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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1479.
Published online 2009 June 6. doi:  10.1107/S1600536809019813
PMCID: PMC2969339

(E)-2-(2-Chloro-3,3,3-trifluoro­prop-1-en­yl)-N-(2,4-dimethyl­phen­yl)-3,3-dimethyl­cyclo­propane-1-carboxamide

Abstract

The title compound, C17H19ClF3NO, crystallizes with three mol­ecules in the asymmetric unit. The aromatic ring makes dihedral angles of 38.69 (13), 46.68 (12) and 50.52 (11)° with the plane of the cyclo­propane ring in the three mol­ecules. The crystal packing is stabilized by inter­molecular N—H(...)O hydrogen bonds.

Related literature

For the synthesis, see: Liu et al. (2006 [triangle]). The title compound is an inter­mediate for the insecticide tefluthrin, see: Punja (1981 [triangle]). Pesticides containing 2,4-dimethyl­benzenamine have the advantage of low toxicity, high activity and low residues (Zhang 2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1479-scheme1.jpg

Experimental

Crystal data

  • C17H19ClF3NO
  • M r = 345.78
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1479-efi1.jpg
  • a = 8.8497 (18) Å
  • b = 12.686 (3) Å
  • c = 23.891 (5) Å
  • α = 98.11 (3)°
  • β = 94.51 (3)°
  • γ = 97.60 (3)°
  • V = 2619.1 (9) Å3
  • Z = 6
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 113 K
  • 0.40 × 0.12 × 0.10 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.907, T max = 0.975
  • 19478 measured reflections
  • 9213 independent reflections
  • 6737 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.137
  • S = 1.01
  • 9213 reflections
  • 684 parameters
  • 81 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019813/bt2966sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019813/bt2966Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the National Natural Science Foundation (No. 20774604)

supplementary crystallographic information

Comment

3-((E)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylic acid is a very important intermediate for tefluthrin, a important insecticide controlling a wide range of soil insect pests in maize,sugar beet, and other crops (Punja 1981). 2,4-dimethylbenzenamine containing pesticides have the advantage of low toxicity, high activity and low residues (Zhang 2005). The structure in this article containing both of two active parts may be show some insecticide activity probably. The present X-ray crystal structure analysis was undertaken in order to study the stereochemistry and crystal packing of the title compound, (I) In this paper, the title compound, (E)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-N-(2,4-dimethylphenyl)- 2,2-dimethylcyclopropanecarboxamide, (I), was synthesized and the structure of (I) was illustrated in Fig. 1. The dihedral angles between the benzene moiety and the cycloprapane groug is 38.6 (6)°. The amide hydrogen was linking with the amide oxygen in another molecule by an intermolecular N—H···O hydrogen bond. The packing can be described as shown in Fig. 2 and Table 1.

Experimental

The title compound (I) was prepared according to the method of Liu et al. (2006). 3-((E)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2- dimethylcyclopropanecarboxylic acid (0.97 g, 4.0 mmol) was dispersed in SOCl2 (19 ml), and a drop of anhydrous DMF was added in. The mixture was heated to reflux for 3 h. SOCl2 was removed by rotoevapor. The crude the product could be directly disolved in anhydrous toluene, mixed with 2,4-dimethylbenzenamine (0.50 g, 4.1 mmol) already. Triethylamine was dropped into the system, After 12 h stirring under room temperature, the reaction mixture was treated with hexane. The product was recrystallized from methanol and ethyl acetate (15:1) over 4 d at ambient temperature, gave rod colourless crystals of (E)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-N– (2,4-dimethylphenyl)- 2,2-dimethylcyclopropanecarboxamide, suitable for X-ray analysis.

Refinement

H atoms were positioned geometrically with C—H = 0.93–0.98 Å and refined using riding model with Uiso(H) = 1.2Ueq(C). The H atom of one N—H was located from difference map and refined freely. The other two were refined using riding model with N-H = 0.91Å and Uiso(H) = 1.2Ueq(N). One CF3 group and one Cl ligand are disordered over two positions with site occupation factors of 0.61 (3)/0.39 (3) and 0.676 (8)/0.324 (8), respectively. Restraints were applied to keep the geometric parameters in a reasonable range.

