12-Bromo-1,2,3,4-tetra­hydro-1,4-ethano­anthracen-11-ol

The title compound, C₁₆H₁₅BrO, contains two non-planar six-membered rings constituting a bicyclic system. One of these rings shares two C atoms with an ethano­anthracene moiety, while the second ring has bromo and hydr­oxy substituents. The bicyclic system has approximate D₃ symmetry. There are two molecules in the asymmetric unit. Two strong hydrogen bonds, with D...A distances of 2.765 (2) and 2.818 (2) Å, are observed between O atoms.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.104
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         10

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

   2 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

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PARST95 (Nardelli, 1995), PLATON (Spek, 2000) and WinGX (Farrugia, 1999).

12-Bromo-1,2,3,4-tetrahydro-1,4-ethanoantracen-11-ol

Crystal data

C16H15BrO	Z = 4
Mr = 303.20	F(000) = 616
Triclinic, P1	Dx = 1.490 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.854 (1) Å	Cell parameters from 4542 reflections
b = 12.316 (1) Å	θ = 1.7–25.6°
c = 12.488 (1) Å	µ = 3.03 mm^−1
α = 79.928 (10)°	T = 293 K
β = 77.248 (10)°	Prism, colourless
γ = 66.719 (10)°	0.15 × 0.07 × 0.06 mm
V = 1351.3 (2) Å^3

Data collection

Nonius KappaCCD diffractometer	4542 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 25.6°, θmin = 1.7°
Detector resolution: 9.0 pixels mm^-1	h = −11→11
φ or ω ? scans	k = −14→14
9387 measured reflections	l = −15→15
5043 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0443P)^2 + 0.8183P] where P = (Fo^2 + 2Fc^2)/3
5043 reflections	(Δ/σ)max = 0.001
325 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.96 e Å^−3

