16β-Bromo-17α-hydroxy­pregn-4-ene-3,20-dione

Wang, S.; Wang, Y.; Nie, Q.; Xiang, A.; Zhou, L.

doi:10.1107/S1600536804031083

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16β-Bromo-17α-hydroxypregn-4-ene-3,20-dione

S. Wang, Y. Wang, Q. Nie, A. Xiang and L. Zhou

The title compound, C₂₁H₂₉BrO₃, is a steroid used as an intermediate in medicine. The asymmetric unit consists of two molecules and the structure contains intermolecular hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031083/is6018sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031083/is6018Isup2.hkl Contains datablock I

CCDC reference: 262299

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.043
wR factor = 0.093
Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.67 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.33 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C41
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br1     ..       3.56 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      37.00 A   3  

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               6647
           Count of symmetry unique reflns         3793
           Completeness (_total/calc)            175.24%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2854
           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
   7 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

16β-Bromo-17α-hydroxypregn-4-ene-3,20-dione top

Crystal data top

C₂₁H₂₉BrO₃	F(000) = 1712
M_r = 409.35	D_x = 1.352 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 22.565 (7) Å	Cell parameters from 2865 reflections
b = 9.393 (3) Å	θ = 2.4–21.6°
c = 21.052 (7) Å	µ = 2.06 mm⁻¹
β = 115.682 (8)°	T = 293 K
V = 4021 (2) Å³	Needle, colorless
Z = 8	0.24 × 0.18 × 0.14 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	6647 independent reflections
Radiation source: fine-focus sealed tube	4103 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −23→26
T_min = 0.605, T_max = 0.749	k = −10→11
10528 measured reflections	l = −23→25

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.093	w = 1/[σ²(F_o²)] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
6647 reflections	Δρ_max = 0.57 e Å⁻³
459 parameters	Δρ_min = −0.50 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2214 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.012 (9)

Special details top

Experimental. The melting point measured by DSC is 469.25 K.

