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In the title compound, C19H14Cl2F3N5O2, which shows insecticidal activity, the dihedral angle between the pyrazole and pyridine rings is 68.15 (16)°. In the crystal structure, the mol­ecules are linked by N—H...O and C—H...O hydrogen bonds and an intra­molecular N—H...O inter­action also occurs. The F atoms of the –CF3 group are disordered over two sets of sites in a 0.800 (8):0.200 (8) ratio.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808037604/hb2777sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808037604/hb2777Isup2.hkl
Contains datablock I

CCDC reference: 712479

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.034
  • wR factor = 0.082
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT431_ALERT_2_A Short Inter HL..A Contact F2' .. F2' .. 2.30 Ang.
Author Response: A disorder artifact

Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O2 .. O2 .. 2.83 Ang.
Alert level C PLAT083_ALERT_2_C SHELXL Second Parameter in WGHT unusually Large. 9.00 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7
Author Response: disorder of C7-F bonds
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT234_ALERT_4_C Large Hirshfeld Difference C3     --  C4      ..       0.11  Ang.

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 25.03 From the CIF: _reflns_number_total 3565 Count of symmetry unique reflns 1944 Completeness (_total/calc) 183.38% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1621 Fraction of Friedel pairs measured 0.834 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 49 PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 42.60 Deg. F2' -C7 -F3 1.555 1.555 1.555
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 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 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Anthranilamide compounds containing an N-pyridyl pyrazole grouping are a new class of inseticides showing potent activity against a broad spectrum of Lepidoptera and no-cross resistance to existing insecticides (Lahm et al., 2003) and their mode of action has been been established (Lahm et al., 2005). Anthranilamides show little effect on mammalian ryanodine receptors and as a result they show excellent insect versus mammalian selectivity. As part of our studies in this area, we now report the crystal structures of the title compound, (I), (Fig. 1) which possesses high insecticidal activity.

The pyrazole ring and pyridine rings are not coplanar, the dihedral angle formed by the least-squares planes of the rings being equal to 68.15 (16)°. The dihedral angle between the mean plane of the pyrazole ring and the plane of the C10/O1/N4 group is 23.4 (2)° and the dihedral angle between the mean plane of the phenyl ring and the plane of the C10/O1/N4 group is 59.9 (2)°.

An intramolecular N—H···O hydrogen bond (Table 1) is observed, which helps to establish the molecular conformation. Intermolecular N—H···O and C—H···O bonds result in a three-dimensional network.

Related literature top

For the synthesis and background to the insecticidal properties of the title compound, see: Lahm et al. (2003, 2005).

Experimental top

The title compound was prepared by the literature method (Lahm et al., 2003). The crude products were purified by silica-gel column chromatography and then grown from acetone to afford colourless blocks of (I).

Anal. Calcd for C12H14N4O3: C, 48.32; H, 2.99; N, 14.83. Found: C, 48.47; H, 3.04; N, 14.66. 1H NMR(CDCl3): 2.19 (s, 3H, CH3), 2.70 (d, J=4.5 Hz, 3H, CH3), 7.30–7.31 (m, 2H, Ph), 7.57 (dd, 1H), 8.05 (d, J=8.1 Hz, 1H), 8.22 (br s, J=4.5 Hz, 1H, NH), 8.46 (d, J=4.8 Hz, 1H), 7.64 (s, 1H), 10.43 (s, 1H, NH).

Refinement top

Although all H atoms were visible in difference maps, they were placed in geometrically calculated positions, with C—H distances in the range 0.93–0.96Å and N—H distances of 0.86 Å, andincluded in the final refinement in the riding model approximation,with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl C). The F atoms of the -CF3 are disordered over two sets of sites in a 0.800 (8):0.200 (8) ratio.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

