4-Nitro-N'-[(1E,2E)-3-phenyl-prop-2-en-1-yl-idene]benzohydrazide.

In the title mol-ecule, C(16)H(13)N(3)O(3), the benzene and phenyl rings are linked through a propenyl-idene hydrazide fragment, C-C(=O)-N(H)-N=C(H)-C(H)=C(H)-, which is fully extended with torsion angles in the range 175.4 (2)-179.9 (2)°. The dihedral angle between the the benzene and phenyl rings is 58.28 (7)°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains along the b axis and additional stabilization is provided by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the synthesis of related compounds, see: Ahmad et al. (2010 ▶); Küçükgüzel et al. (2007 ▶); Navidpour et al. (2006 ▶); Stocks et al. (2004 ▶). For the biological activity of benzohydrazides, see: Zia-ur-Rehman et al. (2009 ▶); Galal et al. (2009 ▶); Bordoloi et al. (2009 ▶). For a related structure, see: Ji & Shi (2008 ▶). For carbohydrazides, see: Rodríguez-Argüelles et al. (2004 ▶).

Experimental

Crystal data

C16H13N3O3

M = 295.29

Monoclinic,

a = 16.4236 (17) Å

b = 5.3360 (5) Å

c = 17.1073 (18) Å

β = 114.578 (5)°

V = 1363.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 123 K

0.22 × 0.15 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.978, T max = 0.990

7965 measured reflections

2398 independent reflections

2194 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.130

S = 1.31

2398 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); 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, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011864/lh5023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011864/lh5023Isup2.hkl

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

C16H13N3O3	F(000) = 616
Mr = 295.29	Dx = 1.439 Mg m−3
Monoclinic, P21/c	Melting point: 516 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.4236 (17) Å	Cell parameters from 5585 reflections
b = 5.3360 (5) Å	θ = 1.0–30.0°
c = 17.1073 (18) Å	µ = 0.10 mm−1
β = 114.578 (5)°	T = 123 K
V = 1363.4 (2) Å3	Prism, yellow
Z = 4	0.22 × 0.15 × 0.10 mm

Nonius KappaCCD diffractometer	2398 independent reflections
Radiation source: fine-focus sealed tube	2194 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω and φ scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −19→19
Tmin = 0.978, Tmax = 0.990	k = −6→6
7965 measured reflections	l = −20→20

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)] = 0.062	Hydrogen site location: difference Fourier map
wR(F2) = 0.130	H-atom parameters constrained
S = 1.31	w = 1/[σ2(Fo2) + (0.0266P)2 + 1.5943P] where P = (Fo2 + 2Fc2)/3
2398 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.22 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
O1	0.03166 (12)	1.0652 (4)	0.43280 (12)	0.0336 (5)
O2	0.08966 (14)	0.7047 (4)	0.42635 (14)	0.0444 (6)
O3	0.42637 (12)	1.3627 (3)	0.78587 (11)	0.0251 (4)
N1	0.09193 (15)	0.9101 (4)	0.45964 (14)	0.0282 (5)
N2	0.44504 (13)	0.9434 (4)	0.81446 (13)	0.0208 (5)
H2N	0.4231	0.7923	0.7981	0.025*
N3	0.52157 (13)	0.9734 (4)	0.88984 (13)	0.0218 (5)
C1	0.32370 (16)	1.0791 (5)	0.68390 (15)	0.0182 (5)
C2	0.25118 (16)	1.2420 (5)	0.65552 (16)	0.0213 (6)
H2	0.2538	1.3906	0.6871	0.026*
C3	0.17520 (17)	1.1907 (5)	0.58186 (16)	0.0229 (6)
H3	0.1255	1.3019	0.5622	0.028*
C4	0.17367 (16)	0.9725 (5)	0.53757 (15)	0.0211 (6)
C5	0.24504 (16)	0.8084 (5)	0.56339 (16)	0.0221 (6)
H5	0.2423	0.6615	0.5310	0.026*
C6	0.32073 (17)	0.8615 (5)	0.63727 (15)	0.0212 (6)
H6	0.3705	0.7505	0.6562	0.025*
C7	0.40351 (16)	1.1446 (5)	0.76550 (16)	0.0204 (6)
C8	0.54992 (17)	0.7684 (5)	0.93255 (16)	0.0224 (6)
H8	0.5171	0.6176	0.9125	0.027*
C9	0.63111 (17)	0.7669 (5)	1.01056 (16)	0.0224 (6)
H9	0.6635	0.9186	1.0302	0.027*
C10	0.66201 (16)	0.5566 (5)	1.05602 (16)	0.0224 (6)
H10	0.6255	0.4117	1.0365	0.027*
C11	0.74637 (16)	0.5263 (5)	1.13289 (15)	0.0199 (5)
C12	0.81544 (17)	0.7031 (5)	1.15687 (16)	0.0221 (6)
H12	0.8087	0.8480	1.1225	0.027*
C13	0.89376 (17)	0.6686 (5)	1.23042 (16)	0.0242 (6)
H13	0.9399	0.7910	1.2464	0.029*
C14	0.90515 (16)	0.4560 (5)	1.28093 (16)	0.0235 (6)
H14	0.9586	0.4336	1.3315	0.028*
C15	0.83804 (16)	0.2771 (5)	1.25705 (16)	0.0223 (6)
H15	0.8458	0.1306	1.2909	0.027*
C16	0.75935 (16)	0.3118 (5)	1.18347 (15)	0.0199 (5)
H16	0.7138	0.1877	1.1674	0.024*

