(E)-3-Methyl-N'-(4-nitro-benzyl-idene)benzohydrazide methanol monosolvate.

The title hydrazone compound, C(15)H(13)N(3)O(3)·CH(3)OH, crystallized as a methanol solvate. The hydrazone mol-ecule has an E configuration about the C=N bond and is almost planar, with a dihedral angle between the benzene rings of 5.3 (3)°. In the crystal, the hydrazone mol-ecules are linked via the methanol solvent mol-ecule through N-H⋯O and O-H⋯O hydrogen bonds, so forming chains propagating along the a-axis direction.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶, 2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H13N3O3·CH4O

M = 315.33

Triclinic,

a = 6.581 (2) Å

b = 10.778 (3) Å

c = 11.778 (3) Å

α = 77.945 (2)°

β = 87.524 (2)°

γ = 76.146 (2)°

V = 793.2 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.13 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.988, T max = 0.990

6084 measured reflections

3197 independent reflections

1656 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.142

S = 1.01

3197 reflections

214 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.16 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 datablock(s) global, I. DOI: 10.1107/S1600536812003868/su2372sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003868/su2372Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003868/su2372Isup3.cml

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

C15H13N3O3·CH4O	Z = 2
Mr = 315.33	F(000) = 332
Triclinic, P1	Dx = 1.320 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.581 (2) Å	Cell parameters from 1091 reflections
b = 10.778 (3) Å	θ = 2.4–24.4°
c = 11.778 (3) Å	µ = 0.10 mm−1
α = 77.945 (2)°	T = 298 K
β = 87.524 (2)°	Cut from needle, yellow
γ = 76.146 (2)°	0.13 × 0.10 × 0.10 mm
V = 793.2 (4) Å3

Bruker SMART CCD area-detector diffractometer	3197 independent reflections
Radiation source: fine-focus sealed tube	1656 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.988, Tmax = 0.990	k = −13→13
6084 measured reflections	l = −14→14

