organic compounds
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
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
Related literature
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
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; 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.
Supporting information
https://doi.org/10.1107/S160053681104949X/bh2396sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104949X/bh2396Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681104949X/bh2396Isup3.cml
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.
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.
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).
Data collection: APEX2 (Bruker, 2004); cell
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).Fig. 1. The molecular structure of the title compound, with 30% probability displacement ellipsoids for non-H atoms. |
C27H19NO2S | Z = 2 |
Mr = 421.49 | F(000) = 440 |
Triclinic, P1 | Dx = 1.395 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4527 (3) Å | Cell parameters from 6046 reflections |
b = 10.7457 (3) Å | θ = 2.2–29.0° |
c = 11.5791 (3) Å | µ = 0.19 mm−1 |
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 |
Bruker Kappa APEXII CCD diffractometer | 5360 independent reflections |
Radiation source: fine-focus sealed tube | 4477 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 0 pixels mm-1 | θmax = 29.1°, θmin = 2.2° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −14→14 |
Tmin = 0.946, Tmax = 0.964 | l = −15→15 |
23737 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-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 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C27H19NO2S | γ = 105.206 (2)° |
Mr = 421.49 | V = 1003.61 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.4527 (3) Å | Mo Kα radiation |
b = 10.7457 (3) Å | µ = 0.19 mm−1 |
c = 11.5791 (3) Å | T = 295 K |
α = 115.592 (1)° | 0.30 × 0.25 × 0.20 mm |
β = 93.324 (2)° |
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 = 0.964 | Rint = 0.027 |
23737 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.38 e Å−3 |
5360 reflections | Δρmin = −0.29 e Å−3 |
281 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.18888 (14) | 0.24807 (14) | 0.29115 (12) | 0.0353 (3) | |
C2 | 0.09995 (18) | 0.17091 (17) | 0.16743 (14) | 0.0485 (3) | |
H2 | 0.1056 | 0.0812 | 0.1079 | 0.058* | |
C3 | 0.0023 (2) | 0.2323 (2) | 0.13579 (16) | 0.0581 (4) | |
