1,5-Bis(3-bromo­thien-2-yl)-3-(2,3,5-trichloro­phen­yl)pentane-1,5-dione

Butcher, R.J.; Jasinski, J.P.; Yathirajan, H.S.; Bindya, S.; Narayana, B.

doi:10.1107/S1600536807030589

1,5-Bis(3-bromothien-2-yl)-3-(2,3,5-trichlorophenyl)pentane-1,5-dione

R. J. Butcher, J. P. Jasinski, H. S. Yathirajan, S. Bindya and B. Narayana

In the title compound, C₁₉H₁₁Br₂Cl₃O₂S₂, the angles between the plane of the 2,3,5-trichlorophenyl ring and those of the two 3-bromothien-2-yl rings are 89.7 (5) and 63.7 (1)°, with a dihedral angle of 77.4 (3)° between the last two planes.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030589/tk2165sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030589/tk2165Isup2.hkl Contains datablock I

CCDC reference: 655049

checkCIF report

Key indicators

Single-crystal X-ray study
T = 103 K
Mean (C-C) = 0.003 Å
R factor = 0.030
wR factor = 0.073
Data-to-parameter ratio = 23.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Cl2    ..  O1A     ..       2.93 Ang.

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.32
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3    ..  S1A     ..       3.44 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.324
            Tmax scaled      0.324 Tmin scaled      0.136

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound, C₁₉H₁₁Br₂Cl₃O₂S₂, is a new derivative with potential in the high efficiency photovoltaic cell arena. Crystals of these types play an important role in electronic and photonic industries such as in the production of high efficiency photovoltaic cells, fabrication of bright and long-lasting light emitting diodes [LED] and in liquid crystal displays [LCD] (Tareen & Kutty, 2001). Present day demand is for large and high quality ferroelectric, piezoelectric single crystals with minimum defects and inhomogenities. In continuation of our work on crystal structures of new organic chalcones (Butcher et al., 2006a; 2006b; Butcher, Yathirajan, Sarojini et al., 2006), the title compound, (I), has been prepared and its crystal structure determined.

Molecules of (I) comprise two five-membered 3-bromothien-2-yl rings at each end of a pentane-1,5-dione group with a 2,3,5-trichlorophenyl ring at the 3-position. The angles between the plane of the 2,3,5-trichlorophenyl ring and the two 3-bromothien-2-yl rings are 89.7 (5)° and 63.7 (1)°, respectively, with a dihedral angle of 77.4 (3)° between the latter planes.

Related literature top

For general background, see: Tareen & Kutty (2001). For related literature on the title compound, see: Baxter et al. (1990); Ng et al. (2006); Yathirajan et al. (2006); Butcher et al. (2006a,b); Butcher, Yathirajan, Sarojini et al. (2006). For crystal structures of a new series of related compounds, see: Baxter et al. (1990); Ng et al. (2006); Yathirajan et al. (2006).

Experimental top

2-Acetyl-3-bromothiophene (20 g, 0.096 mol) in methanol (50 ml) was mixed with 2,3,5-trichlorobenzaldehyde (9.84 g, 0.048 mol) and the mixture was treated with 30% potassium hydroxide solution (10 ml) at 278 K. The reaction mixture was then brought to room temperature and stirred for 6 h. The precipitate was filtered, washed with water, dried and recrytallized from acetone (yield 65%; m.p. 403–405 K). Elemental analysis found: C 37.81, H, 1.72, S, 10.54%; C₁₉H₁₁Br₂Cl₃O₂S₂ requires: C 37.93, H, 1.84, S, 10.66%.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top

Fig. 1. Molecular structure of C₁₉H₁₁Br₂Cl₃O₂S₂, (I), showing atom labeling and 50% probability displacement ellipsoids.

1,5-Bis(3-bromothien-2-yl)-3-(2,3,5-trichlorophenyl)pentane-1,5-dione top

Crystal data top

C₁₉H₁₁Br₂Cl₃O₂S₂	F(000) = 1176
M_r = 601.57	D_x = 1.923 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8105 reflections
a = 9.1380 (7) Å	θ = 2.6–30.7°
b = 16.0009 (11) Å	µ = 4.50 mm⁻¹
c = 14.2139 (10) Å	T = 103 K
β = 90.982 (1)°	Block, colorless
V = 2078.0 (3) Å³	0.47 × 0.36 × 0.25 mm
Z = 4

