4-tert-Butyl-N-[(2,6-dimethyl­phen­yl)carbamothio­yl]benzamide

Yusof, M.S.M.; Arshad, S.; Razak, I.A.; Rahman, A.A.

doi:10.1107/S1600536812034174

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2670

doi:10.1107/S1600536812034174

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4-tert-Butyl-N-[(2,6-dimethylphenyl)carbamothioyl]benzamide

M. Sukeri M. Yusof,^a Suhana Arshad,^b Ibrahim Abdul Razak ^b ^*‡ and Azhar Abdul Rahman ^b §

^aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Menggabang Telipot, 21030 Kuala Terengganu, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 27 July 2012; accepted 1 August 2012; online 11 August 2012)

The asymmetric unit of the title compound, C₂₀H₂₄N₂OS, consists of two crystallographically independent molecules. In each molecule, an intramolecular N—H⋯O hydrogen bond forms an S(6) ring motif. The dihedral angles between the terminal benzene rings in the two molecules are 75.52 (7) and 42.80 (7)°. In the crystal, intermolecular N—H⋯S interactions link the molecules into a chain along the c axis.

Related literature

For related structures, see: Yusof, Mutalib et al. (2012 ); Yusof, Embong et al. (2012a ,b ); Usman et al. (2002 ); Al-abbasi et al. (2010 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₀H₂₄N₂OS
M_r = 340.47
Monoclinic, P 2₁ /c
a = 19.5893 (2) Å
b = 8.8118 (1) Å
c = 23.5034 (2) Å
β = 114.886 (1)°
V = 3680.37 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 K
0.41 × 0.22 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.929, T_max = 0.970
67130 measured reflections
10823 independent reflections
8234 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.120
S = 1.04
10823 reflections
459 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2NA⋯O1A	0.84 (2)	2.06 (2)	2.6972 (19)	133.1 (16)
N2B—H2NB⋯O1B	0.84 (2)	2.08 (2)	2.7183 (19)	132.4 (17)
N2A—H2NA⋯S1B	0.84 (2)	2.715 (17)	3.2598 (12)	124.3 (16)
N2B—H2NB⋯S1Aⁱ	0.84 (2)	2.780 (19)	3.3044 (12)	121.9 (16)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034174/is5176sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034174/is5176Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034174/is5176Isup3.cml

checkCIF report

Comment top

In continuation of our work on synthesis of thiourea derivatives (Yusof, Mutalib et al., 2012; Yusof, Embong et al., 2012a,b) the title compound is prepared and its crystal structure is reported.

The asymmetric unit of the title compound consists of two crystallographically independent molecules A and B (Fig. 1). In both molecules, the intramolecular N2A—H2NA···O1A and N2B—H2NB···O1B hydrogen bonds (Table 1) generate S(6) ring motifs (Bernstein et al., 1995). The dihedral angles between the two terminal benzene rings in molecule A and B are 75.52 (7) and 42.80 (7)°, respectively. The bond lengths and angles are within normal ranges and comparable to the previously reported structures (Usman et al., 2002; Al-abbasi et al., 2010).

The crystal packing is shown in Fig. 2. The intermolecular N2A—H2NA···S1B and N2B—H2NB···S1A interactions (Table 1) link the molecules into a one-dimensional chain along the c axis.

Related literature top

For related structures, see: Yusof, Mutalib et al. (2012); Yusof, Embong et al. (2012a,b); Usman et al. (2002); Al-abbasi et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

30 ml acetone solution of 2,4-dimethylaniline (0.93 g, 7.7 mmol) was added into 30 ml acetone containing 4-tert-butylbenzoyl chloride (1.50 g, 7.7 mmol) and ammonium thiocyanate (0.58 g, 9.5 mmol). The mixture was refluxed for 2.5 hours. The solution was filtered and left to evaporate at room temperature. The yellowish precipitate obtained after a few days was washed with water and cold ethanol. The crystals were obtained by recrystallization from DMF.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels with 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

4-tert-Butyl-N-[(2,6-dimethylphenyl)carbamothioyl]benzamide top

Crystal data top

C₂₀H₂₄N₂OS	F(000) = 1456
M_r = 340.47	D_x = 1.229 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9861 reflections
a = 19.5893 (2) Å	θ = 2.3–30.0°
b = 8.8118 (1) Å	µ = 0.18 mm⁻¹
c = 23.5034 (2) Å	T = 100 K
β = 114.886 (1)°	Block, yellow
V = 3680.37 (6) Å³	0.41 × 0.22 × 0.17 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	10823 independent reflections
Radiation source: fine-focus sealed tube	8234 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −27→27
T_min = 0.929, T_max = 0.970	k = −12→12
67130 measured reflections	l = −33→33