N-[4-Chloro-2-methyl-6-(N-methylcarbamoyl)phenyl]-1-(3-chloro-2- pyridyl)-3-trifluoromethyl-1H-pyrazole-5-carboxamide top
Crystal data top
C19H14Cl2F3N5O2Dx = 1.524 Mg m3
Mr = 472.25Melting point: 492(1) K
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
a = 26.4612 (16) ÅCell parameters from 3952 reflections
b = 32.8657 (19) Åθ = 2.4–23.9°
c = 9.4679 (6) ŵ = 0.37 mm1
V = 8233.9 (9) Å3T = 296 K
Z = 16Block, colourless
F(000) = 38400.24 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD
diffractometer
3565 independent reflections
Radiation source: fine-focus sealed tube3284 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 3124
Tmin = 0.917, Tmax = 0.937k = 3438
10439 measured reflectionsl = 1111
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0387P)2 + 8.8659P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3565 reflectionsΔρmax = 0.18 e Å3
310 parametersΔρmin = 0.20 e Å3
49 restraintsAbsolute structure: Flack (1983), 1621 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (7)
Crystal data top
C19H14Cl2F3N5O2V = 8233.9 (9) Å3
Mr = 472.25Z = 16
Orthorhombic, Fdd2Mo Kα radiation
a = 26.4612 (16) ŵ = 0.37 mm1
b = 32.8657 (19) ÅT = 296 K
c = 9.4679 (6) Å0.24 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD
diffractometer
3565 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
3284 reflections with I > 2σ(I)
Tmin = 0.917, Tmax = 0.937Rint = 0.021
10439 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.082Δρmax = 0.18 e Å3
S = 1.04Δρmin = 0.20 e Å3
3565 reflectionsAbsolute structure: Flack (1983), 1621 Friedel pairs
310 parametersAbsolute structure parameter: 0.01 (7)
49 restraints
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*/UeqOcc. (<1)
Cl10.28309 (3)1.00598 (3)0.40561 (10)0.0647 (3)
Cl20.46782 (4)0.85540 (5)0.17854 (12)0.1075 (5)
F10.39895 (14)1.06805 (12)0.8595 (6)0.1059 (17)0.800 (8)
F20.4312 (2)1.01859 (14)0.9614 (4)0.1148 (18)0.800 (8)
F30.47071 (12)1.04708 (16)0.7981 (5)0.0958 (15)0.800 (8)
F1'0.4028 (5)1.0381 (5)0.9535 (11)0.074 (4)0.200 (8)
F2'0.4714 (4)1.0263 (5)0.8653 (18)0.087 (5)0.200 (8)
F3'0.4283 (7)1.0724 (3)0.7878 (16)0.106 (6)0.200 (8)
O10.36097 (7)0.91496 (6)0.4022 (2)0.0453 (5)
O20.52136 (8)0.96046 (6)0.3535 (3)0.0576 (6)
N10.35642 (9)0.99358 (8)0.7518 (3)0.0445 (6)
N20.34753 (8)0.97021 (6)0.6376 (2)0.0360 (5)
N30.28654 (9)0.92344 (8)0.7109 (3)0.0479 (6)
N40.42127 (8)0.95772 (6)0.3170 (2)0.0342 (5)
H40.43590.98080.32910.041*
N50.56488 (8)0.90701 (7)0.2779 (3)0.0419 (6)
H50.56720.88730.21860.050*
C10.26575 (11)0.96695 (9)0.5174 (3)0.0448 (7)
C20.21856 (11)0.94974 (11)0.5056 (4)0.0566 (9)
H20.19580.95870.43750.068*
C30.20605 (12)0.91908 (11)0.5966 (4)0.0602 (10)
H30.17470.90640.58990.072*
C40.23980 (14)0.90720 (10)0.6975 (4)0.0592 (9)
H4A0.23020.88690.76040.071*