Data collection top

Bruker APEX2 CCD area-detector diffractometer	6056 independent reflections
Radiation source: fine-focus sealed tube	4876 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 0 pixels mm^-1	θ_max = 30.8°, θ_min = 1.9°
φ and ω scans	h = −13→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −21→22
T_min = 0.418, T_max = 1	l = −19→20
23415 measured reflections

Refinement top

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0387P)² + 0.0251P] where P = (F_o² + 2F_c²)/3
6056 reflections	(Δ/σ)_max = 0.002
253 parameters	Δρ_max = 1.11 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

C₁₉H₁₁Br₂Cl₃O₂S₂	V = 2078.0 (3) Å³
M_r = 601.57	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1380 (7) Å	µ = 4.50 mm⁻¹
b = 16.0009 (11) Å	T = 103 K
c = 14.2139 (10) Å	0.47 × 0.36 × 0.25 mm
β = 90.982 (1)°

Data collection top

Bruker APEX2 CCD area-detector diffractometer	6056 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	4876 reflections with I > 2σ(I)
T_min = 0.418, T_max = 1	R_int = 0.049
23415 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.04	Δρ_max = 1.11 e Å⁻³
6056 reflections	Δρ_min = −0.62 e Å⁻³
253 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1A	0.42307 (3)	0.511785 (13)	0.648516 (14)	0.01881 (6)
Br1B	1.12651 (2)	0.381058 (14)	0.725489 (16)	0.02260 (7)
Cl1	0.70399 (6)	0.05547 (3)	0.60137 (3)	0.01631 (10)
Cl2	0.49719 (6)	−0.09934 (3)	0.61154 (3)	0.01831 (11)
Cl3	0.04397 (6)	0.09993 (4)	0.69036 (4)	0.02140 (12)
S1A	0.21611 (7)	0.38361 (3)	0.40676 (4)	0.01961 (12)
S1B	0.83068 (6)	0.25216 (3)	0.91758 (3)	0.01789 (11)
O1A	0.41995 (19)	0.25982 (10)	0.47067 (11)	0.0240 (4)
O1B	0.83649 (17)	0.30796 (10)	0.64807 (10)	0.0211 (3)
C1	0.5688 (2)	0.22485 (12)	0.63890 (13)	0.0131 (4)
H1A	0.6381	0.2155	0.5862	0.016*
C2	0.4658 (2)	0.15015 (12)	0.64167 (13)	0.0127 (4)
C3	0.5207 (2)	0.06961 (12)	0.62640 (13)	0.0126 (4)
C4	0.4291 (2)	−0.00007 (12)	0.63045 (13)	0.0141 (4)
C5	0.2823 (2)	0.00884 (13)	0.64963 (14)	0.0161 (4)
H5A	0.2197	−0.0385	0.6523	0.019*
C6	0.2289 (2)	0.08842 (13)	0.66489 (14)	0.0148 (4)
C7	0.3180 (2)	0.15832 (13)	0.66149 (13)	0.0145 (4)
H7A	0.2779	0.2121	0.6727	0.017*
C1A	0.4946 (2)	0.30930 (12)	0.62241 (13)	0.0145 (4)
H1AA	0.4241	0.3193	0.6733	0.017*
H1AB	0.5697	0.3539	0.6261	0.017*
C2A	0.4146 (2)	0.31545 (13)	0.52842 (14)	0.0151 (4)
C3A	0.3280 (2)	0.39106 (13)	0.50608 (13)	0.0147 (4)
C4A	0.3183 (2)	0.47060 (13)	0.54265 (14)	0.0163 (4)
C5A	0.2239 (3)	0.52417 (14)	0.49206 (15)	0.0224 (5)
H5AA	0.2060	0.5808	0.5085	0.027*
C6A	0.1615 (3)	0.48482 (15)	0.41672 (17)	0.0247 (5)
