Phen­yl(1-phenyl­sulfonyl-1H-indol-2-yl)methanone

Ranjith, S.; SubbiahPandi, A.; Govindan, E.; Dhayalan, V.; MohanaKrishnan, A.K.

doi:10.1107/S1600536811008439

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o844

doi:10.1107/S1600536811008439

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Phenyl(1-phenylsulfonyl-1H-indol-2-yl)methanone

S. Ranjith,^a A. SubbiahPandi,^a ^* E. Govindan,^a V. Dhayalan ^b and A. K. MohanaKrishnan ^b

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: a_sp59@yahoo.in

(Received 13 January 2011; accepted 5 March 2011; online 12 March 2011)

The asymmetric unit of the title compound, C₂₁H₁₅NO₃S, contains two crystallographically independent molecules. As a result of the electron-withdrawing character of the phenylsulfonyl groups, the N—Csp² bond lengths are slightly longer than the anticipated value of approximately 1.35 Å for N atoms with planar configurations. Both unique S atoms have a distorted tetrahedral configuration. In each molecule, the indole ring system is essentially planar (r.m.s. deviations for all non-H atoms of 0.020 and 0.023 Å). In one molecule, the indole ring system makes dihedral angles of 65.7 (8) and 73.4 (8)°, respectively, with the benzene and phenyl rings [62.2 (7) and 72.1 (7)°, respectively, in the other molecule].

Related literature

For the biological activity of compounds containing an indole ring system, see: Ma et al. (2001 ); Zhou et al. (2006 ); Zhao et al. (2002 ); Williams et al. (1993 ). For related structures, see: Chakkaravarthi et al. (2010 ); Kavitha et al. (2010 ). For a discussion of the geometry at the N atom, see: Beddoes et al. (1986 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₁₅NO₃S
M_r = 361.40
Triclinic, $[P \overline 1]$
a = 9.3291 (6) Å
b = 11.1498 (7) Å
c = 17.8134 (10) Å
α = 89.433 (3)°
β = 81.623 (2)°
γ = 71.993 (3)°
V = 1742.13 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.985
30464 measured reflections
8730 independent reflections
6363 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.138
S = 0.99
8730 reflections
470 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008439/nk2081sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008439/nk2081Isup2.hkl

checkCIF report

Comment top

The indole ring system is present in a number of natural products, many of which are found to possess anticancer, antimalarial and antihypertensive activities (Ma et al., 2001; Zhou et al., 2006; Zhao et al., 2002). In addition, phenylsulfonyl indole compounds inhibit the HIV-1 RT enzyme in vitro and HTLVIIIb viral spread in MT-4 human T-lymphoid cells (Williams et al., 1993). Sulfonamide derivates are well known drugs and are used to control diseases caused by bacterial infections. Against this background and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.

X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The bond lengths and angles in (Fig. 1) agree with those observed in other phenylsulfonylindoles (Chakkaravarthi et al., 2010). In both the molecules, the indole ring systems are essentially planar, with r.m.s. deviation of 0.028 and 0.034Å for atoms C6 and C6'. In both the molecules, the sum of bond angles around N1[359.1 (11)°] of the pyrrole ring is in accordance with sp³ hybridization (Beddoes et al., 1986). In molecule A, indole ring system make the dihedral angles of 65.7 (8) and 73.4 (8)°, respectively, with the benzene and phenyl rings and also in molecule B, indole ring system make the dihedral angles of 62.2 (7) and 72.1 (7)°, respectively, with the benzene and phenyl rings.

The S–O, S–C, and S–N distances are 1.421 (1), 1.755 (2) and 1.673 (1) Å, respectively and these values are comparable as observed in similar structures (Chakkaravarthi et al., 2010). As a result of the electron-withdrawing character of the phenylsulfonyl groups, the N–Csp² bond lengths, viz. N1–C1 [1.414 (2) Å], N1'–C1' [1.415 (2) Å], N1–C8 [1.416 (2) Å] and N1'–C8' [1.417 (2) Å], are longer than the mean value of 1.355 (1)Å reported for N atoms with planar configurations (Allen et al., 1987). In both the molecules,the S atom exhibits significant deviation from that of a regular tetrahedron, with the largest deviations being seen for the O–S–O [O1–S1–O2 119.5 (9)° & O1'–S1'–O2' 119.7 (8)°] and O–S–N angles [O1–S1–N1 105.1 (7)° & O1'–S1'–N1' 104.8 (7)°]. The widening of the angles may be due to repulsive interactions between the two short S=O bonds, similar to what is observed in related structures (Kavitha et al., 2010).

