In the title molecule, C
21H
16ClF
3N
4O
2S, all bond lengths and angles are normal. Intermolecular N—H
S hydrogen bonds link the molecules into centrosymmetric dimers. Weak intermolecular C—H
O hydrogen bonds stabilize the crystal packing.
Supporting information
CCDC reference: 629639
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.058
- wR factor = 0.163
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.29
PLAT414_ALERT_2_C Short Intra D-H..H-X H4 .. H10 .. 1.94 Ang.
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
3 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
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
N-{3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoyl}-
N'-(4,6-dimethylpyrimidin-2-yl)thiourea
top
Crystal data top
C21H16ClF3N4O2S | F(000) = 984 |
Mr = 480.89 | Dx = 1.529 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2570 reflections |
a = 15.8533 (15) Å | θ = 2.4–21.4° |
b = 6.9436 (7) Å | µ = 0.34 mm−1 |
c = 19.0716 (18) Å | T = 298 K |
β = 95.648 (2)° | Needle, yellow |
V = 2089.2 (3) Å3 | 0.36 × 0.10 × 0.06 mm |
Z = 4 | |
Data collection top
Bruker SMART Apex CCD area-detector diffractometer | 2763 reflections with I > 2σ(I) |
Radiation source: fine focus sealed Siemens Mo tube | Rint = 0.054 |
Graphite monochromator | θmax = 27.0°, θmin = 1.3° |
0.3° wide ω exposures scans | h = −19→20 |
16915 measured reflections | k = −8→8 |
4519 independent reflections | l = −24→24 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.076P)2 + 0.4678P] where P = (Fo2 + 2Fc2)/3 |
4519 reflections | (Δ/σ)max = 0.004 |
297 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | −0.26183 (19) | 0.5073 (4) | 0.14298 (16) | 0.0428 (7) | |
C2 | −0.2568 (2) | 0.5122 (4) | 0.21606 (16) | 0.0460 (8) | |
H2 | −0.3056 | 0.5243 | 0.2391 | 0.055* | |
C3 | −0.1789 (2) | 0.4988 (4) | 0.25360 (15) | 0.0409 (7) | |
C4 | −0.11881 (17) | 0.4844 (4) | 0.15001 (14) | 0.0332 (6) | |
C5 | −0.3459 (2) | 0.5185 (6) | 0.09966 (18) | 0.0614 (10) | |
H5A | −0.3377 | 0.5596 | 0.0528 | 0.092* | |
H5B | −0.3817 | 0.6092 | 0.1206 | 0.092* | |
H5C | −0.3723 | 0.3939 | 0.0979 | 0.092* | |
C6 | −0.1690 (2) | 0.4995 (5) | 0.33267 (15) | 0.0545 (9) | |
H6A | −0.1505 | 0.3748 | 0.3496 | 0.082* | |
H6B | −0.2224 | 0.5298 | 0.3498 | 0.082* | |
H6C | −0.1277 | 0.5945 | 0.3492 | 0.082* | |
C7 | 0.03678 (18) | 0.4800 (4) | 0.13189 (13) | 0.0341 (6) | |
