Isostructural organic-inorganic hybrid compounds: tri­ethyl­choline tri­bromido­cadmate and tri­ethyl­choline tri­bromido­mercurate

In order to search for new anionic architectures and develop useful organic-inorganic hybrid materials in halometallate systems, two new crystalline organic-inorganic hybrid compounds have been prepared, i.e. catena-poly[tri­ethyl(2-hy­droxy­ethyl)aza­nium [[bromido­cadmate(II)]-di-[mu]-bromido]], {(C₈H₂₀NO)[CdBr₃]}_n, (1), and catena-poly[triethyl(2-hy­droxy­ethyl)aza­nium [[bromido­mercurate(II)]-di-[mu]-bromido]], {(C₈H₂₀NO)[HgBr₃]}_n, (2), and the structures determined by X-ray diffraction analysis. The compounds are isostructural, crystallizing in the space group P2₁/n. The metal centres are five-coordinated by bromide anions, giving a slightly distorted trigonal-bipyramidal geometry. The crystal structures consist of one-dimensional edge-sharing chains of MBr₅ trigonal bipyramids, between which tri­ethyl­choline counter-cations are inter­calated. O-H...Br hydrogen-bonding inter­actions are present between the cations and anions.

Computing details

For both compounds, data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(1) catena-Poly[triethyl(2-hydroxyethyl)azanium [[bromidocadmate(II)]-di-µ-bromido]]

Crystal data

(C8H20NO)[CdBr3]	F(000) = 944
Mr = 498.38	Dx = 2.264 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3337 reflections
a = 10.440 (2) Å	θ = 3.3–27.5°
b = 7.7444 (15) Å	µ = 9.67 mm^−1
c = 18.161 (4) Å	T = 293 K
β = 95.16 (3)°	Block, colourless
V = 1462.4 (5) Å^3	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer	2729 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 27.5°, θmin = 3.3°
ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→10
Tmin = 0.248, Tmax = 0.248	l = −23→23
14640 measured reflections	3 standard reflections every 180 reflections
3337 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 1.0147P] where P = (Fo^2 + 2Fc^2)/3
S = 1.21	(Δ/σ)max < 0.001
3337 reflections	Δρmax = 0.71 e Å^−3
127 parameters	Δρmin = −2.06 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0819 (12)

