(E)-N'-(2-Chloro-5-nitro-benzyl-idene)-3-meth-oxy-benzohydrazide monohydrate.

In the hydrazone mol-ecule of the title compound, C(15)H(12)ClN(3)O(4)·H(2)O, the two benzene rings form a dihedral angle of 3.6 (1)°. In the crystal structure, the solvent water mol-ecules are involved in the formation of inter-molecular N-H⋯O and O-H⋯N hydrogen bonds, which link the mol-ecules into double ribbons extending along the b axis. Inter-molecular π-π inter-actions between the aromatic rings [centroid-centroid distances = 3.712 (3) and 3.672 (3) Å] link these ribbons further into layers parallel to the ab plane.

Related literature

For the crystal structures of hydrazones recently reported by us, see: Liu & You (2010a ▶,b ▶,c ▶); Liu & Wang (2010a ▶,b ▶); Sun et al. (2011 ▶).

Experimental

Crystal data

C15H12ClN3O4·H2O

M = 351.74

Triclinic,

a = 7.176 (2) Å

b = 7.179 (2) Å

c = 15.395 (4) Å

α = 83.820 (18)°

β = 89.953 (18)°

γ = 80.190 (18)°

V = 776.8 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.939, T max = 0.947

4678 measured reflections

3267 independent reflections

2015 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.185

S = 1.02

3267 reflections

222 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.48 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 datablock(s) global, I. DOI: 10.1107/S1600536811020769/cv5103sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020769/cv5103Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020769/cv5103Isup3.cml

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

C15H12ClN3O4·H2O	Z = 2
Mr = 351.74	F(000) = 364
Triclinic, P1	Dx = 1.504 Mg m−3
a = 7.176 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.179 (2) Å	Cell parameters from 887 reflections
c = 15.395 (4) Å	θ = 2.8–25.3°
α = 83.820 (18)°	µ = 0.28 mm−1
β = 89.953 (18)°	T = 298 K
γ = 80.190 (18)°	Block, colourless
V = 776.8 (4) Å3	0.23 × 0.21 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	3267 independent reflections
Radiation source: fine-focus sealed tube	2015 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 27.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.939, Tmax = 0.947	k = −8→9
4678 measured reflections	l = −19→19

