(E)-3-Bromo-N'-(4-methoxy-benzyl-idene)benzohydrazide methanol solvate.

The title compound, C(15)H(13)BrN(2)O(2)·CH(3)OH, was synthesized by the reaction of 4-methoxy-benzaldehyde with an equimolar quantity of 3-bromo-benzohydrazide in methanol. The benzohydrazide mol-ecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 4.0 (2)°. The benzohydrazide and methanol mol-ecules are linked into a chain propagating along the b axis by O-H⋯O, O-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Li & Ban (2009 ▶); Zhu et al. (2009 ▶); Yang (2007 ▶); You et al. (2008 ▶). For hydrazone compounds reported previously by our group, see: Qu et al. (2008 ▶); Yang et al. (2008 ▶); Cao & Lu (2009a ▶,b ▶); Qu & Cao (2009 ▶); Cao & Wang (2009 ▶); Cao (2009 ▶).

Experimental

Crystal data

C15H13BrN2O2·CH4O

M = 365.23

Monoclinic,

a = 13.585 (1) Å

b = 6.715 (1) Å

c = 18.377 (1) Å

β = 104.429 (2)°

V = 1623.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.55 mm−1

T = 298 K

0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.630, T max = 0.672

9539 measured reflections

3539 independent reflections

2132 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.103

S = 1.02

3539 reflections

205 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.52 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030219/ci2872sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030219/ci2872Isup2.hkl

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

C15H13BrN2O2·CH4O	F(000) = 744
Mr = 365.23	Dx = 1.494 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2168 reflections
a = 13.585 (1) Å	θ = 2.7–24.6°
b = 6.715 (1) Å	µ = 2.55 mm−1
c = 18.377 (1) Å	T = 298 K
β = 104.429 (2)°	Block, colourless
V = 1623.5 (3) Å3	0.20 × 0.20 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3539 independent reflections
Radiation source: fine-focus sealed tube	2132 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→17
Tmin = 0.630, Tmax = 0.672	k = −8→8
9539 measured reflections	l = −23→20

