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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-(1,5-Di­phenyl-4-phenyl­sulfonyl-1H-pyrazol-3-yl)ethanone

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
*Correspondence e-mail: hkfun@usm.my

(Received 24 July 2012; accepted 8 August 2012; online 15 August 2012)

The asymmetric unit of the title compound, C23H18N2O3S, contains two mol­ecules with comparable geometries. In one mol­ecule, the pyrazole ring forms dihedral angles of 61.65 (11), 47.88 (11) and 63.20 (14)° with the three benzene rings. The corresponding values for the other mol­ecule are 77.19 (11), 43.55 (11) and 63.56 (15)°. In the crystal, both mol­ecules are linked into inversion dimers by pairs of C—H⋯S hydrogen bonds, generating R22(14) loops in each case.

Related literature

For background to and pharmaceutical applications of pyrazole derivatives, see: Gürsoy et al. (2000[Gürsoy, A., Demirayak, S., Capan, G., Erol, K. & Vural, K. (2000). Eur. J. Med. Chem. 35, 359-364.]); Kurumbail et al. (1996[Kurumbail, R. G., Stevens, A. M., Gierse, J. K., McDonald, J. J., Stegeman, R. A., Pak, J. Y., Gildehaus, D. M., iyashiro, J., Penning, T. D., Seibert, K. C., Isakson, P. & Stallings, W. C. (1996). Nature (London), 384, 644-648.]). For further synthetic details, see: Saleh & Abd El-Rahman (2009[Saleh, T. S. & Abd El-Rahman, N. M. (2009). Ultrason. Sonochem. 16, 237-242.]); Nassar et al. (2011[Nassar, E., Abdel-Aziz, H. A., Ibrahim, H. S. & Mansour, A. M. (2011). Sci. Pharm. 79, 507-524.]).

[Scheme 1]

Experimental

Crystal data
  • C23H18N2O3S

  • Mr = 402.45

  • Triclinic, [P \overline 1]

  • a = 10.4078 (2) Å

  • b = 14.0839 (3) Å

  • c = 14.2468 (3) Å

  • α = 87.595 (2)°

  • β = 80.875 (2)°

  • γ = 86.850 (2)°

  • V = 2057.62 (7) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 1.62 mm−1

  • T = 296 K

  • 0.66 × 0.55 × 0.17 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.415, Tmax = 0.771

  • 19520 measured reflections

  • 6561 independent reflections

  • 5618 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.123

  • S = 1.05

  • 6561 reflections

  • 525 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C11A—H11A⋯O2Ai 0.93 2.59 3.428 (3) 149
C11B—H11B⋯O3Bii 0.93 2.57 3.370 (3) 144
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Pyrazole derivatives have been attracted a great deal of research interest because of their various pharmaceutical applications (Gürsoy et al., 2000). N-arylpyrazoles were found to be a main pharmacophore in the famous anti-inflammatory drugs Celecoxib and SC-558 (Kurumbail et al., 1996). As part of our atudies in this area, we now describe the crystal structure of the title compound.

The asymmetric unit (Fig. 1) of the title compound consists of two independent molecules (A and B), with comparable geometries. In molecule A, pyrazol-3-yl ring (N1A/N2A/C1A-C3A) forms dihedral angles of 61.65 (11), 47.88 (11) and 63.20 (14)° with the three benzene rings (C6A-C11A, C12A-C17A, C18A-C23A), respectively. The corresponding dihedral angles for molecule B are 77.19 (11), 43.55 (11) and 63.56 (15)°, respectively.

In the crystal, Fig. 2, both independent molecules are linked into inversion dimers by pairs of C—H···S hydrogen bonds (Table 1), generating R22(14) loops in each case.

Related literature top

For background to and pharmaceutical applications of pyrazole derivatives, see: Gürsoy et al. (2000); Kurumbail et al. (1996). For further synthetic details, see: Saleh & Abd El-Rahman (2009); Nassar et al. (2011).

Experimental top

The title compound was prepared by the reaction of (Z)-2-oxo-N'-phenylpropanehydrazonoyl chloride with 1-phenyl-2-(phenylsulfonyl)ethanone according to the reported method (Saleh & Abd El-Rahman, 2009; Nassar et al., 2011). Yellow plates were obtained by slowly evaporating an ethanol solution at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model with C–H = 0.93 or 0.96 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied for the methyl groups.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
Fig. 1. The asymmetric unit of the title compound showing 30% probability displacement ellipsoids for non-H atoms.

Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.
1-(1,5-Diphenyl-4-phenylsulfonyl-1H-pyrazol-3-yl)ethanone top
Crystal data top
C23H18N2O3SZ = 4
Mr = 402.45F(000) = 840
Triclinic, P1Dx = 1.299 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 10.4078 (2) ÅCell parameters from 2375 reflections
b = 14.0839 (3) Åθ = 3.1–69.6°
c = 14.2468 (3) ŵ = 1.62 mm1
α = 87.595 (2)°T = 296 K
β = 80.875 (2)°Plate, yellow
γ = 86.850 (2)°0.66 × 0.55 × 0.17 mm
V = 2057.62 (7) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
6561 independent reflections
Radiation source: fine-focus sealed tube5618 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 64.0°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1212
Tmin = 0.415, Tmax = 0.771k = 1615
19520 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.079P)2 + 0.2166P]
where P = (Fo2 + 2Fc2)/3
6561 reflections(Δ/σ)max = 0.001
525 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C23H18N2O3Sγ = 86.850 (2)°
Mr = 402.45V = 2057.62 (7) Å3
Triclinic, P1Z = 4
a = 10.4078 (2) ÅCu Kα radiation
b = 14.0839 (3) ŵ = 1.62 mm1
c = 14.2468 (3) ÅT = 296 K
α = 87.595 (2)°0.66 × 0.55 × 0.17 mm
β = 80.875 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
6561 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
5618 reflections with I > 2σ(I)
Tmin = 0.415, Tmax = 0.771Rint = 0.029
19520 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.05Δρmax = 0.30 e Å3
6561 reflectionsΔρmin = 0.31 e Å3
525 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.37925 (5)0.47575 (3)0.16765 (3)0.05013 (14)
O1A0.13209 (17)0.55466 (13)0.04899 (13)0.0789 (5)
O2A0.36657 (18)0.57364 (10)0.13967 (11)0.0690 (4)
O3A0.49637 (15)0.44031 (12)0.20008 (11)0.0684 (4)
N1A0.39837 (14)0.30565 (11)0.04242 (11)0.0463 (3)
N2A0.31322 (14)0.37098 (11)0.07247 (11)0.0490 (4)
C1A0.28797 (17)0.43418 (13)0.00471 (13)0.0469 (4)
C2A0.35983 (17)0.40841 (13)0.07040 (13)0.0451 (4)
C3A0.43075 (17)0.32531 (13)0.04339 (13)0.0452 (4)
C4A0.19157 (19)0.51359 (14)0.01795 (16)0.0553 (5)
C5A0.1720 (2)0.5387 (2)0.11806 (19)0.0762 (7)
H5AA0.10360.58740.11770.114*
H5AB0.14860.48330.14720.114*
H5AC0.25130.56160.15340.114*
C6A0.52929 (18)0.26530 (13)0.08549 (14)0.0501 (4)
C7A0.4967 (2)0.21668 (15)0.17240 (15)0.0617 (5)
H7AA0.41220.22220.20530.074*
C8A0.5903 (3)0.16043 (17)0.20940 (19)0.0799 (8)
H8AA0.56880.12850.26780.096*
C9A0.7151 (3)0.1510 (2)0.1608 (2)0.0911 (9)
H9AA0.77790.11320.18640.109*
C10A0.7467 (3)0.1976 (2)0.0741 (2)0.0842 (8)
H10A0.83080.19030.04080.101*
C11A0.6548 (2)0.25519 (17)0.03618 (18)0.0644 (5)
H11A0.67710.28700.02220.077*
C12A0.44407 (17)0.22803 (14)0.10297 (14)0.0504 (4)
C13A0.4429 (2)0.13644 (15)0.06638 (18)0.0636 (5)
H13A0.41510.12410.00190.076*
