1-(2,4-Dichloro­phen­yl)-3-(2-thien­yl)prop-2-en-1-one

The thio­phene ring of the title compound, C₁₃H₈Cl₂OS, is disordered. The disorder corresponds to an approximate 180° rotation of the thio­phene ring with respect to the C—C bond linking it to the rest of the mol­ecule. The crystal packing is stabilized by short Cl...Cl and S...O contacts, together with inter­molecular C—H...O and C—H...S inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• Disorder in main residue
• R factor = 0.026
• wR factor = 0.079
• Data-to-parameter ratio = 41.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.62 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.23
PLAT301_ALERT_3_C Main Residue  Disorder .........................      19.00 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A    ..  S1X     ..       2.89 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       1.50 Deg.
              C13  -C10  -S1X     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       2.50 Deg.
              C13X -C10  -S1      1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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 and PLATON (Spek, 2003).

1-(2,4-Dichlorophenyl)-3-(2-thienyl)prop-2-en-1-one

Crystal data

C13H8Cl2OS	F(000) = 576
Mr = 283.15	Dx = 1.577 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9371 reflections
a = 14.1918 (2) Å	θ = 1.6–40.0°
b = 3.8515 (1) Å	µ = 0.70 mm^−1
c = 24.3418 (3) Å	T = 100 K
β = 116.283 (1)°	Block, yellow
V = 1192.96 (4) Å^3	0.62 × 0.59 × 0.33 mm
Z = 4

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	7306 independent reflections
Radiation source: fine-focus sealed tube	6624 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.33 pixels mm^-1	θmax = 40.0°, θmin = 1.6°
ω scans	h = −25→25
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
Tmin = 0.716, Tmax = 0.805	l = −44→42
50586 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0413P)^2 + 0.2466P] where P = (Fo^2 + 2Fc^2)/3
7306 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.61 e Å^−3
109 restraints	Δρmin = −0.28 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	0.094913 (12)	0.20794 (4)	0.242014 (7)	0.01670 (3)
Cl2	0.474856 (13)	0.80436 (5)	0.345244 (7)	0.01948 (4)
O1	0.12963 (4)	0.19017 (17)	0.07624 (3)	0.02345 (11)
C1	0.19652 (4)	0.40456 (15)	0.23203 (3)	0.01327 (8)
C2	0.28282 (5)	0.51240 (16)	0.28507 (3)	0.01453 (9)
H2A	0.2839	0.4846	0.3233	0.017*
C3	0.36734 (5)	0.66255 (16)	0.27960 (3)	0.01434 (9)
C4	0.36834 (5)	0.70057 (17)	0.22307 (3)	0.01568 (9)
H4A	0.4255	0.8013	0.2201	0.019*
C5	0.28209 (5)	0.58469 (17)	0.17120 (3)	0.01548 (9)
