All bond lengths and anlges in the title compound, C
15H
9F
5N
2O
2, an inhibitor of chitin synthesis, are normal. The urea linkage adopts an essentially planar configuration, with an intramolecular N—H
O hydrogen bond. Intermolecular N—H
O hydrogen bonds link two adjacent molecules into a centrosymmetric dimer.
Supporting information
CCDC reference: 253029
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.054
- wR factor = 0.144
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors for C15
Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.68
PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT431_ALERT_2_C Short Inter HL..A Contact F2 .. O2 .. 2.95 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact C2 .. F5' .. 2.96 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 34.30 Deg.
F5 -C15 -F5' 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 42.60 Deg.
F4 -C15 -F4' 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
7 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
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
1-(2,6-Difluorobenzoyl)-3-(4-trifluoromethylphenyl)urea
top
Crystal data top
C15H9F5N2O2 | Z = 2 |
Mr = 344.24 | F(000) = 348 |
Triclinic, P1 | Dx = 1.554 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.244 (7) Å | Cell parameters from 871 reflections |
b = 8.014 (8) Å | θ = 3.1–24.6° |
c = 13.654 (13) Å | µ = 0.15 mm−1 |
α = 91.218 (15)° | T = 293 K |
β = 101.586 (15)° | Needle, colourless |
γ = 108.010 (14)° | 0.38 × 0.26 × 0.12 mm |
V = 735.5 (12) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2578 independent reflections |
Radiation source: fine-focus sealed tube | 1304 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.936, Tmax = 0.983 | k = −9→9 |
3714 measured reflections | l = −12→16 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0626P)2] where P = (Fo2 + 2Fc2)/3 |
2578 reflections | (Δ/σ)max = 0.003 |
245 parameters | Δρmax = 0.18 e Å−3 |
6 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 | Occ. (<1) |
F1 | 0.8365 (3) | 0.1845 (3) | 1.31717 (16) | 0.0814 (8) | |
F2 | 0.2304 (3) | 0.1468 (3) | 1.09702 (15) | 0.0638 (7) | |
F3 | 1.3817 (8) | 0.390 (3) | 0.6363 (5) | 0.119 (4) | 0.68 (2) |
F4 | 1.147 (4) | 0.1564 (9) | 0.5723 (13) | 0.155 (7) | 0.68 (2) |
F5 | 1.133 (2) | 0.4078 (19) | 0.5405 (7) | 0.104 (5) | 0.68 (2) |
F3' | 1.332 (4) | 0.250 (5) | 0.6249 (11) | 0.100 (9) | 0.32 (2) |
F4' | 1.055 (2) | 0.210 (4) | 0.5351 (13) | 0.104 (9) | 0.32 (2) |
F5' | 1.234 (7) | 0.469 (3) | 0.571 (3) | 0.151 (15) | 0.32 (2) |
