research communications
Crystal structures of arylsulfonylation products of 2-alkyl-5-substituted-1H-benzimidazoles
aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, 100170, Tashkent, Uzbekistan, bUrgench State University, Kh. Alimdjan str., 14, 220100, Urgench City, Uzbekistan, cKara-Kalpak State University, acad. Abdirov Str., 1, 742000, Nukus, Uzbekistan, and dTurin Polytechnic University in Tashkent, Kichik Khalka yuli str. 17, 100095, Tashkent, Uzbekistan
*Correspondence e-mail: raxul@mail.ru
Mixed crystals of 1-(4-chlorophenylsulfonyl)-2,5-dimethyl-1H-benzimidazole and 1-(4-chlorophenylsulfonyl)-2,6-dimethyl-1H-benzimidazole (ratio 0.707:0.293; two molecules in the asymmetric unit), 0.707C15H13ClN2O2S·0.293C15H13ClN2O2S, (I), and of 2-n-butyl-1-(4-tert-butylphenylsulfonyl)-5-chloro-1H-benzimidazole and 2-n-butyl-1-(4-tert-butylphenylsulfonyl)-6-chloro-1H-benzimidazole [ratio 0.731 (2):0.269 (2); one molecule in the asymmetric unit], 0.731C21H25ClN2O2S·0.269C21H25ClN2O2S, (II), were obtained from the arylsulfonylation reaction of the corresponding 2-alkylbenzimidazoles. In addition, two products were obtained from the reaction of 2-n-butyl-5-chloro-1H-benzimidazole with 4-methylbenzenesulfonyl chloride. These reaction products were separated by and the of one of the products, 2-n-butyl-5-chloro-1-(4-methylphenylsulfonyl)-1H-benzimidazole (one molecule in the asymmetric unit), C18H19ClN2O2S, (III), was determined. In the crystal structures of (I)–(III), there is a difference in the arrangement of the planar benzimidazole and arylsulfonyl fragments. The formation of weak C—H⋯O hydrogen-bonding interactions is characteristic of all three crystal structures.
1. Chemical context
Benzimidazole derivatives are an important class of heteroaromatic compounds because of their biological and pharmaceutical activities (Keri et al., 2015). The benzimidazole entity has seven positions for substitution of various moieties. The literature describes most biologically active compounds based on benzimidazole derivatives bearing functional groups in positions 1, 2 and/or 5 (or 6) (Bansal & Silakari, 2012). A large number of benzimidazole derivatives have been found to exhibit antibacterial (Elnima et al., 1981), antiviral (Townsend et al., 1995), antifungal (Desai & Desai, 2006), antidiabetic, antiasthmatic (Ramanatham et al., 2008), anti-HIV (Li et al., 2009), anticonvulsant (Bhrigu et al., 2012), antihypertensive (Jain et al., 2013), and antidepressant (Mathew et al., 2016) activities.
In addition, among derivatives of arylsulfonylbenzimidazoles, substances with a variety of biological activities have been reported, such as inhibition of HBV (Li et al., 2007), acting on the NPY Y5 receptor (Tamura et al., 2012), and as antimicrobial and antitubercular (Ranjith et al., 2013), anti-inflammatory and analgesic agents (Gaba et al., 2010).
The synthesis of arylsulfonylbenzimidazoles has therefore attracted the attention of organic chemists. The preparation of an individual substance of this class involves the arylsulfonylation of benzimidazole (Abdireimov et al., 2010), either by an intramolecular Csp2—H amidation using N-iodosuccinimide (Alam et al., 2018), the rearrangement of 7-sulfonamidobenzoxazole with ZnCl2 or Zn(NO3)2 (Tanakit et al., 2012), or the intramolecular amidation of N-tosyl-o-phenylenediamine derivatives (for obtaining 1,2-disubstituted benzimidazoles) (Maiti & Mal, 2015; Hu et al., 2017). The above reactions produce a variety of arylsulfonylbenzimidazole derivatives but there are other conditions that produce two derivatives such as the amination of N′′-aryl-N′-tosyl/N′-methylsulfonylamidines derivatives (Alla et al., 2013). The main reason for two-product formation is the content of the in the phenyl fragment of the starting compound.
In the arylsulfonylation reaction of 2,5-dimethyl-1H-benzimidazole and 2-n-butyl-5-chloro-1H-benzimidazole, the formation of two products was likewise observed, which can be explained by the of benzimidazoles. During the arylsulfonylation reaction of benzimidazole derivatives, the acidic proton of benzimidazole is in equilibrium between positions 1 and 3, and consequently, two isomers are formed (Ranjith et al., 2013).
In the reaction of 2,5-dimethyl-1H-benzimidazole with 4-chlorobenzenesulfonyl chloride in the presence of triethylamine, two products were formed (Fig. 1). After purification of the reaction mixture, the single crystals of the two corresponding components were subjected to structure analysis by X-ray diffraction, showing that mixed crystals of 1-(4-chlorophenylsulfonyl)-2,5-dimethyl-1H-benzimidazole and 1-(4-chlorophenylsulfonyl)-2,6-dimethyl-1H-benzimidazole (I) were obtained. Likewise, mixed crystals of 2-n-butyl-1-(4-tert-butylphenylsulfonyl)-5-chloro-1H-benzimidazole and 2-n-butyl-1-(4-tert-butylphenylsulfonyl)-6-chloro-1H-benzimidazole (II) were obtained from the reaction of 2-n-butyl-5-chloro-1H-benzimidazole and 4-tert-butylbenzenesulfonil chloride. In addition, arylsulfonylation of 2-n-butyl-5-chloro-1H-benzimidazole with 4-methylbenzenesulfonyl chloride also gave two products. To study the structural features, the latter mixture of products was separated using column chromatography. From the separated products, single crystals of 2-n-butyl-5-chloro-1-(4-methylphenylsulfonyl)-1H-benzimidazole (III) were grown.
2. Structural commentary
The I) consists of two molecules: A and B (Fig. 2). Molecule A corresponds to 1-(4-chlorophenylsulfonyl)-2,5-dimethyl-1H-benzimidazole, and for B the allocated molecules are 1-(4-chlorophenylsulfonyl)-2,6-dimethyl-1H-benzimidazole and 1-(4-chlorophenylsulfonyl)-2,5-dimethyl-1H-benzimidazole in the ratio 0.555 (10):0.445 (10) (overall A:B ratio in the crystal of 0.707:0.293). Hence, (I) can be considered as a mixed crystal of the two latter molecules.
of crystal (Crystal (II) is a mixed crystal of 2-n-butyl-1-(4-tert-butylphenylsulfonyl)-5-chloro-1H-benzimidazole and of 2-n-butyl-1-(4-tert-butylphenylsulfonyl)-6-chloro-1H-benzimidazole in the ratio of 0.731 (2):0.269 (2), that differ in the position of the chloro substituent. Here, only one molecule is present in the (Fig. 3).
The III) likewise comprises one molecule, 2-n-butyl-5-chloro-1-(4-methylphenylsulfonyl)-1H-benzimidazole (Fig. 4).
of crystal (The molecules of (I)–(III) consist of two flat fragments, viz. benzimidazole (N1/C2/N3/C3A/C4–C7/C7A) and benzene (C8–C13). The angles between the fragments are 83.4 (1)° for (IA), 79.3 (1)° for (IB), 87.1 (1)° for (II), and 86.6 (1)° for (III). These values do not differ significantly from the previously reported structures of related benzimidazole derivatives (Abdireymov et al., 2011). However, the orientation of the entities along the N1—S1 and S1—C8 bonds is different (Tables 1, 2 and 3).
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3. Supramolecular features
In the crystal packing of (I), two A molecules form a centrosymmetric dimer by weak C14A—H14C⋯O1A hydrogen bonds. A Cl⋯Cl interaction between these dimers [Cl1A⋯Cl1A(2 − x, 1 − y, 1 − z) = 3.304 (3) Å, 0.20 Å less than the sum of the the van der Waals radii] links the molecules into chains running parallel to the b axis. Molecules of B are linked by C4B—H4BA⋯Cl1 hydrogen bonds, which also form chains extending in the same direction (Table 4, Fig. 5). Intermolecular C—H⋯π interactions between these chains consolidate the [C12A—H12A⋯Cg1: H⋯Cg1 = 2.85 Å; C12A—H⋯Cg1 = 3.549 (7) Å; C12A—H⋯Cg1 = 133° (symmetry code for Cg1: 1 + x, y, z; Cg1 is the centroid of the C3B′/C4B--C7B/C7B′ benzene ring); C10B—H10B⋯Cg2: H⋯Cg2 = 2.81 Å; C10B—H⋯Cg2 = 3.558 (6) Å; C10B—H⋯Cg2 = 139° (symmetry code for the Cg2 centroid: −1 + x, − y, − + z; Cg2 is centroid of the C3A′/C4A–C7A/C7A′ benzene ring)].
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In the crystal packing of (II), the formation of a centrosymmetric dimer as the result of an intermolecular C—H⋯π bond is also observed [C4—H4A⋯Cg3: H⋯Cg3 = 2.71 Å; C4—H⋯Cg3 = 3.590 (4) Å; C4—H⋯Cg3 = 158° (symmetry code for Cg3: −x, 1 − y, 1 − z; Cg3 is centroid of the C8–C13 benzene ring)]. These dimers are linked into chains running parallel to the a axis by Cl⋯Cl interactions [Cl1⋯Cl1(−x, 2 − y, 2 − z) = 3.435 (3) Å, 0.06 Å less than the sum of the van der Waals radii] and a weak intermolecular C10—H10A⋯O2 hydrogen bond (Table 5, Fig. 6). Similar C—H⋯π and C—H⋯O interactions were observed in the previously studied mixed crystal of 2-n-butyl-6-chloro-1-(2,4-dimethylbenzenesulfonyl)-1H-benzimidazole and 2-n-butyl-5-chloro-1-(2,4-dimethylbenzenesulfonyl)-1H-benzimidazole (Abdireymov et al., 2011).
In the crystal packing of (III), only weak hydrogen bonds of the type C—H⋯O are observed. Chains parallel to the a axis are formed through intermolecular C12—H12A⋯O1 interactions. Further C18—H18D⋯O2 hydrogen bonds between the formed chains consolidate the packing (Table 6, Fig. 7). Interactions such as Cl⋯Cl and C—H⋯π are not observed in (III).
