N'-[(3-Methyl-2-thien-yl)carbon-yl]isonicotinohydrazide.

In the title compound, C(12)H(11)N(3)O(2)S, the pyridine ring is inclined to the thio-phene ring, forming a dihedral angle of 34.96 (7)°. The mean plane through the hydrazide unit forms dihedral angles of 21.57 (8) and 53.08 (8)°, respectively, with the pyridine and thio-phene rings. The two O atoms are twisted away from each other, as indicated by the C-N-N-C torsion angle of -81.27 (15)°. In the crystal structure, mol-ecules are linked into an extended three-dimensional network by inter-molecular N-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds. The crystal structure also features a short S⋯O [3.2686 (10) Å] inter-action and a weak inter-molecular C-H⋯π inter-action.

Related literature

For general background to and application of isoniazid derivatives, see: Janin (2007 ▶); Maccari et al. (2005 ▶); Slayden et al. (2000 ▶). For the preparation of the title compound, see: Besra et al. (1993 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a closely related structure, see: Naveenkumar et al. (2009 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C12H11N3O2S

M = 261.30

Orthorhombic,

a = 8.9206 (1) Å

b = 10.7552 (2) Å

c = 12.4934 (2) Å

V = 1198.65 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.58 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.861, T max = 0.961

17333 measured reflections

4355 independent reflections

4078 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 1.05

4355 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.43 e Å−3

Absolute structure: Flack (1983 ▶), 1856 Friedel pairs

Flack parameter: −0.04 (6)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033030/is2451sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033030/is2451Isup2.hkl

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

C12H11N3O2S	F(000) = 544
Mr = 261.30	Dx = 1.448 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9634 reflections
a = 8.9206 (1) Å	θ = 2.5–32.7°
b = 10.7552 (2) Å	µ = 0.27 mm−1
c = 12.4934 (2) Å	T = 100 K
V = 1198.65 (3) Å3	Block, colourless
Z = 4	0.58 × 0.20 × 0.15 mm

Bruker SMART APEXII CCD area-detector diffractometer	4355 independent reflections
Radiation source: fine-focus sealed tube	4078 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 32.7°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.861, Tmax = 0.961	k = −14→16
17333 measured reflections	l = −17→18

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0542P)2 + 0.3319P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4355 reflections	Δρmax = 0.79 e Å−3
165 parameters	Δρmin = −0.43 e Å−3
0 restraints	Absolute structure: Flack (1983), 1856 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (6)

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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.

	x	y	z	Uiso*/Ueq
S1	0.26735 (4)	0.98879 (3)	0.04525 (3)	0.01858 (8)
O1	0.29108 (13)	0.48575 (10)	0.02488 (8)	0.0221 (2)
O2	0.01066 (11)	0.69442 (9)	0.07046 (8)	0.01664 (19)
N1	0.03034 (14)	0.21406 (11)	−0.25010 (10)	0.0159 (2)
N2	0.18343 (13)	0.62066 (10)	−0.09379 (9)	0.0137 (2)
H1N2	0.1404	0.6288	−0.1550	0.016*
N3	0.21647 (13)	0.72506 (10)	−0.03274 (9)	0.01367 (19)
H1N3	0.2954	0.7684	−0.0458	0.016*
C1	0.11893 (17)	0.29049 (12)	−0.08076 (11)	0.0165 (2)
H1A	0.1343	0.2764	−0.0081	0.020*
C2	0.05396 (17)	0.19936 (13)	−0.14457 (11)	0.0174 (2)
H2A	0.0255	0.1248	−0.1128	0.021*
C3	0.07732 (15)	0.32069 (12)	−0.29452 (11)	0.0153 (2)
H3A	0.0653	0.3306	−0.3680	0.018*
C4	0.14288 (15)	0.41719 (12)	−0.23723 (11)	0.0143 (2)
H4A	0.1741	0.4894	−0.2716	0.017*
C5	0.16079 (15)	0.40323 (12)	−0.12698 (10)	0.0136 (2)
C6	0.21924 (14)	0.50531 (11)	−0.05670 (10)	0.0138 (2)
C7	0.12212 (14)	0.75769 (11)	0.04814 (11)	0.0125 (2)
C8	0.15680 (15)	0.87488 (12)	0.10399 (11)	0.0142 (2)
C9	0.10620 (16)	0.91137 (14)	0.20356 (11)	0.0177 (2)
C10	0.15852 (18)	1.03210 (14)	0.23047 (13)	0.0209 (3)
H10A	0.1356	1.0716	0.2947	0.025*
C11	0.24567 (18)	1.08445 (13)	0.15288 (12)	0.0214 (3)
H11A	0.2883	1.1631	0.1581	0.026*
C12	0.0117 (2)	0.83596 (16)	0.27738 (13)	0.0259 (3)
H12A	0.0530	0.7538	0.2835	0.039*
H12B	−0.0884	0.8309	0.2496	0.039*
H12C	0.0097	0.8745	0.3466	0.039*

