N'-(3-Thienylmethyl-ene)pyridine-2-carbohydrazide.

The title compound, C(11)H(9)N(3)OS, was prepared to investigate the coordination chemistry of thio-phene-containing ligands as precursors to inter-esting metallopolymers. The mol-ecule is nearly planar. The angle between the thio-phene and pyridine rings is 8.63 (4)° and features the expected trans configuration about the imine bond. The structure is stabilized by a weak inter-molecular N-H⋯O hydrogen bond. The distance between centroids of adjacent thio-phene rings [3.67 (8) Å] suggests the presence of π-π inter-actions.

Related literature

The preparation and coordination chemistry of a similar compound containing a 2-substituted thio­phene were reported previously by El-Motaleb et al. (2005 ▶); however, no structural details were provided. For related literature and structures of other mol­ecules containing the pyridine-2-carbonohydrazide system, see: Klingele & Brooker (2004 ▶); Xie et al. (2006 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

C11H9N3OS

M = 231.27

Monoclinic,

a = 11.6817 (3) Å

b = 9.1454 (3) Å

c = 10.0890 (3) Å

β = 103.230 (1)°

V = 1049.24 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 173 (2) K

0.40 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.908, T max = 0.959

32428 measured reflections

6449 independent reflections

5355 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.109

S = 1.05

6449 reflections

181 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004960/fl2185sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004960/fl2185Isup2.hkl

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

C11H9N3OS	F000 = 480
Mr = 231.27	Dx = 1.464 Mg m−3
Monoclinic, P2(1)/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9922 reflections
a = 11.6817 (3) Å	θ = 2.9–39.5º
b = 9.1454 (3) Å	µ = 0.29 mm−1
c = 10.0890 (3) Å	T = 173 (2) K
β = 103.2300 (10)º	Block, colourless
V = 1049.24 (5) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	6449 independent reflections
Radiation source: fine-focus sealed tube	5355 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 173(2) K	θmax = 40.5º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −21→20
Tmin = 0.908, Tmax = 0.959	k = −16→16
32428 measured reflections	l = −18→14

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0599P)2 + 0.1403P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
6449 reflections	Δρmax = 0.48 e Å−3
181 parameters	Δρmin = −0.44 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
S1	0.463771 (16)	0.23464 (2)	0.454041 (19)	0.02568 (5)
O1	0.85993 (5)	0.78873 (6)	0.23484 (5)	0.02601 (10)
C1	0.58685 (6)	0.33166 (8)	0.52713 (7)	0.02334 (11)
H1	0.6218 (12)	0.3226 (15)	0.6255 (14)	0.038 (3)*
N1	0.76136 (5)	0.59050 (6)	0.38381 (5)	0.01975 (9)
N2	0.86362 (5)	0.66685 (7)	0.43407 (6)	0.02150 (10)
H2	0.8983 (11)	0.6677 (15)	0.5159 (14)	0.041 (3)*
C2	0.62431 (5)	0.41837 (7)	0.43437 (6)	0.01909 (9)
C3	0.54986 (6)	0.40473 (8)	0.30101 (6)	0.02346 (11)
H3	0.5598 (11)	0.4576 (15)	0.2219 (14)	0.038 (3)*
N3	1.06794 (5)	0.77731 (7)	0.55311 (6)	0.02522 (11)
C4	0.45955 (6)	0.30881 (8)	0.29705 (7)	0.02585 (12)
H4	0.4001 (12)	0.2786 (15)	0.2207 (14)	0.039 (3)*
C5	0.72865 (5)	0.50925 (7)	0.47217 (6)	0.02064 (10)
H5	0.7741 (11)	0.5050 (14)	0.5620 (12)	0.032 (3)*
C6	0.90780 (5)	0.75931 (7)	0.35325 (6)	0.01910 (10)
C7	1.02436 (5)	0.82307 (7)	0.42481 (6)	0.01914 (10)
C8	1.08096 (6)	0.92324 (8)	0.35862 (7)	0.02498 (12)
H8	1.0462 (10)	0.9482 (14)	0.2685 (12)	0.030 (3)*
C9	1.18816 (7)	0.98075 (9)	0.42927 (9)	0.02855 (13)
H9	1.2275 (12)	1.0512 (16)	0.3916 (13)	0.040 (3)*
C10	1.23335 (6)	0.93561 (9)	0.56184 (9)	0.02901 (13)
H10	1.3068 (12)	0.9703 (17)	0.6115 (13)	0.042 (4)*
C11	1.17048 (6)	0.83398 (10)	0.61907 (8)	0.02998 (14)
H11	1.2008 (13)	0.7924 (18)	0.7155 (16)	0.050 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.02498 (8)	0.02603 (8)	0.02706 (9)	−0.00757 (5)	0.00809 (6)	−0.00236 (5)
O1	0.0262 (2)	0.0318 (2)	0.01804 (19)	−0.00370 (18)	0.00077 (16)	0.00251 (17)
C1	0.0225 (2)	0.0263 (3)	0.0206 (2)	−0.0040 (2)	0.00363 (19)	0.0013 (2)
N1	0.01699 (19)	0.0214 (2)	0.0198 (2)	−0.00233 (16)	0.00210 (15)	−0.00098 (16)
N2	0.0187 (2)	0.0259 (2)	0.0182 (2)	−0.00545 (17)	0.00069 (16)	0.00143 (17)
C2	0.0182 (2)	0.0192 (2)	0.0193 (2)	−0.00147 (17)	0.00317 (17)	−0.00077 (17)
C3	0.0258 (3)	0.0244 (3)	0.0189 (2)	−0.0053 (2)	0.00249 (19)	−0.00152 (19)
N3	0.0194 (2)	0.0311 (3)	0.0230 (2)	−0.00334 (19)	0.00019 (17)	0.0037 (2)
C4	0.0265 (3)	0.0271 (3)	0.0223 (3)	−0.0072 (2)	0.0022 (2)	−0.0045 (2)
C5	0.0191 (2)	0.0224 (2)	0.0193 (2)	−0.00278 (18)	0.00200 (17)	−0.00012 (18)
C6	0.0181 (2)	0.0202 (2)	0.0184 (2)	−0.00070 (17)	0.00300 (17)	−0.00088 (17)
C7	0.0173 (2)	0.0199 (2)	0.0199 (2)	−0.00059 (17)	0.00357 (17)	−0.00080 (17)
C8	0.0246 (3)	0.0252 (3)	0.0248 (3)	−0.0050 (2)	0.0050 (2)	0.0016 (2)
C9	0.0240 (3)	0.0273 (3)	0.0346 (3)	−0.0067 (2)	0.0072 (2)	0.0005 (2)
C10	0.0191 (2)	0.0302 (3)	0.0355 (3)	−0.0043 (2)	0.0017 (2)	−0.0033 (3)
C11	0.0210 (3)	0.0380 (4)	0.0271 (3)	−0.0042 (2)	−0.0023 (2)	0.0025 (3)

