N'-[(E)-2,6-Dichloro-benzyl-idene]pyrazine-2-carbohydrazide.

The title compound, C(12)H(8)Cl(2)N(4)O, is non-planar, the dihedral angle formed between the pendant pyrazine and benzene rings being 12.55 (11)°. An intra-molecular N-H⋯N hydrogen bond occurs. The amide groups self-associate via N-H⋯O hydrogen bonding, forming supra-molecular chains with base vector [101], which are stabilized by C-H⋯O contacts. C-H⋯N inter-actions are formed orthogonal to the chains.

Related literature

For background to the biological activity of pyrazine derivatives, see: Barlin (1982 ▶); Dolezal et al. (2002 ▶); Krinkova et al. (2002 ▶); Özdemir et al. (2009 ▶); Chaisson et al. (2002 ▶); Gordin et al. (2000 ▶); de Souza et al. (2005 ▶). For related structures, see: Wardell et al. (2008 ▶); Baddeley et al. (2009 ▶).

Experimental

Crystal data

C12H8Cl2N4O

M = 295.12

Monoclinic,

a = 6.9325 (3) Å

b = 24.5997 (13) Å

c = 7.6136 (4) Å

β = 111.709 (3)°

V = 1206.31 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.53 mm−1

T = 120 K

0.26 × 0.08 × 0.02 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.760, T max = 1.000

8211 measured reflections

2108 independent reflections

1858 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.112

S = 1.14

2108 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.34 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DEn class="Chemical">NZO 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053343/lh2969sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053343/lh2969Isup2.hkl

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

C12H8Cl2N4O	F(000) = 600
Mr = 295.12	Dx = 1.625 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11372 reflections
a = 6.9325 (3) Å	θ = 2.9–27.5°
b = 24.5997 (13) Å	µ = 0.53 mm−1
c = 7.6136 (4) Å	T = 120 K
β = 111.709 (3)°	Plate, colourless
V = 1206.31 (10) Å3	0.26 × 0.08 × 0.02 mm
Z = 4

Enraf–Nonius KappaCCD area-detector diffractometer	2108 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1858 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.052
Detector resolution: 9.091 pixels mm-1	θmax = 25.0°, θmin = 3.0°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −29→29
Tmin = 0.760, Tmax = 1.000	l = −9→8
8211 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0128P)2 + 2.8931P] where P = (Fo2 + 2Fc2)/3
2108 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.34 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	0.21383 (14)	0.04241 (3)	−0.00147 (12)	0.0280 (2)
Cl2	0.35539 (13)	0.19347 (3)	0.56395 (11)	0.0216 (2)
O1	0.4468 (3)	0.31301 (9)	0.2140 (3)	0.0211 (5)
N1	0.2594 (4)	0.41462 (11)	−0.2597 (4)	0.0229 (6)
N2	0.2914 (4)	0.30126 (11)	−0.2806 (4)	0.0174 (6)
N3	0.2987 (4)	0.24065 (10)	0.0247 (4)	0.0169 (6)
H3N	0.2381	0.2284	−0.0915	0.020*
N4	0.3326 (4)	0.20678 (11)	0.1769 (4)	0.0177 (6)
C1	0.3138 (4)	0.32651 (13)	−0.1186 (4)	0.0157 (7)
C2	0.2997 (5)	0.38272 (13)	−0.1084 (5)	0.0195 (7)
H2	0.3195	0.3990	0.0102	0.023*
C3	0.2393 (5)	0.38910 (14)	−0.4200 (5)	0.0216 (7)
H3	0.2127	0.4101	−0.5312	0.026*
C4	0.2556 (5)	0.33325 (13)	−0.4310 (4)	0.0202 (7)
H4	0.2409	0.3172	−0.5488	0.024*
C5	0.3600 (5)	0.29311 (12)	0.0566 (4)	0.0150 (6)
C6	0.2611 (5)	0.15869 (13)	0.1347 (4)	0.0171 (7)
H6	0.1945	0.1492	0.0053	0.020*
C7	0.2784 (5)	0.11748 (13)	0.2801 (4)	0.0170 (7)
C8	0.2472 (5)	0.06223 (14)	0.2280 (4)	0.0191 (7)
C9	0.2446 (5)	0.02134 (14)	0.3508 (5)	0.0231 (7)
H9	0.2212	−0.0153	0.3084	0.028*
C10	0.2764 (5)	0.03408 (14)	0.5368 (5)	0.0243 (8)
H10	0.2743	0.0063	0.6227	0.029*
C11	0.3110 (5)	0.08741 (13)	0.5960 (5)	0.0198 (7)
H11	0.3330	0.0963	0.7234	0.024*
C12	0.3142 (5)	0.12832 (13)	0.4710 (5)	0.0184 (7)

