Tetrakis(3,5-di­methyl­pyridine)­dihydrido­silicon dibromide bis(aceto­nitrile) solvate and 3,5-dimethylpyridinium bromide

In the course of an attempt to synthesize tetrakis(3,5-di­methyl­pyridine)­dihydridosilicon dibromide, crystals of its aceto­nitrile disolvate, C₂₈H₃₈N₄Si²⁺·2Br^-·2C₂H₃N, (I), and of 3,5-di­methyl­pyridinium bromide, C₇H₁₀N⁺·Br^-, (II), were obtained in the same reaction flask. They have both been structurally characterized.

Computing details

For both compounds, data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C28H38N4Si^2+·2Br^−·2C2H3N	F(000) = 724
Mr = 700.64	Dx = 1.327 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.636 (2) Å	Cell parameters from 7291 reflections
b = 11.237 (2) Å	θ = 1–25°
c = 16.242 (3) Å	µ = 2.38 mm^−1
β = 94.49 (1)°	T = 173 K
V = 1753.3 (6) Å^3	Block, colourless
Z = 2	0.75 × 0.70 × 0.55 mm

Data collection

Siemens CCD three-circle diffractometer	4345 independent reflections
Radiation source: fine-focus sealed tube	3390 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: empirical (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.185, Tmax = 0.271	k = −14→14
32839 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0451P)^2 + 2.4478P] where P = (Fo^2 + 2Fc^2)/3
4345 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.78 e Å^−3
0 restraints	Δρmin = −0.77 e Å^−3

