9-(Bromo­acet­yl)anthracene

In the title compound, C₁₆H₁₁BrO, the bromo­acetyl group makes an angle of 105.8 (1)° with the anthracene ring system. The crystal packing is consolidated by C—H...π, Br...π and C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.084
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.38
PLAT432_ALERT_2_C Short Inter X...Y Contact  Br1    ..  C1      ..       3.32 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C3     ..  CG3     ..       4.34 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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: CrystalClear (Rigaku Corporation, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.3; Bruno et al., 2002); software used to prepare material for publication: CrystalStructure.

9-(Bromoacetyl)anthracene

Crystal data

C16H11BrO	F(000) = 600.00
Mr = 299.17	Dx = 1.610 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2yn	Cell parameters from 11265 reflections
a = 9.188 (2) Å	θ = 4.9–68.2°
b = 8.218 (2) Å	µ = 4.40 mm^−1
c = 16.628 (4) Å	T = 153 K
β = 100.583 (15)°	Prism, yellow
V = 1234.1 (5) Å^3	0.37 × 0.21 × 0.15 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2015 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.040
ω scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→11
Tmin = 0.262, Tmax = 0.517	k = −9→9
11429 measured reflections	l = −19→20
2195 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.0378P)^2 + 0.9847P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.084	(Δ/σ)max = 0.001
S = 1.11	Δρmax = 0.93 e Å^−3
2195 reflections	Δρmin = −0.39 e Å^−3
164 parameters

Special details

Refinement. Refinement was performed 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	−0.17337 (3)	−0.01862 (4)	0.855301 (17)	0.03370 (13)
O1	−0.1743 (2)	−0.1297 (2)	0.67874 (12)	0.0420 (5)
C1	−0.2457 (2)	0.1577 (3)	0.54214 (16)	0.0270 (6)
C2	−0.3113 (3)	0.2443 (3)	0.47552 (17)	0.0331 (6)
C3	−0.2236 (3)	0.3299 (3)	0.42718 (17)	0.0364 (7)
C4	−0.0749 (3)	0.3237 (3)	0.44565 (16)	0.0318 (6)
C5	−0.0006 (2)	0.2357 (3)	0.51524 (15)	0.0252 (5)
C6	0.1533 (2)	0.2306 (3)	0.53641 (16)	0.0273 (6)
C7	0.2256 (2)	0.1466 (3)	0.60443 (15)	0.0254 (5)
C8	0.3831 (2)	0.1412 (3)	0.62644 (17)	0.0317 (6)
C9	0.4519 (3)	0.0577 (4)	0.69298 (18)	0.0352 (7)
C10	0.3671 (3)	−0.0296 (3)	0.74191 (18)	0.0311 (6)
