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In the title compound, C19H17NO5S, the indole system is not strictly planar and the dihedral angle between the fused rings is 2.1 (1)°. The indole and phenyl rings are orthogonal to each other and the dihedral angle between them is 87.2 (1)°. The mol­ecules are joined into head-to-head dimers by hydrogen bonds involving the butyric acid groups. The centrosymmet­rically related C—H...O hydrogen bond pattern joins the head-to-head dimers into chains running parallel to the c axis. Neighbouring chains are held together by weak C—H...π and π–π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803010596/ww6085sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803010596/ww6085Isup2.hkl
Contains datablock I

CCDC reference: 214854

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.052
  • wR factor = 0.149
  • Data-to-parameter ratio = 17.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

Indole is an important heterocyclic compounds. Its ring system is present in a large number of natural products. Many of these natural products, as well as the synthetic derivatives, show a variety of useful biological properties, such as antibacterial (Okabe & Adachi, 1998), antitumour (Schollmeyer et al., 1995), antidepressant (Grinev et al., 1984), antimicrobial (El-Sayed et al., 1986; Gadaginamath & Patil, 1999) and anti-inflammatory (Rodriguez et al., 1985) activities. 4-(3-Indolyl)butyric acid (IBA) is known to possess growth-regulating activity (Steward & Krikorian, 1971). IBA shows a root-promoting effect in all lemon and lime varieties (Sircar, 1971) and is also effective in bud inhibition in many plants. The interaction of phenylsulfonylindole with the calf-thymus DNA by spectroscopic methods has also been studied (Sivaraman et al., 1996). Indoles have been proved to display high aldose reductose inhibitory activity (Rajeswaran et al., 1999). The structure determination of the title compound, (I), was undertaken as part of our studies on indole derivatives.

The indole system is not strictly planar and the dihedral angle formed by the pyrrole and benzene planes is 2.1 (1)°. The dihedral angle between the indole system and the phenyl ring is 87.2 (1)°. The 4-oxobutyric acid group is characterized by two planes, viz. the 3-oxopropyl group and the acid group. The plane of the indole system makes angles of 36.3 (1) and 68.2 (1)° with the 3-oxopropyl group and the acid group, respectively. Atoms S1, C16 and C17 deviate from the weighted least-squares plane through the indole system by −0.392 (1), 0.072 (3) and −0.108 (2) Å, respectively. Atoms N1 deviates by 0.155 (2) Å from the mean plane passing through atoms C2, C5 and S1. This slight pyramidalization behaviour is also observed in related indole derivatives (Sankaranarayanan et al., 2000, 2001). The bond angles around S1 show distorted tetrahedral geometry. The widening of the O1—S1—O2 angle [120.1 (1)°] from the tetrahedral value is presumably the results of repulsive interactions between the short SO bonds. Similar observations have been noted in the related structure (Sankaranarayanan et al., 2001). The S—C bond distance [1.757 (2) Å] agrees well with the literature value of 1.758 (13) Å (Allen et al., 1987) and S—N [1.698 (2) Å] bond distance is sligtly longer than the literature value of 1.642 (24) Å (Allen et al., 1987). The lengthening of the C—N distances in the pyrrole ring is due to the electron- withdrawing character of the phenylsulfonyl group. The 3-oxopropyl chain bond lengths and angles are in the expected ranges but its conformation is of interest. The torsion angles C2—C3—C17—O3, C4—C3—C17—C18, C3—C17—C18—C19, C17—C18—C19—C20, and C18—C19—C20—O4 are 24.3 (3), 24.7 (3), 171.8 (2), 79.6 (2) and 32.9 (3)°, respectively. C—H···O interactions have been recognized as important secondary interactions and, in many cases, play a dominant role in the molecular conformation (Steiner, 1997). Four such intramolecular interactions can be identified in the present structure. The conformation of the aliphatic chain is governed by two C—H···O intramolecular interactions. Evidence for steric strain is seen at the point where the phenylsulfonyl group joins the indole. The sulfonyl group comprising of atoms O1, O2 and S1, is prevented from lying in the plane of the indole ring by close approach of O1 and H atom bound to C6, while O2 is close to the methyl substituent at C2. Thus, the orientation of the indole subtituent is influenced by weak C6—H6···O1 and C16—H16B···O2 interactions, defined by the torsion angles C6—C5—N1—S1, C5—N1—S1—C10, C16—C2—N1—S1 and C2—N1—S1—C10.

