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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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, M. S. M., Mutalib, S. F. A., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o982.]); Yusof, Embong et al. (2012a[Yusof, M. S. M., Embong, N. F., Arshad, S. & Razak, I. A. (2012a). Acta Cryst. E68, o1029.],b[Yusof, M. S. M., Embong, N. F., Arshad, S. & Razak, I. A. (2012b). Acta Cryst. E68, o1267.]); Usman et al. (2002[Usman, A., Razak, I. A., Satar, S., Kadir, M. A., Yamin, B. M. & Fun, H.-K. (2002). Acta Cryst. E58, o656-o658.]); Al-abbasi et al. (2010[Al-abbasi, A. A., Tan, S. S. & Kassim, M. B. (2010). Acta Cryst. E66, o3181.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C20H24N2OS

  • Mr = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.929, Tmax = 0.970

  • 67130 measured reflections

  • 10823 independent reflections

  • 8234 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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.

Refinement top

N-bound H atoms were located from a difference map and refined freely [N—H = 0.813 (19)–0.84 (2) Å]. The remaining H atoms were positioned geometrically (C—H = 0.93 or 0.96 Å) and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating group model was applied to the methyl groups.

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
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labels with 30% probability displacement ellipsoids.
[Figure 2] 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
C20H24N2OSF(000) = 1456
Mr = 340.47Dx = 1.229 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9861 reflections
a = 19.5893 (2) Åθ = 2.3–30.0°
b = 8.8118 (1) ŵ = 0.18 mm1
c = 23.5034 (2) ÅT = 100 K
β = 114.886 (1)°Block, yellow
V = 3680.37 (6) Å30.41 × 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 tube8234 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ϕ and ω scansθmax = 30.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 2727
Tmin = 0.929, Tmax = 0.970k = 1212
67130 measured reflectionsl = 3333
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0433P)2 + 2.0471P]
where P = (Fo2 + 2Fc2)/3
10823 reflections(Δ/σ)max = 0.001
459 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C20H24N2OSV = 3680.37 (6) Å3
Mr = 340.47Z = 8
Monoclinic, P21/cMo Kα radiation
a = 19.5893 (2) ŵ = 0.18 mm1
b = 8.8118 (1) ÅT = 100 K
c = 23.5034 (2) Å0.41 × 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)
Tmin = 0.929, Tmax = 0.970Rint = 0.044
67130 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.43 e Å3