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
Br1	0.43123 (3)	0.25640 (7)	0.02031 (3)	0.0734 (2)
Br2	0.07052 (4)	−0.31301 (7)	0.42330 (3)	0.0931 (3)
O1	0.25906 (19)	−0.3337 (5)	0.39598 (18)	0.0711 (12)
O2	0.41558 (19)	0.5390 (4)	0.14409 (19)	0.0670 (12)
O3	0.27481 (15)	0.3550 (4)	0.05811 (15)	0.0441 (9)
H3	0.2649	0.4089	0.0826	0.066*
O4	0.20637 (18)	0.5286 (4)	0.11173 (17)	0.0609 (11)
O5	0.0828 (2)	0.0739 (6)	0.5140 (2)	0.0868 (14)
O6	0.20916 (17)	−0.0036 (4)	0.48219 (16)	0.0577 (10)
H6	0.2179	0.0595	0.5118	0.086*
C1	0.3261 (3)	−0.0075 (5)	0.3614 (2)	0.0485 (14)
H1A	0.3522	0.0715	0.3891	0.058*
H1B	0.2820	0.0277	0.3328	0.058*
C2	0.3228 (3)	−0.1232 (6)	0.4116 (3)	0.0616 (17)
H2A	0.3671	−0.1478	0.4452	0.074*
H2B	0.3000	−0.0856	0.4378	0.074*
C3	0.2887 (3)	−0.2532 (7)	0.3735 (3)	0.0562 (15)
C4	0.2947 (2)	−0.2857 (6)	0.3086 (2)	0.0554 (16)
H4	0.2743	−0.3675	0.2840	0.067*
C5	0.3276 (2)	−0.2053 (5)	0.2825 (2)	0.0430 (13)
C6	0.3399 (3)	−0.2607 (6)	0.2214 (2)	0.0567 (15)
H6A	0.3857	−0.2877	0.2385	0.068*
H6B	0.3133	−0.3448	0.2018	0.068*
C7	0.3235 (3)	−0.1497 (5)	0.1644 (3)	0.0549 (15)
H7A	0.2763	−0.1352	0.1420	0.066*
H7B	0.3363	−0.1851	0.1289	0.066*
C8	0.3572 (2)	−0.0071 (5)	0.1916 (2)	0.0387 (12)
H8	0.4049	−0.0220	0.2127	0.046*
C9	0.3378 (2)	0.0476 (5)	0.2500 (2)	0.0358 (12)
H9	0.2897	0.0543	0.2278	0.043*
C10	0.3560 (2)	−0.0614 (5)	0.3122 (2)	0.0363 (12)
C11	0.3631 (3)	0.1984 (5)	0.2749 (2)	0.0474 (13)
H11A	0.4104	0.1945	0.3023	0.057*
H11B	0.3444	0.2314	0.3060	0.057*
C12	0.3470 (3)	0.3077 (5)	0.2153 (2)	0.0405 (13)
H12A	0.3683	0.3975	0.2348	0.049*
H12B	0.2999	0.3239	0.1920	0.049*
C13	0.3708 (2)	0.2533 (6)	0.16113 (19)	0.0338 (11)
C14	0.3462 (2)	0.3358 (5)	0.0901 (2)	0.0368 (12)
C15	0.3535 (2)	0.2239 (5)	0.0393 (2)	0.0395 (14)
H15	0.3141	0.2283	−0.0056	0.047*
C16	0.3560 (3)	0.0755 (5)	0.0722 (2)	0.0431 (14)
H16A	0.3238	0.0119	0.0386	0.052*
H16B	0.3993	0.0333	0.0881	0.052*
C17	0.3398 (2)	0.1060 (5)	0.1350 (2)	0.0356 (12)
H17	0.2921	0.1191	0.1152	0.043*
C18	0.4316 (3)	−0.0779 (6)	0.3549 (3)	0.0581 (16)
H18A	0.4408	−0.1507	0.3899	0.087*
H18B	0.4502	0.0107	0.3775	0.087*
H18C	0.4506	−0.1040	0.3236	0.087*
C19	0.4474 (2)	0.2438 (6)	0.1963 (2)	0.0502 (13)
H19A	0.4657	0.3368	0.2117	0.075*
H19B	0.4620	0.2080	0.1628	0.075*
H19C	0.4617	0.1808	0.2361	0.075*
C20	0.3753 (3)	0.4851 (6)	0.0911 (3)	0.0444 (14)
C21	0.3464 (3)	0.5675 (6)	0.0220 (3)	0.0680 (17)
H21A	0.3115	0.6276	0.0206	0.102*
H21B	0.3295	0.5018	−0.0168	0.102*
H21C	0.3801	0.6250	0.0186	0.102*
C22	0.1278 (3)	0.4831 (6)	0.2246 (3)	0.0532 (15)
H22A	0.1032	0.5407	0.2432	0.064*
H22B	0.1719	0.4717	0.2618	0.064*
