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

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ISSN: 2056-9890

(E)-1-[2-(4-Chloro-2-nitro­styr­yl)-1-phenyl­sulfonyl-1H-indol-3-yl]propan-1-one

aResearch Scholar (Chemistry), Bharathiyar University, Coimbatore 641 046, Tamilnadu, India, bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, cDepartment of Sciences, Chemistry and Materials Research Lab, Amrita Vishwa Vidyapeetham University, Ettimadai, Coimbatore 641 112, India, and dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
*Correspondence e-mail: ryamuna1@gmail.com, chakkaravarthi_2005@yahoo.com

(Received 8 November 2013; accepted 12 November 2013; online 16 November 2013)

In the title compound, C25H19ClN2O5S, the phenyl ring forms dihedral angles of 79.62 (12) and 80.02 (13)° with the indole ring system and the benzene ring, respectively. The nitro group is twisted at an angle of 22.39 (11)° with respect to the attached benzene ring. In the crystal, mol­ecules assemble into double layers in the ab plane via C—H⋯O inter­actions.

Related literature

For the biological activity of indole derivatives, see: Okabe & Adachi (1998[Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386-387.]); Srivastava et al. (2011[Srivastava, Anupam & Pandeya, S. N. (2011). JCPR, 1, 1-17.]). For related structures, see: Chakkaravarthi et al. (2008[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o749.], 2010[Chakkaravarthi, G., Panchatcharam, R., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2010). Acta Cryst. E66, o2957.]).

[Scheme 1]

Experimental

Crystal data
  • C25H19ClN2O5S

  • Mr = 494.93

  • Triclinic, [P \overline 1]

  • a = 8.4658 (3) Å

  • b = 8.6643 (3) Å

  • c = 16.1126 (6) Å

  • α = 84.196 (2)°

  • β = 87.768 (3)°

  • γ = 79.541 (2)°

  • V = 1156.01 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.30 mm−1

  • T = 295 K

  • 0.28 × 0.24 × 0.20 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.922, Tmax = 0.943

  • 25531 measured reflections

  • 6333 independent reflections

  • 4536 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.150

  • S = 1.03

  • 6333 reflections

  • 308 parameters

  • H-atom parameters constrained

  • Δρmax = 0.49 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10⋯O1i 0.93 2.60 3.327 (3) 136
C16—H16B⋯O5ii 0.97 2.37 3.260 (3) 152
Symmetry codes: (i) x, y+1, z; (ii) 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


Experimental top

Synthesis and crystallization top

A solution of 1-(2-(bromo­methyl)-1-(phenyl­sulfonyl)-1H-indol-3-yl)propan-1-one (5 g, 12.31 mmol) and tri­phenyl­phosphine (3.5 g, 13.54 mmol) in dry THF (100 ml) was refluxed for 6 h. After consumption of the starting material, the solvent was removed under vacuum and the solid washed with di­ethyl ether to give the phospho­nium salt. Then, the mixture of phospho­nium salt (8 g, 11.97 mmol), 4-chloro-2-nitro­benzaldehyde (2.45 g, 13.17 mmol) and K2CO3 (3.30 g, 23.95 mmol) in DCM (70 ml) was stirred at room temperature for 24 h. After completion of the reaction (monitored by TLC), it was diluted using DCM (30 ml), washed with water (2 x 100 ml) and dried (Na2SO4). Removal of solvent in vacuo followed by trituration of the crude product with MeOH (20 ml) afforded the title compound.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were positioned geometrically and refined using riding model, with C—H = (0.93–0.97) Å and Uiso(H) = 1.2–1.5Ueq(C). Owing to poor agreement, the (001) reflection was omitted from the final cycles of refinement.

Results and discussion top

In continuation of our studies on indole derivatives which are known to exhibit anti-microbial, anti-biotic, analgesic and anti-cancer activities (Okabe and Adachi, 1998; Srivastava et al., 2011), we herewith report the crystal structure of the title compound (I). The geometric parameters of (I) (Fig. 1) are in close agreement with similar structures (Chakkaravarthi et al., 2008; 2010).

