The title compound, C
13H
7Cl
2F
3N
4O, has normal bond lengths and angles. The crystal packing is stabilized by intermolecular N—H
N hydrogen bonds.
Supporting information
CCDC reference: 245344
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.064
- wR factor = 0.170
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT213_ALERT_2_C Atom F3 has ADP max/min Ratio ............. 3.40 prolat
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.41
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10 - C11 ... 1.44 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
4 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
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: SHELXL97.
N-{3-Cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1
H-pyrazol-5-yl}acetamide
top
Crystal data top
C13H7Cl2F3N4O | F(000) = 1456 |
Mr = 363.13 | Dx = 1.559 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C2yc | Cell parameters from 2156 reflections |
a = 18.8282 (6) Å | θ = 2.6–25.2° |
b = 8.6541 (3) Å | µ = 0.46 mm−1 |
c = 19.0766 (6) Å | T = 298 K |
β = 95.583 (1)° | Block, colorless |
V = 3093.62 (18) Å3 | 0.44 × 0.16 × 0.13 mm |
Z = 8 | |
Data collection top
Bruker SMART APEX area-detector diffractometer | 2768 independent reflections |
Radiation source: fine-focus sealed tube | 2373 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 25.3°, θmin = 2.2° |
Absorption correction: integration (SADABS; Bruker, 2002) | h = −22→20 |
Tmin = 0.824, Tmax = 0.943 | k = −10→8 |
7655 measured reflections | l = −18→22 |
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) = 0.170 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | w = 1/[σ2(Fo2) + (0.079P)2 + 4.3533P] where P = (Fo2 + 2Fc2)/3 |
2768 reflections | (Δ/σ)max = 0.003 |
209 parameters | Δρmax = 0.65 e Å−3 |
0 restraints | Δρmin = −0.52 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 | |
Cl1 | 1.01946 (5) | 0.58378 (11) | 0.11136 (5) | 0.0661 (3) | |
Cl2 | 0.75365 (5) | 0.45026 (11) | 0.00088 (6) | 0.0735 (4) | |
O1 | 0.81662 (19) | 0.4727 (3) | 0.29753 (14) | 0.0835 (9) | |
N1 | 0.88236 (15) | 0.4100 (3) | 0.10069 (13) | 0.0437 (6) | |
N2 | 0.89015 (16) | 0.2609 (3) | 0.08006 (14) | 0.0495 (7) | |
N3 | 0.85589 (17) | 0.5641 (3) | 0.19798 (14) | 0.0515 (7) | |
H3 | 0.8644 | 0.6456 | 0.1744 | 0.062* | |
N4 | 0.8823 (3) | −0.1145 (3) | 0.1390 (2) | 0.0890 (13) | |
F1 | 0.83902 (17) | 0.9102 (3) | −0.14120 (14) | 0.0924 (9) | |
F2 | 0.94540 (17) | 0.8529 (4) | −0.14565 (16) | 0.1202 (12) | |
F3 | 0.9151 (3) | 1.0206 (3) | −0.07088 (16) | 0.1503 (18) | |