Related literature top

For the biological activity of compounds containing an indole ring system, see: Ma et al. (2001); Zhou et al. (2006); Zhao et al. (2002); Williams et al. (1993). For related structures, see: Chakkaravarthi et al. (2010); Kavitha et al. (2010). For a discussion of the geometry at the N atom, see: Beddoes et al. (1986). For standard bond-length data, see: Allen et al. (1987).

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), phenacylbromides (0.45 g, 2.26 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). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The two crystallographically unique molecules. Displacement ellipsoids are drawn at the 30% probability level.

Phenyl(1-phenylsulfonyl-1H-indol-2-yl)methanone top

Crystal data top

C₂₁H₁₅NO₃S	Z = 4
M_r = 361.40	F(000) = 752
Triclinic, P1	D_x = 1.378 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3291 (6) Å	Cell parameters from 8730 reflections
b = 11.1498 (7) Å	θ = 1.2–28.7°
c = 17.8134 (10) Å	µ = 0.21 mm⁻¹
α = 89.433 (3)°	T = 293 K
β = 81.623 (2)°	Block, white
γ = 71.993 (3)°	0.25 × 0.22 × 0.19 mm
V = 1742.13 (18) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	8730 independent reflections
Radiation source: fine-focus sealed tube	6363 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω and ϕ scans	θ_max = 28.7°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.981, T_max = 0.985	k = −14→14
30464 measured reflections	l = −23→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.082P)² + 0.1847P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
8730 reflections	Δρ_max = 0.27 e Å⁻³
470 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.085 (3)

Crystal data top

C₂₁H₁₅NO₃S	γ = 71.993 (3)°
M_r = 361.40	V = 1742.13 (18) Å³
Triclinic, P1	Z = 4
a = 9.3291 (6) Å	Mo Kα radiation
b = 11.1498 (7) Å	µ = 0.21 mm⁻¹
c = 17.8134 (10) Å	T = 293 K
α = 89.433 (3)°	0.25 × 0.22 × 0.19 mm
β = 81.623 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	8730 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6363 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.985	R_int = 0.041
30464 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 0.99	Δρ_max = 0.27 e Å⁻³
8730 reflections	Δρ_min = −0.33 e Å⁻³
470 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

