N′-(5-Bromo-2-hy­droxy­benzyl­idene)-4-nitro­benzohydrazide methanol monosolvate

Liu, W.-H.; Song, S.-J.; Ma, J.-J.

doi:10.1107/S1600536811030108

organic compounds

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Volume 67| Part 8| August 2011| Page o2198

doi:10.1107/S1600536811030108

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N′-(5-Bromo-2-hydroxybenzylidene)-4-nitrobenzohydrazide methanol monosolvate

Wei-Hua Liu,^a Shuang-Ju Song ^a and Jing-Jun Ma ^a ^*

^aHebei Key Laboratory of Bioinorganic Chemistry, College of Sciences, Agricultural University of Hebei, Baoding 071001, People's Republic of China
^*Correspondence e-mail: majingjun71@yahoo.cn

(Received 23 July 2011; accepted 25 July 2011; online 30 July 2011)

In the title compound, C₁₄H₁₀BrN₃O₄·CH₄O, the benzohydrazide molecule is nearly planar [maximum deviation = 0.110 (2) Å]. The mean planes of the two benzene rings make a dihedral angle of 8.4 (3)°. In the benzohydrazide molecule, there is an intramolecular O—H⋯N hydrogen bond and the NH group is hydrogen bonded to the methanol solvent molecule. In the crystal, intermolecular O—H⋯O hydrogen bonds involving the methanol solvent molecule link the benzohydrazide molecules to form chains which propagate along the a axis.

Related literature

For the biological activities of benzohydrazide compounds, see: El-Sayed et al. (2011 ); Horiuchi et al. (2009 ). For coordination compounds of benzohydrazide compounds, see: El-Dissouky et al. (2010 ); Zhang et al. (2010 ). For standard bond distances, see: Allen et al. (1987 ). For related structures, see: Suleiman Gwaram et al. (2010 ); Dai & Mao (2010 ); Ban (2010 ).

Experimental

Crystal data

C₁₄H₁₀BrN₃O₄·CH₄O
M_r = 396.20
Monoclinic, P 2₁ /n
a = 6.660 (2) Å
b = 19.068 (3) Å
c = 12.730 (2) Å
β = 93.222 (2)°
V = 1614.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.58 mm⁻¹
T = 298 K
0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.668, T_max = 0.747
8673 measured reflections
3442 independent reflections
1824 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.101
S = 0.95
3442 reflections
222 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5	0.89 (1)	2.00 (2)	2.875 (4)	166 (4)
O1—H1⋯N1	0.82	2.03	2.737 (4)	143
O1—H1⋯O5ⁱ	0.82	2.51	2.952 (4)	115
O5—H5⋯O2ⁱⁱ	0.82	1.90	2.710 (4)	171
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811030108/su2299sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811030108/su2299Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811030108/su2299Isup3.cml

checkCIF report

Comment top

Benzohydrazide compounds are well known for their biological activities (El-Sayed et al., 2011; Horiuchi et al., 2009). In addition, benzohydrazide compounds have also been used as versatile ligands in coordination chemistry (El-Dissouky et al., 2010, Zhang et al., 2010). As a contribution to a structural study on hydrazone compounds, we present here the crystal structure of the title compound, that was obtained as the product of the reaction of 5-bromosalicylaldehyde with 4-nitrobenzohydrazide in methanol.

The title compound contains a benzohydrazide molecule and a methanol solvent molecule of crystallization (Fig. 1). In the benzohydrazide molecule there is an intramolecular O-H···N hydrogen bond and NH group is hydrogen bonded to the methanol solvate molecule. The bond distances (Allen et al., 1987) and angles are within normal ranges and agree well with the corresponding bond distances and angles reported in closely related compounds (Suleiman Gwaram et al., 2010; Dai & Mao, 2010; Ban, 2010). The benzohydrazide molecule is nearly planar [maximum deviation of 0.110 (2) Å], with the mean planes of the two benzene rings making a dihedral angle of 8.4 (3)°.

In the crystal, intermolecular O—H···O hydrogen bonds involving the methanol solvate molecule link the benzohydrazide molecules to form chains which propagate along along the a axis direction (Table 1, Fig. 2).

Related literature top

For the biological activities of benzohydrazide compounds, see: El-Sayed et al. (2011); Horiuchi et al. (2009). For the coordination compounds of benzohydrazide compounds, see: El-Dissouky et al. (2010); Zhang et al. (2010). For standard bond distances, see: Allen et al. (1987). For the crystal structures of similar compounds, see: Suleiman Gwaram et al. (2010); Dai & Mao (2010); Ban (2010).

