(E)-N'-(5-Bromo-2-methoxy-benzyl-idene)-4-methoxy-benzohydrazide.

In the title compound, C(16)H(15)BrN(2)O(3), the benzohydrazide group is not planar and the mol-ecule exists in a trans configuration with respect to the methyl-idene unit. The dihedral angle between the two substituted benzene rings is 75.6 (2)°. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds involving carbonyl and amine functionalities, to form chains parallel to the c cell axis.

Related literature

For the biological activities of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related structures, see: Yehye et al. (2008 ▶); Fun, Patil, Jebas et al. (2008 ▶); Fun, Patil, Rao et al. (2008 ▶); Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C16H15BrN2O3

M = 363.21

Monoclinic,

a = 12.438 (4) Å

b = 16.684 (6) Å

c = 7.863 (3) Å

β = 108.218 (6)°

V = 1549.8 (9) Å3

Z = 4

Mo Kα radiation

μ = 2.67 mm−1

T = 298 (2) K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.593, T max = 0.620

8697 measured reflections

3245 independent reflections

2068 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.093

S = 1.01

3245 reflections

205 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.47 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/S1600536808035472/bh2202sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035472/bh2202Isup2.hkl

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

C16H15BrN2O3	F000 = 736
Mr = 363.21	Dx = 1.557 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2110 reflections
a = 12.438 (4) Å	θ = 2.4–24.5º
b = 16.684 (6) Å	µ = 2.67 mm−1
c = 7.863 (3) Å	T = 298 (2) K
β = 108.218 (6)º	Block, colorless
V = 1549.8 (9) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3245 independent reflections
Radiation source: fine-focus sealed tube	2068 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.034
T = 298(2) K	θmax = 26.7º
ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 1998)	h = −14→15
Tmin = 0.593, Tmax = 0.620	k = −20→21
8697 measured reflections	l = −9→9

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0407P)2 + 0.1883P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
3245 reflections	Δρmax = 0.50 e Å−3
205 parameters	Δρmin = −0.47 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Br1	−0.31436 (3)	0.22534 (2)	0.94364 (5)	0.07161 (17)
N1	0.10628 (17)	0.23762 (13)	0.8539 (3)	0.0380 (5)
N2	0.19688 (18)	0.26531 (13)	0.8053 (3)	0.0384 (5)
O1	0.01300 (15)	0.01461 (11)	0.7292 (3)	0.0509 (5)
O2	0.26258 (15)	0.33509 (11)	1.0641 (2)	0.0455 (5)
O3	0.61120 (16)	0.44804 (12)	0.6741 (3)	0.0603 (6)
C1	−0.0401 (2)	0.14085 (16)	0.8049 (3)	0.0383 (6)
C2	−0.0634 (2)	0.05851 (16)	0.7802 (3)	0.0414 (7)
C3	−0.1589 (2)	0.02734 (18)	0.8110 (4)	0.0490 (7)
H3	−0.1738	−0.0273	0.7967	0.059*
C4	−0.2318 (2)	0.07627 (19)	0.8625 (4)	0.0498 (8)
H4	−0.2957	0.0548	0.8828	0.060*
C5	−0.2101 (2)	0.15743 (18)	0.8841 (4)	0.0460 (7)
C6	−0.1148 (2)	0.18901 (17)	0.8578 (3)	0.0429 (7)
H6	−0.1000	0.2435	0.8757	0.051*
C7	0.0603 (2)	0.17374 (16)	0.7739 (3)	0.0389 (6)
H7	0.0915	0.1481	0.6953	0.047*
C8	0.2703 (2)	0.31655 (15)	0.9165 (4)	0.0369 (6)
C9	0.3602 (2)	0.34885 (15)	0.8498 (3)	0.0354 (6)
C10	0.3494 (2)	0.35720 (16)	0.6705 (4)	0.0425 (7)
H10	0.2833	0.3400	0.5852	0.051*
C11	0.4338 (2)	0.39027 (18)	0.6149 (4)	0.0493 (7)
H11	0.4246	0.3954	0.4934	0.059*
C12	0.5326 (2)	0.41596 (16)	0.7408 (4)	0.0432 (7)
C13	0.5452 (2)	0.40845 (18)	0.9203 (4)	0.0482 (7)
H13	0.6115	0.4256	1.0054	0.058*
C14	0.4593 (2)	0.37549 (17)	0.9738 (4)	0.0462 (7)
H14	0.4681	0.3711	1.0953	0.055*
C15	0.7161 (3)	0.4720 (2)	0.7978 (5)	0.0739 (11)
H15A	0.7031	0.5129	0.8749	0.111*
H15B	0.7644	0.4926	0.7338	0.111*
H15C	0.7517	0.4267	0.8684	0.111*
C16	−0.0095 (3)	−0.06880 (17)	0.6972 (4)	0.0563 (8)
H16A	−0.0110	−0.0943	0.8059	0.084*
H16B	0.0488	−0.0925	0.6575	0.084*
H16C	−0.0814	−0.0757	0.6068	0.084*
H2	0.212 (2)	0.2407 (14)	0.715 (3)	0.044 (8)*