C8 | 0.13857 (19) | 0.4935 (4) | 0.23998 (14) | 0.0388 (7) | |
C9 | 0.14047 (18) | 0.4845 (4) | 0.31849 (13) | 0.0351 (7) | |
C10 | 0.0700 (2) | 0.4619 (5) | 0.35481 (14) | 0.0447 (8) | |
H10 | 0.0163 | 0.4574 | 0.3304 | 0.054* | |
C11 | 0.0789 (2) | 0.4458 (5) | 0.42726 (16) | 0.0548 (9) | |
H11 | 0.0311 | 0.4287 | 0.4512 | 0.066* | |
C12 | 0.1577 (2) | 0.4547 (5) | 0.46451 (16) | 0.0520 (9) | |
H12 | 0.1634 | 0.4439 | 0.5133 | 0.062* | |
C13 | 0.22785 (19) | 0.4798 (4) | 0.42862 (14) | 0.0413 (7) | |
C14 | 0.22044 (18) | 0.4950 (4) | 0.35638 (14) | 0.0381 (7) | |
H14 | 0.2685 | 0.5122 | 0.3328 | 0.046* | |
C15 | 0.33086 (18) | 0.5781 (5) | 0.52285 (14) | 0.0416 (7) | |
C16 | 0.39963 (19) | 0.5117 (5) | 0.56720 (15) | 0.0458 (8) | |
C17 | 0.4284 (2) | 0.6178 (5) | 0.62583 (15) | 0.0509 (9) | |
H17 | 0.4748 | 0.5749 | 0.6553 | 0.061* | |
C18 | 0.38876 (19) | 0.7871 (5) | 0.64093 (15) | 0.0462 (8) | |
C19 | 0.31994 (19) | 0.8508 (5) | 0.59769 (15) | 0.0467 (8) | |
H19 | 0.2927 | 0.9644 | 0.6082 | 0.056* | |
C20 | 0.29121 (18) | 0.7460 (5) | 0.53853 (14) | 0.0450 (8) | |
H20 | 0.2448 | 0.7896 | 0.5092 | 0.054* | |
C21 | 0.4208 (2) | 0.8978 (6) | 0.70465 (18) | 0.0604 (10) | |
Cl1 | 0.45064 (6) | 0.30105 (15) | 0.54775 (5) | 0.0707 (3) | |
F1 | 0.39814 (15) | 0.8239 (4) | 0.76416 (10) | 0.0873 (8) | |
F2 | 0.39343 (17) | 1.0787 (4) | 0.70438 (13) | 0.0952 (8) | |
F3 | 0.50478 (13) | 0.9058 (4) | 0.71376 (12) | 0.1013 (9) | |
N1 | −0.19239 (15) | 0.4921 (3) | 0.10919 (12) | 0.0383 (6) | |
N2 | −0.10783 (15) | 0.4842 (3) | 0.22027 (11) | 0.0376 (6) | |
N3 | −0.04858 (15) | 0.4751 (4) | 0.11201 (12) | 0.0372 (6) | |
N4 | 0.05750 (15) | 0.4835 (4) | 0.20363 (11) | 0.0372 (6) | |
O1 | 0.20198 (14) | 0.5065 (4) | 0.21112 (11) | 0.0688 (8) | |
O2 | 0.30995 (14) | 0.4725 (3) | 0.46208 (10) | 0.0565 (6) | |
S1 | 0.10378 (5) | 0.47967 (14) | 0.07067 (4) | 0.0525 (3) | |
H3 | −0.062 (2) | 0.477 (5) | 0.0699 (19) | 0.063* | |
H4 | 0.014 (2) | 0.472 (5) | 0.2285 (18) | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0429 (18) | 0.0458 (19) | 0.0398 (17) | −0.0053 (14) | 0.0049 (13) | −0.0019 (14) |
C2 | 0.0431 (18) | 0.057 (2) | 0.0395 (17) | −0.0060 (15) | 0.0132 (14) | −0.0020 (15) |
C3 | 0.0519 (19) | 0.0435 (18) | 0.0287 (15) | −0.0072 (14) | 0.0111 (13) | 0.0014 (13) |
C4 | 0.0383 (16) | 0.0354 (16) | 0.0264 (14) | −0.0027 (12) | 0.0052 (11) | −0.0010 (12) |
