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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 9| September 2013| Pages o1374-o1375

N,N′-Bis(phenyl­carbamo­thio­yl)benzene-1,3-dicarboxamide

aDepartment of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, bDepartment of Molecular Biology, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: mustaqim@usm.my

(Received 2 July 2013; accepted 22 July 2013; online 3 August 2013)

The asymmetric unit of the title compound, C22H18N4O2S2, contains two mol­ecules. In one of them, the dihedral angles between the central benzene ring and the phenyl rings are 16.97 (8) and 20.97 (8)°, while the phenyl rings make a dihedral angle of 37.87 (8)°. In the other mol­ecule, the corresponding values are 34.92 (7), 53.90 (7) and 60.68 (8)°, respectively. In each mol­ecule, two intra­molecular N—H⋯O hydrogen bonds generate S(6) rings and a short C—H⋯S contact also occurs. In the crystal, N—H⋯S, N—H⋯O, C—H⋯O and C—H⋯S inter­actions link the mol­ecules into a three-dimensional network.

Related literature

For biological applications of benzimidazole derivatives, see: Madan et al. (1991[Madan, V. K., Taneja, A. D. & Kudesia, V. P. (1991). J. Indian Chem. Soc. 68, 471-472.]); Fernandez et al. (2005[Fernandez, E. R., Manzano, J. L., Benito, J. J., Hermosa, R., Monte, E. & Criado, J. J. (2005). J. Inorg. Biochem. 99, 1559-1572.]); Kucukguzel et al. (2008[Kucukguzel, I., Tatar, E., Kucukguzel, S. G., Rollas, S. & Clercq, E. D. (2008). Eur. J. Med. Chem. 43, 381-392.]); Saeed et al. (2009[Saeed, A., Abbas, N., Rafique, H., Rashid, S. & Hameed, A. (2009). Chemistry, 18, 152-158.]). For biological properties of thioureas, see: Rauf et al. (2009[Rauf, M. K., Din, I. U., Badshah, A., Geilen, M., Ebihara, M., Vos, D. & Ahmed, S. (2009). J. Inorg. Biochem. 103, 1135-1144.]).

[Scheme 1]

Experimental

Crystal data
  • C22H18N4O2S2

  • Mr = 434.52

  • Triclinic, [P \overline 1]

  • a = 11.1812 (2) Å

  • b = 11.5623 (2) Å

  • c = 16.4471 (2) Å

  • α = 101.420 (1)°

  • β = 98.127 (1)°

  • γ = 101.316 (1)°

  • V = 2007.43 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.29 mm−1

  • T = 100 K

  • 0.47 × 0.33 × 0.11 mm

Data collection
  • Bruker APEX DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.876, Tmax = 0.968

  • 41276 measured reflections

  • 14580 independent reflections

  • 11642 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.122

  • S = 1.03

  • 14580 reflections

  • 573 parameters

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

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1NA⋯O1A 0.83 (2) 1.976 (19) 2.6722 (16) 140.9 (19)
N2A—H2NA⋯S2Bi 0.85 (2) 2.59 (2) 3.4201 (12) 165.0 (19)
N3A—H3NA⋯O2Bii 0.864 (19) 2.31 (2) 2.9715 (15) 133.3 (18)
N4A—H4NA⋯O2A 0.90 (2) 1.86 (2) 2.6064 (17) 138.2 (18)
N1B—H1NB⋯O1B 0.86 (2) 1.88 (2) 2.6248 (17) 144.5 (19)
N2B—H2NB⋯S1Biii 0.834 (19) 2.71 (2) 3.4961 (12) 158.3 (19)
N3B—H3NB⋯S1Ai 0.84 (2) 2.62 (2) 3.4336 (12) 163.0 (18)
N4B—H4NB⋯O2B 0.87 (2) 1.92 (2) 2.6543 (16) 141.1 (19)
C5A—H5AA⋯S1A 0.95 2.51 3.1910 (16) 129
C1B—H1BA⋯S1B 0.95 2.68 3.2693 (15) 121
C4B—H4BA⋯O2Aiv 0.95 2.55 3.4819 (18) 165
C10B—H10B⋯S2Av 0.95 2.84 3.4570 (15) 123
C11B—H11B⋯S2Av 0.95 2.85 3.4687 (15) 123
C14A—H14A⋯O2Bii 0.95 2.35 3.2700 (17) 164
C14B—H14B⋯O1Aii 0.95 2.36 3.2897 (17) 165
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+1, -y+1, -z; (iii) -x, -y+1, -z; (iv) -x+1, -y+1, -z+1; (v) x-1, y+1, z.

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

Thiourea derivatives play an important roles in many biological activities (Madan et al., 1991) such as antimycobacterial agent (Fernandez et al., 2005), antiviral (Kucukguzel et al., 2008), and antibacterial (Saeed et al., 2009). As part of our studies in this area, we now describe the title compound, which contains two thiourea groups from the reaction of 3-acetylbenzoyl isothiocyanate with aniline.

There are two molecules in the asymmetric unit (Fig. 1) of the title compound. For molecule A, the dihedral angles between the aldehyde benzene (C9A—C14A) and the phenyl rings (C1A—C6A & C17A—C22A) are 16.97 (8) and 20.97 (8)°, respectively while the two phenyl rings make a dihedral angle of 37.87 (8)°. In the molecule B, corresponding values are 34.92 (7), 53.90 (7)° and 60.68 (8)° respectively.

