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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(2-Methyl-1-phenyl­sulfonyl-1H-indol-3-yl)phenyl­methyl acetate

aDepartment of 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: manivan_1999@yahoo.com

(Received 22 October 2009; accepted 25 October 2009; online 28 October 2009)

In the title compound, C24H21NO4S, the indole ring system makes dihedral angles of 77.8 (1) and 85.4 (1)°, respectively, with the S- and C-bound phenyl rings. The mol­ecular structure is stabilized by a weak intra­molecular C—H⋯O hydrogen bond. In the crystal, a weak inter­molecular C—H⋯O hydrogen bond and a C—H⋯π inter­action are also observed.

Related literature

For the biological activity of indole derivatives, see: Chai et al. (2006[Chai, H., Zhao, C. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911-917.]); Olgen & Coban (2003[Olgen, S. & Coban, T. (2003). Biol. Pharm. Bull. 26, 736-738.]). For related structures, see: Chakkaravarthi et al. (2007[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.], 2008[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.]).

[Scheme 1]

Experimental

Crystal data
  • C24H21NO4S

  • Mr = 419.48

  • Monoclinic, P 21 /n

  • a = 14.3655 (6) Å

  • b = 8.3432 (4) Å

  • c = 18.6261 (8) Å

  • β = 108.086 (2)°

  • V = 2122.12 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 295 K

  • 0.28 × 0.24 × 0.18 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.951, Tmax = 0.968

  • 23327 measured reflections

  • 4712 independent reflections

  • 3030 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.146

  • S = 1.01

  • 4712 reflections

  • 273 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C13—H13⋯O1 0.93 2.39 2.977 (4) 121
C24—H24B⋯O2i 0.96 2.58 3.429 (4) 147
C15—H15ACg1ii 0.96 2.97 3.590 (3) 124
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x, -y, -z+1. Cg1 is the centroid of the C17–C22 ring.

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

In continuation of our studies of indole derivatives, which are known to exhibit antihepatitis B virus (Chai et al., 2006) and anti-oxidant activity (Olgen & Coban, 2003), we report the crystal structure of the title compound, (I). The bond lengths and bond angles of the title compound are agree with the reported similar structures (Chakkaravarthi et al., 2007,2008).

The phenyl rings C1—C6 and C17—C22 make dihedral angles of 77.8 (1) and 85.4 (1)°, respectively, with the indole ring system. The two phenyl rings are inclined at an angle of 62.2 (1)° with respect to each other. The torsion angles C7—N1—S1—O2 and C14—N1—S1—O1 [-36.8 (2) and 51.1 (2)°, respectively] indicate a syn conformation of the sulfonyl moiety. The sum of the bond angles around N1 [351.2 (2)°] indicates that N1 is sp2-hybridized.

The molecular structure is controlled by a weak intramolecular C—H···O hydrogen bond and the crystal packing of (I) (Fig. 2) is through weak intermolecular C—H···O hydrogen bonds and C—H···π (Table 1) interactions.

Related literature top

For the biological activity of indole derivatives, see: Chai et al. (2006); Olgen & Coban (2003). For related structures, see: Chakkaravarthi et al. (2007, 2008). Cg1 is the centroid of the C17–C22 ring.

Experimental top

To a solution of 1-phenylsulfonyl-(2-methyl-1H-indol-3-yl) (phenyl)methanol (0.5 g, 1.32 mmol) in dry DCM (20 ml) acetic anhydride (0.27 g, 2.64 mmol) and pyridine (0.2 g, 2.52 mmol) were added. It was then stirred at room temperature for 7 h under N2 atmosphere. The reaction mixture was poured over crushed ice (100 g) containing 2 ml of Conc. HCl, extracted with CHCl3 (3 × 10 ml) and dried (Na2SO4). Removal of solvent followed by recrystallization from CDCl3 afforded the compound as crystals.

Refinement top

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for C—H, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl. The components of the anisotropic displacement parameters in direction of the bond of S1and O2; C3 and C4 were restrained to be equal within an effective standard deviation of 0.001 using the DELU command in SHELXL (Sheldrick, 2008).

Structure description top

In continuation of our studies of indole derivatives, which are known to exhibit antihepatitis B virus (Chai et al., 2006) and anti-oxidant activity (Olgen & Coban, 2003), we report the crystal structure of the title compound, (I). The bond lengths and bond angles of the title compound are agree with the reported similar structures (Chakkaravarthi et al., 2007,2008).

