4-Chloro-N'-[(Z)-4-nitro-benzyl-idene]benzohydrazide monohydrate.

In the title compound, C(14)H(10)ClN(3)O(3)·H(2)O, the benzohydrazide group is not planar and the mol-ecule exists in a cis configuration with respect to the methyl-idene unit. The dihedral angle between the two substituted benzene rings is 38.7 (3)°. In the crystal structure, mol-ecules are linked by O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds into a two-dimensional network parallel to the (100) plane. The crystal structure is further stabilized by weak C-H⋯O inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to the activities of hydrazones, see, for example: Bedia et al. (2006 ▶); Rollas & Kouçoukgouzel (2007 ▶).

Experimental

Crystal data

C14H10ClN3O3·H2O

M = 321.72

Monoclinic,

a = 16.3049 (8) Å

b = 6.8783 (4) Å

c = 12.7209 (7) Å

β = 104.122 (4)°

V = 1383.53 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 100.0 (1) K

0.38 × 0.21 × 0.10 mm

Data collection

Bruker SMART APEX2 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.896, T max = 0.971

14031 measured reflections

3172 independent reflections

2558 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.239

S = 1.13

3172 reflections

199 parameters

H-atom parameters constrained

Δρmax = 1.40 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802446X/hb2764sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802446X/hb2764Isup2.hkl

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

C14H10ClN3O3·H2O	F000 = 664
Mr = 321.72	Dx = 1.545 Mg m−3
Monoclinic, P21/c	Melting point: 488 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 16.3049 (8) Å	Cell parameters from 3172 reflections
b = 6.8783 (4) Å	θ = 1.3–27.5º
c = 12.7209 (7) Å	µ = 0.30 mm−1
β = 104.122 (4)º	T = 100.0 (1) K
V = 1383.53 (13) Å3	Needle, colorless
Z = 4	0.38 × 0.21 × 0.10 mm

Bruker SMART APEX2 CCD diffractometer	3172 independent reflections
Radiation source: fine-focus sealed tube	2558 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.044
Detector resolution: 8.33 pixels mm-1	θmax = 27.5º
T = 100.0(1) K	θmin = 1.3º
ω scans	h = −21→21
Absorption correction: Multi-scan(SADABS; Bruker, 2005)	k = −7→8
Tmin = 0.896, Tmax = 0.971	l = −16→16
14031 measured reflections

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)] = 0.086	H-atom parameters constrained
wR(F2) = 0.239	w = 1/[σ2(Fo2) + (0.0417P)2 + 15.1986P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
3172 reflections	Δρmax = 1.40 e Å−3
199 parameters	Δρmin = −0.46 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.79974 (8)	0.8946 (2)	0.59885 (10)	0.0211 (3)
O1	−0.0852 (2)	0.7494 (7)	−0.1492 (3)	0.0312 (10)
O2	−0.0194 (2)	0.9231 (7)	−0.2447 (3)	0.0306 (10)
O3	0.5057 (2)	0.8432 (6)	0.1303 (3)	0.0167 (8)
N1	0.4189 (2)	0.8116 (6)	0.2433 (3)	0.0146 (8)
H1N1	0.4111	0.7946	0.3065	0.017*
N2	0.3494 (3)	0.8265 (6)	0.1565 (3)	0.0154 (9)
N3	−0.0222 (3)	0.8347 (7)	−0.1617 (3)	0.0196 (9)
C1	0.6514 (3)	0.8141 (8)	0.3030 (4)	0.0172 (10)
H1A	0.6578	0.7885	0.2336	0.021*
C2	0.7224 (3)	0.8303 (8)	0.3878 (4)	0.0184 (10)
H2A	0.7761	0.8149	0.3762	0.022*
C3	0.7118 (3)	0.8698 (8)	0.4901 (4)	0.0173 (10)
C4	0.6319 (3)	0.8910 (8)	0.5090 (4)	0.0173 (10)
H4A	0.6259	0.9173	0.5785	0.021*
C5	0.5614 (3)	0.8724 (8)	0.4236 (4)	0.0153 (10)
H5A	0.5077	0.8847	0.4359	0.018*
C6	0.5702 (3)	0.8354 (7)	0.3196 (4)	0.0143 (10)
C7	0.4969 (3)	0.8287 (7)	0.2234 (4)	0.0141 (9)
C8	0.2778 (3)	0.7923 (8)	0.1770 (4)	0.0166 (10)
H8A	0.2749	0.7564	0.2465	0.020*
C9	0.2003 (3)	0.8100 (8)	0.0902 (4)	0.0152 (10)
C10	0.1241 (3)	0.7367 (8)	0.1067 (4)	0.0181 (11)
H10A	0.1230	0.6841	0.1737	0.022*
C11	0.0507 (3)	0.7417 (8)	0.0248 (4)	0.0193 (11)
H11A	0.0005	0.6890	0.0346	0.023*
C12	0.0543 (3)	0.8281 (8)	−0.0724 (4)	0.0171 (10)
C13	0.1275 (3)	0.9111 (8)	−0.0900 (4)	0.0165 (10)
H13A	0.1272	0.9735	−0.1549	0.020*
C14	0.2009 (3)	0.8985 (8)	−0.0080 (4)	0.0168 (10)
H14A	0.2510	0.9496	−0.0187	0.020*
O1W	0.3845 (2)	0.6173 (6)	0.4228 (3)	0.0196 (8)
H1W	0.4181	0.5223	0.4141	0.029*
H2W	0.3862	0.6256	0.4931	0.029*