C5 | 0.0422 (19) | 0.094 (3) | 0.048 (2) | −0.0010 (18) | 0.0047 (15) | −0.0060 (18) |
C6 | 0.063 (2) | 0.075 (2) | 0.0270 (16) | −0.0068 (18) | 0.0132 (14) | 0.0025 (15) |
C7 | 0.0401 (16) | 0.0404 (17) | 0.0213 (13) | −0.0016 (13) | 0.0002 (11) | 0.0002 (11) |
C8 | 0.0410 (17) | 0.0520 (19) | 0.0223 (14) | −0.0037 (14) | −0.0024 (12) | 0.0016 (12) |
C9 | 0.0443 (17) | 0.0391 (17) | 0.0214 (13) | −0.0008 (13) | −0.0003 (12) | 0.0016 (12) |
C10 | 0.0443 (18) | 0.065 (2) | 0.0247 (15) | −0.0048 (15) | 0.0026 (13) | −0.0024 (14) |
C11 | 0.052 (2) | 0.086 (3) | 0.0276 (16) | −0.0102 (18) | 0.0085 (14) | −0.0041 (16) |
C12 | 0.059 (2) | 0.074 (2) | 0.0222 (15) | −0.0016 (17) | 0.0019 (14) | −0.0032 (15) |
C13 | 0.0449 (17) | 0.0508 (19) | 0.0264 (15) | 0.0080 (14) | −0.0050 (13) | −0.0061 (13) |
C14 | 0.0391 (16) | 0.0468 (18) | 0.0279 (14) | 0.0031 (13) | 0.0014 (12) | −0.0038 (12) |
C15 | 0.0382 (16) | 0.066 (2) | 0.0200 (13) | 0.0012 (15) | 0.0009 (11) | 0.0003 (13) |
C16 | 0.0438 (18) | 0.062 (2) | 0.0300 (16) | 0.0057 (15) | −0.0013 (13) | 0.0067 (14) |
C17 | 0.0436 (18) | 0.078 (3) | 0.0284 (15) | −0.0040 (17) | −0.0102 (13) | 0.0059 (16) |
C18 | 0.0410 (17) | 0.067 (2) | 0.0307 (16) | −0.0137 (16) | 0.0053 (13) | −0.0021 (15) |
C19 | 0.0414 (17) | 0.063 (2) | 0.0362 (16) | −0.0023 (15) | 0.0071 (13) | −0.0005 (15) |
C20 | 0.0367 (16) | 0.069 (2) | 0.0282 (15) | 0.0048 (15) | 0.0001 (12) | 0.0038 (14) |
C21 | 0.052 (2) | 0.083 (3) | 0.046 (2) | −0.016 (2) | 0.0002 (16) | −0.0108 (19) |
Cl1 | 0.0697 (6) | 0.0765 (7) | 0.0613 (6) | 0.0222 (5) | −0.0172 (5) | −0.0033 (5) |
F1 | 0.1058 (17) | 0.124 (2) | 0.0327 (11) | −0.0329 (15) | 0.0095 (11) | −0.0098 (12) |
F2 | 0.118 (2) | 0.0856 (18) | 0.0775 (16) | −0.0171 (16) | −0.0155 (14) | −0.0228 (14) |
F3 | 0.0494 (13) | 0.176 (3) | 0.0776 (16) | −0.0351 (15) | 0.0001 (11) | −0.0511 (17) |
N1 | 0.0380 (14) | 0.0499 (16) | 0.0269 (12) | −0.0047 (11) | 0.0019 (10) | 0.0004 (11) |
N2 | 0.0404 (14) | 0.0502 (16) | 0.0224 (12) | −0.0044 (11) | 0.0034 (10) | 0.0007 (10) |
N3 | 0.0397 (14) | 0.0550 (16) | 0.0165 (11) | −0.0031 (11) | −0.0001 (10) | 0.0001 (11) |
N4 | 0.0373 (14) | 0.0558 (16) | 0.0181 (11) | −0.0021 (12) | 0.0009 (9) | 0.0009 (10) |
O1 | 0.0399 (13) | 0.138 (2) | 0.0277 (12) | −0.0108 (14) | 0.0006 (10) | 0.0072 (13) |
O2 | 0.0519 (13) | 0.0865 (17) | 0.0283 (11) | 0.0213 (12) | −0.0102 (9) | −0.0147 (11) |
