(E)-N'-(3,5-Dibromo-2-hydroxy-benzyl-idene)nicotinohydrazide.

In the title Schiff base compound, C(13)H(9)Br(2)N(3)O(2), there is an intra-molecular O-H⋯N hydrogen bond involving the hydroxyl substituent and the adjacent hydrazine N atom. The mol-ecule is almost planar, the dihedral angle between the benzene ring and the pyridine ring being 5.7 (2)°. In the crystal structure, symmetry-related mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains propagating in [001].

Related literature

For related literature on Schiff bases, see: Archibald et al. (1994 ▶); Harada et al. (1999 ▶); Ogawa et al. (1998 ▶). For similar structures, see: Mohd Lair et al. (2009 ▶); Li et al. (2010 ▶); Sun et al. (2009 ▶); Wang et al. (2010 ▶); Wen et al. (2009 ▶).

Experimental

Crystal data

C13H9Br2N3O2

M = 399.05

Monoclinic,

a = 17.013 (4) Å

b = 8.091 (2) Å

c = 10.153 (3) Å

β = 92.194 (13)°

V = 1396.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 5.81 mm−1

T = 298 K

0.23 × 0.21 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.349, T max = 0.390

8024 measured reflections

3023 independent reflections

1933 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.00

3023 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.64 e Å−3

Δρmin = −0.69 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536810006276/su2163sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006276/su2163Isup2.hkl

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

C13H9Br2N3O2	F(000) = 776
Mr = 399.05	Dx = 1.898 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2084 reflections
a = 17.013 (4) Å	θ = 2.4–25.2°
b = 8.091 (2) Å	µ = 5.81 mm−1
c = 10.153 (3) Å	T = 298 K
β = 92.194 (13)°	Block, colourless
V = 1396.6 (6) Å3	0.23 × 0.21 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3023 independent reflections
Radiation source: fine-focus sealed tube	1933 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 27.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −19→21
Tmin = 0.349, Tmax = 0.390	k = −10→10
8024 measured reflections	l = −12→8

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) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0589P)2] where P = (Fo2 + 2Fc2)/3
3023 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.64 e Å−3
1 restraint	Δρmin = −0.69 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.38611 (2)	1.15620 (7)	0.38681 (5)	0.0731 (2)
Br2	0.44353 (2)	0.85756 (6)	0.88313 (4)	0.06341 (18)
N1	0.11733 (17)	0.8462 (3)	0.5380 (3)	0.0393 (7)
N2	0.04257 (16)	0.7852 (4)	0.5483 (3)	0.0402 (7)
N3	−0.16645 (18)	0.5160 (4)	0.5780 (3)	0.0501 (8)
O1	0.22622 (14)	1.0061 (3)	0.4163 (2)	0.0514 (7)
H1	0.1820	0.9696	0.4270	0.077*
O2	0.01730 (14)	0.8169 (3)	0.3293 (2)	0.0508 (7)
C1	0.2459 (2)	0.8814 (4)	0.6310 (3)	0.0383 (8)
C2	0.27257 (19)	0.9725 (4)	0.5231 (3)	0.0377 (8)
C3	0.3494 (2)	1.0292 (4)	0.5283 (3)	0.0437 (9)
C4	0.4001 (2)	0.9964 (4)	0.6347 (3)	0.0455 (9)
H4	0.4512	1.0374	0.6373	0.055*
C5	0.3737 (2)	0.9026 (4)	0.7363 (3)	0.0403 (8)
C6	0.2980 (2)	0.8450 (4)	0.7371 (3)	0.0430 (9)
H6	0.2813	0.7823	0.8076	0.052*
C7	0.1655 (2)	0.8224 (4)	0.6360 (3)	0.0396 (8)
H7	0.1490	0.7673	0.7104	0.048*
C8	−0.00388 (19)	0.7712 (4)	0.4372 (3)	0.0366 (8)
C9	−0.08166 (19)	0.6936 (4)	0.4557 (3)	0.0358 (8)
C10	−0.1424 (2)	0.7215 (5)	0.3642 (4)	0.0492 (9)
H10	−0.1347	0.7889	0.2917	0.059*
C11	−0.2145 (2)	0.6488 (5)	0.3811 (4)	0.0541 (11)
H11	−0.2561	0.6666	0.3207	0.065*
C12	−0.2236 (2)	0.5493 (5)	0.4894 (4)	0.0510 (10)
H12	−0.2727	0.5025	0.5011	0.061*
C13	−0.0972 (2)	0.5869 (4)	0.5595 (3)	0.0417 (9)
H13	−0.0563	0.5637	0.6200	0.050*
H2	0.024 (2)	0.764 (6)	0.629 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0414 (3)	0.1045 (4)	0.0730 (3)	−0.0128 (2)	−0.0014 (2)	0.0354 (3)
Br2	0.0494 (3)	0.0779 (3)	0.0609 (3)	0.0041 (2)	−0.0244 (2)	0.0057 (2)
N1	0.0304 (16)	0.0528 (18)	0.0347 (16)	−0.0058 (13)	0.0011 (12)	−0.0056 (13)
N2	0.0285 (16)	0.0596 (19)	0.0324 (16)	−0.0048 (14)	−0.0016 (12)	−0.0034 (14)
N3	0.0425 (19)	0.057 (2)	0.0510 (19)	−0.0091 (15)	0.0009 (15)	0.0027 (15)
O1	0.0355 (15)	0.079 (2)	0.0393 (14)	−0.0054 (13)	−0.0059 (11)	0.0100 (13)
O2	0.0404 (15)	0.082 (2)	0.0301 (14)	−0.0050 (13)	−0.0007 (11)	0.0079 (13)
C1	0.0308 (19)	0.044 (2)	0.040 (2)	−0.0013 (15)	−0.0025 (15)	−0.0067 (16)
C2	0.0319 (19)	0.047 (2)	0.0344 (18)	0.0030 (15)	−0.0022 (14)	−0.0012 (16)
C3	0.035 (2)	0.051 (2)	0.045 (2)	−0.0012 (16)	−0.0013 (16)	0.0044 (17)
C4	0.030 (2)	0.051 (2)	0.055 (2)	−0.0002 (17)	−0.0051 (17)	−0.0015 (19)
C5	0.036 (2)	0.044 (2)	0.041 (2)	0.0035 (16)	−0.0078 (15)	−0.0012 (17)
C6	0.043 (2)	0.047 (2)	0.039 (2)	0.0002 (17)	−0.0033 (16)	−0.0008 (16)
C7	0.037 (2)	0.044 (2)	0.037 (2)	−0.0012 (15)	−0.0033 (16)	−0.0010 (15)
C8	0.0315 (19)	0.043 (2)	0.0347 (19)	0.0033 (15)	−0.0029 (15)	−0.0034 (16)
C9	0.0322 (19)	0.043 (2)	0.0318 (18)	0.0028 (15)	−0.0015 (14)	−0.0087 (15)
C10	0.042 (2)	0.066 (3)	0.038 (2)	−0.0023 (19)	−0.0067 (17)	0.0071 (19)
C11	0.034 (2)	0.077 (3)	0.050 (2)	0.0003 (19)	−0.0100 (17)	−0.011 (2)
C12	0.037 (2)	0.056 (2)	0.061 (3)	−0.0079 (18)	0.0017 (18)	−0.012 (2)
C13	0.038 (2)	0.047 (2)	0.039 (2)	−0.0013 (17)	−0.0042 (16)	0.0019 (16)

