1-(3-Ammonio-methyl-2,4,6-trimethyl-benz-yl)-3-(2,4,6-trimethyl-phen-yl)imidazol-1-ium dibromide monohydrate.

In the title compound, C(25)H(35)N(3) (2+)·2Br(-)·H(2)O, the dihedral angles between the imidazole ring and the two outer benzene rings are 80.16 (16) and 69.40 (18)°. The component species are linked by N-H⋯Br, O-H⋯Br and C-H⋯Br hydrogen bonds.

Related literature

For carbene ligands and complexes, see: Alcalde et al. (2007 ▶); Douthwaite et al. (2004 ▶); Magill et al. (2001 ▶). For phosphine ligands and complexes, see: Cao et al. (2000 ▶); Liou et al. (1995 ▶); Rybtchinski et al. (1996 ▶, 1999 ▶, 2001 ▶). For a related synthesis, see: Gandelman et al. (1997 ▶). For related literature, see: Caddick et al. (2004 ▶); Hahn (2006 ▶).

Experimental

Crystal data

C25H35N3 2+·2Br−·H2O

M = 555.40

Triclinic,

a = 10.594 (4) Å

b = 10.800 (3) Å

c = 13.193 (4) Å

α = 66.48 (4)°

β = 70.26 (4)°

γ = 80.58 (3)°

V = 1302.0 (9) Å3

Z = 2

Mo Kα radiation

μ = 3.13 mm−1

T = 294 K

0.50 × 0.46 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: spherical (Farrugia, 1999 ▶) T min = 0.303, T max = 0.367

4856 measured reflections

4745 independent reflections

2966 reflections with I > 2σ(I)

R int = 0.007

3 standard reflections every 300 reflections intensity decay: 2.7%

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.203

S = 1.09

4745 reflections

300 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.01 e Å−3

Δρmin = −0.58 e Å−3

Data collection: DIFRAC (Gabe et al., 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012811/zl2182sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012811/zl2182Isup2.hkl

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

C25H35N32+·2Br−·H2O	Z = 2
Mr = 555.40	F(000) = 572
Triclinic, P1	Dx = 1.417 Mg m−3
Hall symbol: -P 1	Melting point: 501 K
a = 10.594 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.800 (3) Å	Cell parameters from 23 reflections
c = 13.193 (4) Å	θ = 4.5–7.8°
α = 66.48 (4)°	µ = 3.13 mm−1
β = 70.26 (4)°	T = 294 K
γ = 80.58 (3)°	Block, colourless
V = 1302.0 (9) Å3	0.50 × 0.46 × 0.40 mm

Enraf–Nonius CAD-4 diffractometer	2966 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.007
graphite	θmax = 25.6°, θmin = 1.8°
ω/2θ scans	h = −12→12
Absorption correction: for a sphere (Farrugia, 1999)	k = −4→13
Tmin = 0.303, Tmax = 0.367	l = −14→15
4856 measured reflections	3 standard reflections every 300 reflections
4745 independent reflections	intensity decay: 2.7%

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)] = 0.065	Hydrogen site location: mixed
wR(F2) = 0.203	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.12P)2 + 0.3033P] where P = (Fo2 + 2Fc2)/3
4745 reflections	(Δ/σ)max < 0.001
300 parameters	Δρmax = 1.01 e Å−3
4 restraints	Δρmin = −0.58 e Å−3

