2-Bromo-N'-[(Z)-2-bromo-benzyl-idene]-5-methoxy-benzohydrazide.

In the title compound, C(15)H(12)Br(2)N(2)O(2), the mol-ecule adopts an E conformation about the C=N double bond and a transoid conformation about the central N-N bond, with a C(=O)-N-N-C(H) dihedral angle of 169.4 (4)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, leading to C(4) chains. The packing also features slipped π-π stacking inter-actions, with a centroid-centroid separation of 3.838 (3) Å and a slippage of 1.19 Å.

Related literature

For related structures and background, see: Narayana et al. (2007 ▶); Butcher et al. (2007 ▶).

Experimental

Crystal data

C15H12Br2N2O2

M = 412.09

Monoclinic,

a = 14.768 (5) Å

b = 12.753 (4) Å

c = 8.227 (3) Å

β = 96.114 (4)°

V = 1540.6 (9) Å3

Z = 4

Mo Kα radiation

μ = 5.27 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.301, T max = 0.419 (expected range = 0.251–0.349)

9369 measured reflections

3515 independent reflections

1902 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.122

S = 0.96

3515 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.81 e Å−3

Data collection: SMART (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809024921/fj2231sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024921/fj2231Isup2.hkl

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

C15H12Br2N2O2	F(000) = 808
Mr = 412.09	Dx = 1.777 Mg m−3
Monoclinic, P21/c	Melting point = 440–442 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.768 (5) Å	Cell parameters from 1776 reflections
b = 12.753 (4) Å	θ = 2.8–22.8°
c = 8.227 (3) Å	µ = 5.27 mm−1
β = 96.114 (4)°	T = 296 K
V = 1540.6 (9) Å3	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	3515 independent reflections
Radiation source: fine-focus sealed tube	1902 reflections with I > 2σ(I)
graphite	Rint = 0.063
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −19→14
Tmin = 0.301, Tmax = 0.419	k = −12→16
9369 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0504P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.001
3515 reflections	Δρmax = 0.57 e Å−3
195 parameters	Δρmin = −0.81 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0145 (10)

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
C1	0.1558 (3)	0.0150 (3)	0.5766 (5)	0.0405 (11)
C2	0.1498 (3)	0.1213 (3)	0.5376 (5)	0.0322 (9)
C3	0.0842 (3)	0.1808 (3)	0.6039 (5)	0.0367 (10)
H3	0.0794	0.2520	0.5796	0.044*
C4	0.0256 (3)	0.1365 (3)	0.7055 (5)	0.0415 (11)
C5	0.0317 (3)	0.0314 (4)	0.7407 (6)	0.0536 (13)
H5	−0.0084	0.0006	0.8065	0.064*
C6	0.0973 (3)	−0.0282 (4)	0.6780 (6)	0.0522 (12)
H6	0.1024	−0.0990	0.7045	0.063*
C7	−0.0958 (3)	0.1633 (4)	0.8725 (6)	0.0655 (15)
H7A	−0.1332	0.1093	0.8189	0.098*
H7B	−0.1339	0.2188	0.9054	0.098*
H7C	−0.0608	0.1347	0.9672	0.098*
C8	0.2084 (3)	0.1719 (3)	0.4227 (5)	0.0356 (10)
C9	0.3247 (3)	0.4087 (4)	0.4401 (5)	0.0406 (10)
H9	0.2985	0.4355	0.5293	0.049*
C10	0.3904 (3)	0.4723 (3)	0.3608 (5)	0.0374 (10)
C11	0.3967 (3)	0.5806 (4)	0.3780 (6)	0.0477 (11)
C12	0.4617 (4)	0.6382 (4)	0.3079 (7)	0.0646 (15)
H12	0.4641	0.7107	0.3198	0.077*
C13	0.5223 (4)	0.5874 (5)	0.2207 (7)	0.0712 (17)
H13	0.5668	0.6254	0.1742	0.085*
C14	0.5179 (4)	0.4814 (5)	0.2017 (7)	0.0708 (16)
H14	0.5590	0.4475	0.1415	0.085*
C15	0.4530 (3)	0.4241 (4)	0.2707 (6)	0.0527 (13)
H15	0.4510	0.3517	0.2568	0.063*
Br1	0.24530 (3)	−0.07259 (4)	0.49919 (6)	0.0578 (2)
Br2	0.31365 (4)	0.65524 (4)	0.49486 (9)	0.0861 (3)
O1	0.2174 (2)	0.1358 (2)	0.2869 (3)	0.0489 (8)
O2	−0.0358 (2)	0.2037 (3)	0.7627 (4)	0.0579 (9)
N1	0.2468 (2)	0.2623 (3)	0.4809 (4)	0.0400 (9)
H1	0.239 (3)	0.277 (3)	0.582 (5)	0.048*
N2	0.3036 (2)	0.3173 (3)	0.3872 (4)	0.0391 (9)

