Some chalcones derived from thio­phene-3-carbaldehyde: synthesis and crystal structures

A series of 3-(3-phenyl­prop-1-ene-3-one-1-yl)thio­phene derivatives containing –OH, –OCH₃, –OCH₂CH₃ and –Br at the para-position of the phenyl ring have been synthesized and their mol­ecular and crystal structures are reported.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 294 K
• R factor = 0.049
• wR factor = 0.134
• Data-to-parameter ratio = 16.0

Structure: 2

• Single-crystal X-ray study
• T = 294 K
• R factor = 0.046
• wR factor = 0.118
• Data-to-parameter ratio = 15.8

Structure: 3

• Single-crystal X-ray study
• T = 294 K
• R factor = 0.047
• wR factor = 0.141
• Data-to-parameter ratio = 16.6

Structure: 4

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.043
• wR factor = 0.107
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

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Datablock: 1


Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         S1 Check
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PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1       --C5       .        6.2 s.u.
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PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT230_ALERT_2_G Hirshfeld Test Diff for    S1A      --C5A      .        6.0 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        25% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         20 Note
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Computing details

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1-(4-Hydroxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one (1)

Crystal data

C13H10O2S	Dx = 1.341 Mg m^−3
Mr = 230.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3900 reflections
a = 11.0808 (5) Å	θ = 3.0–27.0°
b = 9.0251 (5) Å	µ = 0.26 mm^−1
c = 22.8157 (10) Å	T = 294 K
V = 2281.69 (19) Å^3	Block, yellow
Z = 8	0.4 × 0.3 × 0.07 mm
F(000) = 960

Data collection

SuperNova, single source at offset/far, Eos diffractometer	2333 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	1814 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.019
Detector resolution: 15.9631 pixels mm^-1	θmax = 26.4°, θmin = 2.6°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	k = −4→11
Tmin = 0.522, Tmax = 1.000	l = −27→28
9745 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 1.4972P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2333 reflections	Δρmax = 0.20 e Å^−3
146 parameters	Δρmin = −0.35 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
S1	0.89495 (8)	0.20994 (11)	0.39007 (3)	0.0907 (3)
C2	0.8168 (2)	0.3325 (4)	0.43118 (11)	0.0783 (8)
H2	0.749344	0.383495	0.417667	0.094*
C3	0.8629 (2)	0.3490 (3)	0.48637 (9)	0.0533 (6)
C4	0.9650 (2)	0.2575 (3)	0.49383 (11)	0.0637 (7)
H4	1.008933	0.252750	0.528507	0.076*
C5	0.9932 (2)	0.1760 (3)	0.44462 (11)	0.0704 (7)
H5	1.058032	0.110896	0.441931	0.085*
C6	0.8079 (2)	0.4425 (3)	0.53031 (10)	0.0550 (6)
H6	0.738492	0.493292	0.519204	0.066*
C7	0.8460 (2)	0.4637 (3)	0.58489 (9)	0.0521 (5)
H7	0.918191	0.420470	0.596709	0.062*
C8	0.77790 (19)	0.5528 (2)	0.62690 (9)	0.0486 (5)
O9	0.67534 (14)	0.5953 (2)	0.61457 (7)	0.0621 (5)
C10	0.83162 (18)	0.5889 (2)	0.68496 (9)	0.0458 (5)
C11	0.9339 (2)	0.5188 (3)	0.70693 (10)	0.0511 (5)
H11	0.973899	0.449440	0.683877	0.061*
C12	0.9773 (2)	0.5503 (3)	0.76226 (10)	0.0536 (6)
H12	1.044085	0.499832	0.776762	0.064*
C13	0.92110 (19)	0.6570 (2)	0.79603 (9)	0.0477 (5)
C14	0.8212 (2)	0.7312 (3)	0.77412 (10)	0.0545 (6)
H14	0.784258	0.804822	0.796302	0.065*
C15	0.77688 (19)	0.6960 (3)	0.71980 (10)	0.0518 (5)
H15	0.708722	0.744893	0.705920	0.062*
O16	0.95988 (15)	0.6936 (2)	0.85077 (6)	0.0601 (5)
H16	1.025310	0.654151	0.857006	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0964 (6)	0.1162 (8)	0.0596 (4)	0.0193 (5)	−0.0060 (4)	−0.0214 (4)
C2	0.0726 (17)	0.104 (2)	0.0583 (15)	0.0212 (17)	−0.0110 (13)	−0.0091 (15)
C3	0.0502 (12)	0.0622 (14)	0.0475 (12)	0.0007 (11)	0.0014 (10)	0.0023 (11)
C4	0.0598 (14)	0.0797 (17)	0.0515 (13)	0.0102 (13)	−0.0034 (11)	0.0004 (12)
C5	0.0670 (15)	0.0795 (19)	0.0647 (16)	0.0183 (15)	0.0016 (13)	−0.0065 (14)
C6	0.0479 (12)	0.0638 (15)	0.0533 (13)	0.0051 (11)	0.0010 (10)	0.0052 (11)
C7	0.0478 (12)	0.0562 (13)	0.0522 (12)	0.0038 (10)	0.0000 (10)	0.0012 (10)
C8	0.0475 (12)	0.0483 (12)	0.0500 (12)	−0.0017 (10)	0.0024 (9)	0.0060 (10)
O9	0.0497 (9)	0.0816 (12)	0.0550 (9)	0.0138 (9)	−0.0052 (7)	−0.0024 (8)
C10	0.0427 (11)	0.0441 (12)	0.0507 (12)	−0.0017 (9)	0.0037 (9)	0.0038 (9)
C11	0.0498 (12)	0.0477 (12)	0.0558 (13)	0.0051 (10)	−0.0003 (10)	−0.0054 (10)
C12	0.0482 (12)	0.0522 (13)	0.0604 (14)	0.0072 (11)	−0.0063 (10)	−0.0014 (11)
C13	0.0466 (11)	0.0492 (12)	0.0474 (11)	−0.0054 (10)	0.0022 (9)	0.0005 (10)
C14	0.0498 (12)	0.0562 (14)	0.0577 (13)	0.0065 (11)	0.0043 (10)	−0.0082 (11)
C15	0.0442 (11)	0.0523 (13)	0.0590 (13)	0.0079 (10)	−0.0022 (10)	0.0005 (11)
O16	0.0580 (10)	0.0712 (11)	0.0510 (9)	0.0040 (9)	−0.0045 (7)	−0.0082 (8)