Figures

Fig. 1.
The molecular structure of one molecule in the asymmetric unit, drawn with 30% probability ellipsoids. H atoms are drawn as spheres of arbitrary radius.

Crystal data

C17H19ClF3NOF(000) = 1080
Mr = 345.78Dx = 1.315 Mg m3
Triclinic, P1Melting point = 366–368 K
a = 8.8497 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.686 (3) ÅCell parameters from 6424 reflections
c = 23.891 (5) Åθ = 1.7–27.5°
α = 98.11 (3)°µ = 0.25 mm1
β = 94.51 (3)°T = 113 K
γ = 97.60 (3)°Rod, colorless
V = 2619.1 (9) Å30.40 × 0.12 × 0.10 mm
Z = 6

Data collection

Rigaku Saturn CCD area-detector diffractometer9213 independent reflections
Radiation source: rotating anode6737 reflections with I > 2σ(I)
confocalRint = 0.036
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 1.7°
ω and [var phi] scansh = −8→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −14→15
Tmin = 0.907, Tmax = 0.975l = −26→28
19478 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0784P)2] where P = (Fo2 + 2Fc2)/3
9213 reflections(Δ/σ)max = 0.001
684 parametersΔρmax = 0.35 e Å3
81 restraintsΔρmin = −0.39 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
Cl10.1893 (5)0.70100 (11)0.05532 (6)0.0636 (9)0.676 (8)
Cl1'0.2962 (12)0.7294 (6)0.06524 (18)0.080 (2)0.324 (8)
Cl21.16008 (7)0.77856 (6)0.47489 (3)0.0481 (2)
Cl30.09570 (7)0.27758 (5)0.42419 (2)0.03712 (17)
F10.1708 (15)1.0056 (5)0.0636 (4)0.0613 (19)0.61 (3)
F20.2499 (13)0.8969 (8)−0.0009 (4)0.073 (2)0.61 (3)
F30.0176 (9)0.8747 (9)0.0148 (4)0.079 (2)0.61 (3)
F1'0.112 (2)0.9913 (11)0.0630 (6)0.062 (3)0.39 (3)
F2'0.2885 (14)0.9340 (17)0.0156 (8)0.081 (3)0.39 (3)
F3'0.059 (2)0.8424 (12)0.0040 (5)0.089 (4)0.39 (3)
F41.27615 (18)0.95865 (14)0.41326 (7)0.0614 (5)
F51.1713 (2)1.02023 (13)0.48606 (7)0.0680 (5)
F61.0625 (2)1.01829 (12)0.40246 (8)0.0671 (5)
F70.00296 (17)0.46689 (13)0.37332 (8)0.0616 (5)
F80.1468 (2)0.52082 (13)0.45145 (7)0.0659 (5)
F90.23130 (17)0.54775 (11)0.37203 (7)0.0475 (4)
O10.46317 (18)1.02240 (12)0.20361 (6)0.0324 (4)
O20.73814 (19)0.78140 (12)0.30027 (6)0.0336 (4)
O30.58314 (18)0.39807 (12)0.29590 (6)0.0289 (4)
N10.6568 (2)0.93710 (15)0.23332 (8)0.0295 (4)
N20.6703 (2)0.60563 (14)0.26159 (7)0.0246 (4)
N30.6016 (2)0.25305 (15)0.23034 (7)0.0268 (4)
C10.1621 (4)0.9022 (2)0.04166 (11)0.0541 (8)
