organic compounds
4-Methyl-N-(4-methylphenylsulfonyl)-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]benzenesulfonamide
aFacultad de Química, Universidad, Autónoma de Yucatán, Calle 41 No. 421, Col. Industrial, CP 97150, Mérida, Yucatán, Mexico, and bInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México, DF 04510, Mexico
*Correspondence e-mail: gmiron@uady.mx
There are two independent molecules in the 24H22N2O4S3. In each, the sulfonamide N atoms reveal nearly a trigonal-planar geometry with two S atoms of the O=S=O groups and one C atom of the thiazole ring; the angles around the N atoms are between 117.00 (13) and 123.86 (9)°. The methylphenylsulfonyl groups are in anti conformations, forming dihedral angles of 78.00 (7)/72.53 (5) and 77.09 (6)/71.50 (7)° with the trigonal S—N—S planes in the two molecules. The thiazole groups are rotated around the C—N bonds and are almost perpendicular to the S—N—S plane [dihedral angles of 78.00 (7)/72.53 (5) and 77.09 (6)/71.50 (7)°]. In the crystal, pairs of C—H⋯O interactions, with the O atoms of the sulfonamide groups as acceptors, link each of the independent molecules into inversion dimers.
of the title compound, CCCDC reference: 975462
Related literature
For bioactive sulfonamide compounds, see: Annadurai et al. (2012); Farag et al. (2012); Xiao-Long et al. (2009).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 975462
https://doi.org/10.1107/S1600536813032145/kp2458sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032145/kp2458Isup2.hkl
A mixture of 4-p-tolyl-thiazol-2-ylamine (200 mg, 1.05 mmol), 4-methyl-benzenesulfonyl chloride (600 mg, 3.15 mmol), triethyl-amine (0.293 mL, 2.1 mmol) and dimethyl-pyridin-4-yl-amine (12.8 mg, 0.105 mmol) in dichloromethane (0.1 M, 11 mL) was stirred in a 50 mL round bottom flask at room temperature for 12 h, and the reaction was monitored by TLC. Then, the reaction solution was quenched by addition of water with stirring and extracted with dichloromethane. The organic layers were dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was crystallized from acetone to yield single crystals of the title compound (314 mg, 0.63 mmol, 60%).
H atoms were included in calculated position (C—H = 0.93 Å for aromatic H, and C—H = 0.96 Å for methyl H), and refined using a riding model Uiso(H) = 1.2 Ueq of the carrier atoms. In the
10 reflections were considered as disagreeable and were omitted.Sulfonamide thiazoles are structural units frequently found as parts of skeletons of bioactive compounds including antimicrobials agents (Annadurai et al., 2012), anticonvulsant agents (Farag et al., 2012) or inhibitors of Nek2/Hec1 (Xiao-Long et al., 2009). Due to the importance of thiazole derivatives, we synthesized (I) N-[4-(p-tolyl)thiazol-2-yl]-4-methyl-N-(4- methylphenylsulfonyl)benzenesulfonamide, and discuss the geometry of the molecule and its conformation. The compound was obtained by the reaction of 4-p-tolyl-thiazol-2-ylamine in an excess of 4-methyl-benzenesulfonilchloride.
The title compound I crystallized with two independent molecules (A and B) in the
(Fig. 1). The geometries around the N13 and N42 atoms are almost trigonal planar with bonding angles ranging from 117.00° to 123.86°. The sulfonamide nitrogen atoms are bonded to a carbon atom of the thiazole ring and two sulfur atoms of the O=S=O groups, the distances of the C—N bonds are of 1.426 (2) Å for both molecules, and the N—S bonds are between 1.6902 (16) and 1.7040 (17) Å. The thiazole rings are rotated around C—N bond foming the dihedral angles of 85.57 (5)° and 89.28 (5)° with the planes O2S—N—SO2, in molecule A and B, respectively. The methylphenylsulfonyl groups keep anti-conformations forming a dihedral angles of 78.00 (7)°, 72.53 (5)° and 77.09 (6)°, 71.50 (7)° with the trigonal plane S—N—S, in the molecules A and B, respectively. The sulfur atoms of the sulfonamide groups are in a distorted tetrahedral geometry with angles varying from 103.43 (8) to 121.39 (1)°, and S=O bonds from 1.4175 (15) to 1.42358 (14) Å. The thiazole and p-tolyl groups in the molecule B exhibit a coplanar arrangement, while in the molecule A these moieties form an angle of 17.20 (7)° between these planes. Each independent molecule form a dimer arrangement by C—H···O interactions (Table 1, Fig. 2). The crystal packing in the title compound is stabilized by the C—H···O=S intermolecular interactions.For bioactive sulfonamide compounds, see: Annadurai et al. (2012); Farag et al. (2012); Xiao-Long et al. (2009).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C24H22N2O4S3 | Z = 4 |