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
Br1A	0.18114 (4)	0.41367 (3)	0.23878 (3)	0.07370 (14)
Br1B	−0.05286 (4)	1.21397 (3)	0.48453 (3)	0.06830 (13)
O1A	0.42185 (19)	0.13372 (15)	0.37020 (14)	0.0463 (4)
H1AA	0.5031	0.0803	0.3542	0.069*
O1B	0.31819 (19)	1.05122 (15)	0.58449 (15)	0.0488 (4)
H1BB	0.3282	1.0582	0.5170	0.073*
C2A	0.4365 (3)	0.2462 (2)	0.3364 (2)	0.0420 (5)
H2A	0.4673	0.2542	0.2561	0.050*
C2B	0.1718 (2)	1.1266 (2)	0.6286 (2)	0.0401 (5)
H2B	0.1573	1.2091	0.6002	0.048*
C5B	−0.1273 (3)	1.1813 (3)	0.7612 (2)	0.0566 (7)
H5B1	−0.1950	1.1671	0.8263	0.068*
H5B2	−0.1846	1.2494	0.7160	0.068*
C1A	0.2808 (3)	0.3421 (2)	0.3683 (2)	0.0425 (5)
H1A	0.2193	0.3034	0.4202	0.051*
C1B	0.0531 (3)	1.0929 (2)	0.5952 (2)	0.0410 (5)
H1B	0.1054	1.0181	0.5611	0.049*
C3A	0.5481 (3)	0.2642 (2)	0.3921 (2)	0.0443 (5)
H3A	0.6455	0.1985	0.3815	0.053*
C16B	0.1507 (3)	0.9937 (2)	0.79847 (19)	0.0391 (5)
C14B	0.2284 (3)	0.8009 (2)	0.90208 (19)	0.0439 (5)
C15B	0.2441 (3)	0.9111 (2)	0.8642 (2)	0.0448 (5)
H15B	0.3189	0.9274	0.8844	0.054*
C8B	0.0186 (3)	0.8647 (2)	0.8017 (2)	0.0465 (6)
H8B	−0.0565	0.8497	0.7803	0.056*
C6B	−0.0575 (3)	1.0720 (2)	0.6961 (2)	0.0431 (5)
H6B	−0.1348	1.0530	0.6745	0.052*
C7B	0.0357 (3)	0.9703 (2)	0.76680 (19)	0.0407 (5)
C9B	0.1137 (3)	0.7777 (2)	0.8700 (2)	0.0458 (6)
C7A	0.3456 (3)	0.3703 (2)	0.5319 (2)	0.0435 (5)
C8A	0.2722 (3)	0.3917 (2)	0.6371 (2)	0.0497 (6)
H8A	0.1823	0.4562	0.6488	0.060*
C14A	0.4683 (3)	0.2169 (3)	0.7091 (2)	0.0506 (6)
C16A	0.4850 (3)	0.2728 (2)	0.5130 (2)	0.0422 (5)
C4A	0.5630 (3)	0.3832 (2)	0.3407 (3)	0.0557 (7)
H4A1	0.6327	0.3977	0.3750	0.067*
H4A2	0.6020	0.3794	0.2625	0.067*
C3B	0.1515 (3)	1.1149 (2)	0.7540 (2)	0.0427 (5)
H3B	0.2310	1.1286	0.7781	0.051*
C15A	0.5432 (3)	0.1982 (2)	0.5989 (2)	0.0487 (6)
H15A	0.6332	0.1341	0.5856	0.058*
C10B	0.0992 (4)	0.6669 (3)	0.9079 (2)	0.0599 (7)
H10B	0.0252	0.6499	0.8871	0.072*
C9A	0.3322 (3)	0.3163 (2)	0.7281 (2)	0.0504 (6)
C6A	0.2916 (3)	0.4370 (2)	0.4271 (2)	0.0471 (6)
H6A	0.1938	0.5012	0.4427	0.057*
C13B	0.3237 (3)	0.7124 (3)	0.9702 (2)	0.0561 (7)
H13B	0.4001	0.7263	0.9908	0.067*
C12B	0.3051 (4)	0.6075 (3)	1.0058 (2)	0.0640 (8)
H12B	0.3676	0.5507	1.0512	0.077*
C5A	0.4090 (3)	0.4853 (2)	0.3578 (3)	0.0577 (7)
H5A1	0.4150	0.5456	0.3952	0.069*
H5A2	0.3797	0.5215	0.2868	0.069*
C4B	−0.0040 (3)	1.2075 (2)	0.7955 (2)	0.0555 (7)
H4B1	−0.0195	1.2049	0.8752	0.067*
H4B2	−0.0084	1.2866	0.7645	0.067*
C11B	0.1917 (4)	0.5850 (3)	0.9741 (2)	0.0692 (9)
H11B	0.1796	0.5131	0.9986	0.083*
C13A	0.5221 (4)	0.1376 (3)	0.8006 (3)	0.0645 (8)
H13A	0.6101	0.0714	0.7893	0.077*
C12A	0.4455 (5)	0.1576 (4)	0.9059 (3)	0.0785 (10)
H12A	0.4823	0.1052	0.9653	0.094*
C10A	0.2568 (4)	0.3336 (3)	0.8384 (2)	0.0676 (8)
H10A	0.1680	0.3988	0.8519	0.081*
C11A	0.3119 (5)	0.2566 (4)	0.9242 (3)	0.0805 (11)
