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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019007503/lh5905sup1.cif
Contains datablocks 1, 2, 3, 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019007503/lh59051sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019007503/lh59052sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019007503/lh59053sup4.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019007503/lh59054sup5.hkl
Contains datablock 4

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019007503/lh59051sup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019007503/lh59052sup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019007503/lh59053sup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019007503/lh59054sup9.cml
Supplementary material

CCDC references: 1918095; 1918094; 1918093; 1918092

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.049
  • wR factor = 0.134
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of S1 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.909 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 2 Report
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Datablock: 2
Alert level C PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.613 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Datablock: 3
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 --C5 . 6.2 s.u. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.715 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Datablock: 4
Alert level C PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.870 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check 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 PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 2 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 4 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 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 2 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 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

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) top
Crystal data top
C13H10O2SDx = 1.341 Mg m3
Mr = 230.27Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 3900 reflections
a = 11.0808 (5) Åθ = 3.0–27.0°
b = 9.0251 (5) ŵ = 0.26 mm1
c = 22.8157 (10) ÅT = 294 K
V = 2281.69 (19) Å3Block, yellow
Z = 80.4 × 0.3 × 0.07 mm
F(000) = 960
Data collection top
SuperNova, single source at offset/far, Eos
diffractometer
2333 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source1814 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.019
Detector resolution: 15.9631 pixels mm-1θmax = 26.4°, θmin = 2.6°
ω scansh = 1313
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2018)
k = 411
Tmin = 0.522, Tmax = 1.000l = 2728
9745 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.134 w = 1/[σ2(Fo2) + (0.0463P)2 + 1.4972P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2333 reflectionsΔρmax = 0.20 e Å3
146 parametersΔρmin = 0.35 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.89495 (8)0.20994 (11)0.39007 (3)0.0907 (3)
C20.8168 (2)0.3325 (4)0.43118 (11)0.0783 (8)
H20.7493440.3834950.4176670.094*
C30.8629 (2)0.3490 (3)0.48637 (9)0.0533 (6)
C40.9650 (2)0.2575 (3)0.49383 (11)0.0637 (7)
H41.0089330.2527500.5285070.076*
C50.9932 (2)0.1760 (3)0.44462 (11)0.0704 (7)
H51.0580320.1108960.4419310.085*
C60.8079 (2)0.4425 (3)0.53031 (10)0.0550 (6)
H60.7384920.4932920.5192040.066*
C70.8460 (2)0.4637 (3)0.58489 (9)0.0521 (5)
H70.9181910.4204700.5967090.062*
C80.77790 (19)0.5528 (2)0.62690 (9)0.0486 (5)