The phenyl rings C1—C6 and C17—C22 make dihedral angles of 77.8 (1) and 85.4 (1)°, respectively, with the indole ring system. The two phenyl rings are inclined at an angle of 62.2 (1)° with respect to each other. The torsion angles C7—N1—S1—O2 and C14—N1—S1—O1 [-36.8 (2) and 51.1 (2)°, respectively] indicate a syn conformation of the sulfonyl moiety. The sum of the bond angles around N1 [351.2 (2)°] indicates that N1 is sp2-hybridized.

The molecular structure is controlled by a weak intramolecular C—H···O hydrogen bond and the crystal packing of (I) (Fig. 2) is through weak intermolecular C—H···O hydrogen bonds and C—H···π (Table 1) interactions.

For the biological activity of indole derivatives, see: Chai et al. (2006); Olgen & Coban (2003). For related structures, see: Chakkaravarthi et al. (2007, 2008). Cg1 is the centroid of the C17–C22 ring.

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 (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
(2-Methyl-1-phenylsulfonyl-1H-indol-3-yl)phenylmethyl acetate top
Crystal data top
C24H21NO4SF(000) = 880
Mr = 419.48Dx = 1.313 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6715 reflections
a = 14.3655 (6) Åθ = 2.3–25.3°
b = 8.3432 (4) ŵ = 0.18 mm1
c = 18.6261 (8) ÅT = 295 K
β = 108.086 (2)°Block, colourless
V = 2122.12 (16) Å30.28 × 0.24 × 0.18 mm
Z = 4
Data collection top
Bruker Kappa APEXII
diffractometer
4712 independent reflections
Radiation source: fine-focus sealed tube3030 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ω and φ scansθmax = 27.4°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1818
Tmin = 0.951, Tmax = 0.968k = 910
23327 measured reflectionsl = 2324
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0657P)2 + 0.817P]
where P = (Fo2 + 2Fc2)/3
4712 reflections(Δ/σ)max < 0.001
273 parametersΔρmax = 0.26 e Å3
2 restraintsΔρmin = 0.35 e Å3
Crystal data top
C24H21NO4SV = 2122.12 (16) Å3
Mr = 419.48Z = 4
Monoclinic, P21/nMo Kα radiation
a = 14.3655 (6) ŵ = 0.18 mm1
b = 8.3432 (4) ÅT = 295 K
c = 18.6261 (8) Å0.28 × 0.24 × 0.18 mm
β = 108.086 (2)°
Data collection top
Bruker Kappa APEXII
diffractometer
4712 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3030 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.968Rint = 0.043
23327 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0472 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 1.01Δρmax = 0.26 e Å3
4712 reflectionsΔρmin = 0.35 e Å3
273 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.39968 (15)0.2073 (3)0.58199 (12)0.0515 (5)
C20.49717 (19)0.1911 (4)0.58978 (19)0.0807 (8)
H20.53610.28020.58970.097*
C30.5362 (2)0.0363 (4)0.5978 (2)0.0976 (10)
H30.60240.02160.60390.117*
C40.4786 (2)0.0927 (4)0.59684 (17)0.0836 (8)
H40.50560.19490.60140.100*
C50.3827 (2)0.0755 (3)0.58934 (16)0.0741 (7)
H50.34390.16520.58850.089*
C60.34286 (18)0.0747 (3)0.58297 (14)0.0645 (7)
H60.27720.08750.57930.077*
C70.15867 (14)0.3154 (3)0.49542 (11)0.0430 (5)
C80.11839 (14)0.2508 (2)0.42695 (11)0.0416 (5)
