(2E)-1-(3-Bromo-2-thien­yl)-3-(4-chloro­phen­yl)prop-2-en-1-one, a twinned crystal structure

Crystals of the title compound, C₁₃H₁₈BrClOS, appeared to be twinned by an inter­change of the a and c axes. There are two almost identical mol­ecules in the asymmetric unit which are essentially planar and do not show unusual geometric parameters.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.017 Å
• R factor = 0.060
• wR factor = 0.160
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         18

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT128_ALERT_4_C Non-standard setting of Space group Pc      ....    Pn
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Cl1A    ..       3.43 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1A   ..  Cl1     ..       3.58 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.61
           From the CIF: _reflns_number_total               4349
           Count of symmetry unique reflns         2368
           Completeness (_total/calc)            183.66%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1981
           Fraction of Friedel pairs measured     0.837
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

(2E)-1-(3-Bromo-2-thienyl)-3-(4-chlorophenyl)prop-2-en-1-one

Crystal data

C13H8BrClOS	F(000) = 648
Mr = 327.61	Dx = 1.729 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 7620 reflections
a = 17.955 (2) Å	θ = 3.8–25.6°
b = 3.9563 (3) Å	µ = 3.62 mm^−1
c = 17.973 (2) Å	T = 173 K
β = 99.646 (9)°	Plate, yellow
V = 1258.7 (2) Å^3	0.32 × 0.24 × 0.12 mm
Z = 4

Data collection

Stoe IPDS-II two-circle diffractometer	4349 independent reflections
Radiation source: fine-focus sealed tube	4201 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
ω scans	θmax = 25.6°, θmin = 3.8°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −21→21
Tmin = 0.390, Tmax = 0.670	k = −4→4
7621 measured reflections	l = −21→21

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.060	w = 1/[σ^2(Fo^2) + (0.1235P)^2 + 0.2142P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.160	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.90 e Å^−3
4349 reflections	Δρmin = −0.69 e Å^−3
309 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0072 (18)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2001 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.013 (16)