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
Br1	0.59423 (4)	0.11115 (3)	0.18448 (2)	0.04740 (14)
Si1	0.5000	0.0000	0.5000	0.0199 (2)
H1	0.502 (3)	0.053 (3)	0.5730 (19)	0.029 (8)*
N11	0.4049 (2)	0.14032 (19)	0.44785 (13)	0.0209 (4)
C12	0.3822 (3)	0.2368 (3)	0.49314 (17)	0.0261 (6)
H12	0.4135	0.2371	0.5501	0.031*
C13	0.3147 (3)	0.3360 (3)	0.45965 (18)	0.0294 (6)
C13'	0.2906 (4)	0.4435 (3)	0.5117 (2)	0.0463 (9)
H13A	0.1910	0.4509	0.5191	0.069*
H13B	0.3227	0.5149	0.4841	0.069*
H13C	0.3424	0.4348	0.5657	0.069*
C14	0.2698 (3)	0.3325 (3)	0.37583 (18)	0.0296 (6)
H14	0.2205	0.3983	0.3513	0.036*
C15	0.2962 (3)	0.2342 (3)	0.32808 (17)	0.0266 (6)
C15'	0.2540 (4)	0.2312 (3)	0.23679 (19)	0.0407 (8)
H15A	0.3354	0.2473	0.2060	0.061*
H15B	0.1828	0.2920	0.2234	0.061*
H15C	0.2163	0.1526	0.2216	0.061*
C16	0.3652 (3)	0.1391 (3)	0.36667 (18)	0.0261 (6)
H16	0.3852	0.0711	0.3349	0.031*
N21	0.6830 (2)	0.0721 (2)	0.48468 (14)	0.0219 (5)
C22	0.7484 (3)	0.0463 (3)	0.41690 (18)	0.0262 (6)
H22	0.7042	−0.0052	0.3765	0.031*
C23	0.8784 (3)	0.0924 (3)	0.40378 (19)	0.0315 (6)
C23'	0.9475 (4)	0.0621 (4)	0.3263 (2)	0.0473 (9)
H23A	0.9990	0.1315	0.3085	0.071*
H23B	0.8764	0.0397	0.2826	0.071*
H23C	1.0119	−0.0045	0.3374	0.071*
C24	0.9389 (3)	0.1684 (3)	0.4636 (2)	0.0350 (7)
H24	1.0283	0.2008	0.4567	0.042*
C25	0.8719 (3)	0.1984 (3)	0.5333 (2)	0.0333 (7)
C25'	0.9340 (4)	0.2821 (4)	0.5985 (2)	0.0533 (10)
H25A	0.8780	0.3549	0.5985	0.080*
H25B	1.0294	0.3022	0.5867	0.080*
H25C	0.9350	0.2438	0.6527	0.080*
C26	0.7423 (3)	0.1470 (3)	0.54165 (18)	0.0280 (6)
H26	0.6943	0.1655	0.5890	0.034*
N1	0.0894 (4)	0.5963 (4)	0.6810 (3)	0.0832 (14)
C2	0.2016 (5)	0.6212 (3)	0.6741 (3)	0.0503 (9)
C3	0.3456 (4)	0.6544 (3)	0.6640 (3)	0.0499 (9)
H3A	0.3541	0.6802	0.6069	0.075*
H3B	0.4063	0.5857	0.6763	0.075*
H3C	0.3731	0.7196	0.7018	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0436 (2)	0.0472 (2)	0.0509 (2)	0.00162 (16)	0.00004 (15)	−0.01632 (17)
Si1	0.0192 (5)	0.0217 (5)	0.0187 (5)	−0.0016 (4)	−0.0002 (4)	0.0007 (4)
N11	0.0233 (11)	0.0206 (11)	0.0187 (11)	−0.0048 (9)	0.0007 (8)	0.0023 (8)
C12	0.0283 (14)	0.0270 (14)	0.0230 (13)	−0.0027 (11)	0.0010 (11)	0.0023 (11)
C13	0.0322 (15)	0.0269 (15)	0.0293 (15)	−0.0006 (12)	0.0041 (12)	0.0017 (12)
C13'	0.070 (3)	0.0298 (17)	0.0395 (19)	0.0140 (17)	0.0040 (17)	−0.0016 (14)
C14	0.0253 (14)	0.0302 (15)	0.0331 (16)	0.0018 (12)	0.0011 (12)	0.0094 (12)
C15	0.0215 (13)	0.0327 (15)	0.0251 (14)	−0.0033 (11)	−0.0013 (11)	0.0055 (11)
C15'	0.0423 (18)	0.050 (2)	0.0278 (16)	0.0066 (16)	−0.0105 (14)	0.0054 (14)
C16	0.0230 (13)	0.0282 (14)	0.0267 (14)	−0.0022 (11)	−0.0002 (11)	−0.0014 (11)
N21	0.0205 (11)	0.0216 (11)	0.0232 (11)	−0.0023 (9)	−0.0014 (9)	0.0030 (9)
C22	0.0260 (14)	0.0245 (14)	0.0281 (14)	−0.0020 (11)	0.0017 (11)	0.0018 (11)
C23	0.0252 (14)	0.0337 (16)	0.0359 (16)	−0.0012 (12)	0.0050 (12)	0.0060 (13)
C23'	0.0338 (17)	0.062 (2)	0.048 (2)	−0.0074 (17)	0.0170 (15)	−0.0027 (18)
C24	0.0182 (13)	0.0396 (18)	0.0464 (19)	−0.0068 (12)	−0.0024 (13)	0.0089 (14)
C25	0.0258 (15)	0.0369 (17)	0.0356 (16)	−0.0067 (12)	−0.0077 (12)	0.0038 (13)
C25'	0.0387 (19)	0.065 (3)	0.053 (2)	−0.0210 (18)	−0.0113 (17)	−0.011 (2)
C26	0.0241 (14)	0.0329 (15)	0.0262 (14)	−0.0020 (12)	−0.0035 (11)	0.0028 (12)
N1	0.063 (3)	0.077 (3)	0.114 (4)	−0.001 (2)	0.038 (3)	0.030 (3)
C2	0.064 (3)	0.037 (2)	0.052 (2)	0.0054 (18)	0.0178 (19)	0.0083 (16)
C3	0.053 (2)	0.0368 (19)	0.060 (2)	−0.0004 (17)	0.0039 (18)	−0.0132 (17)

Geometric parameters (Å, º)