	U11	U22	U33	U12	U13	U23
Br1	0.0574 (2)	0.0821 (3)	0.0863 (3)	0.00286 (18)	0.0383 (2)	−0.0118 (2)
N1	0.0331 (12)	0.0430 (14)	0.0405 (13)	−0.0059 (10)	0.0154 (10)	−0.0001 (10)
N2	0.0398 (13)	0.0409 (13)	0.0403 (14)	−0.0086 (11)	0.0208 (11)	−0.0065 (11)
O1	0.0498 (12)	0.0413 (11)	0.0670 (14)	−0.0080 (9)	0.0260 (11)	−0.0072 (10)
O2	0.0488 (11)	0.0473 (11)	0.0470 (12)	−0.0117 (9)	0.0244 (10)	−0.0083 (9)
O3	0.0472 (13)	0.0689 (14)	0.0728 (15)	−0.0201 (11)	0.0300 (11)	−0.0025 (12)
C1	0.0363 (15)	0.0414 (16)	0.0361 (15)	−0.0074 (12)	0.0098 (13)	−0.0008 (12)
C2	0.0401 (16)	0.0453 (17)	0.0371 (16)	−0.0058 (13)	0.0098 (13)	−0.0017 (13)
C3	0.0483 (17)	0.0462 (17)	0.0525 (19)	−0.0146 (14)	0.0158 (15)	−0.0021 (14)
C4	0.0411 (17)	0.060 (2)	0.0503 (18)	−0.0150 (15)	0.0176 (15)	0.0009 (15)
C5	0.0404 (16)	0.058 (2)	0.0410 (17)	−0.0019 (14)	0.0145 (14)	0.0009 (14)
C6	0.0437 (16)	0.0433 (16)	0.0412 (17)	−0.0049 (13)	0.0125 (14)	−0.0019 (13)
C7	0.0372 (15)	0.0417 (16)	0.0404 (16)	−0.0035 (13)	0.0158 (13)	−0.0020 (13)
C8	0.0368 (15)	0.0318 (14)	0.0436 (17)	0.0025 (12)	0.0147 (13)	0.0013 (12)
C9	0.0328 (14)	0.0328 (14)	0.0422 (17)	−0.0033 (11)	0.0142 (13)	−0.0010 (12)
C10	0.0350 (15)	0.0479 (17)	0.0422 (17)	−0.0075 (13)	0.0086 (13)	−0.0016 (13)
C11	0.0504 (18)	0.0560 (19)	0.0450 (17)	−0.0098 (14)	0.0201 (15)	0.0023 (14)
C12	0.0365 (16)	0.0385 (15)	0.057 (2)	−0.0043 (12)	0.0184 (15)	−0.0021 (13)
C13	0.0340 (16)	0.0556 (19)	0.054 (2)	−0.0106 (13)	0.0128 (14)	−0.0093 (15)
C14	0.0453 (17)	0.0554 (18)	0.0400 (17)	−0.0063 (14)	0.0165 (14)	−0.0055 (14)
C15	0.048 (2)	0.087 (3)	0.096 (3)	−0.0268 (18)	0.036 (2)	−0.017 (2)
C16	0.062 (2)	0.0428 (18)	0.067 (2)	−0.0070 (15)	0.0239 (17)	−0.0084 (15)

