supplementary materials


kp2458 scheme

Acta Cryst. (2014). E70, o6-o7    [ doi:10.1107/S1600536813032145 ]

4-Methyl-N-(4-methyl­phenyl­sulfon­yl)-N-[4-(4-methyl­phen­yl)-1,3-thia­zol-2-yl]benzene­sulfonamide

R. M. Carballo, S. Hernández-Ortega, N. Padilla-Montaño, R. Reyes-Martínez and G. Mirón-López

Abstract top

There are two independent mol­ecules in the asymmetric unit of the title compound, C24H22N2O4S3. 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.

Comment top

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.

Related literature top

For bioactive sulfonamide compounds, see: Annadurai et al. (2012); Farag et al. (2012); Xiao-Long et al. (2009).

Experimental top

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%).

Refinement top

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 refinement 10 reflections were considered as disagreeable and were omitted.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound (I). All non-hydrogen atoms are shown as ellipsoids with probability level of 40%. Hydrogen atoms are omitted.
[Figure 2] Fig. 2. Hydrogen bonds in the crystal packing of the title compound, shown by dashed lines.
4-Methyl-N-(4-methylphenylsulfonyl)-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]benzenesulfonamide top
Crystal data top
C24H22N2O4S3Z = 4
Mr = 498.61F(000) = 1040
Triclinic, P1Dx = 1.410 Mg m3
a = 8.3322 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.0630 (3) ÅCell parameters from 7195 reflections
c = 23.5756 (6) Åθ = 2.3–25.3°
α = 84.615 (1)°µ = 0.35 mm1
β = 87.022 (1)°T = 298 K
γ = 85.482 (1)°Prism, colourless
V = 2349.46 (10) Å30.44 × 0.38 × 0.28 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
Rint = 0.035
Detector resolution: 0.83 pixels mm-1θmax = 25.4°, θmin = 1.7°
ω scansh = 1010
18770 measured reflectionsk = 1414
8539 independent reflectionsl = 2828
6755 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 0.98Δρmax = 0.23 e Å3
8539 reflectionsΔρmin = 0.28 e Å3
602 parametersExtinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0092 (7)
Crystal data top
C24H22N2O4S3γ = 85.482 (1)°
Mr = 498.61V = 2349.46 (10) Å3
Triclinic, P1Z = 4
a = 8.3322 (2) ÅMo Kα radiation
b = 12.0630 (3) ŵ = 0.35 mm1
c = 23.5756 (6) ÅT = 298 K
α = 84.615 (1)°0.44 × 0.38 × 0.28 mm
β = 87.022 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
6755 reflections with I > 2σ(I)
18770 measured reflectionsRint = 0.035
8539 independent reflectionsθmax = 25.4°
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.104Δρmax = 0.23 e Å3
S = 0.98Δρmin = 0.28 e Å3
8539 reflectionsAbsolute structure: ?
602 parametersAbsolute structure parameter: ?