Si1—H1^i	1.33 (3)	C16—H16	0.9500
Si1—H1	1.33 (3)	N21—C22	1.342 (4)
Si1—N21	1.974 (2)	N21—C26	1.345 (4)
Si1—N21^i	1.974 (2)	C22—C23	1.388 (4)
Si1—N11	1.980 (2)	C22—H22	0.9500
Si1—N11^i	1.980 (2)	C23—C24	1.387 (5)
Si1—H1	1.33 (3)	C23—C23'	1.507 (5)
N11—C12	1.338 (4)	C23'—H23A	0.9800
N11—C16	1.344 (4)	C23'—H23B	0.9800
C12—C13	1.380 (4)	C23'—H23C	0.9800
C12—H12	0.9500	C24—C25	1.387 (5)
C13—C14	1.396 (4)	C24—H24	0.9500
C13—C13'	1.503 (4)	C25—C26	1.392 (4)
C13'—H13A	0.9800	C25—C25'	1.506 (5)
C13'—H13B	0.9800	C25'—H25A	0.9800
C13'—H13C	0.9800	C25'—H25B	0.9800
C14—C15	1.385 (4)	C25'—H25C	0.9800
C14—H14	0.9500	C26—H26	0.9500
C15—C16	1.382 (4)	N1—C2	1.130 (5)
C15—C15'	1.507 (4)	C2—C3	1.459 (6)
C15'—H15A	0.9800	C3—H3A	0.9800
C15'—H15B	0.9800	C3—H3B	0.9800
C15'—H15C	0.9800	C3—H3C	0.9800
H1^i—Si1—H1	180.000 (8)	H15A—C15'—H15B	109.5
H1^i—Si1—N21	91.2 (14)	C15—C15'—H15C	109.5
H1—Si1—N21	88.8 (14)	H15A—C15'—H15C	109.5
H1^i—Si1—N21^i	88.8 (14)	H15B—C15'—H15C	109.5
H1—Si1—N21^i	91.2 (14)	N11—C16—C15	121.8 (3)
N21—Si1—N21^i	180.0	N11—C16—H16	119.1
H1^i—Si1—N11	90.3 (14)	C15—C16—H16	119.1
H1—Si1—N11	89.7 (14)	C22—N21—C26	119.8 (2)
N21—Si1—N11	90.42 (9)	C22—N21—Si1	119.78 (18)
N21^i—Si1—N11	89.58 (9)	C26—N21—Si1	120.38 (19)
H1^i—Si1—N11^i	89.7 (14)	N21—C22—C23	122.2 (3)
H1—Si1—N11^i	90.3 (14)	N21—C22—H22	118.9
N21—Si1—N11^i	89.58 (9)	C23—C22—H22	118.9
N21^i—Si1—N11^i	90.42 (9)	C24—C23—C22	117.2 (3)
N11—Si1—N11^i	180.00 (11)	C24—C23—C23'	122.3 (3)
H1^i—Si1—H1	180.000 (8)	C22—C23—C23'	120.5 (3)
H1—Si1—H1	0 (3)	C23—C23'—H23A	109.5
N21—Si1—H1	88.8 (14)	C23—C23'—H23B	109.5
N21^i—Si1—H1	91.2 (14)	H23A—C23'—H23B	109.5
N11—Si1—H1	89.7 (14)	C23—C23'—H23C	109.5
N11^i—Si1—H1	90.3 (14)	H23A—C23'—H23C	109.5
C12—N11—C16	120.1 (2)	H23B—C23'—H23C	109.5
C12—N11—Si1	120.02 (18)	C23—C24—C25	121.6 (3)
C16—N11—Si1	119.90 (19)	C23—C24—H24	119.2
N11—C12—C13	122.0 (3)	C25—C24—H24	119.2
N11—C12—H12	119.0	C24—C25—C26	117.2 (3)
C13—C12—H12	119.0	C24—C25—C25'	122.8 (3)
