16-[4-(3-Chloro­prop­oxy)-3-methoxy­benzyl­idene]-4-androstene-3,17-dione

In the title compound, C₃₀H₃₇ClO₄, the cyclo­hexene ring A of the steroid nucleus has a 1α-sofa conformation. The cyclo­hexane rings adopt chair conformations. The cyclo­pentane ring adopts a 14β-envelope conformation. The benzyl­idene group has an E configuration with respect to the carbonyl group on the cyclo­pentane ring. The crystal packing is dictated by weak inter­molecular C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.056
• wR factor = 0.153
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C31
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.13

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               4850
           Count of symmetry unique reflns         2768
           Completeness (_total/calc)            175.22%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2082
           Fraction of Friedel pairs measured     0.752
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003) and Qmol (Gans & Shalloway, 2001); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

16-[4-(3-Chloropropoxy)-3-methoxybenzylidene]-4-androstene-3,17-dione

Crystal data

C30H37ClO4	Dx = 1.203 Mg m^−3
Mr = 497.05	Melting point = 438–440 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4170 reflections
a = 8.0046 (4) Å	θ = 4.8–39.7°
b = 17.4763 (9) Å	µ = 0.17 mm^−1
c = 19.6133 (10) Å	T = 273 K
V = 2743.7 (2) Å^3	Needle, yellow
Z = 4	0.10 × 0.08 × 0.04 mm
F(000) = 1064

Data collection

Bruker SMART APEX CCD area detector diffractometer	3335 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 25.0°, θmin = 1.6°
ω scans	h = −9→9
20024 measured reflections	k = −20→20
4850 independent reflections	l = −23→23

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)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.0799P)^2 + 0.3313P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
4850 reflections	Δρmax = 0.29 e Å^−3
320 parameters	Δρmin = −0.16 e Å^−3
40 restraints	Absolute structure: Flack (1983), 2083 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (13)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O3	0.6009 (5)	0.1670 (2)	−0.38108 (15)	0.1491 (12)