Br1—C3	1.892 (4)	C3—C4	1.382 (4)
Br2—C5	1.905 (3)	C4—C5	1.370 (5)
N1—C7	1.278 (4)	C4—H4	0.9300
N1—N2	1.372 (4)	C5—C6	1.371 (5)
N2—C8	1.357 (4)	C6—H6	0.9300
N2—H2	0.901 (10)	C7—H7	0.9300
N3—C12	1.326 (4)	C8—C9	1.483 (5)
N3—C13	1.330 (4)	C9—C10	1.381 (5)
O1—C2	1.344 (4)	C9—C13	1.396 (5)
O1—H1	0.8200	C10—C11	1.377 (5)
O2—C8	1.223 (4)	C10—H10	0.9300
C1—C6	1.401 (5)	C11—C12	1.376 (5)
C1—C2	1.409 (5)	C11—H11	0.9300
C1—C7	1.452 (5)	C12—H12	0.9300
C2—C3	1.384 (5)	C13—H13	0.9300
C7—N1—N2	117.1 (3)	C1—C6—H6	120.3
C8—N2—N1	118.6 (3)	N1—C7—C1	120.0 (3)
C8—N2—H2	122 (3)	N1—C7—H7	120.0
N1—N2—H2	119 (3)	C1—C7—H7	120.0
C12—N3—C13	116.5 (3)	O2—C8—N2	122.5 (3)
C2—O1—H1	109.5	O2—C8—C9	122.4 (3)
C6—C1—C2	119.6 (3)	N2—C8—C9	115.1 (3)
C6—C1—C7	118.3 (3)	C10—C9—C13	116.7 (3)
C2—C1—C7	122.1 (3)	C10—C9—C8	119.6 (3)
O1—C2—C3	119.2 (3)	C13—C9—C8	123.6 (3)
O1—C2—C1	122.4 (3)	C11—C10—C9	119.6 (4)
C3—C2—C1	118.4 (3)	C11—C10—H10	120.2
C4—C3—C2	121.7 (3)	C9—C10—H10	120.2
C4—C3—Br1	118.9 (3)	C12—C11—C10	118.5 (4)
C2—C3—Br1	119.4 (3)	C12—C11—H11	120.8
C5—C4—C3	118.9 (3)	C10—C11—H11	120.8
C5—C4—H4	120.6	N3—C12—C11	124.0 (4)
C3—C4—H4	120.6	N3—C12—H12	118.0
C4—C5—C6	121.9 (3)	C11—C12—H12	118.0
C4—C5—Br2	118.9 (3)	N3—C13—C9	124.6 (3)
C6—C5—Br2	119.2 (3)	N3—C13—H13	117.7
C5—C6—C1	119.4 (3)	C9—C13—H13	117.7
C5—C6—H6	120.3

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.89	2.609 (4)	146
N2—H2···O2i	0.91 (2)	2.14 (2)	3.017 (4)	162 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.89	2.609 (4)	146
N2—H2⋯O2i	0.91 (2)	2.14 (2)	3.017 (4)	162 (3)

Symmetry code: (i) .