4-[2,3-Dibromo-3-(4-bromo-phen-yl)propano-yl]-2-phenyl-1,2,3-oxadiazol-2-ium-5-olate.

In the title compound, C(17)H(11)Br(3)N(2)O(3), the whole mol-ecule is disordered over two positions with a refined occupancy ratio of 0.770 (5):0.230 (5). In the major component, the 1,2,3-oxadiazo-lidine ring is essentially planar [maximum deviation = 0.017 (6) Å] and makes dihedral angles of 22.5 (3) and 70.2 (3)° with the 4-bromo-phenyl and phenyl rings, respectively. In the minor component, the corresponding values are 18.9 (11) and 84.9 (12)°. In the crystal, inter-molecular C-H⋯Br hydrogen bonds link the mol-ecules into ribbons along [010]. There is a short O⋯N contact [2.83 (3) Å] in the minor component. In the major component, the mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond, which forms an S(6) ring motif.

Related literature

For biological activity of sydnones, mesoionic compounds having a 1,2,3-oxadiazole skeleton and bearing an oxygen atom attached to the 5-position, see: Jyothi et al. (2008 ▶); Rai et al. (2007 ▶; 2008 ▶). For a related structure, see: Goh et al. (2010 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H11Br3N2O3

M = 531.01

Monoclinic,

a = 17.6996 (3) Å

b = 5.8322 (1) Å

c = 18.2445 (3) Å

β = 105.973 (1)°

V = 1810.62 (5) Å3

Z = 4

Mo Kα radiation

μ = 6.70 mm−1

T = 100 K

0.43 × 0.38 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.159, T max = 0.505