	U11	U22	U33	U12	U13	U23
O1	0.0222 (10)	0.0422 (12)	0.0276 (10)	0.0033 (9)	0.0016 (8)	0.0063 (9)
O2	0.0420 (13)	0.0311 (12)	0.0397 (12)	−0.0064 (10)	−0.0033 (10)	−0.0095 (10)
O3	0.0251 (10)	0.0190 (10)	0.0251 (10)	−0.0038 (8)	0.0044 (8)	−0.0010 (8)
N1	0.0250 (12)	0.0297 (13)	0.0236 (12)	−0.0064 (11)	0.0038 (10)	0.0034 (10)
N2	0.0172 (10)	0.0185 (11)	0.0199 (11)	−0.0029 (9)	0.0009 (9)	0.0007 (9)
N3	0.0175 (11)	0.0223 (11)	0.0202 (11)	−0.0023 (9)	0.0025 (9)	−0.0020 (9)
C1	0.0183 (12)	0.0175 (12)	0.0183 (12)	−0.0011 (10)	0.0073 (10)	0.0037 (10)
C2	0.0233 (13)	0.0162 (12)	0.0232 (13)	0.0001 (10)	0.0084 (11)	−0.0009 (10)
C3	0.0197 (13)	0.0225 (13)	0.0238 (13)	0.0045 (11)	0.0062 (11)	0.0050 (11)
C4	0.0194 (13)	0.0230 (13)	0.0177 (12)	−0.0033 (11)	0.0045 (10)	0.0041 (10)
C5	0.0245 (14)	0.0199 (13)	0.0204 (13)	−0.0014 (11)	0.0081 (11)	−0.0008 (10)
C6	0.0215 (13)	0.0188 (13)	0.0217 (13)	0.0025 (10)	0.0074 (11)	0.0024 (10)
C7	0.0189 (13)	0.0201 (13)	0.0229 (13)	−0.0010 (10)	0.0093 (11)	−0.0003 (10)
C8	0.0221 (13)	0.0199 (13)	0.0248 (13)	0.0001 (11)	0.0095 (11)	−0.0010 (11)
C9	0.0202 (13)	0.0211 (13)	0.0214 (13)	−0.0027 (11)	0.0041 (10)	−0.0040 (11)
C10	0.0198 (13)	0.0213 (13)	0.0255 (13)	−0.0020 (11)	0.0088 (11)	−0.0034 (11)
C11	0.0190 (13)	0.0211 (13)	0.0199 (12)	0.0013 (10)	0.0083 (10)	−0.0027 (10)
C12	0.0252 (14)	0.0165 (13)	0.0250 (13)	0.0014 (11)	0.0108 (11)	0.0008 (11)
C13	0.0195 (13)	0.0235 (13)	0.0275 (14)	−0.0013 (11)	0.0077 (11)	−0.0021 (11)
C14	0.0182 (13)	0.0265 (14)	0.0217 (13)	0.0052 (11)	0.0043 (10)	−0.0007 (11)
C15	0.0245 (13)	0.0201 (13)	0.0218 (13)	0.0037 (11)	0.0089 (11)	0.0020 (10)
C16	0.0222 (13)	0.0160 (12)	0.0221 (13)	−0.0010 (10)	0.0098 (11)	−0.0016 (10)