In each molecule, three set of S(6) hydrogen rings motif can be observe involving the N—H···O and C—H···S intramolecular interactions. An extensive intermolceular interactions of N—H···S, N—H···O, C—H···O and C—H···S link the molecules into a three-dimensional network (Fig. 2, Table 1).

Related literature top

For biological applications of benzimidazole derivatives, see: Madan et al. (1991); Fernandez et al. (2005); Kucukguzel et al. (2008); Saeed et al. (2009). For related literature [on what subject?], see: Rauf et al. (2009).

Experimental top

Isophthaloyl dichloride (1 mmol) in 15 ml of dry acetone was added drop wise to a suspension of potassium thiocyanate (2 mmol) in 15 ml of dry acetone. The mixture was stirred for 1 h at room temperature and the white potassium chloride (KCl) was filtered. Aniline (2 mmol) in dry acetone (15 ml) was added into the filtrate and heated under reflux for 7 h. The mixture was cooled to room temperature and filtered. The filtrate was poured into ice in a beaker to form solid. The crude was filtered, washed with ethanol and recrystallized from ethanol-acetonitrile (1:1) solution to yield colourless blocks.

Refinement top

N bound H atoms were located from difference Fourier maps and freely refined. The remaining H atoms were positioned geometrically and refined using a riding model with with C–H = 0.95 Å and Uiso(H) = 1.2Ueq(C).

