N-(5-Bromo-pyridin-2-yl)acetamide.

The asymmetric unit of the title compound, C(7)H(7)BrN(2)O, contains two mol-ecules, in one of which the methyl H atoms are disorderd over two orientations in a 0.57 (3):0.43 (3) ratio. The dihedral angles between the pyridine rings and the acetamide groups are 7.27 (11) and 8.46 (11)°. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds generating bifurcated R(2) (1)(5) ring motifs, which in turn lead to [110] chains.

Related literature

For background to the acetyl­ation of amines, see: Greene & Wuts (1999 ▶); Moore et al. (1940 ▶); Suyama & Gerwick (2006 ▶). For a related structure, see: Loureiro et al. (2008 ▶). For further synthetic information, see: Augustine et al. (2011 ▶); Sollogoub et al. (2002 ▶).

Experimental

Crystal data

C7H7BrN2O

M = 215.06

Triclinic,

a = 4.0014 (3) Å

b = 8.7232 (6) Å

c = 23.0626 (18) Å

α = 82.127 (1)°

β = 86.897 (1)°

γ = 85.932 (1)°

V = 794.60 (10) Å3

Z = 4

Mo Kα radiation

μ = 5.11 mm−1

T = 296 K

0.77 × 0.15 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T min = 0.111, T max = 0.665

13194 measured reflections

5134 independent reflections

3193 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.00

5134 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.25 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 datablock(s) global, I. DOI: 10.1107/S1600536811027553/hb5933sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027553/hb5933Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027553/hb5933Isup3.cml

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

C7H7BrN2O	Z = 4
Mr = 215.06	F(000) = 424
Triclinic, P1	Dx = 1.798 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.0014 (3) Å	Cell parameters from 3316 reflections
b = 8.7232 (6) Å	θ = 2.8–30.5°
c = 23.0626 (18) Å	µ = 5.11 mm−1
α = 82.127 (1)°	T = 296 K
β = 86.897 (1)°	Needle, colourless
γ = 85.932 (1)°	0.77 × 0.15 × 0.09 mm
V = 794.60 (10) Å3

Bruker SMART APEXII CCD diffractometer	5134 independent reflections
Radiation source: fine-focus sealed tube	3193 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 31.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
Tmin = 0.111, Tmax = 0.665	k = −12→12
13194 measured reflections	l = −33→33

