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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Ethyl 1-benzene­sulfonyl-2-[(E)-2-(2-methyl­phen­yl)ethen­yl]indole-3-carboxyl­ate

aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, dDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: crystallography2010@gmail.com

(Received 2 January 2011; accepted 12 January 2011; online 22 January 2011)

In the title compound, C26H23NO4S, the phenyl, tolyl and ester groups make dihedral angles of 82.28 (5), 77.67 (6) and 8.52 (6)°, respectively, with the indole ring system. The S atom of the sulfonyl group is displaced by 0.1968 (4) Å from the indole mean plane. The mol­ecular structure is stabilized by weak intra­molecular C—H⋯O inter­actions. The crystal structure structure features short intramolecular C—H⋯O contacts and ππ stacking inter­actions between the phenyl and tolyl groups [centroid–centroid distance = 3.9448 (11) Å].

Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001[Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Giorgi, G., Salvini, L. & Garaliene, V. (2001). Anticancer Drug Des. 16, 167-174.]); Kolocouris et al. (1994[Kolocouris, N., Foscolos, G. B., Kolocouris, A., Marakos, P., Pouli, N., Fytas, G., Ikeda, S. & De Clercq, E. (1994). J. Med. Chem. 37, 2896-2902.]); Merck (1973[Merck (1973). French Patent No. 2 163 554.]). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007[Chakkaravarthi, G., Ramesh, N., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3564.], 2008[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.]).

[Scheme 1]

Experimental

Crystal data
  • C26H23NO4S

  • Mr = 445.51

  • Monoclinic, P 21 /n

  • a = 10.4248 (4) Å

  • b = 8.3629 (3) Å

  • c = 25.2284 (11) Å

  • β = 92.902 (1)°

  • V = 2196.63 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 295 K

  • 0.24 × 0.20 × 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 = 0.958, Tmax = 0.968

  • 22952 measured reflections

  • 4848 independent reflections

  • 3551 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.117

  • S = 1.03

  • 4848 reflections

  • 291 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10⋯O3 0.93 2.48 3.000 (3) 116
C13—H13⋯O1 0.93 2.33 2.908 (3) 120
C16—H16A⋯O1i 0.97 2.56 3.381 (3) 143
Symmetry code: (i) x-1, y, z.

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

Indole derivatives exhibit antihypertensive (Merck, 1973), antitumour (Andreani et al., 2001) and antiviral (Kolocouris et al., 1994) activities. The geometric parameters of the title molecule (Fig. 1) agree well with the reported similar structures (Chakkaravarthi et al. 2007, 2008).

The phenyl ring makes the dihedral angle of 82.28 (5)° with the indole ring system. The benzene ring (C20—C25) forms the dihedral angle of 77.67 (6)° with the indole ring system. The S atom of the sulfonyl group is displaced 0.1968 (4)Å from the indole mean plane. The sum of the bond angles around N1 [358.5 (1)°] indicates that N1 atom is sp2 hybridized. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing exhibits weak intermolecular C—H···O (Fig.2 and Table 1) and ππ interactions [Cg2···Cg4 (1/2 - x,-1/2 + y,1/2 - z) distance of 3.9448 (11) Å; Cg2 and Cg4 are the centroids of C1—C6 ring and C20—C26 ring, respectively] .

Related literature top

For the biological activity of indole derivatives, see: Andreani et al. (2001); Kolocouris et al. (1994); Merck (1973). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007, 2008).

Experimental top

To a suspension of hexane (5 ml) washed NaH (0.29 g, 6.10 mmol) in dry THF (10 ml) at -10° C under N2 atmosphere was slowly added the solution of diethyl (3-(ethoxycarbonyl)-1-phenylsulfonyl-1H-indol-2-yl)methylphosphonate (0.97 g, 2.03 mmol) in dry THF (5 ml) via syringe and stirred for 15 min. Then a solution of 2-methylbenzaldehyde (0.28 g, 2.32 mmol) in dry THF (5 ml) was added and allowed to stir for additional 2 h. After completion of the product formation (monitored by TLC), it was then poured over crushed ice (100 g) containing conc. HCl (3 ml). The solid formed was filtered and recrystalized with MeOH to afford ethyl 2-(2-methylstyryl)-1-phenylsulfonyl -1H-indole-3-carboxylate as bright yellow crystals [0.70 g, 78%; melting point 371–373 K].

Refinement top

H atoms were positioned geometrically and refined using riding model approximation with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H and C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene group and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl group.