C11	0.2171 (3)	−0.0282 (3)	0.72365 (16)	0.0264 (6)
C12	0.1400 (2)	0.0618 (3)	0.65551 (15)	0.0225 (5)
C13	−0.0143 (2)	0.0693 (3)	0.63550 (15)	0.0214 (5)
C14	−0.0884 (2)	0.1515 (3)	0.56525 (15)	0.0216 (5)
C15	−0.1051 (2)	−0.0048 (3)	0.69328 (17)	0.0244 (6)
C16	−0.1062 (2)	0.0987 (3)	0.76817 (15)	0.0259 (6)
H1	−0.3054	0.1006	0.5737	0.032*
H2	−0.4162	0.2477	0.4612	0.040*
H3	−0.2706	0.3919	0.3815	0.044*
H4	−0.0182	0.3788	0.4117	0.038*
H5	0.2106	0.2866	0.5031	0.033*
H6	0.4412	0.1975	0.5937	0.038*
H7	0.5569	0.0576	0.7069	0.042*
H8	0.4160	−0.0895	0.7879	0.037*
H9	0.1623	−0.0882	0.7568	0.032*
H10	−0.1717	0.1937	0.7527	0.031*
H11	−0.0049	0.1401	0.7884	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0381 (2)	0.0346 (2)	0.0319 (2)	0.00418 (13)	0.01562 (14)	0.00675 (12)
O1	0.0500 (12)	0.0381 (14)	0.0421 (11)	−0.0217 (11)	0.0195 (9)	−0.0073 (9)
C1	0.0275 (13)	0.0263 (16)	0.0283 (13)	0.0017 (11)	0.0078 (10)	−0.0044 (11)
C2	0.0274 (14)	0.0364 (18)	0.0333 (14)	0.0056 (12)	−0.0004 (11)	−0.0069 (12)
C3	0.0465 (17)	0.0343 (19)	0.0261 (14)	0.0087 (14)	0.0006 (12)	0.0029 (12)
C4	0.0426 (16)	0.0282 (17)	0.0256 (13)	0.0006 (13)	0.0093 (11)	0.0011 (11)
C5	0.0329 (14)	0.0202 (15)	0.0243 (12)	0.0003 (11)	0.0098 (10)	−0.0029 (10)
C6	0.0292 (13)	0.0271 (16)	0.0289 (13)	−0.0043 (11)	0.0135 (10)	−0.0011 (11)
C7	0.0270 (13)	0.0222 (16)	0.0290 (13)	−0.0026 (11)	0.0104 (10)	−0.0053 (11)
C8	0.0227 (13)	0.0353 (18)	0.0401 (15)	−0.0063 (12)	0.0138 (11)	−0.0074 (12)
C9	0.0202 (13)	0.0443 (19)	0.0409 (16)	−0.0026 (13)	0.0052 (11)	−0.0123 (14)
C10	0.0279 (14)	0.0324 (17)	0.0315 (15)	0.0057 (12)	0.0014 (11)	−0.0066 (12)
C11	0.0290 (14)	0.0249 (16)	0.0261 (13)	0.0009 (11)	0.0071 (11)	−0.0025 (11)
C12	0.0220 (12)	0.0197 (14)	0.0268 (13)	−0.0008 (11)	0.0072 (9)	−0.0062 (11)
C13	0.0229 (12)	0.0177 (14)	0.0250 (12)	−0.0005 (10)	0.0079 (9)	−0.0037 (10)
C14	0.0266 (13)	0.0171 (14)	0.0225 (12)	0.0014 (10)	0.0081 (9)	−0.0037 (10)
C15	0.0204 (12)	0.0246 (16)	0.0284 (14)	0.0017 (10)	0.0047 (10)	0.0045 (10)
C16	0.0253 (13)	0.0258 (16)	0.0290 (13)	−0.0009 (11)	0.0110 (10)	0.0050 (11)

Geometric parameters (Å, º)

Br1—C16	1.933 (2)	C12—C13	1.397 (3)
O1—C15	1.209 (3)	C13—C14	1.411 (3)
C1—C2	1.361 (3)	C13—C15	1.511 (3)
C1—C14	1.427 (3)	C15—C16	1.510 (3)
C2—C3	1.424 (4)	C1—H1	0.950
C3—C4	1.346 (4)	C2—H2	0.950
C4—C5	1.427 (3)	C3—H3	0.950
C5—C6	1.394 (3)	C4—H4	0.950
