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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 4| April 2015| Pages o225-o226
doi:10.1107/S2056989015003813

Crystal structure of 4-meth­­oxy-N-[(pyrrolidin-1-yl)carbo­thio­yl]benzamide

CROSSMARK_Color_square_no_text.svg
Khairi Suhud,a,b Lee Yook Heng,a Siti Aishah Hasbullah,a Musa Ahmadc and Mohammad B. Kassima,d*

aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Selangor, Malaysia, bDepartment of Chemistry, Mathematics & Natural Science Faculty, Universitas Syiah Kuala, Banda Aceh, 23111, Indonesia, cChemical Technology Program, Faculty of Science Technology, Universiti Sains Islam Malaysia, Bandar Baru Nilai, 71800 Nilai, Negeri Sembilan, Malaysia, and dFuel Cell Institute, Universiti Kebangsaan Malaysia, 43600 Selangor, Malaysia
*Correspondence e-mail: mb_kassim@ukm.edu.my

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 10 February 2015; accepted 24 February 2015; online 4 March 2015)

In the title compound, C13H16N2O2S, the pyrrolidine ring has a twisted conformation on the central –CH2–CH2– bond. Its mean plane is inclined to the 4-meth­oxy­benzoyl ring by 72.79 (15)°. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds to the same O-atom acceptor, forming chains along [001]. The chains are linked via slipped parallel π–π inter­actions [inter-centroid distance = 3.7578 (13) Å], forming undulating slabs parallel to (100).

CCDC reference: 1051012

Similar articles

1. Related literature

For thio­urea derivatives containing a carbono­thioyl R–C(=O)—N(H)—C(=S)—N functional group, where R is an alkyl or aryl group, see: Arslan et al. (2006[Arslan, H., Florke, U., Kulcu, N. & Kayhan, E. (2006). Turk. J. Chem. 30, 429-440.]). For copper(II) complexes of similar compounds, see: Kulcu et al. (2005[Kulcu, N., Florke, U. & Arslan, H. (2005). Turk. J. Chem. 29, 1-6.]); Tan et al. (2014[Tan, S. S., Al-abbasi, A. A., Mohamed Tahir, M. I. & Kassim, M. B. (2014). Polyhedron, 68, 287-294.]). For the biological properties of coordination complexes of such compounds, see: Rodríguez-Fernandez et al. (2005[Rodríguez-Fernández, E., Manzano, J. L., Benito, J. J., Hermosa, R., Monte, E. & Criado, J. J. (2005). J. Inorg. Biochem. 99, 1558-1572.]); Cikla et al. (2010[Cikla, P., Kucukguzel, S. G., Kucukguzel, I., Rollas, S., Clercq, E. D., Pannecouque, C., Andrei, G., Snoeck, R., Sahin, F. & Bayrak, O. F. (2010). Pharm. J. 14, 13-20.]). For the crystal structures of similar compounds, see: Al-abbasi et al. (2011[Al-abbasi, A. A., Mohamed Tahir, M. I. & Kassim, M. B. (2011). Acta Cryst. E67, o3414.], 2012[Al-abbasi, A. A., Mohamed Tahir, M. I. & Kassim, M. B. (2012). Acta Cryst. E68, o201.]); Md Nasir et al. (2011[Md Nasir, M. F., Hassan, I. N., Yamin, B. M., Daud, W. R. W. & Kassim, M. B. (2011). Acta Cryst. E67, o1947-o1948.]); Hassan et al. (2008[Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2008). Acta Cryst. E64, o2083.], 2009[Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2009). Acta Cryst. E65, o3078.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C13H16N2O2S

  • Mr = 264.34

  • Monoclinic, P 21 /c

  • a = 11.8548 (12) Å

  • b = 11.4463 (11) Å

  • c = 9.8317 (9) Å

  • β = 93.124 (3)°

  • V = 1332.1 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 296 K

  • 0.50 × 0.41 × 0.15 mm

2.2. Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.890, Tmax = 0.965

  • 17732 measured reflections

  • 2763 independent reflections

  • 2140 reflections with I > 2σ(I)

  • Rint = 0.043

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.130

  • S = 1.07

  • 2763 reflections

  • 169 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O1i 0.83 (3) 2.11 (3) 2.927 (2) 170 (2)
C1—H1⋯O1i 0.93 2.50 3.350 (3) 152
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1051012