H5A	0.2829	0.6034	0.1333	0.019*
C6	0.19382 (4)	0.44028 (16)	0.17413 (3)	0.01350 (8)
C7	0.10596 (5)	0.32523 (17)	0.11409 (3)	0.01574 (9)
C8	−0.00330 (5)	0.38650 (17)	0.10255 (3)	0.01578 (9)
H8A	−0.0175	0.5191	0.1299	0.019*
C9	−0.08325 (5)	0.25130 (17)	0.05240 (3)	0.01533 (9)
H9A	−0.0662	0.1345	0.0246	0.018*
C10	−0.19296 (5)	0.27354 (16)	0.03852 (3)	0.01460 (9)
S1	−0.23704 (2)	0.44872 (8)	0.087969 (14)	0.01577 (5)	0.8399 (12)
C11	−0.36517 (9)	0.3556 (3)	0.03931 (5)	0.01755 (15)	0.8399 (12)
H11A	−0.4216	0.4080	0.0476	0.021*	0.8399 (12)
C12	−0.37514 (7)	0.1951 (3)	−0.01321 (5)	0.01699 (14)	0.8399 (12)
H12A	−0.4390	0.1267	−0.0448	0.020*	0.8399 (12)
C13	−0.2755 (2)	0.1453 (8)	−0.01365 (10)	0.0166 (3)	0.8399 (12)
H13A	−0.2672	0.0385	−0.0455	0.020*	0.8399 (12)
S1X	−0.2904 (3)	0.1161 (11)	−0.02522 (13)	0.0178 (5)	0.1601 (12)
C11X	−0.3822 (6)	0.2336 (19)	−0.0020 (3)	0.0244 (14)*	0.1601 (12)
H11B	−0.4537	0.1926	−0.0252	0.029*	0.1601 (12)
C12X	−0.3436 (5)	0.3877 (17)	0.0518 (3)	0.0199 (12)*	0.1601 (12)
H12B	−0.3845	0.4650	0.0704	0.024*	0.1601 (12)
C13X	−0.2345 (6)	0.423 (2)	0.0777 (4)	0.0211 (16)*	0.1601 (12)
H13B	−0.1939	0.5278	0.1153	0.025*	0.1601 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01488 (6)	0.01794 (6)	0.02006 (6)	−0.00034 (4)	0.01028 (5)	0.00154 (4)
Cl2	0.01698 (6)	0.02248 (7)	0.01651 (6)	−0.00333 (5)	0.00518 (5)	−0.00204 (5)
O1	0.0184 (2)	0.0337 (3)	0.0185 (2)	0.00207 (19)	0.00841 (17)	−0.00800 (19)
C1	0.01291 (19)	0.0132 (2)	0.0155 (2)	0.00113 (15)	0.00794 (16)	0.00024 (16)
C2	0.0154 (2)	0.0153 (2)	0.01397 (19)	0.00067 (17)	0.00751 (17)	0.00032 (16)
C3	0.0136 (2)	0.0145 (2)	0.0144 (2)	0.00046 (16)	0.00579 (17)	−0.00033 (16)
C4	0.0148 (2)	0.0167 (2)	0.0170 (2)	−0.00021 (17)	0.00837 (18)	0.00115 (17)
C5	0.0151 (2)	0.0179 (2)	0.0150 (2)	0.00058 (17)	0.00806 (17)	0.00109 (17)
C6	0.01281 (19)	0.0143 (2)	0.01393 (19)	0.00160 (15)	0.00639 (16)	0.00028 (16)
C7	0.0143 (2)	0.0175 (2)	0.0148 (2)	0.00156 (17)	0.00585 (17)	−0.00116 (17)
C8	0.0137 (2)	0.0166 (2)	0.0161 (2)	0.00162 (17)	0.00567 (17)	−0.00146 (17)
C9	0.0148 (2)	0.0162 (2)	0.0146 (2)	0.00092 (17)	0.00612 (17)	−0.00024 (17)
C10	0.0145 (2)	0.0157 (2)	0.0132 (2)	0.00079 (16)	0.00585 (17)	0.00059 (16)
S1	0.01680 (9)	0.01777 (10)	0.01315 (10)	0.00075 (6)	0.00702 (7)	−0.00137 (7)
C11	0.0140 (3)	0.0207 (4)	0.0186 (4)	0.0011 (3)	0.0078 (3)	0.0001 (3)
C12	0.0150 (3)	0.0184 (3)	0.0147 (3)	−0.0003 (2)	0.0039 (3)	−0.0007 (3)
C13	0.0156 (7)	0.0188 (5)	0.0146 (7)	0.0004 (5)	0.0058 (5)	−0.0007 (5)
S1X	0.0144 (9)	0.0210 (9)	0.0164 (11)	−0.0005 (6)	0.0052 (8)	0.0026 (8)

