N'-(5-Bromo-2-hydr-oxy-3-methoxy-benzyl-idene)isonicotinohydrazide.

The title compound, C(14)H(12)BrN(3)O(3), was prepared by reaction of 5-bromo-3-methoxy-salicylaldehyde and isonicotinohydrazide in methanol. The mol-ecule is not planar and adopts a trans configuration with respect to the C=N bond. There is an intra-molecular O-H⋯N hydrogen bond in the mol-ecule. The dihedral angle between the benzene and pyridine rings is 12.2 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯N hydrogen bonds, forming chains running along the c-axis direction.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background on the biological properties of hydrazones, see: El-Tabl et al. (2008 ▶), Chen et al. (2008 ▶); Alvarez et al. (2008 ▶); Ventura & Martins (2008 ▶); Kalinowski et al. (2008 ▶). For related structures, see: Peng & Hou (2008 ▶); Shan et al. (2008 ▶); Fun et al. (2008 ▶); Yehye et al. (2008 ▶); Ejsmont et al. (2008 ▶); Han et al. (2006 ▶); Lu et al. (2008 ▶).

Experimental

Crystal data

C14H12BrN3O3

M = 350.18

Monoclinic,

a = 7.4937 (9) Å

b = 15.8843 (19) Å

c = 11.7994 (14) Å

β = 99.776 (2)°

V = 1384.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.98 mm−1

T = 298 (2) K

0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.587, T max = 0.616 (expected range = 0.557–0.584)

8003 measured reflections

3013 independent reflections

2299 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.076

S = 1.03

3013 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.41 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/S1600536808029607/sj2539sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029607/sj2539Isup2.hkl

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

C14H12BrN3O3	F(000) = 704
Mr = 350.18	Dx = 1.680 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3223 reflections
a = 7.4937 (9) Å	θ = 2.5–29.2°
b = 15.8843 (19) Å	µ = 2.98 mm−1
c = 11.7994 (14) Å	T = 298 K
β = 99.776 (2)°	Block, colorless
V = 1384.1 (3) Å3	0.20 × 0.18 × 0.18 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3013 independent reflections
Radiation source: fine-focus sealed tube	2299 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.587, Tmax = 0.616	k = −17→20
8003 measured reflections	l = −15→11

