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The title compounds of sulfur, C10H6N2O4S2, (I), and selenium, C10H6N2O4Se2, (II), are isomorphous. The crystallographically centrosymmetric mol­ecules are planar. The bond distances and angles, except for those involving the S and Se atoms, are comparable. The mol­ecules are disposed in layers parallel to the bc plane. The molecular axes differ by 75° for (I) and by 80° for (II) from one layer to the next.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199010100/fg1563sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199010100/fg1563Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199010100/fg1563IIsup3.hkl
Contains datablock plas

CCDC references: 142743; 142744

Comment top

Charge-transfer (CT) complexes and radical cation salts derived from 1,4-dithiine and its derivatives exhibit high electrical conductivities. It has been reported that N,N'-dimethyl-1,4-dithiine-1,2:4,5-tetracarboximide, (I), reacts with various anthracenes via charge-transfer complexes to give Diels–Alder adducts and that, in contrast, the reaction of (I) with acridine gives a stable 1:1 complex which does not give rise to any adducts (Hayakawa et al., 1982). 1,4-Dithiines normally adopt a boat conformation in which the S atoms are tilted towards one another (Howell et al., 1954). However, various molecular-orbital calculations have indicated that the energy barrier between the planar and boat conformers is very small (Galasso, 1981; Saebo et al., 1984; Kao et al., 1985). The observed structural trends for 1,4-dithiines suggest that the planar structure is stabilized by electron-withdrawing substitutents (Hayakawa et al., 1982; Lozac'h, 1989). However, unlike other 1,4-dithiines, the 1:1 complex of (I) and acridine (Yamaguchi & Ueda, 1984) is almost planar. We now report the structural characterization of N,N'-dimethyl-1,4-dithiine-1,2:4,5-tetracarboximide, related to 1,4-dithiines, and N,N'-dimethyl-1,4-diselenine-1,2:4,5-tetracarboximide, (II), in which the S atoms are substituted by Se atoms.

Except for the b value, the other unit-cell dimensions are slightly larger for the Se derivative. In fact, the two compounds, which belong to the same space group, are isomorphous and the molecules are crystallographically centrosymmetric. Both molecules are planar. The diimide atoms (C3, C4, N4, C5, O3 and O5) almost lie in the plane of the six-membered ring. The largest deviations from the least-squares plane are 0.034 (6) and 0.023 (12) Å for the dithiine and diselenine compounds, respectively, and they are close to those reported for the 1:1 1,4-dithiine–acridine complex (Yamaguchi & Ueda, 1984). The bond distances and valence angles in (I), (II) and the above 1:1 1,4-dithiine–acridine complex are comparable.

In both (I) and (II), the conjugated Csp2—Csp2 bond distances C2—C3 and C5—C6 are longer than the usual value of 1.462 Å (International Tables for Crystallography, 1995, Vol. C). A comparable situation has been reported in other structures involving the same tetracarboxylic N,N'-dimethyldiimide group. For example, in the 3,4,5,6-tetrahydrophthalimide (Kirfel, 1975), these distances are 1.489 (5) and 1.486 (5) Å, and in the maleimide (Boubekeur et al., 1991), they are 1.510 (3) and 1.502 (3) Å. This observation may be attributed to the electronic repulsion between the lone pairs of the heteroatom and that of the O atom. These distances tend to increase with an increase in the van der Waals radius and tend towards the Csp3—Csp3 bond distance.

The molecules form layers parallel to the bc plane at intervals of a/2. Within each layer, the planes of the sulfur and selenium molecules are tilted by 40 (1) and 42 (1)° with respect to the bc plane. From one layer to the next the molecular axes differ by 75 (1) and 80 (1)° in (I) and (II), respectively.

The shortest intermolecular distances involve the diimide O5 atom. The contacts, shorter than the sum of the van der Waals radii, are O5···C5i and O5···N4i with values of 2.886 (3) and 2.969 (2) Å in (I), and 2.941 (4) and 2.990 (3) Å in (II) [symmetry code: (i) −1/2 − x, y − 1/2, −1/2 − z].