C23	0.1321 (3)	0.5635 (6)	0.1638 (2)	0.0561 (15)
H23A	0.0881	0.5850	0.1282	0.067*
H23B	0.1552	0.6527	0.1809	0.067*
C24	0.1677 (3)	0.4756 (6)	0.1320 (2)	0.0452 (13)
C25	0.1539 (3)	0.3231 (6)	0.1271 (2)	0.0520 (15)
H25	0.1703	0.2670	0.1020	0.062*
C26	0.1188 (2)	0.2590 (7)	0.1567 (2)	0.0441 (12)
C27	0.1013 (3)	0.1036 (6)	0.1440 (3)	0.0594 (16)
H27A	0.1221	0.0637	0.1161	0.071*
H27B	0.0541	0.0945	0.1169	0.071*
C28	0.1230 (3)	0.0169 (6)	0.2130 (3)	0.0525 (16)
H28A	0.1057	−0.0792	0.2020	0.063*
H28B	0.1706	0.0109	0.2362	0.063*
C29	0.0985 (2)	0.0858 (5)	0.2621 (2)	0.0413 (13)
H29	0.0505	0.0786	0.2410	0.050*
C30	0.1179 (2)	0.2443 (6)	0.2744 (2)	0.0408 (12)
H30	0.1661	0.2464	0.2965	0.049*
C31	0.0955 (3)	0.3363 (6)	0.2056 (2)	0.0437 (14)
C32	0.0968 (3)	0.3122 (6)	0.3280 (2)	0.0558 (16)
H32A	0.0492	0.3159	0.3076	0.067*
H32B	0.1131	0.4092	0.3373	0.067*
C33	0.1225 (3)	0.2296 (5)	0.3985 (2)	0.0551 (15)
H33A	0.1701	0.2368	0.4224	0.066*
H33B	0.1048	0.2720	0.4286	0.066*
C34	0.1027 (2)	0.0732 (5)	0.3863 (2)	0.0448 (13)
C35	0.1386 (2)	−0.0297 (6)	0.4496 (2)	0.0454 (13)
C36	0.1337 (3)	−0.1766 (6)	0.4155 (3)	0.0559 (15)
H36	0.1774	−0.2205	0.4373	0.067*
C37	0.1162 (3)	−0.1515 (6)	0.3363 (2)	0.0518 (14)
H37A	0.1450	−0.2052	0.3220	0.062*
H37B	0.0709	−0.1774	0.3065	0.062*
C38	0.1269 (2)	0.0090 (5)	0.3337 (2)	0.0418 (13)
H38	0.1746	0.0237	0.3545	0.050*
C39	0.0200 (3)	0.3511 (6)	0.1674 (3)	0.0614 (16)
H39A	0.0080	0.4050	0.1249	0.092*
H39B	0.0045	0.3994	0.1976	0.092*
H39C	0.0004	0.2583	0.1561	0.092*
C40	0.0263 (2)	0.0573 (7)	0.3583 (3)	0.0608 (16)
H40A	0.0116	0.1137	0.3867	0.091*
H40B	0.0156	−0.0408	0.3607	0.091*
H40C	0.0050	0.0894	0.3103	0.091*
C41	0.1186 (3)	−0.0197 (7)	0.5123 (3)	0.0639 (17)
C42	0.1534 (4)	−0.1208 (7)	0.5732 (3)	0.109 (3)
H42A	0.1837	−0.0684	0.6133	0.163*
H42B	0.1769	−0.1910	0.5600	0.163*
H42C	0.1215	−0.1672	0.5850	0.163*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0707 (4)	0.0954 (5)	0.0834 (4)	−0.0043 (4)	0.0609 (4)	−0.0067 (4)
Br2	0.1102 (6)	0.0655 (5)	0.0911 (5)	−0.0367 (4)	0.0319 (4)	0.0002 (4)
O1	0.054 (3)	0.084 (3)	0.084 (3)	0.005 (2)	0.038 (2)	0.035 (3)
O2	0.080 (3)	0.051 (3)	0.052 (2)	−0.019 (2)	0.012 (2)	0.000 (2)
O3	0.035 (2)	0.060 (3)	0.0365 (18)	0.0079 (18)	0.0140 (16)	0.0032 (17)
O4	0.063 (3)	0.072 (3)	0.063 (2)	0.005 (2)	0.042 (2)	0.009 (2)
O5	0.091 (4)	0.111 (4)	0.081 (3)	−0.004 (3)	0.058 (3)	−0.004 (3)
O6	0.057 (3)	0.060 (3)	0.048 (2)	−0.0077 (19)	0.015 (2)	−0.0104 (19)
C1	0.060 (4)	0.048 (4)	0.044 (3)	0.005 (3)	0.028 (3)	0.009 (3)
C2	0.069 (4)	0.076 (5)	0.056 (4)	0.017 (4)	0.042 (3)	0.019 (3)
