(E)-4-Meth-oxy-N'-(4-nitro-benzyl-idene)benzohydrazide methanol monosolvate.

The hydrazone mol-ecule of the title compound, C(15)H(13)N(3)O(4)·CH(4)O, is nearly planar, with a dihedral angle between the two benzene rings of 1.2 (4)°. The mol-ecule exists in a trans configuration with respect to the central methyl-idene unit. In the crystal, the benzohydrazide and methanol mol-ecules are linked through inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related structures, see: Ban & Li (2008a ▶,b ▶); Li & Ban (2009a ▶,b ▶); Yehye et al. (2008 ▶); Fun, Patil, Jebas et al., 2008 ▶; Fun, Patil, Rao et al., 2008 ▶; Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C15H13N3O4·CH4O

M = 331.33

Monoclinic,

a = 6.6482 (14) Å

b = 17.730 (3) Å

c = 13.898 (2) Å

β = 95.004 (3)°

V = 1631.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.20 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.980, T max = 0.983

12876 measured reflections

3466 independent reflections

1184 reflections with I > 2σ(I)

R int = 0.115

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.204

S = 0.94

3466 reflections

222 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004701X/rz2522sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004701X/rz2522Isup2.hkl

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

C15H13N3O4·CH4O	F(000) = 696
Mr = 331.33	Dx = 1.349 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 794 reflections
a = 6.6482 (14) Å	θ = 2.7–26.5°
b = 17.730 (3) Å	µ = 0.10 mm−1
c = 13.898 (2) Å	T = 298 K
β = 95.004 (3)°	Block, colourless
V = 1631.9 (5) Å3	0.20 × 0.17 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3466 independent reflections
Radiation source: fine-focus sealed tube	1184 reflections with I > 2σ(I)
graphite	Rint = 0.115
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −8→8
Tmin = 0.980, Tmax = 0.983	k = −22→22
12876 measured reflections	l = −17→17