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Halogen–halogen bonds such as the Cl⋯Cl interactions observed in the crystals of (I) and (II) have been studied by various methods, with the characteristics of such interactions described in the literature (Hathwar et al., 2010; Bui et al., 2009).
4. Database survey
A search in the Cambridge database (version 2022.1.0; Groom et al., 2016) showed that 1-arylsulfonyl-1H-benzimidazoles with one or more substituents in positions 2, 4, 5, 6 resulted in 21 hits. Of these, five are 1-arylsulfonyl-2-alkyl(aryl)-1H-benzimidazole derivatives. The most similar structures are 6-chloro-2-methyl-1-[(4-methylphenyl)sulfonyl]-1H-benzimidazole (MEZDAY; Alla et al., 2013), and the mixed crystals of 2-n-butyl-6-chloro-1-(2,4-dimethylbenzenesulfonyl)-1H-benzimidazole and 2-n-butyl-5-chloro-1-(2,4-dimethylbenzenesulfonyl)-1H-benzimidazole (OCEVEZ; Abdireymov et al., 2011).
5. Synthesis and crystallization
The title compounds were synthesized according to a previously reported procedure (Abdireimov et al., 2010). After purification of the corresponding reaction mixtures, single crystals for X-ray were obtained by evaporation of ethanol solutions at room temperature.
The reaction products of 2-n-butyl-5-chloro-1H-benzimidazole with 4-methylbenzenesulfonyl chloride were separated by in a benzene:acetone (10:1 v:v) system. Colorless crystals of (III) for X-ray analysis were obtained by slow evaporation of an ethanol solution.
6. Refinement
Crystal data, data collection and structure . In the of (I), the C1B site in the (IB) molecule is disordered over two positions (C1B and C1B′). The site occupancy factors refined to a ratio of 0.555 (10):0.445 (10). In the of (II), the Cl site is disordered over two positions (Cl1 and Cl1′), with refined site occupation factors of 0.731 (2):0.269 (2) for the major and minor components. All H atoms bound to C atoms were placed geometrically (with C—H distances of 0.97 Å for CH2, 0.96 Å for CH3 and 0.93 Å for Car) and included in the in a riding-motion approximation with Uiso(H) = 1.2Ueq(C) [Uiso = 1.5Ueq(C) for methyl H atoms].
details are summarized in Table 7Supporting information
https://doi.org/10.1107/S2056989022011070/wm5663sup1.cif
contains datablocks I, II, III, Global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022011070/wm5663Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989022011070/wm5663IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989022011070/wm5663IIIsup4.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989022011070/wm5663Isup5.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022011070/wm5663IIsup6.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022011070/wm5663IIIsup7.cml
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2021); cell
CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2020) and publCIF (Westrip, 2010).0.707C15H13ClN2O2S·0.293C15H13ClN2O2S | F(000) = 1328 |
Mr = 320.78 | Dx = 1.402 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 9.837 (2) Å | Cell parameters from 1714 reflections |
b = 19.674 (4) Å | θ = 3.6–43.7° |
c = 16.046 (3) Å | µ = 3.56 mm−1 |
β = 101.91 (3)° | T = 296 K |
V = 3038.6 (11) Å3 | Prizmatic, colorless |
Z = 8 | 0.60 × 0.40 × 0.30 mm |
Xcalibur, Ruby diffractometer | 5354 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2629 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
Detector resolution: 10.2576 pixels mm-1 | θmax = 66.8°, θmin = 3.6° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −23→23 |
Tmin = 0.482, Tmax = 1.000 | l = −19→17 |
13759 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.065 | H-atom parameters constrained |
wR(F2) = 0.190 | w = 1/[σ2(Fo2) + (0.092P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
5354 reflections | Δρmax = 0.30 e Å−3 |
394 parameters | Δρmin = −0.29 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1A | 0.98039 (16) | 0.10855 (7) | 0.48596 (8) | 0.0759 (4) | |
O1A | 0.8450 (4) | 0.08551 (18) | 0.4479 (2) | 0.0963 (12) | |
O2A | 1.0979 (5) | 0.08877 (19) | 0.4541 (2) | 0.1020 (13) | |
Cl1A | 0.9719 (2) | 0.42170 (7) | 0.52959 (10) | 0.1301 (8) | |
N1A | 1.0069 (4) | 0.08135 (18) | 0.5868 (2) | 0.0695 (11) | |
N3A | 1.1128 (6) | 0.0524 (2) | 0.7190 (3) | 0.0839 (13) | |
C1A | 0.6646 (9) | 0.0576 (4) | 0.8265 (5) | 0.178 (4) | |
H1AA | 0.568434 | 0.062899 | 0.799769 | 0.268* | |
H1AB | 0.689313 | 0.090950 | 0.870784 | 0.268* | |
H1AC | 0.679452 | 0.012922 | 0.850632 | 0.268* | |
C2A | 1.1341 (6) | 0.0658 (2) | 0.6431 (3) | 0.0754 (14) | |
C3A' | 0.9698 (7) | 0.0613 (2) | 0.7144 (4) | 0.0804 (15) | |
C4A | 0.8939 (9) | 0.0536 (3) | 0.7809 (4) | 0.103 (2) | |
H4AA | 0.936901 | 0.039950 | 0.835433 | 0.124* | |
C5A | 0.7550 (9) | 0.0675 (3) | 0.7599 (5) | 0.103 (2) | |
C6A | 0.6906 (8) | 0.0861 (3) | 0.6798 (5) | 0.111 (2) | |
H6AA | 0.595586 | 0.094593 | 0.668762 | 0.133* | |
C7A | 0.7607 (7) | 0.0927 (3) | 0.6149 (4) | 0.0916 (17) | |
H7AA | 0.715480 | 0.105605 | 0.560447 | 0.110* | |
C7A' | 0.9013 (6) | 0.0793 (2) | 0.6338 (3) | 0.0706 (13) | |
C8A | 0.9767 (5) | 0.1967 (2) | 0.4957 (3) | 0.0648 (12) | |
C9A | 0.8527 (6) | 0.2297 (2) | 0.4937 (3) | 0.0809 (15) | |
H9AA | 0.770588 | 0.204821 | 0.485164 | 0.097* | |
C10A | 0.8489 (6) | 0.2996 (3) | 0.5042 (3) | 0.0888 (16) | |
H10A | 0.765648 | 0.322211 | 0.503487 | 0.107* | |
C11A | 0.9722 (8) | 0.3343 (3) | 0.5156 (3) | 0.0836 (16) | |
C12A | 1.0956 (7) | 0.3026 (3) | 0.5166 (3) | 0.0895 (17) | |
H12A | 1.177596 | 0.327482 | 0.523920 | 0.107* | |
C13A | 1.0973 (6) | 0.2332 (3) | 0.5065 (3) | 0.0821 (15) | |
H13A | 1.180961 | 0.210991 | 0.507059 | 0.099* | |
C14A | 1.2700 (6) | 0.0651 (3) | 0.6187 (4) | 0.0952 (17) | |
H14A | 1.340001 | 0.050644 | 0.666258 | 0.143* | |
H14B | 1.291553 | 0.109979 | 0.601750 | 0.143* | |
H14C | 1.267197 | 0.034256 | 0.571991 | 0.143* | |
S1B | 0.27801 (13) | 0.20178 (7) | 0.24317 (7) | 0.0697 (4) | |
O1B | 0.3041 (4) | 0.26502 (18) | 0.20548 (19) | 0.0845 (11) | |