O1 | 0.7504 (4) | 0.1019 (3) | 1.10576 (18) | 0.0705 (9) | |
O2 | 0.6294 (3) | 0.4691 (3) | 0.91549 (17) | 0.0532 (7) | |
N1 | 0.6129 (4) | 0.3144 (3) | 1.05317 (19) | 0.0423 (7) | |
H1 | 0.5380 | 0.3709 | 1.0689 | 0.051* | |
N2 | 0.8163 (4) | 0.2845 (3) | 0.9451 (2) | 0.0464 (8) | |
H2A | 0.8471 | 0.2137 | 0.9870 | 0.056* | |
C1 | 0.6385 (6) | 0.1660 (5) | 1.2996 (3) | 0.0533 (10) | |
C2 | 0.5531 (7) | 0.1497 (5) | 1.3816 (3) | 0.0675 (12) | |
H2 | 0.6261 | 0.1476 | 1.4456 | 0.081* | |
C3 | 0.3525 (7) | 0.1365 (5) | 1.3649 (3) | 0.0705 (13) | |
H3 | 0.2904 | 0.1260 | 1.4189 | 0.085* | |
C4 | 0.2455 (6) | 0.1388 (5) | 1.2703 (3) | 0.0576 (11) | |
H4 | 0.1117 | 0.1294 | 1.2598 | 0.069* | |
C5 | 0.3382 (5) | 0.1551 (4) | 1.1917 (3) | 0.0442 (9) | |
C6 | 0.5403 (5) | 0.1718 (4) | 1.2025 (2) | 0.0394 (9) | |
C7 | 0.6440 (5) | 0.1915 (4) | 1.1161 (2) | 0.0434 (9) | |
C8 | 0.6850 (5) | 0.3623 (4) | 0.9665 (2) | 0.0390 (8) | |
C9 | 0.9079 (5) | 0.3064 (4) | 0.8621 (2) | 0.0375 (8) | |
C10 | 0.8445 (6) | 0.3807 (5) | 0.7762 (3) | 0.0592 (11) | |
H10 | 0.7400 | 0.4263 | 0.7724 | 0.071* | |
C11 | 0.9360 (6) | 0.3873 (5) | 0.6960 (3) | 0.0627 (11) | |
H11 | 0.8919 | 0.4367 | 0.6386 | 0.075* | |
C12 | 1.0931 (5) | 0.3209 (4) | 0.7004 (2) | 0.0456 (9) | |
C13 | 1.1585 (5) | 0.2503 (4) | 0.7871 (2) | 0.0446 (9) | |
H13 | 1.2652 | 0.2076 | 0.7912 | 0.054* | |
C14 | 1.0683 (5) | 0.2422 (4) | 0.8670 (2) | 0.0431 (9) | |
H14 | 1.1139 | 0.1938 | 0.9245 | 0.052* | |
C15 | 1.1837 (7) | 0.3174 (6) | 0.6124 (3) | 0.0641 (12) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0597 (16) | 0.134 (2) | 0.0707 (16) | 0.0553 (15) | 0.0185 (12) | 0.0252 (14) |
F2 | 0.0517 (13) | 0.0832 (16) | 0.0636 (14) | 0.0290 (12) | 0.0154 (11) | 0.0216 (11) |
F3 | 0.075 (4) | 0.216 (12) | 0.094 (4) | 0.060 (5) | 0.053 (3) | 0.046 (6) |
F4 | 0.28 (2) | 0.097 (5) | 0.136 (10) | 0.070 (9) | 0.147 (11) | 0.009 (6) |
F5 | 0.127 (7) | 0.173 (14) | 0.059 (4) | 0.093 (7) | 0.053 (4) | 0.061 (7) |
F3' | 0.109 (13) | 0.18 (2) | 0.073 (8) | 0.113 (16) | 0.055 (9) | 0.041 (12) |
F4' | 0.082 (10) | 0.15 (2) | 0.060 (8) | 0.001 (10) | 0.028 (7) | −0.048 (11) |
F5' | 0.24 (3) | 0.087 (10) | 0.17 (2) | 0.037 (17) | 0.16 (2) | 0.031 (14) |
O1 | 0.102 (2) | 0.089 (2) | 0.0734 (18) | 0.0794 (18) | 0.0572 (16) | 0.0427 (15) |
O2 | 0.0675 (17) | 0.0659 (18) | 0.0565 (15) | 0.0511 (15) | 0.0324 (13) | 0.0274 (13) |
N1 | 0.0534 (19) | 0.0490 (18) | 0.0492 (17) | 0.0369 (15) | 0.0331 (15) | 0.0193 (14) |
N2 | 0.062 (2) | 0.0567 (19) | 0.0473 (17) | 0.0442 (16) | 0.0314 (16) | 0.0232 (14) |
C1 | 0.047 (3) | 0.069 (3) | 0.059 (3) | 0.033 (2) | 0.023 (2) | 0.014 (2) |
C2 | 0.076 (3) | 0.096 (3) | 0.043 (2) | 0.038 (3) | 0.023 (2) | 0.010 (2) |
C3 | 0.080 (3) | 0.088 (3) | 0.063 (3) | 0.034 (3) | 0.046 (3) | 0.013 (2) |
C4 | 0.050 (3) | 0.062 (3) | 0.075 (3) | 0.025 (2) | 0.034 (2) | 0.011 (2) |
C5 | 0.048 (2) | 0.047 (2) | 0.046 (2) | 0.0233 (19) | 0.018 (2) | 0.0106 (17) |
C6 | 0.049 (2) | 0.042 (2) | 0.043 (2) | 0.0274 (18) | 0.0233 (19) | 0.0136 (16) |
C7 | 0.045 (2) | 0.050 (2) | 0.048 (2) | 0.0277 (19) | 0.0198 (18) | 0.0120 (17) |
C8 | 0.040 (2) | 0.040 (2) | 0.046 (2) | 0.0201 (17) | 0.0188 (18) | 0.0077 (16) |
C9 | 0.045 (2) | 0.044 (2) | 0.0355 (18) | 0.0254 (17) | 0.0172 (17) | 0.0096 (15) |
C10 | 0.069 (3) | 0.087 (3) | 0.054 (2) | 0.059 (2) | 0.031 (2) | 0.027 (2) |
C11 | 0.084 (3) | 0.090 (3) | 0.046 (2) | 0.061 (3) | 0.029 (2) | 0.032 (2) |
C12 | 0.050 (2) | 0.055 (2) | 0.043 (2) | 0.0263 (19) | 0.0198 (19) | 0.0107 (17) |
C13 | 0.039 (2) | 0.060 (2) | 0.048 (2) | 0.0291 (19) | 0.0154 (18) | 0.0044 (18) |
C14 | 0.046 (2) | 0.059 (2) | 0.0382 (19) | 0.0344 (19) | 0.0128 (18) | 0.0108 (16) |
C15 | 0.076 (4) | 0.078 (4) | 0.055 (3) | 0.037 (3) | 0.032 (3) | 0.016 (3) |
Geometric parameters (Å, º) top
F1—C1 | 1.366 (4) | C2—H2 | 0.9300 |
F2—C5 | 1.358 (4) | C3—C4 | 1.370 (5) |
F3—C15 | 1.338 (7) | C3—H3 | 0.9300 |
F4—C15 | 1.317 (7) | C4—C5 | 1.364 (5) |
F5—C15 | 1.294 (7) | C4—H4 | 0.9300 |
F3'—C15 | 1.330 (8) | C5—C6 | 1.405 (5) |
F4'—C15 | 1.340 (9) | C6—C7 | 1.507 (5) |
F5'—C15 | 1.327 (9) | C9—C10 | 1.387 (4) |
O1—C7 | 1.229 (4) | C9—C14 | 1.399 (4) |
O2—C8 | 1.227 (4) | C10—C11 | 1.383 (5) |
N1—C7 | 1.362 (4) | C10—H10 | 0.9300 |
N1—C8 | 1.402 (4) | C11—C12 | 1.389 (5) |
N1—H1 | 0.8600 | C11—H11 | 0.9300 |
N2—C8 | 1.360 (4) | C12—C13 | 1.384 (4) |
N2—C9 | 1.413 (4) | C12—C15 | 1.484 (5) |
N2—H2A | 0.8600 | C13—C14 | 1.373 (4) |
C1—C2 | 1.373 (5) | C13—H13 | 0.9300 |
C1—C6 | 1.382 (5) | C14—H14 | 0.9300 |
C2—C3 | 1.395 (5) | | |
| | | |
C7—N1—C8 | 129.5 (3) | C9—C10—H10 | 119.9 |
C7—N1—H1 | 115.3 | C10—C11—C12 | 120.7 (3) |
C8—N1—H1 | 115.3 | C10—C11—H11 | 119.6 |
C8—N2—C9 | 127.6 (3) | C12—C11—H11 | 119.6 |
C8—N2—H2A | 116.2 | C13—C12—C11 | 118.8 (3) |
C9—N2—H2A | 116.2 | C13—C12—C15 | 120.2 (3) |
F1—C1—C2 | 116.9 (4) | C11—C12—C15 | 121.0 (3) |
F1—C1—C6 | 118.4 (3) | C14—C13—C12 | 121.1 (3) |
C2—C1—C6 | 124.7 (4) | C14—C13—H13 | 119.5 |
C1—C2—C3 | 117.3 (4) | C12—C13—H13 | 119.5 |
C1—C2—H2 | 121.3 | C13—C14—C9 | 120.2 (3) |
C3—C2—H2 | 121.3 | C13—C14—H14 | 119.9 |
