N′-[(5-Methyl-2-fur­yl)methyl­ene]thio­phene-2-carbohydrazide

Jiang, J.-H.

doi:10.1107/S1600536810010810

organic compounds

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Volume 66| Part 4| April 2010| Page o924

doi:10.1107/S1600536810010810

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N′-[(5-Methyl-2-furyl)methylene]thiophene-2-carbohydrazide

Jin-He Jiang ^a ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: weifangjjh@126.com

(Received 19 March 2010; accepted 23 March 2010; online 27 March 2010)

In the title compound, C₁₁H₁₀N₂O₂S, the dihedral angle between the five-membered aromatic rings is 10.24 (12)°. In the crystal structure, molecules 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_r = 234.27
Tetragonal, P 4₃
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.087
S = 0.96
2597 reflections
145 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ), 1241 Friedel pairs
Flack parameter: −0.11 (8)

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) $[y, -x+1, z+{\script{1\over 4}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

As part of our ongoing studies of Schiff bases (Jiang, 2010a,b), we have synthesized the title compound (I), and describe its structure here, which occurs in the unusual enantiomorphous space group of P4₃.

The molcular structure of (I) is shown in Fig. 1. In the crystal, the molecules are linked by bifurcated N—H···(O,N) hydrogen bonds (Table 1).

Related literature top

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

Experimental top

A mixture of thiophene-2-carbohydrazide (0.05 mol) and 5-methylfuran-2-carbaldehyde (0.05 mol) was stirred in refluxing ethanol (10 ml) for 4 h to afford the title compound (0.082 mol, yield 82%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (I) showing 30% probability displacement ellipsoids.

N'-[(5-Methyl-2-furyl)methylene]thiophene-2-carbohydrazide top

Crystal data top

C₁₁H₁₀N₂O₂S	D_x = 1.369 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0486P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
2597 reflections	Δρ_max = 0.23 e Å⁻³
145 parameters	Δρ_min = −0.14 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1241 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.11 (8)

Crystal data top

C₁₁H₁₀N₂O₂S	Z = 4
M_r = 234.27	Mo Kα radiation
Tetragonal, P4₃	µ = 0.27 mm⁻¹
a = 8.8037 (12) Å	T = 293 K
c = 14.670 (3) Å	0.25 × 0.20 × 0.19 mm
V = 1137.0 (3) Å³

Data collection top

Bruker SMART CCD diffractometer	2073 reflections with I > 2σ(I)
10087 measured reflections	R_int = 0.044
2597 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.087	Δρ_max = 0.23 e Å⁻³
S = 0.96	Δρ_min = −0.14 e Å⁻³
2597 reflections	Absolute structure: Flack (1983), 1241 Friedel pairs
145 parameters	Absolute structure parameter: −0.11 (8)
1 restraint

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 > 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) y, −x+1, z+1/4.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀N₂O₂S
M_r	234.27
Crystal system, space group	Tetragonal, P4₃
Temperature (K)	293
a, c (Å)	8.8037 (12), 14.670 (3)
V (Å³)	1137.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.25 × 0.20 × 0.19

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10087, 2597, 2073
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.087, 0.96
No. of reflections	2597
No. of parameters	145
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.14
Absolute structure	Flack (1983), 1241 Friedel pairs
Absolute structure parameter	−0.11 (8)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
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) y, −x+1, z+1/4.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jiang, J.-H. (2010a). Acta Cryst. E66, o922. Web of Science CrossRef IUCr Journals Google Scholar
Jiang, J.-H. (2010b). Acta Cryst. E66, o923. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o924

doi:10.1107/S1600536810010810

Open

access