O90.67534 (14)0.5953 (2)0.61457 (7)0.0621 (5)
C100.83162 (18)0.5889 (2)0.68496 (9)0.0458 (5)
C110.9339 (2)0.5188 (3)0.70693 (10)0.0511 (5)
H110.9738990.4494400.6838770.061*
C120.9773 (2)0.5503 (3)0.76226 (10)0.0536 (6)
H121.0440850.4998320.7767620.064*
C130.92110 (19)0.6570 (2)0.79603 (9)0.0477 (5)
C140.8212 (2)0.7312 (3)0.77412 (10)0.0545 (6)
H140.7842580.8048220.7963020.065*
C150.77688 (19)0.6960 (3)0.71980 (10)0.0518 (5)
H150.7087220.7448930.7059200.062*
O160.95988 (15)0.6936 (2)0.85077 (6)0.0601 (5)
H161.0253100.6541510.8570060.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0964 (6)0.1162 (8)0.0596 (4)0.0193 (5)0.0060 (4)0.0214 (4)
C20.0726 (17)0.104 (2)0.0583 (15)0.0212 (17)0.0110 (13)0.0091 (15)
C30.0502 (12)0.0622 (14)0.0475 (12)0.0007 (11)0.0014 (10)0.0023 (11)
C40.0598 (14)0.0797 (17)0.0515 (13)0.0102 (13)0.0034 (11)0.0004 (12)
C50.0670 (15)0.0795 (19)0.0647 (16)0.0183 (15)0.0016 (13)0.0065 (14)
C60.0479 (12)0.0638 (15)0.0533 (13)0.0051 (11)0.0010 (10)0.0052 (11)
C70.0478 (12)0.0562 (13)0.0522 (12)0.0038 (10)0.0000 (10)0.0012 (10)
C80.0475 (12)0.0483 (12)0.0500 (12)0.0017 (10)0.0024 (9)0.0060 (10)
O90.0497 (9)0.0816 (12)0.0550 (9)0.0138 (9)0.0052 (7)0.0024 (8)
C100.0427 (11)0.0441 (12)0.0507 (12)0.0017 (9)0.0037 (9)0.0038 (9)
C110.0498 (12)0.0477 (12)0.0558 (13)0.0051 (10)0.0003 (10)0.0054 (10)
C120.0482 (12)0.0522 (13)0.0604 (14)0.0072 (11)0.0063 (10)0.0014 (11)
C130.0466 (11)0.0492 (12)0.0474 (11)0.0054 (10)0.0022 (9)0.0005 (10)
C140.0498 (12)0.0562 (14)0.0577 (13)0.0065 (11)0.0043 (10)0.0082 (11)
C150.0442 (11)0.0523 (13)0.0590 (13)0.0079 (10)0.0022 (10)0.0005 (11)
O160.0580 (10)0.0712 (11)0.0510 (9)0.0040 (9)0.0045 (7)0.0082 (8)
Geometric parameters (Å, º) top
S1—C21.689 (3)C8—C101.488 (3)
S1—C51.682 (3)C10—C111.392 (3)
C2—H20.9300C10—C151.391 (3)
C2—C31.367 (3)C11—H110.9300
C3—C41.411 (3)C11—C121.380 (3)
C3—C61.446 (3)C12—H120.9300
C4—H40.9300C12—C131.382 (3)
C4—C51.378 (3)C13—C141.387 (3)
C5—H50.9300C13—O161.361 (2)
C6—H60.9300C14—H140.9300
C6—C71.329 (3)C14—C151.370 (3)
C7—H70.9300C15—H150.9300
C7—C81.461 (3)O16—H160.8200
C8—O91.232 (3)
C5—S1—C292.31 (13)O9—C8—C10120.3 (2)
S1—C2—H2123.5C11—C10—C8123.2 (2)
C3—C2—S1113.0 (2)C15—C10—C8119.10 (19)
C3—C2—H2123.5C15—C10—C11117.7 (2)
C2—C3—C4110.3 (2)C10—C11—H11119.4
C2—C3—C6123.0 (2)C12—C11—C10121.3 (2)
C4—C3—C6126.6 (2)C12—C11—H11119.4
C3—C4—H4123.3C11—C12—H12120.1
C5—C4—C3113.3 (2)C11—C12—C13119.8 (2)
C5—C4—H4123.3C13—C12—H12120.1
S1—C5—H5124.5C12—C13—C14119.7 (2)
C4—C5—S1111.0 (2)O16—C13—C12122.6 (2)
C4—C5—H5124.5O16—C13—C14117.8 (2)
C3—C6—H6116.6C13—C14—H14120.0
C7—C6—C3126.9 (2)C15—C14—C13120.0 (2)
C7—C6—H6116.6C15—C14—H14120.0
C6—C7—H7119.0C10—C15—H15119.3
C6—C7—C8122.0 (2)C14—C15—C10121.4 (2)
C8—C7—H7119.0C14—C15—H15119.3
C7—C8—C10119.85 (19)C13—O16—H16109.5
O9—C8—C7119.9 (2)
S1—C2—C3—C40.1 (3)C7—C8—C10—C15167.8 (2)
S1—C2—C3—C6177.0 (2)C8—C10—C11—C12176.7 (2)
C2—S1—C5—C40.5 (3)C8—C10—C15—C14178.6 (2)
C2—C3—C4—C50.3 (4)O9—C8—C10—C11165.4 (2)
C2—C3—C6—C7179.4 (3)O9—C8—C10—C1513.6 (3)
C3—C4—C5—S10.5 (3)C10—C11—C12—C132.3 (4)
C3—C6—C7—C8175.4 (2)C11—C10—C15—C140.5 (3)
C4—C3—C6—C72.7 (4)C11—C12—C13—C140.3 (3)
C5—S1—C2—C30.3 (3)C11—C12—C13—O16179.7 (2)
C6—C3—C4—C5177.3 (2)C12—C13—C14—C151.6 (3)
C6—C7—C8—O99.1 (4)C13—C14—C15—C101.5 (4)
C6—C7—C8—C10172.3 (2)C15—C10—C11—C122.4 (3)
C7—C8—C10—C1113.2 (3)O16—C13—C14—C15178.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O16—H16···O9i0.821.862.667 (2)167
C6—H6···O90.932.462.785 (3)100
C11—H11···O16ii0.932.553.425 (3)157
Symmetry codes: (i) x+1/2, y, z+3/2; (ii) x+2, y1/2, z+3/2.