20140 measured reflections

5243 independent reflections

4218 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.055

S = 1.02

5243 reflections

352 parameters

207 restraints

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040493/sj5039sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040493/sj5039Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H11Br3N2O3	F(000) = 1024
Mr = 531.01	Dx = 1.948 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9198 reflections
a = 17.6996 (3) Å	θ = 2.4–29.8°
b = 5.8322 (1) Å	µ = 6.70 mm−1
c = 18.2445 (3) Å	T = 100 K
β = 105.973 (1)°	Block, yellow
V = 1810.62 (5) Å3	0.43 × 0.38 × 0.12 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5243 independent reflections
Radiation source: fine-focus sealed tube	4218 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −24→24
Tmin = 0.159, Tmax = 0.505	k = −8→7
20140 measured reflections	l = −24→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0238P)2 + 0.3541P] where P = (Fo2 + 2Fc2)/3
5243 reflections	(Δ/σ)max = 0.002
352 parameters	Δρmax = 0.50 e Å−3
207 restraints	Δρmin = −0.37 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1A	0.39809 (10)	0.0392 (3)	0.03443 (10)	0.03273 (19)	0.770 (5)
Br2A	0.46821 (7)	0.55027 (18)	0.23460 (8)	0.0428 (3)	0.770 (5)
Br3A	0.80250 (8)	0.0292 (2)	0.16887 (6)	0.03402 (19)	0.770 (5)
O1A	0.1949 (3)	−0.0068 (9)	0.1943 (3)	0.0282 (8)	0.770 (5)
O2A	0.32784 (19)	−0.0399 (6)	0.2397 (2)	0.0293 (6)	0.770 (5)
O3A	0.30678 (12)	0.5098 (4)	0.06838 (17)	0.0339 (6)	0.770 (5)
N1A	0.1841 (3)	0.2416 (10)	0.1078 (3)	0.0233 (9)	0.770 (5)
N2A	0.1416 (3)	0.1153 (13)	0.1392 (4)	0.0299 (11)	0.770 (5)
C1A	0.1437 (4)	0.3491 (9)	−0.0250 (3)	0.0435 (13)	0.770 (5)
H1AA	0.1703	0.2222	−0.0363	0.052*	0.770 (5)
C2A	0.1033 (3)	0.4963 (9)	−0.0814 (3)	0.0473 (11)	0.770 (5)
H2AA	0.1010	0.4676	−0.1321	0.057*	0.770 (5)
C3A	0.0659 (3)	0.6880 (8)	−0.0620 (3)	0.0416 (10)	0.770 (5)
H3AA	0.0396	0.7889	−0.1000	0.050*	0.770 (5)
C4A	0.0676 (4)	0.7296 (9)	0.0128 (3)	0.0381 (10)	0.770 (5)
H4AA	0.0414	0.8564	0.0248	0.046*	0.770 (5)
C5A	0.1078 (5)	0.5851 (12)	0.0702 (4)	0.0301 (11)	0.770 (5)
H5AA	0.1109	0.6131	0.1211	0.036*	0.770 (5)
C6A	0.1432 (6)	0.3969 (14)	0.0479 (3)	0.0292 (16)	0.770 (5)
C7A	0.2730 (2)	0.0478 (7)	0.1932 (3)	0.0261 (8)	0.770 (5)
C8A	0.26327 (18)	0.2104 (6)	0.1337 (2)	0.0231 (7)	0.770 (5)
C12A	0.54873 (13)	0.3090 (5)	0.14317 (17)	0.0243 (6)	0.770 (5)
C13A	0.57473 (14)	0.1083 (5)	0.18318 (18)	0.0274 (6)	0.770 (5)
H13A	0.5415	0.0287	0.2057	0.033*	0.770 (5)
C14A	0.6501 (2)	0.0248 (8)	0.1899 (3)	0.0292 (8)	0.770 (5)
