Crystal structure and Hirshfeld surface analysis of two iHOFs based on CH⋯NC hydrogen bonding

Two ionic hydrogen-bonded organic frameworks (iHOFs) assembled from 4-cyano-N-(4-cyano­benz­yl)pyridinium, have been crystallized with Br⁻ and an­ti­­mony(III) penta­bromide, [SbBr₅]²⁻, as counter-ions and characterized. These are 4-cyano-N-(4-cyano­benz­yl)pyridinium bromide, C₁₄H₁₀N₃⁺·Br⁻, and bis­[4-cyano-N-(4-cyano­benz­yl)pyridinium] anti­mony(III) penta­bromide, (C₁₄H₁₀N₃)₂[SbBr₅]. The CH⋯NC inter­actions induced by templating anions con­struct disparate frameworks. Hirshfeld surface analysis indicated that these crystals exhibit two types of hydrogen-bonding inter­actions, specifically CH⋯NC and CH⋯Br. Consecutive reverse-parallel CH⋯NC hydrogen-bonding inter­actions in these crystals induced the formation of a large number of CH⋯NC bonds which exhibit both cis and trans configurations.

Computing details

4-Cyano-N-(4-cyanobenzyl)pyridinium bromide (iHOFI)

Crystal data

C14H10N3^+·Br^−	Dx = 1.630 Mg m^−3
Mr = 300.16	Ga Kα radiation, λ = 1.34138 Å
Orthorhombic, Pnma	Cell parameters from 6776 reflections
a = 8.7734 (4) Å	θ = 3.9–59.4°
b = 7.0554 (3) Å	µ = 2.94 mm^−1
c = 19.7544 (10) Å	T = 150 K
V = 1222.79 (10) Å^3	Block, colourless
Z = 4	0.1 × 0.08 × 0.05 mm
F(000) = 600

Data collection

Bruker D8 VENTURE PHOTON III diffractometer	1245 reflections with I > 2σ(I)
Radiation source: MetalJet	Rint = 0.055
φ and ω scans	θmax = 59.4°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −11→11
Tmin = 0.657, Tmax = 0.752	k = −8→9
15238 measured reflections	l = −24→25
1461 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.069	w = 1/[σ^2(Fo^2) + (0.0252P)^2 + 1.2992P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1461 reflections	Δρmax = 0.83 e Å^−3
97 parameters	Δρmin = −0.59 e Å^−3
0 restraints

