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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 3| March 2015| Pages o175-o176

Crystal structure of 3-[(4-benzyl­piperazin-1-yl)meth­yl]-5-(thio­phen-2-yl)-2,3-di­hydro-1,3,4-oxa­diazole-2-thione

CROSSMARK_Color_square_no_text.svg

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riaydh 11451, Saudi Arabia, bKing Abdullah Institute for Nanotechnology (KAIN), King Saud University, Riyadh 11451, Saudi Arabia, cDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and eDepartment of Chemistry, Alva's Institute of Engineering & Technology, Mijar, Moodbidri 574 225, Karnataka, India
*Correspondence e-mail: elemam5@hotmail.com, hfun.c@ksu.edu.sa

Edited by J. Simpson, University of Otago, New Zealand (Received 30 January 2015; accepted 3 February 2015; online 13 February 2015)

The title 1,3,4-oxa­diazole-2-thione derivative, C18H20N4OS2, crystallized with two independent mol­ecules (A and B) in the asymmetric unit. The 2-thienyl rings in both mol­ecules are rotationally disordered over two orientations by approximately 180° about the single C—C bond that connects it to the oxa­diazole thione ring; the ratios of site occupancies for the major and minor components were fixed in the structure refinement at 0.8:0.2 and 0.9:0.1 in mol­ecules A and B, respectively. The 1,3,4-oxa­diazole-2-thione ring forms dihedral angles of 7.71 (16), 10.0 (11) and 77.50 (12)° (mol­ecule A), and 6.5 (3), 6.0 (9) and 55.30 (12)° (mol­ecule B) with the major and minor parts of the disordered thio­phene ring and the mean plane of the adjacent piperazine ring, respectively, resulting in approximately V-shaped conformations for the mol­ecules. The piperazine ring in both mol­ecules adopts a chair conformation. The terminal benzene ring is inclined towards the mean plane of the piperazine ring with N—C—C—C torsion angles of −58.2 (3) and −66.2 (3)° in mol­ecules A and B, respectively. In the crystal, no inter­molecular hydrogen bonds are observed. The crystal packing features short S⋯S contacts [3.4792 (9) Å] and ππ inter­actions [3.661 (3), 3.664 (11) and 3.5727 (10) Å], producing a three-dimensional network.

1. Related literature

For the biological activity of 1,3,4-oxa­diazole derivatives, see: Al-Deeb et al. (2006[Al-Deeb, O. A., Al-Omar, M. A., El-Brollosy, N. R., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2006). Arzneim. Forsch. Drug. Res. 56, 40-47.]); El-Emam et al. (2004[El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113.]); Kadi et al. (2007[Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235-242.]); Padmavathi et al. (2009[Padmavathi, V., Reddy, G. S., Padmaja, A., Kondaiah, P. & Shazia, A. (2009). Eur. J. Med. Chem. 44 2106-2112.]). For the synthesis of the title compound, see: Al-Omar (2010[Al-Omar, M. A. (2010). Molecules, 15, 502-514.]). For related 1,3,4-oxa­diazole structures, see: El-Emam et al. (2012[El-Emam, A. A., Al-Omar, M. A., Ghabbour, H. A., Fun, H.-K. & Chia, T. S. (2012). Acta Cryst. E68, o1345-o1346.], 2013[El-Emam, A. A., Al-Omar, M. A., Al-Obaid, A.-R. M., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o684.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C18H20N4OS2

  • Mr = 372.50

  • Monoclinic, P 21 /c

  • a = 10.6909 (5) Å

  • b = 29.3658 (13) Å

  • c = 15.6179 (6) Å

  • β = 130.283 (2)°

  • V = 3740.4 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.30 mm−1

  • T = 273 K

  • 0.41 × 0.36 × 0.14 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • 88935 measured reflections

  • 11407 independent reflections

  • 10339 reflections with I > 2σ(I)

  • Rint = 0.034

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.122

  • S = 1.19

  • 11407 reflections

  • 485 parameters

  • 18 restraints

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. 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: SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Chemical context top

Considerable attention has been devoted to 1,3,4-oxa­diazole derivatives which have long been known for their diverse chemotherapeutic properties as anti­viral agents against HIV-1 viruses (El-Emam et al., 2004) and to demonstrate anti­bacterial (Padmavathi et al., 2009) and anti-inflammatory properties (Kadi et al., 2007; Al-Deeb et al., 2006). The title compound was synthesized among a series of 2-thienyl-1,3,4-oxa­diazo­les and related derivatives as potential anti­microbial agents (Al-Omar, 2010).

Structural commentary top

The asymmetric unit of the title compound consists of two crystallographically independent molecules (A and B) as shown in Fig. 1. The thio­phene rings has an approximately 180° rotational disorder (atoms of the minor part are labelled with the suffix X and Y for molecules A and B, respectively) about the C2–C3 single bond. The bond lengths and angles are within normal ranges and are comparable with those reported earlier for similar structures (El-Emam et al. 2012, 2013). The ratio of the refined site-occupancy factors of the major and minor parts of the disordered thio­phene ring is 0.8: 0.2 and 0.9 : 0.1 in molecules A and B respectively. The 1,3,4-oxa­diazole-2-thione (O1A/N1A/N2A/C1A/C2A and O1B/N1B/N2B/C1B/C2B) rings form dihedral angles of 7.71 (16), 10.0 (11) and 77.50 (12)° (molecule A); and 6.5 (3), 6.0 (9) and 55.30 (12)° (molecule B) with the major and minor parts of the disordered thio­phene ring and the mean plane of the adjacent piperazine rings (N3A/N4A/C8A–C11A and N3B/N4B/C8B–C11B), resulting in approximately V-shaped conformations for the molecules. The piperazine adopts a chair conformation with puckering parameters: Q = 0.591 (2) Å, θ = 178.50 (19)°, and ϕ = 8(10)° in molecule A and Q = 0.589 (2) Å, θ = 3.10 (19)°, and ϕ = 178 (6)° in molecule B. The terminal benzene rings (C13A–C18A and C13B–C18B) in both the molecules are inclined towards the mean plane of the piperazine ring with torsion angles N4A–C12A–C13A–C14A of -58.2 (3)° and N4B–C12B–C13B–C18B of -66.2 (3)°.

