3-Bromo-N'-(2-hydroxy-benzyl-idene)benzohydrazide.

The title mol-ecule, C(14)H(11)BrN(2)O(2), displays a trans configuration about the C=N and C-N bonds. The dihedral angle between the two benzene rings is 18.5 (3)°. An intra-molecular O-H⋯N hydrogen bond is observed. In the crystal structure, the mol-ecules are linked into a chain along the c axis by N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For related literature, see: Ali et al. (2002 ▶); Allen et al. (1987 ▶); Cukurovali et al. (2002 ▶); Li (2007a ▶,b ▶); Qian et al. (2006 ▶); Qiu et al. (2006 ▶); Tarafder et al. (2002 ▶); Yang (2006 ▶); Yang & Guo (2006 ▶); Zhao (2006 ▶).

Experimental

Crystal data

C14H11BrN2O2

M = 319.16

Monoclinic,

a = 10.9397 (17) Å

b = 13.672 (2) Å

c = 8.8915 (14) Å

β = 95.882 (2)°

V = 1322.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.11 mm−1

T = 298 (2) K

0.32 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.436, T max = 0.456 (expected range = 0.377–0.394)

7853 measured reflections

3029 independent reflections

1997 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.03

3029 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −0.76 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 datablocks global, I. DOI: 10.1107/S1600536808001293/ci2553sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001293/ci2553Isup2.hkl

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

C14H11BrN2O2	F000 = 640
Mr = 319.16	Dx = 1.603 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2541 reflections
a = 10.9397 (17) Å	θ = 2.3–25.8º
b = 13.672 (2) Å	µ = 3.11 mm−1
c = 8.8915 (14) Å	T = 298 (2) K
β = 95.882 (2)º	Block, yellow
V = 1322.8 (4) Å3	0.32 × 0.30 × 0.30 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3029 independent reflections
Radiation source: fine-focus sealed tube	1997 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
T = 298(2) K	θmax = 27.5º
ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −14→11
Tmin = 0.436, Tmax = 0.456	k = −17→17
7853 measured reflections	l = −11→11

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.044P)2 + 0.8938P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3029 reflections	Δρmax = 0.73 e Å−3
176 parameters	Δρmin = −0.76 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.84586 (4)	0.69664 (2)	0.07515 (6)	0.07832 (19)
O1	0.5849 (2)	0.09555 (15)	−0.3004 (2)	0.0534 (5)
H1	0.6305	0.1342	−0.2516	0.080*
O2	0.7840 (2)	0.33361 (14)	−0.1658 (2)	0.0481 (5)
N1	0.7189 (2)	0.16000 (16)	−0.0568 (2)	0.0389 (5)
N2	0.7749 (2)	0.23255 (16)	0.0345 (3)	0.0405 (5)
C1	0.6433 (2)	−0.00290 (19)	−0.0791 (3)	0.0368 (6)
C2	0.5861 (3)	0.0088 (2)	−0.2268 (3)	0.0409 (6)
C3	0.5269 (3)	−0.0700 (2)	−0.3001 (4)	0.0538 (8)
H3	0.4882	−0.0620	−0.3974	0.065*
C4	0.5246 (3)	−0.1593 (2)	−0.2315 (4)	0.0587 (9)
H4	0.4853	−0.2116	−0.2831	0.070*
C5	0.5801 (3)	−0.1726 (2)	−0.0866 (4)	0.0567 (9)
H5	0.5784	−0.2336	−0.0405	0.068*
C6	0.6378 (3)	−0.0954 (2)	−0.0110 (4)	0.0491 (7)
H6	0.6740	−0.1043	0.0873	0.059*
C7	0.7039 (3)	0.07677 (19)	0.0056 (3)	0.0398 (6)
H7	0.7325	0.0676	0.1067	0.048*
C8	0.8024 (3)	0.31817 (18)	−0.0293 (3)	0.0365 (6)
C9	0.8582 (2)	0.39488 (19)	0.0755 (3)	0.0359 (6)
C10	0.8331 (3)	0.4917 (2)	0.0361 (3)	0.0416 (7)
H10	0.7829	0.5067	−0.0518	0.050*
C11	0.8834 (3)	0.5656 (2)	0.1290 (4)	0.0474 (7)
C12	0.9601 (3)	0.5450 (2)	0.2575 (4)	0.0552 (8)
H12	0.9943	0.5954	0.3184	0.066*
C13	0.9855 (3)	0.4493 (2)	0.2948 (3)	0.0572 (9)
H13	1.0377	0.4349	0.3811	0.069*
C14	0.9343 (3)	0.3738 (2)	0.2055 (3)	0.0468 (7)
H14	0.9509	0.3091	0.2329	0.056*
H2	0.778 (4)	0.223 (3)	0.1343 (14)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0724 (3)	0.03681 (19)	0.1239 (4)	0.00291 (16)	0.0012 (2)	−0.01230 (19)
O1	0.0719 (16)	0.0428 (11)	0.0428 (12)	−0.0081 (10)	−0.0072 (10)	0.0057 (9)
O2	0.0717 (14)	0.0422 (10)	0.0285 (11)	−0.0023 (10)	−0.0047 (9)	−0.0005 (8)
N1	0.0472 (14)	0.0350 (11)	0.0338 (12)	−0.0024 (10)	0.0004 (10)	−0.0045 (10)
N2	0.0559 (15)	0.0350 (11)	0.0292 (12)	−0.0041 (11)	−0.0022 (11)	−0.0036 (10)
C1	0.0382 (15)	0.0318 (13)	0.0409 (15)	0.0024 (11)	0.0057 (12)	−0.0011 (11)
C2	0.0441 (16)	0.0392 (14)	0.0397 (16)	−0.0023 (12)	0.0052 (12)	−0.0023 (12)
C3	0.060 (2)	0.0524 (18)	0.0481 (18)	−0.0130 (15)	−0.0005 (15)	−0.0042 (14)
C4	0.060 (2)	0.0435 (16)	0.073 (2)	−0.0143 (15)	0.0066 (18)	−0.0148 (16)
C5	0.060 (2)	0.0345 (15)	0.076 (2)	−0.0035 (14)	0.0107 (18)	0.0042 (15)
C6	0.0550 (18)	0.0398 (15)	0.0517 (18)	0.0034 (13)	0.0019 (14)	0.0053 (13)
C7	0.0452 (16)	0.0388 (14)	0.0342 (15)	0.0032 (12)	−0.0013 (12)	−0.0013 (11)
C8	0.0428 (16)	0.0359 (14)	0.0301 (15)	0.0035 (11)	0.0008 (11)	−0.0004 (11)
C9	0.0397 (15)	0.0373 (14)	0.0304 (14)	−0.0036 (11)	0.0028 (11)	−0.0023 (11)
C10	0.0437 (16)	0.0390 (15)	0.0410 (16)	−0.0004 (12)	−0.0012 (12)	−0.0042 (12)
C11	0.0468 (17)	0.0357 (14)	0.061 (2)	−0.0029 (12)	0.0098 (15)	−0.0069 (13)
C12	0.063 (2)	0.0560 (19)	0.0470 (19)	−0.0200 (16)	0.0056 (16)	−0.0149 (15)
C13	0.066 (2)	0.067 (2)	0.0364 (17)	−0.0203 (17)	−0.0083 (15)	0.0003 (15)
C14	0.0564 (19)	0.0464 (16)	0.0358 (16)	−0.0079 (14)	−0.0036 (14)	0.0043 (12)