O17	−0.0815 (3)	0.19477 (14)	0.07792 (13)	0.1012 (7)
O23	0.7550 (4)	0.08399 (17)	0.24723 (12)	0.1078 (8)
O28	0.6916 (4)	0.13245 (19)	0.36747 (13)	0.1242 (9)
C1	0.2469 (5)	0.1573 (3)	−0.27176 (19)	0.1172 (14)
H1A	0.1275	0.1505	−0.2777	0.141*
H1B	0.2659	0.2098	−0.2579	0.141*
C2	0.3319 (6)	0.1440 (3)	−0.3389 (2)	0.1331 (16)
H2A	0.3005	0.0940	−0.3562	0.160*
H2B	0.2940	0.1820	−0.3714	0.160*
C3	0.5153 (7)	0.1481 (2)	−0.3332 (2)	0.1092 (12)
C4	0.5856 (5)	0.1254 (2)	−0.26801 (18)	0.0919 (10)
H4	0.7011	0.1274	−0.2632	0.110*
C5	0.4967 (4)	0.10190 (18)	−0.21488 (17)	0.0755 (8)
C6	0.5812 (4)	0.0687 (2)	−0.15353 (16)	0.0856 (9)
H6A	0.7006	0.0775	−0.1570	0.103*
H6B	0.5630	0.0138	−0.1528	0.103*
C7	0.5177 (3)	0.10287 (19)	−0.08764 (15)	0.0739 (8)
H7A	0.5504	0.1562	−0.0853	0.089*
H7B	0.5686	0.0764	−0.0495	0.089*
C8	0.3288 (3)	0.09701 (16)	−0.08204 (15)	0.0664 (7)
H8	0.2971	0.0428	−0.0814	0.080*
C9	0.2484 (3)	0.13526 (16)	−0.14412 (15)	0.0711 (7)
H9	0.2849	0.1888	−0.1429	0.085*
C10	0.3076 (4)	0.10340 (18)	−0.21430 (16)	0.0785 (8)
C11	0.0544 (4)	0.1375 (2)	−0.13865 (19)	0.0917 (10)
H11A	0.0102	0.1678	−0.1760	0.110*
H11B	0.0111	0.0860	−0.1433	0.110*
C12	−0.0062 (4)	0.1710 (2)	−0.07186 (18)	0.0892 (10)
H12A	−0.1268	0.1667	−0.0693	0.107*
H12B	0.0227	0.2248	−0.0698	0.107*
C13	0.0728 (3)	0.12900 (17)	−0.01147 (17)	0.0750 (8)
C14	0.2613 (3)	0.13515 (15)	−0.01877 (14)	0.0648 (7)
H14	0.2835	0.1898	−0.0251	0.078*
C15	0.3302 (4)	0.11600 (17)	0.05229 (14)	0.0729 (7)
H15A	0.3378	0.0611	0.0591	0.087*
H15B	0.4394	0.1387	0.0593	0.087*
C16	0.2009 (4)	0.15141 (16)	0.09886 (17)	0.0724 (8)
C17	0.0457 (4)	0.16361 (18)	0.05770 (18)	0.0798 (9)
C18	0.0068 (4)	0.04614 (18)	−0.0066 (2)	0.0967 (11)
H18A	0.0253	0.0204	−0.0491	0.145*
H18B	−0.1106	0.0470	0.0033	0.145*
H18C	0.0648	0.0196	0.0291	0.145*
C19	0.2431 (5)	0.0218 (2)	−0.2260 (2)	0.1176 (13)
H19A	0.2909	0.0016	−0.2671	0.176*
H19B	0.1236	0.0227	−0.2301	0.176*
H19C	0.2744	−0.0099	−0.1882	0.176*
C20	0.2067 (4)	0.17147 (17)	0.16442 (17)	0.0810 (9)
H20	0.1097	0.1948	0.1801	0.097*
C21	0.3354 (4)	0.16378 (17)	0.21572 (17)	0.0788 (8)
C22	0.4889 (4)	0.12775 (18)	0.20450 (16)	0.0780 (8)
