3-Bromo-N'-[(E)-4-hydroxy-benzyl-idene]benzohydrazide.

The title compound, C(14)H(11)BrN(2)O(2), was synthesized by the reaction of 4-hydroxy-benzaldehyde with an equimolar quantity of 3-bromo-benzohydrazide in methanol. The dihedral angle between the two benzene rings is 40.1 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds to form a three-dimensional network.

Related literature

For related structures, see: Cao (2007a ▶,b ▶).

Experimental

Crystal data

C14H11BrN2O2

M = 319.16

Orthorhombic,

a = 7.5576 (11) Å

b = 11.7337 (18) Å

c = 15.021 (2) Å

V = 1332.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.08 mm−1

T = 298 (2) K

0.20 × 0.17 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.577, T max = 0.638

7740 measured reflections

2757 independent reflections

2145 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.059

S = 0.97

2757 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶), with 1154 Friedel pairs

Flack parameter: 0.006 (9)

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/S1600536808015912/sj2509sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015912/sj2509Isup2.hkl

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

C14H11BrN2O2	F000 = 640
Mr = 319.16	Dx = 1.591 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1827 reflections
a = 7.5576 (11) Å	θ = 2.3–24.5º
b = 11.7337 (18) Å	µ = 3.09 mm−1
c = 15.021 (2) Å	T = 298 (2) K
V = 1332.0 (3) Å3	Block, colourless
Z = 4	0.20 × 0.17 × 0.16 mm

Bruker SMART CCD area-detector diffractometer	2757 independent reflections
Radiation source: fine-focus sealed tube	2145 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
T = 298(2) K	θmax = 26.6º
ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.577, Tmax = 0.638	k = −10→14
7740 measured reflections	l = −18→18

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0151P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.059	(Δ/σ)max = 0.001
S = 0.97	Δρmax = 0.17 e Å−3
2757 reflections	Δρmin = −0.29 e Å−3
176 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), with 1154 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.006 (9)
Secondary atom site location: difference Fourier map

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	0.04594 (5)	0.39161 (3)	0.901456 (17)	0.06805 (13)
O1	0.1347 (3)	−0.14174 (14)	0.15827 (10)	0.0414 (5)
H1	0.0663	−0.1163	0.1208	0.062*
O2	0.0446 (3)	0.45672 (13)	0.48129 (10)	0.0435 (4)
N1	0.1134 (3)	0.23480 (18)	0.46451 (12)	0.0380 (6)
N2	0.1329 (3)	0.29110 (18)	0.54514 (12)	0.0372 (5)
C1	0.1401 (3)	0.0602 (2)	0.38450 (14)	0.0310 (6)
C2	0.0757 (3)	0.1044 (2)	0.30437 (14)	0.0343 (6)
H2	0.0339	0.1789	0.3024	0.041*
C3	0.0735 (3)	0.03889 (19)	0.22853 (14)	0.0331 (6)
H3	0.0315	0.0692	0.1754	0.040*
C4	0.1341 (3)	−0.0726 (2)	0.23148 (14)	0.0309 (6)
C5	0.1975 (3)	−0.1177 (2)	0.31015 (15)	0.0357 (6)
H5	0.2381	−0.1925	0.3120	0.043*
C6	0.2003 (3)	−0.0514 (2)	0.38585 (15)	0.0352 (6)
H6	0.2432	−0.0820	0.4387	0.042*
C7	0.1494 (3)	0.1299 (2)	0.46504 (15)	0.0348 (6)
H7	0.1829	0.0958	0.5183	0.042*
C8	0.0976 (3)	0.4039 (2)	0.54681 (14)	0.0339 (6)
C9	0.1227 (3)	0.4615 (2)	0.63473 (15)	0.0333 (6)
C10	0.0837 (3)	0.4069 (2)	0.71421 (14)	0.0373 (6)
H10	0.0457	0.3315	0.7143	0.045*
C11	0.1020 (4)	0.4657 (2)	0.79290 (15)	0.0405 (7)
C12	0.1571 (4)	0.5781 (2)	0.79396 (18)	0.0482 (8)
H12	0.1689	0.6169	0.8476	0.058*
C13	0.1942 (4)	0.6314 (2)	0.7149 (2)	0.0516 (8)
H13	0.2320	0.7068	0.7151	0.062*
C14	0.1760 (4)	0.5743 (2)	0.63504 (17)	0.0425 (7)
H14	0.1995	0.6116	0.5817	0.051*
H2A	0.195 (4)	0.257 (2)	0.5890 (15)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0960 (3)	0.0793 (2)	0.02888 (14)	0.0102 (2)	0.00631 (17)	−0.00726 (16)
O1	0.0589 (13)	0.0376 (10)	0.0276 (8)	0.0034 (9)	−0.0034 (9)	−0.0093 (8)
O2	0.0655 (12)	0.0350 (10)	0.0301 (8)	0.0023 (10)	−0.0072 (10)	0.0018 (8)
N1	0.0566 (16)	0.0338 (13)	0.0237 (10)	0.0039 (11)	−0.0060 (10)	−0.0063 (9)
N2	0.0581 (16)	0.0306 (13)	0.0230 (11)	0.0104 (11)	−0.0077 (10)	−0.0070 (9)
C1	0.0354 (14)	0.0340 (13)	0.0236 (13)	−0.0019 (11)	−0.0012 (10)	−0.0033 (10)
C2	0.0435 (16)	0.0295 (12)	0.0298 (11)	−0.0011 (13)	0.0013 (11)	−0.0003 (11)
C3	0.0424 (16)	0.0334 (14)	0.0235 (11)	0.0021 (12)	−0.0035 (11)	0.0015 (10)
C4	0.0343 (14)	0.0348 (15)	0.0238 (12)	−0.0046 (11)	0.0011 (11)	−0.0070 (10)
C5	0.0470 (17)	0.0258 (14)	0.0343 (12)	0.0036 (13)	−0.0010 (11)	−0.0011 (12)
C6	0.0452 (16)	0.0362 (14)	0.0243 (13)	0.0032 (11)	−0.0068 (11)	0.0013 (11)
C7	0.0414 (15)	0.0393 (17)	0.0238 (11)	0.0003 (13)	−0.0026 (11)	−0.0027 (11)
C8	0.0370 (16)	0.0361 (15)	0.0287 (12)	−0.0032 (13)	0.0000 (10)	−0.0013 (12)
C9	0.0362 (15)	0.0342 (15)	0.0297 (12)	0.0039 (12)	−0.0045 (11)	−0.0069 (11)
C10	0.0434 (17)	0.0381 (14)	0.0304 (12)	0.0049 (13)	−0.0038 (11)	−0.0097 (12)
C11	0.0450 (18)	0.0456 (17)	0.0308 (13)	0.0094 (13)	−0.0012 (11)	−0.0093 (12)
C12	0.0512 (19)	0.055 (2)	0.0388 (15)	0.0096 (15)	−0.0131 (14)	−0.0196 (14)
C13	0.054 (2)	0.0368 (17)	0.0644 (19)	0.0002 (14)	−0.0103 (15)	−0.0221 (15)
C14	0.0483 (18)	0.0370 (17)	0.0421 (15)	−0.0020 (13)	−0.0031 (13)	−0.0037 (12)