S1 | 0.0396 (5) | 0.0965 (7) | 0.0212 (4) | −0.0004 (4) | 0.0019 (3) | −0.0011 (4) |
Geometric parameters (Å, º) top
C1—N1 | 1.333 (4) | C10—H10 | 0.9300 |
C1—C2 | 1.389 (4) | C11—C12 | 1.377 (4) |
C1—C5 | 1.500 (4) | C11—H11 | 0.9300 |
C2—C3 | 1.369 (4) | C12—C13 | 1.373 (4) |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
C3—N2 | 1.351 (4) | C13—C14 | 1.375 (4) |
C3—C6 | 1.501 (4) | C13—O2 | 1.393 (3) |
C4—N2 | 1.334 (3) | C14—H14 | 0.9300 |
C4—N1 | 1.338 (3) | C15—C20 | 1.372 (4) |
C4—N3 | 1.388 (4) | C15—O2 | 1.384 (3) |
C5—H5A | 0.9600 | C15—C16 | 1.391 (4) |
C5—H5B | 0.9600 | C16—C17 | 1.379 (4) |
C5—H5C | 0.9600 | C16—Cl1 | 1.729 (3) |
C6—H6A | 0.9600 | C17—C18 | 1.376 (5) |
C6—H6B | 0.9600 | C17—H17 | 0.9300 |
C6—H6C | 0.9600 | C18—C19 | 1.374 (4) |
C7—N3 | 1.369 (4) | C18—C21 | 1.485 (4) |
C7—N4 | 1.376 (3) | C19—C20 | 1.382 (4) |
C7—S1 | 1.654 (3) | C19—H19 | 0.9300 |
C8—O1 | 1.196 (4) | C20—H20 | 0.9300 |
C8—N4 | 1.401 (4) | C21—F1 | 1.327 (4) |
C8—C9 | 1.496 (4) | C21—F3 | 1.327 (4) |
C9—C10 | 1.381 (4) | C21—F2 | 1.329 (5) |
C9—C14 | 1.398 (4) | N3—H3 | 0.81 (4) |
C10—C11 | 1.379 (4) | N4—H4 | 0.88 (3) |
| | | |
N1—C1—C2 | 121.2 (3) | C11—C12—H12 | 120.4 |
N1—C1—C5 | 118.0 (3) | C12—C13—C14 | 121.0 (3) |
C2—C1—C5 | 120.8 (3) | C12—C13—O2 | 122.2 (3) |
C3—C2—C1 | 118.9 (3) | C14—C13—O2 | 116.5 (3) |
C3—C2—H2 | 120.6 | C13—C14—C9 | 119.8 (3) |
C1—C2—H2 | 120.6 | C13—C14—H14 | 120.1 |
N2—C3—C2 | 120.7 (3) | C9—C14—H14 | 120.1 |
N2—C3—C6 | 117.6 (3) | C20—C15—O2 | 123.8 (2) |
C2—C3—C6 | 121.7 (3) | C20—C15—C16 | 119.8 (3) |
N2—C4—N1 | 127.2 (3) | O2—C15—C16 | 116.3 (3) |
N2—C4—N3 | 119.5 (2) | C17—C16—C15 | 119.5 (3) |
N1—C4—N3 | 113.3 (2) | C17—C16—Cl1 | 120.1 (2) |
C1—C5—H5A | 109.5 | C15—C16—Cl1 | 120.3 (2) |
C1—C5—H5B | 109.5 | C18—C17—C16 | 120.3 (3) |
H5A—C5—H5B | 109.5 | C18—C17—H17 | 119.8 |
C1—C5—H5C | 109.5 | C16—C17—H17 | 119.8 |
H5A—C5—H5C | 109.5 | C19—C18—C17 | 120.1 (3) |
H5B—C5—H5C | 109.5 | C19—C18—C21 | 120.8 (3) |
C3—C6—H6A | 109.5 | C17—C18—C21 | 119.1 (3) |
C3—C6—H6B | 109.5 | C18—C19—C20 | 119.9 (3) |
H6A—C6—H6B | 109.5 | C18—C19—H19 | 120.0 |
C3—C6—H6C | 109.5 | C20—C19—H19 | 120.0 |
H6A—C6—H6C | 109.5 | C15—C20—C19 | 120.3 (3) |
H6B—C6—H6C | 109.5 | C15—C20—H20 | 119.9 |
N3—C7—N4 | 114.1 (2) | C19—C20—H20 | 119.9 |
N3—C7—S1 | 119.37 (19) | F1—C21—F3 | 104.9 (3) |
N4—C7—S1 | 126.5 (2) | F1—C21—F2 | 104.7 (3) |
O1—C8—N4 | 123.2 (3) | F3—C21—F2 | 106.5 (3) |
