(E)-N'-(5-Bromo-2-meth-oxy-benzyl-idene)-2-chloro-benzohydrazide.

In the title compound, C(15)H(12)BrClN(2)O(2), the dihedral angle between the two substituted aromatic rings is 77.8 (3)°. The mol-ecule exists in a trans conformation with respect to the methyl-idene unit. In the crystal structure, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (8)(8) loops.

Related literature

For the crystal structures of some related hydrazone compounds, see: Li (2011a ▶,b ▶); Hashemian et al. (2011 ▶); Lei (2011 ▶); Shalash et al. (2010 ▶). For hydrogen-bond notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H12BrClN2O2

M = 367.63

Monoclinic,

a = 11.312 (2) Å

b = 7.374 (2) Å

c = 17.979 (3) Å

β = 91.972 (3)°

V = 1499.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.93 mm−1

T = 298 K

0.12 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.720, T max = 0.821

5249 measured reflections

2451 independent reflections

1877 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 1.04

2451 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.46 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536811034623/hb6337sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034623/hb6337Isup2.hkl

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

C15H12BrClN2O2	F(000) = 736
Mr = 367.63	Dx = 1.629 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.312 (2) Å	Cell parameters from 1972 reflections
b = 7.374 (2) Å	θ = 3.1–24.9°
c = 17.979 (3) Å	µ = 2.93 mm−1
β = 91.972 (3)°	T = 298 K
V = 1499.0 (5) Å3	Block, colourless
Z = 4	0.12 × 0.10 × 0.07 mm

Bruker SMART CCD diffractometer	2451 independent reflections
Radiation source: fine-focus sealed tube	1877 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.720, Tmax = 0.821	k = −8→6
5249 measured reflections	l = −20→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.678P] where P = (Fo2 + 2Fc2)/3
2451 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.46 e Å−3
1 restraint	Δρmin = −0.46 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	0.68536 (3)	0.08870 (6)	0.13010 (2)	0.05792 (18)
Cl1	0.20872 (10)	0.35802 (17)	0.20909 (7)	0.0738 (4)
N1	0.2386 (2)	0.2805 (4)	0.03030 (15)	0.0362 (6)
N2	0.1252 (2)	0.3513 (4)	0.02797 (16)	0.0405 (7)
O1	0.4312 (2)	0.3783 (4)	−0.14532 (14)	0.0534 (7)
O2	−0.05797 (18)	0.3567 (3)	0.07125 (14)	0.0533 (7)
C1	0.4308 (2)	0.2898 (4)	−0.02015 (18)	0.0358 (7)
C2	0.4949 (3)	0.3117 (5)	−0.08532 (19)	0.0402 (8)
C3	0.6132 (3)	0.2662 (5)	−0.0855 (2)	0.0484 (9)
H3	0.6552	0.2811	−0.1287	0.058*
C4	0.6700 (3)	0.1984 (5)	−0.0217 (2)	0.0468 (9)
H4	0.7496	0.1668	−0.0221	0.056*
C5	0.6074 (3)	0.1783 (5)	0.04254 (19)	0.0401 (8)
C6	0.4885 (3)	0.2236 (4)	0.04331 (19)	0.0390 (8)
H6	0.4472	0.2093	0.0868	0.047*
C7	0.3058 (3)	0.3422 (4)	−0.01972 (19)	0.0375 (8)
H7	0.2752	0.4208	−0.0560	0.045*
C8	0.0425 (2)	0.2909 (4)	0.07350 (18)	0.0362 (7)
C9	0.0717 (2)	0.1349 (4)	0.12478 (18)	0.0348 (8)
C10	0.1435 (3)	0.1509 (5)	0.1879 (2)	0.0445 (9)
C11	0.1611 (3)	0.0055 (7)	0.2367 (2)	0.0578 (11)
H11	0.2078	0.0194	0.2799	0.069*
C12	0.1087 (4)	−0.1580 (6)	0.2202 (3)	0.0627 (12)
H12	0.1215	−0.2560	0.2521	0.075*
C13	0.0377 (4)	−0.1789 (6)	0.1573 (3)	0.0613 (11)
H13	0.0037	−0.2910	0.1465	0.074*
C14	0.0166 (3)	−0.0332 (5)	0.1098 (2)	0.0476 (9)
H14	−0.0338	−0.0464	0.0682	0.057*
C15	0.4912 (4)	0.4085 (6)	−0.2124 (2)	0.0649 (12)
H15A	0.5509	0.4995	−0.2042	0.097*
H15B	0.4357	0.4488	−0.2505	0.097*
H15C	0.5276	0.2977	−0.2278	0.097*
H2	0.109 (4)	0.444 (4)	−0.0024 (19)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0437 (2)	0.0720 (3)	0.0575 (3)	0.00185 (18)	−0.00739 (17)	0.0012 (2)
Cl1	0.0748 (7)	0.0728 (8)	0.0728 (8)	−0.0254 (6)	−0.0124 (6)	−0.0101 (6)
N1	0.0305 (12)	0.0354 (16)	0.0430 (17)	0.0034 (11)	0.0047 (11)	0.0041 (13)
N2	0.0293 (13)	0.0413 (17)	0.051 (2)	0.0057 (11)	0.0055 (12)	0.0133 (14)
O1	0.0489 (14)	0.0648 (18)	0.0473 (16)	0.0000 (12)	0.0109 (12)	0.0140 (13)
O2	0.0318 (12)	0.0558 (16)	0.0728 (19)	0.0101 (11)	0.0087 (11)	0.0244 (14)
C1	0.0330 (15)	0.0330 (18)	0.042 (2)	−0.0017 (13)	0.0054 (14)	−0.0016 (15)
C2	0.0435 (18)	0.035 (2)	0.042 (2)	−0.0066 (15)	0.0062 (15)	−0.0031 (16)
C3	0.0410 (18)	0.051 (2)	0.054 (2)	−0.0043 (16)	0.0197 (17)	−0.0017 (19)
C4	0.0323 (16)	0.048 (2)	0.061 (3)	−0.0004 (15)	0.0104 (16)	−0.0026 (19)
C5	0.0356 (16)	0.0345 (19)	0.050 (2)	−0.0040 (14)	0.0011 (15)	−0.0035 (16)
C6	0.0347 (16)	0.0371 (19)	0.046 (2)	−0.0060 (14)	0.0086 (15)	−0.0037 (16)
C7	0.0392 (17)	0.0310 (18)	0.042 (2)	0.0000 (13)	0.0045 (15)	0.0010 (15)
C8	0.0312 (15)	0.0343 (19)	0.043 (2)	−0.0012 (13)	−0.0012 (13)	0.0042 (15)
C9	0.0285 (15)	0.0348 (19)	0.042 (2)	0.0046 (12)	0.0089 (14)	0.0051 (15)
C10	0.0339 (16)	0.050 (2)	0.049 (2)	0.0010 (15)	0.0013 (16)	−0.0007 (18)
C11	0.047 (2)	0.075 (3)	0.051 (3)	0.014 (2)	0.0002 (17)	0.017 (2)
C12	0.056 (2)	0.062 (3)	0.071 (3)	0.012 (2)	0.012 (2)	0.031 (2)
C13	0.067 (3)	0.039 (2)	0.079 (3)	−0.0035 (19)	0.017 (2)	0.010 (2)
C14	0.0476 (19)	0.044 (2)	0.051 (2)	−0.0011 (16)	0.0098 (17)	0.0049 (18)
C15	0.066 (2)	0.079 (3)	0.050 (3)	−0.011 (2)	0.014 (2)	0.012 (2)