The phenyl ring makes the dihedral angle of 79.62 (12)° with the indole ring system. The phenyl ring (C1—C6) and the benzene ring (C20—C25) are inclined at an angle of 80.02 (13)°. The nitro group is twisted at an angle of 22.39 (11)° with respect to the attached benzene ring (C20—C25). The N1 atom is sp2 hybridised as the bond angles around N1 atom sum 352.4°. Details of the C—H···O inter­actions are given in Table 2 - these lead to layers in the ab plane.

Related literature top

For the biological activity of indole derivatives, see: Okabe & Adachi (1998); Srivastava et al. (2011). For related structures, see: Chakkaravarthi et al. (2008, 2010).

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.
(E)-1-[2-(4-Chloro-2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl]propan-1-one top
Crystal data top
C25H19ClN2O5SZ = 2
Mr = 494.93F(000) = 512
Triclinic, P1Dx = 1.422 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4658 (3) ÅCell parameters from 8917 reflections
b = 8.6643 (3) Åθ = 2.5–28.4°
c = 16.1126 (6) ŵ = 0.30 mm1
α = 84.196 (2)°T = 295 K
β = 87.768 (3)°Block, colourless
γ = 79.541 (2)°0.28 × 0.24 × 0.20 mm
V = 1156.01 (7) Å3
Data collection top
Bruker Kappa APEXII
diffractometer
6333 independent reflections
Radiation source: fine-focus sealed tube4536 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω and ϕ scanθmax = 29.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.922, Tmax = 0.943k = 1111
25531 measured reflectionsl = 2022
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0709P)2 + 0.3517P]
where P = (Fo2 + 2Fc2)/3
6333 reflections(Δ/σ)max < 0.001
308 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.39 e Å3
Crystal data top
C25H19ClN2O5Sγ = 79.541 (2)°
Mr = 494.93V = 1156.01 (7) Å3
Triclinic, P1Z = 2
a = 8.4658 (3) ÅMo Kα radiation
b = 8.6643 (3) ŵ = 0.30 mm1
c = 16.1126 (6) ÅT = 295 K
α = 84.196 (2)°0.28 × 0.24 × 0.20 mm
β = 87.768 (3)°
Data collection top
Bruker Kappa APEXII
diffractometer
6333 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4536 reflections with I > 2σ(I)
Tmin = 0.922, Tmax = 0.943Rint = 0.029
25531 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.150H-atom parameters constrained
S = 1.03Δρmax = 0.49 e Å3
6333 reflectionsΔρmin = 0.39 e Å3
308 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6620 (2)0.1560 (2)0.44142 (11)0.0497 (4)
C20.7468 (3)0.1501 (4)0.51342 (14)0.0765 (7)