C90.18128 (14)0.2795 (3)0.38139 (11)0.0448 (5)
C100.17326 (19)0.2446 (3)0.30680 (13)0.0623 (6)
H100.11930.18940.27620.075*
C110.2471 (2)0.2937 (4)0.27933 (16)0.0780 (8)
H110.24290.27110.22950.094*
C120.3271 (2)0.3760 (4)0.32454 (18)0.0768 (8)
H120.37580.40840.30440.092*
C130.33684 (17)0.4113 (3)0.39800 (16)0.0624 (7)
H130.39130.46620.42830.075*
C140.26243 (14)0.3622 (2)0.42576 (12)0.0450 (5)
C150.11753 (18)0.3291 (4)0.55899 (14)0.0671 (7)
H15A0.05050.29420.54270.101*
H15B0.12070.43880.57520.101*
H15C0.15470.26330.60020.101*
C160.02422 (14)0.1601 (3)0.40188 (11)0.0441 (5)
H160.00230.15240.44430.053*
C170.03687 (14)0.0071 (3)0.37520 (12)0.0462 (5)
C180.10644 (19)0.1056 (3)0.42217 (16)0.0698 (7)
H180.14450.06810.46910.084*
C190.1201 (2)0.2590 (4)0.4002 (2)0.0888 (10)
H190.16750.32400.43240.107*
C200.0652 (3)0.3164 (4)0.3322 (2)0.0871 (9)
H200.07510.41990.31750.105*
C210.0047 (2)0.2208 (4)0.28573 (17)0.0763 (8)
H210.04340.26000.23930.092*
C220.01860 (17)0.0670 (3)0.30661 (13)0.0570 (6)
H220.06610.00280.27400.068*
C230.13810 (17)0.2461 (4)0.33675 (15)0.0638 (7)
C240.1970 (2)0.3458 (4)0.27301 (16)0.0905 (10)
H24A0.26520.33530.26840.136*
H24B0.18630.31070.22710.136*
H24C0.17770.45590.28220.136*
N10.24997 (11)0.3880 (2)0.49744 (10)0.0460 (4)
O10.41254 (12)0.5105 (2)0.55926 (11)0.0776 (6)
O20.31180 (12)0.4240 (2)0.63643 (10)0.0722 (5)
O30.04306 (10)0.25213 (18)0.34207 (8)0.0521 (4)
O40.16788 (13)0.1681 (4)0.37807 (14)0.1077 (8)
S10.34717 (4)0.39792 (7)0.57453 (3)0.0550 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0450 (12)0.0497 (13)0.0509 (12)0.0019 (10)0.0020 (9)0.0002 (10)
C20.0482 (14)0.0716 (19)0.117 (2)0.0010 (13)0.0178 (15)0.0069 (16)
C30.0590 (17)0.089 (2)0.143 (3)0.0230 (13)0.0295 (18)0.018 (2)
C40.091 (2)0.0648 (18)0.093 (2)0.0246 (12)0.0245 (17)0.0178 (15)
C50.0770 (18)0.0534 (16)0.0851 (19)0.0061 (13)0.0152 (15)0.0120 (13)
C60.0546 (14)0.0528 (15)0.0786 (17)0.0003 (11)0.0098 (12)0.0062 (12)
C70.0348 (10)0.0437 (12)0.0481 (11)0.0009 (8)0.0095 (8)0.0012 (9)
C80.0350 (10)0.0425 (11)0.0461 (11)0.0017 (8)0.0110 (8)0.0030 (8)
C90.0403 (11)0.0432 (12)0.0510 (12)0.0054 (9)0.0142 (9)0.0070 (9)
C100.0609 (14)0.0761 (18)0.0529 (13)0.0012 (12)0.0222 (11)0.0023 (12)
C110.0809 (19)0.101 (2)0.0631 (15)0.0118 (17)0.0387 (15)0.0146 (15)
C120.0630 (17)0.089 (2)0.093 (2)0.0123 (15)0.0453 (16)0.0327 (17)
C130.0435 (12)0.0586 (16)0.0878 (18)0.0013 (10)0.0243 (12)0.0209 (13)
C140.0359 (10)0.0392 (12)0.0596 (13)0.0060 (8)0.0146 (9)0.0117 (9)
C150.0537 (14)0.091 (2)0.0574 (14)0.0115 (13)0.0185 (11)0.0183 (13)
C160.0354 (10)0.0514 (13)0.0408 (10)0.0007 (9)0.0050 (8)0.0027 (9)
C170.0374 (10)0.0471 (13)0.0515 (12)0.0045 (9)0.0102 (9)0.0053 (9)
C180.0609 (15)0.0552 (16)0.0789 (17)0.0024 (12)0.0009 (13)0.0109 (13)
C190.082 (2)0.0535 (18)0.121 (3)0.0137 (15)0.0171 (19)0.0200 (17)
C200.103 (2)0.0510 (17)0.120 (3)0.0054 (17)0.052 (2)0.0065 (17)
C210.089 (2)0.0676 (19)0.0777 (18)0.0066 (16)0.0334 (16)0.0204 (15)
C220.0571 (13)0.0588 (15)0.0527 (13)0.0017 (11)0.0135 (11)0.0047 (11)
