(E)-N'-(5-Bromo-2-hy-droxy-benzyl-idene)-3-meth-oxy-benzohydrazide.

In the title compound, C(15)H(13)BrN(2)O(3), the two benzene rings form a dihedral angle of 16.9 (2)°. An intra-molecular O-H⋯N hydrogen bond affects the mol-ecular conformation. In the crystal structure, mol-ecules are linked through N-H⋯O hydrogen bonds into chains running along the a axis.

Related literature

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010 ▶); Zhu et al. (2009 ▶); Jimenez-Pulido et al. (2008 ▶); Raj et al. (2007 ▶); Zhong et al. (2007 ▶). For hydrazones we have reported previously, see: Liu & You (2010a ▶,b ▶,c ▶). For the structures of similar hydrazone compounds, see: Khaledi et al. (2009 ▶); Warad et al. (2009 ▶); Back et al. (2009 ▶); Vijayakumar et al. (2009 ▶). For related structures, see: Cao (2009 ▶); Xu et al. (2009 ▶); Shafiq et al. (2009 ▶).

Experimental

Crystal data

C15H13BrN2O3

M = 349.18

Monoclinic,

a = 6.865 (2) Å

b = 30.726 (3) Å

c = 7.257 (2) Å

β = 104.437 (15)°

V = 1482.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.78 mm−1

T = 298 K

0.27 × 0.25 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.520, T max = 0.567

8593 measured reflections

3079 independent reflections

1832 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.01

3079 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.45 e Å−3

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/S1600536810024001/sj5025sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024001/sj5025Isup2.hkl

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

C15H13BrN2O3	F(000) = 704
Mr = 349.18	Dx = 1.565 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2100 reflections
a = 6.865 (2) Å	θ = 2.6–25.0°
b = 30.726 (3) Å	µ = 2.78 mm−1
c = 7.257 (2) Å	T = 298 K
β = 104.437 (15)°	Block, colourless
V = 1482.2 (7) Å3	0.27 × 0.25 × 0.23 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3079 independent reflections
Radiation source: fine-focus sealed tube	1832 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 26.8°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −5→8
Tmin = 0.520, Tmax = 0.567	k = −37→38
8593 measured reflections	l = −9→9

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) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0443P)2] where P = (Fo2 + 2Fc2)/3
3079 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.45 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	−0.14621 (6)	0.006913 (10)	0.72146 (5)	0.08082 (18)
N1	−0.0463 (3)	0.21192 (6)	0.5786 (3)	0.0474 (5)
N2	0.1078 (3)	0.24188 (7)	0.6071 (3)	0.0486 (6)
O1	−0.4272 (3)	0.18973 (6)	0.5066 (3)	0.0620 (5)
H1	−0.3314	0.2060	0.5117	0.093*
O2	−0.0895 (3)	0.29146 (5)	0.4185 (3)	0.0522 (5)
O3	0.3228 (3)	0.43040 (6)	0.6485 (3)	0.0755 (6)
C1	−0.1528 (4)	0.14004 (8)	0.6243 (3)	0.0415 (6)
C2	−0.3592 (4)	0.14938 (8)	0.5621 (4)	0.0458 (6)
C3	−0.4970 (4)	0.11647 (10)	0.5578 (4)	0.0568 (7)
H3	−0.6336	0.1229	0.5227	0.068*
C4	−0.4370 (5)	0.07446 (9)	0.6041 (4)	0.0599 (8)
H4	−0.5324	0.0526	0.5971	0.072*
C5	−0.2338 (5)	0.06462 (8)	0.6614 (4)	0.0524 (7)
C6	−0.0948 (4)	0.09725 (8)	0.6719 (4)	0.0481 (7)
H6	0.0414	0.0906	0.7119	0.058*
C7	0.0005 (4)	0.17332 (8)	0.6411 (4)	0.0457 (7)
H7	0.1341	0.1666	0.6979	0.055*
C8	0.0728 (4)	0.28138 (8)	0.5248 (4)	0.0419 (6)
C9	0.2439 (4)	0.31261 (8)	0.5746 (3)	0.0400 (6)
C10	0.1979 (4)	0.35642 (8)	0.5838 (3)	0.0423 (6)
H10	0.0642	0.3652	0.5579	0.051*
C11	0.3486 (4)	0.38683 (8)	0.6308 (4)	0.0502 (7)
C12	0.5471 (5)	0.37320 (10)	0.6659 (4)	0.0631 (8)
H12	0.6500	0.3936	0.6975	0.076*
C13	0.5937 (4)	0.33037 (10)	0.6550 (4)	0.0621 (8)
H13	0.7276	0.3219	0.6773	0.074*
C14	0.4423 (4)	0.29916 (9)	0.6106 (4)	0.0507 (7)
H14	0.4738	0.2698	0.6053	0.061*
C15	0.1241 (6)	0.44666 (9)	0.6235 (5)	0.0788 (10)
H15A	0.0484	0.4413	0.4953	0.118*
H15B	0.1290	0.4774	0.6477	0.118*
H15C	0.0605	0.4323	0.7106	0.118*
H2	0.218 (3)	0.2361 (10)	0.700 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.1138 (3)	0.03462 (19)	0.0917 (3)	−0.00088 (16)	0.0212 (2)	0.00419 (16)
N1	0.0508 (13)	0.0366 (12)	0.0480 (13)	−0.0043 (10)	−0.0004 (11)	−0.0010 (10)
N2	0.0427 (14)	0.0343 (12)	0.0584 (16)	−0.0037 (10)	−0.0071 (11)	0.0051 (10)
O1	0.0508 (11)	0.0485 (12)	0.0798 (15)	0.0094 (9)	0.0034 (11)	0.0064 (10)
O2	0.0459 (11)	0.0399 (10)	0.0576 (12)	0.0025 (8)	−0.0118 (9)	0.0016 (9)
O3	0.0952 (17)	0.0360 (12)	0.0915 (17)	−0.0141 (11)	0.0163 (13)	−0.0061 (10)
C1	0.0455 (17)	0.0356 (14)	0.0398 (15)	0.0018 (11)	0.0036 (12)	−0.0031 (11)
C2	0.0503 (18)	0.0417 (15)	0.0416 (15)	0.0045 (13)	0.0044 (13)	−0.0005 (12)
C3	0.0486 (18)	0.059 (2)	0.0592 (19)	−0.0049 (14)	0.0069 (15)	0.0009 (15)
C4	0.068 (2)	0.0556 (19)	0.0536 (19)	−0.0215 (15)	0.0104 (16)	−0.0057 (14)
C5	0.074 (2)	0.0326 (14)	0.0478 (17)	−0.0020 (13)	0.0092 (15)	−0.0011 (12)
C6	0.0494 (17)	0.0400 (15)	0.0506 (17)	0.0037 (12)	0.0045 (13)	0.0006 (12)
C7	0.0455 (17)	0.0367 (15)	0.0493 (17)	0.0011 (12)	0.0014 (13)	−0.0012 (12)
C8	0.0438 (16)	0.0340 (14)	0.0431 (16)	0.0030 (12)	0.0016 (13)	−0.0029 (11)
C9	0.0407 (16)	0.0384 (14)	0.0380 (14)	−0.0012 (11)	0.0042 (12)	−0.0005 (11)
C10	0.0421 (15)	0.0398 (15)	0.0420 (15)	0.0006 (11)	0.0049 (12)	0.0016 (11)
C11	0.059 (2)	0.0419 (16)	0.0476 (17)	−0.0059 (13)	0.0095 (14)	0.0020 (13)
C12	0.059 (2)	0.063 (2)	0.063 (2)	−0.0242 (16)	0.0088 (16)	−0.0016 (16)
C13	0.0425 (18)	0.069 (2)	0.072 (2)	−0.0037 (15)	0.0091 (15)	0.0009 (17)
C14	0.0472 (17)	0.0466 (16)	0.0550 (18)	0.0078 (13)	0.0069 (14)	0.0016 (13)
C15	0.108 (3)	0.0404 (18)	0.092 (3)	0.0104 (18)	0.032 (2)	−0.0006 (16)