1-(4-Methoxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one (2) top
Crystal data top
C14H12O2SF(000) = 512
Mr = 244.30Dx = 1.350 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.4118 (13) ÅCell parameters from 1920 reflections
b = 5.8387 (5) Åθ = 3.2–27.3°
c = 12.6456 (9) ŵ = 0.26 mm1
β = 97.279 (7)°T = 294 K
V = 1201.98 (16) Å3Block, white
Z = 40.45 × 0.3 × 0.15 mm
Data collection top
SuperNova, single source at offset/far, Eos
diffractometer
2457 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source1771 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.021
Detector resolution: 15.9631 pixels mm-1θmax = 26.4°, θmin = 2.5°
ω scansh = 1920
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2018)
k = 47
Tmin = 0.803, Tmax = 1.000l = 1515
5075 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046 w = 1/[σ2(Fo2) + (0.0416P)2 + 0.3903P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.118(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.16 e Å3
2457 reflectionsΔρmin = 0.26 e Å3
156 parametersExtinction correction: SHELXL-2016/4 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0141 (16)
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.04793 (4)0.76040 (12)0.07886 (5)0.0654 (3)
C20.10560 (14)0.9740 (4)0.14100 (16)0.0519 (6)
H20.1165061.1114240.1083360.062*
C30.13426 (12)0.9216 (4)0.24447 (15)0.0421 (5)
C40.10869 (13)0.6985 (4)0.27105 (18)0.0494 (6)
H40.1229050.6315910.3375720.059*
C50.06133 (14)0.5929 (4)0.18926 (18)0.0558 (6)
H50.0390910.4471290.1933700.067*
C60.18106 (12)1.0798 (4)0.31699 (16)0.0463 (5)
H60.1913621.2240360.2904620.056*
C70.21052 (13)1.0373 (4)0.41779 (16)0.0477 (5)
H70.2027520.8927070.4456590.057*
C80.25502 (13)1.2111 (4)0.48691 (17)0.0468 (5)
O90.25416 (11)1.4134 (3)0.46020 (13)0.0657 (5)
C100.30162 (12)1.1378 (4)0.58960 (15)0.0430 (5)
C110.28855 (13)0.9319 (4)0.63854 (16)0.0499 (6)
H110.2497470.8307720.6050980.060*
C120.33136 (13)0.8718 (4)0.73559 (16)0.0522 (6)
H120.3204240.7337920.7677040.063*
C130.39048 (13)1.0180 (4)0.78457 (16)0.0467 (5)
C140.40604 (15)1.2229 (4)0.73538 (19)0.0588 (7)
H140.4467641.3205160.7671180.071*
C150.36170 (15)1.2817 (4)0.64040 (18)0.0565 (6)
H150.3719791.4211950.6091030.068*
O160.43757 (9)0.9765 (3)0.87912 (11)0.0586 (5)
C170.42397 (17)0.7696 (5)0.93373 (19)0.0679 (7)
H17A0.3676310.7623760.9466350.102*
H17B0.4590860.7656331.0004600.102*
H17C0.4360210.6411590.8909140.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0659 (4)0.0704 (5)0.0552 (4)0.0009 (3)0.0104 (3)0.0052 (3)
C20.0571 (13)0.0487 (14)0.0489 (12)0.0044 (11)0.0019 (10)0.0049 (11)
C30.0414 (11)0.0426 (13)0.0418 (11)0.0067 (9)0.0036 (9)0.0015 (10)
C40.0497 (12)0.0462 (14)0.0515 (12)0.0020 (10)0.0033 (10)0.0054 (11)
C50.0510 (13)0.0420 (13)0.0730 (15)0.0027 (11)0.0029 (11)0.0003 (12)
C60.0475 (12)0.0419 (13)0.0489 (12)0.0019 (10)0.0042 (10)0.0038 (10)
C70.0507 (12)0.0444 (13)0.0470 (12)0.0033 (10)0.0027 (10)0.0024 (11)
C80.0487 (12)0.0454 (14)0.0469 (12)0.0009 (10)0.0086 (9)0.0006 (11)
O90.0854 (13)0.0450 (10)0.0631 (10)0.0029 (9)0.0039 (9)0.0039 (9)