Geometric parameters (Å, º)

S1—C2	1.689 (3)	C8—C10	1.488 (3)
S1—C5	1.682 (3)	C10—C11	1.392 (3)
C2—H2	0.9300	C10—C15	1.391 (3)
C2—C3	1.367 (3)	C11—H11	0.9300
C3—C4	1.411 (3)	C11—C12	1.380 (3)
C3—C6	1.446 (3)	C12—H12	0.9300
C4—H4	0.9300	C12—C13	1.382 (3)
C4—C5	1.378 (3)	C13—C14	1.387 (3)
C5—H5	0.9300	C13—O16	1.361 (2)
C6—H6	0.9300	C14—H14	0.9300
C6—C7	1.329 (3)	C14—C15	1.370 (3)
C7—H7	0.9300	C15—H15	0.9300
C7—C8	1.461 (3)	O16—H16	0.8200
C8—O9	1.232 (3)
C5—S1—C2	92.31 (13)	O9—C8—C10	120.3 (2)
S1—C2—H2	123.5	C11—C10—C8	123.2 (2)
C3—C2—S1	113.0 (2)	C15—C10—C8	119.10 (19)
C3—C2—H2	123.5	C15—C10—C11	117.7 (2)
C2—C3—C4	110.3 (2)	C10—C11—H11	119.4
C2—C3—C6	123.0 (2)	C12—C11—C10	121.3 (2)
C4—C3—C6	126.6 (2)	C12—C11—H11	119.4
C3—C4—H4	123.3	C11—C12—H12	120.1
C5—C4—C3	113.3 (2)	C11—C12—C13	119.8 (2)
C5—C4—H4	123.3	C13—C12—H12	120.1
S1—C5—H5	124.5	C12—C13—C14	119.7 (2)
C4—C5—S1	111.0 (2)	O16—C13—C12	122.6 (2)
C4—C5—H5	124.5	O16—C13—C14	117.8 (2)
C3—C6—H6	116.6	C13—C14—H14	120.0
C7—C6—C3	126.9 (2)	C15—C14—C13	120.0 (2)
C7—C6—H6	116.6	C15—C14—H14	120.0
C6—C7—H7	119.0	C10—C15—H15	119.3
C6—C7—C8	122.0 (2)	C14—C15—C10	121.4 (2)
C8—C7—H7	119.0	C14—C15—H15	119.3
C7—C8—C10	119.85 (19)	C13—O16—H16	109.5
O9—C8—C7	119.9 (2)
S1—C2—C3—C4	0.1 (3)	C7—C8—C10—C15	167.8 (2)
S1—C2—C3—C6	−177.0 (2)	C8—C10—C11—C12	−176.7 (2)
C2—S1—C5—C4	0.5 (3)	C8—C10—C15—C14	178.6 (2)
C2—C3—C4—C5	0.3 (4)	O9—C8—C10—C11	165.4 (2)
C2—C3—C6—C7	179.4 (3)	O9—C8—C10—C15	−13.6 (3)
C3—C4—C5—S1	−0.5 (3)	C10—C11—C12—C13	−2.3 (4)
C3—C6—C7—C8	−175.4 (2)	C11—C10—C15—C14	−0.5 (3)
C4—C3—C6—C7	2.7 (4)	C11—C12—C13—C14	0.3 (3)
C5—S1—C2—C3	−0.3 (3)	C11—C12—C13—O16	−179.7 (2)
C6—C3—C4—C5	177.3 (2)	C12—C13—C14—C15	1.6 (3)
C6—C7—C8—O9	9.1 (4)	C13—C14—C15—C10	−1.5 (4)
C6—C7—C8—C10	−172.3 (2)	C15—C10—C11—C12	2.4 (3)
C7—C8—C10—C11	−13.2 (3)	O16—C13—C14—C15	−178.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O16—H16···O9^i	0.82	1.86	2.667 (2)	167
C6—H6···O9	0.93	2.46	2.785 (3)	100
C11—H11···O16^ii	0.93	2.55	3.425 (3)	157

Symmetry codes: (i) x+1/2, y, −z+3/2; (ii) −x+2, y−1/2, −z+3/2.

