N-(6-Bromo-meth-yl-2-pyrid-yl)acetamide.

The title acetamide compound, C(8)H(9)BrN(2)O, crystallizes with three crystallographically independent mol-ecules (A, B and C) in the asymmetric unit. In mol-ecule A, the mean plane through the acetamide unit is inclined at a dihedral angle of 4.40 (11)° with respect to the pyridine ring [10.31 (12) and 2.27 (11)°, respectively, for mol-ecules B and C]. In the crystal structure, mol-ecules are inter-connected into sheets parallel to the ac plane by N-H⋯O, C-H⋯Br, C-H⋯O and C-H⋯N hydrogen bonds. The structure is further stabilized by weak inter-molecular C-H⋯π inter-actions.

Related literature

For general background and applications of acetamide compounds, see: Goswami et al. (2000 ▶, 2005 ▶); Ghosh & Masanta (2006 ▶). For the preparation, see: Goswami et al. (2001 ▶, 2004 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C8H9BrN2O

M = 229.08

Monoclinic,

a = 4.1894 (8) Å

b = 26.219 (5) Å

c = 23.817 (4) Å

β = 94.148 (4)°

V = 2609.2 (8) Å3

Z = 12

Mo Kα radiation

μ = 4.68 mm−1

T = 100 K

0.31 × 0.14 × 0.09 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.323, T max = 0.668

72227 measured reflections

10228 independent reflections

8239 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.100

S = 1.06

10228 reflections

340 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.37 e Å−3

Δρmin = −0.74 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035026/ci5177sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035026/ci5177Isup2.hkl

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

C8H9BrN2O	F(000) = 1368
Mr = 229.08	Dx = 1.750 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9903 reflections
a = 4.1894 (8) Å	θ = 3.0–33.5°
b = 26.219 (5) Å	µ = 4.68 mm−1
c = 23.817 (4) Å	T = 100 K
β = 94.148 (4)°	Plate, brown
V = 2609.2 (8) Å3	0.31 × 0.14 × 0.09 mm
Z = 12

Bruker APEXII DUO CCD area-detector diffractometer	10228 independent reflections
Radiation source: fine-focus sealed tube	8239 reflections with I > 2σ(I)
graphite	Rint = 0.058
φ and ω scans	θmax = 33.7°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
Tmin = 0.323, Tmax = 0.668	k = −40→40
72227 measured reflections	l = −36→36

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.052P)2 + 0.7624P] where P = (Fo2 + 2Fc2)/3
10228 reflections	(Δ/σ)max = 0.005
340 parameters	Δρmax = 1.37 e Å−3
0 restraints	Δρmin = −0.74 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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.

