(E)-N'-(5-Bromo-2-meth-oxy-benzyl-idene)isonicotinohydrazide.

The asymmetric unit of the title compound, C(14)H(12)BrN(3)O(2), contains two independent mol-ecules in which the dihedral angles between the benzene ring and the pyridine ring are 24.4 (6) and 23.7 (6)°. The mol-ecules exist in a trans configuration with respect to the central methyl-idene units. In the crystal, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related structures, see: Ban (2010 ▶); Ban & Li (2008a ▶,b ▶); Li & Ban (2009a ▶,b ▶); Yehye et al. (2008 ▶); Fun et al. (2008a ▶,b ▶); Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶); Yang (2006 ▶).

Experimental

Crystal data

C14H12BrN3O2

M = 334.18

Monoclinic,

a = 10.020 (3) Å

b = 25.732 (2) Å

c = 11.243 (2) Å

β = 102.199 (3)°

V = 2833.4 (10) Å3

Z = 8

Mo Kα radiation

μ = 2.91 mm−1

T = 298 K

0.13 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.704, T max = 0.760

14099 measured reflections

5922 independent reflections

2018 reflections with I > 2σ(I)

R int = 0.114

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.143

S = 0.94

5922 reflections

369 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.43 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/S1600536811017910/sj5145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017910/sj5145Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017910/sj5145Isup3.cml

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

C14H12BrN3O2	F(000) = 1344
Mr = 334.18	Dx = 1.567 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 916 reflections
a = 10.020 (3) Å	θ = 2.5–24.3°
b = 25.732 (2) Å	µ = 2.91 mm−1
c = 11.243 (2) Å	T = 298 K
β = 102.199 (3)°	Block, colourless
V = 2833.4 (10) Å3	0.13 × 0.10 × 0.10 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	5922 independent reflections
Radiation source: fine-focus sealed tube	2018 reflections with I > 2σ(I)
graphite	Rint = 0.114
ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.704, Tmax = 0.760	k = −15→32
14099 measured reflections	l = −12→14