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
Cd1	0.98923 (4)	0.74601 (5)	0.03627 (2)	0.03501 (14)
Br1	0.94600 (6)	0.73423 (7)	0.17217 (3)	0.03691 (17)
Br3	1.18000 (5)	0.55465 (7)	0.00335 (3)	0.03590 (17)
Br2	0.84679 (5)	0.93902 (7)	−0.05617 (3)	0.03613 (17)
N1	0.4909 (4)	0.2992 (5)	0.8204 (2)	0.0230 (9)
C1	0.5249 (5)	0.2059 (7)	0.8930 (3)	0.0319 (13)
H1A	0.5675	0.0986	0.8824	0.038*
H1C	0.5867	0.2760	0.9228	0.038*
C3	0.4216 (5)	0.4678 (6)	0.8326 (3)	0.0279 (12)
H3A	0.3387	0.4410	0.8500	0.034*
H3B	0.4055	0.5256	0.7853	0.034*
C2	0.4154 (6)	0.1639 (7)	0.9391 (3)	0.0365 (13)
H2A	0.4475	0.1567	0.9908	0.044*
H2B	0.3517	0.2554	0.9339	0.044*
C7	0.6140 (5)	0.3404 (7)	0.7856 (3)	0.0345 (13)
H7A	0.5937	0.4182	0.7444	0.041*
H7B	0.6717	0.4008	0.8217	0.041*
C5	0.4020 (5)	0.1844 (7)	0.7700 (3)	0.0291 (12)
H5A	0.4442	0.0742	0.7643	0.035*
H5B	0.3242	0.1628	0.7940	0.035*
C6	0.3649 (7)	0.2594 (8)	0.6937 (4)	0.0461 (16)
H6A	0.3097	0.1798	0.6655	0.069*
H6B	0.4411	0.2789	0.6689	0.069*
H6C	0.3205	0.3668	0.6985	0.069*
C8	0.6837 (6)	0.1850 (9)	0.7582 (4)	0.0538 (19)
H8A	0.7604	0.2223	0.7373	0.081*
H8B	0.6287	0.1261	0.7211	0.081*
H8C	0.7064	0.1081	0.7987	0.081*
C4	0.4912 (7)	0.5936 (8)	0.8869 (4)	0.0532 (18)
H4A	0.4395	0.6951	0.8909	0.080*
H4B	0.5722	0.6251	0.8696	0.080*
H4C	0.5058	0.5397	0.9346	0.080*
O1	0.3576 (4)	0.0053 (6)	0.9162 (3)	0.0496 (12)
H1B	0.2982	−0.0158	0.9415	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.0380 (3)	0.0390 (3)	0.0287 (2)	0.01494 (18)	0.00671 (19)	0.00640 (18)
Br1	0.0481 (4)	0.0355 (3)	0.0284 (3)	−0.0047 (3)	0.0105 (3)	−0.0021 (2)
Br3	0.0226 (3)	0.0369 (3)	0.0475 (4)	0.0045 (2)	−0.0003 (2)	−0.0119 (3)
Br2	0.0323 (3)	0.0354 (3)	0.0396 (4)	0.0017 (2)	−0.0028 (2)	0.0117 (3)
N1	0.018 (2)	0.021 (2)	0.029 (2)	−0.0008 (16)	−0.0009 (18)	−0.0007 (18)
C1	0.032 (3)	0.024 (3)	0.038 (3)	0.003 (2)	−0.008 (3)	0.004 (2)
C3	0.028 (3)	0.021 (2)	0.034 (3)	0.008 (2)	0.000 (2)	−0.003 (2)
C2	0.047 (4)	0.029 (3)	0.033 (3)	0.002 (3)	0.005 (3)	0.004 (3)
C7	0.022 (3)	0.037 (3)	0.046 (4)	−0.001 (2)	0.008 (2)	−0.001 (3)
C5	0.023 (3)	0.029 (3)	0.034 (3)	−0.003 (2)	−0.002 (2)	−0.007 (2)
C6	0.053 (4)	0.050 (4)	0.033 (3)	−0.010 (3)	−0.009 (3)	−0.001 (3)
C8	0.030 (3)	0.061 (4)	0.072 (5)	0.008 (3)	0.018 (3)	−0.005 (4)
C4	0.058 (4)	0.036 (3)	0.063 (5)	0.006 (3)	−0.001 (4)	−0.021 (3)
O1	0.048 (3)	0.049 (3)	0.054 (3)	−0.012 (2)	0.017 (2)	−0.001 (2)

Geometric parameters (Å, º)