O2B | 0.3156 (4) | 0.13910 (19) | 0.2109 (2) | 0.0880 (11) | |
Cl1B | −0.34000 (16) | 0.19051 (12) | 0.27275 (11) | 0.1444 (9) | |
N1B | 0.3639 (4) | 0.2062 (2) | 0.3441 (2) | 0.0664 (10) | |
N3B | 0.4687 (4) | 0.1754 (3) | 0.4773 (3) | 0.0825 (13) | |
C1B | 0.3389 (12) | 0.4565 (5) | 0.4256 (7) | 0.121 (5) | 0.555 (10) |
H1BA | 0.380443 | 0.483598 | 0.473870 | 0.182* | 0.555 (10) |
H1BB | 0.239668 | 0.457241 | 0.419044 | 0.182* | 0.555 (10) |
H1BC | 0.363827 | 0.474586 | 0.375207 | 0.182* | 0.555 (10) |
C1B' | 0.5215 (19) | 0.4175 (7) | 0.5827 (8) | 0.148 (8) | 0.445 (10) |
H1BD | 0.615790 | 0.406184 | 0.608341 | 0.222* | 0.445 (10) |
H1BE | 0.468026 | 0.421590 | 0.626136 | 0.222* | 0.445 (10) |
H1BF | 0.519539 | 0.459796 | 0.552680 | 0.222* | 0.445 (10) |
C2B | 0.4156 (5) | 0.1531 (3) | 0.4014 (3) | 0.0745 (14) | |
C3B' | 0.4514 (5) | 0.2458 (3) | 0.4737 (3) | 0.0742 (14) | |
C4B | 0.4894 (6) | 0.2945 (4) | 0.5384 (3) | 0.0910 (17) | |
H4BA | 0.534228 | 0.281439 | 0.592826 | 0.109* | |
C5B | 0.4594 (7) | 0.3612 (4) | 0.5200 (4) | 0.102 (2) | |
H5BA | 0.484947 | 0.393493 | 0.562622 | 0.122* | 0.555 (10) |
C6B | 0.3917 (7) | 0.3823 (3) | 0.4394 (4) | 0.103 (2) | |
H6BA | 0.370651 | 0.428069 | 0.429278 | 0.123* | 0.445 (10) |
C7B | 0.3553 (6) | 0.3353 (3) | 0.3738 (3) | 0.0843 (16) | |
H7BA | 0.311950 | 0.348838 | 0.319236 | 0.101* | |
C7B' | 0.3864 (5) | 0.2667 (3) | 0.3930 (3) | 0.0692 (13) | |
C8B | 0.1024 (5) | 0.1986 (2) | 0.2501 (2) | 0.0597 (11) | |
C9B | 0.0312 (6) | 0.2576 (3) | 0.2556 (3) | 0.0797 (15) | |
H9BA | 0.075341 | 0.299434 | 0.255486 | 0.096* | |
C10B | −0.1040 (7) | 0.2546 (3) | 0.2612 (4) | 0.0916 (17) | |
H10B | −0.153441 | 0.294480 | 0.264433 | 0.110* | |
C11B | −0.1681 (6) | 0.1931 (4) | 0.2621 (3) | 0.0870 (17) | |
C12B | −0.0993 (6) | 0.1337 (3) | 0.2560 (3) | 0.0829 (15) | |
H12B | −0.144353 | 0.092187 | 0.256028 | 0.099* | |
C13B | 0.0385 (5) | 0.1365 (2) | 0.2499 (3) | 0.0678 (13) | |
H13B | 0.087610 | 0.096660 | 0.245649 | 0.081* | |
C14B | 0.4104 (7) | 0.0798 (3) | 0.3785 (4) | 0.1045 (19) | |
H14D | 0.453652 | 0.053565 | 0.427283 | 0.157* | |
H14E | 0.458839 | 0.072588 | 0.333116 | 0.157* | |
H14F | 0.315348 | 0.065870 | 0.360439 | 0.157* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0993 (11) | 0.0590 (7) | 0.0667 (8) | 0.0013 (7) | 0.0111 (7) | −0.0035 (6) |
O1A | 0.110 (3) | 0.071 (2) | 0.092 (2) | −0.016 (2) | −0.015 (2) | −0.0091 (18) |
O2A | 0.133 (4) | 0.094 (3) | 0.089 (2) | 0.029 (3) | 0.045 (2) | −0.006 (2) |
Cl1A | 0.223 (2) | 0.0559 (8) | 0.1053 (11) | −0.0132 (11) | 0.0190 (12) | 0.0026 (7) |
N1A | 0.081 (3) | 0.059 (2) | 0.068 (2) | 0.000 (2) | 0.014 (2) | 0.0017 (19) |
N3A | 0.113 (4) | 0.063 (3) | 0.067 (3) | 0.000 (3) | −0.001 (3) | 0.003 (2) |
C1A | 0.192 (10) | 0.200 (10) | 0.163 (7) | −0.015 (8) | 0.081 (7) | −0.007 (6) |
C2A | 0.087 (4) | 0.051 (3) | 0.083 (4) | −0.001 (3) | 0.006 (3) | −0.003 (2) |
C3A' | 0.104 (5) | 0.050 (3) | 0.088 (4) | −0.005 (3) | 0.024 (4) | −0.002 (3) |
C4A | 0.153 (7) | 0.069 (4) | 0.092 (4) | −0.014 (4) | 0.036 (5) | 0.006 (3) |
C5A | 0.114 (6) | 0.094 (5) | 0.112 (5) | −0.019 (4) | 0.051 (5) | −0.010 (4) |
C6A | 0.119 (6) | 0.072 (4) | 0.142 (6) | −0.015 (4) | 0.027 (5) | 0.001 (4) |
C7A | 0.091 (5) | 0.078 (4) | 0.109 (4) | −0.017 (3) | 0.029 (4) | 0.007 (3) |
C7A' | 0.087 (4) | 0.048 (2) | 0.074 (3) | −0.007 (3) | 0.011 (3) | 0.002 (2) |
C8A | 0.075 (3) | 0.062 (3) | 0.057 (3) | −0.003 (3) | 0.012 (2) | 0.003 (2) |
C9A | 0.078 (4) | 0.062 (3) | 0.104 (4) | −0.009 (3) | 0.023 (3) | 0.008 (3) |
C10A | 0.093 (4) | 0.067 (3) | 0.114 (4) | 0.009 (3) | 0.038 (3) | 0.011 (3) |
C11A | 0.122 (5) | 0.056 (3) | 0.073 (3) | −0.009 (3) | 0.021 (3) | 0.007 (2) |
C12A | 0.091 (4) | 0.078 (4) | 0.093 (4) | −0.032 (4) | 0.006 (3) | 0.013 (3) |
C13A | 0.072 (4) | 0.078 (4) | 0.099 (4) | −0.007 (3) | 0.022 (3) | 0.017 (3) |
C14A | 0.082 (4) | 0.084 (4) | 0.115 (4) | 0.001 (3) | 0.010 (3) | −0.003 (3) |
S1B | 0.0610 (8) | 0.0857 (9) | 0.0641 (7) | −0.0045 (7) | 0.0167 (6) | −0.0066 (7) |
O1B | 0.086 (3) | 0.101 (3) | 0.067 (2) | −0.022 (2) | 0.0169 (18) | 0.0136 (18) |
O2B | 0.075 (2) | 0.106 (3) | 0.086 (2) | 0.011 (2) | 0.0232 (19) | −0.024 (2) |
Cl1B | 0.0531 (9) | 0.257 (3) | 0.1239 (13) | 0.0122 (12) | 0.0199 (8) | 0.0576 (14) |
N1B | 0.061 (2) | 0.071 (3) | 0.066 (2) | 0.001 (2) | 0.0108 (19) | 0.002 (2) |
N3B | 0.070 (3) | 0.096 (4) | 0.077 (3) | 0.001 (3) | 0.004 (2) | 0.009 (3) |
C1B | 0.130 (11) | 0.073 (8) | 0.147 (10) | −0.005 (7) | −0.004 (8) | −0.036 (7) |
C1B' | 0.25 (2) | 0.110 (12) | 0.090 (10) | −0.073 (13) | 0.046 (12) | −0.033 (9) |
C2B | 0.063 (3) | 0.077 (3) | 0.085 (4) | 0.007 (3) | 0.018 (3) | 0.007 (3) |
C3B' | 0.061 (3) | 0.099 (4) | 0.062 (3) | −0.008 (3) | 0.012 (3) | 0.002 (3) |
C4B | 0.090 (4) | 0.118 (5) | 0.062 (3) | −0.023 (4) | 0.010 (3) | 0.000 (3) |
C5B | 0.119 (6) | 0.100 (5) | 0.086 (4) | −0.027 (4) | 0.020 (4) | −0.021 (4) |
C6B | 0.119 (5) | 0.101 (5) | 0.087 (4) | −0.032 (4) | 0.020 (4) | −0.014 (4) |
C7B | 0.091 (4) | 0.082 (4) | 0.079 (3) | −0.016 (3) | 0.014 (3) | 0.002 (3) |
C7B' | 0.057 (3) | 0.081 (3) | 0.071 (3) | −0.015 (3) | 0.018 (3) | −0.004 (3) |
C8B | 0.063 (3) | 0.065 (3) | 0.053 (2) | −0.001 (2) | 0.015 (2) | −0.002 (2) |
C9B | 0.074 (4) | 0.069 (3) | 0.098 (4) | 0.009 (3) | 0.021 (3) | 0.003 (3) |
C10B | 0.072 (4) | 0.094 (5) | 0.109 (4) | 0.025 (3) | 0.020 (3) | 0.007 (4) |
C11B | 0.057 (3) | 0.137 (6) | 0.064 (3) | 0.011 (4) | 0.006 (2) | 0.027 (3) |
C12B | 0.068 (4) | 0.097 (4) | 0.080 (3) | −0.013 (3) | 0.008 (3) | 0.019 (3) |
C13B | 0.065 (3) | 0.067 (3) | 0.069 (3) | −0.001 (3) | 0.008 (2) | 0.003 (2) |
C14B | 0.104 (5) | 0.084 (4) | 0.118 (5) | 0.011 (4) | 0.006 (4) | 0.003 (4) |
S1A—O2A | 1.412 (4) | S1B—C8B | 1.755 (5) |
S1A—O1A | 1.420 (4) | Cl1B—C11B | 1.735 (6) |
S1A—N1A | 1.673 (4) | N1B—C2B | 1.414 (6) |
S1A—C8A | 1.743 (5) | N1B—C7B' | 1.419 (6) |
Cl1A—C11A | 1.734 (5) | N3B—C2B | 1.297 (6) |
N1A—C7A' | 1.403 (6) | N3B—C3B' | 1.394 (7) |
N1A—C2A | 1.418 (6) | C1B—C6B | 1.549 (12) |