10823 reflectionsΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
S1A0.33613 (2)0.71302 (5)0.125254 (16)0.02173 (9)
O1A0.17289 (6)0.71337 (13)0.21821 (5)0.0218 (2)
N1A0.20809 (7)0.71907 (15)0.13716 (6)0.0175 (2)
N2A0.31610 (7)0.70427 (14)0.23058 (5)0.0151 (2)
C1A0.02289 (8)0.77443 (18)0.13710 (7)0.0205 (3)
H1AA0.03820.79070.17980.025*
C2A0.05243 (9)0.79149 (19)0.09627 (7)0.0222 (3)
H2AA0.08670.82000.11220.027*
C3A0.07793 (8)0.76693 (16)0.03200 (7)0.0170 (3)
C4A0.02428 (9)0.72404 (19)0.01032 (7)0.0229 (3)
H4AA0.03970.70620.03230.028*
C5A0.05104 (9)0.70740 (18)0.05048 (7)0.0222 (3)
H5AA0.08540.67890.03460.027*
C6A0.07568 (8)0.73333 (16)0.11479 (6)0.0159 (3)
C7A0.15550 (8)0.72049 (16)0.16165 (6)0.0160 (3)
C8A0.28677 (8)0.71169 (16)0.16839 (6)0.0157 (3)
C9A0.39627 (8)0.69750 (16)0.26710 (6)0.0136 (3)
C10A0.43051 (8)0.55544 (16)0.28225 (6)0.0154 (3)
C11A0.50857 (8)0.55097 (17)0.31649 (7)0.0188 (3)
H11A0.53320.45800.32700.023*
C12A0.54946 (8)0.68438 (18)0.33479 (7)0.0199 (3)
H12A0.60150.67990.35700.024*
C13A0.51391 (8)0.82473 (17)0.32053 (7)0.0182 (3)
H13A0.54210.91320.33380.022*
C14A0.43598 (8)0.83310 (16)0.28633 (6)0.0150 (3)
C15A0.38419 (9)0.41307 (17)0.26297 (7)0.0222 (3)
H15A0.35610.41200.21820.033*
H15B0.35000.41000.28260.033*
H15C0.41680.32630.27570.033*
C16A0.39558 (9)0.98275 (17)0.27133 (7)0.0213 (3)
H16A0.36610.99040.22690.032*
H16B0.43171.06380.28500.032*
H16C0.36320.98980.29250.032*
C17A0.16009 (8)0.79010 (17)0.01444 (7)0.0199 (3)
C18A0.16415 (10)0.9314 (2)0.05418 (8)0.0301 (4)
H18A0.14731.01860.02730.045*
H18B0.21510.94680.08420.045*
H18C0.13250.91690.07570.045*
C19A0.18877 (9)0.65003 (19)0.05713 (7)0.0248 (3)
H19A0.18650.56260.03200.037*
H19B0.15780.63350.07920.037*
H19C0.23990.66670.08680.037*
C20A0.21171 (9)0.8148 (2)0.01879 (8)0.0313 (4)
H20A0.19710.90590.04340.047*
H20B0.20750.72990.04570.047*
H20C0.26280.82400.01190.047*
S1B0.33713 (2)0.71970 (5)0.375613 (16)0.01977 (9)
O1B0.16877 (6)0.80776 (13)0.45954 (5)0.0227 (2)
N1B0.20713 (7)0.73436 (14)0.38416 (6)0.0156 (2)
N2B0.31391 (7)0.76209 (14)0.47819 (5)0.0151 (2)
C1B0.01921 (8)0.84843 (17)0.36482 (7)0.0188 (3)
H1BA0.03350.91780.39760.023*
C2B0.05593 (8)0.83488 (17)0.32340 (7)0.0194 (3)
H2BA0.09110.89850.32800.023*
C3B0.08026 (8)0.72766 (16)0.27467 (7)0.0159 (3)
C4B0.02515 (8)0.64045 (17)0.26716 (7)0.0196 (3)
H4BA0.03930.57030.23460.024*
C5B0.05073 (8)0.65653 (17)0.30748 (7)0.0188 (3)
H5BA0.08650.59870.30090.023*
C6B0.07355 (8)0.75798 (16)0.35734 (7)0.0156 (3)
C7B0.15330 (8)0.76964 (16)0.40537 (7)0.0159 (3)
C8B0.28580 (8)0.74046 (15)0.41641 (6)0.0147 (3)
