3-Chloro-N'-(4-hy-droxy-3-nitro-benzyl-idene)benzohydrazide methanol disolvate.

In the title compound, C(14)H(10)ClN(3)O(4)·2CH(4)O, the main mol-ecule is in an E configuration with respect to the methyl-idene unit. The dihedral angle between the mean planes of the two benzene rings is 1.9 (3)°. In the crystal, inter-molecular N-H⋯O, O-H⋯O and bifurcated O-H⋯(O, O) hydrogen bonds link the components into sheets parallel to (100). An intra-molecular O-H⋯O hydrogen bond is also present.

Related literature

For the biological applications of hydrazone compounds, see: Ajani et al. (2010 ▶); Avaji et al. (2009 ▶); Fan et al. (2010 ▶); Rasras et al. (2010 ▶). For related hydrazone structures, see: Zhang (2011a ▶,b ▶); Ahmad et al. (2010 ▶); Ban (2010 ▶); Ji & Lu (2010 ▶); Shalash et al. (2010 ▶).

Experimental

Crystal data

C14H10ClN3O4·2CH4O

M = 383.78

Monoclinic,

a = 7.626 (2) Å

b = 18.846 (5) Å

c = 12.739 (3) Å

β = 94.689 (4)°

V = 1824.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 298 K

0.23 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.945, T max = 0.950

7726 measured reflections

3695 independent reflections

1842 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.208

S = 1.06

3695 reflections

243 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.76 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811021568/lh5265sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021568/lh5265Isup2.hkl

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

C14H10ClN3O4·2CH4O	F(000) = 800
Mr = 383.78	Dx = 1.397 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 954 reflections
a = 7.626 (2) Å	θ = 2.5–24.5°
b = 18.846 (5) Å	µ = 0.25 mm−1
c = 12.739 (3) Å	T = 298 K
β = 94.689 (4)°	Block, yellow
V = 1824.6 (8) Å3	0.23 × 0.23 × 0.21 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3695 independent reflections
Radiation source: fine-focus sealed tube	1842 reflections with I > 2σ(I)
graphite	Rint = 0.048
ω scans	θmax = 26.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.945, Tmax = 0.950	k = −22→23
7726 measured reflections	l = −15→8

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0891P)2] where P = (Fo2 + 2Fc2)/3
3695 reflections	(Δ/σ)max = 0.001
243 parameters	Δρmax = 0.76 e Å−3
1 restraint	Δρmin = −0.26 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
Cl1	1.06078 (17)	−0.35391 (5)	0.03312 (9)	0.0708 (4)
N1	0.4832 (5)	0.32118 (17)	−0.0141 (3)	0.0546 (9)
N2	0.7478 (4)	0.02147 (15)	0.0491 (2)	0.0526 (9)
N3	0.7737 (5)	−0.03895 (16)	−0.0091 (2)	0.0518 (9)
O1	0.4617 (5)	0.37833 (14)	0.0290 (2)	0.0781 (10)
O2	0.4421 (4)	0.31188 (15)	−0.1072 (2)	0.0768 (10)
O3	0.5851 (4)	0.32945 (13)	0.21283 (19)	0.0652 (9)
H3A	0.5220	0.3575	0.1780	0.098*
O4	0.8426 (5)	−0.10265 (14)	0.1374 (2)	0.0773 (10)
O5	0.3664 (4)	0.45501 (16)	0.2154 (2)	0.0744 (9)
H5	0.3000	0.4414	0.2587	0.112*
O6	0.6850 (6)	0.5111 (2)	0.2745 (3)	0.1082 (14)
H6	0.5888	0.4937	0.2563	0.162*
C1	0.6684 (5)	0.14309 (18)	0.0505 (3)	0.0474 (10)
C2	0.5915 (5)	0.19991 (18)	−0.0036 (3)	0.0452 (9)
H2	0.5575	0.1957	−0.0751	0.054*
C3	0.5644 (5)	0.26316 (18)	0.0480 (3)	0.0437 (9)
C4	0.6108 (5)	0.27168 (19)	0.1552 (3)	0.0482 (10)
C5	0.6913 (6)	0.2144 (2)	0.2073 (3)	0.0566 (11)
H5A	0.7265	0.2186	0.2787	0.068*
C6	0.7208 (6)	0.1523 (2)	0.1581 (3)	0.0559 (11)
H6A	0.7765	0.1153	0.1959	0.067*
C7	0.6967 (5)	0.07624 (19)	−0.0032 (3)	0.0530 (10)
H7	0.6772	0.0736	−0.0761	0.064*
C8	0.8224 (5)	−0.09925 (19)	0.0410 (3)	0.0495 (10)
C9	0.8502 (5)	−0.16287 (17)	−0.0252 (3)	0.0402 (9)
C10	0.9332 (5)	−0.22067 (18)	0.0246 (3)	0.0459 (9)
H10	0.9724	−0.2180	0.0956	0.055*
C11	0.9576 (5)	−0.28200 (18)	−0.0311 (3)	0.0452 (9)
C12	0.9009 (5)	−0.2878 (2)	−0.1355 (3)	0.0543 (11)
H12	0.9173	−0.3296	−0.1722	0.065*
C13	0.8189 (6)	−0.2303 (2)	−0.1848 (3)	0.0564 (11)
H13	0.7805	−0.2333	−0.2558	0.068*
C14	0.7929 (5)	−0.16866 (19)	−0.1309 (3)	0.0498 (10)
H14	0.7365	−0.1305	−0.1656	0.060*
H3	0.771 (5)	−0.0374 (19)	−0.0792 (9)	0.060*
C15	0.2719 (8)	0.4968 (2)	0.1385 (4)	0.0930 (17)
H15A	0.2107	0.5338	0.1724	0.139*
H15B	0.1885	0.4676	0.0979	0.139*
H15C	0.3520	0.5175	0.0929	0.139*
C16	0.7983 (9)	0.5025 (3)	0.1930 (5)	0.132 (2)
H16A	0.7729	0.5382	0.1402	0.198*
H16B	0.7808	0.4563	0.1620	0.198*
H16C	0.9183	0.5071	0.2215	0.198*

