N-(2-Bromo-benz-yl)cinchoninium bromide.

The title compound {systematic name: 1-(2-bromo-benz-yl)-5-ethenyl-2-[hy-droxy(quinolin-4-yl)meth-yl]-1-aza-bicyclo-[2.2.2]octan-1-ium bromide}, C(26)H(28)BrN(2)O(+)·Br(-), is a chiral quater-nary ammonium salt of one of the Cinchona alkaloids. The planes of the quinoline and of the bromo-benzyl substituent are inclined to one another by 9.11 (9)°. A weak intra-molecular C-H⋯O hydrogen bond occurs. The crystal structure features strong O-H⋯Br hydrogen bonds and weak C-H⋯Br inter-actions.

Related literature

For the structure of cinchonine base and its derivatives, see: Oleksyn et al. (1979 ▶); Dolling et al. (1984 ▶). For crystal structures of other selected Cinchona alkaloid derivatives with bulky substituents at the quinuclidine nitro­gen atom, see: Song et al. (2005 ▶); Kawai et al. (2009 ▶); Jew et al. (2002 ▶); Matoba et al. (2010 ▶). For the effect of the substituent on the activity of the title catalyst, see: Jezierska-Zięba et al. (2010 ▶).

Experimental

Crystal data

C26H28BrN2O+·Br−

M = 544.30

Orthorhombic,

a = 7.2313 (1) Å

b = 16.2545 (1) Å

c = 20.2466 (2) Å

V = 2379.81 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.43 mm−1

T = 295 K

0.2 × 0.15 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor 1997 ▶) T min = 0.547, T max = 0.726

64183 measured reflections

5437 independent reflections

4879 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.071

S = 1.06

5437 reflections

283 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.42 e Å−3

Absolute structure: Flack (1983 ▶), 2320 Friedel pairs

Flack parameter: 0.020 (8)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK; data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203646X/rk2374sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203646X/rk2374Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203646X/rk2374Isup3.mol

Supplementary material file. DOI: 10.1107/S160053681203646X/rk2374Isup4.cml

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

Enhanced figure: interactive version of Fig. 3

C26H28BrN2O+·Br−	Dx = 1.519 Mg m−3
Mr = 544.30	Melting point: 430 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3135 reflections
a = 7.2313 (1) Å	θ = 1.0–27.5°
b = 16.2545 (1) Å	µ = 3.43 mm−1
c = 20.2466 (2) Å	T = 295 K
V = 2379.81 (4) Å3	Prism, colourless
Z = 4	0.2 × 0.15 × 0.1 mm
F(000) = 1104