	x	y	z	U_iso*/U_eq
C1	1.12210 (18)	0.80297 (15)	0.33999 (9)	0.0466 (4)
C1'	1.04606 (17)	0.31674 (14)	0.15061 (8)	0.0427 (3)
C2'	1.1137 (2)	0.19223 (16)	0.16963 (10)	0.0549 (4)
H2'	1.0634	0.1321	0.1694	0.066*
C2	1.1947 (2)	0.67756 (17)	0.31637 (11)	0.0593 (4)
H2	1.1406	0.6201	0.3160	0.071*
C3	1.3500 (2)	0.6420 (2)	0.29356 (11)	0.0679 (5)
H3	1.4015	0.5585	0.2779	0.082*
C3'	1.2583 (2)	0.16248 (19)	0.18871 (10)	0.0620 (5)
H3'	1.3061	0.0802	0.2016	0.074*
C4'	1.3354 (2)	0.25122 (19)	0.18944 (10)	0.0630 (5)
H4'	1.4333	0.2271	0.2022	0.076*
C4	1.4318 (2)	0.7265 (2)	0.29317 (12)	0.0701 (6)
H4	1.5367	0.6987	0.2777	0.084*
C5	1.3603 (2)	0.8508 (2)	0.31527 (11)	0.0621 (5)
H5	1.4157	0.9074	0.3146	0.074*
C5'	1.26861 (18)	0.37364 (18)	0.17157 (10)	0.0559 (4)
H5'	1.3200	0.4330	0.1720	0.067*
C6	1.20280 (18)	0.89080 (16)	0.33877 (9)	0.0486 (4)
C6'	1.12073 (17)	0.40739 (15)	0.15260 (9)	0.0454 (3)
C7	1.09697 (19)	1.00924 (16)	0.36680 (10)	0.0514 (4)
H7	1.1201	1.0840	0.3712	0.062*
C7'	1.02433 (17)	0.52315 (15)	0.12936 (9)	0.0475 (4)
H7'	1.0458	0.5993	0.1265	0.057*
C8'	0.89647 (17)	0.50409 (14)	0.11210 (9)	0.0429 (3)
C8	0.95772 (18)	0.99525 (15)	0.38603 (9)	0.0461 (3)
C9'	0.78298 (17)	0.58882 (14)	0.06981 (9)	0.0439 (3)
C9	0.82428 (18)	1.08384 (16)	0.43345 (9)	0.0493 (4)
C10'	0.74687 (16)	0.72726 (14)	0.08203 (9)	0.0415 (3)
C10	0.79218 (18)	1.22132 (15)	0.42177 (9)	0.0468 (4)
C11	0.72410 (19)	1.30446 (17)	0.48355 (10)	0.0537 (4)
H11	0.7030	1.2735	0.5312	0.064*
C11'	0.74584 (19)	0.78266 (15)	0.15170 (9)	0.0493 (4)
H11'	0.7738	0.7326	0.1925	0.059*
C12'	0.7028 (2)	0.91320 (17)	0.16001 (11)	0.0586 (4)
H12'	0.6983	0.9508	0.2070	0.070*
C12	0.6877 (2)	1.43246 (18)	0.47447 (12)	0.0635 (5)
H12	0.6452	1.4878	0.5163	0.076*
C13	0.7142 (2)	1.47895 (18)	0.40350 (14)	0.0707 (5)
H13	0.6873	1.5656	0.3974	0.085*
C13'	0.6669 (2)	0.98698 (16)	0.09905 (12)	0.0595 (5)
H13'	0.6400	1.0743	0.1047	0.071*
C14'	0.67055 (19)	0.93190 (16)	0.02912 (11)	0.0556 (4)
H14'	0.6486	0.9820	−0.0124	0.067*
C14	0.7801 (3)	1.39750 (19)	0.34158 (13)	0.0721 (6)
H14	0.7972	1.4293	0.2938	0.087*
C15	0.8211 (2)	1.26808 (17)	0.35029 (10)	0.0593 (4)
H15	0.8676	1.2130	0.3087	0.071*
C15'	0.70660 (17)	0.80322 (15)	0.02128 (9)	0.0480 (4)
H15'	0.7041	0.7666	−0.0250	0.058*
C16	0.78168 (17)	0.77029 (15)	0.46542 (9)	0.0460 (3)
C16'	0.76892 (17)	0.26929 (14)	0.03053 (9)	0.0425 (3)
C17'	0.64230 (19)	0.31640 (17)	−0.00556 (10)	0.0525 (4)
H17'	0.5545	0.3754	0.0191	0.063*
C17	0.6358 (2)	0.81398 (18)	0.50410 (11)	0.0604 (4)
H17	0.5582	0.8697	0.4820	0.073*
