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

Akkurt, M.; Yılmaz, Ü.; Küçükbay, H.; Gençaslan, M.; Büyükgüngör, O.

doi:10.1107/S1600536808042761

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages o174-o175

doi:10.1107/S1600536808042761

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

Mehmet Akkurt,^a ^* Ülkü Yılmaz,^b Hasan Küçükbay,^b Mustafa Gençaslan ^a and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, nönü University, 44280 Malatya, Turkey, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 6 November 2008; accepted 15 December 2008; online 20 December 2008)

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

Experimental

Crystal data

C₂₆H₂₆N₂S₂
M_r = 430.63
Orthorhombic, P n a 2₁
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 ) 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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.080
S = 0.97
4983 reflections
271 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 2317 Friedel pairs
Flack parameter: −0.03 (5)

Table 1
Selected bond lengths (Å)

C8—S1	1.6670 (18)
C8—S2	1.6532 (18)
C1—N1	1.393 (2)
C7—N2	1.341 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19B⋯S2ⁱ	0.97	2.87	3.680 (2)	142
C5—H5⋯Cg1ⁱⁱ	0.93	2.70	3.523 (2)	148
Symmetry codes: (i) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg1 is the centroid of the C12–C17 phenyl ring.

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

Supporting information

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

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

checkCIF report

Comment top

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].

Related literature top

For applications of benzimidazole derivatives, see: Hahn & Jahnke (2008); Lappert (2005); Winberg & Coffman (1965); Küçükbay et al. (1996, 1997); Çetinkaya et al. (1994, 1998). For details of the synthesis, see: Yılmaz (2008). For related structures, see: Akkurt et al. (2004, 2005); Öztürk et al. (2003, 2004). Cg1 is the centroid of the C12–C17 phenyl ring.

Experimental top

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%.

Computing details top

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

Figures top

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.

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

Crystal data top

C₂₆H₂₆N₂S₂	F(000) = 912
M_r = 430.63	D_x = 1.219 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 22533 reflections
a = 27.2391 (11) Å	θ = 1.5–27.3°
b = 8.3483 (4) Å	µ = 0.24 mm⁻¹
c = 10.3200 (4) Å	T = 293 K
V = 2346.77 (17) Å³	Prism, red
Z = 4	0.76 × 0.65 × 0.38 mm

Data collection top

Stoe IPDS-2 diffractometer	4983 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3842 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.029
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.8°, θ_min = 1.5°
ω scans	h = −32→34
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
T_min = 0.838, T_max = 0.914	l = −13→12
19766 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0468P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.001
4983 reflections	Δρ_max = 0.10 e Å⁻³
271 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2317 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (5)

Crystal data top

C₂₆H₂₆N₂S₂	V = 2346.77 (17) Å³
M_r = 430.63	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 27.2391 (11) Å	µ = 0.24 mm⁻¹
b = 8.3483 (4) Å	T = 293 K
c = 10.3200 (4) Å	0.76 × 0.65 × 0.38 mm

Data collection top

Stoe IPDS-2 diffractometer	4983 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3842 reflections with I > 2σ(I)
T_min = 0.838, T_max = 0.914	R_int = 0.029
19766 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.080	Δρ_max = 0.10 e Å⁻³
S = 0.97	Δρ_min = −0.19 e Å⁻³
4983 reflections	Absolute structure: Flack (1983), 2317 Friedel pairs
271 parameters	Absolute structure parameter: −0.03 (5)
1 restraint

