C8—H8A	108.8	C10—C25—H25A	109.5
C9—C8—H8B	108.8	C10—C25—H25B	109.5
C7—C8—H8B	108.8	H25A—C25—H25B	109.5
H8A—C8—H8B	107.7	C10—C25—H25C	109.5
C8—C9—C10	114.6 (4)	H25A—C25—H25C	109.5
C8—C9—H9A	108.6	H25B—C25—H25C	109.5
C10—C9—H9A	108.6	C13—C26—H26A	109.5
C8—C9—H9B	108.6	C13—C26—H26B	109.5
C10—C9—H9B	108.6	H26A—C26—H26B	109.5
H9A—C9—H9B	107.6	C13—C26—H26C	109.5
C9—C10—C25	108.5 (3)	H26A—C26—H26C	109.5
C9—C10—C11	109.3 (3)	H26B—C26—H26C	109.5
C25—C10—C11	106.8 (3)	C28—C27—C29	120.2 (4)
C9—C10—C5	110.8 (3)	C28—C27—C17	121.7 (4)
C25—C10—C5	108.7 (3)	C29—C27—C17	118.0 (4)
C11—C10—C5	112.6 (3)	C27—C28—H28A	120.0
C12—C11—C10	117.1 (3)	C27—C28—H28B	120.0
C12—C11—H11A	108.0	H28A—C28—H28B	120.0
C10—C11—H11A	108.0	C27—C29—H29A	109.5
C12—C11—H11B	108.0	C27—C29—H29B	109.5
C10—C11—H11B	108.0	H29A—C29—H29B	109.5
H11A—C11—H11B	107.3	C27—C29—H29C	109.5
C11—C12—C13	110.8 (3)	H29A—C29—H29C	109.5
C11—C12—H12A	109.5	H29B—C29—H29C	109.5
C13—C12—H12A	109.5	C18—C30—H30A	109.5
C11—C12—H12B	109.5	C18—C30—H30B	109.5
C13—C12—H12B	109.5	H30A—C30—H30B	109.5
H12A—C12—H12B	108.1	C18—C30—H30C	109.5
C14—C13—C12	112.8 (3)	H30A—C30—H30C	109.5
C14—C13—C26	103.9 (3)	H30B—C30—H30C	109.5
C12—C13—C26	109.0 (3)	Cl4i—C31—Cl3i	135.2 (9)
C14—C13—C4	112.0 (3)	Cl1—C31—Cl1i	129.0 (8)
C12—C13—C4	106.7 (3)	Cl4i—C31—Cl3	99.6 (7)
C26—C13—C4	112.5 (3)	Cl3i—C31—Cl3	123.0 (9)
C1—C14—C15	122.4 (3)	Cl4i—C31—Cl4	67.6 (10)
C1—C14—C13	121.2 (3)	Cl3i—C31—Cl4	92.0 (6)
C15—C14—C13	116.2 (3)	Cl3—C31—Cl4	97.1 (6)
C14—C15—C16	115.7 (3)	Cl1—C31—Cl2	105.1 (6)
C14—C15—H15A	108.3	Cl1i—C31—Cl2	102.3 (6)
C16—C15—H15A	108.3	Cl1—C31—H31A	105.8
C14—C15—H15B	108.3	Cl1i—C31—H31A	106.8
C16—C15—H15B	108.3	Cl2—C31—H31A	106.1
H15A—C15—H15B	107.4	Cl4i—C31—H31B	50.8
C15—C16—C17	110.0 (3)	Cl3i—C31—H31B	114.2
C15—C16—H16A	109.7	Cl3—C31—H31B	112.6
C17—C16—H16A	109.7	Cl4—C31—H31B	114.0
C15—C16—H16B	109.7	Cl2—C31—H31B	125.2
C17—C16—H16B	109.7
C14—C1—C2—C3	−1.8 (6)	C15—C16—C17—C18	−62.5 (4)
C18—C1—C2—C3	169.8 (3)	C14—C1—C18—C30	97.3 (4)
C1—C2—C3—C4	32.3 (5)	C2—C1—C18—C30	−74.3 (4)
C2—C3—C4—C22	60.6 (4)	C14—C1—C18—C19	−146.7 (4)
C2—C3—C4—C13	−57.6 (4)	C2—C1—C18—C19	41.7 (5)
C2—C3—C4—C5	−176.3 (3)	C14—C1—C18—C17	−24.7 (5)
C3—C4—C5—C6	−60.2 (4)	C2—C1—C18—C17	163.7 (3)
C22—C4—C5—C6	58.9 (4)	C16—C17—C18—C30	−66.4 (4)
C13—C4—C5—C6	−176.9 (3)	C27—C17—C18—C30	61.0 (4)
C3—C4—C5—C10	165.8 (3)	C16—C17—C18—C19	176.2 (3)
C22—C4—C5—C10	−75.1 (4)	C27—C17—C18—C19	−56.5 (4)
C13—C4—C5—C10	49.1 (4)	C16—C17—C18—C1	53.4 (4)
C4—C5—C6—C7	−94.0 (4)	C27—C17—C18—C1	−179.2 (3)
C10—C5—C6—C7	42.5 (4)	C30—C18—C19—C20	178.2 (4)
C5—C6—C7—C23	85.3 (4)	C1—C18—C19—C20	60.8 (5)
