7-Phenyl­sulfonyl-7H-benzofurano[2,3-b]carbazole

Panchatcharam, R.; Dhayalan, V.; Mohanakrishnan, A.K.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536811039705

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2829

doi:10.1107/S1600536811039705

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7-Phenylsulfonyl-7H-benzofurano[2,3-b]carbazole

R. Panchatcharam,^a V. Dhayalan,^b A. K. Mohanakrishnan,^b G. Chakkaravarthi ^c ^* and V. Manivannan ^a

^aCentre for Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com,

(Received 9 September 2011; accepted 27 September 2011; online 5 October 2011)

In the title compound, C₂₄H₁₅NO₃S, the dihedral angle between the phenyl ring and the carbozole system is 74.91 (6)°. The S atom exhibits a distorted tetrahedral geometry [N—S—C = 104.85 (8)°; O—S—O = 119.59 (9)°]. The crystal structure is established by weak intermolecular π–π interactions [centroid–centroid distances = 3.583 (2)–3.782 (2) Å].

Related literature

For the biological activity of carbazole derivatives, see: Ramsewak et al. (1999 ); Tachibana et al. (2001 ). For the structures of closely related compounds, see: Chakkaravarthi et al. (2008a ,b ).

Experimental

Crystal data

C₂₄H₁₅NO₃S
M_r = 397.43
Monoclinic, P 2₁ /c
a = 9.031 (5) Å
b = 10.752 (6) Å
c = 19.217 (5) Å
β = 100.738 (5)°
V = 1833.3 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 295 K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.949, T_max = 0.960
16640 measured reflections
4462 independent reflections
2763 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.112
S = 1.04
4462 reflections
262 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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 global, I. DOI: 10.1107/S1600536811039705/im2318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811039705/im2318Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811039705/im2318Isup3.cml

checkCIF report

Comment top

In continuation of our studies of carbazole derivatives, which are found to possess various biological activities such as antioxidative (Tachibana et al., 2001), anti-inflammatory and antimutagenic (Ramsewak et al., 1999), we report the crystal structure of the title compound (I) (Fig. 1). The geometric parameters of (I) are agree well with similar reported structures [Chakkaravarthi et al. 2008a, 2008b].

The dihedral angle beween the phenyl ring (C1-C6) and the carbozole ring (N1/C7-C18) is 74.91 (6)°. The benzofuran moiety (C15/C19-C24/O3/C16) is almost co-planar [dihedral angle 2.48 (3)°] with the carbazole ring system. In the molecule, the S atom exhibits a distorted tetrahedral [N1-S1-C1 = 104.85 (8)°; O1-S1-O2 = 119.59 (9)°] geometry .

The crystal structure is established by weak intermolecular π–π interactions [Cg1···Cg6 (-x,1-y,1-z) = 3.583 (2) Å; Cg2···Cg6 (1-x,1-y,1-z) = 3.782(2 )Å; Cg4···Cg6 (1-x,1-y,1-z) = 3.730 (2) Å; Cg6···Cg6 (-x,1-y,1-z) = 3.659(2 )Å; Cg1, Cg2, Cg4 and Cg6 are the centroids of the rings (O3/C16/C15/C19/C24), (N1/C7/C12/C13/C18), (C7-C12) and (C19-C24), respectively].

Related literature top

For the biological activity of carbazole derivatives, see: Ramsewak et al. (1999); Tachibana et al. (2001). For the structures of closely related compounds, see: Chakkaravarthi et al. (2008a,b).

Experimental top

To a solution of diethyl-2-((2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl) methylene)malonate (0.2 g, 0.38 mmol) in anhydrous 1,2-dichloroethane (15 mL), anhydrous ZnBr₂ (0.02 g, 0.08 mmol) and benzo[b]furan (0.04 mL, 0.38 mmol) were added. The mixture was then stirred at room temperature for 2 h under N₂ atmosphere. After the solvent was removed,and the residue was quenched with ice-water (50 mL) containing 1 mL of conc.HCl, extracted with chloroform (2 x 10 mL) and dried (Na₂SO₄). Removal of solvent followed by flash column chromatography (n-hexane) led to the isolation of colourless crystals suitable for X-ray diffraction quality after the solvent was evaporated at room temperature (yield: 0.11 g, 73%).