Nonius KappaCCD diffractometer	5437 independent reflections
Radiation source: fine–focus sealed tube	4879 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.7°
CCD rotation images, thick slices scans	h = −9→9
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor 1997)	k = −20→21
Tmin = 0.547, Tmax = 0.726	l = −26→26
64183 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.071	w = 1/[σ2(Fo2) + (0.023P)2 + 1.5842P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
5437 reflections	Δρmax = 0.40 e Å−3
283 parameters	Δρmin = −0.42 e Å−3
0 restraints	Absolute structure: Flack (1983), 2320 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.020 (8)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1B	0.1042 (4)	0.78679 (16)	0.82411 (13)	0.0396 (6)
H1BA	−0.0247	0.7713	0.8194	0.048*
H1BB	0.1776	0.7374	0.8182	0.048*
C2B	0.1337 (4)	0.81793 (16)	0.89340 (13)	0.0393 (6)
C3B	−0.0039 (4)	0.85398 (19)	0.93115 (14)	0.0508 (7)
C4B	0.0243 (5)	0.8774 (2)	0.99629 (16)	0.0647 (9)
H4BA	−0.0705	0.9017	1.0204	0.078*
C5B	0.1937 (5)	0.8641 (3)	1.02470 (16)	0.0701 (11)
H5BA	0.2148	0.8804	1.0681	0.084*
C6B	0.3319 (5)	0.8269 (2)	0.98952 (16)	0.0643 (9)
H6BA	0.4461	0.8174	1.0092	0.077*
C7B	0.3019 (4)	0.8036 (2)	0.92451 (15)	0.0497 (7)
H7BA	0.3964	0.7777	0.9012	0.06*
C2	0.0284 (4)	0.92222 (15)	0.77020 (13)	0.0426 (6)
H2A	0.0258	0.9448	0.8146	0.051*
H2B	−0.0967	0.9064	0.7584	0.051*
C3	0.0976 (5)	0.98821 (17)	0.72183 (15)	0.0514 (8)
H3	0.167	1.0292	0.7472	0.062*
C4	0.2313 (5)	0.94693 (18)	0.67445 (15)	0.0528 (7)
H4	0.2626	0.9844	0.6382	0.063*
C5	0.4058 (4)	0.92317 (19)	0.71277 (18)	0.0577 (8)
H5A	0.4749	0.9723	0.7243	0.069*
H5B	0.484	0.8886	0.6855	0.069*
C6	0.3508 (4)	0.87670 (18)	0.77580 (14)	0.0453 (7)
H6A	0.4327	0.8302	0.7824	0.054*
H6B	0.3613	0.9128	0.8138	0.054*
C7	0.1435 (5)	0.86819 (19)	0.64724 (13)	0.0534 (8)
H7A	0.2132	0.8489	0.6093	0.064*
H7B	0.0178	0.8793	0.6331	0.064*
C8	0.1433 (4)	0.80217 (16)	0.70143 (13)	0.0395 (6)
H8	0.2581	0.7706	0.6967	0.047*
C9	−0.0178 (4)	0.74086 (17)	0.69529 (13)	0.0427 (6)
H9	0.0001	0.696	0.727	0.051*
C10	−0.0719 (7)	1.0313 (2)	0.6916 (2)	0.0775 (11)
H10	−0.1767	1.033	0.7182	0.093*
C11	−0.0879 (8)	1.0640 (3)	0.6368 (2)	0.1018 (16)
H11A	0.0116	1.0645	0.6077	0.122*
H11B	−0.1995	1.0881	0.6247	0.122*
C14	−0.1798 (7)	0.6905 (3)	0.52105 (18)	0.0800 (13)
H14	−0.2847	0.7015	0.496	0.096*
C15	−0.1729 (6)	0.7227 (2)	0.58609 (17)	0.0644 (9)
H15	−0.2684	0.7557	0.6018	0.077*
C16	−0.0262 (5)	0.70516 (17)	0.62510 (14)	0.0487 (7)
C17	0.1183 (5)	0.65446 (18)	0.59904 (14)	0.0508 (7)
C18	0.2769 (5)	0.62946 (19)	0.63382 (17)	0.0600 (9)
H18	0.2882	0.643	0.6783	0.072*
C19	0.4150 (6)	0.5857 (2)	0.6038 (2)	0.0775 (11)
H19	0.5204	0.5712	0.6274	0.093*
C20	0.3970 (7)	0.5627 (3)	0.5368 (2)	0.0876 (14)
H20	0.4914	0.5335	0.5163	0.105*
C21	0.2452 (8)	0.5826 (2)	0.50268 (19)	0.0803 (12)
H21	0.2351	0.5664	0.4588	0.096*
C22	0.1005 (6)	0.6277 (2)	0.53171 (16)	0.0637 (10)
Br2	−0.24868 (5)	0.86541 (3)	0.898389 (19)	0.07787 (13)
N1	0.1527 (3)	0.84692 (14)	0.76881 (10)	0.0357 (5)
N13	−0.0494 (6)	0.6463 (2)	0.49364 (14)	0.0778 (9)
O12	−0.1842 (3)	0.78260 (13)	0.71029 (12)	0.0520 (5)
H12	−0.255 (6)	0.750 (2)	0.7269 (17)	0.062*
Br1	0.55118 (5)	0.661427 (19)	0.789365 (17)	0.05560 (9)