C9B0.39374 (8)0.77562 (16)0.51574 (6)0.0144 (3)
C10B0.43690 (8)0.64373 (16)0.53508 (6)0.0169 (3)
C11B0.51411 (9)0.66015 (18)0.57088 (7)0.0212 (3)
H11B0.54440.57450.58450.025*
C12B0.54591 (9)0.80337 (19)0.58635 (7)0.0231 (3)
H12B0.59760.81290.60970.028*
C13B0.50172 (9)0.93235 (18)0.56754 (7)0.0212 (3)
H13B0.52391.02760.57860.025*
C14B0.42422 (8)0.92070 (16)0.53205 (6)0.0168 (3)
C15B0.40121 (9)0.48993 (17)0.51972 (7)0.0230 (3)
H15D0.43960.41340.53450.035*
H15E0.37340.48070.47510.035*
H15F0.36780.47720.53970.035*
C16B0.37459 (9)1.05825 (18)0.51222 (7)0.0240 (3)
H16D0.34531.05600.46760.036*
H16E0.40511.14810.52340.036*
H16F0.34151.05870.53290.036*
C17B0.16468 (8)0.70816 (17)0.23318 (7)0.0178 (3)
C18B0.20564 (9)0.6758 (2)0.27498 (8)0.0258 (3)
H18D0.18540.58550.29910.039*
H18E0.25830.66170.24920.039*
H18F0.19890.75990.30280.039*
C19B0.18011 (9)0.57519 (18)0.18737 (7)0.0244 (3)
H19D0.16090.48320.21050.037*
H19E0.15570.59350.16010.037*
H19F0.23340.56550.16280.037*
C20B0.19667 (9)0.85460 (18)0.19550 (7)0.0218 (3)
H20D0.24960.84230.17020.033*
H20E0.17160.87480.16890.033*
H20F0.18880.93790.22390.033*
H2NA0.2879 (10)0.707 (2)0.2491 (8)0.022 (5)*
H2NB0.2845 (11)0.776 (2)0.4955 (9)0.031 (5)*
H1NB0.1927 (11)0.720 (2)0.3461 (9)0.027 (5)*
H1NA0.1930 (11)0.727 (2)0.0994 (9)0.030 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.01282 (18)0.0403 (2)0.01273 (16)0.00115 (15)0.00602 (14)0.00031 (14)
O1A0.0139 (5)0.0350 (6)0.0162 (5)0.0015 (4)0.0062 (4)0.0028 (4)
N1A0.0114 (6)0.0274 (6)0.0124 (5)0.0003 (5)0.0036 (5)0.0013 (5)
N2A0.0121 (6)0.0216 (6)0.0130 (5)0.0010 (5)0.0069 (5)0.0005 (4)
C1A0.0135 (7)0.0320 (8)0.0155 (6)0.0011 (6)0.0056 (6)0.0001 (6)
C2A0.0149 (7)0.0319 (8)0.0213 (7)0.0031 (6)0.0092 (6)0.0011 (6)
C3A0.0132 (7)0.0184 (7)0.0184 (7)0.0003 (5)0.0055 (6)0.0018 (5)
C4A0.0150 (8)0.0355 (9)0.0172 (7)0.0002 (6)0.0056 (6)0.0033 (6)
C5A0.0157 (7)0.0317 (8)0.0203 (7)0.0011 (6)0.0088 (6)0.0039 (6)
C6A0.0117 (7)0.0180 (6)0.0166 (6)0.0001 (5)0.0046 (5)0.0016 (5)
C7A0.0141 (7)0.0162 (6)0.0173 (6)0.0007 (5)0.0063 (5)0.0013 (5)
C8A0.0125 (7)0.0182 (6)0.0156 (6)0.0005 (5)0.0051 (5)0.0002 (5)
C9A0.0107 (6)0.0195 (7)0.0109 (6)0.0013 (5)0.0048 (5)0.0009 (5)
C10A0.0161 (7)0.0170 (6)0.0150 (6)0.0009 (5)0.0086 (5)0.0011 (5)
C11A0.0166 (7)0.0222 (7)0.0185 (7)0.0069 (5)0.0083 (6)0.0053 (5)
C12A0.0113 (7)0.0308 (8)0.0158 (6)0.0023 (6)0.0041 (5)0.0022 (5)
C13A0.0154 (7)0.0230 (7)0.0166 (6)0.0034 (5)0.0071 (6)0.0015 (5)
C14A0.0149 (7)0.0173 (6)0.0137 (6)0.0012 (5)0.0069 (5)0.0001 (5)
C15A0.0235 (8)0.0179 (7)0.0267 (8)0.0016 (6)0.0119 (7)0.0002 (6)
C16A0.0227 (8)0.0182 (7)0.0236 (7)0.0037 (6)0.0105 (6)0.0017 (5)