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.65349 (4)	0.750000	0.24449 (2)	0.02461 (12)
N1	0.3682 (3)	0.250000	0.19981 (12)	0.0191 (5)
N2	0.7171 (4)	0.250000	−0.01965 (15)	0.0355 (7)
N3	0.7791 (4)	0.250000	0.53003 (14)	0.0349 (7)
C1	0.4120 (2)	0.4177 (3)	0.17268 (10)	0.0231 (5)
H1	0.379092	0.533022	0.192725	0.028*
C2	0.5038 (2)	0.4218 (3)	0.11626 (10)	0.0232 (4)
H2	0.535449	0.538883	0.097130	0.028*
C3	0.5492 (3)	0.250000	0.08783 (14)	0.0208 (6)
C4	0.6446 (4)	0.250000	0.02813 (15)	0.0264 (7)
C5	0.2776 (3)	0.250000	0.26353 (14)	0.0212 (6)
H5A	0.211507	0.136349	0.264955	0.025*	0.5
H5B	0.211507	0.363651	0.264955	0.025*	0.5
C6	0.3826 (3)	0.250000	0.32356 (14)	0.0199 (6)
C7	0.4332 (2)	0.4210 (3)	0.35092 (11)	0.0248 (5)
H7	0.397935	0.537574	0.332593	0.030*
C8	0.5343 (3)	0.4217 (3)	0.40457 (11)	0.0264 (5)
H8	0.568918	0.538316	0.423071	0.032*
C9	0.5850 (3)	0.250000	0.43138 (15)	0.0233 (7)
C10	0.6925 (4)	0.250000	0.48684 (16)	0.0276 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02063 (17)	0.01648 (17)	0.03671 (19)	0.000	−0.00149 (13)	0.000
N1	0.0165 (12)	0.0193 (13)	0.0216 (11)	0.000	−0.0025 (9)	0.000
N2	0.0462 (18)	0.0288 (17)	0.0315 (15)	0.000	0.0072 (13)	0.000
N3	0.0394 (17)	0.0338 (18)	0.0317 (15)	0.000	−0.0054 (13)	0.000
C1	0.0240 (10)	0.0182 (12)	0.0272 (10)	0.0016 (9)	−0.0015 (8)	0.0000 (8)
C2	0.0266 (11)	0.0175 (11)	0.0256 (10)	−0.0016 (9)	−0.0027 (8)	0.0008 (8)
C3	0.0195 (14)	0.0231 (17)	0.0197 (13)	0.000	−0.0030 (11)	0.000
C4	0.0323 (17)	0.0207 (17)	0.0261 (15)	0.000	−0.0029 (14)	0.000
C5	0.0170 (13)	0.0191 (14)	0.0276 (15)	0.000	0.0033 (11)	0.000
C6	0.0180 (14)	0.0190 (16)	0.0228 (14)	0.000	0.0045 (10)	0.000
C7	0.0264 (11)	0.0170 (12)	0.0310 (11)	−0.0007 (9)	0.0024 (9)	0.0015 (8)
C8	0.0301 (12)	0.0209 (12)	0.0283 (10)	−0.0029 (10)	0.0011 (9)	−0.0027 (8)
C9	0.0210 (15)	0.0258 (18)	0.0232 (14)	0.000	0.0044 (11)	0.000
C10	0.0312 (17)	0.0240 (18)	0.0275 (16)	0.000	0.0067 (13)	0.000

Geometric parameters (Å, º)

N1—C1^i	1.354 (3)	C5—H5A	0.9900
N1—C1	1.354 (3)	C5—H5B	0.9900
N1—C5	1.489 (4)	C5—C6	1.502 (4)
N2—C4	1.138 (4)	C6—C7	1.395 (3)
N3—C10	1.143 (4)	C6—C7^i	1.395 (3)
C1—H1	0.9500	C7—H7	0.9500
C1—C2	1.375 (3)	C7—C8	1.382 (3)
C2—H2	0.9500	C8—H8	0.9500
C2—C3	1.394 (3)	C8—C9	1.395 (3)
C3—C4	1.446 (4)	C9—C10	1.445 (5)
C1^i—N1—C1	121.7 (3)	H5A—C5—H5B	108.2
C1—N1—C5	119.08 (13)	C6—C5—H5A	109.7
C1^i—N1—C5	119.07 (13)	C6—C5—H5B	109.7
N1—C1—H1	119.8	C7^i—C6—C5	120.07 (14)
N1—C1—C2	120.3 (2)	C7—C6—C5	120.07 (14)
C2—C1—H1	119.8	C7—C6—C7^i	119.8 (3)
C1—C2—H2	120.8	C6—C7—H7	119.9
C1—C2—C3	118.4 (2)	C8—C7—C6	120.3 (2)
C3—C2—H2	120.8	C8—C7—H7	119.9
C2^i—C3—C2	120.8 (3)	C7—C8—H8	120.2
C2—C3—C4	119.60 (13)	C7—C8—C9	119.5 (2)
C2^i—C3—C4	119.60 (13)	C9—C8—H8	120.2
N2—C4—C3	178.6 (4)	C8^i—C9—C8	120.5 (3)
N1—C5—H5A	109.7	C8—C9—C10	119.73 (14)
N1—C5—H5B	109.7	C8^i—C9—C10	119.73 (14)
N1—C5—C6	109.9 (2)	N3—C10—C9	179.0 (3)
N1—C1—C2—C3	0.4 (3)	C1—C2—C3—C4	179.5 (2)
N1—C5—C6—C7	89.1 (2)	C5—N1—C1—C2	175.9 (2)
N1—C5—C6—C7^i	−89.1 (2)	C5—C6—C7—C8	−177.6 (2)
C1^i—N1—C1—C2	−0.3 (4)	C6—C7—C8—C9	−0.2 (4)
C1—N1—C5—C6	−88.1 (2)	C7^i—C6—C7—C8	0.7 (4)
C1^i—N1—C5—C6	88.1 (2)	C7—C8—C9—C8^i	−0.2 (4)
C1—C2—C3—C2^i	−0.6 (4)	C7—C8—C9—C10	179.1 (2)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1^ii	0.95	2.79	3.649 (2)	151
C2—H2···N3^iii	0.95	2.57	3.448 (3)	153
C5—H5A···Br1^iv	0.99	2.78	3.6953 (9)	154
C5—H5B···Br1^ii	0.99	2.78	3.6953 (9)	154
C8—H8···N2^v	0.95	2.65	3.516 (3)	151