C100.0458 (11)0.0421 (12)0.0415 (11)0.0038 (10)0.0072 (9)0.0039 (10)
C110.0523 (13)0.0500 (14)0.0455 (12)0.0152 (11)0.0013 (10)0.0011 (11)
C120.0595 (14)0.0490 (14)0.0465 (12)0.0131 (11)0.0007 (10)0.0038 (11)
C130.0449 (12)0.0523 (14)0.0420 (11)0.0022 (10)0.0026 (9)0.0064 (11)
C140.0611 (14)0.0541 (15)0.0578 (14)0.0200 (12)0.0058 (11)0.0068 (12)
C150.0686 (15)0.0452 (14)0.0544 (13)0.0158 (12)0.0027 (11)0.0005 (11)
O160.0583 (10)0.0640 (11)0.0495 (9)0.0088 (8)0.0083 (7)0.0020 (8)
C170.0807 (18)0.0666 (18)0.0513 (14)0.0019 (14)0.0108 (12)0.0017 (13)
Geometric parameters (Å, º) top
S1—C21.697 (2)C10—C111.381 (3)
S1—C51.696 (2)C10—C151.390 (3)
C2—H20.9300C11—H110.9300
C2—C31.368 (3)C11—C121.380 (3)
C3—C41.422 (3)C12—H120.9300
C3—C61.451 (3)C12—C131.379 (3)
C4—H40.9300C13—C141.387 (3)
C4—C51.360 (3)C13—O161.361 (2)
C5—H50.9300C14—H140.9300
C6—H60.9300C14—C151.367 (3)
C6—C71.328 (3)C15—H150.9300
C7—H70.9300O16—C171.423 (3)
C7—C81.471 (3)C17—H17A0.9600
C8—O91.228 (3)C17—H17B0.9600
C8—C101.484 (3)C17—H17C0.9600
C5—S1—C292.07 (11)C15—C10—C8119.1 (2)
S1—C2—H2123.8C10—C11—H11119.0
C3—C2—S1112.49 (18)C12—C11—C10122.0 (2)
C3—C2—H2123.8C12—C11—H11119.0
C2—C3—C4110.8 (2)C11—C12—H12120.3
C2—C3—C6123.5 (2)C13—C12—C11119.5 (2)
C4—C3—C6125.60 (19)C13—C12—H12120.3
C3—C4—H4123.4C12—C13—C14119.44 (19)
C5—C4—C3113.1 (2)O16—C13—C12125.0 (2)
C5—C4—H4123.4O16—C13—C14115.54 (19)
S1—C5—H5124.3C13—C14—H14119.9
C4—C5—S1111.50 (18)C15—C14—C13120.2 (2)
C4—C5—H5124.3C15—C14—H14119.9
C3—C6—H6117.0C10—C15—H15119.3
C7—C6—C3125.9 (2)C14—C15—C10121.4 (2)
C7—C6—H6117.0C14—C15—H15119.3
C6—C7—H7118.8C13—O16—C17118.08 (18)
C6—C7—C8122.3 (2)O16—C17—H17A109.5
C8—C7—H7118.8O16—C17—H17B109.5
C7—C8—C10118.9 (2)O16—C17—H17C109.5
O9—C8—C7120.8 (2)H17A—C17—H17B109.5
O9—C8—C10120.3 (2)H17A—C17—H17C109.5
C11—C10—C8123.42 (19)H17B—C17—H17C109.5
C11—C10—C15117.43 (19)
S1—C2—C3—C41.0 (2)C8—C10—C11—C12178.1 (2)
S1—C2—C3—C6176.32 (16)C8—C10—C15—C14179.6 (2)
C2—S1—C5—C40.02 (19)O9—C8—C10—C11162.0 (2)
C2—C3—C4—C51.1 (3)O9—C8—C10—C1517.9 (3)
C2—C3—C6—C7179.7 (2)C10—C11—C12—C131.6 (4)
C3—C4—C5—S10.6 (3)C11—C10—C15—C140.3 (4)
C3—C6—C7—C8177.8 (2)C11—C12—C13—C140.1 (3)
C4—C3—C6—C73.3 (4)C11—C12—C13—O16178.9 (2)
C5—S1—C2—C30.60 (18)C12—C13—C14—C151.6 (4)
C6—C3—C4—C5176.2 (2)C12—C13—O16—C171.6 (3)
C6—C7—C8—O913.0 (3)C13—C14—C15—C101.4 (4)
C6—C7—C8—C10166.6 (2)C14—C13—O16—C17179.5 (2)
C7—C8—C10—C1118.4 (3)C15—C10—C11—C121.8 (3)
C7—C8—C10—C15161.7 (2)O16—C13—C14—C15179.5 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the S1/C2–C5 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···Cg1i0.932.943.602 (2)129
C11—H11···Cg1ii0.932.993.598 (2)125
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+3/2, z+1/2.
1-(4-Ethoxyphenyl)-3-(thiophen-3-yl)prop-1-en-3-one (3) top
Crystal data top
C15H14O2SF(000) = 544
Mr = 258.32Dx = 1.281 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.5120 (8) ÅCell parameters from 4827 reflections
b = 7.7851 (5) Åθ = 3.3–27.9°
c = 10.4913 (5) ŵ = 0.23 mm1
β = 96.813 (4)°T = 294 K
V = 1339.11 (13) Å3Block, white
Z = 40.5 × 0.35 × 0.15 mm
Data collection top