N3A—C2A | 1.305 (6) | C1B—H1BA | 0.9600 |
N3A—C3A' | 1.404 (7) | C1B—H1BB | 0.9600 |
C1A—C5A | 1.537 (9) | C1B—H1BC | 0.9600 |
C1A—H1AA | 0.9600 | C1B'—C5B | 1.536 (13) |
C1A—H1AB | 0.9600 | C1B'—H1BD | 0.9600 |
C1A—H1AC | 0.9600 | C1B'—H1BE | 0.9600 |
C2A—C14A | 1.469 (7) | C1B'—H1BF | 0.9600 |
C3A'—C7A' | 1.376 (7) | C2B—C14B | 1.487 (7) |
C3A'—C4A | 1.431 (8) | C3B'—C7B' | 1.384 (6) |
C4A—C5A | 1.366 (9) | C3B'—C4B | 1.405 (7) |
C4A—H4AA | 0.9300 | C4B—C5B | 1.364 (8) |
C5A—C6A | 1.361 (9) | C4B—H4BA | 0.9300 |
C6A—C7A | 1.369 (8) | C5B—C6B | 1.390 (8) |
C6A—H6AA | 0.9300 | C5B—H5BA | 0.9300 |
C7A—C7A' | 1.379 (7) | C6B—C7B | 1.391 (7) |
C7A—H7AA | 0.9300 | C6B—H6BA | 0.9300 |
C8A—C13A | 1.367 (7) | C7B—C7B' | 1.404 (7) |
C8A—C9A | 1.376 (7) | C7B—H7BA | 0.9300 |
C9A—C10A | 1.388 (7) | C8B—C9B | 1.368 (6) |
C9A—H9AA | 0.9300 | C8B—C13B | 1.374 (6) |
C10A—C11A | 1.370 (8) | C9B—C10B | 1.353 (7) |
C10A—H10A | 0.9300 | C9B—H9BA | 0.9300 |
C11A—C12A | 1.362 (7) | C10B—C11B | 1.366 (8) |
C12A—C13A | 1.375 (7) | C10B—H10B | 0.9300 |
C12A—H12A | 0.9300 | C11B—C12B | 1.363 (7) |
C13A—H13A | 0.9300 | C12B—C13B | 1.380 (7) |
C14A—H14A | 0.9600 | C12B—H12B | 0.9300 |
C14A—H14B | 0.9600 | C13B—H13B | 0.9300 |
C14A—H14C | 0.9600 | C14B—H14D | 0.9600 |
S1B—O2B | 1.416 (3) | C14B—H14E | 0.9600 |
S1B—O1B | 1.430 (3) | C14B—H14F | 0.9600 |
S1B—N1B | 1.667 (4) | ||
O2A—S1A—O1A | 121.4 (2) | N1B—S1B—C8B | 104.37 (19) |
O2A—S1A—N1A | 106.7 (2) | C2B—N1B—C7B' | 105.4 (4) |
O1A—S1A—N1A | 105.0 (2) | C2B—N1B—S1B | 129.5 (4) |
O2A—S1A—C8A | 109.9 (3) | C7B'—N1B—S1B | 124.8 (3) |
O1A—S1A—C8A | 108.8 (2) | C2B—N3B—C3B' | 106.0 (4) |
N1A—S1A—C8A | 103.5 (2) | C6B—C1B—H1BA | 109.5 |
C7A'—N1A—C2A | 107.8 (4) | C6B—C1B—H1BB | 109.5 |
C7A'—N1A—S1A | 122.9 (4) | H1BA—C1B—H1BB | 109.5 |
C2A—N1A—S1A | 128.8 (4) | C6B—C1B—H1BC | 109.5 |
C2A—N3A—C3A' | 106.1 (5) | H1BA—C1B—H1BC | 109.5 |
C5A—C1A—H1AA | 109.5 | H1BB—C1B—H1BC | 109.5 |
C5A—C1A—H1AB | 109.5 | C5B—C1B'—H1BD | 109.5 |
H1AA—C1A—H1AB | 109.5 | C5B—C1B'—H1BE | 109.5 |
C5A—C1A—H1AC | 109.5 | H1BD—C1B'—H1BE | 109.5 |
H1AA—C1A—H1AC | 109.5 | C5B—C1B'—H1BF | 109.5 |
H1AB—C1A—H1AC | 109.5 | H1BD—C1B'—H1BF | 109.5 |
N3A—C2A—N1A | 110.3 (5) | H1BE—C1B'—H1BF | 109.5 |
N3A—C2A—C14A | 125.3 (5) | N3B—C2B—N1B | 112.5 (5) |
N1A—C2A—C14A | 124.4 (5) | N3B—C2B—C14B | 123.1 (5) |
C7A'—C3A'—N3A | 111.9 (5) | N1B—C2B—C14B | 124.4 (5) |
C7A'—C3A'—C4A | 119.9 (6) | C7B'—C3B'—N3B | 111.3 (5) |
N3A—C3A'—C4A | 128.2 (6) | C7B'—C3B'—C4B | 119.3 (6) |
C5A—C4A—C3A' | 116.4 (6) | N3B—C3B'—C4B | 129.4 (5) |
C5A—C4A—H4AA | 121.8 | C5B—C4B—C3B' | 118.9 (5) |
C3A'—C4A—H4AA | 121.8 | C5B—C4B—H4BA | 120.5 |
C6A—C5A—C4A | 122.2 (7) | C3B'—C4B—H4BA | 120.5 |
C6A—C5A—C1A | 117.9 (8) | C4B—C5B—C6B | 122.0 (6) |
C4A—C5A—C1A | 119.8 (8) | C4B—C5B—C1B' | 120.9 (8) |
C5A—C6A—C7A | 122.4 (7) | C6B—C5B—C1B' | 116.3 (8) |
C5A—C6A—H6AA | 118.8 | C4B—C5B—H5BA | 119.0 |
C7A—C6A—H6AA | 118.8 | C6B—C5B—H5BA | 119.0 |
C6A—C7A—C7A' | 117.0 (6) | C5B—C6B—C7B | 120.2 (6) |
C6A—C7A—H7AA | 121.5 | C5B—C6B—C1B | 119.8 (6) |
C7A'—C7A—H7AA | 121.5 | C7B—C6B—C1B | 119.4 (7) |
C3A'—C7A'—C7A | 122.0 (6) | C5B—C6B—H6BA | 119.9 |
C3A'—C7A'—N1A | 103.8 (5) | C7B—C6B—H6BA | 119.9 |
C7A—C7A'—N1A | 134.1 (5) | C6B—C7B—C7B' | 117.6 (5) |
C13A—C8A—C9A | 119.9 (5) | C6B—C7B—H7BA | 121.2 |
C13A—C8A—S1A | 120.0 (4) | C7B'—C7B—H7BA | 121.2 |
C9A—C8A—S1A | 120.1 (4) | C3B'—C7B'—C7B | 122.0 (5) |
C8A—C9A—C10A | 120.7 (5) | C3B'—C7B'—N1B | 104.9 (5) |
C8A—C9A—H9AA | 119.7 | C7B—C7B'—N1B | 133.1 (5) |
C10A—C9A—H9AA | 119.7 | C9B—C8B—C13B | 121.0 (5) |
C11A—C10A—C9A | 117.7 (5) | C9B—C8B—S1B | 119.8 (4) |
C11A—C10A—H10A | 121.2 | C13B—C8B—S1B | 119.1 (4) |
C9A—C10A—H10A | 121.2 | C10B—C9B—C8B | 119.3 (5) |
C12A—C11A—C10A | 122.4 (5) | C10B—C9B—H9BA | 120.3 |
C12A—C11A—Cl1A | 118.6 (5) | C8B—C9B—H9BA | 120.3 |
C10A—C11A—Cl1A | 119.0 (5) | C9B—C10B—C11B | 120.1 (6) |
C11A—C12A—C13A | 119.1 (5) | C9B—C10B—H10B | 119.9 |
C11A—C12A—H12A | 120.5 | C11B—C10B—H10B | 119.9 |
C13A—C12A—H12A | 120.5 | C12B—C11B—C10B | 121.4 (5) |
C8A—C13A—C12A | 120.3 (6) | C12B—C11B—Cl1B | 119.4 (5) |
C8A—C13A—H13A | 119.8 | C10B—C11B—Cl1B | 119.2 (5) |
C12A—C13A—H13A | 119.8 | C11B—C12B—C13B | 118.8 (5) |
C2A—C14A—H14A | 109.5 | C11B—C12B—H12B | 120.6 |
C2A—C14A—H14B | 109.5 | C13B—C12B—H12B | 120.6 |
H14A—C14A—H14B | 109.5 | C8B—C13B—C12B | 119.3 (5) |
C2A—C14A—H14C | 109.5 | C8B—C13B—H13B | 120.3 |
H14A—C14A—H14C | 109.5 | C12B—C13B—H13B | 120.3 |
H14B—C14A—H14C | 109.5 | C2B—C14B—H14D | 109.5 |
O2B—S1B—O1B | 121.4 (2) | C2B—C14B—H14E | 109.5 |
O2B—S1B—N1B | 106.4 (2) | H14D—C14B—H14E | 109.5 |
O1B—S1B—N1B | 105.5 (2) | C2B—C14B—H14F | 109.5 |
O2B—S1B—C8B | 109.1 (2) | H14D—C14B—H14F | 109.5 |
O1B—S1B—C8B | 108.9 (2) | H14E—C14B—H14F | 109.5 |
O2A—S1A—N1A—C7A' | −166.7 (4) | O1B—S1B—N1B—C2B | −155.2 (4) |
O1A—S1A—N1A—C7A' | −36.6 (4) | C8B—S1B—N1B—C2B | 90.1 (4) |
C8A—S1A—N1A—C7A' | 77.4 (4) | O2B—S1B—N1B—C7B' | 162.2 (4) |
O2A—S1A—N1A—C2A | 22.7 (5) | O1B—S1B—N1B—C7B' | 32.1 (4) |
O1A—S1A—N1A—C2A | 152.7 (4) | C8B—S1B—N1B—C7B' | −82.6 (4) |
C8A—S1A—N1A—C2A | −93.3 (4) | C3B'—N3B—C2B—N1B | 1.2 (6) |
C3A'—N3A—C2A—N1A | −1.9 (5) | C3B'—N3B—C2B—C14B | −178.7 (5) |
C3A'—N3A—C2A—C14A | 178.1 (5) | C7B'—N1B—C2B—N3B | −1.6 (5) |
C7A'—N1A—C2A—N3A | 2.1 (5) | S1B—N1B—C2B—N3B | −175.4 (3) |
S1A—N1A—C2A—N3A | 173.9 (3) | C7B'—N1B—C2B—C14B | 178.3 (5) |
C7A'—N1A—C2A—C14A | −177.8 (4) | S1B—N1B—C2B—C14B | 4.5 (7) |
S1A—N1A—C2A—C14A | −6.0 (7) | C2B—N3B—C3B'—C7B' | −0.4 (6) |
C2A—N3A—C3A'—C7A' | 1.0 (6) | C2B—N3B—C3B'—C4B | 179.5 (5) |
C2A—N3A—C3A'—C4A | −179.1 (5) | C7B'—C3B'—C4B—C5B | 0.9 (8) |
C7A'—C3A'—C4A—C5A | −2.3 (8) | N3B—C3B'—C4B—C5B | −178.9 (6) |
N3A—C3A'—C4A—C5A | 177.9 (5) | C3B'—C4B—C5B—C6B | 0.4 (10) |
C3A'—C4A—C5A—C6A | 1.5 (10) | C3B'—C4B—C5B—C1B' | −168.7 (9) |
C3A'—C4A—C5A—C1A | 177.4 (5) | C4B—C5B—C6B—C7B | −1.6 (10) |
C4A—C5A—C6A—C7A | −0.5 (10) | C1B'—C5B—C6B—C7B | 167.9 (9) |
C1A—C5A—C6A—C7A | −176.5 (6) | C4B—C5B—C6B—C1B | 170.1 (8) |