Experimental top

To a methanol solution (20 ml) of 5-bromosalicylaldehyde (0.1 mmol, 20.1 mg) and 4-nitrobenzohydrazide (0.1 mmol, 18.1 mg), a few drops of acetic acid were added. The mixture was refluxed for 1 h and then cooled to room temperature. The white crystalline solid was collected by filtration, washed with cold methanol and dried in air. Single crystals, suitable for X-ray diffraction, were obtained by slow evaporation of a methanol solution of the product in air.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 the numbering scheme and displacement ellipsoids drawn at the 30% probability level. The N-H···O and O-H···N hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of the title compound, showing the N-H···O and O-H···O hydrogen-bonds (dashed lines) forming the chains propagating in [100]. H-atoms not involved in the hydrogen bonding have been omitted for clarity.

N'-(5-Bromo-2-hydroxybenzylidene)-4-nitrobenzohydrazide methanol monosolvate top

Crystal data top

C₁₄H₁₀BrN₃O₄·CH₄O	F(000) = 800
M_r = 396.20	D_x = 1.630 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.660 (2) Å	Cell parameters from 1199 reflections
b = 19.068 (3) Å	θ = 2.6–24.7°
c = 12.730 (2) Å	µ = 2.58 mm⁻¹
β = 93.222 (2)°	T = 298 K
V = 1614.1 (6) Å³	Block, yellow
Z = 4	0.17 × 0.13 × 0.12 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3442 independent reflections
Radiation source: fine-focus sealed tube	1824 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.668, T_max = 0.747	k = −22→24
8673 measured reflections	l = −10→16

