(E)-N′-[1-(Thio­phen-2-yl)ethyl­idene]isonicotinohydrazide

Dileep, C.S.; Abdoh, M.M.M.; Chakravarthy, M.P.; Mohana, K.N.; Sridhar, M.A.

doi:10.1107/S1600536812039426

organic compounds

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Volume 68| Part 10| October 2012| Page o2972

https://doi.org/10.1107/S1600536812039426

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(E)-N′-[1-(Thiophen-2-yl)ethylidene]isonicotinohydrazide

C. S. Dileep,^a M. M. M Abdoh,^b M. P. Chakravarthy,^c K. N. Mohana ^c and M. A. Sridhar ^a ^*

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, ^bDepartment of Physics, Faculty of Science, An Najah National University, Nablus, West Bank, Palestinian Territories, and ^cDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India
^*Correspondence e-mail: mas@physics.uni-mysore.ac.in

(Received 10 September 2012; accepted 16 September 2012; online 22 September 2012)

In the title compound, C₁₂H₁₁N₃OS, the dihedral angle between the pyridine and thiophene rings is 46.70 (9)° and the C—N—N—C torsion angle is 178.61 (15)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(8) loops.

Related literature

For a related structure, see: Lu et al. (1996 ). For graph-set nomenclature of hydrogen bonds, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₂H₁₁N₃OS
M_r = 245.30
Triclinic, $[P \overline 1]$
a = 3.9466 (1) Å
b = 10.5956 (4) Å
c = 14.3647 (6) Å
α = 74.656 (2)°
β = 82.595 (2)°
γ = 79.426 (2)°
V = 567.39 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.30 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.853, T_max = 0.935
10651 measured reflections
2456 independent reflections
2162 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.104
S = 1.05
2456 reflections
159 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.89 (1)	2.08 (1)	2.9561 (17)	170 (2)
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812039426/hb6959sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039426/hb6959Isup2.hkl

checkCIF report

Comment top

The geometry of C6 atom is distorted trigonal planar geometry as indicated by bond angles O1—C6—N2 = 120.77 (15) Å, (O1—C6—C7) = 119.27 (14) Å, (N2—C6—C7) = 119.96 (13) Å. The bond length of C6 and C7 = 1.496 (2) Å, which is comparable with an equivalent bond length of 1.506 (3) Å for a compound reported earlier (Lu et al., 1996). The crystal structure exhibits intermolecular hydrogen bonds of the type N—H···O with symmetry codes -x, 1 - y, 2 - z.

Related literature top

For a related structure, see: Lu et al. (1996). For graph-set nomenclature of hydrogen bonds, see: Bernstein et al. (1995).

Experimental top

1.37 g (10 mmol) of isoniazide was dissolved by the addition of 15 ml of ethanol in a round bottomed flask. To this 1.1 ml (10 mmol) of 2-Acetyl-thiophene dissolved in 15 ml of ethanol was added. This solution was refluxed for 5 h with stirring and then the solution was concentrated using rotor vaporizer and dried in vacuo and the product obtained was collected. The purity of the compound was confirmed by the TLC. Colourless blocks were recrystallised from methanol solution.

Structure description top

For a related structure, see: Lu et al. (1996). For graph-set nomenclature of hydrogen bonds, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids for non-H atoms drawn at the 50% probability level.
	Fig. 2. The unit-cell packing diagram.

(E)-N'-[1-(Thiophen-2-yl)ethylidene]isonicotinohydrazide top

Crystal data top

C₁₂H₁₁N₃OS	Z = 2
M_r = 245.30	F(000) = 256
Triclinic, P1	D_x = 1.436 Mg m⁻³
a = 3.9466 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5956 (4) Å	Cell parameters from 5900 reflections
c = 14.3647 (6) Å	θ = 2.2–31.0°
α = 74.656 (2)°	µ = 0.27 mm⁻¹
β = 82.595 (2)°	T = 293 K
γ = 79.426 (2)°	Block, colourless
V = 567.39 (4) Å³	0.30 × 0.28 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2456 independent reflections
Radiation source: fine-focus sealed tube	2162 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω and φ scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −5→4
T_min = 0.853, T_max = 0.935	k = −13→13
10651 measured reflections	l = −18→18

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) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0524P)² + 0.2115P] where P = (F_o² + 2F_c²)/3
2456 reflections	(Δ/σ)_max < 0.001
159 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₂H₁₁N₃OS	γ = 79.426 (2)°
M_r = 245.30	V = 567.39 (4) Å³
Triclinic, P1	Z = 2
a = 3.9466 (1) Å	Mo Kα radiation
b = 10.5956 (4) Å	µ = 0.27 mm⁻¹
c = 14.3647 (6) Å	T = 293 K
α = 74.656 (2)°	0.30 × 0.28 × 0.25 mm
β = 82.595 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2456 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2162 reflections with I > 2σ(I)
T_min = 0.853, T_max = 0.935	R_int = 0.022
10651 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.26 e Å⁻³
2456 reflections	Δρ_min = −0.20 e Å⁻³
159 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
C1	0.9693 (5)	0.70554 (18)	0.50027 (13)	0.0472 (4)
H1	1.0867	0.6862	0.4441	0.057*
C2	0.8919 (5)	0.82803 (19)	0.51454 (13)	0.0499 (4)
H2	0.9499	0.9031	0.4691	0.060*
C3	0.7129 (5)	0.83102 (17)	0.60598 (12)	0.0446 (4)
H3	0.6397	0.9080	0.6273	0.053*
C4	0.6596 (4)	0.70697 (14)	0.65967 (11)	0.0323 (3)
C5	0.4812 (4)	0.66887 (14)	0.75589 (10)	0.0310 (3)
C6	0.2859 (4)	0.37449 (15)	0.91748 (11)	0.0351 (3)
C7	0.4383 (4)	0.27417 (13)	0.86131 (10)	0.0310 (3)
C8	0.3769 (4)	0.28667 (15)	0.76656 (11)	0.0387 (4)
H8	0.2533	0.3641	0.7313	0.046*
C9	0.5030 (5)	0.18159 (17)	0.72543 (12)	0.0443 (4)
H9	0.4566	0.1904	0.6620	0.053*
C10	0.7437 (5)	0.05892 (16)	0.86100 (14)	0.0483 (4)
H10	0.8728	−0.0189	0.8939	0.058*
C11	0.6241 (4)	0.15680 (15)	0.90973 (12)	0.0400 (4)
H11	0.6679	0.1439	0.9739	0.048*
C12	0.3178 (5)	0.77498 (15)	0.80545 (12)	0.0415 (4)
H12A	0.0709	0.7799	0.8113	0.062*
H12B	0.3787	0.8585	0.7682	0.062*
H12C	0.3985	0.7549	0.8688	0.062*
N1	0.4799 (3)	0.54402 (12)	0.78951 (9)	0.0342 (3)
N2	0.3047 (4)	0.50324 (12)	0.87852 (9)	0.0380 (3)
N3	0.6861 (4)	0.06878 (14)	0.77044 (11)	0.0473 (4)
O1	0.1424 (4)	0.33773 (12)	0.99877 (9)	0.0522 (3)
S1	0.82822 (12)	0.58973 (4)	0.59655 (3)	0.04475 (15)
H2A	0.188 (5)	0.5583 (17)	0.9127 (13)	0.055 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0532 (10)	0.0516 (10)	0.0356 (8)	−0.0122 (8)	0.0064 (7)	−0.0107 (7)
C2	0.0639 (12)	0.0450 (10)	0.0392 (9)	−0.0203 (8)	0.0043 (8)	−0.0038 (7)
C3	0.0596 (11)	0.0350 (8)	0.0399 (9)	−0.0144 (7)	0.0031 (7)	−0.0094 (7)
C4	0.0362 (8)	0.0286 (7)	0.0326 (7)	−0.0052 (6)	−0.0022 (6)	−0.0087 (6)
C5	0.0339 (7)	0.0276 (7)	0.0319 (7)	−0.0042 (5)	−0.0020 (6)	−0.0091 (6)
C6	0.0424 (8)	0.0286 (7)	0.0313 (7)	−0.0031 (6)	0.0050 (6)	−0.0074 (6)
C7	0.0346 (7)	0.0259 (7)	0.0311 (7)	−0.0068 (5)	0.0054 (6)	−0.0071 (5)
C8	0.0479 (9)	0.0322 (8)	0.0343 (8)	−0.0059 (6)	−0.0018 (7)	−0.0064 (6)
C9	0.0576 (10)	0.0439 (9)	0.0358 (8)	−0.0150 (8)	0.0013 (7)	−0.0154 (7)
C10	0.0560 (11)	0.0309 (8)	0.0542 (10)	0.0054 (7)	−0.0039 (8)	−0.0122 (7)
C11	0.0502 (9)	0.0327 (8)	0.0344 (8)	−0.0008 (7)	−0.0036 (7)	−0.0075 (6)
C12	0.0523 (10)	0.0300 (7)	0.0415 (8)	−0.0063 (7)	0.0073 (7)	−0.0132 (6)
N1	0.0429 (7)	0.0275 (6)	0.0304 (6)	−0.0052 (5)	0.0051 (5)	−0.0082 (5)
N2	0.0510 (8)	0.0263 (6)	0.0332 (7)	−0.0032 (5)	0.0099 (6)	−0.0099 (5)
N3	0.0562 (9)	0.0377 (7)	0.0514 (9)	−0.0066 (6)	0.0049 (7)	−0.0217 (6)
O1	0.0758 (9)	0.0345 (6)	0.0369 (6)	−0.0040 (6)	0.0215 (6)	−0.0084 (5)
S1	0.0584 (3)	0.0344 (2)	0.0389 (2)	−0.00466 (18)	0.00777 (18)	−0.01196 (17)