C5A—C6A—C7A—C7A' | 0.3 (9) | C5B—C6B—C7B—C7B' | 1.5 (9) |
N3A—C3A'—C7A'—C7A | −178.0 (5) | C1B—C6B—C7B—C7B' | −170.2 (7) |
C4A—C3A'—C7A'—C7A | 2.2 (7) | N3B—C3B'—C7B'—C7B | 178.9 (5) |
N3A—C3A'—C7A'—N1A | 0.3 (5) | C4B—C3B'—C7B'—C7B | −0.9 (8) |
C4A—C3A'—C7A'—N1A | −179.6 (4) | N3B—C3B'—C7B'—N1B | −0.6 (6) |
C6A—C7A—C7A'—C3A' | −1.1 (8) | C4B—C3B'—C7B'—N1B | 179.6 (4) |
C6A—C7A—C7A'—N1A | −178.8 (5) | C6B—C7B—C7B'—C3B' | −0.3 (8) |
C2A—N1A—C7A'—C3A' | −1.4 (5) | C6B—C7B—C7B'—N1B | 179.0 (5) |
S1A—N1A—C7A'—C3A' | −173.7 (3) | C2B—N1B—C7B'—C3B' | 1.2 (5) |
C2A—N1A—C7A'—C7A | 176.6 (5) | S1B—N1B—C7B'—C3B' | 175.4 (3) |
S1A—N1A—C7A'—C7A | 4.2 (8) | C2B—N1B—C7B'—C7B | −178.2 (5) |
O2A—S1A—C8A—C13A | −25.6 (5) | S1B—N1B—C7B'—C7B | −4.0 (8) |
O1A—S1A—C8A—C13A | −160.7 (4) | O2B—S1B—C8B—C9B | −161.2 (4) |
N1A—S1A—C8A—C13A | 88.0 (4) | O1B—S1B—C8B—C9B | −26.8 (4) |
O2A—S1A—C8A—C9A | 155.2 (4) | N1B—S1B—C8B—C9B | 85.5 (4) |
O1A—S1A—C8A—C9A | 20.1 (5) | O2B—S1B—C8B—C13B | 18.8 (4) |
N1A—S1A—C8A—C9A | −91.1 (4) | O1B—S1B—C8B—C13B | 153.2 (3) |
C13A—C8A—C9A—C10A | −1.3 (7) | N1B—S1B—C8B—C13B | −94.6 (4) |
S1A—C8A—C9A—C10A | 177.9 (4) | C13B—C8B—C9B—C10B | 0.2 (7) |
C8A—C9A—C10A—C11A | 0.7 (8) | S1B—C8B—C9B—C10B | −179.8 (4) |
C9A—C10A—C11A—C12A | 0.3 (8) | C8B—C9B—C10B—C11B | 0.6 (8) |
C9A—C10A—C11A—Cl1A | −179.6 (4) | C9B—C10B—C11B—C12B | −1.1 (9) |
C10A—C11A—C12A—C13A | −0.6 (8) | C9B—C10B—C11B—Cl1B | 178.0 (4) |
Cl1A—C11A—C12A—C13A | 179.3 (4) | C10B—C11B—C12B—C13B | 0.8 (8) |
C9A—C8A—C13A—C12A | 0.9 (7) | Cl1B—C11B—C12B—C13B | −178.3 (4) |
S1A—C8A—C13A—C12A | −178.2 (4) | C9B—C8B—C13B—C12B | −0.6 (7) |
C11A—C12A—C13A—C8A | 0.0 (8) | S1B—C8B—C13B—C12B | 179.5 (3) |
O2B—S1B—N1B—C2B | −25.1 (5) | C11B—C12B—C13B—C8B | 0.0 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14A—H14C···O1Ai | 0.96 | 2.59 | 3.271 (6) | 128 |
C4B—H4BA···Cl1Bii | 0.93 | 2.95 | 3.800 (6) | 153 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x+1, −y+1/2, z+1/2. |
0.731C21H25ClN2O2S·0.269C21H25ClN2O2S | Z = 2 |
Mr = 404.94 | F(000) = 428 |
Triclinic, P1 | Dx = 1.295 Mg m−3 |
a = 8.2990 (17) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 11.644 (2) Å | Cell parameters from 2307 reflections |
c = 12.279 (3) Å | θ = 4.1–74.7° |
α = 115.85 (3)° | µ = 2.71 mm−1 |
β = 99.03 (3)° | T = 296 K |
γ = 94.96 (3)° | Prizmatic, colorless |
V = 1038.5 (4) Å3 | 0.36 × 0.20 × 0.20 mm |
Xcalibur, Ruby diffractometer | 4179 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 3244 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 10.2576 pixels mm-1 | θmax = 76.2°, θmin = 4.1° |
ω scans | h = −9→10 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −14→14 |
Tmin = 0.842, Tmax = 1.000 | l = −15→10 |
7093 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.0775P)2 + 0.1659P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4179 reflections | Δρmax = 0.31 e Å−3 |
258 parameters | Δρmin = −0.30 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.20524 (7) | 0.60421 (6) | 0.27060 (6) | 0.0616 (2) | |
O1 | 0.1971 (2) | 0.73010 (19) | 0.28074 (18) | 0.0809 (6) | |
O2 | 0.3383 (2) | 0.5409 (2) | 0.22959 (17) | 0.0741 (5) | |
Cl1 | 0.04322 (14) | 0.99456 (11) | 0.86571 (10) | 0.0942 (4) | 0.731 (2) |
Cl1' | 0.0497 (4) | 1.0733 (2) | 0.6922 (3) | 0.0879 (11) | 0.269 (2) |
N1 | 0.2121 (2) | 0.62283 (19) | 0.41511 (18) | 0.0572 (5) | |
N3 | 0.2121 (2) | 0.5667 (2) | 0.56841 (18) | 0.0601 (5) | |
C2 | 0.2365 (3) | 0.5296 (2) | 0.4576 (2) | 0.0557 (5) | |
C3A | 0.1665 (3) | 0.6881 (2) | 0.6048 (2) | 0.0591 (6) | |
C4 | 0.1301 (3) | 0.7689 (3) | 0.7172 (2) | 0.0670 (6) | |
H4A | 0.130286 | 0.743758 | 0.779435 | 0.080* | |
C5 | 0.0938 (3) | 0.8879 (3) | 0.7332 (3) | 0.0752 (7) | |
H5A | 0.066479 | 0.943178 | 0.806841 | 0.090* | 0.269 (2) |
C6 | 0.0972 (3) | 0.9266 (3) | 0.6416 (3) | 0.0790 (8) | |
H6A | 0.074455 | 1.008161 | 0.655985 | 0.095* | 0.731 (2) |
C7 | 0.1332 (3) | 0.8475 (3) | 0.5299 (3) | 0.0718 (7) | |
H7A | 0.135532 | 0.874089 | 0.468797 | 0.086* | |
C7A | 0.1658 (3) | 0.7272 (2) | 0.5125 (2) | 0.0576 (5) | |
C8 | 0.0163 (3) | 0.4999 (2) | 0.1833 (2) | 0.0552 (5) | |
C9 | −0.1303 (3) | 0.5342 (2) | 0.2174 (2) | 0.0608 (6) | |
H9A | −0.129886 | 0.612762 | 0.285345 | 0.073* | |
C10 | −0.2776 (3) | 0.4498 (2) | 0.1488 (2) | 0.0604 (6) | |
H10A | −0.375999 | 0.472137 | 0.172548 | 0.072* | |
C11 | −0.2830 (3) | 0.3321 (2) | 0.0452 (2) | 0.0535 (5) | |
C12 | −0.1335 (3) | 0.3031 (2) | 0.0117 (2) | 0.0618 (6) | |
H12A | −0.133611 | 0.226523 | −0.058291 | 0.074* | |
C13 | 0.0161 (3) | 0.3855 (3) | 0.0801 (2) | 0.0639 (6) | |
H13A | 0.114924 | 0.363844 | 0.056629 | 0.077* | |
C14 | 0.2920 (3) | 0.4038 (2) | 0.3847 (2) | 0.0606 (6) | |
H14A | 0.397881 | 0.421798 | 0.366095 | 0.073* | |
H14B | 0.212373 | 0.353996 | 0.306658 | 0.073* | |
C15 | 0.3087 (3) | 0.3245 (2) | 0.4546 (2) | 0.0621 (6) | |
H15A | 0.201796 | 0.304537 | 0.470730 | 0.074* | |
H15B | 0.385109 | 0.375959 | 0.533893 | 0.074* | |
C16 | 0.3701 (3) | 0.1993 (3) | 0.3853 (3) | 0.0718 (7) | |
H16A | 0.476404 | 0.218735 | 0.367995 | 0.086* | |
H16B | 0.292768 | 0.146655 | 0.306656 | 0.086* | |
C17 | 0.3884 (4) | 0.1230 (3) | 0.4593 (3) | 0.0899 (9) | |
H17A | 0.427770 | 0.044557 | 0.412930 | 0.135* | |
H17B | 0.282801 | 0.101922 | 0.475016 | 0.135* | |
H17C | 0.466057 | 0.174357 | 0.536715 | 0.135* | |
C18 | −0.4480 (3) | 0.2395 (2) | −0.0235 (2) | 0.0624 (6) | |
C19 | −0.5259 (4) | 0.2093 (3) | 0.0686 (3) | 0.0883 (9) | |
H19A | −0.629593 | 0.151107 | 0.025877 | 0.132* | |
H19B | −0.544544 | 0.288199 | 0.132867 | 0.132* | |
H19C | −0.452465 | 0.169645 | 0.104512 | 0.132* | |
C20 | −0.4259 (4) | 0.1129 (3) | −0.1283 (3) | 0.0963 (10) | |
H20A | −0.532500 | 0.059832 | −0.172766 | 0.145* | |
H20B | −0.359814 | 0.067746 | −0.094261 | 0.145* | |
H20C | −0.371667 | 0.131430 | −0.183790 | 0.145* | |
C21 | −0.5653 (3) | 0.3055 (3) | −0.0773 (3) | 0.0812 (8) | |
H21A | −0.669470 | 0.248026 | −0.120107 | 0.122* | |
H21B | −0.517354 | 0.326108 | −0.134204 | 0.122* | |
