1-(4-Bromo­phen­yl)-3-(3,4-dimethoxy­phen­yl)prop-2-en-1-one

Each of the two unique mol­ecules of the title compound, C₁₇H₁₅BrO₃ is essentially planar. The crystal structure is stabilized by intra­molecular and inter­molecular C—H...O hydrogen bonds. These inter­actions link the symmetry-related mol­ecules into infinite chains along the c axis. These chains are then stacked parallel to the b axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.126
• Data-to-parameter ratio = 22.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   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
   2 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: H.K. Fun and I.A. Razak are supervisors of Shea-Lin Ng whereas S. M. Dharmaprakash is supervisor of Venkataraya Shettigar and P. S. Patil in this collaborative pulication. Mangalore University is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

1-(4-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

Crystal data

C17H15BrO3	F(000) = 1408
Mr = 347.20	Dx = 1.574 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8323 reflections
a = 31.3937 (5) Å	θ = 0.7–30.2°
b = 4.0139 (1) Å	µ = 2.81 mm^−1
c = 25.2400 (4) Å	T = 100 K
β = 112.885 (1)°	Block, colourless
V = 2930.17 (10) Å^3	0.34 × 0.22 × 0.17 mm
Z = 8

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	8691 independent reflections
Radiation source: fine-focus sealed tube	6361 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
Detector resolution: 8.33 pixels mm^-1	θmax = 30.2°, θmin = 0.7°
ω scans	h = −44→43
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→5
Tmin = 0.513, Tmax = 0.640	l = −35→35
82050 measured 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0518P)^2 + 4.4325P] where P = (Fo^2 + 2Fc^2)/3
8691 reflections	(Δ/σ)max = 0.001
383 parameters	Δρmax = 1.15 e Å^−3
0 restraints	Δρmin = −0.59 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	0.243195 (12)	0.78363 (9)	0.364808 (14)	0.02544 (9)
O1A	0.43095 (7)	0.0101 (6)	0.56496 (9)	0.0234 (5)
O2A	0.42737 (8)	−0.1186 (6)	0.89719 (9)	0.0220 (5)
O3A	0.35971 (8)	0.1809 (6)	0.81993 (9)	0.0230 (5)
C1A	0.32055 (11)	0.4319 (8)	0.52842 (13)	0.0200 (6)
H1AA	0.3167	0.4102	0.5630	0.024*
C2A	0.28588 (11)	0.5800 (8)	0.48168 (13)	0.0209 (6)
H2AA	0.2591	0.6594	0.4848	0.025*
C3A	0.29201 (11)	0.6068 (8)	0.43056 (13)	0.0191 (6)
C4A	0.33220 (11)	0.5001 (8)	0.42517 (13)	0.0226 (7)
H4AA	0.3361	0.5261	0.3907	0.027*
C5A	0.36633 (11)	0.3536 (8)	0.47250 (13)	0.0208 (6)