Supra­molecular features top

In the crystal, no significant inter­molecular hydrogen bonds are observed. The crystal packing (Fig. 2) is stabilized by a short S···S contact [3.4792 (9) Å] and ππ inter­actions with Cg1···Cg2i distance = 3.661 (3) Å, Cg1···Cg3i distance = 3.664 (11) Å and Cg4···Cg5i distance = 3.5727 (10) Å (symmetry code: (i) X, Y, Z), producing a three-dimensional structure. Cg1–Cg5 are the centroids of the S2A/C3A/C4A/C5A/C6A, S2B/C3B/C4B/C5B/C6B, C3B/S2Y/C6Y/C5Y/C4Y, O1A/C1A/N2A/N1A/C2A and O1B/C1B/N2B/N1B/C2B rings, respectively.

Synthesis and crystallization top

The title compound was prepared by a literature procedure (Al-Omar, 2010) and crystallized from EtOH/CHCl3 (1:1) to yield colorless crystals. M. P.: 101–103°C.

Refinement details top

All H atoms were positioned geometrically (C=H = 0.93 or 0.97 Å) and refined using a riding model with Uiso(H) = 1.2 Ueq(C). The thienyl ring is disordered over two positions and,in the final refinement cycles, the occupancy ratios were fixed in a ratio 0.8: 0.2 for molecule A and 0.9:0.1 for molecule B, respectively. Similarity and rigid-bond restraints were applied to the disordered atoms.