H14A	0.6677	−0.1086	0.2172	0.035*	0.770 (5)
C15A	0.6983 (4)	0.1445 (18)	0.1551 (9)	0.033 (2)	0.770 (5)
C16A	0.6744 (3)	0.3462 (14)	0.1168 (5)	0.0332 (15)	0.770 (5)
H16A	0.7085	0.4278	0.0958	0.040*	0.770 (5)
C17A	0.59879 (19)	0.4272 (7)	0.1096 (2)	0.0267 (7)	0.770 (5)
H17A	0.5817	0.5609	0.0823	0.032*	0.770 (5)
C9A	0.32136 (14)	0.3360 (5)	0.10637 (19)	0.0266 (6)	0.770 (5)
C10A	0.40246 (13)	0.2259 (5)	0.12510 (16)	0.0245 (6)	0.770 (5)
H10A	0.4109	0.1284	0.1704	0.029*	0.770 (5)
C11A	0.46785 (13)	0.4009 (4)	0.13558 (15)	0.0241 (6)	0.770 (5)
H11A	0.4542	0.5140	0.0943	0.029*	0.770 (5)
Br1B	0.3986 (4)	0.0778 (11)	0.0224 (4)	0.0432 (10)	0.230 (5)
Br2B	0.4661 (2)	0.5668 (4)	0.2298 (2)	0.0207 (6)	0.230 (5)
Br3B	0.8041 (3)	0.0491 (10)	0.1649 (3)	0.0645 (14)	0.230 (5)
O1B	0.2081 (8)	−0.011 (3)	0.1999 (11)	0.025 (3)*	0.230 (5)
O2B	0.3419 (6)	−0.015 (2)	0.2543 (7)	0.025 (3)*	0.230 (5)
O3B	0.3133 (5)	0.5587 (14)	0.0938 (5)	0.035 (2)*	0.230 (5)
N1B	0.1956 (8)	0.248 (4)	0.1157 (11)	0.025 (4)*	0.230 (5)
N2B	0.1529 (8)	0.109 (4)	0.1467 (12)	0.016 (3)*	0.230 (5)
C1B	0.1377 (11)	0.305 (3)	−0.0245 (9)	0.021 (3)*	0.230 (5)
H1BA	0.1580	0.1639	−0.0332	0.026*	0.230 (5)
C2B	0.0980 (11)	0.437 (2)	−0.0865 (9)	0.035 (4)*	0.230 (5)
H2BA	0.0960	0.3898	−0.1357	0.042*	0.230 (5)
C3B	0.0620 (10)	0.635 (2)	−0.0751 (9)	0.031 (3)*	0.230 (5)
H3BA	0.0310	0.7161	−0.1164	0.037*	0.230 (5)
C4B	0.0718 (13)	0.714 (3)	−0.0023 (10)	0.031 (4)*	0.230 (5)
H4BA	0.0516	0.8565	0.0055	0.037*	0.230 (5)
C5B	0.112 (2)	0.581 (5)	0.0605 (12)	0.038 (6)*	0.230 (5)
H5BA	0.1144	0.6306	0.1095	0.045*	0.230 (5)
C6B	0.1480 (19)	0.378 (5)	0.0502 (9)	0.022 (5)*	0.230 (5)
C7B	0.2854 (7)	0.064 (3)	0.2074 (7)	0.015 (3)*	0.230 (5)
C8B	0.2729 (6)	0.237 (2)	0.1508 (6)	0.019 (3)*	0.230 (5)
C12B	0.5443 (5)	0.2546 (16)	0.1212 (5)	0.023 (2)*	0.230 (5)
C13B	0.5719 (6)	0.0563 (17)	0.1606 (6)	0.029 (3)*	0.230 (5)
H13B	0.5374	−0.0375	0.1771	0.035*	0.230 (5)
C14B	0.6499 (8)	−0.005 (3)	0.1759 (10)	0.032 (4)*	0.230 (5)
H14B	0.6676	−0.1432	0.2000	0.038*	0.230 (5)
C15B	0.7008 (10)	0.142 (5)	0.155 (3)	0.019 (6)*	0.230 (5)
C16B	0.6757 (10)	0.331 (4)	0.1083 (16)	0.018 (3)*	0.230 (5)
H16B	0.7096	0.4148	0.0875	0.022*	0.230 (5)
C17B	0.5971 (7)	0.388 (2)	0.0948 (8)	0.026 (3)*	0.230 (5)
H17B	0.5786	0.5199	0.0670	0.031*	0.230 (5)
C9B	0.3306 (5)	0.3857 (16)	0.1293 (6)	0.025 (2)*	0.230 (5)
C10B	0.4170 (4)	0.3055 (17)	0.1585 (5)	0.029 (2)	0.230 (5)
H10B	0.4223	0.1566	0.1843	0.035*	0.230 (5)
C11B	0.4576 (4)	0.3139 (16)	0.0966 (5)	0.032 (2)	0.230 (5)
H11B	0.4503	0.4655	0.0725	0.038*	0.230 (5)

