4-Nitro-N'-[(E)-3-pyridylmethyl-idene]benzohydrazide.

In the title moleclue, C(13)H(10)N(4)O(3), the methyl-idene-hydrazide [-C(=O)-N-N=C-] fragment is essentially planar, with a maximum deviation of 0.0228 (7) Å. The mean planes of the benzene and pyridine rings make dihedral angles of 25.44 (6) and 5.47 (7)°, respectively, with the mean plane of the methyl-idene-hydrazide fragment. In the crystal structure, inter-molecular N-H⋯N hydrogen bonds link mol-ecules into chains along the b axis. Additional stabilization is provided by weak inter-molecular C-H⋯O hydrogen bonds. The O atoms of the nitro group are disordered over two sets of sites of equal occupancy.

Related literature

For the synthesis of related compounds, see: Zia-ur-Rehman et al. (2009 ▶). For the biological activity of benzohydrazides, see: Chakraborty & Patel (1996 ▶). For closely related structures, see: Raj et al. (2008 ▶); Fun et al. (2008 ▶); Wang et al. (2008 ▶); Qiu et al. (2009 ▶).

Experimental

Crystal data

C13H10N4O3

M = 270.25

Monoclinic,

a = 14.6158 (3) Å

b = 8.1969 (2) Å

c = 10.3645 (2) Å

β = 100.609 (1)°

V = 1220.49 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.91 mm−1

T = 123 K

0.20 × 0.16 × 0.05 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.839, T max = 0.956

10114 measured reflections

2192 independent reflections

2098 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 1.06

2192 reflections

190 parameters

66 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011244/lh5020sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011244/lh5020Isup2.hkl

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

C13H10N4O3	F(000) = 560
Mr = 270.25	Dx = 1.471 Mg m−3
Monoclinic, P21/c	Melting point: 547 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 14.6158 (3) Å	Cell parameters from 10114 reflections
b = 8.1969 (2) Å	θ = 3.0–68.0°
c = 10.3645 (2) Å	µ = 0.91 mm−1
β = 100.609 (1)°	T = 123 K
V = 1220.49 (5) Å3	Plate, yellow
Z = 4	0.20 × 0.16 × 0.05 mm

Bruker APEXII diffractometer	2192 independent reflections
Radiation source: fine-focus sealed tube	2098 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω and φ scans	θmax = 68.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −17→17
Tmin = 0.839, Tmax = 0.956	k = −9→9
10114 measured reflections	l = −12→12

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: difference Fourier map
wR(F2) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0485P)2 + 0.519P] where P = (Fo2 + 2Fc2)/3
2192 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.26 e Å−3
66 restraints	Δρmin = −0.26 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)
N1	−0.0353 (11)	0.277 (2)	0.3850 (9)	0.0354 (16)	0.50
O1	−0.086 (3)	0.336 (5)	0.295 (3)	0.059 (3)	0.50
O2	−0.0552 (6)	0.1587 (11)	0.4450 (5)	0.0550 (12)	0.50
N1'	−0.0292 (11)	0.259 (2)	0.4237 (9)	0.0354 (16)	0.50
O1'	−0.082 (3)	0.311 (5)	0.321 (3)	0.059 (3)	0.50
O2'	−0.0525 (6)	0.1572 (11)	0.4997 (5)	0.0550 (12)	0.50
O3	0.36776 (6)	0.53420 (11)	0.67517 (8)	0.0267 (2)
N2	0.37145 (6)	0.60961 (12)	0.46461 (9)	0.0179 (2)
H2N	0.3442	0.6031	0.3817	0.022*
N3	0.45517 (6)	0.69107 (12)	0.49965 (9)	0.0183 (2)
N4	0.66815 (7)	1.02086 (12)	0.31200 (10)	0.0203 (2)
C1	0.23641 (8)	0.46958 (15)	0.51171 (12)	0.0203 (3)
C2	0.17661 (9)	0.52595 (17)	0.40038 (13)	0.0261 (3)
H2	0.1965	0.6096	0.3484	0.031*
C3	0.08809 (9)	0.46038 (19)	0.36515 (14)	0.0329 (3)
H3	0.0466	0.4988	0.2898	0.040*
C4	0.06168 (9)	0.33806 (18)	0.44215 (16)	0.0352 (4)
C5	0.11925 (10)	0.27997 (17)	0.55309 (16)	0.0361 (4)
H5	0.0992	0.1953	0.6040	0.043*
C6	0.20687 (9)	0.34797 (16)	0.58836 (14)	0.0280 (3)
H6	0.2472	0.3114	0.6655	0.034*
C7	0.33183 (8)	0.54003 (14)	0.55923 (11)	0.0189 (3)
C8	0.48376 (8)	0.75796 (14)	0.40288 (11)	0.0182 (3)
H8	0.4490	0.7430	0.3168	0.022*
C9	0.56840 (8)	0.85680 (14)	0.42110 (11)	0.0179 (3)
C10	0.59341 (8)	0.92553 (15)	0.30967 (11)	0.0191 (3)
H10	0.5552	0.9035	0.2270	0.023*
C11	0.72083 (8)	1.05187 (15)	0.42965 (12)	0.0212 (3)
H11	0.7744	1.1186	0.4334	0.025*
C12	0.70067 (8)	0.99095 (15)	0.54626 (12)	0.0219 (3)
H12	0.7395	1.0168	0.6277	0.026*
C13	0.62364 (8)	0.89241 (15)	0.54267 (11)	0.0201 (3)
H13	0.6085	0.8497	0.6213	0.024*