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 > 2sigma(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
Br1A	1.14992 (5)	0.418118 (8)	0.367324 (7)	0.02031 (5)
O1A	0.5948 (4)	0.25161 (6)	0.13677 (6)	0.0296 (3)
N1A	1.1052 (4)	0.35205 (6)	0.24649 (6)	0.0167 (3)
N2A	0.9447 (4)	0.27575 (6)	0.20938 (7)	0.0191 (3)
C1A	1.3223 (5)	0.42675 (8)	0.29327 (7)	0.0196 (3)
H1AA	1.3460	0.4628	0.2856	0.024*
H1AB	1.5326	0.4112	0.2939	0.024*
C2A	1.1091 (4)	0.40309 (7)	0.24723 (7)	0.0166 (3)
C3A	0.9351 (5)	0.43276 (7)	0.20772 (7)	0.0186 (3)
H3AA	0.9413	0.4682	0.2095	0.022*
C4A	0.7516 (5)	0.40783 (7)	0.16540 (7)	0.0200 (3)
H4AA	0.6331	0.4267	0.1382	0.024*
C5A	0.7432 (5)	0.35522 (7)	0.16334 (7)	0.0195 (3)
H5AA	0.6212	0.3381	0.1351	0.023*
C6A	0.9266 (4)	0.32861 (7)	0.20556 (7)	0.0171 (3)
C7A	0.7892 (5)	0.24022 (7)	0.17560 (8)	0.0198 (3)
C8A	0.8755 (5)	0.18609 (7)	0.18922 (8)	0.0235 (4)
H8AA	0.7098	0.1639	0.1735	0.035*
H8AB	0.8985	0.1818	0.2293	0.035*
H8AC	1.0738	0.1778	0.1735	0.035*
Br1B	0.14297 (5)	0.058241 (8)	0.203481 (7)	0.02180 (5)
O1B	0.0701 (5)	0.23172 (6)	−0.04493 (7)	0.0359 (4)
N1B	0.2651 (4)	0.12464 (6)	0.08249 (6)	0.0174 (3)
N2B	0.2563 (4)	0.20320 (6)	0.04135 (7)	0.0206 (3)
C1B	0.3307 (5)	0.04503 (8)	0.13130 (8)	0.0209 (3)
H1BA	0.5573	0.0530	0.1351	0.025*
H1BB	0.3086	0.0091	0.1221	0.025*
C2B	0.1736 (4)	0.07590 (7)	0.08467 (7)	0.0170 (3)
C3B	−0.0419 (5)	0.05349 (7)	0.04525 (8)	0.0199 (3)
H3BA	−0.1004	0.0194	0.0482	0.024*
C4B	−0.1672 (5)	0.08373 (8)	0.00115 (8)	0.0215 (4)
H4BA	−0.3132	0.0700	−0.0260	0.026*
C5B	−0.0763 (5)	0.13402 (8)	−0.00257 (8)	0.0209 (3)
H5BA	−0.1573	0.1546	−0.0321	0.025*
C6B	0.1427 (5)	0.15320 (7)	0.03964 (7)	0.0174 (3)
C7B	0.2223 (6)	0.23918 (8)	0.00022 (8)	0.0251 (4)
C8B	0.3835 (7)	0.28927 (9)	0.01365 (10)	0.0352 (5)
H8BA	0.4373	0.3054	−0.0206	0.053*
H8BB	0.5750	0.2836	0.0375	0.053*
H8BC	0.2414	0.3109	0.0327	0.053*
Br1C	1.07629 (5)	0.426384 (8)	1.034127 (8)	0.02481 (6)
O1C	0.3915 (4)	0.28054 (6)	0.79326 (6)	0.0243 (3)
N1C	0.9830 (4)	0.36463 (6)	0.90997 (6)	0.0173 (3)
N2C	0.7488 (4)	0.29499 (6)	0.86856 (7)	0.0201 (3)
C1C	1.2666 (5)	0.43125 (8)	0.96116 (8)	0.0218 (3)
H1CA	1.3315	0.4662	0.9550	0.026*
H1CB	1.4563	0.4100	0.9619	0.026*
C2C	1.0370 (5)	0.41486 (7)	0.91382 (7)	0.0174 (3)
C3C	0.8994 (5)	0.44982 (7)	0.87597 (7)	0.0202 (3)
H3CA	0.9409	0.4845	0.8800	0.024*
C4C	0.6977 (5)	0.43147 (8)	0.83191 (7)	0.0209 (3)
H4CA	0.6031	0.4541	0.8056	0.025*
C5C	0.6360 (5)	0.37991 (7)	0.82678 (7)	0.0194 (3)
H5CA	0.5004	0.3671	0.7975	0.023*
C6C	0.7858 (4)	0.34775 (7)	0.86741 (7)	0.0168 (3)
C7C	0.5659 (5)	0.26431 (7)	0.83320 (7)	0.0196 (3)
C8C	0.5926 (6)	0.20884 (8)	0.84701 (9)	0.0271 (4)
H8CA	0.5007	0.1892	0.8159	0.041*
H8CB	0.4802	0.2018	0.8799	0.041*
H8CC	0.8140	0.1999	0.8541	0.041*
H2NA	1.062 (8)	0.2645 (13)	0.2303 (13)	0.045 (9)*
H2NB	0.372 (8)	0.2135 (12)	0.0743 (12)	0.039 (8)*
H2NC	0.850 (8)	0.2790 (12)	0.8879 (12)	0.033 (8)*