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.036P)2 + 0.0264P] where P = (Fo2 + 2Fc2)/3
5134 reflections	(Δ/σ)max = 0.006
201 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1A	0.84865 (6)	0.73249 (2)	0.465121 (9)	0.05565 (9)
O1A	0.4679 (4)	0.97838 (16)	0.73640 (6)	0.0613 (5)
N1A	0.4235 (5)	0.63040 (18)	0.63081 (7)	0.0492 (4)
N2A	0.3137 (4)	0.75247 (17)	0.71180 (6)	0.0433 (4)
H1NA	0.2221	0.6674	0.7226	0.052*
C1A	0.5431 (6)	0.6264 (2)	0.57599 (9)	0.0509 (5)
H1AA	0.5303	0.5356	0.5595	0.061*
C2A	0.6845 (5)	0.7499 (2)	0.54257 (8)	0.0433 (4)
C3A	0.7046 (6)	0.8840 (2)	0.56632 (9)	0.0517 (5)
H3AA	0.7967	0.9695	0.5444	0.062*
C4A	0.5868 (6)	0.8907 (2)	0.62322 (9)	0.0515 (5)
H4AA	0.6018	0.9801	0.6405	0.062*
C5A	0.4449 (5)	0.7612 (2)	0.65427 (8)	0.0397 (4)
C6A	0.3318 (5)	0.8566 (2)	0.74991 (8)	0.0427 (4)
C7A	0.1744 (6)	0.8125 (3)	0.80974 (9)	0.0568 (6)
H7AA	0.0849	0.6942	0.8167	0.085*	0.57 (3)
H7AB	−0.0154	0.9051	0.8188	0.085*	0.57 (3)
H7AC	0.3210	0.8117	0.8427	0.085*	0.57 (3)
H7AD	0.2003	0.8929	0.8334	0.085*	0.43 (3)
H7AE	0.2826	0.7172	0.8275	0.085*	0.43 (3)
H7AF	−0.0598	0.7992	0.8067	0.085*	0.43 (3)
Br1B	0.14559 (6)	0.24850 (3)	1.034407 (9)	0.05895 (9)
O1B	0.9318 (4)	0.47747 (16)	0.76218 (6)	0.0586 (4)
N1B	0.4457 (5)	0.13387 (19)	0.87208 (7)	0.0566 (5)
N2B	0.6803 (4)	0.25146 (17)	0.78696 (6)	0.0464 (4)
H1NB	0.6598	0.1634	0.7785	0.056*
C1B	0.3245 (7)	0.1341 (2)	0.92681 (10)	0.0594 (6)
H1BA	0.2365	0.0441	0.9461	0.071*
C2B	0.3226 (5)	0.2599 (2)	0.95615 (8)	0.0443 (5)
C3B	0.4515 (6)	0.3934 (2)	0.92795 (9)	0.0513 (5)
H3BA	0.4549	0.4804	0.9471	0.062*
C4B	0.5752 (6)	0.3965 (2)	0.87127 (9)	0.0506 (5)
H4BA	0.6621	0.4857	0.8511	0.061*
C5B	0.5681 (5)	0.2635 (2)	0.84446 (8)	0.0403 (4)
C6B	0.8508 (5)	0.3553 (2)	0.74883 (8)	0.0430 (4)
C7B	0.9337 (6)	0.3063 (2)	0.68947 (8)	0.0535 (5)
H7BA	1.0711	0.3804	0.6667	0.080*
H7BB	0.7302	0.3009	0.6698	0.080*
H7BC	1.0528	0.2062	0.6939	0.080*

	U11	U22	U33	U12	U13	U23
Br1A	0.06525 (17)	0.05384 (14)	0.05063 (13)	−0.01839 (11)	0.01455 (10)	−0.01617 (9)
O1A	0.0935 (13)	0.0446 (8)	0.0504 (8)	−0.0284 (8)	0.0052 (8)	−0.0140 (6)
N1A	0.0661 (12)	0.0349 (8)	0.0487 (9)	−0.0178 (8)	0.0068 (8)	−0.0091 (7)
N2A	0.0546 (11)	0.0322 (8)	0.0439 (9)	−0.0118 (7)	0.0042 (8)	−0.0063 (6)
C1A	0.0665 (15)	0.0360 (9)	0.0532 (11)	−0.0158 (10)	0.0074 (10)	−0.0145 (8)
C2A	0.0470 (12)	0.0400 (10)	0.0445 (10)	−0.0104 (9)	0.0036 (9)	−0.0099 (8)
C3A	0.0658 (15)	0.0391 (10)	0.0520 (11)	−0.0220 (10)	0.0111 (10)	−0.0080 (8)
C4A	0.0726 (16)	0.0332 (9)	0.0519 (11)	−0.0193 (10)	0.0085 (10)	−0.0128 (8)
C5A	0.0407 (11)	0.0332 (9)	0.0463 (10)	−0.0064 (8)	−0.0009 (8)	−0.0074 (7)
C6A	0.0502 (12)	0.0378 (9)	0.0413 (9)	−0.0058 (9)	−0.0029 (8)	−0.0076 (7)
C7A	0.0728 (16)	0.0567 (12)	0.0427 (11)	−0.0150 (12)	0.0061 (10)	−0.0107 (9)
Br1B	0.06627 (17)	0.06192 (15)	0.05093 (13)	−0.02114 (12)	0.01604 (11)	−0.01425 (10)
O1B	0.0785 (11)	0.0464 (8)	0.0529 (8)	−0.0275 (8)	0.0091 (7)	−0.0069 (6)
N1B	0.0841 (14)	0.0414 (9)	0.0473 (9)	−0.0249 (9)	0.0121 (9)	−0.0120 (7)
N2B	0.0627 (12)	0.0340 (8)	0.0443 (9)	−0.0145 (8)	0.0051 (8)	−0.0087 (6)
C1B	0.0811 (17)	0.0427 (11)	0.0564 (12)	−0.0266 (11)	0.0164 (12)	−0.0103 (9)
C2B	0.0432 (12)	0.0468 (10)	0.0444 (10)	−0.0127 (9)	0.0056 (8)	−0.0088 (8)
C3B	0.0667 (15)	0.0384 (10)	0.0517 (11)	−0.0149 (10)	0.0071 (10)	−0.0141 (8)
C4B	0.0701 (15)	0.0328 (9)	0.0500 (11)	−0.0175 (9)	0.0070 (10)	−0.0063 (8)
C5B	0.0452 (12)	0.0333 (9)	0.0438 (10)	−0.0093 (8)	−0.0007 (8)	−0.0073 (7)
C6B	0.0466 (12)	0.0375 (9)	0.0448 (10)	−0.0068 (9)	−0.0016 (8)	−0.0031 (8)
C7B	0.0610 (15)	0.0532 (12)	0.0471 (11)	−0.0127 (11)	0.0065 (10)	−0.0081 (9)

