In the title compound, the 2,5-dichlorothiophene and 2,4-dichlorophenyl rings, linked via a prop-2-en-1-one spacer, make a dihedral angle of 12.24 (15)°. Both the thiophene and benzene rings of adjacent molecules interact attractively in a face-to-face manner, forming zigzag sheets lying parallel to the (011) plane.
Keywords: crystal structure; 2,5-dichlorothiophene ring; 2,4-dichlorophenyl ring; E configuration; Hirshfeld surface analysis
Abstract
The molecular structure of the title compound, C13H6Cl4OS, consists of a 2,5-dichlorothiophene ring and a 2,4-dichlorophenyl ring linked via a prop-2-en-1-one spacer. The dihedral angle between the 2,5-dichlorothiophene ring and the 2,4-dichlorophenyl ring is 12.24 (15)°. The molecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. The molecular conformation is stabilized by intramolecular C—H⋯Cl contacts, producing S(6) and S(5) ring motifs. In the crystal, the molecules are linked along the a-axis direction through face-to-face π-stacking between the thiophene rings and the benzene rings of the molecules in zigzag sheets lying parallel to the bc plane along the c axis. The intermolecular interactions in the crystal packing were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are Cl⋯H/ H⋯Cl (20.8%), followed by Cl⋯Cl (18.7%), C⋯C (11.9%), Cl⋯S/S⋯Cl (10.9%), H⋯H (10.1%), C⋯H/H⋯C (9.3%) and O⋯H/H⋯O (7.6%).
Chemical context
Compounds bearing the 1,3-diphenyl-2-propen-1-one framework and belong to the flavonoid family are commonly called by its generic name ‘chalcone’. These are abundant in nature, ranging from ferns to higher plants, and are considered to be the precursors of flavonoids and isoflavonoids, in which the two aromatic rings are joined by a three carbon α,β-unsaturated carbonyl system. In plants, chalcones are converted to the corresponding (2S)-flavanones in a stereospecific reaction catalysed by the enzyme chalcone isomerase. The chemistry of chalcones remains a fascination among researchers because of the large number of replaceable hydrogen atoms that allows a number of derivatives with a variety of promising biological activities. They are found in fruits and vegetables, which attracted attention because of their pharmacological activities such as anti-inflamatory (Yadav et al., 2011 ▸), antifungal (Mahapatra et al., 2015 ▸), antiviral (Nowakowska, 2007 ▸; Chimenti et al., 2010 ▸; Elarfi &Al-Difar, 2012 ▸), antioxidant (Ferreira et al., 2006 ▸) and anticancer (Stiborova et al., 2011 ▸ activities). The synthesis and antimicrobial evaluation of new chalcones containing a 2,5-dichlorothiophene moiety has been reported (Tomar et al., 2007 ▸). In recent years, chalcones have been used in the field of materials science as non-linear optical devices (Raghavendra et al., 2017 ▸; Chandra Shekhara Shetty et al., 2016 ▸). In view of all the above and as part of our ongoing work (Harrison et al., 2010 ▸; Jasinski et al., 2010 ▸; Dutkiewicz et al., 2010 ▸) herewith we report the crystal and molecular structure of the title compound.
Structural commentary
The title compound, Fig. 1 ▸, is constructed from two aromatic rings (2,5-dichlorothiophene and terminal 2,4-dichlorophenyl rings), which are linked by a C=C—C(=O)—C enone bridge. Probably as a result of the steric repulsion between the chlorine atoms of the adjacent molecules, the C3—C4—C5—O1 and O1—C5—C6—C7 torsion angles about the enone bridge are −11.8 (5) and 0.4 (6)°, respectively. Hence, the dihedral angle between the 2,5-dichlorothiophene ring and the 2,4-dichlorophenyl ring increases to 12.24 (15)°. The bond lengths and angles in the title compound are comparable with those of the related compounds (E)-3-(3,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2yl)prop-2-en-1-one (Ezhilarasi et al., 2015 ▸), (E)-1-(3-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (Escobar et al., 2012 ▸) and (E)-3-(2-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one (Li et al., 2012 ▸). The molecular conformation of the title compound is stabilized by intramolecular C—H⋯Cl contacts (Table 1 ▸), producing S(6) and S(5) ring motifs.