	U11	U22	U33	U12	U13	U23
S1	0.02092 (15)	0.01399 (13)	0.02083 (16)	−0.00198 (11)	0.00366 (12)	−0.00283 (12)
O1	0.0302 (5)	0.0186 (4)	0.0176 (5)	0.0033 (4)	−0.0104 (4)	−0.0021 (4)
O2	0.0134 (4)	0.0166 (4)	0.0200 (5)	−0.0026 (3)	0.0000 (3)	0.0000 (4)
N1	0.0187 (5)	0.0131 (5)	0.0160 (5)	−0.0004 (4)	−0.0017 (4)	−0.0018 (4)
N2	0.0177 (5)	0.0113 (4)	0.0120 (5)	−0.0003 (4)	−0.0028 (4)	−0.0031 (4)
N3	0.0150 (5)	0.0122 (4)	0.0138 (5)	−0.0024 (4)	0.0005 (4)	−0.0046 (4)
C1	0.0229 (6)	0.0140 (6)	0.0125 (5)	0.0003 (5)	−0.0015 (5)	0.0011 (4)
C2	0.0226 (6)	0.0123 (5)	0.0173 (6)	−0.0006 (5)	−0.0006 (5)	0.0004 (5)
C3	0.0182 (6)	0.0163 (6)	0.0114 (5)	−0.0001 (4)	0.0005 (4)	−0.0028 (4)
C4	0.0172 (6)	0.0127 (5)	0.0131 (5)	−0.0014 (4)	−0.0001 (4)	−0.0011 (4)
C5	0.0158 (5)	0.0123 (5)	0.0128 (5)	0.0014 (4)	−0.0015 (4)	−0.0018 (4)
C6	0.0159 (5)	0.0133 (5)	0.0122 (5)	0.0008 (4)	−0.0012 (4)	−0.0018 (4)
C7	0.0129 (5)	0.0123 (5)	0.0124 (5)	0.0012 (4)	−0.0020 (4)	0.0002 (4)
C8	0.0139 (5)	0.0128 (5)	0.0160 (6)	0.0008 (4)	−0.0015 (4)	−0.0016 (4)
C9	0.0180 (6)	0.0188 (6)	0.0165 (6)	0.0005 (5)	−0.0001 (5)	−0.0021 (5)
C10	0.0230 (6)	0.0194 (6)	0.0205 (6)	0.0026 (5)	−0.0022 (5)	−0.0084 (5)
C11	0.0246 (7)	0.0152 (5)	0.0245 (7)	−0.0008 (5)	−0.0006 (5)	−0.0079 (5)
C12	0.0299 (8)	0.0246 (7)	0.0234 (7)	−0.0028 (6)	0.0019 (6)	−0.0040 (6)

