N'-[(5-Methyl-2-fur-yl)methyl-ene]thio-phene-2-carbohydrazide.

In the title compound, C(11)H(10)N(2)O(2)S, the dihedral angle between the five-membered aromatic rings is 10.24 (12)°. In the crystal structure, mol-ecules are linked by bifurcated N-H⋯(O,N) hydrogen bonds, generating [001] chains.

Related literature

For related structures, see: Jiang (2010a ▶,b ▶).

Experimental

Crystal data

C11H10N2O2S

M = 234.27

Tetragonal,

a = 8.8037 (12) Å

c = 14.670 (3) Å

V = 1137.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.25 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD diffractometer

10087 measured reflections

2597 independent reflections

2073 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.087

S = 0.96

2597 reflections

145 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 1241 Friedel pairs

Flack parameter: −0.11 (8)

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010810/hb5367sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010810/hb5367Isup2.hkl

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

C11H10N2O2S	Dx = 1.369 Mg m−3
Mr = 234.27	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 2073 reflections
Hall symbol: P 4cw	θ = 3.3–27.5°
a = 8.8037 (12) Å	µ = 0.27 mm−1
c = 14.670 (3) Å	T = 293 K
V = 1137.0 (3) Å3	Block, colorless
Z = 4	0.25 × 0.20 × 0.19 mm
F(000) = 488

Bruker SMART CCD diffractometer	2073 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
graphite	θmax = 27.5°, θmin = 3.3°
ω scans	h = −11→11
10087 measured reflections	k = −11→11
2597 independent reflections	l = −19→19

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0486P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
2597 reflections	Δρmax = 0.23 e Å−3
145 parameters	Δρmin = −0.14 e Å−3
1 restraint	Absolute structure: Flack (1983), 1241 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.11 (8)

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.

	x	y	z	Uiso*/Ueq
S1	0.12336 (7)	0.93062 (7)	0.06580 (4)	0.06358 (19)
N1	0.44476 (18)	0.45913 (18)	0.09498 (10)	0.0431 (4)
O2	0.51869 (17)	0.17921 (15)	0.03236 (10)	0.0504 (4)
N2	0.40630 (18)	0.59910 (17)	0.12954 (10)	0.0428 (4)
H2A	0.4438	0.6313	0.1801	0.051*
C7	0.3074 (2)	0.6842 (2)	0.08110 (12)	0.0403 (4)
O1	0.25704 (18)	0.64188 (17)	0.00679 (10)	0.0630 (4)
C8	0.2645 (2)	0.8314 (2)	0.12060 (13)	0.0407 (4)
C5	0.5748 (2)	0.2280 (2)	0.11433 (13)	0.0482 (5)
C6	0.5305 (2)	0.3756 (2)	0.14463 (14)	0.0477 (5)
H6A	0.5641	0.4113	0.2008	0.057*
C9	0.3203 (2)	0.9110 (2)	0.19201 (13)	0.0477 (4)
H9A	0.3977	0.8758	0.2296	0.057*
C11	0.1410 (3)	1.0764 (2)	0.14106 (17)	0.0620 (6)
H11A	0.0817	1.1638	0.1392	0.074*
C4	0.6643 (3)	0.1185 (3)	0.15086 (18)	0.0607 (6)
H4A	0.7162	0.1232	0.2060	0.073*
C2	0.5746 (2)	0.0350 (2)	0.01820 (16)	0.0545 (5)
C3	0.6633 (3)	−0.0049 (3)	0.08834 (18)	0.0658 (7)
H3A	0.7148	−0.0965	0.0950	0.079*
C10	0.2494 (3)	1.0520 (2)	0.20326 (15)	0.0561 (5)
H10A	0.2747	1.1209	0.2488	0.067*
C1	0.5204 (3)	−0.0399 (3)	−0.06593 (18)	0.0742 (7)
H1B	0.5641	−0.1396	−0.0703	0.111*
H1C	0.5501	0.0192	−0.1179	0.111*
H1D	0.4117	−0.0481	−0.0642	0.111*

