N'-(2-Hydr-oxy-5-chloro-benzyl-idene)-4-nitro-benzohydrazide methanol solvate.

The title compound, C(14)H(10)ClN(3)O(4)·CH(4)O, was synthesized from the reaction of 5-chloro-salicylaldehyde with 4-nitro-benzohydrazide in methanol. The Schiff base mol-ecule is nearly planar, with a dihedral angle of 9.1 (3)° between the two benzene rings. 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 a axis.

Related literature

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

Experimental

Crystal data

C14H10ClN3O4·CH4O

M = 351.74

Monoclinic,

a = 6.628 (1) Å

b = 18.980 (3) Å

c = 12.521 (2) Å

β = 91.29 (3)°

V = 1574.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 298 (2) K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.947, T max = 0.955

9258 measured reflections

3259 independent reflections

1776 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.147

S = 1.01

3259 reflections

223 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.29 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/S160053680800843X/ci2574sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800843X/ci2574Isup2.hkl

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

C14H10ClN3O4·CH4O	F000 = 728
Mr = 351.74	Dx = 1.484 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1014 reflections
a = 6.628 (1) Å	θ = 2.5–24.3º
b = 18.980 (3) Å	µ = 0.27 mm−1
c = 12.521 (2) Å	T = 298 (2) K
β = 91.29 (3)º	Block, yellow
V = 1574.7 (4) Å3	0.20 × 0.18 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3259 independent reflections
Radiation source: fine-focus sealed tube	1776 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.056
T = 298(2) K	θmax = 26.5º
ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −8→7
Tmin = 0.947, Tmax = 0.955	k = −22→23
9258 measured reflections	l = −15→15