H22	0.5128	0.1088	0.1613	0.094*
C23	0.6052 (4)	0.11945 (19)	0.25509 (17)	0.0844 (9)
C24	0.5702 (5)	0.1457 (2)	0.32061 (19)	0.0963 (10)
C25	0.4207 (6)	0.1825 (2)	0.3323 (2)	0.1069 (12)
H25	0.3974	0.2020	0.3754	0.128*
C26	0.3063 (5)	0.1905 (2)	0.2809 (2)	0.0994 (11)
H26	0.2054	0.2147	0.2903	0.119*
C27	0.7956 (5)	0.0567 (3)	0.18167 (19)	0.1138 (13)
H27A	0.9075	0.0369	0.1819	0.171*
H27B	0.7878	0.0979	0.1494	0.171*
H27C	0.7192	0.0168	0.1691	0.171*
C29	0.6727 (5)	0.1565 (3)	0.43644 (18)	0.1288 (12)
H29A	0.5694	0.1366	0.4553	0.155*
H29B	0.6698	0.2119	0.4390	0.155*
Cl1	1.1549 (2)	0.12117 (10)	0.49276 (8)	0.1449 (7)	0.856 (2)
C30	0.8188 (5)	0.1262 (3)	0.4752 (2)	0.1288 (12)	0.856 (2)
H30A	0.8087	0.1405	0.5228	0.155*	0.856 (2)
H30B	0.8199	0.0708	0.4725	0.155*	0.856 (2)
Cl1A	1.0358 (15)	0.0988 (6)	0.5365 (5)	0.1449 (7)	0.144 (2)
C30A	0.8183 (6)	0.1884 (16)	0.4743 (12)	0.1288 (12)	0.144 (2)
H30C	0.8187	0.2437	0.4701	0.155*	0.144 (2)
H30D	0.8083	0.1757	0.5223	0.155*	0.144 (2)
C31	0.9781 (6)	0.1570 (4)	0.4471 (3)	0.1588 (19)
H31A	0.9767	0.2125	0.4499	0.191*
H31B	0.9876	0.1429	0.3995	0.191*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.180 (3)	0.176 (3)	0.0916 (19)	−0.010 (3)	0.023 (2)	0.0081 (19)
O17	0.0775 (14)	0.1021 (16)	0.1240 (18)	0.0370 (12)	0.0197 (14)	0.0127 (14)
O23	0.0925 (17)	0.146 (2)	0.0851 (16)	0.0231 (16)	0.0009 (14)	0.0125 (15)
O28	0.115 (2)	0.171 (3)	0.0868 (16)	−0.0004 (19)	−0.0063 (16)	−0.0196 (17)
C1	0.102 (3)	0.158 (4)	0.092 (3)	0.020 (3)	−0.028 (2)	0.007 (2)
C2	0.137 (4)	0.174 (5)	0.088 (3)	0.001 (3)	−0.028 (3)	0.007 (3)
C3	0.139 (4)	0.108 (3)	0.081 (3)	−0.008 (3)	0.006 (3)	−0.008 (2)
C4	0.091 (2)	0.097 (2)	0.087 (2)	−0.010 (2)	0.001 (2)	−0.0160 (19)
C5	0.0707 (18)	0.0759 (19)	0.0799 (19)	−0.0051 (16)	−0.0032 (17)	−0.0147 (16)
C6	0.0607 (17)	0.101 (2)	0.095 (2)	0.0088 (16)	−0.0036 (17)	−0.0065 (19)
C7	0.0532 (15)	0.090 (2)	0.0783 (18)	0.0106 (14)	−0.0060 (14)	−0.0023 (16)
C8	0.0514 (14)	0.0624 (15)	0.0854 (19)	0.0022 (12)	−0.0070 (14)	0.0056 (14)
C9	0.0594 (15)	0.0674 (16)	0.0864 (19)	−0.0042 (13)	−0.0100 (15)	−0.0039 (15)
C10	0.0718 (18)	0.0779 (19)	0.086 (2)	−0.0059 (15)	−0.0173 (16)	−0.0060 (16)