	U11	U22	U33	U12	U13	U23
C1B	0.0480 (16)	0.0380 (14)	0.0328 (13)	0.0005 (11)	0.0036 (11)	0.0000 (11)
C2B	0.0437 (14)	0.0398 (15)	0.0344 (13)	−0.0034 (11)	0.0035 (12)	−0.0023 (11)
C3B	0.0480 (16)	0.0590 (19)	0.0454 (15)	−0.0050 (13)	0.0062 (12)	−0.0073 (13)
C4B	0.068 (2)	0.082 (2)	0.0445 (16)	−0.0092 (19)	0.0197 (16)	−0.0180 (16)
C5B	0.083 (3)	0.090 (3)	0.0379 (16)	−0.018 (2)	0.0009 (16)	−0.0157 (17)
C6B	0.059 (2)	0.086 (3)	0.0477 (17)	−0.008 (2)	−0.0115 (16)	−0.0009 (18)
C7B	0.0453 (17)	0.0621 (18)	0.0418 (15)	0.0010 (14)	0.0006 (12)	0.0023 (14)
C2	0.0485 (15)	0.0354 (13)	0.0441 (15)	0.0065 (12)	0.0015 (12)	−0.0036 (10)
C3	0.065 (2)	0.0362 (13)	0.0526 (18)	−0.0020 (13)	0.0017 (15)	0.0007 (12)
C4	0.069 (2)	0.0422 (15)	0.0477 (16)	−0.0098 (16)	0.0070 (16)	0.0069 (13)
C5	0.0567 (19)	0.0487 (16)	0.068 (2)	−0.0120 (13)	0.0198 (17)	−0.0014 (16)
C6	0.0425 (14)	0.0407 (14)	0.0527 (17)	−0.0032 (12)	0.0038 (13)	−0.0053 (13)
C7	0.080 (2)	0.0486 (16)	0.0316 (13)	−0.0104 (17)	0.0094 (14)	0.0025 (12)
C8	0.0498 (15)	0.0366 (13)	0.0320 (13)	−0.0022 (11)	0.0054 (12)	−0.0038 (11)
C9	0.0507 (16)	0.0405 (13)	0.0369 (14)	−0.0038 (12)	−0.0004 (12)	−0.0043 (11)
C10	0.105 (3)	0.055 (2)	0.072 (2)	0.013 (2)	0.007 (2)	0.0189 (17)
C11	0.101 (4)	0.117 (4)	0.088 (3)	0.040 (3)	−0.004 (3)	0.014 (3)
C14	0.109 (3)	0.082 (3)	0.049 (2)	0.001 (2)	−0.027 (2)	−0.0106 (19)
C15	0.077 (2)	0.069 (2)	0.0479 (18)	0.0013 (19)	−0.0131 (17)	−0.0070 (16)
C16	0.067 (2)	0.0406 (14)	0.0389 (14)	−0.0069 (14)	−0.0031 (14)	−0.0022 (11)
C17	0.075 (2)	0.0375 (14)	0.0400 (14)	−0.0082 (14)	0.0042 (14)	−0.0044 (13)
C18	0.081 (3)	0.0424 (16)	0.0566 (18)	−0.0025 (18)	0.0016 (17)	−0.0104 (14)
C19	0.085 (3)	0.059 (2)	0.089 (3)	0.011 (2)	0.005 (2)	−0.014 (2)
C20	0.113 (4)	0.068 (2)	0.082 (3)	0.015 (3)	0.031 (3)	−0.017 (2)
C21	0.122 (4)	0.063 (2)	0.056 (2)	0.006 (3)	0.015 (3)	−0.0161 (18)
C22	0.100 (3)	0.0491 (17)	0.0424 (16)	−0.0123 (19)	0.0058 (17)	−0.0077 (14)
Br2	0.04306 (16)	0.1171 (3)	0.0734 (2)	0.0077 (2)	0.01098 (18)	−0.0085 (2)
N1	0.0380 (11)	0.0334 (11)	0.0357 (11)	−0.0020 (10)	0.0027 (9)	−0.0019 (9)
N13	0.115 (3)	0.073 (2)	0.0450 (14)	−0.002 (2)	−0.0107 (18)	−0.0150 (14)
O12	0.0477 (11)	0.0548 (12)	0.0536 (12)	−0.0049 (9)	0.0028 (11)	−0.0070 (11)
Br1	0.05621 (17)	0.04800 (15)	0.06259 (17)	0.00830 (15)	0.00511 (16)	0.00209 (15)

