(E)-N'-(3,5-Dibromo-2-hydroxy-benzyl-idene)-2-methoxy-benzohydrazide.

The title compound, C(15)H(12)Br(2)N(2)O(3), was synthesized by the reaction of 3,5-dibromo-2-hydroxy-benzaldehyde with an equimolar quantity of 2-methoxy-benzohydrazide in methanol. The dihedral angle between the two benzene rings is 3.4 (2)° and intra-molecular O-H⋯N and N-H⋯O hydrogen bonds are observed in the mol-ecule. The crystal studied was an inversion twin with a 0.513 (19):0.487 (19) domain ratio.

Related literature

For related structures, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Li & Ban (2009 ▶); Zhu et al. (2009 ▶); Yang (2007 ▶); You et al. (2008 ▶). For our previous work in this area, see: Qu et al. (2008 ▶); Yang et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H12Br2N2O3

M = 428.09

Monoclinic,

a = 10.886 (1) Å

b = 12.956 (2) Å

c = 10.965 (2) Å

β = 96.476 (3)°

V = 1536.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 5.29 mm−1

T = 298 K

0.30 × 0.30 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.300, T max = 0.329 (expected range = 0.219–0.240)

4623 measured reflections

2208 independent reflections

1992 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.125

S = 1.05

2208 reflections

204 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.62 e Å−3

Absolute structure: Flack (1983 ▶), 531 Friedel pairs

Flack parameter: 0.513 (19)

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/S1600536809022168/hb5004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022168/hb5004Isup2.hkl

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

C15H12Br2N2O3	F(000) = 840
Mr = 428.09	Dx = 1.850 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2250 reflections
a = 10.886 (1) Å	θ = 2.4–25.9°
b = 12.956 (2) Å	µ = 5.29 mm−1
c = 10.965 (2) Å	T = 298 K
β = 96.476 (3)°	Block, colorless
V = 1536.6 (4) Å3	0.30 × 0.30 × 0.27 mm
Z = 4

Bruker SMART CCD diffractometer	2208 independent reflections
Radiation source: fine-focus sealed tube	1992 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→13
Tmin = 0.300, Tmax = 0.329	k = −16→16
4623 measured reflections	l = −13→13

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0877P)2 + 0.6851P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2208 reflections	Δρmax = 0.35 e Å−3
204 parameters	Δρmin = −0.62 e Å−3
3 restraints	Absolute structure: Flack (1983), 531 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.513 (19)

