1-Tosyl-2-[(1-tosyl-1H-benzimidazol-2-yl)methyl­sulfanyl]-1H-benzimidazole

Al-Mohammed, N.N.; Alias, Y.; Abdullah, Z.; Khaledi, H.

doi:10.1107/S1600536811011822

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1043

doi:10.1107/S1600536811011822

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1-Tosyl-2-[(1-tosyl-1H-benzimidazol-2-yl)methylsulfanyl]-1H-benzimidazole

Nassir N. Al-Mohammed,^a ‡ Yatimah Alias,^a Zanariah Abdullah ^a and Hamid Khaledi ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 29 March 2011; accepted 30 March 2011; online 7 April 2011)

In the title compound, C₂₉H₂₄N₄O₄S₃, the two N-tosylbenzimidazolyl unit are connected through a —S—CH₂— fragment, the dihedral angle between the benzimidazole rings being 76.09 (5)°. The methylthio group is disordered with respect to exchange of the S and C atoms in a 0.547 (4):0.453 (4) ratio. In the crystal, C—H⋯O and C—H⋯π interactions connect adjacent molecules into infinite layers parallel to the ab plane. The crystal packing is further stabilized by a π–π interaction [centroid–centroid separation = 3.5187 (4) Å].

Related literature

For the structures of similar compounds, see: Hayashi et al. (2008 ); Rashid et al. (2006 , 2007 ).

Experimental

Crystal data

C₂₉H₂₄N₄O₄S₃
M_r = 588.70
Triclinic, $[P \overline 1]$
a = 8.2524 (6) Å
b = 13.5905 (10) Å
c = 13.8117 (10) Å
α = 62.5191 (8)°
β = 75.4090 (9)°
γ = 85.9930 (9)°
V = 1327.99 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 100 K
0.38 × 0.35 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.887, T_max = 0.935
8528 measured reflections
4762 independent reflections
4405 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.117
S = 1.05
4762 reflections
382 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C8–C13 and C23–C28 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O4ⁱ	0.95	2.48	3.314 (3)	147
C20—H20⋯O3ⁱⁱ	0.95	2.46	3.386 (3)	164
C25—H25⋯Cg1ⁱⁱⁱ	0.95	2.99	3.744 (3)	138
C15—H15A⋯Cg2^iv	0.99	2.98	3.62 (2)	124
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z; (iii) -x, -y+1, -z; (iv) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011822/pv2404sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011822/pv2404Isup2.hkl

checkCIF report

Comment top

The title compound (Fig. 1) is the N-tosylation product of 2-(thiomethyl-2'-benzimidazolyl)-benzimidazole. The two benzimidazolyl rings are connected through the methythio fragment, making a dihedral angle of 76.09 (5)°. The two N-bound tosyl groups and the benzimidazolyl rings subtend angles of 103.77 (10)° at S1 and 104.48 (10)° at S3 atoms. These values are comparable to those reported for similar structures (Hayashi et al., 2008; Rashid et al., 2006; Rashid et al., 2007). In the crystal, intermolecular C—H···O and C—H···π interactions link the adjacent molecules into polymeric layers parallel to the ab plane. The crystal packing is further stabilized by a π—π interaction formed by the six-membered rings (C8—C13) of anti-parallelly arranged benzimidazole rings related by symmetry of -x, -y, -z + 1 [centroids separation = 3.5187 (4) Å]. Moreover, intramolecular C—H···O and C—H···N hydrogen bonding occurs (Table 1).

Related literature top

For the structures of similar compounds, see: Hayashi et al. (2008); Rashid et al. (2006, 2007).

