N'-(2-Hydr-oxy-4-methoxy-benzyl-idene)isonicotinohydrazide.

The title compound, C(14)H(13)N(3)O(3), was synthesized by the condensation reaction of 2-hydr-oxy-4-methoxy-benzaldehyde with isonicotinohydrazide in a methanol solution. The mol-ecule of the compound displays a trans configuration with respect to the C=N and C-N bonds. The dihedral angle between the benzene and the pyridine rings is 27.3 (2)°. In the crystal, mol-ecules are linked by N-H⋯N inter-actions into zigzag chains with graph-set notation C(7) along [010]. An intra-molecular O-H⋯N hydrogen bond is observed.

Related literature

For Schiff base compounds, see: Fan et al. (2007 ▶); Kim et al. (2005 ▶); Nimitsiriwat et al. (2004 ▶). For their biological activity, see: Chen et al. (1997 ▶); Ren et al. (2002 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Yang (2008 ▶); Zhi (2008 ▶, 2009 ▶); Zhi & Yang (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H13N3O3

M = 271.27

Monoclinic,

a = 8.4704 (11) Å

b = 10.6866 (15) Å

c = 14.848 (2) Å

β = 104.929 (5)°

V = 1298.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.983, T max = 0.985

7591 measured reflections

2814 independent reflections

2148 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.05

2814 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.17 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010020/bx2271sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010020/bx2271Isup2.hkl

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

C14H13N3O3	F(000) = 568
Mr = 271.27	Dx = 1.387 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.4704 (11) Å	Cell parameters from 2534 reflections
b = 10.6866 (15) Å	θ = 2.4–29.9°
c = 14.848 (2) Å	µ = 0.10 mm−1
β = 104.929 (5)°	T = 298 K
V = 1298.7 (3) Å3	Block, colourless
Z = 4	0.17 × 0.15 × 0.15 mm

Bruker SMART 1000 CCD area-detector diffractometer	2814 independent reflections
Radiation source: fine-focus sealed tube	2148 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.983, Tmax = 0.985	k = −11→13
7591 measured reflections	l = −18→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.2097P] where P = (Fo2 + 2Fc2)/3
2814 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.17 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
N1	0.10385 (14)	0.87232 (11)	0.12848 (8)	0.0425 (3)
N2	0.01859 (14)	0.78408 (11)	0.16392 (8)	0.0422 (3)
N3	−0.26459 (16)	0.40486 (11)	0.24523 (9)	0.0491 (3)
O1	0.28189 (15)	0.93517 (9)	0.01927 (8)	0.0554 (3)
H1	0.2284	0.8881	0.0436	0.083*
O2	0.12526 (15)	0.62775 (10)	0.09488 (9)	0.0624 (3)
O3	0.40498 (14)	1.36738 (9)	0.00218 (8)	0.0550 (3)
C1	0.17894 (16)	1.08276 (12)	0.11284 (10)	0.0404 (3)
C2	0.26792 (16)	1.05413 (12)	0.04800 (9)	0.0386 (3)
C3	0.34625 (17)	1.14692 (12)	0.01077 (10)	0.0410 (3)
H3	0.4072	1.1263	−0.0310	0.049*
C4	0.33345 (17)	1.27035 (12)	0.03599 (10)	0.0421 (3)
C5	0.24469 (19)	1.30187 (14)	0.09935 (12)	0.0518 (4)
H5	0.2356	1.3850	0.1159	0.062*
C6	0.17066 (19)	1.20882 (14)	0.13711 (11)	0.0512 (4)
H6	0.1129	1.2301	0.1803	0.061*
C7	0.09706 (17)	0.98671 (13)	0.15257 (10)	0.0446 (3)
H7	0.0393	1.0082	0.1958	0.054*
C8	0.03539 (16)	0.66264 (13)	0.14180 (9)	0.0410 (3)
C9	−0.06727 (16)	0.57305 (12)	0.17959 (9)	0.0365 (3)
C10	−0.12509 (18)	0.46540 (13)	0.13050 (10)	0.0437 (3)
H10	−0.0990	0.4472	0.0748	0.052*
C11	−0.22227 (19)	0.38542 (14)	0.16569 (11)	0.0493 (4)
H11	−0.2607	0.3135	0.1319	0.059*
C12	−0.20463 (18)	0.50811 (13)	0.29267 (10)	0.0454 (3)
H12	−0.2304	0.5231	0.3489	0.054*
C13	−0.10710 (17)	0.59344 (12)	0.26321 (9)	0.0395 (3)
H13	−0.0684	0.6638	0.2989	0.047*
C14	0.4899 (2)	1.34231 (15)	−0.06713 (12)	0.0585 (4)
H14A	0.5817	1.2890	−0.0415	0.088*
H14B	0.5276	1.4196	−0.0873	0.088*
H14C	0.4177	1.3015	−0.1193	0.088*
H2	−0.0540 (19)	0.8096 (18)	0.1945 (12)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0453 (7)	0.0384 (6)	0.0492 (7)	−0.0015 (5)	0.0219 (5)	0.0052 (5)
N2	0.0459 (7)	0.0376 (6)	0.0506 (7)	−0.0014 (5)	0.0261 (5)	0.0030 (5)
N3	0.0577 (8)	0.0419 (7)	0.0544 (7)	−0.0031 (6)	0.0266 (6)	0.0045 (6)
O1	0.0798 (8)	0.0316 (5)	0.0704 (7)	−0.0041 (5)	0.0477 (6)	−0.0036 (5)
O2	0.0732 (7)	0.0502 (6)	0.0831 (8)	−0.0044 (5)	0.0549 (7)	−0.0083 (6)
O3	0.0653 (7)	0.0335 (5)	0.0721 (7)	−0.0032 (5)	0.0281 (6)	0.0067 (5)
C1	0.0385 (7)	0.0357 (7)	0.0496 (8)	0.0020 (6)	0.0161 (6)	0.0012 (6)
C2	0.0426 (7)	0.0323 (7)	0.0424 (7)	0.0012 (5)	0.0135 (6)	0.0006 (6)
C3	0.0459 (7)	0.0371 (7)	0.0429 (7)	0.0003 (6)	0.0167 (6)	0.0019 (6)
C4	0.0420 (7)	0.0330 (7)	0.0497 (8)	0.0006 (6)	0.0091 (6)	0.0053 (6)
C5	0.0568 (9)	0.0310 (7)	0.0722 (10)	0.0026 (6)	0.0247 (8)	−0.0039 (7)
C6	0.0523 (9)	0.0426 (8)	0.0665 (10)	0.0040 (6)	0.0294 (8)	−0.0051 (7)
C7	0.0439 (8)	0.0442 (8)	0.0516 (8)	0.0013 (6)	0.0230 (7)	0.0001 (6)
C8	0.0429 (7)	0.0412 (8)	0.0436 (7)	0.0006 (6)	0.0198 (6)	0.0002 (6)
C9	0.0361 (7)	0.0347 (7)	0.0416 (7)	0.0045 (5)	0.0155 (6)	0.0028 (5)
C10	0.0521 (8)	0.0404 (7)	0.0445 (8)	0.0008 (6)	0.0231 (7)	−0.0031 (6)
C11	0.0574 (9)	0.0406 (8)	0.0541 (9)	−0.0066 (7)	0.0217 (7)	−0.0048 (7)
C12	0.0557 (9)	0.0456 (8)	0.0408 (8)	0.0036 (7)	0.0231 (7)	0.0041 (6)
C13	0.0461 (8)	0.0366 (7)	0.0380 (7)	0.0019 (6)	0.0148 (6)	−0.0003 (6)
C14	0.0664 (10)	0.0444 (9)	0.0713 (11)	−0.0039 (7)	0.0301 (9)	0.0107 (8)