	U11	U22	U33	U12	U13	U23
S1	0.0735 (4)	0.0617 (3)	0.0555 (3)	0.0211 (3)	−0.0203 (3)	−0.0078 (3)
N1	0.0509 (9)	0.0432 (9)	0.0352 (8)	0.0052 (7)	0.0015 (6)	−0.0014 (6)
O2	0.0607 (9)	0.0452 (8)	0.0451 (8)	0.0124 (6)	0.0076 (6)	0.0052 (6)
N2	0.0528 (9)	0.0439 (8)	0.0316 (8)	0.0086 (6)	−0.0065 (7)	−0.0071 (6)
C7	0.0423 (10)	0.0458 (10)	0.0328 (10)	0.0000 (7)	−0.0028 (7)	−0.0029 (7)
O1	0.0864 (11)	0.0568 (9)	0.0458 (8)	0.0139 (8)	−0.0277 (8)	−0.0164 (7)
C8	0.0430 (10)	0.0447 (10)	0.0344 (9)	0.0018 (8)	−0.0003 (7)	−0.0019 (8)
C5	0.0488 (11)	0.0557 (12)	0.0401 (11)	0.0075 (9)	0.0064 (8)	0.0099 (9)
C6	0.0494 (11)	0.0554 (12)	0.0384 (10)	0.0056 (9)	0.0010 (8)	0.0014 (8)
C9	0.0505 (11)	0.0524 (11)	0.0402 (10)	0.0018 (9)	−0.0021 (8)	−0.0080 (8)
C11	0.0805 (16)	0.0496 (13)	0.0559 (14)	0.0165 (11)	0.0038 (12)	−0.0033 (10)
C4	0.0579 (13)	0.0622 (14)	0.0622 (14)	0.0138 (10)	−0.0010 (11)	0.0177 (11)
C2	0.0635 (13)	0.0409 (11)	0.0591 (14)	0.0078 (9)	0.0238 (11)	0.0076 (9)
C3	0.0685 (14)	0.0488 (13)	0.0800 (18)	0.0203 (11)	0.0183 (12)	0.0207 (12)
C10	0.0690 (14)	0.0488 (12)	0.0506 (13)	−0.0005 (10)	0.0065 (11)	−0.0127 (9)
C1	0.0939 (19)	0.0570 (14)	0.0716 (18)	0.0044 (13)	0.0229 (14)	−0.0038 (12)

S1—C11	1.700 (2)	C9—C10	1.399 (3)
S1—C8	1.7187 (19)	C9—H9A	0.9300
N1—C6	1.281 (3)	C11—C10	1.338 (3)
N1—N2	1.375 (2)	C11—H11A	0.9300
O2—C5	1.369 (2)	C4—C3	1.422 (4)
O2—C2	1.377 (2)	C4—H4A	0.9300
N2—C7	1.350 (2)	C2—C3	1.339 (3)
N2—H2A	0.8600	C2—C1	1.479 (3)
C7—O1	1.234 (2)	C3—H3A	0.9300
C7—C8	1.469 (2)	C10—H10A	0.9300
C8—C9	1.353 (3)	C1—H1B	0.9600
C5—C4	1.356 (3)	C1—H1C	0.9600
C5—C6	1.428 (3)	C1—H1D	0.9600
C6—H6A	0.9300
C11—S1—C8	90.80 (11)	C10—C11—S1	112.76 (17)
C6—N1—N2	116.74 (16)	C10—C11—H11A	123.6
C5—O2—C2	107.03 (16)	S1—C11—H11A	123.6
C7—N2—N1	117.51 (15)	C5—C4—C3	106.5 (2)
C7—N2—H2A	121.2	C5—C4—H4A	126.7
N1—N2—H2A	121.2	C3—C4—H4A	126.7
O1—C7—N2	121.93 (17)	C3—C2—O2	109.6 (2)
O1—C7—C8	121.47 (16)	C3—C2—C1	135.5 (2)
N2—C7—C8	116.59 (15)	O2—C2—C1	114.9 (2)
C9—C8—C7	132.01 (18)	C2—C3—C4	107.37 (19)
C9—C8—S1	111.17 (15)	C2—C3—H3A	126.3
C7—C8—S1	116.74 (13)	C4—C3—H3A	126.3
C4—C5—O2	109.5 (2)	C11—C10—C9	112.36 (19)
C4—C5—C6	133.1 (2)	C11—C10—H10A	123.8
O2—C5—C6	117.43 (17)	C9—C10—H10A	123.8
N1—C6—C5	120.43 (19)	C2—C1—H1B	109.5
N1—C6—H6A	119.8	C2—C1—H1C	109.5
C5—C6—H6A	119.8	H1B—C1—H1C	109.5
C8—C9—C10	112.89 (19)	C2—C1—H1D	109.5
C8—C9—H9A	123.6	H1B—C1—H1D	109.5
C10—C9—H9A	123.6	H1C—C1—H1D	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.86	2.30	3.064 (2)	149
N2—H2A···N1i	0.86	2.51	3.218 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.86	2.30	3.064 (2)	149
N2—H2A⋯N1i	0.86	2.51	3.218 (2)	140

Symmetry code: (i) .