Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036343/xu2300sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036343/xu2300Isup2.hkl |
CCDC reference: 290255
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.069
- wR factor = 0.204
- Data-to-parameter ratio = 10.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C17 PLAT431_ALERT_2_B Short Inter HL..A Contact F3' .. F3' .. 2.46 Ang.
Alert level C PLAT213_ALERT_2_C Atom F3' has ADP max/min Ratio ............. 3.20 prola PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.09 PLAT301_ALERT_3_C Main Residue Disorder ......................... 10.00 Perc. 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 ... 6 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ?
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 12
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see: Du et al. (2000); Song et al. (2005); Wang et al. (2004); Zou et al. (2002); Bernstein et al. (1995). For synthesis, see: Song, Wang et al. (2007); Song, Tan & Wang (2007).
The required 2-amino-5-(4-trifluoromethyl-phenyl)-1,3,4-thiadiazole was obtained by dehydration-cyclization of 4-trifluoromethyl-benzoic acid and thiosemicarbozide in presence of phosphorus oxychloride according to a literature method (Song, Wang et al., 2007). The title compound was then prepared according to the procedure reported by Song, Tan & Wang (2007). Suitable crystals were obtained from a methanol–DMF (1:3) solution at room temperature. Elemental analysis: analysis calculated for C17H13F3N4OS: C 53.96, H 3.46, N 14.81%; found: C 54.03, H 3.59, N 14.67%.
Imino H atoms were located in a difference Fourier map and refined as riding in as-found relative positions, Uiso(H) = 1.2Ueq(N). The methyl H atoms were placed in calculated positions with C—H = 0.96 Å and torsion angle was refined to fit the electron density, Uiso(H) = 1.5Ueq(C). Other H atoms were positioned geometrically and constrained to ride on their parent atoms with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). The F atoms of trifluoromethyl group are disordered over two sites, occupancies were initialy refined and fixed at 0.67 and 1/3, respectively; geometry constrains were applied for the disordered group.
1,3,4-Thiadiazole derivatives have been reported to possess broad spectrum bioactivities, such as insecticidal, fungicidal and plant-growth regulating activities (Zou et al., 2002; Song et al., 2005). Urea derivatives have attracted much attention owing to their diverse biological effects (Du et al., 2000; Wang et al., 2004). Furthermore, considerable interest has been shown in fluorine-containing compounds in the field of modern agrochemistry and medicinal chemistry. In our continuing search for biological active urea derivatives as plant-growth regulators, we would like to investigate substituted ureas incorporating both 1,3,4-thiadiazole and CF3 groups, including the title compound.
The crystal structure (Fig. 1) revealed that the three rings in the molecule are essentially coplanar, the dihedral angles formed by the thiadiazole ring with methylbenzene and trifluoromethylbenzene moieties being only 1.4 (2)° and 4.8 (2)°. It is obvious that the molecule is nearly planar, as can be attributed to the presence of the extended π conjugated system throughout the whole molecule. Bond lengths and angles are as expected. In the crystal structure, neighbouring molecules are linked by complementary N—H···N hydrogen bonding into an R22(8) motif (Bernstein et al., 1995), as shown in Fig. 2 and Table 1.
For general background, see: Du et al. (2000); Song et al. (2005); Wang et al. (2004); Zou et al. (2002); Bernstein et al. (1995). For synthesis, see: Song, Wang et al. (2007); Song, Tan & Wang (2007).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.
