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

The title hydrazone compound, C(16)H(15)BrN(2)O(3), adopts an E configuration about the C=N double bond. The mol-ecule is twisted, the dihedral angle between the two substituted benzene rings being 22.0 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains along the c axis.

Related literature

For the biological properties of the hydrazone compounds, see: Khattab et al. (2005 ▶); Küçükgüzel et al. (2003 ▶); Çukurovalı et al. (2006 ▶). For the structures of hydrazone derivatives, see: Fun et al. (2008 ▶); Wei et al. (2009 ▶); Khaledi et al. (2008 ▶); Yang et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H15BrN2O3

M = 363.21

Monoclinic,

a = 13.3286 (3) Å

b = 11.4816 (3) Å

c = 10.1233 (2) Å

β = 99.128 (1)°

V = 1529.59 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.70 mm−1

T = 298 K

0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.614, T max = 0.642

9188 measured reflections

3323 independent reflections

2281 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.096

S = 1.01

3323 reflections

204 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −0.69 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022971/at2816sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022971/at2816Isup2.hkl

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

C16H15BrN2O3	F(000) = 736
Mr = 363.21	Dx = 1.577 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2540 reflections
a = 13.3286 (3) Å	θ = 2.4–27.4°
b = 11.4816 (3) Å	µ = 2.70 mm−1
c = 10.1233 (2) Å	T = 298 K
β = 99.128 (1)°	Block, colourless
V = 1529.59 (6) Å3	0.20 × 0.18 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3323 independent reflections
Radiation source: fine-focus sealed tube	2281 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→15
Tmin = 0.614, Tmax = 0.642	k = −14→12
9188 measured reflections	l = −12→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0398P)2 + 1.0409P] where P = (Fo2 + 2Fc2)/3
3323 reflections	(Δ/σ)max < 0.001
204 parameters	Δρmax = 0.65 e Å−3
1 restraint	Δρmin = −0.68 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	0.36301 (2)	1.06194 (4)	0.08660 (4)	0.07080 (16)
O1	0.67425 (14)	1.12056 (19)	0.5818 (2)	0.0511 (5)
O2	0.80411 (13)	0.73514 (17)	0.15200 (18)	0.0419 (5)
O3	1.01119 (14)	0.80174 (18)	0.4696 (2)	0.0497 (5)
N1	0.72756 (15)	0.88017 (18)	0.3201 (2)	0.0327 (5)
N2	0.80859 (15)	0.80683 (19)	0.3608 (2)	0.0322 (5)
C1	0.61419 (18)	1.0218 (2)	0.3825 (3)	0.0335 (6)
C2	0.60017 (19)	1.1107 (2)	0.4729 (3)	0.0377 (6)
C3	0.5157 (2)	1.1822 (2)	0.4485 (3)	0.0447 (7)
H3	0.5068	1.2409	0.5089	0.054*
C4	0.4447 (2)	1.1667 (3)	0.3350 (3)	0.0484 (7)
H4	0.3873	1.2138	0.3194	0.058*