H6AA	0.0945	0.5110	0.3742	0.030*
C1B	0.6602 (2)	0.22759 (13)	0.73140 (13)	0.0143 (4)
H1BA	0.5994	0.2513	0.7819	0.017*
H1BB	0.6870	0.1698	0.7498	0.017*
C2B	0.7981 (2)	0.27905 (13)	0.72335 (14)	0.0150 (4)
C3B	0.8870 (2)	0.29115 (13)	0.80966 (14)	0.0149 (4)
C4B	1.0196 (2)	0.33041 (13)	0.82200 (15)	0.0174 (4)
C5B	1.0748 (3)	0.32997 (14)	0.91510 (16)	0.0216 (5)
H5BA	1.1645	0.3553	0.9342	0.026*
C6B	0.9842 (3)	0.28887 (15)	0.97444 (16)	0.0236 (5)
H6BA	1.0039	0.2815	1.0397	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1A	0.02604 (13)	0.01413 (10)	0.01631 (10)	−0.00164 (8)	0.00192 (8)	−0.00241 (8)
Br1B	0.01341 (12)	0.02203 (12)	0.03247 (12)	−0.00257 (9)	0.00378 (9)	0.00598 (9)
Cl1	0.0119 (2)	0.0159 (2)	0.0212 (2)	0.00163 (19)	0.00085 (17)	−0.00031 (19)
Cl2	0.0222 (3)	0.0106 (2)	0.0221 (2)	0.00047 (19)	−0.00084 (19)	−0.00063 (18)
Cl3	0.0103 (3)	0.0265 (3)	0.0274 (3)	−0.0004 (2)	0.00133 (19)	0.0049 (2)
S1A	0.0215 (3)	0.0182 (3)	0.0190 (2)	0.0012 (2)	−0.0050 (2)	0.0011 (2)
S1B	0.0161 (3)	0.0215 (3)	0.0161 (2)	−0.0018 (2)	0.00106 (18)	−0.0008 (2)
O1A	0.0350 (10)	0.0158 (7)	0.0209 (7)	0.0063 (7)	−0.0061 (7)	−0.0054 (6)
O1B	0.0175 (9)	0.0255 (8)	0.0204 (7)	−0.0052 (7)	0.0004 (6)	0.0046 (6)
C1	0.0133 (10)	0.0112 (9)	0.0148 (8)	−0.0010 (8)	−0.0004 (7)	0.0005 (7)
C2	0.0139 (10)	0.0125 (9)	0.0115 (8)	−0.0001 (8)	−0.0013 (7)	0.0021 (7)
C3	0.0100 (10)	0.0139 (9)	0.0138 (8)	−0.0003 (8)	−0.0011 (7)	0.0008 (7)
C4	0.0172 (11)	0.0102 (9)	0.0147 (9)	−0.0001 (8)	−0.0031 (7)	−0.0003 (7)
C5	0.0169 (11)	0.0152 (10)	0.0161 (9)	−0.0060 (8)	−0.0038 (8)	0.0017 (8)
C6	0.0079 (10)	0.0207 (10)	0.0157 (9)	−0.0002 (8)	−0.0006 (7)	0.0029 (8)
C7	0.0147 (11)	0.0135 (9)	0.0152 (9)	0.0013 (8)	−0.0005 (7)	0.0005 (8)
C1A	0.0151 (11)	0.0123 (9)	0.0159 (9)	0.0004 (8)	−0.0005 (7)	0.0010 (8)
C2A	0.0149 (11)	0.0133 (9)	0.0172 (9)	−0.0007 (8)	0.0006 (7)	0.0015 (8)
C3A	0.0141 (11)	0.0150 (9)	0.0150 (9)	−0.0017 (8)	0.0027 (7)	0.0029 (8)
C4A	0.0188 (11)	0.0156 (10)	0.0145 (9)	0.0000 (8)	0.0022 (7)	0.0009 (8)
C5A	0.0266 (13)	0.0172 (11)	0.0233 (10)	0.0065 (9)	0.0021 (9)	0.0012 (9)
C6A	0.0229 (13)	0.0224 (11)	0.0287 (11)	0.0076 (10)	−0.0026 (9)	0.0056 (10)
C1B	0.0124 (10)	0.0136 (9)	0.0169 (9)	−0.0014 (8)	−0.0002 (7)	0.0009 (8)
C2B	0.0121 (10)	0.0122 (9)	0.0208 (9)	0.0021 (8)	0.0003 (7)	−0.0004 (8)
C3B	0.0128 (11)	0.0140 (9)	0.0178 (9)	−0.0010 (8)	0.0021 (7)	−0.0024 (8)
C4B	0.0143 (11)	0.0156 (10)	0.0223 (10)	0.0006 (8)	0.0017 (8)	−0.0014 (8)
C5B	0.0157 (12)	0.0213 (11)	0.0276 (11)	−0.0024 (9)	−0.0037 (9)	−0.0046 (9)
C6B	0.0236 (13)	0.0282 (12)	0.0188 (9)	−0.0005 (10)	−0.0044 (8)	−0.0061 (9)

