(E)-4-Bromo-N'-(2-nitro-benzyl-idene)benzohydrazide.

The title compound, C(14)H(10)BrN(3)O(3), was obtained by a condensation reaction between 2-nitro-benzaldehyde and 4-bromo-benzohydrazide. The dihedral angle between the two benzene rings is 4.1 (2)°. The mol-ecule displays an E configuration about the C=N bond. In the crystal, mol-ecules are linked into a chain along [100] by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the biological properties of Schiff base and hydrazone compounds, see: Kucukguzel et al. (2006 ▶); Khattab et al. (2005 ▶); Karthikeyan et al. (2006 ▶); Okabe et al. (1993 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Shan et al. (2008 ▶); Fun et al. (2008 ▶); Ma et al. (2008 ▶); Diao et al. (2008a ▶,b ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C14H10BrN3O3

M = 348.16

Triclinic,

a = 4.8718 (17) Å

b = 6.842 (2) Å

c = 10.709 (4) Å

α = 98.014 (5)°

β = 93.258 (6)°

γ = 97.413 (5)°

V = 349.5 (2) Å3

Z = 1

Mo Kα radiation

μ = 2.95 mm−1

T = 298 (2) K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.590, T max = 0.634

2347 measured reflections

1998 independent reflections

1584 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.064

S = 0.95

1998 reflections

193 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 235 Friedel pairs

Flack parameter: 0.021 (8)

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/S1600536809002165/ci2760sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002165/ci2760Isup2.hkl

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

C14H10BrN3O3	Z = 1
Mr = 348.16	F(000) = 174
Triclinic, P1	Dx = 1.654 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8718 (17) Å	Cell parameters from 1163 reflections
b = 6.842 (2) Å	θ = 2.8–26.3°
c = 10.709 (4) Å	µ = 2.95 mm−1
α = 98.014 (5)°	T = 298 K
β = 93.258 (6)°	Block, colourless
γ = 97.413 (5)°	0.20 × 0.18 × 0.17 mm
V = 349.5 (2) Å3

Bruker SMART CCD area-detector diffractometer	1998 independent reflections
Radiation source: fine-focus sealed tube	1584 reflections with I > 2σ(I)
graphite	Rint = 0.013
ω scans	θmax = 30.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
Tmin = 0.590, Tmax = 0.634	k = −8→8
2347 measured reflections	l = −11→15

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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.064	w = 1/[σ2(Fo2) + (0.0058P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max = 0.001
1998 reflections	Δρmax = 0.22 e Å−3
193 parameters	Δρmin = −0.23 e Å−3
3 restraints	Absolute structure: Flack (1983), 235 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.021 (8)

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	0.28524 (6)	−0.18204 (5)	−0.03061 (4)	0.08281 (18)
O1	0.9938 (4)	0.7003 (4)	0.2644 (2)	0.0599 (6)
O2	0.1064 (8)	1.2188 (6)	0.7780 (3)	0.0860 (11)
O3	0.2286 (10)	0.9674 (5)	0.6631 (3)	0.1064 (15)
N1	0.5685 (5)	0.7559 (4)	0.3185 (2)	0.0399 (5)
H1	0.394 (9)	0.725 (7)	0.293 (4)	0.048*
N2	0.6709 (5)	0.9301 (4)	0.3980 (2)	0.0405 (5)
N3	0.2485 (7)	1.1447 (5)	0.6997 (3)	0.0584 (8)
C1	0.6174 (7)	0.4513 (5)	0.1848 (3)	0.0385 (7)
C2	0.7401 (7)	0.3754 (5)	0.0775 (3)	0.0506 (8)
H2	0.8910	0.4505	0.0495	0.061*
C3	0.6386 (8)	0.1890 (6)	0.0126 (3)	0.0564 (9)
H3	0.7180	0.1400	−0.0602	0.068*
C4	0.4217 (8)	0.0767 (5)	0.0555 (3)	0.0504 (8)
C5	0.2932 (7)	0.1486 (5)	0.1614 (3)	0.0447 (7)
H5	0.1429	0.0722	0.1889	0.054*
C6	0.3932 (6)	0.3357 (5)	0.2250 (3)	0.0420 (7)
H6	0.3090	0.3855	0.2962	0.050*
C7	0.7440 (6)	0.6473 (4)	0.2577 (3)	0.0404 (6)
C8	0.4917 (6)	1.0171 (4)	0.4562 (3)	0.0384 (6)
H8	0.3061	0.9609	0.4479	0.046*
C9	0.5831 (6)	1.2100 (4)	0.5376 (3)	0.0393 (6)
C10	0.4633 (7)	1.2766 (5)	0.6481 (3)	0.0433 (7)
C11	0.5462 (8)	1.4635 (6)	0.7158 (3)	0.0607 (9)
H11	0.4634	1.5029	0.7896	0.073*
C12	0.7486 (9)	1.5906 (6)	0.6752 (4)	0.0660 (10)
H12	0.8015	1.7178	0.7199	0.079*
C13	0.8755 (8)	1.5290 (5)	0.5668 (3)	0.0550 (9)
H13	1.0172	1.6139	0.5397	0.066*
C14	0.7919 (8)	1.3419 (6)	0.4990 (3)	0.0489 (9)
H14	0.8772	1.3031	0.4258	0.059*