C17H13F3N4OS | Z = 2 |
Mr = 378.38 | F(000) = 388 |
Triclinic, P1 | Dx = 1.509 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.478 (1) Å | Cell parameters from 1187 reflections |
b = 8.0133 (14) Å | θ = 2.6–22.1° |
c = 19.351 (3) Å | µ = 0.24 mm−1 |
α = 99.972 (3)° | T = 292 K |
β = 92.435 (4)° | Block, colourless |
γ = 94.290 (3)° | 0.20 × 0.10 × 0.06 mm |
V = 832.9 (2) Å3 |
Bruker SMART CCD area-detector diffractometer | 2203 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
φ and ω scans | h = −6→6 |
4221 measured reflections | k = −6→9 |
2889 independent reflections | l = −22→19 |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.204 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.1058P)2 + 0.1695P] where P = (Fo2 + 2Fc2)/3 |
2889 reflections | (Δ/σ)max = 0.001 |
264 parameters | Δρmax = 0.38 e Å−3 |
12 restraints | Δρmin = −0.32 e Å−3 |
C17H13F3N4OS | γ = 94.290 (3)° |
Mr = 378.38 | V = 832.9 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.478 (1) Å | Mo Kα radiation |
b = 8.0133 (14) Å | µ = 0.24 mm−1 |
c = 19.351 (3) Å | T = 292 K |
α = 99.972 (3)° | 0.20 × 0.10 × 0.06 mm |
β = 92.435 (4)° |
Bruker SMART CCD area-detector diffractometer | 2203 reflections with I > 2σ(I) |
4221 measured reflections | Rint = 0.027 |
2889 independent reflections |
R[F2 > 2σ(F2)] = 0.069 | 12 restraints |
wR(F2) = 0.204 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.38 e Å−3 |
2889 reflections | Δρmin = −0.32 e Å−3 |
264 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.3164 (11) | 0.3797 (7) | −0.3256 (2) | 0.0919 (18) | |
H1A | 0.4439 | 0.3032 | −0.3295 | 0.138* | |
H1B | 0.3728 | 0.4827 | −0.3411 | 0.138* | |
H1C | 0.1747 | 0.3273 | −0.3544 | 0.138* | |
C2 | 0.4087 (7) | 0.5277 (5) | −0.2014 (2) | 0.0517 (10) | |
H2 | 0.5538 | 0.5741 | −0.2163 | 0.062* | |
C3 | 0.2499 (9) | 0.4203 (5) | −0.2499 (2) | 0.0604 (12) | |
C4 | 0.0373 (9) | 0.3538 (6) | −0.2259 (3) | 0.0676 (12) | |
H4 | −0.0733 | 0.2815 | −0.2572 | 0.081* | |
C5 | −0.0134 (8) | 0.3925 (5) | −0.1569 (2) | 0.0642 (11) | |
H5 | −0.1593 | 0.3465 | −0.1423 | 0.077* | |
C6 | 0.1433 (7) | 0.4969 (5) | −0.1082 (2) | 0.0503 (9) | |
H6 | 0.1076 | 0.5197 | −0.0611 | 0.060* | |
C7 | 0.3573 (7) | 0.5676 (4) | −0.13140 (18) | 0.0423 (8) | |
C8 | 0.5228 (6) | 0.7434 (5) | −0.01756 (18) | 0.0424 (8) | |
C9 | 0.7631 (7) | 0.9361 (5) | 0.07428 (18) | 0.0438 (9) | |
C10 | 0.7901 (6) | 1.0522 (4) | 0.19476 (18) | 0.0428 (9) | |
C11 | 0.7676 (7) | 1.1034 (5) | 0.27066 (18) | 0.0463 (9) | |