Figure 1.
The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level. The two intramolecular C—H⋯Cl contacts (see Table1) are shown as dashed lines.
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C6—H6A⋯Cl1 | 0.93 | 2.48 | 3.220 (3) | 136 |
| C7—H7A⋯Cl3 | 0.93 | 2.65 | 3.075 (3) | 108 |
Supramolecular features and Hirshfeld surface analysis
In the crystal, conventional hydrogen bonds are not observed. π-stacking is observed between the thiophene rings (S1/C1–C4, centroid Cg1) of adjacent molecules in the alternating sheets along the [100] direction [Cg1⋯Cg1i,ii: centroid–centroid distance = 3.987 (2) Å, shortest perpendicular distance for the centroid of one ring to the plane of the other = 3.6143 (12) Å, ring-centroid offset = 1.683 Å; symmetry codes: (i) −1 + x, y, z; (i) 1 + x, y, z] and between the benzene rings (C8–C13, centroid Cg2) of the same molecules [Cg2⋯Cg2i,ii: centroid–centroid distance = 3.987 (2) Å, shortest perpendicular distance = 3.5213 (13) Å, offset = 1.869 Å]. As shown Fig. 2 ▸, the molecules are packed to form zigzag sheets lying parallel to (011) along the c-axis direction through face-to-face π-stacking between the thiophene and benzene rings of pairs of adjacent molecules along the [100] direction (Cl⋯S and Cl⋯H interactions; Table 2 ▸ and Fig. 2 ▸). The Cl⋯S contact, at 3.660 (1) Å, is equal to the sum of the van der Waals radii of S and Cl atoms (3.65 Å; Pauling, 1960 ▸).
Figure 2.
A view of the offset face-to-face π-stacking in the title compound, with the thick dashed lines indicating centroid-to-centroid interactions. The Cl⋯H and Cl⋯S interactions are also shown as dashed lines.
Table 2. Summary of short interatomic contacts (Å) in the title compound.
| Contact | Distance | Symmetry operation |
|---|---|---|
| Cl2⋯S1 | 3.660 (1) |
 + x,  − y, 2 − z
|
| H10A⋯Cl4 | 3.03 | − + x, − y, 1 − z
|
| C8⋯C9 | 3.573 (4) | 1 + x, y, z |
Hirshfeld surfaces and fingerprint plots were generated for the title compound using CrystalExplorer (McKinnon et al., 2007 ▸). Hirshfeld surfaces enable the visualization of intermolecular interactions by different colours and colour intensity, representing short or long contacts and indicating the relative strength of the interactions. The overall two-dimensional fingerprint plot for the title compound and those delineated into Cl⋯H/ H⋯Cl, Cl⋯Cl, C⋯C, Cl⋯S/S⋯Cl, H⋯H, C⋯H/H⋯C and O⋯H/H⋯O contacts are illustrated in Fig. 3 ▸; the percentage contributions from the different interatomic contacts to the Hirshfeld surfaces are as follows: Cl⋯H/ H⋯Cl (20.8%), Cl⋯Cl (18.7%), C⋯C (11.9%), Cl⋯S/S⋯Cl (10.9%), H⋯H (10.1%), C⋯H/H⋯C (9.3%) and O⋯H/H⋯O (7.6%). The contributions of the other weak intermolecular contacts to the Hirshfeld surfaces are Cl⋯C/C⋯Cl (3.6%), S⋯C/C⋯S (2.8%), Cl⋯O/O⋯Cl (2.3%), S⋯S (0.9%), O⋯O (0.6%) and C⋯O/O⋯C (0.6%).
Figure 3.
The two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and delineated into (b) Cl⋯H/ H⋯Cl, (c) Cl⋯Cl, (d) C⋯C, (e) Cl⋯S/S⋯Cl, (f) H⋯H, (g) C⋯H/H⋯C and (h) O⋯H/H⋯O interactions.
