(E)-1-(5-Chloro­thio­phen-2-yl)-3-(2,4-di­methyl­phen­yl)prop-2-en-1-one

In the title compound, C₁₅H₁₃ClOS, the olefinic double bond adopts an E configuration. The mol­ecule is nearly planar, as seen by the dihedral angle of 9.07 (8)° between the thio­phene and phenyl rings. The trans configuration of the C=C double bond in the central enone group is confirmed by the C—C=C—C torsion angle of 177.6 (2)°. In the crystal, mol­ecules are linked by weak C—H...O and C—H...S hydrogen bonds, forming chains propagating along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.148
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5839
PLAT023_ALERT_3_C Resolution (too) Low [sin(theta)/Lambda < 0.6]..      64.20 Degree
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.977 Note
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  S1      ..       2.90 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.584         49 Report
PLAT977_ALERT_2_C Check the Negative Difference Density on      H6      -0.63 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H15A      -0.53 eA-3

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.11 Report
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as      mixed Check
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          96 % Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

(E)-1-(5-Chlorothiophen-2-yl)-3-(2,4-dimethylphenyl)prop-2-en-1-one

Crystal data

C15H13ClOS	F(000) = 576
Mr = 276.77	Dx = 1.394 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2120 reflections
a = 15.588 (2) Å	θ = 5.7–64.2°
b = 7.4306 (11) Å	µ = 3.90 mm^−1
c = 11.4165 (17) Å	T = 296 K
β = 94.293 (3)°	Rectangle, green
V = 1318.6 (3) Å^3	0.29 × 0.26 × 0.23 mm
Z = 4

