organic compounds
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—HN hydrogen bonds, which produce dimers located about the crystallographic twofold rotation axes.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022379/kj2013sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022379/kj2013Isup2.hkl |
CCDC reference: 613752
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
C11H12N2S | F(000) = 864 |
Mr = 204.29 | Dx = 1.292 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1838 reflections |
a = 21.697 (6) Å | θ = 2.7–27.0° |
b = 7.860 (2) Å | µ = 0.27 mm−1 |
c = 12.617 (3) Å | T = 298 K |
β = 102.535 (5)° | Block, colourless |
V = 2100.6 (9) Å3 | 0.49 × 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 tube | 1694 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.0°, θmin = 2.7° |
ω scans | h = −27→27 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −10→10 |
Tmin = 0.879, Tmax = 0.958 | l = −16→12 |
6033 measured reflections |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-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 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.47184 (2) | 0.22525 (7) | 0.53729 (4) | 0.0502 (2) | |
N1 | 0.43310 (8) | 0.1742 (2) | 0.31612 (13) | 0.0520 (5) | |
H1A | 0.4420 | 0.1959 | 0.2543 | 0.062* | |
N2 | 0.53299 (7) | 0.2768 (2) | 0.38845 (13) | 0.0469 (4) | |
C1 | 0.34436 (10) | 0.0795 (3) | 0.39428 (18) | 0.0621 (6) | |
H1 | 0.3625 | 0.1236 | 0.4623 | 0.075* | |
C2 | 0.28684 (11) | −0.0025 (4) | 0.3779 (2) | 0.0766 (8) | |
H2 | 0.2671 | −0.0149 | 0.4360 | 0.092* | |
C3 | 0.25826 (12) | −0.0657 (4) | 0.2796 (2) | 0.0741 (7) | |
H3 | 0.2192 | −0.1193 | 0.2697 | 0.089* | |
C4 | 0.28811 (11) | −0.0488 (3) | 0.1951 (2) | 0.0688 (7) | |
H4 | 0.2692 | −0.0921 | 0.1272 | 0.083* | |
C5 | 0.34559 (10) | 0.0311 (3) | 0.20912 (17) | 0.0544 (5) | |
H5 | 0.3650 | 0.0419 | 0.1506 | 0.065* | |
C6 | 0.37495 (9) | 0.0960 (3) | 0.30941 (16) | 0.0456 (5) | |
C7 | 0.47867 (9) | 0.2227 (2) | 0.40357 (16) | 0.0428 (4) | |
C8 | 0.57164 (9) | 0.3268 (3) | 0.48614 (17) | 0.0470 (5) | |
C9 | 0.63545 (10) | 0.3956 (3) | 0.4835 (2) | 0.0658 (6) | |
H9A | 0.6309 | 0.4974 | 0.4404 | 0.099* | |
H9B | 0.6586 | 0.3125 | 0.4523 | 0.099* | |
H9C | 0.6578 | 0.4213 | 0.5561 | 0.099* | |
C10 | 0.54743 (9) | 0.3085 (3) | 0.57466 (16) | 0.0487 (5) | |
C11 | 0.57543 (11) | 0.3512 (3) | 0.69056 (17) | 0.0663 (6) | |
H11A | 0.6190 | 0.3815 | 0.6979 | 0.100* | |
H11B | 0.5723 | 0.2543 | 0.7355 | 0.100* | |
H11C | 0.5529 | 0.4452 | 0.7127 | 0.100* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0505 (3) | 0.0638 (4) | 0.0380 (3) | 0.0021 (2) | 0.0137 (2) | 0.0010 (2) |
N1 | 0.0464 (9) | 0.0739 (12) | 0.0363 (9) | −0.0135 (9) | 0.0106 (7) | −0.0011 (8) |
N2 | 0.0411 (9) | 0.0593 (10) | 0.0409 (9) | −0.0015 (8) | 0.0106 (7) | −0.0020 (8) |
C1 | 0.0549 (13) | 0.0834 (17) | 0.0493 (13) | −0.0153 (12) | 0.0140 (10) | 0.0016 (11) |
C2 | 0.0590 (14) | 0.107 (2) | 0.0666 (16) | −0.0212 (14) | 0.0204 (12) | 0.0135 (15) |
C3 | 0.0516 (13) | 0.0867 (18) | 0.0803 (18) | −0.0229 (13) | 0.0061 (13) | 0.0110 (15) |