SuperNova, single source at offset/far, Eos
diffractometer
2734 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source2162 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.035
Detector resolution: 15.9631 pixels mm-1θmax = 26.4°, θmin = 2.5°
ω scansh = 2020
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2018)
k = 99
Tmin = 0.733, Tmax = 1.000l = 1213
13246 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.0633P)2 + 0.4069P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.141(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.19 e Å3
2734 reflectionsΔρmin = 0.28 e Å3
165 parametersExtinction correction: SHELXL-2016/4 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0073 (17)
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.28921 (3)0.41932 (9)0.57261 (6)0.0697 (3)
C20.35583 (12)0.4427 (3)0.70816 (19)0.0558 (5)
H20.3408520.4816080.7858550.067*
C30.43322 (11)0.3985 (2)0.69052 (17)0.0458 (4)
C40.43736 (12)0.3435 (3)0.56166 (18)0.0551 (5)
H40.4853240.3079320.5313180.066*
C50.36332 (13)0.3486 (3)0.4872 (2)0.0588 (5)
H50.3549210.3172380.4011530.071*
C60.50131 (12)0.4082 (2)0.79107 (18)0.0483 (5)
H60.4898590.4432680.8717630.058*
C70.57803 (12)0.3718 (3)0.77867 (18)0.0518 (5)
H70.5912010.3359930.6991100.062*
C80.64340 (12)0.3860 (3)0.88615 (17)0.0490 (5)
O90.62809 (9)0.3934 (2)0.99739 (13)0.0670 (5)
C100.72986 (12)0.3954 (2)0.85742 (17)0.0476 (5)
C110.75356 (12)0.3597 (3)0.73833 (18)0.0540 (5)
H110.7142510.3290230.6712660.065*
C120.83455 (13)0.3684 (3)0.7166 (2)0.0594 (5)
H120.8492810.3443130.6355920.071*
C130.89322 (13)0.4129 (3)0.8157 (2)0.0568 (5)
C140.87043 (13)0.4512 (3)0.9360 (2)0.0618 (6)
H140.9096750.4830561.0028230.074*
C150.79065 (13)0.4420 (3)0.95555 (19)0.0571 (5)
H150.7761040.4672651.0364270.069*
O160.97471 (9)0.4227 (2)0.80525 (16)0.0762 (5)
C171.00141 (16)0.3853 (4)0.6849 (3)0.0901 (9)
H17A0.9783640.4674140.6210980.108*
H17B0.9836040.2712090.6569900.108*
C181.09277 (17)0.3952 (5)0.6991 (4)0.1138 (13)
H18A1.1119880.3642580.6193070.171*
H18B1.1150250.3174380.7651280.171*
H18C1.1097710.5102230.7217730.171*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0502 (4)0.0898 (5)0.0684 (4)0.0040 (3)0.0052 (3)0.0000 (3)
C20.0549 (12)0.0668 (13)0.0479 (11)0.0079 (10)0.0153 (9)0.0016 (9)
C30.0481 (10)0.0477 (10)0.0430 (10)0.0015 (8)0.0115 (8)0.0017 (8)
C40.0505 (11)0.0663 (13)0.0500 (11)0.0015 (9)0.0128 (9)0.0087 (9)
C50.0619 (13)0.0676 (13)0.0472 (11)0.0005 (10)0.0072 (9)0.0116 (10)
C60.0522 (11)0.0544 (11)0.0397 (9)0.0043 (8)0.0118 (8)0.0013 (8)
C70.0507 (11)0.0654 (13)0.0400 (10)0.0021 (9)0.0090 (8)0.0020 (9)
C80.0506 (11)0.0582 (12)0.0387 (10)0.0054 (9)0.0077 (8)0.0025 (8)
O90.0584 (9)0.1032 (13)0.0407 (8)0.0094 (8)0.0111 (6)0.0024 (7)
C100.0506 (11)0.0527 (11)0.0393 (9)0.0030 (8)0.0047 (8)0.0035 (8)
C110.0491 (11)0.0707 (14)0.0422 (10)0.0022 (9)0.0049 (8)0.0041 (9)
C120.0534 (12)0.0780 (15)0.0476 (11)0.0027 (10)0.0098 (9)0.0075 (10)
C130.0461 (11)0.0669 (14)0.0580 (12)0.0025 (9)0.0089 (9)0.0003 (10)
C140.0550 (12)0.0813 (16)0.0472 (11)0.0048 (11)0.0020 (9)0.0035 (10)