C230.0402 (12)0.0856 (19)0.0601 (14)0.0121 (12)0.0077 (11)0.0171 (13)
C240.0653 (17)0.114 (3)0.0726 (17)0.0443 (17)0.0071 (14)0.0203 (16)
N10.0352 (9)0.0430 (10)0.0556 (10)0.0032 (7)0.0082 (7)0.0001 (8)
O10.0533 (10)0.0505 (11)0.1134 (15)0.0194 (8)0.0033 (9)0.0008 (10)
O20.0649 (10)0.0761 (12)0.0635 (9)0.0035 (9)0.0021 (7)0.0289 (9)
O30.0376 (8)0.0569 (10)0.0549 (9)0.0070 (6)0.0041 (6)0.0029 (7)
O40.0438 (10)0.180 (3)0.1018 (16)0.0050 (13)0.0256 (11)0.0205 (17)
S10.0428 (3)0.0439 (3)0.0671 (4)0.0055 (2)0.0009 (2)0.0092 (3)
Geometric parameters (Å, º) top
C1—C21.369 (3)C14—N11.418 (3)
C1—C61.378 (3)C15—H15A0.9600
C1—S11.747 (2)C15—H15B0.9600
C2—C31.398 (4)C15—H15C0.9600
C2—H20.9300C16—O31.448 (2)
C3—C41.354 (5)C16—C171.510 (3)
C3—H30.9300C16—H160.9800
C4—C51.349 (4)C17—C221.373 (3)
C4—H40.9300C17—C181.377 (3)
C5—C61.368 (4)C18—C191.376 (4)
C5—H50.9300C18—H180.9300
C6—H60.9300C19—C201.354 (5)
C7—C81.339 (3)C19—H190.9300
C7—N11.434 (3)C20—C211.362 (4)
C7—C151.483 (3)C20—H200.9300
C8—C91.438 (3)C21—C221.373 (4)
C8—C161.493 (3)C21—H210.9300
C9—C141.386 (3)C22—H220.9300
C9—C101.389 (3)C23—O41.184 (3)
C10—C111.375 (4)C23—O31.339 (3)
C10—H100.9300C23—C241.481 (4)
C11—C121.379 (4)C24—H24A0.9600
C11—H110.9300C24—H24B0.9600
C12—C131.364 (4)C24—H24C0.9600
C12—H120.9300N1—S11.6653 (17)
C13—C141.386 (3)O1—S11.4181 (18)
C13—H130.9300O2—S11.4137 (19)
C2—C1—C6120.7 (2)H15A—C15—H15C109.5
C2—C1—S1120.0 (2)H15B—C15—H15C109.5
C6—C1—S1119.25 (18)O3—C16—C8107.17 (17)
C1—C2—C3117.7 (3)O3—C16—C17110.88 (16)
C1—C2—H2121.1C8—C16—C17112.41 (17)
C3—C2—H2121.1O3—C16—H16108.8
C4—C3—C2120.7 (3)C8—C16—H16108.8
C4—C3—H3119.7C17—C16—H16108.8
C2—C3—H3119.7C22—C17—C18118.1 (2)
C5—C4—C3121.1 (3)C22—C17—C16123.24 (19)
C5—C4—H4119.4C18—C17—C16118.7 (2)
C3—C4—H4119.4C19—C18—C17120.5 (3)
C4—C5—C6119.5 (3)C19—C18—H18119.7
C4—C5—H5120.2C17—C18—H18119.7
C6—C5—H5120.2C20—C19—C18120.8 (3)
C5—C6—C1120.2 (2)C20—C19—H19119.6
C5—C6—H6119.9C18—C19—H19119.6
C1—C6—H6119.9C19—C20—C21119.2 (3)
C8—C7—N1108.42 (17)C19—C20—H20120.4
C8—C7—C15129.05 (19)C21—C20—H20120.4
N1—C7—C15122.29 (18)C20—C21—C22120.7 (3)
C7—C8—C9109.27 (18)C20—C21—H21119.6
C7—C8—C16125.70 (18)C22—C21—H21119.6
C9—C8—C16125.02 (18)C21—C22—C17120.7 (2)
C14—C9—C10119.6 (2)C21—C22—H22119.6
C14—C9—C8107.29 (18)C17—C22—H22119.6
C10—C9—C8133.1 (2)O4—C23—O3122.6 (2)
C11—C10—C9118.4 (3)O4—C23—C24126.7 (3)
C11—C10—H10120.8O3—C23—C24110.7 (3)
C9—C10—H10120.8C23—C24—H24A109.5
C10—C11—C12121.0 (3)C23—C24—H24B109.5
C10—C11—H11119.5H24A—C24—H24B109.5
C12—C11—H11119.5C23—C24—H24C109.5
C13—C12—C11121.8 (2)H24A—C24—H24C109.5
C13—C12—H12119.1H24B—C24—H24C109.5
C11—C12—H12119.1C14—N1—C7107.05 (16)
C12—C13—C14117.4 (2)C14—N1—S1120.16 (13)
C12—C13—H13121.3C7—N1—S1123.97 (14)
C14—C13—H13121.3C23—O3—C16117.29 (19)
C9—C14—C13121.9 (2)O2—S1—O1119.30 (12)
C9—C14—N1107.96 (17)O2—S1—N1107.07 (10)
C13—C14—N1130.1 (2)O1—S1—N1106.87 (10)
C7—C15—H15A109.5O2—S1—C1109.33 (11)
C7—C15—H15B109.5O1—S1—C1108.81 (11)
H15A—C15—H15B109.5N1—S1—C1104.41 (9)
C7—C15—H15C109.5
C6—C1—C2—C30.7 (4)C8—C16—C17—C1853.1 (3)
