Ethyl 2-(3-phenyl-thio-ureido)-5,6-di-hydro-4H-cyclo-penta-[b]thio-phene-3-carboxyl-ate.

In the title compound, C(17)H(18)N(2)O(2)S(2), the angle between the mean plane defined by the atoms of the 5,6-dihydro-4H-cyclo-penta-[b]thio-phene moiety (r.m.s. deviation = 0.19 Å) and the phenyl ring is 72.8°(2). The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O inter-action, which generates an S(6) ring motif. In the crystal, pairs of N-H⋯S hydrogen bonds link the mol-ecules to form inversion dimers with an R(2) (2)(8) ring motif.

Related literature

For background to 2-amino­thio­phene derivatives, see: Puterová et al. (2010 ▶). For the biological activity of 2-ureido- and 2-thio­ureido-thio­phene-3-carboxyl­ate derivatives, see: Arhin et al. (2006 ▶); Saeed et al. (2010 ▶). For the synthesis of 2-amino­thio­phenes, see: Gewald et al. (1966 ▶). For a related structure, see: Larson & Simonsen (1988 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H18N2O2S2

M = 346.45

Triclinic,

a = 5.0755 (2) Å

b = 12.5088 (6) Å

c = 13.3304 (5) Å

α = 90.562 (3)°

β = 95.711 (3)°

γ = 94.378 (2)°

V = 839.61 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 295 K

0.32 × 0.17 × 0.11 mm

Data collection

Nonius KappaCCD diffractometer

9172 measured reflections

3876 independent reflections

2727 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.129

S = 1.04

3876 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.25 e Å−3

Data collection: COLLECT (Nonius, 1997 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029893/lr2068sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029893/lr2068Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029893/lr2068Isup3.cml

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

C17H18N2O2S2	Z = 2
Mr = 346.45	F(000) = 364
Triclinic, P1	Dx = 1.370 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0755 (2) Å	Cell parameters from 5829 reflections
b = 12.5088 (6) Å	θ = 2.6–27.5°
c = 13.3304 (5) Å	µ = 0.33 mm−1
α = 90.562 (3)°	T = 295 K
β = 95.711 (3)°	Prism, yellow
γ = 94.378 (2)°	0.32 × 0.17 × 0.11 mm
V = 839.61 (6) Å3

Nonius KappaCCD diffractometer	2727 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.041
Horizonally mounted graphite crystal monochromator	θmax = 27.5°, θmin = 3.1°
Detector resolution: 9 pixels mm-1	h = −5→6
CCD rotation images,thick slices scans	k = −16→16
9172 measured reflections	l = −17→17
3876 independent reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.2145P] where P = (Fo2 + 2Fc2)/3
3876 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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	0.55314 (12)	0.02072 (4)	0.67471 (4)	0.05884 (19)
S2	0.35795 (11)	0.09492 (4)	0.87171 (4)	0.05360 (17)
O2	−0.2636 (3)	0.37540 (12)	0.83065 (10)	0.0528 (4)
O1	−0.1299 (3)	0.33086 (13)	0.68141 (10)	0.0607 (4)
N1	0.2196 (3)	0.17647 (13)	0.68280 (11)	0.0469 (4)
H1	0.1318	0.2229	0.6494	0.056*
N2	0.3310 (4)	0.13297 (14)	0.52705 (13)	0.0582 (5)
H2	0.3999	0.0896	0.4885	0.070*
C1	0.1968 (4)	0.17638 (15)	0.78532 (14)	0.0423 (4)
C9	0.1970 (4)	0.21777 (16)	0.47921 (14)	0.0487 (5)
C10	0.3005 (4)	0.32279 (17)	0.49491 (15)	0.0536 (5)
H10	0.4551	0.3384	0.5377	0.064*
C2	0.0363 (4)	0.24425 (15)	0.83011 (13)	0.0425 (4)
C4	−0.0737 (4)	0.2761 (2)	1.02319 (15)	0.0566 (5)
H4A	−0.2659	0.2660	1.0134	0.068*
H4B	−0.0208	0.3521	1.0313	0.068*
C8	0.3604 (4)	0.11405 (15)	0.62679 (15)	0.0466 (4)
C6	0.2245 (5)	0.1327 (2)	1.07959 (16)	0.0670 (6)
H6A	0.4038	0.1475	1.1117	0.080*
H6B	0.1620	0.0597	1.0934	0.080*
C11	0.1727 (5)	0.40396 (19)	0.44669 (17)	0.0635 (6)
H11	0.2408	0.4748	0.4573	0.076*
C15	−0.1225 (4)	0.31881 (16)	0.77266 (14)	0.0459 (4)
C3	0.0489 (4)	0.22821 (16)	0.93666 (14)	0.0468 (4)
C16	−0.4291 (5)	0.45183 (19)	0.77988 (16)	0.0573 (5)
H16A	−0.5613	0.4152	0.7313	0.069*
H16B	−0.3218	0.5036	0.7446	0.069*
C7	0.2103 (4)	0.15241 (18)	0.96808 (15)	0.0533 (5)
C13	−0.1550 (5)	0.2766 (3)	0.36669 (18)	0.0747 (7)
H13	−0.3081	0.2614	0.3229	0.090*
C14	−0.0298 (5)	0.1938 (2)	0.41490 (17)	0.0635 (6)
H14	−0.0979	0.1230	0.4040	0.076*
C12	−0.0536 (5)	0.3809 (2)	0.38337 (18)	0.0704 (7)
H12	−0.1395	0.4362	0.3514	0.084*
C17	−0.5609 (5)	0.5069 (2)	0.85914 (18)	0.0677 (6)
H17A	−0.6727	0.5584	0.8282	0.102*
H17B	−0.4280	0.5428	0.9067	0.102*
H17C	−0.6665	0.4548	0.8934	0.102*
C5	0.0370 (7)	0.2135 (3)	1.11409 (18)	0.0839 (8)
H5A	−0.1079	0.1758	1.1448	0.101*
H5B	0.1328	0.2628	1.1640	0.101*