1-(4-Methoxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one (2)

Crystal data

C14H12O2S	F(000) = 512
Mr = 244.30	Dx = 1.350 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.4118 (13) Å	Cell parameters from 1920 reflections
b = 5.8387 (5) Å	θ = 3.2–27.3°
c = 12.6456 (9) Å	µ = 0.26 mm^−1
β = 97.279 (7)°	T = 294 K
V = 1201.98 (16) Å^3	Block, white
Z = 4	0.45 × 0.3 × 0.15 mm

Data collection

SuperNova, single source at offset/far, Eos diffractometer	2457 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	1771 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.021
Detector resolution: 15.9631 pixels mm^-1	θmax = 26.4°, θmin = 2.5°
ω scans	h = −19→20
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	k = −4→7
Tmin = 0.803, Tmax = 1.000	l = −15→15
5075 measured reflections

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)] = 0.046	w = 1/[σ^2(Fo^2) + (0.0416P)^2 + 0.3903P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.118	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.16 e Å^−3
2457 reflections	Δρmin = −0.26 e Å^−3
156 parameters	Extinction correction: SHELXL-2016/4 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0141 (16)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
S1	0.04793 (4)	0.76040 (12)	0.07886 (5)	0.0654 (3)
C2	0.10560 (14)	0.9740 (4)	0.14100 (16)	0.0519 (6)
H2	0.116506	1.111424	0.108336	0.062*
C3	0.13426 (12)	0.9216 (4)	0.24447 (15)	0.0421 (5)
C4	0.10869 (13)	0.6985 (4)	0.27105 (18)	0.0494 (6)
H4	0.122905	0.631591	0.337572	0.059*
C5	0.06133 (14)	0.5929 (4)	0.18926 (18)	0.0558 (6)
H5	0.039091	0.447129	0.193370	0.067*
C6	0.18106 (12)	1.0798 (4)	0.31699 (16)	0.0463 (5)
H6	0.191362	1.224036	0.290462	0.056*
C7	0.21052 (13)	1.0373 (4)	0.41779 (16)	0.0477 (5)
H7	0.202752	0.892707	0.445659	0.057*
C8	0.25502 (13)	1.2111 (4)	0.48691 (17)	0.0468 (5)
O9	0.25416 (11)	1.4134 (3)	0.46020 (13)	0.0657 (5)
C10	0.30162 (12)	1.1378 (4)	0.58960 (15)	0.0430 (5)
C11	0.28855 (13)	0.9319 (4)	0.63854 (16)	0.0499 (6)
H11	0.249747	0.830772	0.605098	0.060*
C12	0.33136 (13)	0.8718 (4)	0.73559 (16)	0.0522 (6)
H12	0.320424	0.733792	0.767704	0.063*
C13	0.39048 (13)	1.0180 (4)	0.78457 (16)	0.0467 (5)
C14	0.40604 (15)	1.2229 (4)	0.73538 (19)	0.0588 (7)
H14	0.446764	1.320516	0.767118	0.071*
C15	0.36170 (15)	1.2817 (4)	0.64040 (18)	0.0565 (6)
H15	0.371979	1.421195	0.609103	0.068*
O16	0.43757 (9)	0.9765 (3)	0.87912 (11)	0.0586 (5)
C17	0.42397 (17)	0.7696 (5)	0.93373 (19)	0.0679 (7)
H17A	0.367631	0.762376	0.946635	0.102*
H17B	0.459086	0.765633	1.000460	0.102*
H17C	0.436021	0.641159	0.890914	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0659 (4)	0.0704 (5)	0.0552 (4)	0.0009 (3)	−0.0104 (3)	−0.0052 (3)
C2	0.0571 (13)	0.0487 (14)	0.0489 (12)	0.0044 (11)	0.0019 (10)	0.0049 (11)
C3	0.0414 (11)	0.0426 (13)	0.0418 (11)	0.0067 (9)	0.0036 (9)	0.0015 (10)
C4	0.0497 (12)	0.0462 (14)	0.0515 (12)	0.0020 (10)	0.0033 (10)	0.0054 (11)
C5	0.0510 (13)	0.0420 (13)	0.0730 (15)	−0.0027 (11)	0.0029 (11)	−0.0003 (12)
C6	0.0475 (12)	0.0419 (13)	0.0489 (12)	0.0019 (10)	0.0042 (10)	0.0038 (10)
C7	0.0507 (12)	0.0444 (13)	0.0470 (12)	−0.0033 (10)	0.0027 (10)	0.0024 (11)
C8	0.0487 (12)	0.0454 (14)	0.0469 (12)	−0.0009 (10)	0.0086 (9)	0.0006 (11)
O9	0.0854 (13)	0.0450 (10)	0.0631 (10)	−0.0029 (9)	−0.0039 (9)	0.0039 (9)
C10	0.0458 (11)	0.0421 (12)	0.0415 (11)	−0.0038 (10)	0.0072 (9)	−0.0039 (10)
C11	0.0523 (13)	0.0500 (14)	0.0455 (12)	−0.0152 (11)	−0.0013 (10)	−0.0011 (11)
C12	0.0595 (14)	0.0490 (14)	0.0465 (12)	−0.0131 (11)	0.0007 (10)	0.0038 (11)
C13	0.0449 (12)	0.0523 (14)	0.0420 (11)	−0.0022 (10)	0.0026 (9)	−0.0064 (11)
C14	0.0611 (14)	0.0541 (15)	0.0578 (14)	−0.0200 (12)	−0.0058 (11)	−0.0068 (12)
C15	0.0686 (15)	0.0452 (14)	0.0544 (13)	−0.0158 (12)	0.0027 (11)	0.0005 (11)
O16	0.0583 (10)	0.0640 (11)	0.0495 (9)	−0.0088 (8)	−0.0083 (7)	−0.0020 (8)
C17	0.0807 (18)	0.0666 (18)	0.0513 (14)	−0.0019 (14)	−0.0108 (12)	0.0017 (13)