C11	0.0598 (17)	0.108 (3)	0.108 (2)	0.0104 (16)	−0.0182 (17)	−0.004 (2)
C12	0.0522 (15)	0.101 (2)	0.114 (3)	0.0100 (17)	−0.0068 (18)	0.001 (2)
C13	0.0502 (15)	0.0720 (18)	0.103 (2)	0.0065 (13)	0.0012 (15)	0.0043 (17)
C14	0.0510 (14)	0.0595 (15)	0.0840 (19)	0.0018 (12)	−0.0003 (13)	0.0033 (14)
C15	0.0639 (16)	0.0693 (17)	0.0854 (19)	0.0058 (14)	0.0019 (15)	0.0047 (15)
C16	0.0661 (18)	0.0597 (15)	0.091 (2)	0.0095 (13)	0.0141 (16)	0.0061 (15)
C17	0.0645 (18)	0.0681 (18)	0.107 (2)	0.0086 (15)	0.0085 (17)	0.0102 (17)
C18	0.0691 (19)	0.083 (2)	0.138 (3)	−0.0145 (17)	0.010 (2)	−0.004 (2)
C19	0.105 (3)	0.109 (3)	0.138 (3)	−0.030 (2)	0.000 (3)	−0.044 (2)
C20	0.080 (2)	0.0694 (18)	0.093 (2)	0.0121 (16)	0.0153 (18)	0.0026 (16)
C21	0.086 (2)	0.0644 (17)	0.086 (2)	0.0073 (17)	0.0144 (19)	0.0002 (16)
C22	0.084 (2)	0.0756 (19)	0.0744 (19)	−0.0006 (17)	0.0103 (17)	0.0054 (15)
C23	0.087 (2)	0.084 (2)	0.081 (2)	−0.0033 (19)	0.0076 (19)	0.0064 (17)
C24	0.107 (3)	0.099 (3)	0.083 (2)	−0.006 (2)	−0.002 (2)	−0.008 (2)
C25	0.126 (3)	0.104 (3)	0.091 (3)	0.001 (2)	0.017 (3)	−0.025 (2)
C26	0.110 (3)	0.091 (2)	0.097 (3)	0.015 (2)	0.012 (2)	−0.009 (2)
C27	0.096 (3)	0.150 (4)	0.095 (3)	0.040 (2)	0.021 (2)	0.022 (2)
C29	0.136 (3)	0.174 (3)	0.0764 (19)	−0.030 (3)	0.0004 (15)	−0.018 (2)
Cl1	0.1546 (14)	0.1579 (12)	0.1221 (11)	0.0310 (11)	−0.0352 (10)	−0.0105 (10)
C30	0.136 (3)	0.174 (3)	0.0764 (19)	−0.030 (3)	0.0004 (15)	−0.018 (2)
Cl1A	0.1546 (14)	0.1579 (12)	0.1221 (11)	0.0310 (11)	−0.0352 (10)	−0.0105 (10)
C30A	0.136 (3)	0.174 (3)	0.0764 (19)	−0.030 (3)	0.0004 (15)	−0.018 (2)
C31	0.153 (4)	0.191 (5)	0.133 (4)	−0.016 (4)	−0.024 (3)	−0.013 (4)

Geometric parameters (Å, º)

O3—C3	1.209 (5)	C14—H14	0.98
O17—C17	1.221 (3)	C15—C16	1.513 (4)
O23—C23	1.358 (4)	C15—H15A	0.97
O23—C27	1.409 (4)	C15—H15B	0.97
O28—C24	1.358 (4)	C16—C20	1.334 (4)
O28—C29	1.425 (4)	C16—C17	1.497 (4)
C1—C2	1.501 (6)	C18—H18A	0.96
C1—C10	1.547 (5)	C18—H18B	0.96
C1—H1A	0.97	C18—H18C	0.96
C1—H1B	0.97	C19—H19A	0.96
C2—C3	1.474 (6)	C19—H19B	0.96
C2—H2A	0.97	C19—H19C	0.96
C2—H2B	0.97	C20—C21	1.446 (5)
C3—C4	1.451 (5)	C20—H20	0.93
C4—C5	1.327 (4)	C21—C26	1.381 (5)
C4—H4	0.93	C21—C22	1.398 (5)
C5—C6	1.498 (4)	C22—C23	1.368 (5)