	U11	U22	U33	U12	U13	U23
Br1A	0.02104 (9)	0.02320 (9)	0.01647 (8)	−0.00081 (6)	−0.00005 (6)	−0.00327 (6)
O1A	0.0389 (9)	0.0208 (7)	0.0268 (7)	−0.0026 (6)	−0.0141 (6)	−0.0012 (6)
N1A	0.0182 (7)	0.0163 (7)	0.0152 (6)	−0.0005 (5)	−0.0012 (5)	−0.0013 (5)
N2A	0.0228 (8)	0.0159 (7)	0.0177 (7)	0.0005 (6)	−0.0055 (6)	−0.0011 (5)
C1A	0.0198 (8)	0.0209 (8)	0.0181 (7)	−0.0055 (6)	0.0007 (6)	−0.0008 (6)
C2A	0.0166 (8)	0.0171 (7)	0.0163 (7)	−0.0012 (6)	0.0014 (6)	−0.0006 (6)
C3A	0.0233 (9)	0.0161 (7)	0.0163 (7)	0.0004 (6)	0.0015 (6)	0.0022 (6)
C4A	0.0235 (9)	0.0201 (8)	0.0163 (7)	0.0014 (7)	−0.0007 (6)	0.0018 (6)
C5A	0.0238 (9)	0.0194 (8)	0.0146 (7)	0.0004 (6)	−0.0032 (6)	−0.0006 (6)
C6A	0.0187 (8)	0.0175 (8)	0.0148 (7)	0.0001 (6)	−0.0005 (6)	−0.0019 (6)
C7A	0.0234 (9)	0.0171 (8)	0.0186 (7)	−0.0017 (6)	−0.0007 (6)	−0.0022 (6)
C8A	0.0287 (10)	0.0177 (8)	0.0236 (8)	−0.0001 (7)	−0.0020 (7)	−0.0032 (7)
Br1B	0.02550 (10)	0.02243 (10)	0.01691 (8)	0.00067 (7)	−0.00224 (6)	0.00250 (6)
O1B	0.0555 (11)	0.0220 (7)	0.0271 (7)	−0.0039 (7)	−0.0182 (7)	0.0056 (6)
N1B	0.0190 (7)	0.0172 (7)	0.0156 (6)	0.0021 (5)	−0.0022 (5)	−0.0002 (5)
N2B	0.0279 (8)	0.0166 (7)	0.0163 (6)	0.0006 (6)	−0.0051 (6)	−0.0002 (5)
C1B	0.0214 (9)	0.0194 (8)	0.0218 (8)	0.0032 (6)	0.0007 (7)	0.0027 (6)
C2B	0.0175 (8)	0.0177 (8)	0.0157 (7)	0.0022 (6)	0.0008 (6)	0.0002 (6)
C3B	0.0219 (9)	0.0194 (8)	0.0186 (7)	−0.0021 (7)	0.0020 (6)	−0.0033 (6)
C4B	0.0225 (9)	0.0252 (9)	0.0165 (7)	−0.0013 (7)	−0.0018 (6)	−0.0035 (6)
C5B	0.0224 (9)	0.0234 (9)	0.0161 (7)	0.0021 (7)	−0.0032 (6)	−0.0008 (6)
C6B	0.0202 (8)	0.0165 (7)	0.0154 (7)	0.0015 (6)	−0.0005 (6)	−0.0010 (6)
C7B	0.0341 (11)	0.0175 (8)	0.0224 (8)	0.0024 (7)	−0.0064 (7)	0.0018 (7)
C8B	0.0512 (15)	0.0194 (9)	0.0323 (11)	−0.0037 (9)	−0.0145 (10)	0.0049 (8)
Br1C	0.02540 (10)	0.03212 (11)	0.01646 (8)	0.00276 (7)	−0.00162 (7)	−0.00555 (7)
O1C	0.0274 (8)	0.0223 (7)	0.0217 (6)	−0.0020 (5)	−0.0090 (5)	0.0002 (5)
N1C	0.0183 (7)	0.0182 (7)	0.0150 (6)	−0.0008 (5)	−0.0012 (5)	−0.0007 (5)
N2C	0.0254 (8)	0.0161 (7)	0.0175 (7)	−0.0022 (6)	−0.0071 (6)	0.0018 (5)
C1C	0.0219 (9)	0.0223 (8)	0.0210 (8)	−0.0039 (7)	−0.0010 (6)	−0.0019 (7)
C2C	0.0189 (8)	0.0189 (8)	0.0145 (7)	−0.0011 (6)	0.0013 (6)	−0.0009 (6)
C3C	0.0260 (9)	0.0181 (8)	0.0162 (7)	−0.0017 (7)	−0.0004 (6)	−0.0011 (6)
C4C	0.0262 (9)	0.0208 (8)	0.0152 (7)	0.0015 (7)	−0.0025 (6)	0.0032 (6)
C5C	0.0221 (9)	0.0203 (8)	0.0151 (7)	0.0008 (6)	−0.0031 (6)	0.0006 (6)
C6C	0.0186 (8)	0.0174 (8)	0.0142 (7)	0.0000 (6)	−0.0009 (6)	−0.0006 (6)
C7C	0.0210 (9)	0.0198 (8)	0.0177 (7)	−0.0025 (6)	−0.0012 (6)	−0.0019 (6)
C8C	0.0355 (12)	0.0187 (9)	0.0254 (9)	−0.0045 (8)	−0.0099 (8)	0.0008 (7)