Related literature top

For the biological activity of 1,3,4-oxadiazole derivatives, see: Al-Deeb et al. (2006); El-Emam et al. (2004); Kadi et al. (2007); Padmavathi et al. (2009). For the synthesis of the title compound, see: Al-Omar (2010). For related 1,3,4-oxadiazole structures, see: El-Emam et al. (2012, 2013).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); 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 and 50% probability displacement ellipsoids (atoms of the minor part are labelled with the suffix X and Y for molecules A and B, respectively)
[Figure 2] Fig. 2. Crystal packing of the title compound, showing the S···S short contacts and ππ interactions as dashed lines. Only the major components of the thiophene rings are shown. All the H atoms are omitted for clarity.
3-[(4-Benzylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazole-2-thione top
Crystal data top
C18H20N4OS2F(000) = 1568
Mr = 372.50Dx = 1.323 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.6909 (5) ÅCell parameters from 9237 reflections
b = 29.3658 (13) Åθ = 2.4–30.5°
c = 15.6179 (6) ŵ = 0.30 mm1
β = 130.283 (2)°T = 273 K
V = 3740.4 (3) Å3Plate, colourless
Z = 80.41 × 0.36 × 0.14 mm
Data collection top
Bruker APEXII CCD
diffractometer
Rint = 0.034
ϕ and ω scansθmax = 30.6°, θmin = 2.2°
88935 measured reflectionsh = 1515
11407 independent reflectionsk = 4241
10339 reflections with I > 2σ(I)l = 2222
Refinement top
Refinement on F218 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0207P)2 + 3.9136P]
where P = (Fo2 + 2Fc2)/3
S = 1.19(Δ/σ)max = 0.001
11407 reflectionsΔρmax = 0.38 e Å3
485 parametersΔρmin = 0.42 e Å3
Crystal data top
C18H20N4OS2V = 3740.4 (3) Å3
Mr = 372.50Z = 8
Monoclinic, P21/cMo Kα radiation
a = 10.6909 (5) ŵ = 0.30 mm1
b = 29.3658 (13) ÅT = 273 K
c = 15.6179 (6) Å0.41 × 0.36 × 0.14 mm
β = 130.283 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
10339 reflections with I > 2σ(I)
88935 measured reflectionsRint = 0.034
11407 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05918 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.19Δρmax = 0.38 e Å3
11407 reflectionsΔρmin = 0.42 e Å3
485 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S1B0.86597 (6)0.54555 (2)0.95382 (4)0.03328 (11)
O1B0.56261 (15)0.54910 (4)0.88376 (10)0.0241 (2)
N1B0.40511 (17)0.56647 (5)0.70234 (13)0.0242 (3)
N2B0.56914 (17)0.56405 (5)0.75134 (13)0.0240 (3)
N3B0.64150 (18)0.61694 (6)0.66687 (13)0.0260 (3)
N4B0.64546 (19)0.71415 (6)0.67316 (13)0.0310 (3)
C1B0.6665 (2)0.55360 (6)0.86079 (15)0.0241 (3)
C2B0.4084 (2)0.55740 (6)0.78476 (14)0.0219 (3)
C3B0.2721 (2)0.55573 (6)0.78285 (15)0.0225 (3)
C4B0.2698 (4)0.54323 (10)0.8668 (3)0.0270 (6)0.8
H4BA0.36220.53380.93770.032*0.8
C5B0.1129 (8)0.5463 (4)0.8336 (6)0.0365 (16)0.8
H5BA0.08860.53860.87930.044*0.8
C6B0.0010 (6)0.5619 (3)0.7273 (5)0.0358 (13)0.8
H6BA0.10880.56660.69220.043*0.8
S2B0.08174 (8)0.57204 (3)0.66379 (7)0.03174 (14)0.8
C4Y0.122 (2)0.5646 (6)0.7033 (14)0.055 (5)*0.2
H4YA0.08480.57220.63240.066*0.2
C5Y0.015 (3)0.5625 (12)0.725 (2)0.039 (6)*0.2
H5YA0.09660.56940.67470.046*0.2
C6Y0.103 (2)0.5484 (12)0.835 (2)0.023 (4)*0.2
H6YA0.05730.54490.86910.028*0.2
S2Y0.3049 (4)0.53795 (12)0.9013 (3)0.0243 (7)*0.2
C7B0.6198 (2)0.57087 (7)0.68367 (16)0.0270 (4)
H7BA0.72220.55480.71990.032*
H7BB0.53810.55700.61070.032*