O1—C8—C9 | 121.9 (3) | F1—C21—C18 | 113.6 (3) |
N4—C8—C9 | 114.9 (3) | F3—C21—C18 | 112.8 (3) |
C10—C9—C14 | 119.0 (3) | F2—C21—C18 | 113.6 (3) |
C10—C9—C8 | 124.7 (2) | C1—N1—C4 | 115.8 (2) |
C14—C9—C8 | 116.3 (3) | C4—N2—C3 | 116.1 (2) |
C11—C10—C9 | 120.2 (3) | C7—N3—C4 | 132.5 (2) |
C11—C10—H10 | 119.9 | C7—N3—H3 | 115 (3) |
C9—C10—H10 | 119.9 | C4—N3—H3 | 112 (3) |
C12—C11—C10 | 120.8 (3) | C7—N4—C8 | 127.6 (2) |
C12—C11—H11 | 119.6 | C7—N4—H4 | 114 (2) |
C10—C11—H11 | 119.6 | C8—N4—H4 | 118 (2) |
C13—C12—C11 | 119.1 (3) | C15—O2—C13 | 120.0 (2) |
C13—C12—H12 | 120.4 | | |
| | | |
N1—C1—C2—C3 | −0.7 (5) | C16—C15—C20—C19 | 0.8 (5) |
C5—C1—C2—C3 | 179.1 (3) | C18—C19—C20—C15 | 0.3 (5) |
C1—C2—C3—N2 | 1.1 (5) | C19—C18—C21—F1 | 102.3 (4) |
C1—C2—C3—C6 | −178.9 (3) | C17—C18—C21—F1 | −77.1 (4) |
O1—C8—C9—C10 | −177.3 (3) | C19—C18—C21—F3 | −138.6 (4) |
N4—C8—C9—C10 | 2.0 (4) | C17—C18—C21—F3 | 42.1 (5) |
O1—C8—C9—C14 | 0.9 (4) | C19—C18—C21—F2 | −17.3 (5) |
N4—C8—C9—C14 | −179.7 (3) | C17—C18—C21—F2 | 163.4 (3) |
C14—C9—C10—C11 | −1.4 (5) | C2—C1—N1—C4 | −0.8 (4) |
C8—C9—C10—C11 | 176.8 (3) | C5—C1—N1—C4 | 179.4 (3) |
C9—C10—C11—C12 | 0.9 (5) | N2—C4—N1—C1 | 2.3 (4) |
C10—C11—C12—C13 | −0.1 (5) | N3—C4—N1—C1 | −178.0 (3) |
C11—C12—C13—C14 | −0.3 (5) | N1—C4—N2—C3 | −2.0 (4) |
C11—C12—C13—O2 | −174.0 (3) | N3—C4—N2—C3 | 178.3 (3) |
C12—C13—C14—C9 | −0.1 (5) | C2—C3—N2—C4 | 0.2 (4) |
O2—C13—C14—C9 | 173.9 (3) | C6—C3—N2—C4 | −179.9 (3) |
C10—C9—C14—C13 | 1.0 (4) | N4—C7—N3—C4 | 4.4 (5) |
C8—C9—C14—C13 | −177.4 (3) | S1—C7—N3—C4 | −176.0 (2) |
C20—C15—C16—C17 | −1.3 (5) | N2—C4—N3—C7 | −5.9 (5) |
O2—C15—C16—C17 | 174.9 (3) | N1—C4—N3—C7 | 174.3 (3) |
C20—C15—C16—Cl1 | −179.6 (2) | N3—C7—N4—C8 | −178.3 (3) |
O2—C15—C16—Cl1 | −3.4 (4) | S1—C7—N4—C8 | 2.1 (4) |
C15—C16—C17—C18 | 0.8 (5) | O1—C8—N4—C7 | 2.4 (5) |
Cl1—C16—C17—C18 | 179.0 (2) | C9—C8—N4—C7 | −176.9 (3) |
C16—C17—C18—C19 | 0.3 (5) | C20—C15—O2—C13 | −27.8 (5) |
C16—C17—C18—C21 | 179.7 (3) | C16—C15—O2—C13 | 156.2 (3) |
C17—C18—C19—C20 | −0.8 (5) | C12—C13—O2—C15 | −49.3 (4) |
C21—C18—C19—C20 | 179.8 (3) | C14—C13—O2—C15 | 136.8 (3) |
O2—C15—C20—C19 | −175.1 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N2 | 0.88 (3) | 1.93 (4) | 2.671 (3) | 142 (3) |
C19—H19···O1i | 0.93 | 2.55 | 3.155 (4) | 123 |
N3—H3···S1ii | 0.81 (4) | 2.71 (4) | 3.522 (2) | 175 (3) |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, −y+1, −z. |