H20.85700.11310.51400.092*
C30.6662 (4)0.1997 (5)0.58429 (16)0.0984 (11)
H30.72150.19450.63360.118*
C40.5062 (4)0.2564 (4)0.58242 (17)0.0920 (9)
H40.45370.29520.62980.110*
C50.4199 (4)0.2573 (4)0.51124 (19)0.0991 (10)
H50.30930.29230.51150.119*
C60.4985 (3)0.2060 (3)0.43989 (15)0.0781 (7)
H60.44200.20530.39160.094*
C70.6425 (2)0.3393 (2)0.23941 (10)0.0408 (4)
C80.6569 (2)0.4934 (2)0.22907 (10)0.0424 (4)
C90.7938 (2)0.5131 (2)0.27424 (11)0.0439 (4)
C100.8617 (3)0.6446 (2)0.28430 (14)0.0584 (5)
H100.81790.74350.25890.070*
C110.9950 (3)0.6244 (3)0.33266 (18)0.0738 (7)
H111.04050.71130.34120.089*
C121.0626 (3)0.4773 (3)0.36883 (18)0.0771 (7)
H121.15360.46750.40080.093*
C130.9999 (3)0.3449 (3)0.35916 (15)0.0625 (5)
H131.04660.24610.38360.075*
C140.8635 (2)0.3653 (2)0.31128 (11)0.0440 (4)
C150.5596 (2)0.6261 (2)0.17657 (12)0.0516 (5)
C160.5615 (3)0.6198 (3)0.08490 (12)0.0593 (5)
H16A0.50660.53590.07290.071*
H16B0.67220.59270.06570.071*
C170.4848 (4)0.7702 (3)0.03593 (16)0.0880 (8)
H17A0.37100.78840.04690.132*
H17B0.50530.76130.02260.132*
H17C0.52910.85660.05230.132*
C180.5229 (2)0.2611 (2)0.20724 (10)0.0442 (4)
H180.55630.16210.18840.053*
C190.3680 (2)0.3249 (2)0.20359 (11)0.0467 (4)
H190.33520.42500.22120.056*
C200.2462 (2)0.2449 (2)0.17303 (11)0.0453 (4)
C210.2582 (3)0.0828 (2)0.19095 (14)0.0566 (5)
H210.34660.02710.22010.068*
C220.1449 (3)0.0018 (2)0.16730 (14)0.0589 (5)
H220.15800.10700.17960.071*
C230.0107 (2)0.0832 (2)0.12499 (12)0.0518 (4)
C240.0071 (2)0.2427 (2)0.10536 (12)0.0487 (4)
H230.09630.29760.07640.058*
C250.1097 (2)0.3207 (2)0.12932 (11)0.0452 (4)
N10.77198 (17)0.25460 (17)0.28902 (9)0.0427 (3)
N30.0859 (2)0.4903 (2)0.10290 (11)0.0554 (4)
O10.6646 (2)0.00599 (16)0.31000 (9)0.0651 (4)
O20.92318 (19)0.02047 (18)0.37066 (10)0.0682 (4)
O30.4897 (3)0.7364 (2)0.20882 (12)0.1283 (11)
O50.04694 (18)0.55877 (18)0.08461 (11)0.0692 (4)
O60.2012 (2)0.5539 (2)0.09605 (17)0.1115 (9)
S10.76175 (6)0.08992 (5)0.35118 (3)0.04869 (14)
Cl10.13374 (7)0.01698 (7)0.09611 (4)0.07319 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0570 (11)0.0502 (10)0.0409 (9)0.0105 (8)0.0042 (8)0.0040 (7)
C20.0641 (14)0.121 (2)0.0511 (12)0.0321 (14)0.0066 (10)0.0076 (13)
C30.098 (2)0.169 (3)0.0489 (13)0.071 (2)0.0058 (13)0.0239 (17)
C40.114 (3)0.112 (2)0.0570 (15)0.0362 (19)0.0260 (16)0.0210 (15)
C50.0807 (18)0.127 (3)0.0700 (17)0.0174 (18)0.0207 (14)0.0128 (17)