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0328P)2 + 0.5984P] where P = (Fo2 + 2Fc2)/3
3013 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.39 e Å−3
1 restraint	Δρmin = −0.41 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	0.28353 (5)	0.417081 (18)	1.029574 (19)	0.06245 (12)
O1	0.1144 (2)	0.35958 (10)	0.51873 (12)	0.0457 (4)
H1	0.1510	0.3985	0.4832	0.069*
O2	0.0357 (2)	0.24186 (10)	0.65725 (13)	0.0473 (4)
O3	0.2696 (3)	0.49630 (11)	0.27412 (14)	0.0651 (6)
N1	0.2592 (2)	0.50906 (11)	0.49603 (15)	0.0366 (4)
N2	0.3058 (3)	0.57618 (11)	0.43355 (15)	0.0368 (4)
N3	0.3899 (3)	0.77447 (12)	0.10697 (16)	0.0422 (5)
C1	0.2305 (3)	0.45105 (13)	0.67791 (17)	0.0322 (5)
C2	0.1524 (3)	0.37588 (13)	0.63313 (16)	0.0314 (4)
C3	0.1127 (3)	0.31267 (13)	0.70889 (17)	0.0328 (5)
C4	0.1548 (3)	0.32447 (14)	0.82630 (17)	0.0352 (5)
H4	0.1314	0.2823	0.8765	0.042*
C5	0.2323 (3)	0.39986 (14)	0.86841 (17)	0.0370 (5)
C6	0.2695 (3)	0.46250 (14)	0.79697 (17)	0.0375 (5)
H6	0.3208	0.5127	0.8274	0.045*
C7	0.2776 (3)	0.51825 (13)	0.60474 (18)	0.0376 (5)
H7	0.3220	0.5689	0.6378	0.045*
C8	0.3013 (3)	0.56400 (14)	0.31958 (18)	0.0379 (5)
C9	0.3367 (3)	0.64012 (13)	0.25079 (17)	0.0321 (5)
C10	0.2656 (3)	0.63897 (14)	0.13450 (18)	0.0408 (5)
H10	0.1991	0.5929	0.1022	0.049*
C11	0.2945 (3)	0.70697 (15)	0.0670 (2)	0.0449 (6)
H11	0.2445	0.7055	−0.0107	0.054*
C12	0.4597 (3)	0.77448 (14)	0.2190 (2)	0.0395 (5)
H12	0.5287	0.8207	0.2484	0.047*
C13	0.4358 (3)	0.71018 (13)	0.29379 (18)	0.0350 (5)
H13	0.4853	0.7138	0.3714	0.042*
C14	0.0108 (3)	0.17267 (14)	0.7293 (2)	0.0473 (6)
H14A	0.1255	0.1566	0.7732	0.071*
H14B	−0.0397	0.1261	0.6828	0.071*
H14C	−0.0701	0.1886	0.7805	0.071*
H2	0.331 (4)	0.6240 (12)	0.472 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.1005 (3)	0.0644 (2)	0.02233 (13)	−0.01755 (16)	0.01035 (12)	−0.00145 (11)
O1	0.0749 (12)	0.0384 (9)	0.0233 (7)	−0.0087 (8)	0.0068 (7)	−0.0007 (6)
O2	0.0711 (11)	0.0338 (8)	0.0357 (8)	−0.0121 (8)	0.0053 (8)	0.0022 (7)
O3	0.1248 (17)	0.0381 (9)	0.0351 (9)	−0.0254 (10)	0.0207 (10)	−0.0054 (8)
N1	0.0502 (12)	0.0317 (10)	0.0292 (9)	0.0001 (8)	0.0104 (8)	0.0049 (7)
N2	0.0560 (12)	0.0280 (9)	0.0282 (9)	−0.0011 (9)	0.0123 (8)	0.0047 (7)
N3	0.0509 (12)	0.0379 (10)	0.0394 (10)	0.0030 (9)	0.0122 (9)	0.0087 (8)
C1	0.0411 (12)	0.0296 (10)	0.0269 (10)	0.0031 (9)	0.0082 (9)	0.0025 (8)
C2	0.0386 (12)	0.0318 (11)	0.0234 (9)	0.0049 (9)	0.0043 (8)	0.0006 (8)
C3	0.0373 (12)	0.0300 (11)	0.0313 (10)	0.0017 (9)	0.0062 (9)	0.0005 (9)
C4	0.0412 (13)	0.0364 (12)	0.0296 (10)	0.0030 (10)	0.0105 (9)	0.0059 (9)
C5	0.0477 (13)	0.0427 (13)	0.0215 (10)	−0.0004 (10)	0.0078 (9)	−0.0016 (9)
C6	0.0511 (14)	0.0339 (11)	0.0279 (10)	−0.0022 (10)	0.0079 (9)	−0.0036 (9)
C7	0.0523 (14)	0.0302 (11)	0.0309 (11)	−0.0003 (10)	0.0089 (10)	0.0000 (9)
C8	0.0502 (14)	0.0349 (12)	0.0296 (10)	−0.0024 (10)	0.0100 (10)	0.0013 (9)
C9	0.0390 (12)	0.0307 (11)	0.0290 (10)	0.0036 (9)	0.0123 (9)	0.0016 (8)
C10	0.0545 (15)	0.0368 (12)	0.0306 (11)	−0.0033 (11)	0.0059 (10)	−0.0002 (9)
C11	0.0582 (16)	0.0452 (14)	0.0301 (11)	0.0021 (12)	0.0042 (10)	0.0042 (10)
C12	0.0425 (13)	0.0334 (12)	0.0437 (12)	−0.0004 (10)	0.0108 (10)	0.0014 (10)
C13	0.0401 (12)	0.0361 (12)	0.0295 (10)	0.0031 (9)	0.0080 (9)	0.0001 (9)
C14	0.0624 (16)	0.0335 (12)	0.0482 (14)	−0.0057 (11)	0.0158 (12)	0.0047 (11)

