organic compounds
The asymmetric unit of the title compound, C12H12N2OS, contains two crystallographically independent molecules. Both molecules are essentially planar and stabilized by intra- and intermolecular hydrogen-bonding interactions to form one-dimensional zigzag polymeric chains parallel to the c axis.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503326X/at6042sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680503326X/at6042Isup2.hkl |
CCDC reference: 289634
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.055
- wR factor = 0.125
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C18 .. 5.34 su PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
5-Acetyl-4-methyl-2-phenylamino-1,3-thiazole top
Crystal data top
C12H12N2OS | F(000) = 976 |
Mr = 232.30 | Dx = 1.328 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1480 reflections |
a = 12.932 (6) Å | θ = 1.6–26.0° |
b = 7.532 (3) Å | µ = 0.26 mm−1 |
c = 24.322 (11) Å | T = 293 K |
β = 101.236 (9)° | Block, colourless |
V = 2323.6 (18) Å3 | 0.31 × 0.19 × 0.12 mm |
Z = 8 |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4065 independent reflections |
Radiation source: fine-focus sealed tube | 2637 reflections with I > 2σI |
Graphite monochromator | Rint = 0.049 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.0°, θmin = 1.6° |
ω scans | h = −15→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −7→8 |
Tmin = 0.924, Tmax = 0.969 | l = −28→28 |
11081 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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0551P)2 + 0.1476P] where P = (Fo2 + 2Fc2)/3 |
4065 reflections | (Δ/σ)max < 0.001 |
293 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.11715 (6) | 0.17457 (11) | 0.36646 (3) | 0.0531 (3) | |
S2 | 0.95293 (6) | 0.20100 (12) | 0.10301 (3) | 0.0540 (3) | |
O1 | 0.05122 (18) | 0.2456 (3) | 0.47004 (9) | 0.0735 (7) | |
O2 | 1.01763 (18) | 0.0760 (4) | 0.21506 (9) | 0.0862 (8) | |
N1 | 0.21706 (18) | 0.1096 (3) | 0.28282 (10) | 0.0555 (7) | |
H1 | 0.1532 | 0.0887 | 0.2663 | 0.067* | |
N2 | 0.31592 (18) | 0.2238 (3) | 0.36848 (10) | 0.0531 (7) | |
N3 | 0.85371 (19) | 0.3241 (3) | 0.00316 (10) | 0.0534 (7) | |
H3 | 0.9157 | 0.3114 | −0.0041 | 0.064* | |
N4 | 0.75385 (17) | 0.2705 (3) | 0.07319 (10) | 0.0481 (6) | |
C1 | 0.3986 (2) | 0.1147 (5) | 0.26695 (13) | 0.0607 (9) | |
H1A | 0.4229 | 0.1691 | 0.3014 | 0.073* | |
C2 | 0.4678 (3) | 0.0719 (5) | 0.23233 (14) | 0.0711 (10) | |
H2 | 0.5389 | 0.0998 | 0.2436 | 0.085* | |
C3 | 0.4344 (3) | −0.0101 (5) | 0.18215 (14) | 0.0684 (10) | |
H3A | 0.4824 | −0.0400 | 0.1597 | 0.082* | |
C4 | 0.3300 (3) | −0.0480 (4) | 0.16500 (13) | 0.0630 (9) | |
H4 | 0.3065 | −0.1035 | 0.1307 | 0.076* | |
C5 | 0.2594 (2) | −0.0045 (4) | 0.19827 (12) | 0.0561 (8) | |
H5 | 0.1881 | −0.0291 | 0.1861 | 0.067* | |
C6 | 0.2939 (2) | 0.0760 (4) | 0.24995 (12) | 0.0494 (8) | |
C7 | 0.2279 (2) | 0.1693 (4) | 0.33612 (12) | 0.0480 (7) | |
C8 | 0.1957 (2) | 0.2590 (4) | 0.42724 (11) | 0.0483 (8) | |
C9 | 0.2972 (2) | 0.2758 (4) | 0.41969 (12) | 0.0492 (8) | |
C10 | 0.3908 (2) | 0.3428 (5) | 0.46103 (13) | 0.0698 (10) | |
H10A | 0.3816 | 0.4667 | 0.4680 | 0.105* | |
H10B | 0.4535 | 0.3267 | 0.4460 | 0.105* | |
H10C | 0.3971 | 0.2778 | 0.4955 | 0.105* | |
C11 | 0.1428 (3) | 0.2913 (4) | 0.47394 (12) | 0.0542 (8) | |
C12 | 0.2000 (3) | 0.3820 (4) | 0.52584 (13) | 0.0695 (10) | |
H12A | 0.1506 | 0.4156 | 0.5487 | 0.104* | |
H12B | 0.2348 | 0.4861 | 0.5156 | 0.104* | |
H12C | 0.2514 | 0.3025 | 0.5464 | 0.104* | |
C13 | 0.6717 (3) | 0.4057 (4) | −0.03923 (14) | 0.0654 (9) | |
H13 | 0.6463 | 0.3627 | −0.0086 | 0.078* | |
C14 | 0.6035 (3) | 0.4808 (5) | −0.08435 (15) | 0.0791 (11) | |
H14 | 0.5318 | 0.4861 | −0.0839 | 0.095* | |
C15 | 0.6392 (4) | 0.5469 (5) | −0.12930 (15) | 0.0803 (11) | |
H15 | 0.5927 | 0.5988 | −0.1589 | 0.096* | |
C16 | 0.7434 (4) | 0.5360 (5) | −0.13022 (14) | 0.0762 (11) | |
H16 | 0.7681 | 0.5811 | −0.1608 | 0.091* | |
C17 | 0.8135 (3) | 0.4597 (4) | −0.08684 (13) | 0.0662 (9) | |
H17 | 0.8845 | 0.4511 | −0.0886 | 0.079* | |
C18 | 0.7779 (2) | 0.3958 (4) | −0.04052 (12) | 0.0527 (8) | |
C19 | 0.8431 (2) | 0.2716 (4) | 0.05547 (12) | 0.0458 (7) | |
C20 | 0.8721 (2) | 0.1687 (4) | 0.15179 (12) | 0.0479 (7) | |
C21 | 0.7701 (2) | 0.2126 (4) | 0.12766 (12) | 0.0468 (7) | |
C22 | 0.6740 (2) | 0.2028 (5) | 0.15336 (13) | 0.0640 (9) | |
H22A | 0.6567 | 0.0807 | 0.1584 | 0.096* | |
H22B | 0.6161 | 0.2600 | 0.1291 | 0.096* | |
H22C | 0.6877 | 0.2616 | 0.1891 | 0.096* | |
C23 | 0.9225 (3) | 0.1029 (5) | 0.20590 (13) | 0.0592 (9) | |
C24 | 0.8614 (3) | 0.0670 (5) | 0.25108 (13) | 0.0772 (11) | |
H24A | 0.9062 | 0.0092 | 0.2820 | 0.116* | |
H24B | 0.8025 | −0.0083 | 0.2367 | 0.116* | |
H24C | 0.8364 | 0.1771 | 0.2635 | 0.116* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0496 (5) | 0.0584 (6) | 0.0515 (5) | −0.0039 (4) | 0.0107 (4) | −0.0011 (4) |
S2 | 0.0448 (4) | 0.0652 (6) | 0.0529 (5) | −0.0033 (4) | 0.0118 (4) | −0.0034 (4) |
O1 | 0.0670 (15) | 0.0872 (19) | 0.0728 (16) | −0.0034 (14) | 0.0296 (12) | 0.0009 (13) |
O2 | 0.0561 (14) | 0.138 (3) | 0.0579 (15) | 0.0056 (16) | −0.0063 (12) | −0.0029 (14) |