C1B—C2B	1.507 (4)	C7—C8	1.535 (4)
C1B—N1	1.527 (3)	C7—H7A	0.97
C1B—H1BA	0.97	C7—H7B	0.97
C1B—H1BB	0.97	C8—C9	1.538 (4)
C2B—C3B	1.385 (4)	C8—N1	1.548 (3)
C2B—C7B	1.390 (4)	C8—H8	0.98
C3B—C4B	1.388 (4)	C9—O12	1.414 (4)
C3B—Br2	1.899 (3)	C9—C16	1.536 (4)
C4B—C5B	1.370 (5)	C9—H9	0.98
C4B—H4BA	0.93	C10—C11	1.235 (6)
C5B—C6B	1.368 (5)	C10—H10	0.93
C5B—H5BA	0.93	C11—H11A	0.93
C6B—C7B	1.387 (4)	C11—H11B	0.93
C6B—H6BA	0.93	C14—N13	1.309 (5)
C7B—H7BA	0.93	C14—C15	1.418 (5)
C2—N1	1.519 (3)	C14—H14	0.93
C2—C3	1.536 (4)	C15—C16	1.353 (5)
C2—H2A	0.97	C15—H15	0.93
C2—H2B	0.97	C16—C17	1.432 (5)
C3—C4	1.518 (4)	C17—C18	1.406 (5)
C3—C10	1.539 (5)	C17—C22	1.437 (4)
C3—H3	0.98	C18—C19	1.369 (5)
C4—C5	1.531 (5)	C18—H18	0.93
C4—C7	1.531 (4)	C19—C20	1.413 (6)
C4—H4	0.98	C19—H19	0.93
C5—C6	1.535 (4)	C20—C21	1.336 (7)
C5—H5A	0.97	C20—H20	0.93
C5—H5B	0.97	C21—C22	1.405 (6)
C6—N1	1.519 (3)	C21—H21	0.93
C6—H6A	0.97	C22—N13	1.364 (5)
C6—H6B	0.97	O12—H12	0.81 (4)
C2B—C1B—N1	115.8 (2)	C4—C7—H7B	109.9
C2B—C1B—H1BA	108.3	C8—C7—H7B	109.9
N1—C1B—H1BA	108.3	H7A—C7—H7B	108.3
C2B—C1B—H1BB	108.3	C7—C8—C9	113.3 (3)
N1—C1B—H1BB	108.3	C7—C8—N1	107.6 (2)
H1BA—C1B—H1BB	107.4	C9—C8—N1	114.1 (2)
C3B—C2B—C7B	116.8 (3)	C7—C8—H8	107.1
C3B—C2B—C1B	123.7 (3)	C9—C8—H8	107.1
C7B—C2B—C1B	119.3 (3)	N1—C8—H8	107.1
C2B—C3B—C4B	122.3 (3)	O12—C9—C16	110.3 (2)
C2B—C3B—Br2	121.2 (2)	O12—C9—C8	108.4 (2)
C4B—C3B—Br2	116.3 (2)	C16—C9—C8	110.5 (2)
C5B—C4B—C3B	119.2 (3)	O12—C9—H9	109.2
C5B—C4B—H4BA	120.4	C16—C9—H9	109.2
C3B—C4B—H4BA	120.4	C8—C9—H9	109.2
C4B—C5B—C6B	120.3 (3)	C11—C10—C3	128.9 (5)
C4B—C5B—H5BA	119.9	C11—C10—H10	115.6
C6B—C5B—H5BA	119.9	C3—C10—H10	115.6
C5B—C6B—C7B	120.0 (3)	C10—C11—H11A	120
C5B—C6B—H6BA	120	C10—C11—H11B	120
C7B—C6B—H6BA	120	H11A—C11—H11B	120
C6B—C7B—C2B	121.4 (3)	N13—C14—C15	124.8 (4)