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. Molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

7-Phenylsulfonyl-7H-benzofurano[2,3-b]carbazole top

Crystal data top

C₂₄H₁₅NO₃S	F(000) = 824
M_r = 397.43	D_x = 1.440 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4232 reflections
a = 9.031 (5) Å	θ = 2.2–28.3°
b = 10.752 (6) Å	µ = 0.20 mm⁻¹
c = 19.217 (5) Å	T = 295 K
β = 100.738 (5)°	Block, colourless
V = 1833.3 (15) Å³	0.26 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4462 independent reflections
Radiation source: fine-focus sealed tube	2763 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.949, T_max = 0.960	k = −12→14
16640 measured reflections	l = −25→24

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0453P)² + 0.360P] where P = (F_o² + 2F_c²)/3
4462 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₄H₁₅NO₃S	V = 1833.3 (15) Å³
M_r = 397.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.031 (5) Å	µ = 0.20 mm⁻¹
b = 10.752 (6) Å	T = 295 K
c = 19.217 (5) Å	0.26 × 0.22 × 0.20 mm
β = 100.738 (5)°

Data collection top

Bruker Kappa APEXII diffractometer	4462 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2763 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.960	R_int = 0.027
16640 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.112	H-atom parameters constrained
S = 1.04	Δρ_max = 0.23 e Å⁻³
4462 reflections	Δρ_min = −0.30 e Å⁻³
262 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.2652 (2)	0.06505 (18)	0.27600 (9)	0.0556 (5)
C2	0.1266 (2)	0.1058 (2)	0.28782 (11)	0.0751 (6)
H2	0.1027	0.1900	0.2854	0.090*
C3	0.0258 (3)	0.0206 (4)	0.30312 (14)	0.1056 (10)
H3	−0.0677	0.0471	0.3109	0.127*
C4	0.0599 (4)	−0.1031 (4)	0.30715 (13)	0.1126 (12)
H4	−0.0105	−0.1603	0.3173	0.135*
C5	0.1988 (4)	−0.1433 (3)	0.29616 (13)	0.0992 (9)
H5	0.2224	−0.2276	0.2994	0.119*
C6	0.3021 (3)	−0.0594 (2)	0.28043 (11)	0.0713 (6)
H6	0.3958	−0.0861	0.2729	0.086*
C7	0.56766 (19)	0.14212 (16)	0.38858 (10)	0.0522 (5)
C8	0.6548 (2)	0.04173 (18)	0.37621 (13)	0.0661 (6)
H8	0.6619	0.0176	0.3305	0.079*
C9	0.7310 (2)	−0.0212 (2)	0.43485 (15)	0.0789 (7)
H9	0.7893	−0.0900	0.4283	0.095*
C10	0.7227 (2)	0.0153 (2)	0.50279 (14)	0.0761 (6)
H10	0.7770	−0.0279	0.5412	0.091*
C11	0.6352 (2)	0.11476 (18)	0.51438 (12)	0.0641 (5)
H11	0.6297	0.1391	0.5603	0.077*
C12	0.55535 (19)	0.17832 (16)	0.45685 (10)	0.0498 (4)
C13	0.45251 (18)	0.28238 (15)	0.45167 (9)	0.0464 (4)
C14	0.40052 (19)	0.35208 (15)	0.50305 (10)	0.0487 (4)
H14	0.4316	0.3350	0.5510	0.058*
C15	0.30071 (18)	0.44786 (15)	0.48026 (9)	0.0450 (4)
C16	0.2592 (2)	0.47184 (15)	0.40826 (9)	0.0489 (4)
C17	0.3092 (2)	0.40679 (16)	0.35562 (10)	0.0534 (5)
H17	0.2806	0.4264	0.3079	0.064*
C18	0.40576 (19)	0.30960 (15)	0.37963 (9)	0.0473 (4)
C19	0.21968 (19)	0.53778 (15)	0.51514 (10)	0.0485 (4)
