(E)-2-Methyl-5-(thiophen-2-ylmethyl-idene)cyclopentan-1-one.

The exocyclic C=C double-bond in the title compound, C(11)H(12)OS, has an E configuration. The methyl-bearing C atom in the cyclo-pentane ring is disordered over two positions with a site-occupation factor of 0.899 (8) for the major occupied site.

Related literature

For the synthesis of 2-(2-thienyl­idene)cyclo­pentanone, see: Austin et al. (2007 ▶); Tsukerman et al. (1964 ▶).

Experimental

Crystal data

C11H12OS

M = 192.27

Monoclinic,

a = 12.0667 (5) Å

b = 11.0576 (4) Å

c = 7.3003 (3) Å

β = 100.469 (4)°

V = 957.85 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.25 × 0.15 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.931, T max = 0.971

4842 measured reflections

2131 independent reflections

1817 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.104

S = 0.99

2131 reflections

122 parameters

9 restraints

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033708/bt5619sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033708/bt5619Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033708/bt5619Isup3.cml

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

C11H12OS	F(000) = 408
Mr = 192.27	Dx = 1.333 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2335 reflections
a = 12.0667 (5) Å	θ = 2.5–29.2°
b = 11.0576 (4) Å	µ = 0.29 mm−1
c = 7.3003 (3) Å	T = 100 K
β = 100.469 (4)°	Prism, light yellow
V = 957.85 (7) Å3	0.25 × 0.15 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with Atlas detector	2131 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1817 reflections with I > 2σ(I)
mirror	Rint = 0.028
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −12→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→14
Tmin = 0.931, Tmax = 0.971	l = −9→9
4842 measured 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0433P)2 + 0.8843P] where P = (Fo2 + 2Fc2)/3
2131 reflections	(Δ/σ)max = 0.001
122 parameters	Δρmax = 0.57 e Å−3
9 restraints	Δρmin = −0.31 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.46249 (4)	0.03090 (4)	0.23692 (6)	0.01813 (15)
O1	0.83453 (11)	0.32223 (13)	0.2085 (2)	0.0294 (4)
C1	0.32149 (16)	0.06255 (19)	0.1851 (3)	0.0207 (4)
H1	0.2639	0.0080	0.2046	0.025*
C2	0.30192 (15)	0.17578 (18)	0.1124 (3)	0.0207 (4)
H2	0.2287	0.2089	0.0749	0.025*
C3	0.40176 (14)	0.23853 (17)	0.0985 (2)	0.0172 (4)
H3	0.4028	0.3183	0.0504	0.021*
C4	0.49807 (15)	0.17173 (16)	0.1624 (2)	0.0162 (4)
C5	0.61209 (15)	0.21367 (17)	0.1727 (3)	0.0170 (4)
H5	0.6195	0.2946	0.1330	0.020*
C6	0.70943 (15)	0.15444 (17)	0.2306 (3)	0.0181 (4)
C7	0.81999 (16)	0.21558 (19)	0.2394 (3)	0.0245 (4)
C8	0.91401 (17)	0.1245 (2)	0.3085 (3)	0.0251 (7)	0.899 (8)
H8	0.9358	0.1353	0.4463	0.030*	0.899 (8)
C8'	0.8943 (7)	0.1127 (8)	0.187 (2)	0.0251 (7)	0.10
H8'	0.8730	0.1011	0.0492	0.030*	0.101 (8)
C9	0.85457 (16)	0.00382 (19)	0.2756 (3)	0.0286 (5)
H9A	0.8895	−0.0559	0.3697	0.034*	0.899 (8)
H9B	0.8595	−0.0275	0.1503	0.034*	0.899 (8)
H9C	0.9009	−0.0091	0.4006	0.034*	0.101 (8)
H9D	0.8609	−0.0687	0.1988	0.034*	0.101 (8)
C10	0.73056 (16)	0.02545 (17)	0.2918 (3)	0.0197 (4)
H10A	0.6799	−0.0303	0.2097	0.024*
H10B	0.7193	0.0143	0.4217	0.024*
C11	1.01808 (16)	0.1430 (2)	0.2272 (3)	0.0321 (5)
H11A	1.0501	0.2228	0.2636	0.048*	0.899 (8)
H11B	0.9989	0.1381	0.0911	0.048*	0.899 (8)
H11C	1.0734	0.0802	0.2738	0.048*	0.899 (8)
H11D	1.0276	0.2304	0.2461	0.048*	0.101 (8)
H11E	1.0528	0.1179	0.1219	0.048*	0.101 (8)
H11F	1.0544	0.1004	0.3400	0.048*	0.101 (8)

