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

Pöllnitz, A.; Varga, R.A.; Silvestru, A.

doi:10.1107/S1600536811000511

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o411

doi:10.1107/S1600536811000511

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

Alpar Pöllnitz,^a Richard A. Varga ^a ^* and Anca Silvestru ^a

^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 ); 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

Crystal data

C₁₀H₂₀N₂S₄Se
M_r = 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 ) T_min = 0.532, T_max = 0.630
17395 measured reflections
5896 independent reflections
4856 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 2755 Friedel pairs
Flack parameter: 0.007 (7)

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000511/bh2326sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000511/bh2326Isup2.hkl

checkCIF report

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.

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

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

C₁₀H₂₀N₂S₄Se	F(000) = 1536
M_r = 375.52	D_x = 1.464 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3414 reflections
a = 16.0338 (18) Å	θ = 2.4–21.5°
b = 15.6376 (18) Å	µ = 2.68 mm⁻¹
c = 13.5880 (15) Å	T = 297 K
V = 3406.9 (7) Å³	Block, orange
Z = 8	0.27 × 0.26 × 0.19 mm

Data collection top

Bruker SMART APEX diffractometer	5896 independent reflections
Radiation source: fine-focus sealed tube	4856 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→19
T_min = 0.532, T_max = 0.630	k = −18→17
17395 measured reflections	l = −16→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²)] where P = (F_o² + 2F_c²)/3
S = 0.94	(Δ/σ)_max = 0.001
5896 reflections	Δρ_max = 0.36 e Å⁻³
315 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2755 Friedel pairs
0 constraints	Absolute structure parameter: 0.007 (7)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₀H₂₀N₂S₄Se	V = 3406.9 (7) Å³
M_r = 375.52	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 16.0338 (18) Å	µ = 2.68 mm⁻¹
b = 15.6376 (18) Å	T = 297 K
c = 13.5880 (15) Å	0.27 × 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)
T_min = 0.532, T_max = 0.630	R_int = 0.046
17395 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.076	Δρ_max = 0.36 e Å⁻³
S = 0.94	Δρ_min = −0.22 e Å⁻³
5896 reflections	Absolute structure: Flack (1983), 2755 Friedel pairs
315 parameters	Absolute structure parameter: 0.007 (7)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2875 (3)	0.5449 (3)	0.9917 (3)	0.0528 (11)
C2	0.2975 (4)	0.4729 (4)	1.1515 (5)	0.0899 (18)