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
Br1	0.59071 (6)	1.1042 (3)	0.74739 (6)	0.0343 (4)
S1	0.49688 (19)	1.0924 (8)	0.95931 (16)	0.0289 (7)
Cl1	0.3051 (2)	0.1204 (9)	0.38436 (18)	0.0412 (8)
O1	0.3731 (5)	0.796 (3)	0.8607 (5)	0.035 (2)
C1	0.4955 (6)	1.009 (3)	0.8648 (6)	0.0215 (18)
C2	0.5612 (7)	1.120 (3)	0.8454 (7)	0.026 (2)
C3	0.6129 (7)	1.270 (3)	0.9052 (7)	0.029 (2)
H3	0.6610	1.3588	0.9004	0.035*
C4	0.5832 (7)	1.269 (3)	0.9699 (7)	0.029 (2)
H4	0.6086	1.3586	1.0164	0.034*
C5	0.4270 (7)	0.842 (3)	0.8247 (6)	0.022 (2)
C6	0.4217 (7)	0.730 (3)	0.7457 (6)	0.026 (2)
H6	0.4649	0.7526	0.7220	0.031*
C7	0.3597 (8)	0.598 (3)	0.7065 (7)	0.027 (2)
H7	0.3176	0.5792	0.7319	0.033*
C11	0.3482 (6)	0.477 (3)	0.6274 (6)	0.023 (2)
C12	0.4067 (7)	0.478 (3)	0.5852 (6)	0.029 (3)
H12	0.4554	0.5556	0.6075	0.035*
C13	0.3946 (8)	0.367 (3)	0.5111 (8)	0.034 (3)
H13	0.4349	0.3645	0.4829	0.040*
C14	0.3226 (7)	0.258 (3)	0.4780 (6)	0.029 (2)
C15	0.2641 (7)	0.256 (3)	0.5178 (7)	0.028 (2)
H15	0.2154	0.1786	0.4950	0.034*
C16	0.2771 (7)	0.370 (3)	0.5934 (7)	0.028 (3)
H16	0.2366	0.3727	0.6213	0.034*
Br1A	0.48897 (7)	−0.1519 (3)	0.35885 (7)	0.0348 (3)
S1A	0.70292 (17)	−0.0748 (8)	0.26925 (17)	0.0300 (7)
Cl1A	0.12050 (19)	0.7757 (10)	0.06545 (18)	0.0420 (8)
O1A	0.6054 (6)	0.250 (3)	0.1504 (5)	0.038 (2)
C1A	0.6071 (7)	−0.017 (3)	0.2666 (6)	0.022 (2)
C2A	0.5879 (7)	−0.150 (3)	0.3333 (6)	0.023 (2)
C3A	0.6466 (8)	−0.295 (3)	0.3822 (7)	0.034 (3)
H3A	0.6417	−0.3968	0.4290	0.041*
C4A	0.7135 (8)	−0.272 (3)	0.3542 (8)	0.033 (3)
H4A	0.7603	−0.3578	0.3797	0.040*
C5A	0.5673 (7)	0.165 (3)	0.1978 (6)	0.027 (2)
C6A	0.4868 (7)	0.230 (3)	0.1891 (6)	0.027 (2)
H6A	0.4588	0.1335	0.2242	0.033*
C7A	0.4506 (7)	0.423 (3)	0.1325 (7)	0.027 (2)
H7A	0.4801	0.5157	0.0983	0.032*
C11A	0.3695 (7)	0.502 (3)	0.1190 (6)	0.026 (2)
C12A	0.3201 (8)	0.439 (3)	0.1708 (7)	0.029 (3)
H12A	0.3397	0.3412	0.2184	0.035*
C13A	0.2457 (7)	0.514 (4)	0.1548 (7)	0.032 (3)
H13A	0.2137	0.4623	0.1904	0.038*
C14A	0.2152 (8)	0.669 (3)	0.0854 (7)	0.032 (2)
C15A	0.2636 (8)	0.739 (3)	0.0330 (6)	0.030 (2)
H15A	0.2438	0.8382	−0.0143	0.036*
C16A	0.3389 (7)	0.663 (3)	0.0500 (6)	0.025 (2)
H16A	0.3713	0.7193	0.0152	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0374 (8)	0.0389 (7)	0.0302 (7)	−0.0088 (5)	0.0156 (5)	−0.0046 (5)
S1	0.0323 (16)	0.0325 (15)	0.0218 (13)	−0.0023 (12)	0.0039 (11)	−0.0034 (11)
Cl1	0.048 (2)	0.0514 (19)	0.0251 (13)	−0.0050 (15)	0.0081 (13)	−0.0087 (13)
O1	0.025 (5)	0.051 (5)	0.027 (4)	−0.010 (4)	0.002 (3)	−0.004 (4)
C1	0.019 (6)	0.026 (4)	0.020 (5)	0.001 (5)	0.004 (4)	−0.005 (5)
C2	0.028 (7)	0.027 (5)	0.021 (5)	−0.001 (4)	0.002 (5)	0.001 (4)
C3	0.029 (6)	0.027 (6)	0.032 (6)	−0.001 (5)	0.003 (5)	−0.008 (5)
C4	0.025 (6)	0.039 (6)	0.020 (5)	0.001 (5)	−0.001 (4)	−0.001 (5)
C5	0.018 (6)	0.027 (5)	0.023 (5)	0.005 (4)	0.006 (4)	0.005 (4)
C6	0.025 (6)	0.030 (5)	0.024 (5)	−0.005 (5)	0.011 (4)	−0.003 (5)
C7	0.031 (7)	0.024 (5)	0.026 (6)	0.000 (4)	0.004 (5)	0.003 (4)
C11	0.023 (6)	0.017 (5)	0.028 (5)	0.000 (4)	0.001 (4)	0.006 (4)
C12	0.028 (7)	0.031 (6)	0.027 (6)	−0.004 (5)	−0.001 (5)	−0.005 (4)
C13	0.023 (6)	0.047 (8)	0.033 (7)	0.000 (5)	0.011 (5)	0.002 (5)
C14	0.041 (7)	0.023 (5)	0.024 (5)	0.000 (5)	0.009 (4)	0.002 (4)
C15	0.027 (6)	0.030 (6)	0.025 (6)	0.003 (5)	−0.003 (5)	−0.006 (5)
C16	0.019 (6)	0.040 (6)	0.026 (6)	−0.004 (5)	0.002 (5)	0.002 (4)
Br1A	0.0334 (8)	0.0393 (6)	0.0342 (7)	0.0027 (6)	0.0126 (5)	0.0062 (5)
S1A	0.0210 (15)	0.0396 (17)	0.0294 (14)	0.0027 (12)	0.0041 (12)	0.0002 (12)
Cl1A	0.0327 (18)	0.0555 (19)	0.0365 (16)	0.0123 (15)	0.0021 (13)	−0.0006 (15)
O1A	0.036 (5)	0.051 (6)	0.029 (4)	0.001 (4)	0.014 (4)	0.014 (4)
C1A	0.024 (6)	0.019 (4)	0.020 (5)	−0.003 (4)	0.001 (4)	−0.005 (4)
C2A	0.025 (6)	0.025 (5)	0.018 (5)	0.000 (4)	0.001 (4)	−0.010 (4)
C3A	0.046 (8)	0.023 (5)	0.031 (6)	0.007 (5)	0.000 (5)	0.004 (5)
C4A	0.030 (7)	0.030 (6)	0.039 (7)	0.002 (5)	0.002 (5)	0.000 (5)
C5A	0.024 (6)	0.033 (6)	0.022 (5)	0.009 (5)	0.002 (5)	0.007 (4)
C6A	0.027 (6)	0.037 (6)	0.016 (5)	−0.002 (5)	0.000 (4)	0.001 (5)
C7A	0.026 (6)	0.027 (6)	0.027 (6)	0.006 (4)	0.004 (5)	0.003 (4)
C11A	0.024 (6)	0.027 (5)	0.023 (5)	0.003 (5)	−0.003 (4)	−0.007 (5)
C12A	0.038 (7)	0.028 (5)	0.021 (6)	0.004 (5)	0.006 (5)	0.002 (4)
C13A	0.028 (6)	0.037 (6)	0.030 (6)	0.007 (5)	0.006 (5)	0.004 (5)
C14A	0.042 (8)	0.022 (4)	0.030 (6)	0.010 (5)	0.000 (5)	−0.007 (4)
C15A	0.039 (7)	0.028 (5)	0.021 (5)	0.008 (5)	−0.001 (4)	0.002 (5)
C16A	0.034 (7)	0.025 (5)	0.017 (5)	−0.001 (4)	0.005 (5)	0.004 (4)

Geometric parameters (Å, º)

Br1—C2	1.924 (13)	Br1A—C2A	1.907 (12)
S1—C4	1.682 (14)	S1A—C4A	1.697 (14)
S1—C1	1.727 (11)	S1A—C1A	1.727 (12)
Cl1—C14	1.746 (11)	Cl1A—C14A	1.731 (14)
O1—C5	1.264 (16)	O1A—C5A	1.225 (16)
C1—C2	1.358 (18)	C1A—C2A	1.404 (17)
C1—C5	1.471 (16)	C1A—C5A	1.505 (15)
C2—C3	1.427 (17)	C2A—C3A	1.381 (17)
C3—C4	1.357 (18)	C3A—C4A	1.38 (2)
C3—H3	0.9500	C3A—H3A	0.9500
C4—H4	0.9500	C4A—H4A	0.9500
C5—C6	1.476 (15)	C5A—C6A	1.451 (18)
C6—C7	1.320 (18)	C6A—C7A	1.349 (17)
C6—H6	0.9500	C6A—H6A	0.9500
C7—C11	1.481 (15)	C7A—C11A	1.469 (17)
C7—H7	0.9500	C7A—H7A	0.9500
C11—C16	1.387 (17)	C11A—C12A	1.413 (18)
C11—C12	1.395 (16)	C11A—C16A	1.420 (16)
C12—C13	1.385 (17)	C12A—C13A	1.352 (18)
C12—H12	0.9500	C12A—H12A	0.9500
C13—C14	1.397 (18)	C13A—C14A	1.415 (17)
C13—H13	0.9500	C13A—H13A	0.9500
C14—C15	1.367 (17)	C14A—C15A	1.41 (2)
C15—C16	1.414 (16)	C15A—C16A	1.369 (18)
C15—H15	0.9500	C15A—H15A	0.9500
C16—H16	0.9500	C16A—H16A	0.9500
C4—S1—C1	93.0 (6)	C4A—S1A—C1A	92.6 (6)
C2—C1—C5	135.2 (10)	C2A—C1A—C5A	136.9 (11)
C2—C1—S1	108.6 (8)	C2A—C1A—S1A	108.3 (8)
C5—C1—S1	116.1 (9)	C5A—C1A—S1A	114.8 (9)
C1—C2—C3	115.2 (11)	C3A—C2A—C1A	115.4 (11)
C1—C2—Br1	127.5 (9)	C3A—C2A—Br1A	119.2 (10)
C3—C2—Br1	117.3 (9)	C1A—C2A—Br1A	125.5 (9)
C4—C3—C2	110.2 (12)	C4A—C3A—C2A	111.0 (12)
C4—C3—H3	124.9	C4A—C3A—H3A	124.5
C2—C3—H3	124.9	C2A—C3A—H3A	124.5
C3—C4—S1	113.0 (9)	C3A—C4A—S1A	112.7 (10)
C3—C4—H4	123.5	C3A—C4A—H4A	123.7
S1—C4—H4	123.5	S1A—C4A—H4A	123.7
O1—C5—C1	117.6 (10)	O1A—C5A—C6A	122.6 (10)
O1—C5—C6	121.1 (11)	O1A—C5A—C1A	117.3 (11)
C1—C5—C6	121.3 (10)	C6A—C5A—C1A	120.0 (11)
C7—C6—C5	123.1 (11)	C7A—C6A—C5A	121.7 (11)
C7—C6—H6	118.5	C7A—C6A—H6A	119.1
C5—C6—H6	118.5	C5A—C6A—H6A	119.1
C6—C7—C11	127.6 (12)	C6A—C7A—C11A	125.7 (12)
C6—C7—H7	116.2	C6A—C7A—H7A	117.2
C11—C7—H7	116.2	C11A—C7A—H7A	117.2
C16—C11—C12	118.8 (11)	C12A—C11A—C16A	117.4 (11)
C16—C11—C7	119.5 (11)	C12A—C11A—C7A	124.7 (11)
C12—C11—C7	121.7 (11)	C16A—C11A—C7A	117.9 (11)
C13—C12—C11	120.7 (12)	C13A—C12A—C11A	121.9 (11)
C13—C12—H12	119.6	C13A—C12A—H12A	119.0
C11—C12—H12	119.6	C11A—C12A—H12A	119.0
C12—C13—C14	119.5 (12)	C12A—C13A—C14A	120.3 (12)
C12—C13—H13	120.2	C12A—C13A—H13A	119.8
C14—C13—H13	120.2	C14A—C13A—H13A	119.8
C15—C14—C13	121.1 (11)	C15A—C14A—C13A	118.9 (12)
C15—C14—Cl1	118.2 (10)	C15A—C14A—Cl1A	120.4 (9)
C13—C14—Cl1	120.7 (9)	C13A—C14A—Cl1A	120.7 (11)
C14—C15—C16	118.9 (11)	C16A—C15A—C14A	120.2 (10)
C14—C15—H15	120.6	C16A—C15A—H15A	119.9
C16—C15—H15	120.6	C14A—C15A—H15A	119.9
C11—C16—C15	120.9 (12)	C15A—C16A—C11A	121.2 (11)
C11—C16—H16	119.5	C15A—C16A—H16A	119.4
C15—C16—H16	119.5	C11A—C16A—H16A	119.4
C4—S1—C1—C2	−0.1 (9)	C4A—S1A—C1A—C2A	1.1 (9)
C4—S1—C1—C5	−179.8 (9)	C4A—S1A—C1A—C5A	179.2 (9)
C5—C1—C2—C3	179.9 (12)	C5A—C1A—C2A—C3A	−178.8 (13)
S1—C1—C2—C3	0.2 (13)	S1A—C1A—C2A—C3A	−1.2 (13)
C5—C1—C2—Br1	1 (2)	C5A—C1A—C2A—Br1A	3 (2)
S1—C1—C2—Br1	−178.5 (6)	S1A—C1A—C2A—Br1A	−179.9 (6)
C1—C2—C3—C4	−0.3 (15)	C1A—C2A—C3A—C4A	0.8 (15)
Br1—C2—C3—C4	178.6 (9)	Br1A—C2A—C3A—C4A	179.5 (9)
C2—C3—C4—S1	0.2 (14)	C2A—C3A—C4A—S1A	0.1 (14)
C1—S1—C4—C3	−0.1 (10)	C1A—S1A—C4A—C3A	−0.7 (10)
C2—C1—C5—O1	−174.9 (13)	C2A—C1A—C5A—O1A	178.4 (13)
S1—C1—C5—O1	4.8 (14)	S1A—C1A—C5A—O1A	0.9 (15)
C2—C1—C5—C6	6 (2)	C2A—C1A—C5A—C6A	−2 (2)
S1—C1—C5—C6	−174.4 (9)	S1A—C1A—C5A—C6A	−179.9 (9)
O1—C5—C6—C7	5.0 (18)	O1A—C5A—C6A—C7A	−8.0 (19)
C1—C5—C6—C7	−175.8 (11)	C1A—C5A—C6A—C7A	172.9 (11)
C5—C6—C7—C11	−180.0 (11)	C5A—C6A—C7A—C11A	179.9 (11)
C6—C7—C11—C16	−175.1 (12)	C6A—C7A—C11A—C12A	12.1 (19)
C6—C7—C11—C12	2.9 (18)	C6A—C7A—C11A—C16A	−170.0 (12)
C16—C11—C12—C13	−1.3 (18)	C16A—C11A—C12A—C13A	2.9 (19)
C7—C11—C12—C13	−179.4 (11)	C7A—C11A—C12A—C13A	−179.2 (12)
C11—C12—C13—C14	1.0 (19)	C11A—C12A—C13A—C14A	−2 (2)
C12—C13—C14—C15	−0.8 (19)	C12A—C13A—C14A—C15A	1.0 (19)
C12—C13—C14—Cl1	179.3 (10)	C12A—C13A—C14A—Cl1A	−178.3 (10)
C13—C14—C15—C16	0.8 (18)	C13A—C14A—C15A—C16A	−1.3 (18)
Cl1—C14—C15—C16	−179.3 (9)	Cl1A—C14A—C15A—C16A	178.0 (9)
C12—C11—C16—C15	1.3 (17)	C14A—C15A—C16A—C11A	2.5 (18)
C7—C11—C16—C15	179.4 (10)	C12A—C11A—C16A—C15A	−3.2 (17)
C14—C15—C16—C11	−1.1 (18)	C7A—C11A—C16A—C15A	178.7 (11)