H11A	0.2609	0.2695	0.9957	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.0743 (2)	0.0758 (2)	0.0624 (2)	−0.01415 (17)	−0.03110 (16)	0.00682 (16)
Br1B	0.0718 (2)	0.0755 (2)	0.0621 (2)	−0.03199 (17)	−0.02784 (15)	0.01433 (15)
O1A	0.0420 (9)	0.0380 (9)	0.0555 (10)	−0.0128 (7)	−0.0030 (7)	−0.0072 (7)
O1B	0.0368 (9)	0.0463 (10)	0.0515 (10)	−0.0086 (7)	0.0001 (7)	−0.0008 (8)
C2A	0.0418 (12)	0.0401 (12)	0.0398 (12)	−0.0140 (10)	−0.0014 (10)	−0.0029 (10)
C2B	0.0354 (11)	0.0326 (11)	0.0490 (13)	−0.0108 (9)	−0.0042 (10)	−0.0036 (9)
C5B	0.0440 (14)	0.0578 (16)	0.0590 (16)	−0.0103 (12)	0.0013 (12)	−0.0165 (13)
C1A	0.0388 (12)	0.0418 (13)	0.0407 (12)	−0.0105 (10)	−0.0085 (9)	0.0031 (10)
C1B	0.0401 (12)	0.0373 (12)	0.0443 (12)	−0.0120 (9)	−0.0079 (10)	−0.0051 (10)
C3A	0.0363 (12)	0.0422 (13)	0.0507 (14)	−0.0131 (10)	−0.0028 (10)	−0.0042 (10)
C16B	0.0386 (12)	0.0434 (12)	0.0381 (11)	−0.0187 (10)	−0.0023 (9)	−0.0082 (10)
C14B	0.0461 (13)	0.0465 (13)	0.0348 (11)	−0.0139 (10)	−0.0025 (10)	−0.0063 (10)
C15B	0.0419 (13)	0.0558 (15)	0.0415 (12)	−0.0218 (11)	−0.0073 (10)	−0.0076 (11)
C8B	0.0532 (14)	0.0561 (15)	0.0413 (13)	−0.0316 (12)	−0.0084 (11)	−0.0053 (11)
C6B	0.0365 (12)	0.0494 (14)	0.0453 (13)	−0.0174 (10)	−0.0076 (10)	−0.0050 (10)
C7B	0.0406 (12)	0.0463 (13)	0.0378 (12)	−0.0188 (10)	−0.0046 (9)	−0.0069 (10)
C9B	0.0579 (15)	0.0461 (13)	0.0369 (12)	−0.0241 (12)	−0.0033 (10)	−0.0069 (10)
C7A	0.0442 (13)	0.0373 (12)	0.0491 (13)	−0.0151 (10)	−0.0063 (10)	−0.0066 (10)
C8A	0.0548 (15)	0.0435 (13)	0.0522 (15)	−0.0187 (11)	−0.0043 (12)	−0.0129 (11)
C14A	0.0540 (15)	0.0581 (16)	0.0534 (15)	−0.0332 (13)	−0.0186 (12)	0.0023 (12)
C16A	0.0391 (12)	0.0416 (12)	0.0492 (13)	−0.0185 (10)	−0.0073 (10)	−0.0044 (10)
C4A	0.0565 (16)	0.0520 (15)	0.0614 (16)	−0.0294 (13)	0.0014 (13)	−0.0047 (13)
C3B	0.0415 (12)	0.0431 (13)	0.0478 (13)	−0.0186 (10)	−0.0067 (10)	−0.0095 (10)
C15A	0.0392 (12)	0.0520 (14)	0.0583 (15)	−0.0197 (11)	−0.0126 (11)	−0.0016 (12)
C10B	0.087 (2)	0.0559 (16)	0.0462 (15)	−0.0384 (16)	−0.0101 (14)	−0.0030 (12)
C9A	0.0636 (16)	0.0553 (15)	0.0454 (14)	−0.0339 (13)	−0.0081 (12)	−0.0112 (12)
C6A	0.0469 (13)	0.0367 (12)	0.0500 (14)	−0.0092 (10)	−0.0054 (11)	−0.0032 (10)
C13B	0.0545 (16)	0.0619 (17)	0.0427 (14)	−0.0133 (13)	−0.0055 (11)	−0.0049 (12)
C12B	0.079 (2)	0.0494 (16)	0.0460 (15)	−0.0080 (14)	−0.0095 (14)	0.0010 (12)
C5A	0.0695 (18)	0.0437 (14)	0.0606 (17)	−0.0262 (13)	−0.0063 (14)	0.0002 (12)
C4B	0.0562 (16)	0.0477 (15)	0.0603 (16)	−0.0161 (12)	−0.0001 (13)	−0.0196 (13)
C11B	0.109 (3)	0.0477 (16)	0.0483 (16)	−0.0293 (17)	−0.0103 (16)	−0.0021 (13)
C13A	0.0701 (19)	0.077 (2)	0.0615 (18)	−0.0404 (17)	−0.0295 (15)	0.0109 (15)
C12A	0.110 (3)	0.098 (3)	0.0539 (18)	−0.064 (3)	−0.0349 (19)	0.0142 (18)
C10A	0.092 (2)	0.072 (2)	0.0503 (16)	−0.0402 (18)	−0.0069 (15)	−0.0184 (15)
C11A	0.119 (3)	0.095 (3)	0.0469 (17)	−0.059 (3)	−0.0126 (18)	−0.0102 (17)