Geometric parameters (Å, º)

S1—C2	1.697 (2)	C10—C11	1.381 (3)
S1—C5	1.696 (2)	C10—C15	1.390 (3)
C2—H2	0.9300	C11—H11	0.9300
C2—C3	1.368 (3)	C11—C12	1.380 (3)
C3—C4	1.422 (3)	C12—H12	0.9300
C3—C6	1.451 (3)	C12—C13	1.379 (3)
C4—H4	0.9300	C13—C14	1.387 (3)
C4—C5	1.360 (3)	C13—O16	1.361 (2)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C14—C15	1.367 (3)
C6—C7	1.328 (3)	C15—H15	0.9300
C7—H7	0.9300	O16—C17	1.423 (3)
C7—C8	1.471 (3)	C17—H17A	0.9600
C8—O9	1.228 (3)	C17—H17B	0.9600
C8—C10	1.484 (3)	C17—H17C	0.9600
C5—S1—C2	92.07 (11)	C15—C10—C8	119.1 (2)
S1—C2—H2	123.8	C10—C11—H11	119.0
C3—C2—S1	112.49 (18)	C12—C11—C10	122.0 (2)
C3—C2—H2	123.8	C12—C11—H11	119.0
C2—C3—C4	110.8 (2)	C11—C12—H12	120.3
C2—C3—C6	123.5 (2)	C13—C12—C11	119.5 (2)
C4—C3—C6	125.60 (19)	C13—C12—H12	120.3
C3—C4—H4	123.4	C12—C13—C14	119.44 (19)
C5—C4—C3	113.1 (2)	O16—C13—C12	125.0 (2)
C5—C4—H4	123.4	O16—C13—C14	115.54 (19)
S1—C5—H5	124.3	C13—C14—H14	119.9
C4—C5—S1	111.50 (18)	C15—C14—C13	120.2 (2)
C4—C5—H5	124.3	C15—C14—H14	119.9
C3—C6—H6	117.0	C10—C15—H15	119.3
C7—C6—C3	125.9 (2)	C14—C15—C10	121.4 (2)
C7—C6—H6	117.0	C14—C15—H15	119.3
C6—C7—H7	118.8	C13—O16—C17	118.08 (18)
C6—C7—C8	122.3 (2)	O16—C17—H17A	109.5
C8—C7—H7	118.8	O16—C17—H17B	109.5
C7—C8—C10	118.9 (2)	O16—C17—H17C	109.5
O9—C8—C7	120.8 (2)	H17A—C17—H17B	109.5
O9—C8—C10	120.3 (2)	H17A—C17—H17C	109.5
C11—C10—C8	123.42 (19)	H17B—C17—H17C	109.5
C11—C10—C15	117.43 (19)
S1—C2—C3—C4	1.0 (2)	C8—C10—C11—C12	−178.1 (2)
S1—C2—C3—C6	−176.32 (16)	C8—C10—C15—C14	179.6 (2)
C2—S1—C5—C4	−0.02 (19)	O9—C8—C10—C11	162.0 (2)
C2—C3—C4—C5	−1.1 (3)	O9—C8—C10—C15	−17.9 (3)
C2—C3—C6—C7	−179.7 (2)	C10—C11—C12—C13	−1.6 (4)
C3—C4—C5—S1	0.6 (3)	C11—C10—C15—C14	−0.3 (4)
C3—C6—C7—C8	−177.8 (2)	C11—C12—C13—C14	−0.1 (3)
C4—C3—C6—C7	3.3 (4)	C11—C12—C13—O16	−178.9 (2)
C5—S1—C2—C3	−0.60 (18)	C12—C13—C14—C15	1.6 (4)
C6—C3—C4—C5	176.2 (2)	C12—C13—O16—C17	−1.6 (3)
C6—C7—C8—O9	13.0 (3)	C13—C14—C15—C10	−1.4 (4)
C6—C7—C8—C10	−166.6 (2)	C14—C13—O16—C17	179.5 (2)
C7—C8—C10—C11	−18.4 (3)	C15—C10—C11—C12	1.8 (3)
C7—C8—C10—C15	161.7 (2)	O16—C13—C14—C15	−179.5 (2)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the S1/C2–C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1^i	0.93	2.94	3.602 (2)	129
C11—H11···Cg1^ii	0.93	2.99	3.598 (2)	125

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+3/2, z+1/2.

1-(4-Ethoxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one (3)

Crystal data

C15H14O2S	F(000) = 544
Mr = 258.32	Dx = 1.281 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.5120 (8) Å	Cell parameters from 4827 reflections
b = 7.7851 (5) Å	θ = 3.3–27.9°
c = 10.4913 (5) Å	µ = 0.23 mm^−1
β = 96.813 (4)°	T = 294 K
V = 1339.11 (13) Å^3	Block, white
Z = 4	0.5 × 0.35 × 0.15 mm

Data collection

SuperNova, single source at offset/far, Eos diffractometer	2734 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2162 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.035
Detector resolution: 15.9631 pixels mm^-1	θmax = 26.4°, θmin = 2.5°
ω scans	h = −20→20
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	k = −9→9
Tmin = 0.733, Tmax = 1.000	l = −12→13
13246 measured reflections