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3
5922 reflections	(Δ/σ)max < 0.001
369 parameters	Δρmax = 0.32 e Å−3
2 restraints	Δρmin = −0.43 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	0.51353 (8)	0.35943 (3)	0.41403 (8)	0.0813 (3)
Br2	0.03344 (8)	−0.09381 (3)	0.49305 (8)	0.0786 (3)
N1	0.7533 (5)	0.1886 (2)	0.2601 (5)	0.0433 (14)
N2	0.7920 (5)	0.1410 (2)	0.2216 (5)	0.0483 (15)
N3	0.8554 (7)	−0.0399 (2)	0.0738 (5)	0.0570 (17)
N4	0.2636 (5)	0.0667 (2)	0.2875 (5)	0.0469 (15)
N5	0.3008 (5)	0.1126 (2)	0.2381 (5)	0.0455 (15)
N6	0.3357 (8)	0.2873 (2)	0.0375 (6)	0.070 (2)
O1	1.0434 (5)	0.29599 (17)	0.2924 (4)	0.0661 (14)
O2	0.5883 (5)	0.10295 (15)	0.2207 (4)	0.0531 (13)
O3	0.5607 (5)	−0.03865 (16)	0.3491 (4)	0.0627 (14)
O4	0.0906 (5)	0.14763 (16)	0.2208 (5)	0.0675 (15)
C1	0.8234 (7)	0.2757 (2)	0.3160 (6)	0.0396 (17)
C2	0.9269 (8)	0.3125 (3)	0.3234 (6)	0.0504 (19)
C3	0.9065 (7)	0.3632 (3)	0.3589 (6)	0.056 (2)
H3	0.9754	0.3878	0.3643	0.068*
C4	0.7825 (8)	0.3763 (3)	0.3859 (6)	0.056 (2)
H4	0.7671	0.4102	0.4087	0.068*
C5	0.6821 (7)	0.3396 (3)	0.3791 (6)	0.0478 (19)
C6	0.7036 (7)	0.2897 (3)	0.3450 (6)	0.0497 (19)
H6	0.6350	0.2651	0.3417	0.060*
C7	1.1577 (7)	0.3308 (3)	0.3069 (6)	0.070 (2)
H7A	1.1368	0.3586	0.2489	0.105*
H7B	1.2364	0.3123	0.2936	0.105*
H7C	1.1763	0.3449	0.3878	0.105*
C8	0.8473 (7)	0.2231 (2)	0.2755 (6)	0.054 (2)
H8	0.9325	0.2146	0.2606	0.064*
C9	0.7057 (7)	0.1007 (2)	0.2057 (6)	0.0432 (18)
C10	0.7624 (7)	0.0518 (2)	0.1629 (6)	0.0387 (17)
C11	0.6714 (7)	0.0151 (2)	0.1033 (6)	0.052 (2)
H11	0.5777	0.0201	0.0927	0.062*
C12	0.7233 (8)	−0.0294 (3)	0.0596 (6)	0.058 (2)
H12	0.6615	−0.0534	0.0177	0.069*
C13	0.9394 (7)	−0.0048 (3)	0.1323 (6)	0.055 (2)
H13	1.0325	−0.0113	0.1443	0.066*
C14	0.8989 (7)	0.0409 (2)	0.1769 (6)	0.0464 (18)
H14	0.9638	0.0644	0.2165	0.056*
C15	0.3380 (7)	−0.0171 (2)	0.3649 (6)	0.0431 (18)
