N'-(5-Bromo-2-hy-droxy-benzyl-idene)-3-nitro-benzohydrazide methanol mono-solvate.

In the title compound, C(14)H(10)BrN(3)O(4)·CH(4)O, the dihedral angle between the two benzene rings in the hydrazone mol-ecule is 5.8 (3)° and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. An O-H⋯O hydrogen bond occurs between the hydrazone mol-ecule and the methanol solvent mol-ecule. In the crystal, the components are linked by inter-molecular N-H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶, 2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H10BrN3O4·CH4O

M = 396.20

Triclinic,

a = 6.701 (2) Å

b = 9.492 (3) Å

c = 13.011 (3) Å

α = 105.866 (2)°

β = 92.535 (2)°

γ = 94.496 (2)°

V = 791.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.63 mm−1

T = 298 K

0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.726, T max = 0.779

6325 measured reflections

3356 independent reflections

1142 reflections with I > 2σ(I)

R int = 0.109

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.236

S = 0.93

3356 reflections

223 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.83 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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) global, I. DOI: 10.1107/S1600536811042553/qm2037sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042553/qm2037Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042553/qm2037Isup3.cml

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

C14H10BrN3O4·CH4O	Z = 2
Mr = 396.20	F(000) = 400
Triclinic, P1	Dx = 1.662 Mg m−3
a = 6.701 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.492 (3) Å	Cell parameters from 850 reflections
c = 13.011 (3) Å	θ = 2.6–24.3°
α = 105.866 (2)°	µ = 2.63 mm−1
β = 92.535 (2)°	T = 298 K
γ = 94.496 (2)°	Cut from needle, yellow
V = 791.7 (4) Å3	0.13 × 0.12 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	3356 independent reflections
Radiation source: fine-focus sealed tube	1142 reflections with I > 2σ(I)
graphite	Rint = 0.109
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.726, Tmax = 0.779	k = −12→11
6325 measured reflections	l = −16→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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.236	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0975P)2] where P = (Fo2 + 2Fc2)/3
3356 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.56 e Å−3
1 restraint	Δρmin = −0.83 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.86686 (17)	−0.35734 (12)	−0.00940 (10)	0.0719 (6)
N1	0.6581 (10)	0.3028 (8)	0.2164 (6)	0.048 (2)
N2	0.7644 (11)	0.4381 (8)	0.2533 (7)	0.053 (2)
N3	0.6919 (17)	1.0932 (11)	0.4149 (7)	0.065 (3)
O1	0.3298 (9)	0.1075 (7)	0.1801 (6)	0.065 (2)
H1	0.3900	0.1899	0.2010	0.097*
O2	0.4839 (9)	0.5566 (7)	0.2601 (7)	0.075 (2)
O3	0.5095 (13)	1.0768 (8)	0.4134 (7)	0.083 (3)
