N'-[(E)-2-Hy-droxy-5-meth-oxy-benzyl-idene]pyridine-4-carbohydrazide.

In the title compound, C(14)H(13)N(3)O(3), the dihedral angle between the pyridine and benzene rings is 15.17 (18)°. The torsion angle of the -C=N-N-C- system between two aromatic rings is -167.1 (3)°. Intra-molecular O-H⋯N hydrogen bonding generates S(6) rings. In the crystal structure, neighbouring mol-ecules are linked together along the c axis by weak inter-molecular C-H⋯O and N-H⋯O hydrogen bonds, generating R(1) (2)(6) ring motifs.

Related literature

For the tuberculostatic activity of isoniazid (isonicotinylhydrazine) derivatives, see: Janin (2007 ▶); Maccari et al. (2005 ▶). For the synthesis of the isoniazid derivative, see: Lourenco et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H13N3O3

M = 271.27

Monoclinic,

a = 6.1114 (6) Å

b = 29.489 (3) Å

c = 7.4820 (7) Å

β = 96.696 (8)°

V = 1339.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.67 × 0.34 × 0.12 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.962, T max = 0.988

4353 measured reflections

1542 independent reflections

1166 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.114

S = 1.11

1542 reflections

191 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.16 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043382/sj5051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043382/sj5051Isup2.hkl

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

C14H13N3O3	F(000) = 568
Mr = 271.27	Dx = 1.345 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 7613 reflections
a = 6.1114 (6) Å	θ = 2.8–28.0°
b = 29.489 (3) Å	µ = 0.10 mm−1
c = 7.4820 (7) Å	T = 296 K
β = 96.696 (8)°	Prism, colourless
V = 1339.2 (2) Å3	0.67 × 0.34 × 0.12 mm
Z = 4

Stoe IPDS 2 diffractometer	1542 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1166 reflections with I > 2σ(I)
plane graphite	Rint = 0.038
Detector resolution: 6.67 pixels mm-1	θmax = 27.5°, θmin = 2.8°
ω scans	h = −7→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −38→35
Tmin = 0.962, Tmax = 0.988	l = −9→8
4353 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.0582P)2] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
1542 reflections	Δρmax = 0.13 e Å−3
191 parameters	Δρmin = −0.16 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0090 (19)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1	−0.1045 (4)	0.82503 (10)	0.3515 (4)	0.0727 (9)
O2	0.2101 (5)	0.99107 (9)	0.6041 (5)	0.0844 (10)
O3	0.2501 (4)	0.71171 (8)	0.2791 (4)	0.0743 (9)
N1	0.2870 (4)	0.79115 (10)	0.4570 (4)	0.0619 (9)
N2	0.4398 (4)	0.75656 (9)	0.4882 (4)	0.0622 (9)
N3	0.8707 (5)	0.61195 (13)	0.5468 (5)	0.0794 (11)
C1	0.1994 (5)	0.86852 (12)	0.5002 (4)	0.0572 (10)
C2	−0.0172 (5)	0.86497 (12)	0.4151 (5)	0.0599 (11)
C3	−0.1453 (5)	0.90380 (14)	0.3930 (6)	0.0753 (15)
C4	−0.0645 (6)	0.94459 (14)	0.4568 (6)	0.0766 (13)
C5	0.1486 (5)	0.94855 (12)	0.5445 (5)	0.0646 (11)
C6	0.2792 (5)	0.91072 (12)	0.5652 (5)	0.0611 (11)
C7	0.4191 (7)	0.99583 (16)	0.7042 (7)	0.0830 (14)
C8	0.3464 (5)	0.82985 (12)	0.5228 (5)	0.0591 (11)
C9	0.4075 (4)	0.71774 (11)	0.3949 (4)	0.0574 (10)
C10	0.5728 (5)	0.68156 (11)	0.4456 (4)	0.0564 (10)
C11	0.7920 (5)	0.69069 (13)	0.5046 (5)	0.0672 (11)
C12	0.9319 (6)	0.65507 (17)	0.5525 (6)	0.0778 (15)
C13	0.6605 (6)	0.60362 (13)	0.4866 (6)	0.0739 (14)
C14	0.5073 (5)	0.63664 (12)	0.4332 (5)	0.0655 (11)
H1	0.007 (7)	0.8019 (15)	0.363 (6)	0.080 (12)*
H2	0.552 (7)	0.7604 (14)	0.572 (6)	0.079 (11)*
H3	−0.28770	0.90210	0.33400	0.0900*
H4	−0.15340	0.97020	0.44150	0.0920*
H6	0.42200	0.91300	0.62290	0.0730*
H7A	0.53150	0.98860	0.62920	0.1250*
H7B	0.43020	0.97560	0.80540	0.1250*
H7C	0.43790	1.02650	0.74600	0.1250*
H8	0.48570	0.83320	0.58600	0.0710*
H11	0.84350	0.72040	0.51180	0.0810*
H12	1.07860	0.66170	0.59120	0.0940*
H13	0.61430	0.57360	0.48040	0.0880*
H14	0.36330	0.62890	0.38980	0.0790*