Symmetry codes: (ii) x−1/2, −y+3/2, −z+1/2; (iii) −x+3/2, −y+1, z−1/2; (iv) x−1/2, −y+1/2, −z+1/2; (v) −x+3/2, −y+1, z+1/2.

Bis[4-cyano-N-(4-cyanobenzyl)pyridinium] antimony(III) pentabromide (iHOFII)

Crystal data

(C14H10N3)2[SbBr5]	Dx = 1.536 Mg m^−3
Mr = 959.80	Ga Kα radiation, λ = 1.34138 Å
Tetragonal, I4/m	Cell parameters from 9796 reflections
a = 23.8054 (12) Å	θ = 4.6–59.4°
c = 7.3222 (4) Å	µ = 7.57 mm^−1
V = 4149.5 (5) Å^3	T = 150 K
Z = 4	NEEDLE, brown
F(000) = 1820	0.08 × 0.03 × 0.02 mm

Data collection

Bruker D8 VENTURE PHOTON III diffractometer	2327 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.056
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 59.3°, θmin = 4.6°
Tmin = 0.022, Tmax = 0.098	h = −27→30
32444 measured reflections	k = −26→30
2447 independent reflections	l = −9→8

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.073	H-atom parameters constrained
wR(F^2) = 0.220	w = 1/[σ^2(Fo^2) + (0.132P)^2 + 37.369P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
2447 reflections	Δρmax = 2.40 e Å^−3
150 parameters	Δρmin = −1.75 e Å^−3
0 restraints

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.4835 (2)	0.3428 (3)	0.5000	0.0304 (12)
N2	0.6685 (4)	0.2200 (4)	0.5000	0.058 (2)
N3	0.2405 (4)	0.1467 (4)	0.5000	0.061 (2)
C1	0.5073 (2)	0.3297 (2)	0.6587 (7)	0.0358 (11)
H1	0.4903	0.3414	0.7696	0.043*
C2	0.5568 (2)	0.2991 (3)	0.6635 (8)	0.0394 (12)
H2	0.5740	0.2893	0.7762	0.047*
C3	0.5802 (3)	0.2833 (3)	0.5000	0.0328 (15)
C4	0.6308 (3)	0.2486 (4)	0.5000	0.0414 (18)
C5	0.4262 (3)	0.3677 (3)	0.5000	0.0314 (14)
H5A	0.4210	0.3915	0.3903	0.038*	0.5
H5B	0.4210	0.3915	0.6097	0.038*	0.5
C6	0.3839 (3)	0.3206 (3)	0.5000	0.0309 (14)
C7	0.3658 (2)	0.2980 (2)	0.3359 (7)	0.0362 (11)
H7	0.3782	0.3138	0.2237	0.043*
C8	0.3294 (2)	0.2522 (2)	0.3351 (8)	0.0402 (12)
H8	0.3167	0.2366	0.2231	0.048*
C9	0.3120 (3)	0.2298 (3)	0.5000	0.0369 (16)
C10	0.2730 (4)	0.1835 (4)	0.5000	0.046 (2)
Sb1	0.47999 (9)	0.11701 (9)	0.2488 (3)	0.0244 (5)	0.125
Br1	0.46859 (15)	0.18576 (12)	0.5000	0.0377 (7)	0.25
Br2	0.46397 (16)	0.21197 (16)	0.0000	0.0418 (8)	0.25
Br3	0.4986 (2)	0.03254 (14)	0.5000	0.0523 (9)	0.25
Br4	0.5934 (5)	0.1320 (6)	0.218 (2)	0.068 (3)	0.125
Br4A	0.3678 (5)	0.0819 (8)	0.257 (3)	0.113 (7)	0.125
Sb2	0.5000	0.5000	0.05741 (14)	0.0210 (3)	0.5
Br5	0.41593 (3)	0.41812 (3)	0.0000	0.0347 (3)	0.9
Br6	0.5000	0.5000	−0.2922 (2)	0.0239 (4)	0.45
Br7	0.5000	0.5000	0.5000	0.0259 (6)	0.45