Special details top

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) top

	x	y	z	U_iso*/U_eq
S1	0.40082 (2)	0.05062 (6)	0.70350 (5)	0.0832 (2)
S2	0.41878 (3)	0.40688 (8)	0.69551 (5)	0.0985 (2)
N1	0.45770 (5)	0.20086 (16)	0.42158 (13)	0.0518 (4)
N2	0.37896 (5)	0.24163 (16)	0.40602 (13)	0.0523 (4)
C1	0.44694 (6)	0.2097 (2)	0.28979 (15)	0.0503 (5)
C2	0.47649 (7)	0.1962 (2)	0.18080 (17)	0.0611 (6)
C3	0.45312 (8)	0.2108 (2)	0.06250 (18)	0.0666 (7)
C4	0.40275 (7)	0.2357 (2)	0.0538 (2)	0.0677 (7)
C5	0.37380 (7)	0.2486 (2)	0.16044 (17)	0.0612 (6)
C6	0.39687 (6)	0.2360 (2)	0.27995 (16)	0.0499 (5)
C7	0.41636 (6)	0.22176 (19)	0.48903 (16)	0.0513 (5)
C8	0.41218 (7)	0.2261 (2)	0.63249 (17)	0.0623 (6)
C9	0.32764 (6)	0.2696 (2)	0.44304 (19)	0.0591 (6)
C10	0.31416 (6)	0.4459 (2)	0.4397 (2)	0.0645 (6)
C11	0.26262 (7)	0.4742 (2)	0.4912 (2)	0.0763 (8)
C12	0.24982 (6)	0.6493 (2)	0.4969 (2)	0.0661 (6)
C13	0.21865 (8)	0.7177 (3)	0.4061 (2)	0.0804 (8)
C14	0.20761 (9)	0.8780 (4)	0.4092 (3)	0.1013 (11)
C15	0.22701 (12)	0.9732 (3)	0.5006 (4)	0.1107 (13)
C16	0.25833 (11)	0.9111 (4)	0.5923 (3)	0.1060 (11)
C17	0.26948 (8)	0.7491 (3)	0.5899 (2)	0.0858 (9)
C18	0.50755 (6)	0.1851 (2)	0.47476 (18)	0.0579 (6)
C19	0.53581 (7)	0.3405 (2)	0.4620 (2)	0.0730 (7)
C20	0.58916 (7)	0.3220 (3)	0.5025 (2)	0.0796 (8)
C21	0.59723 (7)	0.2812 (2)	0.6424 (2)	0.0680 (7)
C22	0.56779 (9)	0.3408 (3)	0.7394 (2)	0.0944 (10)
C23	0.57637 (14)	0.3030 (5)	0.8670 (3)	0.1282 (14)
C24	0.6143 (2)	0.2054 (6)	0.9002 (4)	0.1497 (19)
C25	0.64464 (17)	0.1496 (3)	0.8060 (5)	0.1379 (18)
C26	0.63577 (9)	0.1846 (3)	0.6778 (3)	0.0989 (10)
H2	0.51010	0.17840	0.18700	0.0730*
H3	0.47150	0.20370	−0.01320	0.0800*
H4	0.38840	0.24380	−0.02770	0.0810*
H5	0.34010	0.26510	0.15370	0.0740*
H9A	0.32220	0.22840	0.52980	0.0710*
H9B	0.30630	0.21130	0.38440	0.0710*
H10A	0.31620	0.48470	0.35130	0.0770*
H10B	0.33750	0.50590	0.49160	0.0770*
H11A	0.23920	0.41940	0.43590	0.0920*
H11B	0.26000	0.42870	0.57750	0.0920*
H13	0.20500	0.65360	0.34180	0.0970*
H14	0.18650	0.92100	0.34740	0.1210*
H15	0.21930	1.08170	0.50190	0.1330*
H16	0.27190	0.97710	0.65540	0.1270*
H17	0.29060	0.70700	0.65200	0.1030*
H18A	0.52490	0.10080	0.42900	0.0690*
H18B	0.50560	0.15530	0.56540	0.0690*
H19A	0.52040	0.42170	0.51550	0.0880*
H19B	0.53450	0.37660	0.37270	0.0880*
H20A	0.60400	0.23880	0.44980	0.0960*
H20B	0.60620	0.42130	0.48370	0.0960*
H22	0.54170	0.40770	0.71830	0.1130*
H23	0.55610	0.34460	0.93120	0.1540*
H24	0.61940	0.17720	0.98630	0.1800*
H25	0.67160	0.08720	0.82830	0.1660*
H26	0.65620	0.14220	0.61420	0.1190*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.1109 (4)	0.0873 (3)	0.0513 (2)	0.0024 (3)	0.0091 (3)	0.0103 (3)
S2	0.1433 (5)	0.0944 (4)	0.0579 (3)	−0.0250 (4)	0.0058 (4)	−0.0251 (3)
N1	0.0519 (8)	0.0605 (8)	0.0429 (7)	0.0010 (6)	−0.0031 (6)	0.0001 (6)
N2	0.0503 (8)	0.0625 (8)	0.0441 (7)	0.0012 (6)	−0.0022 (6)	−0.0033 (6)
C1	0.0572 (10)	0.0544 (9)	0.0394 (8)	0.0040 (7)	−0.0024 (7)	−0.0024 (7)
C2	0.0618 (10)	0.0694 (10)	0.0520 (10)	0.0080 (8)	0.0083 (8)	0.0004 (8)
C3	0.0858 (14)	0.0719 (12)	0.0420 (9)	0.0060 (10)	0.0095 (9)	−0.0037 (8)
C4	0.0844 (14)	0.0778 (13)	0.0410 (9)	0.0022 (10)	−0.0081 (9)	−0.0028 (8)
C5	0.0624 (10)	0.0742 (11)	0.0471 (9)	−0.0003 (8)	−0.0106 (8)	−0.0002 (8)
C6	0.0559 (9)	0.0570 (9)	0.0369 (8)	−0.0006 (7)	−0.0020 (7)	−0.0018 (6)
C7	0.0575 (9)	0.0518 (8)	0.0446 (8)	−0.0019 (7)	−0.0018 (8)	−0.0034 (7)
C8	0.0633 (11)	0.0818 (12)	0.0418 (10)	−0.0001 (9)	−0.0001 (8)	−0.0062 (8)
C9	0.0479 (9)	0.0686 (11)	0.0608 (11)	−0.0019 (7)	0.0050 (8)	0.0002 (8)
C10	0.0541 (9)	0.0686 (11)	0.0709 (11)	0.0011 (8)	0.0114 (9)	−0.0043 (8)
C11	0.0579 (11)	0.0797 (13)	0.0914 (15)	0.0039 (9)	0.0140 (10)	−0.0032 (11)
C12	0.0496 (9)	0.0788 (12)	0.0699 (11)	0.0015 (8)	0.0152 (9)	−0.0109 (10)
C13	0.0646 (12)	0.1008 (16)	0.0759 (14)	0.0096 (11)	0.0135 (10)	−0.0116 (12)
C14	0.0818 (16)	0.110 (2)	0.112 (2)	0.0257 (15)	0.0257 (15)	0.0243 (17)
C15	0.0982 (19)	0.0830 (17)	0.151 (3)	−0.0029 (15)	0.051 (2)	−0.0083 (19)
C16	0.0969 (19)	0.107 (2)	0.114 (2)	−0.0291 (16)	0.0341 (17)	−0.0437 (17)
C17	0.0717 (13)	0.1021 (19)	0.0835 (16)	−0.0096 (12)	0.0062 (12)	−0.0137 (12)
C18	0.0524 (9)	0.0674 (10)	0.0539 (10)	0.0028 (7)	−0.0071 (8)	0.0086 (8)
C19	0.0684 (11)	0.0826 (13)	0.0679 (12)	−0.0119 (10)	−0.0139 (9)	0.0199 (10)
C20	0.0599 (12)	0.1052 (16)	0.0738 (13)	−0.0160 (10)	−0.0057 (10)	0.0108 (12)
C21	0.0585 (11)	0.0676 (11)	0.0779 (13)	−0.0108 (9)	−0.0156 (10)	0.0089 (9)
C22	0.0761 (15)	0.130 (2)	0.0772 (15)	−0.0115 (14)	−0.0137 (12)	−0.0058 (14)
C23	0.118 (2)	0.192 (3)	0.0747 (19)	−0.071 (2)	−0.0107 (18)	−0.006 (2)
C24	0.195 (4)	0.142 (3)	0.112 (3)	−0.098 (3)	−0.080 (3)	0.058 (2)
C25	0.163 (3)	0.0748 (17)	0.176 (4)	−0.0163 (19)	−0.104 (3)	0.037 (2)
C26	0.0874 (16)	0.0754 (13)	0.134 (2)	0.0046 (11)	−0.0398 (16)	−0.0007 (15)