Geometric parameters (Å, º) top

C1—C2	1.341 (3)	C7—C11	1.381 (2)
C1—S1	1.6977 (18)	C8—C9	1.380 (2)
C1—H1	0.9300	C8—H8	0.9300
C2—C3	1.414 (2)	C9—N3	1.328 (2)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.375 (2)	C10—N3	1.323 (2)
C3—H3	0.9300	C10—C11	1.381 (2)
C4—C5	1.458 (2)	C10—H10	0.9300
C4—S1	1.7162 (15)	C11—H11	0.9300
C5—N1	1.2834 (19)	C12—H12A	0.9600
C5—C12	1.492 (2)	C12—H12B	0.9600
C6—O1	1.2270 (18)	C12—H12C	0.9600
C6—N2	1.3425 (19)	N1—N2	1.3745 (17)
C6—C7	1.4956 (19)	N2—H2A	0.888 (9)
C7—C8	1.381 (2)

C2—C1—S1	112.29 (14)	C7—C8—H8	120.8
C2—C1—H1	123.9	N3—C9—C8	124.36 (16)
S1—C1—H1	123.9	N3—C9—H9	117.8
C1—C2—C3	112.91 (16)	C8—C9—H9	117.8
C1—C2—H2	123.5	N3—C10—C11	124.17 (16)
C3—C2—H2	123.5	N3—C10—H10	117.9
C4—C3—C2	112.15 (15)	C11—C10—H10	117.9
C4—C3—H3	123.9	C7—C11—C10	118.75 (15)
C2—C3—H3	123.9	C7—C11—H11	120.6
C3—C4—C5	128.92 (14)	C10—C11—H11	120.6
C3—C4—S1	110.69 (12)	C5—C12—H12A	109.5
C5—C4—S1	120.38 (11)	C5—C12—H12B	109.5
N1—C5—C4	115.18 (13)	H12A—C12—H12B	109.5
N1—C5—C12	126.20 (14)	C5—C12—H12C	109.5
C4—C5—C12	118.62 (13)	H12A—C12—H12C	109.5
O1—C6—N2	120.77 (14)	H12B—C12—H12C	109.5
O1—C6—C7	119.27 (13)	C5—N1—N2	117.49 (12)
N2—C6—C7	119.96 (13)	C6—N2—N1	120.90 (12)
C8—C7—C11	117.96 (13)	C6—N2—H2A	115.3 (14)
C8—C7—C6	123.76 (13)	N1—N2—H2A	123.7 (14)
C11—C7—C6	117.98 (13)	C10—N3—C9	116.26 (14)
C9—C8—C7	118.49 (15)	C1—S1—C4	91.96 (8)
C9—C8—H8	120.8

S1—C1—C2—C3	0.1 (2)	C7—C8—C9—N3	−1.2 (3)
C1—C2—C3—C4	0.2 (3)	C8—C7—C11—C10	1.0 (2)
C2—C3—C4—C5	−178.72 (16)	C6—C7—C11—C10	175.01 (15)
C2—C3—C4—S1	−0.3 (2)	N3—C10—C11—C7	−1.4 (3)
C3—C4—C5—N1	−178.08 (16)	C4—C5—N1—N2	−177.77 (13)
S1—C4—C5—N1	3.7 (2)	C12—C5—N1—N2	1.8 (2)
C3—C4—C5—C12	2.3 (3)	O1—C6—N2—N1	176.75 (16)
S1—C4—C5—C12	−175.92 (12)	C7—C6—N2—N1	−3.7 (2)
O1—C6—C7—C8	130.37 (18)	C5—N1—N2—C6	178.61 (15)
N2—C6—C7—C8	−49.1 (2)	C11—C10—N3—C9	0.5 (3)
O1—C6—C7—C11	−43.3 (2)	C8—C9—N3—C10	0.8 (3)
N2—C6—C7—C11	137.23 (16)	C2—C1—S1—C4	−0.23 (16)
C11—C7—C8—C9	0.2 (2)	C3—C4—S1—C1	0.32 (14)
C6—C7—C8—C9	−173.46 (15)	C5—C4—S1—C1	178.87 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.89 (1)	2.08 (1)	2.9561 (17)	170 (2)

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁N₃OS
M_r	245.30
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	3.9466 (1), 10.5956 (4), 14.3647 (6)
α, β, γ (°)	74.656 (2), 82.595 (2), 79.426 (2)
V (Å³)	567.39 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.28 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.853, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	10651, 2456, 2162
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.104, 1.05
No. of reflections	2456
No. of parameters	159
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)	0.26, −0.20

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.888 (9)	2.078 (10)	2.9561 (17)	170 (2)

Symmetry code: (i) −x, −y+1, −z+2.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lu, Z.-L., Duan, C.-Y., Tian, Y.-P., You, X.-Z., Fun, H.-K. & Sivakumar, K. (1996). Acta Cryst. C52, 1507–1509. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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