C3	0.048 (3)	0.060 (4)	0.061 (3)	0.006 (3)	0.023 (3)	0.021 (4)
C4	0.058 (4)	0.056 (4)	0.048 (3)	−0.011 (3)	0.019 (3)	0.008 (3)
C5	0.047 (3)	0.032 (3)	0.043 (3)	−0.001 (3)	0.014 (3)	0.001 (2)
C6	0.086 (4)	0.031 (3)	0.065 (3)	−0.001 (3)	0.044 (3)	−0.006 (3)
C7	0.086 (4)	0.031 (3)	0.061 (3)	−0.006 (3)	0.044 (3)	−0.016 (3)
C8	0.045 (3)	0.035 (3)	0.038 (3)	0.006 (3)	0.020 (3)	0.002 (3)
C9	0.040 (3)	0.038 (3)	0.030 (3)	−0.001 (2)	0.017 (2)	−0.006 (2)
C10	0.036 (3)	0.041 (3)	0.033 (3)	0.001 (2)	0.017 (3)	0.004 (2)
C11	0.069 (4)	0.046 (3)	0.032 (2)	0.007 (3)	0.027 (3)	0.003 (3)
C12	0.067 (4)	0.026 (3)	0.032 (3)	−0.001 (2)	0.025 (3)	−0.005 (2)
C13	0.036 (3)	0.037 (3)	0.026 (2)	0.004 (3)	0.010 (2)	0.003 (3)
C14	0.026 (3)	0.048 (3)	0.036 (3)	−0.001 (2)	0.012 (2)	−0.004 (2)
C15	0.036 (3)	0.052 (4)	0.032 (2)	−0.005 (3)	0.016 (2)	−0.003 (2)
C16	0.051 (4)	0.041 (4)	0.039 (3)	0.001 (3)	0.021 (3)	−0.009 (3)
C17	0.036 (3)	0.045 (3)	0.030 (3)	0.005 (3)	0.018 (2)	−0.005 (2)
C18	0.050 (4)	0.057 (4)	0.057 (3)	0.004 (3)	0.013 (3)	0.010 (3)
C19	0.040 (3)	0.053 (4)	0.046 (3)	−0.002 (3)	0.008 (2)	−0.003 (3)
C20	0.044 (4)	0.053 (4)	0.040 (3)	0.013 (3)	0.022 (3)	0.007 (3)
C21	0.083 (5)	0.063 (4)	0.055 (3)	−0.006 (3)	0.027 (3)	0.008 (3)
C22	0.063 (4)	0.048 (4)	0.059 (3)	0.002 (3)	0.036 (3)	−0.008 (3)
C23	0.063 (4)	0.057 (4)	0.058 (3)	0.008 (3)	0.035 (3)	0.002 (3)
C24	0.046 (4)	0.053 (4)	0.040 (3)	0.007 (3)	0.022 (3)	−0.001 (3)
C25	0.062 (4)	0.061 (4)	0.044 (3)	0.007 (3)	0.033 (3)	−0.006 (3)
C26	0.046 (3)	0.048 (3)	0.039 (3)	0.006 (3)	0.018 (2)	−0.011 (3)
C27	0.064 (4)	0.067 (5)	0.050 (3)	0.001 (3)	0.027 (3)	−0.013 (3)
C28	0.067 (4)	0.043 (4)	0.046 (3)	−0.003 (3)	0.023 (3)	−0.016 (3)
C29	0.042 (3)	0.041 (3)	0.042 (3)	0.003 (3)	0.018 (3)	−0.008 (3)
C30	0.045 (3)	0.042 (3)	0.041 (3)	0.008 (3)	0.024 (2)	−0.002 (3)
C31	0.048 (4)	0.043 (4)	0.044 (3)	0.005 (3)	0.024 (3)	−0.005 (3)
C32	0.083 (4)	0.044 (4)	0.057 (3)	0.004 (3)	0.045 (3)	−0.006 (3)
C33	0.080 (4)	0.045 (4)	0.056 (3)	0.002 (3)	0.044 (3)	−0.005 (3)
C34	0.049 (4)	0.043 (4)	0.044 (3)	0.003 (3)	0.022 (3)	−0.002 (3)
C35	0.037 (3)	0.046 (4)	0.050 (3)	−0.010 (3)	0.015 (3)	−0.008 (3)
C36	0.046 (4)	0.049 (4)	0.060 (3)	−0.003 (3)	0.010 (3)	0.004 (3)
C37	0.054 (4)	0.038 (3)	0.053 (3)	−0.002 (3)	0.013 (3)	−0.006 (3)
C38	0.031 (3)	0.048 (4)	0.043 (3)	0.002 (2)	0.013 (3)	−0.006 (3)
C39	0.051 (4)	0.069 (4)	0.069 (4)	0.019 (3)	0.030 (3)	0.021 (3)
C40	0.042 (4)	0.080 (5)	0.064 (3)	0.007 (3)	0.026 (3)	0.010 (3)
C41	0.078 (5)	0.058 (4)	0.066 (4)	−0.019 (4)	0.042 (4)	−0.007 (4)
C42	0.191 (8)	0.070 (6)	0.058 (4)	−0.016 (5)	0.047 (5)	0.015 (4)