	U11	U22	U33	U12	U13	U23
Cl1	0.0871 (10)	0.0429 (6)	0.0794 (8)	0.0123 (6)	−0.0122 (6)	0.0061 (5)
N1	0.064 (2)	0.048 (2)	0.051 (2)	0.0092 (17)	0.0017 (17)	0.0028 (16)
N2	0.058 (2)	0.0397 (17)	0.0606 (19)	0.0051 (16)	0.0061 (16)	−0.0027 (15)
N3	0.064 (2)	0.0435 (18)	0.0480 (17)	0.0113 (16)	0.0056 (17)	−0.0019 (15)
O1	0.124 (3)	0.0458 (16)	0.0628 (18)	0.0307 (18)	−0.0022 (18)	−0.0022 (14)
O2	0.104 (3)	0.070 (2)	0.0520 (18)	0.0192 (18)	−0.0196 (17)	−0.0038 (14)
O3	0.095 (3)	0.0486 (16)	0.0492 (15)	0.0114 (16)	−0.0097 (15)	−0.0068 (13)
O4	0.127 (3)	0.0578 (17)	0.0454 (16)	0.0261 (18)	−0.0019 (17)	−0.0041 (13)
O5	0.086 (3)	0.077 (2)	0.0608 (19)	0.0012 (19)	0.0064 (17)	0.0053 (15)
O6	0.140 (4)	0.105 (3)	0.078 (2)	−0.042 (3)	0.000 (2)	−0.014 (2)
C1	0.051 (3)	0.039 (2)	0.052 (2)	0.0008 (19)	0.0063 (19)	0.0016 (17)
C2	0.045 (2)	0.044 (2)	0.047 (2)	−0.0023 (18)	0.0038 (17)	−0.0009 (16)
C3	0.049 (3)	0.0349 (19)	0.047 (2)	0.0026 (18)	0.0043 (18)	0.0056 (15)
C4	0.057 (3)	0.042 (2)	0.044 (2)	−0.0030 (19)	−0.0013 (19)	−0.0009 (17)
C5	0.070 (3)	0.054 (2)	0.043 (2)	0.003 (2)	−0.007 (2)	0.0006 (18)
C6	0.064 (3)	0.047 (2)	0.055 (2)	0.006 (2)	−0.002 (2)	0.0099 (18)
C7	0.060 (3)	0.045 (2)	0.054 (2)	0.001 (2)	0.007 (2)	−0.0011 (18)
C8	0.057 (3)	0.042 (2)	0.049 (2)	0.0069 (19)	0.0000 (19)	−0.0014 (17)
C9	0.039 (2)	0.040 (2)	0.0413 (19)	0.0031 (17)	0.0015 (16)	−0.0003 (15)
C10	0.049 (3)	0.044 (2)	0.044 (2)	0.0033 (19)	0.0000 (18)	−0.0002 (16)
C11	0.044 (2)	0.0346 (19)	0.057 (2)	−0.0009 (17)	0.0000 (18)	0.0045 (16)
C12	0.059 (3)	0.047 (2)	0.056 (2)	0.003 (2)	−0.003 (2)	−0.0118 (18)
C13	0.062 (3)	0.059 (3)	0.047 (2)	0.004 (2)	−0.006 (2)	−0.0042 (19)
C14	0.051 (3)	0.047 (2)	0.050 (2)	0.0079 (19)	−0.0027 (19)	0.0044 (17)
C15	0.113 (5)	0.074 (3)	0.092 (3)	0.034 (3)	0.012 (3)	0.018 (3)
C16	0.136 (6)	0.136 (6)	0.133 (5)	−0.021 (5)	0.061 (5)	−0.028 (5)