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	0.39963 (8)	−0.26669 (6)	−0.15520 (7)	0.0501 (2)
Br2	0.48191 (8)	−0.46448 (6)	0.30371 (8)	0.0556 (3)
O1	0.5231 (5)	−0.0896 (4)	−0.0108 (4)	0.0388 (11)
H1	0.5797	−0.0514	0.0166	0.058*
O2	0.6295 (7)	0.1701 (5)	0.0431 (5)	0.0548 (16)
O3	0.7666 (6)	0.2128 (4)	0.4081 (5)	0.0466 (14)
N1	0.6150 (6)	0.0066 (5)	0.1793 (5)	0.0341 (12)
N2	0.6578 (6)	0.0982 (4)	0.2312 (5)	0.0360 (12)
C1	0.5608 (6)	−0.1684 (5)	0.1883 (6)	0.0300 (13)
C2	0.5188 (6)	−0.1713 (5)	0.0627 (6)	0.0306 (13)
C3	0.4675 (7)	−0.2629 (5)	0.0147 (7)	0.0351 (14)
C4	0.4612 (7)	−0.3510 (5)	0.0854 (8)	0.0389 (15)
H4	0.4296	−0.4122	0.0504	0.047*
C5	0.5026 (7)	−0.3458 (5)	0.2081 (7)	0.0369 (15)
C6	0.5533 (7)	−0.2572 (5)	0.2625 (8)	0.0360 (16)
H6	0.5818	−0.2559	0.3456	0.043*
C7	0.6101 (7)	−0.0736 (5)	0.2472 (6)	0.0343 (14)
H7	0.6369	−0.0714	0.3307	0.041*
C8	0.6631 (7)	0.1797 (6)	0.1527 (6)	0.0332 (14)
C9	0.7136 (7)	0.2793 (5)	0.2082 (7)	0.0354 (15)
C10	0.7100 (8)	0.3626 (6)	0.1268 (8)	0.0458 (18)
H10	0.6764	0.3535	0.0458	0.055*
C11	0.7548 (10)	0.4567 (7)	0.1642 (12)	0.063 (3)
H11	0.7503	0.5115	0.1090	0.076*
C12	0.8069 (9)	0.4715 (7)	0.2835 (11)	0.059 (2)
H12	0.8380	0.5358	0.3088	0.071*
C13	0.8126 (8)	0.3906 (7)	0.3647 (9)	0.052 (2)
H13	0.8486	0.4003	0.4449	0.062*
C14	0.7652 (7)	0.2940 (6)	0.3286 (7)	0.0386 (15)
C15	0.8276 (10)	0.2211 (8)	0.5282 (8)	0.062 (3)
H15A	0.9101	0.2462	0.5248	0.093*
H15B	0.8309	0.1545	0.5668	0.093*
H15C	0.7833	0.2682	0.5748	0.093*
H2	0.692 (9)	0.097 (9)	0.310 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0682 (5)	0.0405 (4)	0.0380 (4)	−0.0037 (4)	−0.0105 (3)	−0.0106 (3)
Br2	0.0651 (5)	0.0333 (4)	0.0706 (6)	0.0050 (4)	0.0171 (4)	0.0194 (4)
O1	0.059 (3)	0.029 (2)	0.027 (2)	−0.007 (2)	−0.006 (2)	0.0006 (18)
O2	0.079 (4)	0.043 (3)	0.039 (3)	−0.015 (3)	−0.011 (3)	0.005 (3)
O3	0.060 (4)	0.044 (3)	0.033 (3)	−0.015 (3)	−0.007 (2)	−0.007 (2)
N1	0.042 (3)	0.030 (3)	0.030 (3)	−0.006 (2)	0.001 (2)	−0.005 (2)
N2	0.050 (3)	0.028 (3)	0.029 (3)	−0.010 (3)	−0.003 (2)	−0.003 (2)
C1	0.034 (3)	0.026 (3)	0.030 (3)	−0.001 (2)	0.002 (2)	0.002 (2)
C2	0.036 (3)	0.024 (3)	0.031 (3)	0.002 (2)	0.000 (3)	0.000 (2)
C3	0.036 (4)	0.034 (3)	0.033 (4)	0.003 (3)	−0.004 (3)	−0.003 (3)
C4	0.038 (4)	0.028 (3)	0.050 (4)	0.002 (3)	0.004 (3)	−0.007 (3)
C5	0.040 (4)	0.028 (3)	0.044 (4)	0.005 (3)	0.010 (3)	0.006 (3)
C6	0.039 (4)	0.026 (3)	0.042 (4)	0.000 (3)	0.002 (3)	0.005 (3)
C7	0.044 (4)	0.029 (3)	0.029 (3)	0.001 (3)	−0.001 (3)	−0.001 (2)
C8	0.035 (3)	0.038 (4)	0.025 (3)	−0.004 (3)	0.000 (3)	−0.004 (3)
C9	0.038 (4)	0.032 (4)	0.038 (4)	−0.005 (3)	0.011 (3)	−0.008 (3)
C10	0.051 (5)	0.040 (4)	0.048 (4)	0.000 (3)	0.010 (3)	0.000 (3)
C11	0.063 (6)	0.034 (4)	0.096 (8)	−0.003 (4)	0.026 (6)	0.005 (5)
C12	0.056 (5)	0.036 (4)	0.088 (7)	−0.013 (4)	0.018 (5)	−0.020 (4)
C13	0.046 (4)	0.046 (5)	0.065 (5)	−0.016 (4)	0.012 (4)	−0.030 (4)
C14	0.035 (4)	0.037 (3)	0.045 (4)	−0.007 (3)	0.008 (3)	−0.013 (3)
C15	0.061 (6)	0.086 (7)	0.037 (4)	−0.011 (5)	−0.005 (4)	−0.007 (4)