N1 | 0.0494 (15) | 0.0694 (19) | 0.0459 (15) | −0.0054 (13) | 0.0046 (12) | −0.0102 (13) |
N2 | 0.0526 (15) | 0.0603 (18) | 0.0450 (15) | −0.0062 (13) | 0.0063 (13) | −0.0029 (13) |
N3 | 0.0544 (15) | 0.0562 (17) | 0.0531 (16) | −0.0069 (14) | 0.0188 (13) | 0.0007 (13) |
N4 | 0.0469 (14) | 0.0500 (16) | 0.0489 (15) | −0.0018 (12) | 0.0132 (12) | 0.0004 (12) |
C1 | 0.058 (2) | 0.079 (3) | 0.0447 (19) | −0.0096 (19) | 0.0086 (16) | −0.0015 (17) |
C2 | 0.061 (2) | 0.096 (3) | 0.060 (2) | −0.012 (2) | 0.0201 (18) | 0.004 (2) |
C3 | 0.071 (2) | 0.077 (3) | 0.063 (2) | 0.002 (2) | 0.0271 (19) | 0.003 (2) |
C4 | 0.083 (3) | 0.061 (2) | 0.0474 (19) | 0.002 (2) | 0.0181 (19) | −0.0032 (16) |
C5 | 0.061 (2) | 0.054 (2) | 0.0512 (19) | −0.0086 (17) | 0.0068 (16) | −0.0033 (16) |
C6 | 0.0556 (19) | 0.048 (2) | 0.0453 (18) | 0.0004 (16) | 0.0113 (15) | 0.0067 (15) |
C7 | 0.0499 (18) | 0.0462 (19) | 0.0462 (18) | 0.0004 (16) | 0.0052 (15) | 0.0018 (15) |
C8 | 0.0547 (19) | 0.0437 (19) | 0.0454 (18) | 0.0001 (15) | 0.0072 (15) | 0.0036 (14) |
C9 | 0.0538 (19) | 0.050 (2) | 0.0435 (18) | −0.0017 (16) | 0.0074 (15) | 0.0004 (15) |
C10 | 0.062 (2) | 0.088 (3) | 0.058 (2) | −0.008 (2) | 0.0063 (17) | −0.0103 (19) |
C11 | 0.068 (2) | 0.044 (2) | 0.053 (2) | 0.0073 (18) | 0.0171 (17) | 0.0084 (15) |
C12 | 0.095 (3) | 0.064 (2) | 0.053 (2) | −0.003 (2) | 0.0237 (19) | −0.0021 (17) |
C13 | 0.062 (2) | 0.069 (3) | 0.060 (2) | −0.0035 (19) | −0.0007 (18) | 0.0108 (18) |
C14 | 0.077 (2) | 0.082 (3) | 0.072 (3) | −0.001 (2) | 0.000 (2) | 0.009 (2) |
C15 | 0.103 (3) | 0.068 (3) | 0.060 (2) | 0.006 (2) | −0.009 (2) | −0.001 (2) |
C16 | 0.124 (3) | 0.061 (2) | 0.047 (2) | 0.004 (3) | 0.024 (2) | 0.0021 (18) |
C17 | 0.087 (2) | 0.059 (2) | 0.056 (2) | −0.002 (2) | 0.021 (2) | −0.0004 (18) |
C18 | 0.062 (2) | 0.045 (2) | 0.0470 (19) | −0.0044 (17) | 0.0026 (16) | −0.0012 (15) |
C19 | 0.0477 (18) | 0.0424 (19) | 0.0491 (19) | −0.0057 (14) | 0.0138 (15) | −0.0062 (14) |
C20 | 0.0488 (18) | 0.051 (2) | 0.0441 (17) | −0.0032 (16) | 0.0096 (14) | −0.0079 (15) |
C21 | 0.0508 (18) | 0.0417 (19) | 0.0509 (19) | −0.0063 (15) | 0.0171 (15) | −0.0052 (15) |
C22 | 0.0556 (19) | 0.075 (3) | 0.066 (2) | −0.0006 (18) | 0.0238 (16) | −0.0012 (19) |
C23 | 0.061 (2) | 0.064 (2) | 0.051 (2) | −0.0051 (19) | 0.0074 (17) | −0.0090 (16) |
C24 | 0.089 (3) | 0.094 (3) | 0.051 (2) | 0.001 (2) | 0.0190 (19) | 0.0063 (19) |
Geometric parameters (Å, º) top
S1—C7 | 1.734 (3) | C9—C10 | 1.502 (4) |
S1—C8 | 1.742 (3) | C10—H10A | 0.9600 |
