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The title compound, C12H12N2S3, was synthesized by the reaction of CS2 and CH3I with 2-amino-4-phenyl-1,3-thiazole in the presence of concentrated aqueous NaOH. The bond lengths and angles are normal. The crystal packing is stabilized by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031382/cv2094sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031382/cv2094Isup2.hkl
Contains datablock I

CCDC reference: 620781

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.106
  • Data-to-parameter ratio = 35.0

checkCIF/PLATON results

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Alert level C PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Dimethyl N-(4-phenyl-1,3-thiazol-2-yl)dithioimidocarbonate top
Crystal data top
C12H12N2S3F(000) = 1168
Mr = 280.45Dx = 1.368 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 7126 reflections
a = 7.6626 (1) Åθ = 3.1–26.5°
b = 18.2969 (3) ŵ = 0.52 mm1
c = 19.4176 (3) ÅT = 293 K
V = 2722.38 (7) Å3Block, colourless
Z = 80.60 × 0.32 × 0.27 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3036 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.044
Graphite monochromatorθmax = 33.8°, θmin = 2.1°
φ and ω scansh = 119
39182 measured reflectionsk = 2827
5387 independent reflectionsl = 2030
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0447P)2 + 0.1433P]
where P = (Fo2 + 2Fc2)/3
5387 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.29321 (6)0.23544 (2)0.26172 (2)0.0556 (1)
S20.48460 (6)0.24004 (2)0.49433 (2)0.0555 (1)
S30.41756 (6)0.39927 (2)0.47679 (2)0.0605 (1)
N10.46470 (15)0.17841 (6)0.36194 (5)0.0479 (3)
N20.39449 (14)0.30625 (6)0.37433 (5)0.0495 (4)
C10.5808 (2)0.03455 (9)0.39178 (9)0.0669 (6)
C20.6474 (3)0.03451 (10)0.40524 (11)0.0839 (7)
C30.6396 (3)0.08817 (9)0.35627 (13)0.0841 (8)
C40.5624 (3)0.07399 (10)0.29420 (11)0.0838 (8)
C50.4948 (2)0.00552 (9)0.28009 (9)0.0704 (6)
C60.50420 (19)0.05003 (8)0.32882 (8)0.0518 (5)
C70.43584 (17)0.12345 (7)0.31418 (7)0.0468 (4)
C80.3464 (2)0.14494 (8)0.25759 (7)0.0563 (5)
C90.39619 (17)0.23975 (7)0.34128 (6)0.0453 (4)
C100.42877 (16)0.31234 (7)0.43912 (7)0.0457 (4)
C110.4811 (3)0.28257 (11)0.57822 (8)0.0774 (7)
C120.3623 (3)0.45495 (9)0.40446 (9)0.0770 (6)
H10.587600.070700.425300.0800*
H20.697700.044400.447800.1010*
H30.686600.134100.365200.1010*
H40.555300.110700.261200.1010*
H50.442700.003400.237700.0840*
H80.317700.114300.221100.0670*
H11A0.510800.247000.612700.1160*
H11B0.366500.301500.587200.1160*
H11C0.564200.321800.579400.1160*
H12A0.351800.504900.418900.1150*
H12B0.253300.438800.385400.1150*
H12C0.452000.451000.370200.1150*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0618 (2)0.0586 (2)0.0464 (2)0.0014 (2)0.0108 (2)0.0035 (1)
S20.0590 (2)0.0620 (2)0.0455 (2)0.0042 (2)0.0061 (2)0.0027 (2)
S30.0770 (3)0.0563 (2)0.0483 (2)0.0008 (2)0.0020 (2)0.0123 (2)
N10.0527 (7)0.0493 (6)0.0418 (5)0.0011 (5)0.0007 (5)0.0049 (4)
N20.0584 (7)0.0475 (6)0.0427 (6)0.0002 (5)0.0012 (5)0.0045 (4)
C10.0695 (11)0.0550 (9)0.0763 (11)0.0011 (8)0.0156 (8)0.0080 (7)
C20.0892 (13)0.0662 (11)0.0964 (14)0.0062 (10)0.0245 (11)0.0034 (10)
C30.0821 (13)0.0518 (10)0.1184 (17)0.0056 (9)0.0055 (12)0.0014 (10)
C40.1093 (16)0.0563 (10)0.0857 (13)0.0018 (10)0.0142 (12)0.0128 (9)
C50.0955 (13)0.0567 (9)0.0589 (9)0.0009 (9)0.0109 (9)0.0067 (7)
C60.0504 (8)0.0487 (8)0.0564 (8)0.0070 (6)0.0095 (7)0.0044 (6)
C70.0477 (7)0.0473 (7)0.0454 (7)0.0077 (6)0.0047 (6)0.0053 (5)