C1 | 0.8994 (3) | 0.8880 (5) | −0.1002 (2) | 0.0735 (12) | |
C2 | 0.8945 (2) | 0.7617 (3) | −0.04721 (16) | 0.0506 (8) | |
C3 | 0.95232 (19) | 0.7347 (3) | 0.00116 (17) | 0.0498 (8) | |
H3A | 0.9936 | 0.7934 | 0.0006 | 0.060* | |
C4 | 0.94806 (18) | 0.6198 (3) | 0.05024 (16) | 0.0446 (7) | |
C5 | 0.88713 (16) | 0.5305 (3) | 0.05079 (14) | 0.0393 (7) | |
C6 | 0.83010 (18) | 0.5599 (3) | 0.00141 (17) | 0.0470 (7) | |
C7 | 0.8332 (2) | 0.6753 (4) | −0.04808 (17) | 0.0524 (8) | |
H7 | 0.7947 | 0.6941 | −0.0813 | 0.063* | |
C8 | 0.86663 (18) | 0.4215 (3) | 0.16857 (16) | 0.0441 (7) | |
C9 | 0.8647 (2) | 0.2742 (3) | 0.19370 (17) | 0.0537 (8) | |
H9 | 0.8558 | 0.2425 | 0.2386 | 0.064* | |
C10 | 0.87919 (19) | 0.1825 (3) | 0.13742 (17) | 0.0500 (8) | |
C11 | 0.8817 (2) | 0.0160 (4) | 0.1367 (2) | 0.0659 (11) | |
C12 | 0.8322 (2) | 0.5814 (4) | 0.26343 (17) | 0.0524 (8) | |
C13 | 0.8274 (2) | 0.7454 (4) | 0.2878 (2) | 0.0666 (10) | |
H13A | 0.8107 | 0.7472 | 0.3337 | 0.100* | |
H13B | 0.7948 | 0.8015 | 0.2554 | 0.100* | |
H13C | 0.8738 | 0.7924 | 0.2899 | 0.100* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0685 (6) | 0.0588 (6) | 0.0672 (6) | −0.0052 (4) | −0.0126 (4) | 0.0037 (4) |
Cl2 | 0.0653 (6) | 0.0512 (6) | 0.1017 (8) | −0.0170 (4) | −0.0037 (5) | 0.0105 (5) |
O1 | 0.146 (3) | 0.0528 (16) | 0.0565 (16) | −0.0066 (17) | 0.0344 (17) | 0.0017 (13) |
N1 | 0.0649 (16) | 0.0236 (12) | 0.0434 (14) | 0.0005 (11) | 0.0094 (12) | 0.0024 (10) |
N2 | 0.0747 (18) | 0.0243 (12) | 0.0511 (15) | 0.0008 (11) | 0.0145 (13) | −0.0008 (11) |
N3 | 0.084 (2) | 0.0264 (12) | 0.0457 (15) | 0.0033 (12) | 0.0120 (13) | 0.0012 (11) |
N4 | 0.157 (4) | 0.0279 (16) | 0.089 (3) | 0.0097 (19) | 0.046 (3) | 0.0071 (15) |
F1 | 0.131 (2) | 0.0687 (16) | 0.0742 (16) | 0.0045 (14) | −0.0066 (15) | 0.0311 (12) |
F2 | 0.119 (2) | 0.153 (3) | 0.095 (2) | 0.006 (2) | 0.0389 (18) | 0.064 (2) |
F3 | 0.289 (5) | 0.0559 (16) | 0.093 (2) | −0.075 (2) | −0.047 (3) | 0.0298 (15) |
C1 | 0.110 (3) | 0.057 (2) | 0.053 (2) | −0.019 (2) | 0.009 (2) | 0.0155 (18) |
C2 | 0.082 (2) | 0.0320 (15) | 0.0385 (16) | −0.0028 (15) | 0.0097 (15) | 0.0010 (13) |
C3 | 0.067 (2) | 0.0339 (16) | 0.0499 (18) | −0.0120 (14) | 0.0115 (15) | −0.0024 (13) |
C4 | 0.0598 (19) | 0.0329 (15) | 0.0407 (16) | −0.0011 (13) | 0.0030 (13) | −0.0020 (12) |
C5 | 0.0587 (18) | 0.0230 (13) | 0.0373 (15) | 0.0003 (12) | 0.0098 (13) | 0.0003 (11) |
C6 | 0.0584 (19) | 0.0298 (14) | 0.0525 (18) | −0.0030 (13) | 0.0034 (15) | −0.0007 (13) |