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015003813/su5083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015003813/su5083Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015003813/su5083Isup3.cml

checkCIF report


Synthesis and crystallization top

Benzoyl chloride (0.01 mol) was slowly added to ammonium thio­cyanate (0.01 mol) in acetone and the mixture was stirred for 30 min at room temperature. A white precipitate of ammonium chloride was filtered off. The filtrate was cooled in an ice bath (278-283 K) for about 15 min. Then, a cold solution (5-10°C) of pyrrolidine (0.01 mol) in acetone was added to the benzoyl iso­thio­cyanate and the mixture was left for 3 h at room temperature. A yellowish solution was formed and the mixture was filtered into a beaker containing some ice cubes. The yellow residue was washed with cold water followed pale-yellow block-like crystals (yield: 85%; m.p. 397-399 K). IR(KBr, cm-1) ν(-NH) 3389; (O—CH3) = 2967; ν(C═Oaliphatic) = 1716, ν(C—Cbenzene) = 1651 and 1424; ν(C═Ostretching) = 1311 and ν(C═S) = 1210 cm-1.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 3. The NH H atom, H1A, was located in a difference Fourier map and freely refined. The C-bound H atoms were included in calculated positions and treated as riding atoms: C–H = 0.93 – 0.97 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms.

Comment top

The title compound, is a derivative of a thiourea compound containing a carbonothioyl R–C(═O)—N(H)—C(═S)—N functional group (Arslan et al., 2006), where R can be either alkyl or aryl group. The C═O and C═S groups can serve as coordination sites upon reaction with metal ions. Such complexes have been found to be biologically active, for example anti-bacterial, anti-fungal (Rodríguez-Fernandez et al., 2005), and anti-cancer (Cikla et al., 2010). The title compound is similar to the previously reported derivatives namely 1,1-diethyl-3-(4-methoxybenzoyl)thiourea (Al-abbasi et al., 2011) and 3-(3-methoxybenzoyl)-1,1-diphenylthiourea (Md Nasir et al., 2011).

Reaction of these organic compounds cis-bis[4-chloro-N-(pyrrolidine-1-carbothioyl)-benzamido] with Cu(II) formed a stable complex compound with a 1:2 ratio. The complex was tested for anti-bacterial activity (Kulcu et al., 2005). Similarly, a 1:3 ratio between copper(II)acetate and 1-benzoyl-(3,3-disubstituted)thiourea derivatives gave a series of copper(III) complexes in which the 1-benzoyl-(3,3-disubstituted)thiourea derivatives were deprotonated prior to the complexation reaction. Hence, 1-benzoyl-(3,3-disubstituted)thiourea derivatives behaved as a bidentate chelate through (O,S) coordination to give neutral cobalt(III) complexes (Tan et al., 2014).Herein we report on the crystal structure of the title compound (MPCB), and compare it to previously reported carbonyl thioureas.

In the title compound, Fig. 1, the 4-methoxybenzoyl and pyrrolidine fragments adopting a trans-cis conformation with respect to the thiono S atom across the C8—N1 bond. The pyrolidine ring (N2/C2-C9) has a twisted conformation on the C10-C11 bond. The benzamide fragment (C1-C7/O1/N1) is approximately planar with a maximum deviation for atom O1 [0.045 (2)°], and it is twisted with respect to the thiourea fragment (S1/N1/N2/C8/C12) [maximum deviation of -0.034 (2)° for N2] with a dihedral angle of 61.81 (7)°.

The C═O [1.220 (2) Å] and C=S [1.662 (2) Å] bond lengths are comparable to those reported for propyl 2-(3-benzoylthioureido)acetate [1.220 (3) Å, 1.658 (3) Å, respectively] (Hassan et al., 2008) and methyl 2-(3-benzoylthioureido)acetate [1.223 (5) Å, 1.661 (4) Å, respectively] (Hassan et al., 2009). Other bond lengths and angles in the molecule are comparable those reported for N-(pyrrolidin-1-ylcarbothioyl) benzamide (Al-abbasi et al., 2012).

In the crystal, molecules are linked by bifurcated N-H···O and C-H···O hydrogen bond forming chains along the c-axis direction (Table 1 and Fig. 2). Further stabilization is afforded by slipped parallel π-π stacking interactions involving the (C1-C6) benzene ring [Cg1···Cg1i = 3.7578 (13) Å; inter-planar distance = 3.6228 (9) Å; slippage = 0.998 Å; symmetry code: (i) -x,+2, -y+1, -z], forming undulating slabs parallel to (100).

Related literature top

For thiourea derivatives containing a carbonothioyl R–C(═ O)—N(H)—C(═S)—N functional group, where R is an alkyl or aryl group, see: Arslan et al. (2006). For copper(II) complexes of similar compounds, see: Kulcu et al. (2005); Tan et al. (2014). For the biological properties of coordination complexes of such compounds, see: Rodríguez-Fernandez et al. (2005); Cikla et al. (2010). For the crystal structures of similar compounds, see: Al-abbasi et al. (2011, 2012); Md Nasir et al. (2011); Hassan et al. (2008, 2009).

Structure description top

The title compound, is a derivative of a thiourea compound containing a carbonothioyl R–C(═O)—N(H)—C(═S)—N functional group (Arslan et al., 2006), where R can be either alkyl or aryl group. The C═O and C═S groups can serve as coordination sites upon reaction with metal ions. Such complexes have been found to be biologically active, for example anti-bacterial, anti-fungal (Rodríguez-Fernandez et al., 2005), and anti-cancer (Cikla et al., 2010). The title compound is similar to the previously reported derivatives namely 1,1-diethyl-3-(4-methoxybenzoyl)thiourea (Al-abbasi et al., 2011) and 3-(3-methoxybenzoyl)-1,1-diphenylthiourea (Md Nasir et al., 2011).

Reaction of these organic compounds cis-bis[4-chloro-N-(pyrrolidine-1-carbothioyl)-benzamido] with Cu(II) formed a stable complex compound with a 1:2 ratio. The complex was tested for anti-bacterial activity (Kulcu et al., 2005). Similarly, a 1:3 ratio between copper(II)acetate and 1-benzoyl-(3,3-disubstituted)thiourea derivatives gave a series of copper(III) complexes in which the 1-benzoyl-(3,3-disubstituted)thiourea derivatives were deprotonated prior to the complexation reaction. Hence, 1-benzoyl-(3,3-disubstituted)thiourea derivatives behaved as a bidentate chelate through (O,S) coordination to give neutral cobalt(III) complexes (Tan et al., 2014).Herein we report on the crystal structure of the title compound (MPCB), and compare it to previously reported carbonyl thioureas.

In the title compound, Fig. 1, the 4-methoxybenzoyl and pyrrolidine fragments adopting a trans-cis conformation with respect to the thiono S atom across the C8—N1 bond. The pyrolidine ring (N2/C2-C9) has a twisted conformation on the C10-C11 bond. The benzamide fragment (C1-C7/O1/N1) is approximately planar with a maximum deviation for atom O1 [0.045 (2)°], and it is twisted with respect to the thiourea fragment (S1/N1/N2/C8/C12) [maximum deviation of -0.034 (2)° for N2] with a dihedral angle of 61.81 (7)°.

The C═O [1.220 (2) Å] and C=S [1.662 (2) Å] bond lengths are comparable to those reported for propyl 2-(3-benzoylthioureido)acetate [1.220 (3) Å, 1.658 (3) Å, respectively] (Hassan et al., 2008) and methyl 2-(3-benzoylthioureido)acetate [1.223 (5) Å, 1.661 (4) Å, respectively] (Hassan et al., 2009). Other bond lengths and angles in the molecule are comparable those reported for N-(pyrrolidin-1-ylcarbothioyl) benzamide (Al-abbasi et al., 2012).

In the crystal, molecules are linked by bifurcated N-H···O and C-H···O hydrogen bond forming chains along the c-axis direction (Table 1 and Fig. 2). Further stabilization is afforded by slipped parallel π-π stacking interactions involving the (C1-C6) benzene ring [Cg1···Cg1i = 3.7578 (13) Å; inter-planar distance = 3.6228 (9) Å; slippage = 0.998 Å; symmetry code: (i) -x,+2, -y+1, -z], forming undulating slabs parallel to (100).