C4 | 0.0596 (14) | 0.0732 (15) | 0.0651 (15) | −0.0123 (12) | −0.0051 (12) | −0.0018 (13) |
C5 | 0.0524 (12) | 0.0609 (13) | 0.0494 (12) | −0.0030 (10) | 0.0099 (10) | 0.0017 (10) |
C6 | 0.0423 (10) | 0.0481 (11) | 0.0452 (11) | −0.0004 (9) | 0.0070 (9) | 0.0045 (9) |
C7 | 0.0436 (10) | 0.0479 (10) | 0.0377 (10) | 0.0018 (9) | 0.0107 (8) | 0.0007 (8) |
C8 | 0.0394 (10) | 0.0534 (12) | 0.0464 (11) | 0.0047 (9) | 0.0058 (9) | −0.0021 (9) |
C9 | 0.0436 (12) | 0.0858 (17) | 0.0659 (15) | −0.0044 (11) | 0.0073 (11) | −0.0067 (13) |
C10 | 0.0461 (11) | 0.0554 (12) | 0.0421 (11) | 0.0077 (9) | 0.0043 (9) | −0.0016 (9) |
C11 | 0.0628 (14) | 0.0874 (17) | 0.0439 (12) | 0.0107 (13) | 0.0007 (11) | −0.0065 (12) |
Geometric parameters (Å, º) top
S1—C7 | 1.726 (2) | C4—C5 | 1.373 (3) |
S1—C10 | 1.733 (2) | C4—H4 | 0.9300 |
N1—C7 | 1.366 (3) | C5—C6 | 1.385 (3) |
N1—C6 | 1.389 (2) | C5—H5 | 0.9300 |
N1—H1A | 0.8600 | C8—C10 | 1.341 (3) |
N2—C7 | 1.305 (2) | C8—C9 | 1.494 (3) |
N2—C8 | 1.389 (3) | C9—H9A | 0.9600 |
C1—C2 | 1.380 (3) | C9—H9B | 0.9600 |
C1—C6 | 1.383 (3) | C9—H9C | 0.9600 |
C1—H1 | 0.9300 | C10—C11 | 1.495 (3) |
C2—C3 | 1.355 (4) | C11—H11A | 0.9600 |
C2—H2 | 0.9300 | C11—H11B | 0.9600 |
C3—C4 | 1.369 (4) | C11—H11C | 0.9600 |
C3—H3 | 0.9300 | ||
C7—S1—C10 | 89.62 (9) | C5—C6—N1 | 116.76 (18) |
C7—N1—C6 | 131.39 (17) | N2—C7—N1 | 119.41 (18) |
C7—N1—H1A | 114.3 | N2—C7—S1 | 114.26 (15) |
C6—N1—H1A | 114.3 | N1—C7—S1 | 126.31 (15) |
C7—N2—C8 | 110.66 (17) | C10—C8—N2 | 116.02 (18) |
C2—C1—C6 | 119.9 (2) | C10—C8—C9 | 126.1 (2) |
C2—C1—H1 | 120.1 | N2—C8—C9 | 117.83 (19) |
C6—C1—H1 | 120.1 | C8—C9—H9A | 109.5 |
C3—C2—C1 | 121.8 (2) | C8—C9—H9B | 109.5 |
C3—C2—H2 | 119.1 | H9A—C9—H9B | 109.5 |
C1—C2—H2 | 119.1 | C8—C9—H9C | 109.5 |
C2—C3—C4 | 118.6 (2) | H9A—C9—H9C | 109.5 |
C2—C3—H3 | 120.7 | H9B—C9—H9C | 109.5 |
C4—C3—H3 | 120.7 | C8—C10—C11 | 129.9 (2) |
C3—C4—C5 | 120.9 (2) | C8—C10—S1 | 109.42 (16) |
C3—C4—H4 | 119.5 | C11—C10—S1 | 120.70 (17) |
C5—C4—H4 | 119.5 | C10—C11—H11A | 109.5 |
C4—C5—C6 | 120.7 (2) | C10—C11—H11B | 109.5 |
C4—C5—H5 | 119.6 | H11A—C11—H11B | 109.5 |
C6—C5—H5 | 119.6 | C10—C11—H11C | 109.5 |
C1—C6—C5 | 118.0 (2) | H11A—C11—H11C | 109.5 |
C1—C6—N1 | 125.20 (19) | H11B—C11—H11C | 109.5 |
C6—C1—C2—C3 | −1.3 (4) | C6—N1—C7—N2 | 172.1 (2) |
C1—C2—C3—C4 | 0.9 (4) | C6—N1—C7—S1 | −9.5 (3) |
C2—C3—C4—C5 | −0.4 (4) | C10—S1—C7—N2 | 0.90 (16) |
C3—C4—C5—C6 | 0.3 (4) | C10—S1—C7—N1 | −177.56 (19) |
C2—C1—C6—C5 | 1.2 (4) | C7—N2—C8—C10 | 1.0 (3) |
C2—C1—C6—N1 | −179.4 (2) | C7—N2—C8—C9 | −178.82 (18) |
C4—C5—C6—C1 | −0.7 (3) | N2—C8—C10—C11 | −179.0 (2) |
C4—C5—C6—N1 | 179.8 (2) | C9—C8—C10—C11 | 0.7 (4) |
C7—N1—C6—C1 | 13.9 (4) | N2—C8—C10—S1 | −0.3 (2) |
C7—N1—C6—C5 | −166.7 (2) | C9—C8—C10—S1 | 179.48 (18) |
C8—N2—C7—N1 | 177.38 (18) | C7—S1—C10—C8 | −0.31 (16) |
C8—N2—C7—S1 | −1.2 (2) | C7—S1—C10—C11 | 178.57 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···S1 | 0.93 | 2.49 | 3.171 (2) | 130 |
N1—H1A···N2i | 0.86 | 2.09 | 2.946 (2) | 173 |
Symmetry code: (i) −x+1, y, −z+1/2. |