	U11	U22	U33	U12	U13	U23
Cl1	0.0164 (6)	0.0226 (7)	0.0194 (6)	−0.0002 (5)	−0.0049 (4)	−0.0009 (5)
O1	0.0116 (17)	0.049 (3)	0.032 (2)	−0.0057 (18)	0.0034 (15)	0.003 (2)
O2	0.022 (2)	0.046 (3)	0.0199 (19)	−0.0012 (19)	−0.0013 (15)	0.0072 (19)
O3	0.0168 (16)	0.023 (2)	0.0106 (15)	−0.0028 (15)	0.0035 (12)	−0.0020 (14)
N1	0.0144 (19)	0.019 (2)	0.0097 (17)	−0.0017 (17)	0.0010 (14)	−0.0001 (17)
N2	0.0141 (19)	0.015 (2)	0.0153 (19)	−0.0017 (16)	−0.0010 (15)	−0.0012 (17)
N3	0.0113 (19)	0.027 (3)	0.019 (2)	0.0000 (18)	0.0008 (16)	0.0010 (19)
C1	0.020 (2)	0.018 (3)	0.015 (2)	0.001 (2)	0.0050 (18)	0.000 (2)
C2	0.014 (2)	0.019 (3)	0.022 (2)	0.001 (2)	0.0038 (19)	0.000 (2)
C3	0.016 (2)	0.015 (3)	0.017 (2)	−0.0024 (19)	−0.0034 (18)	0.002 (2)
C4	0.020 (2)	0.018 (3)	0.013 (2)	−0.001 (2)	0.0028 (18)	−0.001 (2)
C5	0.016 (2)	0.016 (2)	0.015 (2)	0.0005 (19)	0.0049 (17)	−0.0023 (19)
C6	0.015 (2)	0.011 (2)	0.016 (2)	−0.0011 (18)	0.0024 (17)	−0.0006 (19)
C7	0.013 (2)	0.011 (2)	0.018 (2)	0.0008 (18)	0.0025 (18)	−0.0003 (19)
C8	0.018 (2)	0.019 (3)	0.012 (2)	0.000 (2)	0.0015 (18)	0.000 (2)
C9	0.013 (2)	0.016 (2)	0.015 (2)	−0.0001 (19)	0.0026 (17)	−0.001 (2)
C10	0.017 (2)	0.023 (3)	0.015 (2)	0.000 (2)	0.0055 (18)	0.005 (2)
C11	0.014 (2)	0.022 (3)	0.022 (2)	−0.001 (2)	0.0044 (19)	0.003 (2)
C12	0.013 (2)	0.022 (3)	0.015 (2)	0.003 (2)	0.0000 (17)	0.001 (2)
C13	0.015 (2)	0.019 (3)	0.014 (2)	−0.001 (2)	0.0030 (18)	0.000 (2)
C14	0.013 (2)	0.019 (3)	0.018 (2)	0.0011 (19)	0.0031 (18)	−0.001 (2)
O1W	0.0201 (17)	0.028 (2)	0.0111 (15)	0.0008 (16)	0.0047 (13)	−0.0007 (15)

