N'-(5-Bromo-2-hy-droxy-benzyl-idene)-4-nitro-benzohydrazide methanol monosolvate.

In the title compound, C(14)H(10)BrN(3)O(4)·CH(4)O, the benzohydrazide mol-ecule 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 mol-ecule, there is an intra-molecular O-H⋯N hydrogen bond and the NH group is hydrogen bonded to the methanol solvent mol-ecule. In the crystal, inter-molecular O-H⋯O hydrogen bonds involving the methanol solvent mol-ecule link the benzohydrazide mol-ecules 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 = 396.20

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.101

S = 0.95

3442 reflections

222 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.43 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811030108/su2299sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811030108/su2299Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H10BrN3O4·CH4O	F(000) = 800
Mr = 396.20	Dx = 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

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

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(Fo2) + (0.0375P)2] where P = (Fo2 + 2Fc2)/3
3442 reflections	(Δ/σ)max = 0.001
222 parameters	Δρmax = 0.31 e Å−3
1 restraint	Δρmin = −0.43 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) ; (ii) .