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The title compound, C15H5Cl2F3N4O2, is a tricyclic imide with an overall U-shape, each of the three rings being planar. These include a phenyl ring with two chloro and one tri­fluoro­methyl substituents, a central pyrazole ring with a cyano substituent, and a dioxopyrrolidine ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804016678/su6121sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804016678/su6121Isup2.hkl
Contains datablock I

CCDC reference: 248804

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.055
  • wR factor = 0.165
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C1
Alert level C PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10 - C11 ... 1.44 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact F1 .. O1 .. 2.89 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 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

Computing details top

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: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-(2,5-dioxo-2,5-dihydro-1H- pyrrol-1-yl)-1H-pyrazole-3-carbonitrile top
Crystal data top
C15H5Cl2F3N4O2F(000) = 800
Mr = 401.13Dx = 1.622 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3254 reflections
a = 12.8261 (10) Åθ = 2.4–26.0°
b = 8.9942 (7) ŵ = 0.45 mm1
c = 14.6896 (12) ÅT = 298 K
β = 104.217 (1)°Block, colorless
V = 1642.7 (2) Å30.43 × 0.38 × 0.20 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
3225 independent reflections
Radiation source: fine-focus sealed tube2660 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: integration
(SADABS; Bruker, 2002)
h = 1514
Tmin = 0.832, Tmax = 0.916k = 119
9003 measured reflectionsl = 1816
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0945P)2 + 0.8386P]
where P = (Fo2 + 2Fc2)/3
3225 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.72 e Å3
0 restraintsΔρmin = 0.38 e Å3
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
xyzUiso*/Ueq
Cl10.07471 (6)0.47385 (9)0.19496 (6)0.0638 (3)
Cl20.01644 (7)0.75112 (11)0.50326 (5)0.0729 (3)
O10.2530 (2)1.0201 (2)0.49559 (16)0.0758 (7)
O20.1035 (2)0.8294 (3)0.20621 (15)0.0750 (7)
N10.14676 (16)0.6217 (2)0.38311 (15)0.0424 (5)
N30.4332 (2)0.3464 (3)0.5455 (2)0.0739 (8)
N40.17897 (17)0.8822 (2)0.36239 (15)0.0420 (5)
N20.19715 (18)0.4966 (2)0.42196 (17)0.0470 (5)
C20.1867 (2)0.5922 (3)0.2753 (2)0.0497 (6)
C30.1456 (2)0.6599 (3)0.3616 (2)0.0512 (7)
H30.19150.69740.39620.061*
C40.0359 (2)0.6708 (3)0.39517 (18)0.0459 (6)
C50.0337 (2)0.6150 (3)0.34441 (18)0.0407 (6)
C60.0096 (2)0.5478 (3)0.25839 (19)0.0439 (6)
C70.1193 (2)0.5367 (3)0.2231 (2)0.0487 (6)
H70.14760.49250.16500.058*
C80.2144 (2)0.7403 (3)0.39565 (18)0.0411 (5)
C90.3126 (2)0.6927 (3)0.44547 (18)0.0468 (6)
H90.37540.74790.46560.056*
C100.2971 (2)0.5416 (3)0.45920 (19)0.0461 (6)
C110.3738 (2)0.4324 (3)0.5067 (2)0.0538 (7)
C120.1275 (2)0.9176 (3)0.26865 (19)0.0475 (6)
C130.2040 (2)1.0135 (3)0.4153 (2)0.0475 (6)
C140.1575 (2)1.1359 (3)0.3503 (2)0.0539 (7)
H140.15941.23620.36610.065*
C150.1129 (2)1.0806 (3)0.2666 (2)0.0520 (7)
H150.07781.13560.21450.062*
F10.33778 (17)0.5257 (3)0.15503 (17)0.1062 (9)
F20.34456 (19)0.4721 (3)0.2896 (2)0.1064 (9)
F30.35836 (17)0.6960 (3)0.2506 (3)0.1303 (13)
C10.3058 (3)0.5759 (4)0.2407 (2)0.0676 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0598 (5)0.0625 (5)0.0725 (5)0.0009 (3)0.0229 (4)0.0229 (4)