C12 | 0.5630 (9) | 1.0524 (6) | 0.3030 (2) | 0.0731 (13) | |
H12 | 0.4356 | 0.9858 | 0.2758 | 0.088* | |
C13 | 0.5405 (10) | 1.0969 (6) | 0.3743 (2) | 0.0795 (14) | |
H13 | 0.3998 | 1.0615 | 0.3948 | 0.095* | |
C14 | 0.7283 (9) | 1.1941 (5) | 0.4146 (2) | 0.0638 (12) | |
C15 | 0.9277 (10) | 1.2474 (7) | 0.3834 (2) | 0.0781 (14) | |
H15 | 1.0533 | 1.3154 | 0.4107 | 0.094* | |
C16 | 0.9507 (9) | 1.2039 (6) | 0.3120 (2) | 0.0706 (12) | |
H16 | 1.0903 | 1.2428 | 0.2918 | 0.085* | |
C17 | 0.7119 (15) | 1.2439 (9) | 0.4920 (3) | 0.096 (2) | |
F1 | 0.4700 (19) | 1.2214 (17) | 0.5122 (9) | 0.121 (4) | 0.67 |
F2 | 0.829 (2) | 1.1386 (11) | 0.5265 (4) | 0.126 (3) | 0.67 |
F3 | 0.788 (3) | 1.3979 (13) | 0.5189 (5) | 0.147 (6) | 0.67 |
F1' | 0.552 (5) | 1.180 (4) | 0.5166 (18) | 0.138 (9) | 0.33 |
F2' | 0.907 (4) | 1.252 (4) | 0.5279 (10) | 0.181 (12) | 0.33 |
F3' | 0.672 (5) | 1.410 (3) | 0.5021 (11) | 0.163 (12) | 0.33 |
N1 | 0.5294 (5) | 0.6798 (4) | −0.08729 (15) | 0.0476 (8) | |
H1 | 0.6555 | 0.7089 | −0.1080 | 0.057* | |
N2 | 0.7195 (5) | 0.8563 (4) | 0.00599 (14) | 0.0492 (8) | |
H2A | 0.8396 | 0.8756 | −0.0201 | 0.059* | |
N3 | 0.9620 (5) | 1.0398 (4) | 0.09270 (15) | 0.0494 (8) | |
N4 | 0.9775 (6) | 1.1066 (4) | 0.16332 (15) | 0.0495 (8) | |
O1 | 0.3635 (5) | 0.7090 (3) | 0.02018 (13) | 0.0579 (7) | |
S1 | 0.57658 (17) | 0.91409 (12) | 0.14109 (5) | 0.0467 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.139 (5) | 0.089 (4) | 0.044 (2) | 0.022 (3) | −0.004 (3) | −0.004 (2) |
C2 | 0.058 (2) | 0.046 (2) | 0.053 (2) | 0.0083 (18) | 0.0051 (18) | 0.0107 (18) |
C3 | 0.083 (3) | 0.053 (2) | 0.044 (2) | 0.022 (2) | −0.011 (2) | 0.0009 (19) |
C4 | 0.065 (3) | 0.059 (3) | 0.071 (3) | −0.002 (2) | −0.021 (2) | −0.001 (2) |
C5 | 0.052 (3) | 0.061 (3) | 0.078 (3) | 0.003 (2) | −0.002 (2) | 0.011 (2) |
C6 | 0.048 (2) | 0.048 (2) | 0.054 (2) | −0.0001 (17) | 0.0043 (17) | 0.0054 (18) |
C7 | 0.049 (2) | 0.0362 (18) | 0.0413 (19) | 0.0059 (16) | 0.0018 (16) | 0.0049 (15) |
C8 | 0.0359 (19) | 0.049 (2) | 0.0427 (19) | −0.0027 (16) | 0.0104 (15) | 0.0098 (16) |
C9 | 0.045 (2) | 0.046 (2) | 0.0398 (19) | 0.0003 (16) | 0.0062 (15) | 0.0078 (16) |
C10 | 0.045 (2) | 0.0402 (19) | 0.0433 (19) | 0.0026 (16) | 0.0040 (16) | 0.0078 (16) |
C11 | 0.060 (2) | 0.039 (2) | 0.0401 (19) | 0.0041 (17) | 0.0046 (17) | 0.0079 (16) |
C12 | 0.090 (3) | 0.080 (3) | 0.043 (2) | −0.016 (3) | 0.009 (2) | −0.001 (2) |
C13 | 0.103 (4) | 0.086 (4) | 0.046 (2) | −0.013 (3) | 0.017 (2) | 0.007 (2) |
C14 | 0.092 (3) | 0.052 (2) | 0.046 (2) | 0.003 (2) | 0.010 (2) | 0.0050 (19) |