	U11	U22	U33	U12	U13	U23
Br1A	0.0304 (2)	0.0336 (3)	0.0315 (5)	−0.0036 (2)	0.0040 (3)	−0.0067 (3)
Br2A	0.0259 (3)	0.0618 (6)	0.0411 (4)	−0.0048 (3)	0.0101 (3)	−0.0172 (4)
Br3A	0.0247 (4)	0.0442 (3)	0.0324 (3)	0.0101 (2)	0.0065 (2)	−0.0044 (2)
O1A	0.0256 (15)	0.0239 (12)	0.0370 (18)	0.0000 (14)	0.0119 (15)	0.0039 (9)
O2A	0.0259 (13)	0.0293 (13)	0.0317 (16)	0.0041 (11)	0.0061 (11)	0.0065 (12)
O3A	0.0259 (10)	0.0315 (12)	0.0420 (15)	0.0016 (8)	0.0054 (10)	0.0170 (11)
N1A	0.0199 (14)	0.0208 (13)	0.0299 (18)	−0.0014 (13)	0.0080 (12)	−0.0024 (12)
N2A	0.0267 (19)	0.0269 (15)	0.034 (2)	−0.0022 (17)	0.0050 (17)	−0.0016 (12)
C1A	0.047 (2)	0.040 (3)	0.048 (2)	0.004 (2)	0.0208 (15)	0.0047 (19)
C2A	0.054 (2)	0.056 (3)	0.0329 (18)	0.000 (2)	0.0135 (15)	0.0065 (19)
C3A	0.0350 (17)	0.035 (2)	0.046 (3)	−0.0005 (16)	−0.0032 (15)	0.0080 (18)
C4A	0.0311 (17)	0.0349 (19)	0.043 (3)	0.0083 (11)	0.001 (2)	−0.0001 (18)
C5A	0.0250 (17)	0.0277 (19)	0.034 (2)	0.0012 (10)	0.0011 (19)	−0.0035 (15)
C6A	0.022 (2)	0.028 (3)	0.036 (2)	0.0023 (12)	0.0047 (11)	0.0061 (12)
C7A	0.0251 (17)	0.0225 (14)	0.030 (2)	−0.0001 (12)	0.0070 (14)	−0.0037 (15)
C8A	0.0212 (14)	0.0225 (14)	0.0239 (16)	0.0007 (9)	0.0035 (12)	−0.0004 (13)
C12A	0.0218 (11)	0.0239 (13)	0.0265 (14)	−0.0024 (9)	0.0057 (10)	−0.0035 (11)
C13A	0.0254 (12)	0.0295 (14)	0.0277 (15)	−0.0032 (10)	0.0079 (10)	0.0007 (12)
C14A	0.0269 (15)	0.0287 (17)	0.030 (2)	0.0057 (11)	0.0041 (12)	0.0021 (16)
C15A	0.021 (2)	0.045 (3)	0.030 (2)	0.0018 (11)	0.0034 (11)	−0.0086 (12)
C16A	0.0256 (16)	0.045 (3)	0.032 (3)	−0.0077 (12)	0.0123 (13)	−0.005 (2)
C17A	0.0276 (14)	0.0241 (16)	0.0286 (18)	−0.0012 (10)	0.0083 (12)	0.0004 (15)
C9A	0.0225 (12)	0.0277 (14)	0.0279 (15)	−0.0012 (10)	0.0042 (10)	0.0012 (12)
C10A	0.0218 (11)	0.0253 (14)	0.0247 (14)	−0.0001 (9)	0.0035 (10)	0.0024 (10)
C11A	0.0217 (11)	0.0252 (13)	0.0250 (14)	−0.0001 (9)	0.0054 (9)	0.0019 (10)
Br1B	0.0388 (8)	0.057 (2)	0.0294 (14)	−0.0112 (12)	0.0026 (8)	−0.0042 (12)
Br2B	0.0323 (12)	0.0050 (8)	0.0308 (10)	−0.0039 (6)	0.0186 (8)	−0.0053 (6)
Br3B	0.0315 (16)	0.096 (3)	0.070 (2)	0.0027 (15)	0.0214 (14)	−0.0156 (16)
C10B	0.022 (4)	0.029 (5)	0.033 (5)	−0.002 (3)	0.001 (4)	0.004 (4)
C11B	0.027 (4)	0.032 (5)	0.032 (5)	−0.005 (3)	0.001 (3)	0.001 (4)

