3-Chloro-N′-(4-hy­droxy-3-nitro­benzyl­idene)benzohydrazide methanol disolvate

Zhang, Z.

doi:10.1107/S1600536811021568

organic compounds

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Volume 67| Part 7| July 2011| Page o1630

doi:10.1107/S1600536811021568

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3-Chloro-N′-(4-hydroxy-3-nitrobenzylidene)benzohydrazide methanol disolvate

Zhen Zhang ^a ^*

^aExperimental Center, Linyi University, Linyi Shandong 276005, People's Republic of China
^*Correspondence e-mail: zhangzhen_lynu@126.com

(Received 30 May 2011; accepted 4 June 2011; online 11 June 2011)

In the title compound, C₁₄H₁₀ClN₃O₄·2CH₄O, the main molecule is in an E configuration with respect to the methylidene unit. The dihedral angle between the mean planes of the two benzene rings is 1.9 (3)°. In the crystal, intermolecular N—H⋯O, O—H⋯O and bifurcated O—H⋯(O, O) hydrogen bonds link the components into sheets parallel to (100). An intramolecular 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_r = 383.78
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.067
wR(F²) = 0.208
S = 1.06
3695 reflections
243 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811021568/lh5265sup1.cif

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

checkCIF report

Comment top

Hydrazone compounds have received much attention due to their potential applications in biological chemistry (Ajani et al., 2010; Avaji et al., 2009; Fan et al., 2010; Rasras et al., 2010). As a continuation of this work on hydrazone compounds the structure of the title compound is reported herein.

The asymmetric unit of title compound, Fig. 1, contains a hydrazone molecule and two methanol molecules. The hydrazone molecule assumes an E configuration with respect to the methylidene unit. The dihedral angle between the mean planes of the two benzene rings is 1.9 (3)°. The bond lengths are comparable to those observed in similar hydrazone compounds (Zhang, 2011a,b; Ahmad et al., 2010; Ban, 2010; Ji & Lu, 2010; Shalash et al., 2010). In the crystal, intermolecular N—H···O and O—H···O hydrogen bonds link the components into two dimensional sheets parallel to (100). An intramolecular O-H···O hydrogen bond is also present (Table 1, Fig. 2).

Related literature top

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 top

A methanol solution (50 ml) of 3-chlorobenzohydrazide (0.01 mol) and 4-hydroxy-3-nitrobenzaldehyde (0.01 mol) was stirred at room temperature for 30 min to give a yellow solution. Yellow block-shaped single crystals suitable for X-ray diffraction were formed by slow evaporation of the solution in air.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 the title compound, showing displacement ellipsoids at the 30% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The packing of the title compound. Hydrogen bonds are shown as dashed lines. Only H atoms involved in hydrogen bonds are shown.

3-Chloro-N'-(4-hydroxy-3-nitrobenzylidene)benzohydrazide methanol disolvate top

Crystal data top

C₁₄H₁₀ClN₃O₄·2CH₄O	F(000) = 800
M_r = 383.78	D_x = 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

Data collection top

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

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)] = 0.067	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(F_o²) + (0.0891P)²] where P = (F_o² + 2F_c²)/3
3695 reflections	(Δ/σ)_max = 0.001
243 parameters	Δρ_max = 0.76 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₄H₁₀ClN₃O₄·2CH₄O	V = 1824.6 (8) Å³
M_r = 383.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.626 (2) Å	µ = 0.25 mm⁻¹
b = 18.846 (5) Å	T = 298 K
c = 12.739 (3) Å	0.23 × 0.23 × 0.21 mm
β = 94.689 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	3695 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1842 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.950	R_int = 0.048
7726 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	1 restraint
wR(F²) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.76 e Å⁻³
3695 reflections	Δρ_min = −0.26 e Å⁻³
243 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2; (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀ClN₃O₄·2CH₄O
M_r	383.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.626 (2), 18.846 (5), 12.739 (3)
β (°)	94.689 (4)
V (Å³)	1824.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.23 × 0.23 × 0.21

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.945, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	7726, 3695, 1842
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.208, 1.06
No. of reflections	3695
No. of parameters	243
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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	0.893 (10)	1.988 (18)	2.834 (4)	158 (4)
O5—H5···O4ⁱⁱ	0.82	1.96	2.779 (4)	173

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

Acknowledgements

The author thanks the Experimental Center of Linyi University for supporting this work.

References

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Volume 67| Part 7| July 2011| Page o1630

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-Chloro-N′-(4-hy­dr­oxy-3-nitro­benzyl­­idene)benzohydrazide methanol disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Chloro-N′-(4-hydroxy-3-nitrobenzylidene)benzohydrazide methanol disolvate