For thiourea derivatives containing a carbonothioyl R–C(═ O)—N(H)—C(═S)—N functional group, where R is an alkyl or aryl group, see: Arslan et al. (2006). For copper(II) complexes of similar compounds, see: Kulcu et al. (2005); Tan et al. (2014). For the biological properties of coordination complexes of such compounds, see: Rodríguez-Fernandez et al. (2005); Cikla et al. (2010). For the crystal structures of similar compounds, see: Al-abbasi et al. (2011, 2012); Md Nasir et al. (2011); Hassan et al. (2008, 2009).

Synthesis and crystallization top

Benzoyl chloride (0.01 mol) was slowly added to ammonium thio­cyanate (0.01 mol) in acetone and the mixture was stirred for 30 min at room temperature. A white precipitate of ammonium chloride was filtered off. The filtrate was cooled in an ice bath (278-283 K) for about 15 min. Then, a cold solution (5-10°C) of pyrrolidine (0.01 mol) in acetone was added to the benzoyl iso­thio­cyanate and the mixture was left for 3 h at room temperature. A yellowish solution was formed and the mixture was filtered into a beaker containing some ice cubes. The yellow residue was washed with cold water followed pale-yellow block-like crystals (yield: 85%; m.p. 397-399 K). IR(KBr, cm-1) ν(-NH) 3389; (O—CH3) = 2967; ν(C═Oaliphatic) = 1716, ν(C—Cbenzene) = 1651 and 1424; ν(C═Ostretching) = 1311 and ν(C═S) = 1210 cm-1.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 3. The NH H atom, H1A, was located in a difference Fourier map and freely refined. The C-bound H atoms were included in calculated positions and treated as riding atoms: C–H = 0.93 – 0.97 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view along the x axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).
4-Methoxy-N-[(pyrrolidin-1-yl)carbothioyl]benzamide top
Crystal data top
C13H16N2O2SF(000) = 560
Mr = 264.34Dx = 1.318 Mg m−3
Monoclinic, P21/cMelting point = 397–399 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.8548 (12) Åθ = 3.2–26.5°
b = 11.4463 (11) ŵ = 0.24 mm−1
c = 9.8317 (9) ÅT = 296 K
β = 93.124 (3)°Block, pale-yellow
V = 1332.1 (2) Å30.50 × 0.41 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2763 independent reflections
Radiation source: fine-focus sealed tube2140 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ω scanθmax = 26.5°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		h = −14→14
Tmin = 0.890, Tmax = 0.965k = −14→14
17732 measured reflectionsl = −12→12
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0485P)2 + 1.055P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2763 reflectionsΔρmax = 0.26 e Å−3
169 parametersΔρmin = −0.23 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.031 (3)
Crystal data top
C13H16N2O2SV = 1332.1 (2) Å3
Mr = 264.34Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.8548 (12) ŵ = 0.24 mm−1
b = 11.4463 (11) ÅT = 296 K
c = 9.8317 (9) Å0.50 × 0.41 × 0.15 mm
β = 93.124 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2763 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		2140 reflections with I > 2σ(I)
Tmin = 0.890, Tmax = 0.965Rint = 0.043
17732 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.26 e Å−3
2763 reflectionsΔρmin = −0.23 e Å−3
169 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
xyzUiso*/Ueq
S10.72135 (6)0.00137 (5)0.03914 (6)0.0491 (2)
O10.76464 (14)0.29334 (14)0.26290 (14)0.0456 (4)
O20.93009 (16)0.73574 (15)−0.05668 (17)0.0582 (5)
N10.71420 (15)0.23446 (15)0.04921 (17)0.0345 (4)
N20.58223 (15)0.13540 (14)0.17024 (18)0.0383 (4)
C10.80147 (19)0.45074 (19)−0.0520 (2)0.0386 (5)
H10.76890.3985−0.11510.046*
C20.8420 (2)0.5562 (2)−0.0950 (2)0.0472 (6)
H20.83650.5748−0.18720.057*
C30.89105 (18)0.63501 (18)−0.0028 (2)0.0387 (5)
C40.89724 (19)0.60796 (19)0.1342 (2)0.0421 (5)
H40.92830.66100.19730.051*
C50.85703 (19)0.50171 (18)0.1772 (2)0.0383 (5)
H50.86230.48340.26950.046*
C60.80889 (15)0.42189 (16)0.08530 (18)0.0290 (4)
C70.76284 (16)0.31244 (17)0.14072 (18)0.0310 (4)
C80.66841 (17)0.12705 (17)0.09137 (18)0.0320 (4)
C90.5215 (2)0.2428 (2)0.2040 (3)0.0504 (6)
H9A0.50740.29120.12400.060*
H9B0.56400.28770.27310.060*
C100.4126 (2)0.1985 (3)0.2569 (4)0.0705 (8)
H10A0.35590.18710.18320.085*
H10B0.38350.25210.32290.085*
C110.4468 (3)0.0836 (3)0.3227 (4)0.0747 (9)
H11A0.48200.09590.41290.090*
H11B0.38190.03290.32990.090*
C120.5294 (2)0.0320 (2)0.2289 (3)0.0469 (6)
H12A0.5851−0.01590.27870.056*
H12B0.4910−0.01500.15850.056*
C130.9838 (2)0.8187 (2)0.0323 (3)0.0582 (7)
H13A0.92950.85060.09110.087*
H13B1.01490.8804−0.02020.087*
H13C1.04330.78130.08630.087*
H1A0.734 (2)0.234 (2)−0.030 (3)0.048 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0650 (4)0.0340 (3)0.0487 (4)0.0064 (3)0.0070 (3)−0.0051 (2)
O10.0643 (10)0.0483 (9)0.0242 (7)−0.0124 (8)0.0019 (6)0.0034 (6)
O20.0803 (12)0.0404 (9)0.0530 (10)−0.0216 (9)−0.0036 (9)0.0101 (7)
N10.0480 (10)0.0322 (9)0.0237 (8)−0.0064 (7)0.0070 (7)−0.0009 (7)
N20.0454 (10)0.0273 (8)0.0427 (10)−0.0038 (7)0.0077 (8)0.0025 (7)
C10.0527 (13)0.0360 (11)0.0267 (10)−0.0074 (9)−0.0005 (9)−0.0014 (8)
C20.0712 (16)0.0421 (12)0.0279 (10)−0.0107 (11)−0.0019 (10)0.0062 (9)
C30.0428 (11)0.0319 (10)0.0415 (12)−0.0035 (9)0.0028 (9)0.0038 (9)
C40.0489 (12)0.0407 (12)0.0360 (11)−0.0089 (10)−0.0033 (9)−0.0059 (9)
C50.0473 (12)0.0423 (12)0.0250 (9)−0.0068 (9)−0.0010 (8)−0.0006 (8)
C60.0293 (9)0.0306 (9)0.0271 (9)0.0000 (7)0.0030 (7)0.0001 (7)
C70.0350 (10)0.0332 (10)0.0251 (9)0.0007 (8)0.0039 (7)0.0004 (7)
C80.0405 (11)0.0317 (10)0.0236 (9)−0.0024 (8)−0.0011 (8)−0.0005 (7)
C90.0539 (14)0.0379 (12)0.0614 (15)0.0057 (10)0.0207 (11)0.0027 (11)
C100.0517 (15)0.0604 (17)0.101 (2)0.0007 (13)0.0229 (15)−0.0096 (16)
C110.0720 (19)0.0608 (17)0.095 (2)−0.0163 (15)0.0387 (17)0.0083 (16)
C120.0486 (13)0.0379 (11)0.0543 (14)−0.0136 (10)0.0037 (11)0.0074 (10)
C130.0617 (16)0.0372 (13)0.0752 (18)−0.0113 (11)−0.0010 (13)−0.0021 (12)
Geometric parameters (Å, º) top
S1—C81.662 (2)C5—C61.386 (3)
O1—C71.220 (2)C5—H50.9300
O2—C31.361 (2)C6—C71.482 (3)
O2—C131.418 (3)C9—C101.505 (4)
N1—C71.372 (2)C9—H9A0.9700
N1—C81.415 (2)C9—H9B0.9700
N1—H1A0.83 (3)C10—C111.512 (4)
N2—C81.319 (3)C10—H10A0.9700
N2—C121.471 (3)C10—H10B0.9700
N2—C91.472 (3)C11—C121.502 (4)
C1—C21.375 (3)C11—H11A0.9700
C1—C61.387 (3)C11—H11B0.9700
C1—H10.9300C12—H12A0.9700
C2—C31.384 (3)C12—H12B0.9700
C2—H20.9300C13—H13A0.9600
C3—C41.380 (3)C13—H13B0.9600
C4—C51.381 (3)C13—H13C0.9600
C4—H40.9300
C3—O2—C13118.55 (19)N2—C9—C10103.63 (19)
C7—N1—C8121.83 (16)N2—C9—H9A111.0
C7—N1—H1A119.3 (18)C10—C9—H9A111.0
C8—N1—H1A114.0 (18)N2—C9—H9B111.0
C8—N2—C12122.12 (18)C10—C9—H9B111.0
C8—N2—C9126.67 (17)H9A—C9—H9B109.0
C12—N2—C9111.08 (17)C9—C10—C11103.0 (2)
C2—C1—C6120.23 (19)C9—C10—H10A111.2
C2—C1—H1119.9C11—C10—H10A111.2
C6—C1—H1119.9C9—C10—H10B111.2
C1—C2—C3120.82 (19)C11—C10—H10B111.2
C1—C2—H2119.6H10A—C10—H10B109.1
C3—C2—H2119.6C12—C11—C10104.4 (2)
O2—C3—C4124.7 (2)C12—C11—H11A110.9
O2—C3—C2115.90 (19)C10—C11—H11A110.9
C4—C3—C2119.41 (19)C12—C11—H11B110.9
C3—C4—C5119.72 (19)C10—C11—H11B110.9
C3—C4—H4120.1H11A—C11—H11B108.9
C5—C4—H4120.1N2—C12—C11103.30 (19)
C4—C5—C6121.15 (19)N2—C12—H12A111.1
C4—C5—H5119.4C11—C12—H12A111.1
C6—C5—H5119.4N2—C12—H12B111.1
C5—C6—C1118.65 (18)C11—C12—H12B111.1
C5—C6—C7117.66 (17)H12A—C12—H12B109.1
C1—C6—C7123.61 (17)O2—C13—H13A109.5
O1—C7—N1120.88 (18)O2—C13—H13B109.5
O1—C7—C6121.76 (18)H13A—C13—H13B109.5
N1—C7—C6117.32 (16)O2—C13—H13C109.5
N2—C8—N1115.53 (17)H13A—C13—H13C109.5
N2—C8—S1124.18 (15)H13B—C13—H13C109.5
N1—C8—S1120.28 (15)
C6—C1—C2—C30.2 (4)C5—C6—C7—N1179.28 (18)
C13—O2—C3—C41.7 (4)C1—C6—C7—N12.5 (3)
C13—O2—C3—C2−178.4 (2)C12—N2—C8—N1−176.49 (18)
C1—C2—C3—O2178.9 (2)C9—N2—C8—N18.0 (3)
C1—C2—C3—C4−1.2 (4)C12—N2—C8—S14.8 (3)
O2—C3—C4—C5−178.5 (2)C9—N2—C8—S1−170.72 (18)
C2—C3—C4—C51.5 (3)C7—N1—C8—N263.0 (3)
C3—C4—C5—C6−0.9 (3)C7—N1—C8—S1−118.27 (18)
C4—C5—C6—C1−0.1 (3)C8—N2—C9—C10162.6 (2)
C4—C5—C6—C7−177.08 (19)C12—N2—C9—C10−13.4 (3)
C2—C1—C6—C50.5 (3)N2—C9—C10—C1131.6 (3)
C2—C1—C6—C7177.3 (2)C9—C10—C11—C12−38.8 (3)
C8—N1—C7—O1−2.6 (3)C8—N2—C12—C11173.3 (2)
C8—N1—C7—C6179.56 (17)C9—N2—C12—C11−10.5 (3)
C5—C6—C7—O11.5 (3)C10—C11—C12—N230.2 (3)
C1—C6—C7—O1−175.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.83 (3)2.11 (3)2.927 (2)170 (2)
C1—H1···O1i0.932.503.350 (3)152
Symmetry code: (i) x, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.83 (3)2.11 (3)2.927 (2)170 (2)
C1—H1···O1i0.932.503.350 (3)152
Symmetry code: (i) x, −y+1/2, z−1/2.
 

Acknowledgements

The authors thank the Universiti Kebangsaan Malaysia (UKM) for financial support via research grants DIP-2012-11, DLP-2013-001, DPP-2013-043 and DPP-2014-048, and the Ministry of Education, Malaysia for grant FRGS/1/2014/ST01/UKM/02/2.

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ISSN: 2056-9890
Volume 71| Part 4| April 2015| Pages o225-o226
doi:10.1107/S2056989015003813
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