organic compounds
In the title compound, C13H14N2OS, the benzene and thiazole rings make a dihedral angle of 73.44 (10)°. The intermolecular N—HN hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing is further stabilized by van der Waals forces.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501250X/cv6497sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680501250X/cv6497Isup2.hkl |
CCDC reference: 271859
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.122
- Data-to-parameter ratio = 16.6
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 (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
5-acetyl-4-methyl-2-(o-toluidinyl)-1,3-thiazole top
Crystal data top
C13H14N2OS | F(000) = 520 |
Mr = 246.32 | Dx = 1.299 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 871 reflections |
a = 10.797 (2) Å | θ = 2.2–26.5° |
b = 11.571 (2) Å | µ = 0.24 mm−1 |
c = 12.0982 (16) Å | T = 273 K |
β = 123.576 (11)° | Block, colourless |
V = 1259.3 (4) Å3 | 0.41 × 0.40 × 0.33 mm |
Z = 4 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2610 independent reflections |
Radiation source: fine-focus sealed tube | 2343 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.5°, θmin = 2.2° |
ω scans | h = −13→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −14→14 |
Tmin = 0.907, Tmax = 0.924 | l = −14→15 |
6884 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) = 0.122 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0659P)2 + 0.3401P] where P = (Fo2 + 2Fc2)/3 |
2610 reflections | (Δ/σ)max < 0.001 |
157 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.36514 (5) | 0.14029 (4) | 0.09201 (4) | 0.04631 (17) | |
O1 | 0.56321 (19) | 0.21909 (18) | 0.47003 (16) | 0.0833 (6) | |
N1 | 0.11037 (16) | 0.02748 (15) | −0.07959 (14) | 0.0471 (4) | |
H1A | 0.0377 | −0.0165 | −0.0963 | 0.057* | |
N2 | 0.18362 (15) | 0.04675 (12) | 0.14127 (14) | 0.0400 (3) | |
C1 | 0.0342 (2) | 0.14303 (15) | −0.27556 (18) | 0.0450 (4) | |
C2 | 0.0492 (3) | 0.1663 (2) | −0.3802 (2) | 0.0599 (5) | |
H2B | −0.0124 | 0.2212 | −0.4431 | 0.072* | |
C3 | 0.1522 (3) | 0.1106 (2) | −0.3932 (2) | 0.0691 (6) | |
H3A | 0.1592 | 0.1275 | −0.4647 | 0.083* | |
C4 | 0.2453 (3) | 0.0300 (2) | −0.3014 (3) | 0.0683 (6) | |
H4A | 0.3172 | −0.0061 | −0.3090 | 0.082* | |
C5 | 0.2314 (2) | 0.00262 (18) | −0.1972 (2) | 0.0548 (5) | |
H5A | 0.2928 | −0.0530 | −0.1353 | 0.066* | |
C6 | 0.12603 (19) | 0.05827 (15) | −0.18549 (16) | 0.0415 (4) | |
C7 | −0.0755 (3) | 0.2078 (2) | −0.2597 (2) | 0.0646 (6) | |
H7A | −0.1535 | 0.1564 | −0.2754 | 0.097* | |
