N'-(4-Methoxy-benzo-yl)pyridine-2-carbohydrazide.

The crystal structure of the title compound, C(14)H(13)N(3)O(3), exhibits two inter-molecular N-H⋯O hydrogen bonds.

Related literature

For general background to the coordination chemistry of pyridine derivatives, see: Koningsbruggen et al. (1997 ▶); Klingele & Brooker (2003 ▶); Suksrichavalit et al. (2009 ▶). For their biological activity, see: Tozkoparan et al. (2000 ▶); Grénman et al. (2003 ▶); Alagarsamy et al. (2008 ▶); Isloor et al. (2009 ▶). For their syntheses, see: Klingsberg (1958 ▶); Potts (1961 ▶).

Experimental

Crystal data

C14H13N3O3

M = 271.27

Monoclinic,

a = 14.836 (3) Å

b = 11.6078 (17) Å

c = 7.6499 (12) Å

β = 97.137 (11)°

V = 1307.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.25 × 0.20 × 0.18 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.976, T max = 0.982

13109 measured reflections

2957 independent reflections

1909 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.143

S = 1.02

2957 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013437/om2329sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013437/om2329Isup2.hkl

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

C14H13N3O3	F(000) = 568
Mr = 271.27	Dx = 1.378 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.836 (3) Å	Cell parameters from 2772 reflections
b = 11.6078 (17) Å	θ = 2.8–27.5°
c = 7.6499 (12) Å	µ = 0.10 mm−1
β = 97.137 (11)°	T = 293 K
V = 1307.2 (4) Å3	Block, colorless
Z = 4	0.25 × 0.20 × 0.18 mm

Rigaku SCXmini diffractometer	2957 independent reflections
Radiation source: fine-focus sealed tube	1909 reflections with I > 2σ(I)
graphite	Rint = 0.053
CCD_Profile_fitting scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −19→19
Tmin = 0.976, Tmax = 0.982	k = −15→14
13109 measured reflections	l = −9→9

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.0677P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2957 reflections	Δρmax = 0.16 e Å−3
183 parameters	Δρmin = −0.18 e Å−3
0 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: 0.041 (5)

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
C1	0.91128 (11)	0.22439 (14)	0.9042 (2)	0.0411 (4)
C2	0.97228 (12)	0.13505 (15)	0.8969 (2)	0.0543 (5)
H2	0.9527	0.0595	0.9075	0.065*
C3	1.06100 (13)	0.15577 (17)	0.8744 (3)	0.0598 (5)
H3	1.1007	0.0944	0.8668	0.072*
C4	1.09167 (12)	0.26761 (16)	0.8629 (3)	0.0526 (5)
C5	1.03233 (13)	0.35724 (16)	0.8720 (3)	0.0569 (5)
H5	1.0525	0.4328	0.8656	0.068*
C6	0.94239 (12)	0.33527 (15)	0.8909 (2)	0.0520 (5)
H6	0.9023	0.3965	0.8946	0.062*
C7	0.81706 (11)	0.19679 (14)	0.9344 (2)	0.0433 (4)
C8	1.21797 (14)	0.3917 (2)	0.8418 (4)	0.0946 (9)
H8A	1.1887	0.4334	0.7421	0.142*
H8B	1.2819	0.3868	0.8340	0.142*
H8C	1.2083	0.4311	0.9482	0.142*
C9	0.52469 (11)	0.13673 (14)	0.8280 (2)	0.0432 (4)
C10	0.41189 (12)	0.18980 (18)	0.9872 (3)	0.0589 (5)
H10	0.3898	0.2394	1.0674	0.071*
C11	0.35667 (13)	0.10217 (18)	0.9177 (3)	0.0635 (6)
H11	0.2992	0.0919	0.9517	0.076*
C12	0.38794 (14)	0.03054 (18)	0.7977 (3)	0.0679 (6)
H12	0.3516	−0.0289	0.7473	0.081*
C13	0.47394 (13)	0.04696 (16)	0.7517 (3)	0.0572 (5)
H13	0.4970	−0.0015	0.6712	0.069*
C14	0.61801 (12)	0.15765 (15)	0.7797 (2)	0.0448 (4)
N1	0.75270 (10)	0.26729 (12)	0.8514 (2)	0.0500 (4)
H1A	0.7632	0.3096	0.7655	0.075*
N2	0.66187 (9)	0.24618 (13)	0.8666 (2)	0.0507 (4)
H2A	0.6435	0.2881	0.9461	0.076*
N3	0.49533 (9)	0.20769 (13)	0.9461 (2)	0.0507 (4)
O1	0.79830 (8)	0.11775 (10)	1.03016 (15)	0.0530 (4)
O2	0.65007 (9)	0.10076 (11)	0.66877 (17)	0.0590 (4)
O3	1.18109 (9)	0.27954 (12)	0.8433 (2)	0.0759 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0422 (9)	0.0415 (9)	0.0399 (9)	0.0003 (7)	0.0060 (7)	0.0012 (7)
C2	0.0473 (11)	0.0427 (10)	0.0740 (13)	−0.0009 (8)	0.0114 (9)	0.0056 (9)
C3	0.0489 (11)	0.0502 (11)	0.0822 (14)	0.0078 (9)	0.0150 (10)	0.0052 (10)
C4	0.0411 (10)	0.0567 (11)	0.0607 (11)	−0.0028 (8)	0.0090 (8)	0.0078 (9)
C5	0.0511 (11)	0.0447 (10)	0.0752 (14)	−0.0067 (9)	0.0089 (10)	0.0042 (9)
C6	0.0462 (10)	0.0426 (10)	0.0676 (12)	0.0032 (8)	0.0091 (9)	−0.0022 (9)
C7	0.0457 (10)	0.0427 (9)	0.0429 (9)	−0.0025 (8)	0.0117 (8)	−0.0026 (8)
C8	0.0509 (13)	0.0814 (17)	0.153 (3)	−0.0185 (11)	0.0175 (15)	0.0266 (17)
C9	0.0432 (10)	0.0418 (9)	0.0447 (9)	0.0065 (7)	0.0066 (8)	0.0058 (7)
C10	0.0438 (11)	0.0659 (13)	0.0696 (13)	−0.0007 (9)	0.0169 (10)	−0.0102 (10)
C11	0.0418 (10)	0.0664 (13)	0.0831 (14)	−0.0055 (10)	0.0110 (10)	0.0014 (12)
C12	0.0587 (13)	0.0552 (12)	0.0882 (16)	−0.0154 (10)	0.0035 (11)	−0.0051 (11)
C13	0.0620 (12)	0.0468 (10)	0.0631 (12)	0.0005 (9)	0.0095 (10)	−0.0055 (9)
C14	0.0452 (10)	0.0432 (10)	0.0468 (10)	0.0097 (8)	0.0092 (8)	0.0057 (8)
N1	0.0394 (8)	0.0553 (9)	0.0583 (10)	0.0028 (7)	0.0179 (7)	0.0104 (7)
N2	0.0401 (8)	0.0549 (9)	0.0601 (10)	0.0024 (7)	0.0183 (7)	−0.0033 (7)
N3	0.0400 (8)	0.0549 (9)	0.0583 (9)	−0.0009 (7)	0.0105 (7)	−0.0059 (7)
O1	0.0513 (8)	0.0525 (7)	0.0567 (8)	−0.0058 (6)	0.0124 (6)	0.0079 (6)
O2	0.0620 (8)	0.0579 (8)	0.0601 (8)	0.0135 (6)	0.0192 (6)	−0.0035 (6)
O3	0.0428 (7)	0.0719 (10)	0.1157 (13)	−0.0033 (7)	0.0201 (8)	0.0171 (9)