C6B—C7B—H7BA	119.3	N13—C14—H14	117.6
C2B—C7B—H7BA	119.3	C15—C14—H14	117.6
N1—C2—C3	111.0 (2)	C16—C15—C14	119.4 (4)
N1—C2—H2A	109.4	C16—C15—H15	120.3
C3—C2—H2A	109.4	C14—C15—H15	120.3
N1—C2—H2B	109.4	C15—C16—C17	118.6 (3)
C3—C2—H2B	109.4	C15—C16—C9	119.4 (3)
H2A—C2—H2B	108	C17—C16—C9	122.0 (3)
C4—C3—C2	107.6 (2)	C18—C17—C16	125.3 (3)
C4—C3—C10	117.2 (3)	C18—C17—C22	117.4 (3)
C2—C3—C10	108.2 (3)	C16—C17—C22	117.3 (3)
C4—C3—H3	107.9	C19—C18—C17	121.5 (3)
C2—C3—H3	107.9	C19—C18—H18	119.2
C10—C3—H3	107.9	C17—C18—H18	119.2
C3—C4—C5	108.4 (3)	C18—C19—C20	119.8 (4)
C3—C4—C7	109.4 (3)	C18—C19—H19	120.1
C5—C4—C7	108.3 (3)	C20—C19—H19	120.1
C3—C4—H4	110.2	C21—C20—C19	120.5 (4)
C5—C4—H4	110.2	C21—C20—H20	119.7
C7—C4—H4	110.2	C19—C20—H20	119.7
C4—C5—C6	109.4 (2)	C20—C21—C22	121.4 (4)
C4—C5—H5A	109.8	C20—C21—H21	119.3
C6—C5—H5A	109.8	C22—C21—H21	119.3
C4—C5—H5B	109.8	N13—C22—C21	118.1 (3)
C6—C5—H5B	109.8	N13—C22—C17	122.7 (3)
H5A—C5—H5B	108.2	C21—C22—C17	119.2 (4)
N1—C6—C5	108.9 (2)	C2—N1—C6	107.4 (2)
N1—C6—H6A	109.9	C2—N1—C1B	111.48 (19)
C5—C6—H6A	109.9	C6—N1—C1B	110.6 (2)
N1—C6—H6B	109.9	C2—N1—C8	111.7 (2)
C5—C6—H6B	109.9	C6—N1—C8	105.9 (2)
H6A—C6—H6B	108.3	C1B—N1—C8	109.60 (19)
C4—C7—C8	109.1 (2)	C14—N13—C22	117.1 (3)
C4—C7—H7A	109.9	C9—O12—H12	108 (3)
C8—C7—H7A	109.9
N1—C1B—C2B—C3B	94.4 (3)	O12—C9—C16—C17	−175.1 (3)
N1—C1B—C2B—C7B	−91.9 (3)	C8—C9—C16—C17	65.0 (3)
C7B—C2B—C3B—C4B	2.0 (5)	C15—C16—C17—C18	−178.6 (3)
C1B—C2B—C3B—C4B	175.8 (3)	C9—C16—C17—C18	2.3 (5)
C7B—C2B—C3B—Br2	−172.6 (2)	C15—C16—C17—C22	2.1 (4)
C1B—C2B—C3B—Br2	1.3 (4)	C9—C16—C17—C22	−177.0 (3)
C2B—C3B—C4B—C5B	−0.4 (5)	C16—C17—C18—C19	−175.3 (3)
Br2—C3B—C4B—C5B	174.4 (3)	C22—C17—C18—C19	4.1 (5)
C3B—C4B—C5B—C6B	−1.1 (6)	C17—C18—C19—C20	−1.9 (6)
C4B—C5B—C6B—C7B	0.9 (6)	C18—C19—C20—C21	−0.6 (7)