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0433P)² + 2.0471P] where P = (F_o² + 2F_c²)/3
10823 reflections	(Δ/σ)_max = 0.001
459 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₀H₂₄N₂OS	V = 3680.37 (6) Å³
M_r = 340.47	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.5893 (2) Å	µ = 0.18 mm⁻¹
b = 8.8118 (1) Å	T = 100 K
c = 23.5034 (2) Å	0.41 × 0.22 × 0.17 mm
β = 114.886 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	10823 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	8234 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.970	R_int = 0.044
67130 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.43 e Å⁻³
10823 reflections	Δρ_min = −0.24 e Å⁻³
459 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
S1A	0.33613 (2)	0.71302 (5)	0.125254 (16)	0.02173 (9)
O1A	0.17289 (6)	0.71337 (13)	0.21821 (5)	0.0218 (2)
N1A	0.20809 (7)	0.71907 (15)	0.13716 (6)	0.0175 (2)
N2A	0.31610 (7)	0.70427 (14)	0.23058 (5)	0.0151 (2)
C1A	0.02289 (8)	0.77443 (18)	0.13710 (7)	0.0205 (3)
H1AA	0.0382	0.7907	0.1798	0.025*
C2A	−0.05243 (9)	0.79149 (19)	0.09627 (7)	0.0222 (3)
H2AA	−0.0867	0.8200	0.1122	0.027*
C3A	−0.07793 (8)	0.76693 (16)	0.03200 (7)	0.0170 (3)
C4A	−0.02428 (9)	0.72404 (19)	0.01032 (7)	0.0229 (3)
H4AA	−0.0397	0.7062	−0.0323	0.028*
C5A	0.05104 (9)	0.70740 (18)	0.05048 (7)	0.0222 (3)
H5AA	0.0854	0.6789	0.0346	0.027*
C6A	0.07568 (8)	0.73333 (16)	0.11479 (6)	0.0159 (3)
C7A	0.15550 (8)	0.72049 (16)	0.16165 (6)	0.0160 (3)
C8A	0.28677 (8)	0.71169 (16)	0.16839 (6)	0.0157 (3)
C9A	0.39627 (8)	0.69750 (16)	0.26710 (6)	0.0136 (3)
C10A	0.43051 (8)	0.55544 (16)	0.28225 (6)	0.0154 (3)
C11A	0.50857 (8)	0.55097 (17)	0.31649 (7)	0.0188 (3)
H11A	0.5332	0.4580	0.3270	0.023*
C12A	0.54946 (8)	0.68438 (18)	0.33479 (7)	0.0199 (3)
H12A	0.6015	0.6799	0.3570	0.024*
C13A	0.51391 (8)	0.82473 (17)	0.32053 (7)	0.0182 (3)
H13A	0.5421	0.9132	0.3338	0.022*
C14A	0.43598 (8)	0.83310 (16)	0.28633 (6)	0.0150 (3)
C15A	0.38419 (9)	0.41307 (17)	0.26297 (7)	0.0222 (3)
H15A	0.3561	0.4120	0.2182	0.033*
H15B	0.3500	0.4100	0.2826	0.033*
H15C	0.4168	0.3263	0.2757	0.033*
C16A	0.39558 (9)	0.98275 (17)	0.27133 (7)	0.0213 (3)
H16A	0.3661	0.9904	0.2269	0.032*
H16B	0.4317	1.0638	0.2850	0.032*
H16C	0.3632	0.9898	0.2925	0.032*
C17A	−0.16009 (8)	0.79010 (17)	−0.01444 (7)	0.0199 (3)
C18A	−0.16415 (10)	0.9314 (2)	−0.05418 (8)	0.0301 (4)
H18A	−0.1473	1.0186	−0.0273	0.045*
H18B	−0.2151	0.9468	−0.0842	0.045*
H18C	−0.1325	0.9169	−0.0757	0.045*
C19A	−0.18877 (9)	0.65003 (19)	−0.05713 (7)	0.0248 (3)
H19A	−0.1865	0.5626	−0.0320	0.037*
H19B	−0.1578	0.6335	−0.0792	0.037*
H19C	−0.2399	0.6667	−0.0868	0.037*
C20A	−0.21171 (9)	0.8148 (2)	0.01879 (8)	0.0313 (4)
H20A	−0.1971	0.9059	0.0434	0.047*
H20B	−0.2075	0.7299	0.0457	0.047*
H20C	−0.2628	0.8240	−0.0119	0.047*
S1B	0.33713 (2)	0.71970 (5)	0.375613 (16)	0.01977 (9)