	U11	U22	U33	U12	U13	U23
S1	0.0192 (2)	0.0158 (2)	0.0198 (3)	−0.00094 (17)	0.00467 (18)	0.00170 (18)
O1	0.0229 (7)	0.0190 (7)	0.0480 (10)	−0.0013 (6)	0.0112 (7)	0.0039 (7)
C1	0.0185 (9)	0.0236 (10)	0.0199 (9)	−0.0038 (8)	0.0035 (7)	−0.0029 (8)
C2	0.0170 (9)	0.0231 (10)	0.0210 (10)	0.0008 (8)	0.0007 (7)	−0.0021 (8)
C3	0.0192 (9)	0.0165 (9)	0.0151 (9)	−0.0006 (7)	0.0012 (7)	−0.0008 (7)
C4	0.0197 (9)	0.0138 (9)	0.0158 (9)	0.0000 (7)	0.0047 (7)	0.0003 (7)
C5	0.0200 (9)	0.0129 (9)	0.0196 (9)	−0.0007 (7)	0.0081 (7)	0.0008 (7)
C6	0.0191 (9)	0.0159 (9)	0.0205 (9)	−0.0012 (7)	0.0069 (7)	−0.0027 (8)
C7	0.0201 (9)	0.0197 (10)	0.0361 (12)	0.0016 (8)	0.0114 (8)	0.0011 (9)
C8	0.0195 (11)	0.0234 (12)	0.0330 (14)	0.0011 (9)	0.0060 (9)	0.0006 (10)
C8'	0.0195 (11)	0.0234 (12)	0.0330 (14)	0.0011 (9)	0.0060 (9)	0.0006 (10)
C9	0.0195 (9)	0.0220 (10)	0.0413 (13)	0.0022 (8)	−0.0023 (9)	0.0031 (10)
C10	0.0215 (9)	0.0154 (9)	0.0222 (10)	0.0007 (7)	0.0044 (7)	0.0010 (8)
C11	0.0176 (9)	0.0309 (12)	0.0485 (14)	0.0040 (9)	0.0074 (9)	0.0030 (11)