C5B—C6B—C7B—C2B	0.8 (6)	C19—C20—C21—C22	0.8 (7)
C3B—C2B—C7B—C6B	−2.2 (5)	C20—C21—C22—N13	179.5 (4)
C1B—C2B—C7B—C6B	−176.3 (3)	C20—C21—C22—C17	1.5 (6)
N1—C2—C3—C4	16.7 (3)	C18—C17—C22—N13	178.3 (3)
N1—C2—C3—C10	144.2 (3)	C16—C17—C22—N13	−2.3 (5)
C2—C3—C4—C5	−68.9 (3)	C18—C17—C22—C21	−3.8 (5)
C10—C3—C4—C5	169.1 (3)	C16—C17—C22—C21	175.6 (3)
C2—C3—C4—C7	49.0 (3)	C3—C2—N1—C6	49.6 (3)
C10—C3—C4—C7	−73.0 (3)	C3—C2—N1—C1B	170.9 (2)
C3—C4—C5—C6	49.8 (3)	C3—C2—N1—C8	−66.1 (3)
C7—C4—C5—C6	−68.8 (3)	C5—C6—N1—C2	−68.9 (3)
C4—C5—C6—N1	17.4 (3)	C5—C6—N1—C1B	169.2 (2)
C3—C4—C7—C8	−73.6 (3)	C5—C6—N1—C8	50.5 (3)
C5—C4—C7—C8	44.4 (3)	C2B—C1B—N1—C2	−64.3 (3)
C4—C7—C8—C9	150.5 (3)	C2B—C1B—N1—C6	55.2 (3)
C4—C7—C8—N1	23.3 (3)	C2B—C1B—N1—C8	171.6 (2)
C7—C8—C9—O12	−69.4 (3)	C7—C8—N1—C2	41.8 (3)
N1—C8—C9—O12	54.2 (3)	C9—C8—N1—C2	−84.9 (3)
C7—C8—C9—C16	51.5 (3)	C7—C8—N1—C6	−74.9 (3)
N1—C8—C9—C16	175.1 (2)	C9—C8—N1—C6	158.5 (2)
C4—C3—C10—C11	−29.2 (6)	C7—C8—N1—C1B	165.8 (2)
C2—C3—C10—C11	−150.9 (5)	C9—C8—N1—C1B	39.1 (3)
N13—C14—C15—C16	−2.8 (7)	C15—C14—N13—C22	2.6 (6)
C14—C15—C16—C17	0.2 (5)	C21—C22—N13—C14	−177.9 (4)
C14—C15—C16—C9	179.4 (3)	C17—C22—N13—C14	0.0 (6)
O12—C9—C16—C15	5.8 (4)	H12—O12—C9—C8	−149 (3)
C8—C9—C16—C15	−114.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···Br1i	0.81 (4)	2.38 (4)	3.179 (2)	173 (3)
C2—H2A···Br2	0.97	2.91	3.406 (3)	113
C2—H2B···O12	0.97	2.32	2.997 (4)	126
C6—H6A···Br1	0.97	2.88	3.797 (3)	159
C7—H7B···O12	0.97	2.65	3.030 (4)	103
C15—H15···O12	0.93	2.32	2.697 (4)	104
C18—H18···Br1	0.93	2.96	3.758 (4)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O12—H12⋯Br1i	0.81 (4)	2.38 (4)	3.179 (2)	173 (3)
C2—H2B⋯O12	0.97	2.32	2.997 (4)	126
C6—H6A⋯Br1	0.97	2.88	3.797 (3)	159
C18—H18⋯Br1	0.93	2.96	3.758 (4)	145

Symmetry code: (i) .