C17A0.0116 (7)0.0243 (7)0.0204 (7)0.0030 (5)0.0034 (6)0.0032 (6)
C18A0.0241 (9)0.0289 (9)0.0285 (8)0.0018 (7)0.0025 (7)0.0081 (7)
C19A0.0150 (7)0.0289 (8)0.0250 (8)0.0023 (6)0.0030 (6)0.0007 (6)
C20A0.0121 (8)0.0489 (11)0.0294 (8)0.0061 (7)0.0055 (7)0.0008 (7)
S1B0.01337 (18)0.0342 (2)0.01263 (15)0.00004 (14)0.00637 (14)0.00061 (14)
O1B0.0147 (5)0.0346 (6)0.0181 (5)0.0001 (4)0.0063 (4)0.0059 (4)
N1B0.0102 (6)0.0230 (6)0.0125 (5)0.0005 (4)0.0037 (5)0.0006 (4)
N2B0.0110 (6)0.0221 (6)0.0131 (5)0.0007 (4)0.0059 (5)0.0011 (4)
C1B0.0145 (7)0.0207 (7)0.0201 (7)0.0021 (5)0.0064 (6)0.0059 (5)
C2B0.0138 (7)0.0204 (7)0.0242 (7)0.0005 (5)0.0082 (6)0.0055 (6)
C3B0.0116 (7)0.0167 (6)0.0181 (6)0.0018 (5)0.0050 (5)0.0007 (5)
C4B0.0162 (7)0.0214 (7)0.0197 (7)0.0008 (5)0.0061 (6)0.0058 (5)
C5B0.0132 (7)0.0215 (7)0.0206 (7)0.0029 (5)0.0060 (6)0.0031 (5)
C6B0.0116 (7)0.0173 (6)0.0181 (6)0.0005 (5)0.0063 (5)0.0006 (5)
C7B0.0116 (7)0.0173 (6)0.0185 (6)0.0002 (5)0.0059 (5)0.0001 (5)
C8B0.0115 (7)0.0164 (6)0.0157 (6)0.0000 (5)0.0054 (5)0.0013 (5)
C9B0.0114 (7)0.0219 (7)0.0110 (6)0.0014 (5)0.0057 (5)0.0005 (5)
C10B0.0169 (7)0.0209 (7)0.0137 (6)0.0009 (5)0.0073 (5)0.0003 (5)
C11B0.0163 (7)0.0300 (8)0.0177 (7)0.0044 (6)0.0076 (6)0.0040 (6)
C12B0.0122 (7)0.0390 (9)0.0167 (7)0.0034 (6)0.0048 (6)0.0011 (6)
C13B0.0190 (8)0.0286 (8)0.0171 (7)0.0086 (6)0.0086 (6)0.0036 (6)
C14B0.0159 (7)0.0218 (7)0.0145 (6)0.0020 (5)0.0083 (5)0.0013 (5)
C15B0.0248 (8)0.0207 (7)0.0217 (7)0.0001 (6)0.0079 (6)0.0005 (6)
C16B0.0253 (8)0.0218 (7)0.0256 (8)0.0003 (6)0.0114 (7)0.0004 (6)
C17B0.0123 (7)0.0196 (7)0.0190 (6)0.0025 (5)0.0041 (5)0.0026 (5)
C18B0.0164 (8)0.0352 (9)0.0252 (8)0.0066 (6)0.0081 (6)0.0002 (6)
C19B0.0177 (8)0.0244 (8)0.0249 (8)0.0022 (6)0.0028 (6)0.0061 (6)
C20B0.0152 (7)0.0241 (7)0.0230 (7)0.0003 (6)0.0051 (6)0.0005 (6)
Geometric parameters (Å, º) top
S1A—C8A1.6697 (15)S1B—C8B1.6659 (15)
O1A—C7A1.2273 (17)O1B—C7B1.2249 (17)
N1A—C7A1.3754 (19)N1B—C7B1.3784 (19)
N1A—C8A1.4021 (18)N1B—C8B1.4033 (18)
N1A—H1NA0.813 (19)N1B—H1NB0.826 (19)
N2A—C8A1.3282 (17)N2B—C8B1.3323 (17)
N2A—C9A1.4396 (18)N2B—C9B1.4412 (18)
N2A—H2NA0.836 (19)N2B—H2NB0.84 (2)
C1A—C2A1.389 (2)C1B—C2B1.387 (2)
C1A—C6A1.390 (2)C1B—C6B1.399 (2)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.394 (2)C2B—C3B1.4043 (19)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.399 (2)C3B—C4B1.395 (2)
C3A—C17A1.531 (2)C3B—C17B1.5356 (19)
C4A—C5A1.385 (2)C4B—C5B1.394 (2)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.399 (2)C5B—C6B1.3898 (19)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.4905 (19)C6B—C7B1.4970 (19)