	U11	U22	U33	U12	U13	U23
Cl1	0.0433 (5)	0.0230 (5)	0.0214 (5)	−0.0088 (4)	0.0162 (4)	−0.0058 (3)
Cl2	0.0286 (5)	0.0192 (4)	0.0173 (4)	−0.0039 (3)	0.0090 (3)	−0.0028 (3)
O1	0.0247 (12)	0.0195 (12)	0.0159 (12)	−0.0036 (10)	0.0038 (10)	−0.0034 (9)
N1	0.0225 (15)	0.0208 (15)	0.0239 (15)	−0.0005 (12)	0.0067 (12)	0.0021 (12)
N2	0.0185 (14)	0.0170 (14)	0.0149 (13)	−0.0019 (11)	0.0042 (11)	−0.0015 (11)
N3	0.0214 (14)	0.0165 (14)	0.0110 (13)	−0.0020 (11)	0.0036 (11)	0.0011 (10)
N4	0.0210 (14)	0.0170 (14)	0.0150 (14)	0.0006 (11)	0.0066 (12)	0.0035 (11)
C1	0.0103 (15)	0.0203 (17)	0.0128 (16)	−0.0043 (13)	−0.0002 (12)	−0.0008 (12)
C2	0.0185 (16)	0.0174 (16)	0.0199 (17)	0.0018 (13)	0.0038 (14)	0.0000 (13)
C3	0.0198 (17)	0.0225 (18)	0.0193 (17)	−0.0004 (14)	0.0036 (14)	0.0046 (14)
C4	0.0231 (17)	0.0234 (18)	0.0149 (16)	−0.0020 (14)	0.0081 (14)	−0.0027 (13)
C5	0.0150 (15)	0.0174 (16)	0.0120 (15)	0.0017 (13)	0.0044 (13)	0.0008 (12)
C6	0.0174 (16)	0.0203 (17)	0.0106 (15)	0.0001 (13)	0.0018 (13)	0.0020 (13)
C7	0.0133 (15)	0.0187 (16)	0.0188 (16)	0.0006 (13)	0.0056 (13)	0.0026 (13)
C8	0.0196 (17)	0.0232 (17)	0.0161 (17)	−0.0002 (14)	0.0084 (14)	0.0017 (13)
C9	0.0242 (18)	0.0173 (17)	0.0285 (19)	0.0007 (14)	0.0105 (15)	0.0000 (14)
C10	0.0274 (18)	0.0228 (19)	0.0230 (18)	0.0030 (15)	0.0098 (15)	0.0081 (14)
C11	0.0199 (17)	0.0233 (18)	0.0174 (16)	0.0016 (14)	0.0084 (14)	0.0042 (13)
C12	0.0154 (15)	0.0182 (17)	0.0211 (17)	−0.0012 (13)	0.0060 (14)	−0.0013 (13)