H2A	0.2578	0.4655	1.2046	0.108*
H2B	0.3357	0.5184	1.1697	0.108*
C3	0.3460 (5)	0.3900 (6)	1.1355 (9)	0.172 (4)
H3A	0.3078	0.3448	1.1194	0.258*
H3B	0.3757	0.3756	1.1946	0.258*
H3C	0.3849	0.3976	1.0825	0.258*
C4	0.1673 (3)	0.4642 (4)	1.0520 (4)	0.0766 (16)
H4A	0.1626	0.4094	1.0849	0.092*
H4B	0.1542	0.4558	0.9830	0.092*
C5	0.1059 (3)	0.5257 (5)	1.0961 (5)	0.106 (2)
H5A	0.1192	0.5346	1.1642	0.159*
H5B	0.0506	0.5025	1.0907	0.159*
H5C	0.1086	0.5792	1.0616	0.159*
C6	0.5408 (3)	0.7480 (3)	0.7986 (4)	0.0540 (12)
C7	0.6744 (3)	0.7964 (4)	0.8659 (5)	0.0879 (18)
H7A	0.6486	0.7904	0.9301	0.105*
H7B	0.7018	0.8517	0.8639	0.105*
C8	0.7384 (4)	0.7283 (4)	0.8539 (6)	0.104 (2)
H8A	0.7117	0.6734	0.8543	0.156*
H8B	0.7777	0.7314	0.9071	0.156*
H8C	0.7671	0.7362	0.7925	0.156*
C9	0.6213 (4)	0.8503 (4)	0.7051 (5)	0.0860 (18)
H9A	0.5988	0.8232	0.6466	0.103*
H9B	0.6806	0.8588	0.6949	0.103*
C10	0.5794 (4)	0.9369 (4)	0.7195 (7)	0.130 (3)
H10A	0.5209	0.9287	0.7309	0.195*
H10B	0.5872	0.9711	0.6616	0.195*
H10C	0.6038	0.9653	0.7751	0.195*
C11	0.5475 (2)	0.7900 (3)	0.2665 (4)	0.0511 (11)
C12	0.4976 (4)	0.7850 (4)	0.4376 (4)	0.0868 (18)
H12A	0.5448	0.8218	0.4516	0.104*
H12B	0.4982	0.7387	0.4850	0.104*
C13	0.4186 (5)	0.8354 (5)	0.4500 (6)	0.136 (3)
H13A	0.4187	0.8829	0.4053	0.205*
H13B	0.4150	0.8561	0.5164	0.205*
H13C	0.3715	0.7993	0.4364	0.205*
C14	0.4681 (3)	0.6663 (3)	0.3214 (5)	0.0836 (18)
H14A	0.4498	0.6628	0.2535	0.100*
H14B	0.4193	0.6611	0.3632	0.100*
C15	0.5265 (5)	0.5937 (4)	0.3426 (7)	0.127 (3)
H15A	0.5748	0.5984	0.3011	0.190*
H15B	0.4987	0.5405	0.3297	0.190*
H15C	0.5433	0.5958	0.4103	0.190*
C16	0.7525 (3)	1.0497 (3)	0.0838 (3)	0.0551 (12)
C17	0.8189 (3)	1.1743 (4)	0.1579 (5)	0.093 (2)
H17A	0.8760	1.1945	0.1537	0.112*
H17B	0.8135	1.1422	0.2186	0.112*
C18	0.7628 (4)	1.2492 (4)	0.1626 (7)	0.127 (3)
H18A	0.7674	1.2815	0.1028	0.191*
H18B	0.7782	1.2846	0.2174	0.191*
H18C	0.7063	1.2302	0.1707	0.191*
C19	0.8443 (4)	1.1369 (4)	−0.0176 (5)	0.0847 (18)
H19A	0.8535	1.1982	−0.0209	0.102*
H19B	0.8079	1.1213	−0.0717	0.102*
C20	0.9255 (4)	1.0925 (4)	−0.0301 (5)	0.105 (2)
H20A	0.9640	1.1124	0.0188	0.158*
H20B	0.9473	1.1043	−0.0945	0.158*
H20C	0.9175	1.0320	−0.0228	0.158*
N1	0.2536 (3)	0.4961 (2)	1.0614 (3)	0.0615 (11)
N2	0.6087 (2)	0.7942 (2)	0.7896 (3)	0.0598 (10)
N3	0.5070 (3)	0.7493 (3)	0.3382 (3)	0.0637 (11)
N4	0.8028 (2)	1.1167 (3)	0.0749 (3)	0.0633 (11)
S1	0.38904 (8)	0.58095 (9)	1.01289 (10)	0.0616 (3)
S2	0.24068 (9)	0.57133 (9)	0.88656 (11)	0.0775 (4)
S3	0.52830 (8)	0.68637 (9)	0.90454 (10)	0.0632 (3)
S4	0.46334 (8)	0.74428 (10)	0.71483 (10)	0.0758 (4)
S5	0.58959 (8)	0.88991 (8)	0.29503 (10)	0.0669 (4)