C16	0.4437 (7)	−0.0535 (3)	0.3829 (6)	0.0456 (18)
C17	0.4289 (7)	−0.1015 (3)	0.4355 (6)	0.055 (2)
H17	0.4998	−0.1255	0.4484	0.066*
C18	0.3064 (8)	−0.1126 (3)	0.4681 (6)	0.057 (2)
H18	0.2953	−0.1445	0.5040	0.068*
C19	0.2015 (6)	−0.0777 (3)	0.4487 (6)	0.0452 (18)
C20	0.2170 (7)	−0.0301 (3)	0.3968 (6)	0.0473 (18)
H20	0.1450	−0.0065	0.3832	0.057*
C21	0.6772 (7)	−0.0721 (3)	0.3758 (6)	0.072 (2)
H21A	0.6994	−0.0793	0.4615	0.107*
H21B	0.7534	−0.0553	0.3525	0.107*
H21C	0.6571	−0.1040	0.3315	0.107*
C22	0.3574 (7)	0.0332 (3)	0.3104 (6)	0.0483 (19)
H22	0.4416	0.0407	0.2919	0.058*
C23	0.2085 (8)	0.1511 (2)	0.2091 (6)	0.0479 (19)
C24	0.2575 (7)	0.1983 (2)	0.1524 (6)	0.0398 (18)
C25	0.3935 (7)	0.2111 (3)	0.1626 (6)	0.059 (2)
H25	0.4620	0.1904	0.2077	0.071*
C26	0.4257 (8)	0.2552 (3)	0.1049 (7)	0.069 (2)
H26	0.5177	0.2632	0.1137	0.083*
C27	0.2071 (10)	0.2744 (3)	0.0269 (7)	0.073 (3)
H27	0.1409	0.2951	−0.0214	0.087*
C28	0.1643 (7)	0.2316 (3)	0.0838 (6)	0.053 (2)
H28	0.0714	0.2253	0.0755	0.064*
H5	0.388 (2)	0.116 (2)	0.232 (6)	0.080*
H2	0.880 (2)	0.139 (3)	0.214 (6)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0673 (6)	0.0816 (6)	0.0990 (7)	0.0128 (5)	0.0266 (5)	−0.0272 (6)
Br2	0.0568 (6)	0.0881 (7)	0.0920 (7)	−0.0143 (5)	0.0184 (5)	0.0230 (6)
N1	0.038 (4)	0.035 (3)	0.059 (4)	0.002 (3)	0.016 (3)	−0.003 (3)
N2	0.032 (3)	0.034 (3)	0.081 (4)	0.007 (3)	0.018 (3)	−0.001 (3)
N3	0.057 (4)	0.039 (4)	0.078 (5)	0.007 (4)	0.021 (4)	−0.002 (3)
N4	0.047 (4)	0.032 (3)	0.064 (4)	0.000 (3)	0.016 (3)	−0.002 (3)
N5	0.037 (4)	0.030 (3)	0.074 (4)	−0.001 (3)	0.022 (3)	0.007 (3)
N6	0.091 (6)	0.044 (4)	0.076 (5)	−0.012 (4)	0.021 (5)	0.000 (4)
O1	0.050 (3)	0.054 (3)	0.102 (4)	−0.018 (3)	0.032 (3)	−0.016 (3)
O2	0.042 (3)	0.033 (3)	0.090 (4)	−0.002 (2)	0.026 (3)	0.000 (2)
O3	0.050 (3)	0.049 (3)	0.096 (4)	0.013 (3)	0.028 (3)	0.011 (3)