Experimental top

Sodium (0.17 g) was added to a solution of 2-mercaptobenzimidazole (1 g, 6.7 mmol) in anhydrous methanol (20 ml) and the mixture was stirred at room temperature for 20 minutes. To the mixture, 2-chloromethylbenzimidazole (1.11 g, 6.67 mmol) was added dropwise under vigorous stirring, and then left to stir overnight. The solvent was removed under reduced pressure and the remaining liquid was washed with water and crystallized from tetrahydrofuran (THF) to give the white solid of 2-(thiomethyl-2'-benzimidazolyl)-benzimidazole. A solution of p-toluene sulfonyl chloride (0.75 g, 3.91 mmol) in pyridine (5 ml) was added dropwise to a solution of 2-(thiomethyl-2'-benzimidazolyl)-benzimidazole (0.5 g, 1.78 mmol) in pyridine (5 ml) at 273 K, within 2 hr. The mixture was stirred at room temperature overnight and then poured into a beaker containg 100 ml ice water. It was then stirred for another 15 minutes, extracted with dichloromethane and washed with distilled water (3 x 10 ml). The organic layer was dried with magnesium sulfate and evaporated. The obtained solid was recrystallized from toluene to give the colorless crystals of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Only the major component of the disordered methylthio group is depicted.

1-Tosyl-2-[(1-tosyl-1H-benzimidazol-2-yl)methylsulfanyl]-1H- benzimidazole top

Crystal data top

C₂₉H₂₄N₄O₄S₃	Z = 2
M_r = 588.70	F(000) = 612
Triclinic, P1	D_x = 1.472 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2524 (6) Å	Cell parameters from 6545 reflections
b = 13.5905 (10) Å	θ = 2.6–29.6°
c = 13.8117 (10) Å	µ = 0.32 mm⁻¹
α = 62.5191 (8)°	T = 100 K
β = 75.4090 (9)°	Block, colorless
γ = 85.9930 (9)°	0.38 × 0.35 × 0.21 mm
V = 1327.99 (17) Å³

Data collection top

Bruker APEXII CCD diffractometer	4762 independent reflections
Radiation source: fine-focus sealed tube	4405 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 25.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.887, T_max = 0.935	k = −15→16
8528 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0548P)² + 1.7481P] where P = (F_o² + 2F_c²)/3
4762 reflections	(Δ/σ)_max < 0.001
382 parameters	Δρ_max = 0.29 e Å⁻³
4 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₉H₂₄N₄O₄S₃	γ = 85.9930 (9)°
M_r = 588.70	V = 1327.99 (17) Å³
Triclinic, P1	Z = 2
a = 8.2524 (6) Å	Mo Kα radiation
b = 13.5905 (10) Å	µ = 0.32 mm⁻¹
c = 13.8117 (10) Å	T = 100 K
α = 62.5191 (8)°	0.38 × 0.35 × 0.21 mm
β = 75.4090 (9)°