H3 | −0.0599 | 0.1819 | 0.0538 | 0.070* | |
C4 | −0.0052 (2) | 0.3660 (2) | 0.22221 (17) | 0.0591 (4) | |
H4 | −0.0720 | 0.4043 | 0.1979 | 0.071* | |
C5 | 0.08503 (18) | 0.44334 (17) | 0.34419 (16) | 0.0502 (4) | |
H5 | 0.0808 | 0.5344 | 0.4020 | 0.060* | |
C6 | 0.18221 (15) | 0.38411 (14) | 0.37986 (13) | 0.0362 (3) | |
C7 | 0.28394 (14) | 0.43405 (13) | 0.50043 (12) | 0.0338 (3) | |
C8 | 0.35218 (13) | 0.32723 (12) | 0.48302 (11) | 0.0316 (2) | |
C9 | 0.45294 (14) | 0.34082 (13) | 0.58145 (12) | 0.0346 (3) | |
H9 | 0.4977 | 0.2694 | 0.5675 | 0.042* | |
C10 | 0.48713 (14) | 0.46487 (13) | 0.70383 (12) | 0.0331 (3) | |
C11 | 0.42165 (15) | 0.57442 (13) | 0.72159 (12) | 0.0363 (3) | |
C12 | 0.32029 (15) | 0.55734 (14) | 0.61848 (13) | 0.0389 (3) | |
H12 | 0.2776 | 0.6296 | 0.6300 | 0.047* | |
C13 | 0.46254 (17) | 0.70407 (14) | 0.84397 (14) | 0.0444 (3) | |
H13 | 0.4194 | 0.7756 | 0.8538 | 0.053* | |
C14 | 0.56095 (17) | 0.72673 (15) | 0.94549 (13) | 0.0447 (3) | |
C15 | 0.62605 (16) | 0.61556 (14) | 0.93291 (12) | 0.0404 (3) | |
C16 | 0.59082 (15) | 0.48544 (13) | 0.81357 (12) | 0.0367 (3) | |
C17 | 0.65618 (19) | 0.38032 (16) | 0.80598 (14) | 0.0493 (4) | |
H17 | 0.6333 | 0.2943 | 0.7283 | 0.059* | |
C18 | 0.7536 (2) | 0.40075 (19) | 0.91058 (16) | 0.0605 (4) | |
H18 | 0.7960 | 0.3294 | 0.9032 | 0.073* | |
C19 | 0.7880 (2) | 0.52832 (19) | 1.02674 (16) | 0.0625 (5) | |
H19 | 0.8538 | 0.5427 | 1.0976 | 0.075* | |
C20 | 0.7258 (2) | 0.63266 (17) | 1.03758 (14) | 0.0535 (4) | |
H20 | 0.7499 | 0.7176 | 1.1164 | 0.064* | |
C21 | 0.6035 (2) | 0.86763 (18) | 1.07059 (16) | 0.0640 (5) | |
H21A | 0.5506 | 0.9292 | 1.0621 | 0.096* | |
H21B | 0.7091 | 0.9158 | 1.0881 | 0.096* | |
H21C | 0.5777 | 0.8477 | 1.1412 | 0.096* | |
C22 | 0.21436 (14) | −0.03734 (13) | 0.37019 (12) | 0.0345 (3) | |
C23 | 0.27678 (16) | −0.03293 (15) | 0.48342 (14) | 0.0416 (3) | |
H23 | 0.3771 | 0.0189 | 0.5212 | 0.050* | |
C24 | 0.18862 (19) | −0.10623 (18) | 0.53972 (16) | 0.0515 (4) | |
H24 | 0.2293 | −0.1045 | 0.6157 | 0.062* | |
C25 | 0.04021 (19) | −0.18190 (17) | 0.48296 (17) | 0.0540 (4) | |
H25 | −0.0191 | −0.2308 | 0.5214 | 0.065* | |
C26 | −0.02169 (18) | −0.18632 (17) | 0.37012 (17) | 0.0535 (4) | |
H26 | −0.1222 | −0.2380 | 0.3329 | 0.064* | |
C27 | 0.06510 (16) | −0.11417 (15) | 0.31198 (14) | 0.0449 (3) | |
H27 | 0.0243 | −0.1170 | 0.2355 | 0.054* | |
N1 | 0.29778 (12) | 0.21380 (11) | 0.35213 (10) | 0.0351 (2) | |
O1 | 0.26995 (12) | −0.02036 (11) | 0.16013 (9) | 0.0458 (2) | |
O2 | 0.47830 (10) | 0.08335 (10) | 0.34758 (9) | 0.0414 (2) | |
S1 | 0.32587 (3) | 0.05452 (3) | 0.29722 (3) | 0.03372 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0346 (6) | 0.0376 (6) | 0.0340 (6) | 0.0090 (5) | 0.0029 (5) | 0.0189 (5) |
C2 | 0.0535 (9) | 0.0477 (8) | 0.0375 (7) | 0.0172 (7) | −0.0048 (6) | 0.0147 (6) |
C3 | 0.0605 (10) | 0.0640 (10) | 0.0474 (8) | 0.0204 (8) | −0.0091 (7) | 0.0258 (8) |
C4 | 0.0613 (10) | 0.0668 (10) | 0.0589 (10) | 0.0291 (8) | −0.0019 (8) | 0.0345 (8) |
C5 | 0.0558 (9) | 0.0471 (8) | 0.0532 (9) | 0.0225 (7) | 0.0039 (7) | 0.0254 (7) |
C6 | 0.0364 (6) | 0.0360 (6) | 0.0380 (6) | 0.0095 (5) | 0.0049 (5) | 0.0201 (5) |
C7 | 0.0328 (6) | 0.0319 (6) | 0.0362 (6) | 0.0075 (5) | 0.0052 (5) | 0.0173 (5) |
C8 | 0.0317 (6) | 0.0284 (5) | 0.0292 (5) | 0.0056 (4) | 0.0040 (4) | 0.0111 (4) |
C9 | 0.0365 (6) | 0.0309 (6) | 0.0312 (6) | 0.0100 (5) | 0.0020 (5) | 0.0107 (5) |
C10 | 0.0344 (6) | 0.0300 (5) | 0.0302 (6) | 0.0063 (5) | 0.0048 (4) | 0.0121 (5) |
C11 | 0.0382 (7) | 0.0309 (6) | 0.0338 (6) | 0.0081 (5) | 0.0064 (5) | 0.0116 (5) |
C12 | 0.0419 (7) | 0.0319 (6) | 0.0419 (7) | 0.0142 (5) | 0.0064 (5) | 0.0151 (5) |
C13 | 0.0519 (8) | 0.0327 (6) | 0.0407 (7) | 0.0150 (6) | 0.0076 (6) | 0.0096 (5) |
C14 | 0.0512 (8) | 0.0364 (6) | 0.0337 (6) | 0.0094 (6) | 0.0062 (6) | 0.0079 (5) |
C15 | 0.0456 (7) | 0.0355 (6) | 0.0307 (6) | 0.0058 (5) | 0.0041 (5) | 0.0116 (5) |
C16 | 0.0397 (7) | 0.0335 (6) | 0.0306 (6) | 0.0067 (5) | 0.0031 (5) | 0.0125 (5) |
C17 | 0.0613 (9) | 0.0408 (7) | 0.0372 (7) | 0.0178 (7) | −0.0031 (6) | 0.0113 (6) |
C18 | 0.0766 (12) | 0.0516 (9) | 0.0485 (9) | 0.0251 (8) | −0.0101 (8) | 0.0191 (7) |
C19 | 0.0790 (12) | 0.0561 (9) | 0.0422 (8) | 0.0184 (8) | −0.0139 (8) | 0.0187 (7) |
C20 | 0.0673 (10) | 0.0451 (8) | 0.0328 (7) | 0.0099 (7) | −0.0054 (6) | 0.0111 (6) |
C21 | 0.0805 (12) | 0.0458 (8) | 0.0424 (8) | 0.0222 (8) | −0.0008 (8) | 0.0005 (7) |
C22 | 0.0339 (6) | 0.0299 (5) | 0.0355 (6) | 0.0112 (5) | 0.0042 (5) | 0.0114 (5) |
C23 | 0.0374 (7) | 0.0442 (7) | 0.0436 (7) | 0.0138 (6) | 0.0035 (5) | 0.0208 (6) |
C24 | 0.0567 (9) | 0.0550 (8) | 0.0525 (9) | 0.0209 (7) | 0.0130 (7) | 0.0315 (7) |
C25 | 0.0565 (9) | 0.0440 (8) | 0.0647 (10) | 0.0143 (7) | 0.0239 (8) | 0.0276 (7) |
C26 | 0.0391 (8) | 0.0444 (8) | 0.0594 (9) | 0.0033 (6) | 0.0065 (7) | 0.0150 (7) |
C27 | 0.0390 (7) | 0.0409 (7) | 0.0434 (7) | 0.0080 (6) | −0.0013 (6) | 0.0134 (6) |