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0375P)²] where P = (F_o² + 2F_c²)/3
3442 reflections	(Δ/σ)_max = 0.001
222 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₄H₁₀BrN₃O₄·CH₄O	V = 1614.1 (6) Å³
M_r = 396.20	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.660 (2) Å	µ = 2.58 mm⁻¹
b = 19.068 (3) Å	T = 298 K
c = 12.730 (2) Å	0.17 × 0.13 × 0.12 mm
β = 93.222 (2)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3442 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1824 reflections with I > 2σ(I)
T_min = 0.668, T_max = 0.747	R_int = 0.062
8673 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	1 restraint
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.31 e Å⁻³
3442 reflections	Δρ_min = −0.43 e Å⁻³
222 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
Br1	0.68607 (7)	0.04160 (2)	0.91805 (4)	0.06305 (19)
N1	0.9844 (5)	0.36314 (16)	0.8690 (2)	0.0446 (9)
N2	0.8848 (5)	0.42751 (16)	0.8642 (3)	0.0451 (9)
H2	0.7512 (18)	0.427 (2)	0.853 (3)	0.080*
N3	0.5371 (7)	0.74331 (19)	0.8890 (3)	0.0577 (10)
O1	1.2966 (4)	0.26998 (14)	0.8658 (3)	0.0627 (9)
H1	1.2483	0.3094	0.8694	0.094*
O2	1.1708 (4)	0.49115 (14)	0.8668 (2)	0.0563 (8)
O3	0.3577 (5)	0.73870 (16)	0.9023 (3)	0.0786 (10)
O4	0.6261 (5)	0.79787 (17)	0.8773 (3)	0.0821 (11)
O5	0.4668 (4)	0.40586 (15)	0.8042 (3)	0.0661 (9)
H5	0.3706	0.4278	0.8249	0.099*
C1	0.9471 (6)	0.23839 (19)	0.8828 (3)	0.0391 (10)
C2	1.1502 (6)	0.2216 (2)	0.8756 (3)	0.0433 (10)
C3	1.2093 (6)	0.1525 (2)	0.8787 (3)	0.0572 (12)
H3	1.3443	0.1414	0.8733	0.069*
C4	1.0715 (7)	0.0993 (2)	0.8896 (3)	0.0581 (12)
H4	1.1133	0.0528	0.8907	0.070*
C5	0.8718 (6)	0.1156 (2)	0.8989 (3)	0.0448 (10)
C6	0.8105 (6)	0.18444 (19)	0.8959 (3)	0.0424 (10)
H6	0.6755	0.1951	0.9026	0.051*
C7	0.8712 (6)	0.3099 (2)	0.8769 (3)	0.0450 (10)
H7	0.7334	0.3171	0.8791	0.054*
C8	0.9875 (6)	0.4882 (2)	0.8666 (3)	0.0411 (10)
C9	0.8637 (5)	0.55344 (18)	0.8725 (3)	0.0384 (9)
C10	0.6648 (6)	0.55357 (19)	0.8983 (3)	0.0483 (11)
H10	0.6010	0.5113	0.9112	0.058*
C11	0.5605 (6)	0.6152 (2)	0.9052 (3)	0.0518 (11)
H11	0.4274	0.6148	0.9239	0.062*
C12	0.6532 (6)	0.6769 (2)	0.8845 (3)	0.0445 (10)
C13	0.8513 (6)	0.6794 (2)	0.8602 (3)	0.0504 (11)
H13	0.9144	0.7221	0.8488	0.060*
C14	0.9540 (6)	0.61711 (19)	0.8530 (3)	0.0468 (11)
H14	1.0871	0.6178	0.8346	0.056*
C15	0.4336 (8)	0.3910 (2)	0.6962 (4)	0.0810 (16)
H15A	0.5205	0.4196	0.6565	0.122*
H15B	0.2960	0.4008	0.6747	0.122*
H15C	0.4618	0.3424	0.6838	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0601 (3)	0.0462 (3)	0.0829 (4)	−0.0063 (2)	0.0049 (2)	0.0158 (3)
N1	0.042 (2)	0.0374 (19)	0.054 (2)	0.0118 (16)	−0.0029 (17)	0.0009 (16)
N2	0.0325 (18)	0.0361 (18)	0.066 (3)	0.0090 (17)	−0.0054 (18)	−0.0002 (17)
N3	0.074 (3)	0.045 (2)	0.054 (3)	0.017 (2)	0.002 (2)	0.0011 (18)
O1	0.0411 (17)	0.0452 (16)	0.102 (3)	−0.0002 (14)	0.0036 (17)	0.0050 (18)
O2	0.0337 (17)	0.0477 (16)	0.087 (2)	0.0049 (13)	0.0019 (15)	−0.0032 (15)
O3	0.066 (2)	0.071 (2)	0.100 (3)	0.0291 (19)	0.012 (2)	−0.0011 (19)
O4	0.103 (3)	0.0429 (19)	0.101 (3)	0.0126 (19)	0.007 (2)	0.0085 (18)
O5	0.0413 (18)	0.064 (2)	0.092 (3)	0.0117 (15)	−0.0014 (17)	−0.0201 (18)
C1	0.040 (2)	0.040 (2)	0.037 (3)	0.0072 (18)	0.0015 (19)	−0.0007 (18)
C2	0.040 (2)	0.039 (2)	0.051 (3)	0.0014 (19)	−0.005 (2)	0.0023 (19)
C3	0.038 (2)	0.042 (2)	0.091 (4)	0.010 (2)	−0.002 (2)	0.002 (2)
C4	0.057 (3)	0.037 (2)	0.080 (4)	0.007 (2)	0.001 (3)	0.007 (2)
C5	0.043 (3)	0.041 (2)	0.050 (3)	−0.0022 (19)	0.001 (2)	0.009 (2)
C6	0.038 (2)	0.039 (2)	0.051 (3)	−0.0006 (18)	0.002 (2)	0.001 (2)
C7	0.040 (2)	0.042 (2)	0.053 (3)	0.006 (2)	0.004 (2)	−0.002 (2)
C8	0.040 (3)	0.039 (2)	0.043 (3)	0.003 (2)	−0.005 (2)	−0.0016 (19)
C9	0.037 (2)	0.035 (2)	0.044 (3)	0.0050 (17)	0.0002 (19)	0.0004 (18)
C10	0.046 (3)	0.036 (2)	0.064 (3)	−0.0013 (19)	0.007 (2)	−0.006 (2)
C11	0.038 (2)	0.048 (3)	0.070 (3)	0.006 (2)	0.009 (2)	−0.008 (2)
C12	0.054 (3)	0.039 (2)	0.040 (3)	0.012 (2)	−0.004 (2)	−0.0030 (19)
C13	0.052 (3)	0.037 (2)	0.062 (3)	0.002 (2)	0.002 (2)	0.007 (2)
C14	0.037 (2)	0.039 (2)	0.064 (3)	0.0001 (19)	0.002 (2)	0.005 (2)
C15	0.090 (4)	0.070 (3)	0.083 (5)	−0.004 (3)	0.006 (3)	0.001 (3)

