N'-(5-Bromo-2-methoxy-benzyl-idene)-4-hydroxy-benzohydrazide methanol solvate.

In the title hydrazone compound, C(15)H(13)BrN(2)O(3)·CH(3)OH, the methanol solvate is linked to the benzohydrazide molecule through O-H⋯N and O-H⋯O hydrogen bonds. The benzohydrazide mol-ecule adopts an E configuration about the C=N double bond. The mol-ecule is twisted, with a dihedral angle between the two substituted benzene rings of 35.7 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, forming layers parallel to the ac plane.

Related literature

For the biological properties of the hydrazone compounds, see: Khattab (2005 ▶); Küçükgüzel et al. (2003 ▶); Çukurovalı et al. (2006 ▶). For the structures of hydrazone derivatives, see: Fun et al. (2008 ▶); Wei et al. (2009 ▶); Khaledi et al. (2008 ▶); Yang et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H13BrN2O3·CH4O

M = 381.23

Orthorhombic,

a = 11.1886 (7) Å

b = 14.4464 (9) Å

c = 20.5927 (13) Å

V = 3328.5 (4) Å3

Z = 8

Mo Kα radiation

μ = 2.49 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.598, T max = 0.636

19306 measured reflections

3638 independent reflections

2234 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.179

S = 1.06

3638 reflections

214 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.95 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022983/at2817sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022983/at2817Isup2.hkl

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

C15H13BrN2O3·CH4O	F(000) = 1552
Mr = 381.23	Dx = 1.522 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3350 reflections
a = 11.1886 (7) Å	θ = 2.5–24.5°
b = 14.4464 (9) Å	µ = 2.49 mm−1
c = 20.5927 (13) Å	T = 298 K
V = 3328.5 (4) Å3	Block, colourless
Z = 8	0.23 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	3638 independent reflections
Radiation source: fine-focus sealed tube	2234 reflections with I > 2σ(I)
graphite	Rint = 0.054
ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.598, Tmax = 0.636	k = −18→15
19306 measured reflections	l = −23→26

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) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0849P)2 + 4.4269P] where P = (Fo2 + 2Fc2)/3
3638 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.95 e Å−3
1 restraint	Δρmin = −0.82 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	0.82955 (5)	0.03436 (5)	0.73273 (2)	0.0699 (3)
N1	0.7667 (3)	0.1520 (3)	0.48426 (15)	0.0388 (8)
N2	0.7226 (3)	0.1789 (3)	0.42463 (16)	0.0396 (8)
O1	1.1184 (3)	0.1179 (3)	0.49400 (17)	0.0591 (9)
O2	0.5326 (3)	0.1584 (2)	0.45803 (13)	0.0472 (8)
O3	0.4288 (3)	0.2326 (3)	0.16133 (13)	0.0499 (9)
H3	0.4694	0.2697	0.1408	0.075*
O4	0.5525 (4)	0.1537 (3)	0.59007 (15)	0.0589 (10)
H4	0.5657	0.1611	0.5512	0.088*
C1	0.9352 (4)	0.1136 (3)	0.54842 (19)	0.0365 (9)
C2	1.0590 (4)	0.0944 (3)	0.5493 (2)	0.0422 (10)
C3	1.1097 (4)	0.0555 (3)	0.6035 (2)	0.0488 (12)
H3A	1.1908	0.0415	0.6034	0.059*
C4	1.0431 (5)	0.0369 (4)	0.6572 (2)	0.0521 (12)
H4A	1.0784	0.0104	0.6936	0.062*
C5	0.9219 (4)	0.0579 (3)	0.6571 (2)	0.0412 (10)
C6	0.8690 (4)	0.0949 (3)	0.6038 (2)	0.0381 (10)
H6	0.7876	0.1078	0.6044	0.046*
C7	1.2442 (5)	0.1054 (5)	0.4918 (3)	0.0724 (17)
H7A	1.2804	0.1366	0.5279	0.109*
H7B	1.2748	0.1307	0.4520	0.109*
H7C	1.2625	0.0406	0.4939	0.109*
C8	0.8794 (4)	0.1474 (3)	0.48878 (19)	0.0387 (10)
H8	0.9269	0.1655	0.4540	0.046*
C9	0.6031 (4)	0.1770 (3)	0.41462 (18)	0.0348 (9)
C10	0.5622 (3)	0.1963 (3)	0.34754 (18)	0.0324 (9)
C11	0.6285 (4)	0.2436 (3)	0.30120 (19)	0.0366 (9)
H11	0.7031	0.2670	0.3123	0.044*
C12	0.5861 (4)	0.2567 (3)	0.23906 (18)	0.0400 (10)
H12	0.6320	0.2882	0.2086	0.048*
C13	0.4747 (4)	0.2226 (3)	0.22221 (19)	0.0373 (10)
C14	0.4067 (4)	0.1763 (3)	0.26778 (19)	0.0408 (10)
H14	0.3320	0.1531	0.2566	0.049*
C15	0.4499 (4)	0.1648 (3)	0.3298 (2)	0.0397 (10)
H15	0.4026	0.1351	0.3606	0.048*
H2	0.777 (4)	0.182 (4)	0.393 (2)	0.080*
C16	0.5253 (6)	0.0617 (4)	0.6017 (3)	0.0657 (15)
H16A	0.5874	0.0231	0.5844	0.099*
H16B	0.4508	0.0466	0.5811	0.099*
H16C	0.5187	0.0516	0.6476	0.099*