C9A—C14A1.3933 (19)C9B—C14B1.395 (2)
C9A—C10A1.3938 (19)C9B—C10B1.396 (2)
C10A—C11A1.397 (2)C10B—C11B1.395 (2)
C10A—C15A1.502 (2)C10B—C15B1.498 (2)
C11A—C12A1.385 (2)C11B—C12B1.387 (2)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.389 (2)C12B—C13B1.384 (2)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.396 (2)C13B—C14B1.395 (2)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C16A1.501 (2)C14B—C16B1.500 (2)
C15A—H15A0.9600C15B—H15D0.9600
C15A—H15B0.9600C15B—H15E0.9600
C15A—H15C0.9600C15B—H15F0.9600
C16A—H16A0.9600C16B—H16D0.9600
C16A—H16B0.9600C16B—H16E0.9600
C16A—H16C0.9600C16B—H16F0.9600
C17A—C20A1.531 (2)C17B—C19B1.533 (2)
C17A—C18A1.538 (2)C17B—C18B1.534 (2)
C17A—C19A1.540 (2)C17B—C20B1.541 (2)
C18A—H18A0.9600C18B—H18D0.9600
C18A—H18B0.9600C18B—H18E0.9600
C18A—H18C0.9600C18B—H18F0.9600
C19A—H19A0.9600C19B—H19D0.9600
C19A—H19B0.9600C19B—H19E0.9600
C19A—H19C0.9600C19B—H19F0.9600
C20A—H20A0.9600C20B—H20D0.9600
C20A—H20B0.9600C20B—H20E0.9600
C20A—H20C0.9600C20B—H20F0.9600
C7A—N1A—C8A129.29 (12)C7B—N1B—C8B129.01 (12)
C7A—N1A—H1NA117.7 (14)C7B—N1B—H1NB117.4 (13)
C8A—N1A—H1NA112.9 (14)C8B—N1B—H1NB112.9 (13)
C8A—N2A—C9A121.09 (12)C8B—N2B—C9B121.58 (12)
C8A—N2A—H2NA119.9 (12)C8B—N2B—H2NB119.7 (13)
C9A—N2A—H2NA119.0 (12)C9B—N2B—H2NB118.5 (13)
C2A—C1A—C6A120.68 (14)C2B—C1B—C6B120.13 (13)
C2A—C1A—H1AA119.7C2B—C1B—H1BA119.9
C6A—C1A—H1AA119.7C6B—C1B—H1BA119.9
C1A—C2A—C3A121.60 (14)C1B—C2B—C3B121.75 (14)
C1A—C2A—H2AA119.2C1B—C2B—H2BA119.1
C3A—C2A—H2AA119.2C3B—C2B—H2BA119.1
C2A—C3A—C4A117.07 (13)C4B—C3B—C2B117.29 (13)
C2A—C3A—C17A122.80 (13)C4B—C3B—C17B122.80 (13)
C4A—C3A—C17A120.10 (13)C2B—C3B—C17B119.90 (13)
C5A—C4A—C3A121.91 (14)C5B—C4B—C3B121.24 (13)
C5A—C4A—H4AA119.0C5B—C4B—H4BA119.4
C3A—C4A—H4AA119.0C3B—C4B—H4BA119.4
C4A—C5A—C6A120.23 (14)C6B—C5B—C4B120.75 (13)
C4A—C5A—H5AA119.9C6B—C5B—H5BA119.6
C6A—C5A—H5AA119.9C4B—C5B—H5BA119.6
C1A—C6A—C5A118.50 (13)C5B—C6B—C1B118.73 (13)
C1A—C6A—C7A117.18 (13)C5B—C6B—C7B122.92 (13)
C5A—C6A—C7A124.32 (13)C1B—C6B—C7B118.29 (13)
O1A—C7A—N1A122.52 (13)O1B—C7B—N1B123.05 (13)
O1A—C7A—C6A122.06 (13)O1B—C7B—C6B121.73 (13)
N1A—C7A—C6A115.41 (12)N1B—C7B—C6B115.23 (12)
N2A—C8A—N1A116.70 (12)N2B—C8B—N1B116.77 (12)
N2A—C8A—S1A125.15 (11)N2B—C8B—S1B124.77 (11)
N1A—C8A—S1A118.15 (10)N1B—C8B—S1B118.46 (10)
C14A—C9A—C10A122.99 (13)C14B—C9B—C10B122.90 (13)
C14A—C9A—N2A118.55 (12)C14B—C9B—N2B118.22 (13)
C10A—C9A—N2A118.46 (12)C10B—C9B—N2B118.88 (12)
C9A—C10A—C11A117.70 (13)C11B—C10B—C9B117.67 (14)
C9A—C10A—C15A120.56 (13)C11B—C10B—C15B121.13 (14)
C11A—C10A—C15A121.73 (13)C9B—C10B—C15B121.17 (13)