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.025 (3)	0.034 (3)	0.032 (3)	−0.003 (2)	0.000	0.000
N2	0.053 (5)	0.060 (5)	0.060 (5)	0.023 (4)	0.000	0.000
N3	0.069 (6)	0.054 (5)	0.061 (5)	−0.028 (4)	0.000	0.000
C1	0.032 (2)	0.048 (3)	0.028 (2)	0.003 (2)	−0.002 (2)	−0.006 (2)
C2	0.035 (3)	0.053 (3)	0.030 (3)	0.004 (2)	−0.004 (2)	−0.002 (2)
C3	0.029 (3)	0.033 (3)	0.037 (4)	0.004 (3)	0.000	0.000
C4	0.037 (4)	0.045 (4)	0.042 (4)	0.010 (3)	0.000	0.000
C5	0.025 (3)	0.033 (3)	0.035 (4)	0.001 (3)	0.000	0.000
C6	0.026 (3)	0.032 (3)	0.035 (4)	−0.002 (3)	0.000	0.000
C7	0.038 (3)	0.041 (3)	0.029 (3)	−0.007 (2)	0.003 (2)	0.000 (2)
C8	0.041 (3)	0.043 (3)	0.036 (3)	−0.011 (2)	0.000 (2)	−0.005 (2)
C9	0.039 (4)	0.034 (4)	0.038 (4)	−0.003 (3)	0.000	0.000
C10	0.053 (5)	0.046 (5)	0.037 (4)	−0.015 (4)	0.000	0.000
Sb1	0.0232 (10)	0.0202 (10)	0.0299 (12)	0.0005 (8)	−0.0056 (9)	−0.0091 (8)
Br1	0.0503 (18)	0.0232 (13)	0.0396 (17)	0.0016 (12)	0.000	0.000
Br2	0.0516 (19)	0.0536 (19)	0.0202 (13)	0.0145 (15)	0.000	0.000
Br3	0.070 (3)	0.0273 (17)	0.060 (2)	0.0023 (16)	0.000	0.000
Br4	0.034 (3)	0.089 (8)	0.080 (6)	0.009 (3)	0.016 (3)	0.018 (5)
Br4A	0.047 (6)	0.112 (12)	0.180 (17)	−0.026 (6)	−0.045 (8)	0.012 (10)
Sb2	0.0235 (4)	0.0235 (4)	0.0159 (5)	0.000	0.000	0.000
Br5	0.0232 (4)	0.0253 (4)	0.0555 (6)	−0.0053 (3)	0.000	0.000
Br6	0.0301 (6)	0.0301 (6)	0.0113 (9)	0.000	0.000	0.000
Br7	0.0278 (9)	0.0278 (9)	0.0222 (14)	0.000	0.000	0.000

Geometric parameters (Å, º)