C15 | 0.089 (4) | 0.086 (3) | 0.049 (2) | −0.013 (3) | −0.003 (2) | −0.008 (2) |
C16 | 0.074 (3) | 0.076 (3) | 0.054 (3) | −0.007 (2) | 0.002 (2) | −0.003 (2) |
C17 | 0.142 (6) | 0.090 (5) | 0.049 (3) | −0.017 (4) | 0.012 (4) | 0.000 (3) |
F1 | 0.121 (6) | 0.167 (9) | 0.061 (5) | 0.004 (5) | 0.036 (5) | −0.019 (5) |
F2 | 0.184 (9) | 0.154 (7) | 0.044 (4) | 0.017 (6) | −0.002 (4) | 0.031 (5) |
F3 | 0.243 (13) | 0.112 (8) | 0.059 (5) | −0.074 (9) | 0.024 (7) | −0.026 (4) |
F1' | 0.18 (2) | 0.165 (15) | 0.057 (8) | −0.019 (15) | 0.022 (15) | 0.008 (10) |
F2' | 0.167 (18) | 0.29 (4) | 0.066 (9) | 0.09 (2) | −0.046 (11) | −0.047 (18) |
F3' | 0.29 (3) | 0.109 (14) | 0.073 (11) | 0.067 (18) | −0.005 (13) | −0.047 (8) |
N1 | 0.0454 (18) | 0.0529 (19) | 0.0420 (17) | −0.0085 (14) | 0.0128 (14) | 0.0044 (14) |
N2 | 0.0479 (18) | 0.060 (2) | 0.0366 (16) | −0.0112 (15) | 0.0137 (13) | 0.0021 (14) |
N3 | 0.0477 (19) | 0.0543 (19) | 0.0424 (17) | −0.0063 (15) | 0.0092 (13) | 0.0008 (14) |
N4 | 0.0540 (19) | 0.0483 (18) | 0.0426 (17) | −0.0028 (15) | 0.0055 (14) | 0.0006 (14) |
O1 | 0.0574 (17) | 0.0684 (18) | 0.0435 (14) | −0.0139 (13) | 0.0116 (13) | 0.0038 (13) |
S1 | 0.0495 (6) | 0.0502 (6) | 0.0390 (5) | −0.0053 (4) | 0.0075 (4) | 0.0068 (4) |
C1—C3 | 1.511 (6) | C10—C11 | 1.468 (5) |
C1—H1A | 0.9600 | C10—S1 | 1.726 (4) |
C1—H1B | 0.9600 | C11—C16 | 1.372 (6) |
C1—H1C | 0.9600 | C11—C12 | 1.376 (6) |
C2—C7 | 1.383 (5) | C12—C13 | 1.378 (6) |
C2—C3 | 1.385 (6) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—C14 | 1.369 (7) |
C3—C4 | 1.377 (7) | C13—H13 | 0.9300 |
C4—C5 | 1.364 (6) | C14—C15 | 1.348 (7) |
C4—H4 | 0.9300 | C14—C17 | 1.490 (7) |
C5—C6 | 1.369 (6) | C15—C16 | 1.379 (6) |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C6—C7 | 1.389 (5) | C16—H16 | 0.9300 |
C6—H6 | 0.9300 | C17—F1' | 1.15 (3) |
C7—N1 | 1.402 (4) | C17—F2' | 1.24 (2) |
C8—O1 | 1.208 (4) | C17—F3 | 1.284 (12) |
C8—N1 | 1.360 (4) | C17—F2 | 1.344 (12) |
C8—N2 | 1.363 (4) | C17—F3' | 1.35 (2) |
C9—N3 | 1.316 (5) | C17—F1 | 1.405 (14) |
C9—N2 | 1.367 (5) | N1—H1 | 0.8513 |
C9—S1 | 1.706 (3) | N2—H2A | 0.8663 |
C10—N4 | 1.300 (5) | N3—N4 | 1.375 (4) |
C3—C1—H1A | 109.5 | C11—C12—C13 | 122.2 (5) |
C3—C1—H1B | 109.5 | C11—C12—H12 | 118.9 |
H1A—C1—H1B | 109.5 | C13—C12—H12 | 118.9 |
C3—C1—H1C | 109.5 | C14—C13—C12 | 119.1 (5) |
H1A—C1—H1C | 109.5 | C14—C13—H13 | 120.5 |
H1B—C1—H1C | 109.5 | C12—C13—H13 | 120.5 |
C7—C2—C3 | 121.7 (4) | C15—C14—C13 | 119.3 (4) |