N1—C7	1.2791 (18)	C4—C5	1.388 (2)
N1—N2	1.3724 (15)	C5—C6	1.370 (2)
N2—C8	1.3552 (18)	C5—H5	0.9300
N2—H2	0.896 (9)	C6—H6	0.9300
N3—C11	1.3358 (19)	C7—H7	0.9300
N3—C12	1.3369 (19)	C8—C9	1.4963 (18)
O1—C2	1.3558 (16)	C9—C10	1.3823 (19)
O1—H1	0.8200	C9—C13	1.3852 (18)
O2—C8	1.2153 (16)	C10—C11	1.379 (2)
O3—C4	1.3606 (16)	C10—H10	0.9300
O3—C14	1.4247 (19)	C11—H11	0.9300
C1—C6	1.401 (2)	C12—C13	1.3753 (19)
C1—C2	1.4009 (19)	C12—H12	0.9300
C1—C7	1.4468 (19)	C13—H13	0.9300
C2—C3	1.3849 (19)	C14—H14A	0.9600
C3—C4	1.3831 (19)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C7—N1—N2	118.91 (12)	N1—C7—H7	119.9
C8—N2—N1	117.81 (11)	C1—C7—H7	119.9
C8—N2—H2	122.9 (13)	O2—C8—N2	123.59 (13)
N1—N2—H2	118.9 (13)	O2—C8—C9	121.93 (13)
C11—N3—C12	116.24 (12)	N2—C8—C9	114.48 (11)
C2—O1—H1	109.5	C10—C9—C13	117.94 (12)
C4—O3—C14	118.62 (11)	C10—C9—C8	119.73 (12)
C6—C1—C2	117.28 (13)	C13—C9—C8	122.33 (12)
C6—C1—C7	121.09 (13)	C11—C10—C9	118.74 (13)
C2—C1—C7	121.63 (12)	C11—C10—H10	120.6
O1—C2—C3	117.14 (12)	C9—C10—H10	120.6
O1—C2—C1	121.81 (12)	N3—C11—C10	124.11 (14)
C3—C2—C1	121.05 (12)	N3—C11—H11	117.9
C4—C3—C2	119.72 (13)	C10—C11—H11	117.9
C4—C3—H3	120.1	N3—C12—C13	123.88 (13)
C2—C3—H3	120.1	N3—C12—H12	118.1
O3—C4—C3	123.60 (13)	C13—C12—H12	118.1
O3—C4—C5	115.81 (12)	C12—C13—C9	119.06 (13)
C3—C4—C5	120.58 (13)	C12—C13—H13	120.5
C6—C5—C4	119.07 (13)	C9—C13—H13	120.5
C6—C5—H5	120.5	O3—C14—H14A	109.5
C4—C5—H5	120.5	O3—C14—H14B	109.5
C5—C6—C1	122.28 (14)	H14A—C14—H14B	109.5
C5—C6—H6	118.9	O3—C14—H14C	109.5
C1—C6—H6	118.9	H14A—C14—H14C	109.5
N1—C7—C1	120.22 (13)	H14B—C14—H14C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3i	0.90 (1)	2.22 (1)	3.1000 (17)	169 (2)
O1—H1···N1	0.82	1.85	2.5720 (15)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N3i	0.90 (1)	2.22 (1)	3.1000 (17)	169 (2)
O1—H1⋯N1	0.82	1.85	2.5720 (15)	146

Symmetry code: (i) .