N1 | 0.0378 (6) | 0.0323 (5) | 0.0290 (5) | 0.0108 (4) | −0.0012 (4) | 0.0101 (4) |
O1 | 0.0552 (6) | 0.0442 (5) | 0.0280 (5) | 0.0177 (4) | 0.0019 (4) | 0.0078 (4) |
O2 | 0.0335 (5) | 0.0459 (5) | 0.0406 (5) | 0.0156 (4) | 0.0065 (4) | 0.0150 (4) |
S1 | 0.03463 (17) | 0.03321 (16) | 0.02764 (16) | 0.01181 (12) | 0.00277 (11) | 0.00900 (12) |
C1—C2 | 1.3838 (18) | C15—C16 | 1.4172 (17) |
C1—C6 | 1.3981 (18) | C16—C17 | 1.397 (2) |
C1—N1 | 1.4258 (16) | C17—C18 | 1.378 (2) |
C2—C3 | 1.382 (2) | C17—H17 | 0.9300 |
C2—H2 | 0.9300 | C18—C19 | 1.384 (2) |
C3—C4 | 1.374 (3) | C18—H18 | 0.9300 |
C3—H3 | 0.9300 | C19—C20 | 1.361 (2) |
C4—C5 | 1.374 (2) | C19—H19 | 0.9300 |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—C6 | 1.3818 (19) | C21—H21A | 0.9600 |
C5—H5 | 0.9300 | C21—H21B | 0.9600 |
C6—C7 | 1.4451 (17) | C21—H21C | 0.9600 |
C7—C12 | 1.3725 (17) | C22—C23 | 1.3825 (18) |
C7—C8 | 1.4063 (17) | C22—C27 | 1.3872 (18) |
C8—C9 | 1.3729 (16) | C22—S1 | 1.7542 (13) |
C8—N1 | 1.4255 (14) | C23—C24 | 1.379 (2) |
C9—C10 | 1.4065 (16) | C23—H23 | 0.9300 |
C9—H9 | 0.9300 | C24—C25 | 1.376 (2) |
C10—C11 | 1.4139 (18) | C24—H24 | 0.9300 |
C10—C16 | 1.4572 (17) | C25—C26 | 1.377 (2) |
C11—C12 | 1.4010 (18) | C25—H25 | 0.9300 |
C11—C13 | 1.4307 (18) | C26—C27 | 1.382 (2) |
C12—H12 | 0.9300 | C26—H26 | 0.9300 |
C13—C14 | 1.347 (2) | C27—H27 | 0.9300 |
C13—H13 | 0.9300 | N1—S1 | 1.6499 (11) |
C14—C15 | 1.440 (2) | O1—S1 | 1.4223 (9) |
C14—C21 | 1.5069 (19) | O2—S1 | 1.4228 (10) |
C15—C20 | 1.406 (2) | ||
C2—C1—C6 | 121.28 (12) | C15—C16—C10 | 119.28 (12) |
C2—C1—N1 | 130.60 (12) | C18—C17—C16 | 121.74 (14) |
C6—C1—N1 | 108.12 (11) | C18—C17—H17 | 119.1 |
C3—C2—C1 | 117.42 (14) | C16—C17—H17 | 119.1 |
C3—C2—H2 | 121.3 | C17—C18—C19 | 119.51 (16) |
C1—C2—H2 | 121.3 | C17—C18—H18 | 120.2 |
C4—C3—C2 | 121.79 (15) | C19—C18—H18 | 120.2 |
C4—C3—H3 | 119.1 | C20—C19—C18 | 120.24 (15) |
C2—C3—H3 | 119.1 | C20—C19—H19 | 119.9 |
C5—C4—C3 | 120.61 (15) | C18—C19—H19 | 119.9 |
C5—C4—H4 | 119.7 | C19—C20—C15 | 121.79 (14) |
C3—C4—H4 | 119.7 | C19—C20—H20 | 119.1 |
C4—C5—C6 | 119.13 (15) | C15—C20—H20 | 119.1 |
C4—C5—H5 | 120.4 | C14—C21—H21A | 109.5 |
C6—C5—H5 | 120.4 | C14—C21—H21B | 109.5 |
C5—C6—C1 | 119.74 (13) | H21A—C21—H21B | 109.5 |
C5—C6—C7 | 132.16 (13) | C14—C21—H21C | 109.5 |
C1—C6—C7 | 108.06 (11) | H21A—C21—H21C | 109.5 |
C12—C7—C8 | 119.46 (11) | H21B—C21—H21C | 109.5 |
C12—C7—C6 | 132.79 (12) | C23—C22—C27 | 121.37 (13) |
C8—C7—C6 | 107.75 (11) | C23—C22—S1 | 119.60 (10) |