C7—C2—H2 | 119.2 | C15—C14—C17 | 120.0 (5) |
C3—C2—H2 | 119.2 | C13—C14—C17 | 120.7 (5) |
C4—C3—C2 | 117.5 (4) | C14—C15—C16 | 121.9 (5) |
C4—C3—C1 | 123.0 (4) | C14—C15—H15 | 119.0 |
C2—C3—C1 | 119.5 (5) | C16—C15—H15 | 119.0 |
C5—C4—C3 | 120.9 (4) | C11—C16—C15 | 119.9 (4) |
C5—C4—H4 | 119.5 | C11—C16—H16 | 120.0 |
C3—C4—H4 | 119.5 | C15—C16—H16 | 120.0 |
C4—C5—C6 | 122.2 (4) | F1'—C17—F2' | 111.9 (18) |
C4—C5—H5 | 118.9 | F3—C17—F2 | 108.7 (8) |
C6—C5—H5 | 118.9 | F1'—C17—F3' | 105.1 (14) |
C5—C6—C7 | 117.9 (4) | F2'—C17—F3' | 99.8 (14) |
C5—C6—H6 | 121.0 | F3—C17—F1 | 105.8 (8) |
C7—C6—H6 | 121.0 | F2—C17—F1 | 102.3 (7) |
C2—C7—C6 | 119.8 (4) | F1'—C17—C14 | 116.7 (18) |
C2—C7—N1 | 116.8 (3) | F2'—C17—C14 | 116.0 (12) |
C6—C7—N1 | 123.5 (3) | F3—C17—C14 | 116.4 (7) |
O1—C8—N1 | 125.8 (3) | F2—C17—C14 | 110.9 (6) |
O1—C8—N2 | 122.5 (3) | F3'—C17—C14 | 104.9 (11) |
N1—C8—N2 | 111.7 (3) | F1—C17—C14 | 111.7 (8) |
N3—C9—N2 | 120.0 (3) | C8—N1—C7 | 129.2 (3) |
N3—C9—S1 | 114.8 (3) | C8—N1—H1 | 117.4 |
N2—C9—S1 | 125.2 (3) | C7—N1—H1 | 113.4 |
N4—C10—C11 | 121.7 (3) | C8—N2—C9 | 124.2 (3) |
N4—C10—S1 | 115.1 (3) | C8—N2—H2A | 122.7 |
C11—C10—S1 | 123.2 (3) | C9—N2—H2A | 112.7 |
C16—C11—C12 | 117.6 (4) | C9—N3—N4 | 112.1 (3) |
C16—C11—C10 | 121.0 (4) | C10—N4—N3 | 111.6 (3) |
C12—C11—C10 | 121.4 (4) | C9—S1—C10 | 86.44 (17) |
C7—C2—C3—C4 | −0.1 (6) | C13—C14—C17—F2' | 144.9 (19) |
C7—C2—C3—C1 | −179.4 (4) | C15—C14—C17—F3 | 40.9 (12) |
C2—C3—C4—C5 | −0.1 (6) | C13—C14—C17—F3 | −137.9 (10) |
C1—C3—C4—C5 | 179.2 (4) | C15—C14—C17—F2 | −84.0 (8) |
C3—C4—C5—C6 | −0.6 (7) | C13—C14—C17—F2 | 97.2 (9) |
C4—C5—C6—C7 | 1.6 (6) | C15—C14—C17—F3' | 72.7 (14) |
C3—C2—C7—C6 | 1.1 (5) | C13—C14—C17—F3' | −106.1 (13) |
C3—C2—C7—N1 | −179.0 (3) | C15—C14—C17—F1 | 162.5 (7) |
C5—C6—C7—C2 | −1.8 (5) | C13—C14—C17—F1 | −16.3 (10) |
C5—C6—C7—N1 | 178.3 (3) | O1—C8—N1—C7 | 2.1 (6) |
N4—C10—C11—C16 | −3.4 (6) | N2—C8—N1—C7 | −176.8 (3) |
S1—C10—C11—C16 | 175.3 (3) | C2—C7—N1—C8 | 178.2 (3) |
N4—C10—C11—C12 | 176.6 (4) | C6—C7—N1—C8 | −1.9 (6) |
S1—C10—C11—C12 | −4.7 (5) | O1—C8—N2—C9 | 2.9 (6) |
C16—C11—C12—C13 | −1.1 (7) | N1—C8—N2—C9 | −178.1 (3) |
C10—C11—C12—C13 | 178.9 (4) | N3—C9—N2—C8 | 178.1 (3) |
C11—C12—C13—C14 | −0.4 (8) | S1—C9—N2—C8 | −2.1 (5) |
C12—C13—C14—C15 | 1.6 (8) | N2—C9—N3—N4 | −179.2 (3) |
C12—C13—C14—C17 | −179.6 (5) | S1—C9—N3—N4 | 1.0 (4) |
C13—C14—C15—C16 | −1.4 (8) | C11—C10—N4—N3 | 178.8 (3) |
C17—C14—C15—C16 | 179.8 (5) | S1—C10—N4—N3 | 0.0 (4) |
C12—C11—C16—C15 | 1.3 (7) | C9—N3—N4—C10 | −0.6 (4) |