Br1A—C1A	1.9667 (18)	C3B—C4B	1.389 (3)
O1A—C7A	1.224 (2)	C3B—H3BA	0.93
N1A—C6A	1.335 (2)	C4B—C5B	1.377 (3)
N1A—C2A	1.338 (2)	C4B—H4BA	0.93
N2A—C7A	1.365 (2)	C5B—C6B	1.404 (3)
N2A—C6A	1.391 (2)	C5B—H5BA	0.93
N2A—H2NA	0.74 (3)	C7B—C8B	1.501 (3)
C1A—C2A	1.498 (3)	C8B—H8BA	0.96
C1A—H1AA	0.97	C8B—H8BB	0.96
C1A—H1AB	0.97	C8B—H8BC	0.96
C2A—C3A	1.387 (3)	Br1C—C1C	1.968 (2)
C3A—C4A	1.386 (3)	O1C—C7C	1.233 (2)
C3A—H3AA	0.93	N1C—C6C	1.336 (2)
C4A—C5A	1.380 (3)	N1C—C2C	1.338 (2)
C4A—H4AA	0.93	N2C—C7C	1.360 (2)
C5A—C6A	1.406 (2)	N2C—C6C	1.392 (2)
C5A—H5AA	0.93	N2C—H2NC	0.73 (3)
C7A—C8A	1.494 (3)	C1C—C2C	1.491 (3)
C8A—H8AA	0.96	C1C—H1CA	0.97
C8A—H8AB	0.96	C1C—H1CB	0.97
C8A—H8AC	0.96	C2C—C3C	1.382 (3)
Br1B—C1B	1.9722 (19)	C3C—C4C	1.385 (3)
O1B—C7B	1.225 (2)	C3C—H3CA	0.93
N1B—C2B	1.336 (2)	C4C—C5C	1.380 (3)
N1B—C6B	1.338 (2)	C4C—H4CA	0.93
N2B—C7B	1.360 (2)	C5C—C6C	1.398 (2)
N2B—C6B	1.394 (2)	C5C—H5CA	0.93
N2B—H2NB	0.93 (3)	C7C—C8C	1.494 (3)
C1B—C2B	1.489 (3)	C8C—H8CA	0.96
C1B—H1BA	0.97	C8C—H8CB	0.96
C1B—H1BB	0.97	C8C—H8CC	0.96
C2B—C3B	1.385 (3)
C6A—N1A—C2A	118.40 (15)	C5B—C4B—H4BA	119.9
C7A—N2A—C6A	128.33 (16)	C3B—C4B—H4BA	119.9
C7A—N2A—H2NA	113 (3)	C4B—C5B—C6B	117.78 (17)
C6A—N2A—H2NA	118 (3)	C4B—C5B—H5BA	121.1
C2A—C1A—Br1A	111.74 (13)	C6B—C5B—H5BA	121.1
C2A—C1A—H1AA	109.3	N1B—C6B—N2B	113.14 (16)
Br1A—C1A—H1AA	109.3	N1B—C6B—C5B	122.70 (17)
C2A—C1A—H1AB	109.3	N2B—C6B—C5B	124.16 (16)
Br1A—C1A—H1AB	109.3	O1B—C7B—N2B	122.83 (19)
H1AA—C1A—H1AB	107.9	O1B—C7B—C8B	121.62 (19)
N1A—C2A—C3A	123.14 (17)	N2B—C7B—C8B	115.54 (17)
N1A—C2A—C1A	115.46 (16)	C7B—C8B—H8BA	109.5
C3A—C2A—C1A	121.39 (17)	C7B—C8B—H8BB	109.5
C4A—C3A—C2A	117.74 (17)	H8BA—C8B—H8BB	109.5
C4A—C3A—H3AA	121.1	C7B—C8B—H8BC	109.5
C2A—C3A—H3AA	121.1	H8BA—C8B—H8BC	109.5
C5A—C4A—C3A	120.55 (17)	H8BB—C8B—H8BC	109.5
C5A—C4A—H4AA	119.7	C6C—N1C—C2C	118.06 (16)
C3A—C4A—H4AA	119.7	C7C—N2C—C6C	129.32 (16)
C4A—C5A—C6A	117.35 (17)	C7C—N2C—H2NC	109 (2)
C4A—C5A—H5AA	121.3	C6C—N2C—H2NC	121 (2)
C6A—C5A—H5AA	121.3	C2C—C1C—Br1C	111.62 (13)
N1A—C6A—N2A	112.72 (16)	C2C—C1C—H1CA	109.3
N1A—C6A—C5A	122.82 (17)	Br1C—C1C—H1CA	109.3
N2A—C6A—C5A	124.46 (16)	C2C—C1C—H1CB	109.3
O1A—C7A—N2A	122.80 (18)	Br1C—C1C—H1CB	109.3
O1A—C7A—C8A	122.20 (17)	H1CA—C1C—H1CB	108.0
N2A—C7A—C8A	114.99 (17)	N1C—C2C—C3C	123.20 (17)