H5AA	0.3933	0.2793	0.4694	0.025*
C6A	0.36112 (10)	0.3151 (8)	0.52451 (12)	0.0170 (6)
C7A	0.39851 (10)	0.1403 (8)	0.57288 (12)	0.0166 (6)
C8A	0.39496 (11)	0.1302 (8)	0.62956 (13)	0.0193 (6)
H8AA	0.3723	0.2565	0.6353	0.023*
C9A	0.42343 (10)	−0.0555 (8)	0.67281 (13)	0.0176 (6)
H9AA	0.4452	−0.1829	0.6652	0.021*
C10A	0.42390 (10)	−0.0786 (8)	0.73069 (12)	0.0167 (6)
C11A	0.46010 (10)	−0.2441 (8)	0.77313 (13)	0.0183 (6)
H11A	0.4828	−0.3463	0.7636	0.022*
C12A	0.46309 (11)	−0.2600 (8)	0.82989 (13)	0.0188 (6)
H12A	0.4880	−0.3666	0.8579	0.023*
C13A	0.42888 (11)	−0.1167 (8)	0.84413 (13)	0.0186 (6)
C14A	0.39157 (10)	0.0499 (8)	0.80118 (13)	0.0177 (6)
C15A	0.38930 (10)	0.0683 (8)	0.74576 (13)	0.0174 (6)
H15A	0.3647	0.1787	0.7179	0.021*
C16A	0.46284 (12)	−0.3018 (9)	0.94117 (13)	0.0247 (7)
H16A	0.4580	−0.2886	0.9764	0.037*
H16B	0.4925	−0.2088	0.9469	0.037*
H16C	0.4618	−0.5306	0.9297	0.037*
C17A	0.32040 (11)	0.3401 (9)	0.77819 (14)	0.0239 (7)
H17A	0.2999	0.4106	0.7959	0.036*
H17B	0.3046	0.1866	0.7477	0.036*
H17C	0.3302	0.5304	0.7629	0.036*
Br1B	0.259531 (11)	−0.33561 (8)	0.118474 (14)	0.02385 (9)
O1B	0.07025 (8)	0.4369 (6)	0.13351 (9)	0.0243 (5)
O2B	0.07315 (8)	0.6055 (6)	0.46870 (9)	0.0221 (5)
O3B	0.14034 (8)	0.2929 (6)	0.45771 (9)	0.0232 (5)
C1B	0.17931 (11)	0.0004 (8)	0.20441 (13)	0.0215 (6)
H1BA	0.1819	0.0089	0.2424	0.026*
C2B	0.21422 (11)	−0.1457 (8)	0.19182 (13)	0.0201 (6)
H2BA	0.2400	−0.2361	0.2209	0.024*
C3B	0.21002 (11)	−0.1547 (8)	0.13538 (14)	0.0206 (6)
C4B	0.17119 (11)	−0.0309 (9)	0.09097 (13)	0.0231 (7)
H4BA	0.1685	−0.0450	0.0530	0.028*
C5B	0.13667 (11)	0.1138 (8)	0.10435 (13)	0.0210 (6)
H5BA	0.1106	0.1986	0.0750	0.025*
C6B	0.14025 (10)	0.1351 (8)	0.16116 (13)	0.0180 (6)
C7B	0.10246 (11)	0.3079 (8)	0.17312 (13)	0.0189 (6)
C8B	0.10561 (11)	0.3220 (8)	0.23294 (13)	0.0199 (6)
H8BA	0.1284	0.1990	0.2610	0.024*
C9B	0.07659 (10)	0.5065 (8)	0.24799 (13)	0.0184 (6)
H9BA	0.0545	0.6289	0.2189	0.022*
C10B	0.07605 (10)	0.5351 (7)	0.30545 (13)	0.0177 (6)
C11B	0.03993 (11)	0.7034 (8)	0.31231 (13)	0.0182 (6)
H11B	0.0171	0.8003	0.2804	0.022*
C12B	0.03688 (10)	0.7312 (8)	0.36610 (13)	0.0188 (6)
H12B	0.0120	0.8409	0.3696	0.023*
C13B	0.07146 (10)	0.5927 (8)	0.41405 (12)	0.0185 (6)
C14B	0.10847 (10)	0.4181 (8)	0.40762 (13)	0.0186 (6)
C15B	0.11055 (10)	0.3916 (8)	0.35430 (13)	0.0182 (6)
H15B	0.1350	0.2778	0.3505	0.022*
C16B	0.03795 (12)	0.7947 (9)	0.47819 (15)	0.0248 (7)
H16D	0.0433	0.7896	0.5183	0.037*
H16G	0.0082	0.7000	0.4562	0.037*
H16E	0.0388	1.0211	0.4664	0.037*