C4—C3—C2 | 121.1 (4) | C9—C14—H14 | 119.9 |
C4—C3—H3 | 119.5 | F5—C15—F4 | 107.0 (8) |
C2—C3—H3 | 119.5 | F5—C15—F5' | 34.3 (17) |
C5—C4—C3 | 119.0 (4) | F4—C15—F5' | 128.9 (13) |
C5—C4—H4 | 120.5 | F5—C15—F3' | 127.6 (9) |
C3—C4—H4 | 120.5 | F4—C15—F3' | 61.6 (9) |
F2—C5—C4 | 119.3 (3) | F5'—C15—F3' | 110.1 (14) |
F2—C5—C6 | 117.2 (3) | F5—C15—F3 | 102.4 (6) |
C4—C5—C6 | 123.4 (4) | F4—C15—F3 | 106.2 (7) |
C1—C6—C5 | 114.5 (3) | F5'—C15—F3 | 71.1 (15) |
C1—C6—C7 | 121.8 (3) | F3'—C15—F3 | 47.0 (11) |
C5—C6—C7 | 123.6 (3) | F5—C15—F4' | 69.7 (12) |
O1—C7—N1 | 123.6 (3) | F4—C15—F4' | 42.6 (8) |
O1—C7—C6 | 120.8 (3) | F5'—C15—F4' | 101.5 (13) |
N1—C7—C6 | 115.6 (3) | F3'—C15—F4' | 100.6 (10) |
O2—C8—N2 | 124.2 (3) | F3—C15—F4' | 134.0 (8) |
O2—C8—N1 | 119.9 (3) | F5—C15—C12 | 115.4 (6) |
N2—C8—N1 | 116.0 (3) | F4—C15—C12 | 112.7 (5) |
C10—C9—C14 | 118.9 (3) | F5'—C15—C12 | 115.1 (13) |
C10—C9—N2 | 124.2 (3) | F3'—C15—C12 | 115.8 (6) |
C14—C9—N2 | 116.8 (3) | F3—C15—C12 | 112.1 (5) |
C11—C10—C9 | 120.2 (3) | F4'—C15—C12 | 111.9 (8) |
C11—C10—H10 | 119.9 | | |
| | | |
F1—C1—C2—C3 | 178.0 (3) | C8—N2—C9—C10 | −15.5 (5) |
C6—C1—C2—C3 | 0.6 (6) | C8—N2—C9—C14 | 166.9 (3) |
C1—C2—C3—C4 | 0.3 (6) | C14—C9—C10—C11 | 1.4 (5) |
C2—C3—C4—C5 | −0.3 (6) | N2—C9—C10—C11 | −176.1 (4) |
C3—C4—C5—F2 | 176.1 (3) | C9—C10—C11—C12 | −0.4 (6) |
C3—C4—C5—C6 | −0.7 (5) | C10—C11—C12—C13 | −0.9 (6) |
F1—C1—C6—C5 | −178.8 (3) | C10—C11—C12—C15 | 176.1 (4) |
C2—C1—C6—C5 | −1.5 (5) | C11—C12—C13—C14 | 1.3 (5) |
F1—C1—C6—C7 | 2.1 (5) | C15—C12—C13—C14 | −175.9 (3) |
C2—C1—C6—C7 | 179.4 (3) | C12—C13—C14—C9 | −0.2 (5) |
F2—C5—C6—C1 | −175.3 (3) | C10—C9—C14—C13 | −1.1 (5) |
C4—C5—C6—C1 | 1.6 (5) | N2—C9—C14—C13 | 176.6 (3) |
F2—C5—C6—C7 | 3.7 (5) | C13—C12—C15—F5 | −170.8 (9) |
C4—C5—C6—C7 | −179.4 (3) | C11—C12—C15—F5 | 12.2 (10) |
C8—N1—C7—O1 | 1.6 (6) | C13—C12—C15—F4 | 65.8 (15) |
C8—N1—C7—C6 | −179.2 (3) | C11—C12—C15—F4 | −111.2 (14) |
C1—C6—C7—O1 | 46.4 (5) | C13—C12—C15—F5' | −133 (3) |
C5—C6—C7—O1 | −132.6 (4) | C11—C12—C15—F5' | 50 (3) |
C1—C6—C7—N1 | −132.9 (3) | C13—C12—C15—F3' | −2 (2) |
C5—C6—C7—N1 | 48.1 (5) | C11—C12—C15—F3' | −179 (2) |
C9—N2—C8—O2 | −1.6 (6) | C13—C12—C15—F3 | −54.0 (12) |
C9—N2—C8—N1 | 178.7 (3) | C11—C12—C15—F3 | 129.0 (12) |
C7—N1—C8—O2 | 175.2 (3) | C13—C12—C15—F4' | 112.1 (19) |
C7—N1—C8—N2 | −5.1 (5) | C11—C12—C15—F4' | −64.9 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.05 | 2.903 (5) | 170 |
N2—H2A···O1 | 0.86 | 2.01 | 2.703 (4) | 137 |
Symmetry code: (i) −x+1, −y+1, −z+2. |