2-Benzyl­sulfanyl-4-[(4-methyl­phen­yl)sulfan­yl]-6-pentyl­pyrimidine-5-carbonitrile

El-Emam, A.A.; Al-Deeb, O.A.; El-Brollosy, N.R.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812025275

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2054

https://doi.org/10.1107/S1600536812025275

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2-Benzylsulfanyl-4-[(4-methylphenyl)sulfanyl]-6-pentylpyrimidine-5-carbonitrile

Ali A. El-Emam,^a ‡ Omar A. Al-Deeb,^a Nasser R. El-Brollosy,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 1 June 2012; accepted 3 June 2012; online 13 June 2012)

In the title compound, C₂₄H₂₅N₃S₂, the S-bound benzene rings have orthogonal [dihedral angle = 85.31 (9)°] and splayed [67.92 (11)°] orientations with respect to the pyrimidine ring; the dihedral angle between the benzene rings is 48.18 (12)°. The pentyl group has an extended all-trans conformation and lies to one side of the pyrimidine ring [the N_py—C_py—C_p—C_p torsion angle = −85.7 (2)°; py = pyrimidine and p = pentyl].

Related literature

For the chemotherapeutic activity of pyrimidine derivatives see: Ghoshal & Jacob (1997 ); De Corte (2005 ); Al-Omar et al. (2010 ); Al-Abdullah et al. (2011 ); Al-Turkistani et al. (2011 ). For a related pyrimidine structure, see: El-Emam et al. (2012 ).

Experimental

Crystal data

C₂₄H₂₅N₃S₂
M_r = 419.59
Monoclinic, P 2₁ /c
a = 9.9178 (2) Å
b = 8.2235 (2) Å
c = 28.4388 (8) Å
β = 96.115 (2)°
V = 2306.24 (10) Å³
Z = 4
Cu Kα radiation
μ = 2.19 mm⁻¹
T = 294 K
0.40 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.689, T_max = 1.000
9523 measured reflections
4746 independent reflections
3720 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.138
S = 1.03
4746 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812025275/zl2483sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025275/zl2483Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025275/zl2483Isup3.cml

checkCIF report

Comment top

The ability of of pyrimidine derivatives to inhibit vital enzymes responsible for DNA bio-synthesis is the reason behind their chemotherapeutic efficacy. Thus, several pyrimidine non-nucleoside derivatives exhibit anti-cancer (Ghoshal & Jacob, 1997), anti-viral (De Corte, 2005) and anti-bacterial activities (Al-Abdullah et al., 2011). The synthesis and crystal structure determination of the title compound, was undertaken in connection with on-going studies of the chemical, pharmacological and structural properties of pyrimidine derivatives (Al-Omar et al., 2010; Al-Turkistani et al., 2011; El-Emam et al. 2012).

With reference to the pyrimidine ring (r.m.s. deviation = 0.011 Å) in the title compound, Fig. 1, the S1- and S2-bound benzene rings form dihedral angles of 85.31 (9) and 67.92 (11)°, respectively, which indicate an orthogonal and a splayed orientation, respectively; the dihedral angle between the benzene rings is 48.18 (12)°. The pentyl group lies to one side of the pyrimidine ring with the N2—C3—C20—C21 torsion angle being -85.7 (2)°. The remaining chain has an extended all-trans conformation [the C20—C21—C22—C23 and C21—C22—C23—C24 torsion angles are -173.8 (2) and 179.6 (2)°, respectively].

No specific intermolecular interactions are evident in the crystal structure. Globally, molecules lie in layers in the ab plane which stack along the c axis, Fig. 2.

Related literature top

For the chemotherapeutic activity of pyrimidine derivatives see: Ghoshal & Jacob (1997); De Corte (2005); Al-Omar et al. (2010); Al-Abdullah et al. (2011); Al-Turkistani et al. (2011). For a related pyrimidine structure, see: El-Emam et al. (2012).

