N'-(2-Methoxy-benzyl-idene)nicotinohydrazide.

The title compound, C(14)H(13)N(3)O(2), was prepared by the reaction of 2-methoxy-benzyaldehyde with nicotinic acid hydrazide in methanol. The dihedral angle between the benzene and pyridine rings is 5.9 (3)°. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds, leading to the formation of chains along the c axis; adjacent chains are linked via C-H⋯O and C-H⋯N hydrogen bonds.

Related literature

For general background to Schiff base compounds, see: Archibald et al. (1994 ▶); Harada et al. (1999 ▶); Ogawa et al. (1998 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Sun et al. (2009 ▶); Wen et al. (2009 ▶).

Experimental

Crystal data

C14H13N3O2

M = 255.27

Tetragonal,

a = 9.3264 (13) Å

c = 15.594 (3) Å

V = 1356.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.983, T max = 0.985

6623 measured reflections

1519 independent reflections

1313 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.084

S = 1.06

1519 reflections

176 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.09 e Å−3

Δρmin = −0.14 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/S1600536810003831/ci5028sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003831/ci5028Isup2.hkl

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

C14H13N3O2	Dx = 1.250 Mg m−3
Mr = 255.27	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 2214 reflections
Hall symbol: P 4cw	θ = 2.5–25.3°
a = 9.3264 (13) Å	µ = 0.09 mm−1
c = 15.594 (3) Å	T = 298 K
V = 1356.4 (4) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.18 mm
F(000) = 536

Bruker APEXII CCD area-detector diffractometer	1519 independent reflections
Radiation source: fine-focus sealed tube	1313 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→10
Tmin = 0.983, Tmax = 0.985	k = −4→11
6623 measured reflections	l = −19→19

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0427P)2 + 0.084P] where P = (Fo2 + 2Fc2)/3
1519 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.09 e Å−3
2 restraints	Δρmin = −0.14 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	0.54565 (17)	0.50653 (18)	0.21981 (11)	0.0443 (4)
N2	0.41517 (19)	0.53627 (19)	0.18161 (11)	0.0457 (4)
N3	0.0801 (2)	0.6980 (3)	0.03464 (14)	0.0763 (7)
O1	0.84079 (19)	0.3686 (2)	0.05708 (12)	0.0681 (5)
O2	0.33671 (17)	0.66164 (18)	0.29682 (10)	0.0586 (4)
C1	0.7782 (2)	0.4068 (2)	0.20059 (15)	0.0454 (5)
C2	0.8837 (2)	0.3667 (2)	0.14119 (15)	0.0508 (5)
C3	1.0208 (3)	0.3312 (3)	0.1677 (2)	0.0635 (7)
H3	1.0901	0.3046	0.1279	0.076*
C4	1.0535 (3)	0.3360 (3)	0.2543 (2)	0.0662 (7)
H4	1.1455	0.3123	0.2724	0.079*
C5	0.9519 (3)	0.3753 (3)	0.31421 (19)	0.0621 (6)
H5	0.9751	0.3784	0.3722	0.075*
C6	0.8156 (3)	0.4098 (2)	0.28694 (15)	0.0516 (5)
H6	0.7469	0.4358	0.3273	0.062*
C7	0.6357 (2)	0.4433 (2)	0.17089 (15)	0.0466 (5)
H7	0.6091	0.4202	0.1151	0.056*
C8	0.3205 (2)	0.6206 (2)	0.22245 (13)	0.0420 (5)
C9	0.1932 (2)	0.6646 (2)	0.17108 (14)	0.0428 (5)
C10	0.0723 (3)	0.7159 (3)	0.21159 (16)	0.0623 (7)
H10	0.0690	0.7228	0.2710	0.075*
C11	−0.0433 (3)	0.7567 (4)	0.1626 (2)	0.0797 (9)
H11	−0.1265	0.7907	0.1884	0.096*
C12	−0.0339 (3)	0.7463 (4)	0.07564 (19)	0.0779 (9)
H12	−0.1125	0.7749	0.0432	0.093*
C13	0.1914 (3)	0.6590 (3)	0.08281 (14)	0.0571 (6)
H13	0.2732	0.6259	0.0550	0.069*
C14	0.9423 (4)	0.3294 (4)	−0.0070 (2)	0.0921 (11)
H14A	1.0234	0.3926	−0.0041	0.138*
H14B	0.8987	0.3366	−0.0626	0.138*
H14C	0.9734	0.2325	0.0026	0.138*
H2	0.394 (3)	0.496 (3)	0.1309 (11)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0447 (10)	0.0450 (9)	0.0430 (10)	0.0038 (8)	−0.0060 (8)	−0.0027 (8)
N2	0.0473 (10)	0.0510 (10)	0.0387 (10)	0.0048 (8)	−0.0067 (8)	−0.0073 (8)
N3	0.0612 (14)	0.118 (2)	0.0500 (13)	0.0151 (13)	−0.0096 (11)	0.0096 (13)
O1	0.0652 (10)	0.0875 (12)	0.0516 (10)	−0.0048 (9)	0.0080 (9)	−0.0131 (9)
O2	0.0685 (10)	0.0673 (10)	0.0399 (8)	0.0156 (8)	−0.0110 (8)	−0.0140 (8)
C1	0.0491 (12)	0.0404 (11)	0.0468 (12)	−0.0005 (9)	0.0015 (9)	−0.0005 (9)
C2	0.0522 (12)	0.0462 (11)	0.0538 (14)	−0.0060 (9)	0.0038 (10)	−0.0048 (10)
C3	0.0490 (13)	0.0615 (14)	0.0799 (18)	−0.0002 (11)	0.0098 (13)	−0.0091 (13)
C4	0.0479 (13)	0.0646 (16)	0.086 (2)	0.0025 (11)	−0.0054 (14)	0.0038 (14)
C5	0.0647 (15)	0.0641 (15)	0.0576 (15)	0.0002 (12)	−0.0114 (13)	0.0085 (12)
C6	0.0554 (13)	0.0517 (12)	0.0478 (13)	0.0016 (10)	0.0009 (10)	0.0040 (10)
C7	0.0519 (12)	0.0485 (11)	0.0395 (10)	0.0022 (9)	−0.0030 (10)	−0.0042 (9)
C8	0.0492 (11)	0.0405 (10)	0.0361 (11)	0.0013 (8)	−0.0022 (9)	−0.0018 (8)
C9	0.0449 (11)	0.0421 (10)	0.0414 (11)	−0.0001 (8)	−0.0009 (9)	−0.0020 (9)
C10	0.0606 (16)	0.0807 (17)	0.0458 (14)	0.0162 (12)	0.0040 (12)	−0.0068 (13)
C11	0.0526 (14)	0.111 (2)	0.076 (2)	0.0233 (14)	0.0058 (14)	−0.0014 (19)
C12	0.0502 (15)	0.114 (2)	0.0692 (19)	0.0146 (14)	−0.0098 (13)	0.0141 (17)
C13	0.0467 (13)	0.0809 (16)	0.0439 (13)	0.0107 (11)	0.0008 (10)	0.0058 (11)
C14	0.080 (2)	0.127 (3)	0.069 (2)	−0.0180 (19)	0.0249 (16)	−0.0256 (19)

