organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

5-Methyl-12-phenyl­sulfonyl-12H-naphtho­[1,2-b]carbazole

aDepartment of Chemistry, Madras Christian College (Autonomous), Chennai 600 059, Tamil Nadu, India
*Correspondence e-mail: rjkmcc@yahoo.com

(Received 6 November 2011; accepted 19 November 2011; online 30 November 2011)

In the title compound, C27H19NO2S, the naphtho­carbazole unit is approximately planar (r.m.s. deviation = 0.002 Å) except for the N atom, which is displaced by 0.122 (1) Å out of the mean plane. The dihedral angle between the naphtho­carbazole mean plane and the phenyl ring of the phenyl­sulfonyl substituent is 83.16 (3)°. An inter­molecular C—H⋯π inter­action involving the phenyl group and the pyrrole ring is observed in the crystal structure.

Related literature

For the biological activity of indole and carbazole derivatives see: Chai et al. (2006[Chai, H., Zhao, Y., Zhao, C. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911-917.]); Rani et al. (2004[Rani, P., Srivastava, V. K. & Kumar, A. (2004). Eur. J. Med. Chem. 39, 449-452.]); Panwar et al. (2006[Panwar, H., Verma, R. S., Srivastava, V. K. & Kumar, A. (2006). Indian J. Chem. Sect. B, 45, 2099-2104.]); Abele et al. (2003[Abele, E., Abele, R., Dzenitis, O. & Lukevics, E. (2003). Chem. Heterocycl. Compd, 39, 3-35.]). For related structures see: Chakkaravarthi et al. (2007[Chakkaravarthi, G., Ramesh, N., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3564.]); Liu et al. (2007[Liu, Y., Gribble, G. W. & Jasinski, J. P. (2007). Acta Cryst. E63, o738-o740.]).

[Scheme 1]

Experimental

Crystal data
  • C27H19NO2S

  • Mr = 421.49

  • Triclinic, [P \overline 1]

  • a = 9.4527 (3) Å

  • b = 10.7457 (3) Å

  • c = 11.5791 (3) Å

  • α = 115.592 (1)°

  • β = 93.324 (2)°

  • γ = 105.206 (2)°

  • V = 1003.61 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 295 K

  • 0.30 × 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 = 0.946, Tmax = 0.964

  • 23737 measured reflections

  • 5360 independent reflections

  • 4477 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.120

  • S = 1.05

  • 5360 reflections

  • 281 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyrrole ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C25—H25⋯Cg1i 0.93 2.61 3.4770 (2) 156
Symmetry code: (i) -x, -y, -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

Heterocyclic compounds containing pyrrole ring with benzene ring fused to α,β-position with π electrons and lone pair from the nitrogen atom are biologically accepted pharmacophore in medicinal compounds and possesses a wide spectrum of biological activities (Chai et al., 2006). Biological activity includes anticancer, anti-inflammatory (Rani et al., 2004), analgesic, antimicrobial (Panwar et al., 2006) and antifungal (Abele et al., 2003) properties.

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structures (Chakkaravarthi et al., 2007; Liu et al., 2007). The naphtho-carbazole moiety is planar except that the nitrogen atom N1 is 0.122 Å out of the mean plane. Dihedral angle between the mean plane of the naphtho-carbazole moiety and the phenyl group is 83.16 (3)°. The geometry of bonding of sulfur atom is tetrahedral except that angle O1—S1—O2 is 120.40 (6)°. There is a C—H···π interaction between the five membered ring (C1, C6, C7, C8 and N1) and H25i (symmetry code: i = -x, -y, 1 - z) of the phenyl ring. The separation between the H atom and the centroid of the five membered ring is 2.61 Å.

Related literature top

For the biological activity of indole and carbazole derivatives see: Chai et al. (2006); Rani et al. (2004); Panwar et al. (2006); Abele et al. (2003). For related structures see: Chakkaravarthi et al. (2007); Liu et al. (2007).