2 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.21107 (6)0.86099 (4)0.70159 (2)0.04992 (16)
C20.3027 (2)0.73811 (15)0.68033 (8)0.0403 (4)
N30.38103 (19)0.67554 (13)0.71866 (7)0.0418 (4)
C40.3706 (2)0.72444 (16)0.76934 (8)0.0411 (5)
C50.2846 (2)0.82565 (16)0.76730 (9)0.0473 (5)
H50.26830.86950.79780.057*
C60.4503 (2)0.66461 (16)0.81880 (8)0.0424 (5)
C70.4960 (3)0.55130 (18)0.81897 (9)0.0555 (6)
H70.47520.51370.78780.067*
C80.5717 (3)0.49367 (18)0.86461 (9)0.0585 (6)
H80.60000.41770.86380.070*
C90.6060 (3)0.54611 (19)0.91126 (9)0.0532 (5)
C100.5589 (3)0.65886 (18)0.91154 (9)0.0607 (6)
H100.57920.69590.94300.073*
C110.4825 (3)0.71747 (17)0.86615 (9)0.0546 (6)
H110.45240.79310.86740.066*
C120.6947 (3)0.4832 (2)0.96038 (10)0.0776 (8)
H12A0.70160.53160.99010.116*
H12B0.80130.45830.94720.116*
H12C0.63740.41980.97490.116*
N130.29416 (19)0.70889 (13)0.62341 (6)0.0424 (4)
S140.15899 (6)0.61754 (4)0.61109 (2)0.04159 (14)
O10.02760 (15)0.64008 (11)0.65010 (6)0.0485 (3)
O20.13878 (17)0.63097 (12)0.55121 (6)0.0551 (4)
C150.2485 (2)0.48402 (16)0.63075 (8)0.0418 (5)
C160.3208 (2)0.41966 (17)0.58949 (9)0.0495 (5)
H160.32580.44770.55140.059*
C170.3850 (2)0.31386 (17)0.60579 (9)0.0524 (5)
H170.43240.27010.57810.063*
C180.3811 (2)0.27080 (16)0.66211 (10)0.0503 (5)
C190.3084 (3)0.33669 (17)0.70260 (9)0.0537 (6)
H190.30470.30870.74070.064*
C200.2412 (3)0.44314 (16)0.68760 (8)0.0492 (5)
H200.19200.48640.71520.059*
C210.4539 (3)0.15517 (18)0.67975 (12)0.0743 (7)
H21A0.54870.16040.70050.112*
H21B0.48230.11660.64640.112*
H21C0.37700.11480.70350.112*
S220.44065 (6)0.75042 (5)0.57530 (2)0.04896 (16)
O30.55605 (16)0.79107 (15)0.60897 (7)0.0711 (5)
O40.48252 (19)0.66221 (13)0.54054 (6)0.0672 (5)
C230.3487 (2)0.86359 (17)0.53395 (8)0.0429 (5)
C240.2862 (2)0.84817 (18)0.48251 (8)0.0488 (5)
H240.29530.77770.46920.059*
C250.2106 (3)0.93665 (16)0.45099 (9)0.0551 (6)
H250.17110.92570.41590.066*
C260.1920 (2)1.04194 (16)0.47036 (9)0.0550 (6)
C270.2570 (3)1.05608 (18)0.52176 (9)0.0642 (7)
H270.24771.12650.53510.077*
C280.3354 (3)0.96839 (18)0.55381 (10)0.0572 (6)
H280.37870.97970.58820.069*
C290.1023 (3)1.1370 (2)0.43677 (12)0.0802 (8)
H29A0.00541.11810.43170.120*
H29B0.15661.15110.40020.120*
H29C0.09861.20270.45700.120*
S300.28190 (7)1.08557 (4)0.27908 (2)0.05011 (16)
C310.2102 (2)1.04886 (15)0.21732 (8)0.0399 (4)
N320.13792 (19)1.12839 (12)0.18516 (7)0.0408 (4)
C330.1363 (2)1.22799 (14)0.21026 (8)0.0391 (4)
C340.2082 (2)1.21888 (15)0.26092 (9)0.0456 (5)
H340.21621.27810.28300.055*
C350.0581 (2)1.32933 (15)0.18075 (8)0.0401 (4)
C360.0114 (3)1.32644 (17)0.12923 (10)0.0622 (6)
H360.00781.25940.11250.075*
C370.0862 (3)1.42155 (18)0.10196 (11)0.0737 (8)