Data collection top

Bruker APEXII CCD diffractometer	4762 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4405 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.935	R_int = 0.017
8528 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	4 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
4762 reflections	Δρ_min = −0.41 e Å⁻³
382 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.38609 (8)	0.01814 (5)	0.23234 (5)	0.02441 (16)
S2	0.4294 (5)	0.3694 (3)	0.2743 (3)	0.0161 (5)	0.547 (4)
C15	0.445 (2)	0.2467 (15)	0.257 (2)	0.020 (4)	0.547 (4)
H15A	0.4941	0.2670	0.1768	0.024*	0.547 (4)
H15B	0.5227	0.1974	0.3007	0.024*	0.547 (4)
S2'	0.4759 (8)	0.2429 (4)	0.2489 (6)	0.0158 (7)	0.453 (4)
C15'	0.419 (3)	0.3702 (15)	0.2508 (16)	0.032 (4)	0.453 (4)
H15C	0.3390	0.3536	0.3238	0.039*	0.453 (4)
H15D	0.5210	0.4076	0.2474	0.039*	0.453 (4)
S3	0.22947 (7)	0.59437 (4)	0.24425 (5)	0.01762 (15)
O1	0.3429 (3)	−0.09759 (15)	0.30145 (16)	0.0368 (5)
O2	0.5483 (2)	0.06264 (16)	0.21509 (16)	0.0325 (4)
O3	0.3524 (2)	0.55663 (14)	0.30806 (14)	0.0240 (4)
O4	0.2006 (2)	0.70985 (13)	0.18860 (15)	0.0247 (4)
N1	0.2505 (2)	0.08379 (15)	0.29227 (16)	0.0194 (4)
N2	0.1401 (2)	0.21679 (15)	0.33908 (15)	0.0176 (4)
N3	0.2886 (2)	0.55596 (15)	0.14188 (15)	0.0171 (4)
N4	0.3248 (2)	0.42440 (15)	0.08180 (16)	0.0184 (4)
C1	0.3376 (3)	0.05944 (19)	0.10314 (19)	0.0196 (5)
C2	0.3707 (3)	0.1693 (2)	0.0204 (2)	0.0245 (5)
H2	0.4191	0.2222	0.0334	0.029*
C3	0.3317 (3)	0.2000 (2)	−0.0811 (2)	0.0258 (5)
H3	0.3539	0.2748	−0.1382	0.031*
C4	0.2606 (3)	0.1234 (2)	−0.1015 (2)	0.0217 (5)
C5	0.2307 (3)	0.0143 (2)	−0.0176 (2)	0.0248 (5)
H5	0.1836	−0.0389	−0.0307	0.030*
C6	0.2683 (3)	−0.01874 (19)	0.0852 (2)	0.0238 (5)
H6	0.2470	−0.0937	0.1421	0.029*
C7	0.2154 (3)	0.1571 (2)	−0.2115 (2)	0.0275 (5)
H7A	0.2293	0.0947	−0.2295	0.041*
H7B	0.2890	0.2206	−0.2717	0.041*
H7C	0.0985	0.1779	−0.2049	0.041*
C8	0.0772 (3)	0.05618 (19)	0.33644 (18)	0.0209 (5)
C9	−0.0229 (3)	−0.0310 (2)	0.3535 (2)	0.0291 (6)
H9	0.0219	−0.0873	0.3336	0.035*
C10	−0.1929 (4)	−0.0311 (2)	0.4016 (2)	0.0347 (7)
H10	−0.2666	−0.0886	0.4139	0.042*
C11	−0.2576 (3)	0.0506 (2)	0.4321 (2)	0.0301 (6)
H11	−0.3740	0.0469	0.4659	0.036*
C12	−0.1562 (3)	0.1371 (2)	0.41446 (19)	0.0245 (5)
H12	−0.2009	0.1931	0.4350	0.029*
C13	0.0131 (3)	0.13913 (18)	0.36571 (18)	0.0186 (5)
C14	0.2774 (3)	0.18328 (18)	0.29586 (18)	0.0173 (4)
C16	0.0379 (3)	0.51977 (18)	0.32649 (18)	0.0158 (4)
C17	0.0298 (3)	0.42479 (19)	0.42717 (19)	0.0205 (5)
H17	0.1282	0.3987	0.4532	0.025*
C18	−0.1247 (3)	0.36822 (19)	0.48967 (19)	0.0215 (5)
H18	−0.1316	0.3031	0.5591	0.026*
C19	−0.2696 (3)	0.40555 (18)	0.45200 (19)	0.0191 (5)
C20	−0.2574 (3)	0.50082 (19)	0.34960 (19)	0.0198 (5)
H20	−0.3552	0.5264	0.3227	0.024*
C21	−0.1050 (3)	0.55858 (18)	0.28654 (19)	0.0185 (5)
H21	−0.0977	0.6237	0.2171	0.022*
C22	−0.4367 (3)	0.3441 (2)	0.5213 (2)	0.0242 (5)
H22A	−0.5272	0.3933	0.4979	0.036*
H22B	−0.4454	0.3201	0.6012	0.036*
H22C	−0.4463	0.2789	0.5099	0.036*
C23	0.2228 (3)	0.59687 (18)	0.04581 (18)	0.0180 (5)
C24	0.1482 (3)	0.69526 (19)	−0.0111 (2)	0.0235 (5)
H24	0.1322	0.7512	0.0130	0.028*
C25	0.0988 (3)	0.7073 (2)	−0.1043 (2)	0.0270 (5)
H25	0.0469	0.7731	−0.1450	0.032*
C26	0.1228 (3)	0.6259 (2)	−0.1402 (2)	0.0260 (5)
H26	0.0863	0.6368	−0.2043	0.031*
C27	0.1992 (3)	0.5289 (2)	−0.08383 (19)	0.0227 (5)
H27	0.2167	0.4736	−0.1088	0.027*
C28	0.2491 (3)	0.51520 (18)	0.01016 (18)	0.0178 (5)
C29	0.3434 (3)	0.44894 (18)	0.15870 (18)	0.0169 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0326 (3)	0.0210 (3)	0.0251 (3)	0.0125 (2)	−0.0141 (3)	−0.0131 (3)
S2	0.0151 (7)	0.0142 (7)	0.0176 (12)	0.0017 (5)	−0.0032 (8)	−0.0068 (6)
C15	0.015 (7)	0.018 (4)	0.016 (5)	0.010 (3)	−0.002 (4)	−0.002 (3)
S2'	0.0114 (15)	0.0158 (12)	0.0196 (14)	0.0021 (10)	−0.0037 (12)	−0.0078 (9)
C15'	0.036 (8)	0.032 (5)	0.026 (8)	−0.008 (4)	0.007 (4)	−0.017 (5)
S3	0.0140 (3)	0.0182 (3)	0.0225 (3)	0.0000 (2)	−0.0041 (2)	−0.0110 (2)
O1	0.0639 (14)	0.0200 (9)	0.0298 (10)	0.0163 (9)	−0.0213 (9)	−0.0112 (8)
O2	0.0270 (9)	0.0440 (11)	0.0452 (11)	0.0198 (8)	−0.0213 (8)	−0.0320 (10)
O3	0.0165 (8)	0.0313 (9)	0.0294 (9)	0.0016 (7)	−0.0076 (7)	−0.0174 (8)
O4	0.0230 (9)	0.0179 (8)	0.0325 (9)	−0.0025 (7)	−0.0036 (7)	−0.0122 (7)
N1	0.0219 (10)	0.0167 (9)	0.0209 (10)	0.0049 (7)	−0.0082 (8)	−0.0088 (8)
N2	0.0157 (9)	0.0158 (9)	0.0177 (9)	0.0000 (7)	−0.0035 (7)	−0.0050 (8)
N3	0.0153 (9)	0.0166 (9)	0.0171 (9)	0.0006 (7)	−0.0021 (7)	−0.0067 (8)
N4	0.0142 (9)	0.0180 (9)	0.0198 (9)	−0.0022 (7)	−0.0011 (7)	−0.0071 (8)
C1	0.0218 (12)	0.0194 (11)	0.0198 (11)	0.0059 (9)	−0.0062 (9)	−0.0110 (9)
C2	0.0289 (13)	0.0197 (12)	0.0288 (13)	−0.0003 (10)	−0.0117 (10)	−0.0120 (10)
C3	0.0284 (13)	0.0200 (12)	0.0263 (12)	0.0011 (10)	−0.0088 (10)	−0.0075 (10)
C4	0.0181 (11)	0.0273 (12)	0.0221 (12)	0.0065 (9)	−0.0041 (9)	−0.0146 (10)
C5	0.0266 (12)	0.0239 (12)	0.0290 (13)	0.0002 (10)	−0.0054 (10)	−0.0171 (11)
C6	0.0288 (13)	0.0168 (11)	0.0244 (12)	0.0006 (9)	−0.0027 (10)	−0.0102 (10)
C7	0.0286 (13)	0.0326 (14)	0.0274 (13)	0.0086 (11)	−0.0106 (11)	−0.0178 (11)
C8	0.0248 (12)	0.0201 (11)	0.0142 (10)	−0.0011 (9)	−0.0076 (9)	−0.0033 (9)
C9	0.0387 (15)	0.0221 (12)	0.0271 (13)	−0.0040 (11)	−0.0153 (11)	−0.0076 (10)
C10	0.0416 (16)	0.0285 (14)	0.0280 (13)	−0.0144 (12)	−0.0202 (12)	−0.0001 (11)
C11	0.0243 (13)	0.0377 (15)	0.0181 (12)	−0.0101 (11)	−0.0070 (10)	−0.0020 (11)
C12	0.0208 (12)	0.0291 (13)	0.0166 (11)	−0.0051 (10)	−0.0034 (9)	−0.0045 (10)
C13	0.0195 (11)	0.0170 (11)	0.0145 (10)	−0.0019 (9)	−0.0067 (9)	−0.0018 (9)
C14	0.0193 (11)	0.0161 (11)	0.0140 (10)	0.0029 (8)	−0.0052 (8)	−0.0045 (9)
C16	0.0141 (10)	0.0180 (11)	0.0194 (11)	0.0018 (8)	−0.0038 (8)	−0.0123 (9)
C17	0.0164 (11)	0.0234 (12)	0.0215 (11)	0.0046 (9)	−0.0048 (9)	−0.0105 (10)
C18	0.0224 (12)	0.0190 (11)	0.0191 (11)	0.0028 (9)	−0.0054 (9)	−0.0056 (9)
C19	0.0185 (11)	0.0176 (11)	0.0223 (11)	−0.0008 (9)	−0.0016 (9)	−0.0118 (9)
C20	0.0171 (11)	0.0233 (12)	0.0225 (11)	0.0039 (9)	−0.0071 (9)	−0.0127 (10)
C21	0.0176 (11)	0.0165 (11)	0.0203 (11)	0.0015 (9)	−0.0036 (9)	−0.0081 (9)
C22	0.0188 (12)	0.0233 (12)	0.0271 (12)	0.0012 (9)	−0.0030 (10)	−0.0102 (10)
C23	0.0138 (10)	0.0181 (11)	0.0148 (10)	−0.0026 (8)	−0.0014 (8)	−0.0023 (9)
C24	0.0208 (12)	0.0194 (12)	0.0234 (12)	0.0031 (9)	−0.0035 (9)	−0.0055 (10)
C25	0.0226 (12)	0.0248 (13)	0.0199 (12)	0.0019 (10)	−0.0055 (10)	0.0010 (10)
C26	0.0171 (11)	0.0336 (14)	0.0176 (11)	−0.0034 (10)	−0.0034 (9)	−0.0034 (10)
C27	0.0157 (11)	0.0273 (13)	0.0207 (11)	−0.0042 (9)	−0.0001 (9)	−0.0088 (10)
C28	0.0122 (10)	0.0180 (11)	0.0171 (10)	−0.0035 (8)	0.0004 (8)	−0.0044 (9)
C29	0.0115 (10)	0.0157 (11)	0.0163 (10)	−0.0014 (8)	0.0015 (8)	−0.0037 (9)