O4	0.7862 (12)	1.2078 (9)	0.4478 (7)	0.095 (3)
O5	0.1684 (10)	0.3998 (8)	0.3110 (8)	0.080 (2)
H5	0.2535	0.4451	0.2858	0.119*
C1	0.6692 (13)	0.0452 (9)	0.1409 (7)	0.040 (2)
C2	0.4602 (13)	0.0083 (10)	0.1402 (7)	0.045 (3)
C3	0.3811 (13)	−0.1355 (10)	0.0995 (8)	0.052 (3)
H3	0.2446	−0.1599	0.1019	0.062*
C4	0.5030 (15)	−0.2441 (10)	0.0548 (8)	0.058 (3)
H4	0.4491	−0.3409	0.0255	0.069*
C5	0.7013 (14)	−0.2068 (10)	0.0547 (8)	0.051 (3)
C6	0.7845 (13)	−0.0647 (10)	0.0954 (7)	0.045 (3)
H6	0.9214	−0.0428	0.0920	0.054*
C7	0.7583 (13)	0.1925 (10)	0.1837 (8)	0.049 (3)
H7	0.8975	0.2089	0.1880	0.058*
C8	0.6684 (15)	0.5605 (10)	0.2710 (8)	0.050 (3)
C9	0.7917 (13)	0.7039 (10)	0.3036 (8)	0.047 (3)
C10	0.6934 (13)	0.8259 (11)	0.3455 (7)	0.048 (3)
H10	0.5569	0.8164	0.3553	0.058*
C11	0.7981 (15)	0.9610 (10)	0.3723 (8)	0.050 (3)
C12	1.0014 (16)	0.9800 (12)	0.3593 (8)	0.061 (3)
H12	1.0697	1.0735	0.3782	0.073*
C13	1.0973 (15)	0.8607 (13)	0.3191 (9)	0.069 (3)
H13	1.2341	0.8716	0.3102	0.082*
C14	0.9956 (14)	0.7203 (12)	0.2903 (8)	0.060 (3)
H14	1.0640	0.6382	0.2623	0.071*
C15	0.2258 (18)	0.4128 (14)	0.4176 (12)	0.100 (5)
H15A	0.2783	0.5124	0.4524	0.149*
H15B	0.3272	0.3478	0.4208	0.149*
H15C	0.1116	0.3873	0.4530	0.149*
H2	0.893 (5)	0.462 (11)	0.280 (8)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0633 (8)	0.0472 (7)	0.0991 (11)	0.0263 (5)	0.0049 (6)	0.0041 (6)
N1	0.037 (5)	0.039 (5)	0.066 (6)	0.010 (4)	−0.003 (4)	0.010 (4)
N2	0.037 (5)	0.034 (5)	0.079 (6)	0.006 (4)	−0.003 (4)	−0.001 (4)
N3	0.078 (7)	0.050 (6)	0.065 (7)	0.014 (6)	−0.008 (6)	0.011 (5)
O1	0.046 (4)	0.040 (4)	0.105 (6)	0.014 (3)	0.000 (4)	0.011 (4)
O2	0.027 (4)	0.058 (5)	0.138 (7)	0.009 (3)	−0.002 (4)	0.027 (5)
O3	0.072 (6)	0.063 (5)	0.116 (7)	0.032 (4)	0.010 (5)	0.018 (5)
O4	0.089 (6)	0.045 (5)	0.133 (8)	0.013 (5)	−0.015 (5)	−0.003 (5)
O5	0.041 (5)	0.057 (5)	0.135 (8)	0.006 (4)	−0.005 (5)	0.019 (5)
C1	0.033 (5)	0.035 (6)	0.053 (7)	0.006 (4)	0.000 (5)	0.013 (5)
C2	0.038 (6)	0.041 (6)	0.061 (7)	0.019 (5)	0.014 (5)	0.019 (5)
C3	0.034 (5)	0.037 (6)	0.080 (8)	0.003 (5)	0.001 (5)	0.009 (5)
C4	0.060 (7)	0.024 (5)	0.085 (9)	0.004 (5)	−0.008 (6)	0.009 (5)
C5	0.040 (6)	0.039 (6)	0.068 (8)	0.006 (5)	−0.003 (5)	0.005 (5)
C6	0.030 (5)	0.041 (6)	0.061 (7)	0.006 (4)	0.002 (5)	0.009 (5)
C7	0.033 (5)	0.052 (7)	0.064 (7)	0.012 (5)	−0.001 (5)	0.020 (6)
C8	0.045 (7)	0.042 (6)	0.065 (8)	0.016 (5)	0.003 (5)	0.014 (5)
C9	0.034 (6)	0.044 (6)	0.064 (7)	0.015 (5)	0.000 (5)	0.017 (5)
C10	0.034 (5)	0.059 (7)	0.055 (7)	0.018 (5)	0.002 (5)	0.017 (5)
C11	0.056 (7)	0.036 (6)	0.051 (7)	0.004 (5)	−0.004 (5)	0.002 (5)
C12	0.058 (8)	0.057 (7)	0.063 (8)	−0.002 (6)	−0.011 (6)	0.016 (6)
C13	0.039 (6)	0.072 (8)	0.088 (9)	0.011 (6)	−0.005 (6)	0.011 (7)
C14	0.035 (6)	0.064 (8)	0.069 (8)	0.006 (5)	−0.002 (5)	0.001 (6)
C15	0.087 (10)	0.090 (10)	0.109 (12)	0.017 (8)	−0.023 (9)	0.008 (9)

