N'-(5-Bromo-2-methoxy-benzyl-idene)-2-hydroxy-benzohydrazide.

The title Schiff base compound, C(15)H(13)BrN(2)O(3), is derived from the condensation of 5-bromo-2-methoxy-benzaldehyde with 2-hydroxy-benzohydrazide in an ethanol solution. The dihedral angle between the two aromatic rings is 6.9 (9)°. The meth-oxy group is coplanar with the attached ring [C-O-C-C = 3.1 (12)°]. An intra-molecular N-H⋯O hydrogen bond is observed. In the crystal structure, the mol-ecules are linked into chains along the [001] direction by inter-molecular O-H⋯N, O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Lu et al. (2008a ▶,b ▶,c ▶); Nie (2008 ▶); He (2008 ▶); Shi et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H13BrN2O3

M = 349.18

Tetragonal,

a = 15.530 (3) Å

c = 25.308 (2) Å

V = 6103.8 (17) Å3

Z = 16

Mo Kα radiation

μ = 2.70 mm−1

T = 298 (2) K

0.12 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.737, T max = 0.774

25116 measured reflections

3322 independent reflections

1243 reflections with I > 2σ(I)

R int = 0.128

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.226

S = 0.99

3322 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.97 e Å−3

Δρmin = −0.86 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536808030900/ci2679sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030900/ci2679Isup2.hkl

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

C15H13BrN2O3	Dx = 1.520 Mg m−3
Mr = 349.18	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 1836 reflections
Hall symbol: -I 4ad	θ = 2.4–24.3°
a = 15.530 (3) Å	µ = 2.70 mm−1
c = 25.308 (2) Å	T = 298 K
V = 6103.8 (17) Å3	Block, colourless
Z = 16	0.12 × 0.10 × 0.10 mm
F(000) = 2816

Bruker APEXII CCD area-detector diffractometer	3322 independent reflections
Radiation source: fine-focus sealed tube	1243 reflections with I > 2σ(I)
graphite	Rint = 0.128
ω scans	θmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −19→19
Tmin = 0.737, Tmax = 0.774	k = −19→19
25116 measured reflections	l = −32→32

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.226	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0861P)2 + 12.6195P] where P = (Fo2 + 2Fc2)/3
3322 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.97 e Å−3
1 restraint	Δρmin = −0.86 e Å−3

