N'-[(E)-3-Bromo-benzyl-idene]pyrazine-2-carbohydrazide.

In the title compound, C12H9BrN4O, the dihedral angle between the aromatic rings is 12.16 (12)°. An intra-molecular N-H⋯N hydrogen bond closes an S(5) ring. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into C(6) chains propagating in [010]. Very weak aromatic π-π stacking [centroid-centroid separations = 3.9189 (15) and 3.9357 (15) Å] is also observed.

Related literature

For related structures, see: Hameed et al. (2013a ▶,b ▶).

Experimental

Crystal data

C12H9BrN4O

M = 305.14

Monoclinic,

a = 14.4115 (8) Å

b = 6.2128 (3) Å

c = 27.5992 (15) Å

β = 104.379 (2)°

V = 2393.7 (2) Å3

Z = 8

Mo Kα radiation

μ = 3.43 mm−1

T = 296 K

0.34 × 0.25 × 0.23 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.389, T max = 0.506

9373 measured reflections

2415 independent reflections

1670 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.075

S = 1.02

2415 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813027426/hb7147sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813027426/hb7147Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027426/hb7147Isup3.cml

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

C12H9BrN4O	F(000) = 1216
Mr = 305.14	Dx = 1.693 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.4115 (8) Å	Cell parameters from 1670 reflections
b = 6.2128 (3) Å	θ = 1.5–26.3°
c = 27.5992 (15) Å	µ = 3.43 mm−1
β = 104.379 (2)°	T = 296 K
V = 2393.7 (2) Å3	Prism, colorless
Z = 8	0.34 × 0.25 × 0.23 mm

Bruker Kappa APEXII CCD diffractometer	2415 independent reflections
Radiation source: fine-focus sealed tube	1670 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 8.00 pixels mm-1	θmax = 26.3°, θmin = 1.5°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→7
Tmin = 0.389, Tmax = 0.506	l = −34→34
9373 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0348P)2 + 1.0725P] where P = (Fo2 + 2Fc2)/3
2415 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.34 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
Br1	0.62227 (2)	0.43755 (5)	0.23030 (2)	0.07124 (14)
O1	0.34544 (12)	0.8178 (3)	−0.01354 (6)	0.0572 (5)
N1	0.15137 (16)	0.8142 (4)	−0.15404 (8)	0.0650 (6)
N2	0.23320 (14)	0.4402 (3)	−0.10560 (7)	0.0489 (5)
N3	0.35102 (14)	0.4532 (3)	−0.01526 (7)	0.0501 (5)
H3A	0.3313	0.3401	−0.0328	0.060*
N4	0.41296 (14)	0.4300 (3)	0.03159 (7)	0.0470 (5)
C1	0.25220 (16)	0.6348 (4)	−0.08500 (8)	0.0421 (5)
C2	0.21160 (18)	0.8185 (5)	−0.10872 (9)	0.0565 (7)
H2	0.2266	0.9502	−0.0927	0.068*
C3	0.13278 (19)	0.6199 (5)	−0.17444 (10)	0.0620 (8)
H3	0.0911	0.6087	−0.2060	0.074*
C4	0.17254 (18)	0.4358 (5)	−0.15084 (9)	0.0567 (7)
H4	0.1568	0.3041	−0.1668	0.068*
C5	0.32089 (16)	0.6472 (4)	−0.03412 (8)	0.0432 (6)
C6	0.43789 (17)	0.2363 (4)	0.04277 (8)	0.0488 (6)
H6	0.4144	0.1287	0.0195	0.059*
C7	0.50180 (16)	0.1759 (4)	0.09064 (8)	0.0429 (5)
C8	0.52751 (15)	0.3190 (4)	0.13043 (8)	0.0441 (6)
H8	0.5043	0.4593	0.1274	0.053*
C9	0.58834 (16)	0.2486 (4)	0.17454 (8)	0.0457 (6)
C10	0.62372 (18)	0.0415 (4)	0.17990 (10)	0.0557 (7)
H10	0.6649	−0.0027	0.2098	0.067*
C11	0.59711 (19)	−0.0986 (4)	0.14028 (11)	0.0599 (7)
H11	0.6210	−0.2383	0.1434	0.072*
C12	0.53564 (19)	−0.0348 (4)	0.09608 (10)	0.0538 (6)
H12	0.5167	−0.1322	0.0699	0.065*

