catena-Poly[N,N,N',N'-tetra-methyl-ethylendi-ammonium [[tetra-bromido-antimonate(III)]-μ-bromido] hemihydrate].

The asymmetric unit of the title compound {(C6H18N2)2[Sb2Br10]·H2O} n , consists of two tetra-methyl-ethylendi-ammonium cations that are located on centres of inversion, as well as one tetra-methyl-ethylendi-ammonium cation, one water mol-ecule, one distorted octahedral [SbBr6](3-)anion and one bisphenoidal [SbBr4](-) anion in general positions. The [SbBr6](3-) and [SbBr4](-) anions are linked together by two long Sb-Br bonds of 3.2709 (8) and 3.5447 (7) Å into {[Sb2Br10](4-)} n chains along [001]. One of the three tetra-methyl-ethylendi-ammonium cations is disordered and was refined using a split model (occupancy ratio 0.58:0.42). The cations and the water mol-ecule are connected to the {[Sb2Br10](4-)} n polymeric anions by weak N-H ⋯Br and O(water)-H ⋯Br hydrogen bonding.

Related literature

For crystal structures of related organic anti­monate(III) halogenides, see: Bujak & Angel (2005 ▶); Chaabouni et al. (1997 ▶, 1998 ▶). For a similar structure, see: Owczarek et al. (2012 ▶). The bond-valence sum was calculated using the parameters given by Brown & Altermatt (1985 ▶).

Experimental

Crystal data

(C6H18N2)[Sb2Br10]·H2O

M = 1297.06

Orthorhombic,

a = 18.0860 (4) Å

b = 19.1755 (4) Å

c = 19.4619 (4) Å

V = 6749.5 (2) Å3

Z = 8

Mo Kα radiation

μ = 13.45 mm−1

T = 298 K

0.43 × 0.30 × 0.19 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.011, T max = 0.078

65748 measured reflections

10770 independent reflections

5721 reflections with I > 2σ(I)

R int = 0.096

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.089

S = 1.01

10770 reflections

290 parameters

15 restraints

H-atom parameters constrained

Δρmax = 1.92 e Å−3

Δρmin = −1.98 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813028894/nc2318sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028894/nc2318Isup2.hkl

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

(C6H18N2)[Sb2Br10]·H2O	Z = 8
Mr = 1297.06	F(000) = 4784
Orthorhombic, Pbca	Dx = 2.553 Mg m−3
Hall symbol: -P 2ac 2ab	Mo Kα radiation, λ = 0.71073 Å
a = 18.0860 (4) Å	µ = 13.45 mm−1
b = 19.1755 (4) Å	T = 298 K
c = 19.4619 (4) Å	Prismatic, axis [1 0 0], yellow
V = 6749.5 (2) Å3	0.43 × 0.30 × 0.19 mm

Oxford Diffraction Xcalibur Sapphire2 diffractometer	10770 independent reflections
Radiation source: sealed X-ray tube	5721 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.096
Detector resolution: 8.3622 pixels mm-1	θmax = 31.6°, θmin = 3.1°
ω scans	h = −25→26
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −28→26
Tmin = 0.011, Tmax = 0.078	l = −26→28
65748 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.033P)2 + 2.8328P] where P = (Fo2 + 2Fc2)/3
10770 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 1.92 e Å−3
15 restraints	Δρmin = −1.98 e Å−3

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlis RED (Oxford Diffraction, 2009)

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.