Cd1—Br1	2.5503 (9)	C2—H2A	0.9700
Cd1—Br3	2.5950 (8)	C2—H2B	0.9700
Cd1—Br2	2.6105 (9)	C7—C8	1.514 (8)
Cd1—Br3^i	2.9719 (8)	C7—H7A	0.9700
Cd1—Br2^ii	2.9832 (8)	C7—H7B	0.9700
Br3—Cd1^i	2.9719 (8)	C5—C6	1.521 (8)
Br2—Cd1^ii	2.9832 (8)	C5—H5A	0.9700
N1—C7	1.516 (6)	C5—H5B	0.9700
N1—C1	1.518 (7)	C6—H6A	0.9600
N1—C3	1.519 (6)	C6—H6B	0.9600
N1—C5	1.528 (6)	C6—H6C	0.9600
C1—C2	1.511 (8)	C8—H8A	0.9600
C1—H1A	0.9700	C8—H8B	0.9600
C1—H1C	0.9700	C8—H8C	0.9600
C3—C4	1.523 (8)	C4—H4A	0.9600
C3—H3A	0.9700	C4—H4B	0.9600
C3—H3B	0.9700	C4—H4C	0.9600
C2—O1	1.414 (7)	O1—H1B	0.8200
Br1—Cd1—Br3	114.14 (3)	C1—C2—H2B	109.6
Br1—Cd1—Br2	120.18 (3)	H2A—C2—H2B	108.1
Br3—Cd1—Br2	125.69 (3)	C8—C7—N1	114.9 (5)
Br1—Cd1—Br3^i	93.05 (3)	C8—C7—H7A	108.5
Br3—Cd1—Br3^i	87.06 (2)	N1—C7—H7A	108.5
Br2—Cd1—Br3^i	90.06 (3)	C8—C7—H7B	108.5
Br1—Cd1—Br2^ii	93.54 (3)	N1—C7—H7B	108.5
Br3—Cd1—Br2^ii	92.92 (3)	H7A—C7—H7B	107.5
Br2—Cd1—Br2^ii	84.10 (3)	C6—C5—N1	114.5 (4)
Br3^i—Cd1—Br2^ii	172.80 (2)	C6—C5—H5A	108.6
Cd1—Br3—Cd1^i	92.94 (2)	N1—C5—H5A	108.6
Cd1—Br2—Cd1^ii	95.90 (3)	C6—C5—H5B	108.6
C7—N1—C1	108.8 (4)	N1—C5—H5B	108.6
C7—N1—C3	108.2 (4)	H5A—C5—H5B	107.6
C1—N1—C3	111.1 (4)	C5—C6—H6A	109.5
C7—N1—C5	111.4 (4)	C5—C6—H6B	109.5
C1—N1—C5	108.9 (4)	H6A—C6—H6B	109.5
C3—N1—C5	108.5 (4)	C5—C6—H6C	109.5
C2—C1—N1	117.0 (4)	H6A—C6—H6C	109.5
C2—C1—H1A	108.0	H6B—C6—H6C	109.5
N1—C1—H1A	108.0	C7—C8—H8A	109.5
C2—C1—H1C	108.0	C7—C8—H8B	109.5
N1—C1—H1C	108.0	H8A—C8—H8B	109.5
H1A—C1—H1C	107.3	C7—C8—H8C	109.5
N1—C3—C4	116.0 (4)	H8A—C8—H8C	109.5
N1—C3—H3A	108.3	H8B—C8—H8C	109.5
C4—C3—H3A	108.3	C3—C4—H4A	109.5
N1—C3—H3B	108.3	C3—C4—H4B	109.5
C4—C3—H3B	108.3	H4A—C4—H4B	109.5
H3A—C3—H3B	107.4	C3—C4—H4C	109.5
O1—C2—C1	110.4 (5)	H4A—C4—H4C	109.5
O1—C2—H2A	109.6	H4B—C4—H4C	109.5
C1—C2—H2A	109.6	C2—O1—H1B	109.5
O1—C2—H2B	109.6
Br1—Cd1—Br3—Cd1^i	92.02 (3)	C7—N1—C3—C4	−64.0 (6)
Br2—Cd1—Br3—Cd1^i	−87.96 (4)	C1—N1—C3—C4	55.4 (6)
Br3^i—Cd1—Br3—Cd1^i	0.0	C5—N1—C3—C4	175.1 (5)
Br2^ii—Cd1—Br3—Cd1^i	−172.79 (2)	N1—C1—C2—O1	85.9 (6)
Br1—Cd1—Br2—Cd1^ii	90.67 (3)	C1—N1—C7—C8	68.8 (6)
Br3—Cd1—Br2—Cd1^ii	−89.36 (3)	C3—N1—C7—C8	−170.4 (5)
Br3^i—Cd1—Br2—Cd1^ii	−175.78 (2)	C5—N1—C7—C8	−51.2 (6)
Br2^ii—Cd1—Br2—Cd1^ii	0.0	C7—N1—C5—C6	−57.5 (6)
C7—N1—C1—C2	176.0 (5)	C1—N1—C5—C6	−177.5 (5)
C3—N1—C1—C2	57.0 (6)	C3—N1—C5—C6	61.5 (6)
C5—N1—C1—C2	−62.4 (6)

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···Br2^iii	0.82	2.75	3.489 (4)	151

Symmetry code: (iii) −x+1, −y+1, −z+1.

(2) catena-Poly[triethyl(2-hydroxyethyl)azanium [[bromidomercurate(II)]-di-µ-bromido]]

Crystal data

(C8H20NO)[HgBr3]	F(000) = 1072
Mr = 586.57	Dx = 2.666 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3348 reflections
a = 10.373 (2) Å	θ = 3.3–27.5°
b = 7.8620 (16) Å	µ = 18.71 mm^−1
c = 17.984 (4) Å	T = 293 K
β = 94.85 (3)°	Block, colourless
V = 1461.5 (5) Å^3	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer	2404 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.085
Graphite monochromator	θmax = 27.5°, θmin = 3.3°
ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.118, Tmax = 0.118	l = −23→23
14649 measured reflections	3 standard reflections every 180 reflections
3348 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0326P)^2 + 2.2686P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
3348 reflections	Δρmax = 1.11 e Å^−3
127 parameters	Δρmin = −1.57 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0819 (12)