Geometric parameters (Å, º)

Br1A—C1A	1.969 (2)	C7A—C8A	1.366 (4)
Br1B—C1B	1.977 (2)	C7A—C16A	1.427 (3)
O1A—C2A	1.430 (3)	C7A—C6A	1.502 (4)
O1A—H1AA	0.8200	C8A—C9A	1.413 (4)
O1B—C2B	1.420 (3)	C8A—H8A	0.9300
O1B—H1BB	0.8200	C14A—C13A	1.417 (4)
C2A—C3A	1.525 (4)	C14A—C9A	1.421 (4)
C2A—C1A	1.540 (3)	C14A—C15A	1.421 (4)
C2A—H2A	0.9800	C16A—C15A	1.354 (4)
C2B—C3B	1.523 (3)	C4A—C5A	1.540 (4)
C2B—C1B	1.541 (3)	C4A—H4A1	0.9700
C2B—H2B	0.9800	C4A—H4A2	0.9700
C5B—C6B	1.534 (4)	C3B—C4B	1.547 (3)
C5B—C4B	1.534 (4)	C3B—H3B	0.9800
C5B—H5B1	0.9700	C15A—H15A	0.9300
C5B—H5B2	0.9700	C10B—C11B	1.359 (5)
C1A—C6A	1.534 (4)	C10B—H10B	0.9300
C1A—H1A	0.9800	C9A—C10A	1.422 (4)
C1B—C6B	1.530 (3)	C6A—C5A	1.537 (4)
C1B—H1B	0.9800	C6A—H6A	0.9800
C3A—C16A	1.506 (3)	C13B—C12B	1.361 (4)
C3A—C4A	1.543 (4)	C13B—H13B	0.9300
C3A—H3A	0.9800	C12B—C11B	1.400 (5)
C16B—C15B	1.363 (4)	C12B—H12B	0.9300
C16B—C7B	1.421 (3)	C5A—H5A1	0.9700
C16B—C3B	1.501 (3)	C5A—H5A2	0.9700
C14B—C15B	1.414 (4)	C4B—H4B1	0.9700
C14B—C13B	1.419 (4)	C4B—H4B2	0.9700
C14B—C9B	1.420 (4)	C11B—H11B	0.9300
C15B—H15B	0.9300	C13A—C12A	1.374 (5)
C8B—C7B	1.361 (4)	C13A—H13A	0.9300
C8B—C9B	1.413 (4)	C12A—C11A	1.402 (6)
C8B—H8B	0.9300	C12A—H12A	0.9300
C6B—C7B	1.501 (3)	C10A—C11A	1.355 (5)
C6B—H6B	0.9800	C10A—H10A	0.9300
C9B—C10B	1.416 (4)	C11A—H11A	0.9300
C2A—O1A—H1AA	109.5	C9A—C8A—H8A	119.8
C2B—O1B—H1BB	109.5	C13A—C14A—C9A	118.7 (3)
O1A—C2A—C3A	113.2 (2)	C13A—C14A—C15A	122.3 (3)
O1A—C2A—C1A	106.81 (19)	C9A—C14A—C15A	118.9 (2)
C3A—C2A—C1A	108.63 (19)	C15A—C16A—C7A	120.3 (2)
O1A—C2A—H2A	109.4	C15A—C16A—C3A	127.3 (2)
C3A—C2A—H2A	109.4	C7A—C16A—C3A	112.3 (2)
C1A—C2A—H2A	109.4	C5A—C4A—C3A	110.0 (2)
O1B—C2B—C3B	110.1 (2)	C5A—C4A—H4A1	109.7
O1B—C2B—C1B	110.42 (19)	C3A—C4A—H4A1	109.7