C8B0.7695 (2)0.64187 (6)0.77012 (14)0.0256 (3)
H8BA0.87060.62450.81430.031*
H8BB0.73640.64610.81460.031*
C9B0.7969 (2)0.68769 (7)0.74051 (16)0.0302 (4)
H9BA0.88110.70420.80870.036*
H9BB0.83450.68330.69880.036*
C10B0.5211 (3)0.68905 (8)0.56929 (17)0.0386 (5)
H10C0.55860.68480.52750.046*
H10D0.42010.70650.52300.046*
C11B0.4893 (2)0.64320 (7)0.59601 (16)0.0317 (4)
H11C0.44670.64740.63460.038*
H11D0.40790.62670.52690.038*
C12B0.6695 (3)0.75944 (8)0.64694 (19)0.0439 (6)
H12C0.56430.77470.59630.053*
H12D0.71300.75630.60870.053*
C13B0.7846 (2)0.78830 (7)0.75006 (19)0.0365 (5)
C14B0.9356 (3)0.80127 (8)0.7843 (2)0.0442 (5)
H14B0.96560.79200.74280.053*
C15B1.0420 (3)0.82762 (8)0.8787 (2)0.0504 (7)
H15B1.14260.83610.90020.061*
C16B1.0000 (3)0.84134 (8)0.9410 (2)0.0536 (7)
H16B1.07200.85911.00480.064*
C17B0.8495 (3)0.82871 (8)0.9084 (3)0.0533 (6)
H17B0.82050.83790.95050.064*
C18B0.7424 (3)0.80236 (8)0.8128 (2)0.0458 (6)
H18B0.64130.79410.79090.055*
S1A0.40017 (6)0.46380 (2)0.54540 (4)0.02973 (11)
O1A0.22909 (14)0.45426 (4)0.61460 (10)0.0228 (2)
N1A0.41622 (17)0.43676 (5)0.79594 (12)0.0224 (3)
N2A0.48826 (17)0.44323 (5)0.74796 (12)0.0212 (3)
N3A0.71546 (17)0.38885 (5)0.83070 (12)0.0216 (3)
N4A0.7102 (2)0.29173 (5)0.83187 (13)0.0288 (3)
C1A0.3773 (2)0.45354 (6)0.63837 (14)0.0218 (3)
C2A0.2620 (2)0.44351 (6)0.71288 (14)0.0207 (3)
C3A0.1288 (2)0.44023 (6)0.71368 (14)0.0218 (3)
C4A0.0338 (3)0.45153 (8)0.6297 (2)0.0265 (5)0.9
H4AA0.07610.46300.56010.032*0.9
C5A0.1282 (5)0.4435 (2)0.6622 (4)0.0308 (11)0.9
H5AA0.24000.44940.61630.037*0.9
C6A0.0374 (5)0.4264 (2)0.7679 (4)0.0303 (9)0.9
H6AA0.08080.41870.80180.036*0.9
S2A0.16500 (7)0.42031 (2)0.83162 (5)0.02979 (12)0.9
C4X0.125 (2)0.4241 (7)0.7841 (18)0.030 (4)*0.1
H4XA0.21940.41200.85060.036*0.1
C5X0.025 (4)0.424 (2)0.762 (3)0.022 (6)*0.1
H5XA0.04110.41550.81180.027*0.1
C6X0.145 (4)0.4397 (16)0.654 (3)0.010 (5)*0.1
H6XA0.25630.44070.61820.012*0.1
S2X0.0673 (7)0.45671 (18)0.5915 (4)0.0191 (11)*0.1
C7A0.6656 (2)0.43542 (6)0.81358 (15)0.0229 (3)
H7AA0.69850.45060.77570.028*
H7AB0.72440.44970.88640.028*
C8A0.7067 (3)0.36412 (7)0.90800 (16)0.0296 (4)
H8AA0.59300.35990.87410.035*
H8AB0.76090.38150.97660.035*
C9A0.7893 (3)0.31819 (7)0.93468 (16)0.0351 (4)
H9AA0.90420.32250.97170.042*
H9AB0.78280.30160.98540.042*
C10A0.7223 (2)0.31688 (6)0.75678 (15)0.0267 (4)
H10A0.67140.29940.68870.032*
H10B0.83680.32130.79290.032*
C11A0.6385 (2)0.36268 (6)0.72752 (14)0.0218 (3)
H11A0.64800.37920.67820.026*
H11B0.52300.35840.68870.026*
C12A0.7871 (3)0.24680 (7)0.85974 (18)0.0402 (5)
H12A0.78550.23250.91500.048*
H12B0.90080.25060.89330.048*
C13A0.7034 (3)0.21574 (6)0.75928 (17)0.0330 (4)
C14A0.5388 (3)0.20464 (8)0.6944 (2)0.0407 (5)
H14A0.47740.21690.71170.049*
C15A0.4650 (3)0.17530 (8)0.6036 (2)0.0450 (5)
H15A0.35450.16810.56050.054*
C16A0.5548 (3)0.15663 (7)0.5769 (2)0.0433 (5)
H16A0.50490.13720.51570.052*
C17A0.7186 (3)0.16709 (7)0.6416 (2)0.0433 (5)
H17A0.78000.15430.62480.052*
C18A0.7922 (3)0.19659 (7)0.7316 (2)0.0382 (5)
H18A0.90270.20370.77420.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1B0.0208 (2)0.0416 (3)0.0332 (2)0.00472 (18)0.01552 (19)0.0035 (2)
O1B0.0221 (6)0.0267 (6)0.0252 (6)0.0003 (5)0.0160 (5)0.0005 (5)
N1B0.0194 (6)0.0317 (8)0.0249 (7)0.0051 (6)0.0159 (6)0.0065 (6)
N2B0.0185 (6)0.0310 (8)0.0250 (7)0.0034 (5)0.0152 (6)0.0047 (6)