C5—C10	1.514 (5)	C22—H22	0.93
C6—C7	1.512 (4)	C23—C24	1.393 (5)
C6—H6A	0.97	C24—C25	1.378 (5)
C6—H6B	0.97	C25—C26	1.369 (5)
C7—C8	1.520 (4)	C25—H25	0.93
C7—H7A	0.97	C26—H26	0.93
C7—H7B	0.97	C27—H27A	0.96
C8—C14	1.509 (4)	C27—H27B	0.96
C8—C9	1.531 (4)	C27—H27C	0.96
C8—H8	0.98	C29—C30A	1.4900 (10)
C9—C11	1.557 (4)	C29—C30	1.4921 (10)
C9—C10	1.559 (4)	C29—H29A	0.97
C9—H9	0.98	C29—H29B	0.97
C10—C19	1.534 (5)	Cl1—C31	1.788 (6)
C11—C12	1.514 (5)	C30—C31	1.4898 (10)
C11—H11A	0.97	C30—H30A	0.97
C11—H11B	0.97	C30—H30B	0.97
C12—C13	1.530 (4)	Cl1A—C31	2.079 (11)
C12—H12A	0.97	C30A—C31	1.4899 (10)
C12—H12B	0.97	C30A—H30C	0.97
C13—C17	1.501 (5)	C30A—H30D	0.97
C13—C14	1.519 (4)	C31—H31A	0.97
C13—C18	1.544 (4)	C31—H31B	0.97
C14—C15	1.536 (4)
C23—O23—C27	117.5 (3)	C14—C15—H15B	111.3
C24—O28—C29	121.1 (3)	H15A—C15—H15B	109.2
C2—C1—C10	113.8 (3)	C20—C16—C17	120.8 (3)
C2—C1—H1A	108.8	C20—C16—C15	131.7 (3)
C10—C1—H1A	108.8	C17—C16—C15	107.5 (3)
C2—C1—H1B	108.8	O17—C17—C16	125.5 (3)
C10—C1—H1B	108.8	O17—C17—C13	126.4 (3)
H1A—C1—H1B	107.7	C16—C17—C13	108.1 (2)
C3—C2—C1	112.1 (4)	C13—C18—H18A	109.5
C3—C2—H2A	109.2	C13—C18—H18B	109.5
C1—C2—H2A	109.2	H18A—C18—H18B	109.5
C3—C2—H2B	109.2	C13—C18—H18C	109.5
C1—C2—H2B	109.2	H18A—C18—H18C	109.5
H2A—C2—H2B	107.9	H18B—C18—H18C	109.5
O3—C3—C4	122.6 (4)	C10—C19—H19A	109.5
O3—C3—C2	121.2 (4)	C10—C19—H19B	109.5
C4—C3—C2	116.1 (4)	H19A—C19—H19B	109.5
C5—C4—C3	124.6 (4)	C10—C19—H19C	109.5
C5—C4—H4	117.7	H19A—C19—H19C	109.5
C3—C4—H4	117.7	H19B—C19—H19C	109.5
C4—C5—C6	120.6 (3)	C16—C20—C21	132.2 (3)
C4—C5—C10	122.5 (3)	C16—C20—H20	113.9
C6—C5—C10	116.9 (3)	C21—C20—H20	113.9
C5—C6—C7	112.4 (3)	C26—C21—C22	116.5 (3)
C5—C6—H6A	109.1	C26—C21—C20	119.5 (3)
C7—C6—H6A	109.1	C22—C21—C20	123.9 (3)
C5—C6—H6B	109.1	C23—C22—C21	122.1 (3)
C7—C6—H6B	109.1	C23—C22—H22	118.9
H6A—C6—H6B	107.9	C21—C22—H22	118.9
C6—C7—C8	111.7 (3)	O23—C23—C22	124.5 (3)
C6—C7—H7A	109.3	O23—C23—C24	115.6 (3)
C8—C7—H7A	109.3	C22—C23—C24	119.8 (3)
C6—C7—H7B	109.3	O28—C24—C25	126.1 (4)
C8—C7—H7B	109.3	O28—C24—C23	115.1 (4)
H7A—C7—H7B	107.9	C25—C24—C23	118.8 (4)
C14—C8—C7	112.7 (2)	C26—C25—C24	120.4 (3)
C14—C8—C9	108.1 (2)	C26—C25—H25	119.8
