organic compounds
In the title compound, C18H10N2S2, a crystallographic mirror plane passes through the two S atoms. The pentacyclic ring system is folded along the S—S vector and the central dithiine ring adopts a boat conformation.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007793/wn2007sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007793/wn2007Isup2.hkl |
CCDC reference: 605205
Computing details top
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ATOMS (Dowty, 1994); software used to prepare material for publication: CRYSTALS and enCIFer (Allen et al., 2004).
Diquino[3,4 - b;4',3'-e][1,4]dithiine top
Crystal data top
C18H10N2S2 | Dx = 1.488 Mg m−3 |
Mr = 318.42 | Synchrotron radiation, λ = 0.90200 Å |
Orthorhombic, Pmn21 | Cell parameters from 2883 reflections |
a = 23.440 (5) Å | θ = 3.4–34.4° |
b = 7.5873 (15) Å | µ = 0.37 mm−1 |
c = 3.9960 (8) Å | T = 293 K |
V = 710.7 (3) Å3 | Needle, colourless |
Z = 2 | 0.2 × 0.01 × 0.01 mm |
F(000) = 328 |
Data collection top
Siemens SMART CCD diffractometer | 1157 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ω scans | θmax = 34.4°, θmin = 3.4° |
Absorption correction: multi-scan (SADABS; Siemens, 1996) | h = −24→28 |
Tmin = 0.85, Tmax = 0.97 | k = −9→9 |
2883 measured reflections | l = −4→4 |
1157 independent reflections |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = [1-(Fo-Fc)2/36σ2(F)]2/[15.6T0(x) + 20.5T1(x) + 8.37T2(x)]
where Ti are Chebychev polynomials and x = Fc/Fmax (Prince, 1982; Watkin, 1994) |
wR(F2) = 0.077 | (Δ/σ)max = 0.000138 |
S = 0.96 | Δρmax = 0.19 e Å−3 |
1157 reflections | Δρmin = −0.18 e Å−3 |
104 parameters | Absolute structure: Flack (1983), 497 Friedel pairs |
1 restraint | Absolute structure parameter: −0.11 (14) |
Primary atom site location: structure-invariant direct methods |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N | −0.15247 (9) | 0.4208 (3) | 0.6446 (7) | 0.0435 | |
C2 | −0.10638 (12) | 0.3623 (4) | 0.5018 (8) | 0.0408 | |
C3 | −0.05795 (10) | 0.4654 (3) | 0.4219 (7) | 0.0339 | |
C4 | −0.05805 (10) | 0.6406 (3) | 0.5055 (7) | 0.0319 | |
C5 | −0.10680 (10) | 0.7126 (3) | 0.6734 (7) | 0.0323 | |
C6 | −0.11129 (11) | 0.8900 (4) | 0.7789 (7) | 0.0401 | |
C7 | −0.16039 (12) | 0.9493 (4) | 0.9317 (9) | 0.0467 | |
C8 | −0.20638 (12) | 0.8357 (5) | 0.9834 (9) | 0.0513 | |
C9 | −0.20308 (11) | 0.6637 (4) | 0.8901 (9) | 0.0469 | |
C10 | −0.15341 (11) | 0.5955 (4) | 0.7340 (7) | 0.0373 | |
S2 | 0.0000 | 0.77991 (13) | 0.4020 (3) | 0.0383 | |
