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

In the title compound, C(14)H(10)BrClN(2)O, the dihedral angle between the two benzene rings is 11.4 (2)°. In the crystal structure, mol-ecules are connected via inter-molecular N-H⋯O hydrogen bonds into one-dimensional chains running parallel to the c axis.

Related literature

For the biological activity of hydrazones and Schiff bases, see: Bhandari et al. (2008 ▶); Sinha et al. (2008 ▶). For a related structure, see: Pan & Yang (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H10BrClN2O

M = 337.60

Monoclinic,

a = 11.218 (4) Å

b = 13.512 (5) Å

c = 9.200 (3) Å

β = 97.077 (6)°

V = 1383.9 (8) Å3

Z = 4

Mo Kα radiation

μ = 3.16 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T min = 0.491, T max = 0.531

6907 measured reflections

2438 independent reflections

1948 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.03

2438 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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/S1600536809012860/hb2944sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012860/hb2944Isup2.hkl

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

C14H10BrClN2O	F(000) = 672
Mr = 337.60	Dx = 1.620 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2695 reflections
a = 11.218 (4) Å	θ = 2.4–26.2°
b = 13.512 (5) Å	µ = 3.16 mm−1
c = 9.200 (3) Å	T = 298 K
β = 97.077 (6)°	Block, colorless
V = 1383.9 (8) Å3	0.23 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	2438 independent reflections
Radiation source: fine-focus sealed tube	1948 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −13→13
Tmin = 0.491, Tmax = 0.531	k = −10→16
6907 measured reflections	l = −10→10

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0447P)2 + 0.9326P] where P = (Fo2 + 2Fc2)/3
2438 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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	0.45713 (4)	1.17921 (3)	0.84354 (5)	0.07653 (18)
Cl1	0.23484 (10)	0.37589 (7)	0.63350 (10)	0.0790 (3)
N1	0.1872 (2)	0.66418 (16)	0.4378 (2)	0.0423 (5)
N2	0.2302 (2)	0.74288 (16)	0.5254 (2)	0.0419 (5)
H2	0.2331	0.7398	0.6191	0.050*
O1	0.2623 (2)	0.83236 (15)	0.3250 (2)	0.0555 (6)
C1	0.1301 (3)	0.4950 (2)	0.4158 (3)	0.0439 (7)
C2	0.1495 (3)	0.3987 (2)	0.4655 (3)	0.0521 (7)
C3	0.1046 (3)	0.3167 (2)	0.3829 (4)	0.0634 (9)
H3	0.1184	0.2529	0.4190	0.076*
C4	0.0401 (3)	0.3319 (3)	0.2483 (4)	0.0674 (10)
H4	0.0100	0.2781	0.1924	0.081*
C5	0.0197 (3)	0.4264 (3)	0.1954 (4)	0.0670 (10)
H5	−0.0245	0.4358	0.1041	0.080*
C6	0.0637 (3)	0.5072 (3)	0.2759 (4)	0.0558 (8)
H6	0.0497	0.5705	0.2378	0.067*
C7	0.1768 (3)	0.5816 (2)	0.5014 (3)	0.0448 (7)
H7	0.1987	0.5760	0.6019	0.054*
C8	0.2680 (3)	0.82507 (19)	0.4591 (3)	0.0402 (6)
C9	0.3160 (2)	0.90782 (19)	0.5568 (3)	0.0387 (6)
C10	0.3159 (3)	1.0028 (2)	0.4976 (4)	0.0639 (10)
H10	0.2873	1.0121	0.3993	0.077*
C11	0.3572 (4)	1.0832 (2)	0.5811 (4)	0.0687 (10)
H11	0.3549	1.1463	0.5404	0.082*
C12	0.4020 (3)	1.0687 (2)	0.7257 (3)	0.0485 (7)
C13	0.4055 (3)	0.9757 (2)	0.7869 (3)	0.0502 (7)
H13	0.4371	0.9667	0.8844	0.060*
C14	0.3620 (3)	0.8957 (2)	0.7029 (3)	0.0432 (6)
H14	0.3635	0.8330	0.7447	0.052*

	U11	U22	U33	U12	U13	U23
Br1	0.0834 (3)	0.0523 (2)	0.0923 (3)	−0.02495 (18)	0.0047 (2)	−0.02263 (19)
Cl1	0.1214 (8)	0.0504 (5)	0.0598 (6)	0.0029 (5)	−0.0099 (5)	0.0011 (4)
N1	0.0549 (14)	0.0366 (13)	0.0344 (12)	0.0020 (10)	0.0014 (10)	−0.0050 (10)
N2	0.0650 (15)	0.0336 (12)	0.0262 (11)	−0.0013 (10)	0.0018 (10)	−0.0021 (9)
O1	0.0959 (17)	0.0437 (12)	0.0263 (11)	0.0018 (11)	0.0054 (10)	0.0010 (8)
C1	0.0496 (16)	0.0391 (15)	0.0445 (16)	−0.0057 (12)	0.0120 (13)	−0.0079 (13)
C2	0.0590 (19)	0.0442 (17)	0.0542 (18)	−0.0014 (14)	0.0108 (15)	−0.0081 (14)
C3	0.076 (2)	0.0392 (17)	0.077 (3)	−0.0050 (15)	0.017 (2)	−0.0117 (16)
C4	0.076 (2)	0.058 (2)	0.066 (2)	−0.0167 (18)	0.0048 (19)	−0.0232 (18)
C5	0.069 (2)	0.071 (2)	0.058 (2)	−0.0143 (18)	−0.0046 (17)	−0.0136 (18)
C6	0.0590 (19)	0.0543 (19)	0.0540 (19)	−0.0083 (15)	0.0061 (15)	−0.0098 (15)
C7	0.0588 (18)	0.0397 (16)	0.0360 (15)	−0.0021 (13)	0.0058 (13)	−0.0027 (12)
C8	0.0519 (17)	0.0352 (14)	0.0332 (15)	0.0075 (12)	0.0038 (12)	0.0004 (11)
C9	0.0510 (16)	0.0333 (14)	0.0322 (14)	0.0015 (12)	0.0067 (12)	−0.0004 (11)
C10	0.105 (3)	0.0416 (17)	0.0414 (18)	−0.0093 (17)	−0.0061 (17)	0.0104 (14)
C11	0.103 (3)	0.0325 (17)	0.068 (2)	−0.0132 (17)	0.001 (2)	0.0098 (16)
C12	0.0519 (17)	0.0397 (16)	0.0542 (19)	−0.0110 (13)	0.0078 (14)	−0.0071 (14)
C13	0.0638 (19)	0.0464 (17)	0.0384 (16)	−0.0065 (14)	−0.0024 (14)	−0.0024 (13)
C14	0.0570 (17)	0.0341 (14)	0.0381 (15)	−0.0007 (12)	0.0042 (12)	0.0041 (12)