C3B—C2B—C1B	108.62 (19)	C5A—C4A—H4A2	109.7
O1B—C2B—H2B	109.2	C3A—C4A—H4A2	109.7
C3B—C2B—H2B	109.2	H4A1—C4A—H4A2	108.2
C1B—C2B—H2B	109.2	C16B—C3B—C2B	109.28 (19)
C6B—C5B—C4B	110.0 (2)	C16B—C3B—C4B	108.0 (2)
C6B—C5B—H5B1	109.7	C2B—C3B—C4B	107.2 (2)
C4B—C5B—H5B1	109.7	C16B—C3B—H3B	110.8
C6B—C5B—H5B2	109.7	C2B—C3B—H3B	110.8
C4B—C5B—H5B2	109.7	C4B—C3B—H3B	110.8
H5B1—C5B—H5B2	108.2	C16A—C15A—C14A	120.7 (2)
C6A—C1A—C2A	110.9 (2)	C16A—C15A—H15A	119.6
C6A—C1A—Br1A	111.21 (16)	C14A—C15A—H15A	119.6
C2A—C1A—Br1A	111.26 (16)	C11B—C10B—C9B	121.0 (3)
C6A—C1A—H1A	107.8	C11B—C10B—H10B	119.5
C2A—C1A—H1A	107.8	C9B—C10B—H10B	119.5
Br1A—C1A—H1A	107.8	C8A—C9A—C14A	119.3 (2)
C6B—C1B—C2B	111.3 (2)	C8A—C9A—C10A	121.9 (3)
C6B—C1B—Br1B	111.14 (16)	C14A—C9A—C10A	118.7 (3)
C2B—C1B—Br1B	111.28 (16)	C7A—C6A—C1A	103.7 (2)
C6B—C1B—H1B	107.6	C7A—C6A—C5A	109.3 (2)
C2B—C1B—H1B	107.6	C1A—C6A—C5A	110.1 (2)
Br1B—C1B—H1B	107.6	C7A—C6A—H6A	111.2
C16A—C3A—C2A	108.37 (19)	C1A—C6A—H6A	111.2
C16A—C3A—C4A	108.7 (2)	C5A—C6A—H6A	111.2
C2A—C3A—C4A	107.6 (2)	C12B—C13B—C14B	121.0 (3)
C16A—C3A—H3A	110.7	C12B—C13B—H13B	119.5
C2A—C3A—H3A	110.7	C14B—C13B—H13B	119.5
C4A—C3A—H3A	110.7	C13B—C12B—C11B	120.0 (3)
C15B—C16B—C7B	120.4 (2)	C13B—C12B—H12B	120.0
C15B—C16B—C3B	126.8 (2)	C11B—C12B—H12B	120.0
C7B—C16B—C3B	112.8 (2)	C6A—C5A—C4A	109.7 (2)
C15B—C14B—C13B	122.4 (3)	C6A—C5A—H5A1	109.7
C15B—C14B—C9B	118.7 (2)	C4A—C5A—H5A1	109.7
C13B—C14B—C9B	118.8 (2)	C6A—C5A—H5A2	109.7
C16B—C15B—C14B	120.7 (2)	C4A—C5A—H5A2	109.7
C16B—C15B—H15B	119.6	H5A1—C5A—H5A2	108.2
C14B—C15B—H15B	119.6	C5B—C4B—C3B	110.0 (2)
C7B—C8B—C9B	120.6 (2)	C5B—C4B—H4B1	109.7
C7B—C8B—H8B	119.7	C3B—C4B—H4B1	109.7
C9B—C8B—H8B	119.7	C5B—C4B—H4B2	109.7
C7B—C6B—C1B	105.36 (19)	C3B—C4B—H4B2	109.7
