(E)-N′-(2-Chloro-5-nitro­benzyl­idene)-3-meth­oxy­benzohydrazide monohydrate

Liu, S.-Y.; Wang, X.-L.

doi:10.1107/S1600536811020769

organic compounds

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Volume 67| Part 7| July 2011| Page o1625

doi:10.1107/S1600536811020769

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(E)-N′-(2-Chloro-5-nitrobenzylidene)-3-methoxybenzohydrazide monohydrate

Shi-Yong Liu ^a ^* and Xiao-Ling Wang ^b

^aCollege of Chemistry and Pharmacy, Taizhou University, Taizhou Zhejiang 317000, People's Republic of China, and ^bDepartment of Chemistry, Liaoning Normal University, Dalian 116029, People's Republic of China
^*Correspondence e-mail: liushiyong2010@yahoo.cn

(Received 25 May 2011; accepted 30 May 2011; online 11 June 2011)

In the hydrazone molecule of the title compound, C₁₅H₁₂ClN₃O₄·H₂O, the two benzene rings form a dihedral angle of 3.6 (1)°. In the crystal structure, the solvent water molecules are involved in the formation of intermolecular N—H⋯O and O—H⋯N hydrogen bonds, which link the molecules into double ribbons extending along the b axis. Intermolecular π–π interactions 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_r = 351.74
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.185
S = 1.02
3267 reflections
222 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.48 e Å⁻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⋯O1^iv	0.84 (1)	2.30 (3)	3.004 (4)	142 (3)
Symmetry codes: (iii) x, y+1, z; (iv) -x+1, -y+1, -z+2.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020769/cv5103sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811020769/cv5103Isup3.cml

checkCIF report

Comment top

In continuation of our structural studies of hydrazone derivatives (Liu & You, 2010a,b,c; Liu & Wang, 2010a,b; Sun et al., 2011), we present here the title compound (I) (Fig. 1).

In the hydrazone molecule of (I) , two benzene rings form a dihedral angle of 3.6 (1)°. In the crystal structure, the crystalline water molecules are involved in formation of intermolecular N—H···O and O—H···O hydrogen bonds (Table 2), which link the molecules into doubled ribbons extended along b axis (Fig. 2). Intermolecular π–π interactions (Table 1) between the aromatic rings link further these ribbons into layers parallel to ab plane.

Related literature top

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 top

The title compound was prepared by the condensation reaction of 2-chloro-5-nitrobenzaldehyde (1.0 mmol, 0.185 g) and 3-methoxybenzohydrazide (1.0 mmol, 0.166 g) in methanol (50 ml) at ambient temperature. Colourless block-shaped single crystals suitable for X-ray structural determination were obtained by slow evaporation of the solution for a few days.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as spheres of arbitrary radius. Hydrogen bond is shown as a dashed line.
	Fig. 2. A portion of the crystal packing viewed along the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

(E)-N'-(2-Chloro-5-nitrobenzylidene)-3-methoxybenzohydrazide monohydrate top

Crystal data top

C₁₅H₁₂ClN₃O₄·H₂O	Z = 2
M_r = 351.74	F(000) = 364
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0928P)²] where P = (F_o² + 2F_c²)/3
3267 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.36 e Å⁻³
4 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₁₅H₁₂ClN₃O₄·H₂O	γ = 80.190 (18)°
M_r = 351.74	V = 776.8 (4) Å³
Triclinic, P1	Z = 2
a = 7.176 (2) Å	Mo Kα radiation
b = 7.179 (2) Å	µ = 0.28 mm⁻¹
c = 15.395 (4) Å	T = 298 K
α = 83.820 (18)°	0.23 × 0.21 × 0.20 mm
β = 89.953 (18)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3267 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2015 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.947	R_int = 0.032
4678 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	4 restraints
wR(F²) = 0.185	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.36 e Å⁻³
3267 reflections	Δρ_min = −0.48 e Å⁻³
222 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.84 (1)	2.30 (3)	3.004 (4)	142 (3)

Symmetry codes: (iii) x, y+1, z; (iv) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂ClN₃O₄·H₂O
M_r	351.74
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.176 (2), 7.179 (2), 15.395 (4)
α, β, γ (°)	83.820 (18), 89.953 (18), 80.190 (18)
V (Å³)	776.8 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.23 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.939, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	4678, 3267, 2015
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.185, 1.02
No. of reflections	3267
No. of parameters	222
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.48

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Selected interatomic distances (Å) top

Cg1···Cg2ⁱ

3.712 (3)

Cg1···Cg2ⁱⁱ

3.672 (3)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.902 (10)	1.922 (13)	2.813 (4)	169 (4)
O5—H5B···O1ⁱⁱⁱ	0.835 (10)	2.03 (2)	2.783 (3)	150 (4)
O5—H5A···O1^iv	0.837 (10)	2.30 (3)	3.004 (4)	142 (3)

Symmetry codes: (iii) x, y+1, z; (iv) −x+1, −y+1, −z+2.

Acknowledgements

The authors acknowledge the Undergraduate Innovation Group Project of Zhejiang Province (project no. 2010R428015).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, S.-Y. & Wang, X. (2010a). Acta Cryst. E66, o1775. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, S.-Y. & Wang, X. (2010b). Acta Cryst. E66, o1805. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, S.-Y. & You, Z. (2010a). Acta Cryst. E66, o1652. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, S.-Y. & You, Z. (2010b). Acta Cryst. E66, o1658. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, S.-Y. & You, Z. (2010c). Acta Cryst. E66, o1662. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, S.-S., Liu, S.-Y., Zheng, T.-T. & Wang, X.-L. (2011). Acta Cryst. E67, o1624. Web of Science CSD CrossRef IUCr Journals Google Scholar