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 asymmetric unit of the title compound, showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of (I). Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.
N,N'-Bis(phenylcarbamothioyl)benzene-1,3-dicarboxamide top
Crystal data top
C22H18N4O2S2Z = 4
Mr = 434.52F(000) = 904
Triclinic, P1Dx = 1.438 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.1812 (2) ÅCell parameters from 9969 reflections
b = 11.5623 (2) Åθ = 2.6–32.6°
c = 16.4471 (2) ŵ = 0.29 mm1
α = 101.420 (1)°T = 100 K
β = 98.127 (1)°Block, colourless
γ = 101.316 (1)°0.47 × 0.33 × 0.11 mm
V = 2007.43 (6) Å3
Data collection top
Bruker APEX DUO CCD
diffractometer
14580 independent reflections
Radiation source: fine-focus sealed tube11642 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ϕ and ω scansθmax = 32.7°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1616
Tmin = 0.876, Tmax = 0.968k = 1717
41276 measured reflectionsl = 2424
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.060P)2 + 0.666P]
where P = (Fo2 + 2Fc2)/3
14580 reflections(Δ/σ)max = 0.002
573 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C22H18N4O2S2γ = 101.316 (1)°
Mr = 434.52V = 2007.43 (6) Å3
Triclinic, P1Z = 4
a = 11.1812 (2) ÅMo Kα radiation
b = 11.5623 (2) ŵ = 0.29 mm1
c = 16.4471 (2) ÅT = 100 K
α = 101.420 (1)°0.47 × 0.33 × 0.11 mm
β = 98.127 (1)°
Data collection top
Bruker APEX DUO CCD
diffractometer
14580 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
11642 reflections with I > 2σ(I)
Tmin = 0.876, Tmax = 0.968Rint = 0.034
41276 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.53 e Å3
14580 reflectionsΔρmin = 0.28 e Å3
573 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
S1A0.56880 (4)0.73303 (3)0.12090 (2)0.01838 (7)
S2A0.87429 (3)0.08533 (3)0.22615 (2)0.01788 (7)
O1A0.70303 (10)0.43088 (9)0.02345 (6)0.01691 (19)
O2A0.84638 (12)0.45365 (10)0.37157 (6)0.0243 (2)
N1A0.58550 (12)0.49816 (11)0.15304 (7)0.0158 (2)
N2A0.63967 (11)0.60868 (10)0.01410 (7)0.0149 (2)
N3A0.85008 (11)0.31200 (10)0.25405 (7)0.0151 (2)
N4A0.86694 (12)0.23330 (11)0.37280 (7)0.0174 (2)
C1A0.55898 (15)0.34542 (13)0.27844 (9)0.0203 (3)
H1AA0.59310.29850.24400.024*
C2A0.52227 (17)0.29874 (14)0.36505 (9)0.0255 (3)
H2AA0.53140.22010.38950.031*
C3A0.47246 (16)0.36650 (15)0.41579 (9)0.0237 (3)
H3AA0.44750.33480.47500.028*
C4A0.45953 (17)0.48052 (15)0.37945 (9)0.0273 (3)
H4AA0.42540.52710.41420.033*
C5A0.49557 (16)0.52866 (15)0.29272 (9)0.0257 (3)
H5AA0.48580.60720.26850.031*
C6A0.54596 (13)0.46072 (12)0.24196 (8)0.0148 (2)
C7A0.59717 (12)0.60539 (12)0.09913 (8)0.0139 (2)
C8A0.69641 (12)0.52843 (12)0.01927 (8)0.0137 (2)
C9A0.74873 (12)0.56819 (12)0.11167 (8)0.0140 (2)
C10A0.77808 (14)0.68980 (12)0.15500 (8)0.0178 (2)
H10A0.76810.75070.12510.021*
C11A0.82180 (15)0.72217 (13)0.24174 (9)0.0212 (3)
H11A0.84020.80480.27130.025*
C12A0.83832 (14)0.63308 (13)0.28471 (8)0.0197 (3)
H12A0.86580.65480.34420.024*
C13A0.81496 (13)0.51154 (12)0.24138 (8)0.0148 (2)
C14A0.76909 (12)0.47850 (12)0.15455 (8)0.0139 (2)
H14A0.75190.39600.12480.017*
C15A0.83784 (13)0.42367 (12)0.29426 (8)0.0162 (2)
C16A0.86424 (12)0.21278 (12)0.28948 (8)0.0143 (2)
C17A0.86565 (13)0.15044 (13)0.42592 (8)0.0167 (2)
C18A0.92475 (14)0.19911 (14)0.50987 (8)0.0196 (3)
H18A0.96740.28200.52750.024*
C19A0.92110 (15)0.12619 (14)0.56758 (9)0.0218 (3)