The molecules are joined into head-to-head dimers with graph-set R22(8) (Bernstein et al., 1995) by hydrogen bonds involving the carboxylic acid groups. The O5···O4 distance is 2.715 (2) Å. Centrosymmetric hydrogen bonds between atom C15 of the phenyl ring and carbonyl atom O3 of 4-oxobutyric acid form another dimer with graph-set R22(18). This hydrogen bond pattern joins the head-to-head dimers into chains running parallel to c axis. The close edge-to-face interactions are observed between A and Biii and the equivalent pair B and Aiii, with interplanar angle of 88° and centroid-centroid distance of 5.088 (2) Å [symmetry code: (iii) 2 − x, −y, −z]. Face-to-face ring interactions between P (pyrrole) ring and Pv, and ring A and Aiii, are observed which stack in the lattice along a, with centroid-centroid distances of 4.129 (2) and 3.986 (2) Å, respectively [symmetry code: (v) 1 − x, −y, −z].

Experimental top

The title compound was prepared by the Friedel–Crafts acylation of 1-phenylsulfonly-2-methylindole with succinic anhydride in the presence of anhydrous aluminium chloride in dry methylene chloride.

Refinement top

All H atoms were included in calculated positions and allowed to ride on their corresponding parent atoms.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 35% probability displacement elliposids and the atom-numbering scheme.
[Figure 2] Fig. 2. A view of the crystal strucutre of (I), viewed down the a axis.
3-(1-Phenylsulfonyl-2-methylindol-3-ylcarbonyl)propanoic acid top
Crystal data top
C19H17NO5SZ = 2
Mr = 371.40F(000) = 388
Triclinic, P1Dx = 1.423 Mg m3
a = 8.1825 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.9758 (1) ÅCell parameters from 3857 reflections
c = 12.3121 (1) Åθ = 1.8–28.3°
α = 69.281 (1)°µ = 0.22 mm1
β = 72.067 (1)°T = 293 K
γ = 70.878 (1)°Block, colourless
V = 866.92 (2) Å30.46 × 0.42 × 0.24 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3144 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 28.3°, θmin = 1.8°
ω scansh = 108
6104 measured reflectionsk = 1312
4175 independent reflectionsl = 1613
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.091P)2]
where P = (Fo2 + 2Fc2)/3
4175 reflections(Δ/σ)max < 0.001
236 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.48 e Å3
Crystal data top
C19H17NO5Sγ = 70.878 (1)°
Mr = 371.40V = 866.92 (2) Å3
Triclinic, P1Z = 2
a = 8.1825 (2) ÅMo Kα radiation
b = 9.9758 (1) ŵ = 0.22 mm1
c = 12.3121 (1) ÅT = 293 K
α = 69.281 (1)°0.46 × 0.42 × 0.24 mm
β = 72.067 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
3144 reflections with I > 2σ(I)
6104 measured reflectionsRint = 0.025
4175 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 1.03Δρmax = 0.54 e Å3
4175 reflectionsΔρmin = 0.48 e Å3
236 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
xyzUiso*/Ueq
S10.50958 (6)0.07847 (6)0.31671 (4)0.04313 (17)
O10.5320 (2)0.07044 (18)0.38969 (12)0.0594 (4)
O20.34092 (18)0.1803 (2)0.33014 (14)0.0592 (4)
O30.5942 (3)0.38243 (17)0.16717 (15)0.0787 (6)
O40.9696 (2)0.34093 (18)0.41035 (15)0.0667 (5)
O50.7594 (2)0.52339 (17)0.48807 (15)0.0655 (5)
H50.83870.56710.51410.098*
N10.5662 (2)0.06819 (18)0.17460 (13)0.0405 (4)
C20.5299 (2)0.1871 (2)0.07346 (16)0.0402 (4)
C30.6399 (2)0.1493 (2)0.02604 (15)0.0389 (4)
C40.7505 (2)0.0013 (2)0.01113 (16)0.0379 (4)