Mr = 498.61 | F(000) = 1040 |
Triclinic, P1 | Dx = 1.410 Mg m−3 |
a = 8.3322 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.0630 (3) Å | Cell parameters from 7195 reflections |
c = 23.5756 (6) Å | θ = 2.3–25.3° |
α = 84.615 (1)° | µ = 0.35 mm−1 |
β = 87.022 (1)° | T = 298 K |
γ = 85.482 (1)° | Prism, colourless |
V = 2349.46 (10) Å3 | 0.44 × 0.38 × 0.28 mm |
Bruker APEXII CCD area-detector diffractometer | Rint = 0.035 |
Detector resolution: 0.83 pixels mm-1 | θmax = 25.4°, θmin = 1.7° |
ω scans | h = −10→10 |
18770 measured reflections | k = −14→14 |
8539 independent reflections | l = −28→28 |
6755 reflections with I > 2σ(I) |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0613P)2] |
wR(F2) = 0.104 | (Δ/σ)max = 0.002 |
S = 0.98 | Δρmax = 0.23 e Å−3 |
8539 reflections | Δρmin = −0.28 e Å−3 |
602 parameters | Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0092 (7) |
C24H22N2O4S3 | γ = 85.482 (1)° |
Mr = 498.61 | V = 2349.46 (10) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.3322 (2) Å | Mo Kα radiation |
b = 12.0630 (3) Å | µ = 0.35 mm−1 |
c = 23.5756 (6) Å | T = 298 K |
α = 84.615 (1)° | 0.44 × 0.38 × 0.28 mm |
β = 87.022 (1)° |
Bruker APEXII CCD area-detector diffractometer | 6755 reflections with I > 2σ(I) |
18770 measured reflections | Rint = 0.035 |
8539 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 2 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.23 e Å−3 |
8539 reflections | Δρmin = −0.28 e Å−3 |
602 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.21107 (6) | 0.86099 (4) | 0.70159 (2) | 0.04992 (16) | |
C2 | 0.3027 (2) | 0.73811 (15) | 0.68033 (8) | 0.0403 (4) | |
N3 | 0.38103 (19) | 0.67554 (13) | 0.71866 (7) | 0.0418 (4) | |
C4 | 0.3706 (2) | 0.72444 (16) | 0.76934 (8) | 0.0411 (5) | |
C5 | 0.2846 (2) | 0.82565 (16) | 0.76730 (9) | 0.0473 (5) | |
H5 | 0.2683 | 0.8695 | 0.7978 | 0.057* | |
C6 | 0.4503 (2) | 0.66461 (16) | 0.81880 (8) | 0.0424 (5) | |
C7 | 0.4960 (3) | 0.55130 (18) | 0.81897 (9) | 0.0555 (6) | |
H7 | 0.4752 | 0.5137 | 0.7878 | 0.067* | |
C8 | 0.5717 (3) | 0.49367 (18) | 0.86461 (9) | 0.0585 (6) | |
H8 | 0.6000 | 0.4177 | 0.8638 | 0.070* | |
C9 | 0.6060 (3) | 0.54611 (19) | 0.91126 (9) | 0.0532 (5) | |
C10 | 0.5589 (3) | 0.65886 (18) | 0.91154 (9) | 0.0607 (6) | |
H10 | 0.5792 | 0.6959 | 0.9430 | 0.073* | |
C11 | 0.4825 (3) | 0.71747 (17) | 0.86615 (9) | 0.0546 (6) | |
H11 | 0.4524 | 0.7931 | 0.8674 | 0.066* | |
C12 | 0.6947 (3) | 0.4832 (2) | 0.96038 (10) | 0.0776 (8) | |
H12A | 0.7016 | 0.5316 | 0.9901 | 0.116* | |
H12B | 0.8013 | 0.4583 | 0.9472 | 0.116* | |
H12C | 0.6374 | 0.4198 | 0.9749 | 0.116* | |
N13 | 0.29416 (19) | 0.70889 (13) | 0.62341 (6) | 0.0424 (4) | |
S14 | 0.15899 (6) | 0.61754 (4) | 0.61109 (2) | 0.04159 (14) | |
O1 | 0.02760 (15) | 0.64008 (11) | 0.65010 (6) | 0.0485 (3) | |
O2 | 0.13878 (17) | 0.63097 (12) | 0.55121 (6) | 0.0551 (4) | |
C15 | 0.2485 (2) | 0.48402 (16) | 0.63075 (8) | 0.0418 (5) | |
C16 | 0.3208 (2) | 0.41966 (17) | 0.58949 (9) | 0.0495 (5) | |
H16 | 0.3258 | 0.4477 | 0.5514 | 0.059* | |
C17 | 0.3850 (2) | 0.31386 (17) | 0.60579 (9) | 0.0524 (5) | |
H17 | 0.4324 | 0.2701 | 0.5781 | 0.063* | |
C18 | 0.3811 (2) | 0.27080 (16) | 0.66211 (10) | 0.0503 (5) | |
C19 | 0.3084 (3) | 0.33669 (17) | 0.70260 (9) | 0.0537 (6) | |
H19 | 0.3047 | 0.3087 | 0.7407 | 0.064* | |
C20 | 0.2412 (3) | 0.44314 (16) | 0.68760 (8) | 0.0492 (5) | |
H20 | 0.1920 | 0.4864 | 0.7152 | 0.059* | |
C21 | 0.4539 (3) | 0.15517 (18) | 0.67975 (12) | 0.0743 (7) | |