O1B	0.16877 (6)	0.80776 (13)	0.45954 (5)	0.0227 (2)
N1B	0.20713 (7)	0.73436 (14)	0.38416 (6)	0.0156 (2)
N2B	0.31391 (7)	0.76209 (14)	0.47819 (5)	0.0151 (2)
C1B	0.01921 (8)	0.84843 (17)	0.36482 (7)	0.0188 (3)
H1BA	0.0335	0.9178	0.3976	0.023*
C2B	−0.05593 (8)	0.83488 (17)	0.32340 (7)	0.0194 (3)
H2BA	−0.0911	0.8985	0.3280	0.023*
C3B	−0.08026 (8)	0.72766 (16)	0.27467 (7)	0.0159 (3)
C4B	−0.02515 (8)	0.64045 (17)	0.26716 (7)	0.0196 (3)
H4BA	−0.0393	0.5703	0.2346	0.024*
C5B	0.05073 (8)	0.65653 (17)	0.30748 (7)	0.0188 (3)
H5BA	0.0865	0.5987	0.3009	0.023*
C6B	0.07355 (8)	0.75798 (16)	0.35734 (7)	0.0156 (3)
C7B	0.15330 (8)	0.76964 (16)	0.40537 (7)	0.0159 (3)
C8B	0.28580 (8)	0.74046 (15)	0.41641 (6)	0.0147 (3)
C9B	0.39374 (8)	0.77562 (16)	0.51574 (6)	0.0144 (3)
C10B	0.43690 (8)	0.64373 (16)	0.53508 (6)	0.0169 (3)
C11B	0.51411 (9)	0.66015 (18)	0.57088 (7)	0.0212 (3)
H11B	0.5444	0.5745	0.5845	0.025*
C12B	0.54591 (9)	0.80337 (19)	0.58635 (7)	0.0231 (3)
H12B	0.5976	0.8129	0.6097	0.028*
C13B	0.50172 (9)	0.93235 (18)	0.56754 (7)	0.0212 (3)
H13B	0.5239	1.0276	0.5786	0.025*
C14B	0.42422 (8)	0.92070 (16)	0.53205 (6)	0.0168 (3)
C15B	0.40121 (9)	0.48993 (17)	0.51972 (7)	0.0230 (3)
H15D	0.4396	0.4134	0.5345	0.035*
H15E	0.3734	0.4807	0.4751	0.035*
H15F	0.3678	0.4772	0.5397	0.035*
C16B	0.37459 (9)	1.05825 (18)	0.51222 (7)	0.0240 (3)
H16D	0.3453	1.0560	0.4676	0.036*
H16E	0.4051	1.1481	0.5234	0.036*
H16F	0.3415	1.0587	0.5329	0.036*
C17B	−0.16468 (8)	0.70816 (17)	0.23318 (7)	0.0178 (3)
C18B	−0.20564 (9)	0.6758 (2)	0.27498 (8)	0.0258 (3)
H18D	−0.1854	0.5855	0.2991	0.039*
H18E	−0.2583	0.6617	0.2492	0.039*
H18F	−0.1989	0.7599	0.3028	0.039*
C19B	−0.18011 (9)	0.57519 (18)	0.18737 (7)	0.0244 (3)
H19D	−0.1609	0.4832	0.2105	0.037*
H19E	−0.1557	0.5935	0.1601	0.037*
H19F	−0.2334	0.5655	0.1628	0.037*
C20B	−0.19667 (9)	0.85460 (18)	0.19550 (7)	0.0218 (3)
H20D	−0.2496	0.8423	0.1702	0.033*
H20E	−0.1716	0.8748	0.1689	0.033*
H20F	−0.1888	0.9379	0.2239	0.033*
H2NA	0.2879 (10)	0.707 (2)	0.2491 (8)	0.022 (5)*
H2NB	0.2845 (11)	0.776 (2)	0.4955 (9)	0.031 (5)*
H1NB	0.1927 (11)	0.720 (2)	0.3461 (9)	0.027 (5)*
H1NA	0.1930 (11)	0.727 (2)	0.0994 (9)	0.030 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.01282 (18)	0.0403 (2)	0.01273 (16)	−0.00115 (15)	0.00602 (14)	−0.00031 (14)
O1A	0.0139 (5)	0.0350 (6)	0.0162 (5)	0.0015 (4)	0.0062 (4)	0.0028 (4)
N1A	0.0114 (6)	0.0274 (6)	0.0124 (5)	0.0003 (5)	0.0036 (5)	0.0013 (5)
N2A	0.0121 (6)	0.0216 (6)	0.0130 (5)	0.0010 (5)	0.0069 (5)	0.0005 (4)
C1A	0.0135 (7)	0.0320 (8)	0.0155 (6)	0.0011 (6)	0.0056 (6)	0.0001 (6)
C2A	0.0149 (7)	0.0319 (8)	0.0213 (7)	0.0031 (6)	0.0092 (6)	−0.0011 (6)
C3A	0.0132 (7)	0.0184 (7)	0.0184 (7)	0.0003 (5)	0.0055 (6)	0.0018 (5)
C4A	0.0150 (8)	0.0355 (9)	0.0172 (7)	0.0002 (6)	0.0056 (6)	−0.0033 (6)
C5A	0.0157 (7)	0.0317 (8)	0.0203 (7)	0.0011 (6)	0.0088 (6)	−0.0039 (6)