Geometric parameters (Å, º) top

Br1—C15	1.984 (4)	C19—H19C	0.9600
Br2—C36	1.976 (5)	C20—C21	1.523 (7)
O1—C3	1.231 (6)	C21—H21A	0.9600
O2—C20	1.204 (5)	C21—H21B	0.9600
O3—C14	1.463 (5)	C21—H21C	0.9600
O3—H3	0.8200	C22—C23	1.524 (7)
O4—C24	1.231 (6)	C22—C31	1.530 (7)
O5—C41	1.206 (7)	C22—H22A	0.9700
O6—C35	1.456 (5)	C22—H22B	0.9700
O6—H6	0.8200	C23—C24	1.498 (7)
C1—C2	1.540 (7)	C23—H23A	0.9700
C1—C10	1.547 (6)	C23—H23B	0.9700
C1—H1A	0.9700	C24—C25	1.460 (7)
C1—H1B	0.9700	C25—C26	1.344 (6)
C2—C3	1.480 (8)	C25—H25	0.9300
C2—H2A	0.9700	C26—C27	1.505 (7)
C2—H2B	0.9700	C26—C31	1.528 (6)
C3—C4	1.464 (6)	C27—C28	1.549 (7)
C4—C5	1.333 (6)	C27—H27A	0.9700
C4—H4	0.9300	C27—H27B	0.9700
C5—C10	1.510 (6)	C28—C29	1.513 (6)
C5—C6	1.522 (6)	C28—H28A	0.9700
C6—C7	1.509 (7)	C28—H28B	0.9700
C6—H6A	0.9700	C29—C38	1.538 (6)
C6—H6B	0.9700	C29—C30	1.542 (7)
C7—C8	1.524 (7)	C29—H29	0.9800
C7—H7A	0.9700	C30—C32	1.540 (6)
C7—H7B	0.9700	C30—C31	1.570 (6)
C8—C17	1.516 (6)	C30—H30	0.9800
C8—C9	1.561 (6)	C31—C39	1.543 (7)
C8—H8	0.9800	C32—C33	1.548 (6)
C9—C11	1.532 (7)	C32—H32A	0.9700
C9—C10	1.569 (6)	C32—H32B	0.9700
C9—H9	0.9800	C33—C34	1.525 (7)
C10—C18	1.554 (7)	C33—H33A	0.9700
C11—C12	1.539 (6)	C33—H33B	0.9700
C11—H11A	0.9700	C34—C38	1.554 (6)
C11—H11B	0.9700	C34—C35	1.560 (7)
C12—C13	1.542 (5)	C34—C40	1.568 (7)
C12—H12A	0.9700	C35—C36	1.537 (7)
C12—H12B	0.9700	C35—C41	1.571 (7)
C13—C17	1.540 (7)	C36—C37	1.554 (6)
C13—C14	1.557 (6)	C36—H36	0.9800
C13—C19	1.561 (6)	C37—C38	1.531 (7)
C14—C20	1.544 (7)	C37—H37A	0.9700
C14—C15	1.559 (6)	C37—H37B	0.9700
C15—C16	1.546 (7)	C38—H38	0.9800
C15—H15	0.9800	C39—H39A	0.9600
C16—C17	1.543 (6)	C39—H39B	0.9600
C16—H16A	0.9700	C39—H39C	0.9600
C16—H16B	0.9700	C40—H40A	0.9600
C17—H17	0.9800	C40—H40B	0.9600
C18—H18A	0.9600	C40—H40C	0.9600
C18—H18B	0.9600	C41—C42	1.514 (9)
C18—H18C	0.9600	C42—H42A	0.9600
C19—H19A	0.9600	C42—H42B	0.9600
C19—H19B	0.9600	C42—H42C	0.9600