C5—C14	1.437 (3)	C6—H5	0.950
C6—C7	1.386 (3)	C8—H6	0.950
C7—C8	1.427 (3)	C9—H7	0.950
C7—C12	1.439 (3)	C10—H8	0.950
C8—C9	1.356 (3)	C11—H9	0.950
C9—C10	1.420 (4)	C16—H10	0.990
C10—C11	1.356 (3)	C16—H11	0.990
C11—C12	1.428 (3)
Br1···O1	3.073 (2)	C12···H6	3.317
Br1···O1^i	3.493 (2)	C12···H8	3.282
Br1···C1^ii	3.317 (2)	C12···H8^x	3.088
Br1···C2^ii	3.446 (2)	C12···H9	2.067
Br1···C15	2.878 (2)	C12···H9^x	3.567
O1···Br1	3.073 (2)	C12···H11	2.855
O1···Br1^ii	3.493 (2)	C13···H1	2.695
O1···C1	3.259 (3)	C13···H8^x	3.143
O1···C12	3.373 (3)	C13···H9	2.679
O1···C13	2.396 (3)	C13···H10	2.822
O1···C14	3.174 (3)	C13···H11	2.595
O1···C16	2.405 (3)	C14···H1	2.067
O1···C16^ii	3.237 (3)	C14···H2	3.283
C1···Br1^i	3.317 (2)	C14···H4	3.320
C1···O1	3.259 (3)	C14···H5	3.300
C1···C3	2.416 (4)	C14···H8^x	3.403
C1···C4	2.797 (4)	C14···H10	3.361
C1···C5	2.459 (3)	C15···H1	2.598
C1···C7^iii	3.521 (3)	C15···H7^viii	3.196
C1···C13	2.499 (3)	C15···H9	2.582
C1···C15	2.929 (3)	C15···H10	2.058
C2···Br1^i	3.446 (2)	C15···H10^ii	3.440
C2···C4	2.406 (4)	C15···H11	2.058
C2···C5	2.810 (3)	C16···H1	3.411
C2···C8^iii	3.597 (4)	C16···H2^v	3.589
C2···C14	2.425 (3)	C16···H3^v	3.306
C3···C1	2.416 (4)	C16···H7^viii	3.094
C3···C5	2.416 (3)	C16···H8^x	3.329
C3···C11^iii	3.535 (4)	C16···H9	2.942
C3···C14	2.814 (3)	H1···Br1^i	3.3630
C4···C1	2.797 (4)	H1···O1	2.704
C4···C2	2.406 (4)	H1···C2	2.007
C4···C4^iv	3.556 (3)	H1···C3	3.274
C4···C6	2.469 (3)	H1···C5	3.319
C4···C12^iii	3.585 (3)	H1···C8^viii	3.161
C4···C14	2.462 (3)	H1···C9^viii	3.264
C5···C1	2.459 (3)	H1···C13	2.695
C5···C2	2.810 (3)	H1···C14	2.067
C5···C3	2.416 (3)	H1···C15	2.598
C5···C7	2.434 (3)	H1···C16	3.411
C5···C12	2.836 (3)	H1···H2	2.302
C5···C13	2.445 (3)	H1···H5^iii	3.595
C5···C13^iii	3.565 (3)	H1···H6^viii	2.540
C6···C4	2.469 (3)	H1···H7^viii	2.768
C6···C8	2.465 (3)	H1···H10	3.100
C6···C12	2.439 (3)	H2···Br1^i	3.5711
C6···C13	2.789 (3)	H2···Br1^ix	3.4800
C6···C14	2.444 (3)	H2···C1	2.010
C6···C14^iii	3.565 (3)	H2···C3	2.067
C7···C1^iii	3.521 (3)	H2···C4	3.254
C7···C5	2.434 (3)	H2···C8^iii	3.549
C7···C9	2.429 (3)	H2···C9^iii	3.560
C7···C10	2.815 (3)	H2···C14	3.283
C7···C11	2.461 (3)	H2···C16^ix	3.589
C7···C13	2.439 (3)	H2···H1	2.302
C7···C14	2.839 (3)	H2···H3	2.367
C8···C2^iii	3.597 (4)	H2···H6^viii	2.793
C8···C6	2.465 (3)	H2···H11^ix	2.984
C8···C10	2.404 (4)	H3···C1	3.266