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0521P)2 + 0.1129P] where P = (Fo2 + 2Fc2)/3
3197 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.16 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 > 2sigma(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	0.1889 (4)	0.9671 (2)	0.72645 (19)	0.0595 (6)
N2	0.0635 (3)	0.60858 (18)	0.37519 (17)	0.0428 (5)
N3	−0.0125 (3)	0.54614 (19)	0.30155 (17)	0.0429 (5)
O1	0.3766 (4)	0.9541 (2)	0.7382 (2)	0.0971 (8)
O2	0.0567 (4)	1.0440 (2)	0.76810 (18)	0.0821 (7)
O3	0.3165 (3)	0.44974 (17)	0.25767 (16)	0.0646 (6)
O4	0.5393 (3)	0.61678 (18)	0.31310 (17)	0.0612 (5)
H4	0.4607	0.5684	0.3120	0.092*
C1	0.1211 (4)	0.8871 (2)	0.65514 (19)	0.0410 (6)
C2	−0.0872 (4)	0.9129 (2)	0.6271 (2)	0.0458 (6)
H2	−0.1851	0.9761	0.6562	0.055*
C3	−0.1478 (4)	0.8423 (2)	0.55447 (19)	0.0431 (6)
H3A	−0.2884	0.8582	0.5347	0.052*
C4	−0.0020 (4)	0.7481 (2)	0.51068 (19)	0.0377 (6)
C5	0.2076 (4)	0.7219 (2)	0.5439 (2)	0.0468 (6)
H5	0.3062	0.6574	0.5169	0.056*
C6	0.2688 (4)	0.7912 (2)	0.6166 (2)	0.0472 (7)
H6	0.4081	0.7734	0.6394	0.057*
C7	−0.0702 (4)	0.6778 (2)	0.4316 (2)	0.0436 (6)
H7	−0.2122	0.6839	0.4225	0.052*
C8	0.1274 (4)	0.4670 (2)	0.2444 (2)	0.0417 (6)
C9	0.0399 (4)	0.3987 (2)	0.16696 (19)	0.0377 (6)
C10	0.1775 (4)	0.2953 (2)	0.13095 (19)	0.0445 (6)
H10	0.3169	0.2738	0.1544	0.053*
C11	0.1127 (4)	0.2227 (2)	0.0608 (2)	0.0493 (7)
C12	−0.0940 (5)	0.2591 (3)	0.0254 (2)	0.0576 (8)
H12	−0.1409	0.2130	−0.0225	0.069*
C13	−0.2320 (4)	0.3619 (3)	0.0593 (2)	0.0595 (8)
H13	−0.3706	0.3844	0.0343	0.071*
C14	−0.1669 (4)	0.4322 (2)	0.1303 (2)	0.0497 (7)
H14	−0.2612	0.5015	0.1533	0.060*
C15	0.2620 (5)	0.1074 (3)	0.0270 (3)	0.0771 (9)
H15A	0.4032	0.1136	0.0362	0.116*
H15B	0.2378	0.1065	−0.0526	0.116*
H15C	0.2404	0.0284	0.0757	0.116*
C16	0.4510 (5)	0.7410 (3)	0.2475 (3)	0.0846 (10)
H16A	0.3187	0.7760	0.2802	0.127*
H16B	0.4303	0.7347	0.1689	0.127*
H16C	0.5433	0.7976	0.2485	0.127*
H3	−0.1529 (16)	0.558 (3)	0.299 (2)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0752 (19)	0.0521 (15)	0.0576 (15)	−0.0199 (14)	−0.0133 (14)	−0.0169 (12)
N2	0.0393 (12)	0.0414 (12)	0.0558 (13)	−0.0153 (10)	−0.0026 (10)	−0.0204 (10)
N3	0.0328 (12)	0.0458 (12)	0.0584 (13)	−0.0132 (10)	−0.0007 (11)	−0.0247 (11)
O1	0.0775 (17)	0.1043 (18)	0.133 (2)	−0.0269 (14)	−0.0248 (15)	−0.0648 (15)
O2	0.0985 (17)	0.0707 (14)	0.0876 (15)	−0.0095 (13)	−0.0094 (13)	−0.0494 (12)
O3	0.0361 (11)	0.0697 (13)	0.1027 (15)	−0.0120 (9)	−0.0018 (10)	−0.0507 (11)
O4	0.0395 (11)	0.0584 (12)	0.0944 (14)	−0.0167 (9)	−0.0036 (10)	−0.0286 (11)
C1	0.0533 (17)	0.0366 (14)	0.0373 (13)	−0.0173 (13)	−0.0053 (12)	−0.0083 (11)
C2	0.0494 (17)	0.0418 (15)	0.0481 (15)	−0.0072 (13)	0.0028 (12)	−0.0180 (12)
C3	0.0327 (14)	0.0477 (15)	0.0517 (15)	−0.0111 (12)	0.0004 (12)	−0.0146 (13)
C4	0.0355 (15)	0.0381 (13)	0.0429 (14)	−0.0137 (11)	0.0012 (11)	−0.0107 (11)
C5	0.0433 (16)	0.0456 (15)	0.0554 (16)	−0.0094 (12)	0.0018 (13)	−0.0208 (13)
C6	0.0413 (16)	0.0500 (16)	0.0550 (16)	−0.0137 (13)	−0.0076 (12)	−0.0159 (13)
C7	0.0349 (15)	0.0472 (15)	0.0540 (16)	−0.0126 (12)	−0.0011 (12)	−0.0181 (13)
C8	0.0373 (16)	0.0373 (14)	0.0555 (15)	−0.0118 (12)	−0.0010 (12)	−0.0170 (12)
C9	0.0392 (14)	0.0337 (13)	0.0437 (14)	−0.0128 (11)	0.0011 (11)	−0.0107 (11)
C10	0.0421 (16)	0.0465 (15)	0.0494 (15)	−0.0142 (13)	0.0017 (12)	−0.0157 (13)
C11	0.0600 (19)	0.0445 (15)	0.0466 (15)	−0.0124 (14)	0.0022 (13)	−0.0172 (12)
C12	0.070 (2)	0.0539 (17)	0.0579 (17)	−0.0192 (15)	−0.0130 (15)	−0.0235 (14)
C13	0.0524 (18)	0.0615 (18)	0.0689 (18)	−0.0106 (15)	−0.0204 (14)	−0.0220 (15)
C14	0.0467 (17)	0.0447 (15)	0.0605 (17)	−0.0062 (12)	−0.0069 (13)	−0.0209 (13)
C15	0.083 (2)	0.072 (2)	0.085 (2)	−0.0108 (18)	0.0072 (18)	−0.0461 (18)
C16	0.073 (2)	0.080 (2)	0.101 (3)	−0.0284 (19)	−0.0114 (19)	−0.005 (2)