S6	0.56063 (7)	0.75098 (8)	0.15308 (10)	0.0597 (3)
S7	0.70132 (9)	1.03237 (8)	0.19479 (10)	0.0675 (4)
S8	0.73695 (10)	0.97916 (9)	−0.00757 (10)	0.0794 (4)
Se1	0.39627 (3)	0.64649 (3)	0.86143 (4)	0.05358 (13)
Se2	0.64458 (3)	0.90662 (3)	0.13955 (4)	0.05516 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.053 (3)	0.051 (3)	0.055 (3)	0.006 (2)	0.009 (2)	0.002 (2)
C2	0.091 (4)	0.120 (5)	0.058 (4)	−0.010 (4)	−0.002 (4)	0.030 (4)
C3	0.183 (8)	0.161 (8)	0.171 (9)	0.073 (7)	0.025 (8)	0.103 (8)
C4	0.082 (4)	0.083 (4)	0.065 (4)	−0.028 (3)	0.004 (3)	0.002 (3)
C5	0.062 (4)	0.154 (7)	0.101 (5)	−0.020 (4)	0.015 (4)	−0.019 (5)
C6	0.061 (3)	0.052 (3)	0.049 (3)	0.004 (2)	0.010 (2)	−0.007 (2)
C7	0.094 (4)	0.098 (5)	0.071 (4)	−0.043 (4)	−0.007 (4)	−0.022 (4)
C8	0.068 (4)	0.120 (5)	0.123 (6)	−0.009 (4)	−0.018 (4)	0.013 (5)
C9	0.077 (4)	0.089 (5)	0.093 (5)	−0.022 (3)	0.020 (3)	0.005 (4)
C10	0.126 (6)	0.075 (5)	0.188 (9)	−0.001 (4)	0.034 (6)	0.053 (5)
C11	0.043 (2)	0.050 (3)	0.061 (3)	0.004 (2)	0.002 (2)	0.009 (2)
C12	0.108 (4)	0.098 (5)	0.055 (4)	0.016 (4)	0.023 (3)	0.017 (3)
C13	0.151 (6)	0.162 (8)	0.096 (6)	0.070 (6)	0.046 (5)	0.010 (5)
C14	0.083 (4)	0.076 (4)	0.092 (5)	−0.015 (3)	0.017 (3)	0.017 (3)
C15	0.170 (7)	0.070 (4)	0.141 (7)	0.010 (4)	−0.009 (6)	0.035 (5)
C16	0.063 (3)	0.045 (3)	0.057 (3)	−0.005 (2)	−0.004 (3)	0.002 (2)
C17	0.080 (4)	0.084 (4)	0.115 (6)	−0.024 (3)	0.012 (4)	−0.033 (4)
C18	0.088 (4)	0.090 (5)	0.204 (9)	−0.012 (4)	0.050 (5)	−0.042 (5)
C19	0.105 (5)	0.069 (4)	0.080 (4)	−0.035 (3)	0.016 (4)	0.006 (3)
C20	0.110 (5)	0.104 (5)	0.101 (5)	−0.028 (4)	0.036 (5)	−0.018 (4)
N1	0.063 (3)	0.064 (3)	0.058 (3)	−0.004 (2)	0.004 (2)	0.007 (2)
N2	0.062 (2)	0.054 (2)	0.064 (3)	−0.0117 (19)	0.010 (2)	−0.005 (2)
N3	0.072 (3)	0.066 (3)	0.053 (3)	0.001 (2)	0.013 (2)	0.009 (2)
N4	0.068 (3)	0.053 (2)	0.070 (3)	−0.014 (2)	0.003 (2)	−0.002 (2)
S1	0.0544 (7)	0.0774 (9)	0.0529 (8)	−0.0004 (6)	−0.0011 (6)	0.0125 (6)
S2	0.0656 (8)	0.1032 (10)	0.0637 (9)	−0.0092 (8)	−0.0120 (7)	0.0199 (8)
S3	0.0588 (7)	0.0774 (9)	0.0534 (8)	−0.0031 (6)	0.0000 (6)	0.0056 (7)
S4	0.0649 (8)	0.0990 (11)	0.0635 (10)	−0.0127 (7)	−0.0047 (7)	0.0243 (8)
S5	0.0789 (9)	0.0604 (8)	0.0614 (8)	−0.0046 (6)	0.0107 (7)	−0.0104 (7)
S6	0.0708 (7)	0.0561 (7)	0.0522 (7)	−0.0081 (6)	0.0056 (7)	−0.0016 (6)
S7	0.0809 (9)	0.0592 (8)	0.0624 (8)	−0.0170 (7)	0.0135 (7)	−0.0101 (7)
S8	0.1033 (10)	0.0782 (10)	0.0565 (9)	−0.0355 (8)	0.0075 (8)	−0.0147 (7)
Se1	0.0552 (3)	0.0547 (3)	0.0509 (3)	0.0034 (2)	0.0032 (3)	0.0038 (2)
Se2	0.0558 (3)	0.0524 (3)	0.0572 (3)	−0.0074 (2)	0.0025 (3)	−0.0011 (3)

Geometric parameters (Å, º) top

C1—N1	1.332 (6)	C12—C13	1.501 (8)
C1—S2	1.666 (5)	C12—H12A	0.9700
C1—S1	1.747 (5)	C12—H12B	0.9700
C2—N1	1.458 (7)	C13—H13A	0.9600
C2—C3	1.527 (10)	C13—H13B	0.9600
C2—H2A	0.9700	C13—H13C	0.9600
C2—H2B	0.9700	C14—N3	1.457 (7)
C3—H3A	0.9600	C14—C15	1.499 (8)
C3—H3B	0.9600	C14—H14A	0.9700
C3—H3C	0.9600	C14—H14B	0.9700
C4—N1	1.476 (6)	C15—H15A	0.9600
C4—C5	1.501 (8)	C15—H15B	0.9600
C4—H4A	0.9700	C15—H15C	0.9600
C4—H4B	0.9700	C16—N4	1.327 (6)
C5—H5A	0.9600	C16—S8	1.680 (5)
C5—H5B	0.9600	C16—S7	1.738 (5)
C5—H5C	0.9600	C17—N4	1.467 (7)
C6—N2	1.312 (5)	C17—C18	1.478 (8)
C6—S4	1.685 (5)	C17—H17A	0.9700
C6—S3	1.744 (5)	C17—H17B	0.9700
C7—N2	1.479 (7)	C18—H18A	0.9600
C7—C8	1.488 (8)	C18—H18B	0.9600
C7—H7A	0.9700	C18—H18C	0.9600
C7—H7B	0.9700	C19—N4	1.457 (7)
C8—H8A	0.9600	C19—C20	1.485 (8)
C8—H8B	0.9600	C19—H19A	0.9700
C8—H8C	0.9600	C19—H19B	0.9700
C9—N2	1.460 (7)	C20—H20A	0.9600
C9—C10	1.523 (8)	C20—H20B	0.9600
C9—H9A	0.9700	C20—H20C	0.9600
C9—H9B	0.9700	S1—Se1	2.3020 (14)
C10—H10A	0.9600	S3—Se1	2.2833 (13)
C10—H10B	0.9600	S5—Se2	2.3041 (15)
C10—H10C	0.9600	S7—Se2	2.2930 (13)
C11—N3	1.332 (6)	S8—Se2	2.7343 (15)
C11—S6	1.671 (5)	S6—Se2	2.7873 (12)
C11—S5	1.746 (5)	S2—Se1	2.7788 (15)
C12—N3	1.470 (7)	S4—Se1	2.7318 (14)

N1—C1—S2	124.6 (3)	C12—C13—H13A	109.5
N1—C1—S1	116.6 (3)	C12—C13—H13B	109.5
S2—C1—S1	118.7 (3)	H13A—C13—H13B	109.5
N1—C2—C3	109.7 (6)	C12—C13—H13C	109.5
N1—C2—H2A	109.7	H13A—C13—H13C	109.5
C3—C2—H2A	109.7	H13B—C13—H13C	109.5
N1—C2—H2B	109.7	N3—C14—C15	112.2 (5)
C3—C2—H2B	109.7	N3—C14—H14A	109.2
H2A—C2—H2B	108.2	C15—C14—H14A	109.2
C2—C3—H3A	109.5	N3—C14—H14B	109.2
C2—C3—H3B	109.5	C15—C14—H14B	109.2
H3A—C3—H3B	109.5	H14A—C14—H14B	107.9
C2—C3—H3C	109.5	C14—C15—H15A	109.5
H3A—C3—H3C	109.5	C14—C15—H15B	109.5
H3B—C3—H3C	109.5	H15A—C15—H15B	109.5
N1—C4—C5	111.3 (5)	C14—C15—H15C	109.5
N1—C4—H4A	109.4	H15A—C15—H15C	109.5
C5—C4—H4A	109.4	H15B—C15—H15C	109.5
N1—C4—H4B	109.4	N4—C16—S8	122.7 (4)
C5—C4—H4B	109.4	N4—C16—S7	119.3 (4)
H4A—C4—H4B	108.0	S8—C16—S7	118.0 (3)
C4—C5—H5A	109.5	N4—C17—C18	114.4 (6)
C4—C5—H5B	109.5	N4—C17—H17A	108.7
H5A—C5—H5B	109.5	C18—C17—H17A	108.7
C4—C5—H5C	109.5	N4—C17—H17B	108.7
H5A—C5—H5C	109.5	C18—C17—H17B	108.7
H5B—C5—H5C	109.5	H17A—C17—H17B	107.6
N2—C6—S4	124.6 (4)	C17—C18—H18A	109.5
N2—C6—S3	118.4 (4)	C17—C18—H18B	109.5
S4—C6—S3	117.0 (3)	H18A—C18—H18B	109.5
N2—C7—C8	113.4 (5)	C17—C18—H18C	109.5
N2—C7—H7A	108.9	H18A—C18—H18C	109.5
C8—C7—H7A	108.9	H18B—C18—H18C	109.5
N2—C7—H7B	108.9	N4—C19—C20	113.4 (6)
C8—C7—H7B	108.9	N4—C19—H19A	108.9
H7A—C7—H7B	107.7	C20—C19—H19A	108.9
C7—C8—H8A	109.5	N4—C19—H19B	108.9
C7—C8—H8B	109.5	C20—C19—H19B	108.9
H8A—C8—H8B	109.5	H19A—C19—H19B	107.7
C7—C8—H8C	109.5	C19—C20—H20A	109.5
H8A—C8—H8C	109.5	C19—C20—H20B	109.5
H8B—C8—H8C	109.5	H20A—C20—H20B	109.5
N2—C9—C10	111.8 (5)	C19—C20—H20C	109.5
N2—C9—H9A	109.2	H20A—C20—H20C	109.5
C10—C9—H9A	109.2	H20B—C20—H20C	109.5
N2—C9—H9B	109.2	C1—N1—C2	122.8 (4)
C10—C9—H9B	109.2	C1—N1—C4	121.0 (4)
H9A—C9—H9B	107.9	C2—N1—C4	116.2 (4)
C9—C10—H10A	109.5	C6—N2—C9	121.3 (5)
C9—C10—H10B	109.5	C6—N2—C7	122.6 (4)
H10A—C10—H10B	109.5	C9—N2—C7	116.0 (4)
C9—C10—H10C	109.5	C11—N3—C14	121.3 (4)
H10A—C10—H10C	109.5	C11—N3—C12	122.7 (4)
H10B—C10—H10C	109.5	C14—N3—C12	116.0 (5)
N3—C11—S6	124.1 (4)	C16—N4—C19	121.9 (4)
N3—C11—S5	117.0 (4)	C16—N4—C17	121.4 (5)
S6—C11—S5	118.9 (3)	C19—N4—C17	116.7 (4)
N3—C12—C13	112.9 (6)	C1—S1—Se1	92.48 (16)
N3—C12—H12A	109.0	C6—S3—Se1	92.62 (16)
C13—C12—H12A	109.0	C11—S5—Se2	92.63 (16)
N3—C12—H12B	109.0	C16—S7—Se2	92.13 (16)
C13—C12—H12B	109.0	S3—Se1—S1	86.50 (5)
H12A—C12—H12B	107.8	S7—Se2—S5	87.07 (5)

S2—C1—N1—C2	178.6 (4)	C13—C12—N3—C11	92.4 (7)
S1—C1—N1—C2	−0.1 (6)	C13—C12—N3—C14	−86.8 (7)
S2—C1—N1—C4	−3.0 (7)	S8—C16—N4—C19	4.1 (7)
S1—C1—N1—C4	178.4 (4)	S7—C16—N4—C19	−177.0 (4)
C3—C2—N1—C1	−89.6 (7)	S8—C16—N4—C17	−176.3 (4)
C3—C2—N1—C4	91.9 (6)	S7—C16—N4—C17	2.5 (7)
C5—C4—N1—C1	−89.9 (6)	C20—C19—N4—C16	−87.4 (6)
C5—C4—N1—C2	88.7 (6)	C20—C19—N4—C17	93.0 (6)
S4—C6—N2—C9	2.5 (7)	C18—C17—N4—C16	−92.6 (7)
S3—C6—N2—C9	−177.1 (4)	C18—C17—N4—C19	87.0 (7)
S4—C6—N2—C7	179.0 (4)	N1—C1—S1—Se1	176.8 (3)
S3—C6—N2—C7	−0.5 (6)	S2—C1—S1—Se1	−2.0 (3)
C10—C9—N2—C6	84.1 (7)	N2—C6—S3—Se1	174.3 (3)
C10—C9—N2—C7	−92.7 (6)	S4—C6—S3—Se1	−5.3 (3)
C8—C7—N2—C6	88.1 (6)	N3—C11—S5—Se2	179.0 (3)
C8—C7—N2—C9	−95.2 (6)	S6—C11—S5—Se2	−0.6 (3)
S6—C11—N3—C14	−1.7 (7)	N4—C16—S7—Se2	−176.1 (4)
S5—C11—N3—C14	178.8 (4)	S8—C16—S7—Se2	2.8 (3)
S6—C11—N3—C12	179.2 (4)	C6—S3—Se1—S1	−174.55 (15)
S5—C11—N3—C12	−0.4 (6)	C1—S1—Se1—S3	−179.80 (16)
C15—C14—N3—C11	90.1 (7)	C16—S7—Se2—S5	176.19 (17)
C15—C14—N3—C12	−90.7 (6)	C11—S5—Se2—S7	−176.75 (15)

Experimental details

Crystal data
Chemical formula	C₁₀H₂₀N₂S₄Se
M_r	375.52
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	297
a, b, c (Å)	16.0338 (18), 15.6376 (18), 13.5880 (15)
V (Å³)	3406.9 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.68
Crystal size (mm)	0.27 × 0.26 × 0.19

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.532, 0.630
No. of measured, independent and observed [I > 2σ(I)] reflections	17395, 5896, 4856
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.076, 0.94
No. of reflections	5896
No. of parameters	315
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.22
Absolute structure	Flack (1983), 2755 Friedel pairs
Absolute structure parameter	0.007 (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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