C7A—C8A—H8AA	109.5	N1C—C2C—C1C	115.60 (16)
C7A—C8A—H8AB	109.5	C3C—C2C—C1C	121.18 (17)
H8AA—C8A—H8AB	109.5	C2C—C3C—C4C	117.81 (18)
C7A—C8A—H8AC	109.5	C2C—C3C—H3CA	121.1
H8AA—C8A—H8AC	109.5	C4C—C3C—H3CA	121.1
H8AB—C8A—H8AC	109.5	C5C—C4C—C3C	120.48 (17)
C2B—N1B—C6B	118.02 (16)	C5C—C4C—H4CA	119.8
C7B—N2B—C6B	127.83 (16)	C3C—C4C—H4CA	119.8
C7B—N2B—H2NB	115.3 (19)	C4C—C5C—C6C	117.26 (17)
C6B—N2B—H2NB	116.8 (19)	C4C—C5C—H5CA	121.4
C2B—C1B—Br1B	111.85 (13)	C6C—C5C—H5CA	121.4
C2B—C1B—H1BA	109.2	N1C—C6C—N2C	112.20 (16)
Br1B—C1B—H1BA	109.2	N1C—C6C—C5C	123.19 (17)
C2B—C1B—H1BB	109.2	N2C—C6C—C5C	124.62 (16)
Br1B—C1B—H1BB	109.2	O1C—C7C—N2C	123.35 (18)
H1BA—C1B—H1BB	107.9	O1C—C7C—C8C	122.47 (17)
N1B—C2B—C3B	123.66 (17)	N2C—C7C—C8C	114.18 (16)
N1B—C2B—C1B	115.86 (16)	C7C—C8C—H8CA	109.5
C3B—C2B—C1B	120.41 (17)	C7C—C8C—H8CB	109.5
C2B—C3B—C4B	117.55 (18)	H8CA—C8C—H8CB	109.5
C2B—C3B—H3BA	121.2	C7C—C8C—H8CC	109.5
C4B—C3B—H3BA	121.2	H8CA—C8C—H8CC	109.5
C5B—C4B—C3B	120.29 (18)	H8CB—C8C—H8CC	109.5
C6A—N1A—C2A—C3A	0.4 (3)	C2B—N1B—C6B—N2B	−179.55 (16)
C6A—N1A—C2A—C1A	−178.19 (16)	C2B—N1B—C6B—C5B	0.1 (3)
Br1A—C1A—C2A—N1A	−71.41 (19)	C7B—N2B—C6B—N1B	168.3 (2)
Br1A—C1A—C2A—C3A	110.00 (18)	C7B—N2B—C6B—C5B	−11.3 (3)
N1A—C2A—C3A—C4A	−0.5 (3)	C4B—C5B—C6B—N1B	0.3 (3)
C1A—C2A—C3A—C4A	177.93 (17)	C4B—C5B—C6B—N2B	179.93 (19)
C2A—C3A—C4A—C5A	0.3 (3)	C6B—N2B—C7B—O1B	2.6 (4)
C3A—C4A—C5A—C6A	0.1 (3)	C6B—N2B—C7B—C8B	−177.6 (2)
C2A—N1A—C6A—N2A	179.68 (16)	C6C—N1C—C2C—C3C	−0.1 (3)
C2A—N1A—C6A—C5A	0.0 (3)	C6C—N1C—C2C—C1C	−178.23 (17)
C7A—N2A—C6A—N1A	178.45 (19)	Br1C—C1C—C2C—N1C	−73.37 (19)
C7A—N2A—C6A—C5A	−1.9 (3)	Br1C—C1C—C2C—C3C	108.44 (18)
C4A—C5A—C6A—N1A	−0.2 (3)	N1C—C2C—C3C—C4C	−0.4 (3)
C4A—C5A—C6A—N2A	−179.84 (18)	C1C—C2C—C3C—C4C	177.65 (18)
C6A—N2A—C7A—O1A	−2.9 (3)	C2C—C3C—C4C—C5C	0.6 (3)
C6A—N2A—C7A—C8A	176.72 (18)	C3C—C4C—C5C—C6C	−0.3 (3)
C6B—N1B—C2B—C3B	−0.4 (3)	C2C—N1C—C6C—N2C	−179.58 (17)
C6B—N1B—C2B—C1B	176.64 (16)	C2C—N1C—C6C—C5C	0.4 (3)
Br1B—C1B—C2B—N1B	78.77 (19)	C7C—N2C—C6C—N1C	178.90 (19)
Br1B—C1B—C2B—C3B	−104.14 (18)	C7C—N2C—C6C—C5C	−1.1 (3)
N1B—C2B—C3B—C4B	0.2 (3)	C4C—C5C—C6C—N1C	−0.2 (3)
C1B—C2B—C3B—C4B	−176.68 (17)	C4C—C5C—C6C—N2C	179.76 (19)
C2B—C3B—C4B—C5B	0.3 (3)	C6C—N2C—C7C—O1C	−1.6 (3)
C3B—C4B—C5B—C6B	−0.5 (3)	C6C—N2C—C7C—C8C	178.7 (2)