C6A	0.0117 (7)	0.0180 (6)	0.0166 (6)	0.0001 (5)	0.0046 (5)	0.0016 (5)
C7A	0.0141 (7)	0.0162 (6)	0.0173 (6)	0.0007 (5)	0.0063 (5)	0.0013 (5)
C8A	0.0125 (7)	0.0182 (6)	0.0156 (6)	−0.0005 (5)	0.0051 (5)	0.0002 (5)
C9A	0.0107 (6)	0.0195 (7)	0.0109 (6)	0.0013 (5)	0.0048 (5)	0.0009 (5)
C10A	0.0161 (7)	0.0170 (6)	0.0150 (6)	0.0009 (5)	0.0086 (5)	0.0011 (5)
C11A	0.0166 (7)	0.0222 (7)	0.0185 (7)	0.0069 (5)	0.0083 (6)	0.0053 (5)
C12A	0.0113 (7)	0.0308 (8)	0.0158 (6)	0.0023 (6)	0.0041 (5)	0.0022 (5)
C13A	0.0154 (7)	0.0230 (7)	0.0166 (6)	−0.0034 (5)	0.0071 (6)	−0.0015 (5)
C14A	0.0149 (7)	0.0173 (6)	0.0137 (6)	0.0012 (5)	0.0069 (5)	0.0001 (5)
C15A	0.0235 (8)	0.0179 (7)	0.0267 (8)	−0.0016 (6)	0.0119 (7)	0.0002 (6)
C16A	0.0227 (8)	0.0182 (7)	0.0236 (7)	0.0037 (6)	0.0105 (6)	0.0017 (5)
C17A	0.0116 (7)	0.0243 (7)	0.0204 (7)	0.0030 (5)	0.0034 (6)	0.0032 (6)
C18A	0.0241 (9)	0.0289 (9)	0.0285 (8)	0.0018 (7)	0.0025 (7)	0.0081 (7)
C19A	0.0150 (7)	0.0289 (8)	0.0250 (8)	−0.0023 (6)	0.0030 (6)	−0.0007 (6)
C20A	0.0121 (8)	0.0489 (11)	0.0294 (8)	0.0061 (7)	0.0055 (7)	−0.0008 (7)
S1B	0.01337 (18)	0.0342 (2)	0.01263 (15)	0.00004 (14)	0.00637 (14)	−0.00061 (14)
O1B	0.0147 (5)	0.0346 (6)	0.0181 (5)	−0.0001 (4)	0.0063 (4)	−0.0059 (4)
N1B	0.0102 (6)	0.0230 (6)	0.0125 (5)	0.0005 (4)	0.0037 (5)	−0.0006 (4)
N2B	0.0110 (6)	0.0221 (6)	0.0131 (5)	−0.0007 (4)	0.0059 (5)	−0.0011 (4)
C1B	0.0145 (7)	0.0207 (7)	0.0201 (7)	−0.0021 (5)	0.0064 (6)	−0.0059 (5)
C2B	0.0138 (7)	0.0204 (7)	0.0242 (7)	0.0005 (5)	0.0082 (6)	−0.0055 (6)
C3B	0.0116 (7)	0.0167 (6)	0.0181 (6)	−0.0018 (5)	0.0050 (5)	−0.0007 (5)
C4B	0.0162 (7)	0.0214 (7)	0.0197 (7)	−0.0008 (5)	0.0061 (6)	−0.0058 (5)
C5B	0.0132 (7)	0.0215 (7)	0.0206 (7)	0.0029 (5)	0.0060 (6)	−0.0031 (5)
C6B	0.0116 (7)	0.0173 (6)	0.0181 (6)	−0.0005 (5)	0.0063 (5)	0.0006 (5)
C7B	0.0116 (7)	0.0173 (6)	0.0185 (6)	−0.0002 (5)	0.0059 (5)	−0.0001 (5)
C8B	0.0115 (7)	0.0164 (6)	0.0157 (6)	0.0000 (5)	0.0054 (5)	0.0013 (5)
C9B	0.0114 (7)	0.0219 (7)	0.0110 (6)	−0.0014 (5)	0.0057 (5)	−0.0005 (5)
C10B	0.0169 (7)	0.0209 (7)	0.0137 (6)	−0.0009 (5)	0.0073 (5)	0.0003 (5)
C11B	0.0163 (7)	0.0300 (8)	0.0177 (7)	0.0044 (6)	0.0076 (6)	0.0040 (6)
C12B	0.0122 (7)	0.0390 (9)	0.0167 (7)	−0.0034 (6)	0.0048 (6)	0.0011 (6)
C13B	0.0190 (8)	0.0286 (8)	0.0171 (7)	−0.0086 (6)	0.0086 (6)	−0.0036 (6)
C14B	0.0159 (7)	0.0218 (7)	0.0145 (6)	−0.0020 (5)	0.0083 (5)	−0.0013 (5)
C15B	0.0248 (8)	0.0207 (7)	0.0217 (7)	−0.0001 (6)	0.0079 (6)	0.0005 (6)
C16B	0.0253 (8)	0.0218 (7)	0.0256 (8)	0.0003 (6)	0.0114 (7)	0.0004 (6)
C17B	0.0123 (7)	0.0196 (7)	0.0190 (6)	−0.0025 (5)	0.0041 (5)	−0.0026 (5)
C18B	0.0164 (8)	0.0352 (9)	0.0252 (8)	−0.0066 (6)	0.0081 (6)	−0.0002 (6)
C19B	0.0177 (8)	0.0244 (8)	0.0249 (8)	−0.0022 (6)	0.0028 (6)	−0.0061 (6)
C20B	0.0152 (7)	0.0241 (7)	0.0230 (7)	0.0003 (6)	0.0051 (6)	−0.0005 (6)