C9—C8—C7 | 122.08 (11) | C27—C22—S1 | 119.03 (10) |
C9—C8—N1 | 129.99 (11) | C24—C23—C22 | 119.25 (13) |
C7—C8—N1 | 107.94 (10) | C24—C23—H23 | 120.4 |
C8—C9—C10 | 118.68 (12) | C22—C23—H23 | 120.4 |
C8—C9—H9 | 120.7 | C25—C24—C23 | 119.69 (15) |
C10—C9—H9 | 120.7 | C25—C24—H24 | 120.2 |
C9—C10—C11 | 119.69 (11) | C23—C24—H24 | 120.2 |
C9—C10—C16 | 121.78 (12) | C24—C25—C26 | 120.97 (15) |
C11—C10—C16 | 118.52 (11) | C24—C25—H25 | 119.5 |
C12—C11—C10 | 119.97 (12) | C26—C25—H25 | 119.5 |
C12—C11—C13 | 120.35 (12) | C25—C26—C27 | 120.14 (14) |
C10—C11—C13 | 119.66 (12) | C25—C26—H26 | 119.9 |
C7—C12—C11 | 120.07 (12) | C27—C26—H26 | 119.9 |
C7—C12—H12 | 120.0 | C26—C27—C22 | 118.58 (14) |
C11—C12—H12 | 120.0 | C26—C27—H27 | 120.7 |
C14—C13—C11 | 122.69 (14) | C22—C27—H27 | 120.7 |
C14—C13—H13 | 118.7 | C8—N1—C1 | 108.03 (10) |
C11—C13—H13 | 118.7 | C8—N1—S1 | 124.03 (8) |
C13—C14—C15 | 119.35 (12) | C1—N1—S1 | 126.23 (8) |
C13—C14—C21 | 120.28 (14) | O1—S1—O2 | 120.40 (6) |
C15—C14—C21 | 120.37 (14) | O1—S1—N1 | 106.72 (6) |
C20—C15—C16 | 118.27 (14) | O2—S1—N1 | 106.51 (6) |
C20—C15—C14 | 121.30 (13) | O1—S1—C22 | 108.78 (6) |
C16—C15—C14 | 120.43 (12) | O2—S1—C22 | 108.04 (6) |
C17—C16—C15 | 118.46 (12) | N1—S1—C22 | 105.42 (6) |
C17—C16—C10 | 122.26 (12) | ||
C6—C1—C2—C3 | −1.1 (2) | C20—C15—C16—C10 | 179.69 (13) |
N1—C1—C2—C3 | 179.49 (15) | C14—C15—C16—C10 | −0.39 (19) |
C1—C2—C3—C4 | 1.1 (3) | C9—C10—C16—C17 | −3.4 (2) |
C2—C3—C4—C5 | −0.1 (3) | C11—C10—C16—C17 | 177.57 (13) |
C3—C4—C5—C6 | −1.0 (3) | C9—C10—C16—C15 | 177.25 (12) |
C4—C5—C6—C1 | 0.9 (2) | C11—C10—C16—C15 | −1.77 (18) |
C4—C5—C6—C7 | −176.62 (15) | C15—C16—C17—C18 | −0.4 (2) |
C2—C1—C6—C5 | 0.1 (2) | C10—C16—C17—C18 | −179.74 (15) |
N1—C1—C6—C5 | 179.63 (13) | C16—C17—C18—C19 | 0.2 (3) |
C2—C1—C6—C7 | 178.23 (13) | C17—C18—C19—C20 | 0.1 (3) |
N1—C1—C6—C7 | −2.27 (14) | C18—C19—C20—C15 | −0.2 (3) |
C5—C6—C7—C12 | −1.4 (3) | C16—C15—C20—C19 | −0.1 (2) |
C1—C6—C7—C12 | −179.23 (14) | C14—C15—C20—C19 | −179.97 (16) |
C5—C6—C7—C8 | 178.09 (15) | C27—C22—C23—C24 | −0.1 (2) |
C1—C6—C7—C8 | 0.31 (14) | S1—C22—C23—C24 | −179.57 (11) |
C12—C7—C8—C9 | 1.12 (19) | C22—C23—C24—C25 | −0.3 (2) |
C6—C7—C8—C9 | −178.49 (11) | C23—C24—C25—C26 | 0.4 (2) |
C12—C7—C8—N1 | −178.62 (11) | C24—C25—C26—C27 | 0.0 (3) |
C6—C7—C8—N1 | 1.77 (13) | C25—C26—C27—C22 | −0.4 (2) |
C7—C8—C9—C10 | 0.81 (19) | C23—C22—C27—C26 | 0.5 (2) |
N1—C8—C9—C10 | −179.52 (12) | S1—C22—C27—C26 | 179.90 (11) |