C7B—C6B—C5B	108.0 (2)	H4B1—C4B—H4B2	108.2
C1B—C6B—C5B	109.7 (2)	C10B—C11B—C12B	120.9 (3)
C7B—C6B—H6B	111.2	C10B—C11B—H11B	119.6
C1B—C6B—H6B	111.2	C12B—C11B—H11B	119.6
C5B—C6B—H6B	111.2	C12A—C13A—C14A	120.7 (3)
C8B—C7B—C16B	120.1 (2)	C12A—C13A—H13A	119.7
C8B—C7B—C6B	127.0 (2)	C14A—C13A—H13A	119.7
C16B—C7B—C6B	112.9 (2)	C13A—C12A—C11A	120.3 (3)
C8B—C9B—C10B	122.2 (3)	C13A—C12A—H12A	119.9
C8B—C9B—C14B	119.4 (2)	C11A—C12A—H12A	119.9
C10B—C9B—C14B	118.4 (3)	C11A—C10A—C9A	121.1 (3)
C8A—C7A—C16A	120.3 (2)	C11A—C10A—H10A	119.4
C8A—C7A—C6A	126.6 (2)	C9A—C10A—H10A	119.4
C16A—C7A—C6A	113.0 (2)	C10A—C11A—C12A	120.5 (3)
C7A—C8A—C9A	120.4 (2)	C10A—C11A—H11A	119.7
C7A—C8A—H8A	119.8	C12A—C11A—H11A	119.7
O1A—C2A—C1A—C6A	132.7 (2)	C16A—C3A—C4A—C5A	−58.4 (3)
C3A—C2A—C1A—C6A	10.3 (3)	C2A—C3A—C4A—C5A	58.8 (3)
O1A—C2A—C1A—Br1A	−102.96 (19)	C15B—C16B—C3B—C2B	122.8 (3)
C3A—C2A—C1A—Br1A	134.63 (17)	C7B—C16B—C3B—C2B	−58.5 (3)
O1B—C2B—C1B—C6B	127.1 (2)	C15B—C16B—C3B—C4B	−120.9 (3)
C3B—C2B—C1B—C6B	6.2 (3)	C7B—C16B—C3B—C4B	57.8 (3)
O1B—C2B—C1B—Br1B	−108.38 (18)	O1B—C2B—C3B—C16B	−68.5 (2)
C3B—C2B—C1B—Br1B	130.78 (17)	C1B—C2B—C3B—C16B	52.6 (2)
O1A—C2A—C3A—C16A	−67.5 (2)	O1B—C2B—C3B—C4B	174.76 (19)
C1A—C2A—C3A—C16A	50.9 (2)	C1B—C2B—C3B—C4B	−64.2 (2)
O1A—C2A—C3A—C4A	175.11 (19)	C7A—C16A—C15A—C14A	−1.2 (4)
C1A—C2A—C3A—C4A	−66.4 (2)	C3A—C16A—C15A—C14A	−178.6 (2)
C7B—C16B—C15B—C14B	0.0 (3)	C13A—C14A—C15A—C16A	176.9 (3)
C3B—C16B—C15B—C14B	178.6 (2)	C9A—C14A—C15A—C16A	−1.0 (4)
C13B—C14B—C15B—C16B	179.7 (2)	C8B—C9B—C10B—C11B	−179.6 (3)
C9B—C14B—C15B—C16B	0.2 (3)	C14B—C9B—C10B—C11B	0.6 (4)
C2B—C1B—C6B—C7B	−61.2 (2)	C7A—C8A—C9A—C14A	−1.1 (4)
Br1B—C1B—C6B—C7B	174.22 (15)	C7A—C8A—C9A—C10A	−178.0 (3)
C2B—C1B—C6B—C5B	54.8 (3)	C13A—C14A—C9A—C8A	−175.9 (2)