C7—C8—C9	109.4 (2)	C24—C25—H25	119.8
C14—C8—H8	108.9	C25—C26—C21	122.3 (4)
C7—C8—H8	108.9	C25—C26—H26	118.8
C9—C8—H8	108.9	C21—C26—H26	118.8
C8—C9—C11	112.1 (3)	O23—C27—H27A	109.5
C8—C9—C10	114.8 (2)	O23—C27—H27B	109.5
C11—C9—C10	111.9 (2)	H27A—C27—H27B	109.5
C8—C9—H9	105.8	O23—C27—H27C	109.5
C11—C9—H9	105.8	H27A—C27—H27C	109.5
C10—C9—H9	105.8	H27B—C27—H27C	109.5
C5—C10—C19	108.6 (3)	O28—C29—C30A	120.0 (7)
C5—C10—C1	108.6 (3)	O28—C29—C30	107.2 (3)
C19—C10—C1	110.5 (3)	O28—C29—H29A	110.3
C5—C10—C9	108.5 (2)	C30A—C29—H29A	127.7
C19—C10—C9	111.2 (3)	C30—C29—H29A	110.3
C1—C10—C9	109.3 (3)	O28—C29—H29B	110.3
C12—C11—C9	112.9 (3)	C30A—C29—H29B	67.6
C12—C11—H11A	109.0	C30—C29—H29B	110.3
C9—C11—H11A	109.0	H29A—C29—H29B	108.5
C12—C11—H11B	109.0	C31—C30—C29	110.7 (4)
C9—C11—H11B	109.0	C31—C30—H30A	109.5
H11A—C11—H11B	107.8	C29—C30—H30A	109.5
C11—C12—C13	110.6 (3)	C31—C30—H30B	109.5
C11—C12—H12A	109.5	C29—C30—H30B	109.5
C13—C12—H12A	109.5	H30A—C30—H30B	108.1
C11—C12—H12B	109.5	C31—C30A—C29	110.8 (4)
C13—C12—H12B	109.5	C31—C30A—H30C	109.5
H12A—C12—H12B	108.1	C29—C30A—H30C	109.5
C17—C13—C14	101.5 (2)	C31—C30A—H30D	109.5
C17—C13—C12	116.5 (3)	C29—C30A—H30D	109.5
C14—C13—C12	107.7 (2)	H30C—C30A—H30D	108.1
C17—C13—C18	105.8 (3)	C30—C31—Cl1	111.4 (4)
C14—C13—C18	114.3 (2)	C30A—C31—Cl1	129.0 (11)
C12—C13—C18	110.9 (3)	C30—C31—Cl1A	72.6 (4)
C8—C14—C13	113.7 (2)	C30A—C31—Cl1A	94.0 (13)
C8—C14—C15	121.4 (2)	C30—C31—H31A	109.3
C13—C14—C15	104.8 (2)	C30A—C31—H31A	66.6
C8—C14—H14	105.2	Cl1—C31—H31A	109.3
C13—C14—H14	105.2	Cl1A—C31—H31A	116.4
C15—C14—H14	105.2	C30—C31—H31B	109.3
C16—C15—C14	102.3 (2)	C30A—C31—H31B	120.4
C16—C15—H15A	111.3	Cl1—C31—H31B	109.3
C14—C15—H15A	111.3	Cl1A—C31—H31B	132.1
C16—C15—H15B	111.3	H31A—C31—H31B	108.0
C10—C1—C2—C3	−54.6 (6)	C13—C14—C15—C16	−36.2 (3)
C1—C2—C3—O3	−152.3 (4)	C14—C15—C16—C20	−160.8 (3)
C1—C2—C3—C4	30.0 (6)	C14—C15—C16—C17	18.7 (3)
O3—C3—C4—C5	−177.7 (4)	C20—C16—C17—O17	3.6 (5)
C2—C3—C4—C5	−0.1 (6)	C15—C16—C17—O17	−176.0 (3)
C3—C4—C5—C6	170.8 (3)	C20—C16—C17—C13	−174.9 (3)
C3—C4—C5—C10	−6.0 (5)	C15—C16—C17—C13	5.5 (3)
C4—C5—C6—C7	132.3 (3)	C14—C13—C17—O17	154.0 (3)
C10—C5—C6—C7	−50.7 (4)	C12—C13—C17—O17	37.3 (5)