	U11	U22	U33	U12	U13	U23
Br1	0.0841 (2)	0.0729 (2)	0.04238 (16)	−0.00330 (16)	−0.01146 (13)	−0.00346 (13)
O1	0.0665 (11)	0.0511 (11)	0.0501 (10)	−0.0134 (9)	0.0073 (8)	−0.0144 (8)
N1	0.0630 (15)	0.0746 (17)	0.0523 (13)	0.0077 (13)	0.0045 (11)	0.0107 (12)
N2	0.0511 (11)	0.0532 (13)	0.0392 (10)	−0.0028 (11)	0.0048 (9)	−0.0096 (10)
N3	0.0553 (12)	0.0501 (13)	0.0367 (10)	−0.0022 (11)	−0.0042 (9)	−0.0109 (9)
N4	0.0491 (11)	0.0522 (13)	0.0345 (9)	−0.0025 (10)	0.0004 (8)	−0.0063 (9)
C1	0.0402 (13)	0.0502 (15)	0.0365 (11)	−0.0016 (11)	0.0110 (10)	−0.0043 (10)
C2	0.0604 (16)	0.0557 (17)	0.0519 (14)	0.0006 (14)	0.0110 (12)	−0.0003 (13)
C3	0.0508 (16)	0.089 (2)	0.0411 (13)	−0.0007 (15)	0.0011 (12)	0.0039 (14)
C4	0.0538 (15)	0.0694 (19)	0.0416 (13)	−0.0048 (14)	0.0018 (11)	−0.0103 (13)
C5	0.0432 (13)	0.0496 (15)	0.0375 (12)	−0.0041 (12)	0.0113 (10)	−0.0053 (11)
C6	0.0544 (15)	0.0505 (16)	0.0385 (12)	−0.0080 (13)	0.0058 (10)	−0.0083 (11)
C7	0.0425 (13)	0.0453 (15)	0.0408 (12)	−0.0035 (11)	0.0102 (10)	−0.0001 (10)
C8	0.0458 (13)	0.0422 (14)	0.0412 (12)	−0.0002 (11)	0.0048 (10)	0.0016 (11)
C9	0.0432 (13)	0.0499 (15)	0.0418 (12)	−0.0046 (12)	0.0064 (10)	0.0019 (11)
C10	0.0482 (14)	0.0611 (18)	0.0537 (15)	0.0025 (13)	0.0049 (11)	0.0138 (13)
C11	0.0620 (17)	0.0510 (17)	0.0680 (17)	0.0106 (13)	0.0183 (14)	0.0095 (13)
C12	0.0620 (16)	0.0472 (15)	0.0547 (15)	0.0002 (13)	0.0195 (13)	−0.0038 (12)

Br1—C9	1.901 (2)	C3—H3	0.9300
O1—C5	1.213 (3)	C4—H4	0.9300
N1—C3	1.331 (4)	C6—C7	1.459 (3)
N1—C2	1.334 (3)	C6—H6	0.9300
N2—C4	1.335 (3)	C7—C8	1.390 (3)
N2—C1	1.335 (3)	C7—C12	1.392 (4)
N3—C5	1.341 (3)	C8—C9	1.383 (3)
N3—N4	1.384 (2)	C8—H8	0.9300
N3—H3A	0.8600	C9—C10	1.378 (4)
N4—C6	1.272 (3)	C10—C11	1.376 (4)
C1—C2	1.372 (3)	C10—H10	0.9300
C1—C5	1.506 (3)	C11—C12	1.376 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.369 (4)	C12—H12	0.9300
C3—N1—C2	115.5 (2)	N4—C6—C7	122.6 (2)
C4—N2—C1	115.7 (2)	N4—C6—H6	118.7
C5—N3—N4	121.85 (19)	C7—C6—H6	118.7
C5—N3—H3A	119.1	C8—C7—C12	119.9 (2)
N4—N3—H3A	119.1	C8—C7—C6	122.4 (2)
C6—N4—N3	113.77 (18)	C12—C7—C6	117.7 (2)
N2—C1—C2	122.1 (2)	C9—C8—C7	118.7 (2)
N2—C1—C5	117.5 (2)	C9—C8—H8	120.7
C2—C1—C5	120.4 (2)	C7—C8—H8	120.7
N1—C2—C1	122.1 (3)	C10—C9—C8	121.8 (2)
N1—C2—H2	118.9	C10—C9—Br1	118.40 (18)
C1—C2—H2	118.9	C8—C9—Br1	119.78 (19)
N1—C3—C4	122.7 (2)	C11—C10—C9	118.9 (2)
N1—C3—H3	118.7	C11—C10—H10	120.6
C4—C3—H3	118.7	C9—C10—H10	120.6
N2—C4—C3	121.8 (3)	C10—C11—C12	120.9 (2)
N2—C4—H4	119.1	C10—C11—H11	119.6
C3—C4—H4	119.1	C12—C11—H11	119.6
O1—C5—N3	125.1 (2)	C11—C12—C7	119.9 (2)
O1—C5—C1	121.9 (2)	C11—C12—H12	120.1
N3—C5—C1	113.0 (2)	C7—C12—H12	120.1
C5—N3—N4—C6	−176.9 (2)	C2—C1—C5—N3	177.4 (2)
C4—N2—C1—C2	0.3 (4)	N3—N4—C6—C7	−179.2 (2)
C4—N2—C1—C5	−179.6 (2)	N4—C6—C7—C8	10.8 (4)
C3—N1—C2—C1	0.5 (4)	N4—C6—C7—C12	−170.6 (2)
N2—C1—C2—N1	−0.7 (4)	C12—C7—C8—C9	1.3 (3)
C5—C1—C2—N1	179.2 (2)	C6—C7—C8—C9	179.9 (2)
C2—N1—C3—C4	−0.1 (4)	C7—C8—C9—C10	0.0 (4)
C1—N2—C4—C3	0.1 (4)	C7—C8—C9—Br1	−178.32 (17)
N1—C3—C4—N2	−0.3 (4)	C8—C9—C10—C11	−0.4 (4)
N4—N3—C5—O1	1.9 (4)	Br1—C9—C10—C11	177.9 (2)
N4—N3—C5—C1	−178.7 (2)	C9—C10—C11—C12	−0.5 (4)
N2—C1—C5—O1	176.8 (2)	C10—C11—C12—C7	1.8 (4)
C2—C1—C5—O1	−3.1 (4)	C8—C7—C12—C11	−2.3 (4)
N2—C1—C5—N3	−2.7 (3)	C6—C7—C12—C11	179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2	0.86	2.24	2.646 (3)	109
C6—H6···O1i	0.93	2.26	3.150 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N2	0.86	2.24	2.646 (3)	109
C6—H6⋯O1i	0.93	2.26	3.150 (3)	160

Symmetry code: (i) .