Br1B—C1B—C6B—C5B	−69.8 (2)	C15A—C14A—C9A—C8A	2.1 (4)
C4B—C5B—C6B—C7B	56.7 (3)	C13A—C14A—C9A—C10A	1.2 (4)
C4B—C5B—C6B—C1B	−57.6 (3)	C15A—C14A—C9A—C10A	179.1 (2)
C9B—C8B—C7B—C16B	0.4 (4)	C8A—C7A—C6A—C1A	−119.0 (3)
C9B—C8B—C7B—C6B	−178.8 (2)	C16A—C7A—C6A—C1A	58.1 (3)
C15B—C16B—C7B—C8B	−0.3 (3)	C8A—C7A—C6A—C5A	123.6 (3)
C3B—C16B—C7B—C8B	−179.1 (2)	C16A—C7A—C6A—C5A	−59.3 (3)
C15B—C16B—C7B—C6B	179.0 (2)	C2A—C1A—C6A—C7A	−64.7 (2)
C3B—C16B—C7B—C6B	0.2 (3)	Br1A—C1A—C6A—C7A	170.92 (16)
C1B—C6B—C7B—C8B	−122.2 (3)	C2A—C1A—C6A—C5A	52.2 (3)
C5B—C6B—C7B—C8B	120.7 (3)	Br1A—C1A—C6A—C5A	−72.2 (2)
C1B—C6B—C7B—C16B	58.5 (2)	C15B—C14B—C13B—C12B	179.6 (2)
C5B—C6B—C7B—C16B	−58.6 (3)	C9B—C14B—C13B—C12B	−0.9 (4)
C7B—C8B—C9B—C10B	180.0 (2)	C14B—C13B—C12B—C11B	0.8 (4)
C7B—C8B—C9B—C14B	−0.2 (4)	C7A—C6A—C5A—C4A	53.6 (3)
C15B—C14B—C9B—C8B	−0.1 (3)	C1A—C6A—C5A—C4A	−59.7 (3)
C13B—C14B—C9B—C8B	−179.6 (2)	C3A—C4A—C5A—C6A	3.7 (3)
C15B—C14B—C9B—C10B	179.7 (2)	C6B—C5B—C4B—C3B	−0.3 (3)
C13B—C14B—C9B—C10B	0.2 (3)	C16B—C3B—C4B—C5B	−56.2 (3)
C16A—C7A—C8A—C9A	−1.1 (4)	C2B—C3B—C4B—C5B	61.5 (3)
C6A—C7A—C8A—C9A	175.7 (2)	C9B—C10B—C11B—C12B	−0.6 (5)
C8A—C7A—C16A—C15A	2.3 (4)	C13B—C12B—C11B—C10B	−0.1 (5)
C6A—C7A—C16A—C15A	−175.0 (2)	C9A—C14A—C13A—C12A	−1.1 (4)
C8A—C7A—C16A—C3A	−179.9 (2)	C15A—C14A—C13A—C12A	−179.0 (3)
C6A—C7A—C16A—C3A	2.9 (3)	C14A—C13A—C12A—C11A	0.5 (5)
C2A—C3A—C16A—C15A	117.0 (3)	C8A—C9A—C10A—C11A	176.3 (3)
C4A—C3A—C16A—C15A	−126.3 (3)	C14A—C9A—C10A—C11A	−0.6 (4)
C2A—C3A—C16A—C7A	−60.6 (3)	C9A—C10A—C11A—C12A	0.0 (5)
C4A—C3A—C16A—C7A	56.0 (3)	C13A—C12A—C11A—C10A	0.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1AA···O1B^i	0.82	2.05	2.765 (2)	145
O1B—H1BB···O1A^ii	0.82	2.10	2.811 (2)	145

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