Experimental top

To a solution of diethyl-2-((bromomethyl-1-(phenylsulfonyl)-1H- indole-3-yl)methylene)malonate (0.2 g, 0.38 mmol) in dry 1,2-DCE (10 ml), ZnBr2 (0.17 g, 0.75 mmol) and 1-methylnaphthalene (0.06 ml, 0.42 mmol) were added. The reaction mixture was then refluxed for 1 h under nitrogen atmosphere. It was then poured over ice-water (50 ml) containing 2 ml of conc. HCl, extracted with chloroform (3 × 10 ml) and dried over Na2SO4. The removal of solvent followed by flash column chromatographic purification (silica gel, 230–420 mesh, n-hexane/ethyl acetate 96:4) afforded the title carbazole as a colourless solid. Recrystallization was done using CDCl3 as solvent.

Refinement top

H atoms were positioned geometrically and refined using the riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic CH, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for the methyl group.

Structure description top

Heterocyclic compounds containing pyrrole ring with benzene ring fused to α,β-position with π electrons and lone pair from the nitrogen atom are biologically accepted pharmacophore in medicinal compounds and possesses a wide spectrum of biological activities (Chai et al., 2006). Biological activity includes anticancer, anti-inflammatory (Rani et al., 2004), analgesic, antimicrobial (Panwar et al., 2006) and antifungal (Abele et al., 2003) properties.

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structures (Chakkaravarthi et al., 2007; Liu et al., 2007). The naphtho-carbazole moiety is planar except that the nitrogen atom N1 is 0.122 Å out of the mean plane. Dihedral angle between the mean plane of the naphtho-carbazole moiety and the phenyl group is 83.16 (3)°. The geometry of bonding of sulfur atom is tetrahedral except that angle O1—S1—O2 is 120.40 (6)°. There is a C—H···π interaction between the five membered ring (C1, C6, C7, C8 and N1) and H25i (symmetry code: i = -x, -y, 1 - z) of the phenyl ring. The separation between the H atom and the centroid of the five membered ring is 2.61 Å.

For the biological activity of indole and carbazole derivatives see: Chai et al. (2006); Rani et al. (2004); Panwar et al. (2006); Abele et al. (2003). For related structures see: Chakkaravarthi et al. (2007); Liu et al. (2007).