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
Hg1	0.48696 (4)	0.75529 (5)	0.03655 (2)	0.04689 (16)
Br2	0.68530 (8)	0.92145 (11)	0.00256 (5)	0.0431 (3)
Br1	0.34645 (8)	0.58644 (11)	−0.06039 (5)	0.0423 (3)
Br3	0.44772 (10)	0.76597 (11)	0.17318 (5)	0.0448 (3)
N1	0.0088 (6)	0.7950 (7)	0.1785 (3)	0.0221 (14)
O1	0.1437 (6)	0.5042 (8)	0.0819 (4)	0.0520 (17)
H1A	0.2047	0.4833	0.0572	0.078*
C7	−0.0236 (7)	0.7022 (11)	0.1048 (5)	0.034 (2)
H7A	−0.0669	0.5967	0.1153	0.041*
H7B	−0.0849	0.7713	0.0742	0.041*
C3	0.0766 (8)	0.9611 (9)	0.1661 (5)	0.0317 (19)
H3A	0.0941	1.0165	0.2141	0.038*
H3B	0.1594	0.9357	0.1474	0.038*
C2	0.1342 (10)	0.7544 (11)	0.3055 (5)	0.048 (3)
H2A	0.1923	0.6785	0.3336	0.071*
H2B	0.0565	0.7670	0.3304	0.071*
H2C	0.1748	0.8633	0.3016	0.071*
C5	−0.1143 (7)	0.8318 (10)	0.2130 (5)	0.0327 (19)
H5A	−0.1723	0.8913	0.1767	0.039*
H5B	−0.0952	0.9080	0.2549	0.039*
C8	0.0884 (9)	0.6604 (11)	0.0590 (5)	0.043 (2)
H8A	0.0578	0.6546	0.0066	0.051*
H8B	0.1531	0.7494	0.0652	0.051*
C1	0.1015 (7)	0.6828 (10)	0.2289 (5)	0.0301 (19)
H1B	0.0623	0.5717	0.2337	0.036*
H1C	0.1809	0.6672	0.2049	0.036*
C4	0.0067 (8)	1.0846 (11)	0.1139 (6)	0.048 (3)
H4A	0.0583	1.1852	0.1103	0.072*
H4B	−0.0745	1.1144	0.1324	0.072*
H4C	−0.0087	1.0336	0.0654	0.072*
C6	−0.1859 (9)	0.6739 (13)	0.2407 (6)	0.054 (3)
H6A	−0.2636	0.7095	0.2617	0.081*
H6B	−0.1308	0.6158	0.2781	0.081*
H6C	−0.2076	0.5986	0.1995	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.0505 (3)	0.0607 (3)	0.0303 (2)	−0.01604 (19)	0.00843 (18)	−0.00828 (18)
Br2	0.0311 (5)	0.0513 (5)	0.0460 (6)	−0.0040 (4)	−0.0010 (4)	0.0113 (5)
Br1	0.0423 (5)	0.0478 (5)	0.0364 (6)	−0.0028 (4)	0.0004 (4)	−0.0114 (4)
Br3	0.0565 (6)	0.0501 (6)	0.0290 (5)	0.0052 (4)	0.0109 (4)	0.0004 (4)
N1	0.023 (3)	0.027 (3)	0.016 (4)	0.002 (3)	−0.002 (3)	0.001 (3)
O1	0.048 (4)	0.056 (4)	0.054 (5)	0.014 (3)	0.015 (3)	0.000 (4)
C7	0.028 (5)	0.043 (5)	0.029 (5)	0.003 (4)	−0.011 (4)	−0.008 (4)
C3	0.036 (5)	0.026 (4)	0.033 (5)	−0.007 (4)	0.004 (4)	0.002 (4)
C2	0.054 (6)	0.060 (6)	0.026 (5)	0.011 (5)	−0.011 (5)	0.000 (5)
C5	0.025 (4)	0.040 (5)	0.034 (5)	0.007 (4)	0.004 (4)	0.008 (4)
C8	0.062 (6)	0.039 (5)	0.028 (5)	−0.011 (5)	0.015 (5)	−0.005 (4)
C1	0.028 (5)	0.031 (4)	0.030 (5)	0.008 (3)	−0.003 (4)	0.008 (4)
C4	0.045 (6)	0.041 (5)	0.058 (7)	−0.008 (4)	0.001 (5)	0.014 (5)
C6	0.031 (5)	0.073 (7)	0.062 (7)	−0.005 (5)	0.023 (5)	−0.001 (6)