C50.7065 (2)0.0455 (2)0.13608 (16)0.0390 (4)
C60.7942 (3)0.1812 (2)0.20103 (19)0.0515 (5)
H60.76380.21050.28370.062*
C70.9275 (3)0.2708 (2)0.1393 (2)0.0549 (5)
H70.98890.36130.18100.066*
C80.9716 (3)0.2284 (2)0.0158 (2)0.0550 (5)
H81.06070.29150.02390.066*
C90.8852 (3)0.0940 (2)0.04857 (19)0.0497 (5)
H90.91600.06650.13130.060*
C100.6703 (2)0.1553 (2)0.32291 (15)0.0354 (4)
C110.8229 (3)0.0634 (2)0.36120 (17)0.0429 (4)
H110.83930.03870.38700.051*
C120.9508 (2)0.1286 (3)0.35991 (19)0.0490 (5)
H121.05450.06930.38470.059*
C130.9246 (3)0.2797 (2)0.32226 (19)0.0499 (5)
H131.01160.32180.32080.060*
C140.7714 (3)0.3693 (2)0.2868 (2)0.0553 (5)
H140.75440.47140.26250.066*
C150.6419 (3)0.3071 (2)0.2873 (2)0.0481 (5)
H150.53750.36700.26400.058*
C160.3821 (3)0.3227 (3)0.0792 (2)0.0580 (6)
H16A0.41900.38960.10130.087*
H16B0.28050.29550.13740.087*
H16C0.35210.37000.00280.087*
C170.6432 (3)0.2493 (2)0.14853 (17)0.0438 (4)
C180.7129 (3)0.1844 (2)0.25187 (16)0.0450 (4)
H18A0.65510.10680.23680.054*
H18B0.83890.13970.25810.054*
C190.6834 (3)0.2986 (2)0.36994 (17)0.0485 (5)
H19A0.68930.24800.42590.058*
H19B0.56570.36350.35740.058*
C200.8174 (3)0.3898 (2)0.42252 (16)0.0453 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0373 (3)0.0634 (3)0.0339 (2)0.0278 (2)0.00063 (18)0.0130 (2)
O10.0784 (11)0.0707 (10)0.0356 (7)0.0471 (9)0.0023 (7)0.0048 (7)
O20.0301 (7)0.0998 (12)0.0534 (9)0.0213 (7)0.0010 (6)0.0317 (9)
O30.1296 (18)0.0431 (9)0.0502 (9)0.0043 (10)0.0254 (10)0.0082 (7)
O40.0577 (10)0.0624 (10)0.0679 (10)0.0298 (8)0.0220 (8)0.0167 (8)
O50.0639 (10)0.0526 (9)0.0722 (11)0.0240 (8)0.0239 (8)0.0080 (8)
N10.0403 (8)0.0504 (9)0.0327 (7)0.0188 (7)0.0043 (6)0.0099 (7)
C20.0381 (9)0.0477 (10)0.0391 (9)0.0165 (8)0.0090 (7)0.0112 (8)
C30.0432 (10)0.0429 (10)0.0341 (9)0.0177 (8)0.0082 (7)0.0085 (7)
C40.0410 (9)0.0407 (9)0.0359 (9)0.0187 (8)0.0079 (7)0.0078 (7)
C50.0407 (10)0.0438 (10)0.0371 (9)0.0217 (8)0.0078 (7)0.0071 (7)
C60.0611 (13)0.0501 (11)0.0420 (10)0.0216 (10)0.0144 (9)0.0013 (9)
C70.0590 (13)0.0404 (10)0.0622 (13)0.0115 (10)0.0226 (11)0.0036 (9)
C80.0558 (13)0.0473 (12)0.0588 (13)0.0093 (10)0.0094 (10)0.0171 (10)
C90.0561 (12)0.0469 (11)0.0430 (10)0.0157 (9)0.0028 (9)0.0131 (9)
C100.0293 (8)0.0460 (10)0.0314 (8)0.0141 (7)0.0017 (6)0.0111 (7)
C110.0379 (9)0.0437 (10)0.0444 (10)0.0073 (8)0.0100 (8)0.0109 (8)
C120.0302 (9)0.0676 (14)0.0510 (11)0.0071 (9)0.0103 (8)0.0220 (10)
C130.0354 (10)0.0660 (13)0.0576 (12)0.0212 (9)0.0037 (9)0.0257 (11)
C140.0534 (13)0.0479 (11)0.0699 (14)0.0197 (10)0.0155 (11)0.0143 (10)
C150.0405 (10)0.0463 (11)0.0587 (12)0.0095 (8)0.0191 (9)0.0100 (9)
C160.0540 (13)0.0633 (14)0.0521 (12)0.0041 (11)0.0121 (10)0.0196 (11)
C170.0499 (11)0.0420 (10)0.0391 (10)0.0142 (9)0.0111 (8)0.0069 (8)
C180.0560 (12)0.0459 (10)0.0350 (9)0.0259 (9)0.0043 (8)0.0063 (8)
C190.0554 (12)0.0596 (12)0.0349 (9)0.0288 (10)0.0079 (8)0.0067 (9)
C200.0535 (12)0.0495 (11)0.0322 (9)0.0223 (9)0.0095 (8)0.0019 (8)
Geometric parameters (Å, º) top
S1—O21.422 (2)C9—H90.9300
S1—O11.424 (2)C10—C151.379 (3)
S1—N11.698 (2)C10—C111.389 (3)
S1—C101.757 (2)C11—C121.395 (3)
O3—C171.212 (2)C11—H110.9300
O4—C201.215 (3)C12—C131.375 (3)
O5—C201.309 (2)C12—H120.9300
O5—H50.8200C13—C141.374 (3)
N1—C21.414 (2)C13—H130.9300
N1—C51.422 (2)C14—C151.390 (3)
C2—C31.371 (3)C14—H140.9300
C2—C161.497 (3)C15—H150.9300
C3—C41.453 (3)C16—H16A0.9600
C3—C171.483 (2)C16—H16B0.9600
C4—C91.402 (3)C16—H16C0.9600
C4—C51.405 (2)C17—C181.502 (3)
C5—C61.392 (3)C18—C191.527 (3)
C6—C71.377 (3)C18—H18A0.9700
C6—H60.9300C18—H18B0.9700
C7—C81.388 (3)C19—C201.499 (3)
C7—H70.9300C19—H19A0.9700
C8—C91.378 (3)C19—H19B0.9700
C8—H80.9300
O2—S1—O1120.1 (1)C10—C11—H11120.9
O2—S1—N1106.9 (1)C12—C11—H11120.9
O1—S1—N1105.6 (1)C13—C12—C11120.4 (2)
O2—S1—C10109.3 (1)C13—C12—H12119.8
O1—S1—C10109.9 (1)C11—C12—H12119.8
N1—S1—C10103.7 (1)C14—C13—C12120.7 (2)
C20—O5—H5109.5C14—C13—H13119.7
C2—N1—C5108.5 (1)C12—C13—H13119.7
C2—N1—S1125.8 (1)C13—C14—C15120.0 (2)
C5—N1—S1122.6 (1)C13—C14—H14120.0
C3—C2—N1108.5 (2)C15—C14—H14120.0
C3—C2—C16127.8 (2)C10—C15—C14119.1 (2)
N1—C2—C16123.4 (2)C10—C15—H15120.4
C2—C3—C4108.4 (2)C14—C15—H15120.4
C2—C3—C17123.7 (2)C2—C16—H16A109.5
C4—C3—C17127.9 (2)C2—C16—H16B109.5
C9—C4—C5118.3 (2)H16A—C16—H16B109.5
C9—C4—C3134.6 (2)C2—C16—H16C109.5
C5—C4—C3107.1 (2)H16A—C16—H16C109.5
C6—C5—C4122.0 (2)H16B—C16—H16C109.5
C6—C5—N1130.6 (2)O3—C17—C3121.4 (2)
C4—C5—N1107.4 (2)O3—C17—C18119.3 (2)
C7—C6—C5118.1 (2)C3—C17—C18119.3 (2)
C7—C6—H6121.0C17—C18—C19113.0 (2)
C5—C6—H6121.0C17—C18—H18A109.0
C6—C7—C8121.1 (2)C19—C18—H18A109.0
C6—C7—H7119.4C17—C18—H18B109.0
C8—C7—H7119.4C19—C18—H18B109.0
C9—C8—C7120.9 (2)H18A—C18—H18B107.8
C9—C8—H8119.6C20—C19—C18112.6 (2)
C7—C8—H8119.6C20—C19—H19A109.1
C8—C9—C4119.7 (2)C18—C19—H19A109.1
C8—C9—H9120.1C20—C19—H19B109.1
C4—C9—H9120.1C18—C19—H19B109.1
C15—C10—C11121.6 (2)H19A—C19—H19B107.8
C15—C10—S1118.5 (1)O4—C20—O5122.9 (2)
C11—C10—S1119.9 (1)O4—C20—C19122.7 (2)
C10—C11—C12118.2 (2)O5—C20—C19114.4 (2)
O2—S1—N1—C236.8 (2)C5—C6—C7—C80.9 (3)
O1—S1—N1—C2165.8 (2)C6—C7—C8—C91.1 (4)
C10—S1—N1—C278.7 (2)C7—C8—C9—C40.2 (3)
O2—S1—N1—C5165.8 (1)C5—C4—C9—C80.9 (3)
O1—S1—N1—C536.8 (2)C3—C4—C9—C8176.7 (2)
C10—S1—N1—C578.8 (2)O2—S1—C10—C1527.9 (2)
C5—N1—C2—C31.3 (2)O1—S1—C10—C15161.7 (2)
S1—N1—C2—C3161.4 (1)N1—S1—C10—C1585.8 (2)
C5—N1—C2—C16176.0 (2)O2—S1—C10—C11153.2 (2)
S1—N1—C2—C1623.9 (3)O1—S1—C10—C1119.3 (2)
N1—C2—C3—C40.3 (2)N1—S1—C10—C1193.2 (2)
C16—C2—C3—C4174.1 (2)C15—C10—C11—C121.7 (3)
N1—C2—C3—C17178.0 (2)S1—C10—C11—C12177.2 (1)
C16—C2—C3—C177.6 (3)C10—C11—C12—C130.4 (3)
C2—C3—C4—C9179.7 (2)C11—C12—C13—C140.9 (3)
C17—C3—C4—C91.5 (3)C12—C13—C14—C150.8 (3)
C2—C3—C4—C51.9 (2)C11—C10—C15—C141.7 (3)
C17—C3—C4—C5176.4 (2)S1—C10—C15—C14177.2 (2)
C9—C4—C5—C61.1 (3)C13—C14—C15—C100.5 (3)
C3—C4—C5—C6177.1 (2)C2—C3—C17—O324.3 (3)
C9—C4—C5—N1179.1 (2)C4—C3—C17—O3153.7 (2)
C3—C4—C5—N12.7 (2)C2—C3—C17—C18157.3 (2)
C2—N1—C5—C6177.3 (2)C4—C3—C17—C1824.7 (3)
S1—N1—C5—C616.4 (3)O3—C17—C18—C199.8 (3)
C2—N1—C5—C42.5 (2)C3—C17—C18—C19171.8 (2)
S1—N1—C5—C4163.4 (1)C17—C18—C19—C2079.6 (2)
C4—C5—C6—C70.2 (3)C18—C19—C20—O432.9 (3)
N1—C5—C6—C7179.9 (2)C18—C19—C20—O5150.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.932.302.901 (3)122
C16—H16B···O20.962.372.871 (3)112
C16—H16C···O30.962.402.954 (3)117
C18—H18B···O40.972.492.851 (3)102
O5—H5···O4i0.821.902.715 (2)173
C15—H15···O3ii0.932.403.180 (3)142
C8—H8···Cgiii0.933.393.997 (2)125
C9—H9···Cgiii0.933.193.893 (2)134
C19—H19A···Cgiv0.973.043.910 (3)150
Symmetry codes: (i) x+2, y+1, z1; (ii) x+1, y+1, z; (iii) x+2, y, z; (iv) x, y, z1.