C18'	0.6491 (2)	0.27381 (19)	−0.07907 (11)	0.0615 (5)
H18'	0.5651	0.3047	−0.1042	0.074*
C18	0.6068 (3)	0.7732 (2)	0.57678 (12)	0.0728 (6)
H18	0.5088	0.8018	0.6039	0.087*
C19	0.7221 (3)	0.6908 (2)	0.60898 (11)	0.0720 (6)
H19	0.7017	0.6646	0.6580	0.086*
C19'	0.7790 (2)	0.18625 (18)	−0.11532 (10)	0.0595 (4)
H19'	0.7826	0.1588	−0.1649	0.071*
C20	0.8674 (2)	0.64670 (19)	0.56934 (12)	0.0674 (5)
H20	0.9447	0.5904	0.5913	0.081*
C20'	0.9040 (2)	0.13900 (17)	−0.07847 (11)	0.0572 (4)
H20'	0.9913	0.0793	−0.1031	0.069*
C21'	0.89966 (18)	0.18017 (15)	−0.00517 (10)	0.0500 (4)
H21'	0.9835	0.1485	0.0200	0.060*
C21	0.8978 (2)	0.68629 (17)	0.49705 (10)	0.0559 (4)
H21	0.9955	0.6568	0.4697	0.067*
N1	0.96883 (15)	0.86837 (12)	0.36984 (7)	0.0467 (3)
N1'	0.90578 (14)	0.37628 (11)	0.12457 (7)	0.0426 (3)
O1'	0.80070 (16)	0.20614 (12)	0.16827 (7)	0.0645 (4)
O1	0.87435 (16)	0.70347 (13)	0.32343 (7)	0.0672 (4)
O2'	0.62388 (13)	0.41561 (13)	0.14936 (7)	0.0630 (3)
O2	0.69510 (15)	0.91680 (14)	0.35443 (8)	0.0673 (4)
O3	0.74722 (15)	1.04506 (12)	0.48283 (7)	0.0645 (3)
O3'	0.72679 (15)	0.54592 (11)	0.02333 (7)	0.0602 (3)
S1'	0.76114 (4)	0.31681 (4)	0.12514 (2)	0.04706 (13)
S1	0.81966 (5)	0.81457 (4)	0.37162 (2)	0.05089 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0480 (8)	0.0498 (8)	0.0411 (8)	−0.0155 (7)	−0.0035 (6)	0.0043 (7)
C1'	0.0429 (8)	0.0457 (8)	0.0392 (7)	−0.0125 (6)	−0.0073 (6)	0.0004 (6)
C2'	0.0607 (10)	0.0490 (9)	0.0533 (10)	−0.0134 (8)	−0.0115 (8)	0.0090 (7)
C2	0.0634 (11)	0.0521 (10)	0.0576 (10)	−0.0154 (8)	0.0006 (8)	−0.0032 (8)
C3	0.0633 (11)	0.0638 (11)	0.0618 (12)	−0.0044 (9)	0.0048 (9)	0.0003 (9)
C3'	0.0611 (11)	0.0620 (11)	0.0512 (10)	−0.0002 (9)	−0.0134 (8)	0.0085 (8)
C4'	0.0468 (9)	0.0795 (13)	0.0536 (10)	−0.0025 (9)	−0.0160 (8)	−0.0050 (9)
C4	0.0478 (10)	0.0844 (14)	0.0652 (12)	−0.0069 (10)	0.0018 (9)	0.0135 (11)
C5	0.0480 (9)	0.0751 (12)	0.0648 (11)	−0.0225 (9)	−0.0077 (8)	0.0190 (10)
C5'	0.0421 (8)	0.0696 (11)	0.0554 (10)	−0.0145 (8)	−0.0109 (7)	−0.0107 (8)
C6	0.0480 (8)	0.0543 (9)	0.0459 (8)	−0.0189 (7)	−0.0093 (7)	0.0106 (7)
C6'	0.0422 (8)	0.0493 (8)	0.0449 (8)	−0.0135 (7)	−0.0085 (6)	−0.0040 (7)
C7	0.0527 (9)	0.0491 (9)	0.0562 (10)	−0.0207 (7)	−0.0100 (7)	0.0083 (7)
C7'	0.0453 (8)	0.0435 (8)	0.0574 (9)	−0.0176 (7)	−0.0105 (7)	−0.0017 (7)
C8'	0.0432 (8)	0.0393 (7)	0.0479 (8)	−0.0146 (6)	−0.0084 (6)	0.0016 (6)
C8	0.0489 (8)	0.0442 (8)	0.0464 (8)	−0.0151 (7)	−0.0093 (7)	0.0042 (7)
C9'	0.0413 (8)	0.0439 (8)	0.0480 (8)	−0.0145 (6)	−0.0082 (6)	0.0016 (6)
C9	0.0495 (9)	0.0514 (9)	0.0483 (9)	−0.0169 (7)	−0.0092 (7)	0.0025 (7)