C20.2011 (3)0.8357 (2)0.08589 (10)0.0394 (6)
C30.2182 (3)0.8697 (2)0.14038 (10)0.0390 (6)
H30.20400.94040.15250.047*
C40.2583 (3)0.80473 (19)0.18437 (9)0.0330 (6)
H40.23570.72670.17240.040*
C50.4048 (3)0.84262 (18)0.22563 (9)0.0288 (5)
H50.45870.78410.23560.035*
C60.2473 (3)0.84135 (18)0.24663 (9)0.0302 (5)
C70.1860 (3)0.9448 (2)0.26512 (11)0.0389 (6)
H7A0.22030.99710.24180.058*
H7B0.22250.97140.30410.058*
H7C0.07600.93160.26120.058*
C80.2028 (3)0.7533 (2)0.28160 (10)0.0381 (6)
H8A0.24970.77470.31980.057*
H8B0.23710.68810.26530.057*
H8C0.09350.74140.28180.057*
C90.5075 (3)0.94219 (18)0.21988 (9)0.0267 (5)
C100.7772 (3)1.01967 (18)0.22573 (9)0.0283 (5)
C110.8607 (3)1.08240 (19)0.27332 (10)0.0330 (6)
H110.83391.07340.30940.040*
C120.9832 (3)1.1580 (2)0.26734 (11)0.0385 (6)
H121.03821.19980.29950.046*
C131.0253 (3)1.1722 (2)0.21380 (12)0.0391 (6)
C140.9381 (3)1.1105 (2)0.16684 (11)0.0399 (6)
H140.96391.12110.13080.048*
C150.8137 (3)1.03322 (19)0.17109 (10)0.0323 (6)
C160.7241 (3)0.9688 (2)0.11924 (10)0.0481 (7)
H16A0.70260.89490.12470.072*
H16B0.78240.97350.08720.072*
H16C0.62960.99640.11240.072*
C171.1642 (3)1.2511 (2)0.20695 (14)0.0569 (8)
H17A1.25231.21450.20490.085*
H17B1.18171.30790.23890.085*
H17C1.14681.28110.17270.085*
C181.1401 (3)0.9619 (2)0.43435 (11)0.0445 (7)
C191.0569 (3)0.85327 (18)0.43524 (9)0.0280 (5)
C200.9184 (3)0.81789 (18)0.40944 (9)0.0269 (5)
H200.87430.86270.38740.032*
C210.8287 (2)0.71443 (17)0.41270 (8)0.0244 (5)
H210.87930.67080.43700.029*
C220.7221 (2)0.64828 (17)0.36250 (9)0.0259 (5)
H220.71710.57020.36060.031*
C230.6562 (3)0.70290 (19)0.41385 (9)0.0303 (5)
C240.5926 (3)0.6299 (2)0.45425 (10)0.0448 (7)
H24A0.59740.67050.49160.067*
H24B0.65210.57210.45550.067*
H24C0.48800.60080.44120.067*
C250.5733 (3)0.7977 (2)0.40975 (11)0.0436 (7)
H25A0.61300.83660.38110.065*
H25B0.58780.84410.44570.065*
H25C0.46590.77300.39980.065*
C260.7118 (2)0.68547 (17)0.30611 (9)0.0252 (5)
C270.6653 (3)0.62123 (17)0.20348 (8)0.0257 (5)
C280.7859 (3)0.68320 (19)0.18391 (10)0.0328 (6)
H280.86870.71730.20930.039*
C290.7843 (3)0.6947 (2)0.12749 (10)0.0420 (7)
H290.86580.73660.11520.050*
C300.6631 (4)0.6448 (2)0.08916 (10)0.0480 (7)
C310.5446 (3)0.5821 (2)0.10882 (10)0.0421 (7)
H310.46350.54710.08290.050*