C60.0669 (14)0.106 (2)0.0486 (12)0.0085 (14)0.0037 (10)0.0089 (12)
C70.0405 (8)0.0465 (9)0.0314 (7)0.0034 (7)0.0039 (6)0.0038 (6)
C80.0444 (9)0.0458 (9)0.0330 (8)0.0039 (7)0.0042 (7)0.0044 (7)
C90.0421 (9)0.0493 (9)0.0373 (8)0.0004 (7)0.0008 (7)0.0048 (7)
C100.0591 (12)0.0499 (11)0.0654 (13)0.0074 (9)0.0074 (10)0.0043 (9)
C110.0639 (14)0.0660 (14)0.0959 (18)0.0182 (11)0.0190 (13)0.0110 (13)
C120.0568 (13)0.0819 (17)0.0943 (19)0.0116 (12)0.0320 (13)0.0059 (14)
C130.0503 (11)0.0655 (13)0.0677 (13)0.0003 (9)0.0196 (10)0.0001 (10)
C140.0398 (8)0.0495 (9)0.0400 (9)0.0013 (7)0.0029 (7)0.0035 (7)
C150.0597 (11)0.0460 (10)0.0443 (10)0.0046 (8)0.0140 (8)0.0024 (8)
C160.0538 (11)0.0768 (14)0.0393 (9)0.0031 (10)0.0010 (8)0.0057 (9)
C170.117 (2)0.0850 (18)0.0532 (13)0.0059 (16)0.0168 (14)0.0213 (12)
C180.0476 (9)0.0459 (9)0.0369 (8)0.0009 (7)0.0060 (7)0.0045 (7)
C190.0471 (9)0.0481 (10)0.0424 (9)0.0022 (8)0.0022 (7)0.0042 (7)
C200.0412 (9)0.0489 (10)0.0430 (9)0.0024 (7)0.0006 (7)0.0014 (7)
C210.0533 (11)0.0505 (11)0.0612 (12)0.0003 (9)0.0098 (9)0.0045 (9)
C220.0625 (12)0.0478 (10)0.0644 (13)0.0080 (9)0.0033 (10)0.0017 (9)
C230.0503 (10)0.0574 (11)0.0486 (10)0.0131 (9)0.0045 (8)0.0052 (8)
C240.0388 (9)0.0563 (11)0.0482 (10)0.0044 (8)0.0006 (7)0.0001 (8)
C250.0395 (9)0.0479 (9)0.0447 (9)0.0028 (7)0.0035 (7)0.0015 (7)
N10.0420 (7)0.0436 (8)0.0389 (7)0.0004 (6)0.0064 (6)0.0001 (6)
N30.0441 (8)0.0534 (9)0.0655 (10)0.0064 (7)0.0053 (7)0.0068 (8)
O10.0916 (11)0.0455 (7)0.0589 (9)0.0115 (7)0.0143 (8)0.0052 (6)
O20.0624 (9)0.0575 (8)0.0722 (10)0.0174 (7)0.0096 (7)0.0063 (7)
O30.205 (3)0.0840 (13)0.0636 (11)0.0794 (16)0.0502 (14)0.0264 (10)
O50.0509 (8)0.0593 (9)0.0903 (12)0.0050 (7)0.0109 (8)0.0038 (8)
O60.0654 (11)0.0756 (12)0.189 (2)0.0286 (9)0.0420 (13)0.0514 (14)
S10.0554 (3)0.0407 (2)0.0451 (2)0.00326 (19)0.00822 (19)0.00039 (18)
Cl10.0676 (4)0.0741 (4)0.0840 (4)0.0276 (3)0.0047 (3)0.0088 (3)
Geometric parameters (Å, º) top
C1—C61.374 (3)C15—O31.185 (2)
C1—C21.380 (3)C15—C161.483 (3)
C1—S11.747 (2)C16—C171.506 (3)
C2—C31.373 (4)C16—H16A0.9700
C2—H20.9300C16—H16B0.9700
C3—C41.355 (5)C17—H17A0.9600
C3—H30.9300C17—H17B0.9600
C4—C51.383 (5)C17—H17C0.9600
C4—H40.9300C18—C191.329 (3)
C5—C61.378 (4)C18—H180.9300
C5—H50.9300C19—C201.468 (3)
C6—H60.9300C19—H190.9300
C7—C81.355 (3)C20—C211.391 (3)
C7—N11.427 (2)C20—C251.399 (2)
C7—C181.454 (2)C21—C221.373 (3)