	U11	U22	U33	U12	U13	U23
Br1	0.1255 (4)	0.04369 (19)	0.0679 (2)	−0.00267 (18)	0.00284 (18)	−0.01585 (13)
O1	0.0231 (11)	0.0608 (15)	0.0872 (15)	−0.0003 (10)	0.0026 (10)	−0.0128 (12)
O2	0.082 (2)	0.113 (3)	0.074 (2)	0.030 (2)	0.0420 (17)	0.0233 (19)
O3	0.149 (4)	0.068 (3)	0.087 (2)	−0.047 (2)	0.049 (2)	−0.0006 (17)
N1	0.0237 (12)	0.0358 (13)	0.0545 (13)	−0.0004 (10)	−0.0015 (10)	−0.0072 (11)
N2	0.0343 (13)	0.0331 (12)	0.0494 (12)	−0.0022 (10)	−0.0040 (10)	−0.0015 (10)
N3	0.057 (2)	0.068 (2)	0.0476 (14)	−0.0014 (16)	0.0036 (14)	0.0092 (14)
C1	0.0303 (16)	0.0361 (15)	0.0469 (15)	0.0039 (13)	−0.0061 (13)	0.0027 (12)
C2	0.0450 (19)	0.050 (2)	0.0551 (17)	0.0058 (15)	0.0104 (14)	0.0015 (15)
C3	0.067 (2)	0.057 (2)	0.0417 (15)	0.0094 (18)	0.0084 (15)	−0.0075 (14)
C4	0.062 (2)	0.0360 (16)	0.0488 (16)	0.0072 (15)	−0.0087 (15)	−0.0032 (13)
C5	0.0430 (18)	0.0365 (16)	0.0515 (16)	−0.0015 (13)	0.0030 (14)	0.0024 (13)
C6	0.0379 (17)	0.0418 (17)	0.0438 (15)	0.0048 (13)	0.0031 (13)	−0.0008 (13)
C7	0.0318 (16)	0.0389 (16)	0.0484 (14)	0.0018 (12)	−0.0009 (12)	0.0038 (12)
C8	0.0322 (15)	0.0356 (15)	0.0435 (14)	−0.0016 (13)	0.0004 (12)	−0.0006 (12)
C9	0.0385 (16)	0.0325 (15)	0.0444 (14)	−0.0001 (12)	−0.0029 (12)	0.0039 (12)
C10	0.0401 (17)	0.0418 (16)	0.0464 (14)	0.0022 (13)	0.0033 (13)	0.0042 (12)
C11	0.070 (2)	0.053 (2)	0.0542 (17)	0.0114 (19)	0.0013 (17)	−0.0095 (15)
C12	0.079 (3)	0.0351 (17)	0.075 (2)	−0.0046 (18)	−0.004 (2)	−0.0064 (16)
C13	0.058 (2)	0.0404 (19)	0.0614 (19)	−0.0124 (15)	0.0002 (17)	0.0091 (15)
C14	0.0495 (18)	0.041 (2)	0.051 (2)	−0.0091 (15)	0.0001 (17)	0.0075 (18)