The C—H⋯Cl interactions appear as two distinct spikes in the fingerprint plot (Fig. 3 ▸
b) of the title compound, where the sum of Cl⋯H/H⋯Cl interactions comprises 20.8% of the total Hirshfeld surface area of the molecule. The Cl⋯H/H⋯Cl interactions represented by the spikes in the bottom right and left region (d
e + d
i ≃ 2.83 Å) indicate that the hydrogen atoms are in contact with the Cl atoms to build the two-dimensional supramolecular framework [d
e and d
i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (internal) the surface, respectively]. Cl⋯Cl contacts (Fig. 3 ▸
c; 18.7%) are disfavoured when the number of H atoms on the molecular surface is large because of competition with the more attractive H⋯Cl contacts. Cl⋯Cl contacts from a parallel alignment of C—Cl bonds (C10—H10A⋯Cl4iii; (iii) − + x, − y, 1 − z] may be indicated. They are known in the literature as type-I halogen–halogen interactions (Bui et al., 2009 ▸), with both C—Cl⋯Cl angles equal to one another. In the present case, these angles are close to 165°. The C⋯C contacts (Fig. 3 ▸
d); 11.9%) reflect π–π interactions between the above-mentioned aromatic rings. The S⋯Cl contacts (Fig. 3 ▸
e; 10.9%) contracted to a much lesser degree. The C⋯H/H⋯C interactions (Fig. 3 ▸
g) account for 9.3% of the total Hirshfeld surface of the molecules. The scattered points in the breakdown of the fingerprint plot show the π–π stacking interactions. In the fingerprint plot delineated into H⋯O/O⋯H contacts (Fig. 3 ▸
h), the 7.6% contribution to the Hirshfeld surface arises from intermolecular C=O⋯H hydrogen bonding and is viewed as pair of spikes with the tip at de + di ∼ 2.9 Å.
The large number of Cl⋯H/ H⋯Cl, Cl⋯Cl, C⋯C, Cl⋯S/S⋯Cl, H⋯H, C⋯H/H⋯C and O⋯H/H⋯O interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015 ▸).
Database survey
The closest related compounds with the same skeleton and containing a similar bis-chalcone moiety to the title compound but with different substituents on the aromatic rings are: (2E)-1-(5-chlorothiophen-2-yl)-3-(4-ethylphenyl)prop-2-en-1-one [(I); Naik et al., 2015 ▸], (2E)-1-(5-bromothiophen-2-yl)-3-(4-ethylphenyl)prop- 2-en-1-one [(II); Naik et al., 2015 ▸], (2E)-1-(5-chlorothiophen-2-yl)-3-(4-ethoxyphenyl)prop-2-en-1-one [(III); Naik et al., 2015 ▸], (2E)-1-(5-bromothiophen-2-yl)-3-(4-ethoxyphenyl)prop-2-en-1-one [(IV); Naik et al., 2015 ▸], (2E)-3-(4-bromophenyl)-1-(5-chlorothiophen-2-yl)prop-2-en-1-one [(V); Naik et al., 2015 ▸], (2E)-1-(5-bromothiophen-2-yl)-3-(3-methoxyphenyl)prop-2-en-1-one [(VI); Naik et al., 2015 ▸], (E)-1-(5-chlorothiophen-2-yl)-3-(p-tolyl)prop-2-en-1-one [(VII); Kumara et al., 2017 ▸], (E)-1-(5-chlorothiophen-2-yl)-3-(2,4-dimethylphenyl) prop-2-en-1-one [(VIII); Naveen et al., 2016 ▸], (2E)-1-(5-bromothiophen- 2-yl)-3-(2-chlorophenyl)prop-2-en-1-one [(IX); Anitha et al., 2015 ▸], (2E)-1-[4-hydroxy-3-(morpholin-4-ylmethyl)phenyl]-3-(thiophen-2-yl)prop-2-en-1-one [(X); Yesilyurt et al., 2018 ▸] and (E)-1-(2-aminophenyl)-3-(thiophen-2-yl)prop-2-en-1-one [(XI); Chantrapromma et al., 2013 ▸].
In (I) and (II), the structures are isostructural in space group P1, while (III) and (IV) are isostructural in space group P21/c. There are no hydrogen bonds of any kind in the structures of compounds (I) and (II), but in the structures of compounds (III) and (IV), the molecules are linked into C(7) chains by means of C—H⋯O hydrogen bonds. In (V), there are again no hydrogen bonds nor π–π stacking interactions but in (VI), the molecules are linked into C(5) chains by C—H⋯O hydrogen bonds. In each of compounds (I)–(VI), the molecular skeletons are close to planarity, and there are short halogen–halogen contacts in the structures of compounds (II) and (V) and a short Br⋯O contact in the structure of compound (VI).