C5—C6—C7—C8	53.9 (4)	C18—C13—C17—O17	−86.4 (4)
C6—C7—C8—C14	−176.4 (3)	C14—C13—C17—C16	−27.6 (3)
C6—C7—C8—C9	−56.1 (3)	C12—C13—C17—C16	−144.2 (3)
C14—C8—C9—C11	−52.0 (3)	C18—C13—C17—C16	92.0 (3)
C7—C8—C9—C11	−175.1 (3)	C17—C16—C20—C21	177.4 (3)
C14—C8—C9—C10	178.9 (2)	C15—C16—C20—C21	−3.2 (6)
C7—C8—C9—C10	55.8 (3)	C16—C20—C21—C26	179.9 (3)
C4—C5—C10—C19	102.9 (4)	C16—C20—C21—C22	−2.7 (5)
C6—C5—C10—C19	−74.0 (4)	C26—C21—C22—C23	−0.3 (5)
C4—C5—C10—C1	−17.4 (4)	C20—C21—C22—C23	−177.8 (3)
C6—C5—C10—C1	165.7 (3)	C27—O23—C23—C22	2.7 (5)
C4—C5—C10—C9	−136.1 (3)	C27—O23—C23—C24	−179.8 (3)
C6—C5—C10—C9	47.0 (4)	C21—C22—C23—O23	179.0 (3)
C2—C1—C10—C5	47.0 (5)	C21—C22—C23—C24	1.6 (5)
C2—C1—C10—C19	−72.0 (5)	C29—O28—C24—C25	0.4 (6)
C2—C1—C10—C9	165.2 (3)	C29—O28—C24—C23	179.8 (4)
C8—C9—C10—C5	−49.9 (3)	O23—C23—C24—O28	0.3 (5)
C11—C9—C10—C5	−179.1 (3)	C22—C23—C24—O28	177.9 (3)
C8—C9—C10—C19	69.5 (3)	O23—C23—C24—C25	179.8 (3)
C11—C9—C10—C19	−59.7 (4)	C22—C23—C24—C25	−2.6 (5)
C8—C9—C10—C1	−168.2 (3)	O28—C24—C25—C26	−178.2 (4)
C11—C9—C10—C1	62.7 (4)	C23—C24—C25—C26	2.4 (6)
C8—C9—C11—C12	51.5 (4)	C24—C25—C26—C21	−1.1 (6)
C10—C9—C11—C12	−177.9 (3)	C22—C21—C26—C25	0.1 (5)
C9—C11—C12—C13	−53.9 (4)	C20—C21—C26—C25	177.7 (3)
C11—C12—C13—C17	170.7 (3)	C24—O28—C29—C30A	−140.8 (15)
C11—C12—C13—C14	57.5 (3)	C24—O28—C29—C30	174.3 (4)
C11—C12—C13—C18	−68.2 (3)	O28—C29—C30—C31	60.5 (6)
C7—C8—C14—C13	−179.1 (2)	C30A—C29—C30—C31	−55.4 (11)
C9—C8—C14—C13	59.9 (3)	O28—C29—C30A—C31	−28 (3)
C7—C8—C14—C15	−52.6 (4)	C30—C29—C30A—C31	55.4 (11)
C9—C8—C14—C15	−173.5 (2)	C29—C30—C31—C30A	55.3 (11)
C17—C13—C14—C8	174.3 (2)	C29—C30—C31—Cl1	−179.8 (4)
C12—C13—C14—C8	−62.8 (3)	C29—C30—C31—Cl1A	171.8 (5)
C18—C13—C14—C8	60.9 (4)	C29—C30A—C31—C30	−55.5 (11)
C17—C13—C14—C15	39.4 (3)	C29—C30A—C31—Cl1	−135.0 (13)
C12—C13—C14—C15	162.4 (2)	C29—C30A—C31—Cl1A	−114 (2)
C18—C13—C14—C15	−74.0 (3)	C19—C10—C13—C18	5.2 (3)
C8—C14—C15—C16	−166.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O17^i	0.98	2.51	3.430 (3)	156
C27—H27B···O17^ii	0.96	2.43	3.306 (5)	151
C30—H30A···O3^iii	0.97	2.56	3.390 (6)	144

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x+1, y, z; (iii) x, y, z+1.