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)
Sb1	0.626802 (19)	0.755771 (18)	0.520272 (17)	0.02825 (9)
Sb2	0.351898 (18)	0.442769 (18)	0.734954 (18)	0.02673 (9)
Br1	0.54458 (4)	0.65129 (3)	0.59658 (3)	0.04546 (16)
Br2	0.70124 (4)	0.85628 (3)	0.45458 (4)	0.05252 (18)
Br3	0.48610 (3)	0.81097 (4)	0.46063 (3)	0.04992 (18)
Br4	0.75101 (4)	0.70887 (4)	0.57645 (3)	0.0591 (2)
Br5	0.59238 (4)	0.83959 (4)	0.64163 (4)	0.0646 (2)
Br6	0.64208 (4)	0.66424 (3)	0.41346 (3)	0.04907 (17)
Br7	0.50362 (3)	0.48013 (3)	0.70652 (3)	0.03898 (15)
Br8	0.21218 (3)	0.41314 (4)	0.76132 (4)	0.0591 (2)
Br9	0.35219 (3)	0.53266 (3)	0.83085 (3)	0.04420 (16)
Br10	0.31213 (3)	0.53122 (3)	0.64461 (3)	0.04336 (16)
N1	0.6426 (2)	0.6779 (3)	0.7410 (2)	0.0377 (12)
H1	0.6259	0.6911	0.6989	0.045*
N2	0.4676 (3)	0.7303 (3)	0.7326 (3)	0.0423 (12)
H2	0.4908	0.7287	0.6911	0.051*
C1	0.6693 (4)	0.6051 (3)	0.7355 (4)	0.061 (2)
H1A	0.6291	0.5753	0.7222	0.091*
H1B	0.6883	0.5902	0.7791	0.091*
H1C	0.7077	0.6026	0.7015	0.091*
C2	0.7034 (4)	0.7249 (4)	0.7603 (4)	0.065 (2)
H2A	0.6851	0.7718	0.7633	0.098*
H2B	0.7416	0.7225	0.7262	0.098*
H2C	0.723	0.711	0.804	0.098*
C3	0.5793 (4)	0.6819 (4)	0.7901 (3)	0.066 (2)
H3A	0.5544	0.6372	0.7883	0.08*	0.58
H3B	0.6004	0.6859	0.8357	0.08*	0.58
H3C	0.5908	0.6497	0.827	0.08*	0.42
H3D	0.5812	0.7282	0.8099	0.08*	0.42
C4A	0.5236 (6)	0.7339 (6)	0.7848 (5)	0.047 (3)	0.58
H4A	0.5486	0.7783	0.7793	0.056*	0.58
H4B	0.4984	0.7356	0.8288	0.056*	0.58
C5A	0.4178 (12)	0.6752 (8)	0.7351 (13)	0.071 (6)	0.58
H5A	0.3847	0.6781	0.6966	0.107*	0.58
H5B	0.3899	0.6776	0.777	0.107*	0.58
H5C	0.4443	0.6319	0.7333	0.107*	0.58
C6A	0.4223 (7)	0.8015 (6)	0.7363 (7)	0.058 (4)	0.58
H6A	0.4559	0.8402	0.7345	0.087*	0.58
H6B	0.3947	0.8032	0.7784	0.087*	0.58
H6C	0.3888	0.8041	0.6981	0.087*	0.58
C4B	0.5103 (7)	0.6709 (6)	0.7744 (6)	0.031 (3)	0.42
H4C	0.4835	0.6626	0.8167	0.037*	0.42
H4D	0.5079	0.6282	0.7476	0.037*	0.42
C5B	0.3998 (18)	0.6842 (15)	0.7092 (19)	0.080 (10)	0.42
H5E	0.417	0.6468	0.6807	0.12*	0.42
H5F	0.3656	0.7125	0.6838	0.12*	0.42
H5G	0.3756	0.6654	0.749	0.12*	0.42
C6B	0.4477 (2)	0.7858 (2)	0.7706 (2)	0.092 (9)	0.42
H6E	0.4911	0.8112	0.784	0.138*	0.42
H6F	0.4219	0.7702	0.8109	0.138*	0.42
H6G	0.4159	0.8154	0.7441	0.138*	0.42
N3	0.4164 (2)	0.5295 (2)	0.4486 (2)	0.0347 (11)
H3	0.4377	0.5133	0.4094	0.042*
C7	0.4592 (3)	0.4993 (3)	0.5075 (3)	0.0318 (13)
H7A	0.4436	0.4515	0.5154	0.038*
H7B	0.4492	0.5259	0.5489	0.038*
C8	0.3390 (3)	0.5050 (4)	0.4484 (3)	0.0513 (18)
H8A	0.3381	0.4551	0.4524	0.077*
H8B	0.3156	0.5187	0.4062	0.077*
H8C	0.313	0.5253	0.4865	0.077*
C9	0.4198 (4)	0.6065 (3)	0.4455 (4)	0.0596 (19)
H9A	0.389	0.6229	0.4087	0.089*
H9B	0.4699	0.6209	0.4376	0.089*
H9C	0.4027	0.6256	0.4882	0.089*
N4	0.4240 (2)	0.9494 (2)	0.5451 (2)	0.0348 (11)
H4	0.4463	0.9071	0.5405	0.042*
C10	0.4578 (3)	0.9977 (3)	0.4958 (3)	0.0373 (14)
H10A	0.4366	1.0437	0.502	0.045*
H10B	0.4464	0.9824	0.4495	0.045*
C11	0.4316 (4)	0.9720 (4)	0.6179 (3)	0.064 (2)
H11A	0.4058	0.9399	0.6472	0.095*
H11B	0.411	1.0178	0.6232	0.095*
H11C	0.483	0.9728	0.6302	0.095*
C12	0.3444 (3)	0.9408 (4)	0.5294 (4)	0.061 (2)
H12A	0.3231	0.9076	0.5605	0.091*
H12B	0.3389	0.9243	0.4831	0.091*
H12C	0.3198	0.9848	0.5343	0.091*
OW	0.3596 (4)	0.7703 (5)	0.5870 (4)	0.159 (3)
H1W	0.3219	0.7677	0.563	0.238*
H2W	0.3989	0.7757	0.566	0.238*