	U11	U22	U33	U12	U13	U23
N1	0.0219 (18)	0.035 (3)	0.051 (5)	−0.0047 (17)	0.010 (4)	−0.013 (4)
O1	0.027 (3)	0.086 (9)	0.059 (8)	−0.015 (4)	−0.004 (5)	−0.022 (6)
O2	0.0311 (8)	0.0435 (8)	0.093 (4)	−0.0147 (6)	0.018 (3)	0.007 (3)
N1'	0.0219 (18)	0.035 (3)	0.051 (5)	−0.0047 (17)	0.010 (4)	−0.013 (4)
O1'	0.027 (3)	0.086 (9)	0.059 (8)	−0.015 (4)	−0.004 (5)	−0.022 (6)
O2'	0.0311 (8)	0.0435 (8)	0.093 (4)	−0.0147 (6)	0.018 (3)	0.007 (3)
O3	0.0277 (5)	0.0329 (5)	0.0186 (4)	−0.0062 (4)	0.0022 (3)	0.0030 (4)
N2	0.0158 (5)	0.0208 (5)	0.0168 (5)	−0.0024 (4)	0.0021 (4)	−0.0006 (4)
N3	0.0156 (5)	0.0187 (5)	0.0205 (5)	−0.0013 (4)	0.0030 (4)	−0.0014 (4)
N4	0.0184 (5)	0.0215 (5)	0.0215 (5)	0.0005 (4)	0.0053 (4)	0.0010 (4)
C1	0.0192 (6)	0.0194 (6)	0.0240 (6)	−0.0001 (4)	0.0080 (5)	−0.0052 (5)
C2	0.0207 (6)	0.0318 (7)	0.0263 (6)	−0.0023 (5)	0.0058 (5)	−0.0034 (5)
C3	0.0207 (6)	0.0429 (8)	0.0345 (7)	−0.0011 (6)	0.0032 (5)	−0.0121 (6)
C4	0.0184 (6)	0.0315 (7)	0.0579 (9)	−0.0057 (5)	0.0130 (6)	−0.0211 (7)
C5	0.0293 (7)	0.0217 (7)	0.0631 (10)	−0.0037 (5)	0.0234 (7)	−0.0006 (7)
C6	0.0252 (6)	0.0227 (6)	0.0387 (7)	0.0003 (5)	0.0126 (5)	0.0015 (6)
C7	0.0197 (6)	0.0167 (6)	0.0206 (6)	0.0005 (4)	0.0045 (4)	−0.0013 (5)
C8	0.0178 (5)	0.0181 (6)	0.0182 (5)	0.0010 (4)	0.0021 (4)	−0.0005 (4)
C9	0.0170 (6)	0.0163 (6)	0.0206 (6)	0.0023 (4)	0.0040 (4)	−0.0012 (4)
C10	0.0180 (6)	0.0196 (6)	0.0193 (6)	0.0012 (4)	0.0024 (4)	−0.0013 (5)
C11	0.0161 (5)	0.0207 (6)	0.0271 (6)	−0.0016 (4)	0.0045 (5)	−0.0013 (5)
C12	0.0198 (6)	0.0235 (6)	0.0212 (6)	−0.0003 (5)	0.0008 (5)	−0.0029 (5)
C13	0.0208 (6)	0.0210 (6)	0.0191 (6)	0.0016 (5)	0.0050 (5)	0.0004 (5)