O1—N1	1.224 (3)	C6—H6	0.9500
O2—N1	1.228 (3)	C8—C9	1.442 (3)
O3—C7	1.228 (3)	C8—H8	0.9500
N1—C4	1.484 (3)	C9—C10	1.339 (4)
N2—C7	1.358 (3)	C9—H9	0.9500
N2—N3	1.386 (3)	C10—C11	1.470 (3)
N2—H2N	0.8800	C10—H10	0.9500
N3—C8	1.290 (3)	C11—C16	1.397 (3)
C1—C2	1.389 (3)	C11—C12	1.399 (4)
C1—C6	1.398 (3)	C12—C13	1.388 (4)
C1—C7	1.506 (3)	C12—H12	0.9500
C2—C3	1.383 (4)	C13—C14	1.391 (4)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.384 (4)	C14—C15	1.385 (4)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.380 (4)	C15—C16	1.391 (3)
C5—C6	1.384 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
O1—N1—O2	124.5 (2)	N3—C8—C9	120.4 (2)
O1—N1—C4	118.3 (2)	N3—C8—H8	119.8
O2—N1—C4	117.3 (2)	C9—C8—H8	119.8
C7—N2—N3	120.8 (2)	C10—C9—C8	121.6 (2)
C7—N2—H2N	119.6	C10—C9—H9	119.2
N3—N2—H2N	119.6	C8—C9—H9	119.2
C8—N3—N2	113.8 (2)	C9—C10—C11	126.9 (2)
C2—C1—C6	119.9 (2)	C9—C10—H10	116.5
C2—C1—C7	117.9 (2)	C11—C10—H10	116.5
C6—C1—C7	122.2 (2)	C16—C11—C12	118.3 (2)
C3—C2—C1	120.8 (2)	C16—C11—C10	119.3 (2)
C3—C2—H2	119.6	C12—C11—C10	122.4 (2)
C1—C2—H2	119.6	C13—C12—C11	120.6 (2)
C2—C3—C4	118.0 (2)	C13—C12—H12	119.7
C2—C3—H3	121.0	C11—C12—H12	119.7
C4—C3—H3	121.0	C12—C13—C14	120.4 (2)
C5—C4—C3	122.6 (2)	C12—C13—H13	119.8
C5—C4—N1	118.4 (2)	C14—C13—H13	119.8
C3—C4—N1	119.0 (2)	C15—C14—C13	119.6 (2)
C4—C5—C6	118.9 (2)	C15—C14—H14	120.2
C4—C5—H5	120.6	C13—C14—H14	120.2
C6—C5—H5	120.6	C14—C15—C16	120.1 (2)
C5—C6—C1	119.7 (2)	C14—C15—H15	120.0
C5—C6—H6	120.1	C16—C15—H15	120.0
C1—C6—H6	120.1	C15—C16—C11	120.9 (2)
O3—C7—N2	123.9 (2)	C15—C16—H16	119.5
O3—C7—C1	121.9 (2)	C11—C16—H16	119.5
N2—C7—C1	114.1 (2)
C7—N2—N3—C8	175.4 (2)	C2—C1—C7—O3	−33.6 (4)
C6—C1—C2—C3	0.7 (4)	C6—C1—C7—O3	146.9 (3)
C7—C1—C2—C3	−178.9 (2)	C2—C1—C7—N2	144.5 (2)
C1—C2—C3—C4	0.1 (4)	C6—C1—C7—N2	−35.0 (3)
C2—C3—C4—C5	−1.0 (4)	N2—N3—C8—C9	177.3 (2)
C2—C3—C4—N1	178.4 (2)	N3—C8—C9—C10	−179.9 (2)
O1—N1—C4—C5	−174.1 (2)	C8—C9—C10—C11	175.6 (2)
O2—N1—C4—C5	5.8 (3)	C9—C10—C11—C16	165.8 (3)
O1—N1—C4—C3	6.5 (3)	C9—C10—C11—C12	−15.3 (4)
O2—N1—C4—C3	−173.6 (2)	C16—C11—C12—C13	−1.8 (4)
C3—C4—C5—C6	1.1 (4)	C10—C11—C12—C13	179.4 (2)
N1—C4—C5—C6	−178.3 (2)	C11—C12—C13—C14	0.7 (4)
C4—C5—C6—C1	−0.3 (4)	C12—C13—C14—C15	0.5 (4)
C2—C1—C6—C5	−0.6 (4)	C13—C14—C15—C16	−0.7 (4)
C7—C1—C6—C5	178.9 (2)	C14—C15—C16—C11	−0.3 (4)
N3—N2—C7—O3	−4.4 (4)	C12—C11—C16—C15	1.5 (4)
N3—N2—C7—C1	177.5 (2)	C10—C11—C16—C15	−179.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3i	0.88	2.30	3.132 (3)	157
C8—H8···O3i	0.95	2.47	3.296 (3)	146
C14—H14···O1ii	0.95	2.56	3.305 (3)	135
C14—H14···O2iii	0.95	2.54	3.296 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3i	0.88	2.30	3.132 (3)	157
C8—H8⋯O3i	0.95	2.47	3.296 (3)	146
C14—H14⋯O1ii	0.95	2.56	3.305 (3)	135
C14—H14⋯O2iii	0.95	2.54	3.296 (3)	137

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