H19A0.96030.15970.62490.026*
C20A0.86063 (15)0.00499 (14)0.54201 (9)0.0225 (3)
H20A0.86030.04540.58120.027*
C21A0.80024 (15)0.04280 (14)0.45842 (10)0.0228 (3)
H21A0.75770.12580.44110.027*
C22A0.80140 (14)0.02947 (13)0.40006 (9)0.0198 (3)
H22A0.75890.00330.34340.024*
S1B0.04057 (4)0.37065 (3)0.07939 (2)0.01870 (8)
S2B0.48059 (4)1.19306 (3)0.11559 (2)0.01956 (8)
O1B0.13462 (11)0.75257 (9)0.24757 (6)0.0201 (2)
O2B0.30600 (9)0.81658 (9)0.08677 (6)0.01593 (18)
N1B0.13188 (11)0.52187 (11)0.23333 (7)0.0154 (2)
N2B0.08889 (11)0.60964 (10)0.12230 (7)0.0145 (2)
N3B0.36721 (11)1.02400 (10)0.04957 (7)0.0131 (2)
N4B0.45042 (11)0.95054 (10)0.16480 (7)0.0139 (2)
C1B0.18586 (14)0.33048 (13)0.25490 (9)0.0195 (3)
H1BA0.18600.30280.19660.023*
C2B0.21509 (16)0.26110 (14)0.31178 (10)0.0255 (3)
H2BA0.23540.18570.29200.031*
C3B0.21489 (16)0.30126 (15)0.39736 (10)0.0269 (3)
H3BA0.23370.25280.43560.032*
C4B0.18724 (16)0.41160 (16)0.42659 (9)0.0266 (3)
H4BA0.18820.43960.48510.032*
C5B0.15812 (15)0.48148 (14)0.37044 (9)0.0220 (3)
H5BA0.13920.55740.39050.026*
C6B0.15657 (13)0.44021 (12)0.28430 (8)0.0155 (2)
C7B0.09048 (12)0.50324 (12)0.15029 (8)0.0139 (2)
C8B0.11636 (12)0.72663 (12)0.16982 (8)0.0140 (2)
C9B0.12775 (12)0.82365 (11)0.12203 (8)0.0133 (2)
C10B0.08163 (13)0.92559 (12)0.14973 (8)0.0168 (2)
H10B0.03790.92890.19530.020*
C11B0.09979 (13)1.02205 (12)0.11061 (9)0.0173 (2)
H11B0.06441.08930.12720.021*
C12B0.16985 (13)1.01978 (12)0.04711 (8)0.0151 (2)
H12B0.18381.08630.02100.018*
C13B0.21967 (12)0.92008 (11)0.02166 (8)0.0126 (2)
C14B0.19528 (12)0.81962 (11)0.05684 (8)0.0126 (2)
H14B0.22430.74940.03670.015*
C15B0.29979 (12)0.91422 (11)0.04329 (7)0.0127 (2)
C16B0.43319 (12)1.04832 (11)0.11312 (7)0.0126 (2)
C17B0.49238 (12)0.94255 (12)0.24293 (8)0.0135 (2)
C18B0.58498 (13)1.02975 (12)0.25842 (8)0.0168 (2)
H18B0.62571.09960.21520.020*
C19B0.61801 (14)1.01436 (14)0.33785 (9)0.0204 (3)
H19B0.68211.07370.34830.025*
C20B0.55823 (14)0.91338 (14)0.40168 (9)0.0213 (3)
H20B0.57870.90510.45630.026*
C21B0.46833 (14)0.82451 (14)0.38515 (9)0.0211 (3)
H21B0.42830.75430.42830.025*
C22B0.43662 (13)0.83782 (13)0.30554 (8)0.0171 (2)
H22B0.37700.77550.29390.020*
H1NA0.6098 (18)0.4465 (18)0.1306 (12)0.022 (5)*
H2NA0.6244 (18)0.6662 (18)0.0208 (12)0.026 (5)*
H3NA0.8458 (18)0.2974 (17)0.2000 (12)0.023 (5)*
H4NA0.869 (2)0.310 (2)0.3996 (13)0.035 (6)*
H1NB0.1426 (19)0.5963 (19)0.2599 (13)0.030 (5)*
H2NB0.0724 (19)0.6022 (18)0.0702 (12)0.028 (5)*
H3NB0.3662 (18)1.0839 (19)0.0115 (12)0.027 (5)*
H4NB0.4132 (19)0.8814 (19)0.1562 (12)0.027 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.02852 (18)0.01355 (14)0.01349 (14)0.00880 (13)0.00118 (12)0.00214 (11)
S2A0.02273 (17)0.01587 (15)0.01761 (15)0.00915 (13)0.00616 (12)0.00355 (12)
O1A0.0239 (5)0.0119 (4)0.0144 (4)0.0059 (4)0.0023 (4)0.0013 (3)
O2A0.0430 (7)0.0183 (5)0.0123 (4)0.0121 (5)0.0031 (4)0.0018 (4)
N1A0.0224 (6)0.0125 (5)0.0121 (5)0.0067 (4)0.0007 (4)0.0013 (4)
N2A0.0215 (6)0.0129 (5)0.0111 (4)0.0078 (4)0.0027 (4)0.0009 (4)
N3A0.0207 (6)0.0138 (5)0.0113 (4)0.0054 (4)0.0027 (4)0.0027 (4)
N4A0.0251 (6)0.0147 (5)0.0128 (5)0.0068 (5)0.0013 (4)0.0035 (4)
C1A0.0290 (8)0.0156 (6)0.0156 (6)0.0056 (5)0.0030 (5)0.0024 (5)
C2A0.0392 (9)0.0191 (7)0.0163 (6)0.0097 (6)0.0028 (6)0.0017 (5)
C3A0.0311 (8)0.0244 (7)0.0130 (5)0.0068 (6)0.0019 (5)0.0002 (5)
C4A0.0396 (9)0.0255 (8)0.0157 (6)0.0124 (7)0.0034 (6)0.0031 (5)
C5A0.0376 (9)0.0212 (7)0.0157 (6)0.0137 (6)0.0047 (6)0.0015 (5)
C6A0.0167 (6)0.0145 (6)0.0115 (5)0.0027 (5)0.0016 (4)0.0008 (4)
C7A0.0159 (6)0.0130 (5)0.0121 (5)0.0036 (5)0.0018 (4)0.0016 (4)
C8A0.0157 (6)0.0125 (5)0.0131 (5)0.0035 (4)0.0031 (4)0.0032 (4)
C9A0.0168 (6)0.0123 (5)0.0129 (5)0.0045 (5)0.0022 (4)0.0020 (4)
C10A0.0234 (7)0.0123 (5)0.0167 (6)0.0054 (5)0.0001 (5)0.0026 (5)
C11A0.0303 (8)0.0128 (6)0.0170 (6)0.0054 (5)0.0020 (5)0.0005 (5)
C12A0.0274 (7)0.0150 (6)0.0139 (5)0.0053 (5)0.0011 (5)0.0005 (5)
C13A0.0178 (6)0.0132 (5)0.0133 (5)0.0043 (5)0.0021 (4)0.0027 (4)
C14A0.0168 (6)0.0114 (5)0.0129 (5)0.0036 (4)0.0023 (4)0.0014 (4)
C15A0.0201 (6)0.0145 (6)0.0133 (5)0.0043 (5)0.0015 (5)0.0026 (4)
C16A0.0136 (6)0.0150 (6)0.0148 (5)0.0038 (5)0.0023 (4)0.0045 (4)
C17A0.0195 (6)0.0177 (6)0.0148 (5)0.0073 (5)0.0040 (5)0.0047 (5)
C18A0.0242 (7)0.0197 (6)0.0155 (6)0.0058 (5)0.0035 (5)0.0048 (5)
C19A0.0274 (7)0.0255 (7)0.0147 (6)0.0075 (6)0.0060 (5)0.0068 (5)
C20A0.0264 (7)0.0256 (7)0.0215 (6)0.0083 (6)0.0114 (5)0.0126 (6)
C21A0.0267 (8)0.0204 (7)0.0245 (7)0.0057 (6)0.0096 (6)0.0090 (5)
C22A0.0227 (7)0.0190 (6)0.0173 (6)0.0043 (5)0.0035 (5)0.0041 (5)
S1B0.02706 (18)0.01150 (14)0.01460 (14)0.00189 (13)0.00134 (12)0.00244 (11)
S2B0.02636 (18)0.01142 (14)0.02378 (16)0.00391 (13)0.01465 (14)0.00421 (12)
O1B0.0331 (6)0.0156 (5)0.0122 (4)0.0055 (4)0.0074 (4)0.0026 (3)
O2B0.0225 (5)0.0117 (4)0.0144 (4)0.0048 (4)0.0068 (4)0.0020 (3)
N1B0.0206 (6)0.0126 (5)0.0127 (5)0.0034 (4)0.0017 (4)0.0034 (4)
N2B0.0202 (6)0.0131 (5)0.0106 (4)0.0036 (4)0.0032 (4)0.0036 (4)
N3B0.0173 (5)0.0104 (5)0.0115 (4)0.0022 (4)0.0061 (4)0.0009 (4)
N4B0.0174 (5)0.0123 (5)0.0129 (4)0.0040 (4)0.0060 (4)0.0023 (4)
C1B0.0236 (7)0.0176 (6)0.0178 (6)0.0058 (5)0.0015 (5)0.0055 (5)
C2B0.0328 (8)0.0182 (7)0.0249 (7)0.0066 (6)0.0020 (6)0.0082 (6)
C3B0.0314 (8)0.0237 (7)0.0231 (7)0.0004 (6)0.0043 (6)0.0127 (6)
C4B0.0336 (9)0.0292 (8)0.0152 (6)0.0026 (7)0.0008 (6)0.0085 (6)
C5B0.0296 (8)0.0216 (7)0.0147 (6)0.0066 (6)0.0024 (5)0.0043 (5)
C6B0.0162 (6)0.0163 (6)0.0139 (5)0.0027 (5)0.0008 (4)0.0059 (4)
C7B0.0158 (6)0.0131 (5)0.0138 (5)0.0034 (5)0.0035 (4)0.0043 (4)
C8B0.0160 (6)0.0128 (5)0.0140 (5)0.0033 (5)0.0052 (4)0.0031 (4)
C9B0.0158 (6)0.0111 (5)0.0131 (5)0.0026 (4)0.0044 (4)0.0027 (4)
C10B0.0203 (6)0.0150 (6)0.0171 (6)0.0055 (5)0.0089 (5)0.0035 (5)
C11B0.0200 (6)0.0127 (5)0.0218 (6)0.0065 (5)0.0092 (5)0.0039 (5)
C12B0.0179 (6)0.0123 (5)0.0164 (5)0.0039 (5)0.0051 (5)0.0042 (4)
C13B0.0154 (6)0.0104 (5)0.0114 (5)0.0021 (4)0.0033 (4)0.0016 (4)
C14B0.0155 (6)0.0104 (5)0.0119 (5)0.0035 (4)0.0033 (4)0.0014 (4)
C15B0.0161 (6)0.0121 (5)0.0102 (5)0.0036 (4)0.0027 (4)0.0027 (4)
C16B0.0137 (5)0.0132 (5)0.0114 (5)0.0038 (4)0.0032 (4)0.0030 (4)
C17B0.0153 (6)0.0141 (5)0.0123 (5)0.0057 (5)0.0039 (4)0.0027 (4)
C18B0.0178 (6)0.0150 (6)0.0170 (6)0.0020 (5)0.0064 (5)0.0015 (5)
C19B0.0249 (7)0.0200 (6)0.0195 (6)0.0061 (5)0.0117 (5)0.0055 (5)
C20B0.0252 (7)0.0244 (7)0.0159 (6)0.0069 (6)0.0096 (5)0.0036 (5)
C21B0.0229 (7)0.0222 (7)0.0155 (6)0.0047 (6)0.0055 (5)0.0026 (5)
C22B0.0173 (6)0.0150 (6)0.0179 (6)0.0029 (5)0.0062 (5)0.0003 (5)
Geometric parameters (Å, º) top
S1A—C7A1.6636 (14)S1B—C7B1.6715 (13)
S2A—C16A1.6611 (14)S2B—C16B1.6638 (13)
O1A—C8A1.2267 (15)O1B—C8B1.2317 (15)
O2A—C15A1.2346 (15)O2B—C15B1.2312 (15)
N1A—C7A1.3449 (16)N1B—C7B1.3385 (16)
N1A—C6A1.4188 (16)N1B—C6B1.4215 (17)
N1A—H1NA0.83 (2)N1B—H1NB0.86 (2)
N2A—C8A1.3780 (17)N2B—C8B1.3731 (17)
N2A—C7A1.4026 (16)N2B—C7B1.3986 (17)
N2A—H2NA0.85 (2)N2B—H2NB0.83 (2)
N3A—C15A1.3711 (17)N3B—C15B1.3741 (16)
N3A—C16A1.4110 (17)N3B—C16B1.4032 (15)
N3A—H3NA0.864 (19)N3B—H3NB0.84 (2)
N4A—C16A1.3385 (16)N4B—C16B1.3375 (16)
N4A—C17A1.4182 (17)N4B—C17B1.4215 (16)
N4A—H4NA0.90 (2)N4B—H4NB0.87 (2)
C1A—C2A1.3900 (19)C1B—C6B1.384 (2)
C1A—C6A1.3938 (19)C1B—C2B1.393 (2)
C1A—H1AA0.9500C1B—H1BA0.9500
C2A—C3A1.385 (2)C2B—C3B1.392 (2)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.380 (2)C3B—C4B1.381 (2)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.394 (2)C4B—C5B1.388 (2)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.390 (2)C5B—C6B1.3990 (18)
C5A—H5AA0.9500C5B—H5BA0.9500
C8A—C9A1.4932 (17)C8B—C9B1.4879 (18)
C9A—C10A1.3960 (18)C9B—C14B1.3946 (17)
C9A—C14A1.4005 (18)C9B—C10B1.3982 (18)
C10A—C11A1.3907 (19)C10B—C11B1.3898 (19)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.386 (2)C11B—C12B1.3906 (18)
C11A—H11A0.9500C11B—H11B0.9500
C12A—C13A1.3992 (19)C12B—C13B1.3933 (18)
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.3958 (17)C13B—C14B1.3946 (17)
C13A—C15A1.4977 (18)C13B—C15B1.4880 (17)
C14A—H14A0.9500C14B—H14B0.9500
C17A—C22A1.392 (2)C17B—C18B1.3856 (18)
C17A—C18A1.3958 (19)C17B—C22B1.3942 (18)
C18A—C19A1.388 (2)C18B—C19B1.3947 (18)
C18A—H18A0.9500C18B—H18B0.9500
C19A—C20A1.383 (2)C19B—C20B1.386 (2)
C19A—H19A0.9500C19B—H19B0.9500
C20A—C21A1.393 (2)C20B—C21B1.387 (2)
C20A—H20A0.9500C20B—H20B0.9500
C21A—C22A1.392 (2)C21B—C22B1.3916 (18)
C21A—H21A0.9500C21B—H21B0.9500
C22A—H22A0.9500C22B—H22B0.9500
C7A—N1A—C6A131.12 (12)C7B—N1B—C6B131.26 (12)
C7A—N1A—H1NA114.1 (13)C7B—N1B—H1NB113.1 (14)
C6A—N1A—H1NA114.7 (13)C6B—N1B—H1NB115.6 (13)
C8A—N2A—C7A128.61 (11)C8B—N2B—C7B128.08 (11)
C8A—N2A—H2NA116.9 (13)C8B—N2B—H2NB115.2 (14)
C7A—N2A—H2NA114.4 (13)C7B—N2B—H2NB116.6 (14)
C15A—N3A—C16A127.99 (11)C15B—N3B—C16B127.96 (11)
C15A—N3A—H3NA118.0 (13)C15B—N3B—H3NB115.5 (14)
C16A—N3A—H3NA114.0 (13)C16B—N3B—H3NB116.5 (14)
C16A—N4A—C17A128.96 (12)C16B—N4B—C17B128.47 (11)
C16A—N4A—H4NA116.6 (13)C16B—N4B—H4NB114.5 (13)
C17A—N4A—H4NA114.4 (13)C17B—N4B—H4NB114.9 (13)
C2A—C1A—C6A120.28 (14)C6B—C1B—C2B119.28 (13)
C2A—C1A—H1AA119.9C6B—C1B—H1BA120.4
C6A—C1A—H1AA119.9C2B—C1B—H1BA120.4
C3A—C2A—C1A120.24 (14)C3B—C2B—C1B120.57 (15)
C3A—C2A—H2AA119.9C3B—C2B—H2BA119.7
C1A—C2A—H2AA119.9C1B—C2B—H2BA119.7
C4A—C3A—C2A119.32 (13)C4B—C3B—C2B119.95 (14)
C4A—C3A—H3AA120.3C4B—C3B—H3BA120.0
C2A—C3A—H3AA120.3C2B—C3B—H3BA120.0
C3A—C4A—C5A121.22 (15)C3B—C4B—C5B119.92 (14)
C3A—C4A—H4AA119.4C3B—C4B—H4BA120.0
C5A—C4A—H4AA119.4C5B—C4B—H4BA120.0
C6A—C5A—C4A119.37 (14)C4B—C5B—C6B120.07 (14)
C6A—C5A—H5AA120.3C4B—C5B—H5BA120.0
C4A—C5A—H5AA120.3C6B—C5B—H5BA120.0
C5A—C6A—C1A119.56 (12)C1B—C6B—C5B120.19 (12)
C5A—C6A—N1A125.23 (12)C1B—C6B—N1B124.44 (12)
C1A—C6A—N1A115.21 (12)C5B—C6B—N1B115.22 (12)
N1A—C7A—N2A115.00 (11)N1B—C7B—N2B114.03 (11)
N1A—C7A—S1A128.26 (10)N1B—C7B—S1B127.76 (10)
N2A—C7A—S1A116.74 (9)N2B—C7B—S1B118.21 (9)
O1A—C8A—N2A122.67 (12)O1B—C8B—N2B123.30 (12)
O1A—C8A—C9A122.15 (12)O1B—C8B—C9B120.59 (12)
N2A—C8A—C9A115.18 (11)N2B—C8B—C9B116.07 (11)
C10A—C9A—C14A120.18 (12)C14B—C9B—C10B120.33 (12)
C10A—C9A—C8A122.27 (11)C14B—C9B—C8B120.58 (11)
C14A—C9A—C8A117.55 (11)C10B—C9B—C8B118.70 (11)
C11A—C10A—C9A120.28 (12)C11B—C10B—C9B120.02 (12)
C11A—C10A—H10A119.9C11B—C10B—H10B120.0
C9A—C10A—H10A119.9C9B—C10B—H10B120.0
C12A—C11A—C10A119.56 (13)C10B—C11B—C12B119.78 (12)
C12A—C11A—H11A120.2C10B—C11B—H11B120.1
C10A—C11A—H11A120.2C12B—C11B—H11B120.1
C11A—C12A—C13A120.69 (12)C11B—C12B—C13B120.11 (12)
C11A—C12A—H12A119.7C11B—C12B—H12B119.9
C13A—C12A—H12A119.7C13B—C12B—H12B119.9
C14A—C13A—C12A119.85 (12)C12B—C13B—C14B120.44 (11)
C14A—C13A—C15A124.20 (12)C12B—C13B—C15B122.76 (11)
C12A—C13A—C15A115.92 (11)C14B—C13B—C15B116.80 (11)
C13A—C14A—C9A119.34 (12)C9B—C14B—C13B119.13 (11)
C13A—C14A—H14A120.3C9B—C14B—H14B120.4
C9A—C14A—H14A120.3C13B—C14B—H14B120.4
O2A—C15A—N3A122.35 (12)O2B—C15B—N3B123.07 (11)
O2A—C15A—C13A119.77 (12)O2B—C15B—C13B121.40 (11)
N3A—C15A—C13A117.87 (11)N3B—C15B—C13B115.51 (11)
N4A—C16A—N3A114.43 (11)N4B—C16B—N3B115.10 (11)
N4A—C16A—S2A127.03 (10)N4B—C16B—S2B127.79 (10)
N3A—C16A—S2A118.54 (9)N3B—C16B—S2B117.11 (9)
C22A—C17A—C18A120.25 (13)C18B—C17B—C22B119.87 (12)
C22A—C17A—N4A123.49 (12)C18B—C17B—N4B124.05 (12)
C18A—C17A—N4A116.05 (12)C22B—C17B—N4B116.07 (12)
C19A—C18A—C17A119.93 (14)C17B—C18B—C19B119.62 (13)
C19A—C18A—H18A120.0C17B—C18B—H18B120.2
C17A—C18A—H18A120.0C19B—C18B—H18B120.2
C20A—C19A—C18A120.28 (14)C20B—C19B—C18B120.66 (13)
C20A—C19A—H19A119.9C20B—C19B—H19B119.7
C18A—C19A—H19A119.9C18B—C19B—H19B119.7
C19A—C20A—C21A119.58 (13)C19B—C20B—C21B119.51 (12)
C19A—C20A—H20A120.2C19B—C20B—H20B120.2
C21A—C20A—H20A120.2C21B—C20B—H20B120.2
C22A—C21A—C20A120.86 (14)C20B—C21B—C22B120.21 (13)
C22A—C21A—H21A119.6C20B—C21B—H21B119.9
C20A—C21A—H21A119.6C22B—C21B—H21B119.9
C21A—C22A—C17A119.05 (13)C21B—C22B—C17B120.00 (13)
C21A—C22A—H22A120.5C21B—C22B—H22B120.0
C17A—C22A—H22A120.5C17B—C22B—H22B120.0
C6A—C1A—C2A—C3A0.0 (2)C6B—C1B—C2B—C3B0.1 (2)
C1A—C2A—C3A—C4A0.1 (3)C1B—C2B—C3B—C4B0.9 (3)
C2A—C3A—C4A—C5A0.0 (3)C2B—C3B—C4B—C5B0.8 (3)
C3A—C4A—C5A—C6A0.3 (3)C3B—C4B—C5B—C6B0.1 (2)
C4A—C5A—C6A—C1A0.4 (2)C2B—C1B—C6B—C5B0.9 (2)
C4A—C5A—C6A—N1A179.49 (15)C2B—C1B—C6B—N1B176.40 (14)
C2A—C1A—C6A—C5A0.2 (2)C4B—C5B—C6B—C1B1.0 (2)
C2A—C1A—C6A—N1A179.43 (14)C4B—C5B—C6B—N1B176.88 (14)
C7A—N1A—C6A—C5A7.9 (2)C7B—N1B—C6B—C1B25.2 (2)
C7A—N1A—C6A—C1A172.97 (14)C7B—N1B—C6B—C5B159.13 (15)
C6A—N1A—C7A—N2A179.98 (13)C6B—N1B—C7B—N2B174.40 (13)
C6A—N1A—C7A—S1A0.6 (2)C6B—N1B—C7B—S1B6.4 (2)
C8A—N2A—C7A—N1A16.0 (2)C8B—N2B—C7B—N1B4.6 (2)
C8A—N2A—C7A—S1A163.55 (11)C8B—N2B—C7B—S1B174.65 (11)
C7A—N2A—C8A—O1A9.8 (2)C7B—N2B—C8B—O1B8.0 (2)
C7A—N2A—C8A—C9A170.61 (13)C7B—N2B—C8B—C9B169.91 (12)
O1A—C8A—C9A—C10A158.89 (14)O1B—C8B—C9B—C14B132.42 (14)
N2A—C8A—C9A—C10A21.56 (19)N2B—C8B—C9B—C14B45.53 (18)
O1A—C8A—C9A—C14A20.53 (19)O1B—C8B—C9B—C10B40.45 (19)
N2A—C8A—C9A—C14A159.02 (12)N2B—C8B—C9B—C10B141.60 (13)
C14A—C9A—C10A—C11A3.3 (2)C14B—C9B—C10B—C11B1.9 (2)
C8A—C9A—C10A—C11A177.33 (13)C8B—C9B—C10B—C11B174.82 (13)
C9A—C10A—C11A—C12A1.2 (2)C9B—C10B—C11B—C12B3.6 (2)
C10A—C11A—C12A—C13A1.9 (2)C10B—C11B—C12B—C13B1.2 (2)
C11A—C12A—C13A—C14A3.0 (2)C11B—C12B—C13B—C14B2.8 (2)
C11A—C12A—C13A—C15A179.14 (14)C11B—C12B—C13B—C15B177.36 (13)
C12A—C13A—C14A—C9A0.9 (2)C10B—C9B—C14B—C13B2.1 (2)
C15A—C13A—C14A—C9A178.63 (13)C8B—C9B—C14B—C13B170.64 (12)
C10A—C9A—C14A—C13A2.2 (2)C12B—C13B—C14B—C9B4.50 (19)
C8A—C9A—C14A—C13A178.41 (12)C15B—C13B—C14B—C9B175.69 (12)
C16A—N3A—C15A—O2A5.0 (2)C16B—N3B—C15B—O2B13.1 (2)
C16A—N3A—C15A—C13A175.77 (13)C16B—N3B—C15B—C13B168.35 (12)