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0928P)2] where P = (Fo2 + 2Fc2)/3
3267 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.36 e Å−3
4 restraints	Δρmin = −0.48 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.05788 (14)	1.03926 (12)	1.12824 (6)	0.0525 (3)
N1	0.2400 (4)	0.5012 (4)	1.03085 (15)	0.0348 (6)
N2	0.2787 (4)	0.5246 (3)	0.94318 (16)	0.0350 (6)
N3	0.1926 (5)	0.3190 (5)	1.36258 (19)	0.0543 (8)
O1	0.3018 (4)	0.2107 (3)	0.93423 (15)	0.0486 (6)
O2	0.2513 (4)	0.8041 (4)	0.63274 (15)	0.0594 (8)
O3	0.2584 (5)	0.1707 (4)	1.33358 (19)	0.0750 (9)
O4	0.1633 (5)	0.3291 (4)	1.44026 (17)	0.0838 (10)
O5	0.4570 (3)	0.8422 (3)	0.90264 (16)	0.0475 (6)*
C1	0.1635 (4)	0.6554 (4)	1.15934 (19)	0.0322 (7)
C2	0.0887 (4)	0.8238 (4)	1.1940 (2)	0.0350 (7)
C3	0.0387 (5)	0.8259 (5)	1.2810 (2)	0.0435 (8)
H3	−0.0148	0.9392	1.3021	0.052*
C4	0.0690 (5)	0.6595 (5)	1.3356 (2)	0.0448 (8)
H4	0.0350	0.6582	1.3940	0.054*
C5	0.1506 (5)	0.4938 (5)	1.3029 (2)	0.0373 (8)
C6	0.1960 (4)	0.4882 (4)	1.2159 (2)	0.0356 (7)
H6	0.2478	0.3738	1.1954	0.043*
C7	0.2063 (4)	0.6559 (4)	1.0662 (2)	0.0362 (7)
H7	0.2088	0.7708	1.0323	0.043*
C8	0.3063 (4)	0.3706 (4)	0.8984 (2)	0.0335 (7)
C9	0.3373 (4)	0.4103 (4)	0.8024 (2)	0.0327 (7)
C10	0.2874 (4)	0.5904 (4)	0.7584 (2)	0.0366 (7)
H10	0.2378	0.6916	0.7892	0.044*
C11	0.3104 (5)	0.6216 (5)	0.6691 (2)	0.0397 (8)
C12	0.3870 (5)	0.4713 (5)	0.6231 (2)	0.0449 (8)
H12	0.4035	0.4907	0.5631	0.054*
C13	0.4381 (5)	0.2933 (5)	0.6678 (2)	0.0462 (9)
H13	0.4893	0.1925	0.6371	0.055*
C14	0.4157 (5)	0.2598 (5)	0.7561 (2)	0.0396 (8)
H14	0.4524	0.1383	0.7849	0.048*
C15	0.2835 (6)	0.8508 (6)	0.5424 (2)	0.0683 (12)
H15A	0.4162	0.8194	0.5312	0.103*
H15B	0.2414	0.9844	0.5267	0.103*
H15C	0.2148	0.7799	0.5083	0.103*
H2	0.334 (5)	0.624 (4)	0.923 (3)	0.080*
H5A	0.563 (3)	0.822 (5)	0.928 (2)	0.080*
H5B	0.382 (4)	0.931 (4)	0.921 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0666 (7)	0.0353 (5)	0.0513 (6)	0.0039 (4)	0.0017 (4)	−0.0056 (4)
N1	0.0430 (16)	0.0342 (14)	0.0266 (13)	−0.0046 (12)	0.0026 (11)	−0.0043 (11)
N2	0.0474 (17)	0.0316 (14)	0.0263 (13)	−0.0060 (12)	0.0050 (12)	−0.0053 (11)
N3	0.069 (2)	0.057 (2)	0.0384 (18)	−0.0204 (17)	−0.0057 (15)	0.0042 (15)
O1	0.0780 (18)	0.0293 (12)	0.0386 (13)	−0.0088 (12)	0.0036 (12)	−0.0046 (10)
O2	0.085 (2)	0.0501 (15)	0.0335 (13)	0.0100 (14)	0.0089 (13)	0.0051 (11)
O3	0.114 (3)	0.0452 (16)	0.0614 (19)	−0.0077 (17)	−0.0034 (17)	0.0033 (14)
O4	0.133 (3)	0.086 (2)	0.0292 (14)	−0.021 (2)	0.0034 (16)	0.0090 (14)
C1	0.0302 (16)	0.0331 (16)	0.0331 (16)	−0.0038 (13)	−0.0005 (13)	−0.0062 (13)
C2	0.0334 (17)	0.0363 (17)	0.0347 (17)	−0.0030 (13)	−0.0015 (13)	−0.0053 (13)
C3	0.044 (2)	0.045 (2)	0.0417 (19)	−0.0018 (16)	0.0014 (16)	−0.0174 (16)
C4	0.048 (2)	0.060 (2)	0.0297 (17)	−0.0132 (17)	0.0049 (15)	−0.0131 (16)
C5	0.0391 (19)	0.0415 (18)	0.0330 (17)	−0.0134 (15)	−0.0025 (14)	−0.0011 (14)
C6	0.0389 (18)	0.0356 (17)	0.0325 (16)	−0.0047 (14)	0.0004 (14)	−0.0072 (13)
C7	0.0397 (18)	0.0320 (16)	0.0342 (16)	−0.0009 (14)	0.0045 (14)	−0.0008 (13)
C8	0.0372 (18)	0.0305 (16)	0.0331 (16)	−0.0044 (13)	0.0001 (13)	−0.0059 (13)
C9	0.0309 (17)	0.0351 (16)	0.0334 (16)	−0.0064 (13)	0.0002 (13)	−0.0080 (13)
C10	0.0410 (19)	0.0355 (17)	0.0319 (16)	0.0000 (14)	0.0021 (14)	−0.0080 (13)
C11	0.0392 (19)	0.0416 (18)	0.0365 (18)	−0.0020 (15)	0.0026 (15)	−0.0036 (14)
C12	0.051 (2)	0.054 (2)	0.0320 (17)	−0.0110 (17)	0.0133 (16)	−0.0106 (15)
C13	0.056 (2)	0.0410 (19)	0.045 (2)	−0.0088 (16)	0.0150 (17)	−0.0183 (15)
C14	0.046 (2)	0.0347 (17)	0.0379 (18)	−0.0044 (15)	0.0032 (15)	−0.0066 (14)
C15	0.096 (3)	0.067 (3)	0.036 (2)	−0.005 (2)	0.004 (2)	0.0071 (19)