H370.13411.41680.06760.088*
C380.0918 (3)1.52323 (17)0.12436 (11)0.0576 (6)
C390.0221 (3)1.52557 (17)0.17562 (10)0.0586 (6)
H390.02441.59290.19200.070*
C400.0512 (3)1.43090 (15)0.20370 (9)0.0513 (5)
H400.09651.43560.23850.062*
C410.1697 (3)1.62846 (19)0.09396 (13)0.0871 (9)
H41A0.10771.64840.05960.131*
H41B0.17381.68810.11840.131*
H41C0.27711.61560.08470.131*
N420.23294 (19)0.93682 (12)0.20213 (7)0.0427 (4)
S430.39249 (6)0.90607 (4)0.15665 (2)0.04773 (15)
O50.50268 (17)0.98571 (12)0.16599 (7)0.0583 (4)
O60.43414 (19)0.78969 (11)0.16812 (6)0.0624 (4)
C440.3245 (3)0.93295 (16)0.08724 (9)0.0495 (5)
C450.2867 (3)0.84603 (19)0.05707 (10)0.0693 (7)
H450.29660.77290.07360.083*
C460.2344 (3)0.8686 (2)0.00260 (10)0.0729 (7)
H460.21020.80990.01760.088*
C470.2170 (3)0.9760 (2)0.02279 (9)0.0597 (6)
C480.2570 (3)1.0612 (2)0.00777 (10)0.0663 (7)
H480.24731.13420.00890.080*
C490.3109 (3)1.04112 (18)0.06221 (10)0.0586 (6)
H490.33781.09980.08190.070*
C500.1540 (3)1.0004 (2)0.08219 (10)0.0806 (8)
H50A0.07181.06080.08230.121*
H50B0.10960.93500.09330.121*
H50C0.24071.02070.10860.121*
S510.07665 (6)0.85425 (4)0.21475 (2)0.04588 (15)
O70.05860 (17)0.92715 (11)0.22956 (7)0.0609 (4)
O80.0765 (2)0.79145 (11)0.16686 (6)0.0617 (4)
C520.1246 (2)0.76319 (15)0.27528 (8)0.0412 (5)
C530.2258 (3)0.66786 (16)0.26941 (9)0.0521 (5)
H530.27360.65370.23400.063*
C540.2545 (3)0.59416 (17)0.31684 (9)0.0527 (5)
H540.32250.53010.31300.063*
C550.1849 (2)0.61315 (17)0.36979 (9)0.0473 (5)
C560.0841 (3)0.70896 (18)0.37416 (9)0.0544 (6)
H560.03540.72300.40940.065*
C570.0541 (2)0.78400 (17)0.32762 (9)0.0492 (5)
H570.01340.84830.33150.059*
C580.2167 (3)0.53202 (19)0.42073 (10)0.0661 (7)
H58A0.31870.54390.43540.099*
H58B0.21870.45720.40990.099*
H58C0.13290.54300.44960.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0562 (3)0.0432 (3)0.0499 (3)0.0036 (3)0.0051 (3)0.0061 (2)
C20.0424 (11)0.0394 (11)0.0395 (11)0.0056 (9)0.0001 (9)0.0044 (9)
N30.0496 (10)0.0396 (9)0.0364 (9)0.0057 (8)0.0008 (7)0.0035 (7)
C40.0433 (11)0.0419 (11)0.0390 (11)0.0090 (9)0.0011 (9)0.0053 (9)
C50.0532 (12)0.0457 (12)0.0444 (12)0.0041 (10)0.0011 (10)0.0111 (10)
C60.0462 (11)0.0444 (11)0.0373 (11)0.0095 (9)0.0018 (9)0.0035 (9)
C70.0742 (15)0.0514 (13)0.0414 (12)0.0026 (11)0.0050 (11)0.0116 (10)
C80.0770 (16)0.0492 (13)0.0474 (13)0.0061 (12)0.0031 (12)0.0032 (11)
C90.0587 (13)0.0574 (14)0.0423 (12)0.0075 (11)0.0011 (10)0.0047 (10)
C100.0870 (17)0.0552 (14)0.0429 (12)0.0159 (13)0.0137 (12)0.0050 (11)
C110.0755 (15)0.0415 (12)0.0486 (13)0.0082 (11)0.0107 (11)0.0058 (10)
C120.098 (2)0.0774 (18)0.0538 (15)0.0031 (15)0.0145 (14)0.0104 (13)
N130.0477 (9)0.0453 (9)0.0341 (9)0.0068 (8)0.0001 (7)0.0011 (7)