Br1—C5	1.895 (2)	C4—C5	1.386 (3)
O1—C2	1.356 (2)	C4—H4	0.9300
O1—H1	0.8200	C5—C6	1.363 (3)
O2—C3	1.360 (3)	C6—H6	0.9300
O2—C14	1.421 (3)	C7—H7	0.9300
O3—C8	1.207 (3)	C8—C9	1.505 (3)
N1—C7	1.275 (3)	C9—C10	1.385 (3)
N1—N2	1.375 (2)	C9—C13	1.386 (3)
N2—C8	1.353 (3)	C10—C11	1.381 (3)
N2—H2	0.889 (10)	C10—H10	0.9300
N3—C11	1.330 (3)	C11—H11	0.9300
N3—C12	1.336 (3)	C12—C13	1.381 (3)
C1—C2	1.394 (3)	C12—H12	0.9300
C1—C6	1.397 (3)	C13—H13	0.9300
C1—C7	1.454 (3)	C14—H14A	0.9600
C2—C3	1.409 (3)	C14—H14B	0.9600
C3—C4	1.380 (3)	C14—H14C	0.9600
C2—O1—H1	109.5	N1—C7—H7	119.4
C3—O2—C14	117.41 (17)	C1—C7—H7	119.4
C7—N1—N2	117.18 (18)	O3—C8—N2	122.6 (2)
C8—N2—N1	117.15 (18)	O3—C8—C9	121.04 (19)
C8—N2—H2	127 (2)	N2—C8—C9	116.37 (18)
N1—N2—H2	116 (2)	C10—C9—C13	117.73 (19)
C11—N3—C12	116.57 (19)	C10—C9—C8	116.78 (19)
C2—C1—C6	119.70 (19)	C13—C9—C8	125.48 (19)
C2—C1—C7	122.19 (18)	C11—C10—C9	119.3 (2)
C6—C1—C7	118.10 (19)	C11—C10—H10	120.4
O1—C2—C1	122.99 (18)	C9—C10—H10	120.4
O1—C2—C3	117.65 (18)	N3—C11—C10	123.6 (2)
C1—C2—C3	119.35 (18)	N3—C11—H11	118.2
O2—C3—C4	124.68 (19)	C10—C11—H11	118.2
O2—C3—C2	115.10 (18)	N3—C12—C13	124.1 (2)
C4—C3—C2	120.20 (19)	N3—C12—H12	118.0
C3—C4—C5	119.18 (19)	C13—C12—H12	118.0
C3—C4—H4	120.4	C12—C13—C9	118.7 (2)
C5—C4—H4	120.4	C12—C13—H13	120.7
C6—C5—C4	121.76 (19)	C9—C13—H13	120.7
C6—C5—Br1	119.16 (16)	O2—C14—H14A	109.5
C4—C5—Br1	119.06 (16)	O2—C14—H14B	109.5
C5—C6—C1	119.8 (2)	H14A—C14—H14B	109.5
C5—C6—H6	120.1	O2—C14—H14C	109.5
C1—C6—H6	120.1	H14A—C14—H14C	109.5
N1—C7—C1	121.2 (2)	H14B—C14—H14C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3i	0.89 (1)	2.26 (1)	3.126 (3)	166 (3)
O1—H1···N1	0.82	1.93	2.643 (2)	145.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N3i	0.889 (10)	2.255 (13)	3.126 (3)	166 (3)
O1—H1⋯N1	0.82	1.93	2.643 (2)	145

Symmetry code: (i) .