N'-[(E)-4-Hydr-oxy-3-methoxy-benzyl-idene]pyridine-4-carbohydrazide.

In the title compound, C(14)H(13)N(3)O(3), the two six-membered rings are oriented at a dihedral angle of 15.17 (11)° and an intra-molecular O-H⋯O hydrogen bond occurs. In the crystal, mol-ecules inter-act by way of N-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds, thereby generating S(5) chain and R(2) (1)(7) ring motifs.

Related literature

For related structures, see: Liu & Shi (2007 ▶); Shi et al. (2007 ▶); Shafiq et al. (2009 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H13N3O3

M = 271.27

Monoclinic,

a = 14.8543 (10) Å

b = 12.4943 (9) Å

c = 7.7162 (5) Å

β = 116.716 (2)°

V = 1279.20 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.32 × 0.14 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.973, T max = 0.984

7060 measured reflections

1613 independent reflections

1431 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.086

S = 1.04

1613 reflections

183 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044134/hb5177sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044134/hb5177Isup2.hkl

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

C14H13N3O3	F(000) = 568
Mr = 271.27	Dx = 1.409 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1613 reflections
a = 14.8543 (10) Å	θ = 2.2–28.7°
b = 12.4943 (9) Å	µ = 0.10 mm−1
c = 7.7162 (5) Å	T = 296 K
β = 116.716 (2)°	Needle, yellow
V = 1279.20 (15) Å3	0.32 × 0.14 × 0.10 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	1613 independent reflections
Radiation source: fine-focus sealed tube	1431 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 7.40 pixels mm-1	θmax = 28.7°, θmin = 2.2°
ω scans	h = −17→19
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→16
Tmin = 0.973, Tmax = 0.984	l = −10→5
7060 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.2451P] where P = (Fo2 + 2Fc2)/3
1613 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.16 e Å−3
2 restraints	Δρmin = −0.21 e Å−3

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 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
O1	0.20978 (12)	−0.14131 (15)	0.1499 (2)	0.0464 (5)
O2	0.74733 (14)	0.23723 (14)	0.7114 (3)	0.0495 (5)
O3	0.71022 (13)	0.02563 (13)	0.6995 (3)	0.0462 (5)
N1	−0.10456 (14)	−0.14377 (17)	−0.4734 (3)	0.0415 (6)
N2	0.24963 (13)	−0.01999 (16)	−0.0200 (2)	0.0357 (5)
N3	0.34327 (13)	−0.00082 (17)	0.1376 (3)	0.0371 (5)
C1	0.08684 (14)	−0.10723 (18)	−0.1727 (3)	0.0302 (6)
C2	0.03464 (17)	−0.2001 (2)	−0.1794 (3)	0.0400 (7)
C3	−0.06004 (17)	−0.2154 (2)	−0.3320 (4)	0.0455 (8)
C4	−0.05475 (16)	−0.0540 (2)	−0.4634 (3)	0.0387 (6)
C5	0.04083 (16)	−0.03215 (18)	−0.3174 (3)	0.0342 (6)
C6	0.18841 (15)	−0.09215 (18)	−0.0012 (3)	0.0317 (6)
C7	0.38334 (15)	0.08629 (19)	0.1254 (3)	0.0355 (6)
C8	0.48092 (15)	0.12099 (18)	0.2766 (3)	0.0322 (6)
C9	0.54708 (16)	0.05029 (18)	0.4162 (3)	0.0338 (6)
C10	0.63784 (15)	0.08723 (18)	0.5602 (3)	0.0320 (6)
C11	0.66190 (15)	0.19614 (18)	0.5701 (3)	0.0318 (6)
C12	0.59690 (16)	0.26504 (19)	0.4295 (3)	0.0353 (6)
C13	0.50728 (15)	0.22751 (19)	0.2826 (3)	0.0360 (6)
C14	0.70271 (18)	−0.08742 (19)	0.6725 (4)	0.0424 (7)
H2	0.06282	−0.25144	−0.08249	0.0480*
H2A	0.23175	0.01414	−0.12720	0.0428*
H2B	0.77967	0.18945	0.78640	0.0594*
H3	−0.09420	−0.27850	−0.33636	0.0546*
H4	−0.08569	−0.00289	−0.55979	0.0465*
H5	0.07325	0.03162	−0.31695	0.0411*
H7	0.34970	0.12947	0.01696	0.0425*
H9	0.53013	−0.02163	0.41231	0.0405*
H12	0.61341	0.33710	0.43342	0.0424*
H13	0.46457	0.27431	0.18744	0.0432*
H14A	0.70409	−0.10498	0.55254	0.0636*
H14B	0.64062	−0.11205	0.66859	0.0636*
H14C	0.75836	−0.12140	0.77800	0.0636*