Geometric parameters (Å, º) top

Br1—C5	1.901 (4)	C4—C5	1.377 (5)
N1—C7	1.271 (4)	C4—H4	0.9300
N1—N2	1.395 (4)	C5—C6	1.375 (5)
N2—C8	1.343 (5)	C6—H6	0.9300
N2—H2	0.894 (10)	C7—H7	0.9300
N3—O4	1.211 (4)	C8—C9	1.497 (5)
N3—O3	1.219 (4)	C9—C10	1.383 (5)
N3—C12	1.486 (5)	C9—C14	1.384 (5)
O1—C2	1.353 (4)	C10—C11	1.370 (5)
O1—H1	0.8200	C10—H10	0.9300
O2—C8	1.222 (4)	C11—C12	1.362 (5)
O5—C15	1.409 (5)	C11—H11	0.9300
O5—H5	0.8200	C12—C13	1.373 (5)
C1—C6	1.390 (5)	C13—C14	1.377 (5)
C1—C2	1.398 (5)	C13—H13	0.9300
C1—C7	1.456 (5)	C14—H14	0.9300
C2—C3	1.375 (5)	C15—H15A	0.9600
C3—C4	1.379 (5)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600

C7—N1—N2	115.0 (3)	C1—C7—H7	118.4
C8—N2—N1	121.1 (3)	O2—C8—N2	123.1 (4)
C8—N2—H2	121 (3)	O2—C8—C9	121.0 (4)
N1—N2—H2	117 (3)	N2—C8—C9	115.9 (3)
O4—N3—O3	124.7 (4)	C10—C9—C14	118.2 (3)
O4—N3—C12	117.9 (4)	C10—C9—C8	123.4 (3)
O3—N3—C12	117.4 (4)	C14—C9—C8	118.3 (3)
C2—O1—H1	109.5	C11—C10—C9	120.9 (4)
C15—O5—H5	109.5	C11—C10—H10	119.6
C6—C1—C2	118.7 (3)	C9—C10—H10	119.6
C6—C1—C7	118.2 (3)	C12—C11—C10	119.5 (4)
C2—C1—C7	123.1 (4)	C12—C11—H11	120.3
O1—C2—C3	116.7 (3)	C10—C11—H11	120.3
O1—C2—C1	123.7 (3)	C11—C12—C13	121.7 (4)
C3—C2—C1	119.6 (4)	C11—C12—N3	119.1 (4)
C2—C3—C4	121.1 (4)	C13—C12—N3	119.2 (4)
C2—C3—H3	119.5	C12—C13—C14	118.2 (4)
C4—C3—H3	119.5	C12—C13—H13	120.9
C5—C4—C3	119.6 (4)	C14—C13—H13	120.9
C5—C4—H4	120.2	C13—C14—C9	121.5 (4)
C3—C4—H4	120.2	C13—C14—H14	119.2
C6—C5—C4	120.0 (4)	C9—C14—H14	119.2
C6—C5—Br1	121.2 (3)	O5—C15—H15A	109.5
C4—C5—Br1	118.9 (3)	O5—C15—H15B	109.5
C5—C6—C1	121.0 (4)	H15A—C15—H15B	109.5
C5—C6—H6	119.5	O5—C15—H15C	109.5
C1—C6—H6	119.5	H15A—C15—H15C	109.5
N1—C7—C1	123.1 (4)	H15B—C15—H15C	109.5
N1—C7—H7	118.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.89 (1)	2.00 (2)	2.875 (4)	166 (4)
O1—H1···N1	0.82	2.03	2.737 (4)	143
O1—H1···O5ⁱ	0.82	2.51	2.952 (4)	115
O5—H5···O2ⁱⁱ	0.82	1.90	2.710 (4)	171

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀BrN₃O₄·CH₄O
M_r	396.20
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	6.660 (2), 19.068 (3), 12.730 (2)
β (°)	93.222 (2)
V (Å³)	1614.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.58
Crystal size (mm)	0.17 × 0.13 × 0.12

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.668, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	8673, 3442, 1824
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.101, 0.95
No. of reflections	3442
No. of parameters	222
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)	0.31, −0.43

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.894 (10)	2.000 (15)	2.875 (4)	166 (4)
O1—H1···N1	0.82	2.03	2.737 (4)	143
O1—H1···O5ⁱ	0.82	2.51	2.952 (4)	115
O5—H5···O2ⁱⁱ	0.82	1.90	2.710 (4)	171

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

Acknowledgements

This project was sponsored by the Nature Development Foundation of Hebei Province (gant No. B2011204051), the Development Foundation of the Department of Education of Hebei Province (grant No. 2010137) and the Research Development Foundation of the Agricultural University of Hebei.

References

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Volume 67| Part 8| August 2011| Page o2198

doi:10.1107/S1600536811030108

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

N′-(5-Bromo-2-hy­dr­oxy­benzyl­­idene)-4-nitro­benzohydrazide methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(5-Bromo-2-hydroxybenzylidene)-4-nitrobenzohydrazide methanol monosolvate