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ2(Fo2) + (0.0757P)2] where P = (Fo2 + 2Fc2)/3
3466 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.27 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
N1	0.4536 (7)	−0.3135 (2)	0.1424 (3)	0.0634 (12)
N2	0.1193 (5)	0.0260 (2)	0.1132 (2)	0.0453 (9)
N3	0.0063 (5)	0.0908 (2)	0.1112 (3)	0.0460 (9)
O1	0.3670 (6)	−0.3698 (2)	0.1665 (3)	0.0923 (13)
O2	0.6283 (6)	−0.3132 (2)	0.1217 (3)	0.0930 (13)
O3	0.2843 (4)	0.15868 (16)	0.0864 (2)	0.0650 (10)
O4	−0.3188 (4)	0.43167 (16)	0.0795 (2)	0.0709 (10)
O5	0.5933 (4)	0.05685 (17)	0.1482 (3)	0.0642 (10)
H5	0.4898	0.0767	0.1237	0.096*
C1	0.1378 (6)	−0.1068 (2)	0.1293 (3)	0.0424 (11)
C2	0.3344 (6)	−0.1112 (2)	0.1018 (3)	0.0529 (12)
H2	0.3964	−0.0682	0.0801	0.063*
C3	0.4373 (6)	−0.1786 (3)	0.1064 (3)	0.0549 (13)
H3	0.5680	−0.1817	0.0876	0.066*
C4	0.3437 (7)	−0.2407 (2)	0.1391 (3)	0.0493 (12)
C5	0.1521 (7)	−0.2403 (3)	0.1657 (3)	0.0586 (13)
H5A	0.0922	−0.2840	0.1866	0.070*
C6	0.0480 (6)	−0.1719 (3)	0.1607 (3)	0.0563 (13)
H6	−0.0834	−0.1699	0.1786	0.068*
C7	0.0276 (6)	−0.0354 (3)	0.1262 (3)	0.0495 (12)
H7	−0.1100	−0.0350	0.1338	0.059*
C8	0.1041 (7)	0.1569 (2)	0.0971 (3)	0.0461 (11)
C9	−0.0195 (6)	0.2263 (2)	0.0959 (3)	0.0449 (11)
C10	−0.2157 (6)	0.2311 (2)	0.1201 (3)	0.0508 (12)
H10	−0.2785	0.1877	0.1403	0.061*
C11	−0.3223 (6)	0.2981 (2)	0.1153 (3)	0.0535 (12)
H11	−0.4551	0.2998	0.1314	0.064*
C12	−0.2287 (7)	0.3619 (2)	0.0864 (3)	0.0540 (12)
C13	−0.0345 (7)	0.3593 (3)	0.0605 (4)	0.0829 (18)
H13	0.0277	0.4028	0.0402	0.100*
C14	0.0666 (7)	0.2920 (3)	0.0649 (4)	0.0745 (16)
H14	0.1977	0.2904	0.0465	0.089*
C15	−0.5263 (8)	0.4384 (3)	0.0967 (4)	0.0833 (17)
H15A	−0.6078	0.4115	0.0477	0.125*
H15B	−0.5642	0.4907	0.0951	0.125*
H15C	−0.5467	0.4177	0.1589	0.125*
C16	0.5721 (7)	0.0414 (3)	0.2467 (4)	0.0823 (17)
H16A	0.6181	−0.0089	0.2617	0.123*
H16B	0.4327	0.0459	0.2588	0.123*
H16C	0.6512	0.0767	0.2863	0.123*
H3A	−0.128 (2)	0.087 (2)	0.116 (3)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.077 (3)	0.054 (3)	0.060 (3)	0.021 (3)	0.006 (2)	0.000 (2)
N2	0.041 (2)	0.038 (2)	0.056 (2)	0.0098 (19)	0.0024 (17)	0.0028 (18)
N3	0.030 (2)	0.039 (2)	0.069 (3)	0.0102 (19)	0.0049 (19)	0.0039 (19)
O1	0.117 (3)	0.047 (2)	0.115 (3)	0.022 (2)	0.025 (2)	0.015 (2)
O2	0.078 (3)	0.077 (3)	0.128 (3)	0.043 (2)	0.031 (2)	0.021 (2)
O3	0.0322 (17)	0.053 (2)	0.111 (3)	0.0070 (15)	0.0143 (17)	0.0145 (18)
O4	0.056 (2)	0.0407 (19)	0.115 (3)	0.0141 (17)	−0.0002 (19)	−0.0034 (19)
O5	0.0343 (18)	0.056 (2)	0.102 (3)	0.0096 (16)	0.0027 (17)	0.017 (2)
C1	0.037 (3)	0.040 (3)	0.049 (3)	0.002 (2)	0.004 (2)	0.001 (2)
C2	0.050 (3)	0.036 (3)	0.073 (3)	0.004 (2)	0.013 (2)	0.000 (2)
C3	0.037 (3)	0.050 (3)	0.077 (4)	0.005 (2)	0.006 (2)	0.002 (3)
C4	0.058 (3)	0.042 (3)	0.048 (3)	0.017 (2)	0.003 (2)	0.003 (2)
C5	0.061 (3)	0.044 (3)	0.073 (3)	−0.002 (3)	0.017 (3)	0.008 (2)
C6	0.048 (3)	0.052 (3)	0.070 (4)	0.007 (3)	0.017 (2)	0.002 (3)
C7	0.034 (2)	0.051 (3)	0.063 (3)	0.007 (2)	0.004 (2)	0.002 (2)
C8	0.042 (3)	0.044 (3)	0.053 (3)	0.007 (2)	0.001 (2)	0.009 (2)
C9	0.035 (3)	0.044 (3)	0.056 (3)	0.001 (2)	−0.001 (2)	0.002 (2)
C10	0.052 (3)	0.031 (3)	0.071 (3)	0.003 (2)	0.010 (2)	0.007 (2)
C11	0.049 (3)	0.039 (3)	0.074 (3)	0.008 (2)	0.013 (2)	0.009 (2)
C12	0.059 (3)	0.034 (3)	0.067 (3)	0.013 (2)	−0.005 (3)	0.002 (2)
C13	0.051 (3)	0.047 (3)	0.152 (5)	0.005 (3)	0.020 (3)	0.015 (3)
C14	0.037 (3)	0.057 (3)	0.131 (5)	0.003 (3)	0.012 (3)	0.020 (3)
C15	0.091 (4)	0.057 (3)	0.106 (4)	0.036 (3)	0.029 (3)	0.009 (3)
C16	0.069 (4)	0.082 (4)	0.094 (5)	0.006 (3)	−0.009 (3)	−0.002 (3)