C320.5411 (3)0.56908 (18)0.16563 (9)0.0292 (5)
C330.4088 (3)0.5011 (2)0.18502 (10)0.0374 (6)
H33A0.32610.48460.15520.056*
H33B0.37520.53980.21810.056*
H33C0.44070.43550.19410.056*
C340.6602 (5)0.6578 (3)0.02673 (11)0.0816 (12)
H34A0.69630.73130.02360.122*
H34B0.55730.63840.00890.122*
H34C0.72530.61180.00830.122*
C350.1473 (3)0.4760 (2)0.39733 (11)0.0382 (6)
C360.2059 (3)0.37096 (18)0.39228 (9)0.0286 (5)
C370.3284 (2)0.35039 (18)0.36670 (9)0.0281 (5)
H370.38380.40660.35260.034*
C380.3833 (2)0.24578 (17)0.35896 (9)0.0251 (5)
H380.30560.18480.36200.030*
C390.4964 (2)0.22032 (17)0.31554 (8)0.0248 (5)
H390.47780.14580.29600.030*
C400.5456 (2)0.23111 (17)0.37855 (9)0.0253 (5)
C410.6566 (3)0.32675 (19)0.40892 (9)0.0312 (6)
H41A0.75970.31420.40390.047*
H41B0.64300.33660.44870.047*
H41C0.63770.39010.39340.047*
C420.5648 (3)0.12680 (19)0.40059 (10)0.0342 (6)
H42A0.49440.06900.37860.051*
H42B0.54430.13310.43970.051*
H42C0.66780.11230.39740.051*
C430.5625 (2)0.29966 (18)0.28017 (9)0.0243 (5)
C440.6903 (3)0.30899 (18)0.19294 (9)0.0287 (5)
C450.8212 (3)0.38029 (19)0.21508 (10)0.0346 (6)
H450.84840.39420.25410.042*
C460.9112 (3)0.4306 (2)0.17886 (11)0.0428 (7)
H460.99740.47940.19400.051*
C470.8754 (3)0.4096 (2)0.12100 (12)0.0463 (7)
C480.7443 (3)0.3385 (2)0.09992 (11)0.0472 (7)
H480.71860.32460.06080.057*
C490.6486 (3)0.28675 (19)0.13466 (10)0.0356 (6)
C500.5068 (3)0.2126 (2)0.10972 (10)0.0509 (8)
H50A0.49670.15040.12850.076*
H50B0.51310.19070.06990.076*
H50C0.41920.24910.11460.076*
C510.9757 (4)0.4620 (3)0.08105 (13)0.0714 (10)
H51A1.03710.52600.10140.107*
H51B0.91240.48020.05040.107*
H51C1.04140.41280.06600.107*
H1A0.676 (3)0.8827 (14)0.2518 (9)0.039 (7)*
H2A0.638 (3)0.5393 (11)0.2698 (10)0.041 (7)*
H3A0.574 (3)0.1820 (9)0.2195 (10)0.045 (8)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.117 (2)0.0428 (7)0.0307 (6)0.0123 (9)0.0146 (9)−0.0016 (5)
Cl1'0.133 (6)0.090 (3)0.0398 (17)0.073 (4)0.031 (2)0.0199 (19)
Cl20.0293 (3)0.0594 (5)0.0548 (4)−0.0032 (3)−0.0091 (3)0.0227 (3)
Cl30.0333 (3)0.0380 (4)0.0410 (3)0.0003 (3)0.0121 (3)0.0091 (3)
F10.085 (5)0.051 (2)0.054 (2)0.023 (2)−0.003 (3)0.0204 (17)
F20.114 (4)0.075 (4)0.043 (3)0.023 (3)0.035 (3)0.029 (3)
F30.084 (3)0.096 (5)0.056 (3)0.011 (3)−0.026 (3)0.024 (3)
