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
CCDC reference: 620781
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.106
- Data-to-parameter ratio = 35.0
checkCIF/PLATON results
No syntax errors found
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
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
C12H12N2S3 | F(000) = 1168 |
Mr = 280.45 | Dx = 1.368 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 7126 reflections |
a = 7.6626 (1) Å | θ = 3.1–26.5° |
b = 18.2969 (3) Å | µ = 0.52 mm−1 |
c = 19.4176 (3) Å | T = 293 K |
V = 2722.38 (7) Å3 | Block, colourless |
Z = 8 | 0.60 × 0.32 × 0.27 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 3036 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.044 |
Graphite monochromator | θmax = 33.8°, θmin = 2.1° |
φ and ω scans | h = −11→9 |
39182 measured reflections | k = −28→27 |
5387 independent reflections | l = −20→30 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-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 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.29321 (6) | 0.23544 (2) | 0.26172 (2) | 0.0556 (1) | |
S2 | 0.48460 (6) | 0.24004 (2) | 0.49433 (2) | 0.0555 (1) | |
S3 | 0.41756 (6) | 0.39927 (2) | 0.47679 (2) | 0.0605 (1) | |
N1 | 0.46470 (15) | 0.17841 (6) | 0.36194 (5) | 0.0479 (3) | |
N2 | 0.39449 (14) | 0.30625 (6) | 0.37433 (5) | 0.0495 (4) | |
C1 | 0.5808 (2) | 0.03455 (9) | 0.39178 (9) | 0.0669 (6) | |
C2 | 0.6474 (3) | −0.03451 (10) | 0.40524 (11) | 0.0839 (7) | |
C3 | 0.6396 (3) | −0.08817 (9) | 0.35627 (13) | 0.0841 (8) | |
C4 | 0.5624 (3) | −0.07399 (10) | 0.29420 (11) | 0.0838 (8) | |
C5 | 0.4948 (2) | −0.00552 (9) | 0.28009 (9) | 0.0704 (6) | |
C6 | 0.50420 (19) | 0.05003 (8) | 0.32882 (8) | 0.0518 (5) | |
C7 | 0.43584 (17) | 0.12345 (7) | 0.31418 (7) | 0.0468 (4) | |
C8 | 0.3464 (2) | 0.14494 (8) | 0.25759 (7) | 0.0563 (5) | |
C9 | 0.39619 (17) | 0.23975 (7) | 0.34128 (6) | 0.0453 (4) | |
C10 | 0.42877 (16) | 0.31234 (7) | 0.43912 (7) | 0.0457 (4) | |
C11 | 0.4811 (3) | 0.28257 (11) | 0.57822 (8) | 0.0774 (7) | |
C12 | 0.3623 (3) | 0.45495 (9) | 0.40446 (9) | 0.0770 (6) | |
H1 | 0.58760 | 0.07070 | 0.42530 | 0.0800* | |
H2 | 0.69770 | −0.04440 | 0.44780 | 0.1010* | |
H3 | 0.68660 | −0.13410 | 0.36520 | 0.1010* | |
H4 | 0.55530 | −0.11070 | 0.26120 | 0.1010* | |
H5 | 0.44270 | 0.00340 | 0.23770 | 0.0840* | |
H8 | 0.31770 | 0.11430 | 0.22110 | 0.0670* | |
H11A | 0.51080 | 0.24700 | 0.61270 | 0.1160* | |
H11B | 0.36650 | 0.30150 | 0.58720 | 0.1160* | |
H11C | 0.56420 | 0.32180 | 0.57940 | 0.1160* | |
H12A | 0.35180 | 0.50490 | 0.41890 | 0.1150* | |
H12B | 0.25330 | 0.43880 | 0.38540 | 0.1150* | |