N1—O1	1.19 (3)	C2—H2	0.9500
N1—O2	1.213 (16)	C3—C4	1.380 (2)
N1—C4	1.518 (16)	C3—H3	0.9500
N1'—O2'	1.236 (15)	C4—C5	1.379 (2)
N1'—O1'	1.27 (2)	C5—C6	1.383 (2)
N1'—C4	1.460 (17)	C5—H5	0.9500
O3—C7	1.2205 (15)	C6—H6	0.9500
N2—C7	1.3532 (15)	C8—C9	1.4617 (16)
N2—N3	1.3826 (13)	C8—H8	0.9500
N2—H2N	0.8800	C9—C10	1.3929 (16)
N3—C8	1.2788 (15)	C9—C13	1.3964 (16)
N4—C10	1.3397 (16)	C10—H10	0.9500
N4—C11	1.3411 (16)	C11—C12	1.3886 (17)
C1—C6	1.3919 (18)	C11—H11	0.9500
C1—C2	1.3920 (18)	C12—C13	1.3806 (17)
C1—C7	1.5061 (16)	C12—H12	0.9500
C2—C3	1.3865 (18)	C13—H13	0.9500
O1—N1—O2	124 (2)	C4—C5—H5	120.8
O1—N1—C4	125 (2)	C6—C5—H5	120.8
O2—N1—C4	111.0 (8)	C5—C6—C1	120.48 (13)
O2'—N1'—O1'	125 (2)	C5—C6—H6	119.8
O2'—N1'—C4	124.5 (9)	C1—C6—H6	119.8
O1'—N1'—C4	111 (2)	O3—C7—N2	124.48 (11)
C7—N2—N3	119.29 (9)	O3—C7—C1	120.77 (11)
C7—N2—H2N	120.4	N2—C7—C1	114.75 (10)
N3—N2—H2N	120.4	N3—C8—C9	121.82 (10)
C8—N3—N2	113.72 (9)	N3—C8—H8	119.1
C10—N4—C11	117.17 (10)	C9—C8—H8	119.1
C6—C1—C2	119.84 (12)	C10—C9—C13	117.86 (11)
C6—C1—C7	116.99 (11)	C10—C9—C8	117.52 (10)
C2—C1—C7	123.10 (11)	C13—C9—C8	124.57 (11)
C3—C2—C1	120.18 (13)	N4—C10—C9	123.95 (11)
C3—C2—H2	119.9	N4—C10—H10	118.0
C1—C2—H2	119.9	C9—C10—H10	118.0
C4—C3—C2	118.43 (14)	N4—C11—C12	123.02 (11)
C4—C3—H3	120.8	N4—C11—H11	118.5
C2—C3—H3	120.8	C12—C11—H11	118.5
C5—C4—C3	122.72 (12)	C13—C12—C11	119.31 (11)
C5—C4—N1'	110.9 (4)	C13—C12—H12	120.3
C3—C4—N1'	126.3 (4)	C11—C12—H12	120.3
C5—C4—N1	126.4 (4)	C12—C13—C9	118.67 (11)
C3—C4—N1	110.8 (4)	C12—C13—H13	120.7
C4—C5—C6	118.33 (13)	C9—C13—H13	120.7
C7—N2—N3—C8	−177.02 (10)	N1—C4—C5—C6	178.1 (7)
C6—C1—C2—C3	−0.52 (19)	C4—C5—C6—C1	−1.3 (2)
C7—C1—C2—C3	−177.23 (11)	C2—C1—C6—C5	1.50 (19)
C1—C2—C3—C4	−0.57 (19)	C7—C1—C6—C5	178.40 (11)
C2—C3—C4—C5	0.7 (2)	N3—N2—C7—O3	−5.01 (17)
C2—C3—C4—N1'	177.6 (8)	N3—N2—C7—C1	174.08 (9)
C2—C3—C4—N1	−177.4 (6)	C6—C1—C7—O3	−23.95 (17)
O2'—N1'—C4—C5	2.3 (16)	C2—C1—C7—O3	152.85 (12)
O1'—N1'—C4—C5	−180 (2)	C6—C1—C7—N2	156.92 (11)
O2'—N1'—C4—C3	−174.9 (10)	C2—C1—C7—N2	−26.28 (17)
O1'—N1'—C4—C3	3(3)	N2—N3—C8—C9	176.74 (10)
O2'—N1'—C4—N1	168 (6)	N3—C8—C9—C10	−179.54 (11)
O1'—N1'—C4—N1	−14 (4)	N3—C8—C9—C13	−2.28 (18)
O1—N1—C4—C5	174 (3)	C11—N4—C10—C9	−0.60 (17)
O2—N1—C4—C5	−4.7 (15)	C13—C9—C10—N4	1.38 (18)
O1—N1—C4—C3	−8(3)	C8—C9—C10—N4	178.82 (10)
O2—N1—C4—C3	173.3 (9)	C10—N4—C11—C12	−0.44 (17)
O1—N1—C4—N1'	158 (7)	N4—C11—C12—C13	0.65 (18)
O2—N1—C4—N1'	−21 (4)	C11—C12—C13—C9	0.17 (18)
C3—C4—C5—C6	0.2 (2)	C10—C9—C13—C12	−1.11 (17)
N1'—C4—C5—C6	−177.1 (7)	C8—C9—C13—C12	−178.35 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N4i	0.88	2.09	2.9108 (14)	154
C3—H3···O1	0.95	2.37	2.72 (4)	101
C5—H5···O2'	0.95	2.30	2.666 (8)	102
C8—H8···O3ii	0.95	2.50	3.1423 (14)	125
C11—H11···O2iii	0.95	2.49	3.364 (8)	152
C11—H11···O2'iii	0.95	2.52	3.371 (8)	150
C13—H13···O3iv	0.95	2.57	3.1279 (14)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯N4i	0.88	2.09	2.9108 (14)	154
C8—H8⋯O3ii	0.95	2.50	3.1423 (14)	125
C11—H11⋯O2iii	0.95	2.49	3.364 (8)	152
C11—H11⋯O2′iii	0.95	2.52	3.371 (8)	150
C13—H13⋯O3iv	0.95	2.57	3.1279 (14)	118

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