C14A0.4839 (3)0.06240 (19)0.1273 (2)0.0807 (8)
H14A0.48450.00010.10340.097*
C15A0.5233 (2)0.0809 (2)0.2219 (2)0.0815 (8)
H15A0.54990.03100.26220.098*
C16A0.5238 (2)0.1724 (2)0.25782 (19)0.0791 (8)
H16A0.55090.18430.32240.095*
C17A0.4838 (2)0.24787 (17)0.19820 (16)0.0631 (5)
H17A0.48400.31030.22220.076*
C18A0.2489 (2)0.45154 (15)0.25945 (14)0.0570 (5)
C19A0.1353 (3)0.5041 (3)0.2648 (2)0.1044 (11)
H19A0.12430.55170.21910.125*
C20A0.0349 (4)0.4859 (4)0.3395 (3)0.1405 (18)
H20A0.04360.52160.34380.169*
C21A0.0515 (4)0.4165 (3)0.4055 (3)0.1161 (13)
H21A0.01660.40350.45430.139*
C22A0.1662 (4)0.3658 (2)0.4012 (2)0.1059 (12)
H22A0.17750.31960.44810.127*
C23A0.2668 (3)0.38203 (18)0.32767 (18)0.0828 (7)
H23A0.34540.34660.32430.099*
S1B0.10148 (4)0.84479 (3)0.50127 (3)0.04992 (14)
O1B0.33919 (16)0.96467 (12)0.56269 (11)0.0724 (4)
O2B0.00062 (15)0.80155 (12)0.46302 (11)0.0701 (4)
O3B0.06872 (15)0.89164 (12)0.58981 (10)0.0660 (4)
N1B0.17893 (14)1.02892 (11)0.29402 (10)0.0456 (3)
N2B0.24738 (14)1.06815 (11)0.35475 (11)0.0485 (3)
C1B0.24196 (16)1.00752 (13)0.42902 (12)0.0455 (4)
C2B0.16822 (16)0.92861 (13)0.41561 (12)0.0444 (4)
C3B0.12909 (16)0.94527 (13)0.32797 (12)0.0432 (4)
C4B0.31394 (18)1.02748 (15)0.50764 (14)0.0534 (4)
C5B0.3515 (3)1.12733 (18)0.51436 (19)0.0755 (6)
H5BA0.40791.12970.56130.113*
H5BB0.27461.16740.53230.113*
H5BC0.39611.14910.45380.113*
C6B0.04661 (17)0.88993 (13)0.27640 (12)0.0465 (4)
C7B0.0984 (2)0.80847 (16)0.23040 (16)0.0618 (5)
H7BA0.18600.79010.22880.074*
C8B0.0189 (3)0.75462 (18)0.18691 (18)0.0790 (7)
H8BA0.05310.70030.15520.095*
C9B0.1115 (3)0.7818 (2)0.19072 (18)0.0809 (7)
H9BA0.16580.74400.16400.097*
C10B0.1607 (2)0.8637 (2)0.23349 (18)0.0761 (7)
H10B0.24780.88270.23380.091*
C11B0.08225 (19)0.91856 (17)0.27633 (15)0.0591 (5)
H11B0.11610.97460.30500.071*
C12B0.15416 (17)1.08518 (15)0.21182 (13)0.0523 (4)
C13B0.1600 (2)1.0446 (2)0.12513 (15)0.0695 (6)
H13B0.18210.98020.11720.083*
C14B0.1313 (3)1.1044 (3)0.04867 (17)0.0887 (9)
H14B0.13221.07870.01050.106*
C15B0.1021 (3)1.1993 (2)0.0597 (2)0.0861 (8)
H15B0.08441.23780.00810.103*
C16B0.0988 (2)1.2376 (2)0.1462 (2)0.0778 (7)
H16B0.08001.30250.15320.093*
C17B0.1231 (2)1.18103 (16)0.22353 (17)0.0623 (5)
H17B0.11871.20720.28290.075*
C18B0.2234 (2)0.75497 (14)0.51379 (15)0.0569 (5)
C19B0.2700 (3)0.74521 (19)0.59938 (19)0.0809 (7)
H19B0.24420.78910.64650.097*
C20B0.3550 (4)0.6699 (2)0.6142 (3)0.1172 (13)
H20B0.38550.66150.67200.141*
C21B0.3938 (5)0.6080 (3)0.5438 (3)0.149 (2)
H21B0.45350.55840.55320.178*
C22B0.3466 (5)0.6169 (3)0.4582 (3)0.1325 (16)
H22B0.37410.57360.41080.159*
C23B0.2583 (3)0.69079 (18)0.4439 (2)0.0825 (8)
H23B0.22320.69680.38770.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0575 (3)0.0468 (3)0.0485 (3)0.01179 (19)0.01181 (19)0.00416 (19)
O1A0.0801 (11)0.0753 (11)0.0796 (11)0.0198 (8)0.0109 (9)0.0205 (9)
O2A0.0992 (12)0.0461 (8)0.0648 (9)0.0192 (7)0.0175 (8)0.0011 (6)
O3A0.0643 (9)0.0800 (10)0.0671 (9)0.0079 (7)0.0251 (7)0.0113 (8)
N1A0.0460 (8)0.0446 (8)0.0496 (8)0.0011 (6)0.0112 (6)0.0054 (6)
N2A0.0465 (8)0.0496 (9)0.0531 (8)0.0022 (6)0.0140 (6)0.0038 (7)
C1A0.0442 (9)0.0476 (10)0.0499 (10)0.0063 (7)0.0085 (7)0.0043 (8)
C2A0.0459 (9)0.0459 (9)0.0444 (9)0.0073 (7)0.0072 (7)0.0035 (7)
C3A0.0441 (9)0.0456 (9)0.0473 (9)0.0093 (7)0.0086 (7)0.0013 (7)
C4A0.0503 (10)0.0497 (11)0.0678 (12)0.0027 (8)0.0148 (9)0.0038 (9)
C5A0.0716 (14)0.0804 (16)0.0789 (15)0.0166 (12)0.0268 (12)0.0020 (12)
C6A0.0528 (10)0.0441 (10)0.0569 (11)0.0063 (7)0.0180 (8)0.0019 (8)
C7A0.0793 (14)0.0526 (11)0.0568 (11)0.0107 (10)0.0196 (10)0.0002 (9)
C8A0.120 (2)0.0578 (14)0.0723 (15)0.0062 (13)0.0473 (15)0.0048 (11)
C9A0.102 (2)0.0681 (16)0.117 (2)0.0136 (14)0.0672 (19)0.0055 (15)
C10A0.0606 (13)0.0802 (17)0.117 (2)0.0095 (12)0.0341 (14)0.0061 (16)
C11A0.0523 (11)0.0670 (13)0.0765 (14)0.0035 (9)0.0184 (10)0.0009 (11)
C12A0.0408 (9)0.0532 (11)0.0594 (11)0.0023 (7)0.0111 (8)0.0154 (9)
C13A0.0653 (12)0.0557 (12)0.0739 (13)0.0052 (9)0.0236 (10)0.0133 (10)
C14A0.0784 (15)0.0606 (14)0.110 (2)0.0170 (11)0.0371 (15)0.0281 (14)
C15A0.0543 (12)0.0872 (19)0.107 (2)0.0106 (11)0.0152 (12)0.0520 (16)
C16A0.0549 (12)0.112 (2)0.0703 (14)0.0170 (12)0.0035 (10)0.0390 (14)
C17A0.0577 (11)0.0716 (14)0.0615 (12)0.0158 (10)0.0061 (9)0.0159 (10)
C18A0.0694 (12)0.0529 (11)0.0495 (10)0.0108 (9)0.0067 (9)0.0096 (8)
C19A0.094 (2)0.140 (3)0.0670 (16)0.0335 (19)0.0079 (14)0.0078 (17)
C20A0.099 (3)0.213 (5)0.094 (3)0.040 (3)0.017 (2)0.004 (3)
C21A0.119 (3)0.136 (3)0.084 (2)0.040 (2)0.030 (2)0.020 (2)
C22A0.154 (3)0.0703 (17)0.0792 (19)0.0168 (19)0.028 (2)0.0070 (14)
C23A0.115 (2)0.0582 (14)0.0678 (15)0.0011 (13)0.0067 (14)0.0043 (11)
S1B0.0474 (2)0.0543 (3)0.0478 (3)0.00010 (19)0.00929 (18)0.00447 (19)
O1B0.0791 (10)0.0794 (11)0.0653 (9)0.0014 (8)0.0343 (8)0.0017 (8)
O2B0.0605 (8)0.0804 (11)0.0736 (10)0.0217 (7)0.0231 (7)0.0213 (8)
O3B0.0711 (9)0.0729 (10)0.0488 (8)0.0107 (7)0.0016 (6)0.0014 (7)
N1B0.0442 (7)0.0512 (9)0.0424 (7)0.0013 (6)0.0101 (6)0.0003 (6)
N2B0.0456 (8)0.0523 (9)0.0492 (8)0.0026 (6)0.0120 (6)0.0034 (7)
C1B0.0415 (8)0.0500 (10)0.0456 (9)0.0036 (7)0.0096 (7)0.0044 (7)
C2B0.0408 (8)0.0470 (10)0.0453 (9)0.0043 (7)0.0083 (7)0.0022 (7)
C3B0.0391 (8)0.0458 (9)0.0445 (9)0.0030 (7)0.0070 (7)0.0044 (7)
C4B0.0474 (9)0.0642 (12)0.0507 (10)0.0020 (8)0.0137 (8)0.0078 (9)
C5B0.0828 (16)0.0755 (15)0.0771 (15)0.0128 (12)0.0342 (13)0.0123 (12)
C6B0.0472 (9)0.0517 (10)0.0417 (9)0.0027 (7)0.0107 (7)0.0012 (7)
C7B0.0668 (12)0.0583 (12)0.0632 (12)0.0063 (9)0.0200 (10)0.0120 (10)
C8B0.114 (2)0.0614 (14)0.0675 (14)0.0050 (13)0.0299 (14)0.0164 (11)
C9B0.0913 (18)0.0945 (19)0.0668 (14)0.0345 (15)0.0312 (13)0.0069 (13)
C10B0.0548 (12)0.113 (2)0.0660 (14)0.0139 (12)0.0227 (10)0.0072 (13)
C11B0.0488 (10)0.0756 (14)0.0547 (11)0.0011 (9)0.0139 (8)0.0075 (10)
C12B0.0443 (9)0.0660 (12)0.0470 (10)0.0078 (8)0.0097 (7)0.0088 (8)
C13B0.0748 (14)0.0862 (16)0.0480 (11)0.0117 (12)0.0097 (10)0.0034 (10)
C14B0.0884 (17)0.135 (3)0.0470 (12)0.0330 (17)0.0173 (12)0.0137 (14)
C15B0.0750 (16)0.106 (2)0.0809 (18)0.0237 (15)0.0271 (13)0.0418 (16)
C16B0.0700 (14)0.0780 (16)0.0869 (18)0.0091 (12)0.0233 (12)0.0289 (13)
C17B0.0578 (11)0.0610 (13)0.0688 (13)0.0063 (9)0.0143 (10)0.0105 (10)
C18B0.0663 (12)0.0448 (10)0.0624 (12)0.0025 (8)0.0211 (9)0.0005 (9)
C19B0.1076 (19)0.0654 (15)0.0790 (16)0.0189 (13)0.0490 (15)0.0101 (12)
C20B0.156 (3)0.088 (2)0.125 (3)0.042 (2)0.088 (3)0.0128 (19)
C21B0.194 (4)0.102 (3)0.165 (4)0.089 (3)0.099 (4)0.041 (3)
C22B0.190 (4)0.089 (2)0.124 (3)0.071 (3)0.058 (3)0.040 (2)
C23B0.114 (2)0.0610 (14)0.0764 (15)0.0210 (13)0.0317 (15)0.0121 (12)
Geometric parameters (Å, º) top
S1A—O2A1.4239 (16)S1B—O2B1.4315 (16)
S1A—O3A1.4286 (16)S1B—O3B1.4322 (16)
S1A—C2A1.7550 (18)S1B—C2B1.7509 (18)
S1A—C18A1.766 (2)S1B—C18B1.766 (2)
O1A—C4A1.203 (3)O1B—C4B1.203 (3)
N1A—N2A1.347 (2)N1B—C3B1.353 (2)
N1A—C3A1.362 (2)N1B—N2B1.357 (2)
N1A—C12A1.434 (2)N1B—C12B1.436 (2)
N2A—C1A1.326 (2)N2B—C1B1.328 (2)
C1A—C2A1.424 (3)C1B—C2B1.421 (3)
C1A—C4A1.487 (3)C1B—C4B1.487 (2)
C2A—C3A1.384 (3)C2B—C3B1.381 (2)
C3A—C6A1.478 (3)C3B—C6B1.485 (2)
C4A—C5A1.498 (3)C4B—C5B1.491 (3)
C5A—H5AA0.9600C5B—H5BA0.9600
C5A—H5AB0.9600C5B—H5BB0.9600
C5A—H5AC0.9600C5B—H5BC0.9600
C6A—C11A1.384 (3)C6B—C11B1.379 (3)
C6A—C7A1.392 (3)C6B—C7B1.386 (3)
C7A—C8A1.377 (3)C7B—C8B1.384 (3)
C7A—H7AA0.9300C7B—H7BA0.9300
C8A—C9A1.374 (4)C8B—C9B1.383 (4)
C8A—H8AA0.9300C8B—H8BA0.9300
C9A—C10A1.375 (5)C9B—C10B1.364 (4)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—C11A1.381 (3)C10B—C11B1.380 (3)
C10A—H10A0.9300C10B—H10B0.9300
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.371 (3)C12B—C13B1.374 (3)
C12A—C17A1.376 (3)C12B—C17B1.382 (3)
C13A—C14A1.390 (3)C13B—C14B1.409 (4)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.364 (4)C14B—C15B1.365 (5)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.366 (4)C15B—C16B1.360 (4)
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.393 (3)C16B—C17B1.381 (3)
C16A—H16A0.9300C16B—H16B0.9300
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.354 (4)C18B—C23B1.366 (3)
C18A—C23A1.377 (3)C18B—C19B1.381 (3)
C19A—C20A1.394 (5)C19B—C20B1.374 (4)
C19A—H19A0.9300C19B—H19B0.9300
C20A—C21A1.352 (6)C20B—C21B1.354 (5)
C20A—H20A0.9300C20B—H20B0.9300
C21A—C22A1.351 (6)C21B—C22B1.384 (5)
C21A—H21A0.9300C21B—H21B0.9300
C22A—C23A1.379 (4)C22B—C23B1.380 (4)
C22A—H22A0.9300C22B—H22B0.9300
C23A—H23A0.9300C23B—H23B0.9300
O2A—S1A—O3A119.09 (10)O2B—S1B—O3B118.74 (10)
O2A—S1A—C2A107.69 (9)O2B—S1B—C2B106.86 (9)
O3A—S1A—C2A107.24 (9)O3B—S1B—C2B107.65 (9)
O2A—S1A—C18A107.91 (10)O2B—S1B—C18B107.10 (10)
O3A—S1A—C18A107.18 (10)O3B—S1B—C18B108.21 (10)
C2A—S1A—C18A107.20 (9)C2B—S1B—C18B107.85 (9)
N2A—N1A—C3A112.99 (14)C3B—N1B—N2B112.81 (14)
N2A—N1A—C12A117.96 (15)C3B—N1B—C12B128.97 (15)
C3A—N1A—C12A129.04 (15)N2B—N1B—C12B117.60 (15)
C1A—N2A—N1A105.78 (14)C1B—N2B—N1B105.25 (15)
N2A—C1A—C2A110.14 (16)N2B—C1B—C2B110.48 (15)
N2A—C1A—C4A117.29 (16)N2B—C1B—C4B118.93 (17)
C2A—C1A—C4A132.53 (18)C2B—C1B—C4B130.52 (17)
C3A—C2A—C1A105.76 (16)C3B—C2B—C1B105.55 (16)
C3A—C2A—S1A125.25 (14)C3B—C2B—S1B124.47 (14)
C1A—C2A—S1A128.18 (14)C1B—C2B—S1B127.93 (14)
N1A—C3A—C2A105.33 (15)N1B—C3B—C2B105.90 (15)
N1A—C3A—C6A121.10 (16)N1B—C3B—C6B123.22 (15)
C2A—C3A—C6A133.47 (17)C2B—C3B—C6B130.86 (17)
O1A—C4A—C1A121.15 (19)O1B—C4B—C1B120.27 (19)
O1A—C4A—C5A122.17 (19)O1B—C4B—C5B122.72 (19)
C1A—C4A—C5A116.68 (18)C1B—C4B—C5B117.02 (18)
C4A—C5A—H5AA109.5C4B—C5B—H5BA109.5
C4A—C5A—H5AB109.5C4B—C5B—H5BB109.5
H5AA—C5A—H5AB109.5H5BA—C5B—H5BB109.5
C4A—C5A—H5AC109.5C4B—C5B—H5BC109.5
H5AA—C5A—H5AC109.5H5BA—C5B—H5BC109.5
H5AB—C5A—H5AC109.5H5BB—C5B—H5BC109.5
C11A—C6A—C7A119.68 (19)C11B—C6B—C7B120.18 (19)
C11A—C6A—C3A119.30 (18)C11B—C6B—C3B119.87 (17)
C7A—C6A—C3A120.99 (18)C7B—C6B—C3B119.93 (16)
C8A—C7A—C6A119.7 (2)C8B—C7B—C6B119.5 (2)
C8A—C7A—H7AA120.1C8B—C7B—H7BA120.3
C6A—C7A—H7AA120.1C6B—C7B—H7BA120.3
C9A—C8A—C7A120.6 (2)C9B—C8B—C7B119.9 (2)
C9A—C8A—H8AA119.7C9B—C8B—H8BA120.1
C7A—C8A—H8AA119.7C7B—C8B—H8BA120.1
C8A—C9A—C10A119.7 (2)C10B—C9B—C8B120.3 (2)
C8A—C9A—H9AA120.1C10B—C9B—H9BA119.9
C10A—C9A—H9AA120.1C8B—C9B—H9BA119.9
C9A—C10A—C11A120.6 (3)C9B—C10B—C11B120.4 (2)
C9A—C10A—H10A119.7C9B—C10B—H10B119.8
C11A—C10A—H10A119.7C11B—C10B—H10B119.8
C10A—C11A—C6A119.6 (2)C6B—C11B—C10B119.7 (2)
C10A—C11A—H11A120.2C6B—C11B—H11B120.2
C6A—C11A—H11A120.2C10B—C11B—H11B120.2
C13A—C12A—C17A121.5 (2)C13B—C12B—C17B121.5 (2)
C13A—C12A—N1A120.07 (19)C13B—C12B—N1B121.0 (2)
C17A—C12A—N1A118.36 (19)C17B—C12B—N1B117.53 (18)
C12A—C13A—C14A118.8 (2)C12B—C13B—C14B117.3 (3)
C12A—C13A—H13A120.6C12B—C13B—H13B121.3
C14A—C13A—H13A120.6C14B—C13B—H13B121.3
C15A—C14A—C13A120.3 (3)C15B—C14B—C13B121.3 (3)
C15A—C14A—H14A119.9C15B—C14B—H14B119.3
C13A—C14A—H14A119.9C13B—C14B—H14B119.3
C14A—C15A—C16A120.5 (2)C16B—C15B—C14B119.9 (2)
C14A—C15A—H15A119.8C16B—C15B—H15B120.1
C16A—C15A—H15A119.8C14B—C15B—H15B120.1
C15A—C16A—C17A120.3 (3)C15B—C16B—C17B120.6 (3)
C15A—C16A—H16A119.8C15B—C16B—H16B119.7
C17A—C16A—H16A119.8C17B—C16B—H16B119.7
C12A—C17A—C16A118.5 (2)C16B—C17B—C12B119.3 (2)
C12A—C17A—H17A120.7C16B—C17B—H17B120.3
C16A—C17A—H17A120.7C12B—C17B—H17B120.3
C19A—C18A—C23A120.7 (2)C23B—C18B—C19B121.6 (2)
C19A—C18A—S1A120.0 (2)C23B—C18B—S1B119.67 (17)
C23A—C18A—S1A119.15 (19)C19B—C18B—S1B118.33 (18)
C18A—C19A—C20A119.2 (3)C20B—C19B—C18B119.3 (3)
C18A—C19A—H19A120.4C20B—C19B—H19B120.3
C20A—C19A—H19A120.4C18B—C19B—H19B120.3
C21A—C20A—C19A120.1 (4)C21B—C20B—C19B119.4 (3)
C21A—C20A—H20A120.0C21B—C20B—H20B120.3
C19A—C20A—H20A120.0C19B—C20B—H20B120.3
C22A—C21A—C20A120.4 (3)C20B—C21B—C22B121.6 (3)
C22A—C21A—H21A119.8C20B—C21B—H21B119.2
C20A—C21A—H21A119.8C22B—C21B—H21B119.2
C21A—C22A—C23A120.6 (3)C23B—C22B—C21B119.3 (3)
C21A—C22A—H22A119.7C23B—C22B—H22B120.3
C23A—C22A—H22A119.7C21B—C22B—H22B120.3
C18A—C23A—C22A118.9 (3)C18B—C23B—C22B118.7 (3)
C18A—C23A—H23A120.6C18B—C23B—H23B120.6
C22A—C23A—H23A120.6C22B—C23B—H23B120.6
C3A—N1A—N2A—C1A0.7 (2)C3B—N1B—N2B—C1B0.52 (19)
C12A—N1A—N2A—C1A179.55 (16)C12B—N1B—N2B—C1B172.29 (15)
N1A—N2A—C1A—C2A0.3 (2)N1B—N2B—C1B—C2B0.33 (19)
N1A—N2A—C1A—C4A177.81 (16)N1B—N2B—C1B—C4B177.02 (15)
N2A—C1A—C2A—C3A0.2 (2)N2B—C1B—C2B—C3B0.05 (19)
C4A—C1A—C2A—C3A177.90 (19)C4B—C1B—C2B—C3B176.91 (17)
N2A—C1A—C2A—S1A170.16 (14)N2B—C1B—C2B—S1B164.01 (13)
C4A—C1A—C2A—S1A12.1 (3)C4B—C1B—C2B—S1B19.0 (3)
O2A—S1A—C2A—C3A140.84 (17)O2B—S1B—C2B—C3B1.34 (18)
O3A—S1A—C2A—C3A11.55 (19)O3B—S1B—C2B—C3B129.93 (15)
C18A—S1A—C2A—C3A103.27 (17)C18B—S1B—C2B—C3B113.51 (16)
O2A—S1A—C2A—C1A27.3 (2)O2B—S1B—C2B—C1B159.94 (16)
O3A—S1A—C2A—C1A156.63 (17)O3B—S1B—C2B—C1B31.35 (18)
C18A—S1A—C2A—C1A88.55 (18)C18B—S1B—C2B—C1B85.21 (17)
N2A—N1A—C3A—C2A0.8 (2)N2B—N1B—C3B—C2B0.50 (19)
C12A—N1A—C3A—C2A179.49 (17)C12B—N1B—C3B—C2B171.11 (17)
N2A—N1A—C3A—C6A176.07 (16)N2B—N1B—C3B—C6B177.85 (15)
C12A—N1A—C3A—C6A2.6 (3)C12B—N1B—C3B—C6B7.2 (3)
C1A—C2A—C3A—N1A0.56 (19)C1B—C2B—C3B—N1B0.26 (18)
S1A—C2A—C3A—N1A170.93 (13)S1B—C2B—C3B—N1B165.03 (12)
C1A—C2A—C3A—C6A175.76 (19)C1B—C2B—C3B—C6B177.91 (17)
S1A—C2A—C3A—C6A5.4 (3)S1B—C2B—C3B—C6B13.1 (3)
N2A—C1A—C4A—O1A155.7 (2)N2B—C1B—C4B—O1B160.87 (19)
C2A—C1A—C4A—O1A21.9 (3)C2B—C1B—C4B—O1B15.9 (3)
N2A—C1A—C4A—C5A23.8 (3)N2B—C1B—C4B—C5B19.4 (3)
C2A—C1A—C4A—C5A158.6 (2)C2B—C1B—C4B—C5B163.9 (2)
N1A—C3A—C6A—C11A59.4 (2)N1B—C3B—C6B—C11B76.8 (2)
C2A—C3A—C6A—C11A116.5 (2)C2B—C3B—C6B—C11B101.1 (2)
N1A—C3A—C6A—C7A118.7 (2)N1B—C3B—C6B—C7B104.7 (2)
C2A—C3A—C6A—C7A65.5 (3)C2B—C3B—C6B—C7B77.4 (3)
C11A—C6A—C7A—C8A1.3 (3)C11B—C6B—C7B—C8B1.9 (3)
C3A—C6A—C7A—C8A179.28 (19)C3B—C6B—C7B—C8B176.5 (2)
C6A—C7A—C8A—C9A0.8 (4)C6B—C7B—C8B—C9B0.8 (4)
C7A—C8A—C9A—C10A0.4 (4)C7B—C8B—C9B—C10B2.9 (4)
C8A—C9A—C10A—C11A1.1 (4)C8B—C9B—C10B—C11B2.3 (4)
C9A—C10A—C11A—C6A0.6 (4)C7B—C6B—C11B—C10B2.6 (3)
C7A—C6A—C11A—C10A0.6 (3)C3B—C6B—C11B—C10B175.9 (2)
C3A—C6A—C11A—C10A178.6 (2)C9B—C10B—C11B—C6B0.5 (4)
N2A—N1A—C12A—C13A131.36 (19)C3B—N1B—C12B—C13B49.0 (3)
C3A—N1A—C12A—C13A50.0 (3)N2B—N1B—C12B—C13B140.82 (19)
N2A—N1A—C12A—C17A46.2 (2)C3B—N1B—C12B—C17B130.4 (2)
C3A—N1A—C12A—C17A132.4 (2)N2B—N1B—C12B—C17B39.8 (2)
C17A—C12A—C13A—C14A0.5 (3)C17B—C12B—C13B—C14B0.9 (3)
N1A—C12A—C13A—C14A178.02 (19)N1B—C12B—C13B—C14B178.5 (2)
C12A—C13A—C14A—C15A0.7 (3)C12B—C13B—C14B—C15B1.7 (4)
C13A—C14A—C15A—C16A0.5 (4)C13B—C14B—C15B—C16B0.8 (4)
C14A—C15A—C16A—C17A0.1 (4)C14B—C15B—C16B—C17B0.9 (4)
C13A—C12A—C17A—C16A0.2 (3)C15B—C16B—C17B—C12B1.6 (4)
N1A—C12A—C17A—C16A177.69 (18)C13B—C12B—C17B—C16B0.7 (3)
C15A—C16A—C17A—C12A0.0 (3)N1B—C12B—C17B—C16B179.91 (19)
O2A—S1A—C18A—C19A27.2 (3)O2B—S1B—C18B—C23B41.4 (2)
O3A—S1A—C18A—C19A156.6 (2)O3B—S1B—C18B—C23B170.6 (2)
C2A—S1A—C18A—C19A88.6 (3)C2B—S1B—C18B—C23B73.3 (2)
O2A—S1A—C18A—C23A149.70 (19)O2B—S1B—C18B—C19B131.2 (2)
O3A—S1A—C18A—C23A20.3 (2)O3B—S1B—C18B—C19B2.1 (2)
C2A—S1A—C18A—C23A94.6 (2)C2B—S1B—C18B—C19B114.1 (2)
C23A—C18A—C19A—C20A1.2 (5)C23B—C18B—C19B—C20B0.9 (5)
S1A—C18A—C19A—C20A178.0 (3)S1B—C18B—C19B—C20B173.4 (3)
C18A—C19A—C20A—C21A0.1 (7)C18B—C19B—C20B—C21B1.6 (6)
C19A—C20A—C21A—C22A1.7 (7)C19B—C20B—C21B—C22B2.2 (8)
C20A—C21A—C22A—C23A2.1 (6)C20B—C21B—C22B—C23B0.3 (9)
C19A—C18A—C23A—C22A0.8 (4)C19B—C18B—C23B—C22B2.8 (5)
S1A—C18A—C23A—C22A177.6 (2)S1B—C18B—C23B—C22B175.2 (3)
C21A—C22A—C23A—C18A0.8 (5)C21B—C22B—C23B—C18B2.2 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11A—H11A···O2Ai0.932.593.428 (3)149
C11B—H11B···O3Bii0.932.573.370 (3)144
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC23H18N2O3S
Mr402.45
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)10.4078 (2), 14.0839 (3), 14.2468 (3)
α, β, γ (°)87.595 (2), 80.875 (2), 86.850 (2)
V3)2057.62 (7)
Z4
Radiation typeCu Kα
µ (mm1)1.62
Crystal size (mm)0.66 × 0.55 × 0.17
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.415, 0.771
No. of measured, independent and
observed [I > 2σ(I)] reflections
19520, 6561, 5618
Rint0.029
(sin θ/λ)max1)0.583
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.123, 1.05
No. of reflections6561
No. of parameters525
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.31

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11A—H11A···O2Ai0.932.593.428 (3)149
C11B—H11B···O3Bii0.932.573.370 (3)144
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+2, z+1.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160).

References

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