C10'	0.0366 (7)	0.0411 (7)	0.0469 (8)	−0.0125 (6)	−0.0054 (6)	0.0020 (6)
C10	0.0469 (8)	0.0469 (8)	0.0472 (9)	−0.0137 (7)	−0.0110 (7)	−0.0008 (7)
C11	0.0499 (9)	0.0575 (10)	0.0520 (9)	−0.0134 (8)	−0.0085 (7)	−0.0041 (8)
C11'	0.0521 (9)	0.0501 (9)	0.0459 (9)	−0.0169 (7)	−0.0061 (7)	0.0022 (7)
C12'	0.0617 (10)	0.0544 (10)	0.0585 (10)	−0.0194 (8)	−0.0012 (8)	−0.0122 (8)
C12	0.0565 (10)	0.0572 (11)	0.0749 (13)	−0.0128 (9)	−0.0129 (9)	−0.0175 (9)
C13	0.0742 (13)	0.0469 (10)	0.0918 (16)	−0.0160 (9)	−0.0213 (11)	0.0011 (10)
C13'	0.0523 (10)	0.0404 (8)	0.0825 (13)	−0.0135 (7)	−0.0015 (9)	0.0004 (9)
C14'	0.0475 (9)	0.0502 (9)	0.0667 (11)	−0.0122 (7)	−0.0084 (8)	0.0154 (8)
C14	0.0906 (15)	0.0569 (11)	0.0682 (12)	−0.0203 (10)	−0.0163 (11)	0.0143 (10)
C15	0.0727 (12)	0.0522 (10)	0.0505 (10)	−0.0154 (9)	−0.0103 (9)	0.0018 (8)
C15'	0.0441 (8)	0.0505 (9)	0.0480 (9)	−0.0125 (7)	−0.0075 (7)	0.0042 (7)
C16	0.0454 (8)	0.0494 (8)	0.0485 (9)	−0.0218 (7)	−0.0079 (7)	−0.0002 (7)
C16'	0.0414 (7)	0.0425 (8)	0.0492 (8)	−0.0202 (6)	−0.0090 (6)	0.0036 (6)
C17'	0.0431 (8)	0.0557 (9)	0.0591 (10)	−0.0130 (7)	−0.0135 (7)	−0.0017 (8)
C17	0.0479 (9)	0.0646 (11)	0.0661 (11)	−0.0161 (8)	−0.0030 (8)	0.0049 (9)
C18'	0.0569 (10)	0.0734 (12)	0.0590 (11)	−0.0206 (9)	−0.0234 (8)	0.0028 (9)
C18	0.0672 (12)	0.0823 (14)	0.0642 (12)	−0.0260 (11)	0.0116 (10)	−0.0008 (11)
C19	0.0952 (16)	0.0792 (14)	0.0492 (10)	−0.0406 (12)	−0.0055 (10)	0.0034 (10)
C19'	0.0677 (11)	0.0671 (11)	0.0502 (10)	−0.0294 (9)	−0.0108 (8)	−0.0017 (8)
C20	0.0764 (13)	0.0684 (12)	0.0638 (12)	−0.0252 (10)	−0.0255 (10)	0.0125 (10)
C20'	0.0509 (9)	0.0571 (10)	0.0606 (11)	−0.0166 (8)	0.0010 (8)	−0.0061 (8)
C21'	0.0417 (8)	0.0506 (9)	0.0590 (10)	−0.0143 (7)	−0.0116 (7)	0.0040 (7)
C21	0.0479 (9)	0.0632 (10)	0.0577 (10)	−0.0182 (8)	−0.0090 (8)	0.0008 (8)
N1	0.0466 (7)	0.0470 (7)	0.0483 (7)	−0.0194 (6)	−0.0016 (6)	−0.0014 (6)
N1'	0.0433 (7)	0.0406 (6)	0.0490 (7)	−0.0177 (5)	−0.0130 (5)	0.0048 (5)
O1'	0.0880 (9)	0.0694 (8)	0.0565 (7)	−0.0497 (7)	−0.0219 (7)	0.0190 (6)
O1	0.0812 (9)	0.0753 (9)	0.0569 (7)	−0.0428 (7)	−0.0059 (6)	−0.0125 (6)
O2'	0.0451 (6)	0.0798 (9)	0.0639 (8)	−0.0232 (6)	0.0018 (6)	−0.0145 (7)
O2	0.0564 (7)	0.0859 (9)	0.0659 (8)	−0.0249 (7)	−0.0245 (6)	0.0188 (7)
O3	0.0687 (8)	0.0578 (7)	0.0618 (8)	−0.0197 (6)	0.0071 (6)	0.0036 (6)
O3'	0.0687 (8)	0.0488 (7)	0.0688 (8)	−0.0171 (6)	−0.0303 (6)	−0.0006 (6)
S1'	0.0479 (2)	0.0545 (2)	0.0467 (2)	−0.02702 (18)	−0.00772 (17)	0.00296 (17)
S1	0.0513 (2)	0.0616 (3)	0.0474 (2)	−0.0268 (2)	−0.01145 (18)	0.00232 (19)