C8···C11	2.790 (4)	H3···C2	2.067
C8···C12	2.458 (3)	H3···C4	1.996
C9···C7	2.429 (3)	H3···C5	3.274
C9···C11	2.412 (4)	H3···C6^iv	3.479
C9···C12	2.819 (3)	H3···C10^ix	3.057
C10···C7	2.815 (3)	H3···C11^iii	3.542
C10···C8	2.404 (4)	H3···C11^ix	2.837
C10···C12	2.425 (3)	H3···C16^ix	3.306
C11···C3^iii	3.535 (4)	H3···H2	2.367
C11···C7	2.461 (3)	H3···H4	2.283
C11···C8	2.790 (4)	H3···H5^iv	3.252
C11···C9	2.412 (4)	H3···H8^ix	2.996
C11···C13	2.483 (3)	H3···H9^ix	2.610
C11···C15	2.916 (3)	H3···H11^ix	2.424
C11···C16	3.357 (4)	H4···O1^iii	3.249
C12···O1	3.373 (3)	H4···C2	3.263
C12···C4^iii	3.585 (3)	H4···C3	1.992
C12···C5	2.836 (3)	H4···C4^iv	3.404
C12···C6	2.439 (3)	H4···C5	2.066
C12···C8	2.458 (3)	H4···C5^iv	3.386
C12···C9	2.819 (3)	H4···C6	2.658
C12···C10	2.425 (3)	H4···C10^ix	3.086
C12···C14	2.458 (3)	H4···C14	3.320
C12···C15	2.507 (3)	H4···H3	2.283
C12···C16	3.206 (3)	H4···H4^iv	3.512
C13···O1	2.396 (3)	H4···H5	2.476
C13···C1	2.499 (3)	H4···H8^ix	2.673
C13···C5	2.445 (3)	H5···Br1^xii	3.4311
C13···C5^iii	3.565 (3)	H5···O1^iii	3.247
C13···C6	2.789 (3)	H5···C3^iv	3.353
C13···C7	2.439 (3)	H5···C4	2.639
C13···C11	2.483 (3)	H5···C4^iv	3.596
C13···C16	2.514 (3)	H5···C5	2.032
C14···O1	3.174 (3)	H5···C7	2.024
C14···C2	2.425 (3)	H5···C8	2.637
C14···C3	2.814 (3)	H5···C12	3.295
C14···C4	2.462 (3)	H5···C14	3.300
C14···C6	2.444 (3)	H5···H1^iii	3.595
C14···C6^iii	3.565 (3)	H5···H3^iv	3.252
C14···C7	2.839 (3)	H5···H4	2.476
C14···C12	2.458 (3)	H5···H6	2.474
C14···C15	2.515 (3)	H6···Br1^x	3.1700
C14···C16	3.436 (3)	H6···C1^xi	3.166
C15···Br1	2.878 (2)	H6···C2^xi	3.289
C15···C1	2.929 (3)	H6···C6	2.655
C15···C11	2.916 (3)	H6···C7	2.064
C15···C12	2.507 (3)	H6···C9	1.999
C15···C14	2.515 (3)	H6···C10	3.262
C16···O1	2.405 (3)	H6···C12	3.317
C16···O1^i	3.237 (3)	H6···H1^xi	2.540
C16···C11	3.357 (4)	H6···H2^xi	2.793
C16···C12	3.206 (3)	H6···H5	2.474
C16···C13	2.514 (3)	H6···H7	2.294
C16···C14	3.436 (3)	H6···H9^x	3.325
Br1···H1^ii	3.3630	H7···Br1^xi	3.2211
Br1···H2^ii	3.5711	H7···O1^xi	3.018
Br1···H2^v	3.4800	H7···O1^x	3.260
Br1···H5^vi	3.4311	H7···C7	3.286
Br1···H6^vii	3.1700	H7···C8	2.007
Br1···H7^viii	3.2211	H7···C10	2.065
Br1···H10	2.443	H7···C11	3.262
Br1···H10^ii	3.147	H7···C15^xi	3.196
Br1···H11	2.442	H7···C16^xi	3.094
O1···H1	2.704	H7···H1^xi	2.768
O1···H4^iii	3.249	H7···H6	2.294
O1···H5^iii	3.247	H7···H8	2.365
