1-(4-Chloro­phenyl)-3-(2-thienyl)prop-2-en-1-one

The enone fragment, the thio­phene ring and the benzene ring of the title mol­ecule, C₁₃H₉ClOS, are all essentially individually planar. The thio­phene ring is disordered over two sites, corresponding to a rotation of approximately 180° about the single C—C bond to which it is attached. The crystal packing is stabilized by weak inter­molecular C—H...π inter­actions involving thio­phene rings and benzene rings, and mol­ecules are stacked along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• Disorder in main residue
• R factor = 0.031
• wR factor = 0.089
• Data-to-parameter ratio = 33.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT301_ALERT_3_C Main Residue  Disorder .........................      20.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  S1B     ..       3.46 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A    ..  CG1     ..       2.90 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A    ..  CG2     ..       2.90 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A    ..  CG3     ..       2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A   ..  CG3     ..       2.89 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

1-(4-Chlorophenyl)-3-(2-thienyl)prop-2-en-1-one

Crystal data

C13H9ClOS	Z = 2
Mr = 248.71	F(000) = 256
Triclinic, P1	Dx = 1.494 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7956 (1) Å	Cell parameters from 8665 reflections
b = 7.3397 (1) Å	θ = 1.6–37.5°
c = 13.3905 (2) Å	µ = 0.51 mm^−1
α = 78.634 (1)°	T = 100 K
β = 81.928 (1)°	Block, yellow
γ = 88.964 (1)°	0.56 × 0.54 × 0.23 mm
V = 552.87 (1) Å^3