C17B	0.17875 (11)	0.1205 (9)	0.45376 (14)	0.0244 (7)
H17G	0.1996	0.0545	0.4915	0.037*
H17D	0.1945	0.2647	0.4370	0.037*
H17E	0.1679	−0.0736	0.4301	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.02744 (18)	0.02786 (18)	0.01961 (16)	0.00426 (13)	0.00761 (13)	0.00541 (13)
O1A	0.0217 (11)	0.0306 (13)	0.0191 (11)	0.0023 (10)	0.0091 (9)	−0.0015 (10)
O2A	0.0251 (12)	0.0276 (12)	0.0139 (10)	0.0031 (9)	0.0083 (9)	0.0031 (9)
O3A	0.0215 (11)	0.0335 (13)	0.0175 (10)	0.0069 (10)	0.0112 (9)	0.0050 (10)
C1A	0.0226 (15)	0.0229 (16)	0.0165 (14)	−0.0004 (12)	0.0099 (12)	0.0001 (12)
C2A	0.0207 (15)	0.0216 (15)	0.0219 (15)	−0.0005 (12)	0.0101 (12)	−0.0004 (12)
C3A	0.0222 (15)	0.0160 (14)	0.0166 (14)	−0.0019 (12)	0.0049 (12)	−0.0003 (11)
C4A	0.0274 (16)	0.0261 (17)	0.0159 (14)	0.0005 (13)	0.0102 (13)	0.0009 (12)
C5A	0.0191 (14)	0.0277 (17)	0.0181 (14)	−0.0004 (13)	0.0100 (12)	−0.0024 (13)
C6A	0.0175 (14)	0.0174 (14)	0.0154 (13)	−0.0030 (11)	0.0056 (11)	−0.0027 (11)
C7A	0.0184 (14)	0.0171 (14)	0.0137 (13)	−0.0034 (11)	0.0056 (11)	−0.0012 (11)
C8A	0.0224 (15)	0.0199 (15)	0.0179 (14)	−0.0003 (12)	0.0103 (12)	−0.0026 (12)
C9A	0.0199 (14)	0.0159 (14)	0.0208 (14)	−0.0029 (11)	0.0119 (12)	−0.0018 (12)
C10A	0.0190 (14)	0.0153 (14)	0.0159 (13)	−0.0029 (11)	0.0069 (11)	−0.0011 (11)
C11A	0.0180 (14)	0.0170 (14)	0.0200 (14)	0.0007 (11)	0.0076 (12)	0.0002 (11)
C12A	0.0177 (14)	0.0168 (14)	0.0206 (15)	−0.0012 (11)	0.0061 (12)	0.0010 (11)
C13A	0.0211 (15)	0.0186 (15)	0.0166 (14)	−0.0035 (12)	0.0079 (12)	0.0000 (11)
C14A	0.0163 (14)	0.0197 (15)	0.0188 (14)	0.0002 (12)	0.0085 (11)	0.0009 (12)
C15A	0.0167 (14)	0.0169 (14)	0.0179 (14)	0.0008 (11)	0.0060 (11)	0.0014 (11)
C16A	0.0303 (18)	0.0268 (17)	0.0139 (14)	0.0019 (14)	0.0054 (13)	0.0036 (13)
C17A	0.0204 (15)	0.0259 (17)	0.0253 (16)	0.0046 (13)	0.0089 (13)	0.0013 (13)
Br1B	0.02636 (17)	0.02407 (17)	0.02475 (16)	0.00156 (13)	0.01390 (13)	−0.00020 (13)
O1B	0.0241 (11)	0.0312 (13)	0.0172 (10)	0.0020 (10)	0.0077 (9)	0.0034 (10)
O2B	0.0253 (11)	0.0271 (12)	0.0169 (10)	0.0028 (10)	0.0115 (9)	−0.0003 (9)
O3B	0.0237 (12)	0.0314 (13)	0.0134 (10)	0.0065 (10)	0.0061 (9)	0.0013 (9)
C1B	0.0254 (16)	0.0267 (17)	0.0118 (13)	−0.0010 (13)	0.0065 (12)	−0.0007 (12)
C2B	0.0209 (15)	0.0251 (16)	0.0132 (13)	0.0000 (13)	0.0054 (11)	0.0008 (12)
C3B	0.0185 (14)	0.0194 (15)	0.0254 (16)	−0.0030 (12)	0.0102 (12)	−0.0028 (12)
C4B	0.0279 (17)	0.0255 (17)	0.0170 (14)	0.0007 (13)	0.0099 (13)	0.0009 (13)
C5B	0.0257 (16)	0.0227 (16)	0.0136 (13)	−0.0003 (13)	0.0065 (12)	0.0014 (12)