Experimental top

To a solution of 2-(benzylsulfanyl)-4-chloro-6-(n-pentyl)pyrimidine-5-carbonitrile (665 mg, 2 mmol) in dry pyridine (3 ml), 4-thiocresol (248 mg, 2 mmol) was added and the mixture was heated under reflux for 6 h. On cooling, the solvent was then distilled off in vacuo and water (5 ml) was added to the residue. The separated precipitate was collected by filtration, washed with cold water, dried and recrystallized from ethanol to yield 747 mg (89%) of the title compound as colourless crystals. M.p.: 384–386 K. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the title compound in CHCl₃:EtOH (1:1, 5 ml) at room temperature. ¹H NMR (DMSO-d₆, 500.13 MHz): δ 0.85 (t, 3H, CH₃, J = 7.0 Hz), 1.26–1.34 (m, 4H, CH₂CH₂CH₃), 1.64–1.69 (m, 2H, CH₂CH₂CH₂CH₃), 2.27 (s, 3H, Ar—CH₃), 2.76 (t, 2H, CH₂CH₂CH₂CH₂CH₃, J = 7.0 Hz), 4.02 (s, 2H, CH₂S), 6.98–6.99 (m, 2H, Ar—H), 7.21–7.23 (m, 3H, Ar—H), 7.28 (d, 2H, Ar—H, J = 8.0 Hz), 7.51 (d, 2H, Ar—H, J = 8.0 Hz). ¹³C NMR (DMSO-d₆, 125.76 MHz): δ 14.16 (CH₃), 21.29 (CH₂CH₃), 22.29 (ArCH₃), 27.39 (CH₂CH₂CH₃), 31.13 (CH₂CH₂CH₂CH₃), 34.51 (CH₂CH₂CH₂CH₂CH₃), 36.12 (CH₂S), 99.14 (C-5), 114.69 (CN), 122.19, 127.56, 128.74, 129.01, 130.67, 136.20, 137.58, 140.99 (Ar—C), 172.81, 173.15, 173.37 (C-2, C-4 & C-6).

Structure description top

No specific intermolecular interactions are evident in the crystal structure. Globally, molecules lie in layers in the ab plane which stack along the c axis, Fig. 2.

For the chemotherapeutic activity of pyrimidine derivatives see: Ghoshal & Jacob (1997); De Corte (2005); Al-Omar et al. (2010); Al-Abdullah et al. (2011); Al-Turkistani et al. (2011). For a related pyrimidine structure, see: El-Emam et al. (2012).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. A view in projection down the a axis of the unit-cell contents for the title compound.

2-Benzylsulfanyl-4-[(4-methylphenyl)sulfanyl]-6-pentylpyrimidine-5-carbonitrile top

Crystal data top

C₂₄H₂₅N₃S₂	F(000) = 888
M_r = 419.59	D_x = 1.208 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3374 reflections
a = 9.9178 (2) Å	θ = 4.6–76.5°
b = 8.2235 (2) Å	µ = 2.19 mm⁻¹
c = 28.4388 (8) Å	T = 294 K
β = 96.115 (2)°	Prism, colourless
V = 2306.24 (10) Å³	0.40 × 0.20 × 0.10 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4746 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3720 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.017
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.7°, θ_min = 5.6°
ω scan	h = −12→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→10
T_min = 0.689, T_max = 1.000	l = −35→29
9523 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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.0721P)² + 0.1537P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4746 reflections	Δρ_max = 0.18 e Å⁻³
264 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0040 (4)

