N-(2-Chloro-eth-yl)pyrazine-2-carboxamide.

In the title mol-ecule, C(7)H(8)ClN(3)O, the pyrazine and amide groups are almost co-planar [N-C-C-N torsion angle = -2.4 (2) °], a conformation stabilized by an intra-molecular N-H⋯N hydrogen bond. The chloro-ethyl group lies out of the plane [N-C-C-Cl = -65.06 (17) °]. In the crystal, the presence of N-H⋯N hydrogen bonds leads to the formation of a C(6) supra-molecular chain along the b axis. The carbonyl-O atom accepts two C-H⋯O inter-actions. These, plus Cl⋯Cl short contacts [3.3653 (6) Å], consolidate the packing of the chains in the crystal.

Related literature

For the anti­mycobacterial activity of pyrazinamide, see: Chaisson et al. (2002 ▶); Gordin et al. (2000 ▶); de Souza (2006 ▶). For structural studies on n class="Chemical">pyrazinamide derivatives; see: Wardell et al. (2008 ▶); Baddeley et al. (2009 ▶); Howie et al. (2010a ▶,b ▶,c ▶,d ▶).

Experimental

Crystal data

C7H8ClN3O

M = 185.61

Monoclinic,

a = 4.4639 (2) Å

b = 10.6865 (6) Å

c = 17.3583 (9) Å

β = 93.028 (3)°

V = 826.89 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 120 K

0.28 × 0.18 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.631, T max = 0.746

16245 measured reflections

1867 independent reflections

1628 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.110

S = 1.15

1867 reflections

112 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.37 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536810041656/hb5682sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041656/hb5682Isup2.hkl

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

C7H8ClN3O	F(000) = 384
Mr = 185.61	Dx = 1.491 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25954 reflections
a = 4.4639 (2) Å	θ = 2.9–27.5°
b = 10.6865 (6) Å	µ = 0.41 mm−1
c = 17.3583 (9) Å	T = 120 K
β = 93.028 (3)°	Prism, colourless
V = 826.89 (7) Å3	0.28 × 0.18 × 0.03 mm
Z = 4

Nonius KappaCCD diffractometer	1867 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1628 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.044
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −13→13
Tmin = 0.631, Tmax = 0.746	l = −22→22
16245 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.3276P] where P = (Fo2 + 2Fc2)/3
1867 reflections	(Δ/σ)max < 0.001
112 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.37 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.65306 (10)	0.64380 (4)	0.49830 (2)	0.02780 (17)
O1	0.7056 (3)	1.04630 (12)	0.60138 (7)	0.0247 (3)
N1	0.8112 (3)	0.84349 (13)	0.63161 (8)	0.0195 (3)
H1n	0.785 (5)	0.7824 (15)	0.6637 (10)	0.028*
N2	0.4415 (3)	0.85341 (14)	0.75082 (8)	0.0222 (3)
N3	0.1647 (4)	1.07915 (15)	0.78848 (9)	0.0275 (4)
C1	0.6754 (4)	0.95343 (16)	0.64249 (9)	0.0182 (3)
C2	0.4763 (4)	0.95775 (15)	0.70976 (9)	0.0180 (3)
C3	0.2635 (4)	0.86226 (18)	0.80989 (10)	0.0249 (4)
H3	0.2273	0.7897	0.8396	0.030*
C4	0.1292 (4)	0.97467 (19)	0.82923 (10)	0.0264 (4)
H4	0.0087	0.9772	0.8727	0.032*
C5	0.3352 (4)	1.06922 (17)	0.72769 (10)	0.0229 (4)
H5	0.3607	1.1403	0.6959	0.028*
C6	1.0072 (4)	0.82477 (17)	0.56832 (9)	0.0212 (4)
H6A	1.1499	0.7565	0.5821	0.025*
H6B	1.1252	0.9020	0.5613	0.025*
C7	0.8395 (4)	0.79260 (17)	0.49280 (10)	0.0232 (4)
H7A	0.9823	0.7900	0.4511	0.028*
H7B	0.6894	0.8586	0.4799	0.028*