C5	0.4594 (2)	1.0810 (3)	0.2451 (3)	0.0438 (7)
C6	0.54289 (19)	1.0089 (2)	0.2674 (3)	0.0383 (6)
H6	0.5516	0.9515	0.2054	0.046*
C7	0.6646 (3)	1.2090 (3)	0.6772 (4)	0.0734 (11)
H7A	0.6630	1.2839	0.6347	0.110*
H7B	0.7214	1.2054	0.7483	0.110*
H7C	0.6027	1.1974	0.7129	0.110*
C8	0.70088 (18)	0.9428 (2)	0.4122 (3)	0.0340 (6)
H8	0.7366	0.9383	0.4988	0.041*
C9	0.84257 (17)	0.7374 (2)	0.2700 (2)	0.0300 (5)
C10	0.93090 (18)	0.6607 (2)	0.3210 (2)	0.0331 (6)
C11	1.01527 (19)	0.6938 (3)	0.4138 (3)	0.0376 (6)
C12	1.0973 (2)	0.6182 (3)	0.4424 (3)	0.0517 (8)
H12	1.1548	0.6414	0.5010	0.062*
C13	1.0941 (3)	0.5100 (3)	0.3852 (3)	0.0588 (9)
H13	1.1493	0.4600	0.4056	0.071*
C14	1.0107 (3)	0.4748 (3)	0.2987 (3)	0.0576 (9)
H14	1.0080	0.4002	0.2626	0.069*
C15	0.9304 (2)	0.5502 (2)	0.2649 (3)	0.0447 (7)
H15	0.8747	0.5267	0.2034	0.054*
C16	1.0993 (2)	0.8449 (4)	0.5536 (4)	0.0690 (10)
H16A	1.1117	0.7995	0.6342	0.103*
H16B	1.0887	0.9248	0.5757	0.103*
H16C	1.1568	0.8395	0.5076	0.103*
H2	0.830 (3)	0.802 (3)	0.4490 (12)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0439 (2)	0.0908 (3)	0.0690 (3)	0.00890 (18)	−0.01763 (15)	0.0059 (2)
O1	0.0405 (11)	0.0619 (14)	0.0490 (12)	0.0068 (10)	0.0010 (9)	−0.0198 (10)
O2	0.0364 (10)	0.0531 (12)	0.0333 (10)	0.0071 (9)	−0.0033 (8)	−0.0053 (9)
O3	0.0324 (10)	0.0606 (14)	0.0520 (12)	0.0012 (9)	−0.0057 (9)	−0.0146 (10)
N1	0.0240 (10)	0.0347 (12)	0.0372 (12)	0.0022 (9)	−0.0016 (8)	0.0008 (10)
N2	0.0280 (10)	0.0361 (12)	0.0309 (11)	0.0053 (9)	−0.0006 (9)	−0.0003 (10)
C1	0.0268 (12)	0.0352 (14)	0.0387 (14)	0.0005 (10)	0.0050 (10)	0.0012 (11)
C2	0.0302 (13)	0.0409 (15)	0.0433 (15)	−0.0017 (12)	0.0103 (11)	0.0002 (12)
C3	0.0411 (15)	0.0387 (17)	0.0570 (19)	0.0061 (13)	0.0161 (14)	−0.0006 (14)
C4	0.0343 (14)	0.0463 (18)	0.066 (2)	0.0095 (13)	0.0111 (14)	0.0104 (15)
C5	0.0279 (13)	0.0518 (18)	0.0496 (17)	−0.0003 (12)	−0.0007 (12)	0.0129 (14)
C6	0.0322 (13)	0.0392 (15)	0.0424 (15)	0.0007 (12)	0.0022 (11)	0.0018 (13)
C7	0.066 (2)	0.086 (3)	0.067 (2)	0.002 (2)	0.0068 (18)	−0.036 (2)
C8	0.0280 (12)	0.0366 (15)	0.0354 (14)	0.0003 (11)	−0.0003 (10)	−0.0040 (12)
C9	0.0254 (11)	0.0327 (14)	0.0316 (13)	−0.0044 (10)	0.0030 (10)	0.0011 (11)
C10	0.0298 (12)	0.0402 (15)	0.0299 (13)	0.0040 (11)	0.0063 (10)	0.0027 (11)
C11	0.0309 (13)	0.0519 (18)	0.0302 (13)	0.0037 (12)	0.0055 (10)	0.0004 (12)
C12	0.0344 (15)	0.076 (2)	0.0432 (17)	0.0123 (15)	0.0004 (12)	0.0061 (16)
C13	0.0533 (19)	0.069 (2)	0.0544 (19)	0.0303 (18)	0.0104 (15)	0.0104 (18)
C14	0.067 (2)	0.0481 (19)	0.057 (2)	0.0191 (17)	0.0089 (17)	−0.0003 (16)
C15	0.0456 (16)	0.0454 (18)	0.0417 (16)	0.0073 (14)	0.0026 (12)	−0.0025 (13)
C16	0.0376 (17)	0.099 (3)	0.066 (2)	−0.0064 (18)	−0.0055 (15)	−0.033 (2)