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)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0633P)^2 + 0.4069P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.141	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.19 e Å^−3
2734 reflections	Δρmin = −0.28 e Å^−3
165 parameters	Extinction correction: SHELXL-2016/4 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0073 (17)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
S1	0.28921 (3)	0.41932 (9)	0.57261 (6)	0.0697 (3)
C2	0.35583 (12)	0.4427 (3)	0.70816 (19)	0.0558 (5)
H2	0.340852	0.481608	0.785855	0.067*
C3	0.43322 (11)	0.3985 (2)	0.69052 (17)	0.0458 (4)
C4	0.43736 (12)	0.3435 (3)	0.56166 (18)	0.0551 (5)
H4	0.485324	0.307932	0.531318	0.066*
C5	0.36332 (13)	0.3486 (3)	0.4872 (2)	0.0588 (5)
H5	0.354921	0.317238	0.401153	0.071*
C6	0.50131 (12)	0.4082 (2)	0.79107 (18)	0.0483 (5)
H6	0.489859	0.443268	0.871763	0.058*
C7	0.57803 (12)	0.3718 (3)	0.77867 (18)	0.0518 (5)
H7	0.591201	0.335993	0.699110	0.062*
C8	0.64340 (12)	0.3860 (3)	0.88615 (17)	0.0490 (5)
O9	0.62809 (9)	0.3934 (2)	0.99739 (13)	0.0670 (5)
C10	0.72986 (12)	0.3954 (2)	0.85742 (17)	0.0476 (5)
C11	0.75356 (12)	0.3597 (3)	0.73833 (18)	0.0540 (5)
H11	0.714251	0.329023	0.671266	0.065*
C12	0.83455 (13)	0.3684 (3)	0.7166 (2)	0.0594 (5)
H12	0.849281	0.344313	0.635592	0.071*
C13	0.89322 (13)	0.4129 (3)	0.8157 (2)	0.0568 (5)
C14	0.87043 (13)	0.4512 (3)	0.9360 (2)	0.0618 (6)
H14	0.909675	0.483056	1.002823	0.074*
C15	0.79065 (13)	0.4420 (3)	0.95555 (19)	0.0571 (5)
H15	0.776104	0.467265	1.036427	0.069*
O16	0.97471 (9)	0.4227 (2)	0.80525 (16)	0.0762 (5)
C17	1.00141 (16)	0.3853 (4)	0.6849 (3)	0.0901 (9)
H17A	0.978364	0.467414	0.621098	0.108*
H17B	0.983604	0.271209	0.656990	0.108*
C18	1.09277 (17)	0.3952 (5)	0.6991 (4)	0.1138 (13)
H18A	1.111988	0.364258	0.619307	0.171*
H18B	1.115025	0.317438	0.765128	0.171*
H18C	1.109771	0.510223	0.721773	0.171*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0502 (4)	0.0898 (5)	0.0684 (4)	0.0040 (3)	0.0052 (3)	0.0000 (3)
C2	0.0549 (12)	0.0668 (13)	0.0479 (11)	0.0079 (10)	0.0153 (9)	0.0016 (9)
C3	0.0481 (10)	0.0477 (10)	0.0430 (10)	0.0015 (8)	0.0115 (8)	0.0017 (8)
C4	0.0505 (11)	0.0663 (13)	0.0500 (11)	0.0015 (9)	0.0128 (9)	−0.0087 (9)
C5	0.0619 (13)	0.0676 (13)	0.0472 (11)	0.0005 (10)	0.0072 (9)	−0.0116 (10)
C6	0.0522 (11)	0.0544 (11)	0.0397 (9)	0.0043 (8)	0.0118 (8)	0.0013 (8)
C7	0.0507 (11)	0.0654 (13)	0.0400 (10)	0.0021 (9)	0.0090 (8)	−0.0020 (9)
C8	0.0506 (11)	0.0582 (12)	0.0387 (10)	0.0054 (9)	0.0077 (8)	0.0025 (8)
O9	0.0584 (9)	0.1032 (13)	0.0407 (8)	0.0094 (8)	0.0111 (6)	0.0024 (7)
C10	0.0506 (11)	0.0527 (11)	0.0393 (9)	0.0030 (8)	0.0047 (8)	0.0035 (8)
C11	0.0491 (11)	0.0707 (14)	0.0422 (10)	−0.0022 (9)	0.0049 (8)	−0.0041 (9)
C12	0.0534 (12)	0.0780 (15)	0.0476 (11)	−0.0027 (10)	0.0098 (9)	−0.0075 (10)
C13	0.0461 (11)	0.0669 (14)	0.0580 (12)	−0.0025 (9)	0.0089 (9)	0.0003 (10)
C14	0.0550 (12)	0.0813 (16)	0.0472 (11)	−0.0048 (11)	−0.0020 (9)	−0.0035 (10)
C15	0.0553 (12)	0.0759 (14)	0.0398 (10)	0.0003 (10)	0.0045 (9)	−0.0005 (9)
O16	0.0476 (9)	0.1096 (15)	0.0726 (11)	−0.0107 (8)	0.0115 (7)	−0.0139 (9)
C17	0.0590 (15)	0.121 (2)	0.095 (2)	−0.0131 (14)	0.0279 (14)	−0.0264 (17)
C18	0.0593 (16)	0.135 (3)	0.153 (3)	−0.0193 (16)	0.0391 (18)	−0.049 (2)

Geometric parameters (Å, º)