C8—C91.437 (2)C21—H210.9300
C8—C151.493 (2)C22—C231.387 (3)
C9—C101.393 (3)C22—H220.9300
C9—C141.394 (2)C23—C241.369 (3)
C10—C111.371 (3)C23—Cl11.725 (2)
C10—H100.9300C24—C251.382 (3)
C11—C121.379 (4)C24—H230.9300
C11—H110.9300C25—N31.468 (2)
C12—C131.373 (3)N1—S11.6720 (15)
C12—H120.9300N3—O61.202 (2)
C13—C141.388 (3)N3—O51.205 (2)
C13—H130.9300O1—S11.4153 (16)
C14—N11.418 (2)O2—S11.4230 (15)
C6—C1—C2121.4 (2)C17—C16—H16A108.5
C6—C1—S1118.79 (16)C15—C16—H16B108.5
C2—C1—S1119.75 (18)C17—C16—H16B108.5
C3—C2—C1119.1 (3)H16A—C16—H16B107.5
C3—C2—H2120.5C16—C17—H17A109.5
C1—C2—H2120.5C16—C17—H17B109.5
C4—C3—C2120.0 (3)H17A—C17—H17B109.5
C4—C3—H3120.0C16—C17—H17C109.5
C2—C3—H3120.0H17A—C17—H17C109.5
C3—C4—C5121.1 (3)H17B—C17—H17C109.5
C3—C4—H4119.5C19—C18—C7122.80 (17)
C5—C4—H4119.5C19—C18—H18118.6
C6—C5—C4119.6 (3)C7—C18—H18118.6
C6—C5—H5120.2C18—C19—C20123.04 (17)
C4—C5—H5120.2C18—C19—H19118.5
C1—C6—C5118.7 (2)C20—C19—H19118.5
C1—C6—H6120.6C21—C20—C25115.37 (17)
C5—C6—H6120.6C21—C20—C19119.73 (16)
C8—C7—N1108.46 (15)C25—C20—C19124.82 (16)
C8—C7—C18129.63 (15)C22—C21—C20122.68 (18)
N1—C7—C18121.90 (15)C22—C21—H21118.7
C7—C8—C9108.69 (15)C20—C21—H21118.7
C7—C8—C15128.84 (16)C21—C22—C23119.55 (19)
C9—C8—C15122.37 (17)C21—C22—H22120.2
C10—C9—C14119.98 (17)C23—C22—H22120.2
C10—C9—C8132.32 (17)C24—C23—C22120.32 (19)
C14—C9—C8107.70 (16)C24—C23—Cl1119.70 (16)
C11—C10—C9118.2 (2)C22—C23—Cl1119.98 (16)
C11—C10—H10120.9C23—C24—C25118.76 (17)
C9—C10—H10120.9C23—C24—H23120.6
C10—C11—C12121.1 (2)C25—C24—H23120.6
C10—C11—H11119.5C24—C25—C20123.31 (17)
C12—C11—H11119.5C24—C25—N3115.63 (15)
C13—C12—C11122.2 (2)C20—C25—N3121.01 (16)
C13—C12—H12118.9C14—N1—C7107.57 (13)
C11—C12—H12118.9C14—N1—S1120.91 (11)
C12—C13—C14116.9 (2)C7—N1—S1123.89 (12)
C12—C13—H13121.5O6—N3—O5122.39 (18)
C14—C13—H13121.5O6—N3—C25118.61 (16)
C13—C14—C9121.65 (19)O5—N3—C25118.88 (16)
C13—C14—N1130.80 (18)O1—S1—O2120.22 (10)
C9—C14—N1107.55 (14)O1—S1—N1106.22 (8)
O3—C15—C16122.04 (18)O2—S1—N1106.01 (9)
O3—C15—C8119.14 (17)O1—S1—C1109.63 (10)
C16—C15—C8118.71 (16)O2—S1—C1109.04 (10)
C15—C16—C17114.9 (2)N1—S1—C1104.52 (8)
C15—C16—H16A108.5
C6—C1—C2—C31.9 (4)C25—C20—C21—C220.3 (3)
S1—C1—C2—C3178.8 (2)C19—C20—C21—C22177.18 (19)
C1—C2—C3—C41.3 (5)C20—C21—C22—C231.1 (3)
C2—C3—C4—C53.6 (5)C21—C22—C23—C241.4 (3)
C3—C4—C5—C62.7 (5)C21—C22—C23—Cl1179.18 (17)
C2—C1—C6—C52.7 (4)C22—C23—C24—C250.7 (3)