N1—O2	1.214 (3)	C6—H6	0.9300
N1—O1	1.220 (3)	C7—H7	0.9300
N1—C1	1.471 (3)	C8—C9	1.495 (3)
N2—C7	1.271 (3)	C9—C14	1.385 (3)
N2—N3	1.378 (2)	C9—C10	1.387 (3)
N3—C8	1.356 (3)	C10—C11	1.391 (3)
N3—H3	0.902 (10)	C10—H10	0.9300
O3—C8	1.225 (3)	C11—C12	1.380 (3)
O4—C16	1.401 (3)	C11—C15	1.502 (3)
O4—H4	0.8200	C12—C13	1.372 (3)
C1—C2	1.373 (3)	C12—H12	0.9300
C1—C6	1.377 (3)	C13—C14	1.381 (3)
C2—C3	1.385 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.388 (3)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.396 (3)	C15—H15C	0.9600
C4—C7	1.462 (3)	C16—H16A	0.9600
C5—C6	1.376 (3)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
O2—N1—O1	123.5 (2)	N3—C8—C9	116.8 (2)
O2—N1—C1	118.8 (2)	C14—C9—C10	119.1 (2)
O1—N1—C1	117.7 (2)	C14—C9—C8	124.2 (2)
C7—N2—N3	117.05 (19)	C10—C9—C8	116.8 (2)
C8—N3—N2	118.13 (19)	C9—C10—C11	121.8 (2)
C8—N3—H3	125.7 (17)	C9—C10—H10	119.1
N2—N3—H3	116.1 (17)	C11—C10—H10	119.1
C16—O4—H4	109.5	C12—C11—C10	117.6 (2)
C2—C1—C6	122.2 (2)	C12—C11—C15	121.4 (2)
C2—C1—N1	118.7 (2)	C10—C11—C15	121.0 (2)
C6—C1—N1	119.1 (2)	C13—C12—C11	121.4 (2)
C1—C2—C3	118.3 (2)	C13—C12—H12	119.3
C1—C2—H2	120.9	C11—C12—H12	119.3
C3—C2—H2	120.9	C12—C13—C14	120.6 (2)
C2—C3—C4	121.0 (2)	C12—C13—H13	119.7
C2—C3—H3A	119.5	C14—C13—H13	119.7
C4—C3—H3A	119.5	C13—C14—C9	119.5 (2)
C3—C4—C5	119.0 (2)	C13—C14—H14	120.2
C3—C4—C7	119.7 (2)	C9—C14—H14	120.2
C5—C4—C7	121.3 (2)	C11—C15—H15A	109.5
C6—C5—C4	120.3 (2)	C11—C15—H15B	109.5
C6—C5—H5	119.9	H15A—C15—H15B	109.5
C4—C5—H5	119.9	C11—C15—H15C	109.5
C5—C6—C1	119.1 (2)	H15A—C15—H15C	109.5
C5—C6—H6	120.4	H15B—C15—H15C	109.5
C1—C6—H6	120.4	O4—C16—H16A	109.5
N2—C7—C4	120.3 (2)	O4—C16—H16B	109.5
N2—C7—H7	119.8	H16A—C16—H16B	109.5
C4—C7—H7	119.8	O4—C16—H16C	109.5
O3—C8—N3	121.6 (2)	H16A—C16—H16C	109.5
O3—C8—C9	121.5 (2)	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.82	1.98	2.767 (3)	161
N3—H3···O4i	0.90 (1)	1.98 (2)	2.869 (3)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3	0.82	1.98	2.767 (3)	161
N3—H3⋯O4i	0.90 (1)	1.98 (2)	2.869 (3)	167 (3)

Symmetry code: (i) .