N'-(4-Methoxy-benzyl-idene)-4-nitro-benzo-hydrazide methanol solvate.

The title compound, C(15)H(13)N(3)O(4)·CH(4)O, was synthesized from the reaction of 4-methoxy-benzaldehyde with 4-nitro-benzohydrazide in methanol. The benzene rings of the Schiff base mol-ecule are nearly coplanar, making a dihedral angle of 7.0 (3)°. The methanol solvent mol-ecules are linked to the Schiff base mol-ecules by N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds, forming chains running parallel to the b axis.

Related literature

For related structures, see: Brückner et al. (2000 ▶); Diao (2007 ▶); Diao et al. (2007 ▶, 2008 ▶); Harrop et al. (2003 ▶); Huang et al. (2007 ▶); Li et al. (2007 ▶); Ren et al. (2002 ▶).

Experimental

Crystal data

C15H13N3O4·CH4O

M = 331.33

Monoclinic,

a = 14.719 (3) Å

b = 6.631 (2) Å

c = 18.002 (3) Å

β = 113.17 (3)°

V = 1615.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.27 × 0.23 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.973, T max = 0.977

9171 measured reflections

3351 independent reflections

1493 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.172

S = 0.95

3351 reflections

224 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005813/rz2199sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005813/rz2199Isup2.hkl

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

C15H13N3O4·CH4O	F000 = 696
Mr = 331.33	Dx = 1.362 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 670 reflections
a = 14.719 (3) Å	θ = 2.4–24.5º
b = 6.631 (2) Å	µ = 0.10 mm−1
c = 18.002 (3) Å	T = 298 (2) K
β = 113.17 (3)º	Block, yellow
V = 1615.3 (7) Å3	0.27 × 0.23 × 0.23 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3351 independent reflections
Radiation source: fine-focus sealed tube	1493 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.065
T = 298(2) K	θmax = 26.5º
ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −18→18
Tmin = 0.973, Tmax = 0.977	k = −8→7
9171 measured reflections	l = −17→22

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)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.172	w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max < 0.001
3351 reflections	Δρmax = 0.17 e Å−3
224 parameters	Δρmin = −0.17 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0051 (12)

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	0.3893 (2)	0.1141 (5)	0.43054 (18)	0.0628 (8)
N2	0.37993 (17)	0.4842 (3)	0.09474 (14)	0.0480 (6)
N3	0.38196 (16)	0.5979 (3)	0.03071 (14)	0.0481 (6)
O1	0.35466 (19)	−0.0546 (4)	0.41861 (15)	0.0913 (9)
O2	0.4269 (2)	0.1901 (4)	0.49761 (15)	0.0915 (9)
O3	0.38954 (18)	0.7649 (3)	0.16870 (13)	0.0712 (7)
O4	0.37929 (16)	0.8238 (3)	−0.31725 (12)	0.0643 (6)
O5	0.34226 (17)	0.0632 (3)	0.04415 (13)	0.0643 (6)
H5	0.3646	−0.0390	0.0708	0.096*
C1	0.3883 (2)	0.2315 (4)	0.36036 (17)	0.0474 (8)
C2	0.4211 (2)	0.4269 (5)	0.37219 (18)	0.0587 (8)
H2	0.4442	0.4847	0.4234	0.070*
C3	0.4188 (2)	0.5348 (5)	0.30657 (18)	0.0570 (8)
H3	0.4402	0.6680	0.3136	0.068*
C4	0.38535 (19)	0.4503 (4)	0.23005 (16)	0.0433 (7)
C5	0.3527 (2)	0.2511 (4)	0.22030 (18)	0.0500 (8)
H5A	0.3303	0.1916	0.1695	0.060*
C6	0.3537 (2)	0.1412 (4)	0.28616 (18)	0.0520 (8)
H6	0.3311	0.0088	0.2799	0.062*
C7	0.3851 (2)	0.5799 (4)	0.16214 (17)	0.0484 (7)
C8	0.3756 (2)	0.4971 (4)	−0.03121 (18)	0.0492 (7)
H8	0.3686	0.3578	−0.0305	0.059*
C9	0.37877 (19)	0.5910 (4)	−0.10321 (16)	0.0432 (7)
C10	0.3555 (2)	0.4751 (5)	−0.17273 (17)	0.0525 (8)
H10	0.3393	0.3398	−0.1717	0.063*
C11	0.3559 (2)	0.5571 (4)	−0.24324 (18)	0.0535 (8)
H11	0.3389	0.4783	−0.2895	0.064*
C12	0.3818 (2)	0.7574 (4)	−0.24426 (17)	0.0475 (7)
C13	0.4075 (2)	0.8738 (4)	−0.17570 (17)	0.0497 (8)
H13	0.4263	1.0075	−0.1762	0.060*
C14	0.4054 (2)	0.7901 (4)	−0.10576 (17)	0.0495 (8)
H14	0.4221	0.8695	−0.0597	0.059*
C15	0.3969 (2)	1.0303 (5)	−0.3251 (2)	0.0705 (10)
H15A	0.3480	1.1096	−0.3156	0.106*
H15B	0.3933	1.0560	−0.3787	0.106*
H15C	0.4614	1.0657	−0.2864	0.106*
C16	0.2426 (3)	0.0315 (5)	−0.0070 (2)	0.0854 (11)
H16A	0.2053	0.0016	0.0250	0.128*
H16B	0.2380	−0.0796	−0.0425	0.128*
H16C	0.2166	0.1508	−0.0383	0.128*
H2A	0.377 (2)	0.3496 (16)	0.0892 (19)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0707 (18)	0.072 (2)	0.0519 (19)	0.0074 (16)	0.0308 (16)	0.0221 (16)
N2	0.0678 (16)	0.0380 (13)	0.0453 (15)	−0.0013 (12)	0.0298 (13)	0.0086 (12)
N3	0.0634 (15)	0.0436 (14)	0.0426 (15)	0.0012 (12)	0.0266 (13)	0.0089 (12)
O1	0.1079 (19)	0.0897 (19)	0.0742 (18)	−0.0230 (16)	0.0335 (15)	0.0321 (15)
O2	0.137 (2)	0.096 (2)	0.0475 (16)	0.0115 (16)	0.0432 (16)	0.0156 (15)
O3	0.128 (2)	0.0367 (12)	0.0565 (14)	−0.0021 (12)	0.0437 (14)	0.0032 (10)
O4	0.0934 (16)	0.0610 (14)	0.0450 (13)	−0.0019 (12)	0.0342 (12)	0.0065 (11)
O5	0.0883 (16)	0.0432 (13)	0.0554 (15)	−0.0041 (12)	0.0218 (13)	0.0050 (10)
C1	0.0540 (18)	0.0532 (19)	0.0393 (18)	0.0052 (15)	0.0230 (15)	0.0101 (15)
C2	0.081 (2)	0.060 (2)	0.0378 (18)	−0.0057 (18)	0.0263 (16)	−0.0037 (15)
C3	0.080 (2)	0.0474 (18)	0.0464 (19)	−0.0068 (16)	0.0277 (17)	0.0011 (15)
C4	0.0526 (17)	0.0442 (17)	0.0360 (17)	0.0037 (14)	0.0208 (14)	0.0049 (13)
C5	0.0615 (19)	0.0465 (18)	0.0440 (18)	−0.0040 (15)	0.0229 (16)	−0.0025 (14)
C6	0.0664 (19)	0.0466 (18)	0.050 (2)	−0.0042 (15)	0.0306 (16)	0.0039 (15)
C7	0.0634 (19)	0.0404 (18)	0.0434 (18)	−0.0016 (15)	0.0231 (16)	0.0035 (15)
C8	0.0605 (19)	0.0452 (17)	0.0458 (18)	−0.0016 (15)	0.0253 (16)	0.0052 (15)
C9	0.0489 (16)	0.0420 (16)	0.0404 (17)	−0.0004 (14)	0.0194 (14)	0.0058 (13)
C10	0.0657 (19)	0.0420 (17)	0.052 (2)	−0.0042 (14)	0.0247 (16)	−0.0003 (15)
C11	0.072 (2)	0.0487 (19)	0.0405 (18)	−0.0036 (16)	0.0231 (16)	−0.0042 (15)
C12	0.0551 (18)	0.0543 (19)	0.0362 (17)	0.0042 (15)	0.0214 (15)	0.0052 (15)
C13	0.0638 (19)	0.0410 (17)	0.0476 (18)	−0.0050 (14)	0.0254 (16)	0.0036 (14)
C14	0.0620 (19)	0.0472 (19)	0.0417 (18)	−0.0036 (15)	0.0231 (15)	0.0004 (14)
C15	0.087 (2)	0.066 (2)	0.067 (2)	−0.0062 (19)	0.040 (2)	0.0200 (18)
C16	0.092 (3)	0.075 (3)	0.087 (3)	−0.002 (2)	0.032 (2)	0.000 (2)