Experimental top

The title dithiine was synthesized according to the procedure of Draber (1967) from commercial N-methylmaleimide (Lancaster). Ring chlorination of N-methylmaleimide with SOCl2 in the presence of pyridine gave N-methyldichloromaleimide which was further reacted with thiourea in ethanol. The green powder thus obtained (87% yield) was found pure from NMR spectra in DMSO-d6 (H, 13 C). Small dark blue–green needles with a metallic sheen were grown by slow evaporation of a chloroform solution at room temperature. The title diselenine formed in 85% yield when selenourea (Aldrich) instead of thiourea was used in the above procedure. To our knowledge, this compound has not yet been reported. From the olive green powder, a crop of small dark blue–green needles was similarly obtained from a chloroform solution at room temperature. Both the S and Se derivatives are highly solvatochromic, the solutions in halocarbons and aromatics appearing deep blue, and solutions in donor solvents ranging from yellow–green to orange–red.

Computing details top

For both compounds, data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRC-2 and NRC-2A (Ahmed et al., 1973); program(s) used to solve structure: SHELXS96 (Sheldrick, 1990); program(s) used to refine structure: NRCVAX (Gabe et al., 1989) and SHELXL96 (Sheldrick, 1996); molecular graphics: ORTEPII (Johnson, 1976) in NRCVAX; software used to prepare material for publication: NRCVAX and SHELXL96.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) drawing of (I) showing 40% probability displacement ellipsoids and the atomic numbering scheme.
[Figure 2] Fig. 2. Stereoview showing the packing of the molecules of (I).
(I) top
Crystal data top
C10H6N2O4S2F(000) = 288.0
Mr = 282.29Dx = 1.658 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54056 Å
a = 8.905 (3) ÅCell parameters from 25 reflections
b = 5.301 (1) Åθ = 20–25°
c = 12.035 (3) ŵ = 4.39 mm1
β = 95.40 (3)°T = 293 K
V = 565.6 (3) Å3Needle, dark blue–green
Z = 20.72 × 0.13 × 0.07 mm
Data collection top
Nonius CAD-4
diffractometer
954 reflections with I > 2σ(I)
Radiation source: normal-focus xray tubeRint = 0.017
Graphite monochromatorθmax = 69.8°, θmin = 5.9°
ω/2θ scansh = 1010
Absorption correction: integration
(ABSORP in NRCVAX; Gabe et al, 1989)
k = 66
Tmin = 0.347, Tmax = 0.756l = 1414
3926 measured reflections5 standard reflections every 60 min
1071 independent reflections intensity decay: no decay, variation 0.6
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)] = 0.030H-atom parameters constrained
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.0587P)2 + 0.0395P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
1071 reflectionsΔρmax = 0.26 e Å3
84 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL96 (Sheldrick, 1996), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0213 (19)
Crystal data top
C10H6N2O4S2V = 565.6 (3) Å3
Mr = 282.29Z = 2
Monoclinic, P21/nCu Kα radiation
a = 8.905 (3) ŵ = 4.39 mm1
b = 5.301 (1) ÅT = 293 K
c = 12.035 (3) Å0.72 × 0.13 × 0.07 mm
β = 95.40 (3)°
Data collection top
Nonius CAD-4
diffractometer
954 reflections with I > 2σ(I)
Absorption correction: integration
(ABSORP in NRCVAX; Gabe et al, 1989)
Rint = 0.017
Tmin = 0.347, Tmax = 0.7565 standard reflections every 60 min
3926 measured reflections intensity decay: no decay, variation 0.6
1071 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.088H-atom parameters constrained
S = 1.09Δρmax = 0.26 e Å3
1071 reflectionsΔρmin = 0.24 e Å3
84 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. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R-factor_obs 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.

Space group confirmed by PLATON program (Spek, 1995). Data reduction performed using a locally modified version of the NRC-2 program (Ahmed et al., 1973). The structure was solved by direct method using SHELXS96 (Sheldrick, 1990) and difmap synthesis using NRCVAX (Gabe et al. (1989) and SHELXL96 (Sheldrick, 1996). All non-hydrogen atoms anisotropic, hydrogen atoms isotropic. Hydrogen atoms constrained to the parent site using a riding model; SHELXL96 defaults, C—H 0.96 Å. The isotropic factors, Uiso, were adjusted to 50% higher value of the parent site (methyl). A final verification of possible voids was performed using the VOID routine of the PLATON program (Spek, 1995).

[Spek, A·L. (1995). PLATON. Version of July 1995. University of Utrecht, The Netherlands.]

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.13227 (5)0.24707 (8)0.03405 (3)0.0405 (2)
O30.13989 (16)0.1201 (3)0.28970 (12)0.0554 (4)
O50.17507 (15)0.5080 (3)0.19908 (12)0.0509 (4)
N40.01616 (17)0.2247 (3)0.27447 (13)0.0430 (4)
C20.04253 (18)0.0077 (3)0.11467 (14)0.0361 (4)
C30.06608 (19)0.0154 (4)0.23578 (15)0.0406 (4)
C40.0334 (3)0.3094 (5)0.38962 (16)0.0599 (6)
C50.09333 (19)0.3266 (4)0.19146 (15)0.0394 (4)
C60.05317 (18)0.1718 (3)0.08879 (14)0.0359 (4)
H4A0.12940.25520.42440.090*
H4B0.02780.49020.39180.090*
H4C0.04570.23890.42890.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0436 (3)0.0342 (3)0.0442 (3)0.00843 (16)0.00654 (19)0.00373 (17)
O30.0603 (8)0.0546 (9)0.0539 (8)0.0087 (7)0.0189 (7)0.0019 (7)
O50.0516 (7)0.0426 (8)0.0573 (8)0.0111 (6)0.0015 (6)0.0091 (6)
N40.0431 (8)0.0456 (9)0.0406 (8)0.0024 (6)0.0049 (6)0.0105 (7)
C20.0357 (8)0.0322 (8)0.0402 (9)0.0020 (7)0.0024 (7)0.0027 (7)
C30.0384 (9)0.0391 (10)0.0447 (9)0.0041 (7)0.0059 (7)0.0029 (8)
C40.0654 (13)0.0711 (15)0.0443 (11)0.0066 (12)0.0107 (9)0.0196 (10)
C50.0367 (9)0.0347 (9)0.0460 (10)0.0022 (7)0.0006 (7)0.0061 (8)
C60.0357 (8)0.0303 (8)0.0410 (9)0.0007 (7)0.0007 (6)0.0029 (7)
Geometric parameters (Å, º) top
S1—C21.7447 (17)N4—C51.375 (2)
S1—C6i1.7427 (18)C4—H4A0.9600
C2—C31.497 (2)C4—H4B0.9600
C2—C61.334 (2)C4—H4C0.9600
C3—O31.204 (2)C5—O51.204 (2)
C3—N41.386 (2)C5—C61.498 (2)
N4—C41.451 (2)C6—S1i1.7427 (18)
C6i—S1—C296.0 (8)N4—C4—H4B109.5
C6—C2—C3108.7 (2)H4A—C4—H4B109.5
C3—C2—S1120.2 (1)N4—C4—H4C109.5
C6—C2—S1131.2 (2)H4A—C4—H4C109.5
O3—C3—N4126.5 (2)H4B—C4—H4C109.5
O3—C3—C2127.6 (2)O5—C5—N4126.7 (2)
N4—C3—C2105.9 (2)O5—C5—C6126.6 (2)
C3—N4—C4125.0 (2)N4—C5—C6106.7 (2)