C14—O3—H3	109.5	H21B—C21—H21C	109.5
C35—O6—H6	109.5	C23—C22—C31	115.1 (4)
C2—C1—C10	113.2 (4)	C23—C22—H22A	108.5
C2—C1—H1A	108.9	C31—C22—H22A	108.5
C10—C1—H1A	108.9	C23—C22—H22B	108.5
C2—C1—H1B	108.9	C31—C22—H22B	108.5
C10—C1—H1B	108.9	H22A—C22—H22B	107.5
H1A—C1—H1B	107.8	C24—C23—C22	110.1 (4)
C3—C2—C1	112.2 (4)	C24—C23—H23A	109.6
C3—C2—H2A	109.2	C22—C23—H23A	109.6
C1—C2—H2A	109.2	C24—C23—H23B	109.6
C3—C2—H2B	109.2	C22—C23—H23B	109.6
C1—C2—H2B	109.2	H23A—C23—H23B	108.2
H2A—C2—H2B	107.9	O4—C24—C25	122.3 (5)
O1—C3—C4	121.0 (6)	O4—C24—C23	122.1 (5)
O1—C3—C2	122.7 (5)	C25—C24—C23	115.7 (5)
C4—C3—C2	116.2 (5)	C26—C25—C24	123.9 (5)
C5—C4—C3	124.0 (5)	C26—C25—H25	118.1
C5—C4—H4	118.0	C24—C25—H25	118.1
C3—C4—H4	118.0	C25—C26—C27	120.8 (4)
C4—C5—C10	123.4 (4)	C25—C26—C31	123.0 (5)
C4—C5—C6	119.5 (5)	C27—C26—C31	116.2 (4)
C10—C5—C6	117.1 (4)	C26—C27—C28	113.0 (4)
C7—C6—C5	111.4 (4)	C26—C27—H27A	109.0
C7—C6—H6A	109.4	C28—C27—H27A	109.0
C5—C6—H6A	109.4	C26—C27—H27B	109.0
C7—C6—H6B	109.4	C28—C27—H27B	109.0
C5—C6—H6B	109.4	H27A—C27—H27B	107.8
H6A—C6—H6B	108.0	C29—C28—C27	110.8 (5)
C6—C7—C8	113.4 (4)	C29—C28—H28A	109.5
C6—C7—H7A	108.9	C27—C28—H28A	109.5
C8—C7—H7A	108.9	C29—C28—H28B	109.5
C6—C7—H7B	108.9	C27—C28—H28B	109.5
C8—C7—H7B	108.9	H28A—C28—H28B	108.1
H7A—C7—H7B	107.7	C28—C29—C38	110.4 (4)
C17—C8—C7	113.8 (4)	C28—C29—C30	111.5 (4)
C17—C8—C9	108.9 (4)	C38—C29—C30	108.7 (4)
C7—C8—C9	108.7 (4)	C28—C29—H29	108.7
C17—C8—H8	108.4	C38—C29—H29	108.7
C7—C8—H8	108.4	C30—C29—H29	108.7
C9—C8—H8	108.4	C32—C30—C29	111.5 (4)
C11—C9—C8	112.6 (4)	C32—C30—C31	111.7 (4)
C11—C9—C10	113.2 (3)	C29—C30—C31	114.9 (4)
C8—C9—C10	112.4 (4)	C32—C30—H30	106.0
C11—C9—H9	106.0	C29—C30—H30	106.0
C8—C9—H9	106.0	C31—C30—H30	106.0
C10—C9—H9	106.0	C26—C31—C22	109.9 (4)
C5—C10—C1	109.8 (4)	C26—C31—C39	108.5 (4)
C5—C10—C18	108.2 (4)	C22—C31—C39	110.4 (4)
C1—C10—C18	109.5 (4)	C26—C31—C30	107.0 (4)
C5—C10—C9	109.2 (4)	C22—C31—C30	109.2 (4)
C1—C10—C9	108.2 (4)	C39—C31—C30	111.9 (4)
C18—C10—C9	111.9 (4)	C30—C32—C33	112.9 (4)
C9—C11—C12	114.6 (3)	C30—C32—H32A	109.0
C9—C11—H11A	108.6	C33—C32—H32A	109.0
C12—C11—H11A	108.6	C30—C32—H32B	109.0
C9—C11—H11B	108.6	C33—C32—H32B	109.0
C12—C11—H11B	108.6	H32A—C32—H32B	107.8
H11A—C11—H11B	107.6	C34—C33—C32	111.1 (4)