Crystal data top

C₂₄H₂₅N₃S₂	V = 2306.24 (10) Å³
M_r = 419.59	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 9.9178 (2) Å	µ = 2.19 mm⁻¹
b = 8.2235 (2) Å	T = 294 K
c = 28.4388 (8) Å	0.40 × 0.20 × 0.10 mm
β = 96.115 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4746 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3720 reflections with I > 2σ(I)
T_min = 0.689, T_max = 1.000	R_int = 0.017
9523 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
4746 reflections	Δρ_min = −0.24 e Å⁻³
264 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
S1	0.78263 (6)	0.31009 (7)	0.67270 (2)	0.0889 (2)
S2	0.60772 (5)	0.79595 (6)	0.773134 (19)	0.08036 (18)
N1	0.68705 (13)	0.56138 (17)	0.71826 (5)	0.0665 (3)
N2	0.58228 (15)	0.79774 (19)	0.68118 (6)	0.0764 (4)
N3	0.6892 (3)	0.4609 (4)	0.55333 (8)	0.1323 (9)
C1	0.70156 (16)	0.4995 (2)	0.67609 (7)	0.0696 (4)
C2	0.62755 (16)	0.7066 (2)	0.71888 (7)	0.0678 (4)
C3	0.59644 (18)	0.7347 (3)	0.63894 (8)	0.0775 (5)
C4	0.65498 (17)	0.5814 (3)	0.63450 (7)	0.0745 (5)
C5	0.6733 (2)	0.5142 (3)	0.58931 (8)	0.0940 (6)
C6	0.84843 (18)	0.2845 (2)	0.73261 (7)	0.0729 (5)
C7	0.97186 (19)	0.3532 (3)	0.74887 (8)	0.0858 (6)
H7	1.0217	0.4096	0.7283	0.103*
C8	1.0201 (2)	0.3376 (3)	0.79569 (9)	0.0886 (6)
H8	1.1030	0.3847	0.8064	0.106*
C9	0.9493 (2)	0.2538 (3)	0.82738 (8)	0.0825 (5)
C10	0.8272 (2)	0.1824 (3)	0.80980 (8)	0.0846 (6)
H10	0.7786	0.1229	0.8301	0.102*
C11	0.77708 (18)	0.1978 (2)	0.76337 (8)	0.0787 (5)
H11	0.6948	0.1497	0.7525	0.094*
C12	1.0013 (3)	0.2400 (4)	0.87868 (10)	0.1206 (9)
H12A	1.0233	0.1287	0.8861	0.181*
H12B	0.9329	0.2767	0.8977	0.181*
H12C	1.0811	0.3059	0.8851	0.181*
C13	0.6781 (3)	0.6417 (3)	0.81484 (8)	0.0932 (6)
H13A	0.6102	0.5595	0.8189	0.112*
H13B	0.7550	0.5892	0.8028	0.112*
C14	0.7221 (2)	0.7210 (2)	0.86107 (7)	0.0781 (5)
C15	0.8585 (3)	0.7470 (4)	0.87499 (10)	0.1021 (7)
H15	0.9228	0.7152	0.8553	0.123*
C16	0.8998 (3)	0.8197 (4)	0.91789 (13)	0.1233 (10)
H16	0.9918	0.8365	0.9267	0.148*
C17	0.8086 (4)	0.8667 (4)	0.94725 (11)	0.1249 (10)
H17	0.8378	0.9148	0.9761	0.150*
C18	0.6744 (4)	0.8435 (3)	0.93449 (10)	0.1126 (8)
H18	0.6112	0.8762	0.9545	0.135*
C19	0.6317 (2)	0.7711 (3)	0.89167 (9)	0.0911 (6)
H19	0.5394	0.7557	0.8833	0.109*
C20	0.5482 (2)	0.8344 (3)	0.59621 (8)	0.0928 (6)
H20A	0.5996	0.8045	0.5704	0.111*
H20B	0.5653	0.9484	0.6033	0.111*
C21	0.3988 (2)	0.8112 (3)	0.58083 (8)	0.0843 (5)
H21A	0.3462	0.8583	0.6043	0.101*
H21B	0.3785	0.6959	0.5787	0.101*
C22	0.3585 (2)	0.8912 (3)	0.53285 (7)	0.0885 (6)