S2—C19 | 1.731 (3) | C10—H10B | 0.9600 |
S2—C20 | 1.744 (3) | C10—H10C | 0.9600 |
O1—C11 | 1.219 (3) | C11—C12 | 1.498 (4) |
O2—C23 | 1.223 (3) | C12—H12A | 0.9600 |
N1—C7 | 1.354 (4) | C12—H12B | 0.9600 |
N1—C6 | 1.414 (4) | C12—H12C | 0.9600 |
N1—H1 | 0.8600 | C13—C18 | 1.382 (4) |
N2—C7 | 1.317 (3) | C13—C14 | 1.387 (4) |
N2—C9 | 1.371 (3) | C13—H13 | 0.9300 |
N3—C19 | 1.364 (3) | C14—C15 | 1.361 (5) |
N3—C18 | 1.406 (4) | C14—H14 | 0.9300 |
N3—H3 | 0.8600 | C15—C16 | 1.355 (5) |
N4—C19 | 1.309 (3) | C15—H15 | 0.9300 |
N4—C21 | 1.372 (3) | C16—C17 | 1.375 (5) |
C1—C6 | 1.368 (4) | C16—H16 | 0.9300 |
C1—C2 | 1.381 (4) | C17—C18 | 1.384 (4) |
C1—H1A | 0.9300 | C17—H17 | 0.9300 |
C2—C3 | 1.361 (4) | C20—C21 | 1.376 (4) |
C2—H2 | 0.9300 | C20—C23 | 1.438 (4) |
C3—C4 | 1.364 (4) | C21—C22 | 1.497 (4) |
C3—H3A | 0.9300 | C22—H22A | 0.9600 |
C4—C5 | 1.372 (4) | C22—H22B | 0.9600 |
C4—H4 | 0.9300 | C22—H22C | 0.9600 |
C5—C6 | 1.389 (4) | C23—C24 | 1.498 (4) |
C5—H5 | 0.9300 | C24—H24A | 0.9600 |
C8—C9 | 1.367 (4) | C24—H24B | 0.9600 |
C8—C11 | 1.456 (4) | C24—H24C | 0.9600 |
C7—S1—C8 | 88.65 (14) | C11—C12—H12B | 109.5 |
C19—S2—C20 | 88.56 (14) | H12A—C12—H12B | 109.5 |
C7—N1—C6 | 130.4 (2) | C11—C12—H12C | 109.5 |
C7—N1—H1 | 114.8 | H12A—C12—H12C | 109.5 |
C6—N1—H1 | 114.8 | H12B—C12—H12C | 109.5 |
C7—N2—C9 | 110.3 (2) | C18—C13—C14 | 119.0 (3) |
C19—N3—C18 | 129.4 (3) | C18—C13—H13 | 120.5 |
C19—N3—H3 | 115.3 | C14—C13—H13 | 120.5 |
C18—N3—H3 | 115.3 | C15—C14—C13 | 121.5 (4) |
C19—N4—C21 | 109.9 (2) | C15—C14—H14 | 119.3 |
C6—C1—C2 | 119.1 (3) | C13—C14—H14 | 119.3 |
C6—C1—H1A | 120.4 | C16—C15—C14 | 119.0 (4) |
C2—C1—H1A | 120.4 | C16—C15—H15 | 120.5 |
C3—C2—C1 | 121.5 (3) | C14—C15—H15 | 120.5 |
C3—C2—H2 | 119.3 | C15—C16—C17 | 121.4 (3) |
C1—C2—H2 | 119.3 | C15—C16—H16 | 119.3 |
C2—C3—C4 | 119.5 (3) | C17—C16—H16 | 119.3 |
C2—C3—H3A | 120.3 | C16—C17—C18 | 119.7 (3) |
C4—C3—H3A | 120.3 | C16—C17—H17 | 120.1 |
C3—C4—C5 | 120.2 (3) | C18—C17—H17 | 120.1 |
C3—C4—H4 | 119.9 | C13—C18—C17 | 119.3 (3) |
C5—C4—H4 | 119.9 | C13—C18—N3 | 123.6 (3) |
C4—C5—C6 | 120.3 (3) | C17—C18—N3 | 117.1 (3) |
C4—C5—H5 | 119.8 | N4—C19—N3 | 124.3 (3) |
C6—C5—H5 | 119.8 | N4—C19—S2 | 116.1 (2) |
C1—C6—C5 | 119.4 (3) | N3—C19—S2 | 119.6 (2) |
C1—C6—N1 | 123.7 (3) | C21—C20—C23 | 134.4 (3) |
C5—C6—N1 | 116.9 (3) | C21—C20—S2 | 109.2 (2) |
N2—C7—N1 | 126.3 (3) | C23—C20—S2 | 116.5 (2) |
N2—C7—S1 | 115.3 (2) | N4—C21—C20 | 116.2 (2) |
N1—C7—S1 | 118.4 (2) | N4—C21—C22 | 115.8 (3) |
C9—C8—C11 | 134.3 (3) | C20—C21—C22 | 128.0 (3) |