N3B0.0204 (7)0.0353 (8)0.0221 (7)0.0060 (6)0.0137 (6)0.0054 (6)
N4B0.0224 (7)0.0316 (8)0.0254 (8)0.0034 (6)0.0094 (6)0.0073 (6)
C1B0.0237 (8)0.0220 (8)0.0295 (8)0.0013 (6)0.0186 (7)0.0034 (6)
C2B0.0206 (7)0.0219 (8)0.0246 (8)0.0025 (6)0.0153 (7)0.0045 (6)
C3B0.0225 (7)0.0228 (8)0.0261 (8)0.0037 (6)0.0174 (7)0.0054 (6)
C4B0.0241 (13)0.0294 (13)0.0281 (15)0.0001 (10)0.0171 (13)0.0019 (12)
C5B0.041 (2)0.042 (3)0.046 (2)0.0133 (15)0.0372 (19)0.0147 (13)
C6B0.0233 (15)0.056 (2)0.0382 (18)0.0136 (13)0.0243 (15)0.0155 (13)
S2B0.0208 (3)0.0468 (4)0.0288 (3)0.0045 (3)0.0166 (3)0.0058 (3)
C7B0.0259 (8)0.0342 (9)0.0297 (9)0.0057 (7)0.0219 (7)0.0085 (7)
C8B0.0182 (7)0.0303 (9)0.0216 (8)0.0015 (6)0.0099 (7)0.0016 (7)
C9B0.0192 (8)0.0359 (10)0.0273 (9)0.0051 (7)0.0113 (7)0.0011 (7)
C10B0.0272 (9)0.0465 (12)0.0224 (9)0.0055 (8)0.0072 (8)0.0069 (8)
C11B0.0198 (8)0.0413 (11)0.0220 (8)0.0054 (7)0.0081 (7)0.0003 (7)
C12B0.0359 (11)0.0420 (12)0.0372 (11)0.0041 (9)0.0163 (10)0.0159 (9)
C13B0.0266 (9)0.0269 (9)0.0408 (11)0.0001 (7)0.0150 (9)0.0139 (8)
C14B0.0326 (10)0.0374 (11)0.0535 (14)0.0034 (9)0.0238 (10)0.0112 (10)
C15B0.0289 (10)0.0337 (11)0.0622 (16)0.0023 (9)0.0175 (11)0.0104 (11)
C16B0.0430 (13)0.0246 (10)0.0505 (14)0.0019 (9)0.0110 (11)0.0058 (10)
C17B0.0570 (15)0.0327 (12)0.0638 (17)0.0086 (11)0.0363 (14)0.0064 (11)
C18B0.0333 (11)0.0344 (11)0.0604 (15)0.0036 (9)0.0261 (11)0.0099 (10)
S1A0.0307 (2)0.0384 (3)0.0258 (2)0.00467 (19)0.02082 (19)0.00510 (18)
O1A0.0198 (5)0.0271 (6)0.0211 (6)0.0010 (5)0.0130 (5)0.0004 (5)
N1A0.0204 (6)0.0269 (7)0.0221 (7)0.0001 (5)0.0147 (6)0.0013 (5)
N2A0.0195 (6)0.0243 (7)0.0216 (6)0.0011 (5)0.0141 (6)0.0001 (5)
N3A0.0192 (6)0.0242 (7)0.0200 (6)0.0013 (5)0.0120 (6)0.0014 (5)
N4A0.0396 (9)0.0247 (7)0.0245 (7)0.0114 (6)0.0218 (7)0.0063 (6)
C1A0.0209 (7)0.0202 (7)0.0245 (8)0.0012 (6)0.0148 (7)0.0002 (6)
C2A0.0217 (7)0.0200 (7)0.0217 (7)0.0002 (6)0.0146 (6)0.0020 (6)
C3A0.0194 (7)0.0225 (8)0.0230 (8)0.0011 (6)0.0135 (6)0.0024 (6)
C4A0.0231 (10)0.0308 (11)0.0251 (12)0.0005 (8)0.0154 (10)0.0001 (10)
C5A0.0218 (14)0.033 (2)0.0358 (17)0.0034 (13)0.0179 (13)0.0032 (13)
C6A0.0215 (12)0.0390 (17)0.0345 (14)0.0028 (10)0.0200 (11)0.0025 (11)
S2A0.0218 (2)0.0423 (3)0.0259 (3)0.0006 (2)0.0158 (2)0.0029 (2)
C7A0.0170 (7)0.0260 (8)0.0239 (8)0.0023 (6)0.0123 (6)0.0037 (6)
C8A0.0387 (10)0.0305 (9)0.0233 (8)0.0077 (8)0.0218 (8)0.0032 (7)
C9A0.0461 (12)0.0333 (10)0.0218 (8)0.0142 (9)0.0201 (9)0.0061 (7)
C10A0.0304 (9)0.0285 (9)0.0244 (8)0.0067 (7)0.0191 (7)0.0019 (7)
C11A0.0228 (7)0.0235 (8)0.0185 (7)0.0012 (6)0.0130 (6)0.0006 (6)
C12A0.0545 (13)0.0310 (10)0.0327 (10)0.0205 (9)0.0272 (10)0.0101 (8)
C13A0.0525 (12)0.0221 (8)0.0351 (10)0.0144 (8)0.0331 (10)0.0109 (7)
C14A0.0559 (14)0.0341 (11)0.0505 (13)0.0101 (10)0.0427 (12)0.0072 (9)
C15A0.0579 (15)0.0338 (11)0.0504 (14)0.0004 (10)0.0382 (13)0.0051 (10)
C16A0.0722 (17)0.0240 (9)0.0413 (12)0.0055 (10)0.0402 (12)0.0065 (8)
C17A0.0719 (16)0.0300 (10)0.0500 (13)0.0129 (10)0.0493 (13)0.0064 (9)
C18A0.0518 (13)0.0305 (10)0.0456 (12)0.0117 (9)0.0374 (11)0.0063 (9)
Geometric parameters (Å, º) top
S1B—C1B1.6452 (18)S1A—C1A1.6484 (18)
O1B—C2B1.368 (2)O1A—C2A1.372 (2)
O1B—C1B1.377 (2)O1A—C1A1.374 (2)
N1B—C2B1.293 (2)N1A—C2A1.294 (2)
N1B—N2B1.3894 (19)N1A—N2A1.3917 (19)
N2B—C1B1.341 (2)N2A—C1A1.343 (2)
N2B—C7B1.481 (2)N2A—C7A1.478 (2)
N3B—C7B1.425 (2)N3A—C7A1.429 (2)