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 the title compound with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The crystal packing viewed down the b axis. Intermolecular C-H···O interactionshydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
Ethyl 1-benzenesulfonyl-2-[(E)-2-(2-methylphenyl)ethenyl]indole-3-carboxylate top
Crystal data top
C26H23NO4SF(000) = 936
Mr = 445.51Dx = 1.347 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 31039 reflections
a = 10.4248 (4) Åθ = 2.1–31.4°
b = 8.3629 (3) ŵ = 0.18 mm1
c = 25.2284 (11) ÅT = 295 K
β = 92.902 (1)°Block, yellow
V = 2196.63 (15) Å30.24 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker Kappa APEXII
diffractometer
4848 independent reflections
Radiation source: fine-focus sealed tube3551 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω and ϕ scansθmax = 27.1°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1213
Tmin = 0.958, Tmax = 0.968k = 1010
22952 measured reflectionsl = 3232
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0499P)2 + 0.6907P]
where P = (Fo2 + 2Fc2)/3
4848 reflections(Δ/σ)max < 0.001
291 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C26H23NO4SV = 2196.63 (15) Å3
Mr = 445.51Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.4248 (4) ŵ = 0.18 mm1
b = 8.3629 (3) ÅT = 295 K
c = 25.2284 (11) Å0.24 × 0.20 × 0.18 mm
β = 92.902 (1)°
Data collection top
Bruker Kappa APEXII
diffractometer
4848 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3551 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.968Rint = 0.029
22952 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.03Δρmax = 0.25 e Å3
4848 reflectionsΔρmin = 0.28 e Å3
291 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.29596 (16)0.5477 (2)0.13482 (7)0.0434 (4)
C20.33149 (19)0.4055 (2)0.11194 (7)0.0516 (4)
H20.37050.40510.07960.062*
C30.3082 (2)0.2640 (2)0.13788 (8)0.0563 (5)
H30.33140.16720.12290.068*
C40.2511 (2)0.2656 (2)0.18551 (8)0.0582 (5)
H40.23530.16970.20270.070*
C50.2170 (2)0.4074 (3)0.20820 (8)0.0641 (6)
H50.17930.40730.24080.077*
C60.23856 (19)0.5502 (2)0.18277 (8)0.0549 (5)
H60.21470.64660.19780.066*
C70.07971 (18)0.81521 (19)0.06872 (6)0.0439 (4)
C80.00146 (19)0.7883 (2)0.02544 (6)0.0466 (4)
C90.0676 (2)0.7013 (2)0.01332 (7)0.0505 (5)
C100.0332 (2)0.6438 (2)0.06437 (7)0.0644 (6)
H100.04870.66110.07960.077*
C110.1231 (3)0.5617 (3)0.09121 (9)0.0782 (8)
H110.10190.52460.12530.094*
C120.2444 (3)0.5327 (3)0.06897 (9)0.0803 (8)
H120.30200.47330.08790.096*
C130.2824 (3)0.5898 (3)0.01920 (8)0.0698 (6)
H130.36470.57190.00450.084*
C140.1920 (2)0.6752 (2)0.00782 (7)0.0530 (5)
C150.1351 (2)0.8425 (2)0.01525 (7)0.0520 (5)
C160.3192 (2)0.9600 (3)0.04901 (9)0.0683 (6)
H16A0.37490.87000.04010.082*
H16B0.32731.03750.02040.082*
C170.3556 (3)1.0338 (3)0.09964 (11)0.0900 (8)
H17A0.29961.12230.10810.135*
H17B0.34790.95580.12750.135*