	U11	U22	U33	U12	U13	U23
S1	0.0707 (4)	0.0530 (3)	0.0557 (3)	0.0257 (3)	0.0055 (3)	−0.0062 (2)
S2	0.0602 (3)	0.0550 (3)	0.0490 (3)	0.0214 (2)	0.0087 (2)	0.0070 (2)
O2	0.0585 (8)	0.0617 (9)	0.0428 (7)	0.0272 (7)	0.0098 (6)	0.0028 (6)
O1	0.0755 (10)	0.0716 (10)	0.0404 (7)	0.0340 (8)	0.0104 (7)	0.0052 (7)
N1	0.0571 (10)	0.0472 (9)	0.0395 (8)	0.0183 (7)	0.0090 (7)	−0.0002 (7)
N2	0.0839 (13)	0.0522 (10)	0.0443 (9)	0.0294 (9)	0.0165 (9)	−0.0042 (7)
C1	0.0445 (10)	0.0414 (9)	0.0419 (9)	0.0075 (8)	0.0061 (8)	0.0001 (7)
C9	0.0612 (12)	0.0511 (11)	0.0376 (9)	0.0169 (9)	0.0151 (9)	−0.0015 (8)
C10	0.0628 (12)	0.0535 (12)	0.0462 (11)	0.0113 (10)	0.0092 (9)	−0.0018 (9)
C2	0.0430 (9)	0.0469 (10)	0.0388 (9)	0.0080 (8)	0.0062 (7)	0.0016 (7)
C4	0.0593 (12)	0.0712 (14)	0.0419 (10)	0.0127 (11)	0.0123 (9)	−0.0014 (9)
C8	0.0542 (11)	0.0401 (10)	0.0469 (10)	0.0080 (8)	0.0100 (9)	−0.0062 (8)
C6	0.0708 (14)	0.0866 (17)	0.0461 (11)	0.0164 (13)	0.0095 (11)	0.0156 (11)
C11	0.0840 (16)	0.0557 (13)	0.0551 (12)	0.0173 (12)	0.0192 (12)	0.0064 (10)
C15	0.0472 (10)	0.0495 (11)	0.0431 (10)	0.0119 (8)	0.0094 (8)	−0.0015 (8)
C3	0.0480 (10)	0.0530 (11)	0.0401 (10)	0.0066 (9)	0.0062 (8)	0.0001 (8)
C16	0.0640 (13)	0.0641 (13)	0.0481 (11)	0.0295 (11)	0.0071 (10)	0.0053 (9)
C7	0.0558 (12)	0.0611 (13)	0.0453 (10)	0.0139 (10)	0.0089 (9)	0.0065 (9)
C13	0.0649 (15)	0.108 (2)	0.0526 (13)	0.0221 (15)	0.0002 (11)	−0.0051 (13)
C14	0.0652 (14)	0.0703 (15)	0.0556 (13)	0.0062 (12)	0.0090 (11)	−0.0085 (11)
C12	0.0844 (17)	0.0814 (18)	0.0520 (13)	0.0384 (14)	0.0141 (12)	0.0134 (12)
C17	0.0762 (15)	0.0731 (15)	0.0578 (13)	0.0338 (13)	0.0067 (11)	−0.0080 (11)
C5	0.109 (2)	0.103 (2)	0.0471 (13)	0.0402 (18)	0.0182 (14)	0.0121 (13)