Geometric parameters (Å, º) top

C1—C2	1.391 (2)	C12'—C13'	1.373 (3)
C1—C6	1.406 (2)	C12'—H12'	0.9300
C1—N1	1.414 (2)	C12—C13	1.379 (3)
C1'—C6'	1.397 (2)	C12—H12	0.9300
C1'—C2'	1.397 (2)	C13—C14	1.377 (3)
C1'—N1'	1.4150 (18)	C13—H13	0.9300
C2'—C3'	1.378 (3)	C13'—C14'	1.386 (3)
C2'—H2'	0.9300	C13'—H13'	0.9300
C2—C3	1.378 (3)	C14'—C15'	1.372 (2)
C2—H2	0.9300	C14'—H14'	0.9300
C3—C4	1.383 (3)	C14—C15	1.387 (3)
C3—H3	0.9300	C14—H14	0.9300
C3'—C4'	1.393 (3)	C15—H15	0.9300
C3'—H3'	0.9300	C15'—H15'	0.9300
C4'—C5'	1.370 (3)	C16—C17	1.374 (2)
C4'—H4'	0.9300	C16—C21	1.381 (2)
C4—C5	1.372 (3)	C16—S1	1.7551 (16)
C4—H4	0.9300	C16'—C17'	1.384 (2)
C5—C6	1.398 (2)	C16'—C21'	1.384 (2)
C5—H5	0.9300	C16'—S1'	1.7563 (16)
C5'—C6'	1.404 (2)	C17'—C18'	1.383 (3)
C5'—H5'	0.9300	C17'—H17'	0.9300
C6—C7	1.425 (2)	C17—C18	1.385 (3)
C6'—C7'	1.423 (2)	C17—H17	0.9300
C7—C8	1.350 (2)	C18'—C19'	1.375 (3)
C7—H7	0.9300	C18'—H18'	0.9300
C7'—C8'	1.352 (2)	C18—C19	1.374 (3)
C7'—H7'	0.9300	C18—H18	0.9300
C8'—N1'	1.4179 (18)	C19—C20	1.376 (3)
C8'—C9'	1.477 (2)	C19—H19	0.9300
C8—N1	1.416 (2)	C19'—C20'	1.380 (3)
C8—C9	1.479 (2)	C19'—H19'	0.9300
C9'—O3'	1.2158 (19)	C20—C21	1.376 (3)
C9'—C10'	1.486 (2)	C20—H20	0.9300
C9—O3	1.216 (2)	C20'—C21'	1.379 (3)
C9—C10	1.487 (2)	C20'—H20'	0.9300
C10'—C11'	1.389 (2)	C21'—H21'	0.9300
C10'—C15'	1.390 (2)	C21—H21	0.9300
C10—C11	1.388 (2)	N1—S1	1.6734 (13)
C10—C15	1.393 (2)	N1'—S1'	1.6761 (12)
C11—C12	1.375 (2)	O1'—S1'	1.4254 (12)
C11—H11	0.9300	O1—S1	1.4264 (14)
C11'—C12'	1.388 (2)	O2'—S1'	1.4197 (13)
C11'—H11'	0.9300	O2—S1	1.4217 (13)

