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

Vasudhevan, S.; Joel Karunakaran, R.

doi:10.1107/S160053681104949X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3480

https://doi.org/10.1107/S160053681104949X

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

S. Vasudhevan ^a and R. Joel Karunakaran ^a ^*

^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 ); 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

C₂₇H₁₉NO₂S
M_r = 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 ) T_min = 0.946, T_max = 0.964
23737 measured reflections
5360 independent reflections
4477 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.120
S = 1.05
5360 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −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	D⋯A	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 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681104949X/bh2396sup1.cif

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

checkCIF report

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.

Structure description 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).

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

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

C₂₇H₁₉NO₂S	Z = 2
M_r = 421.49	F(000) = 440
Triclinic, P1	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	5360 independent reflections
Radiation source: fine-focus sealed tube	4477 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 0 pixels mm^-1	θ_max = 29.1°, θ_min = 2.2°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
T_min = 0.946, T_max = 0.964	l = −15→15
23737 measured reflections

Refinement top

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(F_o²) + (0.0679P)² + 0.1767P] where P = (F_o² + 2F_c²)/3
5360 reflections	(Δ/σ)_max < 0.001
281 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₇H₁₉NO₂S	γ = 105.206 (2)°
M_r = 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)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5360 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4477 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.964	R_int = 0.027
23737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.05	Δρ_max = 0.38 e Å⁻³
5360 reflections	Δρ_min = −0.29 e Å⁻³
281 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.946, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	23737, 5360, 4477
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	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···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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