Geometric parameters (Å, º) top

S1—O1	1.4260 (19)	C7—H7A	0.9800
S1—O2	1.426 (2)	C7—H7B	0.9800
S1—N1	1.6761 (19)	C7—H7C	0.9800
S1—C1	1.750 (2)	C8—C9	1.386 (3)
S2—C29	1.758 (3)	C8—C13	1.394 (3)
S2—C15	1.781 (14)	C9—C10	1.393 (4)
C15—C14	1.521 (15)	C9—H9	0.9500
C15—H15A	0.9900	C10—C11	1.390 (4)
C15—H15B	0.9900	C10—H10	0.9500
S2'—C14	1.710 (6)	C11—C12	1.383 (4)
S2'—C15'	1.770 (14)	C11—H11	0.9500
C15'—C29	1.487 (14)	C12—C13	1.386 (3)
C15'—H15C	0.9900	C12—H12	0.9500
C15'—H15D	0.9900	C16—C17	1.383 (3)
S3—O3	1.4246 (17)	C16—C21	1.395 (3)
S3—O4	1.4274 (17)	C17—C18	1.390 (3)
S3—N3	1.6756 (19)	C17—H17	0.9500
S3—C16	1.753 (2)	C18—C19	1.394 (3)
N1—C8	1.408 (3)	C18—H18	0.9500
N1—C14	1.410 (3)	C19—C20	1.394 (3)
N2—C14	1.298 (3)	C19—C22	1.508 (3)
N2—C13	1.396 (3)	C20—C21	1.383 (3)
N3—C23	1.416 (3)	C20—H20	0.9500
N3—C29	1.422 (3)	C21—H21	0.9500
N4—C29	1.296 (3)	C22—H22A	0.9800
N4—C28	1.403 (3)	C22—H22B	0.9800
C1—C6	1.385 (3)	C22—H22C	0.9800
C1—C2	1.391 (3)	C23—C28	1.392 (3)
C2—C3	1.383 (3)	C23—C24	1.394 (3)
C2—H2	0.9500	C24—C25	1.383 (4)
C3—C4	1.395 (3)	C24—H24	0.9500
C3—H3	0.9500	C25—C26	1.392 (4)
C4—C5	1.387 (3)	C25—H25	0.9500
C4—C7	1.510 (3)	C26—C27	1.387 (3)
C5—C6	1.387 (3)	C26—H26	0.9500
C5—H5	0.9500	C27—C28	1.388 (3)
C6—H6	0.9500	C27—H27	0.9500