Br1—C5	1.897 (3)	C5—C6	1.386 (4)
Cl1—C10	1.733 (4)	C6—H6	0.9300
N1—C7	1.282 (4)	C7—H7	0.9300
N1—N2	1.384 (3)	C8—C9	1.504 (4)
N2—C8	1.340 (4)	C9—C10	1.377 (5)
N2—H2	0.893 (10)	C9—C14	1.409 (5)
O1—C2	1.368 (4)	C10—C11	1.395 (5)
O1—C15	1.422 (4)	C11—C12	1.371 (6)
O2—C8	1.235 (3)	C11—H11	0.9300
C1—C6	1.384 (5)	C12—C13	1.373 (6)
C1—C2	1.408 (4)	C12—H12	0.9300
C1—C7	1.466 (4)	C13—C14	1.388 (5)
C2—C3	1.380 (5)	C13—H13	0.9300
C3—C4	1.390 (5)	C14—H14	0.9300
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.384 (5)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C7—N1—N2	114.6 (3)	O2—C8—C9	120.2 (3)
C8—N2—N1	121.5 (3)	N2—C8—C9	119.0 (3)
C8—N2—H2	120 (3)	C10—C9—C14	118.5 (3)
N1—N2—H2	119 (3)	C10—C9—C8	123.4 (3)
C2—O1—C15	118.1 (3)	C14—C9—C8	118.0 (3)
C6—C1—C2	119.0 (3)	C9—C10—C11	121.3 (4)
C6—C1—C7	121.1 (3)	C9—C10—Cl1	119.4 (3)
C2—C1—C7	119.9 (3)	C11—C10—Cl1	119.2 (3)
O1—C2—C3	124.7 (3)	C12—C11—C10	119.3 (4)
O1—C2—C1	115.2 (3)	C12—C11—H11	120.4
C3—C2—C1	120.1 (3)	C10—C11—H11	120.4
C2—C3—C4	120.4 (3)	C11—C12—C13	120.8 (4)
C2—C3—H3	119.8	C11—C12—H12	119.6
C4—C3—H3	119.8	C13—C12—H12	119.6
C5—C4—C3	119.5 (3)	C12—C13—C14	120.2 (4)
C5—C4—H4	120.2	C12—C13—H13	119.9
C3—C4—H4	120.2	C14—C13—H13	119.9
C4—C5—C6	120.5 (3)	C13—C14—C9	119.9 (4)
C4—C5—Br1	119.5 (2)	C13—C14—H14	120.1
C6—C5—Br1	120.0 (3)	C9—C14—H14	120.1
C1—C6—C5	120.5 (3)	O1—C15—H15A	109.5
C1—C6—H6	119.8	O1—C15—H15B	109.5
C5—C6—H6	119.8	H15A—C15—H15B	109.5
N1—C7—C1	120.4 (3)	O1—C15—H15C	109.5
N1—C7—H7	119.8	H15A—C15—H15C	109.5
C1—C7—H7	119.8	H15B—C15—H15C	109.5
O2—C8—N2	120.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.89 (1)	1.99 (1)	2.882 (4)	175 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.89 (1)	1.99 (1)	2.882 (4)	175 (4)

Symmetry code: (i) .