Geometric parameters (Å, º)

Cl1—C1	1.7384 (6)	C9—H9A	0.9300
Cl2—C3	1.7379 (6)	C10—C13	1.3827 (19)
O1—C7	1.2275 (8)	C10—C13X	1.444 (7)
C1—C2	1.3924 (8)	C10—S1X	1.670 (2)
C1—C6	1.3999 (8)	C10—S1	1.7210 (7)
C2—C3	1.3900 (9)	S1—C11	1.7119 (12)
C2—H2A	0.9300	C11—C12	1.3696 (16)
C3—C4	1.3901 (9)	C11—H11A	0.9300
C4—C5	1.3868 (9)	C12—C13	1.431 (3)
C4—H4A	0.9300	C12—H12A	0.9300
C5—C6	1.4010 (8)	C13—H13A	0.9300
C5—H5A	0.9300	S1X—C11X	1.695 (8)
C6—C7	1.5076 (8)	C11X—C12X	1.315 (9)
C7—C8	1.4674 (9)	C11X—H11B	0.9300
C8—C9	1.3499 (9)	C12X—C13X	1.397 (10)
C8—H8A	0.9300	C12X—H12B	0.9300
C9—C10	1.4421 (9)	C13X—H13B	0.9300
C2—C1—C6	121.66 (5)	C9—C10—C13X	125.7 (3)
C2—C1—Cl1	116.35 (4)	C13—C10—S1X	1.5 (3)
C6—C1—Cl1	121.94 (5)	C9—C10—S1X	124.08 (16)
C3—C2—C1	118.52 (5)	C13X—C10—S1X	110.2 (4)
C3—C2—H2A	120.7	C13—C10—S1	111.08 (14)
C1—C2—H2A	120.7	C9—C10—S1	123.27 (5)
C2—C3—C4	121.73 (6)	C13X—C10—S1	2.5 (3)
C2—C3—Cl2	119.10 (5)	S1X—C10—S1	112.58 (15)
C4—C3—Cl2	119.17 (5)	C11—S1—C10	92.16 (4)
C5—C4—C3	118.41 (6)	C12—C11—S1	112.30 (7)
C5—C4—H4A	120.8	C12—C11—H11A	123.8
C3—C4—H4A	120.8	S1—C11—H11A	123.8
C4—C5—C6	122.01 (5)	C11—C12—C13	111.92 (10)
C4—C5—H5A	119.0	C11—C12—H12A	124.0
C6—C5—H5A	119.0	C13—C12—H12A	124.0
C1—C6—C5	117.64 (5)	C10—C13—C12	112.54 (19)
C1—C6—C7	126.10 (5)	C10—C13—H13A	123.7
C5—C6—C7	116.22 (5)	C12—C13—H13A	123.7
O1—C7—C8	122.80 (6)	C10—S1X—C11X	92.1 (3)
O1—C7—C6	117.93 (6)	C12X—C11X—S1X	114.1 (6)
C8—C7—C6	119.26 (5)	C12X—C11X—H11B	122.9
C9—C8—C7	120.32 (6)	S1X—C11X—H11B	122.9
C9—C8—H8A	119.8	C11X—C12X—C13X	112.6 (6)
C7—C8—H8A	119.8	C11X—C12X—H12B	123.7
C8—C9—C10	125.23 (6)	C13X—C12X—H12B	123.7
C8—C9—H9A	117.4	C12X—C13X—C10	111.0 (6)
C10—C9—H9A	117.4	C12X—C13X—H13B	124.5
C13—C10—C9	125.58 (14)	C10—C13X—H13B	124.5
C13—C10—C13X	108.7 (4)
C6—C1—C2—C3	0.76 (9)	C8—C9—C10—S1	−5.49 (10)
Cl1—C1—C2—C3	178.28 (5)	C13—C10—S1—C11	−0.46 (15)
C1—C2—C3—C4	−1.27 (9)	C9—C10—S1—C11	−177.55 (6)
C1—C2—C3—Cl2	179.06 (5)	C13X—C10—S1—C11	22 (8)
C2—C3—C4—C5	0.07 (9)	S1X—C10—S1—C11	−0.38 (17)
Cl2—C3—C4—C5	179.74 (5)	C10—S1—C11—C12	0.10 (8)
C3—C4—C5—C6	1.70 (9)	S1—C11—C12—C13	0.28 (17)
C2—C1—C6—C5	0.90 (9)	C9—C10—C13—C12	177.71 (12)
Cl1—C1—C6—C5	−176.47 (5)	C13X—C10—C13—C12	−0.3 (4)
C2—C1—C6—C7	178.45 (6)	S1X—C10—C13—C12	−176 (10)
Cl1—C1—C6—C7	1.07 (9)	S1—C10—C13—C12	0.7 (3)
C4—C5—C6—C1	−2.17 (9)	C11—C12—C13—C10	−0.6 (3)
C4—C5—C6—C7	−179.96 (6)	C13—C10—S1X—C11X	3 (11)
C1—C6—C7—O1	−139.62 (7)	C9—C10—S1X—C11X	177.6 (3)
C5—C6—C7—O1	37.96 (9)	C13X—C10—S1X—C11X	−0.6 (5)
C1—C6—C7—C8	41.99 (9)	S1—C10—S1X—C11X	0.4 (3)
C5—C6—C7—C8	−140.44 (6)	C10—S1X—C11X—C12X	0.1 (6)
O1—C7—C8—C9	9.29 (11)	S1X—C11X—C12X—C13X	0.4 (9)
C6—C7—C8—C9	−172.40 (6)	C11X—C12X—C13X—C10	−0.9 (9)
C7—C8—C9—C10	175.45 (6)	C13—C10—C13X—C12X	0.8 (7)
C8—C9—C10—C13	177.85 (18)	C9—C10—C13X—C12X	−177.2 (4)
C8—C9—C10—C13X	−4.4 (4)	S1X—C10—C13X—C12X	1.0 (7)
C8—C9—C10—S1X	177.66 (19)	S1—C10—C13X—C12X	−157 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Cl1	0.93	2.75	3.123 (1)	105
C8—H8A···S1	0.93	2.83	3.185 (1)	104
C9—H9A···O1	0.93	2.50	2.823 (1)	101
C5—H5A···S1X^i	0.93	2.89	3.787 (4)	162
C9—H9A···O1^ii	0.93	2.54	3.362 (1)	148
C13—H13A···O1^ii	0.93	2.54	3.327 (3)	143

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