Br1A—C2A	1.8914 (18)	C7A—H7AF	0.9600
O1A—C6A	1.223 (2)	Br1B—C2B	1.8951 (18)
N1A—C1A	1.331 (3)	O1B—C6B	1.218 (2)
N1A—C5A	1.338 (2)	N1B—C1B	1.328 (3)
N2A—C6A	1.356 (2)	N1B—C5B	1.331 (2)
N2A—C5A	1.395 (2)	N2B—C6B	1.365 (2)
N2A—H1NA	0.8514	N2B—C5B	1.392 (2)
C1A—C2A	1.374 (3)	N2B—H1NB	0.8288
C1A—H1AA	0.9300	C1B—C2B	1.365 (3)
C2A—C3A	1.367 (3)	C1B—H1BA	0.9300
C3A—C4A	1.378 (3)	C2B—C3B	1.373 (3)
C3A—H3AA	0.9300	C3B—C4B	1.370 (3)
C4A—C5A	1.391 (3)	C3B—H3BA	0.9300
C4A—H4AA	0.9300	C4B—C5B	1.390 (3)
C6A—C7A	1.498 (3)	C4B—H4BA	0.9300
C7A—H7AA	1.1046	C6B—C7B	1.503 (3)
C7A—H7AB	1.1020	C7B—H7BA	0.9600
C7A—H7AC	0.9834	C7B—H7BB	0.9600
C7A—H7AD	0.9601	C7B—H7BC	0.9600
C7A—H7AE	0.9601
C1A—N1A—C5A	117.99 (17)	H7AD—C7A—H7AE	109.5
C6A—N2A—C5A	127.87 (16)	C6A—C7A—H7AF	109.7
C6A—N2A—H1NA	120.4	H7AA—C7A—H7AF	60.9
C5A—N2A—H1NA	111.7	H7AB—C7A—H7AF	59.5
N1A—C1A—C2A	123.21 (18)	H7AC—C7A—H7AF	134.3
N1A—C1A—H1AA	118.4	H7AD—C7A—H7AF	109.5
C2A—C1A—H1AA	118.4	H7AE—C7A—H7AF	109.5
C3A—C2A—C1A	118.88 (18)	C1B—N1B—C5B	118.10 (17)
C3A—C2A—Br1A	121.10 (14)	C6B—N2B—C5B	128.33 (16)
C1A—C2A—Br1A	120.01 (14)	C6B—N2B—H1NB	119.6
C2A—C3A—C4A	119.17 (18)	C5B—N2B—H1NB	111.5
C2A—C3A—H3AA	120.4	N1B—C1B—C2B	123.26 (19)
C4A—C3A—H3AA	120.4	N1B—C1B—H1BA	118.4
C3A—C4A—C5A	118.69 (17)	C2B—C1B—H1BA	118.4
C3A—C4A—H4AA	120.7	C1B—C2B—C3B	118.78 (18)
C5A—C4A—H4AA	120.7	C1B—C2B—Br1B	120.11 (15)
N1A—C5A—C4A	122.06 (18)	C3B—C2B—Br1B	121.12 (15)
N1A—C5A—N2A	113.20 (16)	C4B—C3B—C2B	119.06 (18)
C4A—C5A—N2A	124.74 (16)	C4B—C3B—H3BA	120.5
O1A—C6A—N2A	122.27 (17)	C2B—C3B—H3BA	120.5
O1A—C6A—C7A	122.17 (17)	C3B—C4B—C5B	118.65 (18)
N2A—C6A—C7A	115.57 (17)	C3B—C4B—H4BA	120.7