Geometric parameters (Å, º) top

S1A—C8A	1.6697 (15)	S1B—C8B	1.6659 (15)
O1A—C7A	1.2273 (17)	O1B—C7B	1.2249 (17)
N1A—C7A	1.3754 (19)	N1B—C7B	1.3784 (19)
N1A—C8A	1.4021 (18)	N1B—C8B	1.4033 (18)
N1A—H1NA	0.813 (19)	N1B—H1NB	0.826 (19)
N2A—C8A	1.3282 (17)	N2B—C8B	1.3323 (17)
N2A—C9A	1.4396 (18)	N2B—C9B	1.4412 (18)
N2A—H2NA	0.836 (19)	N2B—H2NB	0.84 (2)
C1A—C2A	1.389 (2)	C1B—C2B	1.387 (2)
C1A—C6A	1.390 (2)	C1B—C6B	1.399 (2)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.394 (2)	C2B—C3B	1.4043 (19)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.399 (2)	C3B—C4B	1.395 (2)
C3A—C17A	1.531 (2)	C3B—C17B	1.5356 (19)
C4A—C5A	1.385 (2)	C4B—C5B	1.394 (2)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.399 (2)	C5B—C6B	1.3898 (19)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.4905 (19)	C6B—C7B	1.4970 (19)
C9A—C14A	1.3933 (19)	C9B—C14B	1.395 (2)
C9A—C10A	1.3938 (19)	C9B—C10B	1.396 (2)
C10A—C11A	1.397 (2)	C10B—C11B	1.395 (2)
C10A—C15A	1.502 (2)	C10B—C15B	1.498 (2)
C11A—C12A	1.385 (2)	C11B—C12B	1.387 (2)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.389 (2)	C12B—C13B	1.384 (2)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.396 (2)	C13B—C14B	1.395 (2)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C16A	1.501 (2)	C14B—C16B	1.500 (2)
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C16A—H16A	0.9600	C16B—H16D	0.9600
C16A—H16B	0.9600	C16B—H16E	0.9600
C16A—H16C	0.9600	C16B—H16F	0.9600
C17A—C20A	1.531 (2)	C17B—C19B	1.533 (2)
C17A—C18A	1.538 (2)	C17B—C18B	1.534 (2)
C17A—C19A	1.540 (2)	C17B—C20B	1.541 (2)
C18A—H18A	0.9600	C18B—H18D	0.9600
C18A—H18B	0.9600	C18B—H18E	0.9600
C18A—H18C	0.9600	C18B—H18F	0.9600
C19A—H19A	0.9600	C19B—H19D	0.9600
C19A—H19B	0.9600	C19B—H19E	0.9600
C19A—H19C	0.9600	C19B—H19F	0.9600
C20A—H20A	0.9600	C20B—H20D	0.9600
C20A—H20B	0.9600	C20B—H20E	0.9600
C20A—H20C	0.9600	C20B—H20F	0.9600

