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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007793/wn2007sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007793/wn2007Isup2.hkl
Contains datablock I

CCDC reference: 605205

Key indicators

  • Single-crystal synchrotron study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.034
  • wR factor = 0.077
  • Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 30.07 Deg.
Author Response: The beam was lost during the data collection, hampering the collection of the higher resolutions scans.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.94
Author Response: The beam was lost during the data collection, hampering the collection of the higher resolutions scans.

Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
Alert level G ABSMU_01 Radiation type not identified. Calculation of _exptl_absorpt_correction_mu not performed. REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 34.42 From the CIF: _reflns_number_total 1157 Count of symmetry unique reflns 856 Completeness (_total/calc) 135.16% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 301 Fraction of Friedel pairs measured 0.352 Are heavy atom types Z>Si present yes
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

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
C18H10N2S2Dx = 1.488 Mg m3
Mr = 318.42Synchrotron radiation, λ = 0.90200 Å
Orthorhombic, Pmn21Cell parameters from 2883 reflections
a = 23.440 (5) Åθ = 3.4–34.4°
b = 7.5873 (15) ŵ = 0.37 mm1
c = 3.9960 (8) ÅT = 293 K
V = 710.7 (3) Å3Needle, colourless
Z = 20.2 × 0.01 × 0.01 mm
F(000) = 328
Data collection top
Siemens SMART CCD
diffractometer
1157 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
ω scansθmax = 34.4°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Siemens, 1996)
h = 2428
Tmin = 0.85, Tmax = 0.97k = 99
2883 measured reflectionsl = 44
1157 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 0.96Δρmax = 0.19 e Å3
1157 reflectionsΔρmin = 0.18 e Å3
104 parametersAbsolute structure: Flack (1983), 497 Friedel pairs
1 restraintAbsolute 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
xyzUiso*/Ueq
N0.15247 (9)0.4208 (3)0.6446 (7)0.0435
C20.10638 (12)0.3623 (4)0.5018 (8)0.0408
C30.05795 (10)0.4654 (3)0.4219 (7)0.0339
C40.05805 (10)0.6406 (3)0.5055 (7)0.0319
C50.10680 (10)0.7126 (3)0.6734 (7)0.0323
C60.11129 (11)0.8900 (4)0.7789 (7)0.0401
C70.16039 (12)0.9493 (4)0.9317 (9)0.0467
C80.20638 (12)0.8357 (5)0.9834 (9)0.0513
C90.20308 (11)0.6637 (4)0.8901 (9)0.0469
C100.15341 (11)0.5955 (4)0.7340 (7)0.0373
S20.00000.77991 (13)0.4020 (3)0.0383
S10.00000.36432 (15)0.2145 (3)0.0431
H210.10560.24630.39320.0591*
H610.08030.96250.68640.0568*
H710.16281.06670.95850.0671*
H810.23920.87951.03810.0733*
H910.23380.58760.87830.0680*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0352 (12)0.0469 (13)0.0485 (17)0.0113 (10)0.0044 (11)0.0064 (12)
C20.0426 (15)0.0398 (15)0.0400 (19)0.0075 (12)0.0075 (13)0.0032 (12)
C30.0342 (11)0.0387 (12)0.0288 (15)0.0019 (10)0.0086 (11)0.0043 (12)
C40.0261 (11)0.0376 (13)0.0318 (15)0.0006 (10)0.0062 (10)0.0102 (11)
C50.0252 (11)0.0408 (14)0.0309 (15)0.0001 (10)0.0065 (10)0.0099 (12)
C60.0318 (12)0.0438 (15)0.045 (2)0.0030 (11)0.0082 (12)0.0060 (14)
C70.0421 (14)0.0516 (17)0.0463 (19)0.0090 (12)0.0072 (15)0.0048 (16)
C80.0363 (14)0.075 (2)0.043 (2)0.0099 (14)0.0024 (13)0.0014 (16)
C90.0294 (12)0.0676 (19)0.0436 (19)0.0061 (12)0.0016 (13)0.0051 (18)
C100.0310 (13)0.0479 (15)0.0332 (17)0.0064 (11)0.0082 (12)0.0077 (15)
S20.0274 (4)0.0362 (4)0.0512 (6)0.00000.00000.0185 (5)
S10.0453 (5)0.0470 (5)0.0371 (6)0.00000.00000.0074 (5)
Geometric parameters (Å, º) top
N—C21.300 (4)C5—C101.429 (3)
N—C101.373 (4)C6—C71.378 (4)
C2—C31.416 (4)C6—H610.984
C2—H210.981C7—C81.396 (4)
C3—C41.371 (4)C7—H710.899
C3—S11.766 (3)C8—C91.359 (5)
C4—C51.433 (4)C8—H810.867
C4—S21.772 (3)C9—C101.419 (4)
C5—C61.414 (4)C9—H910.925
C2—N—C10117.2 (2)C7—C6—H61126.9
N—C2—C3125.2 (3)C6—C7—C8120.6 (3)
N—C2—H21121.1C6—C7—H71115.4
C3—C2—H21112.4C8—C7—H71123.0
C2—C3—C4118.7 (3)C7—C8—C9120.5 (3)
C2—C3—S1118.8 (2)C7—C8—H81119.1
C4—C3—S1122.5 (2)C9—C8—H81119.2
C3—C4—C5119.0 (2)C8—C9—C10121.2 (3)
C3—C4—S2121.3 (2)C8—C9—H91124.7
C5—C4—S2119.6 (2)C10—C9—H91112.9
C4—C5—C6124.2 (2)C5—C10—C9118.4 (3)
C4—C5—C10116.9 (2)C5—C10—N123.0 (3)
C6—C5—C10119.0 (3)C9—C10—N118.7 (2)
C5—C6—C7120.3 (3)C4i—S2—C4100.34 (16)
C5—C6—H61111.4C3—S1—C3i100.52 (18)
Symmetry code: (i) x, y, z.
 

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