C12A—C11A—C10A120.31 (13)C12B—C11B—C10B120.40 (14)
C12A—C11A—H11A119.8C12B—C11B—H11B119.8
C10A—C11A—H11A119.8C10B—C11B—H11B119.8
C11A—C12A—C13A120.99 (14)C13B—C12B—C11B120.81 (14)
C11A—C12A—H12A119.5C13B—C12B—H12B119.6
C13A—C12A—H12A119.5C11B—C12B—H12B119.6
C12A—C13A—C14A120.10 (14)C12B—C13B—C14B120.52 (14)
C12A—C13A—H13A119.9C12B—C13B—H13B119.7
C14A—C13A—H13A119.9C14B—C13B—H13B119.7
C9A—C14A—C13A117.86 (13)C9B—C14B—C13B117.66 (14)
C9A—C14A—C16A120.66 (13)C9B—C14B—C16B120.58 (13)
C13A—C14A—C16A121.47 (13)C13B—C14B—C16B121.76 (14)
C10A—C15A—H15A109.5C10B—C15B—H15D109.5
C10A—C15A—H15B109.5C10B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
C10A—C15A—H15C109.5C10B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
C14A—C16A—H16A109.5C14B—C16B—H16D109.5
C14A—C16A—H16B109.5C14B—C16B—H16E109.5
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
C14A—C16A—H16C109.5C14B—C16B—H16F109.5
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
C20A—C17A—C3A112.14 (13)C19B—C17B—C18B107.82 (13)
C20A—C17A—C18A108.56 (14)C19B—C17B—C3B111.90 (12)
C3A—C17A—C18A108.12 (13)C18B—C17B—C3B109.13 (12)
C20A—C17A—C19A107.93 (13)C19B—C17B—C20B108.92 (12)
C3A—C17A—C19A110.09 (12)C18B—C17B—C20B109.14 (13)
C18A—C17A—C19A109.98 (13)C3B—C17B—C20B109.88 (12)
C17A—C18A—H18A109.5C17B—C18B—H18D109.5
C17A—C18A—H18B109.5C17B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C17A—C18A—H18C109.5C17B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C17A—C19A—H19A109.5C17B—C19B—H19D109.5
C17A—C19A—H19B109.5C17B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C17A—C19A—H19C109.5C17B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
C17A—C20A—H20A109.5C17B—C20B—H20D109.5
C17A—C20A—H20B109.5C17B—C20B—H20E109.5
H20A—C20A—H20B109.5H20D—C20B—H20E109.5
C17A—C20A—H20C109.5C17B—C20B—H20F109.5
H20A—C20A—H20C109.5H20D—C20B—H20F109.5
H20B—C20A—H20C109.5H20E—C20B—H20F109.5
C6A—C1A—C2A—C3A0.6 (2)C6B—C1B—C2B—C3B2.4 (2)
C1A—C2A—C3A—C4A0.1 (2)C1B—C2B—C3B—C4B3.6 (2)
C1A—C2A—C3A—C17A177.84 (15)C1B—C2B—C3B—C17B175.19 (14)
C2A—C3A—C4A—C5A0.4 (2)C2B—C3B—C4B—C5B1.7 (2)
C17A—C3A—C4A—C5A177.56 (15)C17B—C3B—C4B—C5B177.09 (14)
C3A—C4A—C5A—C6A0.1 (2)C3B—C4B—C5B—C6B1.4 (2)
C2A—C1A—C6A—C5A0.9 (2)C4B—C5B—C6B—C1B2.7 (2)
C2A—C1A—C6A—C7A178.83 (14)C4B—C5B—C6B—C7B174.29 (14)
C4A—C5A—C6A—C1A0.6 (2)C2B—C1B—C6B—C5B0.8 (2)
C4A—C5A—C6A—C7A179.15 (14)C2B—C1B—C6B—C7B176.34 (13)
C8A—N1A—C7A—O1A0.8 (2)C8B—N1B—C7B—O1B3.1 (2)
C8A—N1A—C7A—C6A178.44 (13)C8B—N1B—C7B—C6B177.00 (13)
C1A—C6A—C7A—O1A15.5 (2)C5B—C6B—C7B—O1B149.96 (15)
C5A—C6A—C7A—O1A164.77 (15)C1B—C6B—C7B—O1B27.0 (2)
C1A—C6A—C7A—N1A163.75 (13)C5B—C6B—C7B—N1B29.9 (2)