C8—C9—C10—C11 | −2.16 (18) | C9—C8—N1—C1 | 177.12 (12) |
C8—C9—C10—C16 | 178.83 (11) | C7—C8—N1—C1 | −3.17 (13) |
C9—C10—C11—C12 | 1.62 (19) | C9—C8—N1—S1 | 11.21 (19) |
C16—C10—C11—C12 | −179.33 (12) | C7—C8—N1—S1 | −169.08 (9) |
C9—C10—C11—C13 | −176.69 (12) | C2—C1—N1—C8 | −177.19 (14) |
C16—C10—C11—C13 | 2.35 (19) | C6—C1—N1—C8 | 3.37 (14) |
C8—C7—C12—C11 | −1.66 (19) | C2—C1—N1—S1 | −11.7 (2) |
C6—C7—C12—C11 | 177.83 (13) | C6—C1—N1—S1 | 168.89 (9) |
C10—C11—C12—C7 | 0.3 (2) | C8—N1—S1—O1 | −173.31 (10) |
C13—C11—C12—C7 | 178.62 (12) | C1—N1—S1—O1 | 23.37 (13) |
C12—C11—C13—C14 | −179.06 (14) | C8—N1—S1—O2 | −43.51 (11) |
C10—C11—C13—C14 | −0.7 (2) | C1—N1—S1—O2 | 153.16 (11) |
C11—C13—C14—C15 | −1.5 (2) | C8—N1—S1—C22 | 71.12 (11) |
C11—C13—C14—C21 | 178.00 (14) | C1—N1—S1—C22 | −92.20 (11) |
C13—C14—C15—C20 | −178.06 (15) | C23—C22—S1—O1 | 150.21 (11) |
C21—C14—C15—C20 | 2.5 (2) | C27—C22—S1—O1 | −29.23 (13) |
C13—C14—C15—C16 | 2.0 (2) | C23—C22—S1—O2 | 17.93 (13) |
C21—C14—C15—C16 | −177.44 (14) | C27—C22—S1—O2 | −161.51 (11) |
C20—C15—C16—C17 | 0.3 (2) | C23—C22—S1—N1 | −95.64 (11) |
C14—C15—C16—C17 | −179.76 (14) | C27—C22—S1—N1 | 84.91 (11) |
Cg1 is the centroid of the pyrrole ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.93 | 2.31 | 2.9003 (18) | 121 |
C9—H9···O2 | 0.93 | 2.42 | 2.9994 (15) | 120 |
C23—H23···O2 | 0.93 | 2.55 | 2.9088 (18) | 103 |
C25—H25···Cg1i | 0.93 | 2.61 | 3.4770 (2) | 156 |
Symmetry code: (i) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C27H19NO2S |
Mr | 421.49 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 1003.61 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.946, 0.964 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23737, 5360, 4477 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.684 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.120, 1.05 |
No. of reflections | 5360 |
No. of parameters | 281 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.29 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
Cg1 is the centroid of the pyrrole ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.93 | 2.31 | 2.9003 (18) | 121.3 |
C9—H9···O2 | 0.93 | 2.42 | 2.9994 (15) | 120.1 |
C25—H25···Cg1i | 0.93 | 2.61 | 3.4770 (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
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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.
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.