C7 | 0.070 (2) | 0.0372 (17) | 0.0485 (18) | 0.0004 (15) | −0.0031 (15) | 0.0013 (14) |
C8 | 0.0638 (19) | 0.0280 (14) | 0.0409 (16) | 0.0017 (13) | 0.0072 (14) | 0.0000 (12) |
C9 | 0.084 (2) | 0.0318 (16) | 0.0466 (18) | 0.0016 (15) | 0.0155 (16) | 0.0065 (13) |
C10 | 0.070 (2) | 0.0249 (14) | 0.0564 (19) | 0.0011 (14) | 0.0143 (16) | 0.0038 (13) |
C11 | 0.108 (3) | 0.0324 (19) | 0.062 (2) | 0.0022 (18) | 0.028 (2) | 0.0021 (16) |
C12 | 0.074 (2) | 0.0396 (18) | 0.0441 (18) | 0.0027 (15) | 0.0061 (16) | −0.0018 (14) |
C13 | 0.094 (3) | 0.047 (2) | 0.060 (2) | 0.0114 (19) | 0.0130 (19) | −0.0125 (17) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.720 (3) | C2—C3 | 1.377 (5) |
Cl2—C6 | 1.723 (3) | C3—C4 | 1.373 (4) |
O1—C12 | 1.196 (4) | C3—H3A | 0.9300 |
N1—C8 | 1.360 (4) | C4—C5 | 1.384 (4) |
N1—N2 | 1.361 (3) | C5—C6 | 1.381 (4) |
N1—C5 | 1.421 (3) | C6—C7 | 1.379 (4) |
N2—C10 | 1.321 (4) | C7—H7 | 0.9300 |
N3—C12 | 1.375 (4) | C8—C9 | 1.364 (4) |
N3—C8 | 1.378 (4) | C9—C10 | 1.383 (5) |
N3—H3 | 0.8600 | C9—H9 | 0.9300 |
N4—C11 | 1.130 (5) | C10—C11 | 1.441 (5) |
F1—C1 | 1.330 (5) | C12—C13 | 1.499 (5) |
F2—C1 | 1.319 (5) | C13—H13A | 0.9600 |
F3—C1 | 1.298 (5) | C13—H13B | 0.9600 |
C1—C2 | 1.497 (5) | C13—H13C | 0.9600 |
C2—C7 | 1.373 (5) | | |
| | | |
C8—N1—N2 | 112.6 (2) | C7—C6—C5 | 121.2 (3) |
C8—N1—C5 | 128.2 (2) | C7—C6—Cl2 | 119.1 (3) |
N2—N1—C5 | 119.1 (2) | C5—C6—Cl2 | 119.7 (2) |
C10—N2—N1 | 102.6 (2) | C2—C7—C6 | 118.5 (3) |
C12—N3—C8 | 122.7 (3) | C2—C7—H7 | 120.7 |
C12—N3—H3 | 118.6 | C6—C7—H7 | 120.7 |
C8—N3—H3 | 118.6 | N1—C8—C9 | 106.4 (3) |
F3—C1—F2 | 110.6 (4) | N1—C8—N3 | 120.5 (3) |
F3—C1—F1 | 105.7 (4) | C9—C8—N3 | 133.1 (3) |
F2—C1—F1 | 103.0 (3) | C8—C9—C10 | 104.5 (3) |
F3—C1—C2 | 112.4 (3) | C8—C9—H9 | 127.8 |
F2—C1—C2 | 111.3 (4) | C10—C9—H9 | 127.8 |
F1—C1—C2 | 113.3 (4) | N2—C10—C9 | 114.0 (3) |
C7—C2—C3 | 121.6 (3) | N2—C10—C11 | 119.9 (3) |
C7—C2—C1 | 119.8 (3) | C9—C10—C11 | 126.1 (3) |
C3—C2—C1 | 118.6 (3) | N4—C11—C10 | 176.8 (4) |
C4—C3—C2 | 119.0 (3) | O1—C12—N3 | 121.8 (3) |
C4—C3—H3A | 120.5 | O1—C12—C13 | 123.4 (3) |
C2—C3—H3A | 120.5 | N3—C12—C13 | 114.8 (3) |
C3—C4—C5 | 120.8 (3) | C12—C13—H13A | 109.5 |
C3—C4—Cl1 | 120.0 (3) | C12—C13—H13B | 109.5 |
C5—C4—Cl1 | 119.2 (2) | H13A—C13—H13B | 109.5 |
C6—C5—C4 | 118.8 (3) | C12—C13—H13C | 109.5 |
C6—C5—N1 | 119.8 (3) | H13A—C13—H13C | 109.5 |
C4—C5—N1 | 121.4 (3) | H13B—C13—H13C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N4i | 0.86 | 2.22 | 3.060 (4) | 166 |
Symmetry code: (i) x, y+1, z. |