C50.29811 (10)0.95245 (8)0.6209 (3)0.0379 (6)
C60.40279 (10)1.00776 (9)0.7321 (3)0.0434 (7)
C70.42585 (12)1.03518 (11)0.8368 (4)0.0596 (9)
C80.42392 (10)0.99401 (9)0.6056 (3)0.0429 (7)
H80.45581.00000.56950.052*
C90.38752 (10)0.96987 (8)0.5464 (3)0.0346 (6)
C100.38824 (9)0.94496 (7)0.4152 (3)0.0329 (6)
C110.43316 (10)0.93476 (7)0.1941 (3)0.0323 (6)
C120.48281 (9)0.92011 (7)0.1738 (3)0.0319 (6)
C130.49293 (10)0.89622 (9)0.0565 (3)0.0415 (6)
H130.52540.88640.04100.050*
C140.45484 (12)0.88718 (10)0.0367 (3)0.0534 (8)
C150.40693 (11)0.90324 (10)0.0207 (3)0.0507 (8)
H150.38220.89760.08750.061*
C160.39557 (10)0.92751 (9)0.0935 (3)0.0401 (6)
C170.34412 (11)0.94686 (11)0.1030 (4)0.0565 (8)
H17A0.32900.94760.01080.085*
H17B0.34740.97410.13850.085*
H17C0.32320.93130.16560.085*
C180.52432 (10)0.93058 (8)0.2762 (3)0.0334 (6)
C190.60538 (12)0.91391 (11)0.3778 (4)0.0597 (9)
H19A0.62160.93940.35710.090*
H19B0.62960.89230.37080.090*
H19C0.59180.91470.47180.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0572 (5)0.0631 (5)0.0737 (6)0.0044 (4)0.0053 (4)0.0203 (5)
Cl20.0781 (7)0.1621 (12)0.0821 (8)0.0360 (7)0.0273 (6)0.0839 (8)
F10.090 (2)0.090 (2)0.137 (3)0.0050 (19)0.020 (2)0.063 (2)
F20.168 (4)0.117 (3)0.059 (2)0.042 (3)0.040 (2)0.0052 (18)
F30.067 (2)0.132 (3)0.088 (3)0.0499 (19)0.0139 (17)0.043 (2)
F1'0.067 (6)0.095 (6)0.060 (6)0.014 (5)0.009 (4)0.021 (5)
F2'0.072 (6)0.094 (6)0.094 (7)0.004 (5)0.017 (5)0.018 (5)
F3'0.121 (8)0.094 (7)0.103 (7)0.008 (5)0.014 (5)0.004 (5)
O10.0485 (11)0.0440 (11)0.0433 (11)0.0146 (9)0.0108 (10)0.0005 (9)
O20.0434 (12)0.0537 (12)0.0757 (17)0.0105 (10)0.0185 (11)0.0324 (12)
N10.0407 (13)0.0564 (15)0.0365 (13)0.0054 (11)0.0038 (10)0.0095 (11)
N20.0312 (11)0.0441 (12)0.0326 (12)0.0019 (9)0.0043 (9)0.0051 (10)
N30.0511 (15)0.0500 (14)0.0426 (14)0.0052 (12)0.0153 (11)0.0014 (12)
N40.0332 (11)0.0331 (11)0.0364 (13)0.0044 (9)0.0052 (10)0.0030 (10)
N50.0347 (12)0.0433 (13)0.0478 (14)0.0065 (10)0.0059 (10)0.0128 (11)
C10.0378 (16)0.0472 (16)0.0492 (18)0.0027 (13)0.0053 (13)0.0069 (14)
C20.0356 (17)0.067 (2)0.067 (2)0.0003 (15)0.0020 (16)0.0149 (18)
C30.0381 (17)0.068 (2)0.075 (2)0.0137 (16)0.0124 (17)0.022 (2)
C40.065 (2)0.0553 (19)0.058 (2)0.0176 (17)0.0271 (17)0.0078 (16)
C50.0335 (14)0.0422 (15)0.0380 (16)0.0023 (11)0.0100 (12)0.0074 (12)
C60.0380 (16)0.0545 (17)0.0376 (16)0.0054 (13)0.0001 (12)0.0042 (13)
C70.0503 (19)0.077 (2)0.052 (2)0.0108 (18)0.0062 (16)0.0155 (18)
C80.0326 (14)0.0557 (17)0.0405 (16)0.0058 (13)0.0051 (12)0.0010 (13)
C90.0337 (14)0.0392 (14)0.0307 (13)0.0022 (11)0.0021 (11)0.0020 (11)
C100.0288 (13)0.0351 (13)0.0347 (14)0.0006 (11)0.0028 (11)0.0050 (11)
C110.0330 (13)0.0329 (13)0.0310 (14)0.0043 (11)0.0016 (11)0.0042 (10)
C120.0314 (13)0.0310 (12)0.0333 (14)0.0044 (10)0.0008 (11)0.0008 (11)