	U11	U22	U33	U12	U13	U23
C1	0.038 (3)	0.042 (3)	0.042 (3)	−0.002 (2)	0.011 (2)	−0.007 (2)
C2	0.030 (2)	0.037 (2)	0.030 (2)	−0.0044 (18)	0.0070 (18)	−0.0026 (18)
C3	0.038 (2)	0.036 (2)	0.038 (2)	0.0012 (19)	0.0104 (19)	0.0061 (19)
C4	0.036 (2)	0.046 (3)	0.044 (3)	0.000 (2)	0.012 (2)	0.003 (2)
C5	0.056 (3)	0.051 (3)	0.060 (3)	−0.010 (2)	0.034 (3)	0.004 (3)
C6	0.056 (3)	0.038 (3)	0.066 (3)	−0.005 (2)	0.020 (3)	0.008 (2)
C7	0.051 (3)	0.080 (4)	0.071 (4)	−0.002 (3)	0.035 (3)	0.000 (3)
C8	0.035 (2)	0.037 (3)	0.035 (2)	−0.0032 (19)	0.0082 (19)	0.007 (2)
C9	0.037 (2)	0.044 (3)	0.043 (3)	0.003 (2)	0.017 (2)	−0.001 (2)
C10	0.033 (2)	0.039 (3)	0.042 (2)	0.0010 (19)	0.0143 (19)	0.006 (2)
C11	0.037 (2)	0.043 (3)	0.064 (3)	−0.002 (2)	0.011 (2)	0.006 (2)
C12	0.057 (3)	0.056 (3)	0.080 (4)	−0.014 (3)	0.006 (3)	0.019 (3)
C13	0.055 (3)	0.091 (5)	0.070 (4)	−0.022 (3)	0.020 (3)	0.026 (3)
C14	0.051 (3)	0.100 (5)	0.068 (4)	0.001 (3)	0.035 (3)	0.012 (3)
C15	0.048 (3)	0.056 (3)	0.058 (3)	0.005 (2)	0.027 (2)	0.004 (2)
Br1	0.0569 (4)	0.0486 (3)	0.0713 (4)	0.0116 (2)	0.0227 (3)	−0.0006 (2)
Br2	0.0675 (4)	0.0502 (4)	0.1467 (7)	0.0080 (3)	0.0393 (4)	−0.0194 (4)
O1	0.066 (2)	0.050 (2)	0.0337 (17)	−0.0067 (16)	0.0203 (15)	−0.0084 (15)
O2	0.0502 (19)	0.059 (2)	0.071 (2)	0.0080 (17)	0.0370 (17)	0.0058 (18)
N1	0.044 (2)	0.045 (2)	0.035 (2)	−0.0083 (17)	0.0204 (18)	−0.0031 (18)
N2	0.039 (2)	0.044 (2)	0.038 (2)	−0.0050 (17)	0.0188 (16)	0.0016 (17)