C5A—C6A—C7A—N1A16.0 (2)C1B—C6B—C7B—N1B153.11 (13)
C9A—N2A—C8A—N1A179.51 (12)C9B—N2B—C8B—N1B177.78 (12)
C9A—N2A—C8A—S1A0.4 (2)C9B—N2B—C8B—S1B2.5 (2)
C7A—N1A—C8A—N2A0.3 (2)C7B—N1B—C8B—N2B10.6 (2)
C7A—N1A—C8A—S1A179.62 (12)C7B—N1B—C8B—S1B169.63 (12)
C8A—N2A—C9A—C14A89.39 (16)C8B—N2B—C9B—C14B98.87 (16)
C8A—N2A—C9A—C10A91.38 (16)C8B—N2B—C9B—C10B82.20 (17)
C14A—C9A—C10A—C11A2.2 (2)C14B—C9B—C10B—C11B1.7 (2)
N2A—C9A—C10A—C11A178.57 (12)N2B—C9B—C10B—C11B179.41 (12)
C14A—C9A—C10A—C15A176.84 (13)C14B—C9B—C10B—C15B176.33 (14)
N2A—C9A—C10A—C15A2.36 (19)N2B—C9B—C10B—C15B2.5 (2)
C9A—C10A—C11A—C12A0.6 (2)C9B—C10B—C11B—C12B0.1 (2)
C15A—C10A—C11A—C12A178.50 (14)C15B—C10B—C11B—C12B177.96 (14)
C10A—C11A—C12A—C13A1.1 (2)C10B—C11B—C12B—C13B1.1 (2)
C11A—C12A—C13A—C14A1.1 (2)C11B—C12B—C13B—C14B0.6 (2)
C10A—C9A—C14A—C13A2.2 (2)C10B—C9B—C14B—C13B2.1 (2)
N2A—C9A—C14A—C13A178.61 (12)N2B—C9B—C14B—C13B178.98 (12)
C10A—C9A—C14A—C16A176.94 (13)C10B—C9B—C14B—C16B177.36 (13)
N2A—C9A—C14A—C16A2.26 (19)N2B—C9B—C14B—C16B1.5 (2)
C12A—C13A—C14A—C9A0.5 (2)C12B—C13B—C14B—C9B0.9 (2)
C12A—C13A—C14A—C16A178.65 (13)C12B—C13B—C14B—C16B178.56 (14)
C2A—C3A—C17A—C20A10.1 (2)C4B—C3B—C17B—C19B4.6 (2)
C4A—C3A—C17A—C20A172.02 (15)C2B—C3B—C17B—C19B174.13 (14)
C2A—C3A—C17A—C18A109.54 (17)C4B—C3B—C17B—C18B123.81 (15)
C4A—C3A—C17A—C18A68.33 (18)C2B—C3B—C17B—C18B54.90 (18)
C2A—C3A—C17A—C19A130.29 (15)C4B—C3B—C17B—C20B116.55 (15)
C4A—C3A—C17A—C19A51.83 (19)C2B—C3B—C17B—C20B64.74 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2NA···O1A0.84 (2)2.06 (2)2.6972 (19)133.1 (16)
N2B—H2NB···O1B0.84 (2)2.08 (2)2.7183 (19)132.4 (17)
N2A—H2NA···S1B0.84 (2)2.715 (17)3.2598 (12)124.3 (16)
N2B—H2NB···S1Ai0.84 (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 formulaC20H24N2OS
Mr340.47
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)19.5893 (2), 8.8118 (1), 23.5034 (2)
β (°) 114.886 (1)
V3)3680.37 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.41 × 0.22 × 0.17
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.929, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
67130, 10823, 8234
Rint0.044
(sin θ/λ)max1)0.706
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.120, 1.04
No. of reflections10823
No. of parameters459
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N2A—H2NA···O1A0.84 (2)2.06 (2)2.6972 (19)133.1 (16)
N2B—H2NB···O1B0.84 (2)2.08 (2)2.7183 (19)132.4 (17)
N2A—H2NA···S1B0.84 (2)2.715 (17)3.2598 (12)124.3 (16)
N2B—H2NB···S1Ai0.84 (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.

References

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