C2—C1—C6	121.55 (16)	C14—C13—C12	120.26 (18)
C2—C1—N1	131.80 (16)	C14—C13—H13	119.9
C6—C1—N1	106.64 (14)	C12—C13—H13	119.9
C6'—C1'—C2'	121.26 (14)	C12'—C13'—C14'	120.30 (16)
C6'—C1'—N1'	107.10 (13)	C12'—C13'—H13'	119.8
C2'—C1'—N1'	131.59 (14)	C14'—C13'—H13'	119.8
C3'—C2'—C1'	117.05 (17)	C15'—C14'—C13'	119.78 (16)
C3'—C2'—H2'	121.5	C15'—C14'—H14'	120.1
C1'—C2'—H2'	121.5	C13'—C14'—H14'	120.1
C3—C2—C1	117.18 (19)	C13—C14—C15	120.16 (19)
C3—C2—H2	121.4	C13—C14—H14	119.9
C1—C2—H2	121.4	C15—C14—H14	119.9
C2—C3—C4	122.13 (19)	C14—C15—C10	119.49 (18)
C2—C3—H3	118.9	C14—C15—H15	120.3
C4—C3—H3	118.9	C10—C15—H15	120.3
C2'—C3'—C4'	122.34 (17)	C14'—C15'—C10'	120.45 (16)
C2'—C3'—H3'	118.8	C14'—C15'—H15'	119.8
C4'—C3'—H3'	118.8	C10'—C15'—H15'	119.8
C5'—C4'—C3'	120.69 (16)	C17—C16—C21	121.50 (16)
C5'—C4'—H4'	119.7	C17—C16—S1	119.44 (13)
C3'—C4'—H4'	119.7	C21—C16—S1	118.96 (13)
C5—C4—C3	120.89 (18)	C17'—C16'—C21'	121.27 (15)
C5—C4—H4	119.6	C17'—C16'—S1'	119.65 (13)
C3—C4—H4	119.6	C21'—C16'—S1'	118.99 (12)
C4—C5—C6	118.82 (18)	C18'—C17'—C16'	118.61 (16)
C4—C5—H5	120.6	C18'—C17'—H17'	120.7
C6—C5—H5	120.6	C16'—C17'—H17'	120.7
C4'—C5'—C6'	118.42 (17)	C16—C17—C18	118.52 (18)
C4'—C5'—H5'	120.8	C16—C17—H17	120.7
C6'—C5'—H5'	120.8	C18—C17—H17	120.7
C5—C6—C1	119.41 (16)	C19'—C18'—C17'	120.57 (17)
C5—C6—C7	132.82 (17)	C19'—C18'—H18'	119.7
C1—C6—C7	107.72 (14)	C17'—C18'—H18'	119.7
C1'—C6'—C5'	120.22 (15)	C19—C18—C17	120.33 (19)
C1'—C6'—C7'	107.86 (13)	C19—C18—H18	119.8
C5'—C6'—C7'	131.83 (16)	C17—C18—H18	119.8
C8—C7—C6	108.95 (15)	C18—C19—C20	120.59 (18)
C8—C7—H7	125.5	C18—C19—H19	119.7
C6—C7—H7	125.5	C20—C19—H19	119.7
C8'—C7'—C6'	108.73 (14)	C18'—C19'—C20'	120.29 (17)
C8'—C7'—H7'	125.6	C18'—C19'—H19'	119.9
C6'—C7'—H7'	125.6	C20'—C19'—H19'	119.9
C7'—C8'—N1'	108.63 (13)	C21—C20—C19	119.68 (18)
C7'—C8'—C9'	126.66 (14)	C21—C20—H20	120.2
N1'—C8'—C9'	123.14 (13)	C19—C20—H20	120.2
C7—C8—N1	108.47 (14)	C21'—C20'—C19'	120.09 (17)
C7—C8—C9	126.76 (15)	C21'—C20'—H20'	120.0
N1—C8—C9	123.09 (14)	C19'—C20'—H20'	120.0
O3'—C9'—C8'	120.50 (14)	C20'—C21'—C16'	119.15 (15)
O3'—C9'—C10'	121.06 (14)	C20'—C21'—H21'	120.4
C8'—C9'—C10'	118.33 (13)	C16'—C21'—H21'	120.4
O3—C9—C8	120.57 (15)	C20—C21—C16	119.37 (17)
O3—C9—C10	121.10 (15)	C20—C21—H21	120.3
C8—C9—C10	118.26 (14)	C16—C21—H21	120.3
C11'—C10'—C15'	119.57 (14)	C1—N1—C8	108.21 (13)
C11'—C10'—C9'	122.77 (14)	C1—N1—S1	126.37 (11)
C15'—C10'—C9'	117.61 (14)	C8—N1—S1	124.59 (11)
C11—C10—C15	119.75 (16)	C1'—N1'—C8'	107.66 (12)
C11—C10—C9	118.40 (15)	C1'—N1'—S1'	126.32 (10)
C15—C10—C9	121.76 (15)	C8'—N1'—S1'	124.95 (10)
C12—C11—C10	120.12 (17)	O2'—S1'—O1'	119.73 (8)
C12—C11—H11	119.9	O2'—S1'—N1'	107.50 (7)
C10—C11—H11	119.9	O1'—S1'—N1'	104.83 (7)
C12'—C11'—C10'	119.56 (16)	O2'—S1'—C16'	110.44 (8)
C12'—C11'—H11'	120.2	O1'—S1'—C16'	107.87 (8)
C10'—C11'—H11'	120.2	N1'—S1'—C16'	105.46 (7)
C13'—C12'—C11'	120.25 (18)	O2—S1—O1	119.56 (9)
C13'—C12'—H12'	119.9	O2—S1—N1	107.30 (7)
C11'—C12'—H12'	119.9	O1—S1—N1	105.18 (7)
C11—C12—C13	120.17 (18)	O2—S1—C16	110.09 (8)
C11—C12—H12	119.9	O1—S1—C16	108.48 (8)
C13—C12—H12	119.9	N1—S1—C16	105.20 (7)