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	0.13353 (7)	0.23636 (7)	0.44885 (4)	0.1335 (6)
O1	0.0993 (4)	0.3108 (3)	0.2169 (3)	0.1107 (18)
O2	0.2734 (3)	−0.0626 (3)	0.28327 (15)	0.0760 (13)
O3	0.2429 (3)	−0.0129 (3)	0.12353 (14)	0.0729 (13)
H3	0.2527	−0.0072	0.0919	0.109*
N1	0.2045 (3)	0.0897 (4)	0.26121 (18)	0.0624 (14)
N2	0.2295 (4)	0.0325 (3)	0.22229 (18)	0.0642 (14)
C1	0.1451 (4)	0.2232 (4)	0.2860 (3)	0.0715 (19)
C2	0.1073 (5)	0.3000 (6)	0.2705 (4)	0.090 (2)
C3	0.0784 (6)	0.3586 (5)	0.3092 (5)	0.110 (3)
H3A	0.0524	0.4101	0.2993	0.132*
C4	0.0888 (6)	0.3391 (7)	0.3611 (5)	0.114 (3)
H4	0.0705	0.3780	0.3867	0.137*
C5	0.1251 (5)	0.2647 (6)	0.3760 (4)	0.096 (3)
C6	0.1538 (5)	0.2065 (4)	0.3385 (3)	0.080 (2)
H6	0.1794	0.1554	0.3493	0.095*
C7	0.1749 (4)	0.1611 (5)	0.2463 (3)	0.0705 (19)
H7	0.1720	0.1744	0.2105	0.085*
C8	0.2622 (4)	−0.0430 (4)	0.2367 (2)	0.0581 (16)
C9	0.2842 (4)	−0.1056 (4)	0.19439 (19)	0.0512 (15)
C10	0.2728 (4)	−0.0908 (4)	0.1401 (2)	0.0572 (16)
C11	0.2912 (4)	−0.1555 (5)	0.1043 (2)	0.0662 (18)
H11	0.2822	−0.1467	0.0684	0.079*
C12	0.3224 (5)	−0.2320 (5)	0.1218 (3)	0.079 (2)
H12	0.3352	−0.2752	0.0976	0.095*
C13	0.3354 (5)	−0.2465 (5)	0.1747 (3)	0.084 (2)
H13	0.3582	−0.2987	0.1862	0.100*
C14	0.3148 (4)	−0.1842 (4)	0.2101 (2)	0.0687 (18)
H14	0.3217	−0.1952	0.2460	0.082*
C15	0.0626 (6)	0.3886 (6)	0.1961 (5)	0.143 (4)
H15A	0.0062	0.3968	0.2107	0.215*
H15B	0.0585	0.3842	0.1583	0.215*
H15C	0.0985	0.4366	0.2052	0.215*
H2	0.221 (4)	0.050 (4)	0.1888 (9)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.1547 (11)	0.1402 (10)	0.1057 (8)	−0.0250 (7)	0.0402 (6)	−0.0549 (6)
O1	0.108 (5)	0.077 (4)	0.147 (6)	0.014 (3)	−0.005 (4)	0.014 (4)
O2	0.113 (4)	0.083 (3)	0.032 (2)	0.018 (3)	0.002 (2)	0.002 (2)
O3	0.107 (4)	0.078 (3)	0.034 (2)	0.019 (3)	0.007 (2)	0.004 (2)
N1	0.081 (4)	0.059 (4)	0.048 (3)	−0.004 (3)	0.012 (3)	−0.006 (3)
N2	0.092 (4)	0.063 (4)	0.038 (3)	0.006 (3)	0.002 (3)	−0.004 (3)
C1	0.063 (5)	0.061 (5)	0.090 (6)	−0.003 (4)	0.013 (4)	−0.004 (4)
C2	0.078 (5)	0.073 (6)	0.120 (7)	−0.016 (5)	0.006 (5)	0.001 (6)
C3	0.092 (7)	0.057 (5)	0.181 (10)	0.005 (4)	0.019 (7)	−0.010 (7)
C4	0.107 (7)	0.085 (8)	0.150 (10)	−0.009 (6)	0.036 (7)	−0.034 (7)
C5	0.085 (6)	0.075 (6)	0.129 (7)	−0.016 (5)	0.026 (5)	−0.026 (5)
C6	0.082 (5)	0.066 (5)	0.091 (6)	−0.012 (4)	0.020 (4)	−0.025 (4)
C7	0.085 (5)	0.065 (5)	0.061 (4)	−0.004 (4)	0.007 (3)	0.005 (4)
C8	0.066 (4)	0.065 (5)	0.043 (4)	−0.007 (3)	0.007 (3)	−0.001 (3)
C9	0.061 (4)	0.058 (4)	0.034 (3)	−0.009 (3)	0.005 (3)	−0.001 (3)
C10	0.055 (4)	0.072 (5)	0.045 (3)	−0.005 (3)	0.008 (3)	−0.001 (3)
C11	0.074 (5)	0.075 (5)	0.049 (4)	−0.007 (4)	0.008 (3)	−0.008 (4)
C12	0.103 (6)	0.062 (5)	0.073 (5)	−0.007 (4)	0.017 (4)	−0.020 (4)
C13	0.116 (6)	0.067 (5)	0.067 (5)	0.018 (4)	0.015 (4)	0.011 (4)
C14	0.089 (5)	0.066 (5)	0.052 (4)	0.006 (4)	0.013 (3)	0.002 (3)
C15	0.109 (7)	0.100 (7)	0.221 (12)	0.011 (6)	−0.014 (7)	0.048 (7)

