N'-(2-Chloro-5-nitro-benzyl-idene)isonicotinohydrazide.

The title compound, C(13)H(9)ClN(4)O(3), was synthesized by the condensation reaction of 2-chloro-5-nitro-benzaldehyde with isonicotinohydrazide in a methanol solution. The mol-ecule of the compound displays a trans configuration with respect to the C=N and C-N bonds. The dihedral angle between the benzene and pyridine rings is 12.1 (2)°. In the crystal structure, adjacent mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming dimers.

Related literature

For Schiff base compounds, see: Fan et al. (2007 ▶); Kim et al. (2005 ▶); Nimitsiriwat et al. (2004 ▶). For the biological activity of Schiff base compounds, see: Chen et al. (1997 ▶); Ren et al. (2002 ▶). For similar structures, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Yang (2008 ▶); Zhi (2008 ▶); Zhi & Yang (2007 ▶).

Experimental

Crystal data

C13H9ClN4O3

M = 304.69

Tetragonal,

a = 18.586 (3) Å

c = 15.183 (3) Å

V = 5244.9 (15) Å3

Z = 16

Mo Kα radiation

μ = 0.31 mm−1

T = 298 K

0.12 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.964, T max = 0.970

16616 measured reflections

2869 independent reflections

1685 reflections with I > 2σ(I)

R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.131

S = 1.03

2869 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006588/hg2481sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006588/hg2481Isup2.hkl

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

C13H9ClN4O3	Dx = 1.543 Mg m−3
Mr = 304.69	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 1528 reflections
Hall symbol: -I 4ad	θ = 2.2–24.5°
a = 18.586 (3) Å	µ = 0.31 mm−1
c = 15.183 (3) Å	T = 298 K
V = 5244.9 (15) Å3	Block, colorless
Z = 16	0.12 × 0.10 × 0.10 mm
F(000) = 2496

Bruker SMART 1000 CCD area-detector diffractometer	2869 independent reflections
Radiation source: fine-focus sealed tube	1685 reflections with I > 2σ(I)
graphite	Rint = 0.083
ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→22
Tmin = 0.964, Tmax = 0.970	k = −21→23
16616 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0346P)2 + 2.6778P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2869 reflections	Δρmax = 0.17 e Å−3
194 parameters	Δρmin = −0.21 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00084 (18)

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
Cl1	0.14870 (5)	0.28558 (6)	0.06873 (6)	0.0950 (4)
O1	0.24702 (14)	0.38109 (14)	0.46884 (14)	0.0866 (7)
O2	0.17681 (13)	0.29247 (14)	0.49968 (15)	0.0980 (8)
O3	0.36910 (10)	0.56885 (10)	0.18178 (11)	0.0646 (5)
N1	0.29514 (11)	0.44612 (12)	0.16009 (13)	0.0507 (5)
N2	0.33431 (12)	0.47740 (12)	0.09354 (12)	0.0520 (6)
N3	0.50947 (13)	0.62326 (13)	−0.09159 (15)	0.0627 (6)
N4	0.20600 (15)	0.33277 (15)	0.44731 (16)	0.0674 (7)
C1	0.21758 (13)	0.35202 (14)	0.20311 (17)	0.0497 (6)
C2	0.16520 (15)	0.30249 (16)	0.17913 (19)	0.0624 (8)
C3	0.12506 (16)	0.26504 (17)	0.2413 (3)	0.0767 (10)
H3	0.0893	0.2333	0.2231	0.092*
C4	0.13799 (16)	0.27471 (16)	0.3291 (2)	0.0723 (9)
H4	0.1120	0.2494	0.3713	0.087*
C5	0.19049 (14)	0.32300 (14)	0.35332 (18)	0.0540 (7)
C6	0.22899 (13)	0.36163 (14)	0.29285 (16)	0.0505 (6)
H6	0.2632	0.3947	0.3120	0.061*
C7	0.25958 (14)	0.39094 (15)	0.13746 (17)	0.0544 (7)
H7	0.2603	0.3753	0.0793	0.065*
C8	0.37206 (13)	0.53777 (14)	0.11106 (15)	0.0471 (6)
C9	0.41915 (13)	0.56487 (13)	0.03806 (15)	0.0446 (6)
C10	0.41588 (15)	0.54180 (14)	−0.04791 (15)	0.0543 (7)
H10	0.3836	0.5060	−0.0645	0.065*
C11	0.46139 (17)	0.57273 (16)	−0.10915 (17)	0.0643 (8)
H11	0.4580	0.5568	−0.1671	0.077*
C12	0.51235 (15)	0.64389 (16)	−0.00807 (19)	0.0632 (8)
H12	0.5459	0.6789	0.0070	0.076*
C13	0.46919 (15)	0.61719 (15)	0.05767 (17)	0.0588 (7)
H13	0.4737	0.6343	0.1150	0.071*
H2	0.3334 (16)	0.4566 (14)	0.0406 (10)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0684 (6)	0.1253 (8)	0.0914 (6)	0.0108 (5)	−0.0135 (4)	−0.0546 (6)
O1	0.1009 (18)	0.1033 (19)	0.0558 (13)	−0.0094 (15)	−0.0011 (12)	0.0119 (12)
O2	0.1027 (18)	0.1125 (19)	0.0787 (15)	0.0079 (15)	0.0333 (13)	0.0459 (14)
O3	0.0837 (14)	0.0749 (13)	0.0351 (10)	−0.0072 (11)	0.0146 (9)	−0.0096 (9)
N1	0.0517 (13)	0.0618 (14)	0.0385 (11)	0.0045 (11)	0.0075 (10)	0.0043 (10)
N2	0.0645 (14)	0.0606 (15)	0.0308 (11)	0.0020 (12)	0.0090 (10)	−0.0004 (10)
N3	0.0636 (16)	0.0770 (17)	0.0476 (15)	0.0023 (13)	0.0087 (11)	0.0066 (12)
N4	0.0682 (17)	0.0753 (18)	0.0588 (16)	0.0173 (15)	0.0191 (13)	0.0226 (14)
C1	0.0445 (15)	0.0519 (16)	0.0526 (15)	0.0061 (12)	0.0028 (12)	−0.0037 (12)
C2	0.0493 (17)	0.0646 (19)	0.073 (2)	0.0108 (14)	0.0018 (15)	−0.0201 (15)
C3	0.0525 (19)	0.062 (2)	0.116 (3)	−0.0120 (15)	0.0152 (19)	−0.0258 (19)
C4	0.064 (2)	0.0575 (19)	0.095 (3)	−0.0031 (16)	0.0257 (18)	−0.0006 (17)
C5	0.0489 (16)	0.0497 (16)	0.0635 (18)	0.0065 (13)	0.0140 (13)	0.0059 (13)
C6	0.0469 (15)	0.0528 (16)	0.0519 (16)	0.0001 (12)	0.0037 (12)	0.0029 (12)
C7	0.0588 (17)	0.0681 (19)	0.0364 (14)	0.0076 (15)	0.0028 (12)	−0.0043 (13)
C8	0.0546 (16)	0.0541 (16)	0.0325 (13)	0.0091 (13)	0.0035 (11)	0.0015 (11)
C9	0.0470 (15)	0.0507 (15)	0.0359 (13)	0.0129 (12)	0.0034 (11)	0.0023 (11)
C10	0.0679 (18)	0.0570 (16)	0.0378 (14)	−0.0026 (14)	0.0091 (12)	−0.0018 (12)
C11	0.081 (2)	0.074 (2)	0.0377 (15)	0.0014 (18)	0.0124 (14)	−0.0056 (14)
C12	0.0542 (17)	0.078 (2)	0.0572 (18)	−0.0075 (15)	−0.0030 (14)	0.0078 (15)
C13	0.0644 (18)	0.0738 (19)	0.0383 (14)	−0.0027 (15)	−0.0019 (13)	−0.0018 (13)