Br1—C4	1.897 (3)	C4—C5	1.387 (5)
O1—C7	1.219 (4)	C5—C6	1.377 (4)
O2—N3	1.216 (5)	C5—H5	0.93
O3—N3	1.211 (5)	C6—H6	0.93
N1—C7	1.341 (4)	C8—C9	1.478 (4)
N1—N2	1.382 (3)	C8—H8	0.93
N1—H1	0.87 (4)	C9—C14	1.391 (5)
N2—C8	1.264 (4)	C9—C10	1.395 (4)
N3—C10	1.474 (5)	C10—C11	1.378 (4)
C1—C6	1.389 (5)	C11—C12	1.360 (6)
C1—C2	1.393 (5)	C11—H11	0.93
C1—C7	1.493 (4)	C12—C13	1.386 (6)
C2—C3	1.380 (5)	C12—H12	0.93
C2—H2	0.93	C13—C14	1.380 (5)
C3—C4	1.364 (5)	C13—H13	0.93
C3—H3	0.93	C14—H14	0.93
C7—N1—N2	119.9 (2)	O1—C7—N1	122.7 (3)
C7—N1—H1	116 (3)	O1—C7—C1	121.2 (3)
N2—N1—H1	123 (3)	N1—C7—C1	116.0 (2)
C8—N2—N1	115.5 (2)	N2—C8—C9	118.6 (3)
O3—N3—O2	123.8 (4)	N2—C8—H8	120.7
O3—N3—C10	117.7 (3)	C9—C8—H8	120.7
O2—N3—C10	118.5 (4)	C14—C9—C10	116.6 (3)
C6—C1—C2	118.7 (3)	C14—C9—C8	118.6 (3)
C6—C1—C7	122.3 (3)	C10—C9—C8	124.7 (3)
C2—C1—C7	118.8 (3)	C11—C10—C9	121.9 (3)
C3—C2—C1	120.2 (3)	C11—C10—N3	117.4 (3)
C3—C2—H2	119.9	C9—C10—N3	120.7 (3)
C1—C2—H2	119.9	C12—C11—C10	120.3 (3)
C4—C3—C2	119.9 (3)	C12—C11—H11	119.8
C4—C3—H3	120.1	C10—C11—H11	119.8
C2—C3—H3	120.1	C11—C12—C13	119.5 (3)
C3—C4—C5	121.3 (3)	C11—C12—H12	120.3
C3—C4—Br1	120.4 (3)	C13—C12—H12	120.3
C5—C4—Br1	118.3 (3)	C14—C13—C12	120.1 (3)
C6—C5—C4	118.6 (3)	C14—C13—H13	119.9
C6—C5—H5	120.7	C12—C13—H13	119.9
C4—C5—H5	120.7	C13—C14—C9	121.5 (3)
C5—C6—C1	121.3 (3)	C13—C14—H14	119.2
C5—C6—H6	119.4	C9—C14—H14	119.2
C1—C6—H6	119.4
C7—N1—N2—C8	−176.5 (3)	N2—C8—C9—C14	36.5 (4)
C6—C1—C2—C3	0.3 (5)	N2—C8—C9—C10	−147.7 (3)
C7—C1—C2—C3	175.9 (3)	C14—C9—C10—C11	0.1 (4)
C1—C2—C3—C4	−1.6 (5)	C8—C9—C10—C11	−175.8 (3)
C2—C3—C4—C5	2.2 (5)	C14—C9—C10—N3	−177.4 (3)
C2—C3—C4—Br1	−178.6 (3)	C8—C9—C10—N3	6.6 (4)
C3—C4—C5—C6	−1.4 (5)	O3—N3—C10—C11	−160.0 (4)
Br1—C4—C5—C6	179.4 (2)	O2—N3—C10—C11	18.4 (5)
C4—C5—C6—C1	0.1 (4)	O3—N3—C10—C9	17.7 (5)
C2—C1—C6—C5	0.4 (4)	O2—N3—C10—C9	−163.9 (3)
C7—C1—C6—C5	−175.0 (3)	C9—C10—C11—C12	0.6 (5)
N2—N1—C7—O1	−3.6 (4)	N3—C10—C11—C12	178.3 (4)
N2—N1—C7—C1	173.8 (2)	C10—C11—C12—C13	−1.5 (6)
C6—C1—C7—O1	143.2 (3)	C11—C12—C13—C14	1.6 (6)
C2—C1—C7—O1	−32.3 (4)	C12—C13—C14—C9	−0.8 (6)
C6—C1—C7—N1	−34.3 (4)	C10—C9—C14—C13	0.0 (5)
C2—C1—C7—N1	150.3 (3)	C8—C9—C14—C13	176.1 (3)
N1—N2—C8—C9	−176.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.900 (11)	1.909 (19)	2.791 (3)	166 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.900 (11)	1.909 (19)	2.791 (3)	166 (6)

Symmetry code: (i) .