Cl1—C11	1.738 (3)	C5—C6	1.355 (5)
N1—O2	1.214 (4)	C5—H5A	0.9300
N1—O1	1.226 (4)	C6—H6A	0.9300
N1—C3	1.458 (4)	C7—H7	0.9300
N2—C7	1.272 (4)	C8—C9	1.491 (5)
N2—N3	1.382 (4)	C9—C14	1.386 (5)
N3—C8	1.341 (4)	C9—C10	1.387 (4)
N3—H3	0.893 (10)	C10—C11	1.377 (5)
O3—C4	1.336 (4)	C10—H10	0.9300
O3—H3A	0.8200	C11—C12	1.369 (5)
O4—C8	1.227 (4)	C12—C13	1.377 (5)
O5—C15	1.409 (5)	C12—H12	0.9300
O5—H5	0.8200	C13—C14	1.371 (5)
O6—C16	1.413 (6)	C13—H13	0.9300
O6—H6	0.8200	C14—H14	0.9300
C1—C2	1.378 (5)	C15—H15A	0.9600
C1—C6	1.406 (5)	C15—H15B	0.9600
C1—C7	1.458 (5)	C15—H15C	0.9600
C2—C3	1.385 (5)	C16—H16A	0.9600
C2—H2	0.9300	C16—H16B	0.9600
C3—C4	1.392 (5)	C16—H16C	0.9600
C4—C5	1.385 (5)
O2—N1—O1	122.1 (3)	O4—C8—C9	120.8 (3)
O2—N1—C3	119.1 (3)	N3—C8—C9	117.4 (3)
O1—N1—C3	118.8 (3)	C14—C9—C10	118.6 (3)
C7—N2—N3	116.0 (3)	C14—C9—C8	124.4 (3)
C8—N3—N2	119.3 (3)	C10—C9—C8	117.0 (3)
C8—N3—H3	119 (2)	C11—C10—C9	119.9 (3)
N2—N3—H3	121 (2)	C11—C10—H10	120.0
C4—O3—H3A	109.5	C9—C10—H10	120.0
C15—O5—H5	109.5	C12—C11—C10	121.5 (3)
C16—O6—H6	109.5	C12—C11—Cl1	119.3 (3)
C2—C1—C6	117.8 (3)	C10—C11—Cl1	119.1 (3)
C2—C1—C7	120.7 (3)	C11—C12—C13	118.4 (3)
C6—C1—C7	121.5 (3)	C11—C12—H12	120.8
C1—C2—C3	120.4 (3)	C13—C12—H12	120.8
C1—C2—H2	119.8	C14—C13—C12	121.2 (4)
C3—C2—H2	119.8	C14—C13—H13	119.4
C2—C3—C4	122.0 (3)	C12—C13—H13	119.4
C2—C3—N1	117.5 (3)	C13—C14—C9	120.4 (3)
C4—C3—N1	120.6 (3)	C13—C14—H14	119.8
O3—C4—C5	116.8 (3)	C9—C14—H14	119.8
O3—C4—C3	126.6 (3)	O5—C15—H15A	109.5
C5—C4—C3	116.6 (3)	O5—C15—H15B	109.5
C6—C5—C4	122.4 (4)	H15A—C15—H15B	109.5
C6—C5—H5A	118.8	O5—C15—H15C	109.5
C4—C5—H5A	118.8	H15A—C15—H15C	109.5
C5—C6—C1	120.9 (3)	H15B—C15—H15C	109.5
C5—C6—H6A	119.6	O6—C16—H16A	109.5
C1—C6—H6A	119.6	O6—C16—H16B	109.5
N2—C7—C1	120.4 (3)	H16A—C16—H16B	109.5
N2—C7—H7	119.8	O6—C16—H16C	109.5
C1—C7—H7	119.8	H16A—C16—H16C	109.5
O4—C8—N3	121.8 (3)	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1	0.82	1.96	2.618 (4)	137
O3—H3A···O5	0.82	2.26	2.896 (4)	135
O6—H6···O5	0.82	1.88	2.700 (5)	179
N3—H3···O6i	0.89 (1)	1.99 (2)	2.834 (4)	158 (4)
O5—H5···O4ii	0.82	1.96	2.779 (4)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1	0.82	1.96	2.618 (4)	137
O3—H3A⋯O5	0.82	2.26	2.896 (4)	135
O6—H6⋯O5	0.82	1.88	2.700 (5)	179
N3—H3⋯O6i	0.89 (1)	1.99 (2)	2.834 (4)	158 (4)
O5—H5⋯O4ii	0.82	1.96	2.779 (4)	173

Symmetry codes: (i) ; (ii) .