In (VII), the molecule is non-planar, with a dihedral angle of 22.6 (2)° between the aromatic rings. The molecules are linked by pairs of C—H⋯π interactions, forming inversion dimers. There are no other significant intermolecular interactions present. In (VIII), the molecule is nearly planar, the dihedral angle between the thiophene and phenyl rings being 9.07 (8)°. The molecules are linked via weak C—H⋯O and C—H⋯S hydrogen bonds, forming chains propagating along the c-axis direction. In (IX), the thienyl ring is not coplanar with the benzene ring, their planes forming a dihedral angle of 13.2 (4)°. In the crystal, molecules stack along the a-axis direction, with the interplanar separation between the thienyl rings and between the benzene rings being 3.925 (6) Å. In (X), the thiophene ring forms a dihedral angle of 26.04 (9)° with the benzene ring. The molecular conformation is stabilized by an O—H⋯N hydrogen bond. The molecules are connected through C—H⋯O hydrogen bonds, forming wave-like layers parallel to the ab plane, which are further linked into a three-dimensional network by C—H⋯π interactions. In (XI), the molecule is almost planar with a dihedral angle of 3.73 (8)° between the phenyl and thiophene rings. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. Adjacent molecules are linked into dimers in an anti-parallel face-to-face manner by pairs of C—H⋯O interactions. Neighboring dimers are further linked into chains along the c-axis direction by N—H⋯N hydrogen bonds.
Synthesis and crystallization
The title compound was synthesized as per the procedure reported earlier (Kumar et al., 2013a ▸,b ▸; Chidan Kumar et al., 2014 ▸). 1-(2,5-Dichlorothiophen-3-yl)ethanone (0.01 mol) (Harrison et al., 2010 ▸) and 2,4-dichlorobenzaldehyde (0.01 mol) was dissolved in 20 ml methanol. A catalytic amount of NaOH was added to the solution dropwise with vigorous stirring. The reaction mixture was stirred for about 2 h at room temperature. The formed crude products were filtered, washed successively with distilled water and recrystallized from methanol to get the title chalcone. The melting point (381–383 K) was determined by Stuart Scientific (UK) apparatus.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. C-bound H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and U iso(H) = 1.2U eq(C) for C—H. Owing to poor agreement between observed and calculated intensities, twelve outliers (2 7 2, 2 8 0, 2 8 1, 0 1 28, 2 8 23, 0 14 8, 0 0 6, 3 0 29, 1 0 8, 0 17 4, 1 3 27, 2 12 19) were omitted in the final cycles of refinement.
Table 3. Experimental details.
| Crystal data | |
| Chemical formula | C13H6Cl4OS |
| M r | 352.04 |
| Crystal system, space group | Orthorhombic, P212121 |
| Temperature (K) | 294 |
| a, b, c (Å) | 3.9867 (3), 13.4564 (11), 25.573 (2) |
| V (Å3) | 1371.91 (19) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 1.00 |
| Crystal size (mm) | 0.63 × 0.23 × 0.11 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2007 ▸) |
| T min, T max | 0.757, 0.894 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 11402, 4226, 3425 |
| R int | 0.026 |
| (sin θ/λ)max (Å−1) | 0.720 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.038, 0.102, 1.03 |
| No. of reflections | 4226 |
| No. of parameters | 172 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.25, −0.20 |
| Absolute structure | Flack x determined using 1124 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸) |
| Absolute structure parameter | 0.04 (5) |
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989018010976/dx2006sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018010976/dx2006Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989018010976/dx2006Isup3.cml
CCDC reference: 1036797
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors extend their appreciation to the Vidya Vikas Research & Development Centre for the facilities and encouragement.