	U11	U22	U33	U12	U13	U23
O1	0.0555 (12)	0.0673 (16)	0.0905 (19)	0.0003 (11)	−0.0119 (12)	−0.0055 (13)
O2	0.0782 (15)	0.0598 (16)	0.111 (2)	0.0057 (12)	−0.0066 (15)	−0.0122 (16)
O3	0.0669 (13)	0.0602 (14)	0.0864 (19)	0.0021 (11)	−0.0310 (12)	−0.0050 (13)
N1	0.0523 (12)	0.0570 (17)	0.0721 (19)	0.0056 (12)	−0.0115 (12)	0.0015 (14)
N2	0.0541 (12)	0.0544 (16)	0.0716 (18)	0.0064 (12)	−0.0195 (12)	−0.0042 (14)
N3	0.0687 (18)	0.079 (2)	0.090 (2)	0.0237 (16)	0.0069 (15)	0.0059 (19)
C1	0.0511 (15)	0.061 (2)	0.0581 (19)	0.0045 (13)	0.0008 (13)	0.0026 (15)
C2	0.0478 (14)	0.065 (2)	0.066 (2)	−0.0007 (14)	0.0023 (13)	0.0000 (17)
C3	0.0481 (17)	0.078 (3)	0.097 (3)	0.0108 (16)	−0.0031 (18)	0.003 (2)
C4	0.0616 (18)	0.069 (2)	0.096 (3)	0.0148 (17)	−0.0043 (18)	−0.002 (2)
C5	0.0606 (17)	0.058 (2)	0.074 (2)	0.0017 (15)	0.0028 (15)	−0.0040 (18)
C6	0.0495 (15)	0.062 (2)	0.070 (2)	0.0014 (13)	−0.0011 (14)	−0.0002 (16)
C7	0.081 (2)	0.072 (2)	0.093 (3)	−0.0038 (19)	−0.003 (2)	−0.011 (2)
C8	0.0519 (14)	0.059 (2)	0.063 (2)	0.0013 (13)	−0.0081 (13)	0.0011 (16)
C9	0.0458 (13)	0.0562 (19)	0.066 (2)	−0.0026 (12)	−0.0107 (13)	0.0011 (16)
C10	0.0504 (14)	0.0602 (19)	0.0565 (18)	0.0030 (13)	−0.0027 (13)	−0.0032 (16)
C11	0.0520 (15)	0.070 (2)	0.077 (2)	0.0048 (15)	−0.0028 (15)	−0.0028 (19)
C12	0.0548 (16)	0.090 (3)	0.087 (3)	0.0123 (18)	0.0011 (17)	−0.001 (2)
C13	0.074 (2)	0.061 (2)	0.086 (3)	0.0101 (17)	0.007 (2)	−0.0042 (19)
C14	0.0616 (17)	0.058 (2)	0.076 (2)	0.0017 (14)	0.0039 (16)	−0.0093 (18)