H22A	0.3891	1.0033	0.5342	0.106*
H22B	0.4049	0.8360	0.5091	0.106*
C23	0.2100 (2)	0.8882 (4)	0.51799 (9)	0.1024 (7)
H23A	0.1632	0.9429	0.5417	0.123*
H23B	0.1792	0.7762	0.5162	0.123*
C24	0.1729 (3)	0.9695 (4)	0.47047 (8)	0.1191 (9)
H24A	0.0762	0.9674	0.4629	0.179*
H24B	0.2151	0.9124	0.4465	0.179*
H24C	0.2038	1.0802	0.4719	0.179*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0998 (4)	0.0797 (3)	0.0874 (4)	0.0206 (3)	0.0105 (3)	−0.0054 (3)
S2	0.0877 (3)	0.0652 (3)	0.0881 (3)	0.0125 (2)	0.0093 (2)	0.0008 (2)
N1	0.0611 (7)	0.0595 (7)	0.0790 (9)	0.0001 (6)	0.0086 (6)	0.0046 (7)
N2	0.0701 (8)	0.0691 (9)	0.0894 (11)	0.0054 (7)	0.0059 (7)	0.0147 (8)
N3	0.160 (2)	0.153 (2)	0.0858 (13)	0.0146 (18)	0.0225 (14)	−0.0026 (15)
C1	0.0595 (8)	0.0677 (9)	0.0822 (11)	−0.0005 (7)	0.0107 (8)	0.0044 (9)
C2	0.0556 (8)	0.0622 (9)	0.0855 (11)	−0.0011 (7)	0.0069 (7)	0.0079 (8)
C3	0.0629 (9)	0.0820 (12)	0.0871 (13)	−0.0012 (9)	0.0061 (8)	0.0159 (10)
C4	0.0656 (9)	0.0816 (11)	0.0763 (11)	−0.0025 (8)	0.0076 (8)	0.0072 (9)
C5	0.0948 (14)	0.1054 (17)	0.0820 (13)	0.0045 (12)	0.0112 (11)	0.0084 (13)
C6	0.0685 (9)	0.0600 (9)	0.0909 (12)	0.0119 (8)	0.0116 (8)	0.0009 (9)
C7	0.0723 (11)	0.0789 (12)	0.1077 (16)	−0.0043 (9)	0.0165 (11)	0.0062 (11)
C8	0.0663 (10)	0.0827 (12)	0.1157 (17)	−0.0002 (9)	0.0046 (10)	−0.0039 (12)
C9	0.0767 (11)	0.0776 (11)	0.0935 (14)	0.0201 (10)	0.0096 (10)	−0.0055 (10)
C10	0.0753 (11)	0.0795 (12)	0.1015 (15)	0.0072 (9)	0.0207 (10)	0.0103 (11)
C11	0.0645 (9)	0.0689 (10)	0.1023 (15)	0.0031 (8)	0.0074 (9)	0.0035 (10)
C12	0.1118 (19)	0.148 (3)	0.0993 (18)	0.0205 (18)	−0.0022 (14)	−0.0077 (18)
C13	0.1218 (17)	0.0681 (11)	0.0882 (14)	0.0101 (11)	0.0048 (12)	0.0053 (10)
C14	0.0911 (12)	0.0633 (10)	0.0812 (12)	0.0077 (9)	0.0148 (10)	0.0089 (9)
C15	0.0923 (14)	0.1062 (17)	0.1091 (18)	0.0028 (13)	0.0160 (13)	0.0138 (15)
C16	0.114 (2)	0.117 (2)	0.132 (3)	−0.0128 (17)	−0.0209 (19)	0.0136 (19)
C17	0.173 (3)	0.0932 (18)	0.102 (2)	−0.002 (2)	−0.014 (2)	0.0037 (15)
C18	0.160 (3)	0.0864 (15)	0.0962 (17)	0.0159 (17)	0.0345 (17)	−0.0002 (13)
C19	0.0950 (14)	0.0792 (12)	0.1008 (16)	0.0110 (11)	0.0191 (12)	0.0042 (12)
C20	0.0897 (13)	0.0930 (14)	0.0945 (15)	0.0018 (11)	0.0043 (11)	0.0267 (12)
C21	0.0856 (12)	0.0820 (12)	0.0841 (13)	0.0078 (10)	0.0038 (10)	0.0106 (10)
C22	0.0912 (13)	0.0908 (14)	0.0825 (13)	0.0047 (11)	0.0050 (10)	0.0070 (11)
C23	0.0898 (13)	0.1191 (19)	0.0964 (15)	0.0044 (13)	0.0022 (11)	0.0204 (14)
C24	0.1070 (16)	0.148 (2)	0.0972 (17)	−0.0055 (17)	−0.0142 (13)	0.0290 (17)