C6B	0.0195 (14)	0.0167 (14)	0.0163 (14)	−0.0035 (11)	0.0052 (11)	−0.0002 (11)
C7B	0.0193 (15)	0.0168 (14)	0.0189 (14)	−0.0038 (12)	0.0058 (12)	−0.0007 (12)
C8B	0.0204 (15)	0.0226 (16)	0.0175 (14)	0.0004 (12)	0.0082 (12)	0.0014 (12)
C9B	0.0211 (15)	0.0168 (15)	0.0175 (14)	−0.0035 (12)	0.0078 (12)	−0.0002 (11)
C10B	0.0213 (15)	0.0136 (14)	0.0180 (14)	−0.0025 (11)	0.0074 (12)	−0.0015 (11)
C11B	0.0192 (14)	0.0176 (14)	0.0159 (14)	0.0008 (12)	0.0049 (11)	0.0003 (11)
C12B	0.0160 (14)	0.0169 (14)	0.0234 (15)	−0.0006 (11)	0.0078 (12)	−0.0031 (12)
C13B	0.0205 (15)	0.0184 (15)	0.0159 (14)	−0.0028 (12)	0.0064 (12)	−0.0036 (11)
C14B	0.0177 (14)	0.0182 (15)	0.0173 (14)	0.0002 (12)	0.0040 (11)	0.0018 (12)
C15B	0.0195 (14)	0.0167 (14)	0.0195 (14)	−0.0004 (11)	0.0087 (12)	−0.0016 (12)
C16B	0.0283 (17)	0.0263 (17)	0.0261 (16)	0.0035 (14)	0.0174 (14)	−0.0026 (14)
C17B	0.0227 (16)	0.0251 (17)	0.0222 (15)	0.0052 (13)	0.0053 (13)	−0.0011 (13)

Geometric parameters (Å, º)

Br1A—C3A	1.905 (3)	Br1B—C3B	1.908 (3)
O1A—C7A	1.228 (4)	O1B—C7B	1.226 (4)
O2A—C13A	1.358 (4)	O2B—C13B	1.361 (4)
O2A—C16A	1.432 (4)	O2B—C16B	1.436 (4)
O3A—C14A	1.367 (4)	O3B—C14B	1.367 (4)
O3A—C17A	1.425 (4)	O3B—C17B	1.427 (4)
C1A—C2A	1.390 (4)	C1B—C2B	1.385 (4)
C1A—C6A	1.396 (4)	C1B—C6B	1.395 (4)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.381 (4)	C2B—C3B	1.379 (4)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.388 (4)	C3B—C4B	1.388 (4)
C4A—C5A	1.388 (4)	C4B—C5B	1.382 (4)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.393 (4)	C5B—C6B	1.397 (4)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.499 (4)	C6B—C7B	1.503 (4)
C7A—C8A	1.478 (4)	C7B—C8B	1.475 (4)
C8A—C9A	1.337 (4)	C8B—C9B	1.339 (4)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.458 (4)	C9B—C10B	1.461 (4)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C11A	1.390 (4)	C10B—C11B	1.387 (4)
C10A—C15A	1.412 (4)	C10B—C15B	1.409 (4)
C11A—C12A	1.400 (4)	C11B—C12B	1.402 (4)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.383 (4)	C12B—C13B	1.389 (4)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.417 (4)	C13B—C14B	1.419 (4)
C14A—C15A	1.374 (4)	C14B—C15B	1.376 (4)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—H16A	0.9600	C16B—H16D	0.9600
C16A—H16B	0.9600	C16B—H16G	0.9600
C16A—H16C	0.9600	C16B—H16E	0.9600
C17A—H17A	0.9600	C17B—H17G	0.9600
C17A—H17B	0.9600	C17B—H17D	0.9600
C17A—H17C	0.9600	C17B—H17E	0.9600
C13A—O2A—C16A	116.9 (2)	C13B—O2B—C16B	117.4 (2)