C6A—C7A—H7AA	113.6	C5B—C4B—H4BA	120.7
C6A—C7A—H7AB	108.3	N1B—C5B—C4B	122.15 (18)
H7AA—C7A—H7AB	115.1	N1B—C5B—N2B	113.26 (16)
C6A—C7A—H7AC	115.8	C4B—C5B—N2B	124.59 (17)
H7AA—C7A—H7AC	102.8	O1B—C6B—N2B	122.50 (17)
H7AB—C7A—H7AC	100.6	O1B—C6B—C7B	122.78 (17)
C6A—C7A—H7AD	109.4	N2B—C6B—C7B	114.71 (16)
H7AA—C7A—H7AD	136.6	C6B—C7B—H7BA	109.5
H7AB—C7A—H7AD	53.5	C6B—C7B—H7BB	109.5
H7AC—C7A—H7AD	51.1	H7BA—C7B—H7BB	109.5
C6A—C7A—H7AE	109.4	C6B—C7B—H7BC	109.5
H7AA—C7A—H7AE	50.3	H7BA—C7B—H7BC	109.5
H7AB—C7A—H7AE	142.2	H7BB—C7B—H7BC	109.5
H7AC—C7A—H7AE	59.4
C5A—N1A—C1A—C2A	−0.4 (4)	C5B—N1B—C1B—C2B	−0.7 (4)
N1A—C1A—C2A—C3A	0.0 (4)	N1B—C1B—C2B—C3B	0.1 (4)
N1A—C1A—C2A—Br1A	179.81 (18)	N1B—C1B—C2B—Br1B	−179.7 (2)
C1A—C2A—C3A—C4A	0.8 (4)	C1B—C2B—C3B—C4B	0.5 (4)
Br1A—C2A—C3A—C4A	−178.97 (18)	Br1B—C2B—C3B—C4B	−179.66 (18)
C2A—C3A—C4A—C5A	−1.2 (4)	C2B—C3B—C4B—C5B	−0.5 (4)
C1A—N1A—C5A—C4A	0.0 (3)	C1B—N1B—C5B—C4B	0.7 (4)
C1A—N1A—C5A—N2A	−179.75 (19)	C1B—N1B—C5B—N2B	−178.4 (2)
C3A—C4A—C5A—N1A	0.8 (3)	C3B—C4B—C5B—N1B	−0.1 (4)
C3A—C4A—C5A—N2A	−179.5 (2)	C3B—C4B—C5B—N2B	179.0 (2)
C6A—N2A—C5A—N1A	171.58 (19)	C6B—N2B—C5B—N1B	−172.3 (2)
C6A—N2A—C5A—C4A	−8.2 (3)	C6B—N2B—C5B—C4B	8.6 (4)
C5A—N2A—C6A—O1A	1.7 (3)	C5B—N2B—C6B—O1B	0.9 (3)
C5A—N2A—C6A—C7A	−178.2 (2)	C5B—N2B—C6B—C7B	−179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1NA···O1Bi	0.85	2.16	3.001 (2)	169
N2B—H1NB···O1Aii	0.83	2.20	2.985 (2)	159
C7A—H7AA···O1Bi	1.10	2.54	3.476 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H1NA⋯O1Bi	0.85	2.16	3.001 (2)	169
N2B—H1NB⋯O1Aii	0.83	2.20	2.985 (2)	159
C7A—H7AA⋯O1Bi	1.10	2.54	3.476 (3)	142

Symmetry codes: (i) ; (ii) .