Geometric parameters (Å, º)

Hg1—Br3	2.5258 (12)	C2—C1	1.500 (12)
Hg1—Br1	2.5489 (11)	C2—H2A	0.9600
Hg1—Br2	2.5546 (10)	C2—H2B	0.9600
Hg1—Br1^i	3.2036 (11)	C2—H2C	0.9600
Hg1—Br2^ii	3.1518 (11)	C5—C6	1.550 (12)
N1—C5	1.494 (10)	C5—H5A	0.9700
N1—C3	1.509 (9)	C5—H5B	0.9700
N1—C7	1.526 (10)	C8—H8A	0.9700
N1—C1	1.542 (9)	C8—H8B	0.9700
O1—C8	1.402 (10)	C1—H1B	0.9700
O1—H1A	0.8200	C1—H1C	0.9700
C7—C8	1.515 (11)	C4—H4A	0.9600
C7—H7A	0.9700	C4—H4B	0.9600
C7—H7B	0.9700	C4—H4C	0.9600
C3—C4	1.496 (11)	C6—H6A	0.9600
C3—H3A	0.9700	C6—H6B	0.9600
C3—H3B	0.9700	C6—H6C	0.9600
Br3—Hg1—Br1	123.57 (4)	N1—C5—H5A	108.4
Br3—Hg1—Br2	114.52 (4)	C6—C5—H5A	108.4
Br1—Hg1—Br2	121.88 (4)	N1—C5—H5B	108.4
C5—N1—C3	108.6 (6)	C6—C5—H5B	108.4
C5—N1—C7	108.7 (6)	H5A—C5—H5B	107.5
C3—N1—C7	110.9 (6)	O1—C8—C7	110.2 (7)
C5—N1—C1	112.3 (6)	O1—C8—H8A	109.6
C3—N1—C1	107.8 (6)	C7—C8—H8A	109.6
C7—N1—C1	108.5 (6)	O1—C8—H8B	109.6
C8—O1—H1A	109.5	C7—C8—H8B	109.6
C8—C7—N1	117.0 (6)	H8A—C8—H8B	108.1
C8—C7—H7A	108.1	C2—C1—N1	114.0 (6)
N1—C7—H7A	108.1	C2—C1—H1B	108.8
C8—C7—H7B	108.1	N1—C1—H1B	108.8
N1—C7—H7B	108.1	C2—C1—H1C	108.8
H7A—C7—H7B	107.3	N1—C1—H1C	108.8
C4—C3—N1	116.6 (6)	H1B—C1—H1C	107.6
C4—C3—H3A	108.2	C3—C4—H4A	109.5
N1—C3—H3A	108.2	C3—C4—H4B	109.5
C4—C3—H3B	108.2	H4A—C4—H4B	109.5
N1—C3—H3B	108.2	C3—C4—H4C	109.5
H3A—C3—H3B	107.3	H4A—C4—H4C	109.5
C1—C2—H2A	109.5	H4B—C4—H4C	109.5
C1—C2—H2B	109.5	C5—C6—H6A	109.5
H2A—C2—H2B	109.5	C5—C6—H6B	109.5
C1—C2—H2C	109.5	H6A—C6—H6B	109.5
H2A—C2—H2C	109.5	C5—C6—H6C	109.5
H2B—C2—H2C	109.5	H6A—C6—H6C	109.5
N1—C5—C6	115.3 (7)	H6B—C6—H6C	109.5
C5—N1—C7—C8	177.2 (7)	C7—N1—C5—C6	68.3 (9)
C3—N1—C7—C8	57.9 (9)	C1—N1—C5—C6	−51.8 (9)
C1—N1—C7—C8	−60.4 (9)	N1—C7—C8—O1	86.8 (9)
C5—N1—C3—C4	−62.3 (9)	C5—N1—C1—C2	−56.0 (9)
C7—N1—C3—C4	57.1 (9)	C3—N1—C1—C2	63.7 (9)
C1—N1—C3—C4	175.8 (7)	C7—N1—C1—C2	−176.2 (7)
C3—N1—C5—C6	−171.0 (7)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Br1	0.82	2.80	3.507 (6)	146