Br1—C3	1.925 (7)	C5—C6	1.379 (10)
Br2—C5	1.889 (7)	C6—H6	0.9300
O1—C2	1.335 (8)	C7—H7	0.9300
O1—H1	0.8200	C8—C9	1.504 (10)
O2—C8	1.222 (8)	C9—C14	1.388 (11)
O3—C14	1.366 (10)	C9—C10	1.398 (11)
O3—C15	1.411 (11)	C10—C11	1.359 (13)
N1—C7	1.282 (9)	C10—H10	0.9300
N1—N2	1.375 (8)	C11—C12	1.380 (17)
N2—C8	1.367 (9)	C11—H11	0.9300
N2—H2	0.90 (5)	C12—C13	1.372 (14)
C1—C2	1.401 (9)	C12—H12	0.9300
C1—C6	1.417 (9)	C13—C14	1.394 (10)
C1—C7	1.461 (9)	C13—H13	0.9300
C2—C3	1.389 (10)	C15—H15A	0.9600
C3—C4	1.386 (11)	C15—H15B	0.9600
C4—C5	1.372 (11)	C15—H15C	0.9600
C4—H4	0.9300
C2—O1—H1	109.5	O2—C8—N2	120.7 (6)
C14—O3—C15	120.5 (7)	O2—C8—C9	122.7 (6)
C7—N1—N2	119.5 (6)	N2—C8—C9	116.6 (6)
C8—N2—N1	116.3 (5)	C14—C9—C10	118.7 (7)
C8—N2—H2	125 (7)	C14—C9—C8	126.3 (7)
N1—N2—H2	118 (7)	C10—C9—C8	114.9 (7)
C2—C1—C6	120.5 (6)	C11—C10—C9	121.1 (9)
C2—C1—C7	121.3 (6)	C11—C10—H10	119.4
C6—C1—C7	118.1 (6)	C9—C10—H10	119.4
O1—C2—C3	119.2 (6)	C10—C11—C12	120.3 (9)
O1—C2—C1	122.8 (6)	C10—C11—H11	119.8
C3—C2—C1	117.9 (6)	C12—C11—H11	119.8
C4—C3—C2	122.3 (7)	C13—C12—C11	119.6 (8)
C4—C3—Br1	118.8 (5)	C13—C12—H12	120.2
C2—C3—Br1	118.9 (5)	C11—C12—H12	120.2
C5—C4—C3	118.5 (6)	C12—C13—C14	120.9 (9)
C5—C4—H4	120.8	C12—C13—H13	119.6
C3—C4—H4	120.8	C14—C13—H13	119.6
C4—C5—C6	122.4 (6)	O3—C14—C9	118.4 (6)
C4—C5—Br2	117.3 (5)	O3—C14—C13	122.2 (7)
C6—C5—Br2	120.3 (6)	C9—C14—C13	119.4 (8)
C5—C6—C1	118.3 (7)	O3—C15—H15A	109.5
C5—C6—H6	120.9	O3—C15—H15B	109.5
C1—C6—H6	120.9	H15A—C15—H15B	109.5
N1—C7—C1	117.5 (6)	O3—C15—H15C	109.5
N1—C7—H7	121.3	H15A—C15—H15C	109.5
C1—C7—H7	121.3	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.90 (5)	1.97 (9)	2.617 (8)	128 (9)
O1—H1···N1	0.82	1.93	2.535 (7)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.90 (5)	1.97 (9)	2.617 (8)	128 (9)
O1—H1⋯N1	0.82	1.93	2.535 (7)	130