N3B—C11B1.463 (2)N3A—C8A1.463 (2)
N3B—C8B1.468 (2)N3A—C11A1.466 (2)
N4B—C9B1.459 (2)N4A—C10A1.461 (2)
N4B—C12B1.463 (3)N4A—C9A1.463 (2)
N4B—C10B1.467 (3)N4A—C12A1.464 (2)
C2B—C3B1.439 (2)C2A—C3A1.436 (2)
C3B—C4Y1.267 (17)C3A—C4X1.22 (2)
C3B—C4B1.377 (4)C3A—C4A1.380 (3)
C3B—S2B1.7132 (19)C3A—S2A1.7213 (18)
C3B—S2Y1.726 (4)C3A—S2X1.759 (6)
C4B—C5B1.403 (6)C4A—C5A1.411 (4)
C4B—H4BA0.9300C4A—H4AA0.9300
C5B—C6B1.353 (5)C5A—C6A1.360 (4)
C5B—H5BA0.9300C5A—H5AA0.9300
C6B—S2B1.710 (5)C6A—S2A1.709 (4)
C6B—H6BA0.9300C6A—H6AA0.9300
C4Y—C5Y1.395 (18)C4X—C5X1.413 (19)
C4Y—H4YA0.9300C4X—H4XA0.9300
C5Y—C6Y1.384 (15)C5X—C6X1.383 (17)
C5Y—H5YA0.9300C5X—H5XA0.9300
C6Y—S2Y1.716 (18)C6X—S2X1.712 (19)
C6Y—H6YA0.9300C6X—H6XA0.9300
C7B—H7BA0.9700C7A—H7AA0.9700
C7B—H7BB0.9700C7A—H7AB0.9700
C8B—C9B1.512 (3)C8A—C9A1.515 (3)
C8B—H8BA0.9700C8A—H8AA0.9700
C8B—H8BB0.9700C8A—H8AB0.9700
C9B—H9BA0.9700C9A—H9AA0.9700
C9B—H9BB0.9700C9A—H9AB0.9700
C10B—C11B1.512 (3)C10A—C11A1.513 (2)
C10B—H10C0.9700C10A—H10A0.9700
C10B—H10D0.9700C10A—H10B0.9700
C11B—H11C0.9700C11A—H11A0.9700
C11B—H11D0.9700C11A—H11B0.9700
C12B—C13B1.504 (3)C12A—C13A1.510 (3)
C12B—H12C0.9700C12A—H12A0.9700
C12B—H12D0.9700C12A—H12B0.9700
C13B—C18B1.381 (4)C13A—C14A1.387 (3)
C13B—C14B1.386 (3)C13A—C18A1.391 (3)
C14B—C15B1.378 (4)C14A—C15A1.388 (3)
C14B—H14B0.9300C14A—H14A0.9300
C15B—C16B1.369 (4)C15A—C16A1.384 (3)
C15B—H15B0.9300C15A—H15A0.9300
C16B—C17B1.389 (4)C16A—C17A1.375 (4)
C16B—H16B0.9300C16A—H16A0.9300
C17B—C18B1.388 (4)C17A—C18A1.384 (3)
C17B—H17B0.9300C17A—H17A0.9300
C18B—H18B0.9300C18A—H18A0.9300
C2B—O1B—C1B105.92 (13)C2A—O1A—C1A106.11 (13)
C2B—N1B—N2B103.24 (14)C2A—N1A—N2A103.26 (13)
C1B—N2B—N1B112.16 (14)C1A—N2A—N1A112.15 (13)
C1B—N2B—C7B126.86 (15)C1A—N2A—C7A126.78 (14)
N1B—N2B—C7B120.94 (14)N1A—N2A—C7A120.91 (14)
C7B—N3B—C11B113.95 (15)C7A—N3A—C8A114.47 (14)
C7B—N3B—C8B114.72 (15)C7A—N3A—C11A114.82 (14)
C11B—N3B—C8B111.03 (15)C8A—N3A—C11A110.91 (14)
C9B—N4B—C12B111.82 (16)C10A—N4A—C9A108.92 (16)
C9B—N4B—C10B108.63 (17)C10A—N4A—C12A111.72 (16)
C12B—N4B—C10B110.18 (16)C9A—N4A—C12A109.72 (15)
N2B—C1B—O1B105.16 (14)N2A—C1A—O1A105.17 (14)
N2B—C1B—S1B130.80 (14)N2A—C1A—S1A130.72 (13)
O1B—C1B—S1B124.01 (14)O1A—C1A—S1A124.11 (13)
N1B—C2B—O1B113.52 (14)N1A—C2A—O1A113.30 (14)
N1B—C2B—C3B127.69 (16)N1A—C2A—C3A127.53 (16)
O1B—C2B—C3B118.79 (15)O1A—C2A—C3A119.16 (15)
C4Y—C3B—C2B129.5 (7)C4X—C3A—C2A130.0 (9)
C4B—C3B—C2B129.1 (2)C4A—C3A—C2A128.50 (18)
C4B—C3B—S2B111.59 (17)C4A—C3A—S2A111.88 (15)
C2B—C3B—S2B119.30 (13)C2A—C3A—S2A119.61 (13)
C4Y—C3B—S2Y111.4 (7)C4X—C3A—S2X112.0 (10)
C2B—C3B—S2Y119.13 (17)C2A—C3A—S2X117.7 (2)
C3B—C4B—C5B112.6 (4)C3A—C4A—C5A111.8 (3)
C3B—C4B—H4BA123.7C3A—C4A—H4AA124.1
C5B—C4B—H4BA123.7C5A—C4A—H4AA124.1
C6B—C5B—C4B111.8 (5)C6A—C5A—C4A112.5 (4)
C6B—C5B—H5BA124.1C6A—C5A—H5AA123.7
C4B—C5B—H5BA124.1C4A—C5A—H5AA123.7
C5B—C6B—S2B113.2 (4)C5A—C6A—S2A112.7 (3)
C5B—C6B—H6BA123.4C5A—C6A—H6AA123.6
S2B—C6B—H6BA123.4S2A—C6A—H6AA123.6
C6B—S2B—C3B90.74 (19)C6A—S2A—C3A90.99 (14)
C3B—C4Y—C5Y118.1 (15)C3A—C4X—C5X118.3 (18)
C3B—C4Y—H4YA120.9C3A—C4X—H4XA120.8
C5Y—C4Y—H4YA120.9C5X—C4X—H4XA120.8
C6Y—C5Y—C4Y108.0 (19)C6X—C5X—C4X108 (2)
C6Y—C5Y—H5YA126.0C6X—C5X—H5XA126.1
C4Y—C5Y—H5YA126.0C4X—C5X—H5XA126.1
C5Y—C6Y—S2Y112.5 (17)C5X—C6X—S2X112.6 (19)
C5Y—C6Y—H6YA123.7C5X—C6X—H6XA123.7
S2Y—C6Y—H6YA123.7S2X—C6X—H6XA123.7
C6Y—S2Y—C3B89.7 (8)C6X—S2X—C3A88.9 (10)