Br1—C11	1.889 (3)	C5—C6	1.371 (4)
O1—C2	1.354 (3)	C5—H5	0.93
O1—H1	0.82	C6—H6	0.93
O2—C8	1.228 (3)	C7—H7	0.93
N1—C7	1.284 (3)	C8—C9	1.491 (4)
N1—N2	1.384 (3)	C9—C14	1.384 (4)
N2—C8	1.348 (3)	C9—C10	1.390 (4)
N2—H2	0.89 (1)	C10—C11	1.383 (4)
C1—C2	1.404 (4)	C10—H10	0.93
C1—C6	1.406 (4)	C11—C12	1.376 (5)
C1—C7	1.446 (4)	C12—C13	1.372 (5)
C2—C3	1.385 (4)	C12—H12	0.93
C3—C4	1.367 (5)	C13—C14	1.385 (4)
C3—H3	0.93	C13—H13	0.93
C4—C5	1.379 (5)	C14—H14	0.93
C4—H4	0.93
C2—O1—H1	109.5	N1—C7—H7	119.5
C7—N1—N2	116.7 (2)	C1—C7—H7	119.5
C8—N2—N1	118.6 (2)	O2—C8—N2	123.0 (2)
C8—N2—H2	124 (3)	O2—C8—C9	120.8 (2)
N1—N2—H2	117 (3)	N2—C8—C9	116.3 (2)
C2—C1—C6	118.1 (3)	C14—C9—C10	119.7 (3)
C2—C1—C7	122.5 (2)	C14—C9—C8	123.2 (2)
C6—C1—C7	119.4 (3)	C10—C9—C8	117.0 (2)
O1—C2—C3	118.2 (3)	C11—C10—C9	119.2 (3)
O1—C2—C1	122.2 (2)	C11—C10—H10	120.4
C3—C2—C1	119.5 (3)	C9—C10—H10	120.4
C4—C3—C2	121.0 (3)	C12—C11—C10	121.3 (3)
C4—C3—H3	119.5	C12—C11—Br1	120.1 (2)
C2—C3—H3	119.5	C10—C11—Br1	118.6 (2)
C3—C4—C5	120.5 (3)	C13—C12—C11	119.1 (3)
C3—C4—H4	119.7	C13—C12—H12	120.5
C5—C4—H4	119.7	C11—C12—H12	120.5
C6—C5—C4	119.5 (3)	C12—C13—C14	120.9 (3)
C6—C5—H5	120.2	C12—C13—H13	119.6
C4—C5—H5	120.2	C14—C13—H13	119.6
C5—C6—C1	121.3 (3)	C9—C14—C13	119.8 (3)
C5—C6—H6	119.3	C9—C14—H14	120.1
C1—C6—H6	119.3	C13—C14—H14	120.1
N1—C7—C1	121.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.93	2.639 (3)	145
N2—H2···O2i	0.89 (1)	1.934 (15)	2.806 (3)	165 (4)
C7—H7···O2i	0.93	2.45	3.206 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.93	2.639 (3)	145
N2—H2⋯O2i	0.89 (1)	1.934 (15)	2.806 (3)	165 (4)
C7—H7⋯O2i	0.93	2.45	3.206 (3)	139

Symmetry code: (i) .