supplementary crystallographic information
Crystal data
| C13H6Cl4OS | Dx = 1.704 Mg m−3 |
| Mr = 352.04 | Mo Kα radiation, λ = 0.71073 Å |
| Orthorhombic, P212121 | Cell parameters from 4362 reflections |
| a = 3.9867 (3) Å | θ = 2.2–28.5° |
| b = 13.4564 (11) Å | µ = 1.00 mm−1 |
| c = 25.573 (2) Å | T = 294 K |
| V = 1371.91 (19) Å3 | Block, yellow |
| Z = 4 | 0.63 × 0.23 × 0.11 mm |
| F(000) = 704 |
Data collection
| Bruker APEXII CCD diffractometer | 3425 reflections with I > 2σ(I) |
| φ and ω scans | Rint = 0.026 |
| Absorption correction: multi-scan (SADABS; Bruker, 2007) | θmax = 30.8°, θmin = 1.6° |
| Tmin = 0.757, Tmax = 0.894 | h = −5→2 |
| 11402 measured reflections | k = −19→19 |
| 4226 independent reflections | l = −36→36 |
Refinement
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0581P)2 + 0.011P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.102 | (Δ/σ)max = 0.001 |
| S = 1.03 | Δρmax = 0.25 e Å−3 |
| 4226 reflections | Δρmin = −0.20 e Å−3 |
| 172 parameters | Absolute structure: Flack x determined using 1124 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
| 0 restraints | Absolute structure parameter: 0.04 (5) |
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 (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 1.1673 (8) | 0.77797 (19) | 0.84012 (9) | 0.0391 (6) | |
| C2 | 1.2553 (8) | 0.6794 (2) | 0.91880 (10) | 0.0419 (6) | |
| C3 | 1.1115 (8) | 0.6258 (2) | 0.88062 (10) | 0.0410 (6) | |
| H3A | 1.052432 | 0.559246 | 0.884223 | 0.049* | |
| C4 | 1.0587 (8) | 0.6820 (2) | 0.83366 (10) | 0.0382 (6) | |
| C5 | 0.9016 (9) | 0.6327 (2) | 0.78763 (10) | 0.0444 (7) | |
| C6 | 0.7779 (10) | 0.6938 (2) | 0.74420 (11) | 0.0493 (7) | |
| H6A | 0.809837 | 0.762158 | 0.746266 | 0.059* | |
| C7 | 0.6253 (9) | 0.6588 (2) | 0.70264 (10) | 0.0462 (7) | |
| H7A | 0.596005 | 0.590316 | 0.700760 | 0.055* | |
| C8 | 0.4975 (8) | 0.7177 (2) | 0.65917 (10) | 0.0386 (6) | |
| C9 | 0.3384 (8) | 0.67552 (19) | 0.61621 (10) | 0.0403 (6) | |
| C10 | 0.2191 (8) | 0.7316 (2) | 0.57472 (10) | 0.0431 (6) | |
| H10A | 0.112503 | 0.701315 | 0.546561 | 0.052* | |
| C11 | 0.2620 (8) | 0.8330 (2) | 0.57612 (10) | 0.0425 (7) | |
| C12 | 0.4192 (9) | 0.8788 (2) | 0.61805 (11) | 0.0465 (7) | |
| H12A | 0.447771 | 0.947373 | 0.618483 | 0.056* | |
| C13 | 0.5316 (9) | 0.8219 (2) | 0.65879 (11) | 0.0438 (7) | |
| H13A | 0.633719 | 0.852975 | 0.687101 | 0.053* | |
| O1 | 0.8718 (9) | 0.54311 (16) | 0.78790 (9) | 0.0721 (9) | |
| S1 | 1.3313 (2) | 0.80047 (5) | 0.90119 (3) | 0.04511 (19) | |