C11—C12—C13	110.4 (4)	C34—C33—H33A	109.4
C11—C12—H12A	109.6	C32—C33—H33A	109.4
C13—C12—H12A	109.6	C34—C33—H33B	109.4
C11—C12—H12B	109.6	C32—C33—H33B	109.4
C13—C12—H12B	109.6	H33A—C33—H33B	108.0
H12A—C12—H12B	108.1	C33—C34—C38	109.0 (4)
C17—C13—C12	108.2 (3)	C33—C34—C35	116.6 (4)
C17—C13—C14	100.7 (3)	C38—C34—C35	99.0 (4)
C12—C13—C14	116.8 (4)	C33—C34—C40	110.4 (4)
C17—C13—C19	110.8 (4)	C38—C34—C40	111.4 (4)
C12—C13—C19	109.7 (3)	C35—C34—C40	110.0 (4)
C14—C13—C19	110.2 (3)	O6—C35—C36	102.4 (4)
O3—C14—C20	105.7 (4)	O6—C35—C34	110.8 (4)
O3—C14—C13	111.5 (3)	C36—C35—C34	104.5 (4)
C20—C14—C13	117.8 (4)	O6—C35—C41	104.3 (4)
O3—C14—C15	101.0 (3)	C36—C35—C41	117.2 (4)
C20—C14—C15	116.8 (4)	C34—C35—C41	116.7 (4)
C13—C14—C15	102.9 (4)	C35—C36—C37	107.3 (4)
C16—C15—C14	107.1 (3)	C35—C36—Br2	116.8 (4)
C16—C15—Br1	111.4 (3)	C37—C36—Br2	109.3 (3)
C14—C15—Br1	113.6 (3)	C35—C36—H36	107.7
C16—C15—H15	108.2	C37—C36—H36	107.7
C14—C15—H15	108.2	Br2—C36—H36	107.7
Br1—C15—H15	108.2	C38—C37—C36	102.6 (4)
C17—C16—C15	103.9 (4)	C38—C37—H37A	111.2
C17—C16—H16A	111.0	C36—C37—H37A	111.2
C15—C16—H16A	111.0	C38—C37—H37B	111.2
C17—C16—H16B	111.0	C36—C37—H37B	111.2
C15—C16—H16B	111.0	H37A—C37—H37B	109.2
H16A—C16—H16B	109.0	C37—C38—C29	119.5 (4)
C8—C17—C13	115.2 (3)	C37—C38—C34	104.2 (4)
C8—C17—C16	117.8 (4)	C29—C38—C34	113.0 (4)
C13—C17—C16	103.5 (4)	C37—C38—H38	106.4
C8—C17—H17	106.5	C29—C38—H38	106.4
C13—C17—H17	106.5	C34—C38—H38	106.4
C16—C17—H17	106.5	C31—C39—H39A	109.5
C10—C18—H18A	109.5	C31—C39—H39B	109.5
C10—C18—H18B	109.5	H39A—C39—H39B	109.5
H18A—C18—H18B	109.5	C31—C39—H39C	109.5
C10—C18—H18C	109.5	H39A—C39—H39C	109.5
H18A—C18—H18C	109.5	H39B—C39—H39C	109.5
H18B—C18—H18C	109.5	C34—C40—H40A	109.5
C13—C19—H19A	109.5	C34—C40—H40B	109.5
C13—C19—H19B	109.5	H40A—C40—H40B	109.5
H19A—C19—H19B	109.5	C34—C40—H40C	109.5
C13—C19—H19C	109.5	H40A—C40—H40C	109.5
H19A—C19—H19C	109.5	H40B—C40—H40C	109.5
H19B—C19—H19C	109.5	O5—C41—C42	122.6 (6)
O2—C20—C21	120.6 (5)	O5—C41—C35	120.6 (6)
O2—C20—C14	122.8 (4)	C42—C41—C35	116.3 (6)
C21—C20—C14	116.4 (5)	C41—C42—H42A	109.5
C20—C21—H21A	109.5	C41—C42—H42B	109.5
C20—C21—H21B	109.5	H42A—C42—H42B	109.5
H21A—C21—H21B	109.5	C41—C42—H42C	109.5
C20—C21—H21C	109.5	H42A—C42—H42C	109.5
H21A—C21—H21C	109.5	H42B—C42—H42C	109.5