S140.0445 (3)0.0420 (3)0.0381 (3)0.0013 (2)0.0042 (2)0.0050 (2)
O10.0406 (7)0.0500 (8)0.0549 (9)0.0001 (6)0.0021 (6)0.0089 (7)
O20.0681 (10)0.0569 (9)0.0405 (8)0.0041 (7)0.0144 (7)0.0059 (7)
C150.0442 (11)0.0406 (11)0.0409 (11)0.0020 (9)0.0034 (9)0.0048 (9)
C160.0550 (13)0.0512 (13)0.0421 (12)0.0001 (10)0.0004 (10)0.0078 (10)
C170.0543 (13)0.0478 (13)0.0557 (14)0.0035 (10)0.0012 (11)0.0161 (11)
C180.0491 (12)0.0396 (11)0.0636 (14)0.0020 (10)0.0117 (11)0.0085 (11)
C190.0700 (14)0.0450 (12)0.0463 (12)0.0052 (11)0.0106 (11)0.0007 (10)
C200.0624 (13)0.0454 (12)0.0398 (11)0.0003 (10)0.0012 (10)0.0079 (10)
C210.0869 (18)0.0474 (14)0.0889 (19)0.0057 (13)0.0210 (15)0.0068 (13)
S220.0385 (3)0.0630 (4)0.0421 (3)0.0029 (3)0.0012 (2)0.0052 (3)
O30.0409 (8)0.1111 (14)0.0605 (10)0.0190 (9)0.0101 (7)0.0124 (9)
O40.0708 (10)0.0706 (10)0.0521 (9)0.0262 (9)0.0135 (8)0.0011 (8)
C230.0355 (10)0.0507 (12)0.0410 (11)0.0065 (9)0.0047 (9)0.0023 (9)
C240.0484 (12)0.0533 (13)0.0439 (12)0.0022 (10)0.0021 (10)0.0033 (10)
C250.0506 (13)0.0637 (15)0.0484 (13)0.0023 (11)0.0023 (10)0.0076 (11)
C260.0393 (11)0.0575 (14)0.0633 (15)0.0044 (10)0.0119 (11)0.0126 (12)
C270.0676 (15)0.0415 (13)0.0817 (18)0.0110 (11)0.0177 (14)0.0013 (12)
C280.0638 (14)0.0551 (14)0.0543 (14)0.0183 (11)0.0014 (11)0.0040 (11)
C290.0538 (15)0.0697 (16)0.106 (2)0.0090 (13)0.0105 (14)0.0330 (16)
S300.0628 (3)0.0406 (3)0.0472 (3)0.0031 (3)0.0096 (3)0.0078 (2)
C310.0448 (11)0.0307 (10)0.0441 (11)0.0025 (8)0.0014 (9)0.0048 (9)
N320.0477 (9)0.0303 (8)0.0447 (9)0.0046 (7)0.0005 (8)0.0045 (7)
C330.0418 (11)0.0294 (10)0.0464 (11)0.0056 (8)0.0058 (9)0.0064 (8)
C340.0533 (12)0.0352 (11)0.0499 (12)0.0016 (9)0.0021 (10)0.0138 (9)
C350.0414 (11)0.0305 (10)0.0481 (12)0.0048 (8)0.0038 (9)0.0037 (9)
C360.0848 (17)0.0341 (11)0.0700 (16)0.0015 (11)0.0209 (13)0.0089 (11)
C370.099 (2)0.0474 (14)0.0774 (17)0.0050 (13)0.0406 (16)0.0010 (13)
C380.0573 (14)0.0391 (12)0.0754 (16)0.0032 (10)0.0086 (12)0.0024 (11)
C390.0761 (16)0.0300 (11)0.0693 (16)0.0033 (11)0.0016 (13)0.0060 (11)
C400.0676 (14)0.0357 (11)0.0506 (13)0.0023 (10)0.0015 (11)0.0063 (10)
C410.101 (2)0.0458 (14)0.113 (2)0.0006 (14)0.0331 (19)0.0110 (15)
N420.0532 (10)0.0278 (8)0.0475 (10)0.0025 (7)0.0005 (8)0.0058 (7)
S430.0545 (3)0.0376 (3)0.0503 (3)0.0057 (2)0.0025 (2)0.0075 (2)
O50.0498 (9)0.0597 (9)0.0670 (10)0.0061 (7)0.0005 (7)0.0143 (8)
O60.0797 (11)0.0424 (8)0.0624 (10)0.0193 (8)0.0059 (8)0.0084 (7)
C440.0606 (13)0.0402 (11)0.0468 (12)0.0015 (10)0.0025 (10)0.0060 (10)
C450.110 (2)0.0426 (13)0.0558 (15)0.0027 (13)0.0055 (14)0.0105 (11)
C460.104 (2)0.0657 (16)0.0516 (15)0.0078 (15)0.0056 (14)0.0164 (13)