	U11	U22	U33	U12	U13	U23
Br1	0.0692 (4)	0.1010 (5)	0.0395 (3)	−0.0096 (3)	0.0019 (2)	0.0223 (3)
N1	0.039 (2)	0.051 (2)	0.0270 (17)	−0.0015 (17)	−0.0030 (14)	0.0055 (15)
N2	0.037 (2)	0.057 (2)	0.0242 (17)	0.0008 (18)	0.0011 (14)	0.0086 (16)
O1	0.0380 (18)	0.086 (3)	0.053 (2)	0.0017 (18)	0.0135 (15)	0.0008 (18)
O2	0.0429 (17)	0.071 (2)	0.0277 (15)	−0.0026 (16)	0.0035 (13)	0.0088 (14)
O3	0.0448 (18)	0.077 (2)	0.0283 (15)	−0.0177 (17)	−0.0081 (13)	0.0087 (15)
O4	0.080 (3)	0.067 (2)	0.0300 (16)	0.007 (2)	0.0109 (16)	−0.0003 (15)
C1	0.032 (2)	0.045 (3)	0.032 (2)	−0.0008 (19)	−0.0022 (17)	−0.0001 (18)
C2	0.036 (2)	0.048 (3)	0.042 (2)	0.002 (2)	0.0020 (19)	−0.006 (2)
C3	0.033 (2)	0.057 (3)	0.056 (3)	0.005 (2)	−0.006 (2)	−0.003 (2)
C4	0.049 (3)	0.059 (3)	0.048 (3)	0.005 (2)	−0.014 (2)	0.008 (2)
C5	0.044 (3)	0.043 (3)	0.037 (2)	−0.006 (2)	−0.0039 (19)	0.0031 (19)
C6	0.031 (2)	0.048 (3)	0.035 (2)	−0.0042 (19)	−0.0032 (17)	0.0042 (19)
C7	0.040 (3)	0.086 (4)	0.091 (4)	0.002 (3)	0.022 (3)	−0.005 (4)
C8	0.037 (2)	0.049 (3)	0.030 (2)	−0.002 (2)	0.0032 (17)	0.0052 (18)
C9	0.037 (2)	0.041 (2)	0.0264 (19)	0.0014 (19)	0.0022 (16)	0.0027 (17)
C10	0.032 (2)	0.039 (2)	0.0266 (19)	0.0022 (18)	0.0013 (16)	0.0025 (16)
C11	0.032 (2)	0.049 (3)	0.029 (2)	−0.0019 (19)	−0.0015 (16)	0.0012 (19)
C12	0.036 (2)	0.058 (3)	0.026 (2)	−0.008 (2)	0.0002 (17)	0.0042 (18)
C13	0.037 (2)	0.048 (3)	0.0275 (19)	−0.0042 (19)	−0.0018 (17)	0.0002 (18)
C14	0.031 (2)	0.054 (3)	0.037 (2)	−0.007 (2)	−0.0029 (18)	0.007 (2)
C15	0.035 (2)	0.051 (3)	0.033 (2)	−0.003 (2)	0.0062 (17)	0.0095 (19)
C16	0.071 (4)	0.059 (4)	0.067 (4)	0.004 (3)	0.010 (3)	0.006 (3)