H21A | 0.5487 | 0.1604 | 0.7005 | 0.112* | |
H21B | 0.4823 | 0.1166 | 0.6464 | 0.112* | |
H21C | 0.3770 | 0.1148 | 0.7035 | 0.112* | |
S22 | 0.44065 (6) | 0.75042 (5) | 0.57530 (2) | 0.04896 (16) | |
O3 | 0.55605 (16) | 0.79107 (15) | 0.60897 (7) | 0.0711 (5) | |
O4 | 0.48252 (19) | 0.66221 (13) | 0.54054 (6) | 0.0672 (5) | |
C23 | 0.3487 (2) | 0.86359 (17) | 0.53395 (8) | 0.0429 (5) | |
C24 | 0.2862 (2) | 0.84817 (18) | 0.48251 (8) | 0.0488 (5) | |
H24 | 0.2953 | 0.7777 | 0.4692 | 0.059* | |
C25 | 0.2106 (3) | 0.93665 (16) | 0.45099 (9) | 0.0551 (6) | |
H25 | 0.1711 | 0.9257 | 0.4159 | 0.066* | |
C26 | 0.1920 (2) | 1.04194 (16) | 0.47036 (9) | 0.0550 (6) | |
C27 | 0.2570 (3) | 1.05608 (18) | 0.52176 (9) | 0.0642 (7) | |
H27 | 0.2477 | 1.1265 | 0.5351 | 0.077* | |
C28 | 0.3354 (3) | 0.96839 (18) | 0.55381 (10) | 0.0572 (6) | |
H28 | 0.3787 | 0.9797 | 0.5882 | 0.069* | |
C29 | 0.1023 (3) | 1.1370 (2) | 0.43677 (12) | 0.0802 (8) | |
H29A | −0.0054 | 1.1181 | 0.4317 | 0.120* | |
H29B | 0.1566 | 1.1511 | 0.4002 | 0.120* | |
H29C | 0.0986 | 1.2027 | 0.4570 | 0.120* | |
S30 | 0.28190 (7) | 1.08557 (4) | 0.27908 (2) | 0.05011 (16) | |
C31 | 0.2102 (2) | 1.04886 (15) | 0.21732 (8) | 0.0399 (4) | |
N32 | 0.13792 (19) | 1.12839 (12) | 0.18516 (7) | 0.0408 (4) | |
C33 | 0.1363 (2) | 1.22799 (14) | 0.21026 (8) | 0.0391 (4) | |
C34 | 0.2082 (2) | 1.21888 (15) | 0.26092 (9) | 0.0456 (5) | |
H34 | 0.2162 | 1.2781 | 0.2830 | 0.055* | |
C35 | 0.0581 (2) | 1.32933 (15) | 0.18075 (8) | 0.0401 (4) | |
C36 | −0.0114 (3) | 1.32644 (17) | 0.12923 (10) | 0.0622 (6) | |
H36 | −0.0078 | 1.2594 | 0.1125 | 0.075* | |
C37 | −0.0862 (3) | 1.42155 (18) | 0.10196 (11) | 0.0737 (8) | |
H37 | −0.1341 | 1.4168 | 0.0676 | 0.088* | |
C38 | −0.0918 (3) | 1.52323 (17) | 0.12436 (11) | 0.0576 (6) | |
C39 | −0.0221 (3) | 1.52557 (17) | 0.17562 (10) | 0.0586 (6) | |
H39 | −0.0244 | 1.5929 | 0.1920 | 0.070* | |
C40 | 0.0512 (3) | 1.43090 (15) | 0.20370 (9) | 0.0513 (5) | |
H40 | 0.0965 | 1.4356 | 0.2385 | 0.062* | |
C41 | −0.1697 (3) | 1.62846 (19) | 0.09396 (13) | 0.0871 (9) | |
H41A | −0.1077 | 1.6484 | 0.0596 | 0.131* | |
H41B | −0.1738 | 1.6881 | 0.1184 | 0.131* | |
H41C | −0.2771 | 1.6156 | 0.0847 | 0.131* | |
N42 | 0.23294 (19) | 0.93682 (12) | 0.20213 (7) | 0.0427 (4) | |
S43 | 0.39249 (6) | 0.90607 (4) | 0.15665 (2) | 0.04773 (15) | |
O5 | 0.50268 (17) | 0.98571 (12) | 0.16599 (7) | 0.0583 (4) | |
O6 | 0.43414 (19) | 0.78969 (11) | 0.16812 (6) | 0.0624 (4) | |
C44 | 0.3245 (3) | 0.93295 (16) | 0.08724 (9) | 0.0495 (5) | |
C45 | 0.2867 (3) | 0.84603 (19) | 0.05707 (10) | 0.0693 (7) | |
H45 | 0.2966 | 0.7729 | 0.0736 | 0.083* | |
C46 | 0.2344 (3) | 0.8686 (2) | 0.00260 (10) | 0.0729 (7) | |
H46 | 0.2102 | 0.8099 | −0.0176 | 0.088* | |
C47 | 0.2170 (3) | 0.9760 (2) | −0.02279 (9) | 0.0597 (6) | |
C48 | 0.2570 (3) | 1.0612 (2) | 0.00777 (10) | 0.0663 (7) | |
H48 | 0.2473 | 1.1342 | −0.0089 | 0.080* | |
C49 | 0.3109 (3) | 1.04112 (18) | 0.06221 (10) | 0.0586 (6) | |
H49 | 0.3378 | 1.0998 | 0.0819 | 0.070* | |
C50 | 0.1540 (3) | 1.0004 (2) | −0.08219 (10) | 0.0806 (8) | |
H50A | 0.0718 | 1.0608 | −0.0823 | 0.121* | |
H50B | 0.1096 | 0.9350 | −0.0933 | 0.121* | |
H50C | 0.2407 | 1.0207 | −0.1086 | 0.121* | |
S51 | 0.07665 (6) | 0.85425 (4) | 0.21475 (2) | 0.04588 (15) | |
O7 | −0.05860 (17) | 0.92715 (11) | 0.22956 (7) | 0.0609 (4) | |
O8 | 0.0765 (2) | 0.79145 (11) | 0.16686 (6) | 0.0617 (4) | |
C52 | 0.1246 (2) | 0.76319 (15) | 0.27528 (8) | 0.0412 (5) | |
C53 | 0.2258 (3) | 0.66786 (16) | 0.26941 (9) | 0.0521 (5) | |
H53 | 0.2736 | 0.6537 | 0.2340 | 0.063* | |
C54 | 0.2545 (3) | 0.59416 (17) | 0.31684 (9) | 0.0527 (5) | |
H54 | 0.3225 | 0.5301 | 0.3130 | 0.063* | |
C55 | 0.1849 (2) | 0.61315 (17) | 0.36979 (9) | 0.0473 (5) | |
C56 | 0.0841 (3) | 0.70896 (18) | 0.37416 (9) | 0.0544 (6) | |
H56 | 0.0354 | 0.7230 | 0.4094 | 0.065* | |
C57 | 0.0541 (2) | 0.78400 (17) | 0.32762 (9) | 0.0492 (5) | |
H57 | −0.0134 | 0.8483 | 0.3315 | 0.059* | |
C58 | 0.2167 (3) | 0.53202 (19) | 0.42073 (10) | 0.0661 (7) | |
H58A | 0.3187 | 0.5439 | 0.4354 | 0.099* | |