C14A—O3A—C17A	117.2 (2)	C14B—O3B—C17B	116.6 (2)
C2A—C1A—C6A	121.2 (3)	C2B—C1B—C6B	121.2 (3)
C2A—C1A—H1AA	119.4	C2B—C1B—H1BA	119.4
C6A—C1A—H1AA	119.4	C6B—C1B—H1BA	119.4
C3A—C2A—C1A	118.6 (3)	C3B—C2B—C1B	118.8 (3)
C3A—C2A—H2AA	120.7	C3B—C2B—H2BA	120.6
C1A—C2A—H2AA	120.7	C1B—C2B—H2BA	120.6
C2A—C3A—C4A	122.0 (3)	C2B—C3B—C4B	121.7 (3)
C2A—C3A—Br1A	119.1 (2)	C2B—C3B—Br1B	118.8 (2)
C4A—C3A—Br1A	118.9 (2)	C4B—C3B—Br1B	119.4 (2)
C5A—C4A—C3A	118.3 (3)	C5B—C4B—C3B	118.6 (3)
C5A—C4A—H4AA	120.9	C5B—C4B—H4BA	120.7
C3A—C4A—H4AA	120.9	C3B—C4B—H4BA	120.7
C4A—C5A—C6A	121.6 (3)	C4B—C5B—C6B	121.3 (3)
C4A—C5A—H5AA	119.2	C4B—C5B—H5BA	119.4
C6A—C5A—H5AA	119.2	C6B—C5B—H5BA	119.4
C5A—C6A—C1A	118.3 (3)	C1B—C6B—C5B	118.3 (3)
C5A—C6A—C7A	118.5 (3)	C1B—C6B—C7B	123.0 (3)
C1A—C6A—C7A	123.1 (3)	C5B—C6B—C7B	118.7 (3)
O1A—C7A—C8A	121.7 (3)	O1B—C7B—C8B	121.6 (3)
O1A—C7A—C6A	120.2 (3)	O1B—C7B—C6B	119.8 (3)
C8A—C7A—C6A	118.1 (3)	C8B—C7B—C6B	118.6 (3)
C9A—C8A—C7A	121.9 (3)	C9B—C8B—C7B	122.0 (3)
C9A—C8A—H8AA	119.1	C9B—C8B—H8BA	119.0
C7A—C8A—H8AA	119.1	C7B—C8B—H8BA	119.0
C8A—C9A—C10A	126.6 (3)	C8B—C9B—C10B	126.6 (3)
C8A—C9A—H9AA	116.7	C8B—C9B—H9BA	116.7
C10A—C9A—H9AA	116.7	C10B—C9B—H9BA	116.7
C11A—C10A—C15A	118.4 (3)	C11B—C10B—C15B	118.5 (3)
C11A—C10A—C9A	119.3 (3)	C11B—C10B—C9B	119.2 (3)
C15A—C10A—C9A	122.3 (3)	C15B—C10B—C9B	122.3 (3)
C10A—C11A—C12A	121.3 (3)	C10B—C11B—C12B	121.8 (3)
C10A—C11A—H11A	119.4	C10B—C11B—H11B	119.1
C12A—C11A—H11A	119.4	C12B—C11B—H11B	119.1
C13A—C12A—C11A	119.8 (3)	C13B—C12B—C11B	119.2 (3)
C13A—C12A—H12A	120.1	C13B—C12B—H12B	120.4
C11A—C12A—H12A	120.1	C11B—C12B—H12B	120.4
O2A—C13A—C12A	125.6 (3)	O2B—C13B—C12B	125.3 (3)
O2A—C13A—C14A	114.9 (3)	O2B—C13B—C14B	115.1 (3)
C12A—C13A—C14A	119.5 (3)	C12B—C13B—C14B	119.7 (3)
O3A—C14A—C15A	125.2 (3)	O3B—C14B—C15B	125.5 (3)
O3A—C14A—C13A	114.5 (3)	O3B—C14B—C13B	114.4 (3)
C15A—C14A—C13A	120.3 (3)	C15B—C14B—C13B	120.1 (3)
C14A—C15A—C10A	120.7 (3)	C14B—C15B—C10B	120.8 (3)
C14A—C15A—H15A	119.6	C14B—C15B—H15B	119.6
C10A—C15A—H15A	119.6	C10B—C15B—H15B	119.6
O2A—C16A—H16A	109.5	O2B—C16B—H16D	109.5
O2A—C16A—H16B	109.5	O2B—C16B—H16G	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16G	109.5
O2A—C16A—H16C	109.5	O2B—C16B—H16E	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16E	109.5
H16B—C16A—H16C	109.5	H16G—C16B—H16E	109.5
O3A—C17A—H17A	109.5	O3B—C17B—H17G	109.5
O3A—C17A—H17B	109.5	O3B—C17B—H17D	109.5
H17A—C17A—H17B	109.5	H17G—C17B—H17D	109.5
O3A—C17A—H17C	109.5	O3B—C17B—H17E	109.5
H17A—C17A—H17C	109.5	H17G—C17B—H17E	109.5