| Cl1 | 1.1738 (3) | 0.87633 (5) | 0.79734 (3) | 0.0556 (2) | |
| Cl2 | 1.3606 (3) | 0.63887 (6) | 0.98017 (3) | 0.0593 (2) | |
| Cl3 | 0.2772 (3) | 0.54840 (5) | 0.61241 (3) | 0.0639 (3) | |
| Cl4 | 0.1204 (3) | 0.90504 (6) | 0.52453 (3) | 0.0605 (2) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0422 (17) | 0.0375 (11) | 0.0377 (11) | 0.0021 (13) | 0.0062 (12) | −0.0015 (9) |
| C2 | 0.0429 (18) | 0.0443 (13) | 0.0384 (12) | 0.0015 (13) | −0.0020 (11) | 0.0019 (10) |
| C3 | 0.0430 (18) | 0.0392 (12) | 0.0408 (12) | −0.0001 (13) | −0.0012 (12) | 0.0003 (10) |
| C4 | 0.0376 (16) | 0.0406 (12) | 0.0364 (11) | 0.0014 (12) | 0.0021 (11) | −0.0021 (10) |
| C5 | 0.051 (2) | 0.0462 (14) | 0.0362 (12) | −0.0046 (14) | 0.0005 (12) | −0.0046 (10) |
| C6 | 0.059 (2) | 0.0451 (13) | 0.0437 (13) | −0.0026 (15) | −0.0080 (14) | −0.0013 (11) |
| C7 | 0.058 (2) | 0.0429 (13) | 0.0382 (12) | −0.0006 (15) | 0.0010 (14) | −0.0022 (10) |
| C8 | 0.0385 (16) | 0.0415 (13) | 0.0358 (11) | 0.0001 (12) | 0.0045 (11) | −0.0038 (10) |
| C9 | 0.0416 (16) | 0.0380 (11) | 0.0412 (12) | −0.0018 (13) | 0.0027 (13) | −0.0046 (9) |
| C10 | 0.0433 (18) | 0.0481 (13) | 0.0378 (12) | 0.0008 (13) | 0.0001 (12) | −0.0066 (10) |
| C11 | 0.0387 (18) | 0.0488 (14) | 0.0401 (12) | 0.0061 (13) | 0.0018 (11) | 0.0002 (10) |
| C12 | 0.048 (2) | 0.0396 (13) | 0.0522 (15) | −0.0007 (13) | 0.0013 (14) | −0.0061 (11) |
| C13 | 0.0468 (19) | 0.0422 (13) | 0.0426 (13) | −0.0004 (13) | −0.0034 (13) | −0.0080 (11) |
| O1 | 0.123 (3) | 0.0414 (11) | 0.0517 (12) | −0.0110 (15) | −0.0209 (16) | −0.0012 (9) |
| S1 | 0.0504 (5) | 0.0422 (3) | 0.0427 (3) | −0.0035 (3) | −0.0008 (3) | −0.0055 (3) |
| Cl1 | 0.0766 (6) | 0.0403 (3) | 0.0498 (4) | −0.0043 (4) | −0.0001 (4) | 0.0048 (3) |
| Cl2 | 0.0740 (6) | 0.0589 (4) | 0.0450 (3) | −0.0016 (4) | −0.0159 (4) | 0.0056 (3) |
| Cl3 | 0.0883 (8) | 0.0410 (3) | 0.0625 (4) | −0.0127 (4) | −0.0148 (5) | −0.0023 (3) |
| Cl4 | 0.0684 (6) | 0.0556 (4) | 0.0576 (4) | 0.0076 (4) | −0.0106 (4) | 0.0080 (3) |
Geometric parameters (Å, º)
| C1—C4 | 1.372 (4) | C7—C8 | 1.458 (4) |
| C1—Cl1 | 1.717 (3) | C7—H7A | 0.9300 |
| C1—S1 | 1.720 (3) | C8—C9 | 1.390 (4) |
| C2—C3 | 1.343 (4) | C8—C13 | 1.408 (4) |
| C2—Cl2 | 1.714 (3) | C9—C10 | 1.386 (4) |
| C2—S1 | 1.717 (3) | C9—Cl3 | 1.731 (3) |
| C3—C4 | 1.435 (4) | C10—C11 | 1.375 (4) |
| C3—H3A | 0.9300 | C10—H10A | 0.9300 |
| C4—C5 | 1.489 (4) | C11—C12 | 1.387 (4) |
| C5—O1 | 1.212 (4) | C11—Cl4 | 1.732 (3) |