	U11	U22	U33	U12	U13	U23
Sb1	0.0396 (2)	0.02096 (19)	0.02414 (17)	−0.00123 (16)	0.00398 (16)	−0.00193 (15)
Sb2	0.02741 (18)	0.02436 (19)	0.02841 (18)	0.00197 (15)	−0.00144 (15)	0.00237 (16)
Br1	0.0683 (4)	0.0336 (3)	0.0345 (3)	−0.0137 (3)	0.0033 (3)	−0.0023 (3)
Br2	0.0636 (4)	0.0405 (4)	0.0535 (4)	−0.0205 (3)	0.0045 (3)	0.0098 (3)
Br3	0.0512 (4)	0.0541 (4)	0.0444 (4)	0.0098 (3)	−0.0033 (3)	−0.0109 (3)
Br4	0.0503 (4)	0.0776 (5)	0.0493 (4)	0.0205 (4)	−0.0013 (3)	0.0034 (4)
Br5	0.0788 (5)	0.0500 (4)	0.0650 (5)	−0.0101 (4)	0.0015 (4)	−0.0271 (4)
Br6	0.0785 (5)	0.0318 (3)	0.0369 (3)	−0.0005 (3)	0.0089 (3)	−0.0031 (3)
Br7	0.0333 (3)	0.0463 (4)	0.0373 (3)	−0.0007 (3)	0.0038 (2)	0.0046 (3)
Br8	0.0324 (3)	0.0653 (5)	0.0795 (5)	−0.0106 (3)	0.0040 (3)	0.0040 (4)
Br9	0.0542 (4)	0.0467 (4)	0.0318 (3)	0.0074 (3)	−0.0061 (3)	−0.0070 (3)
Br10	0.0519 (4)	0.0484 (4)	0.0298 (3)	0.0162 (3)	−0.0033 (3)	0.0071 (3)
N1	0.036 (3)	0.050 (3)	0.027 (2)	0.008 (2)	−0.004 (2)	−0.001 (2)
N2	0.033 (3)	0.048 (3)	0.046 (3)	0.008 (2)	0.003 (2)	−0.002 (3)
C1	0.060 (5)	0.045 (4)	0.078 (5)	0.021 (3)	−0.009 (4)	−0.005 (4)
C2	0.067 (5)	0.068 (5)	0.060 (5)	−0.019 (4)	0.001 (4)	−0.008 (4)
C3	0.061 (5)	0.100 (7)	0.038 (4)	0.028 (4)	0.011 (3)	0.012 (4)
C4A	0.048 (7)	0.052 (8)	0.039 (6)	0.019 (6)	0.002 (5)	−0.007 (6)
C5A	0.054 (13)	0.050 (9)	0.11 (2)	−0.011 (8)	0.003 (10)	−0.008 (11)
C6A	0.042 (7)	0.041 (7)	0.092 (10)	0.021 (6)	−0.007 (7)	0.008 (7)
C4B	0.050 (9)	0.015 (7)	0.028 (7)	0.004 (6)	0.002 (6)	−0.008 (6)
C5B	0.041 (15)	0.12 (2)	0.07 (2)	−0.020 (13)	−0.018 (11)	0.002 (16)
C6B	0.056 (14)	0.034 (11)	0.19 (3)	0.023 (10)	0.029 (15)	0.003 (15)
N3	0.036 (3)	0.039 (3)	0.029 (3)	−0.001 (2)	0.003 (2)	−0.006 (2)
C7	0.036 (3)	0.034 (3)	0.025 (3)	−0.004 (3)	0.004 (2)	−0.003 (3)
C8	0.031 (3)	0.073 (5)	0.050 (4)	0.002 (3)	−0.003 (3)	−0.002 (4)
C9	0.073 (5)	0.037 (4)	0.068 (5)	0.009 (3)	−0.012 (4)	0.005 (4)
N4	0.038 (3)	0.028 (3)	0.039 (3)	0.008 (2)	0.006 (2)	−0.001 (2)
C10	0.038 (3)	0.045 (4)	0.029 (3)	−0.002 (3)	−0.003 (3)	0.000 (3)
C11	0.062 (4)	0.100 (6)	0.028 (3)	−0.003 (4)	0.001 (3)	0.006 (4)
C12	0.050 (4)	0.065 (5)	0.067 (5)	−0.010 (4)	0.002 (3)	−0.006 (4)
OW	0.128 (6)	0.243 (10)	0.105 (5)	−0.005 (6)	−0.008 (5)	0.028 (6)