C470.0567 (14)0.0750 (16)0.0455 (13)0.0018 (12)0.0096 (11)0.0046 (12)
C480.0803 (17)0.0568 (14)0.0582 (15)0.0015 (13)0.0010 (13)0.0077 (12)
C490.0764 (16)0.0436 (12)0.0558 (14)0.0073 (11)0.0022 (12)0.0030 (11)
C500.0746 (17)0.114 (2)0.0497 (15)0.0005 (16)0.0013 (13)0.0010 (15)
S510.0541 (3)0.0318 (3)0.0524 (3)0.0050 (2)0.0133 (3)0.0005 (2)
O70.0466 (8)0.0460 (8)0.0875 (12)0.0033 (7)0.0084 (8)0.0056 (8)
O80.0960 (12)0.0406 (8)0.0521 (9)0.0172 (8)0.0256 (8)0.0001 (7)
C520.0459 (11)0.0328 (10)0.0462 (11)0.0053 (9)0.0095 (9)0.0034 (9)
C530.0693 (14)0.0417 (12)0.0439 (12)0.0028 (11)0.0012 (11)0.0024 (10)
C540.0622 (14)0.0393 (11)0.0555 (14)0.0046 (10)0.0086 (11)0.0016 (10)
C550.0506 (12)0.0477 (12)0.0455 (12)0.0141 (10)0.0114 (10)0.0005 (10)
C560.0582 (13)0.0598 (14)0.0459 (12)0.0090 (11)0.0022 (10)0.0063 (11)
C570.0492 (12)0.0433 (12)0.0553 (13)0.0007 (10)0.0015 (10)0.0086 (10)
C580.0751 (16)0.0686 (15)0.0541 (14)0.0109 (13)0.0175 (12)0.0095 (12)
Geometric parameters (Å, º) top
S1—C51.700 (2)S30—C341.6998 (19)
S1—C21.7182 (19)S30—C311.7107 (19)
C2—N31.292 (2)C31—N321.295 (2)
C2—N131.426 (2)C31—N421.426 (2)
N3—C41.377 (2)N32—C331.387 (2)
C4—C51.364 (3)C33—C341.355 (3)
C4—C61.473 (3)C33—C351.471 (2)
C5—H50.9300C34—H340.9300
C6—C111.384 (3)C35—C361.377 (3)
C6—C71.389 (3)C35—C401.381 (3)
C7—C81.378 (3)C36—C371.382 (3)
C7—H70.9300C36—H360.9300
C8—C91.372 (3)C37—C381.377 (3)
C8—H80.9300C37—H370.9300
C9—C101.386 (3)C38—C391.371 (3)
C9—C121.516 (3)C38—C411.515 (3)
C10—C111.381 (3)C39—C401.380 (3)
C10—H100.9300C39—H390.9300
C11—H110.9300C40—H400.9300
C12—H12A0.9600C41—H41A0.9600
C12—H12B0.9600C41—H41B0.9600
C12—H12C0.9600C41—H41C0.9600
N13—S141.6902 (16)N42—S511.6985 (17)
N13—S221.6951 (16)N42—S431.7040 (17)
S14—O11.4190 (14)S43—O51.4191 (15)
S14—O21.4232 (14)S43—O61.4235 (14)
S14—C151.7526 (19)S43—C441.752 (2)
C15—C201.384 (3)C44—C491.380 (3)
C15—C161.386 (3)C44—C451.386 (3)
C16—C171.373 (3)C45—C461.374 (3)
C16—H160.9300C45—H450.9300
C17—C181.379 (3)C46—C471.375 (3)
C17—H170.9300C46—H460.9300
C18—C191.384 (3)C47—C481.379 (3)
C18—C211.507 (3)C47—C501.516 (3)
C19—C201.382 (3)C48—C491.375 (3)
C19—H190.9300C48—H480.9300
C20—H200.9300C49—H490.9300
C21—H21A0.9600C50—H50A0.9600
C21—H21B0.9600C50—H50B0.9600
C21—H21C0.9600C50—H50C0.9600
S22—O41.4146 (16)S51—O81.4175 (15)
S22—O31.4219 (15)S51—O71.4233 (15)
S22—C231.7505 (19)S51—C521.7605 (19)
C23—C241.378 (3)C52—C571.375 (3)
C23—C281.383 (3)C52—C531.384 (3)
C24—C251.372 (3)C53—C541.380 (3)
C24—H240.9300C53—H530.9300
C25—C261.3842 (17)C54—C551.380 (3)
C25—H250.9300C54—H540.9300
C26—C271.3831 (17)C55—C561.383 (3)
C26—C291.502 (3)C55—C581.497 (3)
C27—C281.382 (3)C56—C571.376 (3)
C27—H270.9300C56—H560.9300