C7A—N1A—C8A	129.29 (12)	C7B—N1B—C8B	129.01 (12)
C7A—N1A—H1NA	117.7 (14)	C7B—N1B—H1NB	117.4 (13)
C8A—N1A—H1NA	112.9 (14)	C8B—N1B—H1NB	112.9 (13)
C8A—N2A—C9A	121.09 (12)	C8B—N2B—C9B	121.58 (12)
C8A—N2A—H2NA	119.9 (12)	C8B—N2B—H2NB	119.7 (13)
C9A—N2A—H2NA	119.0 (12)	C9B—N2B—H2NB	118.5 (13)
C2A—C1A—C6A	120.68 (14)	C2B—C1B—C6B	120.13 (13)
C2A—C1A—H1AA	119.7	C2B—C1B—H1BA	119.9
C6A—C1A—H1AA	119.7	C6B—C1B—H1BA	119.9
C1A—C2A—C3A	121.60 (14)	C1B—C2B—C3B	121.75 (14)
C1A—C2A—H2AA	119.2	C1B—C2B—H2BA	119.1
C3A—C2A—H2AA	119.2	C3B—C2B—H2BA	119.1
C2A—C3A—C4A	117.07 (13)	C4B—C3B—C2B	117.29 (13)
C2A—C3A—C17A	122.80 (13)	C4B—C3B—C17B	122.80 (13)
C4A—C3A—C17A	120.10 (13)	C2B—C3B—C17B	119.90 (13)
C5A—C4A—C3A	121.91 (14)	C5B—C4B—C3B	121.24 (13)
C5A—C4A—H4AA	119.0	C5B—C4B—H4BA	119.4
C3A—C4A—H4AA	119.0	C3B—C4B—H4BA	119.4
C4A—C5A—C6A	120.23 (14)	C6B—C5B—C4B	120.75 (13)
C4A—C5A—H5AA	119.9	C6B—C5B—H5BA	119.6
C6A—C5A—H5AA	119.9	C4B—C5B—H5BA	119.6
C1A—C6A—C5A	118.50 (13)	C5B—C6B—C1B	118.73 (13)
C1A—C6A—C7A	117.18 (13)	C5B—C6B—C7B	122.92 (13)
C5A—C6A—C7A	124.32 (13)	C1B—C6B—C7B	118.29 (13)
O1A—C7A—N1A	122.52 (13)	O1B—C7B—N1B	123.05 (13)
O1A—C7A—C6A	122.06 (13)	O1B—C7B—C6B	121.73 (13)
N1A—C7A—C6A	115.41 (12)	N1B—C7B—C6B	115.23 (12)
N2A—C8A—N1A	116.70 (12)	N2B—C8B—N1B	116.77 (12)
N2A—C8A—S1A	125.15 (11)	N2B—C8B—S1B	124.77 (11)
N1A—C8A—S1A	118.15 (10)	N1B—C8B—S1B	118.46 (10)
C14A—C9A—C10A	122.99 (13)	C14B—C9B—C10B	122.90 (13)
C14A—C9A—N2A	118.55 (12)	C14B—C9B—N2B	118.22 (13)
C10A—C9A—N2A	118.46 (12)	C10B—C9B—N2B	118.88 (12)
C9A—C10A—C11A	117.70 (13)	C11B—C10B—C9B	117.67 (14)
C9A—C10A—C15A	120.56 (13)	C11B—C10B—C15B	121.13 (14)
C11A—C10A—C15A	121.73 (13)	C9B—C10B—C15B	121.17 (13)
C12A—C11A—C10A	120.31 (13)	C12B—C11B—C10B	120.40 (14)
C12A—C11A—H11A	119.8	C12B—C11B—H11B	119.8
C10A—C11A—H11A	119.8	C10B—C11B—H11B	119.8
C11A—C12A—C13A	120.99 (14)	C13B—C12B—C11B	120.81 (14)
C11A—C12A—H12A	119.5	C13B—C12B—H12B	119.6
C13A—C12A—H12A	119.5	C11B—C12B—H12B	119.6
C12A—C13A—C14A	120.10 (14)	C12B—C13B—C14B	120.52 (14)
C12A—C13A—H13A	119.9	C12B—C13B—H13B	119.7
C14A—C13A—H13A	119.9	C14B—C13B—H13B	119.7
C9A—C14A—C13A	117.86 (13)	C9B—C14B—C13B	117.66 (14)
C9A—C14A—C16A	120.66 (13)	C9B—C14B—C16B	120.58 (13)
C13A—C14A—C16A	121.47 (13)	C13B—C14B—C16B	121.76 (14)
C10A—C15A—H15A	109.5	C10B—C15B—H15D	109.5
C10A—C15A—H15B	109.5	C10B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C10A—C15A—H15C	109.5	C10B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C14A—C16A—H16A	109.5	C14B—C16B—H16D	109.5
C14A—C16A—H16B	109.5	C14B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C14A—C16A—H16C	109.5	C14B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
C20A—C17A—C3A	112.14 (13)	C19B—C17B—C18B	107.82 (13)
C20A—C17A—C18A	108.56 (14)	C19B—C17B—C3B	111.90 (12)
C3A—C17A—C18A	108.12 (13)	C18B—C17B—C3B	109.13 (12)
C20A—C17A—C19A	107.93 (13)	C19B—C17B—C20B	108.92 (12)
C3A—C17A—C19A	110.09 (12)	C18B—C17B—C20B	109.14 (13)
C18A—C17A—C19A	109.98 (13)	C3B—C17B—C20B	109.88 (12)
C17A—C18A—H18A	109.5	C17B—C18B—H18D	109.5
C17A—C18A—H18B	109.5	C17B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
C17A—C18A—H18C	109.5	C17B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
C17A—C19A—H19A	109.5	C17B—C19B—H19D	109.5
C17A—C19A—H19B	109.5	C17B—C19B—H19E	109.5
H19A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
C17A—C19A—H19C	109.5	C17B—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19B—C19A—H19C	109.5	H19E—C19B—H19F	109.5
C17A—C20A—H20A	109.5	C17B—C20B—H20D	109.5
C17A—C20A—H20B	109.5	C17B—C20B—H20E	109.5
H20A—C20A—H20B	109.5	H20D—C20B—H20E	109.5
C17A—C20A—H20C	109.5	C17B—C20B—H20F	109.5
H20A—C20A—H20C	109.5	H20D—C20B—H20F	109.5
H20B—C20A—H20C	109.5	H20E—C20B—H20F	109.5