Br1A—C10A	1.964 (4)	Br1B—C11B	2.010 (12)
Br2A—C11A	2.004 (3)	Br2B—C10B	2.036 (11)
Br3A—C15A	1.913 (5)	Br3B—C15B	1.867 (13)
O1A—N2A	1.374 (5)	O1B—N2B	1.367 (13)
O1A—C7A	1.423 (5)	O1B—C7B	1.407 (13)
O2A—C7A	1.212 (4)	O2B—C7B	1.214 (12)
O3A—C9A	1.215 (3)	O3B—C9B	1.193 (11)
N1A—N2A	1.293 (4)	N1B—N2B	1.334 (14)
N1A—C8A	1.363 (4)	N1B—C8B	1.344 (12)
N1A—C6A	1.450 (5)	N1B—C6B	1.469 (13)
C1A—C6A	1.362 (5)	C1B—C2B	1.386 (14)
C1A—C2A	1.379 (5)	C1B—C6B	1.392 (13)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.393 (5)	C2B—C3B	1.365 (14)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.380 (6)	C3B—C4B	1.370 (14)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.379 (5)	C4B—C5B	1.403 (15)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.379 (6)	C5B—C6B	1.382 (14)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C7A—C8A	1.415 (4)	C7B—C8B	1.419 (12)
C8A—C9A	1.458 (3)	C8B—C9B	1.472 (11)
C12A—C13A	1.390 (3)	C12B—C13B	1.378 (11)
C12A—C17A	1.391 (3)	C12B—C17B	1.400 (12)
C12A—C11A	1.499 (3)	C12B—C11B	1.515 (10)
C13A—C14A	1.393 (4)	C13B—C14B	1.378 (13)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.385 (6)	C14B—C15B	1.374 (14)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C16A	1.374 (6)	C15B—C16B	1.389 (14)
C16A—C17A	1.391 (5)	C16B—C17B	1.384 (14)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—H17A	0.9300	C17B—H17B	0.9300
C9A—C10A	1.523 (3)	C9B—C10B	1.547 (10)
C10A—C11A	1.515 (3)	C10B—C11B	1.497 (11)
C10A—H10A	0.9800	C10B—H10B	0.9800
C11A—H11A	0.9800	C11B—H11B	0.9800
N2A—O1A—C7A	110.4 (4)	N2B—O1B—C7B	113.3 (12)
N2A—N1A—C8A	116.0 (4)	N2B—N1B—C8B	113.0 (11)
N2A—N1A—C6A	117.4 (5)	N2B—N1B—C6B	113.1 (17)
C8A—N1A—C6A	126.6 (5)	C8B—N1B—C6B	133.9 (18)
N1A—N2A—O1A	104.6 (4)	N1B—N2B—O1B	103.6 (12)
C6A—C1A—C2A	117.4 (5)	C2B—C1B—C6B	122.0 (14)
C6A—C1A—H1AA	121.3	C2B—C1B—H1BA	119.0
C2A—C1A—H1AA	121.3	C6B—C1B—H1BA	119.0
C1A—C2A—C3A	119.7 (4)	C3B—C2B—C1B	119.9 (14)
C1A—C2A—H2AA	120.1	C3B—C2B—H2BA	120.1
C3A—C2A—H2AA	120.1	C1B—C2B—H2BA	120.1
C4A—C3A—C2A	120.6 (4)	C2B—C3B—C4B	119.5 (14)
C4A—C3A—H3AA	119.7	C2B—C3B—H3BA	120.2
C2A—C3A—H3AA	119.7	C4B—C3B—H3BA	120.2
C5A—C4A—C3A	120.6 (4)	C3B—C4B—C5B	120.4 (15)
C5A—C4A—H4AA	119.7	C3B—C4B—H4BA	119.8
C3A—C4A—H4AA	119.7	C5B—C4B—H4BA	119.8
C4A—C5A—C6A	116.4 (5)	C6B—C5B—C4B	120.8 (16)
C4A—C5A—H5AA	121.8	C6B—C5B—H5BA	119.6
C6A—C5A—H5AA	121.8	C4B—C5B—H5BA	119.6
C1A—C6A—C5A	125.1 (5)	C5B—C6B—C1B	117.0 (13)
C1A—C6A—N1A	118.2 (5)	C5B—C6B—N1B	121.1 (16)