S1—C8	1.671 (2)	C4—H4B	0.9700
S2—C7	1.728 (2)	C6—C7	1.505 (3)
S2—C1	1.7310 (19)	C6—C5	1.537 (4)
O2—C15	1.337 (2)	C6—H6A	0.9700
O2—C16	1.449 (2)	C6—H6B	0.9700
O1—C15	1.224 (2)	C11—C12	1.366 (4)
N1—C8	1.363 (2)	C11—H11	0.9300
N1—C1	1.383 (2)	C3—C7	1.343 (3)
N1—H1	0.8600	C16—C17	1.495 (3)
N2—C8	1.348 (3)	C16—H16A	0.9700
N2—C9	1.425 (3)	C16—H16B	0.9700
N2—H2	0.8600	C13—C12	1.374 (4)
C1—C2	1.391 (3)	C13—C14	1.386 (4)
C9—C14	1.377 (3)	C13—H13	0.9300
C9—C10	1.383 (3)	C14—H14	0.9300
C10—C11	1.377 (3)	C12—H12	0.9300
C10—H10	0.9300	C17—H17A	0.9600
C2—C3	1.432 (3)	C17—H17B	0.9600
C2—C15	1.453 (3)	C17—H17C	0.9600
C4—C3	1.504 (3)	C5—H5A	0.9700
C4—C5	1.532 (3)	C5—H5B	0.9700
C4—H4A	0.9700
C7—S2—C1	90.32 (9)	C10—C11—H11	119.9
C15—O2—C16	116.57 (15)	O1—C15—O2	122.23 (17)
C8—N1—C1	129.72 (17)	O1—C15—C2	125.21 (17)
C8—N1—H1	115.1	O2—C15—C2	112.56 (16)
C1—N1—H1	115.1	C7—C3—C2	112.96 (18)
C8—N2—C9	126.40 (16)	C7—C3—C4	111.40 (18)
C8—N2—H2	116.8	C2—C3—C4	135.63 (18)
C9—N2—H2	116.8	O2—C16—C17	107.08 (17)
N1—C1—C2	122.14 (17)	O2—C16—H16A	110.3
N1—C1—S2	125.40 (14)	C17—C16—H16A	110.3
C2—C1—S2	112.45 (14)	O2—C16—H16B	110.3
C14—C9—C10	120.6 (2)	C17—C16—H16B	110.3
C14—C9—N2	119.4 (2)	H16A—C16—H16B	108.6
C10—C9—N2	119.87 (19)	C3—C7—C6	114.13 (19)
C11—C10—C9	119.5 (2)	C3—C7—S2	113.40 (16)
C11—C10—H10	120.3	C6—C7—S2	132.46 (17)
C9—C10—H10	120.3	C12—C13—C14	120.2 (2)
C1—C2—C3	110.87 (17)	C12—C13—H13	119.9
C1—C2—C15	122.59 (16)	C14—C13—H13	119.9
C3—C2—C15	126.54 (17)	C9—C14—C13	119.1 (2)
C3—C4—C5	103.25 (18)	C9—C14—H14	120.5
C3—C4—H4A	111.1	C13—C14—H14	120.5
C5—C4—H4A	111.1	C11—C12—C13	120.4 (2)
C3—C4—H4B	111.1	C11—C12—H12	119.8
C5—C4—H4B	111.1	C13—C12—H12	119.8
H4A—C4—H4B	109.1	C16—C17—H17A	109.5
N2—C8—N1	114.24 (17)	C16—C17—H17B	109.5
N2—C8—S1	121.58 (14)	H17A—C17—H17B	109.5
N1—C8—S1	124.18 (15)	C16—C17—H17C	109.5
C7—C6—C5	101.64 (19)	H17A—C17—H17C	109.5
C7—C6—H6A	111.4	H17B—C17—H17C	109.5
C5—C6—H6A	111.4	C4—C5—C6	109.55 (19)
C7—C6—H6B	111.4	C4—C5—H5A	109.8
C5—C6—H6B	111.4	C6—C5—H5A	109.8
H6A—C6—H6B	109.3	C4—C5—H5B	109.8
C12—C11—C10	120.3 (2)	C6—C5—H5B	109.8
C12—C11—H11	119.9	H5A—C5—H5B	108.2

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.86	2.61	3.415 (2)	157
N1—H1···O1	0.86	2.04	2.719 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.86	2.61	3.415 (2)	157
N1—H1⋯O1	0.86	2.04	2.719 (2)	136

Symmetry code: (i) .