C6'—C1'—C2'—C3'	−1.4 (2)	C13'—C14'—C15'—C10'	−3.2 (2)
N1'—C1'—C2'—C3'	175.84 (16)	C11'—C10'—C15'—C14'	2.0 (2)
C6—C1—C2—C3	1.7 (3)	C9'—C10'—C15'—C14'	179.39 (14)
N1—C1—C2—C3	−176.50 (17)	C21'—C16'—C17'—C18'	−0.8 (2)
C1—C2—C3—C4	−0.6 (3)	S1'—C16'—C17'—C18'	−177.48 (14)
C1'—C2'—C3'—C4'	0.1 (3)	C21—C16—C17—C18	0.8 (3)
C2'—C3'—C4'—C5'	0.6 (3)	S1—C16—C17—C18	177.02 (16)
C2—C3—C4—C5	−0.5 (3)	C16'—C17'—C18'—C19'	0.2 (3)
C3—C4—C5—C6	0.4 (3)	C16—C17—C18—C19	−0.1 (3)
C3'—C4'—C5'—C6'	0.1 (3)	C17—C18—C19—C20	−0.6 (3)
C4—C5—C6—C1	0.7 (3)	C17'—C18'—C19'—C20'	0.5 (3)
C4—C5—C6—C7	177.74 (18)	C18—C19—C20—C21	0.5 (3)
C2—C1—C6—C5	−1.8 (2)	C18'—C19'—C20'—C21'	−0.5 (3)
N1—C1—C6—C5	176.81 (15)	C19'—C20'—C21'—C16'	−0.2 (3)
C2—C1—C6—C7	−179.50 (16)	C17'—C16'—C21'—C20'	0.8 (2)
N1—C1—C6—C7	−0.91 (17)	S1'—C16'—C21'—C20'	177.51 (13)
C2'—C1'—C6'—C5'	2.1 (2)	C19—C20—C21—C16	0.2 (3)
N1'—C1'—C6'—C5'	−175.76 (14)	C17—C16—C21—C20	−0.9 (3)
C2'—C1'—C6'—C7'	179.13 (15)	S1—C16—C21—C20	−177.14 (14)
N1'—C1'—C6'—C7'	1.29 (17)	C2—C1—N1—C8	178.72 (17)
C4'—C5'—C6'—C1'	−1.4 (2)	C6—C1—N1—C8	0.33 (17)
C4'—C5'—C6'—C7'	−177.59 (17)	C2—C1—N1—S1	−11.4 (3)
C5—C6—C7—C8	−176.10 (18)	C6—C1—N1—S1	170.23 (11)
C1—C6—C7—C8	1.19 (19)	C7—C8—N1—C1	0.41 (18)
C1'—C6'—C7'—C8'	−1.27 (18)	C9—C8—N1—C1	−165.74 (14)
C5'—C6'—C7'—C8'	175.31 (17)	C7—C8—N1—S1	−169.71 (12)
C6'—C7'—C8'—N1'	0.73 (18)	C9—C8—N1—S1	24.1 (2)
C6'—C7'—C8'—C9'	−165.23 (15)	C6'—C1'—N1'—C8'	−0.86 (16)
C6—C7—C8—N1	−0.98 (18)	C2'—C1'—N1'—C8'	−178.39 (16)
C6—C7—C8—C9	164.52 (15)	C6'—C1'—N1'—S1'	−169.40 (11)
C7'—C8'—C9'—O3'	139.58 (18)	C2'—C1'—N1'—S1'	13.1 (2)
N1'—C8'—C9'—O3'	−24.5 (2)	C7'—C8'—N1'—C1'	0.08 (17)
C7'—C8'—C9'—C10'	−36.7 (2)	C9'—C8'—N1'—C1'	166.64 (14)
N1'—C8'—C9'—C10'	159.25 (14)	C7'—C8'—N1'—S1'	168.82 (12)
C7—C8—C9—O3	−135.37 (19)	C9'—C8'—N1'—S1'	−24.6 (2)
N1—C8—C9—O3	28.2 (2)	C1'—N1'—S1'—O2'	137.76 (13)
C7—C8—C9—C10	41.5 (2)	C8'—N1'—S1'—O2'	−28.89 (15)
N1—C8—C9—C10	−154.98 (15)	C1'—N1'—S1'—O1'	9.35 (15)
O3'—C9'—C10'—C11'	149.60 (16)	C8'—N1'—S1'—O1'	−157.30 (13)
C8'—C9'—C10'—C11'	−34.2 (2)	C1'—N1'—S1'—C16'	−104.39 (13)
O3'—C9'—C10'—C15'	−27.7 (2)	C8'—N1'—S1'—C16'	88.95 (14)
C8'—C9'—C10'—C15'	148.56 (14)	C17'—C16'—S1'—O2'	−8.10 (15)
O3—C9—C10—C11	27.8 (2)	C21'—C16'—S1'—O2'	175.18 (12)
C8—C9—C10—C11	−148.99 (15)	C17'—C16'—S1'—O1'	124.45 (13)
O3—C9—C10—C15	−148.71 (18)	C21'—C16'—S1'—O1'	−52.28 (14)
C8—C9—C10—C15	34.5 (2)	C17'—C16'—S1'—N1'	−123.95 (13)
C15—C10—C11—C12	−1.1 (3)	C21'—C16'—S1'—N1'	59.33 (13)
C9—C10—C11—C12	−177.72 (16)	C1—N1—S1—O2	−140.16 (13)
C15'—C10'—C11'—C12'	0.8 (2)	C8—N1—S1—O2	28.17 (15)
C9'—C10'—C11'—C12'	−176.44 (15)	C1—N1—S1—O1	−11.85 (15)
C10'—C11'—C12'—C13'	−2.4 (3)	C8—N1—S1—O1	156.48 (13)
C10—C11—C12—C13	2.1 (3)	C1—N1—S1—C16	102.62 (14)
C11—C12—C13—C14	−1.4 (3)	C8—N1—S1—C16	−89.06 (14)
C11'—C12'—C13'—C14'	1.2 (3)	C17—C16—S1—O2	13.85 (17)
C12'—C13'—C14'—C15'	1.6 (3)	C21—C16—S1—O2	−169.87 (14)
C12—C13—C14—C15	−0.4 (3)	C17—C16—S1—O1	−118.69 (15)
C13—C14—C15—C10	1.4 (3)	C21—C16—S1—O1	57.58 (15)
C11—C10—C15—C14	−0.6 (3)	C17—C16—S1—N1	129.16 (15)
C9—C10—C15—C14	175.87 (18)	C21—C16—S1—N1	−54.56 (15)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅NO₃S
M_r	361.40
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.3291 (6), 11.1498 (7), 17.8134 (10)
α, β, γ (°)	89.433 (3), 81.623 (2), 71.993 (3)
V (Å³)	1742.13 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	30464, 8730, 6363
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.138, 0.99
No. of reflections	8730
No. of parameters	470
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

SR and ASP thank the Technology Business Incubator (TBI), the CAS in Crystallography and Biophysics, University of Madras, Chennai, and the Department of Science and Technology (DST) for the data collection.

References

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