S1—C1	1.7067 (7)	N3—C11	1.3347 (9)
S1—C4	1.7133 (8)	N3—C7	1.3446 (9)
O1—C6	1.2274 (8)	C4—H4	0.953 (14)
C1—C2	1.3724 (9)	C5—H5	0.941 (12)
C1—H1	0.987 (13)	C6—C7	1.5052 (8)
N1—C5	1.2841 (8)	C7—C8	1.3873 (9)
N1—N2	1.3764 (7)	C8—C9	1.3944 (10)
N2—C6	1.3559 (8)	C8—H8	0.935 (12)
N2—H2	0.832 (14)	C9—C10	1.3838 (12)
C2—C3	1.4306 (9)	C9—H9	0.922 (14)
C2—C5	1.4523 (8)	C10—C11	1.3895 (11)
C3—C4	1.3655 (10)	C10—H10	0.944 (14)
C3—H3	0.963 (14)	C11—H11	1.029 (15)
H4···N1i	2.591 (14)	H5···O1ii	2.609 (12)
C1—S1—C4	92.11 (3)	C2—C5—H5	119.0 (8)
C2—C1—S1	111.98 (5)	O1—C6—N2	124.80 (6)
C2—C1—H1	127.7 (8)	O1—C6—C7	122.86 (6)
S1—C1—H1	120.3 (8)	N2—C6—C7	112.34 (5)
C5—N1—N2	114.13 (5)	N3—C7—C8	123.49 (6)
C6—N2—N1	120.83 (5)	N3—C7—C6	116.28 (5)
C6—N2—H2	115.1 (9)	C8—C7—C6	120.23 (6)
N1—N2—H2	123.7 (9)	C7—C8—C9	118.31 (7)
C1—C2—C3	111.77 (6)	C7—C8—H8	118.7 (7)
C1—C2—C5	122.07 (6)	C9—C8—H8	123.0 (7)
C3—C2—C5	126.15 (6)	C10—C9—C8	118.74 (7)
C4—C3—C2	112.51 (6)	C10—C9—H9	119.4 (8)
C4—C3—H3	122.5 (8)	C8—C9—H9	121.8 (8)
C2—C3—H3	124.9 (8)	C9—C10—C11	118.70 (7)
C11—N3—C7	117.26 (6)	C9—C10—H10	120.8 (8)
C3—C4—S1	111.64 (5)	C11—C10—H10	120.5 (8)
C3—C4—H4	128.8 (8)	N3—C11—C10	123.50 (7)
S1—C4—H4	119.6 (8)	N3—C11—H11	113.8 (9)
N1—C5—C2	120.94 (6)	C10—C11—H11	122.7 (8)
N1—C5—H5	120.0 (8)
C4—S1—C1—C2	−0.15 (6)	C11—N3—C7—C8	0.86 (11)
C5—N1—N2—C6	−178.74 (6)	C11—N3—C7—C6	−179.13 (7)
S1—C1—C2—C3	0.21 (8)	O1—C6—C7—N3	−177.94 (7)
S1—C1—C2—C5	−178.92 (5)	N2—C6—C7—N3	1.78 (8)
C1—C2—C3—C4	−0.17 (9)	O1—C6—C7—C8	2.06 (10)
C5—C2—C3—C4	178.92 (7)	N2—C6—C7—C8	−178.21 (6)
C2—C3—C4—S1	0.05 (8)	N3—C7—C8—C9	−0.69 (11)
C1—S1—C4—C3	0.05 (6)	C6—C7—C8—C9	179.30 (6)
N2—N1—C5—C2	−178.20 (6)	C7—C8—C9—C10	0.02 (11)
C1—C2—C5—N1	−179.36 (6)	C8—C9—C10—C11	0.42 (12)
C3—C2—C5—N1	1.64 (11)	C7—N3—C11—C10	−0.38 (13)
N1—N2—C6—O1	3.95 (11)	C9—C10—C11—N3	−0.25 (13)
N1—N2—C6—C7	−175.76 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ii	0.83 (1)	2.38 (1)	3.0717 (8)	140 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.83 (1)	2.38 (1)	3.0717 (8)	140 (1)

Symmetry code: (i) .