C28—H280.9300C57—H570.9300
C29—H29A0.9600C58—H58A0.9600
C29—H29B0.9600C58—H58B0.9600
C29—H29C0.9600C58—H58C0.9600
C5—S1—C288.51 (9)C34—S30—C3188.39 (9)
N3—C2—N13122.53 (17)N32—C31—N42122.52 (17)
N3—C2—S1115.95 (14)N32—C31—S30116.37 (14)
N13—C2—S1121.50 (14)N42—C31—S30121.10 (14)
C2—N3—C4110.23 (16)C31—N32—C33109.64 (16)
C5—C4—N3114.31 (17)C34—C33—N32114.17 (16)
C5—C4—C6127.27 (18)C34—C33—C35127.37 (17)
N3—C4—C6118.42 (16)N32—C33—C35118.45 (17)
C4—C5—S1110.99 (15)C33—C34—S30111.43 (14)
C4—C5—H5124.5C33—C34—H34124.3
S1—C5—H5124.5S30—C34—H34124.3
C11—C6—C7117.75 (18)C36—C35—C40117.44 (18)
C11—C6—C4122.21 (18)C36—C35—C33121.25 (17)
C7—C6—C4120.04 (17)C40—C35—C33121.31 (18)
C8—C7—C6121.09 (19)C35—C36—C37121.1 (2)
C8—C7—H7119.5C35—C36—H36119.5
C6—C7—H7119.5C37—C36—H36119.5
C9—C8—C7121.3 (2)C38—C37—C36121.7 (2)
C9—C8—H8119.3C38—C37—H37119.2
C7—C8—H8119.3C36—C37—H37119.2
C8—C9—C10117.7 (2)C39—C38—C37116.9 (2)
C8—C9—C12121.1 (2)C39—C38—C41121.0 (2)
C10—C9—C12121.2 (2)C37—C38—C41122.0 (2)
C11—C10—C9121.5 (2)C38—C39—C40122.0 (2)
C11—C10—H10119.3C38—C39—H39119.0
C9—C10—H10119.3C40—C39—H39119.0
C10—C11—C6120.6 (2)C39—C40—C35120.9 (2)
C10—C11—H11119.7C39—C40—H40119.6
C6—C11—H11119.7C35—C40—H40119.6
C9—C12—H12A109.5C38—C41—H41A109.5
C9—C12—H12B109.5C38—C41—H41B109.5
H12A—C12—H12B109.5H41A—C41—H41B109.5
C9—C12—H12C109.5C38—C41—H41C109.5
H12A—C12—H12C109.5H41A—C41—H41C109.5
H12B—C12—H12C109.5H41B—C41—H41C109.5
C2—N13—S14117.79 (13)C31—N42—S51118.07 (13)
C2—N13—S22117.50 (13)C31—N42—S43116.99 (13)
S14—N13—S22123.86 (9)S51—N42—S43122.71 (9)
O1—S14—O2120.91 (8)O5—S43—O6120.77 (9)
O1—S14—N13104.42 (8)O5—S43—N42103.42 (8)
O2—S14—N13105.63 (8)O6—S43—N42105.94 (9)
O1—S14—C15108.55 (9)O5—S43—C44109.09 (10)
O2—S14—C15109.88 (9)O6—S43—C44109.59 (9)
N13—S14—C15106.39 (8)N42—S43—C44107.04 (9)
C20—C15—C16120.91 (18)C49—C44—C45119.8 (2)
C20—C15—S14118.98 (15)C49—C44—S43119.79 (17)
C16—C15—S14120.08 (15)C45—C44—S43120.39 (17)
C17—C16—C15118.92 (19)C46—C45—C44119.6 (2)
C17—C16—H16120.5C46—C45—H45120.2
C15—C16—H16120.5C44—C45—H45120.2
C16—C17—C18121.72 (19)C45—C46—C47121.6 (2)
C16—C17—H17119.1C45—C46—H46119.2
C18—C17—H17119.1C47—C46—H46119.2
C17—C18—C19118.33 (18)C46—C47—C48117.9 (2)
C17—C18—C21121.4 (2)C46—C47—C50121.1 (2)
C19—C18—C21120.3 (2)C48—C47—C50121.0 (2)
C20—C19—C18121.4 (2)C49—C48—C47121.9 (2)
C20—C19—H19119.3C49—C48—H48119.1
C18—C19—H19119.3C47—C48—H48119.1
C19—C20—C15118.67 (19)C48—C49—C44119.2 (2)
C19—C20—H20120.7C48—C49—H49120.4
C15—C20—H20120.7C44—C49—H49120.4
C18—C21—H21A109.5C47—C50—H50A109.5
C18—C21—H21B109.5C47—C50—H50B109.5
H21A—C21—H21B109.5H50A—C50—H50B109.5
C18—C21—H21C109.5C47—C50—H50C109.5
H21A—C21—H21C109.5H50A—C50—H50C109.5