Cg1 and Cg2 are the centroids of the C2A–C6A/N1A and C2C–C6C/N1C pyridine rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2NA···O1Ci	0.74 (3)	2.29 (3)	3.022 (2)	172 (4)
N2B—H2NB···O1A	0.93 (3)	1.97 (3)	2.885 (2)	166 (3)
N2C—H2NC···O1Bii	0.73 (3)	2.18 (3)	2.900 (2)	169 (3)
C1B—H1BA···Br1Biii	0.97	2.85	3.716 (2)	149
C8B—H8BB···O1A	0.96	2.50	3.159 (3)	125
C8C—H8CA···N1Aiv	0.96	2.50	3.427 (3)	162
C1A—H1AB···Cg1iii	0.97	2.88	3.612 (2)	133
C1C—H1CB···Cg2iii	0.97	2.81	3.447 (2)	124

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2A–C6A/N1A and C2C–C6C/N1C pyridine rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2NA⋯O1Ci	0.74 (3)	2.29 (3)	3.022 (2)	172 (4)
N2B—H2NB⋯O1A	0.93 (3)	1.97 (3)	2.885 (2)	166 (3)
N2C—H2NC⋯O1Bii	0.73 (3)	2.18 (3)	2.900 (2)	169 (3)
C1B—H1BA⋯Br1Biii	0.97	2.85	3.716 (2)	149
C8B—H8BB⋯O1A	0.96	2.50	3.159 (3)	125
C8C—H8CA⋯N1Aiv	0.96	2.50	3.427 (3)	162
C1A—H1AB⋯Cg1iii	0.97	2.88	3.612 (2)	133
C1C—H1CB⋯Cg2iii	0.97	2.81	3.447 (2)	124

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