O1—S1—O2	120.60 (12)	C11—C10—H10	119.1
O1—S1—N1	106.15 (11)	C9—C10—H10	119.1
O2—S1—N1	105.55 (10)	C12—C11—C10	121.4 (2)
O1—S1—C1	108.87 (11)	C12—C11—H11	119.3
O2—S1—C1	110.46 (11)	C10—C11—H11	119.3
N1—S1—C1	103.77 (10)	C11—C12—C13	117.5 (2)
C29—S2—C15	96.0 (8)	C11—C12—H12	121.2
C14—C15—S2	113.2 (10)	C13—C12—H12	121.2
C14—C15—H15A	108.9	C12—C13—C8	120.6 (2)
S2—C15—H15A	108.9	C12—C13—N2	128.5 (2)
C14—C15—H15B	108.9	C8—C13—N2	110.8 (2)
S2—C15—H15B	108.9	N2—C14—N1	112.32 (19)
H15A—C15—H15B	107.8	N2—C14—C15	121.5 (6)
C14—S2'—C15'	97.1 (9)	N1—C14—C15	126.1 (6)
C29—C15'—S2'	115.7 (9)	N2—C14—S2'	128.0 (2)
C29—C15'—H15C	108.3	N1—C14—S2'	119.7 (2)
S2'—C15'—H15C	108.3	C15—C14—S2'	6.5 (7)
C29—C15'—H15D	108.3	C17—C16—C21	121.3 (2)
S2'—C15'—H15D	108.3	C17—C16—S3	120.80 (17)
H15C—C15'—H15D	107.4	C21—C16—S3	117.91 (17)
O3—S3—O4	120.56 (10)	C16—C17—C18	118.9 (2)
O3—S3—N3	106.26 (10)	C16—C17—H17	120.6
O4—S3—N3	105.40 (10)	C18—C17—H17	120.6
O3—S3—C16	109.64 (10)	C17—C18—C19	121.0 (2)
O4—S3—C16	109.22 (10)	C17—C18—H18	119.5
N3—S3—C16	104.48 (10)	C19—C18—H18	119.5
C8—N1—C14	106.02 (18)	C20—C19—C18	118.9 (2)
C8—N1—S1	124.86 (16)	C20—C19—C22	120.7 (2)
C14—N1—S1	128.62 (16)	C18—C19—C22	120.5 (2)
C14—N2—C13	106.02 (19)	C21—C20—C19	121.0 (2)
C23—N3—C29	105.04 (18)	C21—C20—H20	119.5
C23—N3—S3	124.58 (15)	C19—C20—H20	119.5
C29—N3—S3	124.38 (15)	C20—C21—C16	119.0 (2)
C29—N4—C28	105.61 (19)	C20—C21—H21	120.5
C6—C1—C2	121.3 (2)	C16—C21—H21	120.5
C6—C1—S1	119.01 (18)	C19—C22—H22A	109.5
C2—C1—S1	119.63 (18)	C19—C22—H22B	109.5
C3—C2—C1	118.6 (2)	H22A—C22—H22B	109.5
C3—C2—H2	120.7	C19—C22—H22C	109.5
C1—C2—H2	120.7	H22A—C22—H22C	109.5
C2—C3—C4	121.4 (2)	H22B—C22—H22C	109.5
C2—C3—H3	119.3	C28—C23—C24	122.1 (2)
C4—C3—H3	119.3	C28—C23—N3	105.19 (19)
C5—C4—C3	118.5 (2)	C24—C23—N3	132.7 (2)
C5—C4—C7	120.1 (2)	C25—C24—C23	116.6 (2)
C3—C4—C7	121.5 (2)	C25—C24—H24	121.7
C4—C5—C6	121.4 (2)	C23—C24—H24	121.7
C4—C5—H5	119.3	C24—C25—C26	121.9 (2)
C6—C5—H5	119.3	C24—C25—H25	119.0
C1—C6—C5	118.8 (2)	C26—C25—H25	119.0
C1—C6—H6	120.6	C27—C26—C25	121.0 (2)
C5—C6—H6	120.6	C27—C26—H26	119.5
C4—C7—H7A	109.5	C25—C26—H26	119.5
C4—C7—H7B	109.5	C26—C27—C28	117.9 (2)
H7A—C7—H7B	109.5	C26—C27—H27	121.0
C4—C7—H7C	109.5	C28—C27—H27	121.0
H7A—C7—H7C	109.5	C27—C28—C23	120.5 (2)
H7B—C7—H7C	109.5	C27—C28—N4	128.5 (2)
C9—C8—C13	122.5 (2)	C23—C28—N4	111.05 (19)
C9—C8—N1	132.7 (2)	N4—C29—N3	113.03 (19)
C13—C8—N1	104.79 (19)	N4—C29—C15'	120.7 (6)
C8—C9—C10	116.1 (3)	N3—C29—C15'	126.3 (6)
C8—C9—H9	121.9	N4—C29—S2	128.5 (2)
C10—C9—H9	121.9	N3—C29—S2	118.49 (19)
C11—C10—C9	121.8 (2)	C15'—C29—S2	7.8 (7)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C8–C13 and C23–C28 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.95	2.50	2.886 (3)	105
C9—H9···O1	0.95	2.58	3.094 (4)	114
C15—H15A···N4	0.99	2.48	2.86 (2)	102
C15′—H15C···N2	0.99	2.47	2.84 (3)	102
C24—H24···O4	0.95	2.43	2.991 (3)	118
C6—H6···O4ⁱ	0.95	2.48	3.314 (3)	147
C20—H20···O3ⁱⁱ	0.95	2.46	3.386 (3)	164
C25—H25···Cg1ⁱⁱⁱ	0.95	2.99	3.744 (3)	138
C15—H15A···Cg2^iv	0.99	2.98	3.62 (2)	124