Cl20.0624 (5)0.1038 (7)0.0518 (5)0.0124 (4)0.0125 (4)0.0270 (4)
O10.1045 (19)0.0587 (13)0.0508 (13)0.0126 (13)0.0068 (12)0.0060 (10)
O20.118 (2)0.0511 (12)0.0475 (12)0.0037 (13)0.0035 (12)0.0022 (10)
N10.0388 (11)0.0354 (11)0.0493 (12)0.0013 (8)0.0041 (9)0.0018 (9)
N30.0594 (16)0.0695 (18)0.086 (2)0.0165 (14)0.0055 (14)0.0238 (15)
N40.0444 (11)0.0363 (11)0.0430 (11)0.0006 (9)0.0062 (9)0.0030 (8)
N20.0448 (12)0.0370 (11)0.0555 (13)0.0049 (9)0.0053 (10)0.0044 (9)
C20.0418 (14)0.0516 (16)0.0527 (15)0.0017 (12)0.0057 (12)0.0050 (12)
C30.0441 (14)0.0582 (17)0.0519 (15)0.0032 (12)0.0130 (12)0.0012 (13)
C40.0477 (14)0.0462 (14)0.0420 (13)0.0031 (11)0.0076 (11)0.0025 (11)
C50.0390 (12)0.0333 (12)0.0475 (14)0.0000 (10)0.0058 (10)0.0028 (10)
C60.0464 (14)0.0382 (13)0.0470 (14)0.0002 (10)0.0114 (11)0.0041 (11)
C70.0496 (15)0.0474 (15)0.0449 (14)0.0029 (12)0.0033 (11)0.0044 (11)
C80.0433 (13)0.0374 (13)0.0419 (13)0.0020 (10)0.0092 (10)0.0015 (10)
C90.0396 (13)0.0476 (15)0.0502 (14)0.0019 (11)0.0052 (11)0.0043 (11)
C100.0432 (14)0.0466 (15)0.0467 (14)0.0046 (11)0.0075 (11)0.0041 (11)
C110.0464 (15)0.0547 (16)0.0570 (16)0.0044 (13)0.0062 (12)0.0098 (14)
C120.0521 (15)0.0448 (14)0.0433 (14)0.0017 (12)0.0074 (11)0.0037 (12)
C130.0511 (15)0.0414 (14)0.0492 (16)0.0050 (11)0.0106 (12)0.0021 (11)
C140.0631 (18)0.0375 (14)0.0618 (17)0.0002 (12)0.0170 (14)0.0000 (12)
C150.0566 (16)0.0429 (14)0.0552 (16)0.0049 (12)0.0110 (13)0.0111 (12)
F10.0554 (12)0.166 (3)0.0843 (16)0.0098 (14)0.0077 (11)0.0255 (16)
F20.0670 (14)0.127 (2)0.125 (2)0.0303 (13)0.0226 (14)0.0100 (16)
F30.0502 (12)0.0894 (17)0.232 (4)0.0135 (11)0.0024 (16)0.036 (2)
C10.0466 (17)0.082 (2)0.069 (2)0.0020 (16)0.0042 (15)0.0034 (18)
Geometric parameters (Å, º) top
Cl1—C61.725 (3)C4—C51.390 (4)
Cl2—C41.724 (3)C5—C61.388 (4)
O1—C131.194 (4)C6—C71.379 (4)
O2—C121.194 (3)C7—H70.9300
N1—N21.352 (3)C8—C91.361 (4)
N1—C81.359 (3)C9—C101.395 (4)
N1—C51.423 (3)C9—H90.9300
N3—C111.136 (4)C10—C111.443 (4)
N4—C81.401 (3)C12—C151.477 (4)
N4—C131.407 (3)C13—C141.483 (4)
N4—C121.410 (3)C14—C151.319 (4)
N2—C101.327 (3)C14—H140.9300
C2—C71.381 (4)C15—H150.9300
C2—C31.389 (4)F1—C11.305 (4)
C2—C11.495 (4)F2—C11.345 (4)
C3—C41.375 (4)F3—C11.300 (4)
C3—H30.9300
N2—N1—C8111.9 (2)C9—C8—N4130.7 (2)
N2—N1—C5117.93 (19)C8—C9—C10103.8 (2)
C8—N1—C5129.9 (2)C8—C9—H9128.1
C8—N4—C13124.2 (2)C10—C9—H9128.1
C8—N4—C12125.5 (2)N2—C10—C9113.3 (2)
C13—N4—C12109.8 (2)N2—C10—C11117.8 (2)
C10—N2—N1103.5 (2)C9—C10—C11128.9 (3)
C7—C2—C3121.1 (3)N3—C11—C10178.7 (3)
C7—C2—C1120.2 (3)O2—C12—N4124.8 (3)
C3—C2—C1118.7 (3)O2—C12—C15129.5 (3)
C4—C3—C2118.9 (3)N4—C12—C15105.7 (2)
C4—C3—H3120.5O1—C13—N4125.5 (3)
C2—C3—H3120.5O1—C13—C14129.0 (3)
C3—C4—C5121.2 (2)N4—C13—C14105.5 (2)
C3—C4—Cl2119.5 (2)C15—C14—C13109.5 (3)
C5—C4—Cl2119.3 (2)C15—C14—H14125.3
C6—C5—C4118.6 (2)C13—C14—H14125.3
C6—C5—N1121.5 (2)C14—C15—C12109.4 (2)
C4—C5—N1119.8 (2)C14—C15—H15125.3
C7—C6—C5121.2 (2)C12—C15—H15125.3
C7—C6—Cl1119.1 (2)F3—C1—F1110.3 (3)
C5—C6—Cl1119.7 (2)F3—C1—F2104.3 (3)
C6—C7—C2119.0 (2)F1—C1—F2101.8 (3)
C6—C7—H7120.5F3—C1—C2113.3 (3)
C2—C7—H7120.5F1—C1—C2114.5 (3)
N1—C8—C9107.6 (2)F2—C1—C2111.6 (3)
N1—C8—N4121.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O1i0.932.503.380 (4)157
C14—H14···N2ii0.932.493.410 (3)170
Symmetry codes: (i) x1/2, y+3/2, z1/2; (ii) x, y+1, z.
 

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