Cl1—C3	1.741 (5)	C5—C6	1.389 (7)
O1—N3	1.226 (6)	C5—H5A	0.9300
O2—N3	1.228 (6)	C6—C7	1.488 (6)
O3—C7	1.232 (6)	C8—C9	1.466 (6)
N1—C7	1.361 (6)	C8—H8A	0.9300
N1—N2	1.379 (5)	C9—C14	1.391 (7)
N1—H1N1	0.8525	C9—C10	1.404 (7)
N2—C8	1.279 (6)	C10—C11	1.383 (7)
N3—C12	1.469 (6)	C10—H10A	0.9300
C1—C2	1.380 (7)	C11—C12	1.387 (7)
C1—C6	1.399 (7)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.390 (7)
C2—C3	1.382 (7)	C13—C14	1.384 (7)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.388 (7)	C14—H14A	0.9300
C4—C5	1.381 (6)	O1W—H1W	0.8771
C4—H4A	0.9300	O1W—H2W	0.8898
C7—N1—N2	117.9 (4)	O3—C7—N1	121.2 (4)
C7—N1—H1N1	123.2	O3—C7—C6	122.0 (4)
N2—N1—H1N1	118.9	N1—C7—C6	116.8 (4)
C8—N2—N1	115.9 (4)	N2—C8—C9	119.6 (4)
O1—N3—O2	123.8 (4)	N2—C8—H8A	120.2
O1—N3—C12	117.7 (4)	C9—C8—H8A	120.2
O2—N3—C12	118.5 (4)	C14—C9—C10	119.4 (4)
C2—C1—C6	121.2 (5)	C14—C9—C8	121.3 (4)
C2—C1—H1A	119.4	C10—C9—C8	119.3 (4)
C6—C1—H1A	119.4	C11—C10—C9	120.9 (5)
C1—C2—C3	118.6 (5)	C11—C10—H10A	119.6
C1—C2—H2A	120.7	C9—C10—H10A	119.6
C3—C2—H2A	120.7	C10—C11—C12	117.7 (5)
C2—C3—C4	121.4 (4)	C10—C11—H11A	121.1
C2—C3—Cl1	120.0 (4)	C12—C11—H11A	121.1
C4—C3—Cl1	118.6 (4)	C11—C12—C13	123.0 (4)
C5—C4—C3	119.3 (5)	C11—C12—N3	119.3 (4)
C5—C4—H4A	120.3	C13—C12—N3	117.7 (4)
C3—C4—H4A	120.3	C14—C13—C12	118.1 (5)
C4—C5—C6	120.4 (5)	C14—C13—H13A	120.9
C4—C5—H5A	119.8	C12—C13—H13A	120.9
C6—C5—H5A	119.8	C13—C14—C9	120.6 (5)
C5—C6—C1	119.0 (4)	C13—C14—H14A	119.7
C5—C6—C7	122.7 (4)	C9—C14—H14A	119.7
C1—C6—C7	118.2 (4)	H1W—O1W—H2W	107.9
C7—N1—N2—C8	174.0 (5)	N1—N2—C8—C9	178.3 (4)
C6—C1—C2—C3	−0.5 (8)	N2—C8—C9—C14	−12.5 (8)
C1—C2—C3—C4	0.8 (8)	N2—C8—C9—C10	167.7 (5)
C1—C2—C3—Cl1	−179.2 (4)	C14—C9—C10—C11	3.6 (8)
C2—C3—C4—C5	−0.1 (8)	C8—C9—C10—C11	−176.7 (5)
Cl1—C3—C4—C5	179.8 (4)	C9—C10—C11—C12	−2.4 (8)
C3—C4—C5—C6	−0.8 (8)	C10—C11—C12—C13	−1.0 (8)
C4—C5—C6—C1	1.1 (8)	C10—C11—C12—N3	179.5 (5)
C4—C5—C6—C7	−175.3 (5)	O1—N3—C12—C11	−5.5 (8)
C2—C1—C6—C5	−0.4 (8)	O2—N3—C12—C11	175.2 (5)
C2—C1—C6—C7	176.2 (5)	O1—N3—C12—C13	174.9 (5)
N2—N1—C7—O3	−5.1 (7)	O2—N3—C12—C13	−4.4 (8)
N2—N1—C7—C6	173.0 (4)	C11—C12—C13—C14	3.1 (8)
C5—C6—C7—O3	162.0 (5)	N3—C12—C13—C14	−177.3 (5)
C1—C6—C7—O3	−14.4 (8)	C12—C13—C14—C9	−1.9 (8)
C5—C6—C7—N1	−16.1 (7)	C10—C9—C14—C13	−1.3 (8)
C1—C6—C7—N1	167.5 (5)	C8—C9—C14—C13	178.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O3i	0.88	1.93	2.794 (5)	168
O1W—H2W···O3ii	0.89	2.29	2.898 (5)	126
O1W—H2W···N2ii	0.89	2.32	3.185 (5)	163
N1—H1N1···O1W	0.85	2.04	2.818 (5)	151
C2—H2A···O1iii	0.93	2.40	3.329 (6)	176
C14—H14A···O1Wiv	0.93	2.51	3.322 (6)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O3i	0.88	1.93	2.794 (5)	168
O1W—H2W⋯O3ii	0.89	2.29	2.898 (5)	126
O1W—H2W⋯N2ii	0.89	2.32	3.185 (5)	163
N1—H1N1⋯O1W	0.85	2.04	2.818 (5)	151
C2—H2A⋯O1iii	0.93	2.40	3.329 (6)	176
C14—H14A⋯O1Wiv	0.93	2.51	3.322 (6)	146

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .