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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o488.
Published online 2008 January 23. doi:  10.1107/S1600536807068705
PMCID: PMC2960420

1′-Phenyl-6′-thia­cyclo­heptane-1-spiro-2′-perhydro­pyrrolizine-3′-spiro-3′′-indoline-2,2′′-dione

Abstract

The thia­zolidine ring and the pyrrolidine ring in the title compound, C25H26N2O2S, both adopt an envelope conformation. The seven-membered ring has a twist-chair conformation. The crystal packing is stabilized by inter­molecular N—H(...)O hydrogen bonds.

Related literature

For related literature, see: Amal Raj et al. (2003 [triangle]); Cremer & Pople (1975 [triangle]); Kumar et al. (2006 [triangle]); Nardelli (1983 [triangle]); Si et al. (2005 [triangle]).

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Object name is e-64-0o488-scheme1.jpg

Experimental

Crystal data

  • C25H26N2O2S
  • M r = 418.54
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o488-efi1.jpg
  • a = 8.9846 (10) Å
  • b = 10.3564 (11) Å
  • c = 12.8124 (14) Å
  • α = 80.147 (2)°
  • β = 71.012 (2)°
  • γ = 67.497 (2)°
  • V = 1040.0 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.18 mm−1
  • T = 293 (2) K
  • 0.26 × 0.25 × 0.23 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 11582 measured reflections
  • 4697 independent reflections
  • 3880 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.157
  • S = 1.08
  • 4697 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068705/bt2666sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068705/bt2666Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

DG thanks the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship. Financial support from the University Grants Commission (UGC–SAP) and the Department of Science and Technology (DST–FIST), Government of India, is acknowledged by DV for providing facilities to the department.

supplementary crystallographic information

Comment

It has been reported that pyrrolidine derivatives reduce Coxsackievirus B3 replication through inhibition of the Ubiquitin-Proteasome pathway (Si et al., 2005). They are found to have antimicrobial and antifungal activity against various pathogens except Bacillus subtilis (Amal Raj et al., 2003). As the derivatives of pyrrolidine and oxindole are of pharmacological importance, we have undertaken the X-ray crystal structure determination of the title compound.

The bond lengths and bond angles of the title compound are comparable with a similar structure (Kumar et al., 2006). The sum of the bond angles around N1 atom [341.8 (5)°] indicates sp3 hybridization. The dihedral angle between the phenyl ring and the six membered in the oxindole moiety is 40.5 (1)°.

The thiazolidine ring adopts an envelope conformation with S1 atom deviating by 0.764 (1) Å. The pyrrolidine ring (N1/C1—C4) adopts an envelope conformation with C2 atom deviating by -0.655 (2) Å. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for the pyrrolidine ring, five membered ring (N2/C7/C1/C13/C8) in the oxindole moiety and the thiazolidine ring are q2 = 0.424 (2), 0.068 (2), 0.443 (2) Å, [var phi] = 80.4 (3), 264.7 (18), 355.5 (3)° and Δs(C2) = 7.7 (2), Δ2(N2) = 0.9 (3), Δs(S1) = 5.9 (2).

The crystal packing is stabilized by intermolecular N—H···O hydrogen bonds generating a centrosymmetric dimeric ring motif [R22(8)].

Experimental

A mixture of isatin (0.147 g, 1 mmol), thiaproline, (0.135 g, 1 mmol) and benzylidenecycloheptanone (1 mmol) in methanol (20 ml) was refluxed until the disappearance of the starting materials. The reaction mixture was then concentrated in vacuo and extracted with water (50 ml) and dichloromethane (50 ml). The organic layer was washed with brine solution, dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography with hexane-ethylacetate (8:2) mixture to get title compound. The pure compound was recrystallized from ethanol.

Figures

Fig. 1.
The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids.
Fig. 2.
The packing of the title compound, viewed down the a axis, H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C25H26N2O2SZ = 2
Mr = 418.54F000 = 444
Triclinic, P1Dx = 1.337 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.9846 (10) ÅCell parameters from 2358 reflections
b = 10.3564 (11) Åθ = 1.7–25.0º
c = 12.8124 (14) ŵ = 0.18 mm1
α = 80.147 (2)ºT = 293 (2) K
β = 71.012 (2)ºBlock, colorless
γ = 67.497 (2)º0.26 × 0.25 × 0.23 mm
V = 1040.0 (2) Å3

Data collection

Bruker SMART CCD area-detector diffractometer3880 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Monochromator: graphiteθmax = 28.0º
T = 293(2) Kθmin = 1.7º
ω scansh = −11→11
Absorption correction: nonek = −13→13
11582 measured reflectionsl = −16→16
4697 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.157  w = 1/[σ2(Fo2) + (0.0833P)2 + 0.2981P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
4697 reflectionsΔρmax = 0.36 e Å3
271 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
C10.2327 (2)0.71980 (19)0.35784 (14)0.0267 (4)
C20.1643 (2)0.84561 (18)0.27522 (14)0.0245 (4)
C30.2629 (2)0.93969 (19)0.27834 (14)0.0275 (4)
H30.38070.89160.23860.033*
C40.2543 (2)0.9308 (2)0.39991 (15)0.0309 (4)
H40.15031.00220.43860.037*
C50.4043 (3)0.9465 (3)0.4219 (2)0.0486 (6)
H5A0.36750.99610.48870.058*
H5B0.45680.99890.36070.058*
C60.3716 (3)0.7143 (3)0.4993 (2)0.0477 (6)
H6A0.40630.61460.49180.057*
H6B0.32560.73250.57730.057*
C70.1116 (2)0.63856 (19)0.41978 (14)0.0283 (4)
C80.3423 (3)0.4830 (2)0.31052 (16)0.0340 (4)
C90.4440 (3)0.3632 (2)0.25409 (19)0.0474 (6)
H90.41180.28550.26480.057*
C100.5958 (3)0.3639 (3)0.1810 (2)0.0552 (7)
H100.66650.28570.14040.066*
C110.6440 (3)0.4783 (3)0.1674 (2)0.0521 (6)
H110.74820.47500.11930.063*
C120.5404 (3)0.5984 (2)0.22390 (18)0.0410 (5)
H120.57410.67520.21410.049*
C130.3852 (2)0.6016 (2)0.29553 (15)0.0311 (4)
C140.2143 (3)0.79473 (19)0.15917 (15)0.0312 (4)
C150.1212 (3)0.7116 (2)0.13959 (18)0.0435 (5)
H15A0.06940.67110.20930.052*
H15B0.19900.63600.09200.052*
C16−0.0142 (4)0.8082 (3)0.0852 (2)0.0584 (7)
H16A0.03700.85840.02160.070*
H16B−0.05760.75140.05880.070*
C17−0.1593 (3)0.9132 (3)0.1619 (2)0.0600 (7)
H17A−0.22340.86310.21720.072*
H17B−0.23260.97630.11930.072*
C18−0.1110 (3)1.0007 (2)0.22123 (19)0.0433 (5)
H18A−0.21131.07770.25380.052*
H18B−0.03391.04060.16690.052*
C19−0.0288 (2)0.9197 (2)0.31231 (15)0.0307 (4)
H19A−0.07930.84970.34740.037*
H19B−0.05610.98440.36790.037*
C200.2132 (2)1.0876 (2)0.22729 (15)0.0300 (4)
C210.3124 (3)1.1172 (2)0.12397 (17)0.0393 (5)
H210.40701.04590.08760.047*
C220.2726 (3)1.2504 (3)0.07487 (19)0.0503 (6)
H220.34061.26810.00600.060*
C230.1336 (4)1.3570 (2)0.1268 (2)0.0512 (6)
H230.10511.44610.09240.061*
C240.0365 (3)1.3313 (2)0.2302 (2)0.0477 (6)
H24−0.05651.40390.26650.057*
C250.0765 (3)1.1980 (2)0.28063 (18)0.0385 (5)
H250.01101.18220.35110.046*
N10.2471 (2)0.79135 (17)0.44146 (12)0.0312 (4)
N20.1822 (2)0.50686 (17)0.38528 (14)0.0365 (4)
H20.13470.44510.40660.044*
O1−0.02147 (18)0.68469 (15)0.49036 (11)0.0377 (3)
O20.3167 (2)0.82744 (17)0.08308 (11)0.0449 (4)
S10.55069 (8)0.77332 (8)0.43717 (6)0.0609 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0286 (9)0.0307 (9)0.0235 (8)−0.0144 (8)−0.0074 (7)0.0014 (7)
C20.0295 (9)0.0258 (9)0.0194 (8)−0.0125 (7)−0.0066 (7)0.0012 (7)
C30.0301 (9)0.0301 (9)0.0234 (9)−0.0143 (8)−0.0045 (7)−0.0014 (7)
C40.0358 (10)0.0354 (10)0.0264 (9)−0.0176 (8)−0.0091 (8)−0.0014 (8)
C50.0577 (15)0.0605 (15)0.0485 (13)−0.0368 (12)−0.0255 (11)0.0027 (11)
C60.0591 (15)0.0524 (14)0.0437 (12)−0.0251 (12)−0.0296 (11)0.0099 (10)
C70.0345 (10)0.0316 (10)0.0220 (8)−0.0166 (8)−0.0096 (7)0.0051 (7)
C80.0395 (11)0.0309 (10)0.0289 (9)−0.0104 (9)−0.0115 (8)0.0039 (8)
C90.0591 (15)0.0308 (11)0.0446 (12)−0.0088 (10)−0.0154 (11)0.0015 (9)
C100.0559 (15)0.0376 (12)0.0446 (13)0.0071 (11)−0.0077 (11)−0.0015 (10)
C110.0362 (12)0.0530 (15)0.0435 (13)−0.0005 (11)−0.0028 (10)0.0044 (11)
C120.0337 (11)0.0433 (12)0.0383 (11)−0.0108 (9)−0.0075 (9)0.0052 (9)
C130.0316 (10)0.0327 (10)0.0259 (9)−0.0092 (8)−0.0100 (8)0.0043 (7)
C140.0404 (11)0.0272 (9)0.0255 (9)−0.0110 (8)−0.0103 (8)0.0001 (7)
C150.0661 (15)0.0409 (12)0.0357 (11)−0.0268 (11)−0.0212 (10)−0.0010 (9)
C160.0824 (19)0.0688 (17)0.0485 (14)−0.0382 (15)−0.0401 (14)0.0050 (12)
C170.0601 (16)0.0745 (18)0.0625 (16)−0.0296 (14)−0.0409 (14)0.0135 (14)
C180.0408 (12)0.0444 (12)0.0435 (12)−0.0107 (10)−0.0202 (10)0.0068 (10)
C190.0298 (10)0.0352 (10)0.0259 (9)−0.0123 (8)−0.0075 (8)0.0028 (8)
C200.0372 (10)0.0313 (10)0.0273 (9)−0.0189 (8)−0.0090 (8)0.0001 (7)
C210.0471 (12)0.0397 (11)0.0316 (10)−0.0215 (10)−0.0057 (9)0.0000 (9)
C220.0710 (17)0.0501 (14)0.0367 (12)−0.0360 (13)−0.0131 (11)0.0110 (10)
C230.0764 (17)0.0352 (12)0.0554 (14)−0.0290 (12)−0.0331 (13)0.0147 (10)
C240.0562 (14)0.0318 (11)0.0581 (14)−0.0125 (10)−0.0222 (12)−0.0057 (10)
C250.0442 (12)0.0363 (11)0.0350 (10)−0.0169 (9)−0.0070 (9)−0.0037 (9)
N10.0371 (9)0.0375 (9)0.0259 (8)−0.0184 (7)−0.0141 (7)0.0032 (7)
N20.0430 (10)0.0299 (8)0.0372 (9)−0.0191 (7)−0.0074 (8)0.0041 (7)
O10.0382 (8)0.0393 (8)0.0332 (7)−0.0206 (6)−0.0002 (6)0.0013 (6)
O20.0558 (10)0.0530 (9)0.0247 (7)−0.0257 (8)0.0002 (7)−0.0059 (6)
S10.0454 (4)0.0753 (5)0.0743 (5)−0.0243 (3)−0.0318 (3)0.0007 (4)

Geometric parameters (Å, °)

C1—N11.466 (2)C12—C131.389 (3)
C1—C131.534 (3)C12—H120.9300
C1—C71.560 (2)C14—O21.206 (2)
C1—C21.592 (2)C14—C151.505 (3)
C2—C141.531 (2)C15—C161.532 (3)
C2—C191.547 (3)C15—H15A0.9700
C2—C31.560 (2)C15—H15B0.9700
C3—C201.516 (3)C16—C171.514 (4)
C3—C41.523 (2)C16—H16A0.9700
C3—H30.9800C16—H16B0.9700
C4—N11.469 (2)C17—C181.530 (3)
C4—C51.535 (3)C17—H17A0.9700
C4—H40.9800C17—H17B0.9700
C5—S11.796 (3)C18—C191.537 (3)
C5—H5A0.9700C18—H18A0.9700
C5—H5B0.9700C18—H18B0.9700
C6—N11.445 (3)C19—H19A0.9700
C6—S11.830 (2)C19—H19B0.9700
C6—H6A0.9700C20—C251.389 (3)
C6—H6B0.9700C20—C211.394 (3)
C7—O11.217 (2)C21—C221.378 (3)
C7—N21.349 (2)C21—H210.9300
C8—C91.381 (3)C22—C231.370 (4)
C8—C131.388 (3)C22—H220.9300
C8—N21.400 (3)C23—C241.375 (4)
C9—C101.382 (3)C23—H230.9300
C9—H90.9300C24—C251.385 (3)
C10—C111.377 (4)C24—H240.9300
C10—H100.9300C25—H250.9300
C11—C121.386 (3)N2—H20.8600
C11—H110.9300
N1—C1—C13120.41 (15)O2—C14—C2121.75 (17)
N1—C1—C7106.89 (14)C15—C14—C2118.00 (17)
C13—C1—C7100.64 (14)C14—C15—C16109.25 (18)
N1—C1—C2102.68 (14)C14—C15—H15A109.8
C13—C1—C2111.37 (14)C16—C15—H15A109.8
C7—C1—C2115.44 (14)C14—C15—H15B109.8
C14—C2—C19108.15 (15)C16—C15—H15B109.8
C14—C2—C3111.12 (14)H15A—C15—H15B108.3
C19—C2—C3113.41 (15)C17—C16—C15113.6 (2)
C14—C2—C1110.81 (14)C17—C16—H16A108.8
C19—C2—C1113.62 (14)C15—C16—H16A108.8
C3—C2—C199.60 (13)C17—C16—H16B108.8
C20—C3—C4114.20 (15)C15—C16—H16B108.8
C20—C3—C2118.60 (15)H16A—C16—H16B107.7
C4—C3—C2103.40 (14)C16—C17—C18115.7 (2)
C20—C3—H3106.6C16—C17—H17A108.4
C4—C3—H3106.6C18—C17—H17A108.4
C2—C3—H3106.6C16—C17—H17B108.4
N1—C4—C3104.86 (14)C18—C17—H17B108.4
N1—C4—C5109.38 (17)H17A—C17—H17B107.4
C3—C4—C5114.85 (16)C17—C18—C19114.69 (19)
N1—C4—H4109.2C17—C18—H18A108.6
C3—C4—H4109.2C19—C18—H18A108.6
C5—C4—H4109.2C17—C18—H18B108.6
C4—C5—S1107.24 (15)C19—C18—H18B108.6
C4—C5—H5A110.3H18A—C18—H18B107.6
S1—C5—H5A110.3C18—C19—C2116.35 (16)
C4—C5—H5B110.3C18—C19—H19A108.2
S1—C5—H5B110.3C2—C19—H19A108.2
H5A—C5—H5B108.5C18—C19—H19B108.2
N1—C6—S1107.08 (15)C2—C19—H19B108.2
N1—C6—H6A110.3H19A—C19—H19B107.4
S1—C6—H6A110.3C25—C20—C21117.67 (18)
N1—C6—H6B110.3C25—C20—C3123.12 (17)
S1—C6—H6B110.3C21—C20—C3119.15 (18)
H6A—C6—H6B108.6C22—C21—C20121.1 (2)
O1—C7—N2125.70 (17)C22—C21—H21119.5
O1—C7—C1125.71 (17)C20—C21—H21119.5
N2—C7—C1108.54 (16)C23—C22—C21120.4 (2)
C9—C8—C13123.1 (2)C23—C22—H22119.8
C9—C8—N2126.65 (19)C21—C22—H22119.8
C13—C8—N2110.23 (17)C22—C23—C24119.5 (2)
C8—C9—C10117.0 (2)C22—C23—H23120.2
C8—C9—H9121.5C24—C23—H23120.2
C10—C9—H9121.5C23—C24—C25120.4 (2)
C11—C10—C9121.1 (2)C23—C24—H24119.8
C11—C10—H10119.5C25—C24—H24119.8
C9—C10—H10119.5C24—C25—C20120.8 (2)
C10—C11—C12121.4 (2)C24—C25—H25119.6
C10—C11—H11119.3C20—C25—H25119.6
C12—C11—H11119.3C6—N1—C1117.96 (17)
C11—C12—C13118.6 (2)C6—N1—C4112.11 (16)
C11—C12—H12120.7C1—N1—C4111.66 (14)
C13—C12—H12120.7C7—N2—C8111.73 (16)
C8—C13—C12118.80 (19)C7—N2—H2124.1
C8—C13—C1108.37 (16)C8—N2—H2124.1
C12—C13—C1132.51 (18)C5—S1—C688.36 (11)
O2—C14—C15120.06 (18)
N1—C1—C2—C14154.06 (15)C3—C2—C14—O2−0.4 (3)
C13—C1—C2—C1423.9 (2)C1—C2—C14—O2−110.2 (2)
C7—C1—C2—C14−90.04 (18)C19—C2—C14—C15−50.3 (2)
N1—C1—C2—C19−83.94 (17)C3—C2—C14—C15−175.42 (17)
C13—C1—C2—C19145.89 (16)C1—C2—C14—C1574.8 (2)
C7—C1—C2—C1932.0 (2)O2—C14—C15—C16−75.9 (3)
N1—C1—C2—C336.98 (16)C2—C14—C15—C1699.2 (2)
C13—C1—C2—C3−93.19 (16)C14—C15—C16—C17−70.3 (3)
C7—C1—C2—C3152.88 (15)C15—C16—C17—C1852.0 (3)
C14—C2—C3—C2074.5 (2)C16—C17—C18—C19−71.4 (3)
C19—C2—C3—C20−47.6 (2)C17—C18—C19—C287.6 (2)
C1—C2—C3—C20−168.64 (15)C14—C2—C19—C18−34.2 (2)
C14—C2—C3—C4−157.92 (15)C3—C2—C19—C1889.6 (2)
C19—C2—C3—C480.01 (17)C1—C2—C19—C18−157.62 (16)
C1—C2—C3—C4−41.06 (17)C4—C3—C20—C25−42.5 (3)
C20—C3—C4—N1160.57 (15)C2—C3—C20—C2579.8 (2)
C2—C3—C4—N130.29 (18)C4—C3—C20—C21134.67 (19)
C20—C3—C4—C5−79.4 (2)C2—C3—C20—C21−103.0 (2)
C2—C3—C4—C5150.37 (17)C25—C20—C21—C22−2.2 (3)
N1—C4—C5—S122.4 (2)C3—C20—C21—C22−179.53 (19)
C3—C4—C5—S1−95.20 (18)C20—C21—C22—C23−0.2 (4)
N1—C1—C7—O145.1 (2)C21—C22—C23—C242.1 (4)
C13—C1—C7—O1171.63 (18)C22—C23—C24—C25−1.5 (4)
C2—C1—C7—O1−68.4 (2)C23—C24—C25—C20−1.0 (3)
N1—C1—C7—N2−132.43 (16)C21—C20—C25—C242.8 (3)
C13—C1—C7—N2−5.90 (18)C3—C20—C25—C24−179.97 (19)
C2—C1—C7—N2114.09 (17)S1—C6—N1—C1101.84 (17)
C13—C8—C9—C100.9 (3)S1—C6—N1—C4−30.0 (2)
N2—C8—C9—C10177.8 (2)C13—C1—N1—C6−27.7 (2)
C8—C9—C10—C111.4 (4)C7—C1—N1—C686.0 (2)
C9—C10—C11—C12−1.9 (4)C2—C1—N1—C6−152.11 (16)
C10—C11—C12—C130.1 (4)C13—C1—N1—C4104.30 (18)
C9—C8—C13—C12−2.7 (3)C7—C1—N1—C4−142.00 (16)
N2—C8—C13—C12179.99 (17)C2—C1—N1—C4−20.10 (19)
C9—C8—C13—C1171.59 (19)C3—C4—N1—C6128.85 (18)
N2—C8—C13—C1−5.7 (2)C5—C4—N1—C65.2 (2)
C11—C12—C13—C82.1 (3)C3—C4—N1—C1−6.0 (2)
C11—C12—C13—C1−170.5 (2)C5—C4—N1—C1−129.71 (17)
N1—C1—C13—C8123.82 (18)O1—C7—N2—C8−174.57 (18)
C7—C1—C13—C86.88 (19)C1—C7—N2—C83.0 (2)
C2—C1—C13—C8−116.00 (16)C9—C8—N2—C7−175.5 (2)
N1—C1—C13—C12−63.0 (3)C13—C8—N2—C71.8 (2)
C7—C1—C13—C12−179.9 (2)C4—C5—S1—C6−33.23 (16)
C2—C1—C13—C1257.2 (3)N1—C6—S1—C536.70 (17)
C19—C2—C14—O2124.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.042.859 (2)160

Symmetry codes: (i) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2666).

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