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 30% probability displacement ellipsoids for non-H atoms.
5-Methyl-12-phenylsulfonyl-12H-naphtho[1,2-b]carbazole top
Crystal data top
C27H19NO2SZ = 2
Mr = 421.49F(000) = 440
Triclinic, P1Dx = 1.395 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4527 (3) ÅCell parameters from 6046 reflections
b = 10.7457 (3) Åθ = 2.2–29.0°
c = 11.5791 (3) ŵ = 0.19 mm1
α = 115.592 (1)°T = 295 K
β = 93.324 (2)°Prism, colourless
γ = 105.206 (2)°0.30 × 0.25 × 0.20 mm
V = 1003.61 (5) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5360 independent reflections
Radiation source: fine-focus sealed tube4477 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 0 pixels mm-1θmax = 29.1°, θmin = 2.2°
ω and φ scansh = 1212
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.946, Tmax = 0.964l = 1515
23737 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0679P)2 + 0.1767P]
where P = (Fo2 + 2Fc2)/3
5360 reflections(Δ/σ)max < 0.001
281 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C27H19NO2Sγ = 105.206 (2)°
Mr = 421.49V = 1003.61 (5) Å3
Triclinic, P1Z = 2
a = 9.4527 (3) ÅMo Kα radiation
b = 10.7457 (3) ŵ = 0.19 mm1
c = 11.5791 (3) ÅT = 295 K
α = 115.592 (1)°0.30 × 0.25 × 0.20 mm
β = 93.324 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5360 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4477 reflections with I > 2σ(I)
Tmin = 0.946, Tmax = 0.964Rint = 0.027
23737 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.05Δρmax = 0.38 e Å3
5360 reflectionsΔρmin = 0.29 e Å3
281 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.18888 (14)0.24807 (14)0.29115 (12)0.0353 (3)
C20.09995 (18)0.17091 (17)0.16743 (14)0.0485 (3)
H20.10560.08120.10790.058*
C30.0023 (2)0.2323 (2)0.13579 (16)0.0581 (4)
H30.05990.18190.05380.070*
C40.0052 (2)0.3660 (2)0.22221 (17)0.0591 (4)
H40.07200.40430.19790.071*
C50.08503 (18)0.44334 (17)0.34419 (16)0.0502 (4)
H50.08080.53440.40200.060*
C60.18221 (15)0.38411 (14)0.37986 (13)0.0362 (3)
C70.28394 (14)0.43405 (13)0.50043 (12)0.0338 (3)
C80.35218 (13)0.32723 (12)0.48302 (11)0.0316 (2)
C90.45294 (14)0.34082 (13)0.58145 (12)0.0346 (3)
H90.49770.26940.56750.042*
C100.48713 (14)0.46487 (13)0.70383 (12)0.0331 (3)
C110.42165 (15)0.57442 (13)0.72159 (12)0.0363 (3)
C120.32029 (15)0.55734 (14)0.61848 (13)0.0389 (3)
H120.27760.62960.63000.047*
C130.46254 (17)0.70407 (14)0.84397 (14)0.0444 (3)
H130.41940.77560.85380.053*
C140.56095 (17)0.72673 (15)0.94549 (13)0.0447 (3)
C150.62605 (16)0.61556 (14)0.93291 (12)0.0404 (3)
C160.59082 (15)0.48544 (13)0.81357 (12)0.0367 (3)
C170.65618 (19)0.38032 (16)0.80598 (14)0.0493 (4)
H170.63330.29430.72830.059*
C180.7536 (2)0.40075 (19)0.91058 (16)0.0605 (4)
H180.79600.32940.90320.073*
C190.7880 (2)0.52832 (19)1.02674 (16)0.0625 (5)
H190.85380.54271.09760.075*
C200.7258 (2)0.63266 (17)1.03758 (14)0.0535 (4)
H200.74990.71761.11640.064*
C210.6035 (2)0.86763 (18)1.07059 (16)0.0640 (5)
H21A0.55060.92921.06210.096*
H21B0.70910.91581.08810.096*
H21C0.57770.84771.14120.096*
C220.21436 (14)0.03734 (13)0.37019 (12)0.0345 (3)
C230.27678 (16)0.03293 (15)0.48342 (14)0.0416 (3)
H230.37710.01890.52120.050*
C240.18862 (19)0.10623 (18)0.53972 (16)0.0515 (4)
H240.22930.10450.61570.062*
C250.04021 (19)0.18190 (17)0.48296 (17)0.0540 (4)
H250.01910.23080.52140.065*
C260.02169 (18)0.18632 (17)0.37012 (17)0.0535 (4)
H260.12220.23800.33290.064*
C270.06510 (16)0.11417 (15)0.31198 (14)0.0449 (3)
H270.02430.11700.23550.054*
N10.29778 (12)0.21380 (11)0.35213 (10)0.0351 (2)
O10.26995 (12)0.02036 (11)0.16013 (9)0.0458 (2)
O20.47830 (10)0.08335 (10)0.34758 (9)0.0414 (2)
S10.32587 (3)0.05452 (3)0.29722 (3)0.03372 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0346 (6)0.0376 (6)0.0340 (6)0.0090 (5)0.0029 (5)0.0189 (5)
C20.0535 (9)0.0477 (8)0.0375 (7)0.0172 (7)0.0048 (6)0.0147 (6)
C30.0605 (10)0.0640 (10)0.0474 (8)0.0204 (8)0.0091 (7)0.0258 (8)
C40.0613 (10)0.0668 (10)0.0589 (10)0.0291 (8)0.0019 (8)0.0345 (8)
C50.0558 (9)0.0471 (8)0.0532 (9)0.0225 (7)0.0039 (7)0.0254 (7)
C60.0364 (6)0.0360 (6)0.0380 (6)0.0095 (5)0.0049 (5)0.0201 (5)
C70.0328 (6)0.0319 (6)0.0362 (6)0.0075 (5)0.0052 (5)0.0173 (5)
C80.0317 (6)0.0284 (5)0.0292 (5)0.0056 (4)0.0040 (4)0.0111 (4)
C90.0365 (6)0.0309 (6)0.0312 (6)0.0100 (5)0.0020 (5)0.0107 (5)
C100.0344 (6)0.0300 (5)0.0302 (6)0.0063 (5)0.0048 (4)0.0121 (5)
C110.0382 (7)0.0309 (6)0.0338 (6)0.0081 (5)0.0064 (5)0.0116 (5)
C120.0419 (7)0.0319 (6)0.0419 (7)0.0142 (5)0.0064 (5)0.0151 (5)
C130.0519 (8)0.0327 (6)0.0407 (7)0.0150 (6)0.0076 (6)0.0096 (5)
C140.0512 (8)0.0364 (6)0.0337 (6)0.0094 (6)0.0062 (6)0.0079 (5)
C150.0456 (7)0.0355 (6)0.0307 (6)0.0058 (5)0.0041 (5)0.0116 (5)
C160.0397 (7)0.0335 (6)0.0306 (6)0.0067 (5)0.0031 (5)0.0125 (5)
C170.0613 (9)0.0408 (7)0.0372 (7)0.0178 (7)0.0031 (6)0.0113 (6)
C180.0766 (12)0.0516 (9)0.0485 (9)0.0251 (8)0.0101 (8)0.0191 (7)
C190.0790 (12)0.0561 (9)0.0422 (8)0.0184 (8)0.0139 (8)0.0187 (7)
C200.0673 (10)0.0451 (8)0.0328 (7)0.0099 (7)0.0054 (6)0.0111 (6)
C210.0805 (12)0.0458 (8)0.0424 (8)0.0222 (8)0.0008 (8)0.0005 (7)
C220.0339 (6)0.0299 (5)0.0355 (6)0.0112 (5)0.0042 (5)0.0114 (5)
C230.0374 (7)0.0442 (7)0.0436 (7)0.0138 (6)0.0035 (5)0.0208 (6)
C240.0567 (9)0.0550 (8)0.0525 (9)0.0209 (7)0.0130 (7)0.0315 (7)
C250.0565 (9)0.0440 (8)0.0647 (10)0.0143 (7)0.0239 (8)0.0276 (7)
C260.0391 (8)0.0444 (8)0.0594 (9)0.0033 (6)0.0065 (7)0.0150 (7)
C270.0390 (7)0.0409 (7)0.0434 (7)0.0080 (6)0.0013 (6)0.0134 (6)
N10.0378 (6)0.0323 (5)0.0290 (5)0.0108 (4)0.0012 (4)0.0101 (4)
O10.0552 (6)0.0442 (5)0.0280 (5)0.0177 (4)0.0019 (4)0.0078 (4)
O20.0335 (5)0.0459 (5)0.0406 (5)0.0156 (4)0.0065 (4)0.0150 (4)
S10.03463 (17)0.03321 (16)0.02764 (16)0.01181 (12)0.00277 (11)0.00900 (12)
Geometric parameters (Å, º) top
C1—C21.3838 (18)C15—C161.4172 (17)
C1—C61.3981 (18)C16—C171.397 (2)
C1—N11.4258 (16)C17—C181.378 (2)
C2—C31.382 (2)C17—H170.9300
C2—H20.9300C18—C191.384 (2)
C3—C41.374 (3)C18—H180.9300
C3—H30.9300C19—C201.361 (2)
C4—C51.374 (2)C19—H190.9300
C4—H40.9300C20—H200.9300
C5—C61.3818 (19)C21—H21A0.9600
C5—H50.9300C21—H21B0.9600
C6—C71.4451 (17)C21—H21C0.9600
C7—C121.3725 (17)C22—C231.3825 (18)
C7—C81.4063 (17)C22—C271.3872 (18)
C8—C91.3729 (16)C22—S11.7542 (13)
C8—N11.4255 (14)C23—C241.379 (2)
C9—C101.4065 (16)C23—H230.9300
C9—H90.9300C24—C251.376 (2)
C10—C111.4139 (18)C24—H240.9300
C10—C161.4572 (17)C25—C261.377 (2)
C11—C121.4010 (18)C25—H250.9300
C11—C131.4307 (18)C26—C271.382 (2)
C12—H120.9300C26—H260.9300
C13—C141.347 (2)C27—H270.9300
C13—H130.9300N1—S11.6499 (11)
C14—C151.440 (2)O1—S11.4223 (9)
C14—C211.5069 (19)O2—S11.4228 (10)
C15—C201.406 (2)
C2—C1—C6121.28 (12)C15—C16—C10119.28 (12)
C2—C1—N1130.60 (12)C18—C17—C16121.74 (14)
C6—C1—N1108.12 (11)C18—C17—H17119.1
C3—C2—C1117.42 (14)C16—C17—H17119.1
C3—C2—H2121.3C17—C18—C19119.51 (16)
C1—C2—H2121.3C17—C18—H18120.2
C4—C3—C2121.79 (15)C19—C18—H18120.2
C4—C3—H3119.1C20—C19—C18120.24 (15)
C2—C3—H3119.1C20—C19—H19119.9
C5—C4—C3120.61 (15)C18—C19—H19119.9
C5—C4—H4119.7C19—C20—C15121.79 (14)
C3—C4—H4119.7C19—C20—H20119.1
C4—C5—C6119.13 (15)C15—C20—H20119.1
C4—C5—H5120.4C14—C21—H21A109.5
C6—C5—H5120.4C14—C21—H21B109.5
C5—C6—C1119.74 (13)H21A—C21—H21B109.5
C5—C6—C7132.16 (13)C14—C21—H21C109.5
C1—C6—C7108.06 (11)H21A—C21—H21C109.5
C12—C7—C8119.46 (11)H21B—C21—H21C109.5
C12—C7—C6132.79 (12)C23—C22—C27121.37 (13)
C8—C7—C6107.75 (11)C23—C22—S1119.60 (10)
C9—C8—C7122.08 (11)C27—C22—S1119.03 (10)
C9—C8—N1129.99 (11)C24—C23—C22119.25 (13)
C7—C8—N1107.94 (10)C24—C23—H23120.4
C8—C9—C10118.68 (12)C22—C23—H23120.4
C8—C9—H9120.7C25—C24—C23119.69 (15)
C10—C9—H9120.7C25—C24—H24120.2
C9—C10—C11119.69 (11)C23—C24—H24120.2
C9—C10—C16121.78 (12)C24—C25—C26120.97 (15)
C11—C10—C16118.52 (11)C24—C25—H25119.5
C12—C11—C10119.97 (12)C26—C25—H25119.5
C12—C11—C13120.35 (12)C25—C26—C27120.14 (14)
C10—C11—C13119.66 (12)C25—C26—H26119.9
C7—C12—C11120.07 (12)C27—C26—H26119.9
C7—C12—H12120.0C26—C27—C22118.58 (14)
C11—C12—H12120.0C26—C27—H27120.7
C14—C13—C11122.69 (14)C22—C27—H27120.7
C14—C13—H13118.7C8—N1—C1108.03 (10)
C11—C13—H13118.7C8—N1—S1124.03 (8)
C13—C14—C15119.35 (12)C1—N1—S1126.23 (8)
C13—C14—C21120.28 (14)O1—S1—O2120.40 (6)
C15—C14—C21120.37 (14)O1—S1—N1106.72 (6)
C20—C15—C16118.27 (14)O2—S1—N1106.51 (6)
C20—C15—C14121.30 (13)O1—S1—C22108.78 (6)
C16—C15—C14120.43 (12)O2—S1—C22108.04 (6)
C17—C16—C15118.46 (12)N1—S1—C22105.42 (6)
C17—C16—C10122.26 (12)
C6—C1—C2—C31.1 (2)C20—C15—C16—C10179.69 (13)
N1—C1—C2—C3179.49 (15)C14—C15—C16—C100.39 (19)
C1—C2—C3—C41.1 (3)C9—C10—C16—C173.4 (2)
C2—C3—C4—C50.1 (3)C11—C10—C16—C17177.57 (13)
C3—C4—C5—C61.0 (3)C9—C10—C16—C15177.25 (12)
C4—C5—C6—C10.9 (2)C11—C10—C16—C151.77 (18)
C4—C5—C6—C7176.62 (15)C15—C16—C17—C180.4 (2)
C2—C1—C6—C50.1 (2)C10—C16—C17—C18179.74 (15)
N1—C1—C6—C5179.63 (13)C16—C17—C18—C190.2 (3)
C2—C1—C6—C7178.23 (13)C17—C18—C19—C200.1 (3)
N1—C1—C6—C72.27 (14)C18—C19—C20—C150.2 (3)
C5—C6—C7—C121.4 (3)C16—C15—C20—C190.1 (2)
C1—C6—C7—C12179.23 (14)C14—C15—C20—C19179.97 (16)
C5—C6—C7—C8178.09 (15)C27—C22—C23—C240.1 (2)
C1—C6—C7—C80.31 (14)S1—C22—C23—C24179.57 (11)
C12—C7—C8—C91.12 (19)C22—C23—C24—C250.3 (2)
C6—C7—C8—C9178.49 (11)C23—C24—C25—C260.4 (2)
C12—C7—C8—N1178.62 (11)C24—C25—C26—C270.0 (3)
C6—C7—C8—N11.77 (13)C25—C26—C27—C220.4 (2)
C7—C8—C9—C100.81 (19)C23—C22—C27—C260.5 (2)
N1—C8—C9—C10179.52 (12)S1—C22—C27—C26179.90 (11)
C8—C9—C10—C112.16 (18)C9—C8—N1—C1177.12 (12)
C8—C9—C10—C16178.83 (11)C7—C8—N1—C13.17 (13)
C9—C10—C11—C121.62 (19)C9—C8—N1—S111.21 (19)
C16—C10—C11—C12179.33 (12)C7—C8—N1—S1169.08 (9)
C9—C10—C11—C13176.69 (12)C2—C1—N1—C8177.19 (14)
C16—C10—C11—C132.35 (19)C6—C1—N1—C83.37 (14)
C8—C7—C12—C111.66 (19)C2—C1—N1—S111.7 (2)
C6—C7—C12—C11177.83 (13)C6—C1—N1—S1168.89 (9)
C10—C11—C12—C70.3 (2)C8—N1—S1—O1173.31 (10)
C13—C11—C12—C7178.62 (12)C1—N1—S1—O123.37 (13)
C12—C11—C13—C14179.06 (14)C8—N1—S1—O243.51 (11)
C10—C11—C13—C140.7 (2)C1—N1—S1—O2153.16 (11)
C11—C13—C14—C151.5 (2)C8—N1—S1—C2271.12 (11)
C11—C13—C14—C21178.00 (14)C1—N1—S1—C2292.20 (11)
C13—C14—C15—C20178.06 (15)C23—C22—S1—O1150.21 (11)
C21—C14—C15—C202.5 (2)C27—C22—S1—O129.23 (13)
C13—C14—C15—C162.0 (2)C23—C22—S1—O217.93 (13)
C21—C14—C15—C16177.44 (14)C27—C22—S1—O2161.51 (11)
C20—C15—C16—C170.3 (2)C23—C22—S1—N195.64 (11)
C14—C15—C16—C17179.76 (14)C27—C22—S1—N184.91 (11)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the pyrrole ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.312.9003 (18)121
C9—H9···O20.932.422.9994 (15)120
C23—H23···O20.932.552.9088 (18)103
C25—H25···Cg1i0.932.613.4770 (2)156
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC27H19NO2S
Mr421.49
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)9.4527 (3), 10.7457 (3), 11.5791 (3)
α, β, γ (°)115.592 (1), 93.324 (2), 105.206 (2)
V3)1003.61 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.946, 0.964
No. of measured, independent and
observed [I > 2σ(I)] reflections
23737, 5360, 4477
Rint0.027
(sin θ/λ)max1)0.684
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.120, 1.05
No. of reflections5360
No. of parameters281
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.29

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

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the pyrrole ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.312.9003 (18)121.3
C9—H9···O20.932.422.9994 (15)120.1
C25—H25···Cg1i0.932.613.4770 (2)156.0
Symmetry code: (i) x, y, z+1.
 

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Madras, Chennai, for the X-ray data collection.

References

First citationAbele, E., Abele, R., Dzenitis, O. & Lukevics, E. (2003). Chem. Heterocycl. Compd, 39, 3–35.  CrossRef CAS Google Scholar
First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChai, H., Zhao, Y., Zhao, C. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911–917.  Web of Science CrossRef PubMed CAS Google Scholar
First citationChakkaravarthi, G., Ramesh, N., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3564.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLiu, Y., Gribble, G. W. & Jasinski, J. P. (2007). Acta Cryst. E63, o738–o740.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationPanwar, H., Verma, R. S., Srivastava, V. K. & Kumar, A. (2006). Indian J. Chem. Sect. B, 45, 2099–2104.  Google Scholar
First citationRani, P., Srivastava, V. K. & Kumar, A. (2004). Eur. J. Med. Chem. 39, 449–452.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds