N′-(3,5-Dichloro-2-hy­droxy­benzyl­idene)-4-nitro­benzohydrazide methanol solvate

Zhu, H.-Y.

doi:10.1107/S1600536810036184

organic compounds

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Volume 66| Part 10| October 2010| Page o2562

doi:10.1107/S1600536810036184

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N′-(3,5-Dichloro-2-hydroxybenzylidene)-4-nitrobenzohydrazide methanol solvate

Hai-Yun Zhu ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013, People's Republic of China
^*Correspondence e-mail: zhuzhuhaiyun@126.com

(Received 6 September 2010; accepted 8 September 2010; online 15 September 2010)

In the title compound, C₁₄H₉Cl₂N₃O₄·CH₄O, the dihedral angle between the two benzene rings in the hydrazone molecule is 6.3 (3)°. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation. In the crystal, centrosymmetrically related molecules are linked through intermolecular O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For general background to hydrazone compounds, see: Rasras et al. (2010 ); Fan et al. (2010 ); Ajani et al. (2010 ); Avaji et al. (2009 ). For the crystal structures of related hydrazone compounds, see: Khaledi et al. (2010 ); Han et al. (2010 ); Hussain et al. (2010 ); Ji & Lu (2010 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₉Cl₂N₃O₄·CH₄O
M_r = 386.18
Monoclinic, P 2₁ /n
a = 7.415 (3) Å
b = 13.408 (3) Å
c = 16.674 (2) Å
β = 99.716 (3)°
V = 1634.0 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 298 K
0.15 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.938, T_max = 0.958
8410 measured reflections
3467 independent reflections
2099 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.124
S = 1.02
3467 reflections
232 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.92	2.633 (3)	145
N2—H2⋯O5	0.90 (1)	1.91 (1)	2.793 (3)	167 (3)
O5—H5⋯O2ⁱ	0.82	2.15	2.903 (3)	153
Symmetry code: (i) -x+1, -y, -z+1.

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/S1600536810036184/rz2485sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036184/rz2485Isup2.hkl

checkCIF report

Comment top

In recent years, considerable interest has been focused on the preparation and biological properties of hydrazone compounds (Rasras et al., 2010; Fan et al., 2010; Ajani et al., 2010; Avaji et al., 2009). The crystal structures of a number of hydrazone compounds have been reported (Khaledi et al., 2010; Han et al., 2010; Hussain et al., 2010; Ji & Lu, 2010). The author reports in this paper the title new hydrazone compound.

The asymmetric unit of the title compound (Fig. 1) consists of a hydrazone molecule and a methanol molecule. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 6.3 (3)°. There is an intramolecular O—H···N hydrogen bond (Table 1) stabilizing the conformation of the hydrazone molecule. All bond lengths are within normal values (Allen et al., 1987), and are comparable with those in the similar hydrazone compounds as cited above. In the crystal structure (Fig. 2), centrosymmetrically related molecules are linked through intermolecular O—H···O and N—H···O hydrogen bonds (Table 1).

Related literature top

For general background to hydrazone compounds, see: Rasras et al. (2010); Fan et al. (2010); Ajani et al. (2010); Avaji et al. (2009). For the crystal structures of related hydrazone compounds, see: Khaledi et al. (2010); Han et al. (2010); Hussain et al. (2010); Ji & Lu (2010). For reference bond-length data, see: Allen et al. (1987).

Experimental top

3,5-Dichlorosalicylaldehyde (0.191 g, 1 mmol) and 4-nitrobenzohydrazide (0.181 g, 1 mmol) were dissolved in 30 ml absolute methanol. The mixture was stirred at reflux for 10 min, and cooled to room temperature. The clear yellow solution was left to slowly evaporate in air for a week, yielding yellow needle crystals of the title compound suitable for X-ray analysis.

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 30% probability displacement ellipsoids for non-hydrogen atoms. Hydrogen bonds are drawn as dashed lines.
	Fig. 2. The molecular packing of the title compound viewed along the c axis. Hydrogen atoms not involved in hydrogen bonds (dashed lines) are omitted for clarity.

N'-(3,5-Dichloro-2-hydroxybenzylidene)-4-nitrobenzohydrazide methanol solvate top

Crystal data top

C₁₄H₉Cl₂N₃O₄·CH₄O	F(000) = 792
M_r = 386.18	D_x = 1.570 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1245 reflections
a = 7.415 (3) Å	θ = 2.4–24.5°
b = 13.408 (3) Å	µ = 0.43 mm⁻¹
c = 16.674 (2) Å	T = 298 K
β = 99.716 (3)°	Cut from needle, yellow
V = 1634.0 (8) Å³	0.15 × 0.13 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3467 independent reflections
Radiation source: fine-focus sealed tube	2099 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scans	θ_max = 27.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.938, T_max = 0.958	k = −14→17
8410 measured reflections	l = −21→17

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0478P)² + 0.0676P] where P = (F_o² + 2F_c²)/3
3467 reflections	(Δ/σ)_max < 0.001
232 parameters	Δρ_max = 0.21 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₄H₉Cl₂N₃O₄·CH₄O	V = 1634.0 (8) Å³
M_r = 386.18	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.415 (3) Å	µ = 0.43 mm⁻¹
b = 13.408 (3) Å	T = 298 K
c = 16.674 (2) Å	0.15 × 0.13 × 0.10 mm
β = 99.716 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3467 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2099 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.958	R_int = 0.046
8410 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	1 restraint
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.21 e Å⁻³
3467 reflections	Δρ_min = −0.31 e Å⁻³
232 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	0.46614 (12)	−0.21402 (6)	0.15195 (5)	0.0565 (3)
Cl2	0.37115 (12)	0.17025 (6)	0.06479 (5)	0.0538 (3)
N1	0.2955 (3)	−0.01141 (17)	0.40697 (13)	0.0378 (6)
N2	0.2663 (3)	0.02375 (17)	0.48171 (14)	0.0388 (6)
N3	0.0804 (4)	0.1043 (3)	0.84113 (17)	0.0567 (8)
O1	0.3717 (3)	−0.14918 (14)	0.30523 (12)	0.0481 (6)
H1	0.3572	−0.1275	0.3497	0.072*
O2	0.2382 (3)	−0.13351 (15)	0.52776 (12)	0.0552 (6)
O3	0.0317 (4)	0.1905 (2)	0.84516 (15)	0.0786 (8)
O4	0.1004 (4)	0.0463 (2)	0.89825 (15)	0.0911 (9)
O5	0.4237 (3)	0.21205 (16)	0.51288 (15)	0.0619 (7)
H5	0.5275	0.2100	0.5021	0.093*
C1	0.3366 (4)	0.0260 (2)	0.27209 (16)	0.0329 (6)
C2	0.3712 (4)	−0.0733 (2)	0.25280 (16)	0.0356 (7)
C3	0.4095 (4)	−0.0933 (2)	0.17535 (16)	0.0349 (7)
C4	0.4077 (4)	−0.0197 (2)	0.11735 (17)	0.0410 (7)
H4	0.4311	−0.0353	0.0657	0.049*
C5	0.3705 (4)	0.0773 (2)	0.13695 (16)	0.0370 (7)
C6	0.3342 (4)	0.1002 (2)	0.21322 (16)	0.0363 (7)
H6	0.3079	0.1656	0.2256	0.044*
C7	0.3046 (4)	0.0552 (2)	0.35267 (16)	0.0373 (7)
H7	0.2908	0.1223	0.3647	0.045*
C8	0.2371 (4)	−0.0435 (2)	0.53888 (17)	0.0369 (7)
C9	0.1972 (4)	−0.0003 (2)	0.61643 (16)	0.0332 (7)
C10	0.1438 (4)	0.0976 (2)	0.62461 (17)	0.0395 (7)
H10	0.1332	0.1406	0.5803	0.047*
C11	0.1061 (4)	0.1320 (2)	0.69819 (18)	0.0440 (8)
H11	0.0710	0.1978	0.7040	0.053*
C12	0.1216 (4)	0.0669 (2)	0.76247 (17)	0.0405 (7)
C13	0.1716 (4)	−0.0309 (2)	0.75640 (17)	0.0439 (8)
H13	0.1796	−0.0737	0.8008	0.053*
C14	0.2096 (4)	−0.0643 (2)	0.68295 (17)	0.0400 (7)
H14	0.2439	−0.1304	0.6777	0.048*
C15	0.3910 (5)	0.3073 (2)	0.5430 (2)	0.0592 (9)
H15A	0.4591	0.3147	0.5970	0.089*
H15B	0.2628	0.3147	0.5444	0.089*
H15C	0.4288	0.3574	0.5082	0.089*
H2	0.300 (5)	0.0871 (11)	0.494 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0704 (6)	0.0374 (5)	0.0641 (6)	0.0041 (4)	0.0181 (4)	−0.0126 (4)
Cl2	0.0633 (6)	0.0514 (5)	0.0479 (5)	−0.0048 (4)	0.0127 (4)	0.0148 (4)
N1	0.0435 (15)	0.0393 (14)	0.0321 (13)	−0.0018 (12)	0.0109 (11)	−0.0040 (11)
N2	0.0501 (16)	0.0345 (14)	0.0334 (13)	−0.0035 (13)	0.0120 (11)	−0.0031 (11)
N3	0.0562 (19)	0.072 (2)	0.0457 (18)	−0.0123 (17)	0.0203 (14)	−0.0134 (16)
O1	0.0704 (16)	0.0325 (12)	0.0429 (12)	−0.0015 (11)	0.0138 (12)	0.0040 (9)
O2	0.0864 (18)	0.0301 (12)	0.0527 (14)	−0.0008 (12)	0.0223 (12)	−0.0067 (10)
O3	0.098 (2)	0.076 (2)	0.0684 (18)	0.0053 (17)	0.0328 (15)	−0.0264 (15)
O4	0.143 (3)	0.093 (2)	0.0445 (15)	−0.0060 (19)	0.0359 (16)	−0.0005 (15)
O5	0.0673 (17)	0.0488 (14)	0.0767 (17)	−0.0132 (12)	0.0326 (14)	−0.0180 (12)
C1	0.0328 (16)	0.0336 (16)	0.0335 (15)	−0.0002 (13)	0.0089 (12)	−0.0015 (12)
C2	0.0350 (17)	0.0346 (17)	0.0375 (16)	−0.0021 (13)	0.0065 (13)	0.0027 (13)
C3	0.0342 (17)	0.0311 (16)	0.0406 (16)	0.0007 (13)	0.0094 (13)	−0.0066 (13)
C4	0.0444 (19)	0.0441 (18)	0.0354 (16)	−0.0056 (15)	0.0095 (13)	−0.0027 (14)
C5	0.0375 (17)	0.0383 (17)	0.0357 (16)	−0.0036 (14)	0.0081 (13)	0.0039 (13)
C6	0.0371 (17)	0.0290 (15)	0.0423 (17)	0.0011 (13)	0.0056 (13)	0.0008 (13)
C7	0.0401 (18)	0.0323 (16)	0.0406 (16)	0.0026 (14)	0.0099 (13)	−0.0024 (13)
C8	0.0384 (18)	0.0350 (17)	0.0378 (16)	−0.0028 (14)	0.0078 (13)	−0.0025 (14)
C9	0.0307 (16)	0.0351 (16)	0.0344 (15)	−0.0016 (13)	0.0075 (12)	−0.0028 (13)
C10	0.0459 (19)	0.0368 (17)	0.0387 (17)	0.0034 (14)	0.0157 (14)	0.0019 (13)
C11	0.048 (2)	0.0404 (18)	0.0461 (18)	0.0010 (15)	0.0150 (15)	−0.0044 (15)
C12	0.0340 (17)	0.054 (2)	0.0356 (16)	−0.0081 (15)	0.0132 (13)	−0.0094 (15)
C13	0.048 (2)	0.047 (2)	0.0368 (17)	−0.0054 (16)	0.0068 (14)	0.0039 (14)
C14	0.0417 (18)	0.0332 (17)	0.0458 (18)	−0.0059 (14)	0.0094 (14)	−0.0009 (14)
C15	0.058 (2)	0.047 (2)	0.074 (2)	0.0044 (17)	0.0156 (18)	−0.0058 (18)