H58B | 0.2187 | 0.4572 | 0.4099 | 0.099* | |
H58C | 0.1329 | 0.5430 | 0.4496 | 0.099* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0562 (3) | 0.0432 (3) | 0.0499 (3) | 0.0036 (3) | −0.0051 (3) | −0.0061 (2) |
C2 | 0.0424 (11) | 0.0394 (11) | 0.0395 (11) | −0.0056 (9) | 0.0001 (9) | −0.0044 (9) |
N3 | 0.0496 (10) | 0.0396 (9) | 0.0364 (9) | −0.0057 (8) | −0.0008 (7) | −0.0035 (7) |
C4 | 0.0433 (11) | 0.0419 (11) | 0.0390 (11) | −0.0090 (9) | 0.0011 (9) | −0.0053 (9) |
C5 | 0.0532 (12) | 0.0457 (12) | 0.0444 (12) | −0.0041 (10) | −0.0011 (10) | −0.0111 (10) |
C6 | 0.0462 (11) | 0.0444 (11) | 0.0373 (11) | −0.0095 (9) | 0.0018 (9) | −0.0035 (9) |
C7 | 0.0742 (15) | 0.0514 (13) | 0.0414 (12) | 0.0026 (11) | −0.0050 (11) | −0.0116 (10) |
C8 | 0.0770 (16) | 0.0492 (13) | 0.0474 (13) | 0.0061 (12) | −0.0031 (12) | −0.0032 (11) |
C9 | 0.0587 (13) | 0.0574 (14) | 0.0423 (12) | −0.0075 (11) | −0.0011 (10) | 0.0047 (10) |
C10 | 0.0870 (17) | 0.0552 (14) | 0.0429 (12) | −0.0159 (13) | −0.0137 (12) | −0.0050 (11) |
C11 | 0.0755 (15) | 0.0415 (12) | 0.0486 (13) | −0.0082 (11) | −0.0107 (11) | −0.0058 (10) |
C12 | 0.098 (2) | 0.0774 (18) | 0.0538 (15) | 0.0031 (15) | −0.0145 (14) | 0.0104 (13) |
N13 | 0.0477 (9) | 0.0453 (9) | 0.0341 (9) | −0.0068 (8) | 0.0001 (7) | −0.0011 (7) |
S14 | 0.0445 (3) | 0.0420 (3) | 0.0381 (3) | 0.0013 (2) | −0.0042 (2) | −0.0050 (2) |
O1 | 0.0406 (7) | 0.0500 (8) | 0.0549 (9) | −0.0001 (6) | 0.0021 (6) | −0.0089 (7) |
O2 | 0.0681 (10) | 0.0569 (9) | 0.0405 (8) | 0.0041 (7) | −0.0144 (7) | −0.0059 (7) |
C15 | 0.0442 (11) | 0.0406 (11) | 0.0409 (11) | −0.0020 (9) | −0.0034 (9) | −0.0048 (9) |
C16 | 0.0550 (13) | 0.0512 (13) | 0.0421 (12) | 0.0001 (10) | 0.0004 (10) | −0.0078 (10) |
C17 | 0.0543 (13) | 0.0478 (13) | 0.0557 (14) | 0.0035 (10) | 0.0012 (11) | −0.0161 (11) |
C18 | 0.0491 (12) | 0.0396 (11) | 0.0636 (14) | −0.0020 (10) | −0.0117 (11) | −0.0085 (11) |
C19 | 0.0700 (14) | 0.0450 (12) | 0.0463 (12) | −0.0052 (11) | −0.0106 (11) | 0.0007 (10) |
C20 | 0.0624 (13) | 0.0454 (12) | 0.0398 (11) | −0.0003 (10) | −0.0012 (10) | −0.0079 (10) |
C21 | 0.0869 (18) | 0.0474 (14) | 0.0889 (19) | 0.0057 (13) | −0.0210 (15) | −0.0068 (13) |
S22 | 0.0385 (3) | 0.0630 (4) | 0.0421 (3) | 0.0029 (3) | 0.0012 (2) | 0.0052 (3) |
O3 | 0.0409 (8) | 0.1111 (14) | 0.0605 (10) | −0.0190 (9) | −0.0101 (7) | 0.0124 (9) |
O4 | 0.0708 (10) | 0.0706 (10) | 0.0521 (9) | 0.0262 (9) | 0.0135 (8) | 0.0011 (8) |
C23 | 0.0355 (10) | 0.0507 (12) | 0.0410 (11) | −0.0065 (9) | 0.0047 (9) | 0.0023 (9) |
C24 | 0.0484 (12) | 0.0533 (13) | 0.0439 (12) | −0.0022 (10) | 0.0021 (10) | −0.0033 (10) |
C25 | 0.0506 (13) | 0.0637 (15) | 0.0484 (13) | −0.0023 (11) | −0.0023 (10) | 0.0076 (11) |
C26 | 0.0393 (11) | 0.0575 (14) | 0.0633 (15) | −0.0044 (10) | 0.0119 (11) | 0.0126 (12) |
C27 | 0.0676 (15) | 0.0415 (13) | 0.0817 (18) | −0.0110 (11) | 0.0177 (14) | −0.0013 (12) |
C28 | 0.0638 (14) | 0.0551 (14) | 0.0543 (14) | −0.0183 (11) | 0.0014 (11) | −0.0040 (11) |
C29 | 0.0538 (15) | 0.0697 (16) | 0.106 (2) | 0.0090 (13) | 0.0105 (14) | 0.0330 (16) |
S30 | 0.0628 (3) | 0.0406 (3) | 0.0472 (3) | 0.0031 (3) | −0.0096 (3) | −0.0078 (2) |
C31 | 0.0448 (11) | 0.0307 (10) | 0.0441 (11) | −0.0025 (8) | 0.0014 (9) | −0.0048 (9) |
N32 | 0.0477 (9) | 0.0303 (8) | 0.0447 (9) | −0.0046 (7) | 0.0005 (8) | −0.0045 (7) |
C33 | 0.0418 (11) | 0.0294 (10) | 0.0464 (11) | −0.0056 (8) | 0.0058 (9) | −0.0064 (8) |
C34 | 0.0533 (12) | 0.0352 (11) | 0.0499 (12) | −0.0016 (9) | −0.0021 (10) | −0.0138 (9) |
C35 | 0.0414 (11) | 0.0305 (10) | 0.0481 (12) | −0.0048 (8) | 0.0038 (9) | −0.0037 (9) |
C36 | 0.0848 (17) | 0.0341 (11) | 0.0700 (16) | −0.0015 (11) | −0.0209 (13) | −0.0089 (11) |
C37 | 0.099 (2) | 0.0474 (14) | 0.0774 (17) | −0.0050 (13) | −0.0406 (16) | −0.0010 (13) |
C38 | 0.0573 (14) | 0.0391 (12) | 0.0754 (16) | −0.0032 (10) | −0.0086 (12) | 0.0024 (11) |
C39 | 0.0761 (16) | 0.0300 (11) | 0.0693 (16) | −0.0033 (11) | 0.0016 (13) | −0.0060 (11) |
C40 | 0.0676 (14) | 0.0357 (11) | 0.0506 (13) | −0.0023 (10) | −0.0015 (11) | −0.0063 (10) |