N1—C1^i	1.330 (6)	Sb1—Br4^ii	2.736 (15)
N1—C1	1.330 (6)	Sb1—Br4	2.733 (11)
N1—C5	1.488 (9)	Sb1—Br4A^iii	2.453 (19)
N2—C4	1.127 (11)	Sb1—Br4A	2.800 (14)
N3—C10	1.169 (12)	Br1—Sb1^i	2.477 (3)
C1—H1	0.9500	Br2—Sb1^iv	2.928 (4)
C1—C2	1.386 (8)	Br3—Sb1^i	2.761 (3)
C2—H2	0.9500	Br3—Br3^v	1.550 (7)
C2—C3	1.372 (7)	Br4—Sb1^iii	2.736 (15)
C3—C2^i	1.372 (7)	Br4—Br4A^iii	0.33 (3)
C3—C4	1.461 (10)	Br4A—Sb1^ii	2.454 (19)
C5—H5A	0.9900	Br4A—Br4^ii	0.33 (3)
C5—H5B	0.9900	Sb2—Sb2^vi	0.841 (2)
C5—C6	1.507 (10)	Sb2—Br5^vii	2.8251 (8)
C6—C7	1.386 (6)	Sb2—Br5	2.8251 (8)
C6—C7^i	1.386 (6)	Sb2—Br5^vi	2.8251 (8)
C7—H7	0.9500	Sb2—Br5^viii	2.8251 (8)
C7—C8	1.394 (7)	Sb2—Br6	2.560 (2)
C8—H8	0.9500	Sb2—Br6^vi	1.719 (2)
C8—C9	1.383 (7)	Br5—Sb2^vi	2.8251 (8)
C9—C8^i	1.383 (7)	Br6—Sb2^vi	1.719 (2)
C9—C10	1.442 (11)	Br6—Br7^ix	1.5213 (18)
Sb1—Br1	2.477 (3)	Br7—Br6^vi	1.5214 (18)
Sb1—Br2	2.928 (4)	Br7—Br6^x	1.5214 (18)
Sb1—Br3	2.761 (3)
C1^i—N1—C1	121.7 (6)	Br4^ii—Sb1—Br4A	6.8 (5)
C1^i—N1—C5	119.0 (3)	Br4A^iii—Sb1—Br1	91.3 (4)
C1—N1—C5	119.0 (3)	Br4A—Sb1—Br2	96.8 (4)
N1—C1—H1	119.7	Br4A^iii—Sb1—Br2	90.3 (5)
N1—C1—C2	120.5 (5)	Br4A^iii—Sb1—Br3	87.7 (5)
C2—C1—H1	119.7	Br4A^iii—Sb1—Br4^ii	174.6 (7)
C1—C2—H2	121.1	Br4A^iii—Sb1—Br4	4.0 (7)
C3—C2—C1	117.8 (5)	Br4A^iii—Sb1—Br4A	171.1 (5)
C3—C2—H2	121.1	Sb1^i—Br1—Sb1	95.89 (15)
C2—C3—C2^i	121.5 (7)	Sb1^iv—Br2—Sb1	76.95 (12)
C2^i—C3—C4	119.3 (4)	Sb1—Br3—Sb1^i	83.54 (13)
C2—C3—C4	119.3 (4)	Br3^v—Br3—Sb1^i	137.27 (10)
N2—C4—C3	177.3 (10)	Br3^v—Br3—Sb1	137.27 (10)
N1—C5—H5A	110.0	Sb1—Br4—Sb1^iii	93.9 (4)
N1—C5—H5B	110.0	Br4A^iii—Br4—Sb1	31 (6)
N1—C5—C6	108.3 (6)	Br4A^iii—Br4—Sb1^iii	98 (5)
H5A—C5—H5B	108.4	Sb1^ii—Br4A—Sb1	98.8 (5)
C6—C5—H5A	110.0	Br4^ii—Br4A—Sb1	76 (5)
C6—C5—H5B	110.0	Br4^ii—Br4A—Sb1^ii	145 (6)
C7^i—C6—C5	119.8 (3)	Sb2^vi—Sb2—Br5^vii	81.44 (2)
C7—C6—C5	119.8 (3)	Sb2^vi—Sb2—Br5^viii	81.44 (2)
C7^i—C6—C7	120.3 (7)	Sb2^vi—Sb2—Br5	81.44 (2)
C6—C7—H7	120.0	Sb2^vi—Sb2—Br5^vi	81.44 (2)
C6—C7—C8	120.1 (5)	Sb2^vi—Sb2—Br6^vi	180.0