C14A—C13A—C15A—O2A160.83 (14)C12B—C13B—C15B—O2B153.15 (13)
C12A—C13A—C15A—O2A17.0 (2)C14B—C13B—C15B—O2B26.65 (18)
C14A—C13A—C15A—N3A20.0 (2)C12B—C13B—C15B—N3B28.24 (18)
C12A—C13A—C15A—N3A162.26 (13)C14B—C13B—C15B—N3B151.96 (12)
C17A—N4A—C16A—N3A172.02 (13)C17B—N4B—C16B—N3B167.44 (12)
C17A—N4A—C16A—S2A7.3 (2)C17B—N4B—C16B—S2B12.7 (2)
C15A—N3A—C16A—N4A0.7 (2)C15B—N3B—C16B—N4B13.00 (19)
C15A—N3A—C16A—S2A178.72 (11)C15B—N3B—C16B—S2B167.09 (11)
C16A—N4A—C17A—C22A34.1 (2)C16B—N4B—C17B—C18B39.0 (2)
C16A—N4A—C17A—C18A151.23 (14)C16B—N4B—C17B—C22B142.51 (14)
C22A—C17A—C18A—C19A1.0 (2)C22B—C17B—C18B—C19B2.7 (2)
N4A—C17A—C18A—C19A175.86 (13)N4B—C17B—C18B—C19B178.90 (13)
C17A—C18A—C19A—C20A0.9 (2)C17B—C18B—C19B—C20B0.7 (2)
C18A—C19A—C20A—C21A1.8 (2)C18B—C19B—C20B—C21B2.7 (2)
C19A—C20A—C21A—C22A0.9 (2)C19B—C20B—C21B—C22B1.3 (2)
C20A—C21A—C22A—C17A1.0 (2)C20B—C21B—C22B—C17B2.1 (2)
C18A—C17A—C22A—C21A1.9 (2)C18B—C17B—C22B—C21B4.1 (2)
N4A—C17A—C22A—C21A176.41 (13)N4B—C17B—C22B—C21B177.38 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O1A0.83 (2)1.976 (19)2.6722 (16)140.9 (19)
N2A—H2NA···S2Bi0.85 (2)2.59 (2)3.4201 (12)165.0 (19)
N3A—H3NA···O2Bii0.864 (19)2.31 (2)2.9715 (15)133.3 (18)
N4A—H4NA···O2A0.90 (2)1.86 (2)2.6064 (17)138.2 (18)
N1B—H1NB···O1B0.86 (2)1.88 (2)2.6248 (17)144.5 (19)
N2B—H2NB···S1Biii0.834 (19)2.71 (2)3.4961 (12)158.3 (19)
N3B—H3NB···S1Ai0.84 (2)2.62 (2)3.4336 (12)163.0 (18)
N4B—H4NB···O2B0.87 (2)1.92 (2)2.6543 (16)141.1 (19)
C5A—H5AA···S1A0.952.513.1910 (16)129
C1B—H1BA···S1B0.952.683.2693 (15)121
C4B—H4BA···O2Aiv0.952.553.4819 (18)165
C10B—H10B···S2Av0.952.843.4570 (15)123
C11B—H11B···S2Av0.952.853.4687 (15)123
C14A—H14A···O2Bii0.952.353.2700 (17)164
C14B—H14B···O1Aii0.952.363.2897 (17)165
Symmetry codes: (i) x+1, y+2, z; (ii) x+1, y+1, z; (iii) x, y+1, z; (iv) x+1, y+1, z+1; (v) x1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O1A0.83 (2)1.976 (19)2.6722 (16)140.9 (19)
N2A—H2NA···S2Bi0.85 (2)2.59 (2)3.4201 (12)165.0 (19)
N3A—H3NA···O2Bii0.864 (19)2.31 (2)2.9715 (15)133.3 (18)
N4A—H4NA···O2A0.90 (2)1.86 (2)2.6064 (17)138.2 (18)
N1B—H1NB···O1B0.86 (2)1.88 (2)2.6248 (17)144.5 (19)
N2B—H2NB···S1Biii0.834 (19)2.71 (2)3.4961 (12)158.3 (19)
N3B—H3NB···S1Ai0.84 (2)2.62 (2)3.4336 (12)163.0 (18)
N4B—H4NB···O2B0.87 (2)1.92 (2)2.6543 (16)141.1 (19)
C5A—H5AA···S1A0.952.513.1910 (16)129
C1B—H1BA···S1B0.952.683.2693 (15)121
C4B—H4BA···O2Aiv0.952.553.4819 (18)165
C10B—H10B···S2Av0.952.843.4570 (15)123
C11B—H11B···S2Av0.952.853.4687 (15)123
C14A—H14A···O2Bii0.952.353.2700 (17)164
C14B—H14B···O1Aii0.952.363.2897 (17)165
Symmetry codes: (i) x+1, y+2, z; (ii) x+1, y+1, z; (iii) x, y+1, z; (iv) x+1, y+1, z+1; (v) x1, y+1, z.
 

Footnotes

Additional correspondence author, e-mail: nzainab@frst.unimas.my.

Acknowledgements

ZN, MAMA and HH thank Universiti Malaysia Sarawak and the Ministry of Science, Technology and Innovation, MOSTI, for financing this project through FRGS/01 (14)/743/2010 (29). WSHWZ thanks Yayasan Tunku Abdul Rahman for providing a scholarship for her postgraduate studies. MMR thanks Universiti Sains Malaysia (USM) for the research facilities and USM Short Term Grant (No. 304/PFIZIK/6312078).

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Volume 69| Part 9| September 2013| Pages o1374-o1375
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