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The title compound, C14H12N2S4, crystallizes in the monoclinic space group P21/c. The mol­ecule is centrosymmetric; the two thia­zole rings are parallel to each other, while the thia­zole and the benzene planes are almost perpendicular to each other, forming a dihedral angle of 100.6 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022377/ac6022sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022377/ac6022Isup2.hkl
Contains datablock I

CCDC reference: 202988

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.086
  • Data-to-parameter ratio = 16.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.875 1.000 Tmin' and Tmax expected: 0.881 0.906 RR' = 0.900 Please check that your absorption correction is appropriate. HYDTR_01 Alert C The hydrogen treatment should only be one of the following keywords * refall * refxyz * refU * noref * undef * constr * none * mixed Hydrogen treatment given as const General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.906 Tmax scaled 0.906 Tmin scaled 0.792
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997) and SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,2'-[1,4-phenylenebis(methylenethio)]dithiazole top
Crystal data top
C14H12N2S4F(000) = 348
Mr = 336.50? # Insert any comments here.
Monoclinic, P21/cDx = 1.484 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.366 (3) ÅCell parameters from 567 reflections
b = 15.411 (6) Åθ = 2.6–26.2°
c = 7.679 (3) ŵ = 0.62 mm1
β = 91.331 (7)°T = 293 K
V = 753.2 (5) Å3Prism, colourless
Z = 20.20 × 0.18 × 0.16 mm
Data collection top
Bruker CCD area-detector
diffractometer
1518 independent reflections
Radiation source: fine-focus sealed tube1074 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan
SADABS (Bruker, 1997)
h = 77
Tmin = 0.875, Tmax = 1.000k = 1519
3479 measured reflectionsl = 97
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086Const
S = 1.04 w = 1/[σ2(Fo2) + (0.0327P)2 + 0.1354P]
where P = (Fo2 + 2Fc2)/3
1518 reflections(Δ/σ)max < 0.001
91 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. ? #Insert any special details here.

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
S10.26130 (10)0.22553 (4)0.51522 (9)0.0484 (2)
S20.70899 (11)0.24959 (4)0.38669 (10)0.0528 (2)
N10.4669 (3)0.37404 (13)0.4779 (3)0.0532 (6)
C10.4746 (4)0.29021 (16)0.4611 (3)0.0394 (6)
C20.6565 (5)0.40912 (18)0.4280 (4)0.0604 (8)
H20.68100.46860.43090.072*
C30.8021 (4)0.35339 (18)0.3758 (4)0.0585 (8)
H30.93510.36880.33880.070*
C40.3503 (4)0.11827 (15)0.4543 (4)0.0530 (7)
H4A0.39340.11810.33400.064*
H4B0.46940.10100.52750.064*
C50.1698 (4)0.05625 (15)0.4777 (4)0.0438 (6)
C60.1553 (4)0.00672 (16)0.6271 (4)0.0501 (7)
H60.25920.01090.71380.060*
C70.0126 (4)0.04910 (16)0.3511 (4)0.0494 (7)
H70.01980.08220.25020.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0384 (4)0.0437 (4)0.0636 (5)0.0005 (3)0.0091 (3)0.0051 (3)
S20.0428 (4)0.0439 (4)0.0723 (5)0.0008 (3)0.0125 (3)0.0032 (3)
N10.0508 (14)0.0388 (13)0.0700 (15)0.0032 (10)0.0023 (12)0.0025 (11)
C10.0371 (14)0.0398 (14)0.0412 (14)0.0025 (10)0.0024 (11)0.0008 (11)
C20.0609 (19)0.0401 (15)0.080 (2)0.0067 (14)0.0018 (17)0.0020 (14)
C30.0487 (17)0.0530 (17)0.074 (2)0.0083 (14)0.0097 (16)0.0065 (14)
C40.0422 (15)0.0443 (15)0.0731 (18)0.0008 (12)0.0119 (14)0.0075 (14)
C50.0385 (14)0.0328 (13)0.0606 (17)0.0011 (10)0.0107 (14)0.0064 (12)
C60.0465 (16)0.0463 (15)0.0572 (17)0.0010 (12)0.0019 (14)0.0041 (13)
C70.0536 (18)0.0421 (14)0.0528 (16)0.0011 (12)0.0081 (15)0.0021 (12)
Geometric parameters (Å, º) top
S1—C11.743 (3)C4—C51.509 (3)
S1—C41.812 (3)C4—H4A0.9700
S2—C31.709 (3)C4—H4B0.9700
S2—C11.727 (2)C5—C71.383 (4)
N1—C11.299 (3)C5—C61.383 (4)
N1—C21.385 (3)C6—C7i1.385 (4)
C2—C31.332 (4)C6—H60.9300
C2—H20.9300C7—C6i1.385 (4)
C3—H30.9300C7—H70.9300
C1—S1—C4102.13 (12)S1—C4—H4A110.2
C3—S2—C188.87 (13)C5—C4—H4B110.2
C1—N1—C2109.0 (2)S1—C4—H4B110.2
N1—C1—S2115.36 (18)H4A—C4—H4B108.5
N1—C1—S1120.89 (19)C7—C5—C6118.6 (2)
S2—C1—S1123.74 (14)C7—C5—C4120.5 (2)
C3—C2—N1116.7 (2)C6—C5—C4120.9 (3)
C3—C2—H2121.7C5—C6—C7i120.6 (3)
N1—C2—H2121.7C5—C6—H6119.7
C2—C3—S2110.1 (2)C7i—C6—H6119.7
C2—C3—H3124.9C5—C7—C6i120.8 (2)
S2—C3—H3124.9C5—C7—H7119.6
C5—C4—S1107.66 (17)C6i—C7—H7119.6
C5—C4—H4A110.2
C2—N1—C1—S20.4 (3)C1—S2—C3—C20.4 (2)
C2—N1—C1—S1179.33 (19)C1—S1—C4—C5174.31 (19)
C3—S2—C1—N10.5 (2)S1—C4—C5—C781.2 (3)
C3—S2—C1—S1179.37 (17)S1—C4—C5—C697.5 (2)
C4—S1—C1—N1176.5 (2)C7—C5—C6—C7i0.3 (4)
C4—S1—C1—S24.72 (19)C4—C5—C6—C7i179.0 (2)
C1—N1—C2—C30.1 (4)C6—C5—C7—C6i0.3 (4)
N1—C2—C3—S20.3 (4)C4—C5—C7—C6i179.0 (2)
Symmetry code: (i) x, y, z+1.
 

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