S1—C1—C2—C3178.1 (2)C22—C17—C18—C190.6 (4)
C1—C2—C3—C40.8 (5)C16—C17—C18—C19179.7 (2)
C2—C3—C4—C51.1 (5)C17—C18—C19—C200.3 (5)
C3—C4—C5—C60.3 (5)C18—C19—C20—C210.5 (5)
C4—C5—C6—C11.9 (4)C19—C20—C21—C221.1 (5)
C2—C1—C6—C52.1 (4)C20—C21—C22—C170.8 (4)
S1—C1—C6—C5179.5 (2)C18—C17—C22—C210.1 (3)
N1—C7—C8—C90.4 (2)C16—C17—C22—C21179.1 (2)
C15—C7—C8—C9174.1 (2)C9—C14—N1—C70.9 (2)
N1—C7—C8—C16178.36 (18)C13—C14—N1—C7178.2 (2)
C15—C7—C8—C167.1 (4)C9—C14—N1—S1149.55 (15)
C7—C8—C9—C140.9 (2)C13—C14—N1—S133.1 (3)
C16—C8—C9—C14177.81 (19)C8—C7—N1—C140.3 (2)
C7—C8—C9—C10177.2 (2)C15—C7—N1—C14175.3 (2)
C16—C8—C9—C104.0 (4)C8—C7—N1—S1147.47 (16)
C14—C9—C10—C110.1 (4)C15—C7—N1—S137.6 (3)
C8—C9—C10—C11178.1 (2)O4—C23—O3—C160.8 (4)
C9—C10—C11—C120.2 (4)C24—C23—O3—C16179.9 (2)
C10—C11—C12—C130.4 (5)C8—C16—O3—C23146.89 (19)
C11—C12—C13—C140.5 (4)C17—C16—O3—C2390.1 (2)
C10—C9—C14—C130.3 (3)C14—N1—S1—O2179.98 (16)
C8—C9—C14—C13178.72 (19)C7—N1—S1—O236.81 (19)
C10—C9—C14—N1177.35 (19)C14—N1—S1—O151.11 (18)
C8—C9—C14—N11.1 (2)C7—N1—S1—O1165.73 (17)
C12—C13—C14—C90.4 (3)C14—N1—S1—C164.10 (17)
C12—C13—C14—N1176.6 (2)C7—N1—S1—C179.06 (18)
C7—C8—C16—O3115.6 (2)C2—C1—S1—O2117.5 (2)
C9—C8—C16—O365.9 (2)C6—C1—S1—O259.9 (2)
C7—C8—C16—C17122.4 (2)C2—C1—S1—O114.3 (3)
C9—C8—C16—C1756.2 (3)C6—C1—S1—O1168.25 (19)
O3—C16—C17—C227.9 (3)C2—C1—S1—N1128.2 (2)
C8—C16—C17—C22127.9 (2)C6—C1—S1—N154.4 (2)
O3—C16—C17—C18173.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O10.932.392.977 (4)121
C24—H24B···O2i0.962.583.429 (4)147
C15—H15A···Cg1ii0.962.973.590 (3)124
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC24H21NO4S
Mr419.48
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)14.3655 (6), 8.3432 (4), 18.6261 (8)
β (°) 108.086 (2)
V3)2122.12 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.28 × 0.24 × 0.18
Data collection
DiffractometerBruker Kappa APEXII
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.951, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections
23327, 4712, 3030
Rint0.043
(sin θ/λ)max1)0.647
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.146, 1.01
No. of reflections4712
No. of parameters273
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.35

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O10.932.392.977 (4)121
C24—H24B···O2i0.962.583.429 (4)147
C15—H15A···Cg1ii0.962.973.590 (3)124
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x, y, z+1.
 

Acknowledgements

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

References

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChai, H., Zhao, C. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911–917.  Web of Science CrossRef PubMed CAS Google Scholar
First citationChakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationChakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationOlgen, S. & Coban, T. (2003). Biol. Pharm. Bull. 26, 736–738.  CrossRef PubMed 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

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