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
Br1	0.05853 (7)	0.78890 (7)	0.34382 (7)	0.0653 (3)
Br2	0.53218 (8)	0.62059 (8)	0.28647 (7)	0.0652 (3)
O1	0.3386 (6)	0.7953 (7)	0.1251 (4)	0.0685 (14)
H1O1	0.272 (4)	0.815 (8)	0.170 (4)	0.07 (3)*
H1O2	0.397 (5)	0.764 (8)	0.157 (5)	0.07 (3)*
N1	0.3013 (5)	0.4016 (4)	0.4497 (4)	0.0341 (10)
H1N	0.383 (3)	0.438 (6)	0.413 (5)	0.056 (19)*
N2	0.3043 (4)	0.0868 (4)	0.1764 (4)	0.0308 (9)
N3	0.1566 (4)	0.2120 (4)	0.0972 (4)	0.0336 (10)
C1	0.3488 (5)	0.1091 (5)	0.3941 (5)	0.0326 (11)
C2	0.4293 (5)	0.0520 (5)	0.3132 (4)	0.0303 (11)
C3	0.5697 (5)	0.0588 (5)	0.2778 (5)	0.0339 (12)
C4	0.6263 (5)	0.1238 (5)	0.3225 (5)	0.0342 (12)
H4	0.7193	0.1254	0.3010	0.041*
C5	0.5505 (5)	0.1865 (5)	0.3978 (4)	0.0301 (11)
C6	0.4093 (5)	0.1809 (5)	0.4329 (4)	0.0305 (11)
C7	0.3254 (5)	0.2517 (5)	0.5130 (5)	0.0341 (12)
H7A	0.3699	0.2408	0.5694	0.041*
H7B	0.2395	0.2089	0.5548	0.041*
C8	0.2255 (6)	0.4298 (6)	0.3664 (5)	0.0455 (14)
H8A	0.2643	0.3772	0.3187	0.068*
H8B	0.2294	0.5241	0.3183	0.068*
H8C	0.1336	0.4064	0.4081	0.068*
C9	0.2247 (6)	0.4663 (6)	0.5380 (6)	0.0473 (15)
H9A	0.2131	0.5616	0.4984	0.071*
H9B	0.2745	0.4511	0.5909	0.071*
H9C	0.1384	0.4267	0.5802	0.071*
C10	0.1998 (5)	0.0854 (6)	0.4431 (5)	0.0398 (13)
H10A	0.1537	0.1555	0.3948	0.060*
H10B	0.1678	0.0864	0.5201	0.060*
H10C	0.1833	−0.0006	0.4455	0.060*
C11	0.6620 (6)	−0.0024 (6)	0.1924 (5)	0.0444 (14)
H11A	0.6464	−0.0971	0.2215	0.067*
H11B	0.7537	0.0100	0.1826	0.067*
H11C	0.6444	0.0413	0.1191	0.067*
C12	0.6214 (6)	0.2566 (6)	0.4402 (5)	0.0385 (12)
H12A	0.6090	0.3526	0.4046	0.058*
H12B	0.7154	0.2326	0.4202	0.058*
H12C	0.5850	0.2292	0.5229	0.058*
C13	0.3650 (6)	−0.0154 (5)	0.2643 (5)	0.0351 (12)
H13A	0.4318	−0.0707	0.2286	0.042*
H13B	0.2960	−0.0741	0.3265	0.042*
C14	0.1737 (5)	0.1112 (5)	0.1895 (4)	0.0302 (11)
H14	0.1052	0.0644	0.2539	0.036*
C15	0.3735 (6)	0.1725 (6)	0.0688 (5)	0.0421 (14)
H15	0.4663	0.1750	0.0371	0.050*
C16	0.2853 (6)	0.2512 (6)	0.0174 (5)	0.0437 (14)
H16	0.3042	0.3187	−0.0562	0.052*
C17	0.0284 (5)	0.2702 (5)	0.0807 (5)	0.0350 (12)
C18	−0.0477 (5)	0.3458 (6)	0.1462 (5)	0.0378 (12)
C19	−0.1741 (6)	0.3945 (6)	0.1334 (5)	0.0417 (13)
H19	−0.2271	0.4449	0.1764	0.050*
C20	−0.2221 (5)	0.3696 (6)	0.0589 (5)	0.0414 (13)
C21	−0.1385 (6)	0.3010 (6)	−0.0093 (6)	0.0489 (15)
H21	−0.1682	0.2895	−0.0636	0.059*
C22	−0.0132 (6)	0.2492 (6)	−0.0001 (5)	0.0423 (13)
C23	0.0000 (7)	0.3743 (7)	0.2297 (6)	0.0521 (16)
H23A	−0.0364	0.4603	0.2334	0.078*
H23B	0.0963	0.3757	0.2037	0.078*
H23C	−0.0292	0.3050	0.3052	0.078*
C24	−0.3623 (7)	0.4168 (8)	0.0498 (8)	0.066 (2)
H24A	−0.4166	0.4323	0.1187	0.099*
H24B	−0.4016	0.3488	0.0413	0.099*
H24C	−0.3575	0.4993	−0.0164	0.099*
C25	0.0750 (8)	0.1756 (9)	−0.0766 (8)	0.073 (2)
H25A	0.0258	0.1644	−0.1215	0.109*
H25B	0.1022	0.0886	−0.0293	0.109*
H25C	0.1529	0.2271	−0.1278	0.109*

	U11	U22	U33	U12	U13	U23
Br1	0.0458 (4)	0.0520 (4)	0.0827 (6)	−0.0118 (3)	0.0013 (3)	−0.0227 (4)
Br2	0.0657 (5)	0.0598 (5)	0.0600 (5)	−0.0090 (3)	−0.0138 (4)	−0.0137 (4)
O1	0.058 (3)	0.106 (4)	0.053 (3)	−0.005 (3)	−0.016 (3)	−0.039 (3)
N1	0.036 (2)	0.034 (2)	0.040 (3)	−0.0018 (19)	−0.012 (2)	−0.020 (2)
N2	0.037 (2)	0.028 (2)	0.032 (2)	0.0007 (18)	−0.0126 (19)	−0.0136 (19)
N3	0.033 (2)	0.034 (2)	0.030 (2)	−0.0029 (18)	−0.0117 (19)	−0.0063 (19)
C1	0.031 (3)	0.030 (3)	0.034 (3)	−0.004 (2)	−0.010 (2)	−0.009 (2)
C2	0.035 (3)	0.024 (2)	0.033 (3)	−0.004 (2)	−0.012 (2)	−0.008 (2)
C3	0.036 (3)	0.026 (3)	0.037 (3)	0.003 (2)	−0.011 (2)	−0.009 (2)
C4	0.028 (3)	0.030 (3)	0.042 (3)	−0.003 (2)	−0.012 (2)	−0.009 (2)
C5	0.037 (3)	0.022 (2)	0.033 (3)	−0.004 (2)	−0.019 (2)	−0.003 (2)
C6	0.037 (3)	0.028 (3)	0.027 (3)	−0.006 (2)	−0.011 (2)	−0.007 (2)
C7	0.042 (3)	0.032 (3)	0.031 (3)	−0.001 (2)	−0.014 (2)	−0.011 (2)
C8	0.061 (4)	0.035 (3)	0.050 (4)	0.004 (3)	−0.036 (3)	−0.012 (3)
C9	0.051 (3)	0.044 (3)	0.056 (4)	0.004 (3)	−0.011 (3)	−0.033 (3)
C10	0.034 (3)	0.047 (3)	0.048 (3)	0.000 (2)	−0.013 (3)	−0.027 (3)
C11	0.037 (3)	0.050 (3)	0.053 (4)	0.000 (3)	−0.009 (3)	−0.030 (3)
C12	0.042 (3)	0.034 (3)	0.046 (3)	−0.007 (2)	−0.018 (3)	−0.015 (3)
C13	0.043 (3)	0.027 (3)	0.040 (3)	0.001 (2)	−0.020 (2)	−0.013 (2)
C14	0.027 (3)	0.033 (3)	0.029 (3)	−0.007 (2)	−0.007 (2)	−0.009 (2)
C15	0.029 (3)	0.052 (3)	0.033 (3)	−0.004 (3)	−0.005 (2)	−0.007 (3)
C16	0.037 (3)	0.052 (3)	0.033 (3)	−0.012 (3)	−0.008 (2)	−0.005 (3)
C17	0.033 (3)	0.036 (3)	0.033 (3)	−0.005 (2)	−0.010 (2)	−0.009 (2)
C18	0.039 (3)	0.037 (3)	0.033 (3)	−0.004 (2)	−0.011 (2)	−0.009 (2)
C19	0.040 (3)	0.037 (3)	0.039 (3)	0.001 (2)	−0.010 (3)	−0.008 (3)
C20	0.034 (3)	0.036 (3)	0.051 (4)	−0.006 (2)	−0.017 (3)	−0.007 (3)
C21	0.054 (4)	0.047 (3)	0.056 (4)	−0.004 (3)	−0.034 (3)	−0.013 (3)
C22	0.045 (3)	0.043 (3)	0.045 (3)	−0.003 (3)	−0.019 (3)	−0.017 (3)
C23	0.050 (4)	0.067 (4)	0.045 (4)	0.007 (3)	−0.018 (3)	−0.027 (3)
C24	0.049 (4)	0.057 (4)	0.099 (6)	0.004 (3)	−0.044 (4)	−0.021 (4)
C25	0.075 (5)	0.090 (6)	0.084 (6)	0.022 (4)	−0.042 (4)	−0.059 (5)

O1—H1O1	0.81 (6)	C10—H10C	0.9600
O1—H1O2	0.82 (6)	C11—H11A	0.9600
N1—C8	1.482 (7)	C11—H11B	0.9600
N1—C7	1.521 (7)	C11—H11C	0.9600
N1—C9	1.526 (7)	C12—H12A	0.9600
N1—H1N	0.90 (5)	C12—H12B	0.9600
N2—C14	1.330 (6)	C12—H12C	0.9600
N2—C15	1.371 (7)	C13—H13A	0.9700
N2—C13	1.492 (7)	C13—H13B	0.9700
N3—C14	1.314 (6)	C14—H14	0.9300
N3—C16	1.418 (7)	C15—C16	1.328 (8)
N3—C17	1.449 (7)	C15—H15	0.9300
C1—C6	1.405 (7)	C16—H16	0.9300
C1—C2	1.409 (7)	C17—C22	1.387 (8)
C1—C10	1.512 (7)	C17—C18	1.393 (8)
C2—C3	1.406 (7)	C18—C19	1.396 (8)
C2—C13	1.497 (7)	C18—C23	1.503 (8)
C3—C4	1.380 (8)	C19—C20	1.376 (9)
C3—C11	1.517 (7)	C19—H19	0.9300
C4—C5	1.382 (7)	C20—C21	1.386 (9)
C4—H4	0.9300	C20—C24	1.518 (8)
C5—C6	1.412 (7)	C21—C22	1.379 (8)
C5—C12	1.503 (7)	C21—H21	0.9300
C6—C7	1.510 (7)	C22—C25	1.511 (9)
C7—H7A	0.9700	C23—H23A	0.9600
C7—H7B	0.9700	C23—H23B	0.9600
C8—H8A	0.9600	C23—H23C	0.9600
C8—H8B	0.9600	C24—H24A	0.9600
C8—H8C	0.9600	C24—H24B	0.9600
C9—H9A	0.9600	C24—H24C	0.9600
C9—H9B	0.9600	C25—H25A	0.9600
C9—H9C	0.9600	C25—H25B	0.9600
C10—H10A	0.9600	C25—H25C	0.9600
C10—H10B	0.9600
H1O1—O1—H1O2	109 (6)	H11A—C11—H11C	109.5
C8—N1—C7	113.5 (4)	H11B—C11—H11C	109.5
C8—N1—C9	108.8 (4)	C5—C12—H12A	109.5
C7—N1—C9	109.4 (4)	C5—C12—H12B	109.5
C8—N1—H1N	111 (4)	H12A—C12—H12B	109.5
C7—N1—H1N	107 (4)	C5—C12—H12C	109.5
C9—N1—H1N	108 (4)	H12A—C12—H12C	109.5
C14—N2—C15	108.3 (4)	H12B—C12—H12C	109.5
C14—N2—C13	125.8 (4)	N2—C13—C2	110.9 (4)
C15—N2—C13	125.9 (4)	N2—C13—H13A	109.5
C14—N3—C16	107.7 (4)	C2—C13—H13A	109.5
C14—N3—C17	125.5 (4)	N2—C13—H13B	109.5
C16—N3—C17	126.7 (4)	C2—C13—H13B	109.5
C6—C1—C2	119.5 (5)	H13A—C13—H13B	108.1
C6—C1—C10	120.9 (5)	N3—C14—N2	109.3 (4)
C2—C1—C10	119.5 (5)	N3—C14—H14	125.3
C3—C2—C1	120.1 (5)	N2—C14—H14	125.3
C3—C2—C13	120.0 (5)	C16—C15—N2	108.4 (5)
C1—C2—C13	119.9 (5)	C16—C15—H15	125.8
C4—C3—C2	118.8 (5)	N2—C15—H15	125.8
C4—C3—C11	118.5 (5)	C15—C16—N3	106.2 (5)
C2—C3—C11	122.7 (5)	C15—C16—H16	126.9
C3—C4—C5	122.7 (5)	N3—C16—H16	126.9
C3—C4—H4	118.6	C22—C17—C18	122.7 (5)
C5—C4—H4	118.6	C22—C17—N3	118.7 (5)
C4—C5—C6	118.7 (5)	C18—C17—N3	118.6 (5)
C4—C5—C12	118.8 (5)	C17—C18—C19	117.4 (5)
C6—C5—C12	122.6 (5)	C17—C18—C23	122.8 (5)
C1—C6—C5	120.0 (4)	C19—C18—C23	119.7 (5)
C1—C6—C7	120.9 (5)	C20—C19—C18	121.6 (5)
C5—C6—C7	119.1 (4)	C20—C19—H19	119.2
C6—C7—N1	113.2 (4)	C18—C19—H19	119.2
C6—C7—H7A	108.9	C19—C20—C21	118.3 (5)
N1—C7—H7A	108.9	C19—C20—C24	121.4 (6)
C6—C7—H7B	108.9	C21—C20—C24	120.4 (6)
N1—C7—H7B	108.9	C22—C21—C20	122.9 (6)
H7A—C7—H7B	107.8	C22—C21—H21	118.6
N1—C8—H8A	109.5	C20—C21—H21	118.6
N1—C8—H8B	109.5	C21—C22—C17	116.9 (5)
H8A—C8—H8B	109.5	C21—C22—C25	121.1 (6)
N1—C8—H8C	109.5	C17—C22—C25	122.0 (5)
H8A—C8—H8C	109.5	C18—C23—H23A	109.5
H8B—C8—H8C	109.5	C18—C23—H23B	109.5
N1—C9—H9A	109.5	H23A—C23—H23B	109.5
N1—C9—H9B	109.5	C18—C23—H23C	109.5
H9A—C9—H9B	109.5	H23A—C23—H23C	109.5
N1—C9—H9C	109.5	H23B—C23—H23C	109.5
H9A—C9—H9C	109.5	C20—C24—H24A	109.5
H9B—C9—H9C	109.5	C20—C24—H24B	109.5
C1—C10—H10A	109.5	H24A—C24—H24B	109.5
C1—C10—H10B	109.5	C20—C24—H24C	109.5
H10A—C10—H10B	109.5	H24A—C24—H24C	109.5
C1—C10—H10C	109.5	H24B—C24—H24C	109.5
H10A—C10—H10C	109.5	C22—C25—H25A	109.5
H10B—C10—H10C	109.5	C22—C25—H25B	109.5
C3—C11—H11A	109.5	H25A—C25—H25B	109.5
C3—C11—H11B	109.5	C22—C25—H25C	109.5
H11A—C11—H11B	109.5	H25A—C25—H25C	109.5
C3—C11—H11C	109.5	H25B—C25—H25C	109.5
C6—C1—C2—C3	4.4 (7)	C17—N3—C14—N2	−178.2 (5)
C10—C1—C2—C3	−172.1 (5)	C15—N2—C14—N3	−2.5 (6)
C6—C1—C2—C13	−175.3 (5)	C13—N2—C14—N3	176.9 (4)
C10—C1—C2—C13	8.2 (7)	C14—N2—C15—C16	1.5 (6)
C1—C2—C3—C4	−0.9 (7)	C13—N2—C15—C16	−177.9 (5)
C13—C2—C3—C4	178.8 (5)	N2—C15—C16—N3	0.0 (7)