H21C | −0.582711 | 0.383612 | −0.011331 | 0.122* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0507 (3) | 0.0742 (4) | 0.0618 (4) | −0.0055 (3) | 0.0076 (2) | 0.0371 (3) |
O1 | 0.0868 (13) | 0.0788 (12) | 0.0784 (12) | −0.0125 (10) | 0.0024 (10) | 0.0469 (10) |
O2 | 0.0465 (9) | 0.1040 (14) | 0.0744 (11) | 0.0001 (9) | 0.0150 (8) | 0.0448 (10) |
Cl1 | 0.0803 (7) | 0.0877 (7) | 0.0813 (7) | 0.0190 (5) | 0.0135 (5) | 0.0095 (5) |
Cl1' | 0.098 (2) | 0.0607 (15) | 0.0895 (19) | 0.0184 (13) | −0.0046 (15) | 0.0282 (13) |
N1 | 0.0497 (10) | 0.0615 (11) | 0.0589 (11) | 0.0008 (8) | 0.0075 (8) | 0.0290 (9) |
N3 | 0.0553 (11) | 0.0673 (12) | 0.0596 (11) | 0.0095 (9) | 0.0113 (9) | 0.0312 (9) |
C2 | 0.0417 (11) | 0.0633 (13) | 0.0627 (13) | 0.0009 (9) | 0.0062 (9) | 0.0323 (11) |
C3A | 0.0427 (11) | 0.0686 (14) | 0.0644 (14) | 0.0046 (10) | 0.0083 (10) | 0.0308 (12) |
C4 | 0.0541 (13) | 0.0750 (16) | 0.0634 (14) | 0.0091 (12) | 0.0089 (11) | 0.0256 (12) |
C5 | 0.0519 (13) | 0.0718 (17) | 0.0780 (17) | 0.0038 (12) | 0.0058 (12) | 0.0170 (14) |
C6 | 0.0609 (15) | 0.0585 (15) | 0.098 (2) | 0.0067 (12) | 0.0031 (14) | 0.0237 (15) |
C7 | 0.0638 (15) | 0.0655 (15) | 0.0821 (18) | 0.0021 (12) | 0.0048 (13) | 0.0352 (14) |
C7A | 0.0398 (10) | 0.0630 (13) | 0.0653 (14) | −0.0009 (9) | 0.0030 (9) | 0.0295 (11) |
C8 | 0.0464 (11) | 0.0637 (13) | 0.0569 (12) | 0.0026 (10) | 0.0067 (9) | 0.0313 (11) |
C9 | 0.0560 (13) | 0.0583 (13) | 0.0601 (13) | 0.0090 (10) | 0.0105 (10) | 0.0207 (11) |
C10 | 0.0451 (11) | 0.0671 (14) | 0.0662 (14) | 0.0127 (10) | 0.0126 (10) | 0.0273 (12) |
C11 | 0.0495 (11) | 0.0557 (12) | 0.0582 (12) | 0.0063 (9) | 0.0093 (9) | 0.0300 (10) |
C12 | 0.0569 (13) | 0.0634 (14) | 0.0583 (13) | 0.0077 (11) | 0.0146 (10) | 0.0214 (11) |
C13 | 0.0492 (12) | 0.0779 (16) | 0.0645 (14) | 0.0112 (11) | 0.0189 (11) | 0.0304 (12) |
C14 | 0.0509 (12) | 0.0641 (14) | 0.0638 (14) | 0.0034 (10) | 0.0112 (10) | 0.0281 (11) |
C15 | 0.0502 (12) | 0.0635 (14) | 0.0694 (15) | 0.0031 (10) | 0.0079 (11) | 0.0306 (12) |
C16 | 0.0567 (14) | 0.0671 (15) | 0.0841 (18) | 0.0084 (12) | 0.0067 (12) | 0.0311 (13) |
C17 | 0.086 (2) | 0.0736 (18) | 0.109 (2) | 0.0114 (15) | 0.0045 (18) | 0.0464 (18) |
C18 | 0.0547 (13) | 0.0609 (14) | 0.0672 (14) | −0.0009 (10) | 0.0074 (11) | 0.0293 (11) |
C19 | 0.0721 (18) | 0.101 (2) | 0.095 (2) | −0.0168 (16) | 0.0100 (15) | 0.0567 (19) |
C20 | 0.078 (2) | 0.0700 (18) | 0.103 (2) | −0.0111 (15) | 0.0108 (17) | 0.0137 (17) |
C21 | 0.0565 (15) | 0.094 (2) | 0.089 (2) | −0.0063 (14) | −0.0062 (13) | 0.0480 (17) |
S1—O2 | 1.417 (2) | C11—C18 | 1.529 (3) |
S1—O1 | 1.425 (2) | C12—C13 | 1.390 (3) |
S1—N1 | 1.682 (2) | C12—H12A | 0.9300 |
S1—C8 | 1.758 (2) | C13—H13A | 0.9300 |
Cl1—C5 | 1.705 (3) | C14—C15 | 1.511 (3) |
Cl1'—C6 | 1.652 (4) | C14—H14A | 0.9700 |
N1—C2 | 1.410 (3) | C14—H14B | 0.9700 |
N1—C7A | 1.419 (3) | C15—C16 | 1.514 (4) |
N3—C2 | 1.292 (3) | C15—H15A | 0.9700 |
N3—C3A | 1.391 (3) | C15—H15B | 0.9700 |
C2—C14 | 1.504 (3) | C16—C17 | 1.525 (4) |
C3A—C4 | 1.389 (3) | C16—H16A | 0.9700 |
C3A—C7A | 1.395 (3) | C16—H16B | 0.9700 |
C4—C5 | 1.379 (4) | C17—H17A | 0.9600 |
C4—H4A | 0.9300 | C17—H17B | 0.9600 |
C5—C6 | 1.385 (4) | C17—H17C | 0.9600 |
C5—H5A | 0.9300 | C18—C20 | 1.526 (4) |
C6—C7 | 1.376 (4) | C18—C21 | 1.531 (4) |
C6—H6A | 0.9300 | C18—C19 | 1.536 (4) |
C7—C7A | 1.380 (4) | C19—H19A | 0.9600 |
C7—H7A | 0.9300 | C19—H19B | 0.9600 |
C8—C13 | 1.381 (3) | C19—H19C | 0.9600 |
C8—C9 | 1.384 (3) | C20—H20A | 0.9600 |
C9—C10 | 1.385 (3) | C20—H20B | 0.9600 |
C9—H9A | 0.9300 | C20—H20C | 0.9600 |
C10—C11 | 1.396 (3) | C21—H21A | 0.9600 |
C10—H10A | 0.9300 | C21—H21B | 0.9600 |
C11—C12 | 1.391 (3) | C21—H21C | 0.9600 |
O2—S1—O1 | 120.61 (12) | C8—C13—H13A | 120.4 |
O2—S1—N1 | 106.88 (11) | C12—C13—H13A | 120.4 |
O1—S1—N1 | 104.49 (12) | C2—C14—C15 | 111.9 (2) |
O2—S1—C8 | 109.43 (12) | C2—C14—H14A | 109.2 |
O1—S1—C8 | 109.75 (12) | C15—C14—H14A | 109.2 |
N1—S1—C8 | 104.34 (10) | C2—C14—H14B | 109.2 |
C2—N1—C7A | 105.92 (19) | C15—C14—H14B | 109.2 |
C2—N1—S1 | 127.14 (17) | H14A—C14—H14B | 107.9 |
C7A—N1—S1 | 126.12 (17) | C14—C15—C16 | 113.1 (2) |
C2—N3—C3A | 106.4 (2) | C14—C15—H15A | 109.0 |
N3—C2—N1 | 112.3 (2) | C16—C15—H15A | 109.0 |
N3—C2—C14 | 123.6 (2) | C14—C15—H15B | 109.0 |
N1—C2—C14 | 124.0 (2) | C16—C15—H15B | 109.0 |
C4—C3A—N3 | 128.4 (2) | H15A—C15—H15B | 107.8 |
C4—C3A—C7A | 120.5 (2) | C15—C16—C17 | 111.7 (3) |
N3—C3A—C7A | 111.1 (2) | C15—C16—H16A | 109.3 |
C5—C4—C3A | 117.6 (3) | C17—C16—H16A | 109.3 |
C5—C4—H4A | 121.2 | C15—C16—H16B | 109.3 |
C3A—C4—H4A | 121.2 | C17—C16—H16B | 109.3 |
C4—C5—C6 | 121.2 (3) | H16A—C16—H16B | 107.9 |
C4—C5—Cl1 | 122.1 (3) | C16—C17—H17A | 109.5 |
C6—C5—Cl1 | 116.7 (2) | C16—C17—H17B | 109.5 |
C4—C5—H5A | 119.4 | H17A—C17—H17B | 109.5 |
C6—C5—H5A | 119.4 | C16—C17—H17C | 109.5 |
C7—C6—C5 | 121.8 (3) | H17A—C17—H17C | 109.5 |
C7—C6—Cl1' | 130.0 (3) | H17B—C17—H17C | 109.5 |
C5—C6—Cl1' | 108.2 (3) | C20—C18—C11 | 111.8 (2) |
C7—C6—H6A | 119.1 | C20—C18—C21 | 109.2 (3) |
C5—C6—H6A | 119.1 | C11—C18—C21 | 109.0 (2) |
C6—C7—C7A | 117.1 (3) | C20—C18—C19 | 109.0 (3) |
C6—C7—H7A | 121.4 | C11—C18—C19 | 109.1 (2) |
C7A—C7—H7A | 121.4 | C21—C18—C19 | 108.5 (2) |
C7—C7A—C3A | 121.7 (2) | C18—C19—H19A | 109.5 |
C7—C7A—N1 | 133.9 (2) | C18—C19—H19B | 109.5 |
C3A—C7A—N1 | 104.3 (2) | H19A—C19—H19B | 109.5 |
C13—C8—C9 | 120.9 (2) | C18—C19—H19C | 109.5 |
C13—C8—S1 | 119.42 (18) | H19A—C19—H19C | 109.5 |
C9—C8—S1 | 119.72 (18) | H19B—C19—H19C | 109.5 |
C8—C9—C10 | 118.9 (2) | C18—C20—H20A | 109.5 |
C8—C9—H9A | 120.6 | C18—C20—H20B | 109.5 |
C10—C9—H9A | 120.6 | H20A—C20—H20B | 109.5 |
C9—C10—C11 | 122.1 (2) | C18—C20—H20C | 109.5 |
C9—C10—H10A | 119.0 | H20A—C20—H20C | 109.5 |
C11—C10—H10A | 119.0 | H20B—C20—H20C | 109.5 |
C12—C11—C10 | 117.2 (2) | C18—C21—H21A | 109.5 |
C12—C11—C18 | 122.9 (2) | C18—C21—H21B | 109.5 |
C10—C11—C18 | 119.9 (2) | H21A—C21—H21B | 109.5 |
C13—C12—C11 | 121.8 (2) | C18—C21—H21C | 109.5 |