S1—C11	1.7041 (14)	C3—C4	1.3898 (18)
S1—C8	1.7355 (14)	C3—H3A	0.9300
O1—C6	1.2222 (15)	C4—C5	1.3948 (19)
O2—C7	1.2367 (15)	C4—H4A	0.9300
N1—C3	1.3412 (18)	C5—C6	1.4994 (18)
N1—C2	1.3445 (18)	C7—C8	1.4736 (17)
N2—C6	1.3623 (16)	C8—C9	1.3803 (19)
N2—N3	1.3890 (14)	C9—C10	1.420 (2)
N2—H1N2	0.8600	C9—C12	1.489 (2)
N3—C7	1.3611 (17)	C10—C11	1.364 (2)
N3—H1N3	0.8600	C10—H10A	0.9300
C1—C2	1.3899 (19)	C11—H11A	0.9300
C1—C5	1.3940 (18)	C12—H12A	0.9600
C1—H1A	0.9300	C12—H12B	0.9600
C2—H2A	0.9300	C12—H12C	0.9600
C11—S1—C8	91.61 (7)	O1—C6—C5	123.00 (12)
C3—N1—C2	117.21 (12)	N2—C6—C5	112.71 (11)
C6—N2—N3	119.98 (11)	O2—C7—N3	121.52 (11)
C6—N2—H1N2	120.0	O2—C7—C8	122.19 (12)
N3—N2—H1N2	120.0	N3—C7—C8	116.25 (11)
C7—N3—N2	119.00 (11)	C9—C8—C7	126.96 (13)
C7—N3—H1N3	120.5	C9—C8—S1	111.48 (10)
N2—N3—H1N3	120.5	C7—C8—S1	121.53 (10)
C2—C1—C5	119.18 (12)	C8—C9—C10	111.46 (13)
C2—C1—H1A	120.4	C8—C9—C12	126.03 (14)
C5—C1—H1A	120.4	C10—C9—C12	122.50 (13)
N1—C2—C1	123.01 (13)	C11—C10—C9	113.35 (13)
N1—C2—H2A	118.5	C11—C10—H10A	123.3
C1—C2—H2A	118.5	C9—C10—H10A	123.3
N1—C3—C4	123.85 (12)	C10—C11—S1	112.10 (11)
N1—C3—H3A	118.1	C10—C11—H11A	124.0
C4—C3—H3A	118.1	S1—C11—H11A	124.0
C3—C4—C5	118.45 (12)	C9—C12—H12A	109.5
C3—C4—H4A	120.8	C9—C12—H12B	109.5
C5—C4—H4A	120.8	H12A—C12—H12B	109.5
C1—C5—C4	118.16 (12)	C9—C12—H12C	109.5
C1—C5—C6	119.18 (11)	H12A—C12—H12C	109.5
C4—C5—C6	122.64 (12)	H12B—C12—H12C	109.5
O1—C6—N2	124.29 (12)
C6—N2—N3—C7	−81.27 (15)	N2—N3—C7—C8	−175.15 (11)
C3—N1—C2—C1	2.3 (2)	O2—C7—C8—C9	21.3 (2)
C5—C1—C2—N1	0.6 (2)	N3—C7—C8—C9	−161.26 (13)
C2—N1—C3—C4	−2.5 (2)	O2—C7—C8—S1	−156.60 (11)
N1—C3—C4—C5	−0.2 (2)	N3—C7—C8—S1	20.83 (16)
C2—C1—C5—C4	−3.4 (2)	C11—S1—C8—C9	−0.12 (11)
C2—C1—C5—C6	175.06 (12)	C11—S1—C8—C7	178.09 (12)
C3—C4—C5—C1	3.2 (2)	C7—C8—C9—C10	−178.07 (13)
C3—C4—C5—C6	−175.20 (12)	S1—C8—C9—C10	0.02 (15)
N3—N2—C6—O1	−6.2 (2)	C7—C8—C9—C12	3.3 (2)
N3—N2—C6—C5	173.77 (11)	S1—C8—C9—C12	−178.58 (13)
C1—C5—C6—O1	32.1 (2)	C8—C9—C10—C11	0.12 (19)
C4—C5—C6—O1	−149.49 (14)	C12—C9—C10—C11	178.78 (14)
C1—C5—C6—N2	−147.86 (13)	C9—C10—C11—S1	−0.21 (17)
C4—C5—C6—N2	30.54 (18)	C8—S1—C11—C10	0.19 (12)
N2—N3—C7—O2	2.30 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N1i	0.86	2.14	2.9068 (17)	149
N3—H1N3···O2ii	0.86	1.99	2.8034 (15)	158
C4—H4A···O1iii	0.93	2.58	3.2047 (17)	125
C10—H10A···O2iv	0.93	2.51	3.3928 (19)	159
C11—H11A···Cg1v	0.93	2.80	3.3760 (17)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N1i	0.86	2.14	2.9068 (17)	149
N3—H1N3⋯O2ii	0.86	1.99	2.8034 (15)	158
C4—H4A⋯O1iii	0.93	2.58	3.2047 (17)	125
C10—H10A⋯O2iv	0.93	2.51	3.3928 (19)	159
C11—H11A⋯Cg1v	0.93	2.80	3.3760 (17)	121

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 is centroid of the C1/C2/N1/C3–C5 ring.