O1···H7^viii	3.018	H7···H10^xi	2.711
O1···H7^vii	3.260	H7···H10^vii	3.201
O1···H9	3.145	H7···H11^vii	3.467
O1···H10	2.927	H8···C3^v	3.557
O1···H10^ii	2.450	H8···C4^v	3.403
O1···H11	3.102	H8···C5^vii	3.528
C1···H2	2.010	H8···C6^vii	3.436
C1···H3	3.266	H8···C7^vii	3.234
C1···H6^viii	3.166	H8···C8	3.255
C1···H10	3.454	H8···C9	2.063
C2···H1	2.007	H8···C11	2.004
C2···H3	2.067	H8···C12	3.282
C2···H4	3.263	H8···C12^vii	3.088
C2···H6^viii	3.289	H8···C13^vii	3.143
C2···H11^ix	3.422	H8···C14^vii	3.403
C3···H1	3.274	H8···C16^vii	3.329
C3···H2	2.067	H8···H3^v	2.996
C3···H4	1.992	H8···H4^v	2.673
C3···H5^iv	3.353	H8···H7	2.365
C3···H8^ix	3.557	H8···H9	2.293
C3···H9^ix	3.542	H8···H10^vii	3.119
C3···H11^ix	3.142	H8···H11^vii	2.756
C4···H2	3.254	H9···O1	3.145
C4···H3	1.996	H9···C3^v	3.542
C4···H4^iv	3.404	H9···C7	3.320
C4···H5	2.639	H9···C7^vii	3.203
C4···H5^iv	3.596	H9···C8^vii	3.031
C4···H8^ix	3.403	H9···C9	3.268
C5···H1	3.319	H9···C9^vii	3.254
C5···H3	3.274	H9···C10	2.001
C5···H4	2.066	H9···C12	2.067
C5···H4^iv	3.386	H9···C12^vii	3.567
C5···H5	2.032	H9···C13	2.679
C5···H8^x	3.528	H9···C15	2.582
C6···H3^iv	3.479	H9···C16	2.942
C6···H4	2.658	H9···H3^v	2.610
C6···H6	2.655	H9···H6^vii	3.325
C6···H8^x	3.436	H9···H8	2.293
C7···H5	2.024	H9···H11	2.541
C7···H6	2.064	H10···Br1	2.443
C7···H7	3.286	H10···Br1^i	3.147
C7···H8^x	3.234	H10···O1	2.927
C7···H9	3.320	H10···O1^i	2.450
C7···H9^x	3.203	H10···C1	3.454
C8···H1^xi	3.161	H10···C9^viii	3.596
C8···H2^iii	3.549	H10···C10^x	3.594
C8···H5	2.637	H10···C13	2.822
C8···H7	2.007	H10···C14	3.361
C8···H8	3.255	H10···C15	2.058
C8···H9^x	3.031	H10···C15^i	3.440
C9···H1^xi	3.264	H10···H1	3.100
C9···H2^iii	3.560	H10···H7^viii	2.711
C9···H6	1.999	H10···H7^x	3.201
C9···H8	2.063	H10···H8^x	3.119
C9···H9	3.268	H10···H11	1.600
C9···H9^x	3.254	H11···Br1	2.442
C9···H10^xi	3.596	H11···O1	3.102
C9···H11^vii	3.472	H11···C2^v	3.422
C10···H3^v	3.057	H11···C3^v	3.142
C10···H4^v	3.086	H11···C9^x	3.472
C10···H6	3.262	H11···C10^x	3.076
C10···H7	2.065	H11···C11	2.836
C10···H9	2.001	H11···C12	2.855
C10···H10^vii	3.594	H11···C13	2.595
C10···H11^vii	3.076	H11···C15	2.058
C11···H3^iii	3.542	H11···H2^v	2.984
C11···H3^v	2.837	H11···H3^v	2.424
C11···H7	3.262	H11···H7^x	3.467
C11···H8	2.004	H11···H8^x	2.756
C11···H11	2.836	H11···H9	2.541
C12···H5	3.295	H11···H10	1.600
C2—C1—C14	120.9 (2)	C13—C15—C16	112.7 (2)