C41 | 0.101 (2) | 0.0458 (14) | 0.113 (2) | 0.0006 (14) | −0.0331 (19) | 0.0110 (15) |
N42 | 0.0532 (10) | 0.0278 (8) | 0.0475 (10) | −0.0025 (7) | −0.0005 (8) | −0.0058 (7) |
S43 | 0.0545 (3) | 0.0376 (3) | 0.0503 (3) | 0.0057 (2) | −0.0025 (2) | −0.0075 (2) |
O5 | 0.0498 (9) | 0.0597 (9) | 0.0670 (10) | −0.0061 (7) | −0.0005 (7) | −0.0143 (8) |
O6 | 0.0797 (11) | 0.0424 (8) | 0.0624 (10) | 0.0193 (8) | −0.0059 (8) | −0.0084 (7) |
C44 | 0.0606 (13) | 0.0402 (11) | 0.0468 (12) | 0.0015 (10) | 0.0025 (10) | −0.0060 (10) |
C45 | 0.110 (2) | 0.0426 (13) | 0.0558 (15) | −0.0027 (13) | −0.0055 (14) | −0.0105 (11) |
C46 | 0.104 (2) | 0.0657 (16) | 0.0516 (15) | −0.0078 (15) | −0.0056 (14) | −0.0164 (13) |
C47 | 0.0567 (14) | 0.0750 (16) | 0.0455 (13) | −0.0018 (12) | 0.0096 (11) | −0.0046 (12) |
C48 | 0.0803 (17) | 0.0568 (14) | 0.0582 (15) | −0.0015 (13) | 0.0010 (13) | 0.0077 (12) |
C49 | 0.0764 (16) | 0.0436 (12) | 0.0558 (14) | −0.0073 (11) | −0.0022 (12) | −0.0030 (11) |
C50 | 0.0746 (17) | 0.114 (2) | 0.0497 (15) | −0.0005 (16) | 0.0013 (13) | 0.0010 (15) |
S51 | 0.0541 (3) | 0.0318 (3) | 0.0524 (3) | −0.0050 (2) | −0.0133 (3) | 0.0005 (2) |
O7 | 0.0466 (8) | 0.0460 (8) | 0.0875 (12) | 0.0033 (7) | −0.0084 (8) | 0.0056 (8) |
O8 | 0.0960 (12) | 0.0406 (8) | 0.0521 (9) | −0.0172 (8) | −0.0256 (8) | −0.0001 (7) |
C52 | 0.0459 (11) | 0.0328 (10) | 0.0462 (11) | −0.0053 (9) | −0.0095 (9) | −0.0034 (9) |
C53 | 0.0693 (14) | 0.0417 (12) | 0.0439 (12) | 0.0028 (11) | −0.0012 (11) | −0.0024 (10) |
C54 | 0.0622 (14) | 0.0393 (11) | 0.0555 (14) | 0.0046 (10) | −0.0086 (11) | −0.0016 (10) |
C55 | 0.0506 (12) | 0.0477 (12) | 0.0455 (12) | −0.0141 (10) | −0.0114 (10) | −0.0005 (10) |
C56 | 0.0582 (13) | 0.0598 (14) | 0.0459 (12) | −0.0090 (11) | 0.0022 (10) | −0.0063 (11) |
C57 | 0.0492 (12) | 0.0433 (12) | 0.0553 (13) | −0.0007 (10) | −0.0015 (10) | −0.0086 (10) |
C58 | 0.0751 (16) | 0.0686 (15) | 0.0541 (14) | −0.0109 (13) | −0.0175 (12) | 0.0095 (12) |
S1—C5 | 1.700 (2) | S30—C34 | 1.6998 (19) |
S1—C2 | 1.7182 (19) | S30—C31 | 1.7107 (19) |
C2—N3 | 1.292 (2) | C31—N32 | 1.295 (2) |
C2—N13 | 1.426 (2) | C31—N42 | 1.426 (2) |
N3—C4 | 1.377 (2) | N32—C33 | 1.387 (2) |
C4—C5 | 1.364 (3) | C33—C34 | 1.355 (3) |
C4—C6 | 1.473 (3) | C33—C35 | 1.471 (2) |
C5—H5 | 0.9300 | C34—H34 | 0.9300 |
C6—C11 | 1.384 (3) | C35—C36 | 1.377 (3) |
C6—C7 | 1.389 (3) | C35—C40 | 1.381 (3) |
C7—C8 | 1.378 (3) | C36—C37 | 1.382 (3) |
C7—H7 | 0.9300 | C36—H36 | 0.9300 |
C8—C9 | 1.372 (3) | C37—C38 | 1.377 (3) |
C8—H8 | 0.9300 | C37—H37 | 0.9300 |
C9—C10 | 1.386 (3) | C38—C39 | 1.371 (3) |
C9—C12 | 1.516 (3) | C38—C41 | 1.515 (3) |
C10—C11 | 1.381 (3) | C39—C40 | 1.380 (3) |
C10—H10 | 0.9300 | C39—H39 | 0.9300 |
C11—H11 | 0.9300 | C40—H40 | 0.9300 |
C12—H12A | 0.9600 | C41—H41A | 0.9600 |
C12—H12B | 0.9600 | C41—H41B | 0.9600 |
C12—H12C | 0.9600 | C41—H41C | 0.9600 |
N13—S14 | 1.6902 (16) | N42—S51 | 1.6985 (17) |
N13—S22 | 1.6951 (16) | N42—S43 | 1.7040 (17) |
S14—O1 | 1.4190 (14) | S43—O5 | 1.4191 (15) |
S14—O2 | 1.4232 (14) | S43—O6 | 1.4235 (14) |
S14—C15 | 1.7526 (19) | S43—C44 | 1.752 (2) |
C15—C20 | 1.384 (3) | C44—C49 | 1.380 (3) |
C15—C16 | 1.386 (3) | C44—C45 | 1.386 (3) |
C16—C17 | 1.373 (3) | C45—C46 | 1.374 (3) |
C16—H16 | 0.9300 | C45—H45 | 0.9300 |
C17—C18 | 1.379 (3) | C46—C47 | 1.375 (3) |
C17—H17 | 0.9300 | C46—H46 | 0.9300 |
C18—C19 | 1.384 (3) | C47—C48 | 1.379 (3) |
C18—C21 | 1.507 (3) | C47—C50 | 1.516 (3) |
C19—C20 | 1.382 (3) | C48—C49 | 1.375 (3) |
C19—H19 | 0.9300 | C48—H48 | 0.9300 |
C20—H20 | 0.9300 | C49—H49 | 0.9300 |
C21—H21A | 0.9600 | C50—H50A | 0.9600 |
C21—H21B | 0.9600 | C50—H50B | 0.9600 |
C21—H21C | 0.9600 | C50—H50C | 0.9600 |
S22—O4 | 1.4146 (16) | S51—O8 | 1.4175 (15) |
S22—O3 | 1.4219 (15) | S51—O7 | 1.4233 (15) |
S22—C23 | 1.7505 (19) | S51—C52 | 1.7605 (19) |
C23—C24 | 1.378 (3) | C52—C57 | 1.375 (3) |
C23—C28 | 1.383 (3) | C52—C53 | 1.384 (3) |
C24—C25 | 1.372 (3) | C53—C54 | 1.380 (3) |
C24—H24 | 0.9300 | C53—H53 | 0.9300 |