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.043P)2 + 0.516P] where P = (Fo2 + 2Fc2)/3
3539 reflections	(Δ/σ)max = 0.001
205 parameters	Δρmax = 0.41 e Å−3
1 restraint	Δρmin = −0.52 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	0.53424 (3)	0.09750 (6)	−0.18341 (2)	0.09185 (19)
O1	0.26855 (15)	0.2642 (3)	−0.02385 (11)	0.0608 (5)
O2	−0.19847 (15)	0.3318 (3)	0.21672 (11)	0.0595 (5)
O3	0.20352 (18)	0.5573 (3)	0.06465 (12)	0.0676 (6)
H3	0.2041	0.4585	0.0385	0.101*
N1	0.21308 (16)	−0.0152 (3)	0.02088 (12)	0.0460 (5)
N2	0.14486 (16)	0.0932 (3)	0.04946 (12)	0.0477 (5)
C1	0.34289 (18)	−0.0397 (4)	−0.04807 (14)	0.0410 (6)
C2	0.3955 (2)	0.0578 (4)	−0.09241 (14)	0.0470 (6)
H2	0.3858	0.1937	−0.1011	0.056*
C3	0.4622 (2)	−0.0442 (4)	−0.12395 (15)	0.0504 (7)
C4	0.4778 (2)	−0.2432 (4)	−0.11248 (16)	0.0573 (8)
H4	0.5230	−0.3111	−0.1341	0.069*
C5	0.4257 (2)	−0.3414 (4)	−0.06842 (17)	0.0560 (7)
H5	0.4360	−0.4773	−0.0602	0.067*
C6	0.3584 (2)	−0.2429 (4)	−0.03613 (15)	0.0488 (7)
H6	0.3236	−0.3120	−0.0065	0.059*
C7	0.27195 (19)	0.0826 (4)	−0.01586 (14)	0.0446 (6)
C8	0.0896 (2)	−0.0058 (4)	0.08234 (15)	0.0485 (6)
H8	0.0978	−0.1432	0.0862	0.058*
C9	0.01344 (18)	0.0883 (4)	0.11444 (14)	0.0430 (6)
C10	−0.0341 (2)	−0.0209 (4)	0.15986 (15)	0.0488 (7)
H10	−0.0179	−0.1549	0.1683	0.059*
C11	−0.1040 (2)	0.0628 (4)	0.19264 (15)	0.0519 (7)
H11	−0.1342	−0.0137	0.2232	0.062*
C12	−0.12967 (19)	0.2614 (4)	0.18031 (14)	0.0451 (6)
C13	−0.0856 (2)	0.3731 (4)	0.13385 (15)	0.0474 (6)
H13	−0.1038	0.5058	0.1242	0.057*
C14	−0.0142 (2)	0.2866 (4)	0.10182 (15)	0.0474 (6)
H14	0.0159	0.3630	0.0711	0.057*
C15	−0.2213 (2)	0.5384 (4)	0.21096 (18)	0.0662 (9)
H15A	−0.1611	0.6134	0.2330	0.099*
H15B	−0.2728	0.5674	0.2370	0.099*
H15C	−0.2455	0.5742	0.1590	0.099*
C16	0.2481 (3)	0.5111 (5)	0.13973 (19)	0.0749 (9)
H16A	0.3160	0.4636	0.1445	0.112*
H16B	0.2088	0.4098	0.1563	0.112*
H16C	0.2500	0.6283	0.1700	0.112*
H1	0.210 (2)	−0.1474 (16)	0.0258 (17)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.1033 (3)	0.0942 (3)	0.0980 (3)	−0.0125 (2)	0.0627 (2)	0.0055 (2)
O1	0.0810 (14)	0.0302 (11)	0.0831 (14)	0.0074 (9)	0.0428 (11)	0.0037 (9)
O2	0.0673 (12)	0.0512 (11)	0.0699 (13)	0.0065 (9)	0.0358 (10)	0.0029 (10)
O3	0.1030 (16)	0.0346 (11)	0.0763 (15)	0.0028 (11)	0.0434 (13)	−0.0005 (10)
N1	0.0513 (13)	0.0327 (11)	0.0584 (14)	0.0025 (10)	0.0218 (11)	−0.0012 (11)
N2	0.0514 (13)	0.0417 (12)	0.0538 (14)	0.0046 (10)	0.0202 (11)	−0.0054 (11)
C1	0.0431 (14)	0.0351 (14)	0.0431 (15)	0.0001 (11)	0.0075 (12)	−0.0043 (11)
C2	0.0519 (16)	0.0369 (14)	0.0515 (16)	−0.0012 (12)	0.0112 (13)	0.0010 (12)
C3	0.0512 (16)	0.0540 (18)	0.0481 (16)	−0.0026 (13)	0.0163 (13)	−0.0029 (13)
C4	0.0560 (18)	0.0532 (18)	0.0635 (19)	0.0122 (14)	0.0167 (15)	−0.0099 (15)
C5	0.0638 (19)	0.0358 (15)	0.0686 (19)	0.0104 (13)	0.0172 (16)	−0.0023 (14)
C6	0.0544 (17)	0.0328 (14)	0.0599 (17)	0.0010 (12)	0.0153 (14)	0.0017 (12)
C7	0.0483 (15)	0.0376 (16)	0.0471 (15)	0.0051 (12)	0.0105 (12)	−0.0003 (12)
C8	0.0520 (17)	0.0381 (14)	0.0564 (17)	0.0032 (13)	0.0153 (14)	−0.0028 (13)
C9	0.0411 (14)	0.0406 (15)	0.0453 (15)	−0.0004 (12)	0.0071 (12)	−0.0041 (12)
C10	0.0567 (17)	0.0361 (14)	0.0548 (16)	0.0020 (12)	0.0161 (14)	0.0028 (13)
C11	0.0606 (18)	0.0443 (16)	0.0555 (17)	−0.0027 (13)	0.0231 (14)	0.0082 (13)
C12	0.0454 (15)	0.0463 (16)	0.0459 (15)	−0.0012 (12)	0.0158 (12)	−0.0027 (12)
C13	0.0538 (16)	0.0339 (14)	0.0559 (17)	0.0038 (12)	0.0165 (13)	0.0013 (12)
C14	0.0537 (16)	0.0397 (15)	0.0520 (16)	−0.0033 (12)	0.0189 (13)	0.0029 (13)
C15	0.073 (2)	0.059 (2)	0.073 (2)	0.0194 (16)	0.0303 (17)	−0.0001 (16)
C16	0.086 (2)	0.064 (2)	0.078 (3)	−0.0032 (18)	0.028 (2)	−0.0082 (19)

