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The crystal structure of the title compound (systematic name: 2H-1-benzothiopyran-2-thione), C9H6S2, also known as di­thio­coumarin, has been determined. The mol­ecule is essentially planar and the structure is stabilized via S...S and C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026984/ob6428sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026984/ob6428Isup2.hkl
Contains datablock I

CCDC reference: 255953

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.027
  • wR factor = 0.077
  • Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.45 PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. S2 .. 2.89 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. C2 .. 2.93 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. H7 .. 2.53 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. H6 .. 2.57 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C2 .. H7 .. 3.42 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997), POV-RAY for Windows (The POV-RAY Team, 2004), WinGX (Version 1.64.05; Farrugia, 1999) and Mercury for Linux (Taylor & Macrae, 2001; Bruno et al., 2002); software used to prepare material for publication: PLATON (Spek, 2003).

2H-thiochromene-2-thione top
Crystal data top
C9H6S2Z = 2
Mr = 178.28F(000) = 184
Triclinic, P1Dx = 1.516 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4427 (13) ÅCell parameters from 3853 reflections
b = 7.5697 (13) Åθ = 2.7–25.4°
c = 8.2490 (14) ŵ = 0.60 mm1
α = 83.270 (2)°T = 90 K
β = 67.445 (2)°Block, dark red
γ = 65.599 (2)°0.40 × 0.26 × 0.06 mm
V = 390.39 (12) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1417 independent reflections
Radiation source: fine-focus sealed tube1348 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
φ and ω scansθmax = 25.4°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.805, Tmax = 0.967k = 99
3853 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0487P)2 + 0.1946P]
where P = (Fo2 + 2Fc2)/3
1417 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.23 e Å3
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. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.24851 (7)0.44672 (6)0.13788 (6)0.02186 (16)
S20.20901 (6)0.28024 (5)0.47810 (5)0.01425 (15)
C10.2476 (2)0.2558 (2)0.2600 (2)0.0155 (3)
C20.2772 (2)0.0745 (2)0.1937 (2)0.0172 (3)
C30.2870 (2)0.0854 (2)0.2830 (2)0.0165 (3)
C40.2792 (2)0.2796 (2)0.5471 (2)0.0160 (3)
C50.2594 (2)0.2988 (2)0.7201 (2)0.0179 (4)
C60.2248 (2)0.1407 (2)0.8175 (2)0.0167 (4)
C70.2094 (2)0.0345 (2)0.7423 (2)0.0150 (3)
C80.2299 (2)0.0546 (2)0.5658 (2)0.0123 (3)
C90.2655 (2)0.1029 (2)0.4654 (2)0.0133 (3)
H20.293 (3)0.071 (3)0.075 (3)0.023 (5)*
H30.307 (3)0.195 (3)0.228 (2)0.009 (4)*
H40.304 (3)0.386 (3)0.474 (3)0.021 (5)*
H50.268 (3)0.406 (3)0.775 (3)0.013 (4)*
H60.214 (3)0.156 (3)0.930 (3)0.018 (5)*
H70.182 (3)0.138 (3)0.813 (2)0.013 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0259 (3)0.0192 (3)0.0185 (3)0.00920 (19)0.00775 (19)0.00694 (17)
S20.0172 (2)0.0113 (2)0.0148 (2)0.00607 (17)0.00631 (17)0.00139 (15)
C10.0102 (7)0.0185 (8)0.0153 (8)0.0046 (6)0.0040 (6)0.0027 (6)
C20.0138 (8)0.0225 (9)0.0141 (8)0.0055 (6)0.0048 (6)0.0025 (6)
C30.0110 (7)0.0212 (8)0.0163 (8)0.0048 (6)0.0037 (6)0.0065 (7)
C40.0119 (7)0.0127 (8)0.0225 (8)0.0041 (6)0.0055 (6)0.0023 (6)
C50.0137 (8)0.0140 (8)0.0242 (9)0.0056 (6)0.0067 (7)0.0065 (7)
C60.0136 (8)0.0206 (9)0.0144 (9)0.0055 (7)0.0058 (6)0.0037 (7)
C70.0126 (7)0.0162 (8)0.0150 (8)0.0048 (6)0.0046 (6)0.0008 (6)
C80.0093 (7)0.0116 (7)0.0150 (8)0.0036 (6)0.0042 (6)0.0011 (6)
C90.0086 (7)0.0138 (8)0.0162 (8)0.0035 (6)0.0041 (6)0.0005 (6)
Geometric parameters (Å, º) top
S1—C11.6626 (16)C7—C81.402 (2)
S2—C11.7298 (17)C8—C91.406 (2)
S2—C81.7440 (16)C4—C91.408 (2)
C1—C21.437 (2)C2—H20.94 (2)
C2—C31.331 (2)C3—H30.925 (19)
C3—C91.447 (2)C4—H40.98 (2)
C4—C51.374 (2)C5—H50.87 (2)
C5—C61.398 (2)C6—H60.90 (2)
C6—C71.376 (2)C7—H70.935 (19)
C1—S2—C8106.14 (8)C4—C5—H5123.7 (13)
C2—C1—S1123.56 (13)C6—C5—H5116.6 (13)
C2—C1—S2119.14 (12)C7—C6—C5120.75 (15)
S1—C1—S2117.30 (10)C7—C6—H6120.7 (12)
C3—C2—C1126.17 (15)C5—C6—H6118.5 (12)
C3—C2—H2118.5 (12)C6—C7—C8119.67 (15)
C1—C2—H2115.3 (12)C6—C7—H7118.2 (11)
C2—C3—C9125.00 (15)C8—C7—H7122.2 (11)
C2—C3—H3119.4 (11)C7—C8—C9120.41 (14)
C9—C3—H3115.6 (11)C7—C8—S2117.47 (12)
C5—C4—C9121.05 (15)C9—C8—S2122.12 (12)
C5—C4—H4122.8 (11)C8—C9—C4118.34 (15)
C9—C4—H4116.1 (11)C8—C9—C3121.36 (14)
C4—C5—C6119.78 (15)C4—C9—C3120.30 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···S2i0.98 (2)2.89 (3)3.716 (2)143 (2)
C2—H2···C2ii0.94 (2)2.93 (2)3.479 (2)119 (2)
S2···S2iii??3.427 (1)?
C2—H2···H7iv0.94 (2)2.53 (3)3.42 (2)158
C2—H2···H6iv0.94 (2)2.57 (4)3.22 (3)127
Symmetry codes: (i) x, y1, z; (ii) x+1, y, z; (iii) x, y+1, z+1; (iv) x, y, z1.
 

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