C1—C6	1.375 (2)	C8—H8C	0.9600
C1—C2	1.382 (2)	C9—N3	1.335 (2)
C1—C7	1.480 (2)	C9—C13	1.373 (2)
C2—C3	1.370 (2)	C10—N3	1.331 (2)
C2—H2	0.9300	C10—C11	1.371 (3)
C3—C4	1.382 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.362 (3)
C4—O3	1.361 (2)	C11—H11	0.9300
C4—C5	1.370 (3)	C12—C13	1.378 (3)
C5—C6	1.384 (2)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—O2	1.2179 (19)
C7—O1	1.2276 (19)	C14—N2	1.347 (2)
C7—N1	1.354 (2)	C14—C9	1.496 (2)
C8—O3	1.413 (3)	N1—N2	1.389 (2)
C8—H8A	0.9600	N1—H1A	0.8500
C8—H8B	0.9600	N2—H2A	0.8500
C6—C1—C2	118.15 (16)	O2—C14—N2	123.43 (16)
C6—C1—C7	123.11 (15)	O2—C14—C9	122.51 (16)
C2—C1—C7	118.67 (15)	N2—C14—C9	114.04 (14)
C3—C2—C1	121.17 (17)	N3—C9—C13	123.25 (16)
C3—C2—H2	119.4	N3—C9—C14	117.16 (15)
C1—C2—H2	119.4	C13—C9—C14	119.59 (16)
C2—C3—C4	120.13 (17)	N3—C10—C11	123.56 (18)
C2—C3—H3	119.9	N3—C10—H10	118.2
C4—C3—H3	119.9	C11—C10—H10	118.2
O3—C4—C5	124.74 (17)	C12—C11—C10	118.49 (18)
O3—C4—C3	115.84 (17)	C12—C11—H11	120.8
C5—C4—C3	119.42 (17)	C10—C11—H11	120.8
C4—C5—C6	119.96 (17)	C11—C12—C13	119.42 (18)
C4—C5—H5	120.0	C11—C12—H12	120.3
C6—C5—H5	120.0	C13—C12—H12	120.3
C1—C6—C5	121.14 (16)	C9—C13—C12	118.22 (18)
C1—C6—H6	119.4	C9—C13—H13	120.9
C5—C6—H6	119.4	C12—C13—H13	120.9
O1—C7—N1	122.17 (16)	C7—N1—N2	119.30 (14)
O1—C7—C1	122.91 (16)	C7—N1—H1A	121.7
N1—C7—C1	114.89 (15)	N2—N1—H1A	116.1
O3—C8—H8A	109.5	C14—N2—N1	120.53 (14)
O3—C8—H8B	109.5	C14—N2—H2A	127.8
H8A—C8—H8B	109.5	N1—N2—H2A	111.0
O3—C8—H8C	109.5	C10—N3—C9	117.05 (16)
H8A—C8—H8C	109.5	C4—O3—C8	118.60 (16)
H8B—C8—H8C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.85	2.11	2.9479 (19)	168
N2—H2A···O2ii	0.85	2.13	2.938 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.85	2.11	2.9479 (19)	168
N2—H2A⋯O2ii	0.85	2.13	2.938 (2)	159

Symmetry codes: (i) ; (ii) .