C13—C12—H12A | 119.1 | H21A—C21—H21C | 109.5 |
C11—C12—H12A | 119.1 | H21B—C21—H21C | 109.5 |
C8—C13—C12 | 119.2 (2) | ||
O2—S1—N1—C2 | −44.7 (2) | S1—N1—C7A—C7 | −13.3 (4) |
O1—S1—N1—C2 | −173.60 (18) | C2—N1—C7A—C3A | 0.1 (2) |
C8—S1—N1—C2 | 71.2 (2) | S1—N1—C7A—C3A | 170.24 (15) |
O2—S1—N1—C7A | 147.17 (18) | O2—S1—C8—C13 | −9.6 (2) |
O1—S1—N1—C7A | 18.3 (2) | O1—S1—C8—C13 | 124.9 (2) |
C8—S1—N1—C7A | −96.96 (19) | N1—S1—C8—C13 | −123.6 (2) |
C3A—N3—C2—N1 | 1.0 (2) | O2—S1—C8—C9 | 171.52 (18) |
C3A—N3—C2—C14 | 178.5 (2) | O1—S1—C8—C9 | −54.0 (2) |
C7A—N1—C2—N3 | −0.7 (2) | N1—S1—C8—C9 | 57.5 (2) |
S1—N1—C2—N3 | −170.73 (16) | C13—C8—C9—C10 | 2.2 (4) |
C7A—N1—C2—C14 | −178.2 (2) | S1—C8—C9—C10 | −178.88 (19) |
S1—N1—C2—C14 | 11.8 (3) | C8—C9—C10—C11 | −1.1 (4) |
C2—N3—C3A—C4 | −178.7 (2) | C9—C10—C11—C12 | −0.9 (4) |
C2—N3—C3A—C7A | −0.9 (3) | C9—C10—C11—C18 | 177.0 (2) |
N3—C3A—C4—C5 | 177.6 (2) | C10—C11—C12—C13 | 1.8 (4) |
C7A—C3A—C4—C5 | 0.0 (3) | C18—C11—C12—C13 | −176.1 (2) |
C3A—C4—C5—C6 | −1.5 (4) | C9—C8—C13—C12 | −1.4 (4) |
C3A—C4—C5—Cl1 | 178.72 (19) | S1—C8—C13—C12 | 179.73 (19) |
C4—C5—C6—C7 | 1.4 (4) | C11—C12—C13—C8 | −0.7 (4) |
Cl1—C5—C6—C7 | −178.7 (2) | N3—C2—C14—C15 | 2.2 (3) |
C4—C5—C6—Cl1' | −179.4 (2) | N1—C2—C14—C15 | 179.46 (19) |
C5—C6—C7—C7A | 0.1 (4) | C2—C14—C15—C16 | −178.03 (19) |
Cl1'—C6—C7—C7A | −178.9 (2) | C14—C15—C16—C17 | 179.0 (2) |
C6—C7—C7A—C3A | −1.6 (4) | C12—C11—C18—C20 | 1.7 (4) |
C6—C7—C7A—N1 | −177.5 (2) | C10—C11—C18—C20 | −176.1 (2) |
C4—C3A—C7A—C7 | 1.5 (3) | C12—C11—C18—C21 | −119.2 (3) |
N3—C3A—C7A—C7 | −176.4 (2) | C10—C11—C18—C21 | 63.0 (3) |
C4—C3A—C7A—N1 | 178.5 (2) | C12—C11—C18—C19 | 122.4 (3) |
N3—C3A—C7A—N1 | 0.5 (2) | C10—C11—C18—C19 | −55.4 (3) |
C2—N1—C7A—C7 | 176.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···O2i | 0.93 | 2.67 | 3.595 (3) | 176 |
Symmetry code: (i) x−1, y, z. |
C18H19ClN2O2S | Z = 2 |
Mr = 362.86 | F(000) = 380 |
Triclinic, P1 | Dx = 1.359 Mg m−3 |
a = 8.1491 (16) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 10.039 (2) Å | Cell parameters from 4862 reflections |
c = 12.485 (3) Å | θ = 4.9–76.1° |
α = 112.23 (3)° | µ = 3.11 mm−1 |
β = 105.49 (3)° | T = 297 K |
γ = 96.02 (3)° | Prizmatic, colorless |
V = 886.5 (4) Å3 | 0.40 × 0.34 × 0.28 mm |
Xcalibur, Ruby diffractometer | 3662 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 3088 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 10.2576 pixels mm-1 | θmax = 76.7°, θmin = 4.9° |
ω scans | h = −10→7 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −12→12 |
Tmin = 0.394, Tmax = 1.000 | l = −15→15 |
8070 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.0949P)2 + 0.1961P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
3662 reflections | Δρmax = 0.62 e Å−3 |
219 parameters | Δρmin = −0.56 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.14167 (6) | 0.68003 (5) | 0.49351 (5) | 0.05023 (18) | |
Cl1 | −0.14634 (10) | 1.03713 (9) | 0.10476 (6) | 0.0805 (2) | |
O1 | −0.0423 (2) | 0.61981 (18) | 0.44279 (18) | 0.0639 (5) | |
O2 | 0.2329 (2) | 0.71457 (18) | 0.61788 (16) | 0.0621 (4) | |
N1 | 0.1723 (2) | 0.84081 (18) | 0.47964 (17) | 0.0484 (4) | |
N3 | 0.2844 (2) | 1.07202 (19) | 0.51200 (17) | 0.0502 (4) | |
C2 | 0.2986 (2) | 0.9753 (2) | 0.5575 (2) | 0.0463 (4) | |
C3A | 0.1486 (3) | 1.0042 (2) | 0.40047 (19) | 0.0467 (4) | |
C4 | 0.0822 (3) | 1.0625 (2) | 0.3172 (2) | 0.0544 (5) | |
H4A | 0.126985 | 1.159347 | 0.332202 | 0.065* | |
C5 | −0.0529 (3) | 0.9701 (3) | 0.2118 (2) | 0.0569 (5) | |
C6 | −0.1219 (3) | 0.8249 (3) | 0.1868 (2) | 0.0612 (6) | |
H6A | −0.211662 | 0.765974 | 0.113421 | 0.073* | |
C7 | −0.0585 (3) | 0.7670 (3) | 0.2698 (2) | 0.0592 (5) | |
H7A | −0.104578 | 0.670410 | 0.254779 | 0.071* | |
C7A | 0.0771 (3) | 0.8598 (2) | 0.3767 (2) | 0.0477 (4) | |
C8 | 0.2445 (3) | 0.5723 (2) | 0.3976 (2) | 0.0484 (5) | |
C9 | 0.1471 (3) | 0.4447 (3) | 0.2933 (2) | 0.0623 (6) | |
H9A | 0.027067 | 0.414879 | 0.274444 | 0.075* | |
C10 | 0.2313 (4) | 0.3638 (3) | 0.2186 (2) | 0.0684 (6) | |
H10A | 0.167128 | 0.277938 | 0.149341 | 0.082* | |
C11 | 0.4103 (3) | 0.4072 (3) | 0.2443 (2) | 0.0611 (6) | |
C12 | 0.5044 (3) | 0.5332 (3) | 0.3486 (2) | 0.0614 (6) | |
H12A | 0.624448 | 0.562930 | 0.367126 | 0.074* | |
C13 | 0.4237 (3) | 0.6159 (2) | 0.4260 (2) | 0.0569 (5) | |
H13A | 0.488914 | 0.700014 | 0.496580 | 0.068* | |
C14 | 0.4290 (3) | 1.0024 (2) | 0.6776 (2) | 0.0523 (5) | |
H14A | 0.506517 | 0.935467 | 0.663068 | 0.063* | |
H14B | 0.367723 | 0.980399 | 0.727873 | 0.063* | |
C15 | 0.5380 (3) | 1.1608 (3) | 0.7474 (2) | 0.0544 (5) | |
H15A | 0.605879 | 1.180599 | 0.699777 | 0.065* | |
H15B | 0.460274 | 1.228107 | 0.756961 | 0.065* | |
C16 | 0.6611 (4) | 1.1901 (3) | 0.8731 (2) | 0.0674 (6) | |
H16A | 0.593770 | 1.165935 | 0.919366 | 0.081* | |
H16B | 0.742375 | 1.125984 | 0.863339 | 0.081* | |
C17 | 0.7634 (5) | 1.3493 (4) | 0.9447 (3) | 0.0946 (10) | |
H17A | 0.836419 | 1.363259 | 1.024234 | 0.142* | |
H17B | 0.683530 | 1.413398 | 0.953948 | 0.142* | |
H17C | 0.834961 | 1.372367 | 0.901381 | 0.142* | |
C18 | 0.5008 (5) | 0.3202 (4) | 0.1594 (3) | 0.0903 (10) | |
H18D | 0.621201 | 0.334121 | 0.205306 | 0.135* | |
H18A | 0.494375 | 0.354141 | 0.096386 | 0.135* | |
H18B | 0.444249 | 0.217126 | 0.122491 | 0.135* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0441 (3) | 0.0451 (3) | 0.0725 (4) | 0.0097 (2) | 0.0245 (2) | 0.0332 (2) |
Cl1 | 0.0847 (5) | 0.0901 (5) | 0.0704 (4) | 0.0155 (4) | 0.0130 (3) | 0.0477 (4) |
O1 | 0.0460 (8) | 0.0580 (9) | 0.1005 (13) | 0.0095 (7) | 0.0315 (8) | 0.0428 (9) |
O2 | 0.0709 (10) | 0.0570 (9) | 0.0736 (10) | 0.0155 (8) | 0.0317 (8) | 0.0382 (8) |
N1 | 0.0427 (8) | 0.0424 (8) | 0.0655 (10) | 0.0093 (7) | 0.0184 (7) | 0.0285 (8) |
N3 | 0.0503 (9) | 0.0421 (8) | 0.0611 (10) | 0.0093 (7) | 0.0198 (8) | 0.0243 (8) |
C2 | 0.0408 (9) | 0.0434 (9) | 0.0604 (11) | 0.0107 (8) | 0.0220 (9) | 0.0241 (9) |
C3A | 0.0455 (10) | 0.0422 (10) | 0.0582 (11) | 0.0122 (8) | 0.0230 (9) | 0.0229 (8) |