C25—C26 | 1.3842 (17) | C54—C55 | 1.380 (3) |
C25—H25 | 0.9300 | C54—H54 | 0.9300 |
C26—C27 | 1.3831 (17) | C55—C56 | 1.383 (3) |
C26—C29 | 1.502 (3) | C55—C58 | 1.497 (3) |
C27—C28 | 1.382 (3) | C56—C57 | 1.376 (3) |
C27—H27 | 0.9300 | C56—H56 | 0.9300 |
C28—H28 | 0.9300 | C57—H57 | 0.9300 |
C29—H29A | 0.9600 | C58—H58A | 0.9600 |
C29—H29B | 0.9600 | C58—H58B | 0.9600 |
C29—H29C | 0.9600 | C58—H58C | 0.9600 |
C5—S1—C2 | 88.51 (9) | C34—S30—C31 | 88.39 (9) |
N3—C2—N13 | 122.53 (17) | N32—C31—N42 | 122.52 (17) |
N3—C2—S1 | 115.95 (14) | N32—C31—S30 | 116.37 (14) |
N13—C2—S1 | 121.50 (14) | N42—C31—S30 | 121.10 (14) |
C2—N3—C4 | 110.23 (16) | C31—N32—C33 | 109.64 (16) |
C5—C4—N3 | 114.31 (17) | C34—C33—N32 | 114.17 (16) |
C5—C4—C6 | 127.27 (18) | C34—C33—C35 | 127.37 (17) |
N3—C4—C6 | 118.42 (16) | N32—C33—C35 | 118.45 (17) |
C4—C5—S1 | 110.99 (15) | C33—C34—S30 | 111.43 (14) |
C4—C5—H5 | 124.5 | C33—C34—H34 | 124.3 |
S1—C5—H5 | 124.5 | S30—C34—H34 | 124.3 |
C11—C6—C7 | 117.75 (18) | C36—C35—C40 | 117.44 (18) |
C11—C6—C4 | 122.21 (18) | C36—C35—C33 | 121.25 (17) |
C7—C6—C4 | 120.04 (17) | C40—C35—C33 | 121.31 (18) |
C8—C7—C6 | 121.09 (19) | C35—C36—C37 | 121.1 (2) |
C8—C7—H7 | 119.5 | C35—C36—H36 | 119.5 |
C6—C7—H7 | 119.5 | C37—C36—H36 | 119.5 |
C9—C8—C7 | 121.3 (2) | C38—C37—C36 | 121.7 (2) |
C9—C8—H8 | 119.3 | C38—C37—H37 | 119.2 |
C7—C8—H8 | 119.3 | C36—C37—H37 | 119.2 |
C8—C9—C10 | 117.7 (2) | C39—C38—C37 | 116.9 (2) |
C8—C9—C12 | 121.1 (2) | C39—C38—C41 | 121.0 (2) |
C10—C9—C12 | 121.2 (2) | C37—C38—C41 | 122.0 (2) |
C11—C10—C9 | 121.5 (2) | C38—C39—C40 | 122.0 (2) |
C11—C10—H10 | 119.3 | C38—C39—H39 | 119.0 |
C9—C10—H10 | 119.3 | C40—C39—H39 | 119.0 |
C10—C11—C6 | 120.6 (2) | C39—C40—C35 | 120.9 (2) |
C10—C11—H11 | 119.7 | C39—C40—H40 | 119.6 |
C6—C11—H11 | 119.7 | C35—C40—H40 | 119.6 |
C9—C12—H12A | 109.5 | C38—C41—H41A | 109.5 |
C9—C12—H12B | 109.5 | C38—C41—H41B | 109.5 |
H12A—C12—H12B | 109.5 | H41A—C41—H41B | 109.5 |
C9—C12—H12C | 109.5 | C38—C41—H41C | 109.5 |
H12A—C12—H12C | 109.5 | H41A—C41—H41C | 109.5 |
H12B—C12—H12C | 109.5 | H41B—C41—H41C | 109.5 |
C2—N13—S14 | 117.79 (13) | C31—N42—S51 | 118.07 (13) |
C2—N13—S22 | 117.50 (13) | C31—N42—S43 | 116.99 (13) |
S14—N13—S22 | 123.86 (9) | S51—N42—S43 | 122.71 (9) |
O1—S14—O2 | 120.91 (8) | O5—S43—O6 | 120.77 (9) |
O1—S14—N13 | 104.42 (8) | O5—S43—N42 | 103.42 (8) |
O2—S14—N13 | 105.63 (8) | O6—S43—N42 | 105.94 (9) |
O1—S14—C15 | 108.55 (9) | O5—S43—C44 | 109.09 (10) |
O2—S14—C15 | 109.88 (9) | O6—S43—C44 | 109.59 (9) |
N13—S14—C15 | 106.39 (8) | N42—S43—C44 | 107.04 (9) |
C20—C15—C16 | 120.91 (18) | C49—C44—C45 | 119.8 (2) |
C20—C15—S14 | 118.98 (15) | C49—C44—S43 | 119.79 (17) |
C16—C15—S14 | 120.08 (15) | C45—C44—S43 | 120.39 (17) |
C17—C16—C15 | 118.92 (19) | C46—C45—C44 | 119.6 (2) |
C17—C16—H16 | 120.5 | C46—C45—H45 | 120.2 |
C15—C16—H16 | 120.5 | C44—C45—H45 | 120.2 |
C16—C17—C18 | 121.72 (19) | C45—C46—C47 | 121.6 (2) |
C16—C17—H17 | 119.1 | C45—C46—H46 | 119.2 |
C18—C17—H17 | 119.1 | C47—C46—H46 | 119.2 |
C17—C18—C19 | 118.33 (18) | C46—C47—C48 | 117.9 (2) |
C17—C18—C21 | 121.4 (2) | C46—C47—C50 | 121.1 (2) |
C19—C18—C21 | 120.3 (2) | C48—C47—C50 | 121.0 (2) |
C20—C19—C18 | 121.4 (2) | C49—C48—C47 | 121.9 (2) |
C20—C19—H19 | 119.3 | C49—C48—H48 | 119.1 |
C18—C19—H19 | 119.3 | C47—C48—H48 | 119.1 |
C19—C20—C15 | 118.67 (19) | C48—C49—C44 | 119.2 (2) |
C19—C20—H20 | 120.7 | C48—C49—H49 | 120.4 |
C15—C20—H20 | 120.7 | C44—C49—H49 | 120.4 |
C18—C21—H21A | 109.5 | C47—C50—H50A | 109.5 |
C18—C21—H21B | 109.5 | C47—C50—H50B | 109.5 |
H21A—C21—H21B | 109.5 | H50A—C50—H50B | 109.5 |
C18—C21—H21C | 109.5 | C47—C50—H50C | 109.5 |
H21A—C21—H21C | 109.5 | H50A—C50—H50C | 109.5 |
H21B—C21—H21C | 109.5 | H50B—C50—H50C | 109.5 |
O4—S22—O3 | 121.39 (10) | O8—S51—O7 | 121.16 (10) |
O4—S22—N13 | 107.88 (9) | O8—S51—N42 | 105.89 (9) |
O3—S22—N13 | 103.99 (9) | O7—S51—N42 | 105.46 (8) |
O4—S22—C23 | 109.14 (9) | O8—S51—C52 | 108.98 (9) |
O3—S22—C23 | 108.52 (10) | O7—S51—C52 | 108.32 (10) |
N13—S22—C23 | 104.60 (8) | N42—S51—C52 | 106.01 (8) |
