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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o174–o175.
Published online 2008 December 20. doi:  10.1107/S1600536808042761
PMCID: PMC2968085

1,3-Bis(3-phenyl­prop­yl)-1H-benzimidazol-3-ium-2-carbodithio­ate

Abstract

The title compound, C26H26N2S2, was synthesized from bis­[1,3-bis­(3-phenyl­prop­yl)benzimidazolidine-2-yl­idene] and CS2 in toluene. The mol­ecular structure is composed of a benzimidazole ring system with two phenyl­propyl substituents and a dithio­carboxyl­ate group in the 2-position. The benzimidazole unit is essentially planar, with a maximum atomic deviation of 0.008 (2) Å, and makes dihedral angles of 72.72 (10) and 27.62 (12)°, with the two phenyl rings. The dihedral angle between the two phenyl rings is 55.98 (15)°. The mol­ecular packing is stabilized by a C—H(...)S inter­molecular hydrogen-bonding inter­action and a C—H(...)π inter­action between a benzene H atom and the phenyl ring of a neighbouring mol­ecule.

Related literature

For applications of benzimidazole derivatives, see: Hahn & Jahnke (2008 [triangle]); Lappert (2005 [triangle]); Winberg & Coffman (1965 [triangle]); Küçükbay et al. (1996 [triangle], 1997 [triangle]); Çetinkaya et al. (1994 [triangle], 1998 [triangle]). For details of the synthesis, see: Yılmaz (2008 [triangle]). For related structures, see: Akkurt et al. (2004 [triangle], 2005 [triangle]); Öztürk et al. (2003 [triangle], 2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o174-scheme1.jpg

Experimental

Crystal data

  • C26H26N2S2
  • M r = 430.63
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o174-efi1.jpg
  • a = 27.2391 (11) Å
  • b = 8.3483 (4) Å
  • c = 10.3200 (4) Å
  • V = 2346.77 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 293 (2) K
  • 0.76 × 0.65 × 0.38 mm

Data collection

  • Stoe IPDS-2 diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.838, T max = 0.914
  • 19766 measured reflections
  • 4983 independent reflections
  • 3842 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.080
  • S = 0.97
  • 4983 reflections
  • 271 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.10 e Å−3
  • Δρmin = −0.19 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2317 Friedel pairs
  • Flack parameter: −0.03 (5)

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 [triangle]); program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042761/kj2110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042761/kj2110Isup2.hkl

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-2 diffractometer (purchased under grant F.279 of the University Research Fund). HK and ÜY thank the İnönü University Research Fund (Directed project BAPB-2008/59) for financial support of this study.

supplementary crystallographic information

Comment

Benzimidazole derivatives consistute an important class of heterocyclic compounds for their biological activities. They also are an important source for electron-rich olefin synthesis. Electron rich olefins are an important research subject for their versatile reactions. Since electron rich olefins are powerful nucleophilic compounds, they have been used as reducing agents, and are a source of carbine transation metal complexes and formylating agents for the proton active compounds (Hahn & Jahnke, 2008; Lappert, 2005). They are readily converted by carbon disulfide to red coloured stable dithioquaternary salts. (Winberg & Coffman,1965). Electron rich olefins have also been used as catalysts for cyloin type C—C coupling reactions. In a number of previous papers (Çetinkaya et al., 1994; Küçükbay et al., 1996; Küçükbay et al., 1997; Çetinkaya, et al., 1998) we reported the synthesis of some benzimidazole derived electron rich olefins.

The objective of this study was to elucidate the crystal structure of the title compound and to compare it with those of related benzimidazole derivatives reported previously (Akkurt et al., 2004; Öztürk et al., 2004; Akkurt et al., 2005).

The ORTEP diagram of the title molecule with numbering scheme is shown in Fig. 1. The molecular structure of the title compound is composed of a benzimidazole ring with two phenylpropyl substituents and a dithiocarboxylate group in the 2-position. In the title molecule the C–S bonds are nearly equal in length. The N1–C7 and N2–C7 bond lengths in the benzimidazole ring agree well with several related benzimidazole derivatives (Öztürk et al., 2003; Akkurt et al., 2004). The benzimidazole unit (N1/N2/C1–C7) is essentially, with a maximum deviation from the least-squares plane of 0.008 (2) Å for C6. The benzimidazole ring makes dihedral angles of 72.72 (10) and 27.62 (12)°, with the two phenyl rings (C12–C17) and (C21–C26), respectively. The dihedral angle between the two phenyl rings is 55.98 (15)°.

The the molecular packing in the solid state is stabilized by a C–H···S type intermolecular hydrogen bonding interactions and a C—H···π interaction between a benzene H atom and the phenyl ring of neighbouring molecules, with a C5—H5···Cg1ii separation of 2.70 Å [Table 2; Cg1 is the C12—C17 phenyl ring, symmetry code: (ii) -x + 1/2, y - 1/2, z - 1/2].

Experimental

All experiments were performed under argon using freshly distilled dry solvents. CS2 (0.1 ml, 1.60 mmol) was added to a solution of bis[1,3-di(3-phenylpropyl)benzimidazolidine-2-ylidene] (0.55 g, 0.78 mmol) (Yılmaz, 2008) in toluene (5 ml). A red precipitate formed instantly. The red compound was washed twice with Et2O and crystallized from EtOH. [Yield: 0.60 g, 90%; m.p: 383–384 ° K]. Analysis calculated for C26H26N2S2: C 72.56, H 6.05, N 6.05, S 14.88%; found: C 71.99, H 5.93, N 6.30, S 14.18%.

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 and C—H = 0.97 Å, and with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
View of the title molecule, with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.

Crystal data

C26H26N2S2F(000) = 912
Mr = 430.63Dx = 1.219 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 22533 reflections
a = 27.2391 (11) Åθ = 1.5–27.3°
b = 8.3483 (4) ŵ = 0.24 mm1
c = 10.3200 (4) ÅT = 293 K
V = 2346.77 (17) Å3Prism, red
Z = 40.76 × 0.65 × 0.38 mm

Data collection

Stoe IPDS-2 diffractometer4983 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3842 reflections with I > 2σ(I)
plane graphiteRint = 0.029
Detector resolution: 6.67 pixels mm-1θmax = 26.8°, θmin = 1.5°
ω scansh = −32→34
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −10→10
Tmin = 0.838, Tmax = 0.914l = −13→12
19766 measured 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)] = 0.032H-atom parameters constrained
wR(F2) = 0.080w = 1/[σ2(Fo2) + (0.0468P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
4983 reflectionsΔρmax = 0.10 e Å3
271 parametersΔρmin = −0.19 e Å3
1 restraintAbsolute structure: Flack (1983), 2317 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.03 (5)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S10.40082 (2)0.05062 (6)0.70350 (5)0.0832 (2)
S20.41878 (3)0.40688 (8)0.69551 (5)0.0985 (2)
N10.45770 (5)0.20086 (16)0.42158 (13)0.0518 (4)
N20.37896 (5)0.24163 (16)0.40602 (13)0.0523 (4)
C10.44694 (6)0.2097 (2)0.28979 (15)0.0503 (5)
C20.47649 (7)0.1962 (2)0.18080 (17)0.0611 (6)
C30.45312 (8)0.2108 (2)0.06250 (18)0.0666 (7)
C40.40275 (7)0.2357 (2)0.0538 (2)0.0677 (7)
C50.37380 (7)0.2486 (2)0.16044 (17)0.0612 (6)
C60.39687 (6)0.2360 (2)0.27995 (16)0.0499 (5)
C70.41636 (6)0.22176 (19)0.48903 (16)0.0513 (5)
C80.41218 (7)0.2261 (2)0.63249 (17)0.0623 (6)
C90.32764 (6)0.2696 (2)0.44304 (19)0.0591 (6)
C100.31416 (6)0.4459 (2)0.4397 (2)0.0645 (6)
C110.26262 (7)0.4742 (2)0.4912 (2)0.0763 (8)
C120.24982 (6)0.6493 (2)0.4969 (2)0.0661 (6)
C130.21865 (8)0.7177 (3)0.4061 (2)0.0804 (8)
C140.20761 (9)0.8780 (4)0.4092 (3)0.1013 (11)
C150.22701 (12)0.9732 (3)0.5006 (4)0.1107 (13)
C160.25833 (11)0.9111 (4)0.5923 (3)0.1060 (11)
C170.26948 (8)0.7491 (3)0.5899 (2)0.0858 (9)
C180.50755 (6)0.1851 (2)0.47476 (18)0.0579 (6)
C190.53581 (7)0.3405 (2)0.4620 (2)0.0730 (7)
C200.58916 (7)0.3220 (3)0.5025 (2)0.0796 (8)
C210.59723 (7)0.2812 (2)0.6424 (2)0.0680 (7)
C220.56779 (9)0.3408 (3)0.7394 (2)0.0944 (10)
C230.57637 (14)0.3030 (5)0.8670 (3)0.1282 (14)
C240.6143 (2)0.2054 (6)0.9002 (4)0.1497 (19)
C250.64464 (17)0.1496 (3)0.8060 (5)0.1379 (18)
C260.63577 (9)0.1846 (3)0.6778 (3)0.0989 (10)
H20.510100.178400.187000.0730*
H30.471500.20370−0.013200.0800*
H40.388400.24380−0.027700.0810*
H50.340100.265100.153700.0740*
H9A0.322200.228400.529800.0710*
H9B0.306300.211300.384400.0710*
H10A0.316200.484700.351300.0770*
H10B0.337500.505900.491600.0770*
H11A0.239200.419400.435900.0920*
H11B0.260000.428700.577500.0920*
H130.205000.653600.341800.0970*
H140.186500.921000.347400.1210*
H150.219301.081700.501900.1330*
H160.271900.977100.655400.1270*
H170.290600.707000.652000.1030*
H18A0.524900.100800.429000.0690*
H18B0.505600.155300.565400.0690*
H19A0.520400.421700.515500.0880*
H19B0.534500.376600.372700.0880*
H20A0.604000.238800.449800.0960*
H20B0.606200.421300.483700.0960*
H220.541700.407700.718300.1130*
H230.556100.344600.931200.1540*
H240.619400.177200.986300.1800*
H250.671600.087200.828300.1660*
H260.656200.142200.614200.1190*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.1109 (4)0.0873 (3)0.0513 (2)0.0024 (3)0.0091 (3)0.0103 (3)
S20.1433 (5)0.0944 (4)0.0579 (3)−0.0250 (4)0.0058 (4)−0.0251 (3)
N10.0519 (8)0.0605 (8)0.0429 (7)0.0010 (6)−0.0031 (6)0.0001 (6)
N20.0503 (8)0.0625 (8)0.0441 (7)0.0012 (6)−0.0022 (6)−0.0033 (6)
C10.0572 (10)0.0544 (9)0.0394 (8)0.0040 (7)−0.0024 (7)−0.0024 (7)
C20.0618 (10)0.0694 (10)0.0520 (10)0.0080 (8)0.0083 (8)0.0004 (8)
C30.0858 (14)0.0719 (12)0.0420 (9)0.0060 (10)0.0095 (9)−0.0037 (8)
C40.0844 (14)0.0778 (13)0.0410 (9)0.0022 (10)−0.0081 (9)−0.0028 (8)
C50.0624 (10)0.0742 (11)0.0471 (9)−0.0003 (8)−0.0106 (8)−0.0002 (8)
C60.0559 (9)0.0570 (9)0.0369 (8)−0.0006 (7)−0.0020 (7)−0.0018 (6)
C70.0575 (9)0.0518 (8)0.0446 (8)−0.0019 (7)−0.0018 (8)−0.0034 (7)
C80.0633 (11)0.0818 (12)0.0418 (10)−0.0001 (9)−0.0001 (8)−0.0062 (8)
C90.0479 (9)0.0686 (11)0.0608 (11)−0.0019 (7)0.0050 (8)0.0002 (8)
C100.0541 (9)0.0686 (11)0.0709 (11)0.0011 (8)0.0114 (9)−0.0043 (8)
C110.0579 (11)0.0797 (13)0.0914 (15)0.0039 (9)0.0140 (10)−0.0032 (11)
C120.0496 (9)0.0788 (12)0.0699 (11)0.0015 (8)0.0152 (9)−0.0109 (10)
C130.0646 (12)0.1008 (16)0.0759 (14)0.0096 (11)0.0135 (10)−0.0116 (12)
C140.0818 (16)0.110 (2)0.112 (2)0.0257 (15)0.0257 (15)0.0243 (17)
C150.0982 (19)0.0830 (17)0.151 (3)−0.0029 (15)0.051 (2)−0.0083 (19)
C160.0969 (19)0.107 (2)0.114 (2)−0.0291 (16)0.0341 (17)−0.0437 (17)
C170.0717 (13)0.1021 (19)0.0835 (16)−0.0096 (12)0.0062 (12)−0.0137 (12)
C180.0524 (9)0.0674 (10)0.0539 (10)0.0028 (7)−0.0071 (8)0.0086 (8)
C190.0684 (11)0.0826 (13)0.0679 (12)−0.0119 (10)−0.0139 (9)0.0199 (10)
C200.0599 (12)0.1052 (16)0.0738 (13)−0.0160 (10)−0.0057 (10)0.0108 (12)
C210.0585 (11)0.0676 (11)0.0779 (13)−0.0108 (9)−0.0156 (10)0.0089 (9)
C220.0761 (15)0.130 (2)0.0772 (15)−0.0115 (14)−0.0137 (12)−0.0058 (14)
C230.118 (2)0.192 (3)0.0747 (19)−0.071 (2)−0.0107 (18)−0.006 (2)
C240.195 (4)0.142 (3)0.112 (3)−0.098 (3)−0.080 (3)0.058 (2)
C250.163 (3)0.0748 (17)0.176 (4)−0.0163 (19)−0.104 (3)0.037 (2)
C260.0874 (16)0.0754 (13)0.134 (2)0.0046 (11)−0.0398 (16)−0.0007 (15)

Geometric parameters (Å, °)

S1—C81.6670 (18)C23—C241.360 (7)
S2—C81.6532 (18)C24—C251.358 (7)
N1—C11.393 (2)C25—C261.376 (6)
N1—C71.335 (2)C2—H20.9300
N1—C181.471 (2)C3—H30.9300
N2—C61.390 (2)C4—H40.9300
N2—C71.341 (2)C5—H50.9300
N2—C91.468 (2)C9—H9A0.9700
C1—C21.388 (2)C9—H9B0.9700
C1—C61.385 (2)C10—H10A0.9700
C2—C31.382 (3)C10—H10B0.9700
C3—C41.391 (3)C11—H11A0.9700
C4—C51.358 (3)C11—H11B0.9700
C5—C61.388 (2)C13—H130.9300
C7—C81.485 (2)C14—H140.9300
C9—C101.517 (2)C15—H150.9300
C10—C111.520 (3)C16—H160.9300
C11—C121.504 (2)C17—H170.9300
C12—C131.388 (3)C18—H18A0.9700
C12—C171.379 (3)C18—H18B0.9700
C13—C141.372 (4)C19—H19A0.9700
C14—C151.342 (5)C19—H19B0.9700
C15—C161.376 (5)C20—H20A0.9700
C16—C171.386 (4)C20—H20B0.9700
C18—C191.514 (2)C22—H220.9300
C19—C201.520 (3)C23—H230.9300
C20—C211.500 (3)C24—H240.9300
C21—C221.376 (3)C25—H250.9300
C21—C261.373 (3)C26—H260.9300
C22—C231.374 (4)
S1···N13.5268 (15)C21···H18B2.8200
S1···N23.5103 (14)C22···H18B2.9100
S2···N13.4747 (15)C22···H19A2.7300
S2···N23.4648 (15)C24···H10Bi2.9000
S2···C19i3.680 (2)H2···C182.9700
S1···H24ii2.9900H2···S1ii3.0900
S1···H2iii3.0900H4···C13iv3.0000
S1···H9A3.1600H4···C14iv2.9200
S2···H10B3.1600H5···C93.0100
S2···H19Bi2.8700H5···H9B2.5900
N1···S13.5268 (15)H5···C12iv3.0900
N1···S23.4747 (15)H5···C13iv3.0400
N1···N22.1776 (19)H5···C14iv2.9900
N2···S13.5103 (14)H5···C15iv2.9800
N2···S23.4648 (15)H5···C16iv3.0100
N2···N12.1776 (19)H5···C17iv3.0600
C2···C193.533 (3)H9A···S13.1600
C3···C18ii3.590 (2)H9A···C82.6700
C4···C14iv3.560 (3)H9A···H11B2.4300
C5···C14iv3.579 (3)H9B···C52.9700
C6···C25ii3.423 (3)H9B···H52.5900
C10···C24v3.527 (5)H9B···H11A2.5800
C14···C5vi3.579 (3)H10B···S23.1600
C14···C4vi3.560 (3)H10B···C172.9300
C18···C3iii3.590 (2)H10B···C24v2.9000
C18···C223.441 (3)H11A···H9B2.5800
C19···C23.533 (3)H11A···H132.3700
C19···S2v3.680 (2)H11B···H9A2.4300
C22···C183.441 (3)H11B···H172.5900
C24···C10i3.527 (5)H13···H11A2.3700
C25···C6iii3.423 (3)H13···H16iv2.5000
C1···H19B2.8900H16···H13vi2.5000
C2···H18A2.9900H17···H11B2.5900
C2···H19B2.9500H18A···C22.9900
C3···H18Aii3.0000H18A···H20A2.4500
C4···H20Bv2.9600H18A···C3iii3.0000
C5···H9B2.9700H18B···C82.7000
C8···H18B2.7000H18B···C212.8200
C8···H9A2.6700H18B···C222.9100
C9···H53.0100H19A···C222.7300
C12···H5vi3.0900H19A···H222.1700
C13···H5vi3.0400H19B···C12.8900
C13···H4vi3.0000H19B···C22.9500
C14···H4vi2.9200H19B···S2v2.8700
C14···H5vi2.9900H20A···H18A2.4500
C15···H5vi2.9800H20A···H262.3600
C16···H5vi3.0100H20B···C4i2.9600
C17···H5vi3.0600H22···C192.7100
C17···H10B2.9300H22···H19A2.1700
C18···H22.9700H24···S1iii2.9900
C19···H222.7100H26···H20A2.3600
C1—N1—C7108.94 (13)C6—C5—H5122.00
C1—N1—C18124.29 (14)N2—C9—H9A109.00
C7—N1—C18126.57 (14)N2—C9—H9B109.00
C6—N2—C7109.09 (13)C10—C9—H9A109.00
C6—N2—C9125.67 (14)C10—C9—H9B109.00
C7—N2—C9125.22 (14)H9A—C9—H9B108.00
N1—C1—C2131.68 (16)C9—C10—H10A109.00
N1—C1—C6106.68 (14)C9—C10—H10B109.00
C2—C1—C6121.64 (15)C11—C10—H10A109.00
C1—C2—C3116.21 (17)C11—C10—H10B109.00
C2—C3—C4121.64 (18)H10A—C10—H10B108.00
C3—C4—C5122.17 (18)C10—C11—H11A109.00
C4—C5—C6116.81 (17)C10—C11—H11B109.00
N2—C6—C1106.40 (14)C12—C11—H11A109.00
N2—C6—C5132.07 (16)C12—C11—H11B109.00
C1—C6—C5121.53 (16)H11A—C11—H11B108.00
N1—C7—N2108.89 (14)C12—C13—H13119.00
N1—C7—C8125.98 (15)C14—C13—H13119.00
N2—C7—C8125.12 (15)C13—C14—H14120.00
S1—C8—S2130.51 (11)C15—C14—H14120.00
S1—C8—C7115.53 (12)C14—C15—H15120.00
S2—C8—C7113.96 (12)C16—C15—H15120.00
N2—C9—C10112.26 (13)C15—C16—H16120.00
C9—C10—C11111.50 (14)C17—C16—H16120.00
C10—C11—C12112.27 (14)C12—C17—H17119.00
C11—C12—C13121.03 (18)C16—C17—H17119.00
C11—C12—C17121.63 (18)N1—C18—H18A109.00
C13—C12—C17117.32 (18)N1—C18—H18B109.00
C12—C13—C14121.3 (2)C19—C18—H18A109.00
C13—C14—C15120.5 (3)C19—C18—H18B109.00
C14—C15—C16120.3 (3)H18A—C18—H18B108.00
C15—C16—C17119.4 (3)C18—C19—H19A109.00
C12—C17—C16121.1 (2)C18—C19—H19B109.00
N1—C18—C19111.12 (14)C20—C19—H19A109.00
C18—C19—C20112.03 (16)C20—C19—H19B109.00
C19—C20—C21115.34 (17)H19A—C19—H19B108.00
C20—C21—C22122.21 (18)C19—C20—H20A108.00
C20—C21—C26120.1 (2)C19—C20—H20B108.00
C22—C21—C26117.7 (2)C21—C20—H20A108.00
C21—C22—C23121.0 (3)C21—C20—H20B108.00
C22—C23—C24120.6 (3)H20A—C20—H20B107.00
C23—C24—C25119.2 (4)C21—C22—H22119.00
C24—C25—C26120.6 (4)C23—C22—H22119.00
C21—C26—C25121.0 (3)C22—C23—H23120.00
C1—C2—H2122.00C24—C23—H23120.00
C3—C2—H2122.00C23—C24—H24120.00
C2—C3—H3119.00C25—C24—H24120.00
C4—C3—H3119.00C24—C25—H25120.00
C3—C4—H4119.00C26—C25—H25120.00
C5—C4—H4119.00C21—C26—H26120.00
C4—C5—H5122.00C25—C26—H26119.00
C7—N1—C1—C2179.97 (18)C4—C5—C6—C1−0.7 (2)
C18—N1—C1—C24.8 (3)N1—C7—C8—S289.55 (19)
C7—N1—C1—C6−0.39 (18)N2—C7—C8—S190.04 (19)
C18—N1—C1—C6−175.53 (14)N1—C7—C8—S1−91.39 (19)
C1—N1—C7—N20.86 (18)N2—C7—C8—S2−89.03 (19)
C18—N1—C7—N2175.86 (14)N2—C9—C10—C11−174.26 (15)
C1—N1—C7—C8−177.91 (15)C9—C10—C11—C12176.22 (16)
C18—N1—C7—C8−2.9 (3)C10—C11—C12—C13104.4 (2)
C7—N1—C18—C19−101.35 (19)C10—C11—C12—C17−73.8 (2)
C1—N1—C18—C1972.9 (2)C11—C12—C13—C14−178.7 (2)
C9—N2—C7—N1−179.33 (14)C13—C12—C17—C160.2 (3)
C6—N2—C7—C8177.78 (15)C17—C12—C13—C14−0.4 (3)
C6—N2—C7—N1−1.00 (18)C11—C12—C17—C16178.4 (2)
C9—N2—C6—C1179.06 (15)C12—C13—C14—C150.3 (4)
C9—N2—C7—C8−0.6 (2)C13—C14—C15—C160.1 (5)
C9—N2—C6—C5−2.3 (3)C14—C15—C16—C17−0.3 (5)
C7—N2—C9—C1097.6 (2)C15—C16—C17—C120.2 (4)
C7—N2—C6—C5179.42 (18)N1—C18—C19—C20−173.65 (15)
C6—N2—C9—C10−80.5 (2)C18—C19—C20—C21−64.2 (2)
C7—N2—C6—C10.74 (18)C19—C20—C21—C22−35.6 (3)
C6—C1—C2—C30.1 (2)C19—C20—C21—C26146.1 (2)
N1—C1—C2—C3179.71 (17)C20—C21—C22—C23−179.2 (3)
N1—C1—C6—C5−179.06 (15)C26—C21—C22—C23−0.9 (4)
C2—C1—C6—N2179.47 (15)C20—C21—C26—C25178.1 (2)
N1—C1—C6—N2−0.21 (18)C22—C21—C26—C25−0.3 (4)
C2—C1—C6—C50.6 (3)C21—C22—C23—C240.0 (5)
C1—C2—C3—C4−0.7 (2)C22—C23—C24—C252.1 (7)
C2—C3—C4—C50.6 (3)C23—C24—C25—C26−3.2 (6)
C3—C4—C5—C60.1 (3)C24—C25—C26—C212.4 (5)
C4—C5—C6—N2−179.24 (17)

Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) −x+1, −y, z−1/2; (iii) −x+1, −y, z+1/2; (iv) −x+1/2, y−1/2, z−1/2; (v) −x+1, −y+1, z−1/2; (vi) −x+1/2, y+1/2, z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C19—H19B···S2v0.972.873.680 (2)142
C5—H5···Cg1iv0.932.703.523 (2)148

Symmetry codes: (v) −x+1, −y+1, z−1/2; (iv) −x+1/2, y−1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2110).

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