2-Methyl-N′-[1-(2-pyrid­yl)ethyl­idene]benzohydrazide

Tang, C.-B.

doi:10.1107/S1600536810054267

organic compounds

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Volume 67| Part 2| February 2011| Page o271

doi:10.1107/S1600536810054267

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2-Methyl-N′-[1-(2-pyridyl)ethylidene]benzohydrazide

Chun-Bao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
^*Correspondence e-mail: tangchunbao@yahoo.com.cn

(Received 20 December 2010; accepted 25 December 2010; online 8 January 2011)

In the title compound, C₁₅H₁₅N₃O, the dihedral angle between the pyridine and benzene rings is 36.3 (2)°. In the crystal, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ); Pyta et al. (2010 ); Angelusiu et al. (2010 ). For related structures, see: Fun et al. (2008 ); Singh & Singh (2010 ); Ahmad et al. (2010 ); Tang (2010 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₅N₃O
M_r = 253.30
Orthorhombic, P b c n
a = 19.296 (3) Å
b = 8.1417 (18) Å
c = 17.294 (3) Å
V = 2716.8 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.984, T_max = 0.986
13661 measured reflections
2966 independent reflections
1539 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.158
S = 1.02
2966 reflections
177 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.91 (1)	2.05 (1)	2.937 (2)	165 (3)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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/S1600536810054267/sj5083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054267/sj5083Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds have received much attention in biological and structural chemistry in the last few years (Rasras et al., 2010; Pyta et al., 2010; Angelusiu et al., 2010; Fun et al., 2008; Singh & Singh, 2010; Ahmad et al., 2010). In the present paper, the author reports the crystal structure of the new title hydrazone compound (Fig. 1).

In the title compound, the dihedral angle between the pyridine and the benzene rings is 36.3 (2)°. The torsion angles C1—C8—N1—N2, C8—N1—N2—C9, and N1—N2—C9—C10 are 7.8 (2), 3.6 (2), and 1.5 (2)°, respectively. Bond lengths in the molecules are normal (Allen et al., 1987) and comparable to those in the similar compound the author reported recently (Tang, 2010).

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the b axis (Fig. 2).

Related literature top

For general background to hydrazones, see: Rasras et al. (2010); Pyta et al. (2010); Angelusiu et al. (2010). For related structures, see: Fun et al. (2008); Singh & Singh (2010); Ahmad et al. (2010); Tang (2010). For reference bond-length data, see: Allen et al. (1987).

Experimental top

2-Acetylpyridine (0.1 mmol, 12.1 mg) and 2-methylbenzohydrazide (0.1 mmol, 15.0 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. Colourless block-shaped crystals of the compound were formed by slow evaporation of the solvent over several days.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Molecular packing of the title compound, with hydrogen bonds shown as dashed lines.

2-Methyl-N'-[1-(2-pyridyl)ethylidene]benzohydrazide top

Crystal data top

C₁₅H₁₅N₃O	D_x = 1.239 Mg m⁻³
M_r = 253.30	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 1243 reflections
a = 19.296 (3) Å	θ = 2.5–24.6°
b = 8.1417 (18) Å	µ = 0.08 mm⁻¹
c = 17.294 (3) Å	T = 298 K
V = 2716.8 (9) Å³	Block, colourless
Z = 8	0.20 × 0.20 × 0.18 mm
F(000) = 1072

Data collection top

Bruker SMART CCD area-detector diffractometer	2966 independent reflections
Radiation source: fine-focus sealed tube	1539 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
T_min = 0.984, T_max = 0.986	k = −10→10
13661 measured reflections	l = −13→22