Sb1—Br1	2.9035 (7)	C6A—H6A	0.96
Sb1—Br2	2.6762 (7)	C6A—H6B	0.96
Sb1—Br3	2.9906 (7)	C6A—H6C	0.96
Sb1—Br4	2.6553 (7)	C4B—H4C	0.97
Sb1—Br5	2.9240 (8)	C4B—H4D	0.97
Sb1—Br6	2.7347 (7)	C5B—H5E	0.96
Br5—Sb2i	3.2709 (8)	C5B—H5F	0.96
Sb2—Br6ii	3.5447 (7)	C5B—H5G	0.96
Sb2—Br7	2.8895 (6)	C6B—H6E	0.96
Sb2—Br8	2.6403 (7)	C6B—H6F	0.96
Sb2—Br9	2.5405 (7)	C6B—H6G	0.96
Sb2—Br10	2.5466 (7)	N3—C8	1.477 (7)
N1—C2	1.471 (7)	N3—C9	1.479 (7)
N1—C1	1.480 (7)	N3—C7	1.500 (6)
N1—C3	1.493 (8)	N3—H3	0.91
N1—H1	0.91	C7—C7ii	1.503 (10)
N2—C6B	1.345 (7)	C7—H7A	0.97
N2—C5A	1.389 (19)	C7—H7B	0.97
N2—C4A	1.437 (10)	C8—H8A	0.96
N2—C5B	1.58 (2)	C8—H8B	0.96
N2—C6A	1.596 (11)	C8—H8C	0.96
N2—C4B	1.598 (13)	C9—H9A	0.96
N2—H2	0.91	C9—H9B	0.96
C1—H1A	0.96	C9—H9C	0.96
C1—H1B	0.96	N4—C10	1.467 (7)
C1—H1C	0.96	N4—C12	1.480 (7)
C2—H2A	0.96	N4—C11	1.487 (7)
C2—H2B	0.96	N4—H4	0.91
C2—H2C	0.96	C10—C10iii	1.537 (10)
C3—C4B	1.302 (13)	C10—H10A	0.97
C3—C4A	1.422 (11)	C10—H10B	0.97
C3—H3A	0.97	C11—H11A	0.96
C3—H3B	0.97	C11—H11B	0.96
C3—H3C	0.97	C11—H11C	0.96
C3—H3D	0.97	C12—H12A	0.96
C4A—H4A	0.97	C12—H12B	0.96
C4A—H4B	0.97	C12—H12C	0.96
C5A—H5A	0.96	OW—H1W	0.828
C5A—H5B	0.96	OW—H2W	0.8264
C5A—H5C	0.96
Br1—Sb1—Br2	177.35 (2)	H3A—C3—H3D	147.2
Br1—Sb1—Br3	90.40 (2)	H3B—C3—H3D	63.1
Br1—Sb1—Br4	89.37 (2)	H3C—C3—H3D	106.3
Br1—Sb1—Br5	81.78 (2)	C3—C4A—N2	121.0 (9)
Br1—Sb1—Br6	89.87 (2)	C3—C4A—H4A	107.1
Br2—Sb1—Br3	89.30 (2)	N2—C4A—H4A	107.1
Br2—Sb1—Br4	90.86 (3)	C3—C4A—H4B	107.1
Br2—Sb1—Br5	95.57 (2)	N2—C4A—H4B	107.1
Br2—Sb1—Br6	92.77 (2)	H4A—C4A—H4B	106.8
Br3—Sb1—Br4	178.37 (2)	N2—C5A—H5A	109.5
Br3—Sb1—Br5	86.43 (2)	N2—C5A—H5B	109.5
Br3—Sb1—Br6	91.03 (2)	H5A—C5A—H5B	109.5
Br4—Sb1—Br5	91.93 (2)	N2—C5A—H5C	109.5
