N'-(5-Bromo-2-methoxy-benzyl-idene)-3,4-methyl-enedioxy-benzohydrazide.

In the title mol-ecule, C(16)H(13)BrN(2)O(4), the two benzene rings form a dihedral angle of 74.9 (2)°. In the crystal, mol-ecules are linked via inter-molecular N-H⋯O hydrogen bonds into chains propagating along the c axis.

Related literature

For the biological activity of hydrazone derivatives, see: Khattab (2005 ▶); Küçükgüzel et al. (2003 ▶); Cukurovali et al. (2006 ▶). For the crystal structures of related compounds, see: Fun et al. (2008 ▶); Wei et al. (2009 ▶); Khaledi et al. (2008 ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

C16H13BrN2O4

M = 377.19

Monoclinic,

a = 12.678 (1) Å

b = 16.217 (2) Å

c = 7.846 (2) Å

β = 104.804 (3)°

V = 1559.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.66 mm−1

T = 298 K

0.30 × 0.28 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.503, T max = 0.534 (expected range = 0.460–0.488)

8368 measured reflections

3110 independent reflections

1932 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.096

S = 1.04

3110 reflections

212 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.47 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/S1600536809022818/cv2572sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022818/cv2572Isup2.hkl

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

C16H13BrN2O4	F(000) = 760
Mr = 377.19	Dx = 1.606 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2058 reflections
a = 12.678 (1) Å	θ = 2.5–24.5°
b = 16.217 (2) Å	µ = 2.66 mm−1
c = 7.846 (2) Å	T = 298 K
β = 104.804 (3)°	Block, colourless
V = 1559.6 (5) Å3	0.30 × 0.28 × 0.27 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3110 independent reflections
Radiation source: fine-focus sealed tube	1932 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 26.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→15
Tmin = 0.503, Tmax = 0.534	k = −19→19
8368 measured reflections	l = −9→4