Br1—C5	1.902 (3)	C6—H6	0.9300
O1—C2	1.363 (3)	C7—H7A	0.9600
O1—C7	1.421 (4)	C7—H7B	0.9600
O2—C9	1.223 (3)	C7—H7C	0.9600
O3—C11	1.367 (3)	C8—H8	0.9300
O3—C16	1.425 (3)	C9—C10	1.495 (3)
N1—C8	1.273 (3)	C10—C15	1.390 (4)
N1—N2	1.380 (3)	C10—C11	1.398 (3)
N2—C9	1.348 (3)	C11—C12	1.389 (4)
N2—H2	0.894 (10)	C12—C13	1.369 (5)
C1—C6	1.390 (4)	C12—H12	0.9300
C1—C2	1.402 (4)	C13—C14	1.363 (5)
C1—C8	1.462 (3)	C13—H13	0.9300
C2—C3	1.383 (4)	C14—C15	1.377 (4)
C3—C4	1.380 (4)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.376 (4)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.376 (4)	C16—H16C	0.9600
C2—O1—C7	118.5 (2)	N1—C8—C1	120.2 (2)
C11—O3—C16	118.6 (2)	N1—C8—H8	119.9
C8—N1—N2	115.0 (2)	C1—C8—H8	119.9
C9—N2—N1	119.2 (2)	O2—C9—N2	123.0 (2)
C9—N2—H2	124 (2)	O2—C9—C10	120.7 (2)
N1—N2—H2	116 (2)	N2—C9—C10	116.3 (2)
C6—C1—C2	118.7 (2)	C15—C10—C11	118.3 (2)
C6—C1—C8	121.3 (2)	C15—C10—C9	116.3 (2)
C2—C1—C8	120.0 (2)	C11—C10—C9	125.3 (2)
O1—C2—C3	124.0 (3)	O3—C11—C12	124.2 (3)
O1—C2—C1	115.7 (2)	O3—C11—C10	116.3 (2)
C3—C2—C1	120.3 (3)	C12—C11—C10	119.5 (3)
C4—C3—C2	120.3 (3)	C13—C12—C11	120.5 (3)
C4—C3—H3	119.9	C13—C12—H12	119.7
C2—C3—H3	119.9	C11—C12—H12	119.7
C5—C4—C3	119.5 (3)	C14—C13—C12	120.6 (3)
C5—C4—H4	120.3	C14—C13—H13	119.7
C3—C4—H4	120.3	C12—C13—H13	119.7
C6—C5—C4	121.2 (3)	C13—C14—C15	119.7 (3)
C6—C5—Br1	119.3 (2)	C13—C14—H14	120.1
C4—C5—Br1	119.5 (2)	C15—C14—H14	120.1
C5—C6—C1	120.1 (3)	C14—C15—C10	121.3 (3)
C5—C6—H6	120.0	C14—C15—H15	119.4
C1—C6—H6	120.0	C10—C15—H15	119.4
O1—C7—H7A	109.5	O3—C16—H16A	109.5
O1—C7—H7B	109.5	O3—C16—H16B	109.5
H7A—C7—H7B	109.5	H16A—C16—H16B	109.5
O1—C7—H7C	109.5	O3—C16—H16C	109.5
H7A—C7—H7C	109.5	H16A—C16—H16C	109.5
H7B—C7—H7C	109.5	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.89 (1)	2.18 (2)	2.997 (3)	152 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.894 (10)	2.179 (19)	2.997 (3)	152 (3)

Symmetry code: (i) .