S1—C1—C6—C5179.7 (2)Cl1—C23—C24—C25179.79 (14)
C4—C5—C6—C10.4 (5)C23—C24—C25—C200.1 (3)
N1—C7—C8—C91.87 (19)C23—C24—C25—N3177.42 (17)
C18—C7—C8—C9179.19 (17)C21—C20—C25—C240.4 (3)
N1—C7—C8—C15174.39 (17)C19—C20—C25—C24176.37 (17)
C18—C7—C8—C154.6 (3)C21—C20—C25—N3177.05 (18)
C7—C8—C9—C10179.8 (2)C19—C20—C25—N36.2 (3)
C15—C8—C9—C103.2 (3)C13—C14—N1—C7179.4 (2)
C7—C8—C9—C140.9 (2)C9—C14—N1—C71.50 (18)
C15—C8—C9—C14175.62 (16)C13—C14—N1—S128.8 (3)
C14—C9—C10—C111.5 (3)C9—C14—N1—S1152.11 (13)
C8—C9—C10—C11179.8 (2)C8—C7—N1—C142.11 (19)
C9—C10—C11—C121.6 (4)C18—C7—N1—C14178.85 (15)
C10—C11—C12—C130.7 (4)C8—C7—N1—S1151.63 (13)
C11—C12—C13—C140.3 (4)C18—C7—N1—S129.3 (2)
C12—C13—C14—C90.4 (3)C24—C25—N3—O6155.4 (2)
C12—C13—C14—N1179.3 (2)C20—C25—N3—O622.2 (3)
C10—C9—C14—C130.5 (3)C24—C25—N3—O520.7 (3)
C8—C9—C14—C13179.57 (18)C20—C25—N3—O5161.72 (19)
C10—C9—C14—N1178.64 (17)C14—N1—S1—O1178.89 (13)
C8—C9—C14—N10.39 (19)C7—N1—S1—O135.43 (16)
C7—C8—C15—O3121.1 (3)C14—N1—S1—O249.93 (15)
C9—C8—C15—O363.1 (3)C7—N1—S1—O2164.38 (14)
C7—C8—C15—C1662.5 (3)C14—N1—S1—C165.22 (15)
C9—C8—C15—C16113.3 (2)C7—N1—S1—C180.47 (15)
O3—C15—C16—C176.7 (4)C6—C1—S1—O137.0 (2)
C8—C15—C16—C17169.6 (2)C2—C1—S1—O1139.98 (19)
C8—C7—C18—C1939.8 (3)C6—C1—S1—O2170.50 (19)
N1—C7—C18—C19141.39 (18)C2—C1—S1—O26.5 (2)
C7—C18—C19—C20178.51 (16)C6—C1—S1—N176.5 (2)
C18—C19—C20—C2137.1 (3)C2—C1—S1—N1106.5 (2)
C18—C19—C20—C25146.33 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O1i0.932.603.327 (3)136
C16—H16B···O5ii0.972.373.260 (3)152
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O1i0.932.603.327 (3)136
C16—H16B···O5ii0.972.373.260 (3)152
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.
 

Acknowledgements

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

References

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o749.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationChakkaravarthi, G., Panchatcharam, R., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2010). Acta Cryst. E66, o2957.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationOkabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386–387.  Web of Science CSD CrossRef IUCr Journals 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
First citationSrivastava, Anupam & Pandeya, S. N. (2011). JCPR, 1, 1–17.  Google Scholar

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