Br1—C5	1.910 (9)	C4—C5	1.348 (12)
N1—C7	1.273 (10)	C4—H4	0.9300
N1—N2	1.370 (10)	C5—C6	1.370 (11)
N2—C8	1.342 (11)	C6—H6	0.9300
N2—H2	0.901 (10)	C7—H7	0.9300
N3—O4	1.175 (10)	C8—C9	1.481 (13)
N3—O3	1.219 (10)	C9—C10	1.370 (12)
N3—C11	1.477 (12)	C9—C14	1.387 (12)
O1—C2	1.349 (9)	C10—C11	1.360 (12)
O1—H1	0.8200	C10—H10	0.9300
O2—C8	1.235 (10)	C11—C12	1.384 (13)
O5—C15	1.392 (13)	C12—C13	1.338 (13)
O5—H5	0.8200	C12—H12	0.9300
C1—C6	1.366 (11)	C13—C14	1.393 (13)
C1—C2	1.416 (12)	C13—H13	0.9300
C1—C7	1.427 (12)	C14—H14	0.9300
C2—C3	1.375 (12)	C15—H15A	0.9600
C3—C4	1.383 (12)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C7—N1—N2	117.1 (8)	C1—C7—H7	118.2
C8—N2—N1	119.9 (8)	O2—C8—N2	122.4 (9)
C8—N2—H2	109 (7)	O2—C8—C9	119.9 (8)
N1—N2—H2	130 (7)	N2—C8—C9	117.7 (8)
O4—N3—O3	123.5 (10)	C10—C9—C14	119.5 (9)
O4—N3—C11	118.9 (10)	C10—C9—C8	116.8 (8)
O3—N3—C11	117.6 (9)	C14—C9—C8	123.7 (9)
C2—O1—H1	109.5	C11—C10—C9	119.1 (9)
C15—O5—H5	109.5	C11—C10—H10	120.4
C6—C1—C2	117.8 (8)	C9—C10—H10	120.4
C6—C1—C7	120.2 (8)	C10—C11—C12	122.3 (9)
C2—C1—C7	122.0 (8)	C10—C11—N3	119.4 (9)
O1—C2—C3	116.6 (8)	C12—C11—N3	118.3 (9)
O1—C2—C1	123.4 (8)	C13—C12—C11	118.4 (10)
C3—C2—C1	120.0 (8)	C13—C12—H12	120.8
C2—C3—C4	120.5 (9)	C11—C12—H12	120.8
C2—C3—H3	119.7	C12—C13—C14	121.1 (10)
C4—C3—H3	119.7	C12—C13—H13	119.5
C5—C4—C3	118.7 (9)	C14—C13—H13	119.5
C5—C4—H4	120.6	C9—C14—C13	119.5 (10)
C3—C4—H4	120.6	C9—C14—H14	120.2
C4—C5—C6	122.0 (9)	C13—C14—H14	120.2
C4—C5—Br1	118.2 (7)	O5—C15—H15A	109.5
C6—C5—Br1	119.7 (7)	O5—C15—H15B	109.5
C1—C6—C5	120.9 (8)	H15A—C15—H15B	109.5
C1—C6—H6	119.6	O5—C15—H15C	109.5
C5—C6—H6	119.6	H15A—C15—H15C	109.5
N1—C7—C1	123.7 (8)	H15B—C15—H15C	109.5
N1—C7—H7	118.2

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5i	0.90 (1)	2.04 (5)	2.854 (10)	150 (9)
O5—H5···O2	0.82	1.90	2.701 (10)	166.
O1—H1···N1	0.82	1.99	2.700 (10)	144.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5i	0.90 (1)	2.04 (5)	2.854 (10)	150 (9)
O5—H5⋯O2	0.82	1.90	2.701 (10)	166
O1—H1⋯N1	0.82	1.99	2.700 (10)	144

Symmetry code: (i) .