Geometric parameters (Å, º) top

Cl1—C3	1.733 (3)	C4—C5	1.380 (4)
Cl2—C5	1.733 (3)	C4—H4	0.9300
N1—C7	1.282 (3)	C5—C6	1.378 (4)
N1—N2	1.383 (3)	C6—H6	0.9300
N2—C8	1.356 (4)	C7—H7	0.9300
N2—H2	0.898 (10)	C8—C9	1.492 (4)
N3—O3	1.217 (4)	C9—C10	1.385 (4)
N3—O4	1.219 (3)	C9—C14	1.393 (4)
N3—C12	1.483 (4)	C10—C11	1.383 (4)
O1—C2	1.341 (3)	C10—H10	0.9300
O1—H1	0.8200	C11—C12	1.372 (4)
O2—C8	1.221 (3)	C11—H11	0.9300
O5—C15	1.409 (3)	C12—C13	1.371 (4)
O5—H5	0.8200	C13—C14	1.377 (4)
C1—C6	1.396 (4)	C13—H13	0.9300
C1—C2	1.403 (4)	C14—H14	0.9300
C1—C7	1.457 (4)	C15—H15A	0.9600
C2—C3	1.394 (4)	C15—H15B	0.9600
C3—C4	1.380 (4)	C15—H15C	0.9600

C7—N1—N2	115.7 (2)	C1—C7—H7	120.0
C8—N2—N1	118.3 (2)	O2—C8—N2	123.0 (3)
C8—N2—H2	123 (2)	O2—C8—C9	121.5 (3)
N1—N2—H2	116 (2)	N2—C8—C9	115.4 (2)
O3—N3—O4	124.2 (3)	C10—C9—C14	119.1 (3)
O3—N3—C12	118.5 (3)	C10—C9—C8	123.7 (3)
O4—N3—C12	117.3 (3)	C14—C9—C8	117.1 (3)
C2—O1—H1	109.5	C11—C10—C9	120.5 (3)
C15—O5—H5	109.5	C11—C10—H10	119.8
C6—C1—C2	119.7 (2)	C9—C10—H10	119.8
C6—C1—C7	118.2 (3)	C12—C11—C10	118.6 (3)
C2—C1—C7	122.1 (3)	C12—C11—H11	120.7
O1—C2—C3	118.6 (3)	C10—C11—H11	120.7
O1—C2—C1	123.4 (3)	C13—C12—C11	122.6 (3)
C3—C2—C1	118.0 (2)	C13—C12—N3	119.2 (3)
C4—C3—C2	122.1 (3)	C11—C12—N3	118.2 (3)
C4—C3—Cl1	119.0 (2)	C12—C13—C14	118.4 (3)
C2—C3—Cl1	118.9 (2)	C12—C13—H13	120.8
C5—C4—C3	119.1 (3)	C14—C13—H13	120.8
C5—C4—H4	120.4	C13—C14—C9	120.8 (3)
C3—C4—H4	120.4	C13—C14—H14	119.6
C6—C5—C4	120.4 (3)	C9—C14—H14	119.6
C6—C5—Cl2	120.3 (2)	O5—C15—H15A	109.5
C4—C5—Cl2	119.3 (2)	O5—C15—H15B	109.5
C5—C6—C1	120.6 (3)	H15A—C15—H15B	109.5
C5—C6—H6	119.7	O5—C15—H15C	109.5
C1—C6—H6	119.7	H15A—C15—H15C	109.5
N1—C7—C1	120.0 (3)	H15B—C15—H15C	109.5
N1—C7—H7	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.92	2.633 (3)	145
N2—H2···O5	0.90 (1)	1.91 (1)	2.793 (3)	167 (3)
O5—H5···O2ⁱ	0.82	2.15	2.903 (3)	153

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₉Cl₂N₃O₄·CH₄O
M_r	386.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.415 (3), 13.408 (3), 16.674 (2)
β (°)	99.716 (3)
V (Å³)	1634.0 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.15 × 0.13 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.938, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	8410, 3467, 2099
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.124, 1.02
No. of reflections	3467
No. of parameters	232
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)	0.21, −0.31

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
O1—H1···N1	0.82	1.92	2.633 (3)	144.6
N2—H2···O5	0.898 (10)	1.910 (13)	2.793 (3)	167 (3)
O5—H5···O2ⁱ	0.82	2.15	2.903 (3)	153.3

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

This work was supported by the Science Research Foundation of Baoji University of Arts and Sciences (grant No. ZK085).

References

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Volume 66| Part 10| October 2010| Page o2562

doi:10.1107/S1600536810036184

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

N′-(3,5-Di­chloro-2-hy­dr­oxy­benzyl­­idene)-4-nitro­benzohydrazide methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(3,5-Dichloro-2-hydroxybenzylidene)-4-nitrobenzohydrazide methanol solvate