C10—C11—C16—C15 | −178.7 (4) | N3—C9—S1—C10 | −0.8 (3) |
C14—C15—C16—C11 | −0.1 (8) | N2—C9—S1—C10 | 179.4 (3) |
C15—C14—C17—F1' | −171.5 (17) | N4—C10—S1—C9 | 0.4 (3) |
C13—C14—C17—F1' | 9.7 (18) | C11—C10—S1—C9 | −178.4 (3) |
C15—C14—C17—F2' | −36 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N3i | 0.87 | 1.99 | 2.829 (4) | 162 |
Symmetry code: (i) −x+2, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C17H13F3N4OS |
Mr | 378.38 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 292 |
a, b, c (Å) | 5.478 (1), 8.0133 (14), 19.351 (3) |
α, β, γ (°) | 99.972 (3), 92.435 (4), 94.290 (3) |
V (Å3) | 832.9 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.20 × 0.10 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4221, 2889, 2203 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.204, 1.10 |
No. of reflections | 2889 |
No. of parameters | 264 |
No. of restraints | 12 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.32 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2001), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N3i | 0.87 | 1.99 | 2.829 (4) | 162 |
Symmetry code: (i) −x+2, −y+2, −z. |
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1,3,4-Thiadiazole derivatives have been reported to possess broad spectrum bioactivities, such as insecticidal, fungicidal and plant-growth regulating activities (Zou et al., 2002; Song et al., 2005). Urea derivatives have attracted much attention owing to their diverse biological effects (Du et al., 2000; Wang et al., 2004). Furthermore, considerable interest has been shown in fluorine-containing compounds in the field of modern agrochemistry and medicinal chemistry. In our continuing search for biological active urea derivatives as plant-growth regulators, we would like to investigate substituted ureas incorporating both 1,3,4-thiadiazole and CF3 groups, including the title compound.
The crystal structure (Fig. 1) revealed that the three rings in the molecule are essentially coplanar, the dihedral angles formed by the thiadiazole ring with methylbenzene and trifluoromethylbenzene moieties being only 1.4 (2)° and 4.8 (2)°. It is obvious that the molecule is nearly planar, as can be attributed to the presence of the extended π conjugated system throughout the whole molecule. Bond lengths and angles are as expected. In the crystal structure, neighbouring molecules are linked by complementary N—H···N hydrogen bonding into an R22(8) motif (Bernstein et al., 1995), as shown in Fig. 2 and Table 1.