C1—C2—C3	120.4 (2)	Br1—C16—C15	112.85 (19)
C2—C3—C4	120.6 (2)	C2—C1—H1	119.6
C3—C4—C5	121.2 (2)	C14—C1—H1	119.6
C4—C5—C6	122.1 (2)	C1—C2—H2	119.8
C4—C5—C14	118.5 (2)	C3—C2—H2	119.8
C6—C5—C14	119.4 (2)	C2—C3—H3	119.7
C5—C6—C7	122.2 (2)	C4—C3—H3	119.7
C6—C7—C8	122.4 (2)	C3—C4—H4	119.4
C6—C7—C12	119.4 (2)	C5—C4—H4	119.4
C8—C7—C12	118.2 (2)	C5—C6—H5	118.9
C7—C8—C9	121.6 (2)	C7—C6—H5	118.9
C8—C9—C10	120.0 (2)	C7—C8—H6	119.2
C9—C10—C11	120.6 (2)	C9—C8—H6	119.2
C10—C11—C12	121.2 (2)	C8—C9—H7	120.0
C7—C12—C11	118.3 (2)	C10—C9—H7	120.0
C7—C12—C13	118.6 (2)	C9—C10—H8	119.7
C11—C12—C13	123.1 (2)	C11—C10—H8	119.7
C12—C13—C14	122.1 (2)	C10—C11—H9	119.4
C12—C13—C15	119.0 (2)	C12—C11—H9	119.4
C14—C13—C15	118.8 (2)	Br1—C16—H10	109.0
C1—C14—C5	118.4 (2)	Br1—C16—H11	109.0
C1—C14—C13	123.4 (2)	C15—C16—H10	109.0
C5—C14—C13	118.2 (2)	C15—C16—H11	109.0
O1—C15—C13	123.2 (2)	H10—C16—H11	107.8
O1—C15—C16	124.1 (2)
C2—C1—C14—C5	−1.5 (4)	C12—C7—C8—C9	0.6 (4)
C2—C1—C14—C13	177.3 (2)	C7—C8—C9—C10	1.1 (4)
C14—C1—C2—C3	0.4 (4)	C8—C9—C10—C11	−1.2 (4)
C1—C2—C3—C4	1.4 (4)	C9—C10—C11—C12	−0.6 (4)
C2—C3—C4—C5	−1.9 (4)	C10—C11—C12—C7	2.4 (4)
C3—C4—C5—C6	−178.6 (2)	C10—C11—C12—C13	−178.7 (2)
C3—C4—C5—C14	0.7 (4)	C7—C12—C13—C14	2.6 (3)
C4—C5—C6—C7	179.4 (2)	C7—C12—C13—C15	−173.9 (2)
C4—C5—C14—C1	1.0 (3)	C11—C12—C13—C14	−176.4 (2)
C4—C5—C14—C13	−177.9 (2)	C11—C12—C13—C15	7.1 (4)
C6—C5—C14—C1	−179.7 (2)	C12—C13—C14—C1	178.4 (2)
C6—C5—C14—C13	1.4 (3)	C12—C13—C14—C5	−2.8 (3)
C14—C5—C6—C7	0.0 (3)	C12—C13—C15—O1	−107.4 (3)
C5—C6—C7—C8	−179.9 (2)	C12—C13—C15—C16	75.8 (3)
C5—C6—C7—C12	−0.2 (4)	C14—C13—C15—O1	76.0 (3)
C6—C7—C8—C9	−179.7 (2)	C14—C13—C15—C16	−100.8 (2)
C6—C7—C12—C11	178.0 (2)	C15—C13—C14—C1	−5.1 (3)
C6—C7—C12—C13	−1.1 (3)	C15—C13—C14—C5	173.7 (2)
C8—C7—C12—C11	−2.3 (3)	O1—C15—C16—Br1	19.3 (3)
C8—C7—C12—C13	178.6 (2)	C13—C15—C16—Br1	−163.94 (16)

Symmetry codes: (i) −x−1/2, y+1/2, −z+3/2; (ii) −x−1/2, y−1/2, −z+3/2; (iii) −x, −y, −z+1; (iv) −x, −y+1, −z+1; (v) x+1/2, −y+1/2, z+1/2; (vi) x−1/2, −y+1/2, z+1/2; (vii) −x+1/2, y−1/2, −z+3/2; (viii) x−1, y, z; (ix) x−1/2, −y+1/2, z−1/2; (x) −x+1/2, y+1/2, −z+3/2; (xi) x+1, y, z; (xii) x+1/2, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg3^ix	0.95	3.64	4.345	133
C10—H8···Cg2^x	0.95	2.99	3.865	153
C16—H10···O1^i	0.99	2.45	3.237 (3)	136

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