Cl1—C2	1.735 (3)	C4—C5	1.380 (5)
N1—C7	1.275 (4)	C4—H4	0.9300
N1—N2	1.376 (3)	C5—C6	1.381 (4)
N2—C8	1.351 (4)	C6—H6	0.9300
N2—H2	0.902 (10)	C7—H7	0.9300
N3—O3	1.219 (4)	C8—C9	1.499 (4)
N3—O4	1.222 (4)	C9—C10	1.383 (4)
N3—C5	1.461 (4)	C9—C14	1.396 (4)
O1—C8	1.225 (3)	C10—C11	1.383 (4)
O2—C11	1.365 (4)	C10—H10	0.9300
O2—C15	1.424 (4)	C11—C12	1.389 (5)
O5—H5A	0.837 (10)	C12—C13	1.376 (5)
O5—H5B	0.835 (10)	C12—H12	0.9300
C1—C6	1.391 (4)	C13—C14	1.369 (5)
C1—C2	1.397 (4)	C13—H13	0.9300
C1—C7	1.467 (4)	C14—H14	0.9300
C2—C3	1.388 (4)	C15—H15A	0.9600
C3—C4	1.370 (5)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
Cg1···Cg2i	3.712 (3)	Cg1···Cg2ii	3.672 (3)
C7—N1—N2	114.2 (2)	C1—C7—H7	119.5
C8—N2—N1	119.0 (2)	O1—C8—N2	121.7 (3)
C8—N2—H2	118 (3)	O1—C8—C9	122.8 (3)
N1—N2—H2	118 (3)	N2—C8—C9	115.5 (3)
O3—N3—O4	122.8 (3)	C10—C9—C14	119.4 (3)
O3—N3—C5	119.1 (3)	C10—C9—C8	121.9 (3)
O4—N3—C5	118.1 (3)	C14—C9—C8	118.7 (3)
C11—O2—C15	118.6 (3)	C9—C10—C11	120.7 (3)
H5A—O5—H5B	113 (2)	C9—C10—H10	119.7
C6—C1—C2	117.9 (3)	C11—C10—H10	119.7
C6—C1—C7	121.3 (3)	O2—C11—C10	115.3 (3)
C2—C1—C7	120.8 (3)	O2—C11—C12	124.9 (3)
C3—C2—C1	121.9 (3)	C10—C11—C12	119.8 (3)
C3—C2—Cl1	117.9 (2)	C13—C12—C11	118.9 (3)
C1—C2—Cl1	120.2 (2)	C13—C12—H12	120.5
C4—C3—C2	119.4 (3)	C11—C12—H12	120.5
C4—C3—H3	120.3	C14—C13—C12	122.0 (3)
C2—C3—H3	120.3	C14—C13—H13	119.0
C3—C4—C5	119.1 (3)	C12—C13—H13	119.0
C3—C4—H4	120.5	C13—C14—C9	119.2 (3)
C5—C4—H4	120.5	C13—C14—H14	120.4
C4—C5—C6	122.3 (3)	C9—C14—H14	120.4
C4—C5—N3	118.8 (3)	O2—C15—H15A	109.5
C6—C5—N3	119.0 (3)	O2—C15—H15B	109.5
C5—C6—C1	119.3 (3)	H15A—C15—H15B	109.5
C5—C6—H6	120.3	O2—C15—H15C	109.5
C1—C6—H6	120.3	H15A—C15—H15C	109.5
N1—C7—C1	121.0 (3)	H15B—C15—H15C	109.5
N1—C7—H7	119.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.90 (1)	1.92 (1)	2.813 (4)	169 (4)
O5—H5B···O1iii	0.84 (1)	2.03 (2)	2.783 (3)	150 (4)
O5—H5A···O1iv	0.84 (1)	2.30 (3)	3.004 (4)	142 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5	0.90 (1)	1.92 (1)	2.813 (4)	169 (4)
O5—H5B⋯O1iii	0.84 (1)	2.03 (2)	2.783 (3)	150 (4)
O5—H5A⋯O1iv	0.84 (1)	2.30 (3)	3.004 (4)	142 (3)

Symmetry codes: (iii) ; (iv) .