S1—C2	1.701 (2)	C11—H11	0.9300
S1—C5	1.692 (2)	C11—C12	1.385 (3)
C2—H2	0.9300	C12—H12	0.9300
C2—C3	1.357 (3)	C12—C13	1.379 (3)
C3—C4	1.427 (3)	C13—C14	1.392 (3)
C3—C6	1.450 (3)	C13—O16	1.365 (3)
C4—H4	0.9300	C14—H14	0.9300
C4—C5	1.371 (3)	C14—C15	1.359 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	O16—C17	1.416 (3)
C6—C7	1.319 (3)	C17—H17A	0.9700
C7—H7	0.9300	C17—H17B	0.9700
C7—C8	1.470 (3)	C17—C18	1.500 (4)
C8—O9	1.224 (2)	C18—H18A	0.9600
C8—C10	1.496 (3)	C18—H18B	0.9600
C10—C11	1.381 (3)	C18—H18C	0.9600
C10—C15	1.398 (3)
C5—S1—C2	92.34 (10)	C12—C11—H11	119.3
S1—C2—H2	123.7	C11—C12—H12	120.2
C3—C2—S1	112.62 (15)	C13—C12—C11	119.60 (19)
C3—C2—H2	123.7	C13—C12—H12	120.2
C2—C3—C4	110.92 (18)	C12—C13—C14	119.8 (2)
C2—C3—C6	123.30 (17)	O16—C13—C12	124.39 (19)
C4—C3—C6	125.79 (17)	O16—C13—C14	115.84 (19)
C3—C4—H4	123.5	C13—C14—H14	120.1
C5—C4—C3	113.01 (18)	C15—C14—C13	119.78 (19)
C5—C4—H4	123.5	C15—C14—H14	120.1
S1—C5—H5	124.4	C10—C15—H15	119.1
C4—C5—S1	111.11 (15)	C14—C15—C10	121.80 (19)
C4—C5—H5	124.4	C14—C15—H15	119.1
C3—C6—H6	117.0	C13—O16—C17	118.30 (18)
C7—C6—C3	126.00 (18)	O16—C17—H17A	110.0
C7—C6—H6	117.0	O16—C17—H17B	110.0
C6—C7—H7	118.8	O16—C17—C18	108.5 (2)
C6—C7—C8	122.31 (18)	H17A—C17—H17B	108.4
C8—C7—H7	118.8	C18—C17—H17A	110.0
C7—C8—C10	118.74 (16)	C18—C17—H17B	110.0
O9—C8—C7	121.26 (18)	C17—C18—H18A	109.5
O9—C8—C10	119.99 (17)	C17—C18—H18B	109.5
C11—C10—C8	123.51 (17)	C17—C18—H18C	109.5
C11—C10—C15	117.56 (18)	H18A—C18—H18B	109.5
C15—C10—C8	118.92 (17)	H18A—C18—H18C	109.5
C10—C11—H11	119.3	H18B—C18—H18C	109.5
C10—C11—C12	121.47 (19)
S1—C2—C3—C4	−0.1 (2)	C8—C10—C15—C14	179.3 (2)
S1—C2—C3—C6	179.55 (15)	O9—C8—C10—C11	168.8 (2)
C2—S1—C5—C4	−0.05 (18)	O9—C8—C10—C15	−10.9 (3)
C2—C3—C4—C5	0.1 (3)	C10—C11—C12—C13	0.3 (3)
C2—C3—C6—C7	−177.9 (2)	C11—C10—C15—C14	−0.4 (3)
C3—C4—C5—S1	0.0 (2)	C11—C12—C13—C14	−1.0 (3)
C3—C6—C7—C8	179.75 (18)	C11—C12—C13—O16	178.9 (2)
C4—C3—C6—C7	1.8 (3)	C12—C13—C14—C15	1.0 (3)
C5—S1—C2—C3	0.11 (18)	C12—C13—O16—C17	0.2 (3)
C6—C3—C4—C5	−179.58 (19)	C13—C14—C15—C10	−0.3 (4)
C6—C7—C8—O9	17.1 (3)	C13—O16—C17—C18	−177.0 (2)
C6—C7—C8—C10	−161.57 (19)	C14—C13—O16—C17	−179.9 (2)
C7—C8—C10—C11	−12.6 (3)	C15—C10—C11—C12	0.4 (3)
C7—C8—C10—C15	167.75 (19)	O16—C13—C14—C15	−178.9 (2)
C8—C10—C11—C12	−179.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O9^i	0.93	2.47	3.324 (2)	153

Symmetry code: (i) −x+1, −y+1, −z+2.

1-(4-Bromophenyl)-3-(thiophen-3-yl)prop-1-en-3-one (4)

Crystal data

C13H9BrOS	F(000) = 584
Mr = 293.17	Dx = 1.667 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.1245 (7) Å	Cell parameters from 4399 reflections
b = 14.2016 (13) Å	θ = 2.9–27.3°
c = 5.8809 (4) Å	µ = 3.67 mm^−1
β = 98.081 (6)°	T = 293 K
V = 1167.93 (15) Å^3	Plate, yellow
Z = 4	0.4 × 0.4 × 0.05 mm

Data collection

SuperNova, single source at offset/far, Eos diffractometer	2392 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	1683 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.045
Detector resolution: 15.9631 pixels mm^-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −17→17
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	k = −17→17
Tmin = 0.367, Tmax = 1.000	l = −7→7
12050 measured reflections

Refinement

Refinement on F^2	20 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0407P)^2 + 0.7623P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
2392 reflections	Δρmax = 0.40 e Å^−3
158 parameters	Δρmin = −0.46 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1A	0.07255 (13)	0.3898 (2)	0.4329 (4)	0.0574 (6)	0.702 (4)
S1B	0.1418 (5)	0.3457 (7)	0.2749 (13)	0.0574 (6)	0.298 (4)
C2A	0.1532 (7)	0.412 (2)	0.663 (3)	0.048 (3)	0.702 (4)
H2A	0.137355	0.439712	0.795694	0.058*	0.702 (4)
C2B	0.2476 (16)	0.341 (5)	0.438 (6)	0.048 (3)	0.298 (4)
H2B	0.301123	0.310516	0.397088	0.058*	0.298 (4)
C3	0.2452 (2)	0.3858 (2)	0.6388 (5)	0.0417 (8)
C4A	0.2461 (7)	0.3456 (17)	0.416 (2)	0.048 (3)	0.702 (4)
H4A	0.302496	0.326195	0.365401	0.058*	0.702 (4)
C4B	0.1551 (18)	0.422 (5)	0.664 (6)	0.048 (3)	0.298 (4)
H4B	0.142572	0.455562	0.792513	0.058*	0.298 (4)
C5A	0.1586 (7)	0.3375 (9)	0.2809 (18)	0.053 (3)	0.702 (4)
H5A	0.146845	0.309732	0.136500	0.063*	0.702 (4)
C5B	0.0855 (10)	0.4021 (19)	0.475 (3)	0.053 (3)	0.298 (4)
H5B	0.020804	0.416891	0.461047	0.063*	0.298 (4)
C6	0.3264 (2)	0.3933 (2)	0.8186 (6)	0.0451 (8)
H6	0.313682	0.414696	0.960622	0.054*
C7	0.4168 (2)	0.3729 (2)	0.8023 (6)	0.0485 (9)
H7	0.433284	0.356673	0.659823	0.058*
C8	0.4916 (3)	0.3752 (2)	1.0027 (6)	0.0460 (8)
O9	0.4718 (2)	0.3764 (2)	1.1988 (4)	0.0676 (8)
C10	0.5938 (2)	0.3754 (2)	0.9658 (5)	0.0403 (8)
C11	0.6238 (2)	0.4075 (2)	0.7646 (6)	0.0451 (8)
H11	0.578794	0.428136	0.644229	0.054*
C12	0.7202 (3)	0.4092 (3)	0.7410 (6)	0.0470 (8)
H12	0.740087	0.432427	0.607649	0.056*
C13	0.7860 (2)	0.3760 (2)	0.9180 (6)	0.0434 (8)
C14	0.7584 (3)	0.3438 (3)	1.1203 (6)	0.0491 (9)
H14	0.803570	0.322082	1.239069	0.059*
C15	0.6624 (2)	0.3447 (2)	1.1429 (6)	0.0447 (8)
H15	0.643292	0.324227	1.279603	0.054*
Br16	0.91660 (3)	0.37156 (4)	0.88024 (8)	0.0730 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0459 (8)	0.0718 (14)	0.0532 (11)	0.0051 (8)	0.0029 (6)	−0.0014 (9)
S1B	0.0459 (8)	0.0718 (14)	0.0532 (11)	0.0051 (8)	0.0029 (6)	−0.0014 (9)
C2A	0.044 (4)	0.056 (10)	0.045 (4)	0.006 (4)	0.010 (3)	−0.004 (4)
C2B	0.044 (4)	0.056 (10)	0.045 (4)	0.006 (4)	0.010 (3)	−0.004 (4)
C3	0.0453 (19)	0.0398 (19)	0.0417 (18)	−0.0020 (15)	0.0115 (15)	0.0021 (15)
C4A	0.052 (4)	0.051 (5)	0.043 (5)	−0.002 (3)	0.013 (3)	−0.006 (5)
C4B	0.052 (4)	0.051 (5)	0.043 (5)	−0.002 (3)	0.013 (3)	−0.006 (5)
C5A	0.058 (6)	0.055 (5)	0.051 (4)	0.015 (4)	0.025 (4)	−0.013 (3)
C5B	0.058 (6)	0.055 (5)	0.051 (4)	0.015 (4)	0.025 (4)	−0.013 (3)
C6	0.045 (2)	0.051 (2)	0.0416 (19)	−0.0044 (16)	0.0107 (15)	−0.0040 (15)
C7	0.047 (2)	0.054 (2)	0.0452 (19)	−0.0018 (17)	0.0105 (16)	−0.0068 (16)
C8	0.0447 (19)	0.050 (2)	0.045 (2)	0.0020 (16)	0.0112 (16)	−0.0036 (16)
O9	0.0531 (16)	0.107 (3)	0.0450 (15)	0.0056 (14)	0.0139 (12)	0.0000 (14)
C10	0.0455 (19)	0.0372 (18)	0.0386 (18)	−0.0011 (15)	0.0075 (15)	−0.0038 (14)
C11	0.049 (2)	0.050 (2)	0.0350 (18)	0.0028 (17)	0.0007 (15)	0.0004 (15)
C12	0.054 (2)	0.051 (2)	0.0366 (18)	−0.0055 (17)	0.0101 (16)	0.0013 (16)
C13	0.0382 (18)	0.045 (2)	0.048 (2)	−0.0061 (15)	0.0075 (15)	−0.0056 (16)
C14	0.051 (2)	0.050 (2)	0.0426 (19)	−0.0004 (17)	−0.0036 (16)	0.0041 (16)
C15	0.050 (2)	0.048 (2)	0.0363 (18)	−0.0041 (17)	0.0062 (15)	0.0021 (15)
Br16	0.0430 (3)	0.0970 (4)	0.0803 (4)	−0.0074 (2)	0.0128 (2)	0.0047 (2)