O1—C2	1.356 (5)	C5—C6	1.370 (5)
O2—C5	1.369 (5)	C9—C10	1.488 (4)
O2—C7	1.410 (6)	C10—C11	1.387 (4)
O3—C9	1.230 (4)	C10—C14	1.384 (5)
O1—H1	0.96 (4)	C11—C12	1.375 (6)
N1—N2	1.384 (4)	C13—C14	1.377 (5)
N1—C8	1.279 (5)	C3—H3	0.9300
N2—C9	1.343 (4)	C4—H4	0.9300
N3—C13	1.334 (5)	C6—H6	0.9300
N3—C12	1.325 (6)	C7—H7A	0.9600
N2—H2	0.88 (4)	C7—H7B	0.9600
C1—C6	1.403 (5)	C7—H7C	0.9600
C1—C2	1.404 (4)	C8—H8	0.9300
C1—C8	1.449 (5)	C11—H11	0.9300
C2—C3	1.386 (5)	C12—H12	0.9300
C3—C4	1.365 (6)	C13—H13	0.9300
C4—C5	1.393 (5)	C14—H14	0.9300
O1···N1	2.628 (4)	C7···H6	2.5200
O1···C10i	3.347 (4)	C8···H1	2.42 (4)
O2···C7ii	3.409 (6)	C11···H2	2.61 (4)
O3···N2i	2.872 (4)	C12···H3viii	3.0600
O3···C12iii	3.418 (5)	C14···H12iii	3.0900
O3···N1	2.691 (4)	H1···N1	1.80 (4)
O3···C8i	3.188 (4)	H1···C8	2.42 (4)
O1···H12iv	2.6100	H2···C11	2.61 (4)
O2···H13v	2.6500	H2···H8	2.1900
O2···H7Bii	2.9100	H2···H11	2.2300
O3···H14	2.6400	H2···O3vi	2.03 (4)
O3···H2i	2.03 (4)	H3···N3iv	2.8500
O3···H8i	2.4300	H3···C12iv	3.0600
N1···O1	2.628 (4)	H4···H7Aiii	2.5700
N1···O3	2.691 (4)	H6···C7	2.5200
N1···C11i	3.431 (5)	H6···H7A	2.3300
N2···O3vi	2.872 (4)	H6···H7B	2.2900
N1···H1	1.80 (4)	H6···H8	2.4100
N2···H11	2.6700	H7A···C6	2.7800
N3···H7Cvii	2.9300	H7A···H4xi	2.5700
N3···H3viii	2.8500	H7A···H6	2.3300
C1···C14ix	3.576 (5)	H7B···C6	2.7100
C5···C7ii	3.590 (6)	H7B···H6	2.2900
C6···C13ix	3.344 (6)	H7B···O2x	2.9100
C7···O2x	3.409 (6)	H7C···C5x	3.0900
C7···C5x	3.590 (6)	H7C···N3v	2.9300
C8···O3vi	3.188 (4)	H8···H2	2.1900
C10···O1vi	3.347 (4)	H8···H6	2.4100
C11···N1vi	3.431 (5)	H8···O3vi	2.4300
C12···O3xi	3.418 (5)	H11···N2	2.6700
C13···C6xii	3.344 (6)	H11···H2	2.2300
C14···C1xii	3.576 (5)	H12···C14xi	3.0900
C5···H7Cii	3.0900	H12···O1viii	2.6100
C6···H7A	2.7800	H13···O2vii	2.6500
C6···H7B	2.7100	H14···O3	2.6400
C5—O2—C7	117.5 (3)	C10—C11—C12	118.9 (3)
C2—O1—H1	110 (3)	N3—C12—C11	124.1 (4)
N2—N1—C8	115.9 (3)	N3—C13—C14	124.3 (4)