Br1—C5	1.899 (4)	C5—C6	1.357 (6)
N1—C8	1.266 (6)	C6—H6	0.9300
N1—N2	1.379 (4)	C7—H7A	0.9600
N2—C9	1.354 (6)	C7—H7B	0.9600
N2—H2	0.89 (4)	C7—H7C	0.9600
O1—C2	1.362 (5)	C8—H8	0.9300
O1—C7	1.420 (6)	C9—C10	1.481 (5)
O2—C9	1.222 (5)	C10—C15	1.385 (6)
O3—C13	1.363 (5)	C10—C11	1.388 (6)
O3—H3	0.8200	C11—C12	1.378 (5)
O4—C16	1.385 (6)	C11—H11	0.9300
O4—H4	0.8200	C12—C13	1.384 (6)
C1—C6	1.386 (6)	C12—H12	0.9300
C1—C2	1.413 (6)	C13—C14	1.381 (6)
C1—C8	1.462 (6)	C14—C15	1.377 (6)
C2—C3	1.371 (6)	C14—H14	0.9300
C3—C4	1.361 (7)	C15—H15	0.9300
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.389 (7)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C8—N1—N2	115.9 (3)	N1—C8—C1	120.3 (4)
C9—N2—N1	118.9 (3)	N1—C8—H8	119.8
C9—N2—H2	124 (4)	C1—C8—H8	119.8
N1—N2—H2	115 (4)	O2—C9—N2	122.0 (4)
C2—O1—C7	118.6 (4)	O2—C9—C10	121.7 (4)
C13—O3—H3	109.5	N2—C9—C10	116.3 (3)
C16—O4—H4	109.5	C15—C10—C11	117.7 (4)
C6—C1—C2	118.3 (4)	C15—C10—C9	117.6 (3)
C6—C1—C8	121.9 (4)	C11—C10—C9	124.7 (4)
C2—C1—C8	119.7 (4)	C12—C11—C10	121.5 (4)
O1—C2—C3	125.5 (4)	C12—C11—H11	119.3
O1—C2—C1	114.7 (4)	C10—C11—H11	119.3
C3—C2—C1	119.8 (4)	C11—C12—C13	119.6 (4)
C4—C3—C2	121.0 (4)	C11—C12—H12	120.2
C4—C3—H3A	119.5	C13—C12—H12	120.2
C2—C3—H3A	119.5	O3—C13—C14	117.9 (4)
C3—C4—C5	119.4 (4)	O3—C13—C12	122.2 (4)
C3—C4—H4A	120.3	C14—C13—C12	119.9 (4)
C5—C4—H4A	120.3	C15—C14—C13	119.7 (4)
C6—C5—C4	120.8 (4)	C15—C14—H14	120.1
C6—C5—Br1	119.8 (3)	C13—C14—H14	120.1
C4—C5—Br1	119.4 (3)	C14—C15—C10	121.5 (4)
C5—C6—C1	120.6 (4)	C14—C15—H15	119.2
C5—C6—H6	119.7	C10—C15—H15	119.2
C1—C6—H6	119.7	O4—C16—H16A	109.5
O1—C7—H7A	109.5	O4—C16—H16B	109.5
O1—C7—H7B	109.5	H16A—C16—H16B	109.5
H7A—C7—H7B	109.5	O4—C16—H16C	109.5
O1—C7—H7C	109.5	H16A—C16—H16C	109.5
H7A—C7—H7C	109.5	H16B—C16—H16C	109.5
H7B—C7—H7C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.89 (4)	2.16 (5)	3.009 (4)	158 (5)
O4—H4···N1	0.82	2.64	3.239 (5)	131
O4—H4···O2	0.82	1.96	2.729 (4)	157
O3—H3···O4ii	0.82	1.78	2.602 (5)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.89 (4)	2.16 (5)	3.009 (4)	158 (5)
O4—H4⋯N1	0.82	2.64	3.239 (5)	131
O4—H4⋯O2	0.82	1.96	2.729 (4)	157
O3—H3⋯O4ii	0.82	1.78	2.602 (5)	175

Symmetry codes: (i) ; (ii) .