C5—N4—C3110.8 (2)C2—C6—C5107.8 (2)
C5—N4—C4123.9 (2)C2—C6—S1i132.8 (2)
N4—C4—H4A109.5C5—C6—S1i119.3 (2)
C6i—S1—C2—C60.5 (2)C4—N4—C5—O56.1 (3)
C6i—S1—C2—C3178.1 (2)C3—N4—C5—C61.7 (2)
C6—C2—C3—O3176.6 (2)C4—N4—C5—C6175.2 (2)
S1—C2—C3—O32.2 (3)C3—C2—C6—C51.7 (19)
C6—C2—C3—N42.7 (2)S1—C2—C6—C5179.7 (1)
S1—C2—C3—N4178.5 (1)C3—C2—C6—S1i178.1 (1)
O3—C3—N4—C5176.7 (2)S1—C2—C6—S1i0.6 (3)
C2—C3—N4—C52.7 (2)O5—C5—C6—C2178.6 (2)
O3—C3—N4—C43.3 (3)N4—C5—C6—C20.1 (2)
C2—C3—N4—C4176.1 (2)O5—C5—C6—S1i1.6 (3)
C3—N4—C5—O5179.6 (2)N4—C5—C6—S1i179.7 (1)
Symmetry code: (i) x, y, z.
(II) top
Crystal data top
C10H6N2O4Se2F(000) = 360.0
Mr = 376.09Dx = 2.103 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54056 Å
a = 9.173 (2) ÅCell parameters from 25 reflections
b = 5.302 (1) Åθ = 20–25°
c = 12.239 (4) ŵ = 7.90 mm1
β = 93.69 (2)°T = 293 K
V = 594.0 (3) Å3Plate, dark blue–green
Z = 20.50 × 0.10 × 0.04 mm
Data collection top
Nonius CAD-4
diffractometer
Rint = 0.030
Graphite monochromatorθmax = 69.8°, θmin = 5.9°
ω/2θ scansh = 1111
Absorption correction: integration
(ABSORP in NRCVAX; Gabe et al, 1989)
k = 66
Tmin = 0.263, Tmax = 0.736l = 1414
4037 measured reflections5 standard reflections every 60 min
1129 independent reflections intensity decay: none
896 reflections with I > 2σ(I)
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)] = 0.026H-atom parameters constrained
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.0431P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.003
1129 reflectionsΔρmax = 0.47 e Å3
84 parametersΔρmin = 0.47 e Å3
0 restraintsExtinction correction: SHELXL96 (Sheldrick, 1996), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0032 (4)
Crystal data top
C10H6N2O4Se2V = 594.0 (3) Å3
Mr = 376.09Z = 2
Monoclinic, P21/nCu Kα radiation
a = 9.173 (2) ŵ = 7.90 mm1
b = 5.302 (1) ÅT = 293 K
c = 12.239 (4) Å0.50 × 0.10 × 0.04 mm
β = 93.69 (2)°
Data collection top
Nonius CAD-4
diffractometer
896 reflections with I > 2σ(I)
Absorption correction: integration
(ABSORP in NRCVAX; Gabe et al, 1989)
Rint = 0.030
Tmin = 0.263, Tmax = 0.7365 standard reflections every 60 min
4037 measured reflections intensity decay: none
1129 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.073H-atom parameters constrained
S = 1.08Δρmax = 0.47 e Å3
1129 reflectionsΔρmin = 0.47 e Å3
84 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. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R-factor_obs 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.

