N′-(2-Methoxy­benzyl­idene)nicotinohydrazide

Wang, P.; Li, C.; Su, Y.-Q.

doi:10.1107/S1600536810003831

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o542

doi:10.1107/S1600536810003831

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N′-(2-Methoxybenzylidene)nicotinohydrazide

Ping Wang,^a Cong Li ^a and Yong-Qing Su ^a ^*

^aFaculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650092, People's Republic of China
^*Correspondence e-mail: yongqing_su@163.com

(Received 29 January 2010; accepted 31 January 2010; online 6 February 2010)

The title compound, C₁₄H₁₃N₃O₂, was prepared by the reaction of 2-methoxybenzyaldehyde with nicotinic acid hydrazide in methanol. The dihedral angle between the benzene and pyridine rings is 5.9 (3)°. In the crystal structure, molecules are linked by intermolecular 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_r = 255.27
Tetragonal, P 4₃
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.084
S = 1.06
1519 reflections
176 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.14 e Å⁻³

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) $[-y+1, x, z-{\script{1\over 4}}]$ ; (ii) $[y+1, -x+1, z+{\script{1\over 4}}]$ ; (iii) $[y-1, -x+1, z+{\script{1\over 4}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003831/ci5028sup1.cif

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

checkCIF report

Comment top

Schiff bases have been received much attention in recent years (Ogawa et al., 1998; Archibald et al., 1994; Harada et al., 1999). As a further investigation of the structures of Schiff base compounds, the title new compound is reported here.

In the title compound, the dihedral angle between the benzene ring and the pyridine ring is 5.9 (3)°. All the bond lengths are comparable with the similar Schiff bases reported previously (Wen et al., 2009; Mohd Lair et al., 2009; Sun et al., 2009).

In the crystal structure, molecules form chains running along the c axis through intermolecular N—H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

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 top

2-Methoxybenzaldehyde (1.0 mmol, 136 mg) and nicotinic acid hydrazide (1.0 mmol, 137 mg) were dissolved in methanol (30 ml). The mixture was stirred at room temperature for 1 h to give a colourless solution. After keeping the solution in air for 3 d, colourless block shaped crystals were formed.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

N'-(2-Methoxybenzylidene)nicotinohydrazide top

Crystal data top

C₁₄H₁₃N₃O₂	D_x = 1.250 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0427P)² + 0.084P] where P = (F_o² + 2F_c²)/3
1519 reflections	(Δ/σ)_max = 0.001
176 parameters	Δρ_max = 0.09 e Å⁻³
2 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₄H₁₃N₃O₂	Z = 4
M_r = 255.27	Mo Kα radiation
Tetragonal, P4₃	µ = 0.09 mm⁻¹
a = 9.3264 (13) Å	T = 298 K
c = 15.594 (3) Å	0.20 × 0.20 × 0.18 mm
V = 1356.4 (4) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	1519 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1313 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.985	R_int = 0.028
6623 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	2 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.09 e Å⁻³
1519 reflections	Δρ_min = −0.14 e Å⁻³
176 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −y+1, x, z−1/4; (ii) y+1, −x+1, z+1/4; (iii) y−1, −x+1, z+1/4.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₃O₂
M_r	255.27
Crystal system, space group	Tetragonal, P4₃
Temperature (K)	298
a, c (Å)	9.3264 (13), 15.594 (3)
V (Å³)	1356.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.983, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	6623, 1519, 1313
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.084, 1.06
No. of reflections	1519
No. of parameters	176
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.09, −0.14

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −y+1, x, z−1/4; (ii) y+1, −x+1, z+1/4; (iii) y−1, −x+1, z+1/4.

Acknowledgements

The authors acknowledge support by the Science and Technology Department of Yunnan Province, the Program of Yunnan Province's Young-Middle Aged Reserve Scientific and Technological Principal Culture Plan (grant No. 2006PY01–50) and the fund of Yunnan Province's Applied Research Plan (grant No. 2006E0032M).

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