C6A—C1A—C2A—C3A	0.6 (2)	C6B—C1B—C2B—C3B	2.4 (2)
C1A—C2A—C3A—C4A	0.1 (2)	C1B—C2B—C3B—C4B	−3.6 (2)
C1A—C2A—C3A—C17A	−177.84 (15)	C1B—C2B—C3B—C17B	175.19 (14)
C2A—C3A—C4A—C5A	−0.4 (2)	C2B—C3B—C4B—C5B	1.7 (2)
C17A—C3A—C4A—C5A	177.56 (15)	C17B—C3B—C4B—C5B	−177.09 (14)
C3A—C4A—C5A—C6A	0.1 (2)	C3B—C4B—C5B—C6B	1.4 (2)
C2A—C1A—C6A—C5A	−0.9 (2)	C4B—C5B—C6B—C1B	−2.7 (2)
C2A—C1A—C6A—C7A	178.83 (14)	C4B—C5B—C6B—C7B	174.29 (14)
C4A—C5A—C6A—C1A	0.6 (2)	C2B—C1B—C6B—C5B	0.8 (2)
C4A—C5A—C6A—C7A	−179.15 (14)	C2B—C1B—C6B—C7B	−176.34 (13)
C8A—N1A—C7A—O1A	−0.8 (2)	C8B—N1B—C7B—O1B	−3.1 (2)
C8A—N1A—C7A—C6A	178.44 (13)	C8B—N1B—C7B—C6B	177.00 (13)
C1A—C6A—C7A—O1A	15.5 (2)	C5B—C6B—C7B—O1B	−149.96 (15)
C5A—C6A—C7A—O1A	−164.77 (15)	C1B—C6B—C7B—O1B	27.0 (2)
C1A—C6A—C7A—N1A	−163.75 (13)	C5B—C6B—C7B—N1B	29.9 (2)
C5A—C6A—C7A—N1A	16.0 (2)	C1B—C6B—C7B—N1B	−153.11 (13)
C9A—N2A—C8A—N1A	−179.51 (12)	C9B—N2B—C8B—N1B	−177.78 (12)
C9A—N2A—C8A—S1A	0.4 (2)	C9B—N2B—C8B—S1B	2.5 (2)
C7A—N1A—C8A—N2A	0.3 (2)	C7B—N1B—C8B—N2B	10.6 (2)
C7A—N1A—C8A—S1A	−179.62 (12)	C7B—N1B—C8B—S1B	−169.63 (12)
C8A—N2A—C9A—C14A	89.39 (16)	C8B—N2B—C9B—C14B	98.87 (16)
C8A—N2A—C9A—C10A	−91.38 (16)	C8B—N2B—C9B—C10B	−82.20 (17)
C14A—C9A—C10A—C11A	−2.2 (2)	C14B—C9B—C10B—C11B	−1.7 (2)
N2A—C9A—C10A—C11A	178.57 (12)	N2B—C9B—C10B—C11B	179.41 (12)
C14A—C9A—C10A—C15A	176.84 (13)	C14B—C9B—C10B—C15B	176.33 (14)
N2A—C9A—C10A—C15A	−2.36 (19)	N2B—C9B—C10B—C15B	−2.5 (2)
C9A—C10A—C11A—C12A	0.6 (2)	C9B—C10B—C11B—C12B	0.1 (2)
C15A—C10A—C11A—C12A	−178.50 (14)	C15B—C10B—C11B—C12B	−177.96 (14)
C10A—C11A—C12A—C13A	1.1 (2)	C10B—C11B—C12B—C13B	1.1 (2)
C11A—C12A—C13A—C14A	−1.1 (2)	C11B—C12B—C13B—C14B	−0.6 (2)
C10A—C9A—C14A—C13A	2.2 (2)	C10B—C9B—C14B—C13B	2.1 (2)
N2A—C9A—C14A—C13A	−178.61 (12)	N2B—C9B—C14B—C13B	−178.98 (12)
C10A—C9A—C14A—C16A	−176.94 (13)	C10B—C9B—C14B—C16B	−177.36 (13)
N2A—C9A—C14A—C16A	2.26 (19)	N2B—C9B—C14B—C16B	1.5 (2)