Br1—C5	1.900 (10)	C5—C6	1.385 (10)
O1—C2	1.373 (10)	C6—H6	0.93
O1—C15	1.436 (9)	C7—H7	0.93
O2—C8	1.230 (7)	C8—C9	1.485 (8)
O3—C10	1.362 (7)	C9—C14	1.370 (8)
O3—H3	0.82	C9—C10	1.405 (7)
N1—C7	1.259 (7)	C10—C11	1.383 (8)
N1—N2	1.381 (7)	C11—C12	1.356 (9)
N2—C8	1.330 (7)	C11—H11	0.93
N2—H2	0.90 (3)	C12—C13	1.373 (10)
C1—C6	1.360 (10)	C12—H12	0.93
C1—C2	1.386 (10)	C13—C14	1.357 (9)
C1—C7	1.467 (9)	C13—H13	0.93
C2—C3	1.411 (12)	C14—H14	0.93
C3—C4	1.356 (13)	C15—H15A	0.96
C3—H3A	0.93	C15—H15B	0.96
C4—C5	1.340 (12)	C15—H15C	0.96
C4—H4	0.93
C2—O1—C15	120.1 (8)	O2—C8—N2	122.4 (5)
C10—O3—H3	109.5	O2—C8—C9	119.7 (6)
C7—N1—N2	117.0 (5)	N2—C8—C9	117.9 (5)
C8—N2—N1	118.6 (5)	C14—C9—C10	118.3 (5)
C8—N2—H2	125 (4)	C14—C9—C8	117.0 (5)
N1—N2—H2	116 (4)	C10—C9—C8	124.7 (6)
C6—C1—C2	118.7 (7)	O3—C10—C11	121.0 (5)
C6—C1—C7	120.9 (7)	O3—C10—C9	119.3 (5)
C2—C1—C7	120.4 (8)	C11—C10—C9	119.7 (6)
O1—C2—C1	115.0 (8)	C12—C11—C10	119.7 (6)
O1—C2—C3	125.4 (9)	C12—C11—H11	120.1
C1—C2—C3	119.6 (9)	C10—C11—H11	120.1
C4—C3—C2	119.3 (9)	C11—C12—C13	121.1 (6)
C4—C3—H3A	120.3	C11—C12—H12	119.5
C2—C3—H3A	120.3	C13—C12—H12	119.5
C5—C4—C3	121.1 (9)	C14—C13—C12	119.4 (7)
C5—C4—H4	119.5	C14—C13—H13	120.3
C3—C4—H4	119.5	C12—C13—H13	120.3
C4—C5—C6	120.3 (9)	C13—C14—C9	121.8 (6)
C4—C5—Br1	120.2 (8)	C13—C14—H14	119.1
C6—C5—Br1	119.5 (8)	C9—C14—H14	119.1
C1—C6—C5	121.0 (8)	O1—C15—H15A	109.5
C1—C6—H6	119.5	O1—C15—H15B	109.5
C5—C6—H6	119.5	H15A—C15—H15B	109.5
N1—C7—C1	119.2 (6)	O1—C15—H15C	109.5
N1—C7—H7	120.4	H15A—C15—H15C	109.5
C1—C7—H7	120.4	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.90 (3)	1.95 (5)	2.606 (6)	129 (5)
O3—H3···N1i	0.82	2.56	3.159 (6)	130
O3—H3···O2i	0.82	1.81	2.590 (5)	157
C6—H6···O3ii	0.93	2.55	3.471 (8)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.90 (3)	1.95 (5)	2.606 (6)	129 (5)
O3—H3⋯N1i	0.82	2.56	3.159 (6)	130
O3—H3⋯O2i	0.82	1.81	2.590 (5)	157
C6—H6⋯O3ii	0.93	2.55	3.471 (8)	174

Symmetry codes: (i) ; (ii) .