C1—C6	1.378 (6)	C8—N1	1.350 (5)
C1—C2	1.394 (6)	C9—N2	1.272 (5)
C1—Br1	1.892 (4)	C9—C10	1.469 (6)
C2—C3	1.387 (5)	C9—H9	0.9300
C2—C8	1.495 (5)	C10—C15	1.388 (6)
C3—C4	1.386 (5)	C10—C11	1.390 (6)
C3—H3	0.9300	C11—C12	1.382 (6)
C4—O2	1.367 (5)	C11—Br2	1.894 (5)
C4—C5	1.373 (6)	C12—C13	1.369 (8)
C5—C6	1.375 (6)	C12—H12	0.9300
C5—H5	0.9300	C13—C14	1.361 (8)
C6—H6	0.9300	C13—H13	0.9300
C7—O2	1.427 (5)	C14—C15	1.375 (7)
C7—H7A	0.9600	C14—H14	0.9300
C7—H7B	0.9600	C15—H15	0.9300
C7—H7C	0.9600	N1—N2	1.388 (4)
C8—O1	1.229 (5)	N1—H1	0.87 (4)
C6—C1—C2	120.0 (4)	N2—C9—C10	120.3 (4)
C6—C1—Br1	118.2 (3)	N2—C9—H9	119.9
C2—C1—Br1	121.8 (3)	C10—C9—H9	119.9
C3—C2—C1	118.2 (3)	C15—C10—C11	116.9 (4)
C3—C2—C8	119.2 (4)	C15—C10—C9	120.1 (4)
C1—C2—C8	122.6 (3)	C11—C10—C9	122.9 (4)
C4—C3—C2	121.4 (4)	C12—C11—C10	121.9 (4)
C4—C3—H3	119.3	C12—C11—Br2	117.4 (4)
C2—C3—H3	119.3	C10—C11—Br2	120.7 (3)
O2—C4—C5	124.8 (4)	C13—C12—C11	119.2 (5)
O2—C4—C3	115.6 (4)	C13—C12—H12	120.4
C5—C4—C3	119.6 (4)	C11—C12—H12	120.4
C4—C5—C6	119.6 (4)	C14—C13—C12	120.3 (5)
C4—C5—H5	120.2	C14—C13—H13	119.9
C6—C5—H5	120.2	C12—C13—H13	119.9
C5—C6—C1	121.2 (4)	C13—C14—C15	120.5 (5)
C5—C6—H6	119.4	C13—C14—H14	119.7
C1—C6—H6	119.4	C15—C14—H14	119.7
O2—C7—H7A	109.5	C14—C15—C10	121.2 (5)
O2—C7—H7B	109.5	C14—C15—H15	119.4
H7A—C7—H7B	109.5	C10—C15—H15	119.4
O2—C7—H7C	109.5	C4—O2—C7	118.1 (4)
H7A—C7—H7C	109.5	C8—N1—N2	119.4 (3)
H7B—C7—H7C	109.5	C8—N1—H1	115 (3)
O1—C8—N1	124.1 (4)	N2—N1—H1	125 (3)
O1—C8—C2	122.7 (4)	C9—N2—N1	114.5 (3)
N1—C8—C2	113.2 (4)
C6—C1—C2—C3	0.2 (6)	N2—C9—C10—C11	160.4 (4)
Br1—C1—C2—C3	−177.8 (3)	C15—C10—C11—C12	0.5 (7)
C6—C1—C2—C8	−177.3 (4)	C9—C10—C11—C12	177.2 (4)
Br1—C1—C2—C8	4.7 (6)	C15—C10—C11—Br2	178.8 (3)
C1—C2—C3—C4	−0.3 (6)	C9—C10—C11—Br2	−4.4 (6)
C8—C2—C3—C4	177.2 (4)	C10—C11—C12—C13	−0.8 (8)
C2—C3—C4—O2	180.0 (4)	Br2—C11—C12—C13	−179.2 (4)
C2—C3—C4—C5	−0.6 (7)	C11—C12—C13—C14	0.8 (8)
O2—C4—C5—C6	−179.0 (4)	C12—C13—C14—C15	−0.5 (9)
C3—C4—C5—C6	1.7 (7)	C13—C14—C15—C10	0.2 (8)
C4—C5—C6—C1	−1.8 (8)	C11—C10—C15—C14	−0.2 (7)
C2—C1—C6—C5	0.9 (7)	C9—C10—C15—C14	−177.0 (5)
Br1—C1—C6—C5	179.0 (4)	C5—C4—O2—C7	2.8 (7)
C3—C2—C8—O1	−127.5 (4)	C3—C4—O2—C7	−177.8 (4)
C1—C2—C8—O1	50.0 (6)	O1—C8—N1—N2	−2.9 (6)
C3—C2—C8—N1	50.2 (5)	C2—C8—N1—N2	179.5 (3)
C1—C2—C8—N1	−132.4 (4)	C10—C9—N2—N1	174.9 (4)
N2—C9—C10—C15	−23.0 (7)	C8—N1—N2—C9	169.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.87 (4)	2.07 (4)	2.906 (4)	160 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.87 (4)	2.07 (4)	2.906 (4)	160 (4)

Symmetry code: (i) .