N1—O1	1.213 (3)	C5—H5A	0.9300
N1—O2	1.222 (3)	C6—H6	0.9300
N1—C1	1.479 (4)	C8—C9	1.455 (4)
N2—C7	1.345 (3)	C8—H8	0.9300
N2—N3	1.388 (3)	C9—C14	1.383 (4)
N2—H2A	0.897 (10)	C9—C10	1.392 (4)
N3—C8	1.271 (3)	C10—C11	1.383 (4)
O3—C7	1.232 (3)	C10—H10	0.9300
O4—C12	1.372 (3)	C11—C12	1.384 (4)
O4—C15	1.411 (3)	C11—H11	0.9300
O5—C16	1.407 (4)	C12—C13	1.376 (4)
O5—H5	0.8200	C13—C14	1.388 (4)
C1—C6	1.366 (4)	C13—H13	0.9300
C1—C2	1.370 (4)	C14—H14	0.9300
C2—C3	1.370 (4)	C15—H15A	0.9600
C2—H2	0.9300	C15—H15B	0.9600
C3—C4	1.386 (4)	C15—H15C	0.9600
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.392 (4)	C16—H16B	0.9600
C4—C7	1.493 (4)	C16—H16C	0.9600
C5—C6	1.387 (4)
O1—N1—O2	123.4 (3)	C9—C8—H8	118.7
O1—N1—C1	118.2 (3)	C14—C9—C10	118.0 (3)
O2—N1—C1	118.4 (3)	C14—C9—C8	123.2 (3)
C7—N2—N3	118.7 (2)	C10—C9—C8	118.8 (3)
C7—N2—H2A	123 (2)	C11—C10—C9	121.3 (3)
N3—N2—H2A	118 (2)	C11—C10—H10	119.3
C8—N3—N2	115.1 (2)	C9—C10—H10	119.3
C12—O4—C15	118.0 (2)	C10—C11—C12	119.3 (3)
C16—O5—H5	109.5	C10—C11—H11	120.3
C6—C1—C2	122.6 (3)	C12—C11—H11	120.3
C6—C1—N1	118.6 (3)	O4—C12—C13	125.0 (3)
C2—C1—N1	118.7 (3)	O4—C12—C11	114.6 (3)
C1—C2—C3	118.2 (3)	C13—C12—C11	120.4 (3)
C1—C2—H2	120.9	C12—C13—C14	119.5 (3)
C3—C2—H2	120.9	C12—C13—H13	120.2
C2—C3—C4	121.6 (3)	C14—C13—H13	120.2
C2—C3—H3	119.2	C9—C14—C13	121.3 (3)
C4—C3—H3	119.2	C9—C14—H14	119.3
C3—C4—C5	118.6 (3)	C13—C14—H14	119.3
C3—C4—C7	117.8 (3)	O4—C15—H15A	109.5
C5—C4—C7	123.6 (3)	O4—C15—H15B	109.5
C6—C5—C4	120.2 (3)	H15A—C15—H15B	109.5
C6—C5—H5A	119.9	O4—C15—H15C	109.5
C4—C5—H5A	119.9	H15A—C15—H15C	109.5
C1—C6—C5	118.7 (3)	H15B—C15—H15C	109.5
C1—C6—H6	120.7	O5—C16—H16A	109.5
C5—C6—H6	120.7	O5—C16—H16B	109.5
O3—C7—N2	122.6 (3)	H16A—C16—H16B	109.5
O3—C7—C4	120.8 (3)	O5—C16—H16C	109.5
N2—C7—C4	116.6 (2)	H16A—C16—H16C	109.5
N3—C8—C9	122.6 (3)	H16B—C16—H16C	109.5
N3—C8—H8	118.7

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5	0.897 (10)	2.049 (13)	2.921 (3)	164 (3)
O5—H5···N3i	0.82	2.56	3.167 (3)	133
O5—H5···O3i	0.82	2.10	2.863 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5	0.897 (10)	2.049 (13)	2.921 (3)	164 (3)
O5—H5⋯N3i	0.82	2.56	3.167 (3)	133
O5—H5⋯O3i	0.82	2.10	2.863 (3)	154

Symmetry code: (i) .