N3B—C7B—N2B115.96 (15)N3A—C7A—N2A115.75 (14)
N3B—C7B—H7BA108.3N3A—C7A—H7AA108.3
N2B—C7B—H7BA108.3N2A—C7A—H7AA108.3
N3B—C7B—H7BB108.3N3A—C7A—H7AB108.3
N2B—C7B—H7BB108.3N2A—C7A—H7AB108.3
H7BA—C7B—H7BB107.4H7AA—C7A—H7AB107.4
N3B—C8B—C9B109.59 (15)N3A—C8A—C9A109.39 (15)
N3B—C8B—H8BA109.8N3A—C8A—H8AA109.8
C9B—C8B—H8BA109.8C9A—C8A—H8AA109.8
N3B—C8B—H8BB109.8N3A—C8A—H8AB109.8
C9B—C8B—H8BB109.8C9A—C8A—H8AB109.8
H8BA—C8B—H8BB108.2H8AA—C8A—H8AB108.2
N4B—C9B—C8B110.47 (15)N4A—C9A—C8A110.51 (15)
N4B—C9B—H9BA109.6N4A—C9A—H9AA109.5
C8B—C9B—H9BA109.6C8A—C9A—H9AA109.5
N4B—C9B—H9BB109.6N4A—C9A—H9AB109.5
C8B—C9B—H9BB109.6C8A—C9A—H9AB109.5
H9BA—C9B—H9BB108.1H9AA—C9A—H9AB108.1
N4B—C10B—C11B110.30 (16)N4A—C10A—C11A110.44 (14)
N4B—C10B—H10C109.6N4A—C10A—H10A109.6
C11B—C10B—H10C109.6C11A—C10A—H10A109.6
N4B—C10B—H10D109.6N4A—C10A—H10B109.6
C11B—C10B—H10D109.6C11A—C10A—H10B109.6
H10C—C10B—H10D108.1H10A—C10A—H10B108.1
N3B—C11B—C10B109.84 (16)N3A—C11A—C10A109.39 (14)
N3B—C11B—H11C109.7N3A—C11A—H11A109.8
C10B—C11B—H11C109.7C10A—C11A—H11A109.8
N3B—C11B—H11D109.7N3A—C11A—H11B109.8
C10B—C11B—H11D109.7C10A—C11A—H11B109.8
H11C—C11B—H11D108.2H11A—C11A—H11B108.2
N4B—C12B—C13B112.51 (17)N4A—C12A—C13A113.20 (17)
N4B—C12B—H12C109.1N4A—C12A—H12A108.9
C13B—C12B—H12C109.1C13A—C12A—H12A108.9
N4B—C12B—H12D109.1N4A—C12A—H12B108.9
C13B—C12B—H12D109.1C13A—C12A—H12B108.9
H12C—C12B—H12D107.8H12A—C12A—H12B107.8
C18B—C13B—C14B118.5 (2)C14A—C13A—C18A118.5 (2)
C18B—C13B—C12B120.8 (2)C14A—C13A—C12A121.40 (19)
C14B—C13B—C12B120.7 (2)C18A—C13A—C12A120.1 (2)
C15B—C14B—C13B121.2 (3)C13A—C14A—C15A120.5 (2)
C15B—C14B—H14B119.4C13A—C14A—H14A119.8
C13B—C14B—H14B119.4C15A—C14A—H14A119.8
C16B—C15B—C14B120.1 (2)C16A—C15A—C14A120.4 (3)
C16B—C15B—H15B119.9C16A—C15A—H15A119.8
C14B—C15B—H15B119.9C14A—C15A—H15A119.8
C15B—C16B—C17B119.7 (3)C17A—C16A—C15A119.4 (2)
C15B—C16B—H16B120.1C17A—C16A—H16A120.3
C17B—C16B—H16B120.1C15A—C16A—H16A120.3
C18B—C17B—C16B119.8 (3)C16A—C17A—C18A120.3 (2)
C18B—C17B—H17B120.1C16A—C17A—H17A119.8
C16B—C17B—H17B120.1C18A—C17A—H17A119.8
C13B—C18B—C17B120.6 (2)C17A—C18A—C13A120.9 (2)
C13B—C18B—H18B119.7C17A—C18A—H18A119.5
C17B—C18B—H18B119.7C13A—C18A—H18A119.5
C2B—N1B—N2B—C1B0.15 (19)C2A—N1A—N2A—C1A0.09 (19)
C2B—N1B—N2B—C7B177.93 (16)C2A—N1A—N2A—C7A175.66 (15)
N1B—N2B—C1B—O1B0.04 (19)N1A—N2A—C1A—O1A0.61 (18)
C7B—N2B—C1B—O1B177.65 (16)C7A—N2A—C1A—O1A175.86 (15)
N1B—N2B—C1B—S1B178.23 (14)N1A—N2A—C1A—S1A179.50 (13)
C7B—N2B—C1B—S1B0.6 (3)C7A—N2A—C1A—S1A4.2 (3)
C2B—O1B—C1B—N2B0.08 (18)C2A—O1A—C1A—N2A0.86 (17)
C2B—O1B—C1B—S1B178.50 (13)C2A—O1A—C1A—S1A179.24 (13)
N2B—N1B—C2B—O1B0.21 (19)N2A—N1A—C2A—O1A0.50 (18)
N2B—N1B—C2B—C3B179.12 (17)N2A—N1A—C2A—C3A178.47 (16)
C1B—O1B—C2B—N1B0.19 (19)C1A—O1A—C2A—N1A0.88 (19)
C1B—O1B—C2B—C3B179.20 (15)C1A—O1A—C2A—C3A178.17 (15)
N1B—C2B—C3B—C4Y3.6 (11)N1A—C2A—C3A—C4X12.6 (14)
O1B—C2B—C3B—C4Y175.7 (11)O1A—C2A—C3A—C4X166.3 (14)
N1B—C2B—C3B—C4B175.1 (2)N1A—C2A—C3A—C4A173.0 (2)
O1B—C2B—C3B—C4B5.6 (3)O1A—C2A—C3A—C4A8.1 (3)
N1B—C2B—C3B—S2B6.3 (3)N1A—C2A—C3A—S2A6.5 (3)
O1B—C2B—C3B—S2B172.95 (12)O1A—C2A—C3A—S2A172.39 (12)
N1B—C2B—C3B—S2Y174.4 (2)N1A—C2A—C3A—S2X173.9 (2)
O1B—C2B—C3B—S2Y6.3 (3)O1A—C2A—C3A—S2X7.2 (3)
C4Y—C3B—C4B—C5B1.6 (10)C4X—C3A—C4A—C5A4.5 (11)
C2B—C3B—C4B—C5B179.5 (5)C2A—C3A—C4A—C5A179.9 (3)
S2B—C3B—C4B—C5B0.9 (5)S2A—C3A—C4A—C5A0.4 (4)
S2Y—C3B—C4B—C5B176.9 (15)S2X—C3A—C4A—C5A175.8 (14)
C3B—C4B—C5B—C6B1.4 (10)C3A—C4A—C5A—C6A0.4 (6)
C4B—C5B—C6B—S2B1.3 (10)C4A—C5A—C6A—S2A1.0 (7)
C5B—C6B—S2B—C3B0.7 (7)C5A—C6A—S2A—C3A1.0 (5)
C4Y—C3B—S2B—C6B13 (5)C4X—C3A—S2A—C6A24 (5)
C4B—C3B—S2B—C6B0.1 (3)C4A—C3A—S2A—C6A0.8 (3)
C2B—C3B—S2B—C6B178.9 (3)C2A—C3A—S2A—C6A179.6 (3)
S2Y—C3B—S2B—C6B0.3 (3)S2X—C3A—S2A—C6A0.1 (3)
C4B—C3B—C4Y—C5Y4 (2)C4A—C3A—C4X—C5X3 (3)
C2B—C3B—C4Y—C5Y176.7 (18)C2A—C3A—C4X—C5X178 (3)
S2B—C3B—C4Y—C5Y163 (6)S2A—C3A—C4X—C5X154 (7)
S2Y—C3B—C4Y—C5Y5 (2)S2X—C3A—C4X—C5X5 (4)
C3B—C4Y—C5Y—C6Y3 (4)C3A—C4X—C5X—C6X6 (6)
C4Y—C5Y—C6Y—S2Y1 (4)C4X—C5X—C6X—S2X5 (6)
C5Y—C6Y—S2Y—C3B3 (3)C5X—C6X—S2X—C3A2 (4)
C4Y—C3B—S2Y—C6Y4.6 (16)C4X—C3A—S2X—C6X1 (2)
C4B—C3B—S2Y—C6Y0.3 (17)C4A—C3A—S2X—C6X8 (2)
C2B—C3B—S2Y—C6Y177.1 (13)C2A—C3A—S2X—C6X175.9 (17)
S2B—C3B—S2Y—C6Y2.1 (13)S2A—C3A—S2X—C6X3.6 (17)
C11B—N3B—C7B—N2B68.0 (2)C8A—N3A—C7A—N2A70.88 (19)
C8B—N3B—C7B—N2B61.6 (2)C11A—N3A—C7A—N2A59.11 (19)
C1B—N2B—C7B—N3B98.4 (2)C1A—N2A—C7A—N3A98.7 (2)
N1B—N2B—C7B—N3B84.2 (2)N1A—N2A—C7A—N3A76.1 (2)
C7B—N3B—C8B—C9B172.08 (15)C7A—N3A—C8A—C9A170.33 (16)
C11B—N3B—C8B—C9B56.94 (19)C11A—N3A—C8A—C9A57.8 (2)
C12B—N4B—C9B—C8B177.67 (18)C10A—N4A—C9A—C8A59.8 (2)
C10B—N4B—C9B—C8B60.5 (2)C12A—N4A—C9A—C8A177.65 (19)
N3B—C8B—C9B—N4B59.0 (2)N3A—C8A—C9A—N4A58.7 (2)
C9B—N4B—C10B—C11B60.3 (2)C9A—N4A—C10A—C11A59.9 (2)
C12B—N4B—C10B—C11B176.93 (19)C12A—N4A—C10A—C11A178.73 (17)
C7B—N3B—C11B—C10B171.68 (16)C7A—N3A—C11A—C10A170.34 (14)
C8B—N3B—C11B—C10B56.9 (2)C8A—N3A—C11A—C10A57.95 (18)
N4B—C10B—C11B—N3B58.7 (2)N4A—C10A—C11A—N3A59.00 (19)
C9B—N4B—C12B—C13B64.3 (3)C10A—N4A—C12A—C13A64.0 (2)
C10B—N4B—C12B—C13B174.8 (2)C9A—N4A—C12A—C13A175.08 (19)
N4B—C12B—C13B—C18B66.2 (3)N4A—C12A—C13A—C14A58.2 (3)
N4B—C12B—C13B—C14B113.6 (2)N4A—C12A—C13A—C18A123.5 (2)
C18B—C13B—C14B—C15B0.0 (3)C18A—C13A—C14A—C15A0.4 (3)
C12B—C13B—C14B—C15B179.9 (2)C12A—C13A—C14A—C15A178.7 (2)
C13B—C14B—C15B—C16B0.3 (4)C13A—C14A—C15A—C16A0.2 (3)
C14B—C15B—C16B—C17B0.2 (4)C14A—C15A—C16A—C17A0.5 (3)
C15B—C16B—C17B—C18B0.2 (4)C15A—C16A—C17A—C18A1.0 (3)
C14B—C13B—C18B—C17B0.3 (3)C16A—C17A—C18A—C13A0.8 (3)
C12B—C13B—C18B—C17B179.5 (2)C14A—C13A—C18A—C17A0.1 (3)
C16B—C17B—C18B—C13B0.4 (4)C12A—C13A—C18A—C17A178.27 (19)

Experimental details

Crystal data
Chemical formulaC18H20N4OS2
Mr372.50
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)10.6909 (5), 29.3658 (13), 15.6179 (6)
β (°) 130.283 (2)
V3)3740.4 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.30
Crystal size (mm)0.41 × 0.36 × 0.14
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
88935, 11407, 10339
Rint0.034
(sin θ/λ)max1)0.716
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.122, 1.19
No. of reflections11407
No. of parameters485
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.42

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick 2008), SHELXL2013 (Sheldrick, 2015), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

 

Footnotes

Thomson Reuters ResearcherID: C-3194-2011.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for funding this work through the Research Group Project No. RGP-274. CSCK thanks Universiti Sains Malaysia (USM) for a postdoctoral research fellowship.

References

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Volume 71| Part 3| March 2015| Pages o175-o176
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