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

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ISSN: 2056-9890

A new ortho­rhom­bic polymorph of 1,1′-seleno­bis­­(N,N-di­ethyl­sulfanecarbo­thio­amide)

aFaculty of Chemistry and Chemical Engineering, Babes-Bolyai University, 11 Arany Janos St., RO-400028, Cluj Napoca, Romania
*Correspondence e-mail: richy@chem.ubbcluj.ro

(Received 15 November 2010; accepted 5 January 2011; online 15 January 2011)

The title compound [systematic name: N,N-dieth­yl({[(diethyl­carbamothio­yl)sulfan­yl]selan­yl}sulfan­yl)carbothio­amide], C10H20N2S4Se, crystallizes in a new form in the space group Pca21: the previously reported polymorph crystallizes in the space group P212121. The new phase contains two independent mol­ecules in the asymmetric unit. The Se atoms are tetra­coordinated, with a distorted square-planar geometry. The ligands coordinate asymmetrically to the Se atoms, with one strong Se—S bond [range 2.2833 (13)–2.3041 (15) Å] and one weaker bond [range 2.7318 (14)–2.7873 (12) Å].

Related literature

For the characterization of the P212121 polymorph, see: Conde et al. (1970[Conde, A., Bernier, F., López-Castro, A. & Márquez, R. (1970). Acta Cryst. B26, 2135.]); Husebye & Helland-Madsen (1970[Husebye, S. & Helland-Madsen, G. (1970). Acta Chem. Scand. 24, 2273-2284.]); Sugihara (1985[Sugihara, A. (1985). Kagaku To Kogyo (Osaka), 59, 319-322.]). For the benzene solvate, see: Klapötke et al. (2008[Klapötke, T. M., Krumm, B. & Scherr, M. (2008). Inorg. Chem. 47, 4712-4722.]). For the synthesis of bis­(o-formyl­phen­yl)selenide acetal, see: Panda et al. (2001[Panda, A., Menon, S. C., Singh, H. B. & Butcher, R. J. (2001). J. Organomet. Chem. 623, 87-94.]).

[Scheme 1]

Experimental

Crystal data
  • C10H20N2S4Se

  • Mr = 375.52

  • Orthorhombic, P c a 21

  • a = 16.0338 (18) Å

  • b = 15.6376 (18) Å

  • c = 13.5880 (15) Å

  • V = 3406.9 (7) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 2.68 mm−1

  • T = 297 K

  • 0.27 × 0.26 × 0.19 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.532, Tmax = 0.630

  • 17395 measured reflections

  • 5896 independent reflections

  • 4856 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.076

  • S = 0.94

  • 5896 reflections

  • 315 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.22 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2755 Friedel pairs

  • Flack parameter: 0.007 (7)

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

In the crystal, the title compound contains two independent molecules in the asymmetric unit, with only slight differences in the bond distances and bond angles between the two molecules (Fig. 1). Both Se atoms are tetracoordinated with four S atoms arranged in a distorted square-planar geometry. The distortion of the coordination geometry is the result of the small bite and asymmetric coordination of the ligands. Each ligand coordinates strongly to the corresponding Se center through one S atom [range 2.2833 (13)–2.3041 (15) Å] and forms a weaker interaction through the second S atom [range 2.7318 (14)–2.7873 (12) Å].

The molecular structure is similar to the ones published (Klapötke et al., 2008; Sugihara, 1985; Husebye & Helland-Madsen, 1970; Conde et al., 1970) in terms of structure parameters. Only one difference can be observed between the title compound and the benzene solvate (Klapötke et al., 2008), the position of the Et groups from the ligands. While in the title compound the organic fragments from the same ligand are on the opposite sides of the coordination plane, in the benzene solvate they are on the same side.

Related literature top

For the characterization of the P212121 polymorph, see: Conde et al. (1970); Husebye & Helland-Madsen (1970); Sugihara (1985). For the benzene solvate, see: Klapötke et al. (2008). For the synthesis of bis(o-formylphenyl)selenide acetal, see: Panda et al. (2001).

Experimental top

The title compound was recovered as unreacted material after the reaction described for the synthesis of bis(o-formylphenyl)selenide acetal by Panda et al. (2001). Recrystallization from diethylether at -20°C over 72 h afforded suitable crystals.

Refinement top

All hydrogen atoms were placed in calculated positions using a riding model, with C—H = 0.96–0.97 Å and with Uiso= 1.2 or 1.5Ueq (C) for H. The methyl groups were allowed to rotate but not to tip.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
N,N- diethyl({[(diethylcarbamothioyl)sulfanyl]selanyl}sulfanyl)carbothioamide top
Crystal data top
C10H20N2S4SeF(000) = 1536
Mr = 375.52Dx = 1.464 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 3414 reflections
a = 16.0338 (18) Åθ = 2.4–21.5°
b = 15.6376 (18) ŵ = 2.68 mm1
c = 13.5880 (15) ÅT = 297 K
V = 3406.9 (7) Å3Block, orange
Z = 80.27 × 0.26 × 0.19 mm
Data collection top
Bruker SMART APEX
diffractometer
5896 independent reflections
Radiation source: fine-focus sealed tube4856 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ϕ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1819
Tmin = 0.532, Tmax = 0.630k = 1817
17395 measured reflectionsl = 1615
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)] = 0.038H-atom parameters constrained
wR(F2) = 0.076 w = 1/[σ2(Fo2)]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.001
5896 reflectionsΔρmax = 0.36 e Å3
315 parametersΔρmin = 0.22 e Å3
1 restraintAbsolute structure: Flack (1983), 2755 Friedel pairs
0 constraintsAbsolute structure parameter: 0.007 (7)
Primary atom site location: structure-invariant direct methods
Crystal data top
C10H20N2S4SeV = 3406.9 (7) Å3
Mr = 375.52Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 16.0338 (18) ŵ = 2.68 mm1
b = 15.6376 (18) ÅT = 297 K
c = 13.5880 (15) Å0.27 × 0.26 × 0.19 mm
Data collection top
Bruker SMART APEX
diffractometer
5896 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
4856 reflections with I > 2σ(I)
Tmin = 0.532, Tmax = 0.630Rint = 0.046
17395 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.076Δρmax = 0.36 e Å3
S = 0.94Δρmin = 0.22 e Å3
5896 reflectionsAbsolute structure: Flack (1983), 2755 Friedel pairs
315 parametersAbsolute structure parameter: 0.007 (7)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2875 (3)0.5449 (3)0.9917 (3)0.0528 (11)
C20.2975 (4)0.4729 (4)1.1515 (5)0.0899 (18)
H2A0.25780.46551.20460.108*
H2B0.33570.51841.16970.108*
C30.3460 (5)0.3900 (6)1.1355 (9)0.172 (4)
H3A0.30780.34481.11940.258*
H3B0.37570.37561.19460.258*
H3C0.38490.39761.08250.258*
C40.1673 (3)0.4642 (4)1.0520 (4)0.0766 (16)
H4A0.16260.40941.08490.092*
H4B0.15420.45580.98300.092*
C50.1059 (3)0.5257 (5)1.0961 (5)0.106 (2)
H5A0.11920.53461.16420.159*
H5B0.05060.50251.09070.159*
H5C0.10860.57921.06160.159*
C60.5408 (3)0.7480 (3)0.7986 (4)0.0540 (12)
C70.6744 (3)0.7964 (4)0.8659 (5)0.0879 (18)
H7A0.64860.79040.93010.105*
H7B0.70180.85170.86390.105*
C80.7384 (4)0.7283 (4)0.8539 (6)0.104 (2)
H8A0.71170.67340.85430.156*
H8B0.77770.73140.90710.156*
H8C0.76710.73620.79250.156*
C90.6213 (4)0.8503 (4)0.7051 (5)0.0860 (18)
H9A0.59880.82320.64660.103*
H9B0.68060.85880.69490.103*
C100.5794 (4)0.9369 (4)0.7195 (7)0.130 (3)
H10A0.52090.92870.73090.195*
H10B0.58720.97110.66160.195*
H10C0.60380.96530.77510.195*
C110.5475 (2)0.7900 (3)0.2665 (4)0.0511 (11)
C120.4976 (4)0.7850 (4)0.4376 (4)0.0868 (18)
H12A0.54480.82180.45160.104*
H12B0.49820.73870.48500.104*
C130.4186 (5)0.8354 (5)0.4500 (6)0.136 (3)
H13A0.41870.88290.40530.205*
H13B0.41500.85610.51640.205*
H13C0.37150.79930.43640.205*
C140.4681 (3)0.6663 (3)0.3214 (5)0.0836 (18)
H14A0.44980.66280.25350.100*
H14B0.41930.66110.36320.100*
C150.5265 (5)0.5937 (4)0.3426 (7)0.127 (3)
H15A0.57480.59840.30110.190*
H15B0.49870.54050.32970.190*
H15C0.54330.59580.41030.190*
C160.7525 (3)1.0497 (3)0.0838 (3)0.0551 (12)
C170.8189 (3)1.1743 (4)0.1579 (5)0.093 (2)
H17A0.87601.19450.15370.112*
H17B0.81351.14220.21860.112*
C180.7628 (4)1.2492 (4)0.1626 (7)0.127 (3)
H18A0.76741.28150.10280.191*
H18B0.77821.28460.21740.191*
H18C0.70631.23020.17070.191*
C190.8443 (4)1.1369 (4)0.0176 (5)0.0847 (18)
H19A0.85351.19820.02090.102*
H19B0.80791.12130.07170.102*
C200.9255 (4)1.0925 (4)0.0301 (5)0.105 (2)
H20A0.96401.11240.01880.158*
H20B0.94731.10430.09450.158*
H20C0.91751.03200.02280.158*
N10.2536 (3)0.4961 (2)1.0614 (3)0.0615 (11)
N20.6087 (2)0.7942 (2)0.7896 (3)0.0598 (10)
N30.5070 (3)0.7493 (3)0.3382 (3)0.0637 (11)
N40.8028 (2)1.1167 (3)0.0749 (3)0.0633 (11)
S10.38904 (8)0.58095 (9)1.01289 (10)0.0616 (3)
S20.24068 (9)0.57133 (9)0.88656 (11)0.0775 (4)
S30.52830 (8)0.68637 (9)0.90454 (10)0.0632 (3)
S40.46334 (8)0.74428 (10)0.71483 (10)0.0758 (4)
S50.58959 (8)0.88991 (8)0.29503 (10)0.0669 (4)
S60.56063 (7)0.75098 (8)0.15308 (10)0.0597 (3)
S70.70132 (9)1.03237 (8)0.19479 (10)0.0675 (4)
S80.73695 (10)0.97916 (9)0.00757 (10)0.0794 (4)
Se10.39627 (3)0.64649 (3)0.86143 (4)0.05358 (13)
Se20.64458 (3)0.90662 (3)0.13955 (4)0.05516 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.053 (3)0.051 (3)0.055 (3)0.006 (2)0.009 (2)0.002 (2)
C20.091 (4)0.120 (5)0.058 (4)0.010 (4)0.002 (4)0.030 (4)
C30.183 (8)0.161 (8)0.171 (9)0.073 (7)0.025 (8)0.103 (8)
C40.082 (4)0.083 (4)0.065 (4)0.028 (3)0.004 (3)0.002 (3)
C50.062 (4)0.154 (7)0.101 (5)0.020 (4)0.015 (4)0.019 (5)
C60.061 (3)0.052 (3)0.049 (3)0.004 (2)0.010 (2)0.007 (2)
C70.094 (4)0.098 (5)0.071 (4)0.043 (4)0.007 (4)0.022 (4)
C80.068 (4)0.120 (5)0.123 (6)0.009 (4)0.018 (4)0.013 (5)
C90.077 (4)0.089 (5)0.093 (5)0.022 (3)0.020 (3)0.005 (4)
C100.126 (6)0.075 (5)0.188 (9)0.001 (4)0.034 (6)0.053 (5)
C110.043 (2)0.050 (3)0.061 (3)0.004 (2)0.002 (2)0.009 (2)
C120.108 (4)0.098 (5)0.055 (4)0.016 (4)0.023 (3)0.017 (3)
C130.151 (6)0.162 (8)0.096 (6)0.070 (6)0.046 (5)0.010 (5)
C140.083 (4)0.076 (4)0.092 (5)0.015 (3)0.017 (3)0.017 (3)
C150.170 (7)0.070 (4)0.141 (7)0.010 (4)0.009 (6)0.035 (5)
C160.063 (3)0.045 (3)0.057 (3)0.005 (2)0.004 (3)0.002 (2)
C170.080 (4)0.084 (4)0.115 (6)0.024 (3)0.012 (4)0.033 (4)
C180.088 (4)0.090 (5)0.204 (9)0.012 (4)0.050 (5)0.042 (5)
C190.105 (5)0.069 (4)0.080 (4)0.035 (3)0.016 (4)0.006 (3)
C200.110 (5)0.104 (5)0.101 (5)0.028 (4)0.036 (5)0.018 (4)
N10.063 (3)0.064 (3)0.058 (3)0.004 (2)0.004 (2)0.007 (2)
N20.062 (2)0.054 (2)0.064 (3)0.0117 (19)0.010 (2)0.005 (2)
N30.072 (3)0.066 (3)0.053 (3)0.001 (2)0.013 (2)0.009 (2)
N40.068 (3)0.053 (2)0.070 (3)0.014 (2)0.003 (2)0.002 (2)
S10.0544 (7)0.0774 (9)0.0529 (8)0.0004 (6)0.0011 (6)0.0125 (6)
S20.0656 (8)0.1032 (10)0.0637 (9)0.0092 (8)0.0120 (7)0.0199 (8)
S30.0588 (7)0.0774 (9)0.0534 (8)0.0031 (6)0.0000 (6)0.0056 (7)
S40.0649 (8)0.0990 (11)0.0635 (10)0.0127 (7)0.0047 (7)0.0243 (8)
S50.0789 (9)0.0604 (8)0.0614 (8)0.0046 (6)0.0107 (7)0.0104 (7)
S60.0708 (7)0.0561 (7)0.0522 (7)0.0081 (6)0.0056 (7)0.0016 (6)
S70.0809 (9)0.0592 (8)0.0624 (8)0.0170 (7)0.0135 (7)0.0101 (7)
S80.1033 (10)0.0782 (10)0.0565 (9)0.0355 (8)0.0075 (8)0.0147 (7)
Se10.0552 (3)0.0547 (3)0.0509 (3)0.0034 (2)0.0032 (3)0.0038 (2)
Se20.0558 (3)0.0524 (3)0.0572 (3)0.0074 (2)0.0025 (3)0.0011 (3)
Geometric parameters (Å, º) top
C1—N11.332 (6)C12—C131.501 (8)
C1—S21.666 (5)C12—H12A0.9700
C1—S11.747 (5)C12—H12B0.9700
C2—N11.458 (7)C13—H13A0.9600
C2—C31.527 (10)C13—H13B0.9600
C2—H2A0.9700C13—H13C0.9600
C2—H2B0.9700C14—N31.457 (7)
C3—H3A0.9600C14—C151.499 (8)
C3—H3B0.9600C14—H14A0.9700
C3—H3C0.9600C14—H14B0.9700
C4—N11.476 (6)C15—H15A0.9600
C4—C51.501 (8)C15—H15B0.9600
C4—H4A0.9700C15—H15C0.9600
C4—H4B0.9700C16—N41.327 (6)
C5—H5A0.9600C16—S81.680 (5)
C5—H5B0.9600C16—S71.738 (5)
C5—H5C0.9600C17—N41.467 (7)
C6—N21.312 (5)C17—C181.478 (8)
C6—S41.685 (5)C17—H17A0.9700
C6—S31.744 (5)C17—H17B0.9700
C7—N21.479 (7)C18—H18A0.9600
C7—C81.488 (8)C18—H18B0.9600
C7—H7A0.9700C18—H18C0.9600
C7—H7B0.9700C19—N41.457 (7)
C8—H8A0.9600C19—C201.485 (8)
C8—H8B0.9600C19—H19A0.9700
C8—H8C0.9600C19—H19B0.9700
C9—N21.460 (7)C20—H20A0.9600
C9—C101.523 (8)C20—H20B0.9600
C9—H9A0.9700C20—H20C0.9600
C9—H9B0.9700S1—Se12.3020 (14)
C10—H10A0.9600S3—Se12.2833 (13)
C10—H10B0.9600S5—Se22.3041 (15)
C10—H10C0.9600S7—Se22.2930 (13)
C11—N31.332 (6)S8—Se22.7343 (15)
C11—S61.671 (5)S6—Se22.7873 (12)
C11—S51.746 (5)S2—Se12.7788 (15)
C12—N31.470 (7)S4—Se12.7318 (14)
N1—C1—S2124.6 (3)C12—C13—H13A109.5
N1—C1—S1116.6 (3)C12—C13—H13B109.5
S2—C1—S1118.7 (3)H13A—C13—H13B109.5
N1—C2—C3109.7 (6)C12—C13—H13C109.5
N1—C2—H2A109.7H13A—C13—H13C109.5
C3—C2—H2A109.7H13B—C13—H13C109.5
N1—C2—H2B109.7N3—C14—C15112.2 (5)
C3—C2—H2B109.7N3—C14—H14A109.2
H2A—C2—H2B108.2C15—C14—H14A109.2
C2—C3—H3A109.5N3—C14—H14B109.2
C2—C3—H3B109.5C15—C14—H14B109.2
H3A—C3—H3B109.5H14A—C14—H14B107.9
C2—C3—H3C109.5C14—C15—H15A109.5
H3A—C3—H3C109.5C14—C15—H15B109.5
H3B—C3—H3C109.5H15A—C15—H15B109.5
N1—C4—C5111.3 (5)C14—C15—H15C109.5
N1—C4—H4A109.4H15A—C15—H15C109.5
C5—C4—H4A109.4H15B—C15—H15C109.5
N1—C4—H4B109.4N4—C16—S8122.7 (4)
C5—C4—H4B109.4N4—C16—S7119.3 (4)
H4A—C4—H4B108.0S8—C16—S7118.0 (3)
C4—C5—H5A109.5N4—C17—C18114.4 (6)
C4—C5—H5B109.5N4—C17—H17A108.7
H5A—C5—H5B109.5C18—C17—H17A108.7
C4—C5—H5C109.5N4—C17—H17B108.7
H5A—C5—H5C109.5C18—C17—H17B108.7
H5B—C5—H5C109.5H17A—C17—H17B107.6
N2—C6—S4124.6 (4)C17—C18—H18A109.5
N2—C6—S3118.4 (4)C17—C18—H18B109.5
S4—C6—S3117.0 (3)H18A—C18—H18B109.5
N2—C7—C8113.4 (5)C17—C18—H18C109.5
N2—C7—H7A108.9H18A—C18—H18C109.5
C8—C7—H7A108.9H18B—C18—H18C109.5
N2—C7—H7B108.9N4—C19—C20113.4 (6)
C8—C7—H7B108.9N4—C19—H19A108.9
H7A—C7—H7B107.7C20—C19—H19A108.9
C7—C8—H8A109.5N4—C19—H19B108.9
C7—C8—H8B109.5C20—C19—H19B108.9
H8A—C8—H8B109.5H19A—C19—H19B107.7
C7—C8—H8C109.5C19—C20—H20A109.5
H8A—C8—H8C109.5C19—C20—H20B109.5
H8B—C8—H8C109.5H20A—C20—H20B109.5
N2—C9—C10111.8 (5)C19—C20—H20C109.5
N2—C9—H9A109.2H20A—C20—H20C109.5
C10—C9—H9A109.2H20B—C20—H20C109.5
N2—C9—H9B109.2C1—N1—C2122.8 (4)
C10—C9—H9B109.2C1—N1—C4121.0 (4)
H9A—C9—H9B107.9C2—N1—C4116.2 (4)
C9—C10—H10A109.5C6—N2—C9121.3 (5)
C9—C10—H10B109.5C6—N2—C7122.6 (4)
H10A—C10—H10B109.5C9—N2—C7116.0 (4)
C9—C10—H10C109.5C11—N3—C14121.3 (4)
H10A—C10—H10C109.5C11—N3—C12122.7 (4)
H10B—C10—H10C109.5C14—N3—C12116.0 (5)
N3—C11—S6124.1 (4)C16—N4—C19121.9 (4)
N3—C11—S5117.0 (4)C16—N4—C17121.4 (5)
S6—C11—S5118.9 (3)C19—N4—C17116.7 (4)
N3—C12—C13112.9 (6)C1—S1—Se192.48 (16)
N3—C12—H12A109.0C6—S3—Se192.62 (16)
C13—C12—H12A109.0C11—S5—Se292.63 (16)
N3—C12—H12B109.0C16—S7—Se292.13 (16)
C13—C12—H12B109.0S3—Se1—S186.50 (5)
H12A—C12—H12B107.8S7—Se2—S587.07 (5)
S2—C1—N1—C2178.6 (4)C13—C12—N3—C1192.4 (7)
S1—C1—N1—C20.1 (6)C13—C12—N3—C1486.8 (7)
S2—C1—N1—C43.0 (7)S8—C16—N4—C194.1 (7)
S1—C1—N1—C4178.4 (4)S7—C16—N4—C19177.0 (4)
C3—C2—N1—C189.6 (7)S8—C16—N4—C17176.3 (4)
C3—C2—N1—C491.9 (6)S7—C16—N4—C172.5 (7)
C5—C4—N1—C189.9 (6)C20—C19—N4—C1687.4 (6)
C5—C4—N1—C288.7 (6)C20—C19—N4—C1793.0 (6)
S4—C6—N2—C92.5 (7)C18—C17—N4—C1692.6 (7)
S3—C6—N2—C9177.1 (4)C18—C17—N4—C1987.0 (7)
S4—C6—N2—C7179.0 (4)N1—C1—S1—Se1176.8 (3)
S3—C6—N2—C70.5 (6)S2—C1—S1—Se12.0 (3)
C10—C9—N2—C684.1 (7)N2—C6—S3—Se1174.3 (3)
C10—C9—N2—C792.7 (6)S4—C6—S3—Se15.3 (3)
C8—C7—N2—C688.1 (6)N3—C11—S5—Se2179.0 (3)
C8—C7—N2—C995.2 (6)S6—C11—S5—Se20.6 (3)
S6—C11—N3—C141.7 (7)N4—C16—S7—Se2176.1 (4)
S5—C11—N3—C14178.8 (4)S8—C16—S7—Se22.8 (3)
S6—C11—N3—C12179.2 (4)C6—S3—Se1—S1174.55 (15)
S5—C11—N3—C120.4 (6)C1—S1—Se1—S3179.80 (16)
C15—C14—N3—C1190.1 (7)C16—S7—Se2—S5176.19 (17)
C15—C14—N3—C1290.7 (6)C11—S5—Se2—S7176.75 (15)

Experimental details

Crystal data
Chemical formulaC10H20N2S4Se
Mr375.52
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)297
a, b, c (Å)16.0338 (18), 15.6376 (18), 13.5880 (15)
V3)3406.9 (7)
Z8
Radiation typeMo Kα
µ (mm1)2.68
Crystal size (mm)0.27 × 0.26 × 0.19
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.532, 0.630
No. of measured, independent and
observed [I > 2σ(I)] reflections
17395, 5896, 4856
Rint0.046
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.076, 0.94
No. of reflections5896
No. of parameters315
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.22
Absolute structureFlack (1983), 2755 Friedel pairs
Absolute structure parameter0.007 (7)

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

 

Acknowledgements

Financial support from the National University Research Council of Romania (Research Project PNII-ID-2404/2008) is greatly appreciated.

References

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