H7B | −0.1171 | 0.2703 | −0.3223 | 0.097* | |
H7C | −0.0260 | 0.2381 | −0.1712 | 0.097* | |
C8 | 0.20538 (17) | 0.06492 (14) | 0.04581 (16) | 0.0385 (4) | |
C9 | 0.4052 (2) | 0.14896 (15) | 0.25331 (18) | 0.0444 (4) | |
C10 | 0.29605 (19) | 0.09372 (15) | 0.25821 (17) | 0.0417 (4) | |
C11 | 0.5305 (2) | 0.21665 (18) | 0.3561 (2) | 0.0554 (5) | |
C12 | 0.6173 (3) | 0.2869 (2) | 0.3164 (3) | 0.0784 (7) | |
H12A | 0.7008 | 0.3222 | 0.3937 | 0.118* | |
H12B | 0.5544 | 0.3459 | 0.2549 | 0.118* | |
H12C | 0.6520 | 0.2375 | 0.2753 | 0.118* | |
C13 | 0.2875 (2) | 0.0832 (2) | 0.37681 (19) | 0.0589 (5) | |
H13A | 0.1870 | 0.0666 | 0.3486 | 0.088* | |
H13B | 0.3187 | 0.1545 | 0.4255 | 0.088* | |
H13C | 0.3514 | 0.0218 | 0.4326 | 0.088* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0391 (3) | 0.0552 (3) | 0.0480 (3) | −0.00770 (18) | 0.0262 (2) | 0.00222 (19) |
O1 | 0.0629 (10) | 0.1168 (15) | 0.0560 (10) | −0.0252 (10) | 0.0240 (8) | −0.0206 (9) |
N1 | 0.0389 (7) | 0.0656 (10) | 0.0388 (8) | −0.0114 (7) | 0.0227 (7) | −0.0005 (7) |
N2 | 0.0366 (7) | 0.0460 (8) | 0.0405 (7) | −0.0021 (6) | 0.0233 (6) | 0.0006 (6) |
C1 | 0.0450 (9) | 0.0461 (9) | 0.0432 (9) | −0.0075 (8) | 0.0239 (8) | −0.0054 (7) |
C2 | 0.0674 (13) | 0.0632 (12) | 0.0469 (11) | −0.0074 (11) | 0.0302 (10) | 0.0066 (9) |
C3 | 0.0853 (16) | 0.0842 (16) | 0.0587 (13) | −0.0201 (14) | 0.0530 (13) | −0.0069 (12) |
C4 | 0.0736 (14) | 0.0789 (15) | 0.0838 (16) | −0.0071 (12) | 0.0633 (14) | −0.0124 (13) |
C5 | 0.0518 (11) | 0.0582 (11) | 0.0638 (12) | 0.0012 (9) | 0.0379 (10) | 0.0021 (9) |
C6 | 0.0407 (9) | 0.0484 (9) | 0.0399 (9) | −0.0093 (7) | 0.0250 (8) | −0.0045 (7) |
C7 | 0.0597 (12) | 0.0661 (13) | 0.0663 (13) | 0.0122 (11) | 0.0337 (11) | 0.0028 (11) |
C8 | 0.0335 (8) | 0.0419 (9) | 0.0430 (9) | 0.0003 (7) | 0.0229 (7) | 0.0043 (7) |
C9 | 0.0392 (9) | 0.0467 (10) | 0.0455 (9) | −0.0013 (7) | 0.0222 (8) | −0.0001 (7) |
C10 | 0.0403 (9) | 0.0421 (9) | 0.0432 (9) | 0.0020 (7) | 0.0235 (8) | 0.0010 (7) |
C11 | 0.0432 (10) | 0.0576 (12) | 0.0575 (12) | −0.0057 (9) | 0.0229 (9) | −0.0081 (9) |
C12 | 0.0642 (14) | 0.0787 (16) | 0.0871 (17) | −0.0309 (12) | 0.0385 (13) | −0.0175 (13) |
C13 | 0.0619 (12) | 0.0750 (14) | 0.0470 (10) | −0.0110 (11) | 0.0347 (10) | −0.0091 (10) |
Geometric parameters (Å, º) top
S1—C8 | 1.7269 (16) | C4—H4A | 0.9300 |
S1—C9 | 1.7527 (19) | C5—C6 | 1.381 (3) |
O1—C11 | 1.219 (3) | C5—H5A | 0.9300 |
N1—C8 | 1.349 (2) | C7—H7A | 0.9600 |
N1—C6 | 1.427 (2) | C7—H7B | 0.9600 |
N1—H1A | 0.8600 | C7—H7C | 0.9600 |
N2—C8 | 1.317 (2) | C9—C10 | 1.370 (2) |
N2—C10 | 1.368 (2) | C9—C11 | 1.459 (3) |