F1'0.079 (7)0.073 (5)0.045 (3)0.048 (4)0.002 (5)0.015 (4)
F2'0.102 (5)0.098 (7)0.061 (6)0.030 (5)0.028 (4)0.044 (5)
F3'0.125 (7)0.096 (6)0.040 (4)0.029 (5)−0.033 (4)0.002 (4)
F40.0499 (10)0.0660 (11)0.0605 (10)−0.0260 (9)0.0196 (8)0.0072 (8)
F50.0725 (12)0.0559 (11)0.0570 (10)−0.0266 (10)0.0097 (9)−0.0234 (8)
F60.0767 (13)0.0301 (9)0.0916 (13)−0.0089 (9)−0.0045 (11)0.0217 (9)
F70.0323 (9)0.0486 (10)0.1070 (14)0.0136 (8)0.0011 (9)0.0182 (9)
F80.0949 (15)0.0419 (10)0.0622 (11)0.0163 (10)0.0288 (10)−0.0058 (8)
F90.0457 (9)0.0296 (8)0.0698 (10)0.0068 (7)0.0119 (8)0.0123 (7)
O10.0370 (9)0.0228 (9)0.0399 (9)0.0114 (7)0.0008 (7)0.0081 (7)
O20.0490 (10)0.0204 (9)0.0299 (8)0.0023 (8)−0.0064 (7)0.0065 (7)
O30.0403 (9)0.0182 (8)0.0286 (8)0.0021 (7)0.0085 (7)0.0048 (6)
N10.0299 (11)0.0238 (11)0.0372 (11)0.0058 (9)0.0013 (9)0.0125 (9)
N20.0300 (10)0.0218 (10)0.0213 (9)0.0011 (8)0.0015 (8)0.0047 (8)
N30.0357 (11)0.0216 (10)0.0253 (10)0.0085 (9)0.0061 (8)0.0052 (8)
C10.068 (2)0.059 (2)0.0385 (16)0.0153 (18)0.0077 (16)0.0139 (15)
C20.0487 (16)0.0383 (15)0.0350 (14)0.0110 (13)0.0112 (12)0.0103 (11)
C30.0480 (16)0.0288 (14)0.0379 (14)0.0046 (12)−0.0073 (12)0.0041 (11)
C40.0421 (14)0.0229 (12)0.0315 (12)0.0031 (11)−0.0060 (11)0.0025 (10)
C50.0332 (13)0.0227 (12)0.0321 (12)0.0099 (10)0.0000 (10)0.0060 (9)
C60.0271 (12)0.0287 (13)0.0335 (12)0.0051 (10)−0.0038 (10)0.0032 (10)
C70.0331 (14)0.0405 (15)0.0434 (14)0.0113 (12)0.0019 (11)0.0027 (12)
C80.0328 (14)0.0400 (15)0.0398 (14)−0.0004 (12)−0.0021 (11)0.0093 (11)
C90.0350 (13)0.0232 (12)0.0219 (11)0.0074 (10)0.0008 (9)0.0013 (9)
C100.0288 (12)0.0244 (12)0.0355 (13)0.0105 (10)0.0030 (10)0.0114 (10)
C110.0297 (13)0.0359 (14)0.0354 (13)0.0120 (11)−0.0007 (10)0.0071 (11)
C120.0290 (13)0.0337 (14)0.0503 (16)0.0054 (11)−0.0066 (12)0.0027 (12)
C130.0264 (13)0.0344 (15)0.0605 (17)0.0111 (11)0.0010 (12)0.0164 (13)
C140.0422 (15)0.0427 (16)0.0445 (15)0.0194 (13)0.0146 (12)0.0212 (12)
C150.0369 (14)0.0275 (13)0.0352 (13)0.0099 (11)0.0019 (11)0.0099 (10)
C160.066 (2)0.0431 (17)0.0362 (14)0.0103 (15)0.0080 (13)0.0065 (12)
C170.0334 (15)0.0533 (19)0.088 (2)0.0025 (14)0.0046 (15)0.0278 (17)
C180.0459 (16)0.0425 (16)0.0371 (14)−0.0138 (14)0.0049 (12)−0.0031 (12)
C190.0290 (12)0.0322 (13)0.0208 (11)−0.0016 (10)0.0034 (9)0.0026 (9)