H12C | 0.45200 | 0.45100 | 0.37020 | 0.1150* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0618 (2) | 0.0586 (2) | 0.0464 (2) | −0.0014 (2) | −0.0108 (2) | −0.0035 (1) |
S2 | 0.0590 (2) | 0.0620 (2) | 0.0455 (2) | 0.0042 (2) | −0.0061 (2) | 0.0027 (2) |
S3 | 0.0770 (3) | 0.0563 (2) | 0.0483 (2) | 0.0008 (2) | −0.0020 (2) | −0.0123 (2) |
N1 | 0.0527 (7) | 0.0493 (6) | 0.0418 (5) | −0.0011 (5) | −0.0007 (5) | −0.0049 (4) |
N2 | 0.0584 (7) | 0.0475 (6) | 0.0427 (6) | 0.0002 (5) | −0.0012 (5) | −0.0045 (4) |
C1 | 0.0695 (11) | 0.0550 (9) | 0.0763 (11) | 0.0011 (8) | −0.0156 (8) | −0.0080 (7) |
C2 | 0.0892 (13) | 0.0662 (11) | 0.0964 (14) | 0.0062 (10) | −0.0245 (11) | 0.0034 (10) |
C3 | 0.0821 (13) | 0.0518 (10) | 0.1184 (17) | 0.0056 (9) | 0.0055 (12) | 0.0014 (10) |
C4 | 0.1093 (16) | 0.0563 (10) | 0.0857 (13) | 0.0018 (10) | 0.0142 (12) | −0.0128 (9) |
C5 | 0.0955 (13) | 0.0567 (9) | 0.0589 (9) | −0.0009 (9) | 0.0109 (9) | −0.0067 (7) |
C6 | 0.0504 (8) | 0.0487 (8) | 0.0564 (8) | −0.0070 (6) | 0.0095 (7) | −0.0044 (6) |
C7 | 0.0477 (7) | 0.0473 (7) | 0.0454 (7) | −0.0077 (6) | 0.0047 (6) | −0.0053 (5) |
C8 | 0.0602 (9) | 0.0576 (8) | 0.0510 (8) | −0.0090 (7) | −0.0045 (7) | −0.0100 (6) |
C9 | 0.0481 (8) | 0.0497 (7) | 0.0382 (6) | −0.0034 (6) | 0.0003 (5) | −0.0024 (5) |
C10 | 0.0433 (7) | 0.0512 (8) | 0.0425 (6) | −0.0001 (6) | 0.0008 (6) | −0.0039 (5) |
C11 | 0.0994 (13) | 0.0904 (13) | 0.0424 (8) | 0.0020 (11) | −0.0156 (9) | −0.0011 (8) |
C12 | 0.1032 (13) | 0.0535 (9) | 0.0742 (11) | 0.0109 (9) | −0.0185 (10) | −0.0044 (8) |
Geometric parameters (Å, º) top
S1—C8 | 1.7072 (15) | C5—C6 | 1.391 (2) |
S1—C9 | 1.7365 (13) | C6—C7 | 1.470 (2) |
S2—C10 | 1.7557 (14) | C7—C8 | 1.3534 (19) |
S2—C11 | 1.8054 (17) | C1—H1 | 0.9300 |
S3—C10 | 1.7528 (13) | C2—H2 | 0.9300 |
S3—C12 | 1.7860 (18) | C3—H3 | 0.9300 |
N1—C7 | 1.3857 (17) | C4—H4 | 0.9300 |
N1—C9 | 1.3024 (17) | C5—H5 | 0.9300 |
N2—C9 | 1.3757 (17) | C8—H8 | 0.9300 |
N2—C10 | 1.2900 (17) | C11—H11A | 0.9600 |
C1—C2 | 1.388 (3) | C11—H11B | 0.9600 |
C1—C6 | 1.385 (2) | C11—H11C | 0.9600 |
C2—C3 | 1.368 (3) | C12—H12A | 0.9600 |
C3—C4 | 1.367 (3) | C12—H12B | 0.9600 |
C4—C5 | 1.383 (3) | C12—H12C | 0.9600 |
| | | |
S1···N1 | 2.5695 (11) | C7···H8iv | 3.0100 |
S1···C9i | 3.6416 (13) | C8···H5 | 2.7200 |
S2···N1 | 2.8114 (11) | C9···H11Av | 3.0900 |
S1···H4ii | 3.0800 | H1···N1 | 2.5100 |
S3···H11B | 2.8200 | H2···S3ix | 3.1700 |
S3···H11C | 2.6900 | H3···H11Ax | 2.6000 |
S3···H2iii | 3.1700 | H4···S1viii | 3.0800 |
N1···S1 | 2.5695 (11) | H5···C8 | 2.7200 |
N1···S2 | 2.8114 (11) | H5···H8 | 2.2700 |
N1···H1 | 2.5100 | H5···H12Cviii | 2.4400 |
N2···H12B | 2.6600 | H8···C5 | 2.8200 |
N2···H12C | 2.6900 | H8···H5 | 2.2700 |
C6···C8iv | 3.565 (2) | H8···C6i | 2.8400 |
C7···C8iv | 3.463 (2) | H8···C7i | 3.0100 |