C20	0.2091 (2)	0.56435 (19)	0.58450 (10)	0.0620 (5)
H20	0.2654	0.5200	0.6218	0.074*
C21	0.1136 (2)	0.6577 (2)	0.59692 (12)	0.0690 (6)
H21	0.1056	0.6764	0.6433	0.083*
C22	0.0298 (2)	0.7241 (2)	0.54246 (12)	0.0693 (6)
H22	−0.0343	0.7864	0.5527	0.083*
C23	0.0385 (2)	0.70030 (18)	0.47297 (12)	0.0656 (5)
H23	−0.0179	0.7450	0.4358	0.079*
C24	0.1350 (2)	0.60726 (16)	0.46146 (10)	0.0530 (4)
N1	0.47915 (16)	0.22546 (13)	0.33891 (8)	0.0525 (4)
O1	0.50962 (17)	0.11440 (14)	0.22963 (8)	0.0782 (4)
O2	0.31857 (18)	0.27874 (12)	0.22364 (7)	0.0715 (4)
O3	0.15849 (15)	0.57003 (11)	0.39524 (7)	0.0602 (4)
S1	0.39665 (6)	0.17516 (5)	0.25941 (2)	0.05766 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0605 (11)	0.0645 (12)	0.0413 (10)	−0.0043 (10)	0.0086 (9)	0.0010 (9)
C2	0.0644 (13)	0.0969 (17)	0.0653 (14)	−0.0057 (12)	0.0157 (11)	−0.0002 (12)
C3	0.0810 (18)	0.158 (3)	0.0819 (19)	−0.047 (2)	0.0259 (15)	−0.0159 (19)
C4	0.129 (3)	0.150 (3)	0.0561 (15)	−0.087 (3)	0.0089 (16)	−0.0030 (17)
C5	0.139 (3)	0.0823 (17)	0.0648 (16)	−0.0455 (19)	−0.0103 (17)	0.0090 (13)
C6	0.0848 (15)	0.0645 (13)	0.0602 (13)	−0.0085 (12)	0.0019 (11)	−0.0012 (10)
C7	0.0395 (9)	0.0463 (9)	0.0719 (13)	−0.0024 (8)	0.0132 (9)	−0.0024 (9)
C8	0.0517 (11)	0.0588 (12)	0.0893 (16)	0.0051 (10)	0.0176 (11)	−0.0117 (11)
C9	0.0531 (12)	0.0608 (13)	0.120 (2)	0.0159 (10)	0.0103 (14)	−0.0057 (14)
C10	0.0565 (13)	0.0655 (13)	0.0987 (19)	0.0121 (11)	−0.0048 (12)	0.0068 (13)
C11	0.0524 (11)	0.0604 (12)	0.0752 (14)	0.0034 (10)	0.0003 (10)	0.0000 (11)
C12	0.0392 (9)	0.0440 (9)	0.0650 (12)	−0.0040 (8)	0.0069 (9)	−0.0012 (9)
C13	0.0418 (9)	0.0418 (9)	0.0558 (11)	−0.0055 (7)	0.0098 (8)	0.0002 (8)
C14	0.0491 (10)	0.0473 (10)	0.0490 (10)	−0.0033 (8)	0.0071 (8)	−0.0003 (8)
C15	0.0452 (9)	0.0417 (9)	0.0498 (10)	−0.0049 (8)	0.0135 (8)	−0.0017 (8)
C16	0.0524 (10)	0.0423 (9)	0.0552 (11)	0.0031 (8)	0.0184 (9)	0.0071 (8)
C17	0.0645 (11)	0.0503 (10)	0.0486 (11)	0.0042 (9)	0.0188 (9)	0.0075 (8)
C18	0.0484 (10)	0.0423 (9)	0.0550 (11)	−0.0011 (8)	0.0191 (8)	−0.0002 (8)
C19	0.0474 (10)	0.0426 (9)	0.0576 (10)	−0.0065 (7)	0.0153 (8)	−0.0034 (7)
C20	0.0657 (12)	0.0640 (12)	0.0568 (12)	−0.0010 (10)	0.0128 (10)	−0.0071 (10)
C21	0.0743 (14)	0.0698 (13)	0.0676 (14)	0.0015 (11)	0.0248 (12)	−0.0170 (11)
C22	0.0698 (13)	0.0582 (12)	0.0861 (16)	0.0087 (10)	0.0305 (12)	−0.0119 (11)
C23	0.0705 (13)	0.0547 (11)	0.0756 (14)	0.0148 (10)	0.0245 (11)	0.0038 (10)
C24	0.0590 (11)	0.0453 (10)	0.0589 (11)	−0.0005 (8)	0.0222 (8)	0.0000 (8)
N1	0.0514 (8)	0.0495 (8)	0.0597 (9)	0.0029 (7)	0.0188 (8)	−0.0034 (7)
O1	0.0858 (10)	0.0817 (10)	0.0794 (10)	0.0048 (8)	0.0476 (8)	−0.0124 (8)
O2	0.1036 (11)	0.0625 (8)	0.0527 (8)	0.0097 (8)	0.0257 (8)	0.0121 (7)
O3	0.0742 (9)	0.0538 (7)	0.0562 (8)	0.0178 (7)	0.0216 (7)	0.0103 (6)
S1	0.0692 (3)	0.0567 (3)	0.0535 (3)	0.0019 (2)	0.0282 (2)	0.0007 (2)