Data collection

Bruker X8 Proteum diffractometer	2149 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2120 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.050
Detector resolution: 18.4 pixels mm^-1	θmax = 64.2°, θmin = 5.7°
φ and ω scans	h = −18→17
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −7→8
Tmin = 0.397, Tmax = 0.467	l = −12→13
9075 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.1085P)^2 + 0.5955P] where P = (Fo^2 + 2Fc^2)/3
2149 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.87 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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
Cl1	0.22467 (3)	0.94779 (7)	0.40476 (4)	0.0210 (2)
S1	0.39687 (3)	0.81834 (7)	0.35033 (4)	0.0179 (2)
O1	0.57439 (10)	0.7025 (2)	0.32391 (14)	0.0240 (5)
C1	0.32622 (13)	0.8762 (3)	0.45189 (19)	0.0163 (6)
C2	0.36001 (14)	0.8625 (3)	0.56508 (19)	0.0181 (6)
C3	0.44560 (15)	0.8010 (3)	0.5701 (2)	0.0174 (6)
C4	0.47497 (13)	0.7695 (3)	0.46152 (19)	0.0155 (6)
C5	0.56000 (14)	0.7119 (3)	0.42881 (19)	0.0170 (6)
C6	0.62517 (14)	0.6691 (3)	0.5239 (2)	0.0172 (6)
C7	0.70203 (14)	0.6053 (3)	0.49961 (19)	0.0179 (7)
C8	0.77481 (14)	0.5622 (3)	0.58247 (19)	0.0163 (7)
C9	0.77421 (14)	0.6023 (3)	0.7026 (2)	0.0187 (6)
C10	0.84389 (15)	0.5652 (3)	0.7802 (2)	0.0192 (7)
C11	0.91834 (14)	0.4879 (3)	0.7412 (2)	0.0185 (6)
C12	0.91894 (14)	0.4460 (3)	0.6227 (2)	0.0185 (7)
C13	0.84913 (14)	0.4818 (3)	0.5421 (2)	0.0173 (6)
C14	0.85383 (15)	0.4288 (3)	0.4153 (2)	0.0218 (7)
C15	0.99642 (15)	0.4547 (3)	0.8251 (2)	0.0232 (7)
H2	0.33040	0.89010	0.63050	0.0220*
H3	0.47900	0.78340	0.64010	0.0210*
H6	0.61300	0.68640	0.60160	0.0210*
H7	0.71000	0.58610	0.42070	0.0210*
H9	0.72560	0.65510	0.73040	0.0220*
H10	0.84140	0.59190	0.85950	0.0230*
H12	0.96760	0.39200	0.59600	0.0220*
H14A	0.90930	0.37800	0.40460	0.0330*
H14B	0.84510	0.53310	0.36630	0.0330*
H14C	0.81000	0.34140	0.39420	0.0330*
H15A	1.02790	0.35360	0.79840	0.0350*
H15B	0.97840	0.43010	0.90200	0.0350*
H15C	1.03260	0.55950	0.82810	0.0350*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0149 (4)	0.0250 (4)	0.0222 (4)	0.0028 (2)	−0.0046 (2)	0.0022 (2)
S1	0.0155 (4)	0.0266 (4)	0.0112 (4)	0.0009 (2)	−0.0024 (2)	−0.0011 (2)
O1	0.0188 (9)	0.0397 (10)	0.0134 (9)	0.0036 (7)	0.0011 (6)	−0.0022 (6)
C1	0.0136 (10)	0.0163 (11)	0.0185 (11)	−0.0008 (8)	−0.0014 (8)	0.0001 (8)
C2	0.0175 (11)	0.0218 (11)	0.0151 (11)	0.0002 (9)	0.0013 (8)	−0.0008 (9)
C3	0.0175 (11)	0.0199 (11)	0.0141 (11)	−0.0009 (8)	−0.0025 (9)	0.0031 (8)
C4	0.0152 (11)	0.0147 (10)	0.0160 (11)	−0.0026 (8)	−0.0022 (8)	0.0004 (8)
C5	0.0171 (11)	0.0177 (10)	0.0159 (11)	−0.0031 (8)	−0.0011 (9)	−0.0018 (8)
C6	0.0171 (11)	0.0201 (11)	0.0142 (11)	−0.0006 (8)	0.0006 (9)	−0.0006 (8)
C7	0.0202 (12)	0.0187 (11)	0.0148 (11)	−0.0020 (9)	0.0014 (9)	0.0005 (9)
C8	0.0155 (12)	0.0150 (11)	0.0182 (11)	−0.0034 (8)	−0.0005 (9)	0.0016 (8)
C9	0.0179 (11)	0.0194 (11)	0.0189 (11)	−0.0003 (8)	0.0027 (9)	−0.0007 (9)
C10	0.0221 (12)	0.0192 (11)	0.0161 (11)	−0.0040 (8)	0.0001 (9)	0.0001 (8)
C11	0.0182 (11)	0.0131 (10)	0.0237 (12)	−0.0046 (8)	−0.0021 (9)	0.0036 (9)
C12	0.0155 (11)	0.0143 (11)	0.0258 (13)	−0.0005 (8)	0.0016 (9)	0.0009 (8)
C13	0.0175 (11)	0.0143 (10)	0.0202 (12)	−0.0035 (8)	0.0022 (9)	0.0001 (8)
C14	0.0204 (12)	0.0241 (12)	0.0211 (12)	0.0015 (8)	0.0032 (10)	−0.0031 (9)
C15	0.0228 (12)	0.0198 (12)	0.0258 (13)	−0.0007 (9)	−0.0060 (10)	0.0011 (9)

Geometric parameters (Å, º)

Cl1—C1	1.718 (2)	C11—C15	1.512 (3)
S1—C1	1.713 (2)	C12—C13	1.397 (3)
S1—C4	1.730 (2)	C13—C14	1.507 (3)
O1—C5	1.237 (3)	C2—H2	0.9300
C1—C2	1.362 (3)	C3—H3	0.9300
C2—C3	1.407 (3)	C6—H6	0.9300
C3—C4	1.373 (3)	C7—H7	0.9300
C4—C5	1.468 (3)	C9—H9	0.9300
C5—C6	1.465 (3)	C10—H10	0.9300
C6—C7	1.337 (3)	C12—H12	0.9300
C7—C8	1.457 (3)	C14—H14A	0.9600
C8—C9	1.404 (3)	C14—H14B	0.9600
C8—C13	1.411 (3)	C14—H14C	0.9600
C9—C10	1.377 (3)	C15—H15A	0.9600
C10—C11	1.397 (3)	C15—H15B	0.9600
C11—C12	1.389 (3)	C15—H15C	0.9600
C1—S1—C4	90.50 (10)	C1—C2—H2	124.00
Cl1—C1—S1	119.33 (13)	C3—C2—H2	124.00
Cl1—C1—C2	127.02 (17)	C2—C3—H3	123.00
S1—C1—C2	113.63 (16)	C4—C3—H3	123.00
C1—C2—C3	111.2 (2)	C5—C6—H6	120.00
C2—C3—C4	113.4 (2)	C7—C6—H6	120.00
S1—C4—C3	111.27 (16)	C6—C7—H7	116.00
S1—C4—C5	118.28 (16)	C8—C7—H7	116.00
C3—C4—C5	130.4 (2)	C8—C9—H9	119.00
O1—C5—C4	119.7 (2)	C10—C9—H9	119.00
O1—C5—C6	122.6 (2)	C9—C10—H10	120.00
C4—C5—C6	117.65 (19)	C11—C10—H10	120.00
C5—C6—C7	120.4 (2)	C11—C12—H12	119.00
C6—C7—C8	127.6 (2)	C13—C12—H12	119.00
C7—C8—C9	121.7 (2)	C13—C14—H14A	110.00
C7—C8—C13	120.0 (2)	C13—C14—H14B	110.00
C9—C8—C13	118.3 (2)	C13—C14—H14C	109.00
C8—C9—C10	121.6 (2)	H14A—C14—H14B	109.00
C9—C10—C11	120.7 (2)	H14A—C14—H14C	109.00
C10—C11—C12	118.0 (2)	H14B—C14—H14C	109.00
C10—C11—C15	120.9 (2)	C11—C15—H15A	109.00
C12—C11—C15	121.1 (2)	C11—C15—H15B	110.00
C11—C12—C13	122.5 (2)	C11—C15—H15C	109.00
C8—C13—C12	118.9 (2)	H15A—C15—H15B	109.00
C8—C13—C14	121.6 (2)	H15A—C15—H15C	109.00
C12—C13—C14	119.4 (2)	H15B—C15—H15C	109.00
C4—S1—C1—Cl1	179.60 (15)	C6—C7—C8—C9	−6.7 (4)
C4—S1—C1—C2	0.98 (19)	C6—C7—C8—C13	174.8 (2)
C1—S1—C4—C3	−0.93 (18)	C7—C8—C9—C10	−178.5 (2)
C1—S1—C4—C5	−178.14 (18)	C13—C8—C9—C10	0.1 (3)
Cl1—C1—C2—C3	−179.26 (17)	C7—C8—C13—C12	178.4 (2)
S1—C1—C2—C3	−0.8 (3)	C7—C8—C13—C14	−3.5 (3)
C1—C2—C3—C4	0.0 (3)	C9—C8—C13—C12	−0.2 (3)
C2—C3—C4—S1	0.7 (3)	C9—C8—C13—C14	177.9 (2)
C2—C3—C4—C5	177.5 (2)	C8—C9—C10—C11	0.8 (3)
S1—C4—C5—O1	1.2 (3)	C9—C10—C11—C12	−1.5 (3)
S1—C4—C5—C6	−179.34 (16)	C9—C10—C11—C15	177.2 (2)
C3—C4—C5—O1	−175.4 (2)	C10—C11—C12—C13	1.4 (3)
C3—C4—C5—C6	4.1 (4)	C15—C11—C12—C13	−177.3 (2)
O1—C5—C6—C7	−4.7 (3)	C11—C12—C13—C8	−0.5 (3)
C4—C5—C6—C7	175.9 (2)	C11—C12—C13—C14	−178.7 (2)
C5—C6—C7—C8	177.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1^i	0.93	2.48	3.400 (3)	169
C3—H3···S1^i	0.93	2.90	3.459 (2)	120

Symmetry code: (i) x, −y+3/2, z+1/2.