Br1—C5	1.888 (3)	C6—H6	0.9300
N1—C7	1.278 (3)	C7—H7	0.9300
N1—N2	1.378 (3)	C8—C9	1.477 (3)
N2—C8	1.352 (3)	C9—C10	1.381 (4)
N2—H2	0.890 (10)	C9—C14	1.385 (4)
O1—C2	1.355 (3)	C10—C11	1.372 (4)
O1—C16	1.426 (3)	C10—H10	0.9300
O2—C8	1.233 (3)	C11—C12	1.383 (4)
O3—C12	1.355 (3)	C11—H11	0.9300
O3—C15	1.419 (4)	C12—C13	1.377 (4)
C1—C6	1.386 (4)	C13—C14	1.379 (4)
C1—C2	1.405 (4)	C13—H13	0.9300
C1—C7	1.453 (3)	C14—H14	0.9300
C2—C3	1.386 (4)	C15—H15A	0.9600
C3—C4	1.371 (4)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.381 (4)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.371 (4)	C16—H16C	0.9600
C7—N1—N2	115.0 (2)	C10—C9—C14	117.8 (2)
C8—N2—N1	118.5 (2)	C10—C9—C8	123.9 (2)
C8—N2—H2	122.6 (17)	C14—C9—C8	118.2 (2)
N1—N2—H2	117.5 (17)	C11—C10—C9	121.8 (3)
C2—O1—C16	117.6 (2)	C11—C10—H10	119.1
C12—O3—C15	117.8 (2)	C9—C10—H10	119.1
C6—C1—C2	118.7 (2)	C10—C11—C12	119.6 (3)
C6—C1—C7	121.5 (2)	C10—C11—H11	120.2
C2—C1—C7	119.8 (2)	C12—C11—H11	120.2
O1—C2—C3	124.6 (3)	O3—C12—C13	124.6 (2)
O1—C2—C1	115.9 (2)	O3—C12—C11	115.6 (3)
C3—C2—C1	119.5 (3)	C13—C12—C11	119.7 (3)
C4—C3—C2	120.7 (3)	C12—C13—C14	119.9 (3)
C4—C3—H3	119.7	C12—C13—H13	120.0
C2—C3—H3	119.7	C14—C13—H13	120.0
C3—C4—C5	119.9 (3)	C13—C14—C9	121.2 (3)
C3—C4—H4	120.0	C13—C14—H14	119.4
C5—C4—H4	120.0	C9—C14—H14	119.4
C6—C5—C4	120.2 (3)	O3—C15—H15A	109.5
C6—C5—Br1	120.0 (2)	O3—C15—H15B	109.5
C4—C5—Br1	119.8 (2)	H15A—C15—H15B	109.5
C5—C6—C1	121.0 (3)	O3—C15—H15C	109.5
C5—C6—H6	119.5	H15A—C15—H15C	109.5
C1—C6—H6	119.5	H15B—C15—H15C	109.5
N1—C7—C1	120.5 (2)	O1—C16—H16A	109.5
N1—C7—H7	119.7	O1—C16—H16B	109.5
C1—C7—H7	119.7	H16A—C16—H16B	109.5
O2—C8—N2	122.1 (2)	O1—C16—H16C	109.5
O2—C8—C9	122.2 (2)	H16A—C16—H16C	109.5
N2—C8—C9	115.7 (2)	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.890 (10)	1.966 (12)	2.835 (3)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.890 (10)	1.966 (12)	2.835 (3)	165 (2)

Symmetry code: (i) .