N1—C7	1.279 (3)	C5—C6	1.379 (3)
N1—N2	1.383 (2)	C5—H5	0.93
N2—C8	1.343 (3)	C6—H6	0.93
N2—H2	0.897 (10)	C7—H7	0.93
N3—C12	1.320 (4)	C8—C9	1.489 (3)
N3—C13	1.332 (3)	C9—C13	1.378 (3)
O1—C2	1.371 (3)	C9—C10	1.378 (3)
O1—C14	1.424 (3)	C10—C11	1.375 (4)
O2—C8	1.231 (2)	C10—H10	0.93
C1—C6	1.391 (3)	C11—C12	1.362 (4)
C1—C2	1.402 (3)	C11—H11	0.93
C1—C7	1.448 (3)	C12—H12	0.93
C2—C3	1.385 (3)	C13—H13	0.93
C3—C4	1.385 (4)	C14—H14A	0.96
C3—H3	0.93	C14—H14B	0.96
C4—C5	1.380 (4)	C14—H14C	0.96
C4—H4	0.93
C7—N1—N2	114.42 (17)	C1—C7—H7	119.3
C8—N2—N1	119.46 (17)	O2—C8—N2	123.23 (19)
C8—N2—H2	120.9 (19)	O2—C8—C9	121.28 (18)
N1—N2—H2	119.6 (19)	N2—C8—C9	115.49 (17)
C12—N3—C13	116.6 (2)	C13—C9—C10	117.4 (2)
C2—O1—C14	118.3 (2)	C13—C9—C8	122.5 (2)
C6—C1—C2	118.0 (2)	C10—C9—C8	120.1 (2)
C6—C1—C7	122.3 (2)	C11—C10—C9	118.9 (2)
C2—C1—C7	119.7 (2)	C11—C10—H10	120.6
O1—C2—C3	123.9 (2)	C9—C10—H10	120.6
O1—C2—C1	115.1 (2)	C12—C11—C10	118.8 (3)
C3—C2—C1	121.0 (2)	C12—C11—H11	120.6
C4—C3—C2	119.1 (2)	C10—C11—H11	120.6
C4—C3—H3	120.4	N3—C12—C11	124.0 (3)
C2—C3—H3	120.4	N3—C12—H12	118.0
C5—C4—C3	121.1 (2)	C11—C12—H12	118.0
C5—C4—H4	119.4	N3—C13—C9	124.3 (2)
C3—C4—H4	119.4	N3—C13—H13	117.9
C6—C5—C4	119.1 (3)	C9—C13—H13	117.9
C6—C5—H5	120.4	O1—C14—H14A	109.5
C4—C5—H5	120.4	O1—C14—H14B	109.5
C5—C6—C1	121.7 (2)	H14A—C14—H14B	109.5
C5—C6—H6	119.2	O1—C14—H14C	109.5
C1—C6—H6	119.2	H14A—C14—H14C	109.5
N1—C7—C1	121.4 (2)	H14B—C14—H14C	109.5
N1—C7—H7	119.3

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.90 (1)	2.05 (2)	2.897 (2)	157 (3)
C4—H4···O1ii	0.93	2.58	3.469 (3)	160
C11—H11···N3iii	0.93	2.53	3.429 (4)	164
C13—H13···N1i	0.93	2.56	3.487 (3)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.90 (1)	2.05 (2)	2.897 (2)	157 (3)
C4—H4⋯O1ii	0.93	2.58	3.469 (3)	160
C11—H11⋯N3iii	0.93	2.53	3.429 (4)	164
C13—H13⋯N1i	0.93	2.56	3.487 (3)	176

Symmetry codes: (i) ; (ii) ; (iii) .