H21B—C21—H21C109.5H50B—C50—H50C109.5
O4—S22—O3121.39 (10)O8—S51—O7121.16 (10)
O4—S22—N13107.88 (9)O8—S51—N42105.89 (9)
O3—S22—N13103.99 (9)O7—S51—N42105.46 (8)
O4—S22—C23109.14 (9)O8—S51—C52108.98 (9)
O3—S22—C23108.52 (10)O7—S51—C52108.32 (10)
N13—S22—C23104.60 (8)N42—S51—C52106.01 (8)
C24—C23—C28120.01 (19)C57—C52—C53120.39 (19)
C24—C23—S22120.34 (16)C57—C52—S51119.64 (15)
C28—C23—S22119.63 (16)C53—C52—S51119.86 (16)
C25—C24—C23120.1 (2)C54—C53—C52119.0 (2)
C25—C24—H24120.0C54—C53—H53120.5
C23—C24—H24120.0C52—C53—H53120.5
C24—C25—C26121.3 (2)C55—C54—C53121.7 (2)
C24—C25—H25119.4C55—C54—H54119.2
C26—C25—H25119.4C53—C54—H54119.2
C27—C26—C25117.8 (2)C54—C55—C56117.89 (19)
C27—C26—C29121.4 (2)C54—C55—C58121.0 (2)
C25—C26—C29120.8 (2)C56—C55—C58121.1 (2)
C28—C27—C26121.8 (2)C57—C56—C55121.6 (2)
C28—C27—H27119.1C57—C56—H56119.2
C26—C27—H27119.1C55—C56—H56119.2
C27—C28—C23119.0 (2)C52—C57—C56119.44 (19)
C27—C28—H28120.5C52—C57—H57120.3
C23—C28—H28120.5C56—C57—H57120.3
C26—C29—H29A109.5C55—C58—H58A109.5
C26—C29—H29B109.5C55—C58—H58B109.5
H29A—C29—H29B109.5H58A—C58—H58B109.5
C26—C29—H29C109.5C55—C58—H58C109.5
H29A—C29—H29C109.5H58A—C58—H58C109.5
H29B—C29—H29C109.5H58B—C58—H58C109.5
C5—S1—C2—N30.20 (16)C34—S30—C31—N320.38 (16)
C5—S1—C2—N13178.73 (16)C34—S30—C31—N42179.08 (17)
N13—C2—N3—C4179.31 (17)N42—C31—N32—C33178.92 (17)
S1—C2—N3—C40.4 (2)S30—C31—N32—C330.2 (2)
C2—N3—C4—C51.0 (2)C31—N32—C33—C340.1 (2)
C2—N3—C4—C6178.96 (17)C31—N32—C33—C35179.46 (16)
N3—C4—C5—S11.1 (2)N32—C33—C34—S300.4 (2)
C6—C4—C5—S1178.80 (16)C35—C33—C34—S30179.67 (15)
C2—S1—C5—C40.73 (16)C31—S30—C34—C330.41 (16)
C5—C4—C6—C1117.2 (3)C34—C33—C35—C36179.7 (2)
N3—C4—C6—C11162.9 (2)N32—C33—C35—C360.4 (3)
C5—C4—C6—C7162.9 (2)C34—C33—C35—C400.2 (3)
N3—C4—C6—C717.0 (3)N32—C33—C35—C40179.45 (19)
C11—C6—C7—C80.3 (3)C40—C35—C36—C370.6 (3)
C4—C6—C7—C8179.6 (2)C33—C35—C36—C37179.3 (2)
C6—C7—C8—C90.7 (4)C35—C36—C37—C381.3 (4)
C7—C8—C9—C101.4 (3)C36—C37—C38—C391.2 (4)
C7—C8—C9—C12177.7 (2)C36—C37—C38—C41178.4 (2)
C8—C9—C10—C111.1 (4)C37—C38—C39—C400.3 (4)
C12—C9—C10—C11178.0 (2)C41—C38—C39—C40179.2 (2)
C9—C10—C11—C60.2 (4)C38—C39—C40—C350.4 (4)
C7—C6—C11—C100.6 (3)C36—C35—C40—C390.3 (3)
C4—C6—C11—C10179.4 (2)C33—C35—C40—C39179.84 (19)
N3—C2—N13—S1481.0 (2)N32—C31—N42—S5181.3 (2)
S1—C2—N13—S14100.19 (16)S30—C31—N42—S51100.11 (16)
N3—C2—N13—S2288.9 (2)N32—C31—N42—S4382.2 (2)
S1—C2—N13—S2289.99 (16)S30—C31—N42—S4396.38 (16)
C2—N13—S14—O133.22 (15)C31—N42—S43—O526.11 (16)
S22—N13—S14—O1157.66 (10)S51—N42—S43—O5171.21 (10)
C2—N13—S14—O2161.73 (13)C31—N42—S43—O6154.07 (14)
S22—N13—S14—O229.15 (13)S51—N42—S43—O643.24 (13)
C2—N13—S14—C1581.50 (15)C31—N42—S43—C4489.03 (15)