C200.0320 (13)0.0242 (12)0.0235 (11)0.0022 (10)−0.0011 (9)0.0039 (9)
C210.0273 (12)0.0238 (12)0.0208 (11)0.0002 (10)−0.0026 (9)0.0050 (9)
C220.0308 (12)0.0201 (12)0.0247 (11)−0.0005 (10)−0.0036 (9)0.0037 (9)
C230.0257 (12)0.0338 (14)0.0281 (12)−0.0015 (11)−0.0007 (10)0.0007 (10)
C240.0396 (15)0.0579 (18)0.0295 (13)−0.0167 (14)0.0032 (11)0.0038 (12)
C250.0327 (14)0.0542 (18)0.0411 (14)0.0111 (13)0.0020 (11)−0.0065 (12)
C260.0246 (12)0.0226 (12)0.0276 (11)0.0038 (10)−0.0010 (9)0.0031 (9)
C270.0327 (13)0.0225 (12)0.0232 (11)0.0076 (10)0.0030 (10)0.0044 (9)
C280.0355 (14)0.0318 (14)0.0325 (13)0.0057 (11)0.0035 (10)0.0088 (10)
C290.0512 (17)0.0420 (16)0.0358 (14)0.0062 (13)0.0152 (12)0.0112 (12)
C300.070 (2)0.0449 (17)0.0302 (14)0.0081 (15)0.0089 (13)0.0076 (12)
C310.0575 (18)0.0361 (15)0.0286 (13)0.0062 (13)−0.0080 (12)−0.0015 (11)
C320.0352 (13)0.0243 (12)0.0282 (12)0.0085 (10)−0.0008 (10)0.0023 (9)
C330.0348 (14)0.0352 (14)0.0386 (13)0.0010 (11)−0.0066 (11)0.0024 (11)
C340.123 (3)0.088 (3)0.0298 (16)−0.003 (2)0.0082 (18)0.0152 (16)
C350.0344 (14)0.0333 (14)0.0475 (15)0.0055 (12)0.0086 (12)0.0053 (12)
C360.0260 (12)0.0263 (13)0.0322 (12)0.0000 (10)0.0022 (10)0.0033 (10)
C370.0261 (12)0.0290 (13)0.0271 (11)−0.0031 (10)−0.0025 (10)0.0062 (10)
C380.0229 (11)0.0235 (12)0.0285 (11)−0.0005 (10)0.0018 (9)0.0065 (9)
C390.0294 (12)0.0189 (11)0.0259 (11)0.0017 (9)0.0016 (9)0.0052 (9)
C400.0228 (11)0.0257 (12)0.0281 (11)0.0005 (10)0.0026 (9)0.0090 (9)
C410.0284 (12)0.0351 (14)0.0287 (12)−0.0032 (11)−0.0015 (10)0.0092 (10)
C420.0329 (13)0.0341 (14)0.0382 (13)0.0028 (11)0.0024 (11)0.0174 (11)
C430.0250 (12)0.0249 (13)0.0236 (11)0.0054 (10)−0.0008 (9)0.0058 (9)
C440.0374 (13)0.0251 (12)0.0294 (12)0.0152 (11)0.0111 (10)0.0091 (10)
C450.0371 (14)0.0328 (14)0.0385 (13)0.0144 (11)0.0099 (11)0.0090 (11)
C460.0383 (15)0.0393 (16)0.0565 (17)0.0129 (12)0.0189 (13)0.0130 (13)
C470.0493 (17)0.0477 (17)0.0544 (17)0.0228 (14)0.0296 (14)0.0221 (14)
C480.0652 (19)0.0542 (18)0.0323 (14)0.0277 (16)0.0201 (13)0.0147 (13)
C490.0490 (16)0.0320 (14)0.0305 (13)0.0189 (12)0.0106 (11)0.0051 (10)
C500.069 (2)0.0530 (18)0.0292 (13)0.0110 (16)0.0025 (13)0.0020 (12)
C510.078 (2)0.081 (3)0.070 (2)0.021 (2)0.0440 (19)0.0300 (19)