C8···C7i | 3.463 (2) | H11A···C9vi | 3.0900 |
C8···C6i | 3.565 (2) | H11A···H3x | 2.6000 |
C9···S1iv | 3.6416 (13) | H11B···S3 | 2.8200 |
C9···C11v | 3.568 (3) | H11C···S3 | 2.6900 |
C11···C9vi | 3.568 (3) | H12B···N2 | 2.6600 |
C4···H12Bvii | 3.0100 | H12B···C4xi | 3.0100 |
C5···H12Bvii | 2.9700 | H12B···C5xi | 2.9700 |
C5···H12Cviii | 3.0500 | H12B···C6xi | 3.0400 |
C5···H8 | 2.8200 | H12C···N2 | 2.6900 |
C6···H12Bvii | 3.0400 | H12C···C5ii | 3.0500 |
C6···H8iv | 2.8400 | H12C···H5ii | 2.4400 |
| | | |
C8—S1—C9 | 88.70 (7) | C6—C1—H1 | 120.00 |
C10—S2—C11 | 102.86 (8) | C1—C2—H2 | 120.00 |
C10—S3—C12 | 101.60 (7) | C3—C2—H2 | 120.00 |
C7—N1—C9 | 110.79 (10) | C2—C3—H3 | 120.00 |
C9—N2—C10 | 121.97 (11) | C4—C3—H3 | 120.00 |
C2—C1—C6 | 120.54 (16) | C3—C4—H4 | 120.00 |
C1—C2—C3 | 120.43 (19) | C5—C4—H4 | 120.00 |
C2—C3—C4 | 119.69 (17) | C4—C5—H5 | 120.00 |
C3—C4—C5 | 120.56 (18) | C6—C5—H5 | 120.00 |
C4—C5—C6 | 120.52 (16) | S1—C8—H8 | 124.00 |
C1—C6—C5 | 118.23 (14) | C7—C8—H8 | 124.00 |
C1—C6—C7 | 120.57 (14) | S2—C11—H11A | 109.00 |
C5—C6—C7 | 121.20 (14) | S2—C11—H11B | 109.00 |
N1—C7—C6 | 118.49 (12) | S2—C11—H11C | 110.00 |
N1—C7—C8 | 114.42 (12) | H11A—C11—H11B | 110.00 |
C6—C7—C8 | 127.09 (13) | H11A—C11—H11C | 109.00 |
S1—C8—C7 | 111.38 (11) | H11B—C11—H11C | 109.00 |
S1—C9—N1 | 114.71 (9) | S3—C12—H12A | 109.00 |
S1—C9—N2 | 116.80 (9) | S3—C12—H12B | 110.00 |
N1—C9—N2 | 128.49 (11) | S3—C12—H12C | 109.00 |
S2—C10—S3 | 116.16 (8) | H12A—C12—H12B | 109.00 |
S2—C10—N2 | 125.46 (10) | H12A—C12—H12C | 110.00 |
S3—C10—N2 | 118.39 (10) | H12B—C12—H12C | 109.00 |
C2—C1—H1 | 120.00 | | |
| | | |
C8—S1—C9—N2 | −179.22 (11) | C2—C1—C6—C5 | 0.5 (2) |
C9—S1—C8—C7 | −0.08 (12) | C6—C1—C2—C3 | 0.5 (3) |
C8—S1—C9—N1 | 0.40 (11) | C2—C1—C6—C7 | −179.14 (16) |
C11—S2—C10—N2 | −171.29 (13) | C1—C2—C3—C4 | −1.4 (3) |
C11—S2—C10—S3 | 8.04 (11) | C2—C3—C4—C5 | 1.1 (3) |
C12—S3—C10—N2 | −1.54 (13) | C3—C4—C5—C6 | 0.0 (3) |
C12—S3—C10—S2 | 179.09 (10) | C4—C5—C6—C7 | 178.89 (16) |
C9—N1—C7—C8 | 0.54 (17) | C4—C5—C6—C1 | −0.8 (2) |
C7—N1—C9—N2 | 178.98 (13) | C5—C6—C7—N1 | −173.55 (13) |
C9—N1—C7—C6 | 179.97 (12) | C1—C6—C7—N1 | 6.1 (2) |
C7—N1—C9—S1 | −0.60 (14) | C5—C6—C7—C8 | 5.8 (2) |
C9—N2—C10—S3 | −178.37 (10) | C1—C6—C7—C8 | −174.52 (15) |
C10—N2—C9—N1 | −16.3 (2) | C6—C7—C8—S1 | −179.61 (12) |
C10—N2—C9—S1 | 163.31 (10) | N1—C7—C8—S1 | −0.24 (16) |
C9—N2—C10—S2 | 0.94 (18) | | |
Symmetry codes: (i) x−1/2, 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) x−1/2, −y+1/2, −z+1; (vi) x+1/2, −y+1/2, −z+1; (vii) −x+1/2, y−1/2, z; (viii) −x+1, y−1/2, −z+1/2; (ix) −x+3/2, y−1/2, z; (x) −x+1, −y, −z+1; (xi) −x+1/2, y+1/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···N1 | 0.93 | 2.51 | 2.838 (2) | 101 |