N′-(2-Chloro-5-nitro­benzyl­idene)-3-hydroxy­benzohydrazide methanol solvate

Zhou, Z.

doi:10.1107/S1600536808019636

organic compounds

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Volume 64| Part 8| August 2008| Page o1383

doi:10.1107/S1600536808019636

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N′-(2-Chloro-5-nitrobenzylidene)-3-hydroxybenzohydrazide methanol solvate

Zhi Zhou ^a ^*

^aDepartment of Chemistry, Kaili College, Kaili Guizhou 556000, People's Republic of China
^*Correspondence e-mail: zhou82zhi@126.com

(Received 13 June 2008; accepted 27 June 2008; online 5 July 2008)

In the title compound, C₁₄H₁₀ClN₃O₄·CH₃OH, the dihedral angle between the two benzene rings is 33.9 (2)°. In the crystal structure, the methanol solvent molecules are linked to the Schiff base molecules through intermolecular N—H⋯O and O—H⋯O hydrogen bonds. Molecules are further linked through intermolecular 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_r = 351.74
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.121
S = 1.01
3316 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536808019636/rz2226sup1.cif

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

checkCIF report

Comment top

Recently, we have reported two metal complexes with Schiff base ligands (Zhou & Tang, 2007; Zhou & Xiao, 2007). We report herein the crystal structure of the title Schiff base compound (Fig. 1).

The title compound consists of a Schiff base molecule and a methanol molecule of crystallization. The dihedral angle between the two benzene rings is 33.9 (2)°. All bond lengths are comparable to those found in similar compounds (Ali et al., 2007; Nie, 2008; He, 2008; Butcher et al., 2007; Jing & Yu, 2007). In the crystal structure, the methanol molecules are linked to the Schiff base molecules through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1). Molecules are further linked through intermolecular O—H···O and O—H···N hydrogen bonds to form chains running along the b axis (Fig. 2).

Related literature top

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 top

2-Chloro-5-nitrobenzaldehyde (1.0 mmol, 167.1 mg) and 3-hydroxybenzohydrazide (1.0 mmol, 152.1 mg) were dissolved in methanol (30 ml). The mixture was stirred at reflux for 30 min to give a colourless solution. After keeping the solution in air for a few days, colourless block-shaped crystals were formed.

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 the title compound, with displacement ellipsoids drawn at the 30% probability level. Hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title copound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

N'-(2-Chloro-5-nitrobenzylidene)-3-hydroxybenzohydrazide methanol solvate top

Crystal data top

C₁₄H₁₀ClN₃O₄·CH₄O	F(000) = 728
M_r = 351.74	D_x = 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 = 2.3–24.5°
b = 11.945 (2) Å	µ = 0.27 mm⁻¹
c = 17.650 (3) Å	T = 298 K
β = 99.886 (2)°	Block, colourless
V = 1602.6 (7) Å³	0.27 × 0.23 × 0.22 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3316 independent reflections
Radiation source: fine-focus sealed tube	2396 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 26.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.931, T_max = 0.943	k = −14→14
12656 measured reflections	l = −21→22

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0596P)² + 0.2859P] where P = (F_o² + 2F_c²)/3
3316 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₁₀ClN₃O₄·CH₄O	V = 1602.6 (7) Å³
M_r = 351.74	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.716 (3) Å	µ = 0.27 mm⁻¹
b = 11.945 (2) Å	T = 298 K
c = 17.650 (3) Å	0.27 × 0.23 × 0.22 mm
β = 99.886 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3316 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2396 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.943	R_int = 0.034
12656 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.18 e Å⁻³
3316 reflections	Δρ_min = −0.22 e Å⁻³
223 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	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀ClN₃O₄·CH₄O
M_r	351.74
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.716 (3), 11.945 (2), 17.650 (3)
β (°)	99.886 (2)
V (Å³)	1602.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.27 × 0.23 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.931, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	12656, 3316, 2396
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.121, 1.01
No. of reflections	3316
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.22

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3ⁱ	0.82	1.91	2.7237 (19)	169.4
O4—H4···N2ⁱ	0.82	2.62	3.118 (2)	120.4
O5—H5···O3ⁱ	0.82	2.00	2.817 (2)	175.2
N3—H3B···O5	0.81 (3)	2.05 (3)	2.854 (2)	173 (3)

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

Acknowledgements

The author thanks Kaili College for financial support.

References

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