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

Experimental details

Crystal data
Chemical formula	C₂₉H₂₄N₄O₄S₃
M_r	588.70
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.2524 (6), 13.5905 (10), 13.8117 (10)
α, β, γ (°)	62.5191 (8), 75.4090 (9), 85.9930 (9)
V (Å³)	1327.99 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.38 × 0.35 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.887, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	8528, 4762, 4405
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.117, 1.05
No. of reflections	4762
No. of parameters	382
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.41

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C8–C13 and C23–C28 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.95	2.50	2.886 (3)	105
C9—H9···O1	0.95	2.58	3.094 (4)	114
C15—H15A···N4	0.99	2.48	2.86 (2)	102
C15'—H15C···N2	0.99	2.47	2.84 (3)	102
C24—H24···O4	0.95	2.43	2.991 (3)	118
C6—H6···O4ⁱ	0.95	2.48	3.314 (3)	147
C20—H20···O3ⁱⁱ	0.95	2.46	3.386 (3)	164
C25—H25···Cg1ⁱⁱⁱ	0.95	2.99	3.744 (3)	138
C15—H15A···Cg2^iv	0.99	2.98	3.62 (2)	124

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

Footnotes

‡Additional correspondence author, e-mail: m_nassir1971@yahoo.com.

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant No. FP001/2010 A).

References

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