C10—C1—C2—C3	−53.5 (6)	C31—C22—C23—C24	−56.3 (6)
C1—C2—C3—O1	−152.0 (5)	C22—C23—C24—O4	−141.4 (5)
C1—C2—C3—C4	30.9 (7)	C22—C23—C24—C25	38.3 (6)
O1—C3—C4—C5	−178.1 (5)	O4—C24—C25—C26	171.1 (5)
C2—C3—C4—C5	−0.9 (8)	C23—C24—C25—C26	−8.6 (7)
C3—C4—C5—C10	−7.5 (8)	C24—C25—C26—C27	174.4 (5)
C3—C4—C5—C6	170.3 (5)	C24—C25—C26—C31	−6.7 (8)
C4—C5—C6—C7	132.8 (5)	C25—C26—C27—C28	125.7 (5)
C10—C5—C6—C7	−49.3 (6)	C31—C26—C27—C28	−53.3 (6)
C5—C6—C7—C8	52.6 (6)	C26—C27—C28—C29	51.9 (6)
C6—C7—C8—C17	−178.8 (4)	C27—C28—C29—C38	−173.5 (5)
C6—C7—C8—C9	−57.2 (5)	C27—C28—C29—C30	−52.5 (6)
C17—C8—C9—C11	−49.1 (5)	C28—C29—C30—C32	−176.4 (4)
C7—C8—C9—C11	−173.6 (4)	C38—C29—C30—C32	−54.5 (5)
C17—C8—C9—C10	−178.3 (4)	C28—C29—C30—C31	55.2 (5)
C7—C8—C9—C10	57.2 (5)	C38—C29—C30—C31	177.1 (4)
C4—C5—C10—C1	−14.8 (6)	C25—C26—C31—C22	−9.8 (7)
C6—C5—C10—C1	167.3 (4)	C27—C26—C31—C22	169.1 (4)
C4—C5—C10—C18	104.7 (5)	C25—C26—C31—C39	111.0 (5)
C6—C5—C10—C18	−73.2 (5)	C27—C26—C31—C39	−70.1 (6)
C4—C5—C10—C9	−133.3 (5)	C25—C26—C31—C30	−128.2 (5)
C6—C5—C10—C9	48.8 (5)	C27—C26—C31—C30	50.8 (6)
C2—C1—C10—C5	44.3 (6)	C23—C22—C31—C26	41.3 (6)
C2—C1—C10—C18	−74.5 (6)	C23—C22—C31—C39	−78.3 (5)
C2—C1—C10—C9	163.4 (4)	C23—C22—C31—C30	158.3 (4)
C11—C9—C10—C5	178.6 (4)	C32—C30—C31—C26	−179.8 (4)
C8—C9—C10—C5	−52.5 (5)	C29—C30—C31—C26	−51.5 (5)
C11—C9—C10—C1	59.1 (5)	C32—C30—C31—C22	61.3 (5)
C8—C9—C10—C1	−172.0 (4)	C29—C30—C31—C22	−170.4 (4)
C11—C9—C10—C18	−61.6 (5)	C32—C30—C31—C39	−61.2 (6)
C8—C9—C10—C18	67.3 (5)	C29—C30—C31—C39	67.2 (5)
C8—C9—C11—C12	50.3 (6)	C29—C30—C32—C33	53.9 (6)
C10—C9—C11—C12	179.1 (4)	C31—C30—C32—C33	−175.9 (4)
C9—C11—C12—C13	−53.5 (5)	C30—C32—C33—C34	−54.3 (6)
C11—C12—C13—C17	55.4 (5)	C32—C33—C34—C38	55.0 (5)
C11—C12—C13—C14	168.1 (4)	C32—C33—C34—C35	165.9 (4)
C11—C12—C13—C19	−65.7 (5)	C32—C33—C34—C40	−67.6 (5)
C17—C13—C14—O3	66.8 (4)	C33—C34—C35—O6	−45.9 (5)
C12—C13—C14—O3	−50.1 (5)	C38—C34—C35—O6	70.7 (5)
C19—C13—C14—O3	−176.1 (4)	C40—C34—C35—O6	−172.6 (4)
C17—C13—C14—C20	−170.8 (4)	C33—C34—C35—C36	−155.5 (4)
C12—C13—C14—C20	72.3 (5)	C38—C34—C35—C36	−38.9 (5)
C19—C13—C14—C20	−53.7 (5)	C40—C34—C35—C36	77.8 (5)
C17—C13—C14—C15	−40.7 (4)	C33—C34—C35—C41	73.3 (6)
C12—C13—C14—C15	−157.6 (4)	C38—C34—C35—C41	−170.1 (4)
C19—C13—C14—C15	76.4 (5)	C40—C34—C35—C41	−53.4 (6)
O3—C14—C15—C16	−94.9 (4)	O6—C35—C36—C37	−98.2 (4)
C20—C14—C15—C16	151.1 (4)	C34—C35—C36—C37	17.4 (5)
C13—C14—C15—C16	20.4 (4)	C41—C35—C36—C37	148.3 (5)
O3—C14—C15—Br1	141.6 (3)	O6—C35—C36—Br2	138.7 (3)
C20—C14—C15—Br1	27.6 (5)	C34—C35—C36—Br2	−105.7 (4)
C13—C14—C15—Br1	−103.1 (3)	C41—C35—C36—Br2	25.2 (6)
C14—C15—C16—C17	8.0 (5)	C35—C36—C37—C38	11.9 (5)
Br1—C15—C16—C17	132.8 (3)	Br2—C36—C37—C38	139.5 (4)
C7—C8—C17—C13	177.6 (4)	C36—C37—C38—C29	−164.4 (4)
C9—C8—C17—C13	56.1 (5)	C36—C37—C38—C34	−37.2 (5)
C7—C8—C17—C16	−59.6 (6)	C28—C29—C38—C37	−55.9 (6)
C9—C8—C17—C16	178.9 (4)	C30—C29—C38—C37	−178.6 (4)
C12—C13—C17—C8	−60.1 (5)	C28—C29—C38—C34	−179.0 (4)
C14—C13—C17—C8	176.8 (4)	C30—C29—C38—C34	58.3 (5)
C19—C13—C17—C8	60.2 (5)	C33—C34—C38—C37	169.7 (4)
C12—C13—C17—C16	169.8 (4)	C35—C34—C38—C37	47.4 (5)
C14—C13—C17—C16	46.7 (4)	C40—C34—C38—C37	−68.2 (5)
C19—C13—C17—C16	−69.9 (4)	C33—C34—C38—C29	−59.1 (6)
C15—C16—C17—C8	−162.5 (4)	C35—C34—C38—C29	178.7 (4)
C15—C16—C17—C13	−33.9 (5)	C40—C34—C38—C29	63.0 (5)
O3—C14—C20—O2	125.3 (5)	O6—C35—C41—O5	114.6 (6)
C13—C14—C20—O2	−0.1 (7)	C36—C35—C41—O5	−133.1 (6)
C15—C14—C20—O2	−123.4 (5)	C34—C35—C41—O5	−8.0 (8)
O3—C14—C20—C21	−50.1 (5)	O6—C35—C41—C42	−57.9 (6)
C13—C14—C20—C21	−175.5 (4)	C36—C35—C41—C42	54.5 (7)
C15—C14—C20—C21	61.2 (6)	C34—C35—C41—C42	179.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O1ⁱ	0.82	2.04	2.836 (5)	163
O3—H3···O4	0.82	2.02	2.798 (5)	158

Symmetry code: (i) −x+1/2, y+1/2, −z+1.

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