O4	0.036 (3)	0.045 (3)	0.127 (5)	0.002 (3)	0.032 (3)	0.003 (3)
C1	0.038 (4)	0.034 (4)	0.051 (5)	−0.009 (4)	0.018 (4)	−0.004 (4)
C2	0.049 (5)	0.035 (5)	0.069 (6)	−0.007 (4)	0.018 (4)	−0.012 (4)
C3	0.058 (5)	0.040 (5)	0.074 (6)	−0.021 (4)	0.022 (4)	−0.002 (4)
C4	0.070 (6)	0.033 (4)	0.070 (6)	−0.007 (4)	0.022 (5)	−0.015 (4)
C5	0.051 (5)	0.047 (5)	0.044 (5)	0.002 (4)	0.006 (4)	0.001 (4)
C6	0.039 (5)	0.039 (5)	0.072 (6)	−0.008 (4)	0.014 (4)	−0.008 (4)
C7	0.043 (5)	0.078 (6)	0.094 (6)	−0.020 (4)	0.029 (4)	0.000 (5)
C8	0.053 (5)	0.034 (4)	0.077 (6)	−0.004 (4)	0.021 (4)	−0.011 (4)
C9	0.039 (5)	0.033 (4)	0.059 (5)	0.004 (4)	0.013 (4)	0.003 (4)
C10	0.035 (4)	0.031 (4)	0.055 (5)	0.003 (3)	0.020 (4)	0.007 (4)
C11	0.035 (4)	0.030 (4)	0.090 (6)	0.001 (4)	0.015 (4)	−0.004 (4)
C12	0.058 (6)	0.033 (5)	0.083 (6)	−0.004 (4)	0.018 (5)	0.000 (4)
C13	0.042 (5)	0.043 (5)	0.083 (6)	0.006 (4)	0.018 (4)	−0.003 (5)
C14	0.045 (5)	0.033 (4)	0.063 (5)	−0.002 (4)	0.017 (4)	−0.009 (4)
C15	0.040 (5)	0.033 (4)	0.058 (5)	0.003 (4)	0.015 (4)	−0.008 (4)
C16	0.053 (5)	0.034 (4)	0.053 (5)	−0.009 (4)	0.018 (4)	−0.005 (4)
C17	0.047 (5)	0.050 (5)	0.069 (6)	0.009 (4)	0.013 (4)	0.000 (4)
C18	0.067 (6)	0.042 (5)	0.058 (5)	0.000 (4)	0.008 (4)	0.003 (4)
C19	0.034 (4)	0.045 (5)	0.054 (5)	−0.005 (4)	0.004 (4)	0.006 (4)
C20	0.042 (5)	0.043 (5)	0.059 (5)	0.003 (4)	0.017 (4)	0.000 (4)
C21	0.053 (5)	0.079 (6)	0.085 (6)	0.033 (5)	0.020 (4)	−0.002 (5)
C22	0.046 (5)	0.041 (5)	0.063 (5)	0.001 (4)	0.023 (4)	0.000 (4)
C23	0.045 (5)	0.033 (5)	0.069 (5)	0.001 (4)	0.021 (4)	0.002 (4)
C24	0.039 (4)	0.028 (4)	0.052 (5)	0.000 (4)	0.008 (4)	−0.013 (4)
C25	0.052 (5)	0.048 (5)	0.078 (6)	−0.002 (4)	0.016 (4)	0.000 (5)
C26	0.062 (6)	0.052 (5)	0.092 (7)	−0.010 (5)	0.012 (5)	0.011 (5)
C27	0.106 (8)	0.046 (6)	0.063 (6)	0.013 (5)	0.011 (6)	0.015 (5)
C28	0.045 (5)	0.045 (5)	0.066 (5)	0.011 (4)	0.004 (4)	0.005 (4)