Geometric parameters (Å, º) top

S1—C8	1.6670 (18)	C23—C24	1.360 (7)
S2—C8	1.6532 (18)	C24—C25	1.358 (7)
N1—C1	1.393 (2)	C25—C26	1.376 (6)
N1—C7	1.335 (2)	C2—H2	0.9300
N1—C18	1.471 (2)	C3—H3	0.9300
N2—C6	1.390 (2)	C4—H4	0.9300
N2—C7	1.341 (2)	C5—H5	0.9300
N2—C9	1.468 (2)	C9—H9A	0.9700
C1—C2	1.388 (2)	C9—H9B	0.9700
C1—C6	1.385 (2)	C10—H10A	0.9700
C2—C3	1.382 (3)	C10—H10B	0.9700
C3—C4	1.391 (3)	C11—H11A	0.9700
C4—C5	1.358 (3)	C11—H11B	0.9700
C5—C6	1.388 (2)	C13—H13	0.9300
C7—C8	1.485 (2)	C14—H14	0.9300
C9—C10	1.517 (2)	C15—H15	0.9300
C10—C11	1.520 (3)	C16—H16	0.9300
C11—C12	1.504 (2)	C17—H17	0.9300
C12—C13	1.388 (3)	C18—H18A	0.9700
C12—C17	1.379 (3)	C18—H18B	0.9700
C13—C14	1.372 (4)	C19—H19A	0.9700
C14—C15	1.342 (5)	C19—H19B	0.9700
C15—C16	1.376 (5)	C20—H20A	0.9700
C16—C17	1.386 (4)	C20—H20B	0.9700
C18—C19	1.514 (2)	C22—H22	0.9300
C19—C20	1.520 (3)	C23—H23	0.9300
C20—C21	1.500 (3)	C24—H24	0.9300
C21—C22	1.376 (3)	C25—H25	0.9300
C21—C26	1.373 (3)	C26—H26	0.9300
C22—C23	1.374 (4)

S1···N1	3.5268 (15)	C21···H18B	2.8200
S1···N2	3.5103 (14)	C22···H18B	2.9100
S2···N1	3.4747 (15)	C22···H19A	2.7300
S2···N2	3.4648 (15)	C24···H10Bⁱ	2.9000
S2···C19ⁱ	3.680 (2)	H2···C18	2.9700
S1···H24ⁱⁱ	2.9900	H2···S1ⁱⁱ	3.0900
S1···H2ⁱⁱⁱ	3.0900	H4···C13^iv	3.0000
S1···H9A	3.1600	H4···C14^iv	2.9200
S2···H10B	3.1600	H5···C9	3.0100
S2···H19Bⁱ	2.8700	H5···H9B	2.5900
N1···S1	3.5268 (15)	H5···C12^iv	3.0900
N1···S2	3.4747 (15)	H5···C13^iv	3.0400
N1···N2	2.1776 (19)	H5···C14^iv	2.9900
N2···S1	3.5103 (14)	H5···C15^iv	2.9800
N2···S2	3.4648 (15)	H5···C16^iv	3.0100
N2···N1	2.1776 (19)	H5···C17^iv	3.0600
C2···C19	3.533 (3)	H9A···S1	3.1600
C3···C18ⁱⁱ	3.590 (2)	H9A···C8	2.6700
C4···C14^iv	3.560 (3)	H9A···H11B	2.4300
C5···C14^iv	3.579 (3)	H9B···C5	2.9700
C6···C25ⁱⁱ	3.423 (3)	H9B···H5	2.5900
C10···C24^v	3.527 (5)	H9B···H11A	2.5800
C14···C5^vi	3.579 (3)	H10B···S2	3.1600
C14···C4^vi	3.560 (3)	H10B···C17	2.9300
C18···C3ⁱⁱⁱ	3.590 (2)	H10B···C24^v	2.9000
C18···C22	3.441 (3)	H11A···H9B	2.5800
C19···C2	3.533 (3)	H11A···H13	2.3700
C19···S2^v	3.680 (2)	H11B···H9A	2.4300
C22···C18	3.441 (3)	H11B···H17	2.5900
C24···C10ⁱ	3.527 (5)	H13···H11A	2.3700
C25···C6ⁱⁱⁱ	3.423 (3)	H13···H16^iv	2.5000
C1···H19B	2.8900	H16···H13^vi	2.5000
C2···H18A	2.9900	H17···H11B	2.5900
C2···H19B	2.9500	H18A···C2	2.9900
C3···H18Aⁱⁱ	3.0000	H18A···H20A	2.4500
C4···H20B^v	2.9600	H18A···C3ⁱⁱⁱ	3.0000
C5···H9B	2.9700	H18B···C8	2.7000
C8···H18B	2.7000	H18B···C21	2.8200
C8···H9A	2.6700	H18B···C22	2.9100
C9···H5	3.0100	H19A···C22	2.7300
C12···H5^vi	3.0900	H19A···H22	2.1700
C13···H5^vi	3.0400	H19B···C1	2.8900
C13···H4^vi	3.0000	H19B···C2	2.9500
C14···H4^vi	2.9200	H19B···S2^v	2.8700
C14···H5^vi	2.9900	H20A···H18A	2.4500
C15···H5^vi	2.9800	H20A···H26	2.3600
C16···H5^vi	3.0100	H20B···C4ⁱ	2.9600
C17···H5^vi	3.0600	H22···C19	2.7100
C17···H10B	2.9300	H22···H19A	2.1700
C18···H2	2.9700	H24···S1ⁱⁱⁱ	2.9900
C19···H22	2.7100	H26···H20A	2.3600

C1—N1—C7	108.94 (13)	C6—C5—H5	122.00
C1—N1—C18	124.29 (14)	N2—C9—H9A	109.00
C7—N1—C18	126.57 (14)	N2—C9—H9B	109.00
C6—N2—C7	109.09 (13)	C10—C9—H9A	109.00
C6—N2—C9	125.67 (14)	C10—C9—H9B	109.00
C7—N2—C9	125.22 (14)	H9A—C9—H9B	108.00
N1—C1—C2	131.68 (16)	C9—C10—H10A	109.00
N1—C1—C6	106.68 (14)	C9—C10—H10B	109.00
C2—C1—C6	121.64 (15)	C11—C10—H10A	109.00
C1—C2—C3	116.21 (17)	C11—C10—H10B	109.00
C2—C3—C4	121.64 (18)	H10A—C10—H10B	108.00
C3—C4—C5	122.17 (18)	C10—C11—H11A	109.00
C4—C5—C6	116.81 (17)	C10—C11—H11B	109.00
N2—C6—C1	106.40 (14)	C12—C11—H11A	109.00
N2—C6—C5	132.07 (16)	C12—C11—H11B	109.00
C1—C6—C5	121.53 (16)	H11A—C11—H11B	108.00
N1—C7—N2	108.89 (14)	C12—C13—H13	119.00
N1—C7—C8	125.98 (15)	C14—C13—H13	119.00
N2—C7—C8	125.12 (15)	C13—C14—H14	120.00
S1—C8—S2	130.51 (11)	C15—C14—H14	120.00
S1—C8—C7	115.53 (12)	C14—C15—H15	120.00
S2—C8—C7	113.96 (12)	C16—C15—H15	120.00
N2—C9—C10	112.26 (13)	C15—C16—H16	120.00
C9—C10—C11	111.50 (14)	C17—C16—H16	120.00
C10—C11—C12	112.27 (14)	C12—C17—H17	119.00
C11—C12—C13	121.03 (18)	C16—C17—H17	119.00
C11—C12—C17	121.63 (18)	N1—C18—H18A	109.00
C13—C12—C17	117.32 (18)	N1—C18—H18B	109.00
C12—C13—C14	121.3 (2)	C19—C18—H18A	109.00
C13—C14—C15	120.5 (3)	C19—C18—H18B	109.00
C14—C15—C16	120.3 (3)	H18A—C18—H18B	108.00
C15—C16—C17	119.4 (3)	C18—C19—H19A	109.00
C12—C17—C16	121.1 (2)	C18—C19—H19B	109.00
N1—C18—C19	111.12 (14)	C20—C19—H19A	109.00
C18—C19—C20	112.03 (16)	C20—C19—H19B	109.00
C19—C20—C21	115.34 (17)	H19A—C19—H19B	108.00
C20—C21—C22	122.21 (18)	C19—C20—H20A	108.00
C20—C21—C26	120.1 (2)	C19—C20—H20B	108.00
C22—C21—C26	117.7 (2)	C21—C20—H20A	108.00
C21—C22—C23	121.0 (3)	C21—C20—H20B	108.00
C22—C23—C24	120.6 (3)	H20A—C20—H20B	107.00
C23—C24—C25	119.2 (4)	C21—C22—H22	119.00
C24—C25—C26	120.6 (4)	C23—C22—H22	119.00
C21—C26—C25	121.0 (3)	C22—C23—H23	120.00
C1—C2—H2	122.00	C24—C23—H23	120.00
C3—C2—H2	122.00	C23—C24—H24	120.00
C2—C3—H3	119.00	C25—C24—H24	120.00
C4—C3—H3	119.00	C24—C25—H25	120.00
C3—C4—H4	119.00	C26—C25—H25	120.00
C5—C4—H4	119.00	C21—C26—H26	120.00
C4—C5—H5	122.00	C25—C26—H26	119.00