Br1—C11	1.896 (3)	C5—C6	1.378 (3)
O1—C4	1.367 (3)	C5—H5	0.9300
O1—H1	0.8200	C6—H6	0.9300
O2—C8	1.230 (3)	C7—H7	0.9300
N1—C7	1.260 (3)	C8—C9	1.495 (3)
N1—N2	1.387 (2)	C9—C14	1.384 (4)
N2—C8	1.351 (3)	C9—C10	1.387 (3)
N2—H2A	0.904 (10)	C10—C11	1.376 (3)
C1—C6	1.386 (3)	C10—H10	0.9300
C1—C2	1.398 (3)	C11—C12	1.382 (4)
C1—C7	1.462 (3)	C12—C13	1.371 (4)
C2—C3	1.374 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.381 (4)
C3—C4	1.386 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.381 (3)
C4—O1—H1	109.5	N1—C7—H7	119.0
C7—N1—N2	115.88 (19)	C1—C7—H7	119.0
C8—N2—N1	117.51 (19)	O2—C8—N2	122.9 (2)
C8—N2—H2A	121.7 (19)	O2—C8—C9	121.4 (2)
N1—N2—H2A	119 (2)	N2—C8—C9	115.7 (2)
C6—C1—C2	118.5 (2)	C14—C9—C10	120.1 (2)
C6—C1—C7	120.0 (2)	C14—C9—C8	118.2 (2)
C2—C1—C7	121.4 (2)	C10—C9—C8	121.7 (2)
C3—C2—C1	120.7 (2)	C11—C10—C9	119.1 (2)
C3—C2—H2	119.7	C11—C10—H10	120.5
C1—C2—H2	119.7	C9—C10—H10	120.5
C2—C3—C4	119.8 (2)	C10—C11—C12	121.3 (2)
C2—C3—H3	120.1	C10—C11—Br1	119.1 (2)
C4—C3—H3	120.1	C12—C11—Br1	119.65 (19)
O1—C4—C5	117.4 (2)	C13—C12—C11	119.1 (2)
O1—C4—C3	122.4 (2)	C13—C12—H12	120.4
C5—C4—C3	120.2 (2)	C11—C12—H12	120.4
C6—C5—C4	119.7 (2)	C12—C13—C14	120.7 (3)
C6—C5—H5	120.2	C12—C13—H13	119.6
C4—C5—H5	120.2	C14—C13—H13	119.6
C5—C6—C1	121.1 (2)	C13—C14—C9	119.7 (3)
C5—C6—H6	119.5	C13—C14—H14	120.1
C1—C6—H6	119.5	C9—C14—H14	120.1
N1—C7—C1	122.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.95	2.750 (2)	166
O1—H1···N1i	0.82	2.56	3.003 (3)	116
N2—H2A···O1ii	0.904 (10)	2.136 (14)	3.007 (3)	162 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.95	2.750 (2)	166
O1—H1⋯N1i	0.82	2.56	3.003 (3)	116
N2—H2A⋯O1ii	0.904 (10)	2.136 (14)	3.007 (3)	162 (3)

Symmetry codes: (i) ; (ii) .