Br1—C5	1.884 (7)	C8—H8	0.9300
Br2—C19	1.900 (6)	C9—C10	1.500 (8)
N1—C8	1.279 (7)	C10—C14	1.373 (8)
N1—N2	1.382 (6)	C10—C11	1.384 (8)
N2—C9	1.337 (8)	C11—C12	1.390 (8)
N2—H2	0.900 (10)	C11—H11	0.9300
N3—C13	1.313 (8)	C12—H12	0.9300
N3—C12	1.326 (8)	C13—C14	1.372 (8)
N4—C22	1.262 (7)	C13—H13	0.9300
N4—N5	1.388 (6)	C14—H14	0.9300
N5—C23	1.347 (8)	C15—C20	1.376 (8)
N5—H5	0.901 (10)	C15—C16	1.395 (8)
N6—C27	1.312 (9)	C15—C22	1.464 (8)
N6—C26	1.335 (8)	C16—C17	1.391 (8)
O1—C2	1.354 (8)	C17—C18	1.384 (9)
O1—C7	1.437 (7)	C17—H17	0.9300
O2—C9	1.224 (7)	C18—C19	1.364 (8)
O3—C16	1.361 (7)	C18—H18	0.9300
O3—C21	1.430 (7)	C19—C20	1.381 (8)
O4—C23	1.219 (7)	C20—H20	0.9300
C1—C6	1.358 (8)	C21—H21A	0.9600
C1—C2	1.394 (8)	C21—H21B	0.9600
C1—C8	1.463 (8)	C21—H21C	0.9600
C2—C3	1.392 (8)	C22—H22	0.9300
C3—C4	1.382 (9)	C23—C24	1.502 (8)
C3—H3	0.9300	C24—C28	1.377 (8)
C4—C5	1.371 (8)	C24—C25	1.383 (8)
C4—H4	0.9300	C25—C26	1.378 (9)
C5—C6	1.369 (8)	C25—H25	0.9300
C6—H6	0.9300	C26—H26	0.9300
C7—H7A	0.9600	C27—C28	1.386 (9)
C7—H7B	0.9600	C27—H27	0.9300
C7—H7C	0.9600	C28—H28	0.9300
C8—N1—N2	114.2 (5)	N3—C13—C14	124.4 (7)
C9—N2—N1	120.9 (5)	N3—C13—H13	117.8
C9—N2—H2	124 (4)	C14—C13—H13	117.8
N1—N2—H2	115 (4)	C13—C14—C10	119.9 (6)
C13—N3—C12	116.0 (6)	C13—C14—H14	120.1
C22—N4—N5	114.3 (6)	C10—C14—H14	120.1
C23—N5—N4	119.6 (6)	C20—C15—C16	118.9 (6)
C23—N5—H5	122 (4)	C20—C15—C22	121.7 (6)
N4—N5—H5	118 (4)	C16—C15—C22	119.3 (6)
C27—N6—C26	115.3 (7)	O3—C16—C17	122.9 (6)
C2—O1—C7	119.0 (5)	O3—C16—C15	116.4 (6)
C16—O3—C21	119.1 (5)	C17—C16—C15	120.7 (7)
C6—C1—C2	119.3 (6)	C18—C17—C16	118.5 (7)
C6—C1—C8	122.2 (6)	C18—C17—H17	120.7
C2—C1—C8	118.6 (6)	C16—C17—H17	120.7
O1—C2—C3	123.7 (6)	C19—C18—C17	121.1 (7)
O1—C2—C1	116.3 (6)	C19—C18—H18	119.4
C3—C2—C1	120.1 (7)	C17—C18—H18	119.4
C4—C3—C2	119.1 (6)	C18—C19—C20	120.0 (6)
C4—C3—H3	120.4	C18—C19—Br2	120.7 (6)
C2—C3—H3	120.4	C20—C19—Br2	119.3 (5)
C5—C4—C3	120.1 (6)	C15—C20—C19	120.6 (6)
C5—C4—H4	120.0	C15—C20—H20	119.7
C3—C4—H4	120.0	C19—C20—H20	119.7
C6—C5—C4	120.4 (6)	O3—C21—H21A	109.5
C6—C5—Br1	120.9 (6)	O3—C21—H21B	109.5
C4—C5—Br1	118.7 (6)	H21A—C21—H21B	109.5
C1—C6—C5	121.1 (6)	O3—C21—H21C	109.5
C1—C6—H6	119.5	H21A—C21—H21C	109.5
C5—C6—H6	119.5	H21B—C21—H21C	109.5
O1—C7—H7A	109.5	N4—C22—C15	122.1 (6)
O1—C7—H7B	109.5	N4—C22—H22	119.0
H7A—C7—H7B	109.5	C15—C22—H22	119.0
O1—C7—H7C	109.5	O4—C23—N5	123.5 (6)
H7A—C7—H7C	109.5	O4—C23—C24	121.0 (6)
H7B—C7—H7C	109.5	N5—C23—C24	115.4 (6)
N1—C8—C1	121.3 (6)	C28—C24—C25	115.9 (6)
N1—C8—H8	119.4	C28—C24—C23	119.8 (6)
C1—C8—H8	119.4	C25—C24—C23	124.3 (6)
O2—C9—N2	123.9 (6)	C26—C25—C24	118.8 (7)
O2—C9—C10	121.6 (6)	C26—C25—H25	120.6
N2—C9—C10	114.5 (6)	C24—C25—H25	120.6
C14—C10—C11	117.0 (6)	N6—C26—C25	125.5 (8)
C14—C10—C9	124.8 (6)	N6—C26—H26	117.3
C11—C10—C9	118.2 (6)	C25—C26—H26	117.3
C10—C11—C12	118.4 (6)	N6—C27—C28	123.6 (7)
C10—C11—H11	120.8	N6—C27—H27	118.2
C12—C11—H11	120.8	C28—C27—H27	118.2
N3—C12—C11	124.3 (7)	C24—C28—C27	120.9 (7)
N3—C12—H12	117.9	C24—C28—H28	119.5
C11—C12—H12	117.9	C27—C28—H28	119.5

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O2	0.90 (1)	2.06 (2)	2.939 (7)	164 (6)
N2—H2···O4i	0.90 (1)	2.11 (2)	2.999 (7)	168 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O2	0.90 (1)	2.06 (2)	2.939 (7)	164 (6)
N2—H2⋯O4i	0.90 (1)	2.11 (2)	2.999 (7)	168 (6)

Symmetry code: (i) .