C130.0357 (14)0.0499 (16)0.0391 (15)0.0027 (12)0.0002 (12)0.0068 (13)
C140.0502 (18)0.069 (2)0.0405 (17)0.0035 (16)0.0066 (13)0.0218 (16)
C150.0422 (17)0.071 (2)0.0392 (17)0.0054 (15)0.0108 (13)0.0092 (16)
C160.0319 (14)0.0501 (16)0.0383 (16)0.0040 (12)0.0012 (11)0.0034 (13)
C170.0365 (15)0.085 (2)0.0481 (19)0.0068 (16)0.0051 (14)0.0040 (16)
C180.0335 (14)0.0308 (13)0.0359 (15)0.0015 (11)0.0003 (11)0.0020 (11)
C190.0393 (17)0.073 (2)0.067 (2)0.0107 (15)0.0141 (15)0.0186 (19)
Geometric parameters (Å, º) top
Cl1—C11.725 (3)C2—H20.9300
Cl2—C141.736 (3)C3—C41.365 (5)
F1—C71.311 (4)C3—H30.9300
F2—C71.307 (4)C4—H4A0.9300
F3—C71.303 (4)C6—C81.397 (4)
F1'—C71.266 (8)C6—C71.472 (4)
F2'—C71.269 (8)C8—C91.368 (4)
F3'—C71.310 (8)C8—H80.9300
O1—C101.228 (3)C9—C101.488 (4)
O2—C181.227 (3)C11—C161.397 (4)
N1—C61.326 (4)C11—C121.412 (4)
N1—N21.347 (3)C12—C131.387 (4)
N2—C91.366 (3)C12—C181.505 (3)
N2—C51.441 (3)C13—C141.372 (4)
N3—C51.315 (4)C13—H130.9300
N3—C41.353 (4)C14—C151.382 (4)
N4—C101.343 (3)C15—C161.377 (4)
N4—C111.423 (3)C15—H150.9300
N4—H40.8600C16—C171.505 (4)
N5—C181.324 (3)C17—H17A0.9600
N5—C191.447 (4)C17—H17B0.9600
N5—H50.8600C17—H17C0.9600
C1—C21.375 (4)C19—H19A0.9600
C1—C51.386 (4)C19—H19B0.9600
C2—C31.367 (5)C19—H19C0.9600
C6—N1—N2104.4 (2)F3—C7—C6111.8 (3)
N1—N2—C9112.1 (2)F2—C7—C6113.4 (3)
N1—N2—C5118.5 (2)F3'—C7—C6110.7 (7)
C9—N2—C5129.1 (2)F1—C7—C6112.9 (3)
C5—N3—C4116.0 (3)C9—C8—C6104.9 (2)
C10—N4—C11123.0 (2)C9—C8—H8127.5
C10—N4—H4118.5C6—C8—H8127.5
C11—N4—H4118.5N2—C9—C8106.3 (2)
C18—N5—C19121.1 (2)N2—C9—C10122.9 (2)
C18—N5—H5119.5C8—C9—C10130.7 (2)
C19—N5—H5119.5O1—C10—N4124.3 (2)
C2—C1—C5118.5 (3)O1—C10—C9121.2 (2)
C2—C1—Cl1119.8 (3)N4—C10—C9114.5 (2)
C5—C1—Cl1121.7 (2)C16—C11—C12120.8 (2)
C3—C2—C1118.1 (3)C16—C11—N4119.4 (2)
C3—C2—H2120.9C12—C11—N4119.8 (2)
C1—C2—H2120.9C13—C12—C11118.8 (2)
C4—C3—C2119.6 (3)C13—C12—C18120.3 (2)
C4—C3—H3120.2C11—C12—C18120.9 (2)
C2—C3—H3120.2C14—C13—C12119.7 (3)
N3—C4—C3123.4 (3)C14—C13—H13120.1
N3—C4—H4A118.3C12—C13—H13120.1
C3—C4—H4A118.3C13—C14—C15121.4 (3)
N3—C5—C1124.3 (3)C13—C14—Cl2118.8 (2)
N3—C5—N2115.7 (3)C15—C14—Cl2119.8 (2)
C1—C5—N2119.9 (2)C16—C15—C14120.5 (3)
N1—C6—C8112.2 (3)C16—C15—H15119.7
N1—C6—C7120.2 (3)C14—C15—H15119.7
C8—C6—C7127.6 (3)C15—C16—C11118.6 (3)
F1'—C7—F2'106.9 (8)C15—C16—C17119.3 (3)
F1'—C7—F3131.5 (6)C11—C16—C17122.1 (3)
F2'—C7—F342.6 (7)C16—C17—H17A109.5
F1'—C7—F245.3 (7)C16—C17—H17B109.5
F2'—C7—F267.0 (8)H17A—C17—H17B109.5
F3—C7—F2106.3 (4)C16—C17—H17C109.5
F1'—C7—F3'105.2 (8)H17A—C17—H17C109.5
F2'—C7—F3'104.1 (8)H17B—C17—H17C109.5
F3—C7—F3'64.8 (8)O2—C18—N5120.9 (2)
F2—C7—F3'134.7 (7)O2—C18—C12121.4 (2)
F1'—C7—F162.1 (7)N5—C18—C12117.7 (2)
F2'—C7—F1132.1 (7)N5—C19—H19A109.5
F3—C7—F1107.1 (4)N5—C19—H19B109.5
F2—C7—F1104.8 (4)H19A—C19—H19B109.5