Geometric parameters (Å, º) top

S1—C1	1.7601 (19)	C13—H13A	0.9700
S1—C6	1.771 (2)	C13—H13B	0.9700
S2—C2	1.739 (2)	C14—C19	1.377 (3)
S2—C13	1.824 (2)	C14—C15	1.385 (3)
N1—C1	1.325 (2)	C15—C16	1.381 (4)
N1—C2	1.333 (2)	C15—H15	0.9300
N2—C3	1.329 (3)	C16—C17	1.352 (5)
N2—C2	1.345 (2)	C16—H16	0.9300
N3—C5	1.140 (3)	C17—C18	1.355 (4)
C1—C4	1.396 (3)	C17—H17	0.9300
C3—C4	1.399 (3)	C18—C19	1.381 (4)
C3—C20	1.501 (3)	C18—H18	0.9300
C4—C5	1.428 (3)	C19—H19	0.9300
C6—C7	1.383 (3)	C20—C21	1.511 (3)
C6—C11	1.381 (3)	C20—H20A	0.9700
C7—C8	1.372 (3)	C20—H20B	0.9700
C7—H7	0.9300	C21—C22	1.529 (3)
C8—C9	1.384 (3)	C21—H21A	0.9700
C8—H8	0.9300	C21—H21B	0.9700
C9—C10	1.390 (3)	C22—C23	1.489 (3)
C9—C12	1.499 (3)	C22—H22A	0.9700
C10—C11	1.366 (3)	C22—H22B	0.9700
C10—H10	0.9300	C23—C24	1.518 (3)
C11—H11	0.9300	C23—H23A	0.9700
C12—H12A	0.9600	C23—H23B	0.9700
C12—H12B	0.9600	C24—H24A	0.9600
C12—H12C	0.9600	C24—H24B	0.9600
C13—C14	1.491 (3)	C24—H24C	0.9600

C1—S1—C6	100.16 (9)	C19—C14—C13	122.7 (2)
C2—S2—C13	102.22 (9)	C15—C14—C13	120.3 (2)
C1—N1—C2	116.55 (16)	C16—C15—C14	120.5 (3)
C3—N2—C2	116.38 (17)	C16—C15—H15	119.7
N1—C1—C4	121.56 (17)	C14—C15—H15	119.7
N1—C1—S1	118.93 (13)	C17—C16—C15	121.0 (3)
C4—C1—S1	119.50 (15)	C17—C16—H16	119.5
N1—C2—N2	126.81 (19)	C15—C16—H16	119.5
N1—C2—S2	118.82 (14)	C16—C17—C18	119.8 (3)
N2—C2—S2	114.34 (14)	C16—C17—H17	120.1
N2—C3—C4	121.19 (18)	C18—C17—H17	120.1
N2—C3—C20	117.6 (2)	C17—C18—C19	119.8 (3)
C4—C3—C20	121.2 (2)	C17—C18—H18	120.1
C1—C4—C3	117.46 (18)	C19—C18—H18	120.1
C1—C4—C5	120.89 (19)	C14—C19—C18	121.8 (3)
C3—C4—C5	121.57 (19)	C14—C19—H19	119.1
N3—C5—C4	179.3 (3)	C18—C19—H19	119.1
C7—C6—C11	119.6 (2)	C3—C20—C21	112.55 (18)
C7—C6—S1	119.71 (16)	C3—C20—H20A	109.1
C11—C6—S1	120.65 (16)	C21—C20—H20A	109.1
C8—C7—C6	119.4 (2)	C3—C20—H20B	109.1
C8—C7—H7	120.3	C21—C20—H20B	109.1
C6—C7—H7	120.3	H20A—C20—H20B	107.8
C7—C8—C9	122.0 (2)	C20—C21—C22	111.03 (18)
C7—C8—H8	119.0	C20—C21—H21A	109.4
C9—C8—H8	119.0	C22—C21—H21A	109.4
C8—C9—C10	117.3 (2)	C20—C21—H21B	109.4
C8—C9—C12	121.7 (2)	C22—C21—H21B	109.4
C10—C9—C12	121.0 (2)	H21A—C21—H21B	108.0
C11—C10—C9	121.5 (2)	C23—C22—C21	113.75 (19)
C11—C10—H10	119.3	C23—C22—H22A	108.8
C9—C10—H10	119.3	C21—C22—H22A	108.8
C10—C11—C6	120.11 (19)	C23—C22—H22B	108.8
C10—C11—H11	119.9	C21—C22—H22B	108.8
C6—C11—H11	119.9	H22A—C22—H22B	107.7
C9—C12—H12A	109.5	C22—C23—C24	112.6 (2)
C9—C12—H12B	109.5	C22—C23—H23A	109.1
H12A—C12—H12B	109.5	C24—C23—H23A	109.1
C9—C12—H12C	109.5	C22—C23—H23B	109.1
H12A—C12—H12C	109.5	C24—C23—H23B	109.1
H12B—C12—H12C	109.5	H23A—C23—H23B	107.8
C14—C13—S2	108.96 (14)	C23—C24—H24A	109.5
C14—C13—H13A	109.9	C23—C24—H24B	109.5
S2—C13—H13A	109.9	H24A—C24—H24B	109.5
C14—C13—H13B	109.9	C23—C24—H24C	109.5
S2—C13—H13B	109.9	H24A—C24—H24C	109.5
H13A—C13—H13B	108.3	H24B—C24—H24C	109.5
C19—C14—C15	117.1 (2)

