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In the title compound, C
11H
11FN
2S, the dihedral angle between the least-squares planes of the fluoroaniline and 1,3-thiazole fragments is 46.47 (17)°. The molecules form dimers by N—H
N hydrogen bonds. There are no significant π–π interactions in the crystal structure.
Supporting information
CCDC reference: 618298
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.064
- wR factor = 0.152
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C11 H11 F N2 S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
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-(4-Fluoroanalino)-4,5-dimethyl-1,3-thiazole
top
Crystal data top
C11H11FN2S | F(000) = 464 |
Mr = 222.28 | Dx = 1.368 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1132 reflections |
a = 11.915 (5) Å | θ = 1.7–25.0° |
b = 4.0811 (17) Å | µ = 0.28 mm−1 |
c = 22.546 (9) Å | T = 298 K |
β = 100.151 (7)° | Slab, colourless |
V = 1079.2 (8) Å3 | 0.50 × 0.24 × 0.09 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 1887 independent reflections |
Radiation source: fine-focus sealed tube | 1423 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.0°, θmin = 1.7° |
ω scan | h = −10→14 |
Absorption correction: multi-scan SADABS (Bruker, 2000) | k = −4→4 |
Tmin = 0.872, Tmax = 0.975 | l = −26→24 |
5081 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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0668P)2 + 0.3409P] where P = (Fo2 + 2Fc2)/3 |
1887 reflections | (Δ/σ)max < 0.001 |
138 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F1 | −0.52902 (18) | 1.0963 (7) | 0.33147 (11) | 0.0941 (9) | |
S1 | −0.00061 (7) | 0.8311 (2) | 0.33806 (4) | 0.0520 (4) | |
N1 | −0.0987 (2) | 0.6902 (8) | 0.43523 (11) | 0.0528 (8) | |
H1A | −0.0911 | 0.6330 | 0.4724 | 0.063* | |
N2 | 0.0923 (2) | 0.5529 (7) | 0.43685 (11) | 0.0429 (7) | |
C1 | −0.2546 (3) | 0.7026 (10) | 0.34901 (14) | 0.0545 (10) | |
H1B | −0.2132 | 0.5695 | 0.3272 | 0.065* | |
C2 | −0.3624 (3) | 0.8077 (11) | 0.32293 (15) | 0.0622 (11) | |
H2B | −0.3930 | 0.7545 | 0.2833 | 0.075* | |
C3 | −0.4224 (3) | 0.9912 (11) | 0.35695 (16) | 0.0601 (11) | |
C4 | −0.3800 (3) | 1.0800 (10) | 0.41488 (16) | 0.0615 (11) | |
H4A | −0.4236 | 1.2024 | 0.4373 | 0.074* | |
C5 | −0.2708 (3) | 0.9832 (9) | 0.43933 (14) | 0.0504 (9) | |
H5A | −0.2393 | 1.0476 | 0.4783 | 0.060* | |
C6 | −0.2079 (3) | 0.7934 (8) | 0.40709 (13) | 0.0422 (8) | |
C7 | −0.0040 (3) | 0.6720 (8) | 0.40943 (12) | 0.0411 (8) | |
C8 | 0.1751 (3) | 0.5835 (8) | 0.40082 (14) | 0.0421 (8) | |
C9 | 0.1418 (3) | 0.7256 (8) | 0.34664 (14) | 0.0450 (9) | |
C10 | 0.2933 (3) | 0.4572 (10) | 0.42383 (16) | 0.0580 (10) | |
H10A | 0.3444 | 0.5365 | 0.3986 | 0.087* | |
H10B | 0.2927 | 0.2220 | 0.4232 | 0.087* | |
H10C | 0.3183 | 0.5324 | 0.4644 | 0.087* | |
C11 | 0.2079 (3) | 0.7896 (11) | 0.29697 (15) | 0.0648 (11) | |
H11A | 0.2842 | 0.7081 | 0.3085 | 0.097* | |
H11B | 0.2102 | 1.0211 | 0.2897 | 0.097* | |
H11C | 0.1716 | 0.6806 | 0.2609 | 0.097* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0466 (14) | 0.141 (3) | 0.0855 (17) | 0.0142 (15) | −0.0135 (12) | 0.0066 (16) |
S1 | 0.0521 (6) | 0.0630 (6) | 0.0382 (5) | −0.0017 (5) | 0.0009 (4) | 0.0113 (4) |
N1 | 0.0463 (18) | 0.078 (2) | 0.0331 (15) | 0.0127 (16) | 0.0028 (12) | 0.0074 (15) |
N2 | 0.0432 (17) | 0.0502 (17) | 0.0343 (14) | 0.0041 (13) | 0.0039 (12) | 0.0019 (12) |