C4 | 0.0597 (12) | 0.0490 (11) | 0.0634 (13) | 0.0147 (9) | 0.0250 (10) | 0.0296 (10) |
C5 | 0.0552 (12) | 0.0670 (13) | 0.0589 (12) | 0.0204 (10) | 0.0231 (10) | 0.0331 (11) |
C6 | 0.0533 (12) | 0.0599 (13) | 0.0629 (13) | 0.0095 (10) | 0.0143 (10) | 0.0225 (11) |
C7 | 0.0517 (12) | 0.0490 (11) | 0.0711 (14) | 0.0043 (9) | 0.0145 (10) | 0.0255 (10) |
C7A | 0.0425 (9) | 0.0455 (10) | 0.0630 (12) | 0.0131 (8) | 0.0233 (9) | 0.0267 (9) |
C8 | 0.0450 (10) | 0.0423 (10) | 0.0648 (12) | 0.0098 (8) | 0.0188 (9) | 0.0295 (9) |
C9 | 0.0453 (11) | 0.0576 (13) | 0.0753 (15) | 0.0025 (9) | 0.0133 (10) | 0.0262 (11) |
C10 | 0.0627 (14) | 0.0648 (14) | 0.0627 (14) | 0.0085 (11) | 0.0129 (11) | 0.0186 (11) |
C11 | 0.0617 (13) | 0.0694 (14) | 0.0608 (13) | 0.0233 (11) | 0.0214 (11) | 0.0337 (11) |
C12 | 0.0434 (11) | 0.0690 (14) | 0.0779 (15) | 0.0151 (10) | 0.0232 (10) | 0.0350 (12) |
C13 | 0.0435 (10) | 0.0492 (11) | 0.0724 (14) | 0.0061 (9) | 0.0166 (10) | 0.0229 (10) |
C14 | 0.0499 (11) | 0.0518 (11) | 0.0603 (12) | 0.0132 (9) | 0.0203 (9) | 0.0275 (10) |
C15 | 0.0482 (11) | 0.0567 (12) | 0.0573 (12) | 0.0088 (9) | 0.0187 (9) | 0.0233 (10) |
C16 | 0.0634 (14) | 0.0746 (16) | 0.0594 (14) | 0.0156 (12) | 0.0189 (11) | 0.0244 (12) |
C17 | 0.085 (2) | 0.092 (2) | 0.0710 (18) | −0.0069 (17) | 0.0106 (15) | 0.0157 (16) |
C18 | 0.088 (2) | 0.118 (3) | 0.0685 (17) | 0.0433 (19) | 0.0335 (16) | 0.0324 (17) |
S1—O2 | 1.4163 (19) | C10—C11 | 1.390 (4) |
S1—O1 | 1.4235 (17) | C10—H10A | 0.9300 |
S1—N1 | 1.6875 (17) | C11—C12 | 1.379 (4) |
S1—C8 | 1.747 (2) | C11—C18 | 1.510 (4) |
Cl1—C5 | 1.751 (2) | C12—C13 | 1.379 (3) |
N1—C7A | 1.405 (3) | C12—H12A | 0.9300 |
N1—C2 | 1.417 (3) | C13—H13A | 0.9300 |
N3—C2 | 1.298 (3) | C14—C15 | 1.523 (3) |
N3—C3A | 1.389 (3) | C14—H14A | 0.9700 |
C2—C14 | 1.494 (3) | C14—H14B | 0.9700 |
C3A—C7A | 1.391 (3) | C15—C16 | 1.518 (3) |
C3A—C4 | 1.394 (3) | C15—H15A | 0.9700 |
C4—C5 | 1.376 (3) | C15—H15B | 0.9700 |
C4—H4A | 0.9300 | C16—C17 | 1.513 (4) |
C5—C6 | 1.388 (4) | C16—H16A | 0.9700 |
C6—C7 | 1.383 (4) | C16—H16B | 0.9700 |
C6—H6A | 0.9300 | C17—H17A | 0.9600 |
C7—C7A | 1.387 (3) | C17—H17B | 0.9600 |
C7—H7A | 0.9300 | C17—H17C | 0.9600 |
C8—C13 | 1.386 (3) | C18—H18D | 0.9600 |
C8—C9 | 1.392 (3) | C18—H18A | 0.9600 |
C9—C10 | 1.373 (4) | C18—H18B | 0.9600 |
C9—H9A | 0.9300 | ||
O2—S1—O1 | 120.39 (11) | C12—C11—C10 | 118.6 (2) |
O2—S1—N1 | 105.87 (10) | C12—C11—C18 | 120.3 (2) |
O1—S1—N1 | 105.72 (10) | C10—C11—C18 | 121.2 (3) |
O2—S1—C8 | 110.71 (10) | C11—C12—C13 | 121.2 (2) |
O1—S1—C8 | 109.53 (11) | C11—C12—H12A | 119.4 |
N1—S1—C8 | 103.00 (9) | C13—C12—H12A | 119.4 |
C7A—N1—C2 | 106.35 (17) | C12—C13—C8 | 119.4 (2) |
C7A—N1—S1 | 123.54 (15) | C12—C13—H13A | 120.3 |
C2—N1—S1 | 129.95 (15) | C8—C13—H13A | 120.3 |
C2—N3—C3A | 106.66 (17) | C2—C14—C15 | 112.90 (19) |
N3—C2—N1 | 111.37 (19) | C2—C14—H14A | 109.0 |
N3—C2—C14 | 124.58 (19) | C15—C14—H14A | 109.0 |
N1—C2—C14 | 124.04 (18) | C2—C14—H14B | 109.0 |
N3—C3A—C7A | 110.97 (19) | C15—C14—H14B | 109.0 |
N3—C3A—C4 | 128.68 (19) | H14A—C14—H14B | 107.8 |
C7A—C3A—C4 | 120.4 (2) | C16—C15—C14 | 112.5 (2) |
C5—C4—C3A | 116.9 (2) | C16—C15—H15A | 109.1 |
C5—C4—H4A | 121.6 | C14—C15—H15A | 109.1 |
C3A—C4—H4A | 121.6 | C16—C15—H15B | 109.1 |
C4—C5—C6 | 122.8 (2) | C14—C15—H15B | 109.1 |
C4—C5—Cl1 | 119.36 (19) | H15A—C15—H15B | 107.8 |
C6—C5—Cl1 | 117.79 (19) | C17—C16—C15 | 112.5 (3) |
C7—C6—C5 | 120.6 (2) | C17—C16—H16A | 109.1 |
C7—C6—H6A | 119.7 | C15—C16—H16A | 109.1 |
C5—C6—H6A | 119.7 | C17—C16—H16B | 109.1 |
C6—C7—C7A | 116.9 (2) | C15—C16—H16B | 109.1 |
C6—C7—H7A | 121.6 | H16A—C16—H16B | 107.8 |
C7A—C7—H7A | 121.6 | C16—C17—H17A | 109.5 |
C7—C7A—C3A | 122.4 (2) | C16—C17—H17B | 109.5 |
C7—C7A—N1 | 133.0 (2) | H17A—C17—H17B | 109.5 |
C3A—C7A—N1 | 104.63 (18) | C16—C17—H17C | 109.5 |
C13—C8—C9 | 120.5 (2) | H17A—C17—H17C | 109.5 |
C13—C8—S1 | 119.27 (17) | H17B—C17—H17C | 109.5 |
C9—C8—S1 | 120.27 (17) | C11—C18—H18D | 109.5 |
C10—C9—C8 | 118.9 (2) | C11—C18—H18A | 109.5 |
C10—C9—H9A | 120.6 | H18D—C18—H18A | 109.5 |
C8—C9—H9A | 120.6 | C11—C18—H18B | 109.5 |
C9—C10—C11 | 121.5 (2) | H18D—C18—H18B | 109.5 |
C9—C10—H10A | 119.2 | H18A—C18—H18B | 109.5 |
C11—C10—H10A | 119.2 | ||
O2—S1—N1—C7A | −167.75 (16) | C4—C3A—C7A—N1 | −178.69 (18) |
O1—S1—N1—C7A | −38.97 (19) | C2—N1—C7A—C7 | 178.3 (2) |
C8—S1—N1—C7A | 75.96 (18) | S1—N1—C7A—C7 | 2.5 (3) |
O2—S1—N1—C2 | 17.4 (2) | C2—N1—C7A—C3A | −1.5 (2) |
O1—S1—N1—C2 | 146.22 (19) | S1—N1—C7A—C3A | −177.31 (14) |
C8—S1—N1—C2 | −98.86 (19) | O2—S1—C8—C13 | −48.5 (2) |
C3A—N3—C2—N1 | −0.8 (2) | O1—S1—C8—C13 | 176.40 (18) |
C3A—N3—C2—C14 | −179.80 (18) | N1—S1—C8—C13 | 64.3 (2) |
C7A—N1—C2—N3 | 1.5 (2) | O2—S1—C8—C9 | 131.96 (19) |
S1—N1—C2—N3 | 176.97 (15) | O1—S1—C8—C9 | −3.1 (2) |
C7A—N1—C2—C14 | −179.54 (18) | N1—S1—C8—C9 | −115.25 (19) |
S1—N1—C2—C14 | −4.0 (3) | C13—C8—C9—C10 | −0.6 (4) |
C2—N3—C3A—C7A | −0.2 (2) | S1—C8—C9—C10 | 178.9 (2) |
C2—N3—C3A—C4 | 179.5 (2) | C8—C9—C10—C11 | −0.7 (4) |
N3—C3A—C4—C5 | 179.2 (2) | C9—C10—C11—C12 | 1.3 (4) |
C7A—C3A—C4—C5 | −1.1 (3) | C9—C10—C11—C18 | −177.9 (3) |
C3A—C4—C5—C6 | −0.3 (3) | C10—C11—C12—C13 | −0.5 (4) |
C3A—C4—C5—Cl1 | 178.52 (16) | C18—C11—C12—C13 | 178.7 (3) |
C4—C5—C6—C7 | 1.3 (4) | C11—C12—C13—C8 | −0.7 (4) |
Cl1—C5—C6—C7 | −177.49 (19) | C9—C8—C13—C12 | 1.3 (3) |
C5—C6—C7—C7A | −0.9 (4) | S1—C8—C13—C12 | −178.24 (18) |
C6—C7—C7A—C3A | −0.5 (3) | N3—C2—C14—C15 | 4.0 (3) |
C6—C7—C7A—N1 | 179.8 (2) | N1—C2—C14—C15 | −174.85 (19) |
N3—C3A—C7A—C7 | −178.8 (2) | C2—C14—C15—C16 | 175.97 (18) |
C4—C3A—C7A—C7 | 1.5 (3) | C14—C15—C16—C17 | −177.4 (2) |
N3—C3A—C7A—N1 | 1.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···O1i | 0.93 | 2.55 | 3.467 (3) | 170 |
C18—H18D···O2ii | 0.96 | 2.46 | 3.199 (4) | 133 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1. |
Acknowledgements
We are especially grateful to Professor B. Tashkhodzhaev for help in discussing the results.
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