H17C0.44271.07100.09600.135*
C180.05757 (17)0.9015 (2)0.11824 (6)0.0458 (4)
H180.10210.99650.12470.055*
C190.02112 (18)0.8527 (2)0.15390 (6)0.0479 (4)
H190.06170.75490.14790.057*
C200.05081 (16)0.9393 (2)0.20259 (7)0.0445 (4)
C210.07577 (16)0.8570 (2)0.24966 (6)0.0460 (4)
C220.10097 (19)0.9451 (3)0.29430 (7)0.0570 (5)
H220.11760.89170.32550.068*
C230.1022 (2)1.1089 (3)0.29386 (8)0.0644 (6)
H230.11811.16520.32460.077*
C240.0800 (2)1.1895 (3)0.24804 (9)0.0644 (6)
H240.08161.30070.24750.077*
C250.05529 (19)1.1053 (2)0.20262 (8)0.0543 (5)
H250.04141.16070.17150.065*
C260.0706 (2)0.6777 (2)0.25305 (8)0.0594 (5)
H26A0.09290.64420.28780.089*
H26B0.01460.64170.24650.089*
H26C0.13040.63260.22700.089*
N10.20131 (15)0.75147 (17)0.05839 (6)0.0494 (4)
O10.43527 (14)0.70935 (19)0.07195 (6)0.0717 (4)
O20.31983 (13)0.85612 (15)0.13962 (5)0.0603 (4)
O30.19140 (16)0.8300 (2)0.02733 (6)0.0866 (5)
O40.18768 (13)0.90745 (18)0.05650 (5)0.0618 (4)
S10.32570 (5)0.72867 (5)0.10266 (2)0.05081 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0433 (9)0.0401 (8)0.0464 (9)0.0039 (7)0.0009 (7)0.0010 (7)
C20.0587 (12)0.0467 (10)0.0492 (10)0.0004 (8)0.0014 (9)0.0044 (8)
C30.0654 (13)0.0397 (9)0.0624 (12)0.0005 (9)0.0099 (10)0.0035 (8)
C40.0644 (13)0.0464 (10)0.0625 (12)0.0059 (9)0.0087 (10)0.0116 (9)
C50.0771 (15)0.0591 (12)0.0571 (12)0.0003 (11)0.0132 (10)0.0104 (10)
C60.0661 (12)0.0454 (10)0.0538 (11)0.0034 (9)0.0104 (9)0.0007 (8)
C70.0591 (11)0.0362 (8)0.0371 (8)0.0067 (8)0.0108 (8)0.0032 (7)
C80.0653 (12)0.0390 (9)0.0363 (9)0.0110 (8)0.0094 (8)0.0019 (7)
C90.0780 (14)0.0366 (9)0.0380 (9)0.0125 (9)0.0134 (9)0.0027 (7)
C100.1043 (17)0.0483 (11)0.0412 (10)0.0157 (11)0.0112 (10)0.0031 (9)
C110.146 (3)0.0495 (12)0.0414 (11)0.0110 (14)0.0231 (14)0.0058 (9)
C120.139 (2)0.0523 (12)0.0534 (13)0.0117 (14)0.0431 (15)0.0011 (10)
C130.0991 (17)0.0592 (12)0.0537 (12)0.0121 (12)0.0293 (12)0.0066 (10)
C140.0827 (14)0.0383 (9)0.0396 (9)0.0030 (9)0.0199 (9)0.0045 (7)
C150.0654 (12)0.0482 (10)0.0426 (10)0.0170 (9)0.0037 (9)0.0007 (8)
C160.0565 (13)0.0702 (14)0.0784 (15)0.0075 (11)0.0065 (11)0.0081 (12)
C170.0768 (17)0.0912 (18)0.104 (2)0.0034 (14)0.0249 (15)0.0120 (16)
C180.0572 (11)0.0414 (9)0.0389 (9)0.0050 (8)0.0039 (8)0.0034 (7)
C190.0635 (12)0.0429 (9)0.0376 (9)0.0074 (8)0.0051 (8)0.0013 (7)
C200.0440 (10)0.0504 (10)0.0390 (9)0.0034 (8)0.0024 (7)0.0036 (7)
C210.0398 (9)0.0587 (11)0.0394 (9)0.0019 (8)0.0019 (7)0.0001 (8)
C220.0562 (12)0.0771 (14)0.0380 (9)0.0023 (10)0.0074 (8)0.0026 (9)
C230.0654 (13)0.0780 (15)0.0504 (11)0.0045 (11)0.0079 (10)0.0189 (11)
C240.0672 (14)0.0521 (11)0.0745 (14)0.0019 (10)0.0106 (11)0.0151 (10)
C250.0615 (12)0.0514 (10)0.0507 (10)0.0026 (9)0.0085 (9)0.0002 (9)
C260.0654 (13)0.0607 (12)0.0528 (11)0.0022 (10)0.0115 (10)0.0078 (9)
N10.0647 (10)0.0456 (8)0.0386 (8)0.0016 (7)0.0102 (7)0.0027 (6)
O10.0589 (9)0.0704 (10)0.0881 (11)0.0103 (7)0.0267 (8)0.0072 (8)
O20.0694 (9)0.0408 (7)0.0699 (9)0.0097 (6)0.0036 (7)0.0054 (6)
O30.0824 (11)0.1226 (15)0.0535 (9)0.0018 (10)0.0107 (8)0.0151 (9)
O40.0587 (9)0.0764 (9)0.0504 (8)0.0003 (7)0.0037 (6)0.0047 (7)
S10.0530 (3)0.0423 (2)0.0579 (3)0.0081 (2)0.0101 (2)0.0021 (2)
Geometric parameters (Å, º) top
C1—C61.377 (3)C15—O41.318 (2)
C1—C21.381 (2)C16—O41.444 (2)
C1—S11.7523 (17)C16—C171.485 (3)
C2—C31.379 (3)C16—H16A0.9700
C2—H20.9300C16—H16B0.9700
C3—C41.368 (3)C17—H17A0.9600
C3—H30.9300C17—H17B0.9600
C4—C51.371 (3)C17—H17C0.9600
C4—H40.9300C18—C191.313 (2)
C5—C61.379 (3)C18—H180.9300
C5—H50.9300C19—C201.472 (2)
C6—H60.9300C19—H190.9300
C7—C81.366 (2)C20—C251.389 (3)
C7—N11.412 (2)C20—C211.408 (2)
C7—C181.471 (2)C21—C221.382 (3)
C8—C91.440 (2)C21—C261.503 (3)
C8—C151.475 (3)C22—C231.370 (3)
C9—C141.394 (3)C22—H220.9300
C9—C101.404 (3)C23—C241.368 (3)
C10—C111.368 (3)C23—H230.9300
C10—H100.9300C24—C251.380 (3)
C11—C121.379 (4)C24—H240.9300
C11—H110.9300C25—H250.9300
C12—C131.383 (3)C26—H26A0.9600
C12—H120.9300C26—H26B0.9600
C13—C141.388 (3)C26—H26C0.9600
C13—H130.9300N1—S11.6789 (17)
C14—N11.425 (2)O1—S11.4217 (14)
C15—O31.202 (2)O2—S11.4194 (14)
C6—C1—C2121.21 (17)C17—C16—H16B110.3
C6—C1—S1119.25 (13)H16A—C16—H16B108.5
C2—C1—S1119.54 (14)C16—C17—H17A109.5
C3—C2—C1118.89 (18)C16—C17—H17B109.5
C3—C2—H2120.6H17A—C17—H17B109.5
C1—C2—H2120.6C16—C17—H17C109.5
C4—C3—C2120.21 (18)H17A—C17—H17C109.5
C4—C3—H3119.9H17B—C17—H17C109.5
C2—C3—H3119.9C19—C18—C7124.04 (16)
C3—C4—C5120.57 (18)C19—C18—H18118.0
C3—C4—H4119.7C7—C18—H18118.0
C5—C4—H4119.7C18—C19—C20125.73 (17)
C4—C5—C6120.19 (19)C18—C19—H19117.1
C4—C5—H5119.9C20—C19—H19117.1
C6—C5—H5119.9C25—C20—C21118.73 (16)
C1—C6—C5118.93 (18)C25—C20—C19120.03 (16)
C1—C6—H6120.5C21—C20—C19121.24 (16)
C5—C6—H6120.5C22—C21—C20118.50 (18)
C8—C7—N1108.42 (15)C22—C21—C26119.57 (17)
C8—C7—C18129.95 (17)C20—C21—C26121.89 (16)
N1—C7—C18121.54 (16)C23—C22—C21121.92 (19)
C7—C8—C9108.39 (18)C23—C22—H22119.0
C7—C8—C15129.07 (16)C21—C22—H22119.0
C9—C8—C15122.45 (17)C24—C23—C22119.83 (19)
C14—C9—C10119.08 (19)C24—C23—H23120.1
C14—C9—C8107.85 (16)C22—C23—H23120.1
C10—C9—C8133.1 (2)C23—C24—C25119.8 (2)
C11—C10—C9118.5 (2)C23—C24—H24120.1
C11—C10—H10120.8C25—C24—H24120.1
C9—C10—H10120.8C24—C25—C20121.19 (19)
C10—C11—C12121.6 (2)C24—C25—H25119.4
C10—C11—H11119.2C20—C25—H25119.4
C12—C11—H11119.2C21—C26—H26A109.5
C11—C12—C13121.6 (2)C21—C26—H26B109.5
C11—C12—H12119.2H26A—C26—H26B109.5
C13—C12—H12119.2C21—C26—H26C109.5
C12—C13—C14116.9 (2)H26A—C26—H26C109.5
C12—C13—H13121.5H26B—C26—H26C109.5
C14—C13—H13121.5C7—N1—C14108.25 (16)
C13—C14—C9122.30 (19)C7—N1—S1126.20 (12)
C13—C14—N1130.7 (2)C14—N1—S1124.06 (14)
C9—C14—N1106.99 (16)C15—O4—C16116.92 (16)
O3—C15—O4122.5 (2)O2—S1—O1120.39 (9)
O3—C15—C8122.88 (19)O2—S1—N1107.11 (8)
O4—C15—C8114.58 (16)O1—S1—N1105.37 (9)
O4—C16—C17107.22 (19)O2—S1—C1109.27 (8)