C150.0553 (12)0.0759 (14)0.0398 (10)0.0003 (10)0.0045 (9)0.0005 (9)
O160.0476 (9)0.1096 (15)0.0726 (11)0.0107 (8)0.0115 (7)0.0139 (9)
C170.0590 (15)0.121 (2)0.095 (2)0.0131 (14)0.0279 (14)0.0264 (17)
C180.0593 (16)0.135 (3)0.153 (3)0.0193 (16)0.0391 (18)0.049 (2)
Geometric parameters (Å, º) top
S1—C21.701 (2)C11—H110.9300
S1—C51.692 (2)C11—C121.385 (3)
C2—H20.9300C12—H120.9300
C2—C31.357 (3)C12—C131.379 (3)
C3—C41.427 (3)C13—C141.392 (3)
C3—C61.450 (3)C13—O161.365 (3)
C4—H40.9300C14—H140.9300
C4—C51.371 (3)C14—C151.359 (3)
C5—H50.9300C15—H150.9300
C6—H60.9300O16—C171.416 (3)
C6—C71.319 (3)C17—H17A0.9700
C7—H70.9300C17—H17B0.9700
C7—C81.470 (3)C17—C181.500 (4)
C8—O91.224 (2)C18—H18A0.9600
C8—C101.496 (3)C18—H18B0.9600
C10—C111.381 (3)C18—H18C0.9600
C10—C151.398 (3)
C5—S1—C292.34 (10)C12—C11—H11119.3
S1—C2—H2123.7C11—C12—H12120.2
C3—C2—S1112.62 (15)C13—C12—C11119.60 (19)
C3—C2—H2123.7C13—C12—H12120.2
C2—C3—C4110.92 (18)C12—C13—C14119.8 (2)
C2—C3—C6123.30 (17)O16—C13—C12124.39 (19)
C4—C3—C6125.79 (17)O16—C13—C14115.84 (19)
C3—C4—H4123.5C13—C14—H14120.1
C5—C4—C3113.01 (18)C15—C14—C13119.78 (19)
C5—C4—H4123.5C15—C14—H14120.1
S1—C5—H5124.4C10—C15—H15119.1
C4—C5—S1111.11 (15)C14—C15—C10121.80 (19)
C4—C5—H5124.4C14—C15—H15119.1
C3—C6—H6117.0C13—O16—C17118.30 (18)
C7—C6—C3126.00 (18)O16—C17—H17A110.0
C7—C6—H6117.0O16—C17—H17B110.0
C6—C7—H7118.8O16—C17—C18108.5 (2)
C6—C7—C8122.31 (18)H17A—C17—H17B108.4
C8—C7—H7118.8C18—C17—H17A110.0
C7—C8—C10118.74 (16)C18—C17—H17B110.0
O9—C8—C7121.26 (18)C17—C18—H18A109.5
O9—C8—C10119.99 (17)C17—C18—H18B109.5
C11—C10—C8123.51 (17)C17—C18—H18C109.5
C11—C10—C15117.56 (18)H18A—C18—H18B109.5
C15—C10—C8118.92 (17)H18A—C18—H18C109.5
C10—C11—H11119.3H18B—C18—H18C109.5
C10—C11—C12121.47 (19)
S1—C2—C3—C40.1 (2)C8—C10—C15—C14179.3 (2)
S1—C2—C3—C6179.55 (15)O9—C8—C10—C11168.8 (2)
C2—S1—C5—C40.05 (18)O9—C8—C10—C1510.9 (3)
C2—C3—C4—C50.1 (3)C10—C11—C12—C130.3 (3)
C2—C3—C6—C7177.9 (2)C11—C10—C15—C140.4 (3)
C3—C4—C5—S10.0 (2)C11—C12—C13—C141.0 (3)
C3—C6—C7—C8179.75 (18)C11—C12—C13—O16178.9 (2)
C4—C3—C6—C71.8 (3)C12—C13—C14—C151.0 (3)
C5—S1—C2—C30.11 (18)C12—C13—O16—C170.2 (3)
C6—C3—C4—C5179.58 (19)C13—C14—C15—C100.3 (4)
C6—C7—C8—O917.1 (3)C13—O16—C17—C18177.0 (2)
C6—C7—C8—C10161.57 (19)C14—C13—O16—C17179.9 (2)
C7—C8—C10—C1112.6 (3)C15—C10—C11—C120.4 (3)
C7—C8—C10—C15167.75 (19)O16—C13—C14—C15178.9 (2)
C8—C10—C11—C12179.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O9i0.932.473.324 (2)153
Symmetry code: (i) x+1, y+1, z+2.
1-(4-Bromophenyl)-3-(thiophen-3-yl)prop-1-en-3-one (4) top
Crystal data top
C13H9BrOSF(000) = 584
Mr = 293.17Dx = 1.667 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.1245 (7) ÅCell parameters from 4399 reflections
b = 14.2016 (13) Åθ = 2.9–27.3°
c = 5.8809 (4) ŵ = 3.67 mm1
β = 98.081 (6)°T = 293 K
V = 1167.93 (15) Å3Plate, yellow
Z = 40.4 × 0.4 × 0.05 mm
Data collection top
SuperNova, single source at offset/far, Eos
diffractometer
2392 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source1683 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.045
Detector resolution: 15.9631 pixels mm-1θmax = 26.4°, θmin = 2.9°