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0397P)2 + 0.3363P] where P = (Fo2 + 2Fc2)/3
3110 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.26 e Å−3
1 restraint	Δρmin = −0.47 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	0.79365 (3)	0.77734 (2)	0.01187 (6)	0.08050 (19)
O1	0.47896 (16)	0.98772 (12)	0.2718 (3)	0.0551 (6)
O2	0.23491 (16)	0.66086 (12)	−0.0682 (3)	0.0495 (5)
O3	−0.13891 (18)	0.56492 (16)	0.0073 (3)	0.0777 (7)
O4	−0.1167 (2)	0.54766 (14)	0.3048 (4)	0.0750 (7)
N1	0.38458 (18)	0.76267 (14)	0.1294 (3)	0.0420 (6)
N2	0.29501 (19)	0.73440 (14)	0.1821 (3)	0.0427 (6)
C1	0.5282 (2)	0.86061 (18)	0.1769 (4)	0.0426 (7)
C2	0.5525 (2)	0.94368 (18)	0.2108 (4)	0.0434 (7)
C3	0.6454 (2)	0.9767 (2)	0.1762 (4)	0.0542 (8)
H3	0.6603	1.0327	0.1944	0.065*
C4	0.7157 (3)	0.9274 (2)	0.1152 (4)	0.0561 (8)
H4	0.7787	0.9498	0.0939	0.067*
C5	0.6934 (2)	0.8455 (2)	0.0857 (4)	0.0504 (8)
C6	0.6000 (2)	0.81226 (19)	0.1145 (4)	0.0482 (8)
H6	0.5848	0.7566	0.0918	0.058*
C7	0.4292 (2)	0.82617 (17)	0.2101 (4)	0.0423 (7)
H7	0.3982	0.8514	0.2922	0.051*
C8	0.2255 (2)	0.68194 (17)	0.0780 (4)	0.0392 (7)
C9	0.1363 (2)	0.64994 (16)	0.1497 (4)	0.0382 (7)
C10	0.0401 (2)	0.62571 (18)	0.0293 (4)	0.0495 (8)
H10	0.0306	0.6312	−0.0917	0.059*
C11	−0.0387 (2)	0.59384 (18)	0.0980 (5)	0.0490 (8)
C12	−0.0262 (2)	0.58422 (18)	0.2737 (5)	0.0521 (8)
C13	0.0667 (3)	0.6066 (2)	0.3945 (4)	0.0583 (9)
H13	0.0750	0.5994	0.5148	0.070*
C14	0.1485 (2)	0.64061 (18)	0.3280 (4)	0.0480 (7)
H14	0.2131	0.6576	0.4060	0.058*
C15	−0.1939 (3)	0.5446 (2)	0.1383 (6)	0.0819 (12)
H15A	−0.2524	0.5835	0.1351	0.098*
H15B	−0.2250	0.4897	0.1173	0.098*
C16	0.5016 (3)	1.07233 (19)	0.3115 (4)	0.0610 (9)
H16A	0.5691	1.0773	0.4005	0.092*
H16B	0.4437	1.0961	0.3538	0.092*
H16C	0.5073	1.1008	0.2070	0.092*
H2	0.278 (3)	0.7609 (18)	0.271 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0737 (3)	0.0813 (3)	0.1027 (3)	0.0049 (2)	0.0521 (2)	−0.0014 (2)
O1	0.0564 (13)	0.0467 (13)	0.0667 (14)	−0.0076 (10)	0.0240 (12)	−0.0086 (11)
O2	0.0570 (13)	0.0515 (12)	0.0467 (12)	−0.0134 (10)	0.0255 (11)	−0.0098 (10)
O3	0.0461 (14)	0.0882 (18)	0.098 (2)	−0.0217 (13)	0.0169 (14)	−0.0130 (15)
O4	0.0626 (15)	0.0723 (17)	0.105 (2)	−0.0207 (13)	0.0492 (16)	0.0006 (15)
N1	0.0403 (13)	0.0441 (15)	0.0456 (15)	−0.0083 (11)	0.0186 (12)	−0.0008 (12)
N2	0.0427 (14)	0.0452 (14)	0.0465 (15)	−0.0125 (12)	0.0226 (12)	−0.0047 (12)
C1	0.0418 (17)	0.0469 (18)	0.0389 (17)	−0.0100 (14)	0.0097 (14)	0.0029 (14)
C2	0.0441 (17)	0.0469 (18)	0.0390 (17)	−0.0061 (14)	0.0104 (14)	0.0006 (14)
C3	0.0524 (19)	0.0492 (19)	0.062 (2)	−0.0178 (15)	0.0176 (17)	−0.0060 (16)
C4	0.0467 (18)	0.064 (2)	0.061 (2)	−0.0142 (16)	0.0199 (17)	0.0026 (18)
C5	0.0470 (18)	0.056 (2)	0.0521 (19)	−0.0026 (15)	0.0204 (16)	0.0014 (16)
C6	0.0516 (18)	0.0436 (17)	0.0513 (19)	−0.0060 (15)	0.0165 (16)	0.0023 (15)
C7	0.0441 (17)	0.0437 (18)	0.0420 (17)	−0.0062 (14)	0.0164 (14)	−0.0020 (14)
C8	0.0405 (16)	0.0356 (16)	0.0446 (17)	−0.0027 (13)	0.0168 (14)	0.0003 (14)
C9	0.0357 (15)	0.0357 (15)	0.0455 (17)	−0.0015 (12)	0.0148 (14)	0.0006 (14)
C10	0.0450 (18)	0.055 (2)	0.0494 (19)	−0.0050 (15)	0.0141 (16)	−0.0023 (16)
C11	0.0330 (16)	0.0450 (18)	0.069 (2)	−0.0062 (14)	0.0126 (16)	−0.0056 (16)
C12	0.0466 (19)	0.0402 (17)	0.079 (2)	−0.0097 (15)	0.0341 (18)	−0.0024 (17)
C13	0.070 (2)	0.062 (2)	0.052 (2)	−0.0107 (18)	0.0309 (19)	0.0063 (17)
C14	0.0442 (17)	0.0503 (19)	0.0515 (19)	−0.0075 (14)	0.0158 (15)	0.0019 (15)
C15	0.048 (2)	0.075 (3)	0.128 (4)	−0.0163 (19)	0.031 (3)	−0.006 (3)
C16	0.072 (2)	0.047 (2)	0.067 (2)	−0.0021 (17)	0.0240 (19)	−0.0059 (17)