O4—C16—H16A110.3O1—S1—C1108.67 (9)
C17—C16—H16A110.3N1—S1—C1104.91 (8)
O4—C16—H16B110.3
C6—C1—C2—C30.2 (3)C18—C19—C20—C21146.01 (19)
S1—C1—C2—C3179.60 (15)C25—C20—C21—C221.4 (3)
C1—C2—C3—C40.2 (3)C19—C20—C21—C22178.96 (17)
C2—C3—C4—C50.4 (3)C25—C20—C21—C26178.99 (18)
C3—C4—C5—C60.8 (3)C19—C20—C21—C261.4 (3)
C2—C1—C6—C50.3 (3)C20—C21—C22—C230.0 (3)
S1—C1—C6—C5179.13 (16)C26—C21—C22—C23177.64 (19)
C4—C5—C6—C10.8 (3)C21—C22—C23—C241.0 (3)
N1—C7—C8—C91.62 (18)C22—C23—C24—C250.6 (3)
C18—C7—C8—C9178.34 (16)C23—C24—C25—C200.8 (3)
N1—C7—C8—C15174.87 (16)C21—C20—C25—C241.8 (3)
C18—C7—C8—C151.8 (3)C19—C20—C25—C24178.52 (18)
C7—C8—C9—C140.51 (19)C8—C7—N1—C143.13 (18)
C15—C8—C9—C14177.28 (15)C18—C7—N1—C14179.82 (14)
C7—C8—C9—C10179.41 (18)C8—C7—N1—S1169.56 (12)
C15—C8—C9—C102.6 (3)C18—C7—N1—S113.4 (2)
C14—C9—C10—C111.0 (3)C13—C14—N1—C7177.09 (18)
C8—C9—C10—C11179.08 (19)C9—C14—N1—C73.40 (18)
C9—C10—C11—C121.0 (3)C13—C14—N1—S110.3 (3)
C10—C11—C12—C132.2 (4)C9—C14—N1—S1170.19 (12)
C11—C12—C13—C141.2 (3)O3—C15—O4—C161.7 (3)
C12—C13—C14—C90.9 (3)C8—C15—O4—C16178.92 (16)
C12—C13—C14—N1178.54 (18)C17—C16—O4—C15177.89 (18)
C10—C9—C14—C132.0 (3)C7—N1—S1—O232.90 (16)
C8—C9—C14—C13178.05 (17)C14—N1—S1—O2162.70 (14)
C10—C9—C14—N1177.54 (15)C7—N1—S1—O1162.21 (14)
C8—C9—C14—N12.39 (18)C14—N1—S1—O133.38 (16)
C7—C8—C15—O3169.53 (19)C7—N1—S1—C183.16 (15)
C9—C8—C15—O36.5 (3)C14—N1—S1—C181.24 (15)
C7—C8—C15—O49.8 (3)C6—C1—S1—O217.63 (18)
C9—C8—C15—O4174.12 (15)C2—C1—S1—O2161.76 (15)
C8—C7—C18—C1967.2 (3)C6—C1—S1—O1150.76 (16)
N1—C7—C18—C19116.4 (2)C2—C1—S1—O128.63 (18)
C7—C18—C19—C20176.79 (17)C6—C1—S1—N196.93 (16)
C18—C19—C20—C2534.3 (3)C2—C1—S1—N183.68 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O30.932.483.000 (3)116
C13—H13···O10.932.332.908 (3)120
C16—H16A···O1i0.972.563.381 (3)143
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC26H23NO4S
Mr445.51
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)10.4248 (4), 8.3629 (3), 25.2284 (11)
β (°) 92.902 (1)
V3)2196.63 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.24 × 0.20 × 0.18
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.958, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections
22952, 4848, 3551
Rint0.029
(sin θ/λ)max1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.117, 1.03
No. of reflections4848
No. of parameters291
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.28

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
C10—H10···O30.932.483.000 (3)116
C13—H13···O10.932.332.908 (3)120
C16—H16A···O1i0.972.563.381 (3)143
Symmetry code: (i) x1, y, z.
 

Acknowledgements

CR wishes to acknowledge AMET University management, India, for their kind support.

References

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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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