ω scansh = 1717
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2018)
k = 1717
Tmin = 0.367, Tmax = 1.000l = 77
12050 measured reflections
Refinement top
Refinement on F220 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0407P)2 + 0.7623P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2392 reflectionsΔρmax = 0.40 e Å3
158 parametersΔρmin = 0.46 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S1A0.07255 (13)0.3898 (2)0.4329 (4)0.0574 (6)0.702 (4)
S1B0.1418 (5)0.3457 (7)0.2749 (13)0.0574 (6)0.298 (4)
C2A0.1532 (7)0.412 (2)0.663 (3)0.048 (3)0.702 (4)
H2A0.1373550.4397120.7956940.058*0.702 (4)
C2B0.2476 (16)0.341 (5)0.438 (6)0.048 (3)0.298 (4)
H2B0.3011230.3105160.3970880.058*0.298 (4)
C30.2452 (2)0.3858 (2)0.6388 (5)0.0417 (8)
C4A0.2461 (7)0.3456 (17)0.416 (2)0.048 (3)0.702 (4)
H4A0.3024960.3261950.3654010.058*0.702 (4)
C4B0.1551 (18)0.422 (5)0.664 (6)0.048 (3)0.298 (4)
H4B0.1425720.4555620.7925130.058*0.298 (4)
C5A0.1586 (7)0.3375 (9)0.2809 (18)0.053 (3)0.702 (4)
H5A0.1468450.3097320.1365000.063*0.702 (4)
C5B0.0855 (10)0.4021 (19)0.475 (3)0.053 (3)0.298 (4)
H5B0.0208040.4168910.4610470.063*0.298 (4)
C60.3264 (2)0.3933 (2)0.8186 (6)0.0451 (8)
H60.3136820.4146960.9606220.054*
C70.4168 (2)0.3729 (2)0.8023 (6)0.0485 (9)
H70.4332840.3566730.6598230.058*
C80.4916 (3)0.3752 (2)1.0027 (6)0.0460 (8)
O90.4718 (2)0.3764 (2)1.1988 (4)0.0676 (8)
C100.5938 (2)0.3754 (2)0.9658 (5)0.0403 (8)
C110.6238 (2)0.4075 (2)0.7646 (6)0.0451 (8)
H110.5787940.4281360.6442290.054*
C120.7202 (3)0.4092 (3)0.7410 (6)0.0470 (8)
H120.7400870.4324270.6076490.056*
C130.7860 (2)0.3760 (2)0.9180 (6)0.0434 (8)
C140.7584 (3)0.3438 (3)1.1203 (6)0.0491 (9)
H140.8035700.3220821.2390690.059*
C150.6624 (2)0.3447 (2)1.1429 (6)0.0447 (8)
H150.6432920.3242271.2796030.054*
Br160.91660 (3)0.37156 (4)0.88024 (8)0.0730 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0459 (8)0.0718 (14)0.0532 (11)0.0051 (8)0.0029 (6)0.0014 (9)
S1B0.0459 (8)0.0718 (14)0.0532 (11)0.0051 (8)0.0029 (6)0.0014 (9)
C2A0.044 (4)0.056 (10)0.045 (4)0.006 (4)0.010 (3)0.004 (4)
C2B0.044 (4)0.056 (10)0.045 (4)0.006 (4)0.010 (3)0.004 (4)
C30.0453 (19)0.0398 (19)0.0417 (18)0.0020 (15)0.0115 (15)0.0021 (15)
C4A0.052 (4)0.051 (5)0.043 (5)0.002 (3)0.013 (3)0.006 (5)
C4B0.052 (4)0.051 (5)0.043 (5)0.002 (3)0.013 (3)0.006 (5)
C5A0.058 (6)0.055 (5)0.051 (4)0.015 (4)0.025 (4)0.013 (3)
C5B0.058 (6)0.055 (5)0.051 (4)0.015 (4)0.025 (4)0.013 (3)
C60.045 (2)0.051 (2)0.0416 (19)0.0044 (16)0.0107 (15)0.0040 (15)
C70.047 (2)0.054 (2)0.0452 (19)0.0018 (17)0.0105 (16)0.0068 (16)
C80.0447 (19)0.050 (2)0.045 (2)0.0020 (16)0.0112 (16)0.0036 (16)
O90.0531 (16)0.107 (3)0.0450 (15)0.0056 (14)0.0139 (12)0.0000 (14)
C100.0455 (19)0.0372 (18)0.0386 (18)0.0011 (15)0.0075 (15)0.0038 (14)
C110.049 (2)0.050 (2)0.0350 (18)0.0028 (17)0.0007 (15)0.0004 (15)
C120.054 (2)0.051 (2)0.0366 (18)0.0055 (17)0.0101 (16)0.0013 (16)
C130.0382 (18)0.045 (2)0.048 (2)0.0061 (15)0.0075 (15)0.0056 (16)
C140.051 (2)0.050 (2)0.0426 (19)0.0004 (17)0.0036 (16)0.0041 (16)
C150.050 (2)0.048 (2)0.0363 (18)0.0041 (17)0.0062 (15)0.0021 (15)
