9α-Bromo-11β-hydroxy­pregna-1,4,16-triene-3,20-dione

The 3-one ring of the title compound, C₂₁H₂₅BrO₃, is almost planar. Pairs of mol­ecules are connected by O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.024
• wR factor = 0.051
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



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           27.48
           From the CIF: _reflns_number_total               4156
           Count of symmetry unique reflns         2394
           Completeness (_total/calc)            173.60%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1762
           Fraction of Friedel pairs measured     0.736
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          S

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

   6 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

9α-Bromo-11β-hydroxypregna-1,4,16-triene-3,20-dione

Crystal data

C21H25BrO3	F(000) = 840.00
Mr = 405.33	Dx = 1.480 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 16127 reflections
a = 8.255 (2) Å	θ = 3.1–27.5°
b = 10.438 (2) Å	µ = 2.28 mm^−1
c = 21.110 (6) Å	T = 298 K
V = 1819.0 (8) Å^3	Chunk, colorless
Z = 4	0.38 × 0.33 × 0.24 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	3557 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.031
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR: Higashi, 1995)	h = −10→10
Tmin = 0.398, Tmax = 0.578	k = −13→13
17983 measured reflections	l = −27→27
4156 independent reflections

Refinement

Refinement on F^2	(Δ/σ)max < 0.001
R[F^2 > 2σ(F^2)] = 0.024	Δρmax = 0.55 e Å^−3
wR(F^2) = 0.051	Δρmin = −0.40 e Å^−3
S = 1.00	Extinction correction: Larson (1970), equation 22
4156 reflections	Extinction coefficient: 189 (13)
228 parameters	Absolute structure: Flack (1983), 1767 Friedel Pairs
H-atom parameters constrained	Absolute structure parameter: −0.004 (6)
w = 1/[0.5700σ(Fo^2)]/(4Fo^2)

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Br1	0.41025 (3)	0.73795 (2)	0.600290 (10)	0.04109 (5)
O1	0.1757 (2)	0.79117 (13)	0.80947 (6)	0.0571 (5)
O2	0.54909 (18)	0.36593 (12)	0.62190 (6)	0.0451 (4)
O3	0.8209 (2)	0.42879 (17)	0.41433 (8)	0.0634 (5)
C1	0.3964 (2)	0.55799 (18)	0.72360 (9)	0.0394 (5)
C2	0.3600 (2)	0.6401 (2)	0.76950 (10)	0.0432 (6)
C3	0.2091 (2)	0.71067 (18)	0.76862 (10)	0.0406 (6)
C4	0.0980 (2)	0.68286 (18)	0.71690 (9)	0.0385 (5)
C5	0.1316 (2)	0.60000 (17)	0.67021 (9)	0.0336 (5)
C6	0.0164 (2)	0.5723 (2)	0.61692 (10)	0.0417 (6)
C7	0.0978 (2)	0.57982 (19)	0.55165 (9)	0.0399 (5)
C8	0.2615 (2)	0.51021 (18)	0.54920 (9)	0.0302 (5)
C9	0.3741 (2)	0.54715 (13)	0.60445 (9)	0.0277 (4)
C10	0.2875 (2)	0.52429 (17)	0.66992 (9)	0.0309 (5)
C11	0.5491 (2)	0.49392 (17)	0.59867 (10)	0.0340 (5)
C12	0.6219 (2)	0.50117 (18)	0.53186 (9)	0.0344 (5)
C13	0.5063 (2)	0.45353 (17)	0.48048 (9)	0.0318 (5)
C14	0.3488 (2)	0.53117 (19)	0.48684 (9)	0.0317 (5)
C15	0.2625 (2)	0.5112 (2)	0.42315 (10)	0.0472 (6)
C16	0.4084 (2)	0.50830 (19)	0.38019 (9)	0.0440 (5)
C17	0.5446 (2)	0.48119 (17)	0.41135 (10)	0.0359 (5)
C18	0.4798 (2)	0.30707 (18)	0.48454 (10)	0.0431 (6)
C19	0.2393 (2)	0.38032 (18)	0.68074 (11)	0.0457 (6)
C20	0.7062 (2)	0.46202 (18)	0.38278 (11)	0.0417 (6)
C21	0.7249 (3)	0.4847 (2)	0.31281 (11)	0.0565 (7)
H1	0.4974	0.5186	0.7251	0.047*
H2	0.4325	0.6525	0.8027	0.052*
H4	−0.0014	0.7247	0.7162	0.046*
H8	0.2395	0.4183	0.5528	0.036*
H11	0.6184	0.5448	0.6268	0.041*
H14	0.3823	0.6212	0.4871	0.038*
H16	0.4038	0.5237	0.3368	0.053*
H61	−0.0271	0.4867	0.6226	0.050*
H62	−0.0711	0.6342	0.6184	0.050*
H71	0.1151	0.6693	0.5412	0.048*
H72	0.0261	0.5414	0.5206	0.048*
H121	0.7192	0.4492	0.5308	0.041*
H122	0.6495	0.5896	0.5229	0.041*
H151	0.2027	0.4313	0.4220	0.057*
H152	0.1902	0.5816	0.4131	0.057*
H181	0.4352	0.2857	0.5252	0.052*
H182	0.4063	0.2807	0.4518	0.052*
H183	0.5816	0.2639	0.4791	0.052*
H191	0.1803	0.3726	0.7197	0.055*
H192	0.1727	0.3516	0.6463	0.055*
H193	0.3354	0.3288	0.6828	0.055*
H201	0.6541	0.3408	0.6351	0.055*
H211	0.6519	0.5512	0.2997	0.068*
H212	0.7005	0.4073	0.2902	0.068*
H213	0.8343	0.5102	0.3039	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.04715 (12)	0.02859 (9)	0.04754 (12)	−0.00685 (8)	0.00604 (11)	−0.00107 (9)
O1	0.0565 (10)	0.0633 (9)	0.0516 (10)	0.0027 (7)	−0.0034 (8)	−0.0265 (8)
O2	0.0425 (9)	0.0429 (7)	0.0500 (9)	0.0088 (6)	−0.0039 (7)	0.0143 (6)
O3	0.0472 (10)	0.0856 (11)	0.0573 (12)	0.0213 (9)	0.0110 (8)	0.0100 (8)
C1	0.0340 (11)	0.0490 (10)	0.0352 (11)	0.0020 (10)	−0.0054 (10)	0.0015 (8)
C2	0.0384 (13)	0.0574 (12)	0.0338 (12)	−0.0056 (9)	−0.0024 (9)	−0.0044 (10)
C3	0.0425 (13)	0.0431 (11)	0.0362 (11)	−0.0064 (9)	0.0052 (9)	−0.0042 (9)
C4	0.0304 (11)	0.0459 (10)	0.0390 (11)	0.0019 (9)	0.0050 (10)	−0.0027 (8)
C5	0.0304 (11)	0.0374 (9)	0.0332 (11)	−0.0053 (7)	0.0018 (8)	0.0027 (8)
C6	0.0270 (10)	0.0585 (12)	0.0396 (13)	−0.0008 (9)	−0.0015 (9)	−0.0067 (9)
C7	0.0278 (10)	0.0568 (11)	0.0350 (11)	0.0066 (10)	−0.0065 (10)	−0.0044 (8)
C8	0.0276 (10)	0.0346 (9)	0.0285 (10)	−0.0020 (7)	−0.0029 (8)	−0.0020 (7)
C9	0.0273 (9)	0.0240 (7)	0.0319 (10)	−0.0031 (5)	0.0002 (8)	0.0005 (7)
C10	0.0316 (11)	0.0324 (9)	0.0287 (10)	−0.0014 (8)	−0.0008 (8)	−0.0012 (7)
C11	0.0290 (10)	0.0371 (9)	0.0360 (10)	−0.0008 (7)	−0.0038 (9)	0.0024 (9)
C12	0.0277 (11)	0.0358 (9)	0.0398 (11)	0.0012 (8)	0.0009 (9)	0.0020 (8)
C13	0.0289 (10)	0.0333 (9)	0.0333 (11)	0.0026 (7)	0.0008 (8)	0.0019 (8)
C14	0.0289 (10)	0.0367 (10)	0.0295 (11)	0.0026 (7)	−0.0011 (8)	−0.0004 (8)
C15	0.0393 (13)	0.0661 (14)	0.0360 (12)	0.0099 (10)	−0.0051 (10)	−0.0011 (10)
C16	0.0510 (13)	0.0530 (11)	0.0280 (10)	0.0069 (11)	0.0009 (11)	−0.0011 (8)
C17	0.0404 (12)	0.0333 (9)	0.0340 (12)	0.0036 (7)	0.0069 (9)	0.0012 (8)
C18	0.0471 (13)	0.0368 (10)	0.0456 (13)	0.0015 (9)	0.0024 (10)	−0.0016 (9)
C19	0.0473 (13)	0.0429 (11)	0.0471 (13)	−0.0057 (9)	0.0105 (11)	0.0092 (9)
C20	0.0472 (13)	0.0320 (9)	0.0459 (13)	0.0049 (9)	0.0100 (11)	0.0007 (8)
C21	0.0559 (16)	0.0621 (14)	0.0517 (15)	0.0061 (12)	0.0224 (13)	−0.0015 (11)

Geometric parameters (Å, º)

Br1—C9	2.0158 (14)	C20—C21	1.504 (3)
O1—C3	1.235 (2)	O2—H201	0.947
O2—C11	1.423 (2)	C1—H1	0.930
O3—C20	1.209 (2)	C2—H2	0.930
C1—C2	1.328 (2)	C4—H4	0.930
C1—C10	1.489 (2)	C6—H61	0.970
C2—C3	1.447 (3)	C6—H62	0.970
C3—C4	1.455 (2)	C7—H71	0.970
C4—C5	1.340 (2)	C7—H72	0.970
C5—C6	1.501 (2)	C8—H8	0.980
C5—C10	1.510 (2)	C11—H11	0.980
C6—C7	1.535 (2)	C12—H121	0.970
C7—C8	1.535 (2)	C12—H122	0.970
C8—C9	1.541 (2)	C14—H14	0.980
C8—C14	1.517 (2)	C15—H151	0.970
C9—C10	1.574 (2)	C15—H152	0.970
C9—C11	1.553 (2)	C16—H16	0.930
C10—C19	1.571 (2)	C18—H181	0.960
C11—C12	1.535 (2)	C18—H182	0.960
C12—C13	1.528 (2)	C18—H183	0.960
C13—C14	1.539 (2)	C19—H191	0.960
C13—C17	1.521 (2)	C19—H192	0.960
C13—C18	1.547 (2)	C19—H193	0.960
C14—C15	1.536 (2)	C21—H211	0.960
C15—C16	1.508 (3)	C21—H212	0.960
C16—C17	1.333 (3)	C21—H213	0.960
C17—C20	1.477 (3)
Br1···O3	3.5694 (17)	H16···H4	2.960
Br1···C20	3.574 (2)	H16···H191	2.786
O1···O2	2.806 (2)	H61···O1	2.780
O1···C16	3.533 (2)	H61···C11	3.535
O1···C19	3.556 (2)	H61···C12	3.477
O1···C21	3.507 (2)	H61···H11	2.990
O2···O1	2.806 (2)	H61···H121	2.880
O2···C2	3.372 (2)	H61···H122	3.565
O2···C3	3.457 (2)	H61···H182	3.250
O3···Br1	3.5694 (17)	H61···H183	3.501
O3···C18	3.513 (2)	H61···H201	3.052
C2···O2	3.372 (2)	H62···C11	3.485
C2···C16	3.573 (3)	H62···C12	3.418
C3···O2	3.457 (2)	H62···H11	2.734
C3···C16	3.422 (2)	H62···H14	3.410
C16···O1	3.533 (2)	H62···H121	3.185
C16···C2	3.573 (3)	H62···H122	3.098
C16···C3	3.422 (2)	H71···Br1	3.566
C18···O3	3.513 (2)	H71···H14	2.972
C19···O1	3.556 (2)	H71···H122	2.871
C20···Br1	3.5741 (19)	H72···Br1	3.568
C21···O1	3.507 (2)	H72···O3	3.047
Br1···H71	3.566	H72···C12	3.372
Br1···H72	3.568	H72···H121	2.719
Br1···H152	2.995	H72···H122	3.150
Br1···H213	3.376	H72···H182	3.553
O1···H11	3.423	H72···H183	3.220
O1···H16	3.401	H121···C6	3.313
O1···H61	2.780	H121···C7	3.438
O1···H151	3.471	H121···C18	3.448
O1···H182	3.170	H121···H61	2.880
O1···H191	3.120	H121···H62	3.185
O1···H192	3.089	H121···H72	2.719
O1···H201	1.901	H121···H181	3.253
O1···H211	2.838	H121···H182	2.877
O1···H213	3.426	H122···H14	3.584
O2···H2	2.743	H122···H61	3.565
O2···H151	3.477	H122···H62	3.098
O3···H2	3.228	H122···H71	2.871
O3···H72	3.047	H122···H72	3.150
O3···H151	3.156	H151···O1	3.471
O3···H152	3.441	H151···O2	3.477
O3···H181	2.745	H151···O3	3.156
O3···H192	3.420	H151···C2	3.345
O3···H193	3.384	H151···H2	2.891
C1···H16	3.547	H151···H181	3.354
C1···H213	2.885	H151···H183	3.083
C2···H16	3.112	H151···H201	3.111
C2···H151	3.345	H152···Br1	2.995
C2···H193	3.348	H152···O3	3.441
C2···H201	2.908	H152···H2	3.526
C2···H213	3.060	H181···O3	2.745
C3···H16	2.988	H181···H121	3.253
C3···H201	2.694	H181···H151	3.354
C3···H211	2.912	H181···H183	2.966
C3···H213	3.449	H182···O1	3.170
C4···H16	3.325	H182···H8	3.448
C4···H191	3.315	H182···H61	3.250
C4···H211	2.833	H182···H72	3.553
C4···H212	3.058	H182···H121	2.877
C6···H11	3.305	H182···H183	3.086
C6···H121	3.313	H182···H192	3.321
C7···H121	3.438	H182···H201	3.051
C8···H183	3.279	H183···C8	3.279
C11···H61	3.535	H183···C18	3.456
C11···H62	3.485	H183···H8	2.402
C12···H61	3.477	H183···H61	3.501
C12···H62	3.418	H183···H72	3.220
C12···H72	3.372	H183···H151	3.083
C15···H2	3.461	H183···H181	2.966
C16···H4	3.530	H183···H182	3.086
C18···H8	3.278	H183···H192	3.005
C18···H121	3.448	H191···O1	3.120
C18···H183	3.456	H191···C4	3.315
C18···H192	3.592	H191···H4	2.528
C19···H4	3.350	H191···H16	2.786
C19···H212	3.081	H191···H211	3.316
C20···H192	3.342	H191···H212	2.934
C20···H193	3.503	H192···O1	3.089
C21···H1	2.947	H192···O3	3.420
C21···H2	3.178	H192···C18	3.592
C21···H4	3.513	H192···C20	3.342
C21···H193	3.399	H192···H4	3.490
H1···C21	2.947	H192···H182	3.321
H1···H211	3.375	H192···H183	3.005
H1···H212	2.951	H192···H212	3.025
H1···H213	2.188	H193···O3	3.384
H2···O2	2.743	H193···C2	3.348
H2···O3	3.228	H193···C20	3.503
H2···C15	3.461	H193···C21	3.399
H2···C21	3.178	H193···H2	2.674
H2···H16	3.407	H193···H212	2.763
H2···H151	2.891	H193···H213	3.550
H2···H152	3.526	H201···O1	1.901
H2···H193	2.674	H201···C2	2.908
H2···H201	2.470	H201···C3	2.694
H2···H212	3.104	H201···H2	2.470
H2···H213	2.568	H201···H61	3.052
H4···C16	3.530	H201···H151	3.111
H4···C19	3.350	H201···H182	3.051
H4···C21	3.513	H211···O1	2.838
H4···H16	2.960	H211···C3	2.912
H4···H191	2.528	H211···C4	2.833
H4···H192	3.490	H211···H1	3.375
H4···H211	2.680	H211···H4	2.680
H4···H211	3.598	H211···H4	3.598
H4···H212	2.653	H211···H191	3.316
H8···C18	3.278	H212···C4	3.058
H8···H182	3.448	H212···C19	3.081
H8···H183	2.402	H212···H1	2.951
H11···O1	3.423	H212···H2	3.104
H11···C6	3.305	H212···H4	2.653
H11···H61	2.990	H212···H191	2.934
H11···H62	2.734	H212···H192	3.025
H14···H62	3.410	H212···H193	2.763
H14···H71	2.972	H213···Br1	3.376
H14···H122	3.584	H213···O1	3.426
H16···O1	3.401	H213···C1	2.885
H16···C1	3.547	H213···C2	3.060
H16···C2	3.112	H213···C3	3.449
H16···C3	2.988	H213···H1	2.188
H16···C4	3.325	H213···H2	2.568
H16···H2	3.407	H213···H193	3.550
C2—C1—C10	124.8 (2)	C3—C4—H4	118.3
C1—C2—C3	120.9 (2)	C5—C4—H4	118.3
O1—C3—C2	121.96 (19)	C5—C6—H61	108.7
O1—C3—C4	121.25 (19)	C5—C6—H62	108.7
C2—C3—C4	116.79 (17)	C7—C6—H61	108.7
C3—C4—C5	123.38 (19)	C7—C6—H62	108.7
C4—C5—C6	123.01 (18)	H61—C6—H62	109.5
C4—C5—C10	121.12 (17)	C6—C7—H71	108.6
C6—C5—C10	115.83 (16)	C6—C7—H72	108.6
C5—C6—C7	112.70 (16)	C8—C7—H71	108.6
C6—C7—C8	113.03 (16)	C8—C7—H72	108.6
C7—C8—C9	112.78 (15)	H71—C7—H72	109.5
C7—C8—C14	112.28 (15)	C7—C8—H8	107.3
C9—C8—C14	109.53 (15)	C9—C8—H8	107.3
Br1—C9—C8	107.68 (11)	C14—C8—H8	107.3
Br1—C9—C10	104.79 (10)	O2—C11—H11	107.5
Br1—C9—C11	102.26 (10)	C9—C11—H11	107.5
C8—C9—C10	110.65 (14)	C12—C11—H11	107.5
C8—C9—C11	114.36 (15)	C11—C12—H121	108.6
C10—C9—C11	115.94 (15)	C11—C12—H122	108.6
C1—C10—C5	112.83 (15)	C13—C12—H121	108.6
C1—C10—C9	110.98 (15)	C13—C12—H122	108.6
C1—C10—C19	105.56 (15)	H121—C12—H122	109.5
C5—C10—C9	108.14 (14)	C8—C14—H14	105.5
C5—C10—C19	106.50 (16)	C13—C14—H14	105.5
C9—C10—C19	112.80 (14)	C15—C14—H14	105.5