S1—C1	1.7107 (19)	C8—H8	1.0000
S1—C4	1.7293 (18)	C8'—C9	1.487 (9)
O1—C7	1.219 (2)	C8'—C11	1.506 (9)
C1—C2	1.364 (3)	C8'—H8'	1.0000
C1—H1	0.9500	C9—C10	1.541 (3)
C2—C3	1.410 (3)	C9—H9A	0.9900
C2—H2	0.9500	C9—H9B	0.9900
C3—C4	1.384 (3)	C9—H9C	0.9900
C3—H3	0.9500	C9—H9D	0.9900
C4—C5	1.441 (2)	C10—H10A	0.9900
C5—C6	1.344 (3)	C10—H10B	0.9900
C5—H5	0.9500	C11—H11A	0.9800
C6—C7	1.487 (3)	C11—H11B	0.9800
C6—C10	1.503 (3)	C11—H11C	0.9800
C7—C8	1.533 (3)	C11—H11D	0.9800
C7—C8'	1.539 (9)	C11—H11E	0.9800
C8—C11	1.497 (3)	C11—H11F	0.9800
C8—C9	1.513 (3)
C1—S1—C4	92.29 (9)	C7—C8'—H8'	106.8
C2—C1—S1	111.64 (14)	C8'—C9—C10	107.6 (3)
C2—C1—H1	124.2	C8—C9—C10	106.86 (17)
S1—C1—H1	124.2	C8—C9—H9A	110.3
C1—C2—C3	112.96 (17)	C10—C9—H9A	110.3
C1—C2—H2	123.5	C8'—C9—H9B	78.6
C3—C2—H2	123.5	C8—C9—H9B	110.3
C4—C3—C2	112.91 (17)	C10—C9—H9B	110.3
C4—C3—H3	123.5	H9A—C9—H9B	108.6
C2—C3—H3	123.5	C8'—C9—H9C	110.2
C3—C4—C5	125.52 (17)	C10—C9—H9C	110.2
C3—C4—S1	110.19 (13)	C8'—C9—H9D	110.2
C5—C4—S1	124.24 (14)	C10—C9—H9D	110.2
C6—C5—C4	129.13 (17)	H9C—C9—H9D	108.5
C6—C5—H5	115.4	C6—C10—C9	103.84 (15)
C4—C5—H5	115.4	C6—C10—H10A	111.0
C5—C6—C7	121.20 (17)	C9—C10—H10A	111.0
C5—C6—C10	130.35 (17)	C6—C10—H10B	111.0
C7—C6—C10	108.45 (16)	C9—C10—H10B	111.0
O1—C7—C6	126.17 (18)	H10A—C10—H10B	109.0
O1—C7—C8	125.02 (18)	C8—C11—H11A	109.5
C6—C7—C8	108.67 (17)	C8—C11—H11B	109.5
O1—C7—C8'	124.0 (4)	H11A—C11—H11B	109.5
C6—C7—C8'	102.2 (4)	C8—C11—H11C	109.5
C11—C8—C9	117.7 (2)	C8'—C11—H11C	119.9
C11—C8—C7	113.82 (19)	H11A—C11—H11C	109.5
C9—C8—C7	103.08 (16)	H11B—C11—H11C	109.5
C11—C8—H8	107.2	C8'—C11—H11D	109.5
C9—C8—H8	107.2	H11B—C11—H11D	101.3
C7—C8—H8	107.2	C8'—C11—H11E	109.5
C9—C8'—C11	118.8 (8)	H11A—C11—H11E	105.3
C9—C8'—C7	104.0 (6)	H11D—C11—H11E	109.5
C11—C8'—C7	112.9 (7)	C8'—C11—H11F	109.5
C9—C8'—H8'	106.8	H11D—C11—H11F	109.5
C11—C8'—H8'	106.8	H11E—C11—H11F	109.5
C4—S1—C1—C2	0.45 (16)	O1—C7—C8'—C9	172.1 (4)
S1—C1—C2—C3	−0.2 (2)	C6—C7—C8'—C9	−36.9 (9)
C1—C2—C3—C4	−0.2 (2)	C8—C7—C8'—C9	68.5 (8)
C2—C3—C4—C5	−177.31 (17)	O1—C7—C8'—C11	42.1 (12)
C2—C3—C4—S1	0.5 (2)	C6—C7—C8'—C11	−167.0 (7)
C1—S1—C4—C3	−0.56 (15)	C8—C7—C8'—C11	−61.6 (8)
C1—S1—C4—C5	177.32 (16)	C11—C8'—C9—C8	59.1 (9)
C3—C4—C5—C6	−179.18 (19)	C7—C8'—C9—C8	−67.4 (8)
S1—C4—C5—C6	3.3 (3)	C11—C8'—C9—C10	153.4 (7)
C4—C5—C6—C7	−177.08 (18)	C7—C8'—C9—C10	27.0 (9)
C4—C5—C6—C10	3.9 (3)	C11—C8—C9—C8'	−58.8 (6)
C5—C6—C7—O1	4.8 (3)	C7—C8—C9—C8'	67.4 (6)
C10—C6—C7—O1	−176.0 (2)	C11—C8—C9—C10	−155.4 (2)
C5—C6—C7—C8	−179.48 (18)	C7—C8—C9—C10	−29.2 (2)
C10—C6—C7—C8	−0.3 (2)	C5—C6—C10—C9	161.5 (2)
C5—C6—C7—C8'	−145.3 (6)	C7—C6—C10—C9	−17.6 (2)
C10—C6—C7—C8'	33.9 (6)	C8'—C9—C10—C6	−6.5 (7)
O1—C7—C8—C11	−37.2 (3)	C8—C9—C10—C6	29.4 (2)
C6—C7—C8—C11	146.97 (19)	C9—C8—C11—C8'	57.6 (6)
C8'—C7—C8—C11	63.0 (6)	C7—C8—C11—C8'	−63.1 (6)
O1—C7—C8—C9	−165.9 (2)	C9—C8'—C11—C8	−60.2 (9)
C6—C7—C8—C9	18.3 (2)	C7—C8'—C11—C8	61.9 (8)
C8'—C7—C8—C9	−65.7 (5)