| C5—C6 | 1.467 (4) | C12—C13 | 1.368 (4) |
| C6—C7 | 1.312 (4) | C12—H12A | 0.9300 |
| C6—H6A | 0.9300 | C13—H13A | 0.9300 |
| C4—C1—Cl1 | 130.8 (2) | C8—C7—H7A | 117.1 |
| C4—C1—S1 | 113.3 (2) | C9—C8—C13 | 116.5 (3) |
| Cl1—C1—S1 | 115.92 (16) | C9—C8—C7 | 122.7 (3) |
| C3—C2—Cl2 | 126.8 (2) | C13—C8—C7 | 120.9 (3) |
| C3—C2—S1 | 113.3 (2) | C10—C9—C8 | 122.6 (3) |
| Cl2—C2—S1 | 119.95 (17) | C10—C9—Cl3 | 116.5 (2) |
| C2—C3—C4 | 112.8 (3) | C8—C9—Cl3 | 120.8 (2) |
| C2—C3—H3A | 123.6 | C11—C10—C9 | 118.5 (3) |
| C4—C3—H3A | 123.6 | C11—C10—H10A | 120.7 |
| C1—C4—C3 | 110.5 (2) | C9—C10—H10A | 120.7 |
| C1—C4—C5 | 130.3 (2) | C10—C11—C12 | 121.2 (3) |
| C3—C4—C5 | 119.2 (3) | C10—C11—Cl4 | 119.7 (2) |
| O1—C5—C6 | 121.9 (3) | C12—C11—Cl4 | 119.2 (2) |
| O1—C5—C4 | 118.7 (3) | C13—C12—C11 | 119.2 (3) |
| C6—C5—C4 | 119.3 (3) | C13—C12—H12A | 120.4 |
| C7—C6—C5 | 124.6 (3) | C11—C12—H12A | 120.4 |
| C7—C6—H6A | 117.7 | C12—C13—C8 | 122.0 (3) |
| C5—C6—H6A | 117.7 | C12—C13—H13A | 119.0 |
| C6—C7—C8 | 125.7 (3) | C8—C13—H13A | 119.0 |
| C6—C7—H7A | 117.1 | C2—S1—C1 | 90.24 (13) |
| Cl2—C2—C3—C4 | −179.6 (2) | C13—C8—C9—C10 | 0.3 (5) |
| S1—C2—C3—C4 | 0.7 (4) | C7—C8—C9—C10 | −179.5 (3) |
| Cl1—C1—C4—C3 | 178.6 (3) | C13—C8—C9—Cl3 | −179.3 (3) |
| S1—C1—C4—C3 | 0.2 (4) | C7—C8—C9—Cl3 | 0.9 (4) |
| Cl1—C1—C4—C5 | −2.0 (6) | C8—C9—C10—C11 | 0.4 (5) |
| S1—C1—C4—C5 | 179.6 (3) | Cl3—C9—C10—C11 | 179.9 (3) |
| C2—C3—C4—C1 | −0.6 (4) | C9—C10—C11—C12 | −0.3 (5) |
| C2—C3—C4—C5 | 179.9 (3) | C9—C10—C11—Cl4 | 179.2 (2) |
| C1—C4—C5—O1 | 168.9 (4) | C10—C11—C12—C13 | −0.3 (5) |
| C3—C4—C5—O1 | −11.8 (5) | Cl4—C11—C12—C13 | −179.9 (3) |
| C1—C4—C5—C6 | −13.1 (5) | C11—C12—C13—C8 | 1.0 (5) |
| C3—C4—C5—C6 | 166.3 (3) | C9—C8—C13—C12 | −1.0 (5) |
| O1—C5—C6—C7 | 0.4 (6) | C7—C8—C13—C12 | 178.8 (3) |
| C4—C5—C6—C7 | −177.6 (3) | C3—C2—S1—C1 | −0.5 (3) |
| C5—C6—C7—C8 | 179.5 (3) | Cl2—C2—S1—C1 | 179.8 (2) |
| C6—C7—C8—C9 | 179.9 (4) | C4—C1—S1—C2 | 0.1 (3) |
| C6—C7—C8—C13 | 0.1 (5) | Cl1—C1—S1—C2 | −178.5 (2) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C6—H6A···Cl1 | 0.93 | 2.48 | 3.220 (3) | 136 |
| C7—H7A···Cl3 | 0.93 | 2.65 | 3.075 (3) | 108 |
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989018010976/dx2006sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018010976/dx2006Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989018010976/dx2006Isup3.cml
CCDC reference: 1036797
Additional supporting information: crystallographic information; 3D view; checkCIF report