S22—N13—S14—C1587.62 (12)S51—N42—S43—C4473.65 (13)
O1—S14—C15—C2029.21 (19)O5—S43—C44—C4931.6 (2)
O2—S14—C15—C20163.45 (16)O6—S43—C44—C49165.88 (17)
N13—S14—C15—C2082.66 (18)N42—S43—C44—C4979.7 (2)
O1—S14—C15—C16148.83 (16)O5—S43—C44—C45147.44 (19)
O2—S14—C15—C1614.6 (2)O6—S43—C44—C4513.2 (2)
N13—S14—C15—C1699.30 (17)N42—S43—C44—C45101.3 (2)
C20—C15—C16—C170.3 (3)C49—C44—C45—C460.6 (4)
S14—C15—C16—C17177.72 (15)S43—C44—C45—C46179.7 (2)
C15—C16—C17—C180.9 (3)C44—C45—C46—C470.6 (4)
C16—C17—C18—C190.8 (3)C45—C46—C47—C481.3 (4)
C16—C17—C18—C21179.1 (2)C45—C46—C47—C50178.0 (2)
C17—C18—C19—C200.1 (3)C46—C47—C48—C490.8 (4)
C21—C18—C19—C20179.8 (2)C50—C47—C48—C49178.5 (2)
C18—C19—C20—C150.4 (3)C47—C48—C49—C440.4 (4)
C16—C15—C20—C190.3 (3)C45—C44—C49—C481.1 (4)
S14—C15—C20—C19178.36 (16)S43—C44—C49—C48179.84 (18)
C2—N13—S22—O4139.80 (14)C31—N42—S51—O8139.98 (14)
S14—N13—S22—O429.35 (13)S43—N42—S51—O822.53 (13)
C2—N13—S22—O39.68 (16)C31—N42—S51—O710.41 (16)
S14—N13—S22—O3159.47 (11)S43—N42—S51—O7152.09 (11)
C2—N13—S22—C23104.10 (15)C31—N42—S51—C52104.33 (15)
S14—N13—S22—C2386.76 (12)S43—N42—S51—C5293.16 (12)
O4—S22—C23—C2418.53 (19)O8—S51—C52—C57145.10 (16)
O3—S22—C23—C24152.78 (16)O7—S51—C52—C5711.44 (19)
N13—S22—C23—C2496.69 (17)N42—S51—C52—C57101.34 (17)
O4—S22—C23—C28163.06 (17)O8—S51—C52—C5331.22 (19)
O3—S22—C23—C2828.81 (19)O7—S51—C52—C53164.87 (16)
N13—S22—C23—C2881.72 (18)N42—S51—C52—C5382.35 (17)
C28—C23—C24—C250.1 (3)C57—C52—C53—C540.0 (3)
S22—C23—C24—C25178.32 (16)S51—C52—C53—C54176.25 (16)
C23—C24—C25—C261.5 (3)C52—C53—C54—C550.1 (3)
C24—C25—C26—C272.2 (3)C53—C54—C55—C560.1 (3)
C24—C25—C26—C29177.18 (19)C53—C54—C55—C58179.68 (19)
C25—C26—C27—C281.3 (3)C54—C55—C56—C570.4 (3)
C29—C26—C27—C28178.0 (2)C58—C55—C56—C57179.97 (19)
C26—C27—C28—C230.2 (3)C53—C52—C57—C560.3 (3)
C24—C23—C28—C270.9 (3)S51—C52—C57—C56175.97 (15)
S22—C23—C28—C27177.50 (16)C55—C56—C57—C520.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C29—H29B···O3i0.962.543.148 (3)122
C50—H50C···O5ii0.962.473.397 (3)162
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C29—H29B···O3i0.962.543.148 (3)122
C50—H50C···O5ii0.962.473.397 (3)162
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+2, z.
Acknowledgements top

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.

references
References top

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Farag, A. A., Abd-Alrahman, S. N., Ahmed, G. F., Ammar, R. M., Ammar, Y. A. & Abbas, S. Y. (2012). Arch. Pharm. Chem. Life Sci. 345, 703–712.

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Spek, A. L. (2009). Acta Cryst. D65, 148–155.

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