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In the title compund, C11H12N2S, the whole mol­ecule is essentially planar except for methyl H atoms, with a maximum deviation of 0.160 (2) Å for the aniline N atom. The mol­ecule is stabilized by π–π inter­actions and inter­molecular N—H...N hydrogen bonds, which produce dimers located about the crystallographic twofold rotation axes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022379/kj2013sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022379/kj2013Isup2.hkl
Contains datablock I

CCDC reference: 613752

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.120
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

2-Anilino-4,5-dimethyl-1,3-thiazole top
Crystal data top
C11H12N2SF(000) = 864
Mr = 204.29Dx = 1.292 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1838 reflections
a = 21.697 (6) Åθ = 2.7–27.0°
b = 7.860 (2) ŵ = 0.27 mm1
c = 12.617 (3) ÅT = 298 K
β = 102.535 (5)°Block, colourless
V = 2100.6 (9) Å30.49 × 0.20 × 0.16 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2276 independent reflections
Radiation source: fine-focus sealed tube1694 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 83.66 pixels mm-1θmax = 27.0°, θmin = 2.7°
ω scansh = 2727
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 1010
Tmin = 0.879, Tmax = 0.958l = 1612
6033 measured reflections
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0623P)2 + 0.7325P]
where P = (Fo2 + 2Fc2)/3
2276 reflections(Δ/σ)max < 0.001
129 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.16 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.47184 (2)0.22525 (7)0.53729 (4)0.0502 (2)
N10.43310 (8)0.1742 (2)0.31612 (13)0.0520 (5)
H1A0.44200.19590.25430.062*
N20.53299 (7)0.2768 (2)0.38845 (13)0.0469 (4)
C10.34436 (10)0.0795 (3)0.39428 (18)0.0621 (6)
H10.36250.12360.46230.075*
C20.28684 (11)0.0025 (4)0.3779 (2)0.0766 (8)
H20.26710.01490.43600.092*
C30.25826 (12)0.0657 (4)0.2796 (2)0.0741 (7)
H30.21920.11930.26970.089*
C40.28811 (11)0.0488 (3)0.1951 (2)0.0688 (7)
H40.26920.09210.12720.083*
C50.34559 (10)0.0311 (3)0.20912 (17)0.0544 (5)
H50.36500.04190.15060.065*
C60.37495 (9)0.0960 (3)0.30941 (16)0.0456 (5)
C70.47867 (9)0.2227 (2)0.40357 (16)0.0428 (4)
C80.57164 (9)0.3268 (3)0.48614 (17)0.0470 (5)
C90.63545 (10)0.3956 (3)0.4835 (2)0.0658 (6)
H9A0.63090.49740.44040.099*
H9B0.65860.31250.45230.099*
H9C0.65780.42130.55610.099*
C100.54743 (9)0.3085 (3)0.57466 (16)0.0487 (5)
C110.57543 (11)0.3512 (3)0.69056 (17)0.0663 (6)
H11A0.61900.38150.69790.100*
H11B0.57230.25430.73550.100*
H11C0.55290.44520.71270.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0505 (3)0.0638 (4)0.0380 (3)0.0021 (2)0.0137 (2)0.0010 (2)