O2—C11—C9	107.97 (14)	C14—C15—H151	112.0
O2—C11—C12	111.29 (15)	C14—C15—H152	112.0
C9—C11—C12	114.75 (15)	C16—C15—H151	112.0
C11—C12—C13	113.09 (15)	C16—C15—H152	112.0
C12—C13—C14	107.13 (14)	H151—C15—H152	109.5
C12—C13—C17	119.34 (15)	C15—C16—H16	123.8
C12—C13—C18	111.76 (15)	C17—C16—H16	123.8
C14—C13—C17	99.16 (14)	C13—C18—H181	109.5
C14—C13—C18	113.34 (15)	C13—C18—H182	109.5
C17—C13—C18	105.68 (15)	C13—C18—H183	109.5
C8—C14—C13	113.67 (15)	H181—C18—H182	109.5
C8—C14—C15	121.33 (16)	H181—C18—H183	109.5
C13—C14—C15	104.14 (15)	H182—C18—H183	109.5
C14—C15—C16	99.14 (17)	C10—C19—H191	109.5
C15—C16—C17	112.41 (17)	C10—C19—H192	109.5
C13—C17—C16	109.79 (17)	C10—C19—H193	109.5
C13—C17—C20	123.60 (17)	H191—C19—H192	109.5
C16—C17—C20	126.08 (19)	H191—C19—H193	109.5
O3—C20—C17	121.4 (2)	H192—C19—H193	109.5
O3—C20—C21	120.4 (2)	C20—C21—H211	109.5
C17—C20—C21	118.19 (19)	C20—C21—H212	109.5
C11—O2—H201	111.2	C20—C21—H213	109.5
C2—C1—H1	117.6	H211—C21—H212	109.5
C10—C1—H1	117.6	H211—C21—H213	109.5
C1—C2—H2	119.5	H212—C21—H213	109.5
C3—C2—H2	119.5
C2—C1—C10—C5	3.6 (2)	C8—C9—C10—C1	179.18 (14)
C2—C1—C10—C9	125.1 (2)	C8—C9—C10—C5	−56.56 (17)
C2—C1—C10—C19	−112.4 (2)	C8—C9—C10—C19	60.96 (19)
C10—C1—C2—C3	−3.5 (3)	C8—C9—C11—O2	−83.27 (18)
C1—C2—C3—O1	−177.1 (2)	C8—C9—C11—C12	41.5 (2)
C1—C2—C3—C4	2.6 (2)	C10—C9—C11—O2	47.32 (19)
O1—C3—C4—C5	177.37 (19)	C10—C9—C11—C12	172.06 (14)
C2—C3—C4—C5	−2.3 (2)	C11—C9—C10—C1	46.85 (19)
C3—C4—C5—C6	−179.77 (18)	C11—C9—C10—C5	171.10 (14)
C3—C4—C5—C10	2.7 (2)	C11—C9—C10—C19	−71.4 (2)
C4—C5—C6—C7	131.0 (2)	O2—C11—C12—C13	76.27 (19)
C4—C5—C10—C1	−3.1 (2)	C9—C11—C12—C13	−46.7 (2)
C4—C5—C10—C9	−126.23 (18)	C11—C12—C13—C14	55.29 (19)
C4—C5—C10—C19	112.3 (2)	C11—C12—C13—C17	166.66 (15)
C6—C5—C10—C1	179.26 (16)	C11—C12—C13—C18	−69.4 (2)
C6—C5—C10—C9	56.1 (2)	C12—C13—C14—C8	−63.47 (19)
C6—C5—C10—C19	−65.4 (2)	C12—C13—C14—C15	162.43 (15)
C10—C5—C6—C7	−51.4 (2)	C12—C13—C17—C16	−141.51 (17)
C5—C6—C7—C8	45.8 (2)	C12—C13—C17—C20	46.4 (2)
C6—C7—C8—C9	−49.2 (2)	C14—C13—C17—C16	−25.86 (19)
C6—C7—C8—C14	−173.56 (16)	C14—C13—C17—C20	162.03 (17)
C7—C8—C9—Br1	−58.92 (17)	C17—C13—C14—C8	171.85 (15)
C7—C8—C9—C10	55.06 (18)	C17—C13—C14—C15	37.75 (18)
C7—C8—C9—C11	−171.81 (14)	C18—C13—C14—C8	60.3 (2)
C7—C8—C14—C13	−175.04 (15)	C18—C13—C14—C15	−73.83 (19)
C7—C8—C14—C15	−49.7 (2)	C18—C13—C17—C16	91.66 (18)
C9—C8—C14—C13	58.85 (19)	C18—C13—C17—C20	−80.5 (2)
C9—C8—C14—C15	−175.76 (16)	C8—C14—C15—C16	−165.38 (17)
C14—C8—C9—Br1	66.90 (15)	C13—C14—C15—C16	−35.73 (19)
C14—C8—C9—C10	−179.12 (14)	C14—C15—C16—C17	20.5 (2)
C14—C8—C9—C11	−45.98 (19)	C15—C16—C17—C13	3.5 (2)
Br1—C9—C10—C1	−65.03 (15)	C15—C16—C17—C20	175.38 (18)
Br1—C9—C10—C5	59.23 (15)	C13—C17—C20—O3	−3.9 (2)
Br1—C9—C10—C19	176.75 (13)	C13—C17—C20—C21	175.99 (17)
Br1—C9—C11—O2	160.66 (12)	C16—C17—C20—O3	−174.7 (2)
Br1—C9—C11—C12	−74.61 (15)	C16—C17—C20—C21	5.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O(2)—H(201)···O(1)^i	0.95	1.90	2.806 (2)	159

Symmetry code: (i) −x+1, y−1/2, −z+3/2.