C12—C13—C14	117.5 (3)	C26—C25—C25'	120.0 (3)
C12—C13—C13'	121.1 (3)	C25—C25'—H25A	109.5
C14—C13—C13'	121.4 (3)	C25—C25'—H25B	109.5
C13—C13'—H13A	109.5	H25A—C25'—H25B	109.5
C13—C13'—H13B	109.5	C25—C25'—H25C	109.5
H13A—C13'—H13B	109.5	H25A—C25'—H25C	109.5
C13—C13'—H13C	109.5	H25B—C25'—H25C	109.5
H13A—C13'—H13C	109.5	N21—C26—C25	121.9 (3)
H13B—C13'—H13C	109.5	N21—C26—H26	119.1
C15—C14—C13	120.8 (3)	C25—C26—H26	119.1
C15—C14—H14	119.6	N1—C2—C3	179.0 (5)
C13—C14—H14	119.6	C2—C3—H3A	109.5
C16—C15—C14	117.7 (3)	C2—C3—H3B	109.5
C16—C15—C15'	120.8 (3)	H3A—C3—H3B	109.5
C14—C15—C15'	121.4 (3)	C2—C3—H3C	109.5
C15—C15'—H15A	109.5	H3A—C3—H3C	109.5
C15—C15'—H15B	109.5	H3B—C3—H3C	109.5
H1^i—Si1—N11—C12	−175.8 (14)	H1^i—Si1—N21—C22	−2.9 (14)
H1—Si1—N11—C12	4.2 (14)	H1—Si1—N21—C22	177.1 (14)
N21—Si1—N11—C12	−84.6 (2)	N11—Si1—N21—C22	−93.2 (2)
N21^i—Si1—N11—C12	95.4 (2)	N11^i—Si1—N21—C22	86.8 (2)
H1^i—Si1—N11—C16	3.2 (14)	H1^i—Si1—N21—C26	176.9 (14)
H1—Si1—N11—C16	−176.8 (14)	H1—Si1—N21—C26	−3.1 (14)
N21—Si1—N11—C16	94.3 (2)	N11—Si1—N21—C26	86.6 (2)
N21^i—Si1—N11—C16	−85.7 (2)	N11^i—Si1—N21—C26	−93.4 (2)
C16—N11—C12—C13	2.0 (4)	C26—N21—C22—C23	1.6 (4)
Si1—N11—C12—C13	−179.1 (2)	Si1—N21—C22—C23	−178.6 (2)
N11—C12—C13—C14	0.1 (4)	N21—C22—C23—C24	−0.8 (4)
N11—C12—C13—C13'	−179.9 (3)	N21—C22—C23—C23'	−179.4 (3)
C12—C13—C14—C15	−1.9 (4)	C22—C23—C24—C25	−0.7 (5)
C13'—C13—C14—C15	178.1 (3)	C23'—C23—C24—C25	177.9 (3)
C13—C14—C15—C16	1.5 (4)	C23—C24—C25—C26	1.3 (5)
C13—C14—C15—C15'	−177.3 (3)	C23—C24—C25—C25'	−179.0 (3)
C12—N11—C16—C15	−2.3 (4)	C22—N21—C26—C25	−0.9 (4)
Si1—N11—C16—C15	178.7 (2)	Si1—N21—C26—C25	179.3 (2)
C14—C15—C16—N11	0.6 (4)	C24—C25—C26—N21	−0.5 (4)
C15'—C15—C16—N11	179.4 (3)	C25'—C25—C26—N21	179.8 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15′—H15A···Br1	0.98	2.97	3.705 (4)	133
C25′—H25A···Br1^ii	0.98	3.19	3.850 (4)	126
C3—H3B···Br1^ii	0.98	2.85	3.825 (4)	171
C3—H3C···Br1^iii	0.98	2.65	3.621 (4)	170

