The title compound, C18H9Cl2F3N4O, is a tricyclic amide with an overall U-shaped molecule.
Supporting information
CCDC reference: 298568
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.050
- wR factor = 0.120
- Data-to-parameter ratio = 11.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C18
| Author Response: see _publ_section_exptl_refinement
|
Alert level B
PLAT213_ALERT_2_B Atom F1 has ADP max/min Ratio ............. 4.10 prolat
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT213_ALERT_2_C Atom F2 has ADP max/min Ratio ............. 3.20 prolat
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10 - C11 ... 1.44 Ang.
PLAT731_ALERT_1_C Bond Calc 0.82(3), Rep 0.820(10) ...... 3.00 su-Rat
O1 -H1A 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.82(3), Rep 0.820(10) ...... 3.00 su-Rat
O1 -H1A 1.555 1.555
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.21
From the CIF: _reflns_number_total 2928
Count of symmetry unique reflns 1734
Completeness (_total/calc) 168.86%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1194
Fraction of Friedel pairs measured 0.689
Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXTL (Bruker, 2002).
1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-[(2-hydroxybenzylidene)amino]-
1
H-pyrazole-3-carbonitrile
top
Crystal data top
C18H9Cl2F3N4O | F(000) = 428 |
Mr = 425.19 | Dx = 1.558 Mg m−3 |
Monoclinic, P21 | Melting point: 446(1) K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4482 (9) Å | Cell parameters from 3113 reflections |
b = 9.3760 (11) Å | θ = 1.6–25.2° |
c = 13.1365 (16) Å | µ = 0.41 mm−1 |
β = 98.820 (2)° | T = 298 K |
V = 906.53 (19) Å3 | Block, colorless |
Z = 2 | 0.28 × 0.22 × 0.18 mm |
Data collection top
Bruker APEX area-detector diffractometer | 2928 independent reflections |
Radiation source: fine-focus sealed tube | 2687 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 25.2°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −8→7 |
Tmin = 0.899, Tmax = 0.930 | k = −8→11 |
4838 measured reflections | l = −15→14 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0637P)2 + 0.4065P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2928 reflections | Δρmax = 0.32 e Å−3 |
258 parameters | Δρmin = −0.29 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 3100 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.15 (9) |
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 >
2σ(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 | |
Cl1 | 0.57302 (16) | 0.16934 (13) | 0.62208 (9) | 0.0630 (4) | |
Cl2 | 0.02080 (13) | 0.20922 (13) | 0.84394 (8) | 0.0559 (3) | |
F1 | 0.4767 (10) | −0.2267 (6) | 0.9667 (6) | 0.231 (4) | |
F2 | 0.7255 (8) | −0.1614 (7) | 0.9367 (3) | 0.173 (3) | |