Geometric parameters (Å, º) top

Br1A—C4A	1.888 (2)	C6—C7	1.385 (3)
Br1B—C4B	1.881 (2)	C7—H7A	0.9500
Cl1—C3	1.733 (2)	C1A—C2A	1.515 (3)
Cl2—C4	1.728 (2)	C1A—H1AA	0.9900
Cl3—C6	1.744 (2)	C1A—H1AB	0.9900
S1A—C6A	1.701 (2)	C2A—C3A	1.478 (3)
S1A—C3A	1.733 (2)	C3A—C4A	1.378 (3)
S1B—C6B	1.711 (2)	C4A—C5A	1.405 (3)
S1B—C3B	1.742 (2)	C5A—C6A	1.359 (3)
O1A—C2A	1.212 (2)	C5A—H5AA	0.9500
O1B—C2B	1.222 (2)	C6A—H6AA	0.9500
C1—C2	1.523 (3)	C1B—C2B	1.512 (3)
C1—C1A	1.528 (3)	C1B—H1BA	0.9900
C1—C1B	1.546 (3)	C1B—H1BB	0.9900
C1—H1A	1.0000	C2B—C3B	1.473 (3)
C2—C7	1.391 (3)	C3B—C4B	1.373 (3)
C2—C3	1.401 (3)	C4B—C5B	1.408 (3)
C3—C4	1.396 (3)	C5B—C6B	1.361 (3)
C4—C5	1.381 (3)	C5B—H5BA	0.9500
C5—C6	1.382 (3)	C6B—H6BA	0.9500
C5—H5A	0.9500

C6A—S1A—C3A	92.10 (11)	C3A—C2A—C1A	119.43 (17)
C6B—S1B—C3B	92.33 (11)	C4A—C3A—C2A	135.45 (19)
C2—C1—C1A	115.15 (17)	C4A—C3A—S1A	109.28 (15)
C2—C1—C1B	108.98 (15)	C2A—C3A—S1A	115.17 (15)
C1A—C1—C1B	109.70 (16)	C3A—C4A—C5A	114.39 (19)
C2—C1—H1A	107.6	C3A—C4A—Br1A	126.02 (16)
C1A—C1—H1A	107.6	C5A—C4A—Br1A	119.55 (16)
C1B—C1—H1A	107.6	C6A—C5A—C4A	111.5 (2)
C7—C2—C3	118.00 (19)	C6A—C5A—H5AA	124.3
C7—C2—C1	122.32 (18)	C4A—C5A—H5AA	124.3
C3—C2—C1	119.65 (19)	C5A—C6A—S1A	112.74 (18)
C4—C3—C2	120.77 (19)	C5A—C6A—H6AA	123.6
C4—C3—Cl1	119.11 (16)	S1A—C6A—H6AA	123.6
C2—C3—Cl1	120.12 (16)	C2B—C1B—C1	112.93 (16)
C5—C4—C3	120.71 (19)	C2B—C1B—H1BA	109.0
C5—C4—Cl2	118.63 (16)	C1—C1B—H1BA	109.0
C3—C4—Cl2	120.66 (17)	C2B—C1B—H1BB	109.0
C4—C5—C6	118.25 (19)	C1—C1B—H1BB	109.0
C4—C5—H5A	120.9	H1BA—C1B—H1BB	107.8
C6—C5—H5A	120.9	O1B—C2B—C3B	121.1 (2)
C5—C6—C7	122.0 (2)	O1B—C2B—C1B	121.62 (18)
C5—C6—Cl3	118.43 (17)	C3B—C2B—C1B	117.21 (17)
C7—C6—Cl3	119.62 (17)	C4B—C3B—C2B	129.74 (19)
C6—C7—C2	120.31 (19)	C4B—C3B—S1B	108.96 (15)
C6—C7—H7A	119.8	C2B—C3B—S1B	121.30 (16)
C2—C7—H7A	119.8	C3B—C4B—C5B	114.8 (2)
C2A—C1A—C1	113.50 (16)	C3B—C4B—Br1B	124.89 (16)
C2A—C1A—H1AA	108.9	C5B—C4B—Br1B	120.35 (17)
C1—C1A—H1AA	108.9	C6B—C5B—C4B	111.9 (2)
C2A—C1A—H1AB	108.9	C6B—C5B—H5BA	124.1
C1—C1A—H1AB	108.9	C4B—C5B—H5BA	124.1
H1AA—C1A—H1AB	107.7	C5B—C6B—S1B	112.07 (17)
O1A—C2A—C3A	118.89 (18)	C5B—C6B—H6BA	124.0
O1A—C2A—C1A	121.68 (19)	S1B—C6B—H6BA	124.0

C1A—C1—C2—C7	−22.0 (3)	C6A—S1A—C3A—C4A	0.15 (17)
C1B—C1—C2—C7	101.8 (2)	C6A—S1A—C3A—C2A	−176.73 (17)
C1A—C1—C2—C3	159.82 (17)	C2A—C3A—C4A—C5A	175.8 (2)
C1B—C1—C2—C3	−76.4 (2)	S1A—C3A—C4A—C5A	−0.2 (2)
C7—C2—C3—C4	0.4 (3)	C2A—C3A—C4A—Br1A	−2.0 (4)
C1—C2—C3—C4	178.70 (17)	S1A—C3A—C4A—Br1A	−178.02 (12)
C7—C2—C3—Cl1	179.98 (14)	C3A—C4A—C5A—C6A	0.1 (3)
C1—C2—C3—Cl1	−1.7 (2)	Br1A—C4A—C5A—C6A	178.10 (17)
C2—C3—C4—C5	0.0 (3)	C4A—C5A—C6A—S1A	0.0 (3)
Cl1—C3—C4—C5	−179.60 (15)	C3A—S1A—C6A—C5A	−0.1 (2)
C2—C3—C4—Cl2	179.97 (14)	C2—C1—C1B—C2B	160.27 (17)
Cl1—C3—C4—Cl2	0.4 (2)	C1A—C1—C1B—C2B	−72.8 (2)
C3—C4—C5—C6	−0.2 (3)	C1—C1B—C2B—O1B	−6.3 (3)
Cl2—C4—C5—C6	179.84 (14)	C1—C1B—C2B—C3B	175.29 (17)
C4—C5—C6—C7	0.0 (3)	O1B—C2B—C3B—C4B	−2.4 (4)
C4—C5—C6—Cl3	−179.34 (15)	C1B—C2B—C3B—C4B	176.0 (2)
C5—C6—C7—C2	0.4 (3)	O1B—C2B—C3B—S1B	178.49 (17)
Cl3—C6—C7—C2	179.73 (14)	C1B—C2B—C3B—S1B	−3.1 (3)
C3—C2—C7—C6	−0.6 (3)	C6B—S1B—C3B—C4B	−0.16 (17)
C1—C2—C7—C6	−178.85 (17)	C6B—S1B—C3B—C2B	179.10 (18)
C2—C1—C1A—C2A	−62.4 (2)	C2B—C3B—C4B—C5B	−179.5 (2)
C1B—C1—C1A—C2A	174.27 (17)	S1B—C3B—C4B—C5B	−0.3 (2)
C1—C1A—C2A—O1A	−4.9 (3)	C2B—C3B—C4B—Br1B	−0.2 (3)
C1—C1A—C2A—C3A	175.17 (18)	S1B—C3B—C4B—Br1B	178.98 (12)
O1A—C2A—C3A—C4A	−164.8 (2)	C3B—C4B—C5B—C6B	0.8 (3)
C1A—C2A—C3A—C4A	15.1 (4)	Br1B—C4B—C5B—C6B	−178.53 (17)
O1A—C2A—C3A—S1A	11.0 (3)	C4B—C5B—C6B—S1B	−0.9 (3)
C1A—C2A—C3A—S1A	−169.05 (15)	C3B—S1B—C6B—C5B	0.6 (2)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₁Br₂Cl₃O₂S₂
M_r	601.57
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	103
a, b, c (Å)	9.1380 (7), 16.0009 (11), 14.2139 (10)
β (°)	90.982 (1)
V (Å³)	2078.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.50
Crystal size (mm)	0.47 × 0.36 × 0.25

Data collection
Diffractometer	Bruker APEX2 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.418, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	23415, 6056, 4876
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.720

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.073, 1.04
No. of reflections	6056
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.11, −0.62

Computer programs: APEX2 (Bruker, 2006), APEX2, SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXTL (Bruker, 2000).

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1,5-Bis(3-bromo­thien-2-yl)-3-(2,3,5-trichloro­phen­yl)pentane-1,5-dione

Supporting information

Key indicators

checkCIF/PLATON results

1,5-Bis(3-bromothien-2-yl)-3-(2,3,5-trichlorophenyl)pentane-1,5-dione