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0624P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
3259 reflections	Δρmax = 0.23 e Å−3
223 parameters	Δρmin = −0.29 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
Cl1	0.68929 (13)	0.04557 (4)	0.92197 (7)	0.0738 (3)
N1	0.5353 (5)	0.73926 (13)	0.88443 (19)	0.0595 (7)
N2	0.8868 (3)	0.42344 (11)	0.86323 (19)	0.0495 (6)
N3	0.9879 (3)	0.35976 (11)	0.86989 (17)	0.0478 (6)
O1	0.3541 (4)	0.73510 (11)	0.89719 (19)	0.0807 (7)
O2	0.6246 (4)	0.79469 (11)	0.87488 (19)	0.0824 (7)
O3	1.1727 (3)	0.48808 (10)	0.86669 (16)	0.0623 (6)
O4	1.2997 (3)	0.26460 (10)	0.87161 (18)	0.0659 (6)
H4	1.2520	0.3044	0.8735	0.099*
O5	0.4676 (3)	0.40021 (11)	0.80587 (18)	0.0674 (6)
H5	0.3727	0.4232	0.8281	0.101*
C1	0.6514 (4)	0.67373 (13)	0.8806 (2)	0.0470 (7)
C2	0.5546 (4)	0.61164 (14)	0.9009 (2)	0.0548 (8)
H2	0.4187	0.6113	0.9177	0.066*
C3	0.6617 (4)	0.54978 (14)	0.8959 (2)	0.0518 (8)
H3	0.5977	0.5074	0.9108	0.062*
C4	0.8634 (4)	0.54947 (13)	0.8691 (2)	0.0426 (6)
C5	0.9558 (4)	0.61350 (14)	0.8499 (2)	0.0521 (7)
H5A	1.0915	0.6143	0.8327	0.063*
C6	0.8517 (5)	0.67595 (14)	0.8558 (2)	0.0549 (8)
H6	0.9156	0.7187	0.8432	0.066*
C7	0.9882 (4)	0.48478 (14)	0.8649 (2)	0.0443 (6)
C8	0.8723 (4)	0.30647 (14)	0.8789 (2)	0.0488 (7)
H8	0.7338	0.3140	0.8806	0.059*
C9	0.9467 (4)	0.23460 (13)	0.8868 (2)	0.0443 (7)
C10	1.1506 (4)	0.21677 (14)	0.8820 (2)	0.0499 (7)
C11	1.2063 (5)	0.14648 (15)	0.8879 (3)	0.0635 (9)
H11	1.3419	0.1344	0.8842	0.076*
C12	1.0660 (5)	0.09492 (15)	0.8992 (2)	0.0607 (8)
H12	1.1058	0.0480	0.9025	0.073*
C13	0.8651 (4)	0.11224 (14)	0.9058 (2)	0.0503 (7)
C14	0.8072 (4)	0.18097 (14)	0.8996 (2)	0.0497 (7)
H14	0.6711	0.1922	0.9042	0.060*
C15	0.4413 (6)	0.38939 (17)	0.6953 (3)	0.0850 (11)
H15A	0.3767	0.4298	0.6636	0.127*
H15B	0.3587	0.3485	0.6830	0.127*
H15C	0.5704	0.3824	0.6637	0.127*
H2A	0.7515 (16)	0.4223 (17)	0.856 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0638 (6)	0.0528 (5)	0.1047 (7)	−0.0066 (4)	−0.0002 (5)	0.0189 (4)
N1	0.071 (2)	0.0480 (16)	0.0598 (16)	0.0150 (14)	0.0003 (14)	−0.0022 (12)
N2	0.0387 (13)	0.0391 (12)	0.0704 (16)	0.0081 (12)	−0.0020 (12)	0.0003 (11)
N3	0.0466 (15)	0.0393 (13)	0.0575 (15)	0.0082 (11)	−0.0014 (11)	0.0002 (11)
O1	0.0651 (17)	0.0686 (15)	0.1087 (19)	0.0264 (13)	0.0099 (14)	−0.0013 (12)
O2	0.099 (2)	0.0440 (13)	0.1044 (19)	0.0093 (13)	0.0000 (15)	0.0054 (12)
O3	0.0380 (13)	0.0549 (12)	0.0939 (16)	0.0046 (10)	0.0008 (11)	−0.0051 (11)
O4	0.0451 (13)	0.0489 (12)	0.1037 (17)	0.0004 (10)	0.0008 (12)	0.0042 (12)
O5	0.0445 (13)	0.0623 (14)	0.0952 (17)	0.0103 (10)	−0.0024 (11)	−0.0156 (11)
C1	0.053 (2)	0.0405 (15)	0.0476 (16)	0.0108 (13)	−0.0011 (14)	−0.0005 (12)
C2	0.0428 (17)	0.0491 (17)	0.073 (2)	0.0058 (14)	0.0056 (15)	−0.0036 (15)
C3	0.0441 (18)	0.0399 (15)	0.071 (2)	0.0018 (13)	0.0055 (15)	−0.0016 (13)
C4	0.0378 (16)	0.0421 (15)	0.0479 (16)	0.0023 (12)	−0.0013 (12)	−0.0007 (12)
C5	0.0388 (17)	0.0523 (17)	0.0653 (19)	−0.0020 (14)	0.0007 (14)	0.0024 (14)
C6	0.055 (2)	0.0425 (16)	0.067 (2)	−0.0003 (14)	−0.0032 (16)	0.0048 (14)
C7	0.0377 (17)	0.0446 (15)	0.0505 (17)	0.0030 (13)	−0.0018 (13)	−0.0017 (13)
C8	0.0412 (17)	0.0454 (16)	0.0599 (18)	0.0082 (13)	0.0017 (14)	0.0011 (13)
C9	0.0389 (16)	0.0425 (15)	0.0514 (17)	0.0040 (12)	−0.0009 (13)	0.0010 (12)
C10	0.0435 (18)	0.0461 (16)	0.0600 (18)	0.0012 (14)	−0.0002 (14)	0.0021 (14)
C11	0.0441 (18)	0.0485 (17)	0.098 (2)	0.0127 (15)	0.0008 (16)	0.0038 (17)
C12	0.058 (2)	0.0437 (17)	0.080 (2)	0.0052 (15)	−0.0042 (16)	0.0064 (15)
C13	0.0495 (18)	0.0420 (15)	0.0594 (18)	−0.0005 (13)	−0.0024 (14)	0.0065 (13)
C14	0.0379 (17)	0.0496 (16)	0.0616 (18)	0.0062 (13)	0.0014 (13)	0.0011 (14)
C15	0.092 (3)	0.076 (2)	0.087 (3)	0.000 (2)	0.006 (2)	−0.003 (2)