Br4—Sb1—Br6	90.58 (2)	H5A—C5A—H5C	109.5
Br5—Sb1—Br6	171.25 (2)	H5B—C5A—H5C	109.5
Br5iv—Sb2—Br6ii	103.81 (2)	N2—C6A—H6A	109.5
Br5iv—Sb2—Br7	89.89 (2)	N2—C6A—H6B	109.5
Br5iv—Sb2—Br8	91.26 (2)	H6A—C6A—H6B	109.5
Br5iv—Sb2—Br9	82.55 (2)	N2—C6A—H6C	109.5
Br5iv—Sb2—Br10	175.44 (2)	H6A—C6A—H6C	109.5
Br6ii—Sb2—Br7	87.61 (2)	H6B—C6A—H6C	109.5
Br6ii—Sb2—Br8	93.62 (2)	C3—C4B—N2	117.8 (10)
Br6ii—Sb2—Br9	172.43 (2)	C3—C4B—H4C	107.9
Br6ii—Sb2—Br10	80.31 (2)	N2—C4B—H4C	107.9
Br7—Sb2—Br8	178.07 (3)	C3—C4B—H4D	107.9
Br7—Sb2—Br9	88.31 (2)	N2—C4B—H4D	107.9
Br7—Sb2—Br10	88.33 (2)	H4C—C4B—H4D	107.2
Br8—Sb2—Br9	90.30 (2)	N2—C5B—H5E	109.5
Br8—Sb2—Br10	90.41 (2)	N2—C5B—H5F	109.5
Br9—Sb2—Br10	93.20 (2)	H5E—C5B—H5F	109.5
Sb2i—Br5—Sb1	149.32 (3)	N2—C5B—H5G	109.5
Sb2ii—Br6—Sb1	173.75 (3)	H5E—C5B—H5G	109.5
C2—N1—C1	110.7 (5)	H5F—C5B—H5G	109.5
C2—N1—C3	112.2 (5)	N2—C6B—H6E	109.5
C1—N1—C3	110.2 (5)	N2—C6B—H6F	109.5
C2—N1—H1	107.9	H6E—C6B—H6F	109.5
C1—N1—H1	107.9	N2—C6B—H6G	109.5
C3—N1—H1	107.9	H6E—C6B—H6G	109.5
C6B—N2—C5A	114.1 (12)	H6F—C6B—H6G	109.5
C6B—N2—C4A	76.2 (5)	C8—N3—C9	110.9 (5)
C5A—N2—C4A	118.1 (10)	C8—N3—C7	111.6 (4)
C6B—N2—C5B	113.2 (15)	C9—N3—C7	113.3 (4)
C5A—N2—C5B	23.1 (17)	C8—N3—H3	106.9
C4A—N2—C5B	141.2 (13)	C9—N3—H3	106.9
C6B—N2—C6A	32.9 (5)	C7—N3—H3	106.9
C5A—N2—C6A	108.4 (10)	N3—C7—C7ii	110.5 (5)
C4A—N2—C6A	106.8 (7)	N3—C7—H7A	109.6
C5B—N2—C6A	95.3 (13)	C7ii—C7—H7A	109.6
C6B—N2—C4B	114.4 (6)	N3—C7—H7B	109.6
C5A—N2—C4B	75.8 (9)	C7ii—C7—H7B	109.6
C4A—N2—C4B	48.3 (6)	H7A—C7—H7B	108.1
C5B—N2—C4B	97.1 (11)	N3—C8—H8A	109.5
C6A—N2—C4B	146.8 (8)	N3—C8—H8B	109.5
C6B—N2—H2	129.6	H8A—C8—H8B	109.5
C5A—N2—H2	107.7	N3—C8—H8C	109.5
C4A—N2—H2	107.7	H8A—C8—H8C	109.5