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	5770 independent reflections
Radiation source: fine-focus sealed tube	5316 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 8.33 pixels mm^-1	θmax = 37.5°, θmin = 1.6°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
Tmin = 0.810, Tmax = 0.892	l = −22→22
28531 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0455P)^2 + 0.1565P] where P = (Fo^2 + 2Fc^2)/3
5770 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.96 e Å^−3
0 restraints	Δρmin = −0.86 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.60400 (3)	0.27687 (3)	0.462496 (13)	0.02085 (5)
O1	0.28076 (9)	0.71158 (9)	0.01951 (4)	0.01932 (10)
C1	0.73297 (11)	0.51495 (9)	0.16487 (5)	0.01417 (10)
H1A	0.8577	0.5266	0.1120	0.017*
C2	0.75767 (11)	0.41275 (9)	0.26219 (5)	0.01457 (10)
H2A	0.8968	0.3530	0.2743	0.017*
C3	0.57153 (11)	0.40139 (9)	0.34088 (5)	0.01395 (10)
C4	0.35991 (11)	0.48730 (9)	0.32491 (5)	0.01458 (10)
H4A	0.2378	0.4795	0.3787	0.017*
C5	0.33496 (11)	0.58483 (9)	0.22705 (5)	0.01363 (10)
H5A	0.1936	0.6406	0.2148	0.016*
C6	0.52080 (11)	0.60004 (9)	0.14654 (5)	0.01264 (9)
C7	0.47991 (11)	0.70026 (9)	0.04204 (5)	0.01372 (10)
C8	0.68235 (11)	0.78410 (9)	−0.03095 (5)	0.01502 (10)
H8A	0.8255	0.7927	−0.0082	0.018*
C9	0.65982 (11)	0.84822 (9)	−0.13066 (5)	0.01373 (10)
H9A	0.5172	0.8286	−0.1513	0.016*
C10	0.83865 (11)	0.94470 (9)	−0.20798 (5)	0.01370 (10)
S1A	1.0876 (2)	1.0284 (2)	−0.18189 (11)	0.01370 (16)	0.4802 (12)
C12A	1.0662 (17)	1.1045 (18)	−0.3684 (10)	0.0198 (11)	0.4802 (12)
H12A	1.1215	1.1597	−0.4360	0.024*	0.4802 (12)
C11A	1.1842 (11)	1.1039 (8)	−0.2865 (3)	0.0157 (6)	0.4802 (12)
H11A	1.3339	1.1547	−0.2993	0.019*	0.4802 (12)
C13A	0.80765 (5)	0.99226 (4)	−0.33091 (2)	0.01874 (7)	0.4802 (12)
H13A	0.6898	0.9664	−0.3668	0.022*	0.4802 (12)
S1B	0.80765 (5)	0.99226 (4)	−0.33091 (2)	0.01874 (7)	0.5198 (12)
C13B	1.0571 (9)	1.0142 (8)	−0.1938 (4)	0.0147 (5)	0.5198 (12)
H13B	1.1188	1.0008	−0.1323	0.018*	0.5198 (12)
C11B	1.0277 (15)	1.0939 (16)	−0.3719 (9)	0.0188 (9)	0.5198 (12)
H11B	1.0634	1.1386	−0.4423	0.023*	0.5198 (12)
C12B	1.1788 (11)	1.1230 (9)	−0.3080 (3)	0.0176 (6)	0.5198 (12)
H12C	1.3189	1.1892	−0.3248	0.021*	0.5198 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02433 (9)	0.02232 (8)	0.01409 (7)	0.00457 (6)	−0.00354 (5)	0.00100 (5)
O1	0.0135 (2)	0.0276 (3)	0.0160 (2)	−0.00159 (17)	−0.00344 (16)	−0.00098 (18)
C1	0.0122 (2)	0.0163 (2)	0.0140 (2)	0.00020 (18)	−0.00089 (17)	−0.00360 (19)
C2	0.0129 (2)	0.0154 (2)	0.0156 (2)	0.00131 (18)	−0.00237 (18)	−0.00325 (19)
C3	0.0154 (2)	0.0135 (2)	0.0129 (2)	0.00058 (18)	−0.00262 (18)	−0.00182 (18)
C4	0.0136 (2)	0.0159 (2)	0.0133 (2)	0.00029 (18)	−0.00030 (17)	−0.00173 (18)
C5	0.0119 (2)	0.0146 (2)	0.0139 (2)	0.00010 (17)	−0.00105 (17)	−0.00207 (18)
C6	0.0122 (2)	0.0135 (2)	0.0122 (2)	−0.00114 (17)	−0.00149 (16)	−0.00258 (17)
C7	0.0136 (2)	0.0153 (2)	0.0121 (2)	−0.00143 (18)	−0.00158 (17)	−0.00252 (18)
C8	0.0142 (2)	0.0173 (2)	0.0131 (2)	−0.00291 (19)	−0.00139 (18)	−0.00190 (19)
C9	0.0133 (2)	0.0138 (2)	0.0136 (2)	−0.00082 (18)	−0.00127 (17)	−0.00172 (18)
C10	0.0136 (2)	0.0129 (2)	0.0141 (2)	−0.00023 (17)	−0.00066 (17)	−0.00223 (18)
S1A	0.0122 (3)	0.0157 (2)	0.0134 (4)	−0.0004 (2)	−0.0035 (2)	−0.0021 (2)
C12A	0.023 (2)	0.0176 (11)	0.016 (2)	−0.0015 (15)	0.0023 (16)	−0.0004 (11)
C11A	0.0120 (7)	0.0159 (13)	0.0191 (16)	−0.0013 (8)	−0.0016 (12)	−0.0037 (12)
C13A	0.01665 (12)	0.01743 (12)	0.01990 (13)	−0.00056 (8)	0.00040 (8)	−0.00029 (9)
S1B	0.01665 (12)	0.01743 (12)	0.01990 (13)	−0.00056 (8)	0.00040 (8)	−0.00029 (9)
C13B	0.0139 (13)	0.0190 (11)	0.0115 (10)	0.0015 (8)	−0.0043 (7)	−0.0021 (7)
C11B	0.027 (3)	0.0180 (16)	0.0117 (8)	0.0029 (17)	−0.0033 (18)	−0.0023 (9)
C12B	0.0153 (8)	0.0172 (11)	0.0185 (15)	−0.0006 (7)	0.0014 (11)	−0.0016 (11)

Geometric parameters (Å, º)