Experimental details

Crystal data
Chemical formulaC19H17NO5S
Mr371.40
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.1825 (2), 9.9758 (1), 12.3121 (1)
α, β, γ (°)69.281 (1), 72.067 (1), 70.878 (1)
V3)866.92 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.46 × 0.42 × 0.24
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6104, 4175, 3144
Rint0.025
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.149, 1.03
No. of reflections4175
No. of parameters236
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.54, 0.48

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top
S1—O21.422 (2)O4—C201.215 (3)
S1—O11.424 (2)O5—C201.309 (2)
S1—N11.698 (2)N1—C21.414 (2)
S1—C101.757 (2)N1—C51.422 (2)
O3—C171.212 (2)
O2—S1—O1120.1 (1)N1—S1—C10103.7 (1)
O2—S1—N1106.9 (1)C2—N1—C5108.5 (1)
O1—S1—N1105.6 (1)C2—N1—S1125.8 (1)
O2—S1—C10109.3 (1)C5—N1—S1122.6 (1)
O1—S1—C10109.9 (1)
C10—S1—N1—C278.7 (2)S1—N1—C2—C1623.9 (3)
C10—S1—N1—C578.8 (2)S1—N1—C5—C616.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.932.302.901 (3)122
C16—H16B···O20.962.372.871 (3)112
C16—H16C···O30.962.402.954 (3)117
C18—H18B···O40.972.492.851 (3)102
O5—H5···O4i0.821.902.715 (2)173
C15—H15···O3ii0.932.403.180 (3)142
C8—H8···Cgiii0.933.393.997 (2)125
C9—H9···Cgiii0.933.193.893 (2)134
C19—H19A···Cgiv0.973.043.910 (3)150
Symmetry codes: (i) x+2, y+1, z1; (ii) x+1, y+1, z; (iii) x+2, y, z; (iv) x, y, z1.
 

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