C12A—C13A—C14A—C9A	−0.5 (2)	C12B—C13B—C14B—C9B	−0.9 (2)
C12A—C13A—C14A—C16A	178.65 (13)	C12B—C13B—C14B—C16B	178.56 (14)
C2A—C3A—C17A—C20A	−10.1 (2)	C4B—C3B—C17B—C19B	4.6 (2)
C4A—C3A—C17A—C20A	172.02 (15)	C2B—C3B—C17B—C19B	−174.13 (14)
C2A—C3A—C17A—C18A	109.54 (17)	C4B—C3B—C17B—C18B	123.81 (15)
C4A—C3A—C17A—C18A	−68.33 (18)	C2B—C3B—C17B—C18B	−54.90 (18)
C2A—C3A—C17A—C19A	−130.29 (15)	C4B—C3B—C17B—C20B	−116.55 (15)
C4A—C3A—C17A—C19A	51.83 (19)	C2B—C3B—C17B—C20B	64.74 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2NA···O1A	0.84 (2)	2.06 (2)	2.6972 (19)	133.1 (16)
N2B—H2NB···O1B	0.84 (2)	2.08 (2)	2.7183 (19)	132.4 (17)
N2A—H2NA···S1B	0.84 (2)	2.715 (17)	3.2598 (12)	124.3 (16)
N2B—H2NB···S1Aⁱ	0.84 (2)	2.780 (19)	3.3044 (12)	121.9 (16)

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄N₂OS
M_r	340.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	19.5893 (2), 8.8118 (1), 23.5034 (2)
β (°)	114.886 (1)
V (Å³)	3680.37 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.41 × 0.22 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.929, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	67130, 10823, 8234
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.120, 1.04
No. of reflections	10823
No. of parameters	459
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.24

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2NA···O1A	0.84 (2)	2.06 (2)	2.6972 (19)	133.1 (16)
N2B—H2NB···O1B	0.84 (2)	2.08 (2)	2.7183 (19)	132.4 (17)
N2A—H2NA···S1B	0.84 (2)	2.715 (17)	3.2598 (12)	124.3 (16)
N2B—H2NB···S1Aⁱ	0.84 (2)	2.780 (19)	3.3044 (12)	121.9 (16)

Symmetry code: (i) x, −y+3/2, z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

§Thomson Reuters ResearcherID: B-3333-2011.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Grant No.1001/PFIZIK/811151 and Universiti Malaysia Terengganu FRGS Research Grant 59166 to conduct this work.

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