N10.0464 (9)0.0739 (12)0.0363 (9)0.0135 (9)0.0106 (7)0.0011 (8)
N20.0411 (9)0.0593 (10)0.0409 (9)0.0015 (8)0.0106 (7)0.0020 (8)
C10.0549 (13)0.0834 (17)0.0493 (13)0.0153 (12)0.0140 (10)0.0016 (11)
C20.0590 (14)0.107 (2)0.0666 (16)0.0212 (14)0.0204 (12)0.0135 (15)
C30.0516 (13)0.0867 (18)0.0803 (18)0.0229 (13)0.0061 (13)0.0110 (15)
C40.0596 (14)0.0732 (15)0.0651 (15)0.0123 (12)0.0051 (12)0.0018 (13)
C50.0524 (12)0.0609 (13)0.0494 (12)0.0030 (10)0.0099 (10)0.0017 (10)
C60.0423 (10)0.0481 (11)0.0452 (11)0.0004 (9)0.0070 (9)0.0045 (9)
C70.0436 (10)0.0479 (10)0.0377 (10)0.0018 (9)0.0107 (8)0.0007 (8)
C80.0394 (10)0.0534 (12)0.0464 (11)0.0047 (9)0.0058 (9)0.0021 (9)
C90.0436 (12)0.0858 (17)0.0659 (15)0.0044 (11)0.0073 (11)0.0067 (13)
C100.0461 (11)0.0554 (12)0.0421 (11)0.0077 (9)0.0043 (9)0.0016 (9)
C110.0628 (14)0.0874 (17)0.0439 (12)0.0107 (13)0.0007 (11)0.0065 (12)
Geometric parameters (Å, º) top
S1—C71.726 (2)C4—C51.373 (3)
S1—C101.733 (2)C4—H40.9300
N1—C71.366 (3)C5—C61.385 (3)
N1—C61.389 (2)C5—H50.9300
N1—H1A0.8600C8—C101.341 (3)
N2—C71.305 (2)C8—C91.494 (3)
N2—C81.389 (3)C9—H9A0.9600
C1—C21.380 (3)C9—H9B0.9600
C1—C61.383 (3)C9—H9C0.9600
C1—H10.9300C10—C111.495 (3)
C2—C31.355 (4)C11—H11A0.9600
C2—H20.9300C11—H11B0.9600
C3—C41.369 (4)C11—H11C0.9600
C3—H30.9300
C7—S1—C1089.62 (9)C5—C6—N1116.76 (18)
C7—N1—C6131.39 (17)N2—C7—N1119.41 (18)
C7—N1—H1A114.3N2—C7—S1114.26 (15)
C6—N1—H1A114.3N1—C7—S1126.31 (15)
C7—N2—C8110.66 (17)C10—C8—N2116.02 (18)
C2—C1—C6119.9 (2)C10—C8—C9126.1 (2)
C2—C1—H1120.1N2—C8—C9117.83 (19)
C6—C1—H1120.1C8—C9—H9A109.5
C3—C2—C1121.8 (2)C8—C9—H9B109.5
C3—C2—H2119.1H9A—C9—H9B109.5
C1—C2—H2119.1C8—C9—H9C109.5
C2—C3—C4118.6 (2)H9A—C9—H9C109.5
C2—C3—H3120.7H9B—C9—H9C109.5
C4—C3—H3120.7C8—C10—C11129.9 (2)
C3—C4—C5120.9 (2)C8—C10—S1109.42 (16)
C3—C4—H4119.5C11—C10—S1120.70 (17)
C5—C4—H4119.5C10—C11—H11A109.5
C4—C5—C6120.7 (2)C10—C11—H11B109.5
C4—C5—H5119.6H11A—C11—H11B109.5
C6—C5—H5119.6C10—C11—H11C109.5
C1—C6—C5118.0 (2)H11A—C11—H11C109.5
C1—C6—N1125.20 (19)H11B—C11—H11C109.5
C6—C1—C2—C31.3 (4)C6—N1—C7—N2172.1 (2)
C1—C2—C3—C40.9 (4)C6—N1—C7—S19.5 (3)
C2—C3—C4—C50.4 (4)C10—S1—C7—N20.90 (16)
C3—C4—C5—C60.3 (4)C10—S1—C7—N1177.56 (19)
C2—C1—C6—C51.2 (4)C7—N2—C8—C101.0 (3)
C2—C1—C6—N1179.4 (2)C7—N2—C8—C9178.82 (18)
C4—C5—C6—C10.7 (3)N2—C8—C10—C11179.0 (2)
C4—C5—C6—N1179.8 (2)C9—C8—C10—C110.7 (4)
C7—N1—C6—C113.9 (4)N2—C8—C10—S10.3 (2)
C7—N1—C6—C5166.7 (2)C9—C8—C10—S1179.48 (18)
C8—N2—C7—N1177.38 (18)C7—S1—C10—C80.31 (16)
C8—N2—C7—S11.2 (2)C7—S1—C10—C11178.57 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···S10.932.493.171 (2)130
N1—H1A···N2i0.862.092.946 (2)173
Symmetry code: (i) x+1, y, z+1/2.
 

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