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

(II)

Crystal data

C7H10N^+·Br^−	Z = 2
Mr = 188.07	F(000) = 188
Triclinic, P1	Dx = 1.546 Mg m^−3
a = 7.504 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.144 (3) Å	Cell parameters from 5969 reflections
c = 8.522 (3) Å	θ = 1–25°
α = 117.80 (1)°	µ = 5.00 mm^−1
β = 113.43 (1)°	T = 173 K
γ = 93.01 (1)°	Needle, colourless
V = 404.1 (2) Å^3	0.60 × 0.10 × 0.10 mm

Data collection

Siemens CCD three-circle diffractometer	1789 independent reflections
Radiation source: fine-focus sealed tube	1531 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
ω scans	θmax = 27.1°, θmin = 2.9°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.153, Tmax = 0.635	k = −10→10
9982 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0461P)^2 + 0.3351P] where P = (Fo^2 + 2Fc^2)/3
1789 reflections	(Δ/σ)max < 0.001
88 parameters	Δρmax = 0.78 e Å^−3
0 restraints	Δρmin = −0.54 e Å^−3

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
Br1	0.23326 (6)	0.62640 (6)	0.86779 (6)	0.03320 (16)
N1	0.3894 (5)	0.3508 (5)	0.5736 (5)	0.0301 (7)
H1	0.346 (8)	0.424 (8)	0.661 (8)	0.049 (14)*
C2	0.2725 (6)	0.3105 (6)	0.3858 (6)	0.0277 (8)
H2	0.1549	0.3534	0.3558	0.033*
C3	0.3238 (6)	0.2065 (5)	0.2363 (6)	0.0261 (8)
C31	0.2022 (7)	0.1651 (7)	0.0277 (6)	0.0371 (10)
H31A	0.1633	0.0254	−0.0699	0.056*
H31B	0.2838	0.2359	0.0005	0.056*
H31C	0.0797	0.2067	0.0154	0.056*
C4	0.4962 (6)	0.1453 (6)	0.2888 (6)	0.0274 (8)
H4	0.5333	0.0717	0.1881	0.033*
C5	0.6166 (6)	0.1890 (5)	0.4858 (6)	0.0281 (8)
C51	0.8076 (6)	0.1287 (7)	0.5429 (7)	0.0429 (11)
H51A	0.7972	0.0142	0.4229	0.064*
H51B	0.8249	0.0974	0.6450	0.064*
H51C	0.9248	0.2353	0.5977	0.064*
C6	0.5561 (6)	0.2946 (6)	0.6266 (6)	0.0334 (9)
H6	0.6333	0.3276	0.7620	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0309 (2)	0.0419 (3)	0.0282 (2)	0.01640 (18)	0.01609 (17)	0.01742 (19)
N1	0.0393 (19)	0.0230 (17)	0.0289 (18)	0.0087 (15)	0.0215 (16)	0.0101 (15)
C2	0.0264 (19)	0.028 (2)	0.031 (2)	0.0101 (16)	0.0156 (17)	0.0161 (18)
C3	0.0231 (18)	0.025 (2)	0.0281 (19)	0.0040 (15)	0.0109 (16)	0.0140 (17)
C31	0.035 (2)	0.048 (3)	0.026 (2)	0.013 (2)	0.0119 (18)	0.020 (2)
C4	0.0258 (19)	0.026 (2)	0.029 (2)	0.0070 (16)	0.0145 (16)	0.0127 (17)
C5	0.0249 (19)	0.0218 (19)	0.030 (2)	0.0016 (15)	0.0080 (16)	0.0127 (17)
C51	0.028 (2)	0.044 (3)	0.048 (3)	0.014 (2)	0.009 (2)	0.025 (2)
C6	0.034 (2)	0.031 (2)	0.026 (2)	0.0007 (18)	0.0078 (17)	0.0143 (18)

Geometric parameters (Å, º)

N1—C6	1.335 (5)	C31—H31C	0.9800
N1—C2	1.343 (5)	C4—C5	1.402 (5)
N1—H1	0.90 (5)	C4—H4	0.9500
C2—C3	1.381 (5)	C5—C6	1.377 (6)
C2—H2	0.9500	C5—C51	1.508 (6)
C3—C4	1.392 (5)	C51—H51A	0.9800
C3—C31	1.491 (5)	C51—H51B	0.9800
C31—H31A	0.9800	C51—H51C	0.9800
C31—H31B	0.9800	C6—H6	0.9500
C6—N1—C2	123.5 (4)	C3—C4—C5	122.0 (4)
C6—N1—H1	124 (3)	C3—C4—H4	119.0
C2—N1—H1	113 (3)	C5—C4—H4	119.0
N1—C2—C3	119.8 (4)	C6—C5—C4	117.0 (4)
N1—C2—H2	120.1	C6—C5—C51	121.4 (4)
C3—C2—H2	120.1	C4—C5—C51	121.5 (4)
C2—C3—C4	117.4 (4)	C5—C51—H51A	109.5
C2—C3—C31	121.4 (4)	C5—C51—H51B	109.5
C4—C3—C31	121.2 (4)	H51A—C51—H51B	109.5
C3—C31—H31A	109.5	C5—C51—H51C	109.5
C3—C31—H31B	109.5	H51A—C51—H51C	109.5
H31A—C31—H31B	109.5	H51B—C51—H51C	109.5
C3—C31—H31C	109.5	N1—C6—C5	120.3 (4)
H31A—C31—H31C	109.5	N1—C6—H6	119.9
H31B—C31—H31C	109.5	C5—C6—H6	119.9
C6—N1—C2—C3	−0.3 (6)	C3—C4—C5—C6	0.6 (6)
N1—C2—C3—C4	0.9 (5)	C3—C4—C5—C51	−177.6 (4)
N1—C2—C3—C31	−177.7 (4)	C2—N1—C6—C5	−0.2 (6)
C2—C3—C4—C5	−1.0 (6)	C4—C5—C6—N1	0.1 (6)
C31—C3—C4—C5	177.6 (4)	C51—C5—C6—N1	178.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br1	0.90 (5)	2.27 (5)	3.172 (4)	175 (4)
C51—H51C···Br1^i	0.98	2.99	3.929 (5)	161
C2—H2···Br1^ii	0.95	2.84	3.749 (4)	160
C31—H31C···Br1^ii	0.98	3.05	3.980 (5)	160
C6—H6···Br1^iii	0.95	2.73	3.657 (4)	166

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