Cl1—C3	1.7366 (7)	C9—C10	1.4436 (9)
O1—C7	1.2307 (8)	C9—H9A	0.9300
C1—C2	1.3945 (9)	C10—C13B	1.424 (4)
C1—C6	1.3996 (9)	C10—C13A	1.6486 (7)
C1—H1A	0.9300	C10—S1A	1.6852 (11)
C2—C3	1.3894 (9)	S1A—C11A	1.438 (5)
C2—H2A	0.9300	C12A—C11A	1.370 (12)
C3—C4	1.3929 (9)	C12A—C13A	1.687 (9)
C4—C5	1.3893 (9)	C12A—H12A	0.9300
C4—H4A	0.9300	C11A—H11A	0.9300
C5—C6	1.4020 (9)	C13A—H13A	0.9300
C5—H5A	0.9300	C13B—C12B	1.646 (7)
C6—C7	1.4955 (9)	C13B—H13B	0.9300
C7—C8	1.4756 (9)	C11B—C12B	1.354 (11)
C8—C9	1.3492 (9)	C11B—H11B	0.9300
C8—H8A	0.9300	C12B—H12C	0.9300
C2—C1—C6	120.11 (6)	C8—C9—H9A	117.3
C2—C1—H1A	119.9	C10—C9—H9A	117.3
C6—C1—H1A	119.9	C13B—C10—C9	128.1 (2)
C3—C2—C1	119.10 (6)	C13B—C10—C13A	110.0 (2)
C3—C2—H2A	120.4	C9—C10—C13A	121.83 (5)
C1—C2—H2A	120.4	C9—C10—S1A	124.09 (7)
C2—C3—C4	121.81 (6)	C13A—C10—S1A	114.01 (6)
C2—C3—Cl1	119.04 (5)	C11A—S1A—C10	96.9 (3)
C4—C3—Cl1	119.15 (5)	C11A—C12A—C13A	111.4 (8)
C5—C4—C3	118.67 (6)	C11A—C12A—H12A	124.3
C5—C4—H4A	120.7	C13A—C12A—H12A	124.3
C3—C4—H4A	120.7	C12A—C11A—S1A	123.1 (6)
C4—C5—C6	120.66 (6)	C12A—C11A—H11A	118.5
C4—C5—H5A	119.7	S1A—C11A—H11A	118.5
C6—C5—H5A	119.7	C10—C13A—C12A	94.4 (4)
C1—C6—C5	119.61 (6)	C10—C13A—H13A	132.8
C1—C6—C7	122.26 (6)	C12A—C13A—H13A	132.8
C5—C6—C7	118.07 (6)	C10—C13B—C12B	106.3 (3)
O1—C7—C8	122.03 (6)	C10—C13B—H13B	126.8
O1—C7—C6	119.68 (6)	C12B—C13B—H13B	126.8
C8—C7—C6	118.29 (6)	C12B—C11B—H11B	119.7
C9—C8—C7	120.00 (6)	C11B—C12B—C13B	103.9 (6)
C9—C8—H8A	120.0	C11B—C12B—H12C	128.0
C7—C8—H8A	120.0	C13B—C12B—H12C	128.0
C8—C9—C10	125.46 (6)
C6—C1—C2—C3	−1.84 (10)	C8—C9—C10—C13B	−9.6 (3)
C1—C2—C3—C4	0.84 (10)	C8—C9—C10—C13A	171.39 (6)
C1—C2—C3—Cl1	−179.07 (5)	C8—C9—C10—S1A	−12.02 (12)
C2—C3—C4—C5	0.78 (10)	C13B—C10—S1A—C11A	25 (4)
Cl1—C3—C4—C5	−179.30 (5)	C9—C10—S1A—C11A	179.9 (3)
C3—C4—C5—C6	−1.42 (10)	C13A—C10—S1A—C11A	−3.3 (3)
C2—C1—C6—C5	1.21 (10)	C13A—C12A—C11A—S1A	−4.4 (13)
C2—C1—C6—C7	−175.78 (6)	C10—S1A—C11A—C12A	4.7 (9)
C4—C5—C6—C1	0.45 (10)	C13B—C10—C13A—C12A	−1.0 (5)
C4—C5—C6—C7	177.56 (6)	C9—C10—C13A—C12A	178.2 (5)
C1—C6—C7—O1	152.83 (7)	S1A—C10—C13A—C12A	1.3 (5)
C5—C6—C7—O1	−24.21 (9)	C11A—C12A—C13A—C10	1.3 (9)
C1—C6—C7—C8	−27.58 (9)	C9—C10—C13B—C12B	−176.2 (3)
C5—C6—C7—C8	155.39 (6)	C13A—C10—C13B—C12B	2.9 (4)
O1—C7—C8—C9	−11.43 (11)	S1A—C10—C13B—C12B	−150 (4)
C6—C7—C8—C9	168.99 (6)	C10—C13B—C12B—C11B	−3.4 (8)
C7—C8—C9—C10	175.33 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···Cg1^i	0.93	2.90	3.559 (3)	129
C2—H2A···Cg2^i	0.93	2.90	3.538 (3)	127
C5—H5A···Cg1^ii	0.93	2.84	3.467 (3)	126
C5—H5A···Cg2^ii	0.93	2.82	3.475 (3)	128
C9—H9A···Cg3^iii	0.93	2.98	3.528 (1)	119
C12B—H12C···Cg3^iv	0.93	2.87	3.518 (6)	128
C11A—H11A···Cg3^iv	0.93	2.89	3.501 (6)	124

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+1, −z; (iv) −x+2, −y+2, −z.