	U11	U22	U33	U12	U13	U23
Cl1	0.0327 (3)	0.0252 (3)	0.0255 (3)	−0.00579 (17)	0.00184 (18)	−0.00416 (17)
O1	0.0294 (7)	0.0222 (7)	0.0229 (6)	−0.0018 (5)	0.0045 (5)	0.0058 (5)
N1	0.0221 (7)	0.0200 (8)	0.0164 (7)	−0.0010 (6)	0.0025 (5)	0.0017 (5)
N2	0.0248 (8)	0.0230 (8)	0.0190 (7)	−0.0010 (6)	0.0023 (6)	0.0019 (6)
N3	0.0312 (8)	0.0271 (9)	0.0245 (8)	−0.0003 (6)	0.0048 (6)	−0.0055 (6)
C1	0.0173 (7)	0.0210 (8)	0.0163 (7)	−0.0040 (6)	−0.0011 (6)	−0.0017 (6)
C2	0.0190 (8)	0.0194 (8)	0.0152 (7)	−0.0036 (6)	−0.0014 (6)	−0.0013 (6)
C3	0.0293 (9)	0.0279 (10)	0.0179 (8)	−0.0026 (7)	0.0042 (7)	0.0026 (7)
C4	0.0282 (9)	0.0333 (10)	0.0181 (8)	−0.0029 (8)	0.0047 (7)	−0.0031 (7)
C5	0.0272 (9)	0.0211 (9)	0.0206 (8)	−0.0024 (7)	0.0028 (7)	−0.0015 (7)
C6	0.0189 (8)	0.0253 (9)	0.0199 (8)	−0.0018 (7)	0.0046 (6)	−0.0006 (7)
C7	0.0273 (9)	0.0237 (9)	0.0190 (8)	−0.0025 (7)	0.0044 (7)	0.0011 (7)

Cl1—C7	1.7997 (19)	C2—C5	1.390 (2)
O1—C1	1.234 (2)	C3—C4	1.391 (3)
N1—C1	1.340 (2)	C3—H3	0.9500
N1—C6	1.454 (2)	C4—H4	0.9500
N1—H1n	0.870 (10)	C5—H5	0.9500
N2—C3	1.334 (2)	C6—C7	1.514 (2)
N2—C2	1.337 (2)	C6—H6A	0.9900
N3—C4	1.336 (3)	C6—H6B	0.9900
N3—C5	1.338 (2)	C7—H7A	0.9900
C1—C2	1.505 (2)	C7—H7B	0.9900
C1—N1—C6	121.46 (14)	C3—C4—H4	119.0
C1—N1—H1N	119.4 (14)	N3—C5—C2	121.86 (17)
C6—N1—H1N	119.1 (14)	N3—C5—H5	119.1
C3—N2—C2	116.20 (15)	C2—C5—H5	119.1
C4—N3—C5	116.09 (16)	N1—C6—C7	113.30 (14)
O1—C1—N1	124.03 (15)	N1—C6—H6A	108.9
O1—C1—C2	120.73 (15)	C7—C6—H6A	108.9
N1—C1—C2	115.24 (14)	N1—C6—H6B	108.9
N2—C2—C5	121.91 (15)	C7—C6—H6B	108.9
N2—C2—C1	118.55 (15)	H6A—C6—H6B	107.7
C5—C2—C1	119.53 (15)	C6—C7—Cl1	111.32 (12)
N2—C3—C4	121.91 (17)	C6—C7—H7A	109.4
N2—C3—H3	119.0	Cl1—C7—H7A	109.4
C4—C3—H3	119.0	C6—C7—H7B	109.4
N3—C4—C3	121.95 (16)	Cl1—C7—H7B	109.4
N3—C4—H4	119.0	H7A—C7—H7B	108.0
C6—N1—C1—O1	−0.6 (2)	C2—N2—C3—C4	−2.0 (3)
C6—N1—C1—C2	179.20 (13)	C5—N3—C4—C3	0.4 (3)
C3—N2—C2—C5	0.1 (2)	N2—C3—C4—N3	1.8 (3)
C3—N2—C2—C1	179.85 (15)	C4—N3—C5—C2	−2.3 (3)
O1—C1—C2—N2	177.44 (15)	N2—C2—C5—N3	2.2 (3)
N1—C1—C2—N2	−2.4 (2)	C1—C2—C5—N3	−177.58 (15)
O1—C1—C2—C5	−2.8 (2)	C1—N1—C6—C7	−83.3 (2)
N1—C1—C2—C5	177.37 (15)	N1—C6—C7—Cl1	−65.06 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···N2	0.87 (2)	2.34 (2)	2.7162 (19)	107 (1)
N1—H1n···N3i	0.87 (2)	2.33 (2)	3.146 (2)	156 (2)
C5—H5···N2ii	0.95	2.60	3.212 (2)	123
C7—H7A···O1iii	0.99	2.44	3.180 (2)	131
C7—H7B···O1iv	0.99	2.42	3.337 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯N2	0.87 (2)	2.34 (2)	2.7162 (19)	107 (1)
N1—H1n⋯N3i	0.87 (2)	2.33 (2)	3.146 (2)	156 (2)
C5—H5⋯N2ii	0.95	2.60	3.212 (2)	123
C7—H7A⋯O1iii	0.99	2.44	3.180 (2)	131
C7—H7B⋯O1iv	0.99	2.42	3.337 (2)	153

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