C5A—C6A—N1A	116.6 (5)	C1B—C6B—N1B	122.0 (16)
O2A—C7A—C8A	136.4 (4)	O2B—C7B—O1B	122.8 (12)
O2A—C7A—O1A	119.3 (4)	O2B—C7B—C8B	135.8 (12)
C8A—C7A—O1A	104.3 (3)	O1B—C7B—C8B	101.4 (10)
N1A—C8A—C7A	104.6 (3)	N1B—C8B—C7B	108.4 (10)
N1A—C8A—C9A	124.7 (3)	N1B—C8B—C9B	122.3 (10)
C7A—C8A—C9A	130.6 (3)	C7B—C8B—C9B	129.3 (10)
C13A—C12A—C17A	119.4 (2)	C13B—C12B—C17B	118.1 (9)
C13A—C12A—C11A	121.3 (2)	C13B—C12B—C11B	122.1 (8)
C17A—C12A—C11A	119.4 (2)	C17B—C12B—C11B	119.3 (9)
C12A—C13A—C14A	120.7 (3)	C14B—C13B—C12B	121.0 (11)
C12A—C13A—H13A	119.6	C14B—C13B—H13B	119.5
C14A—C13A—H13A	119.6	C12B—C13B—H13B	119.5
C15A—C14A—C13A	118.7 (4)	C15B—C14B—C13B	118.6 (13)
C15A—C14A—H14A	120.7	C15B—C14B—H14B	120.7
C13A—C14A—H14A	120.7	C13B—C14B—H14B	120.7
C16A—C15A—C14A	121.5 (5)	C14B—C15B—C16B	122.9 (15)
C16A—C15A—Br3A	121.3 (4)	C14B—C15B—Br3B	119.4 (12)
C14A—C15A—Br3A	117.1 (4)	C16B—C15B—Br3B	115.5 (12)
C15A—C16A—C17A	119.5 (5)	C17B—C16B—C15B	115.8 (14)
C15A—C16A—H16A	120.2	C17B—C16B—H16B	122.1
C17A—C16A—H16A	120.2	C15B—C16B—H16B	122.1
C12A—C17A—C16A	120.2 (4)	C16B—C17B—C12B	122.7 (13)
C12A—C17A—H17A	119.9	C16B—C17B—H17B	118.7
C16A—C17A—H17A	119.9	C12B—C17B—H17B	118.7
O3A—C9A—C8A	123.7 (2)	O3B—C9B—C8B	123.4 (9)
O3A—C9A—C10A	121.3 (2)	O3B—C9B—C10B	121.6 (9)
C8A—C9A—C10A	114.9 (2)	C8B—C9B—C10B	115.0 (8)
C11A—C10A—C9A	112.6 (2)	C11B—C10B—C9B	111.4 (7)
C11A—C10A—Br1A	109.35 (19)	C11B—C10B—Br2B	104.3 (7)
C9A—C10A—Br1A	103.21 (18)	C9B—C10B—Br2B	101.7 (6)
C11A—C10A—H10A	110.5	C11B—C10B—H10B	112.9
C9A—C10A—H10A	110.5	C9B—C10B—H10B	112.9
Br1A—C10A—H10A	110.5	Br2B—C10B—H10B	112.9
C12A—C11A—C10A	116.6 (2)	C10B—C11B—C12B	115.3 (7)
C12A—C11A—Br2A	107.83 (17)	C10B—C11B—Br1B	102.5 (7)
C10A—C11A—Br2A	102.68 (17)	C12B—C11B—Br1B	109.8 (6)
C12A—C11A—H11A	109.8	C10B—C11B—H11B	109.7
C10A—C11A—H11A	109.8	C12B—C11B—H11B	109.7
Br2A—C11A—H11A	109.8	Br1B—C11B—H11B	109.7
C8A—N1A—N2A—O1A	3.2 (9)	C8B—N1B—N2B—O1B	−6(3)
C6A—N1A—N2A—O1A	−178.2 (6)	C6B—N1B—N2B—O1B	174 (2)
C7A—O1A—N2A—N1A	−1.8 (9)	C7B—O1B—N2B—N1B	5(3)
C6A—C1A—C2A—C3A	1.7 (10)	C6B—C1B—C2B—C3B	−6(3)
C1A—C2A—C3A—C4A	−1.3 (8)	C1B—C2B—C3B—C4B	6(3)
C2A—C3A—C4A—C5A	1.5 (10)	C2B—C3B—C4B—C5B	−6(4)
C3A—C4A—C5A—C6A	−2.0 (13)	C3B—C4B—C5B—C6B	5(5)
C2A—C1A—C6A—C5A	−2.4 (15)	C4B—C5B—C6B—C1B	−4(6)
C2A—C1A—C6A—N1A	178.8 (7)	C4B—C5B—C6B—N1B	175 (3)
C4A—C5A—C6A—C1A	2.5 (17)	C2B—C1B—C6B—C5B	4(5)
C4A—C5A—C6A—N1A	−178.6 (8)	C2B—C1B—C6B—N1B	−175 (2)
N2A—N1A—C6A—C1A	−109.4 (10)	N2B—N1B—C6B—C5B	84 (4)