Cl1—C2	1.733 (3)	C3—H3	0.9300
O1—N4	1.222 (3)	C4—C5	1.376 (4)
O2—N4	1.220 (3)	C4—H4	0.9300
O3—C8	1.221 (3)	C5—C6	1.368 (3)
N1—C7	1.268 (3)	C6—H6	0.9300
N1—N2	1.374 (3)	C7—H7	0.9300
N2—C8	1.350 (3)	C8—C9	1.499 (3)
N2—H2	0.892 (10)	C9—C10	1.375 (3)
N3—C11	1.324 (4)	C9—C13	1.378 (3)
N3—C12	1.326 (3)	C10—C11	1.382 (4)
N4—C5	1.467 (4)	C10—H10	0.9300
C1—C2	1.388 (4)	C11—H11	0.9300
C1—C6	1.391 (3)	C12—C13	1.373 (4)
C1—C7	1.458 (4)	C12—H12	0.9300
C2—C3	1.390 (4)	C13—H13	0.9300
C3—C4	1.367 (4)
C7—N1—N2	114.8 (2)	C5—C6—H6	119.6
C8—N2—N1	118.8 (2)	C1—C6—H6	119.6
C8—N2—H2	123 (2)	N1—C7—C1	119.7 (2)
N1—N2—H2	118 (2)	N1—C7—H7	120.2
C11—N3—C12	115.2 (2)	C1—C7—H7	120.2
O2—N4—O1	123.7 (3)	O3—C8—N2	122.9 (2)
O2—N4—C5	118.1 (3)	O3—C8—C9	121.2 (2)
O1—N4—C5	118.3 (2)	N2—C8—C9	115.9 (2)
C2—C1—C6	116.7 (2)	C10—C9—C13	117.1 (2)
C2—C1—C7	121.7 (3)	C10—C9—C8	124.8 (2)
C6—C1—C7	121.6 (2)	C13—C9—C8	118.1 (2)
C1—C2—C3	122.0 (3)	C9—C10—C11	118.8 (3)
C1—C2—Cl1	119.9 (2)	C9—C10—H10	120.6
C3—C2—Cl1	118.1 (2)	C11—C10—H10	120.6
C4—C3—C2	120.1 (3)	N3—C11—C10	124.9 (3)
C4—C3—H3	119.9	N3—C11—H11	117.5
C2—C3—H3	119.9	C10—C11—H11	117.5
C3—C4—C5	118.1 (3)	N3—C12—C13	124.6 (3)
C3—C4—H4	120.9	N3—C12—H12	117.7
C5—C4—H4	120.9	C13—C12—H12	117.7
C6—C5—C4	122.3 (3)	C12—C13—C9	119.5 (2)
C6—C5—N4	119.0 (3)	C12—C13—H13	120.3
C4—C5—N4	118.7 (3)	C9—C13—H13	120.3
C5—C6—C1	120.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.89 (1)	2.19 (1)	3.055 (3)	164 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.892 (10)	2.187 (13)	3.055 (3)	164 (3)

Symmetry code: (i) .