C80.0602 (9)0.0576 (8)0.0510 (8)0.0090 (7)0.0045 (7)0.0100 (6)
C90.0481 (8)0.0497 (7)0.0382 (6)0.0034 (6)0.0003 (5)0.0024 (5)
C100.0433 (7)0.0512 (8)0.0425 (6)0.0001 (6)0.0008 (6)0.0039 (5)
C110.0994 (13)0.0904 (13)0.0424 (8)0.0020 (11)0.0156 (9)0.0011 (8)
C120.1032 (13)0.0535 (9)0.0742 (11)0.0109 (9)0.0185 (10)0.0044 (8)
Geometric parameters (Å, º) top
S1—C81.7072 (15)C5—C61.391 (2)
S1—C91.7365 (13)C6—C71.470 (2)
S2—C101.7557 (14)C7—C81.3534 (19)
S2—C111.8054 (17)C1—H10.9300
S3—C101.7528 (13)C2—H20.9300
S3—C121.7860 (18)C3—H30.9300
N1—C71.3857 (17)C4—H40.9300
N1—C91.3024 (17)C5—H50.9300
N2—C91.3757 (17)C8—H80.9300
N2—C101.2900 (17)C11—H11A0.9600
C1—C21.388 (3)C11—H11B0.9600
C1—C61.385 (2)C11—H11C0.9600
C2—C31.368 (3)C12—H12A0.9600
C3—C41.367 (3)C12—H12B0.9600
C4—C51.383 (3)C12—H12C0.9600
S1···N12.5695 (11)C7···H8iv3.0100
S1···C9i3.6416 (13)C8···H52.7200
S2···N12.8114 (11)C9···H11Av3.0900
S1···H4ii3.0800H1···N12.5100
S3···H11B2.8200H2···S3ix3.1700
S3···H11C2.6900H3···H11Ax2.6000
S3···H2iii3.1700H4···S1viii3.0800
N1···S12.5695 (11)H5···C82.7200
N1···S22.8114 (11)H5···H82.2700
N1···H12.5100H5···H12Cviii2.4400
N2···H12B2.6600H8···C52.8200
N2···H12C2.6900H8···H52.2700
C6···C8iv3.565 (2)H8···C6i2.8400
C7···C8iv3.463 (2)H8···C7i3.0100
C8···C7i3.463 (2)H11A···C9vi3.0900
C8···C6i3.565 (2)H11A···H3x2.6000
C9···S1iv3.6416 (13)H11B···S32.8200
C9···C11v3.568 (3)H11C···S32.6900
C11···C9vi3.568 (3)H12B···N22.6600
C4···H12Bvii3.0100H12B···C4xi3.0100
C5···H12Bvii2.9700H12B···C5xi2.9700
C5···H12Cviii3.0500H12B···C6xi3.0400
C5···H82.8200H12C···N22.6900
C6···H12Bvii3.0400H12C···C5ii3.0500
C6···H8iv2.8400H12C···H5ii2.4400
C8—S1—C988.70 (7)C6—C1—H1120.00
C10—S2—C11102.86 (8)C1—C2—H2120.00
C10—S3—C12101.60 (7)C3—C2—H2120.00
C7—N1—C9110.79 (10)C2—C3—H3120.00
C9—N2—C10121.97 (11)C4—C3—H3120.00
C2—C1—C6120.54 (16)C3—C4—H4120.00
C1—C2—C3120.43 (19)C5—C4—H4120.00
C2—C3—C4119.69 (17)C4—C5—H5120.00
C3—C4—C5120.56 (18)C6—C5—H5120.00
C4—C5—C6120.52 (16)S1—C8—H8124.00
C1—C6—C5118.23 (14)C7—C8—H8124.00
C1—C6—C7120.57 (14)S2—C11—H11A109.00
C5—C6—C7121.20 (14)S2—C11—H11B109.00
N1—C7—C6118.49 (12)S2—C11—H11C110.00
N1—C7—C8114.42 (12)H11A—C11—H11B110.00
C6—C7—C8127.09 (13)H11A—C11—H11C109.00
S1—C8—C7111.38 (11)H11B—C11—H11C109.00
S1—C9—N1114.71 (9)S3—C12—H12A109.00
S1—C9—N2116.80 (9)S3—C12—H12B110.00
N1—C9—N2128.49 (11)S3—C12—H12C109.00
S2—C10—S3116.16 (8)H12A—C12—H12B109.00
S2—C10—N2125.46 (10)H12A—C12—H12C110.00
S3—C10—N2118.39 (10)H12B—C12—H12C109.00
C2—C1—H1120.00
C8—S1—C9—N2179.22 (11)C2—C1—C6—C50.5 (2)
C9—S1—C8—C70.08 (12)C6—C1—C2—C30.5 (3)
C8—S1—C9—N10.40 (11)C2—C1—C6—C7179.14 (16)
C11—S2—C10—N2171.29 (13)C1—C2—C3—C41.4 (3)
C11—S2—C10—S38.04 (11)C2—C3—C4—C51.1 (3)
C12—S3—C10—N21.54 (13)C3—C4—C5—C60.0 (3)
C12—S3—C10—S2179.09 (10)C4—C5—C6—C7178.89 (16)
C9—N1—C7—C80.54 (17)C4—C5—C6—C10.8 (2)
C7—N1—C9—N2178.98 (13)C5—C6—C7—N1173.55 (13)
C9—N1—C7—C6179.97 (12)C1—C6—C7—N16.1 (2)
C7—N1—C9—S10.60 (14)C5—C6—C7—C85.8 (2)
C9—N2—C10—S3178.37 (10)C1—C6—C7—C8174.52 (15)
C10—N2—C9—N116.3 (2)C6—C7—C8—S1179.61 (12)
C10—N2—C9—S1163.31 (10)N1—C7—C8—S10.24 (16)
C9—N2—C10—S20.94 (18)
Symmetry codes: (i) x1/2, y, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+3/2, y+1/2, z; (iv) x+1/2, y, z+1/2; (v) x1/2, y+1/2, z+1; (vi) x+1/2, y+1/2, z+1; (vii) x+1/2, y1/2, z; (viii) x+1, y1/2, z+1/2; (ix) x+3/2, y1/2, z; (x) x+1, y, z+1; (xi) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···N10.932.512.838 (2)101
 

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