C1—C2 | 1.389 (3) | C10—C13 | 1.493 (2) |
C1—C6 | 1.392 (3) | C11—C12 | 1.506 (3) |
C1—C7 | 1.500 (3) | C12—H12A | 0.9600 |
C2—C3 | 1.367 (3) | C12—H12B | 0.9600 |
C2—H2B | 0.9300 | C12—H12C | 0.9600 |
C3—C4 | 1.370 (4) | C13—H13A | 0.9600 |
C3—H3A | 0.9300 | C13—H13B | 0.9600 |
C4—C5 | 1.387 (3) | C13—H13C | 0.9600 |
C8—S1—C9 | 88.65 (8) | H7A—C7—H7C | 109.5 |
C8—N1—C6 | 122.38 (14) | H7B—C7—H7C | 109.5 |
C8—N1—H1A | 118.8 | N2—C8—N1 | 122.80 (15) |
C6—N1—H1A | 118.8 | N2—C8—S1 | 115.32 (13) |
C8—N2—C10 | 110.92 (14) | N1—C8—S1 | 121.89 (13) |
C2—C1—C6 | 117.26 (18) | C10—C9—C11 | 128.87 (18) |
C2—C1—C7 | 121.21 (19) | C10—C9—S1 | 109.45 (13) |
C6—C1—C7 | 121.53 (17) | C11—C9—S1 | 121.41 (14) |
C3—C2—C1 | 121.7 (2) | N2—C10—C9 | 115.67 (16) |
C3—C2—H2B | 119.1 | N2—C10—C13 | 118.07 (16) |
C1—C2—H2B | 119.1 | C9—C10—C13 | 126.24 (17) |
C2—C3—C4 | 120.42 (19) | O1—C11—C9 | 121.89 (19) |
C2—C3—H3A | 119.8 | O1—C11—C12 | 120.4 (2) |
C4—C3—H3A | 119.8 | C9—C11—C12 | 117.72 (19) |
C3—C4—C5 | 119.5 (2) | C11—C12—H12A | 109.5 |
C3—C4—H4A | 120.3 | C11—C12—H12B | 109.5 |
C5—C4—H4A | 120.3 | H12A—C12—H12B | 109.5 |
C6—C5—C4 | 119.8 (2) | C11—C12—H12C | 109.5 |
C6—C5—H5A | 120.1 | H12A—C12—H12C | 109.5 |
C4—C5—H5A | 120.1 | H12B—C12—H12C | 109.5 |
C5—C6—C1 | 121.29 (17) | C10—C13—H13A | 109.5 |
C5—C6—N1 | 119.26 (17) | C10—C13—H13B | 109.5 |
C1—C6—N1 | 119.45 (16) | H13A—C13—H13B | 109.5 |
C1—C7—H7A | 109.5 | C10—C13—H13C | 109.5 |
C1—C7—H7B | 109.5 | H13A—C13—H13C | 109.5 |
H7A—C7—H7B | 109.5 | H13B—C13—H13C | 109.5 |
C1—C7—H7C | 109.5 | ||
C6—C1—C2—C3 | −1.6 (3) | C6—N1—C8—S1 | −7.2 (2) |
C7—C1—C2—C3 | 177.8 (2) | C9—S1—C8—N2 | −0.46 (14) |
C1—C2—C3—C4 | −0.5 (4) | C9—S1—C8—N1 | 179.65 (16) |
C2—C3—C4—C5 | 1.9 (4) | C8—S1—C9—C10 | 0.56 (14) |
C3—C4—C5—C6 | −1.2 (3) | C8—S1—C9—C11 | −173.98 (16) |
C4—C5—C6—C1 | −0.9 (3) | C8—N2—C10—C9 | 0.3 (2) |
C4—C5—C6—N1 | 178.55 (18) | C8—N2—C10—C13 | 178.77 (16) |
C2—C1—C6—C5 | 2.3 (3) | C11—C9—C10—N2 | 173.43 (18) |
C7—C1—C6—C5 | −177.03 (18) | S1—C9—C10—N2 | −0.6 (2) |
C2—C1—C6—N1 | −177.21 (17) | C11—C9—C10—C13 | −4.9 (3) |
C7—C1—C6—N1 | 3.5 (3) | S1—C9—C10—C13 | −178.96 (16) |
C8—N1—C6—C5 | 77.9 (2) | C10—C9—C11—O1 | 9.9 (3) |
C8—N1—C6—C1 | −102.6 (2) | S1—C9—C11—O1 | −176.69 (18) |
C10—N2—C8—N1 | −179.90 (16) | C10—C9—C11—C12 | −168.5 (2) |
C10—N2—C8—S1 | 0.21 (19) | S1—C9—C11—C12 | 4.9 (3) |
C6—N1—C8—N2 | 172.96 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13B···O1 | 0.96 | 2.50 | 2.982 (4) | 111 |
N1—H1A···N2i | 0.86 | 2.17 | 2.958 (3) | 153 |
Symmetry code: (i) −x, −y, −z. |