Geometric parameters (Å, º) top

C1—C6	1.378 (3)	C13—C18	1.401 (2)
C1—C2	1.385 (3)	C14—C15	1.385 (2)
C1—S1	1.747 (2)	C14—H14	0.9300
C2—C3	1.362 (4)	C15—C16	1.389 (2)
C2—H2	0.9300	C15—C19	1.450 (2)
C3—C4	1.364 (5)	C16—C17	1.373 (2)
C3—H3	0.9300	C16—O3	1.385 (2)
C4—C5	1.380 (4)	C17—C18	1.384 (2)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.372 (3)	C18—N1	1.436 (2)
C5—H5	0.9300	C19—C24	1.383 (3)
C6—H6	0.9300	C19—C20	1.384 (3)
C7—C8	1.382 (3)	C20—C21	1.373 (3)
C7—C12	1.392 (3)	C20—H20	0.9300
C7—N1	1.438 (2)	C21—C22	1.372 (3)
C8—C9	1.383 (3)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.376 (3)
C9—C10	1.379 (3)	C22—H22	0.9300
C9—H9	0.9300	C23—C24	1.371 (3)
C10—C11	1.372 (3)	C23—H23	0.9300
C10—H10	0.9300	C24—O3	1.388 (2)
C11—C12	1.383 (3)	N1—S1	1.6606 (16)
C11—H11	0.9300	O1—S1	1.4187 (14)
C12—C13	1.446 (2)	O2—S1	1.4246 (15)
C13—C14	1.389 (2)

C6—C1—C2	120.9 (2)	C13—C14—H14	121.2
C6—C1—S1	120.30 (17)	C14—C15—C16	119.48 (16)
C2—C1—S1	118.76 (17)	C14—C15—C19	134.79 (17)
C3—C2—C1	118.9 (3)	C16—C15—C19	105.73 (15)
C3—C2—H2	120.6	C17—C16—O3	123.35 (16)
C1—C2—H2	120.6	C17—C16—C15	125.07 (16)
C2—C3—C4	121.1 (3)	O3—C16—C15	111.57 (15)
C2—C3—H3	119.5	C16—C17—C18	114.34 (17)
C4—C3—H3	119.5	C16—C17—H17	122.8
C3—C4—C5	119.9 (3)	C18—C17—H17	122.8
C3—C4—H4	120.1	C17—C18—C13	122.85 (16)
C5—C4—H4	120.1	C17—C18—N1	128.31 (16)
C6—C5—C4	120.2 (3)	C13—C18—N1	108.79 (15)
C6—C5—H5	119.9	C24—C19—C20	118.62 (17)
C4—C5—H5	119.9	C24—C19—C15	105.78 (16)
C5—C6—C1	119.1 (2)	C20—C19—C15	135.59 (18)
C5—C6—H6	120.5	C21—C20—C19	118.47 (19)
C1—C6—H6	120.5	C21—C20—H20	120.8
C8—C7—C12	121.89 (19)	C19—C20—H20	120.8
C8—C7—N1	129.50 (18)	C22—C21—C20	121.5 (2)
C12—C7—N1	108.60 (15)	C22—C21—H21	119.2
C7—C8—C9	117.0 (2)	C20—C21—H21	119.2
C7—C8—H8	121.5	C21—C22—C23	121.32 (19)
C9—C8—H8	121.5	C21—C22—H22	119.3
C10—C9—C8	121.7 (2)	C23—C22—H22	119.3
C10—C9—H9	119.1	C24—C23—C22	116.4 (2)
C8—C9—H9	119.1	C24—C23—H23	121.8
C11—C10—C9	120.7 (2)	C22—C23—H23	121.8
C11—C10—H10	119.7	C23—C24—C19	123.60 (18)
C9—C10—H10	119.7	C23—C24—O3	124.67 (17)
C10—C11—C12	119.0 (2)	C19—C24—O3	111.72 (15)
C10—C11—H11	120.5	C18—N1—C7	106.65 (14)
C12—C11—H11	120.5	C18—N1—S1	122.20 (12)
C11—C12—C7	119.59 (17)	C7—N1—S1	120.42 (12)
C11—C12—C13	132.08 (18)	C16—O3—C24	105.18 (14)
C7—C12—C13	108.34 (16)	O1—S1—O2	119.59 (9)
C14—C13—C18	120.67 (16)	O1—S1—N1	106.74 (9)
C14—C13—C12	131.80 (17)	O2—S1—N1	106.63 (8)
C18—C13—C12	107.53 (15)	O1—S1—C1	109.01 (10)
C15—C14—C13	117.56 (17)	O2—S1—C1	109.01 (10)
C15—C14—H14	121.2	N1—S1—C1	104.85 (8)