F3 | 0.6085 (6) | −0.0645 (5) | 1.0487 (2) | 0.1061 (14) | |
O1 | 0.7325 (4) | 0.4444 (4) | 0.8452 (3) | 0.0605 (9) | |
H1A | 0.630 (3) | 0.424 (6) | 0.817 (4) | 0.068 (17)* | |
N1 | 0.4377 (5) | 0.4632 (4) | 0.7035 (3) | 0.0429 (8) | |
N2 | 0.2163 (4) | 0.2811 (4) | 0.6683 (2) | 0.0405 (8) | |
N3 | 0.0534 (4) | 0.2493 (4) | 0.6125 (2) | 0.0431 (8) | |
N4 | −0.2993 (6) | 0.3791 (5) | 0.4402 (4) | 0.0701 (12) | |
C1 | 0.7946 (6) | 0.5568 (5) | 0.7965 (4) | 0.0499 (11) | |
C2 | 0.6899 (6) | 0.6236 (5) | 0.7116 (3) | 0.0454 (10) | |
C3 | 0.7623 (7) | 0.7431 (5) | 0.6691 (4) | 0.0601 (13) | |
H3A | 0.6942 | 0.7894 | 0.6136 | 0.072* | |
C4 | 0.9294 (7) | 0.7930 (7) | 0.7071 (5) | 0.0720 (16) | |
H4A | 0.9749 | 0.8732 | 0.6781 | 0.086* | |
C5 | 1.0323 (7) | 0.7247 (7) | 0.7888 (5) | 0.0775 (17) | |
H5A | 1.1482 | 0.7581 | 0.8137 | 0.093* | |
C6 | 0.9669 (6) | 0.6095 (6) | 0.8335 (4) | 0.0671 (15) | |
H6A | 1.0376 | 0.5654 | 0.8891 | 0.081* | |
C7 | 0.5132 (6) | 0.5714 (5) | 0.6672 (3) | 0.0466 (10) | |
H7A | 0.4511 | 0.6180 | 0.6099 | 0.056* | |
C8 | 0.2715 (6) | 0.4177 (5) | 0.6519 (3) | 0.0421 (9) | |
C9 | 0.1366 (6) | 0.4773 (5) | 0.5820 (3) | 0.0482 (11) | |
H9A | 0.1330 | 0.5686 | 0.5541 | 0.058* | |
C10 | 0.0064 (5) | 0.3703 (5) | 0.5623 (3) | 0.0448 (10) | |
C11 | −0.1651 (6) | 0.3769 (5) | 0.4945 (4) | 0.0491 (11) | |
C12 | 0.3053 (5) | 0.1799 (5) | 0.7387 (3) | 0.0382 (8) | |
C13 | 0.4711 (5) | 0.1219 (4) | 0.7268 (3) | 0.0427 (9) | |
C14 | 0.5593 (6) | 0.0266 (5) | 0.7975 (3) | 0.0487 (11) | |
H14A | 0.6724 | −0.0099 | 0.7893 | 0.058* | |
C15 | 0.4788 (6) | −0.0133 (5) | 0.8794 (3) | 0.0466 (10) | |
C16 | 0.3110 (6) | 0.0396 (4) | 0.8923 (3) | 0.0419 (9) | |
H16A | 0.2562 | 0.0096 | 0.9477 | 0.050* | |
C17 | 0.2255 (5) | 0.1361 (4) | 0.8235 (3) | 0.0393 (9) | |
C18 | 0.5705 (9) | −0.1170 (6) | 0.9572 (4) | 0.0728 (16) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0595 (7) | 0.0707 (9) | 0.0637 (7) | −0.0028 (6) | 0.0256 (5) | 0.0026 (6) |
Cl2 | 0.0391 (5) | 0.0666 (8) | 0.0625 (6) | 0.0054 (5) | 0.0098 (5) | 0.0028 (6) |
F1 | 0.234 (7) | 0.090 (3) | 0.306 (8) | −0.053 (4) | −0.164 (6) | 0.120 (4) |
F2 | 0.205 (5) | 0.237 (6) | 0.080 (2) | 0.180 (5) | 0.034 (3) | 0.041 (3) |
F3 | 0.119 (3) | 0.137 (3) | 0.0554 (19) | 0.057 (3) | −0.0071 (18) | 0.012 (2) |
O1 | 0.0440 (19) | 0.065 (2) | 0.068 (2) | 0.0016 (17) | −0.0086 (16) | 0.0071 (18) |
N1 | 0.0438 (19) | 0.037 (2) | 0.0459 (19) | −0.0043 (16) | 0.0016 (15) | 0.0027 (16) |
N2 | 0.0347 (17) | 0.0377 (19) | 0.0463 (19) | −0.0062 (15) | −0.0026 (14) | 0.0076 (15) |
N3 | 0.0364 (17) | 0.044 (2) | 0.0458 (19) | −0.0053 (15) | −0.0029 (14) | 0.0032 (15) |
N4 | 0.049 (2) | 0.073 (3) | 0.080 (3) | 0.000 (2) | −0.018 (2) | 0.016 (2) |
C1 | 0.040 (2) | 0.050 (3) | 0.060 (3) | 0.004 (2) | 0.008 (2) | −0.014 (2) |
C2 | 0.042 (2) | 0.048 (3) | 0.046 (2) | −0.0069 (19) | 0.0067 (18) | −0.0090 (19) |
C3 | 0.060 (3) | 0.056 (3) | 0.066 (3) | −0.013 (2) | 0.016 (2) | −0.003 (2) |
C4 | 0.063 (3) | 0.071 (4) | 0.087 (4) | −0.030 (3) | 0.028 (3) | −0.024 (3) |
C5 | 0.048 (3) | 0.082 (4) | 0.106 (4) | −0.032 (3) | 0.022 (3) | −0.033 (4) |
C6 | 0.039 (3) | 0.077 (4) | 0.082 (4) | 0.003 (2) | −0.003 (2) | −0.028 (3) |
C7 | 0.048 (2) | 0.043 (3) | 0.047 (2) | −0.004 (2) | 0.0017 (19) | 0.005 (2) |
C8 | 0.042 (2) | 0.041 (2) | 0.041 (2) | −0.0059 (18) | 0.0010 (18) | 0.0064 (18) |
C9 | 0.047 (2) | 0.043 (3) | 0.052 (2) | 0.000 (2) | 0.000 (2) | 0.010 (2) |
C10 | 0.037 (2) | 0.051 (3) | 0.044 (2) | −0.002 (2) | −0.0013 (17) | 0.004 (2) |
C11 | 0.044 (3) | 0.044 (3) | 0.058 (3) | 0.000 (2) | 0.003 (2) | 0.003 (2) |
C12 | 0.0338 (18) | 0.035 (2) | 0.0429 (19) | −0.0028 (16) | −0.0040 (15) | 0.0006 (17) |
C13 | 0.041 (2) | 0.042 (2) | 0.044 (2) | −0.0050 (18) | 0.0034 (17) | −0.0060 (18) |
C14 | 0.036 (2) | 0.051 (3) | 0.055 (3) | 0.0088 (19) | −0.0056 (19) | −0.007 (2) |
C15 | 0.053 (3) | 0.041 (2) | 0.041 (2) | 0.004 (2) | −0.0066 (19) | −0.0049 (18) |
C16 | 0.049 (2) | 0.039 (2) | 0.036 (2) | −0.0038 (19) | 0.0029 (17) | 0.0020 (18) |
C17 | 0.037 (2) | 0.034 (2) | 0.047 (2) | −0.0050 (17) | 0.0038 (17) | −0.0053 (18) |
C18 | 0.093 (4) | 0.055 (3) | 0.063 (3) | 0.025 (3) | −0.012 (3) | 0.005 (3) |
Geometric parameters (Å, º) top
Cl1—C13 | 1.728 (4) | C3—H3A | 0.9300 |
Cl2—C17 | 1.730 (4) | C4—C5 | 1.378 (9) |
F1—C18 | 1.260 (8) | C4—H4A | 0.9300 |
F2—C18 | 1.294 (7) | C5—C6 | 1.354 (8) |
F3—C18 | 1.290 (6) | C5—H5A | 0.9300 |
O1—C1 | 1.351 (6) | C6—H6A | 0.9300 |
O1—Cl2i | 3.080 (4) | C7—H7A | 0.9300 |
O1—H1A | 0.82 (1) | C8—C9 | 1.372 (6) |
N1—C7 | 1.286 (5) | C9—C10 | 1.392 (6) |
N1—C8 | 1.385 (5) | C9—H9A | 0.9300 |
N2—N3 | 1.352 (4) | C10—C11 | 1.442 (6) |
N2—C8 | 1.372 (5) | C12—C13 | 1.379 (6) |
N2—C12 | 1.417 (5) | C12—C17 | 1.403 (5) |
N3—C10 | 1.332 (5) | C13—C14 | 1.381 (6) |
N4—C11 | 1.135 (6) | C14—C15 | 1.362 (7) |
C1—C6 | 1.391 (6) | C14—H14A | 0.9300 |
C1—C2 | 1.407 (7) | C15—C16 | 1.379 (6) |
C2—C3 | 1.397 (7) | C15—C18 | 1.497 (6) |
C2—C7 | 1.440 (6) | C16—C17 | 1.365 (6) |
C3—C4 | 1.350 (7) | C16—H16A | 0.9300 |
| | | |
C1—O1—Cl2i | 105.4 (3) | C8—C9—C10 | 104.3 (4) |
C1—O1—H1A | 110 (4) | C8—C9—H9A | 127.8 |
Cl2i—O1—H1A | 116 (4) | C10—C9—H9A | 127.8 |
C7—N1—C8 | 118.1 (4) | N3—C10—C9 | 113.5 (3) |
N3—N2—C8 | 112.7 (3) | N3—C10—C11 | 118.9 (4) |
N3—N2—C12 | 119.8 (3) | C9—C10—C11 | 127.6 (4) |
C8—N2—C12 | 127.3 (3) | N4—C11—C10 | 178.4 (5) |
C10—N3—N2 | 103.1 (3) | C13—C12—C17 | 118.1 (4) |
O1—C1—C6 | 118.5 (4) | C13—C12—N2 | 121.8 (4) |
O1—C1—C2 | 122.2 (4) | C17—C12—N2 | 120.1 (4) |
C6—C1—C2 | 119.3 (5) | C12—C13—C14 | 121.4 (4) |
C3—C2—C1 | 118.2 (4) | C12—C13—Cl1 | 119.9 (3) |
C3—C2—C7 | 119.8 (4) | C14—C13—Cl1 | 118.7 (3) |
C1—C2—C7 | 122.1 (4) | C15—C14—C13 | 119.1 (4) |
C4—C3—C2 | 121.4 (5) | C15—C14—H14A | 120.4 |
C4—C3—H3A | 119.3 | C13—C14—H14A | 120.4 |
C2—C3—H3A | 119.3 | C14—C15—C16 | 121.0 (4) |
C3—C4—C5 | 119.9 (5) | C14—C15—C18 | 120.4 (4) |
C3—C4—H4A | 120.1 | C16—C15—C18 | 118.6 (4) |
C5—C4—H4A | 120.1 | C17—C16—C15 | 119.9 (4) |
C6—C5—C4 | 120.8 (5) | C17—C16—H16A | 120.0 |
C6—C5—H5A | 119.6 | C15—C16—H16A | 120.0 |
C4—C5—H5A | 119.6 | C16—C17—C12 | 120.4 (4) |
C5—C6—C1 | 120.5 (5) | C16—C17—Cl2 | 119.7 (3) |
C5—C6—H6A | 119.7 | C12—C17—Cl2 | 119.8 (3) |
C1—C6—H6A | 119.7 | F1—C18—F3 | 105.7 (7) |
N1—C7—C2 | 122.9 (4) | F1—C18—F2 | 106.5 (6) |
N1—C7—H7A | 118.5 | F3—C18—F2 | 104.0 (5) |
C2—C7—H7A | 118.5 | F1—C18—C15 | 113.0 (5) |
C9—C8—N2 | 106.3 (4) | F3—C18—C15 | 113.6 (4) |
C9—C8—N1 | 135.1 (4) | F2—C18—C15 | 113.3 (5) |
N2—C8—N1 | 118.5 (4) | | |
| | | |
C8—N2—N3—C10 | −1.1 (4) | C8—C9—C10—N3 | −1.6 (5) |
C12—N2—N3—C10 | 175.5 (4) | C8—C9—C10—C11 | 179.5 (4) |
Cl2i—O1—C1—C6 | −55.7 (4) | N3—N2—C12—C13 | 117.0 (4) |
Cl2i—O1—C1—C2 | 125.6 (4) | C8—N2—C12—C13 | −66.9 (6) |
O1—C1—C2—C3 | 177.1 (4) | N3—N2—C12—C17 | −63.2 (5) |
C6—C1—C2—C3 | −1.5 (6) | C8—N2—C12—C17 | 112.9 (5) |
O1—C1—C2—C7 | −3.6 (6) | C17—C12—C13—C14 | −1.8 (6) |
C6—C1—C2—C7 | 177.8 (4) | N2—C12—C13—C14 | 178.0 (4) |
C1—C2—C3—C4 | 0.9 (7) | C17—C12—C13—Cl1 | 178.6 (3) |
C7—C2—C3—C4 | −178.3 (5) | N2—C12—C13—Cl1 | −1.6 (6) |
C2—C3—C4—C5 | 0.5 (8) | C12—C13—C14—C15 | 1.5 (7) |
C3—C4—C5—C6 | −1.4 (8) | Cl1—C13—C14—C15 | −178.9 (3) |
C4—C5—C6—C1 | 0.8 (8) | C13—C14—C15—C16 | 0.2 (7) |
O1—C1—C6—C5 | −178.0 (4) | C13—C14—C15—C18 | 179.7 (4) |
C2—C1—C6—C5 | 0.7 (7) | C14—C15—C16—C17 | −1.6 (6) |
C8—N1—C7—C2 | −176.8 (4) | C18—C15—C16—C17 | 178.9 (4) |
C3—C2—C7—N1 | −179.0 (4) | C15—C16—C17—C12 | 1.2 (6) |
C1—C2—C7—N1 | 1.8 (7) | C15—C16—C17—Cl2 | −176.5 (3) |
N3—N2—C8—C9 | 0.2 (5) | C13—C12—C17—C16 | 0.4 (6) |
C12—N2—C8—C9 | −176.2 (4) | N2—C12—C17—C16 | −179.4 (4) |
N3—N2—C8—N1 | −179.2 (4) | C13—C12—C17—Cl2 | 178.2 (3) |
C12—N2—C8—N1 | 4.4 (6) | N2—C12—C17—Cl2 | −1.6 (5) |
C7—N1—C8—N2 | 159.9 (4) | C14—C15—C18—F1 | −122.0 (7) |
C7—N1—C8—C9 | −19.2 (7) | C16—C15—C18—F1 | 57.5 (8) |
N2—C8—C9—C10 | 0.8 (5) | C14—C15—C18—F3 | 117.7 (6) |
N1—C8—C9—C10 | −180.0 (5) | C16—C15—C18—F3 | −62.7 (7) |
N2—N3—C10—C9 | 1.7 (5) | C14—C15—C18—F2 | −0.6 (8) |
N2—N3—C10—C11 | −179.3 (4) | C16—C15—C18—F2 | 178.9 (5) |
Symmetry code: (i) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N1 | 0.82 (1) | 1.94 (3) | 2.658 (5) | 146 (5) |