N'-(2-Chloro-5-nitro-benzyl-idene)-3-hydroxy-benzohydrazide methanol solvate.

In the title compound, C(14)H(10)ClN(3)O(4)·CH(3)OH, the dihedral angle between the two benzene rings is 33.9 (2)°. In the crystal structure, the methanol solvent mol-ecules are linked to the Schiff base mol-ecules through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds. Mol-ecules are further linked through inter-molecular O-H⋯O and O-H⋯N hydrogen bonds, forming chains running along the b axis.

Related literature

For related structures, see: Zhou & Tang (2007 ▶); Zhou & Xiao (2007 ▶). For related literature, see: Ali et al. (2007 ▶); Butcher et al. (2007 ▶); He (2008 ▶); Jing & Yu (2007 ▶); Nie (2008 ▶).

Experimental

Crystal data

C14H10ClN3O4·CH4O

M = 351.74

Monoclinic,

a = 7.716 (3) Å

b = 11.945 (2) Å

c = 17.650 (3) Å

β = 99.886 (2)°

V = 1602.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 298 (2) K

0.27 × 0.23 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.931, T max = 0.943

12656 measured reflections

3316 independent reflections

2396 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.121

S = 1.01

3316 reflections

223 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536808019636/rz2226sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019636/rz2226Isup2.hkl