S1 | 0.0000 | 0.36432 (15) | 0.2145 (3) | 0.0431 | |
H21 | −0.1056 | 0.2463 | 0.3932 | 0.0591* | |
H61 | −0.0803 | 0.9625 | 0.6864 | 0.0568* | |
H71 | −0.1628 | 1.0667 | 0.9585 | 0.0671* | |
H81 | −0.2392 | 0.8795 | 1.0381 | 0.0733* | |
H91 | −0.2338 | 0.5876 | 0.8783 | 0.0680* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N | 0.0352 (12) | 0.0469 (13) | 0.0485 (17) | −0.0113 (10) | −0.0044 (11) | 0.0064 (12) |
C2 | 0.0426 (15) | 0.0398 (15) | 0.0400 (19) | −0.0075 (12) | −0.0075 (13) | 0.0032 (12) |
C3 | 0.0342 (11) | 0.0387 (12) | 0.0288 (15) | −0.0019 (10) | −0.0086 (11) | 0.0043 (12) |
C4 | 0.0261 (11) | 0.0376 (13) | 0.0318 (15) | −0.0006 (10) | −0.0062 (10) | 0.0102 (11) |
C5 | 0.0252 (11) | 0.0408 (14) | 0.0309 (15) | 0.0001 (10) | −0.0065 (10) | 0.0099 (12) |
C6 | 0.0318 (12) | 0.0438 (15) | 0.045 (2) | 0.0030 (11) | −0.0082 (12) | 0.0060 (14) |
C7 | 0.0421 (14) | 0.0516 (17) | 0.0463 (19) | 0.0090 (12) | −0.0072 (15) | −0.0048 (16) |
C8 | 0.0363 (14) | 0.075 (2) | 0.043 (2) | 0.0099 (14) | 0.0024 (13) | −0.0014 (16) |
C9 | 0.0294 (12) | 0.0676 (19) | 0.0436 (19) | −0.0061 (12) | −0.0016 (13) | 0.0051 (18) |
C10 | 0.0310 (13) | 0.0479 (15) | 0.0332 (17) | −0.0064 (11) | −0.0082 (12) | 0.0077 (15) |
S2 | 0.0274 (4) | 0.0362 (4) | 0.0512 (6) | 0.0000 | 0.0000 | 0.0185 (5) |
S1 | 0.0453 (5) | 0.0470 (5) | 0.0371 (6) | 0.0000 | 0.0000 | −0.0074 (5) |
Geometric parameters (Å, º) top
N—C2 | 1.300 (4) | C5—C10 | 1.429 (3) |
N—C10 | 1.373 (4) | C6—C7 | 1.378 (4) |
C2—C3 | 1.416 (4) | C6—H61 | 0.984 |
C2—H21 | 0.981 | C7—C8 | 1.396 (4) |
C3—C4 | 1.371 (4) | C7—H71 | 0.899 |
C3—S1 | 1.766 (3) | C8—C9 | 1.359 (5) |
C4—C5 | 1.433 (4) | C8—H81 | 0.867 |
C4—S2 | 1.772 (3) | C9—C10 | 1.419 (4) |
C5—C6 | 1.414 (4) | C9—H91 | 0.925 |
C2—N—C10 | 117.2 (2) | C7—C6—H61 | 126.9 |
N—C2—C3 | 125.2 (3) | C6—C7—C8 | 120.6 (3) |
N—C2—H21 | 121.1 | C6—C7—H71 | 115.4 |
C3—C2—H21 | 112.4 | C8—C7—H71 | 123.0 |
C2—C3—C4 | 118.7 (3) | C7—C8—C9 | 120.5 (3) |
C2—C3—S1 | 118.8 (2) | C7—C8—H81 | 119.1 |
C4—C3—S1 | 122.5 (2) | C9—C8—H81 | 119.2 |
C3—C4—C5 | 119.0 (2) | C8—C9—C10 | 121.2 (3) |
C3—C4—S2 | 121.3 (2) | C8—C9—H91 | 124.7 |
C5—C4—S2 | 119.6 (2) | C10—C9—H91 | 112.9 |
C4—C5—C6 | 124.2 (2) | C5—C10—C9 | 118.4 (3) |
C4—C5—C10 | 116.9 (2) | C5—C10—N | 123.0 (3) |
C6—C5—C10 | 119.0 (3) | C9—C10—N | 118.7 (2) |
C5—C6—C7 | 120.3 (3) | C4i—S2—C4 | 100.34 (16) |
C5—C6—H61 | 111.4 | C3—S1—C3i | 100.52 (18) |
Symmetry code: (i) −x, y, z. |