C8A—N1A—C6A—C1A	69.1 (12)	C8B—N1B—C6B—C5B	−96 (4)
N2A—N1A—C6A—C5A	71.7 (12)	N2B—N1B—C6B—C1B	−96 (4)
C8A—N1A—C6A—C5A	−109.9 (10)	C8B—N1B—C6B—C1B	83 (4)
N2A—O1A—C7A—O2A	178.0 (6)	N2B—O1B—C7B—O2B	176 (2)
N2A—O1A—C7A—C8A	−0.1 (7)	N2B—O1B—C7B—C8B	−2(2)
N2A—N1A—C8A—C7A	−3.3 (8)	N2B—N1B—C8B—C7B	5(3)
C6A—N1A—C8A—C7A	178.3 (6)	C6B—N1B—C8B—C7B	−175 (2)
N2A—N1A—C8A—C9A	−179.6 (6)	N2B—N1B—C8B—C9B	−176.1 (18)
C6A—N1A—C8A—C9A	2.0 (9)	C6B—N1B—C8B—C9B	4(4)
O2A—C7A—C8A—N1A	−175.7 (6)	O2B—C7B—C8B—N1B	−180 (2)
O1A—C7A—C8A—N1A	1.8 (5)	O1B—C7B—C8B—N1B	−1(2)
O2A—C7A—C8A—C9A	0.3 (9)	O2B—C7B—C8B—C9B	1(3)
O1A—C7A—C8A—C9A	177.9 (4)	O1B—C7B—C8B—C9B	179.6 (15)
C17A—C12A—C13A—C14A	0.0 (5)	C17B—C12B—C13B—C14B	2.2 (16)
C11A—C12A—C13A—C14A	−179.9 (3)	C11B—C12B—C13B—C14B	173.7 (11)
C12A—C13A—C14A—C15A	−0.8 (10)	C12B—C13B—C14B—C15B	4(3)
C13A—C14A—C15A—C16A	2.3 (18)	C13B—C14B—C15B—C16B	−11 (5)
C13A—C14A—C15A—Br3A	177.9 (6)	C13B—C14B—C15B—Br3B	−173 (2)
C14A—C15A—C16A—C17A	−3(2)	C14B—C15B—C16B—C17B	11 (6)
Br3A—C15A—C16A—C17A	−178.4 (8)	Br3B—C15B—C16B—C17B	174 (2)
C13A—C12A—C17A—C16A	−0.7 (7)	C15B—C16B—C17B—C12B	−5(4)
C11A—C12A—C17A—C16A	179.2 (5)	C13B—C12B—C17B—C16B	−2(2)
C15A—C16A—C17A—C12A	2.2 (13)	C11B—C12B—C17B—C16B	−173.4 (18)
N1A—C8A—C9A—O3A	14.4 (6)	N1B—C8B—C9B—O3B	19 (2)
C7A—C8A—C9A—O3A	−160.9 (4)	C7B—C8B—C9B—O3B	−162.4 (13)
N1A—C8A—C9A—C10A	−162.3 (4)	N1B—C8B—C9B—C10B	−163.2 (16)
C7A—C8A—C9A—C10A	22.4 (6)	C7B—C8B—C9B—C10B	15.8 (17)
O3A—C9A—C10A—C11A	34.0 (4)	O3B—C9B—C10B—C11B	−48.6 (13)
C8A—C9A—C10A—C11A	−149.2 (3)	C8B—C9B—C10B—C11B	133.2 (10)
O3A—C9A—C10A—Br1A	−83.8 (3)	O3B—C9B—C10B—Br2B	62.0 (10)
C8A—C9A—C10A—Br1A	93.0 (3)	C8B—C9B—C10B—Br2B	−116.1 (8)
C13A—C12A—C11A—C10A	−37.9 (4)	C9B—C10B—C11B—C12B	175.8 (7)
C17A—C12A—C11A—C10A	142.2 (3)	Br2B—C10B—C11B—C12B	66.9 (8)
C13A—C12A—C11A—Br2A	76.9 (3)	C9B—C10B—C11B—Br1B	−64.9 (8)
C17A—C12A—C11A—Br2A	−103.0 (3)	Br2B—C10B—C11B—Br1B	−173.8 (4)
C9A—C10A—C11A—C12A	−171.6 (2)	C13B—C12B—C11B—C10B	51.9 (13)
Br1A—C10A—C11A—C12A	−57.5 (3)	C17B—C12B—C11B—C10B	−136.7 (10)
C9A—C10A—C11A—Br2A	70.8 (2)	C13B—C12B—C11B—Br1B	−63.2 (10)
Br1A—C10A—C11A—Br2A	−175.09 (13)	C17B—C12B—C11B—Br1B	108.2 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C10A—H10A···O2A	0.98	2.40	3.168 (4)	135
C14A—H14A···Br3Ai	0.93	2.91	3.809 (5)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10A—H10A⋯O2A	0.98	2.40	3.168 (4)	135
C14A—H14A⋯Br3Ai	0.93	2.91	3.809 (5)	163

Symmetry code: (i) .