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

C14H10ClN3O4·CH4O	F000 = 728
Mr = 351.74	Dx = 1.458 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2947 reflections
a = 7.716 (3) Å	θ = 2.3–24.5º
b = 11.945 (2) Å	µ = 0.27 mm−1
c = 17.650 (3) Å	T = 298 (2) K
β = 99.886 (2)º	Block, colourless
V = 1602.6 (7) Å3	0.27 × 0.23 × 0.22 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3316 independent reflections
Radiation source: fine-focus sealed tube	2396 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.034
T = 298(2) K	θmax = 26.5º
ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.931, Tmax = 0.943	k = −14→14
12656 measured reflections	l = −21→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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.2859P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3316 reflections	Δρmax = 0.18 e Å−3
223 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.27705 (9)	0.68944 (5)	0.42450 (4)	0.0774 (2)
O1	−0.1188 (3)	1.16001 (18)	0.30340 (10)	0.0978 (7)
O2	0.0033 (3)	1.21390 (16)	0.41618 (12)	0.0859 (6)
O3	0.4707 (2)	1.09327 (11)	0.70885 (8)	0.0623 (4)
O4	0.6995 (2)	0.71117 (11)	0.91382 (8)	0.0607 (4)
H4	0.6479	0.6690	0.8808	0.091*
O5	0.6192 (3)	0.69826 (13)	0.66034 (11)	0.0897 (6)
H5	0.5907	0.6645	0.6968	0.135*
N1	−0.0240 (3)	1.14400 (19)	0.36561 (12)	0.0652 (5)
N2	0.3857 (2)	0.95587 (12)	0.58923 (8)	0.0428 (4)
N3	0.4964 (2)	0.92397 (13)	0.65533 (9)	0.0424 (4)
C1	0.2405 (2)	0.90699 (16)	0.46380 (10)	0.0439 (5)
C2	0.1934 (3)	0.82357 (18)	0.40857 (12)	0.0534 (5)
C3	0.0788 (3)	0.8448 (2)	0.34054 (13)	0.0684 (7)
H3	0.0502	0.7880	0.3045	0.082*
C4	0.0082 (3)	0.9485 (2)	0.32639 (12)	0.0663 (7)
H4A	−0.0690	0.9633	0.2810	0.080*
C5	0.0531 (3)	1.03136 (19)	0.38052 (11)	0.0533 (5)
C6	0.1661 (3)	1.01296 (17)	0.44857 (10)	0.0468 (5)
H6	0.1927	1.0705	0.4841	0.056*
C7	0.3601 (3)	0.88397 (16)	0.53602 (11)	0.0460 (5)
H7	0.4179	0.8154	0.5428	0.055*
C8	0.5280 (2)	0.99647 (15)	0.71415 (10)	0.0429 (4)
C9	0.6354 (2)	0.95567 (15)	0.78653 (10)	0.0409 (4)
C10	0.6158 (2)	0.84831 (15)	0.81342 (10)	0.0414 (4)
H10	0.5366	0.7992	0.7849	0.050*
C11	0.7141 (3)	0.81385 (16)	0.88285 (11)	0.0451 (5)
C12	0.8325 (3)	0.88781 (18)	0.92424 (11)	0.0536 (5)
H12	0.9003	0.8652	0.9704	0.064*
C13	0.8499 (3)	0.99430 (19)	0.89738 (12)	0.0591 (6)
H13	0.9295	1.0432	0.9259	0.071*
C14	0.7518 (3)	1.03021 (17)	0.82898 (11)	0.0511 (5)
H14	0.7633	1.1029	0.8116	0.061*
C15	0.6536 (4)	0.6218 (2)	0.60542 (17)	0.0899 (9)
H15A	0.6769	0.6613	0.5609	0.135*
H15B	0.5535	0.5739	0.5911	0.135*
H15C	0.7542	0.5775	0.6263	0.135*
H3B	0.538 (3)	0.862 (2)	0.6593 (14)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0721 (4)	0.0661 (4)	0.0918 (5)	0.0006 (3)	0.0077 (3)	−0.0362 (3)
O1	0.1037 (15)	0.1191 (16)	0.0612 (11)	0.0065 (12)	−0.0124 (10)	0.0357 (11)
O2	0.0977 (14)	0.0643 (11)	0.0857 (13)	0.0020 (10)	−0.0123 (11)	0.0069 (10)
O3	0.0989 (12)	0.0348 (8)	0.0464 (8)	0.0086 (7)	−0.0068 (8)	−0.0028 (6)
O4	0.0881 (12)	0.0414 (8)	0.0441 (8)	−0.0011 (7)	−0.0130 (7)	0.0061 (6)
O5	0.1570 (19)	0.0489 (10)	0.0750 (12)	0.0195 (10)	0.0527 (12)	0.0041 (8)
N1	0.0607 (12)	0.0783 (14)	0.0543 (12)	−0.0043 (10)	0.0038 (10)	0.0231 (11)
N2	0.0519 (10)	0.0387 (8)	0.0355 (8)	−0.0009 (7)	0.0013 (7)	−0.0009 (7)
N3	0.0523 (10)	0.0363 (8)	0.0357 (8)	0.0010 (7)	−0.0005 (7)	−0.0004 (7)
C1	0.0437 (11)	0.0531 (12)	0.0356 (10)	−0.0079 (8)	0.0087 (8)	−0.0059 (8)
C2	0.0507 (12)	0.0624 (13)	0.0489 (12)	−0.0078 (10)	0.0132 (10)	−0.0157 (10)
C3	0.0644 (15)	0.0928 (19)	0.0463 (13)	−0.0128 (14)	0.0050 (11)	−0.0305 (13)
C4	0.0610 (14)	0.097 (2)	0.0378 (11)	−0.0051 (13)	0.0000 (10)	−0.0035 (12)
C5	0.0506 (12)	0.0699 (14)	0.0396 (11)	−0.0102 (10)	0.0080 (9)	0.0053 (10)
C6	0.0508 (11)	0.0549 (12)	0.0343 (10)	−0.0117 (9)	0.0061 (8)	−0.0001 (8)
C7	0.0541 (12)	0.0415 (10)	0.0413 (10)	−0.0005 (9)	0.0054 (9)	−0.0035 (8)
C8	0.0526 (11)	0.0343 (10)	0.0403 (10)	−0.0041 (8)	0.0041 (9)	−0.0002 (8)
C9	0.0476 (11)	0.0382 (10)	0.0359 (9)	−0.0012 (8)	0.0041 (8)	−0.0030 (7)
C10	0.0477 (11)	0.0377 (10)	0.0359 (10)	−0.0013 (8)	−0.0012 (8)	−0.0065 (8)
C11	0.0540 (12)	0.0415 (11)	0.0376 (10)	0.0039 (8)	0.0020 (9)	−0.0016 (8)
C12	0.0553 (13)	0.0621 (13)	0.0379 (10)	−0.0032 (10)	−0.0075 (9)	−0.0019 (9)
C13	0.0626 (14)	0.0634 (14)	0.0462 (12)	−0.0232 (11)	−0.0049 (10)	−0.0094 (10)
C14	0.0627 (13)	0.0434 (11)	0.0449 (11)	−0.0141 (9)	0.0026 (10)	−0.0020 (9)
C15	0.109 (2)	0.0755 (18)	0.095 (2)	0.0083 (16)	0.0456 (18)	−0.0195 (16)