C24—C23—C28 | 120.01 (19) | C57—C52—C53 | 120.39 (19) |
C24—C23—S22 | 120.34 (16) | C57—C52—S51 | 119.64 (15) |
C28—C23—S22 | 119.63 (16) | C53—C52—S51 | 119.86 (16) |
C25—C24—C23 | 120.1 (2) | C54—C53—C52 | 119.0 (2) |
C25—C24—H24 | 120.0 | C54—C53—H53 | 120.5 |
C23—C24—H24 | 120.0 | C52—C53—H53 | 120.5 |
C24—C25—C26 | 121.3 (2) | C55—C54—C53 | 121.7 (2) |
C24—C25—H25 | 119.4 | C55—C54—H54 | 119.2 |
C26—C25—H25 | 119.4 | C53—C54—H54 | 119.2 |
C27—C26—C25 | 117.8 (2) | C54—C55—C56 | 117.89 (19) |
C27—C26—C29 | 121.4 (2) | C54—C55—C58 | 121.0 (2) |
C25—C26—C29 | 120.8 (2) | C56—C55—C58 | 121.1 (2) |
C28—C27—C26 | 121.8 (2) | C57—C56—C55 | 121.6 (2) |
C28—C27—H27 | 119.1 | C57—C56—H56 | 119.2 |
C26—C27—H27 | 119.1 | C55—C56—H56 | 119.2 |
C27—C28—C23 | 119.0 (2) | C52—C57—C56 | 119.44 (19) |
C27—C28—H28 | 120.5 | C52—C57—H57 | 120.3 |
C23—C28—H28 | 120.5 | C56—C57—H57 | 120.3 |
C26—C29—H29A | 109.5 | C55—C58—H58A | 109.5 |
C26—C29—H29B | 109.5 | C55—C58—H58B | 109.5 |
H29A—C29—H29B | 109.5 | H58A—C58—H58B | 109.5 |
C26—C29—H29C | 109.5 | C55—C58—H58C | 109.5 |
H29A—C29—H29C | 109.5 | H58A—C58—H58C | 109.5 |
H29B—C29—H29C | 109.5 | H58B—C58—H58C | 109.5 |
C5—S1—C2—N3 | 0.20 (16) | C34—S30—C31—N32 | 0.38 (16) |
C5—S1—C2—N13 | −178.73 (16) | C34—S30—C31—N42 | 179.08 (17) |
N13—C2—N3—C4 | 179.31 (17) | N42—C31—N32—C33 | −178.92 (17) |
S1—C2—N3—C4 | 0.4 (2) | S30—C31—N32—C33 | −0.2 (2) |
C2—N3—C4—C5 | −1.0 (2) | C31—N32—C33—C34 | −0.1 (2) |
C2—N3—C4—C6 | 178.96 (17) | C31—N32—C33—C35 | −179.46 (16) |
N3—C4—C5—S1 | 1.1 (2) | N32—C33—C34—S30 | 0.4 (2) |
C6—C4—C5—S1 | −178.80 (16) | C35—C33—C34—S30 | 179.67 (15) |
C2—S1—C5—C4 | −0.73 (16) | C31—S30—C34—C33 | −0.41 (16) |
C5—C4—C6—C11 | −17.2 (3) | C34—C33—C35—C36 | −179.7 (2) |
N3—C4—C6—C11 | 162.9 (2) | N32—C33—C35—C36 | −0.4 (3) |
C5—C4—C6—C7 | 162.9 (2) | C34—C33—C35—C40 | 0.2 (3) |
N3—C4—C6—C7 | −17.0 (3) | N32—C33—C35—C40 | 179.45 (19) |
C11—C6—C7—C8 | −0.3 (3) | C40—C35—C36—C37 | −0.6 (3) |
C4—C6—C7—C8 | 179.6 (2) | C33—C35—C36—C37 | 179.3 (2) |
C6—C7—C8—C9 | −0.7 (4) | C35—C36—C37—C38 | 1.3 (4) |
C7—C8—C9—C10 | 1.4 (3) | C36—C37—C38—C39 | −1.2 (4) |
C7—C8—C9—C12 | −177.7 (2) | C36—C37—C38—C41 | 178.4 (2) |
C8—C9—C10—C11 | −1.1 (4) | C37—C38—C39—C40 | 0.3 (4) |
C12—C9—C10—C11 | 178.0 (2) | C41—C38—C39—C40 | −179.2 (2) |
C9—C10—C11—C6 | 0.2 (4) | C38—C39—C40—C35 | 0.4 (4) |
C7—C6—C11—C10 | 0.6 (3) | C36—C35—C40—C39 | −0.3 (3) |
C4—C6—C11—C10 | −179.4 (2) | C33—C35—C40—C39 | 179.84 (19) |
N3—C2—N13—S14 | 81.0 (2) | N32—C31—N42—S51 | −81.3 (2) |
S1—C2—N13—S14 | −100.19 (16) | S30—C31—N42—S51 | 100.11 (16) |
N3—C2—N13—S22 | −88.9 (2) | N32—C31—N42—S43 | 82.2 (2) |
S1—C2—N13—S22 | 89.99 (16) | S30—C31—N42—S43 | −96.38 (16) |
C2—N13—S14—O1 | 33.22 (15) | C31—N42—S43—O5 | 26.11 (16) |
S22—N13—S14—O1 | −157.66 (10) | S51—N42—S43—O5 | −171.21 (10) |
C2—N13—S14—O2 | 161.73 (13) | C31—N42—S43—O6 | 154.07 (14) |
S22—N13—S14—O2 | −29.15 (13) | S51—N42—S43—O6 | −43.24 (13) |
C2—N13—S14—C15 | −81.50 (15) | C31—N42—S43—C44 | −89.03 (15) |
S22—N13—S14—C15 | 87.62 (12) | S51—N42—S43—C44 | 73.65 (13) |
O1—S14—C15—C20 | −29.21 (19) | O5—S43—C44—C49 | −31.6 (2) |
O2—S14—C15—C20 | −163.45 (16) | O6—S43—C44—C49 | −165.88 (17) |
N13—S14—C15—C20 | 82.66 (18) | N42—S43—C44—C49 | 79.7 (2) |
O1—S14—C15—C16 | 148.83 (16) | O5—S43—C44—C45 | 147.44 (19) |
O2—S14—C15—C16 | 14.6 (2) | O6—S43—C44—C45 | 13.2 (2) |
N13—S14—C15—C16 | −99.30 (17) | N42—S43—C44—C45 | −101.3 (2) |
C20—C15—C16—C17 | 0.3 (3) | C49—C44—C45—C46 | −0.6 (4) |
S14—C15—C16—C17 | −177.72 (15) | S43—C44—C45—C46 | −179.7 (2) |
C15—C16—C17—C18 | −0.9 (3) | C44—C45—C46—C47 | −0.6 (4) |
C16—C17—C18—C19 | 0.8 (3) | C45—C46—C47—C48 | 1.3 (4) |
C16—C17—C18—C21 | −179.1 (2) | C45—C46—C47—C50 | −178.0 (2) |
C17—C18—C19—C20 | −0.1 (3) | C46—C47—C48—C49 | −0.8 (4) |
C21—C18—C19—C20 | 179.8 (2) | C50—C47—C48—C49 | 178.5 (2) |
C18—C19—C20—C15 | −0.4 (3) | C47—C48—C49—C44 | −0.4 (4) |
C16—C15—C20—C19 | 0.3 (3) | C45—C44—C49—C48 | 1.1 (4) |
S14—C15—C20—C19 | 178.36 (16) | S43—C44—C49—C48 | −179.84 (18) |