C2—N1—C1—C4	−0.9 (2)	C6—C7—C8—C9	0.4 (3)
C2—N1—C1—S1	178.62 (12)	C7—C8—C9—C10	1.2 (3)
C6—S1—C1—N1	−10.82 (15)	C7—C8—C9—C12	−178.7 (2)
C6—S1—C1—C4	168.75 (14)	C8—C9—C10—C11	−1.7 (3)
C1—N1—C2—N2	−0.9 (3)	C12—C9—C10—C11	178.3 (2)
C1—N1—C2—S2	−179.06 (12)	C9—C10—C11—C6	0.6 (3)
C3—N2—C2—N1	1.2 (3)	C7—C6—C11—C10	1.1 (3)
C3—N2—C2—S2	179.48 (13)	S1—C6—C11—C10	−178.29 (15)
C13—S2—C2—N1	−1.69 (16)	C2—S2—C13—C14	156.66 (16)
C13—S2—C2—N2	179.92 (14)	S2—C13—C14—C19	75.3 (2)
C2—N2—C3—C4	0.2 (3)	S2—C13—C14—C15	−104.8 (2)
C2—N2—C3—C20	−179.37 (16)	C19—C14—C15—C16	0.2 (4)
N1—C1—C4—C3	2.2 (3)	C13—C14—C15—C16	−179.7 (2)
S1—C1—C4—C3	−177.32 (13)	C14—C15—C16—C17	0.1 (5)
N1—C1—C4—C5	179.03 (17)	C15—C16—C17—C18	−0.4 (5)
S1—C1—C4—C5	−0.5 (2)	C16—C17—C18—C19	0.4 (4)
N2—C3—C4—C1	−1.9 (3)	C15—C14—C19—C18	−0.2 (3)
C20—C3—C4—C1	177.73 (17)	C13—C14—C19—C18	179.6 (2)
N2—C3—C4—C5	−178.63 (18)	C17—C18—C19—C14	0.0 (4)
C20—C3—C4—C5	1.0 (3)	N2—C3—C20—C21	−85.7 (2)
C1—S1—C6—C7	−85.01 (17)	C4—C3—C20—C21	94.7 (2)
C1—S1—C6—C11	94.37 (16)	C3—C20—C21—C22	−170.5 (2)
C11—C6—C7—C8	−1.6 (3)	C20—C21—C22—C23	−173.8 (2)
S1—C6—C7—C8	177.82 (16)	C21—C22—C23—C24	179.6 (2)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₅N₃S₂
M_r	419.59
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	9.9178 (2), 8.2235 (2), 28.4388 (8)
β (°)	96.115 (2)
V (Å³)	2306.24 (10)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.19
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.689, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9523, 4746, 3720
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.138, 1.03
No. of reflections	4746
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.24

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Footnotes

‡Additional correspondence author, e-mail: elemam5@hotmail.com.

Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, is greatly appreciated. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM·C/HIR/MOHE/SC/12).

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