C8—C7—H7	120.0	Sb2^vi—Sb2—Br6	0.000 (1)
C7—C8—H8	120.5	Br5^vii—Sb2—Br5	88.731 (6)
C9—C8—C7	119.0 (5)	Br5^vi—Sb2—Br5^viii	88.731 (6)
C9—C8—H8	120.5	Br5^vi—Sb2—Br5^vii	88.731 (6)
C8^i—C9—C8	121.6 (7)	Br5^viii—Sb2—Br5	88.732 (6)
C8—C9—C10	119.2 (4)	Br5^vi—Sb2—Br5	162.89 (4)
C8^i—C9—C10	119.2 (4)	Br5^vii—Sb2—Br5^viii	162.89 (4)
N3—C10—C9	178.7 (11)	Br6—Sb2—Br5^viii	81.44 (2)
Br1—Sb1—Br2	86.42 (9)	Br6^vi—Sb2—Br5	98.56 (2)
Br1—Sb1—Br3	90.25 (10)	Br6—Sb2—Br5^vii	81.44 (2)
Br1—Sb1—Br4	94.8 (3)	Br6^vi—Sb2—Br5^viii	98.56 (2)
Br1—Sb1—Br4^ii	87.8 (3)	Br6—Sb2—Br5	81.44 (2)
Br1—Sb1—Br4A	94.4 (4)	Br6^vi—Sb2—Br5^vii	98.56 (2)
Br3—Sb1—Br2	176.05 (12)	Br6—Sb2—Br5^vi	81.44 (2)
Br3—Sb1—Br4A	85.5 (4)	Br6^vi—Sb2—Br5^vi	98.56 (2)
Br4—Sb1—Br2	88.6 (3)	Br6^vi—Sb2—Br6	180.0
Br4^ii—Sb1—Br2	95.0 (3)	Sb2—Br5—Sb2^vi	17.11 (4)
Br4—Sb1—Br3	89.6 (3)	Sb2^vi—Br6—Sb2	0.0
Br4^ii—Sb1—Br3	87.0 (3)	Br7^ix—Br6—Sb2	180.0
Br4—Sb1—Br4^ii	175.6 (4)	Br7^ix—Br6—Sb2^vi	180.0
Br4—Sb1—Br4A	169.5 (5)	Br6^vi—Br7—Br6^x	180.0
N1—C1—C2—C3	0.4 (9)	C1—C2—C3—C4	−176.9 (7)
N1—C5—C6—C7^i	88.2 (6)	C5—N1—C1—C2	170.6 (6)
N1—C5—C6—C7	−88.2 (6)	C5—C6—C7—C8	176.1 (6)
C1^i—N1—C1—C2	−3.4 (11)	C6—C7—C8—C9	−0.2 (10)
C1^i—N1—C5—C6	87.1 (5)	C7^i—C6—C7—C8	−0.2 (11)
C1—N1—C5—C6	−87.1 (5)	C7—C8—C9—C8^i	0.7 (12)
C1—C2—C3—C2^i	2.6 (12)	C7—C8—C9—C10	178.1 (7)

Symmetry codes: (i) x, y, −z+1; (ii) −y+1/2, x−1/2, −z+1/2; (iii) y+1/2, −x+1/2, −z+1/2; (iv) x, y, −z; (v) −x+1, −y, −z+1; (vi) −x+1, −y+1, −z; (vii) y, −x+1, −z; (viii) −y+1, x, z; (ix) x, y, z−1; (x) x, y, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br5^x	0.95	3.05	3.924 (4)	153
C2—H2···N3^xi	0.95	2.49	3.397 (7)	160
C5—H5A···Br5	0.99	2.93	3.8568 (19)	157
C5—H5A···Br6^xii	0.99	3.27	3.910 (5)	124
C5—H5B···Br5	0.99	2.93	3.8568 (19)	157
C5—H5B···Br6	0.99	3.27	3.910 (5)	124
C7—H7···Br5	0.95	3.11	3.960 (4)	149
C8—H8···N2^xiii	0.95	2.46	3.371 (6)	161

Symmetry codes: (x) x, y, z+1; (xi) y+1/2, −x+1/2, z+1/2; (xii) −x+1, −y+1, z; (xiii) −y+1/2, x−1/2, z−1/2.