Cl1—C8	1.745 (3)	C3—C4	1.384 (5)
Cl2—C12	1.732 (3)	C3—H3	0.9500
O1—C5	1.227 (4)	C4—H4	0.9500
N1—C3	1.333 (4)	C6—C7	1.473 (4)
N1—C2	1.335 (4)	C6—H6	0.9500
N2—C4	1.335 (4)	C7—C12	1.407 (4)
N2—C1	1.338 (4)	C7—C8	1.410 (5)
N3—C5	1.352 (4)	C8—C9	1.378 (5)
N3—N4	1.375 (3)	C9—C10	1.386 (5)
N3—H3N	0.8800	C9—H9	0.9500
N4—C6	1.277 (4)	C10—C11	1.379 (5)
C1—C2	1.390 (4)	C10—H10	0.9500
C1—C5	1.497 (4)	C11—C12	1.391 (4)
C2—H2	0.9500	C11—H11	0.9500
C3—N1—C2	115.5 (3)	N4—C6—C7	122.2 (3)
C4—N2—C1	116.0 (3)	N4—C6—H6	118.9
C5—N3—N4	118.8 (3)	C7—C6—H6	118.9
C5—N3—H3N	120.6	C12—C7—C8	115.0 (3)
N4—N3—H3N	120.6	C12—C7—C6	125.5 (3)
C6—N4—N3	114.8 (3)	C8—C7—C6	119.4 (3)
N2—C1—C2	121.8 (3)	C9—C8—C7	123.5 (3)
N2—C1—C5	118.7 (3)	C9—C8—Cl1	116.4 (3)
C2—C1—C5	119.5 (3)	C7—C8—Cl1	120.0 (2)
N1—C2—C1	122.2 (3)	C8—C9—C10	119.4 (3)
N1—C2—H2	118.9	C8—C9—H9	120.3
C1—C2—H2	118.9	C10—C9—H9	120.3
N1—C3—C4	122.7 (3)	C11—C10—C9	119.5 (3)
N1—C3—H3	118.7	C11—C10—H10	120.3
C4—C3—H3	118.7	C9—C10—H10	120.3
N2—C4—C3	121.8 (3)	C10—C11—C12	120.6 (3)
N2—C4—H4	119.1	C10—C11—H11	119.7
C3—C4—H4	119.1	C12—C11—H11	119.7
O1—C5—N3	124.4 (3)	C11—C12—C7	121.9 (3)
O1—C5—C1	121.2 (3)	C11—C12—Cl2	115.6 (2)
N3—C5—C1	114.5 (3)	C7—C12—Cl2	122.5 (2)
C5—N3—N4—C6	176.7 (3)	N4—C6—C7—C12	19.9 (5)
C4—N2—C1—C2	0.2 (4)	N4—C6—C7—C8	−163.6 (3)
C4—N2—C1—C5	−178.4 (3)	C12—C7—C8—C9	2.0 (5)
C3—N1—C2—C1	−1.8 (5)	C6—C7—C8—C9	−174.9 (3)
N2—C1—C2—N1	1.3 (5)	C12—C7—C8—Cl1	−176.8 (2)
C5—C1—C2—N1	179.9 (3)	C6—C7—C8—Cl1	6.3 (4)
C2—N1—C3—C4	1.0 (5)	C7—C8—C9—C10	−0.8 (5)
C1—N2—C4—C3	−1.1 (4)	Cl1—C8—C9—C10	178.1 (3)
N1—C3—C4—N2	0.5 (5)	C8—C9—C10—C11	−0.3 (5)
N4—N3—C5—O1	0.7 (5)	C9—C10—C11—C12	0.0 (5)
N4—N3—C5—C1	−179.4 (3)	C10—C11—C12—C7	1.3 (5)
N2—C1—C5—O1	155.9 (3)	C10—C11—C12—Cl2	179.0 (3)
C2—C1—C5—O1	−22.7 (4)	C8—C7—C12—C11	−2.2 (4)
N2—C1—C5—N3	−24.0 (4)	C6—C7—C12—C11	174.4 (3)
C2—C1—C5—N3	157.4 (3)	C8—C7—C12—Cl2	−179.8 (2)
N3—N4—C6—C7	−178.3 (3)	C6—C7—C12—Cl2	−3.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···O1i	0.88	2.26	3.003 (3)	142
N3—H3n···N2	0.88	2.41	2.746 (4)	103
C6—H6···O1i	0.95	2.43	3.214 (4)	140
C10—H10···N1ii	0.95	2.53	3.448 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3n⋯O1i	0.88	2.26	3.003 (3)	142
N3—H3n⋯N2	0.88	2.41	2.746 (4)	103
C6—H6⋯O1i	0.95	2.43	3.214 (4)	140
C10—H10⋯N1ii	0.95	2.53	3.448 (4)	162

Symmetry codes: (i) ; (ii) .