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0493P)² + 0.5475P] where P = (F_o² + 2F_c²)/3
2966 reflections	(Δ/σ)_max < 0.001
177 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₅H₁₅N₃O	V = 2716.8 (9) Å³
M_r = 253.30	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 19.296 (3) Å	µ = 0.08 mm⁻¹
b = 8.1417 (18) Å	T = 298 K
c = 17.294 (3) Å	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2966 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1539 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.986	R_int = 0.069
13661 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	1 restraint
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.17 e Å⁻³
2966 reflections	Δρ_min = −0.17 e Å⁻³
177 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 > 2sigma(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	0.26051 (10)	0.9439 (2)	0.05651 (11)	0.0451 (5)
N2	0.28738 (9)	1.0589 (2)	0.00578 (11)	0.0450 (5)
N3	0.43437 (11)	1.1437 (2)	−0.10682 (12)	0.0623 (6)
O1	0.17755 (8)	1.12421 (19)	0.09416 (11)	0.0613 (5)
C1	0.16962 (11)	0.8519 (3)	0.14164 (13)	0.0423 (5)
C2	0.10054 (12)	0.8104 (3)	0.12641 (14)	0.0513 (6)
C3	0.07187 (15)	0.6857 (4)	0.17027 (18)	0.0751 (9)
H3	0.0266	0.6531	0.1602	0.090*
C4	0.10778 (18)	0.6085 (4)	0.22804 (19)	0.0832 (10)
H4	0.0866	0.5263	0.2569	0.100*
C5	0.17470 (16)	0.6520 (3)	0.24329 (16)	0.0689 (8)
H5	0.1990	0.6005	0.2829	0.083*
C6	0.20621 (13)	0.7725 (3)	0.19965 (14)	0.0536 (6)
H6	0.2521	0.8007	0.2092	0.064*
C7	0.05886 (13)	0.8927 (4)	0.06421 (16)	0.0682 (8)
H7A	0.0192	0.8263	0.0520	0.102*
H7B	0.0870	0.9060	0.0188	0.102*
H7C	0.0437	0.9984	0.0820	0.102*
C8	0.20235 (11)	0.9857 (3)	0.09561 (13)	0.0423 (5)
C9	0.34432 (13)	1.0263 (3)	−0.02897 (14)	0.0508 (6)
C10	0.36834 (13)	1.1545 (3)	−0.08374 (13)	0.0499 (6)
C11	0.32524 (14)	1.2794 (3)	−0.10794 (15)	0.0644 (7)
H11	0.2792	1.2825	−0.0921	0.077*
C12	0.35119 (18)	1.3991 (4)	−0.15583 (18)	0.0836 (10)
H12	0.3231	1.4851	−0.1723	0.100*
C13	0.41887 (19)	1.3901 (4)	−0.17897 (18)	0.0831 (10)
H13	0.4377	1.4695	−0.2114	0.100*
C14	0.45800 (16)	1.2616 (4)	−0.15322 (16)	0.0735 (9)
H14	0.5040	1.2561	−0.1690	0.088*
C15	0.38792 (17)	0.8767 (4)	−0.0182 (2)	0.1043 (13)
H15A	0.4022	0.8692	0.0349	0.156*
H15B	0.4281	0.8838	−0.0508	0.156*
H15C	0.3615	0.7810	−0.0317	0.156*
H1	0.2784 (13)	0.8410 (17)	0.0589 (16)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0503 (11)	0.0302 (10)	0.0547 (12)	0.0008 (9)	0.0072 (10)	0.0072 (10)
N2	0.0514 (11)	0.0343 (10)	0.0492 (12)	−0.0062 (9)	0.0018 (10)	0.0042 (9)
N3	0.0678 (14)	0.0579 (14)	0.0611 (14)	−0.0096 (11)	0.0209 (11)	−0.0052 (11)
O1	0.0568 (10)	0.0342 (9)	0.0930 (14)	0.0044 (8)	0.0086 (9)	0.0081 (9)
C1	0.0511 (14)	0.0319 (12)	0.0438 (13)	−0.0001 (10)	0.0069 (11)	−0.0016 (10)
C2	0.0489 (14)	0.0517 (15)	0.0533 (15)	−0.0068 (11)	0.0079 (12)	−0.0033 (12)
C3	0.0606 (17)	0.083 (2)	0.081 (2)	−0.0229 (16)	0.0119 (16)	0.0115 (18)
C4	0.090 (2)	0.078 (2)	0.082 (2)	−0.0174 (18)	0.0242 (19)	0.0276 (18)
C5	0.088 (2)	0.0617 (18)	0.0567 (17)	0.0042 (16)	0.0064 (15)	0.0158 (14)
C6	0.0614 (15)	0.0422 (14)	0.0573 (16)	0.0013 (12)	0.0007 (13)	0.0023 (12)
C7	0.0512 (15)	0.082 (2)	0.0719 (18)	−0.0008 (14)	−0.0049 (14)	0.0016 (16)
C8	0.0439 (13)	0.0300 (12)	0.0531 (14)	−0.0024 (10)	−0.0038 (11)	0.0020 (11)
C9	0.0557 (14)	0.0390 (14)	0.0576 (15)	0.0000 (11)	0.0078 (12)	0.0013 (12)
C10	0.0613 (16)	0.0434 (14)	0.0450 (14)	−0.0095 (12)	0.0070 (12)	−0.0049 (11)
C11	0.0624 (16)	0.0629 (17)	0.0678 (18)	−0.0059 (14)	−0.0004 (14)	0.0220 (15)
C12	0.092 (2)	0.081 (2)	0.078 (2)	−0.0112 (18)	−0.0011 (18)	0.0332 (18)
C13	0.105 (3)	0.081 (2)	0.0635 (19)	−0.032 (2)	0.0128 (18)	0.0146 (17)
C14	0.084 (2)	0.075 (2)	0.0621 (19)	−0.0227 (18)	0.0271 (16)	−0.0054 (17)
C15	0.090 (2)	0.076 (2)	0.147 (3)	0.0296 (18)	0.052 (2)	0.046 (2)