Cl1—C2	1.732 (2)	C4—C5	1.378 (3)
O1—N1	1.225 (2)	C4—H4A	0.9300
O2—N1	1.214 (3)	C5—C6	1.375 (3)
O3—C8	1.236 (2)	C6—H6	0.9300
O4—C11	1.355 (2)	C7—H7	0.9300
O4—H4	0.8200	C8—C9	1.481 (2)
O5—C15	1.390 (3)	C9—C10	1.385 (3)
O5—H5	0.8200	C9—C14	1.389 (3)
N1—C5	1.477 (3)	C10—C11	1.388 (3)
N2—C7	1.263 (2)	C10—H10	0.9300
N2—N3	1.376 (2)	C11—C12	1.385 (3)
N3—C8	1.342 (2)	C12—C13	1.372 (3)
N3—H3B	0.81 (3)	C12—H12	0.9300
C1—C6	1.397 (3)	C13—C14	1.379 (3)
C1—C2	1.398 (3)	C13—H13	0.9300
C1—C7	1.466 (3)	C14—H14	0.9300
C2—C3	1.387 (3)	C15—H15A	0.9600
C3—C4	1.358 (4)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C11—O4—H4	109.5	C1—C7—H7	119.5
C15—O5—H5	109.5	O3—C8—N3	122.02 (17)
O2—N1—O1	123.6 (2)	O3—C8—C9	120.89 (16)
O2—N1—C5	118.83 (18)	N3—C8—C9	117.09 (16)
O1—N1—C5	117.5 (2)	C10—C9—C14	120.50 (17)
C7—N2—N3	115.93 (16)	C10—C9—C8	121.50 (16)
C8—N3—N2	118.75 (15)	C14—C9—C8	117.94 (17)
C8—N3—H3B	120.6 (18)	C9—C10—C11	120.11 (17)
N2—N3—H3B	120.6 (18)	C9—C10—H10	119.9
C6—C1—C2	117.57 (18)	C11—C10—H10	119.9
C6—C1—C7	120.92 (17)	O4—C11—C12	117.23 (17)
C2—C1—C7	121.49 (18)	O4—C11—C10	123.60 (17)
C3—C2—C1	121.6 (2)	C12—C11—C10	119.16 (18)
C3—C2—Cl1	118.32 (17)	C13—C12—C11	120.26 (18)
C1—C2—Cl1	120.09 (16)	C13—C12—H12	119.9
C4—C3—C2	120.1 (2)	C11—C12—H12	119.9
C4—C3—H3	119.9	C12—C13—C14	121.29 (18)
C2—C3—H3	119.9	C12—C13—H13	119.4
C3—C4—C5	118.8 (2)	C14—C13—H13	119.4
C3—C4—H4A	120.6	C13—C14—C9	118.66 (19)
C5—C4—H4A	120.6	C13—C14—H14	120.7
C6—C5—C4	122.5 (2)	C9—C14—H14	120.7
C6—C5—N1	118.48 (19)	O5—C15—H15A	109.5
C4—C5—N1	119.0 (2)	O5—C15—H15B	109.5
C5—C6—C1	119.39 (19)	H15A—C15—H15B	109.5
C5—C6—H6	120.3	O5—C15—H15C	109.5
C1—C6—H6	120.3	H15A—C15—H15C	109.5
N2—C7—C1	120.94 (18)	H15B—C15—H15C	109.5
N2—C7—H7	119.5

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3i	0.82	1.91	2.7237 (19)	169
O4—H4···N2i	0.82	2.62	3.118 (2)	120
O5—H5···O3i	0.82	2.00	2.817 (2)	175
N3—H3B···O5	0.81 (3)	2.05 (3)	2.854 (2)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3i	0.82	1.91	2.7237 (19)	169
O4—H4⋯N2i	0.82	2.62	3.118 (2)	120
O5—H5⋯O3i	0.82	2.00	2.817 (2)	175
N3—H3B⋯O5	0.81 (3)	2.05 (3)	2.854 (2)	173 (3)

Symmetry code: (i) .