	U11	U22	U33	U12	U13	U23
O1	0.0372 (9)	0.0570 (11)	0.0298 (8)	−0.0070 (8)	0.0015 (7)	0.0075 (7)
O2	0.0341 (8)	0.0373 (9)	0.0468 (9)	−0.0080 (7)	−0.0086 (7)	0.0022 (8)
O3	0.0347 (8)	0.0346 (9)	0.0433 (9)	−0.0031 (7)	−0.0056 (7)	0.0066 (7)
N1	0.0238 (8)	0.0486 (12)	0.0369 (10)	−0.0013 (8)	0.0001 (7)	−0.0017 (8)
N2	0.0252 (9)	0.0448 (11)	0.0234 (8)	−0.0053 (8)	−0.0013 (7)	0.0011 (7)
N3	0.0233 (8)	0.0481 (11)	0.0253 (8)	−0.0042 (8)	−0.0021 (7)	−0.0012 (8)
C1	0.0226 (9)	0.0371 (11)	0.0235 (9)	−0.0011 (8)	0.0037 (8)	−0.0041 (8)
C2	0.0317 (12)	0.0392 (12)	0.0366 (11)	−0.0011 (9)	0.0042 (10)	0.0068 (10)
C3	0.0302 (12)	0.0441 (14)	0.0484 (13)	−0.0087 (10)	0.0054 (10)	0.0025 (11)
C4	0.0258 (10)	0.0455 (13)	0.0316 (10)	0.0017 (9)	0.0011 (8)	0.0037 (9)
C5	0.0260 (10)	0.0387 (12)	0.0295 (10)	−0.0028 (9)	0.0050 (8)	−0.0021 (9)
C6	0.0242 (9)	0.0376 (12)	0.0240 (9)	0.0021 (8)	0.0027 (8)	−0.0028 (8)
C7	0.0257 (10)	0.0421 (12)	0.0281 (10)	−0.0004 (9)	0.0028 (8)	0.0005 (9)
C8	0.0230 (9)	0.0403 (12)	0.0269 (9)	−0.0028 (9)	0.0055 (8)	−0.0015 (9)
C9	0.0280 (10)	0.0311 (11)	0.0327 (10)	−0.0059 (8)	0.0052 (8)	0.0006 (8)
C10	0.0258 (9)	0.0326 (11)	0.0291 (9)	−0.0010 (8)	0.0048 (8)	0.0027 (8)
C11	0.0242 (9)	0.0343 (11)	0.0296 (10)	−0.0037 (8)	0.0055 (8)	−0.0018 (8)
C12	0.0323 (11)	0.0304 (11)	0.0358 (11)	−0.0033 (9)	0.0087 (9)	−0.0007 (9)
C13	0.0295 (11)	0.0387 (12)	0.0305 (10)	0.0035 (9)	0.0053 (9)	0.0039 (9)
C14	0.0352 (12)	0.0342 (12)	0.0485 (13)	0.0013 (10)	0.0105 (10)	0.0065 (10)