Geometric parameters (Å, º) top

N1—C8	1.354 (3)	C6—H6	0.9300
N1—N2	1.384 (2)	C7—H7A	0.9600
N1—H1	0.907 (10)	C7—H7B	0.9600
N2—C9	1.280 (3)	C7—H7C	0.9600
N3—C14	1.332 (3)	C9—C10	1.484 (3)
N3—C10	1.338 (3)	C9—C15	1.492 (3)
O1—C8	1.225 (2)	C10—C11	1.379 (3)
C1—C6	1.386 (3)	C11—C12	1.374 (4)
C1—C2	1.400 (3)	C11—H11	0.9300
C1—C8	1.490 (3)	C12—C13	1.368 (4)
C2—C3	1.383 (3)	C12—H12	0.9300
C2—C7	1.501 (3)	C13—C14	1.365 (4)
C3—C4	1.369 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.365 (4)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.379 (3)	C15—H15C	0.9600
C5—H5	0.9300

C8—N1—N2	117.17 (17)	H7B—C7—H7C	109.5
C8—N1—H1	121.7 (17)	O1—C8—N1	123.0 (2)
N2—N1—H1	120.7 (18)	O1—C8—C1	121.2 (2)
C9—N2—N1	118.60 (19)	N1—C8—C1	115.71 (19)
C14—N3—C10	117.3 (2)	N2—C9—C10	114.9 (2)
C6—C1—C2	120.6 (2)	N2—C9—C15	126.5 (2)
C6—C1—C8	120.8 (2)	C10—C9—C15	118.5 (2)
C2—C1—C8	118.7 (2)	N3—C10—C11	122.2 (2)
C3—C2—C1	117.1 (2)	N3—C10—C9	116.2 (2)
C3—C2—C7	120.4 (2)	C11—C10—C9	121.6 (2)
C1—C2—C7	122.5 (2)	C12—C11—C10	119.1 (3)
C4—C3—C2	122.3 (3)	C12—C11—H11	120.4
C4—C3—H3	118.8	C10—C11—H11	120.4
C2—C3—H3	118.8	C13—C12—C11	119.1 (3)
C5—C4—C3	120.1 (3)	C13—C12—H12	120.4
C5—C4—H4	120.0	C11—C12—H12	120.4
C3—C4—H4	120.0	C14—C13—C12	118.3 (3)
C4—C5—C6	119.7 (3)	C14—C13—H13	120.9
C4—C5—H5	120.1	C12—C13—H13	120.9
C6—C5—H5	120.1	N3—C14—C13	124.0 (3)
C5—C6—C1	120.2 (2)	N3—C14—H14	118.0
C5—C6—H6	119.9	C13—C14—H14	118.0
C1—C6—H6	119.9	C9—C15—H15A	109.5
C2—C7—H7A	109.5	C9—C15—H15B	109.5
C2—C7—H7B	109.5	H15A—C15—H15B	109.5
H7A—C7—H7B	109.5	C9—C15—H15C	109.5
C2—C7—H7C	109.5	H15A—C15—H15C	109.5
H7A—C7—H7C	109.5	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.91 (1)	2.05 (1)	2.937 (2)	165 (3)

Symmetry code: (i) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅N₃O
M_r	253.30
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	19.296 (3), 8.1417 (18), 17.294 (3)
V (Å³)	2716.8 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.984, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	13661, 2966, 1539
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.158, 1.02
No. of reflections	2966
No. of parameters	177
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
N1—H1···O1ⁱ	0.907 (10)	2.051 (12)	2.937 (2)	165 (3)

Symmetry code: (i) −x+1/2, y−1/2, z.

Acknowledgements

Financial support from the Jiaying University research fund is gratefully acknowledged.

References

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