C1 | 0.048 (2) | 0.071 (3) | 0.0437 (19) | −0.0036 (19) | 0.0054 (16) | −0.0090 (18) |
C2 | 0.049 (2) | 0.094 (3) | 0.0396 (19) | −0.015 (2) | −0.0035 (17) | −0.001 (2) |
C3 | 0.039 (2) | 0.082 (3) | 0.055 (2) | −0.001 (2) | −0.0032 (18) | 0.010 (2) |
C4 | 0.051 (2) | 0.072 (3) | 0.061 (2) | 0.008 (2) | 0.0079 (19) | −0.0058 (19) |
C5 | 0.049 (2) | 0.059 (2) | 0.0389 (19) | 0.0030 (19) | −0.0036 (16) | −0.0023 (16) |
C6 | 0.0393 (19) | 0.051 (2) | 0.0342 (17) | −0.0045 (16) | 0.0012 (14) | 0.0046 (15) |
C7 | 0.044 (2) | 0.043 (2) | 0.0346 (17) | −0.0028 (16) | 0.0029 (14) | −0.0015 (15) |
C8 | 0.042 (2) | 0.040 (2) | 0.0430 (18) | −0.0028 (15) | 0.0040 (15) | −0.0064 (15) |
C9 | 0.046 (2) | 0.049 (2) | 0.0380 (18) | −0.0091 (16) | 0.0028 (14) | 0.0000 (15) |
C10 | 0.056 (2) | 0.063 (2) | 0.054 (2) | 0.006 (2) | 0.0090 (17) | −0.0004 (19) |
C11 | 0.064 (3) | 0.084 (3) | 0.047 (2) | −0.018 (2) | 0.0108 (17) | 0.005 (2) |
Geometric parameters (Å, º) top
F1—C3 | 1.368 (4) | C4—C5 | 1.379 (5) |
S1—C9 | 1.728 (4) | C4—H4A | 0.9300 |
S1—C7 | 1.742 (3) | C5—C6 | 1.372 (5) |
N1—C7 | 1.359 (4) | C5—H5A | 0.9300 |
N1—C6 | 1.408 (4) | C8—C9 | 1.347 (4) |
N1—H1A | 0.8600 | C8—C10 | 1.503 (4) |
N2—C7 | 1.299 (4) | C9—C11 | 1.501 (5) |
N2—C8 | 1.390 (4) | C10—H10A | 0.9600 |
C1—C6 | 1.380 (4) | C10—H10B | 0.9600 |
C1—C2 | 1.383 (5) | C10—H10C | 0.9600 |
C1—H1B | 0.9300 | C11—H11A | 0.9600 |
C2—C3 | 1.362 (5) | C11—H11B | 0.9600 |
C2—H2B | 0.9300 | C11—H11C | 0.9600 |
C3—C4 | 1.364 (5) | | |
| | | |
C9—S1—C7 | 89.20 (15) | C1—C6—N1 | 122.2 (3) |
C7—N1—C6 | 126.5 (3) | N2—C7—N1 | 123.2 (3) |
C7—N1—H1A | 116.8 | N2—C7—S1 | 114.6 (2) |
C6—N1—H1A | 116.8 | N1—C7—S1 | 122.1 (2) |
C7—N2—C8 | 110.3 (3) | C9—C8—N2 | 116.2 (3) |
C6—C1—C2 | 120.6 (3) | C9—C8—C10 | 124.7 (3) |
C6—C1—H1B | 119.7 | N2—C8—C10 | 119.1 (3) |
C2—C1—H1B | 119.7 | C8—C9—C11 | 129.9 (3) |
C3—C2—C1 | 118.1 (3) | C8—C9—S1 | 109.6 (3) |
C3—C2—H2B | 120.9 | C11—C9—S1 | 120.5 (3) |
C1—C2—H2B | 120.9 | C8—C10—H10A | 109.5 |
C2—C3—C4 | 122.9 (3) | C8—C10—H10B | 109.5 |
C2—C3—F1 | 118.5 (3) | H10A—C10—H10B | 109.5 |
C4—C3—F1 | 118.6 (4) | C8—C10—H10C | 109.5 |
C3—C4—C5 | 118.1 (4) | H10A—C10—H10C | 109.5 |
C3—C4—H4A | 121.0 | H10B—C10—H10C | 109.5 |
C5—C4—H4A | 121.0 | C9—C11—H11A | 109.5 |
C6—C5—C4 | 121.0 (3) | C9—C11—H11B | 109.5 |
C6—C5—H5A | 119.5 | H11A—C11—H11B | 109.5 |
C4—C5—H5A | 119.5 | C9—C11—H11C | 109.5 |
C5—C6—C1 | 119.2 (3) | H11A—C11—H11C | 109.5 |
C5—C6—N1 | 118.6 (3) | H11B—C11—H11C | 109.5 |
| | | |
C6—C1—C2—C3 | −2.6 (6) | C8—N2—C7—S1 | −0.3 (4) |
C1—C2—C3—C4 | 1.2 (6) | C6—N1—C7—N2 | −175.1 (3) |
C1—C2—C3—F1 | 179.9 (4) | C6—N1—C7—S1 | 9.0 (5) |
C2—C3—C4—C5 | 1.1 (6) | C9—S1—C7—N2 | 0.2 (3) |
F1—C3—C4—C5 | −177.6 (3) | C9—S1—C7—N1 | 176.5 (3) |
C3—C4—C5—C6 | −2.2 (6) | C7—N2—C8—C9 | 0.2 (4) |
C4—C5—C6—C1 | 0.9 (6) | C7—N2—C8—C10 | −179.4 (3) |
C4—C5—C6—N1 | −177.3 (3) | N2—C8—C9—C11 | −178.6 (3) |
C2—C1—C6—C5 | 1.6 (6) | C10—C8—C9—C11 | 0.9 (6) |
C2—C1—C6—N1 | 179.7 (3) | N2—C8—C9—S1 | 0.0 (4) |
C7—N1—C6—C5 | −140.6 (4) | C10—C8—C9—S1 | 179.5 (3) |
C7—N1—C6—C1 | 41.3 (5) | C7—S1—C9—C8 | −0.1 (3) |
C8—N2—C7—N1 | −176.5 (3) | C7—S1—C9—C11 | 178.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···S1 | 0.93 | 2.72 | 3.124 (4) | 107 |
N1—H1A···N2i | 0.86 | 2.18 | 3.038 (4) | 172 |
Symmetry code: (i) −x, −y+1, −z+1. |
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