H17B—C17A—H17C	109.5	H17D—C17B—H17E	109.5
C6A—C1A—C2A—C3A	0.7 (5)	C6B—C1B—C2B—C3B	0.4 (5)
C1A—C2A—C3A—C4A	−2.0 (5)	C1B—C2B—C3B—C4B	−2.1 (5)
C1A—C2A—C3A—Br1A	176.1 (2)	C1B—C2B—C3B—Br1B	176.9 (2)
C2A—C3A—C4A—C5A	1.9 (5)	C2B—C3B—C4B—C5B	2.0 (5)
Br1A—C3A—C4A—C5A	−176.2 (2)	Br1B—C3B—C4B—C5B	−176.9 (2)
C3A—C4A—C5A—C6A	−0.5 (5)	C3B—C4B—C5B—C6B	−0.3 (5)
C4A—C5A—C6A—C1A	−0.8 (5)	C2B—C1B—C6B—C5B	1.2 (5)
C4A—C5A—C6A—C7A	177.2 (3)	C2B—C1B—C6B—C7B	−177.5 (3)
C2A—C1A—C6A—C5A	0.7 (5)	C4B—C5B—C6B—C1B	−1.2 (5)
C2A—C1A—C6A—C7A	−177.2 (3)	C4B—C5B—C6B—C7B	177.5 (3)
C5A—C6A—C7A—O1A	−6.1 (4)	C1B—C6B—C7B—O1B	176.0 (3)
C1A—C6A—C7A—O1A	171.8 (3)	C5B—C6B—C7B—O1B	−2.6 (4)
C5A—C6A—C7A—C8A	174.0 (3)	C1B—C6B—C7B—C8B	−3.0 (5)
C1A—C6A—C7A—C8A	−8.1 (4)	C5B—C6B—C7B—C8B	178.3 (3)
O1A—C7A—C8A—C9A	−8.6 (5)	O1B—C7B—C8B—C9B	−7.6 (5)
C6A—C7A—C8A—C9A	171.3 (3)	C6B—C7B—C8B—C9B	171.4 (3)
C7A—C8A—C9A—C10A	178.4 (3)	C7B—C8B—C9B—C10B	179.0 (3)
C8A—C9A—C10A—C11A	−170.4 (3)	C8B—C9B—C10B—C11B	−171.7 (3)
C8A—C9A—C10A—C15A	8.1 (5)	C8B—C9B—C10B—C15B	6.9 (5)
C15A—C10A—C11A—C12A	−1.4 (5)	C15B—C10B—C11B—C12B	−0.5 (5)
C9A—C10A—C11A—C12A	177.1 (3)	C9B—C10B—C11B—C12B	178.2 (3)
C10A—C11A—C12A—C13A	1.8 (5)	C10B—C11B—C12B—C13B	1.4 (5)
C16A—O2A—C13A—C12A	−3.9 (5)	C16B—O2B—C13B—C12B	−4.1 (5)
C16A—O2A—C13A—C14A	176.3 (3)	C16B—O2B—C13B—C14B	176.6 (3)
C11A—C12A—C13A—O2A	179.1 (3)	C11B—C12B—C13B—O2B	179.0 (3)
C11A—C12A—C13A—C14A	−1.1 (5)	C11B—C12B—C13B—C14B	−1.7 (5)
C17A—O3A—C14A—C15A	2.0 (5)	C17B—O3B—C14B—C15B	−0.1 (5)
C17A—O3A—C14A—C13A	−177.6 (3)	C17B—O3B—C14B—C13B	−178.8 (3)
O2A—C13A—C14A—O3A	−0.4 (4)	O2B—C13B—C14B—O3B	−0.6 (4)
C12A—C13A—C14A—O3A	179.8 (3)	C12B—C13B—C14B—O3B	−180.0 (3)
O2A—C13A—C14A—C15A	−180.0 (3)	O2B—C13B—C14B—C15B	−179.4 (3)
C12A—C13A—C14A—C15A	0.2 (5)	C12B—C13B—C14B—C15B	1.2 (5)
O3A—C14A—C15A—C10A	−179.4 (3)	O3B—C14B—C15B—C10B	−179.0 (3)
C13A—C14A—C15A—C10A	0.2 (5)	C13B—C14B—C15B—C10B	−0.3 (5)
C11A—C10A—C15A—C14A	0.4 (5)	C11B—C10B—C15B—C14B	−0.1 (5)
C9A—C10A—C15A—C14A	−178.1 (3)	C9B—C10B—C15B—C14B	−178.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9A—H9AA···O1A	0.93	2.51	2.835 (4)	100
C4A—H4AA···O3A^i	0.93	2.34	3.180 (4)	151
C12A—H12A···O1A^ii	0.93	2.58	3.478 (4)	162
C16A—H16C···O2A^iii	0.96	2.59	3.501 (4)	158
C9B—H9BA···O1B	0.93	2.51	2.832 (4)	100
C4B—H4BA···O3B^i	0.93	2.44	3.260 (4)	148
C12B—H12B···O1B^iv	0.93	2.58	3.467 (4)	159
C16B—H16E···O2B^v	0.96	2.57	3.475 (4)	157

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y−1, z; (iv) −x, y+1/2, −z+1/2; (v) x, y+1, z.