F3'—C7—F146.8 (8)N5—C19—H19C109.5
F1'—C7—C6115.8 (6)H19A—C19—H19C109.5
F2'—C7—C6113.3 (7)H19B—C19—H19C109.5
C6—N1—N2—C90.5 (3)N1—N2—C9—C10177.2 (2)
C6—N1—N2—C5175.3 (2)C5—N2—C9—C108.7 (4)
C5—C1—C2—C30.1 (4)C6—C8—C9—N20.2 (3)
Cl1—C1—C2—C3179.5 (3)C6—C8—C9—C10176.6 (3)
C1—C2—C3—C41.5 (5)C11—N4—C10—O18.6 (4)
C5—N3—C4—C31.0 (4)C11—N4—C10—C9170.3 (2)
C2—C3—C4—N32.0 (5)N2—C9—C10—O122.0 (4)
C4—N3—C5—C10.5 (4)C8—C9—C10—O1154.0 (3)
C4—N3—C5—N2178.7 (2)N2—C9—C10—N4159.1 (2)
C2—C1—C5—N31.0 (4)C8—C9—C10—N424.9 (4)
Cl1—C1—C5—N3178.5 (2)C10—N4—C11—C1664.7 (3)
C2—C1—C5—N2179.1 (3)C10—N4—C11—C12116.2 (3)
Cl1—C1—C5—N20.4 (4)C16—C11—C12—C133.9 (4)
N1—N2—C5—N369.8 (3)N4—C11—C12—C13177.1 (2)
C9—N2—C5—N3116.4 (3)C16—C11—C12—C18175.2 (2)
N1—N2—C5—C1108.4 (3)N4—C11—C12—C183.8 (3)
C9—N2—C5—C165.4 (4)C11—C12—C13—C140.3 (4)
N2—N1—C6—C80.4 (3)C18—C12—C13—C14179.4 (3)
N2—N1—C6—C7179.6 (3)C12—C13—C14—C153.7 (5)
N1—C6—C7—F1'11.8 (10)C12—C13—C14—Cl2177.2 (2)
C8—C6—C7—F1'169.1 (10)C13—C14—C15—C162.8 (5)
N1—C6—C7—F2'135.8 (10)Cl2—C14—C15—C16178.0 (3)
C8—C6—C7—F2'45.1 (11)C14—C15—C16—C111.4 (4)
N1—C6—C7—F3177.9 (4)C14—C15—C16—C17175.9 (3)
C8—C6—C7—F31.1 (6)C12—C11—C16—C154.7 (4)
N1—C6—C7—F261.9 (5)N4—C11—C16—C15176.2 (2)
C8—C6—C7—F2119.0 (5)C12—C11—C16—C17172.5 (3)
N1—C6—C7—F3'107.7 (10)N4—C11—C16—C176.6 (4)
C8—C6—C7—F3'71.4 (11)C19—N5—C18—O24.6 (4)
N1—C6—C7—F157.1 (5)C19—N5—C18—C12177.1 (3)
C8—C6—C7—F1122.0 (4)C13—C12—C18—O2157.4 (3)
N1—C6—C8—C90.2 (3)C11—C12—C18—O221.8 (4)
C7—C6—C8—C9179.3 (3)C13—C12—C18—N521.0 (4)
N1—N2—C9—C80.4 (3)C11—C12—C18—N5159.9 (2)
C5—N2—C9—C8174.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O20.862.372.673 (3)101
N4—H4···O2i0.862.253.107 (3)176
N5—H5···O1ii0.862.162.915 (3)146
C8—H8···O2i0.932.503.168 (4)129
Symmetry codes: (i) x+1, y+2, z; (ii) x+1/4, y+7/4, z1/4.

Experimental details

Crystal data
Chemical formulaC19H14Cl2F3N5O2
Mr472.25
Crystal system, space groupOrthorhombic, Fdd2
Temperature (K)296
a, b, c (Å)26.4612 (16), 32.8657 (19), 9.4679 (6)
V3)8233.9 (9)
Z16
Radiation typeMo Kα
µ (mm1)0.37
Crystal size (mm)0.24 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.917, 0.937
No. of measured, independent and
observed [I > 2σ(I)] reflections
10439, 3565, 3284
Rint0.021
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.082, 1.04
No. of reflections3565
No. of parameters310
No. of restraints49
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.20
Absolute structureFlack (1983), 1621 Friedel pairs
Absolute structure parameter0.01 (7)

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O20.862.372.673 (3)101
N4—H4···O2i0.862.253.107 (3)176
N5—H5···O1ii0.862.162.915 (3)146
C8—H8···O2i0.932.503.168 (4)129
Symmetry codes: (i) x+1, y+2, z; (ii) x+1/4, y+7/4, z1/4.
 

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