Br160.0430 (3)0.0970 (4)0.0803 (4)0.0074 (2)0.0128 (2)0.0047 (2)
Geometric parameters (Å, º) top
S1A—C2A1.671 (8)C6—H60.9300
C2A—H2A0.9300C6—C71.325 (5)
S1B—C2B1.661 (16)C7—H70.9300
C2B—H2B0.9300C7—C81.469 (5)
C2A—C31.378 (9)C8—O91.224 (4)
C2B—C31.347 (16)C8—C101.489 (5)
C4A—H4A0.9300C10—C111.389 (5)
C4B—H4B0.9300C10—C151.390 (5)
S1A—C5A1.770 (8)C11—H110.9300
C4A—C5A1.378 (11)C11—C121.388 (5)
C5A—H5A0.9300C12—H120.9300
S1B—C5B1.708 (15)C12—C131.378 (5)
C4B—C5B1.407 (16)C13—C141.381 (5)
C5B—H5B0.9300C13—Br161.890 (3)
C3—C4A1.431 (8)C14—H140.9300
C3—C4B1.400 (16)C14—C151.381 (5)
C3—C61.451 (5)C15—H150.9300
C4A—C5A—S1A107.3 (6)C7—C6—C3127.0 (3)
C4B—C5B—S1B107.4 (9)C7—C6—H6116.5
S1A—C2A—H2A122.9C6—C7—H7119.0
S1B—C2B—H2B124.6C6—C7—C8121.9 (3)
C5A—C4A—C3116.0 (7)C8—C7—H7119.0
C5A—C4A—H4A122.0C7—C8—C10119.1 (3)
C5B—C4B—H4B123.6O9—C8—C7121.5 (3)
C2A—S1A—C5A92.8 (4)O9—C8—C10119.5 (3)
S1A—C5A—H5A126.3C11—C10—C8122.9 (3)
C4A—C5A—H5A126.3C11—C10—C15118.5 (3)
C2B—S1B—C5B95.2 (7)C15—C10—C8118.6 (3)
C4B—C5B—H5B126.3C10—C11—H11119.6
S1B—C5B—H5B126.3C12—C11—C10120.8 (3)
C2A—C3—C4A109.4 (5)C12—C11—H11119.6
C2B—C3—C4B113.8 (9)C11—C12—H12120.5
C4A—C3—C6126.0 (4)C13—C12—C11119.1 (3)
C4B—C3—C6122.2 (7)C13—C12—H12120.5
C2B—C3—C6124.0 (7)C12—C13—C14121.5 (3)
C2A—C3—C6124.5 (5)C12—C13—Br16119.2 (3)
C3—C6—H6116.5C14—C13—Br16119.3 (3)
C3—C2A—S1A114.3 (5)C13—C14—H14120.7
C3—C2B—S1B110.7 (9)C15—C14—C13118.7 (3)
C3—C2A—H2A122.9C15—C14—H14120.7
C3—C2B—H2B124.6C10—C15—H15119.3
C3—C4A—H4A122.0C14—C15—C10121.5 (3)
C3—C4B—H4B123.6C14—C15—H15119.3
C3—C4B—C5B112.7 (11)
C2A—S1A—C5A—C4A3 (2)C6—C3—C4B—C5B176 (3)
C2B—S1B—C5B—C4B4 (5)C6—C7—C8—O915.6 (6)
C5B—S1B—C2B—C34 (5)C6—C7—C8—C10164.9 (3)
C5A—S1A—C2A—C32 (2)C7—C8—C10—C1124.4 (5)
S1A—C2A—C3—C4A0 (2)C7—C8—C10—C15157.6 (3)
S1B—C2B—C3—C4B2 (5)C8—C10—C11—C12177.8 (3)
S1B—C2B—C3—C6179.7 (18)C8—C10—C15—C14179.4 (3)
S1A—C2A—C3—C6176.6 (10)O9—C8—C10—C11156.0 (4)
C2A—C3—C6—C7177.0 (17)O9—C8—C10—C1522.0 (5)
C2B—C3—C6—C713 (4)C10—C11—C12—C131.8 (5)
C4A—C3—C6—C76.9 (15)C11—C10—C15—C141.3 (5)
C4B—C3—C6—C7170 (4)C11—C12—C13—C142.0 (5)
C2A—C3—C4A—C5A3 (2)C11—C12—C13—Br16176.5 (3)
C2B—C3—C4B—C5B1 (6)C12—C13—C14—C150.5 (5)
C3—C4B—C5B—S1B4 (7)C13—C14—C15—C101.2 (5)
C3—C4A—C5A—S1A4 (2)C15—C10—C11—C120.2 (5)
C3—C6—C7—C8174.3 (3)Br16—C13—C14—C15177.9 (3)
C6—C3—C4A—C5A173.8 (12)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the major- and minor-disorder components of the thiophene ring, respectively.
D—H···AD—HH···AD···AD—H···A
C5A—H5A···Cg1i0.932.803.493 (14)132
C5A—H5A···Cg2i0.932.853.52 (2)130
Symmetry code: (i) x, y+1/2, z1/2.
Percentage contributions of interatomic contacts to the Hirshfeld surfaces for compounds (1-4). top
Contact1234
H···H28.833.544.528.5
S···H/H···S13.011.610.23.9
C···H/H···C30.433.922.132.6
O···H/H···O18.515.813.811.1
C···C3.20.74.52.4
C···S/S···C3.70.93.50.0
S···S0.01.50.00.0
S···O/O···S0.30.00.10.0
C···O/O···C1.81.61.01.0
O···O0.00.60.00.0
Br···S/S···Br2.8
Br···C/C···Br0.6
Br···H/H···Br16.5
Br···O/O···Br0.0
Br···Br0.5
 

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