Br1—C3	1.895 (3)	C6—H6	0.93
O1—C7	1.227 (3)	C8—C9	1.456 (3)
O2—C12	1.363 (3)	C8—H8	0.93
O2—C15	1.420 (3)	C9—C10	1.385 (4)
O3—C16	1.396 (4)	C9—C14	1.387 (3)
O3—H3	0.82	C10—C11	1.366 (4)
N1—C7	1.340 (3)	C10—H10	0.93
N1—N2	1.381 (3)	C11—C12	1.382 (4)
N1—H1	0.895 (10)	C11—H11	0.93
N2—C8	1.264 (3)	C12—C13	1.380 (3)
C1—C2	1.376 (3)	C13—C14	1.381 (3)
C1—C6	1.390 (4)	C13—H13	0.93
C1—C7	1.496 (3)	C14—H14	0.93
C2—C3	1.374 (3)	C15—H15A	0.96
C2—H2	0.93	C15—H15B	0.96
C3—C4	1.361 (4)	C15—H15C	0.96
C4—C5	1.370 (4)	C16—H16A	0.96
C4—H4	0.93	C16—H16B	0.96
C5—C6	1.376 (4)	C16—H16C	0.96
C5—H5	0.93
C12—O2—C15	117.8 (2)	C10—C9—C14	117.5 (2)
C16—O3—H3	109.5	C10—C9—C8	119.9 (2)
C7—N1—N2	118.3 (2)	C14—C9—C8	122.6 (2)
C7—N1—H1	126 (2)	C11—C10—C9	121.8 (2)
N2—N1—H1	115 (2)	C11—C10—H10	119.1
C8—N2—N1	116.1 (2)	C9—C10—H10	119.1
C2—C1—C6	118.7 (2)	C10—C11—C12	120.0 (2)
C2—C1—C7	117.0 (2)	C10—C11—H11	120.0
C6—C1—C7	124.4 (2)	C12—C11—H11	120.0
C3—C2—C1	120.4 (2)	O2—C12—C13	124.9 (2)
C3—C2—H2	119.8	O2—C12—C11	115.5 (2)
C1—C2—H2	119.8	C13—C12—C11	119.6 (2)
C4—C3—C2	121.2 (2)	C12—C13—C14	119.6 (2)
C4—C3—Br1	119.9 (2)	C12—C13—H13	120.2
C2—C3—Br1	118.9 (2)	C14—C13—H13	120.2
C3—C4—C5	118.7 (2)	C13—C14—C9	121.5 (2)
C3—C4—H4	120.7	C13—C14—H14	119.3
C5—C4—H4	120.7	C9—C14—H14	119.3
C4—C5—C6	121.3 (3)	O2—C15—H15A	109.5
C4—C5—H5	119.3	O2—C15—H15B	109.5
C6—C5—H5	119.3	H15A—C15—H15B	109.5
C5—C6—C1	119.6 (3)	O2—C15—H15C	109.5
C5—C6—H6	120.2	H15A—C15—H15C	109.5
C1—C6—H6	120.2	H15B—C15—H15C	109.5
O1—C7—N1	122.5 (2)	O3—C16—H16A	109.5
O1—C7—C1	120.5 (2)	O3—C16—H16B	109.5
N1—C7—C1	117.0 (2)	H16A—C16—H16B	109.5
N2—C8—C9	122.1 (2)	O3—C16—H16C	109.5
N2—C8—H8	118.9	H16A—C16—H16C	109.5
C9—C8—H8	118.9	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.82	2.07	2.831 (3)	154
O3—H3···N2	0.82	2.60	3.211 (3)	132
N1—H1···O3i	0.90 (1)	2.12 (1)	2.993 (3)	166 (3)
C6—H6···O3i	0.93	2.49	3.406 (4)	168
C8—H8···O3i	0.93	2.56	3.370 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1	0.82	2.07	2.831 (3)	154
O3—H3⋯N2	0.82	2.60	3.211 (3)	132
N1—H1⋯O3i	0.90 (1)	2.12 (1)	2.993 (3)	166 (3)
C6—H6⋯O3i	0.93	2.49	3.406 (4)	168
C8—H8⋯O3i	0.93	2.56	3.370 (3)	146

Symmetry code: (i) .