C6—C1—C2—C3	−0.8 (3)	C14—C15—C19—C24	−178.82 (18)
S1—C1—C2—C3	−177.82 (18)	C16—C15—C19—C24	0.71 (18)
C1—C2—C3—C4	0.3 (4)	C14—C15—C19—C20	0.0 (3)
C2—C3—C4—C5	0.5 (4)	C16—C15—C19—C20	179.6 (2)
C3—C4—C5—C6	−0.7 (4)	C24—C19—C20—C21	0.7 (3)
C4—C5—C6—C1	0.2 (3)	C15—C19—C20—C21	−178.03 (19)
C2—C1—C6—C5	0.6 (3)	C19—C20—C21—C22	0.0 (3)
S1—C1—C6—C5	177.56 (16)	C20—C21—C22—C23	−0.4 (3)
C12—C7—C8—C9	−0.6 (3)	C21—C22—C23—C24	0.1 (3)
N1—C7—C8—C9	178.78 (18)	C22—C23—C24—C19	0.7 (3)
C7—C8—C9—C10	−1.0 (3)	C22—C23—C24—O3	179.87 (18)
C8—C9—C10—C11	1.4 (3)	C20—C19—C24—C23	−1.1 (3)
C9—C10—C11—C12	−0.1 (3)	C15—C19—C24—C23	177.98 (17)
C10—C11—C12—C7	−1.4 (3)	C20—C19—C24—O3	179.64 (15)
C10—C11—C12—C13	178.13 (18)	C15—C19—C24—O3	−1.28 (19)
C8—C7—C12—C11	1.7 (3)	C17—C18—N1—C7	179.74 (17)
N1—C7—C12—C11	−177.71 (15)	C13—C18—N1—C7	2.44 (18)
C8—C7—C12—C13	−177.86 (15)	C17—C18—N1—S1	−35.9 (2)
N1—C7—C12—C13	2.68 (19)	C13—C18—N1—S1	146.81 (13)
C11—C12—C13—C14	−0.1 (3)	C8—C7—N1—C18	177.44 (17)
C7—C12—C13—C14	179.43 (17)	C12—C7—N1—C18	−3.16 (18)
C11—C12—C13—C18	179.31 (18)	C8—C7—N1—S1	32.3 (2)
C7—C12—C13—C18	−1.15 (19)	C12—C7—N1—S1	−148.30 (13)
C18—C13—C14—C15	0.5 (2)	C17—C16—O3—C24	178.58 (16)
C12—C13—C14—C15	179.87 (16)	C15—C16—O3—C24	−0.83 (19)
C13—C14—C15—C16	−1.2 (2)	C23—C24—O3—C16	−177.93 (17)
C13—C14—C15—C19	178.28 (17)	C19—C24—O3—C16	1.32 (19)
C14—C15—C16—C17	0.3 (3)	C18—N1—S1—O1	169.12 (13)
C19—C15—C16—C17	−179.32 (17)	C7—N1—S1—O1	−51.20 (15)
C14—C15—C16—O3	179.70 (14)	C18—N1—S1—O2	40.22 (15)
C19—C15—C16—O3	0.08 (18)	C7—N1—S1—O2	179.89 (12)
O3—C16—C17—C18	−178.05 (15)	C18—N1—S1—C1	−75.31 (15)
C15—C16—C17—C18	1.3 (3)	C7—N1—S1—C1	64.37 (15)
C16—C17—C18—C13	−2.0 (3)	C6—C1—S1—O1	19.30 (19)
C16—C17—C18—N1	−178.95 (16)	C2—C1—S1—O1	−163.68 (15)
C14—C13—C18—C17	1.2 (3)	C6—C1—S1—O2	151.45 (16)
C12—C13—C18—C17	−178.32 (16)	C2—C1—S1—O2	−31.52 (18)
C14—C13—C18—N1	178.66 (14)	C6—C1—S1—N1	−94.69 (17)
C12—C13—C18—N1	−0.84 (18)	C2—C1—S1—N1	82.34 (17)

Experimental details

Crystal data
Chemical formula	C₂₄H₁₅NO₃S
M_r	397.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	9.031 (5), 10.752 (6), 19.217 (5)
β (°)	100.738 (5)
V (Å³)	1833.3 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.949, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	16640, 4462, 2763
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.112, 1.04
No. of reflections	4462
No. of parameters	262
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.30

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

Acknowledgements

The authors wish to acknowledge SAIF, IIT, Madras, for the data collection.

References

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