C9—C8—S1 | 109.6 (2) | C21—C22—H22A | 109.5 |
C11—C8—S1 | 116.0 (2) | C21—C22—H22B | 109.5 |
C8—C9—N2 | 116.1 (3) | H22A—C22—H22B | 109.5 |
C8—C9—C10 | 127.7 (3) | C21—C22—H22C | 109.5 |
N2—C9—C10 | 116.2 (3) | H22A—C22—H22C | 109.5 |
C9—C10—H10A | 109.5 | H22B—C22—H22C | 109.5 |
C9—C10—H10B | 109.5 | O2—C23—C20 | 119.0 (3) |
H10A—C10—H10B | 109.5 | O2—C23—C24 | 119.5 (3) |
C9—C10—H10C | 109.5 | C20—C23—C24 | 121.6 (3) |
H10A—C10—H10C | 109.5 | C23—C24—H24A | 109.5 |
H10B—C10—H10C | 109.5 | C23—C24—H24B | 109.5 |
O1—C11—C8 | 119.3 (3) | H24A—C24—H24B | 109.5 |
O1—C11—C12 | 120.5 (3) | C23—C24—H24C | 109.5 |
C8—C11—C12 | 120.2 (3) | H24A—C24—H24C | 109.5 |
C11—C12—H12A | 109.5 | H24B—C24—H24C | 109.5 |
C6—C1—C2—C3 | −1.0 (5) | C18—C13—C14—C15 | −1.0 (6) |
C1—C2—C3—C4 | 1.3 (5) | C13—C14—C15—C16 | 1.1 (6) |
C2—C3—C4—C5 | −0.3 (5) | C14—C15—C16—C17 | 0.1 (6) |
C3—C4—C5—C6 | −1.0 (5) | C15—C16—C17—C18 | −1.4 (5) |
C2—C1—C6—C5 | −0.3 (5) | C14—C13—C18—C17 | −0.4 (5) |
C2—C1—C6—N1 | 178.2 (3) | C14—C13—C18—N3 | 179.3 (3) |
C4—C5—C6—C1 | 1.3 (5) | C16—C17—C18—C13 | 1.6 (5) |
C4—C5—C6—N1 | −177.3 (3) | C16—C17—C18—N3 | −178.2 (3) |
C7—N1—C6—C1 | −5.6 (5) | C19—N3—C18—C13 | −8.2 (5) |
C7—N1—C6—C5 | 172.9 (3) | C19—N3—C18—C17 | 171.5 (3) |
C9—N2—C7—N1 | 179.7 (3) | C21—N4—C19—N3 | −179.4 (3) |
C9—N2—C7—S1 | −1.0 (3) | C21—N4—C19—S2 | 0.6 (3) |
C6—N1—C7—N2 | 5.8 (5) | C18—N3—C19—N4 | 4.3 (5) |
C6—N1—C7—S1 | −173.5 (2) | C18—N3—C19—S2 | −175.7 (2) |
C8—S1—C7—N2 | 0.6 (2) | C20—S2—C19—N4 | −0.6 (2) |
C8—S1—C7—N1 | 180.0 (2) | C20—S2—C19—N3 | 179.3 (2) |
C7—S1—C8—C9 | 0.0 (2) | C19—S2—C20—C21 | 0.5 (2) |
C7—S1—C8—C11 | −178.5 (2) | C19—S2—C20—C23 | 179.7 (3) |
C11—C8—C9—N2 | 177.6 (3) | C19—N4—C21—C20 | −0.1 (4) |
S1—C8—C9—N2 | −0.5 (3) | C19—N4—C21—C22 | −179.4 (2) |
C11—C8—C9—C10 | −1.8 (6) | C23—C20—C21—N4 | −179.3 (3) |
S1—C8—C9—C10 | −179.9 (3) | S2—C20—C21—N4 | −0.3 (3) |
C7—N2—C9—C8 | 1.0 (4) | C23—C20—C21—C22 | −0.1 (6) |
C7—N2—C9—C10 | −179.6 (3) | S2—C20—C21—C22 | 178.9 (3) |
C9—C8—C11—O1 | −172.2 (3) | C21—C20—C23—O2 | 180.0 (3) |
S1—C8—C11—O1 | 5.8 (4) | S2—C20—C23—O2 | 1.1 (4) |
C9—C8—C11—C12 | 8.6 (5) | C21—C20—C23—C24 | −0.1 (6) |
S1—C8—C11—C12 | −173.3 (2) | S2—C20—C23—C24 | −179.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···N2 | 0.93 | 2.37 | 2.991 (4) | 124 |
C13—H13···N4 | 0.93 | 2.30 | 2.917 (4) | 123 |
N1—H1···O2i | 0.86 | 1.95 | 2.788 (4) | 166 |
N3—H3···O1ii | 0.86 | 2.02 | 2.872 (4) | 171 |
C5—H5···O2i | 0.93 | 2.57 | 3.288 (4) | 135 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, −y+1/2, z−1/2. |