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ISSN: 2056-9890

(1-Phenyl­sulfonyl-1H-indol-2-yl)(thio­phen-2-yl)methanone

aDepartment of Chemistry, AMET University, Kanathur, Chennai 603 112, India, bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and cDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: crystallography2010@gmail.com, phdguna@gmail.com

(Received 28 December 2010; accepted 15 February 2011; online 26 February 2011)

The crystal studied of the title compound, C19H13NO3S2, was found to be a non-merohedral twin with a domain ratio of 0.877 (3):0.123 (3). There are two independent mol­ecules in the asymmetric unit. The dihedral angles between the mean plane of the indole ring system and the phenyl­sulfonyl ring are 71.67 (13) and 71.95 (13)° in the two mol­ecules while the indole unit and the thiophene ring make dihedral angles of 54.91 (12) and 56.92 (13)° in the two molecules. The crystal packing is stabilized by weak C—H⋯π inter­actions.

Related literature

For biological activity of chromenopyrrole, see: Ma et al. (2001[Ma, C., Liu, X., Li, X., Flippen-Anderson, J., Yu, S. & Cook, J. M. (2001). J. Org. Chem. 66, 4525-4542.]); Zhao et al. (2002[Zhao, S., Liao, X. & Cook, J. M. (2002). Org. Lett. 4, 687-690.]); Zhou et al. (2006[Zhou, H., Liao, X., Yin, W., Ma, J. & Cook, J. M. (2006). J. Org. Chem. 71, 251-259.]); Rajeswaran et al. (1999[Rajeswaran, W. G., Labroo, R. B., Cohen, L. A. & King, M. M. (1999). J. Org. Chem. 64, 1369-1371.]); For related structures, see: Chakkaravarthi et al. (2007[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3673.]); Gunasekaran et al. (2009[Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o1856.]); Saravanan et al. (2010[Saravanan, B., Dhayalan, V., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2010). Acta Cryst. E66, o1509.]).

[Scheme 1]

Experimental

Crystal data
  • C19H13NO3S2

  • Mr = 367.42

  • Triclinic, [P \overline 1]

  • a = 9.3605 (5) Å

  • b = 10.8455 (5) Å

  • c = 17.5482 (9) Å

  • α = 88.716 (3)°

  • β = 80.425 (2)°

  • γ = 71.467 (2)°

  • V = 1664.68 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.34 mm−1

  • T = 295 K

  • 0.35 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.924, Tmax = 0.951

  • 36289 measured reflections

  • 8039 independent reflections

  • 6195 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.077

  • wR(F2) = 0.245

  • S = 1.07

  • 8039 reflections

  • 453 parameters

  • H-atom parameters constrained

  • Δρmax = 0.55 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C20–C25 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C17—H17⋯Cg8i 0.93 2.88 3.693 (6) 147
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Indole derivatives are found to possess anticancer, antimalarial and antihypertensive activities (Ma et al., 2001; Zhou et al., 2006; Zhao et al., 2002). In addition, Indoles have been proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure(Chakkaravarthi et al., 2007; Gunasekaran et al., 2009; Saravanan et al., 2010). The compound is non-merohedrally twinned, the suggested transformation matrix is (-1 0 0, 0 - 1 0, -0.664 0.110 1). The dihedral angle between the nine membered indole moiety and the thiophene ring is 54.91 (12) ° for molecule (I) and 56.92 (13) ° for molecule (II) respectively. The torsion angles O1—S1—N1—C1 and O2—S1—N1—C8 in molecule (I), O4—S3—N2—C20 and O5—S3—N2—C27 in molecule (II) [-9.8 (4) ° and 27.7 (4) ° for molecule (I), 9.1 (4) ° and -27.2 (4) ° for molecule (II), respectively] indicates the syn conformation of the sulfonyl moiety.

The sum of bond angles around N1 and N2 are 358.9 (3) ° and 358.6 (3) ° respectively, indicates the sp2 hybridization state of atoms N1 and N2. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak C—H···π [C17—H17···Cg8(1 - x, 1 - y, 1 - z) distance of 3.693 (6)Å (Cg8 is the centroid of the ring defined by the atoms C20—C25)] interactions.

Related literature top

For biological activity of chromenopyrrole, see: Ma et al. (2001); Zhao et al. (2002); Zhou et al. (2006); Rajeswaran et al. (1999); For related structures, see: Chakkaravarthi et al. (2007); Gunasekaran et al. (2009); Saravanan et al. (2010)

Experimental top

To a solution of N-(2-Formylphenyl)benzenesulfonamide (0.5 g, 1.91 mmol) in dry CH3CN (20 ml), K2CO3 (0.8 g, 5.79 mmol), 2-bromo-1-(thiophen-2-yl) ethanone (0.5 g, 2.43 mmol) were added. The reaction mixture was stirred at room temperature for 6 h under N2 atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml), extracted with chloroform (3 x 10 ml) and dried (Na2SO4). Removal of solvent followed by the residue was dissolved in CH3CN (20 ml), Conc.HCl (3 ml) was added. The reaction mixture was then refluxed for 2 h. It was then poured over ice-water (50 ml), extracted with CHCl3 (3 x 10 ml) and dried (Na2SO4). Removal of solvent followed by crystallization from methanol afforded the compound as a colorless crystal.

Refinement top

H atoms were positioned geometrically and refined using riding model with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
(1-Phenylsulfonyl-1H-indol-2-yl)(thiophen-2-yl)methanone top
Crystal data top
C19H13NO3S2Z = 4
Mr = 367.42F(000) = 760
Triclinic, P1Dx = 1.466 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3605 (5) ÅCell parameters from 6464 reflections
b = 10.8455 (5) Åθ = 2.4–27.8°
c = 17.5482 (9) ŵ = 0.34 mm1
α = 88.716 (3)°T = 295 K
β = 80.425 (2)°Block, colourless
γ = 71.467 (2)°0.35 × 0.25 × 0.20 mm
V = 1664.68 (15) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
8039 independent reflections
Radiation source: fine-focus sealed tube6195 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 0 pixels mm-1θmax = 28.0°, θmin = 1.2°
ω and ϕ scansh = 1212
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.924, Tmax = 0.951l = 2323
36289 measured reflections
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)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.245H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.092P)2 + 4.8598P]
where P = (Fo2 + 2Fc2)/3
8039 reflections(Δ/σ)max < 0.001
453 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C19H13NO3S2γ = 71.467 (2)°
Mr = 367.42V = 1664.68 (15) Å3
Triclinic, P1Z = 4
a = 9.3605 (5) ÅMo Kα radiation
b = 10.8455 (5) ŵ = 0.34 mm1
c = 17.5482 (9) ÅT = 295 K
α = 88.716 (3)°0.35 × 0.25 × 0.20 mm
β = 80.425 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
8039 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
6195 reflections with I > 2σ(I)
Tmin = 0.924, Tmax = 0.951Rint = 0.040
36289 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0770 restraints
wR(F2) = 0.245H-atom parameters constrained
S = 1.07Δρmax = 0.55 e Å3
8039 reflectionsΔρmin = 0.37 e Å3
453 parameters
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.

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 > σ(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
C10.4481 (5)0.1880 (4)0.3523 (2)0.0356 (8)
C20.3808 (6)0.3165 (4)0.3334 (3)0.0465 (10)
H20.43090.37810.33320.056*
C30.2370 (6)0.3476 (5)0.3150 (3)0.0538 (12)
H30.18890.43260.30210.065*
C40.1597 (6)0.2562 (5)0.3149 (3)0.0565 (13)
H40.06140.28160.30310.068*
C50.2277 (5)0.1307 (5)0.3320 (3)0.0504 (11)
H50.17680.06980.33140.061*
C60.3763 (5)0.0933 (4)0.3507 (3)0.0404 (9)
C70.4734 (5)0.0266 (4)0.3714 (3)0.0431 (10)
H70.45270.10510.37360.052*
C80.6014 (5)0.0084 (4)0.3877 (3)0.0376 (9)
C90.7171 (5)0.0981 (4)0.4277 (3)0.0380 (9)
C100.7561 (5)0.2365 (4)0.4090 (2)0.0366 (8)
C110.7462 (5)0.2983 (4)0.3425 (3)0.0408 (9)
H110.70740.25530.30030.049*
C120.8028 (6)0.4352 (5)0.3473 (3)0.0530 (12)
H120.80710.49300.30800.064*
C130.8501 (6)0.4731 (5)0.4156 (3)0.0561 (13)
H130.88800.55970.42850.067*
C140.7289 (5)0.2305 (4)0.4700 (3)0.0383 (9)
C150.8555 (5)0.1793 (5)0.5050 (3)0.0493 (11)
H150.94340.11910.47850.059*
C160.8498 (6)0.2187 (5)0.5801 (3)0.0552 (12)
H160.93350.18300.60490.066*
C170.7217 (6)0.3102 (5)0.6184 (3)0.0537 (12)
H170.71900.33730.66870.064*
C180.5971 (6)0.3618 (5)0.5823 (3)0.0493 (11)
H180.51040.42380.60860.059*
C190.5985 (5)0.3231 (4)0.5072 (3)0.0442 (10)
H190.51430.35830.48280.053*
N10.5908 (4)0.1243 (3)0.3762 (2)0.0371 (7)
O20.8724 (4)0.0828 (4)0.3479 (2)0.0562 (9)
O10.6943 (5)0.3007 (4)0.3310 (2)0.0583 (9)
O30.7730 (4)0.0590 (3)0.4761 (2)0.0539 (9)
S10.73502 (13)0.18488 (11)0.37382 (7)0.0413 (3)
S20.83327 (16)0.34647 (13)0.47492 (8)0.0544 (3)
C200.3630 (5)0.6980 (4)0.1576 (2)0.0421 (9)
C210.2888 (7)0.8279 (5)0.1809 (3)0.0569 (13)
H210.34250.88670.18150.068*
C220.1326 (7)0.8653 (5)0.2032 (3)0.0645 (15)
H220.08010.95190.21800.077*
C230.0509 (6)0.7792 (6)0.2043 (3)0.0642 (15)
H230.05420.80780.22120.077*
C240.1237 (6)0.6514 (6)0.1808 (3)0.0575 (13)
H240.06840.59380.18070.069*
C250.2827 (5)0.6092 (5)0.1569 (3)0.0448 (10)
C260.3888 (5)0.4867 (4)0.1316 (3)0.0440 (10)
H260.36600.40970.12810.053*
C270.5280 (5)0.5000 (4)0.1135 (3)0.0408 (9)
C280.6673 (5)0.4060 (4)0.0691 (3)0.0418 (9)
C290.6939 (5)0.2679 (4)0.0865 (3)0.0408 (9)
C300.6482 (6)0.2140 (5)0.1540 (3)0.0525 (12)
H300.58640.26200.19740.063*
C310.7070 (8)0.0763 (6)0.1495 (4)0.0739 (17)
H310.68790.02280.18940.089*
C320.7944 (7)0.0321 (5)0.0798 (5)0.0729 (18)
H320.84150.05580.06660.087*
C330.7163 (5)0.7268 (4)0.0347 (3)0.0405 (9)
C340.8649 (6)0.6794 (5)0.0023 (3)0.0543 (12)
H340.93820.62080.02210.065*
C350.9052 (7)0.7184 (6)0.0750 (4)0.0673 (15)
H351.00550.68520.10060.081*
C360.7982 (8)0.8063 (6)0.1101 (3)0.0643 (15)
H360.82640.83340.15940.077*
C370.6495 (7)0.8549 (5)0.0735 (3)0.0593 (13)
H370.57720.91440.09790.071*
C380.6077 (6)0.8155 (5)0.0007 (3)0.0500 (11)
H380.50710.84830.02450.060*
N20.5175 (4)0.6304 (3)0.1284 (2)0.0415 (8)
O40.6061 (5)0.8001 (4)0.1772 (2)0.0609 (10)
O50.7862 (4)0.5782 (4)0.1510 (2)0.0586 (9)
O60.7506 (4)0.4410 (3)0.0187 (2)0.0563 (9)
S30.66525 (14)0.68399 (12)0.13007 (7)0.0450 (3)
S40.80927 (17)0.15141 (14)0.01948 (9)0.0630 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.038 (2)0.033 (2)0.034 (2)0.0084 (16)0.0079 (16)0.0043 (15)
C20.052 (3)0.034 (2)0.048 (3)0.0044 (18)0.009 (2)0.0024 (18)
C30.054 (3)0.043 (3)0.051 (3)0.004 (2)0.012 (2)0.006 (2)
C40.043 (3)0.065 (3)0.053 (3)0.001 (2)0.016 (2)0.005 (2)
C50.037 (2)0.055 (3)0.060 (3)0.012 (2)0.015 (2)0.000 (2)
C60.038 (2)0.038 (2)0.046 (2)0.0112 (17)0.0076 (17)0.0050 (18)
C70.043 (2)0.034 (2)0.056 (3)0.0142 (18)0.0142 (19)0.0015 (19)
C80.037 (2)0.0271 (19)0.048 (2)0.0079 (15)0.0099 (17)0.0018 (16)
C90.035 (2)0.036 (2)0.042 (2)0.0094 (16)0.0083 (16)0.0012 (17)
C100.038 (2)0.0288 (19)0.043 (2)0.0084 (15)0.0103 (17)0.0036 (16)
C110.043 (2)0.030 (2)0.048 (2)0.0081 (17)0.0082 (18)0.0000 (17)
C120.053 (3)0.035 (2)0.067 (3)0.007 (2)0.012 (2)0.006 (2)
C130.051 (3)0.034 (2)0.080 (4)0.009 (2)0.012 (2)0.013 (2)
C140.040 (2)0.032 (2)0.046 (2)0.0149 (17)0.0091 (17)0.0033 (17)
C150.037 (2)0.055 (3)0.057 (3)0.0115 (19)0.012 (2)0.005 (2)
C160.053 (3)0.057 (3)0.062 (3)0.018 (2)0.025 (2)0.002 (2)
C170.067 (3)0.053 (3)0.050 (3)0.029 (2)0.014 (2)0.002 (2)
C180.048 (3)0.042 (2)0.055 (3)0.012 (2)0.004 (2)0.012 (2)
C190.038 (2)0.037 (2)0.056 (3)0.0097 (17)0.0105 (19)0.0022 (19)
N10.0380 (17)0.0296 (16)0.046 (2)0.0119 (14)0.0123 (15)0.0019 (14)
O20.0428 (18)0.064 (2)0.058 (2)0.0176 (16)0.0042 (15)0.0177 (17)
O10.075 (2)0.056 (2)0.059 (2)0.0395 (19)0.0159 (18)0.0106 (17)
O30.060 (2)0.0457 (18)0.059 (2)0.0120 (16)0.0263 (17)0.0055 (15)
S10.0414 (6)0.0411 (6)0.0455 (6)0.0193 (4)0.0053 (4)0.0028 (4)
S20.0567 (7)0.0483 (7)0.0547 (7)0.0088 (5)0.0171 (6)0.0126 (5)
C200.048 (2)0.040 (2)0.033 (2)0.0095 (18)0.0001 (17)0.0041 (17)
C210.064 (3)0.039 (2)0.055 (3)0.009 (2)0.008 (2)0.003 (2)
C220.062 (3)0.045 (3)0.064 (3)0.005 (2)0.010 (3)0.000 (2)
C230.047 (3)0.063 (3)0.063 (3)0.000 (2)0.009 (2)0.010 (3)
C240.041 (3)0.064 (3)0.064 (3)0.016 (2)0.002 (2)0.010 (3)
C250.042 (2)0.045 (2)0.047 (2)0.0137 (19)0.0083 (19)0.0121 (19)
C260.048 (2)0.037 (2)0.047 (2)0.0145 (19)0.0047 (19)0.0015 (18)
C270.043 (2)0.036 (2)0.042 (2)0.0111 (17)0.0076 (18)0.0010 (17)
C280.040 (2)0.043 (2)0.041 (2)0.0105 (18)0.0063 (17)0.0031 (18)
C290.040 (2)0.033 (2)0.045 (2)0.0063 (17)0.0058 (17)0.0075 (17)
C300.061 (3)0.040 (2)0.049 (3)0.006 (2)0.006 (2)0.001 (2)
C310.073 (4)0.044 (3)0.097 (5)0.010 (3)0.012 (3)0.012 (3)
C320.058 (3)0.039 (3)0.115 (5)0.006 (2)0.013 (3)0.015 (3)
C330.043 (2)0.040 (2)0.043 (2)0.0207 (18)0.0083 (18)0.0027 (18)
C340.043 (2)0.059 (3)0.059 (3)0.015 (2)0.005 (2)0.001 (2)
C350.059 (3)0.074 (4)0.067 (4)0.027 (3)0.009 (3)0.001 (3)
C360.085 (4)0.066 (4)0.048 (3)0.037 (3)0.002 (3)0.006 (3)
C370.071 (4)0.053 (3)0.060 (3)0.021 (3)0.027 (3)0.016 (2)
C380.046 (2)0.052 (3)0.054 (3)0.016 (2)0.011 (2)0.005 (2)
N20.0423 (19)0.0351 (18)0.044 (2)0.0114 (15)0.0004 (15)0.0031 (15)
O40.076 (3)0.058 (2)0.055 (2)0.0302 (19)0.0089 (18)0.0104 (17)
O50.055 (2)0.064 (2)0.061 (2)0.0171 (17)0.0240 (17)0.0103 (18)
O60.055 (2)0.051 (2)0.054 (2)0.0133 (16)0.0062 (16)0.0019 (16)
S30.0491 (6)0.0461 (6)0.0439 (6)0.0193 (5)0.0107 (5)0.0003 (5)
S40.0559 (8)0.0545 (8)0.0683 (9)0.0081 (6)0.0023 (6)0.0222 (7)
Geometric parameters (Å, º) top
C1—C21.393 (6)C20—C211.394 (6)
C1—C61.398 (6)C20—C251.399 (7)
C1—N11.423 (5)C20—N21.410 (6)
C2—C31.371 (7)C21—C221.377 (8)
C2—H20.9300C21—H210.9300
C3—C41.401 (8)C22—C231.381 (9)
C3—H30.9300C22—H220.9300
C4—C51.357 (7)C23—C241.373 (8)
C4—H40.9300C23—H230.9300
C5—C61.411 (6)C24—C251.403 (7)
C5—H50.9300C24—H240.9300
C6—C71.409 (6)C25—C261.410 (6)
C7—C81.350 (6)C26—C271.342 (6)
C7—H70.9300C26—H260.9300
C8—N11.422 (5)C27—N21.414 (6)
C8—C91.472 (6)C27—C281.483 (6)
C9—O31.216 (5)C28—O61.216 (6)
C9—C101.458 (6)C28—C291.472 (6)
C10—C111.390 (6)C29—C301.373 (7)
C10—S21.717 (4)C29—S41.710 (4)
C11—C121.415 (6)C30—C311.417 (7)
C11—H110.9300C30—H300.9300
C12—C131.357 (8)C31—C321.356 (10)
C12—H120.9300C31—H310.9300
C13—S21.693 (6)C32—S41.678 (7)
C13—H130.9300C32—H320.9300
C14—C151.378 (6)C33—C341.371 (7)
C14—C191.382 (6)C33—C381.381 (7)
C14—S11.757 (4)C33—S31.757 (5)
C15—C161.382 (7)C34—C351.367 (8)
C15—H150.9300C34—H340.9300
C16—C171.371 (8)C35—C361.365 (9)
C16—H160.9300C35—H350.9300
C17—C181.375 (7)C36—C371.372 (9)
C17—H170.9300C36—H360.9300
C18—C191.388 (7)C37—C381.371 (8)
C18—H180.9300C37—H370.9300
C19—H190.9300C38—H380.9300
N1—S11.674 (3)N2—S31.666 (4)
O2—S11.417 (4)O4—S31.423 (4)
O1—S11.427 (4)O5—S31.424 (4)
C2—C1—C6122.4 (4)C21—C20—C25121.7 (5)
C2—C1—N1131.5 (4)C21—C20—N2131.5 (5)
C6—C1—N1106.1 (3)C25—C20—N2106.8 (4)
C3—C2—C1116.7 (5)C22—C21—C20117.1 (5)
C3—C2—H2121.7C22—C21—H21121.5
C1—C2—H2121.7C20—C21—H21121.5
C2—C3—C4122.5 (5)C21—C22—C23122.4 (5)
C2—C3—H3118.7C21—C22—H22118.8
C4—C3—H3118.7C23—C22—H22118.8
C5—C4—C3120.2 (5)C24—C23—C22120.5 (5)
C5—C4—H4119.9C24—C23—H23119.8
C3—C4—H4119.9C22—C23—H23119.8
C4—C5—C6119.5 (5)C23—C24—C25119.0 (5)
C4—C5—H5120.2C23—C24—H24120.5
C6—C5—H5120.2C25—C24—H24120.5
C1—C6—C7109.0 (4)C20—C25—C24119.3 (5)
C1—C6—C5118.6 (4)C20—C25—C26108.2 (4)
C7—C6—C5132.3 (4)C24—C25—C26132.5 (5)
C8—C7—C6108.6 (4)C27—C26—C25108.4 (4)
C8—C7—H7125.7C27—C26—H26125.8
C6—C7—H7125.7C25—C26—H26125.8
C7—C8—N1108.6 (4)C26—C27—N2109.3 (4)
C7—C8—C9126.8 (4)C26—C27—C28127.3 (4)
N1—C8—C9123.1 (4)N2—C27—C28122.2 (4)
O3—C9—C10121.8 (4)O6—C28—C29122.1 (4)
O3—C9—C8121.5 (4)O6—C28—C27121.6 (4)
C10—C9—C8116.7 (4)C29—C28—C27116.2 (4)
C11—C10—C9129.9 (4)C30—C29—C28129.0 (4)
C11—C10—S2111.6 (3)C30—C29—S4111.7 (3)
C9—C10—S2118.4 (3)C28—C29—S4119.1 (3)
C10—C11—C12111.2 (4)C29—C30—C31111.7 (5)
C10—C11—H11124.4C29—C30—H30124.1
C12—C11—H11124.4C31—C30—H30124.1
C13—C12—C11112.6 (5)C32—C31—C30111.7 (6)
C13—C12—H12123.7C32—C31—H31124.2
C11—C12—H12123.7C30—C31—H31124.2
C12—C13—S2113.1 (4)C31—C32—S4113.5 (4)
C12—C13—H13123.5C31—C32—H32123.3
S2—C13—H13123.5S4—C32—H32123.3
C15—C14—C19121.7 (4)C34—C33—C38120.3 (5)
C15—C14—S1119.8 (4)C34—C33—S3120.2 (4)
C19—C14—S1118.4 (3)C38—C33—S3119.3 (4)
C14—C15—C16119.0 (5)C35—C34—C33119.9 (5)
C14—C15—H15120.5C35—C34—H34120.1
C16—C15—H15120.5C33—C34—H34120.1
C17—C16—C15120.5 (5)C36—C35—C34120.0 (5)
C17—C16—H16119.8C36—C35—H35120.0
C15—C16—H16119.8C34—C35—H35120.0
C16—C17—C18119.9 (5)C35—C36—C37120.6 (5)
C16—C17—H17120.1C35—C36—H36119.7
C18—C17—H17120.1C37—C36—H36119.7
C17—C18—C19121.1 (5)C38—C37—C36119.9 (5)
C17—C18—H18119.4C38—C37—H37120.1
C19—C18—H18119.4C36—C37—H37120.1
C14—C19—C18117.9 (4)C37—C38—C33119.4 (5)
C14—C19—H19121.1C37—C38—H38120.3
C18—C19—H19121.1C33—C38—H38120.3
C8—N1—C1107.6 (3)C20—N2—C27107.2 (4)
C8—N1—S1125.1 (3)C20—N2—S3126.1 (3)
C1—N1—S1126.2 (3)C27—N2—S3125.3 (3)
O2—S1—O1120.2 (2)O4—S3—O5119.6 (2)
O2—S1—N1107.27 (19)O4—S3—N2105.7 (2)
O1—S1—N1105.2 (2)O5—S3—N2107.4 (2)
O2—S1—C14109.9 (2)O4—S3—C33108.0 (2)
O1—S1—C14107.8 (2)O5—S3—C33109.9 (2)
N1—S1—C14105.41 (19)N2—S3—C33105.2 (2)
C13—S2—C1091.4 (2)C32—S4—C2991.5 (3)
C6—C1—C2—C31.9 (7)C25—C20—C21—C220.3 (8)
N1—C1—C2—C3177.6 (4)N2—C20—C21—C22176.6 (5)
C1—C2—C3—C40.0 (7)C20—C21—C22—C231.4 (9)
C2—C3—C4—C51.3 (8)C21—C22—C23—C241.9 (10)
C3—C4—C5—C60.7 (8)C22—C23—C24—C251.2 (9)
C2—C1—C6—C7179.1 (4)C21—C20—C25—C240.4 (7)
N1—C1—C6—C71.2 (5)N2—C20—C25—C24177.9 (4)
C2—C1—C6—C52.5 (7)C21—C20—C25—C26179.3 (5)
N1—C1—C6—C5177.2 (4)N2—C20—C25—C263.2 (5)
C4—C5—C6—C11.2 (7)C23—C24—C25—C200.1 (8)
C4—C5—C6—C7179.1 (5)C23—C24—C25—C26178.5 (5)
C1—C6—C7—C81.4 (5)C20—C25—C26—C273.0 (5)
C5—C6—C7—C8176.6 (5)C24—C25—C26—C27178.3 (5)
C6—C7—C8—N11.1 (5)C25—C26—C27—N21.5 (5)
C6—C7—C8—C9165.5 (4)C25—C26—C27—C28165.7 (4)
C7—C8—C9—O3138.0 (5)C26—C27—C28—O6135.6 (5)
N1—C8—C9—O326.8 (7)N2—C27—C28—O630.2 (7)
C7—C8—C9—C1039.3 (7)C26—C27—C28—C2941.2 (7)
N1—C8—C9—C10155.9 (4)N2—C27—C28—C29153.0 (4)
O3—C9—C10—C11157.1 (5)O6—C28—C29—C30155.8 (5)
C8—C9—C10—C1125.6 (7)C27—C28—C29—C3027.5 (7)
O3—C9—C10—S220.2 (6)O6—C28—C29—S418.3 (6)
C8—C9—C10—S2157.1 (3)C27—C28—C29—S4158.4 (3)
C9—C10—C11—C12177.3 (4)C28—C29—C30—C31175.4 (5)
S2—C10—C11—C120.1 (5)S4—C29—C30—C310.9 (6)
C10—C11—C12—C131.1 (6)C29—C30—C31—C320.4 (8)
C11—C12—C13—S21.7 (6)C30—C31—C32—S40.4 (8)
C19—C14—C15—C162.0 (7)C38—C33—C34—C351.1 (8)
S1—C14—C15—C16178.4 (4)S3—C33—C34—C35176.6 (4)
C14—C15—C16—C171.8 (8)C33—C34—C35—C361.2 (9)
C15—C16—C17—C180.9 (8)C34—C35—C36—C370.8 (9)
C16—C17—C18—C190.1 (8)C35—C36—C37—C380.3 (9)
C15—C14—C19—C181.2 (7)C36—C37—C38—C330.2 (8)
S1—C14—C19—C18177.7 (4)C34—C33—C38—C370.5 (7)
C17—C18—C19—C140.3 (7)S3—C33—C38—C37176.2 (4)
C7—C8—N1—C10.3 (5)C21—C20—N2—C27179.5 (5)
C9—C8—N1—C1166.9 (4)C25—C20—N2—C272.3 (5)
C7—C8—N1—S1168.3 (3)C21—C20—N2—S313.4 (7)
C9—C8—N1—S124.5 (6)C25—C20—N2—S3169.5 (3)
C2—C1—N1—C8179.8 (5)C26—C27—N2—C200.5 (5)
C6—C1—N1—C80.6 (5)C28—C27—N2—C20168.5 (4)
C2—C1—N1—S111.4 (7)C26—C27—N2—S3167.8 (3)
C6—C1—N1—S1169.0 (3)C28—C27—N2—S324.2 (6)
C8—N1—S1—O227.6 (4)C20—N2—S3—O49.0 (4)
C1—N1—S1—O2138.9 (4)C27—N2—S3—O4156.0 (4)
C8—N1—S1—O1156.7 (4)C20—N2—S3—O5137.7 (4)
C1—N1—S1—O19.8 (4)C27—N2—S3—O527.2 (4)
C8—N1—S1—C1489.5 (4)C20—N2—S3—C33105.2 (4)
C1—N1—S1—C14104.0 (4)C27—N2—S3—C3389.9 (4)
C15—C14—S1—O27.8 (4)C34—C33—S3—O4119.1 (4)
C19—C14—S1—O2175.7 (3)C38—C33—S3—O456.5 (4)
C15—C14—S1—O1125.0 (4)C34—C33—S3—O513.0 (5)
C19—C14—S1—O151.6 (4)C38—C33—S3—O5171.3 (4)
C15—C14—S1—N1123.1 (4)C34—C33—S3—N2128.4 (4)
C19—C14—S1—N160.4 (4)C38—C33—S3—N256.0 (4)
C12—C13—S2—C101.4 (4)C31—C32—S4—C290.8 (5)
C11—C10—S2—C130.7 (4)C30—C29—S4—C321.0 (4)
C9—C10—S2—C13178.5 (4)C28—C29—S4—C32176.1 (4)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C20–C25 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.332.879 (6)117
C15—H15···O20.932.562.932 (6)104
C21—H21···O40.932.332.878 (7)117
C34—H34···O50.932.582.950 (7)104
C17—H17···Cg8i0.932.883.693 (6)147
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC19H13NO3S2
Mr367.42
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)9.3605 (5), 10.8455 (5), 17.5482 (9)
α, β, γ (°)88.716 (3), 80.425 (2), 71.467 (2)
V3)1664.68 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.34
Crystal size (mm)0.35 × 0.25 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.924, 0.951
No. of measured, independent and
observed [I > 2σ(I)] reflections
36289, 8039, 6195
Rint0.040
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.077, 0.245, 1.07
No. of reflections8039
No. of parameters453
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.55, 0.37

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C20–C25 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.332.879 (6)117
C15—H15···O20.932.562.932 (6)104
C21—H21···O40.932.332.878 (7)117
C34—H34···O50.932.582.950 (7)104
C17—H17···Cg8i0.932.883.693 (6)147
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

CK thanks AMET University management for their kind support.

References

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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhao, S., Liao, X. & Cook, J. M. (2002). Org. Lett. 4, 687–690.  Web of Science CrossRef PubMed CAS Google Scholar
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