N1—O1	1.214 (4)	C5—H5A	0.9300
N1—O2	1.221 (5)	C6—H6	0.9300
N1—C4	1.482 (5)	C7—H7	0.9300
N2—C7	1.269 (5)	C8—C9	1.479 (5)
N2—N3	1.372 (4)	C9—C10	1.377 (5)
N3—C8	1.363 (5)	C9—C14	1.383 (5)
N3—H3A	0.902 (10)	C10—C11	1.383 (5)
O3—C8	1.221 (4)	C10—H10	0.9300
O4—C12	1.374 (5)	C11—C12	1.367 (5)
O4—C15	1.426 (5)	C11—H11	0.9300
O5—C16	1.415 (5)	C12—C13	1.371 (6)
O5—H5	0.8200	C13—C14	1.369 (6)
C1—C6	1.386 (5)	C13—H13	0.9300
C1—C2	1.395 (5)	C14—H14	0.9300
C1—C7	1.461 (5)	C15—H15A	0.9600
C2—C3	1.376 (5)	C15—H15B	0.9600
C2—H2	0.9300	C15—H15C	0.9600
C3—C4	1.362 (5)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.357 (5)	C16—H16C	0.9600
C5—C6	1.395 (5)
O1—N1—O2	123.5 (4)	N3—C8—C9	116.5 (4)
O1—N1—C4	118.7 (4)	C10—C9—C14	116.8 (4)
O2—N1—C4	117.7 (5)	C10—C9—C8	125.8 (4)
C7—N2—N3	116.9 (3)	C14—C9—C8	117.4 (4)
C8—N3—N2	117.2 (3)	C9—C10—C11	122.2 (4)
C8—N3—H3A	124 (3)	C9—C10—H10	118.9
N2—N3—H3A	119 (3)	C11—C10—H10	118.9
C12—O4—C15	119.1 (4)	C12—C11—C10	118.7 (4)
C16—O5—H5	109.5	C12—C11—H11	120.7
C6—C1—C2	118.6 (4)	C10—C11—H11	120.6
C6—C1—C7	120.1 (4)	C11—C12—C13	120.9 (4)
C2—C1—C7	121.3 (4)	C11—C12—O4	123.9 (4)
C3—C2—C1	120.6 (4)	C13—C12—O4	115.2 (4)
C3—C2—H2	119.7	C14—C13—C12	119.2 (5)
C1—C2—H2	119.7	C14—C13—H13	120.4
C4—C3—C2	118.5 (4)	C12—C13—H13	120.4
C4—C3—H3	120.7	C13—C14—C9	122.2 (4)
C2—C3—H3	120.7	C13—C14—H14	118.9
C5—C4—C3	123.6 (4)	C9—C14—H14	118.9
C5—C4—N1	118.0 (4)	O4—C15—H15A	109.5
C3—C4—N1	118.4 (4)	O4—C15—H15B	109.5
C4—C5—C6	117.7 (4)	H15A—C15—H15B	109.5
C4—C5—H5A	121.2	O4—C15—H15C	109.5
C6—C5—H5A	121.2	H15A—C15—H15C	109.5
C1—C6—C5	120.9 (4)	H15B—C15—H15C	109.5
C1—C6—H6	119.5	O5—C16—H16A	109.5
C5—C6—H6	119.5	O5—C16—H16B	109.5
N2—C7—C1	120.1 (4)	H16A—C16—H16B	109.5
N2—C7—H7	120.0	O5—C16—H16C	109.5
C1—C7—H7	120.0	H16A—C16—H16C	109.5
O3—C8—N3	121.7 (4)	H16B—C16—H16C	109.5
O3—C8—C9	121.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O3	0.82	2.03	2.812 (4)	159
O5—H5···N2	0.82	2.61	3.194 (4)	129
N3—H3A···O5i	0.90 (1)	2.02 (2)	2.900 (4)	166 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O3	0.82	2.03	2.812 (4)	159
O5—H5⋯N2	0.82	2.61	3.194 (4)	129
N3—H3A⋯O5i	0.90 (1)	2.02 (2)	2.900 (4)	166 (4)

Symmetry code: (i) .