C7—N1—C1—C2	179.97 (18)	C4—C5—C6—C1	−0.7 (2)
C18—N1—C1—C2	4.8 (3)	N1—C7—C8—S2	89.55 (19)
C7—N1—C1—C6	−0.39 (18)	N2—C7—C8—S1	90.04 (19)
C18—N1—C1—C6	−175.53 (14)	N1—C7—C8—S1	−91.39 (19)
C1—N1—C7—N2	0.86 (18)	N2—C7—C8—S2	−89.03 (19)
C18—N1—C7—N2	175.86 (14)	N2—C9—C10—C11	−174.26 (15)
C1—N1—C7—C8	−177.91 (15)	C9—C10—C11—C12	176.22 (16)
C18—N1—C7—C8	−2.9 (3)	C10—C11—C12—C13	104.4 (2)
C7—N1—C18—C19	−101.35 (19)	C10—C11—C12—C17	−73.8 (2)
C1—N1—C18—C19	72.9 (2)	C11—C12—C13—C14	−178.7 (2)
C9—N2—C7—N1	−179.33 (14)	C13—C12—C17—C16	0.2 (3)
C6—N2—C7—C8	177.78 (15)	C17—C12—C13—C14	−0.4 (3)
C6—N2—C7—N1	−1.00 (18)	C11—C12—C17—C16	178.4 (2)
C9—N2—C6—C1	179.06 (15)	C12—C13—C14—C15	0.3 (4)
C9—N2—C7—C8	−0.6 (2)	C13—C14—C15—C16	0.1 (5)
C9—N2—C6—C5	−2.3 (3)	C14—C15—C16—C17	−0.3 (5)
C7—N2—C9—C10	97.6 (2)	C15—C16—C17—C12	0.2 (4)
C7—N2—C6—C5	179.42 (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—C1	0.74 (18)	C19—C20—C21—C22	−35.6 (3)
C6—C1—C2—C3	0.1 (2)	C19—C20—C21—C26	146.1 (2)
N1—C1—C2—C3	179.71 (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—N2	179.47 (15)	C20—C21—C26—C25	178.1 (2)
N1—C1—C6—N2	−0.21 (18)	C22—C21—C26—C25	−0.3 (4)
C2—C1—C6—C5	0.6 (3)	C21—C22—C23—C24	0.0 (5)
C1—C2—C3—C4	−0.7 (2)	C22—C23—C24—C25	2.1 (7)
C2—C3—C4—C5	0.6 (3)	C23—C24—C25—C26	−3.2 (6)
C3—C4—C5—C6	0.1 (3)	C24—C25—C26—C21	2.4 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···S2^v	0.97	2.87	3.680 (2)	142
C5—H5···Cg1^iv	0.93	2.70	3.523 (2)	148

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₆N₂S₂
M_r	430.63
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	27.2391 (11), 8.3483 (4), 10.3200 (4)
V (Å³)	2346.77 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.76 × 0.65 × 0.38

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.838, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	19766, 4983, 3842
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.080, 0.97
No. of reflections	4983
No. of parameters	271
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.19
Absolute structure	Flack (1983), 2317 Friedel pairs
Absolute structure parameter	−0.03 (5)

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

S1—C8	1.6670 (18)	N1—C1	1.393 (2)
S2—C8	1.6532 (18)	N2—C7	1.341 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···S2ⁱ	0.97	2.87	3.680 (2)	142
C5—H5···Cg1ⁱⁱ	0.93	2.70	3.523 (2)	148

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

Acknowledgements

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.

References

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