Space group confirmed by PLATON program (Spek, 1995). Data reduction performed using a locally modified version of the NRC-2 program (Ahmed et al., 1973). The structure was solved by direct method using SHELXS96 (Sheldrick, 1990) and difmap synthesis using NRCVAX (Gabe et al. (1989) and SHELXL96 (Sheldrick, 1996). All non-hydrogen atoms anisotropic, hydrogen atoms isotropic. Hydrogen atoms constrained to the parent site using a riding model; SHELXL96 defaults, C—H 0.96 Å. The isotropic factors, Uiso, were adjusted to 50% higher value of the parent site. A final verification of possible voids was performed using the VOID routine of the PLATON program (Spek, 1995).

[Spek, A·L. (1995). PLATON. Version of July 1995. University of Utrecht, The Netherlands.]

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Se10.14205 (3)0.25110 (6)0.04102 (2)0.04304 (17)
O50.1828 (2)0.5080 (5)0.19372 (18)0.0546 (6)
O30.1372 (3)0.0906 (5)0.29443 (18)0.0582 (7)
N40.0211 (3)0.2422 (5)0.2730 (2)0.0454 (7)
C20.0392 (3)0.0056 (6)0.1197 (2)0.0363 (6)
C30.0620 (3)0.0376 (6)0.2394 (2)0.0434 (7)
C40.0408 (4)0.3325 (9)0.3851 (3)0.0636 (10)
C50.0991 (3)0.3340 (7)0.1899 (2)0.0426 (7)
C60.0568 (3)0.1750 (6)0.0909 (2)0.0366 (6)
H4A0.13400.41410.39590.095*
H4B0.03530.45040.39890.095*
H4C0.03660.19250.43460.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.0425 (2)0.0439 (2)0.0433 (2)0.00626 (14)0.00761 (14)0.00293 (15)
O30.0621 (14)0.0688 (18)0.0456 (12)0.0086 (13)0.0188 (10)0.0044 (12)
O50.0519 (13)0.0546 (15)0.0567 (13)0.0129 (11)0.0003 (10)0.0100 (11)
N40.0427 (14)0.0569 (18)0.0371 (13)0.0028 (12)0.0051 (10)0.0152 (12)
C20.0374 (14)0.0377 (15)0.0340 (14)0.0047 (13)0.0026 (10)0.0027 (12)
C30.0399 (15)0.051 (2)0.0396 (15)0.0057 (14)0.0079 (12)0.0044 (14)
C40.059 (2)0.092 (3)0.0406 (17)0.004 (2)0.0065 (15)0.0248 (19)
C50.0384 (15)0.0466 (17)0.0419 (16)0.0044 (14)0.0044 (12)0.0096 (14)
C60.0369 (14)0.0382 (16)0.0346 (14)0.0019 (12)0.0018 (11)0.0043 (12)
Geometric parameters (Å, º) top
Se1—C21.882 (3)C5—C61.506 (4)
Se1—C6i1.885 (3)C3—N41.374 (4)
O3—C31.205 (4)C5—N41.369 (4)
O5—C51.200 (4)N4—C41.454 (4)
C2—C31.503 (4)C4—H4A0.9600
C2—C61.322 (4)C4—H4B0.9600
C6—Se1i1.885 (3)C4—H4C0.9600
C6i—Se1—C293.5 (1)O3—C3—C2127.0 (3)
C6—C2—C3108.7 (3)N4—C3—C2105.7 (2)
C3—C2—Se1118.9 (2)C5—N4—C3111.4 (2)
C6—C2—Se1132.4 (2)C5—N4—C4123.0 (3)
C2—C6—C5107.9 (3)C3—N4—C4125.1 (3)
C2—C6—Se1i134.0 (2)N4—C4—H4A109.5
C5—C6—Se1i118.1 (2)N4—C4—H4B109.5
O5—C5—N4127.4 (3)H4A—C4—H4B109.5
O5—C5—C6126.3 (3)N4—C4—H4C109.5
N4—C5—C6106.2 (3)H4A—C4—H4C109.5
O3—C3—N4127.3 (3)H4B—C4—H4C109.5
C3—C2—C6—C51.8 (3)Se1—C2—C3—O32.7 (4)
Se1—C2—C6—C5179.0 (2)C6—C2—C3—N43.1 (3)
C3—C2—C6—Se1i179.1 (2)Se1—C2—C3—N4177.6 (2)
Se1—C2—C6—Se1i0.2 (5)O5—C5—N4—C3178.8 (3)
C2i—Se1i—C6—C20.1 (4)C6—C5—N4—C32.2 (3)
C2i—Se1i—C6—C5178.9 (2)O5—C5—N4—C46.3 (6)
C2—C6—C5—O5179.1 (3)C6—C5—N4—C4174.7 (3)
Se1i—C6—C5—O50.2 (5)O3—C3—N4—C5176.6 (3)
C2—C6—C5—N40.1 (3)C2—C3—N4—C53.2 (3)
Se1i—C6—C5—N4179.2 (2)O3—C3—N4—C44.3 (5)
C6—C2—C3—O3176.7 (3)C2—C3—N4—C4175.5 (3)
Symmetry code: (i) x, y, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC10H6N2O4S2C10H6N2O4Se2
Mr282.29376.09
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)293293
a, b, c (Å)8.905 (3), 5.301 (1), 12.035 (3)9.173 (2), 5.302 (1), 12.239 (4)
β (°) 95.40 (3) 93.69 (2)
V3)565.6 (3)594.0 (3)
Z22
Radiation typeCu KαCu Kα
µ (mm1)4.397.90
Crystal size (mm)0.72 × 0.13 × 0.070.50 × 0.10 × 0.04
Data collection
DiffractometerNonius CAD-4
diffractometer
Nonius CAD-4
diffractometer
Absorption correctionIntegration
(ABSORP in NRCVAX; Gabe et al, 1989)
Integration
(ABSORP in NRCVAX; Gabe et al, 1989)
Tmin, Tmax0.347, 0.7560.263, 0.736
No. of measured, independent and
observed [I > 2σ(I)] reflections
3926, 1071, 954 4037, 1129, 896
Rint0.0170.030
(sin θ/λ)max1)0.6090.609
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.088, 1.09 0.026, 0.073, 1.08
No. of reflections10711129
No. of parameters8484
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.240.47, 0.47

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, NRC-2 and NRC-2A (Ahmed et al., 1973), SHELXS96 (Sheldrick, 1990), NRCVAX (Gabe et al., 1989) and SHELXL96 (Sheldrick, 1996), ORTEPII (Johnson, 1976) in NRCVAX, NRCVAX and SHELXL96.

Selected geometric parameters (Å, º) for (I) top
S1—C21.7447 (17)C3—N41.386 (2)
S1—C6i1.7427 (18)N4—C41.451 (2)
C2—C31.497 (2)N4—C51.375 (2)
C2—C61.334 (2)C5—O51.204 (2)
C3—O31.204 (2)C5—C61.498 (2)
C6i—S1—C296.0 (8)C5—N4—C3110.8 (2)
C6—C2—C3108.7 (2)C5—N4—C4123.9 (2)
C3—C2—S1120.2 (1)O5—C5—N4126.7 (2)
C6—C2—S1131.2 (2)O5—C5—C6126.6 (2)
O3—C3—N4126.5 (2)N4—C5—C6106.7 (2)
O3—C3—C2127.6 (2)C2—C6—C5107.8 (2)
N4—C3—C2105.9 (2)C2—C6—S1i132.8 (2)
C3—N4—C4125.0 (2)C5—C6—S1i119.3 (2)
Symmetry code: (i) x, y, z.
Selected geometric parameters (Å, º) for (II) top
Se1—C21.882 (3)C2—C61.322 (4)
Se1—C6i1.885 (3)C5—C61.506 (4)
O3—C31.205 (4)C3—N41.374 (4)
O5—C51.200 (4)C5—N41.369 (4)
C2—C31.503 (4)N4—C41.454 (4)
C6i—Se1—C293.5 (1)O5—C5—C6126.3 (3)
C6—C2—C3108.7 (3)N4—C5—C6106.2 (3)
C3—C2—Se1118.9 (2)O3—C3—N4127.3 (3)
C6—C2—Se1132.4 (2)O3—C3—C2127.0 (3)
C2—C6—C5107.9 (3)N4—C3—C2105.7 (2)
C2—C6—Se1i134.0 (2)C5—N4—C3111.4 (2)
C5—C6—Se1i118.1 (2)C5—N4—C4123.0 (3)
O5—C5—N4127.4 (3)C3—N4—C4125.1 (3)
Symmetry code: (i) x, y, z.
 

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