Geometric parameters (Å, º)

S1A—C2A	1.671 (8)	C6—H6	0.9300
C2A—H2A	0.9300	C6—C7	1.325 (5)
S1B—C2B	1.661 (16)	C7—H7	0.9300
C2B—H2B	0.9300	C7—C8	1.469 (5)
C2A—C3	1.378 (9)	C8—O9	1.224 (4)
C2B—C3	1.347 (16)	C8—C10	1.489 (5)
C4A—H4A	0.9300	C10—C11	1.389 (5)
C4B—H4B	0.9300	C10—C15	1.390 (5)
S1A—C5A	1.770 (8)	C11—H11	0.9300
C4A—C5A	1.378 (11)	C11—C12	1.388 (5)
C5A—H5A	0.9300	C12—H12	0.9300
S1B—C5B	1.708 (15)	C12—C13	1.378 (5)
C4B—C5B	1.407 (16)	C13—C14	1.381 (5)
C5B—H5B	0.9300	C13—Br16	1.890 (3)
C3—C4A	1.431 (8)	C14—H14	0.9300
C3—C4B	1.400 (16)	C14—C15	1.381 (5)
C3—C6	1.451 (5)	C15—H15	0.9300
C4A—C5A—S1A	107.3 (6)	C7—C6—C3	127.0 (3)
C4B—C5B—S1B	107.4 (9)	C7—C6—H6	116.5
S1A—C2A—H2A	122.9	C6—C7—H7	119.0
S1B—C2B—H2B	124.6	C6—C7—C8	121.9 (3)
C5A—C4A—C3	116.0 (7)	C8—C7—H7	119.0
C5A—C4A—H4A	122.0	C7—C8—C10	119.1 (3)
C5B—C4B—H4B	123.6	O9—C8—C7	121.5 (3)
C2A—S1A—C5A	92.8 (4)	O9—C8—C10	119.5 (3)
S1A—C5A—H5A	126.3	C11—C10—C8	122.9 (3)
C4A—C5A—H5A	126.3	C11—C10—C15	118.5 (3)
C2B—S1B—C5B	95.2 (7)	C15—C10—C8	118.6 (3)
C4B—C5B—H5B	126.3	C10—C11—H11	119.6
S1B—C5B—H5B	126.3	C12—C11—C10	120.8 (3)
C2A—C3—C4A	109.4 (5)	C12—C11—H11	119.6
C2B—C3—C4B	113.8 (9)	C11—C12—H12	120.5
C4A—C3—C6	126.0 (4)	C13—C12—C11	119.1 (3)
C4B—C3—C6	122.2 (7)	C13—C12—H12	120.5
C2B—C3—C6	124.0 (7)	C12—C13—C14	121.5 (3)
C2A—C3—C6	124.5 (5)	C12—C13—Br16	119.2 (3)
C3—C6—H6	116.5	C14—C13—Br16	119.3 (3)
C3—C2A—S1A	114.3 (5)	C13—C14—H14	120.7
C3—C2B—S1B	110.7 (9)	C15—C14—C13	118.7 (3)
C3—C2A—H2A	122.9	C15—C14—H14	120.7
C3—C2B—H2B	124.6	C10—C15—H15	119.3
C3—C4A—H4A	122.0	C14—C15—C10	121.5 (3)
C3—C4B—H4B	123.6	C14—C15—H15	119.3
C3—C4B—C5B	112.7 (11)
C2A—S1A—C5A—C4A	−3 (2)	C6—C3—C4B—C5B	−176 (3)
C2B—S1B—C5B—C4B	4 (5)	C6—C7—C8—O9	15.6 (6)
C5B—S1B—C2B—C3	−4 (5)	C6—C7—C8—C10	−164.9 (3)
C5A—S1A—C2A—C3	2 (2)	C7—C8—C10—C11	24.4 (5)
S1A—C2A—C3—C4A	0 (2)	C7—C8—C10—C15	−157.6 (3)
S1B—C2B—C3—C4B	2 (5)	C8—C10—C11—C12	177.8 (3)
S1B—C2B—C3—C6	179.7 (18)	C8—C10—C15—C14	−179.4 (3)
S1A—C2A—C3—C6	−176.6 (10)	O9—C8—C10—C11	−156.0 (4)
C2A—C3—C6—C7	−177.0 (17)	O9—C8—C10—C15	22.0 (5)
C2B—C3—C6—C7	13 (4)	C10—C11—C12—C13	1.8 (5)
C4A—C3—C6—C7	6.9 (15)	C11—C10—C15—C14	−1.3 (5)
C4B—C3—C6—C7	−170 (4)	C11—C12—C13—C14	−2.0 (5)
C2A—C3—C4A—C5A	−3 (2)	C11—C12—C13—Br16	176.5 (3)
C2B—C3—C4B—C5B	1 (6)	C12—C13—C14—C15	0.5 (5)
C3—C4B—C5B—S1B	−4 (7)	C13—C14—C15—C10	1.2 (5)
C3—C4A—C5A—S1A	4 (2)	C15—C10—C11—C12	−0.2 (5)
C3—C6—C7—C8	−174.3 (3)	Br16—C13—C14—C15	−177.9 (3)
C6—C3—C4A—C5A	173.8 (12)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the major- and minor-disorder components of the thiophene ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5A—H5A···Cg1^i	0.93	2.80	3.493 (14)	132
C5A—H5A···Cg2^i	0.93	2.85	3.52 (2)	130

Symmetry code: (i) x, −y+1/2, z−1/2.