C1—C2—C3—C11	179.1 (5)	C14—N3—C16—C15	−1.5 (6)
C13—C2—C3—C11	−1.3 (8)	C17—N3—C16—C15	179.2 (5)
C2—C3—C4—C5	−2.2 (8)	C14—N3—C17—C22	−110.0 (6)
C11—C3—C4—C5	177.8 (5)	C16—N3—C17—C22	69.2 (7)
C3—C4—C5—C6	1.7 (8)	C14—N3—C17—C18	70.5 (7)
C3—C4—C5—C12	−179.0 (5)	C16—N3—C17—C18	−110.3 (6)
C2—C1—C6—C5	−4.9 (7)	C22—C17—C18—C19	4.0 (8)
C10—C1—C6—C5	171.5 (5)	N3—C17—C18—C19	−176.5 (5)
C2—C1—C6—C7	175.7 (4)	C22—C17—C18—C23	−177.0 (6)
C10—C1—C6—C7	−7.9 (8)	N3—C17—C18—C23	2.5 (8)
C4—C5—C6—C1	1.9 (7)	C17—C18—C19—C20	−0.3 (8)
C12—C5—C6—C1	−177.4 (5)	C23—C18—C19—C20	−179.3 (6)
C4—C5—C6—C7	−178.6 (5)	C18—C19—C20—C21	−3.7 (9)
C12—C5—C6—C7	2.1 (7)	C18—C19—C20—C24	176.9 (6)
C1—C6—C7—N1	−97.4 (6)	C19—C20—C21—C22	4.4 (9)
C5—C6—C7—N1	83.1 (6)	C24—C20—C21—C22	−176.3 (6)
C8—N1—C7—C6	62.4 (6)	C20—C21—C22—C17	−0.9 (9)
C9—N1—C7—C6	−175.9 (4)	C20—C21—C22—C25	−179.7 (7)
C14—N2—C13—C2	−109.4 (6)	C18—C17—C22—C21	−3.4 (9)
C15—N2—C13—C2	69.9 (6)	N3—C17—C22—C21	177.1 (5)
C3—C2—C13—N2	−104.4 (5)	C18—C17—C22—C25	175.4 (6)
C1—C2—C13—N2	75.3 (6)	N3—C17—C22—C25	−4.1 (9)
C16—N3—C14—N2	2.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···Br1	0.81 (6)	2.58 (3)	3.355 (6)	160 (8)
O1—H1O2···Br2	0.82 (6)	2.49 (6)	3.283 (6)	165 (7)
N1—H1N···Br2	0.90 (5)	2.40 (3)	3.238 (5)	154 (6)
C9—H9B···Br2i	0.96	2.85	3.792 (7)	167
C12—H12A···Br2	0.96	2.82	3.765 (7)	168
C14—H14···Br1ii	0.93	2.79	3.436 (6)	128
C16—H16···Br2iii	0.93	2.81	3.597 (6)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯Br1	0.81 (6)	2.58 (3)	3.355 (6)	160 (8)
O1—H1O2⋯Br2	0.82 (6)	2.49 (6)	3.283 (6)	165 (7)
N1—H1N⋯Br2	0.90 (5)	2.40 (3)	3.238 (5)	154 (6)
C9—H9B⋯Br2i	0.96	2.85	3.792 (7)	167
C12—H12A⋯Br2	0.96	2.82	3.765 (7)	168
C14—H14⋯Br1ii	0.93	2.79	3.436 (6)	128
C16—H16⋯Br2iii	0.93	2.81	3.597 (6)	143

Symmetry codes: (i) ; (ii) ; (iii) .