Cl1—C13	1.735 (3)	C4—C5	1.384 (3)
N1—O2	1.215 (3)	C4—C7	1.482 (4)
N1—O1	1.217 (3)	C5—C6	1.374 (4)
N1—C1	1.464 (3)	C5—H5A	0.93
N2—C7	1.344 (3)	C6—H6	0.93
N2—N3	1.384 (3)	C8—C9	1.453 (3)
N2—H2A	0.899 (10)	C8—H8	0.93
N3—C8	1.275 (3)	C9—C14	1.387 (4)
O3—C7	1.225 (3)	C9—C10	1.396 (4)
O4—C10	1.350 (3)	C10—C11	1.386 (4)
O4—H4	0.82	C11—C12	1.360 (4)
O5—C15	1.407 (4)	C11—H11	0.93
O5—H5	0.82	C12—C13	1.375 (4)
C1—C2	1.368 (4)	C12—H12	0.93
C1—C6	1.371 (4)	C13—C14	1.362 (3)
C2—C3	1.374 (3)	C14—H14	0.93
C2—H2	0.93	C15—H15A	0.96
C3—C4	1.386 (4)	C15—H15B	0.96
C3—H3	0.93	C15—H15C	0.96
O2—N1—O1	123.6 (3)	N2—C7—C4	116.0 (2)
O2—N1—C1	118.3 (3)	N3—C8—C9	123.2 (3)
O1—N1—C1	118.0 (3)	N3—C8—H8	118.4
C7—N2—N3	121.0 (2)	C9—C8—H8	118.4
C7—N2—H2A	121 (2)	C14—C9—C10	118.4 (2)
N3—N2—H2A	118 (2)	C14—C9—C8	118.1 (2)
C8—N3—N2	114.0 (2)	C10—C9—C8	123.5 (3)
C10—O4—H4	109.5	O4—C10—C11	117.2 (3)
C15—O5—H5	109.5	O4—C10—C9	123.6 (2)
C2—C1—C6	121.9 (3)	C11—C10—C9	119.2 (3)
C2—C1—N1	118.5 (3)	C12—C11—C10	121.1 (3)
C6—C1—N1	119.6 (3)	C12—C11—H11	119.4
C1—C2—C3	118.9 (3)	C10—C11—H11	119.4
C1—C2—H2	120.6	C11—C12—C13	120.0 (3)
C3—C2—H2	120.6	C11—C12—H12	120.0
C2—C3—C4	121.1 (3)	C13—C12—H12	120.0
C2—C3—H3	119.4	C14—C13—C12	119.8 (3)
C4—C3—H3	119.4	C14—C13—Cl1	121.1 (2)
C5—C4—C3	118.1 (2)	C12—C13—Cl1	119.1 (2)
C5—C4—C7	118.2 (2)	C13—C14—C9	121.5 (3)
C3—C4—C7	123.7 (2)	C13—C14—H14	119.3
C6—C5—C4	121.6 (3)	C9—C14—H14	119.3
C6—C5—H5A	119.2	O5—C15—H15A	109.5
C4—C5—H5A	119.2	O5—C15—H15B	109.5
C1—C6—C5	118.4 (3)	H15A—C15—H15B	109.5
C1—C6—H6	120.8	O5—C15—H15C	109.5
C5—C6—H6	120.8	H15A—C15—H15C	109.5
O3—C7—N2	122.9 (2)	H15B—C15—H15C	109.5
O3—C7—C4	121.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N3	0.82	2.04	2.745 (3)	144
O4—H4···O5i	0.82	2.47	2.930 (3)	116
O5—H5···O3ii	0.82	1.88	2.692 (3)	171
N2—H2A···O5	0.899 (10)	2.016 (13)	2.888 (3)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N3	0.82	2.04	2.745 (3)	144
O4—H4⋯O5i	0.82	2.47	2.930 (3)	116
O5—H5⋯O3ii	0.82	1.88	2.692 (3)	171
N2—H2A⋯O5	0.899 (10)	2.016 (13)	2.888 (3)	163 (3)

Symmetry codes: (i) ; (ii) .