Br1—C5	1.888 (3)	C5—C6	1.373 (4)
N1—C7	1.282 (3)	C6—H6	0.9300
N1—N2	1.379 (3)	C7—H7	0.9300
N2—C8	1.347 (3)	C8—C9	1.490 (3)
N2—H2	0.898 (10)	C9—C14	1.384 (3)
O1—C2	1.350 (3)	C9—C10	1.388 (3)
O1—H1	0.8200	C10—C11	1.373 (3)
O2—C8	1.226 (3)	C10—H10	0.9300
O3—C11	1.361 (3)	C11—C12	1.387 (4)
O3—C15	1.421 (4)	C12—C13	1.361 (4)
C1—C6	1.392 (3)	C12—H12	0.9300
C1—C2	1.405 (3)	C13—C14	1.392 (4)
C1—C7	1.451 (3)	C13—H13	0.9300
C2—C3	1.380 (4)	C14—H14	0.9300
C3—C4	1.371 (4)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.386 (4)	C15—H15C	0.9600
C4—H4	0.9300
C7—N1—N2	116.7 (2)	O2—C8—N2	122.7 (2)
C8—N2—N1	119.3 (2)	O2—C8—C9	121.9 (2)
C8—N2—H2	122.3 (19)	N2—C8—C9	115.5 (2)
N1—N2—H2	117.0 (19)	C14—C9—C10	120.3 (2)
C2—O1—H1	109.5	C14—C9—C8	122.2 (2)
C11—O3—C15	118.5 (2)	C10—C9—C8	117.5 (2)
C6—C1—C2	118.4 (2)	C11—C10—C9	120.4 (2)
C6—C1—C7	119.2 (2)	C11—C10—H10	119.8
C2—C1—C7	122.4 (2)	C9—C10—H10	119.8
O1—C2—C3	118.8 (2)	O3—C11—C10	125.8 (3)
O1—C2—C1	122.0 (2)	O3—C11—C12	115.1 (2)
C3—C2—C1	119.2 (2)	C10—C11—C12	119.0 (3)
C4—C3—C2	121.5 (3)	C13—C12—C11	121.0 (3)
C4—C3—H3	119.3	C13—C12—H12	119.5
C2—C3—H3	119.3	C11—C12—H12	119.5
C3—C4—C5	119.8 (3)	C12—C13—C14	120.5 (3)
C3—C4—H4	120.1	C12—C13—H13	119.8
C5—C4—H4	120.1	C14—C13—H13	119.8
C6—C5—C4	119.4 (3)	C9—C14—C13	118.7 (3)
C6—C5—Br1	119.7 (2)	C9—C14—H14	120.6
C4—C5—Br1	120.9 (2)	C13—C14—H14	120.6
C5—C6—C1	121.6 (3)	O3—C15—H15A	109.5
C5—C6—H6	119.2	O3—C15—H15B	109.5
C1—C6—H6	119.2	H15A—C15—H15B	109.5
N1—C7—C1	120.6 (2)	O3—C15—H15C	109.5
N1—C7—H7	119.7	H15A—C15—H15C	109.5
C1—C7—H7	119.7	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.625 (3)	146
N2—H2···O2i	0.90 (1)	1.98 (1)	2.852 (3)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.625 (3)	146
N2—H2⋯O2i	0.90 (1)	1.98 (1)	2.852 (3)	163 (3)

Symmetry code: (i) .