Br1—C5	1.884 (3)	C4—H4	0.9300
O1—C2	1.355 (3)	C5—C6	1.371 (4)
O1—C16	1.420 (4)	C6—H6	0.9300
O2—C8	1.232 (3)	C7—H7	0.9300
O3—C11	1.370 (3)	C8—C9	1.479 (4)
O3—C15	1.420 (4)	C9—C14	1.376 (4)
O4—C12	1.367 (3)	C9—C10	1.395 (4)
O4—C15	1.419 (5)	C10—C11	1.353 (4)
N1—C7	1.264 (3)	C10—H10	0.9300
N1—N2	1.382 (3)	C11—C12	1.356 (4)
N2—C8	1.341 (4)	C12—C13	1.359 (4)
N2—H2	0.89 (3)	C13—C14	1.389 (4)
C1—C6	1.382 (4)	C13—H13	0.9300
C1—C2	1.392 (4)	C14—H14	0.9300
C1—C7	1.458 (4)	C15—H15A	0.9700
C2—C3	1.383 (4)	C15—H15B	0.9700
C3—C4	1.372 (4)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.366 (4)	C16—H16C	0.9600
C2—O1—C16	117.9 (2)	C14—C9—C10	120.5 (3)
C11—O3—C15	105.4 (3)	C14—C9—C8	121.8 (3)
C12—O4—C15	105.3 (3)	C10—C9—C8	117.6 (3)
C7—N1—N2	114.6 (2)	C11—C10—C9	116.4 (3)
C8—N2—N1	119.4 (2)	C11—C10—H10	121.8
C8—N2—H2	122 (2)	C9—C10—H10	121.8
N1—N2—H2	117 (2)	C10—C11—C12	122.9 (3)
C6—C1—C2	118.9 (3)	C10—C11—O3	127.2 (3)
C6—C1—C7	121.4 (3)	C12—C11—O3	109.9 (3)
C2—C1—C7	119.6 (3)	C11—C12—C13	122.2 (3)
O1—C2—C3	124.2 (3)	C11—C12—O4	110.2 (3)
O1—C2—C1	116.1 (2)	C13—C12—O4	127.5 (3)
C3—C2—C1	119.7 (3)	C12—C13—C14	116.2 (3)
C4—C3—C2	120.3 (3)	C12—C13—H13	121.9
C4—C3—H3	119.8	C14—C13—H13	121.9
C2—C3—H3	119.8	C9—C14—C13	121.7 (3)
C5—C4—C3	120.1 (3)	C9—C14—H14	119.2
C5—C4—H4	119.9	C13—C14—H14	119.2
C3—C4—H4	119.9	O4—C15—O3	107.9 (3)
C4—C5—C6	120.3 (3)	O4—C15—H15A	110.1
C4—C5—Br1	119.7 (2)	O3—C15—H15A	110.1
C6—C5—Br1	119.9 (3)	O4—C15—H15B	110.1
C5—C6—C1	120.7 (3)	O3—C15—H15B	110.1
C5—C6—H6	119.7	H15A—C15—H15B	108.4
C1—C6—H6	119.7	O1—C16—H16A	109.5
N1—C7—C1	121.2 (3)	O1—C16—H16B	109.5
N1—C7—H7	119.4	H16A—C16—H16B	109.5
C1—C7—H7	119.4	O1—C16—H16C	109.5
O2—C8—N2	122.5 (2)	H16A—C16—H16C	109.5
O2—C8—C9	121.5 (3)	H16B—C16—H16C	109.5
N2—C8—C9	116.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.89 (3)	1.96 (3)	2.841 (3)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.89 (3)	1.96 (3)	2.841 (3)	168 (3)

Symmetry code: (i) .