N1—N2—C9	119.0 (3)	C10—C14—C13	118.4 (3)
C12—N3—C13	116.4 (4)	C2—C3—H3	120.00
C9—N2—H2	122 (3)	C4—C3—H3	120.00
N1—N2—H2	119 (3)	C3—C4—H4	119.00
C2—C1—C6	119.6 (3)	C5—C4—H4	119.00
C2—C1—C8	122.2 (3)	C1—C6—H6	120.00
C6—C1—C8	118.2 (3)	C5—C6—H6	120.00
O1—C2—C3	118.8 (3)	O2—C7—H7A	109.00
O1—C2—C1	122.4 (3)	O2—C7—H7B	109.00
C1—C2—C3	118.8 (3)	O2—C7—H7C	109.00
C2—C3—C4	120.7 (3)	H7A—C7—H7B	109.00
C3—C4—C5	121.3 (4)	H7A—C7—H7C	109.00
C4—C5—C6	119.0 (3)	H7B—C7—H7C	110.00
O2—C5—C4	115.9 (3)	N1—C8—H8	120.00
O2—C5—C6	125.1 (3)	C1—C8—H8	120.00
C1—C6—C5	120.6 (3)	C10—C11—H11	121.00
N1—C8—C1	120.9 (3)	C12—C11—H11	121.00
O3—C9—N2	123.0 (3)	N3—C12—H12	118.00
O3—C9—C10	121.9 (3)	C11—C12—H12	118.00
N2—C9—C10	115.1 (2)	N3—C13—H13	118.00
C11—C10—C14	117.9 (3)	C14—C13—H13	118.00
C9—C10—C11	122.9 (3)	C10—C14—H14	121.00
C9—C10—C14	119.1 (3)	C13—C14—H14	121.00
C7—O2—C5—C6	−4.1 (6)	O1—C2—C3—C4	179.3 (4)
C7—O2—C5—C4	175.8 (4)	C2—C3—C4—C5	0.5 (6)
N2—N1—C8—C1	−179.4 (3)	C3—C4—C5—O2	−179.3 (4)
C8—N1—N2—C9	−167.1 (3)	C3—C4—C5—C6	0.6 (6)
N1—N2—C9—C10	−176.4 (3)	O2—C5—C6—C1	179.5 (3)
N1—N2—C9—O3	1.7 (5)	C4—C5—C6—C1	−0.4 (5)
C13—N3—C12—C11	1.5 (6)	O3—C9—C10—C14	−30.5 (4)
C12—N3—C13—C14	−0.7 (6)	O3—C9—C10—C11	149.2 (3)
C8—C1—C6—C5	178.8 (3)	N2—C9—C10—C14	147.6 (3)
C6—C1—C2—C3	1.8 (5)	N2—C9—C10—C11	−32.7 (4)
C2—C1—C6—C5	−0.8 (5)	C14—C10—C11—C12	−1.8 (5)
C8—C1—C2—O1	1.3 (5)	C9—C10—C11—C12	178.5 (3)
C8—C1—C2—C3	−177.8 (3)	C9—C10—C14—C13	−177.8 (3)
C6—C1—C2—O1	−179.2 (3)	C11—C10—C14—C13	2.5 (5)
C2—C1—C8—N1	3.7 (5)	C10—C11—C12—N3	−0.3 (6)
C6—C1—C8—N1	−175.9 (3)	N3—C13—C14—C10	−1.4 (6)
C1—C2—C3—C4	−1.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.96 (4)	1.80 (4)	2.628 (4)	142 (4)
N2—H2···O3vi	0.88 (4)	2.03 (4)	2.872 (4)	161 (4)
C8—H8···O3vi	0.93	2.43	3.188 (4)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.96 (4)	1.80 (4)	2.628 (4)	142 (4)
N2—H2⋯O3i	0.88 (4)	2.03 (4)	2.872 (4)	161 (4)
C8—H8⋯O3i	0.93	2.43	3.188 (4)	139

Symmetry code: (i) .