C5B—N2—H2	94.8	H8B—C8—H8C	109.5
C6A—N2—H2	107.7	N3—C9—H9A	109.5
C4B—N2—H2	101.8	N3—C9—H9B	109.5
N1—C1—H1A	109.5	H9A—C9—H9B	109.5
N1—C1—H1B	109.5	N3—C9—H9C	109.5
H1A—C1—H1B	109.5	H9A—C9—H9C	109.5
N1—C1—H1C	109.5	H9B—C9—H9C	109.5
H1A—C1—H1C	109.5	C10—N4—C12	109.9 (4)
H1B—C1—H1C	109.5	C10—N4—C11	113.6 (5)
N1—C2—H2A	109.5	C12—N4—C11	108.7 (5)
N1—C2—H2B	109.5	C10—N4—H4	108.2
H2A—C2—H2B	109.5	C12—N4—H4	108.2
N1—C2—H2C	109.5	C11—N4—H4	108.2
H2A—C2—H2C	109.5	N4—C10—C10iii	112.4 (6)
H2B—C2—H2C	109.5	N4—C10—H10A	109.1
C4B—C3—C4A	54.4 (7)	C10iii—C10—H10A	109.1
C4B—C3—N1	125.2 (8)	N4—C10—H10B	109.1
C4A—C3—N1	122.3 (7)	C10iii—C10—H10B	109.1
C4B—C3—H3A	53.3	H10A—C10—H10B	107.9
C4A—C3—H3A	106.8	N4—C11—H11A	109.5
N1—C3—H3A	106.8	N4—C11—H11B	109.5
C4B—C3—H3B	127.2	H11A—C11—H11B	109.5
C4A—C3—H3B	106.8	N4—C11—H11C	109.5
N1—C3—H3B	106.8	H11A—C11—H11C	109.5
H3A—C3—H3B	106.6	H11B—C11—H11C	109.5
C4B—C3—H3C	106	N4—C12—H12A	109.5
C4A—C3—H3C	130.7	N4—C12—H12B	109.5
N1—C3—H3C	106	H12A—C12—H12B	109.5
H3A—C3—H3C	64.1	N4—C12—H12C	109.5
H3B—C3—H3C	44.6	H12A—C12—H12C	109.5
C4B—C3—H3D	106	H12B—C12—H12C	109.5
C4A—C3—H3D	53.9	H1W—OW—H2W	115.9
N1—C3—H3D	106

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br1	0.91	2.59	3.362 (4)	143
N2—H2···Br1	0.91	2.56	3.353 (5)	146
N3—H3···Br7ii	0.91	2.5	3.352 (4)	157
N4—H4···Br3	0.91	2.52	3.318 (4)	147
OW—H1W···Br4v	0.83	3.03	3.759 (7)	148
OW—H2W···Br3	0.83	2.67	3.449 (7)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Br1	0.91	2.59	3.362 (4)	143
N2—H2⋯Br1	0.91	2.56	3.353 (5)	146
N3—H3⋯Br7i	0.91	2.5	3.352 (4)	157
N4—H4⋯Br3	0.91	2.52	3.318 (4)	147
OW—H1W⋯Br4ii	0.83	3.03	3.759 (7)	148
OW—H2W⋯Br3	0.83	2.67	3.449 (7)	157

Symmetry codes: (i) ; (ii) .