Br1—C12	1.903 (3)	C5—C6	1.377 (4)
Cl1—C2	1.742 (3)	C5—H5	0.9300
N1—C7	1.272 (4)	C6—H6	0.9300
N1—N2	1.385 (3)	C7—H7	0.9300
N2—C8	1.359 (3)	C8—C9	1.493 (4)
N2—H2	0.8600	C9—C14	1.388 (4)
O1—C8	1.232 (3)	C9—C10	1.394 (4)
C1—C2	1.388 (4)	C10—C11	1.378 (5)
C1—C6	1.415 (4)	C10—H10	0.9300
C1—C7	1.470 (4)	C11—C12	1.377 (5)
C2—C3	1.401 (4)	C11—H11	0.9300
C3—C4	1.371 (5)	C12—C13	1.376 (4)
C3—H3	0.9300	C13—C14	1.383 (4)
C4—C5	1.375 (5)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C7—N1—N2	116.8 (2)	N1—C7—H7	120.1
C8—N2—N1	118.2 (2)	C1—C7—H7	120.1
C8—N2—H2	120.9	O1—C8—N2	122.3 (3)
N1—N2—H2	120.9	O1—C8—C9	120.9 (2)
C2—C1—C6	116.9 (3)	N2—C8—C9	116.8 (2)
C2—C1—C7	122.6 (3)	C14—C9—C10	117.9 (3)
C6—C1—C7	120.5 (3)	C14—C9—C8	123.9 (2)
C1—C2—C3	122.1 (3)	C10—C9—C8	118.1 (2)
C1—C2—Cl1	120.3 (2)	C11—C10—C9	121.6 (3)
C3—C2—Cl1	117.5 (3)	C11—C10—H10	119.2
C4—C3—C2	119.1 (3)	C9—C10—H10	119.2
C4—C3—H3	120.5	C12—C11—C10	118.9 (3)
C2—C3—H3	120.5	C12—C11—H11	120.5
C3—C4—C5	120.3 (3)	C10—C11—H11	120.5
C3—C4—H4	119.8	C13—C12—C11	121.0 (3)
C5—C4—H4	119.8	C13—C12—Br1	119.5 (2)
C4—C5—C6	120.9 (3)	C11—C12—Br1	119.5 (2)
C4—C5—H5	119.5	C12—C13—C14	119.6 (3)
C6—C5—H5	119.5	C12—C13—H13	120.2
C5—C6—C1	120.7 (3)	C14—C13—H13	120.2
C5—C6—H6	119.7	C13—C14—C9	120.9 (3)
C1—C6—H6	119.7	C13—C14—H14	119.6
N1—C7—C1	119.9 (3)	C9—C14—H14	119.6
C7—N1—N2—C8	165.4 (3)	N1—N2—C8—C9	−178.9 (2)
C6—C1—C2—C3	−0.9 (5)	O1—C8—C9—C14	−157.9 (3)
C7—C1—C2—C3	180.0 (3)	N2—C8—C9—C14	22.8 (4)
C6—C1—C2—Cl1	177.7 (2)	O1—C8—C9—C10	21.4 (4)
C7—C1—C2—Cl1	−1.4 (4)	N2—C8—C9—C10	−158.0 (3)
C1—C2—C3—C4	0.5 (5)	C14—C9—C10—C11	−1.6 (5)
Cl1—C2—C3—C4	−178.1 (3)	C8—C9—C10—C11	179.1 (3)
C2—C3—C4—C5	−0.2 (6)	C9—C10—C11—C12	1.4 (6)
C3—C4—C5—C6	0.3 (6)	C10—C11—C12—C13	−0.1 (6)
C4—C5—C6—C1	−0.7 (6)	C10—C11—C12—Br1	−179.0 (3)
C2—C1—C6—C5	1.0 (5)	C11—C12—C13—C14	−1.0 (5)
C7—C1—C6—C5	−179.9 (3)	Br1—C12—C13—C14	177.9 (2)
N2—N1—C7—C1	179.2 (2)	C12—C13—C14—C9	0.8 (5)
C2—C1—C7—N1	160.0 (3)	C10—C9—C14—C13	0.5 (5)
C6—C1—C7—N1	−19.1 (4)	C8—C9—C14—C13	179.7 (3)
N1—N2—C8—O1	1.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	2.12	2.918 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.12	2.918 (3)	154

Symmetry code: (i) .