C2—N13—S22—O4 | 139.80 (14) | C31—N42—S51—O8 | 139.98 (14) |
S14—N13—S22—O4 | −29.35 (13) | S43—N42—S51—O8 | −22.53 (13) |
C2—N13—S22—O3 | 9.68 (16) | C31—N42—S51—O7 | 10.41 (16) |
S14—N13—S22—O3 | −159.47 (11) | S43—N42—S51—O7 | −152.09 (11) |
C2—N13—S22—C23 | −104.10 (15) | C31—N42—S51—C52 | −104.33 (15) |
S14—N13—S22—C23 | 86.76 (12) | S43—N42—S51—C52 | 93.16 (12) |
O4—S22—C23—C24 | 18.53 (19) | O8—S51—C52—C57 | −145.10 (16) |
O3—S22—C23—C24 | 152.78 (16) | O7—S51—C52—C57 | −11.44 (19) |
N13—S22—C23—C24 | −96.69 (17) | N42—S51—C52—C57 | 101.34 (17) |
O4—S22—C23—C28 | −163.06 (17) | O8—S51—C52—C53 | 31.22 (19) |
O3—S22—C23—C28 | −28.81 (19) | O7—S51—C52—C53 | 164.87 (16) |
N13—S22—C23—C28 | 81.72 (18) | N42—S51—C52—C53 | −82.35 (17) |
C28—C23—C24—C25 | −0.1 (3) | C57—C52—C53—C54 | 0.0 (3) |
S22—C23—C24—C25 | 178.32 (16) | S51—C52—C53—C54 | −176.25 (16) |
C23—C24—C25—C26 | −1.5 (3) | C52—C53—C54—C55 | 0.1 (3) |
C24—C25—C26—C27 | 2.2 (3) | C53—C54—C55—C56 | 0.1 (3) |
C24—C25—C26—C29 | −177.18 (19) | C53—C54—C55—C58 | 179.68 (19) |
C25—C26—C27—C28 | −1.3 (3) | C54—C55—C56—C57 | −0.4 (3) |
C29—C26—C27—C28 | 178.0 (2) | C58—C55—C56—C57 | −179.97 (19) |
C26—C27—C28—C23 | −0.2 (3) | C53—C52—C57—C56 | −0.3 (3) |
C24—C23—C28—C27 | 0.9 (3) | S51—C52—C57—C56 | 175.97 (15) |
S22—C23—C28—C27 | −177.50 (16) | C55—C56—C57—C52 | 0.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C29—H29B···O3i | 0.96 | 2.54 | 3.148 (3) | 122 |
C50—H50C···O5ii | 0.96 | 2.47 | 3.397 (3) | 162 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C29—H29B···O3i | 0.96 | 2.54 | 3.148 (3) | 122 |
C50—H50C···O5ii | 0.96 | 2.47 | 3.397 (3) | 162 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+2, −z. |
Acknowledgements
This work was funded by PIFI-2011. The authors from the Universidad Autónoma de Yucatán are grateful to the Instituto de Química, Universidad Nacional Autónoma de México, for permission to the perform the X-ray analysis. We thank Br Hector Peniche Pavia for his participation in the synthetic procedure.
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Sulfonamide thiazoles are structural units frequently found as parts of skeletons of bioactive compounds including antimicrobials agents (Annadurai et al., 2012), anticonvulsant agents (Farag et al., 2012) or inhibitors of Nek2/Hec1 (Xiao-Long et al., 2009). Due to the importance of thiazole derivatives, we synthesized (I) N-[4-(p-tolyl)thiazol-2-yl]-4-methyl-N-(4- methylphenylsulfonyl)benzenesulfonamide, and discuss the geometry of the molecule and its conformation. The compound was obtained by the reaction of 4-p-tolyl-thiazol-2-ylamine in an excess of 4-methyl-benzenesulfonilchloride.
The title compound I crystallized with two independent molecules (A and B) in the asymmetric unit (Fig. 1). The geometries around the N13 and N42 atoms are almost trigonal planar with bonding angles ranging from 117.00° to 123.86°. The sulfonamide nitrogen atoms are bonded to a carbon atom of the thiazole ring and two sulfur atoms of the O=S=O groups, the distances of the C—N bonds are of 1.426 (2) Å for both molecules, and the N—S bonds are between 1.6902 (16) and 1.7040 (17) Å. The thiazole rings are rotated around C—N bond foming the dihedral angles of 85.57 (5)° and 89.28 (5)° with the planes O2S—N—SO2, in molecule A and B, respectively. The methylphenylsulfonyl groups keep anti-conformations forming a dihedral angles of 78.00 (7)°, 72.53 (5)° and 77.09 (6)°, 71.50 (7)° with the trigonal plane S—N—S, in the molecules A and B, respectively. The sulfur atoms of the sulfonamide groups are in a distorted tetrahedral geometry with angles varying from 103.43 (8) to 121.39 (1)°, and S=O bonds from 1.4175 (15) to 1.42358 (14) Å. The thiazole and p-tolyl groups in the molecule B exhibit a coplanar arrangement, while in the molecule A these moieties form an angle of 17.20 (7)° between these planes. Each independent molecule form a dimer arrangement by C—H···O interactions (Table 1, Fig. 2). The crystal packing in the title compound is stabilized by the C—H···O=S intermolecular interactions.