C5—C6—C7—C8	−40.2 (5)	C17—C18—C19—C20	−60.7 (5)
C5—C6—C7—C24	−160.5 (3)	C18—C19—C20—C21	−177.8 (4)
C23—C7—C8—C9	−82.4 (4)	C19—C20—C21—O4	64.4 (7)
C6—C7—C8—C9	43.8 (5)	C19—C20—C21—O3	−113.9 (5)
C24—C7—C8—C9	163.3 (3)	C8—C7—C23—O2	−6.2 (5)
C7—C8—C9—C10	−55.0 (5)	C6—C7—C23—O2	−131.8 (4)
C8—C9—C10—C25	−63.0 (4)	C24—C7—C23—O2	111.5 (5)
C8—C9—C10—C11	−179.1 (3)	C8—C7—C23—O1	177.5 (3)
C8—C9—C10—C5	56.3 (4)	C6—C7—C23—O1	52.0 (5)
C6—C5—C10—C9	−47.5 (4)	C24—C7—C23—O1	−64.8 (4)
C4—C5—C10—C9	89.1 (4)	C16—C17—C27—C28	37.4 (5)
C6—C5—C10—C25	71.6 (4)	C18—C17—C27—C28	−88.4 (5)
C4—C5—C10—C25	−151.8 (3)	C16—C17—C27—C29	−139.0 (4)
C6—C5—C10—C11	−170.3 (3)	C18—C17—C27—C29	95.2 (4)
C4—C5—C10—C11	−33.6 (4)	Cl4i—C31—Cl1—C31i	116.2 (8)
C9—C10—C11—C12	−88.7 (4)	Cl3i—C31—Cl1—C31i	−23 (4)
C25—C10—C11—C12	154.1 (4)	Cl1i—C31—Cl1—C31i	48.8 (10)
C5—C10—C11—C12	34.9 (5)	Cl3—C31—Cl1—C31i	−58.6 (5)
C10—C11—C12—C13	−52.2 (5)	Cl4—C31—Cl1—C31i	48.8 (6)
C11—C12—C13—C14	−171.7 (3)	Cl2—C31—Cl1—C31i	−71.3 (5)
C11—C12—C13—C26	−56.9 (4)	Cl4i—C31—Cl2—C31i	90 (3)
C11—C12—C13—C4	64.9 (4)	Cl3i—C31—Cl2—C31i	−95.7 (11)
C3—C4—C13—C14	55.0 (4)	Cl1—C31—Cl2—C31i	72.3 (11)
C22—C4—C13—C14	−60.9 (4)	Cl1i—C31—Cl2—C31i	−64.2 (9)
C5—C4—C13—C14	173.1 (3)	Cl3—C31—Cl2—C31i	62.1 (10)
C3—C4—C13—C12	178.9 (3)	Cl4—C31—Cl2—C31i	−18.6 (7)
C22—C4—C13—C12	63.0 (4)	Cl4i—C31—Cl3—C31i	99.5 (8)
C5—C4—C13—C12	−63.0 (4)	Cl3i—C31—Cl3—C31i	−65.9 (11)
C3—C4—C13—C26	−61.7 (4)	Cl1—C31—Cl3—C31i	103.9 (6)
C22—C4—C13—C26	−177.6 (3)	Cl1i—C31—Cl3—C31i	−6.6 (11)
C5—C4—C13—C26	56.4 (4)	Cl4—C31—Cl3—C31i	31.2 (7)
C2—C1—C14—C15	174.5 (3)	Cl2—C31—Cl3—C31i	−90.1 (6)
C18—C1—C14—C15	3.5 (6)	Cl4i—C31—Cl4—C31i	−134.0 (15)
C2—C1—C14—C13	0.2 (6)	Cl3i—C31—Cl4—C31i	87.1 (11)
C18—C1—C14—C13	−170.9 (3)	Cl1—C31—Cl4—C31i	−79.0 (12)
C12—C13—C14—C1	−148.5 (4)	Cl1i—C31—Cl4—C31i	101.0 (12)
C26—C13—C14—C1	93.6 (4)	Cl3—C31—Cl4—C31i	−36.5 (11)
C4—C13—C14—C1	−28.1 (5)	Cl2—C31—Cl4—C31i	24.5 (8)
C12—C13—C14—C15	36.8 (4)	C31i—C31—Cl4—Cl4i	134.0 (15)
C26—C13—C14—C15	−81.0 (4)	Cl3i—C31—Cl4—Cl4i	−138.9 (10)
C4—C13—C14—C15	157.2 (3)	Cl1—C31—Cl4—Cl4i	55.0 (7)
C1—C14—C15—C16	−11.2 (5)	Cl1i—C31—Cl4—Cl4i	−125.0 (10)
C13—C14—C15—C16	163.4 (3)	Cl3—C31—Cl4—Cl4i	97.5 (8)
C14—C15—C16—C17	40.8 (5)	Cl2—C31—Cl4—Cl4i	158.5 (9)
C15—C16—C17—C27	168.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.82	1.81	2.621 (6)	168
O3—H3···O2i	0.82	1.85	2.670 (4)	176
C22—H22B···O1	0.96	2.56	3.380 (5)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.82	1.81	2.621 (6)	168
O3—H3⋯O2i	0.82	1.85	2.670 (4)	176
C22—H22B⋯O1	0.96	2.56	3.380 (5)	144

Symmetry code: (i) .