O1—C6	1.227 (3)	C8—C13	1.382 (3)
O2—C11	1.349 (3)	C8—C9	1.398 (3)
O3—C10	1.366 (3)	C9—C10	1.385 (3)
O3—C14	1.425 (3)	C10—C11	1.400 (3)
O2—H2B	0.8200	C11—C12	1.382 (3)
N1—C3	1.334 (3)	C12—C13	1.386 (3)
N1—C4	1.327 (3)	C2—H2	0.9300
N2—C6	1.334 (3)	C3—H3	0.9300
N2—N3	1.396 (3)	C4—H4	0.9300
N3—C7	1.264 (3)	C5—H5	0.9300
N2—H2A	0.8600	C7—H7	0.9300
C1—C5	1.381 (3)	C9—H9	0.9300
C1—C2	1.384 (3)	C12—H12	0.9300
C1—C6	1.506 (3)	C13—H13	0.9300
C2—C3	1.383 (4)	C14—H14A	0.9600
C4—C5	1.386 (3)	C14—H14B	0.9600
C7—C8	1.459 (3)	C14—H14C	0.9600
C10—O3—C14	117.5 (2)	O2—C11—C10	122.6 (2)
C11—O2—H2B	109.00	C10—C11—C12	119.5 (2)
C3—N1—C4	117.5 (2)	C11—C12—C13	120.5 (2)
N3—N2—C6	118.82 (17)	C8—C13—C12	120.5 (2)
N2—N3—C7	113.6 (2)	C1—C2—H2	120.00
C6—N2—H2A	121.00	C3—C2—H2	120.00
N3—N2—H2A	121.00	N1—C3—H3	119.00
C2—C1—C5	118.3 (2)	C2—C3—H3	119.00
C2—C1—C6	117.45 (19)	N1—C4—H4	118.00
C5—C1—C6	124.2 (2)	C5—C4—H4	118.00
C1—C2—C3	119.1 (2)	C1—C5—H5	121.00
N1—C3—C2	123.0 (2)	C4—C5—H5	121.00
N1—C4—C5	123.7 (2)	N3—C7—H7	119.00
C1—C5—C4	118.5 (2)	C8—C7—H7	119.00
O1—C6—N2	123.0 (2)	C8—C9—H9	120.00
N2—C6—C1	116.85 (18)	C10—C9—H9	120.00
O1—C6—C1	120.1 (2)	C11—C12—H12	120.00
N3—C7—C8	121.9 (2)	C13—C12—H12	120.00
C7—C8—C13	118.5 (2)	C8—C13—H13	120.00
C7—C8—C9	122.0 (2)	C12—C13—H13	120.00
C9—C8—C13	119.5 (2)	O3—C14—H14A	109.00
C8—C9—C10	120.1 (2)	O3—C14—H14B	109.00
O3—C10—C9	125.6 (2)	O3—C14—H14C	109.00
O3—C10—C11	114.4 (2)	H14A—C14—H14B	109.00
C9—C10—C11	120.0 (2)	H14A—C14—H14C	109.00
O2—C11—C12	118.0 (2)	H14B—C14—H14C	110.00
C14—O3—C10—C9	14.0 (4)	N1—C4—C5—C1	−0.7 (4)
C14—O3—C10—C11	−165.5 (2)	N3—C7—C8—C9	16.8 (4)
C4—N1—C3—C2	−0.6 (4)	N3—C7—C8—C13	−162.1 (2)
C3—N1—C4—C5	1.3 (4)	C7—C8—C9—C10	−178.3 (2)
C6—N2—N3—C7	−162.0 (2)	C13—C8—C9—C10	0.6 (4)
N3—N2—C6—O1	1.4 (3)	C7—C8—C13—C12	176.7 (2)
N3—N2—C6—C1	177.92 (19)	C9—C8—C13—C12	−2.3 (4)
N2—N3—C7—C8	179.5 (2)	C8—C9—C10—O3	−177.3 (2)
C5—C1—C2—C3	1.5 (4)	C8—C9—C10—C11	2.2 (4)
C6—C1—C2—C3	178.3 (2)	O3—C10—C11—O2	−3.1 (3)
C2—C1—C5—C4	−0.8 (3)	O3—C10—C11—C12	176.2 (2)
C6—C1—C5—C4	−177.4 (2)	C9—C10—C11—O2	177.4 (2)
C2—C1—C6—O1	−21.5 (3)	C9—C10—C11—C12	−3.4 (4)
C2—C1—C6—N2	161.9 (2)	O2—C11—C12—C13	−179.0 (2)
C5—C1—C6—O1	155.1 (2)	C10—C11—C12—C13	1.7 (4)
C5—C1—C6—N2	−21.5 (3)	C11—C12—C13—C8	1.1 (4)
C1—C2—C3—N1	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O3	0.82	2.25	2.694 (2)	114
N2—H2A···O1i	0.86	2.25	3.089 (2)	164
O2—H2B···N1ii	0.82	1.96	2.703 (3)	150
C5—H5···O1i	0.93	2.55	3.410 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O3	0.82	2.25	2.694 (2)	114
N2—H2A⋯O1i	0.86	2.25	3.089 (2)	164
O2—H2B⋯N1ii	0.82	1.96	2.703 (3)	150
C5—H5⋯O1i	0.93	2.55	3.410 (3)	153

Symmetry codes: (i) ; (ii) .