Geometric parameters (Å, °)

Cl1—C21.748 (3)C21—C231.517 (3)
Cl1'—C21.717 (4)C21—C221.537 (3)
Cl2—C191.725 (2)C21—H210.9800
Cl3—C361.732 (2)C22—C261.489 (3)
F1—C11.332 (6)C22—C231.518 (3)
F2—C11.327 (6)C22—H220.9800
F3—C11.364 (6)C23—C251.500 (4)
F1'—C11.318 (8)C23—C241.519 (3)
F2'—C11.365 (8)C24—H24A0.9600
F3'—C11.306 (8)C24—H24B0.9600
F4—C181.344 (3)C24—H24C0.9600
F5—C181.336 (3)C25—H25A0.9600
F6—C181.328 (3)C25—H25B0.9600
F7—C351.342 (3)C25—H25C0.9600
F8—C351.337 (3)C27—C281.391 (3)
F9—C351.339 (3)C27—C321.395 (3)
O1—C91.238 (3)C28—C291.376 (3)
O2—C261.238 (2)C28—H280.9300
O3—C431.237 (3)C29—C301.376 (4)
N1—C91.347 (3)C29—H290.9300
N1—C101.433 (3)C30—C311.384 (4)
N1—H1A0.897 (10)C30—C341.522 (4)
N2—C261.352 (3)C31—C321.392 (3)
N2—C271.428 (3)C31—H310.9300
N2—H2A0.905 (10)C32—C331.503 (3)
N3—C431.344 (3)C33—H33A0.9600
N3—C441.435 (3)C33—H33B0.9600
N3—H3A0.897 (10)C33—H33C0.9600
C1—C21.489 (4)C34—H34A0.9600
C2—C31.303 (3)C34—H34B0.9600
C3—C41.474 (3)C34—H34C0.9600
C3—H30.9300C35—C361.486 (3)
C4—C61.509 (3)C36—C371.324 (3)
C4—C51.544 (3)C37—C381.465 (3)
C4—H40.9800C37—H370.9300
C5—C91.485 (3)C38—C401.519 (3)
C5—C61.517 (3)C38—C391.529 (3)
C5—H50.9800C38—H380.9800
C6—C71.508 (3)C39—C431.494 (3)
C6—C81.516 (3)C39—C401.516 (3)
C7—H7A0.9600C39—H390.9800
C7—H7B0.9600C40—C411.512 (3)
C7—H7C0.9600C40—C421.516 (3)
C8—H8A0.9600C41—H41A0.9600
C8—H8B0.9600C41—H41B0.9600
C8—H8C0.9600C41—H41C0.9600
C10—C111.389 (3)C42—H42A0.9600
C10—C151.397 (3)C42—H42B0.9600
C11—C121.380 (3)C42—H42C0.9600
C11—H110.9300C44—C451.390 (3)
C12—C131.389 (4)C44—C491.391 (3)
C12—H120.9300C45—C461.385 (3)
C13—C141.387 (4)C45—H450.9300
C13—C171.514 (3)C46—C471.374 (4)
C14—C151.394 (3)C46—H460.9300
C14—H140.9300C47—C481.384 (4)
C15—C161.490 (3)C47—C511.516 (3)
C16—H16A0.9600C48—C491.398 (3)
C16—H16B0.9600C48—H480.9300
C16—H16C0.9600C49—C501.492 (4)
C17—H17A0.9600C50—H50A0.9600
C17—H17B0.9600C50—H50B0.9600
C17—H17C0.9600C50—H50C0.9600
C18—C191.478 (3)C51—H51A0.9600
C19—C201.320 (3)C51—H51B0.9600
C20—C211.456 (3)C51—H51C0.9600
C20—H200.9300
C9—N1—C10122.98 (19)C25—C23—C21120.5 (2)
C9—N1—H1A115.2 (16)C25—C23—C22120.9 (2)
C10—N1—H1A121.3 (16)C21—C23—C2260.85 (14)
C26—N2—C27124.14 (18)C25—C23—C24113.8 (2)
C26—N2—H2A116.9 (16)C21—C23—C24114.8 (2)
C27—N2—H2A118.9 (16)C22—C23—C24116.1 (2)
C43—N3—C44124.30 (19)C23—C24—H24A109.5
C43—N3—H3A119.3 (16)C23—C24—H24B109.5
C44—N3—H3A116.4 (16)H24A—C24—H24B109.5
F3'—C1—F1'111.1 (7)C23—C24—H24C109.5
F3'—C1—F283.6 (6)H24A—C24—H24C109.5
F1'—C1—F2123.1 (8)H24B—C24—H24C109.5
F3'—C1—F1129.4 (7)C23—C25—H25A109.5
F1'—C1—F122.7 (7)C23—C25—H25B109.5
F2—C1—F1107.4 (5)H25A—C25—H25B109.5
F3'—C1—F327.2 (6)C23—C25—H25C109.5
F1'—C1—F384.6 (6)H25A—C25—H25C109.5
F2—C1—F3103.2 (5)H25B—C25—H25C109.5
F1—C1—F3104.9 (5)O2—C26—N2122.58 (19)
F3'—C1—F2'109.1 (8)O2—C26—C22123.05 (19)
F1'—C1—F2'105.9 (8)N2—C26—C22114.37 (18)
F2—C1—F2'26.4 (6)C28—C27—C32120.00 (19)
F1—C1—F2'85.8 (7)C28—C27—N2120.8 (2)
F3—C1—F2'124.4 (7)C32—C27—N2119.17 (19)
F3'—C1—C2107.5 (7)C29—C28—C27120.9 (2)
F1'—C1—C2112.6 (7)C29—C28—H28119.6
F2—C1—C2114.1 (4)C27—C28—H28119.6
F1—C1—C2111.6 (5)C28—C29—C30120.5 (2)
F3—C1—C2114.8 (4)C28—C29—H29119.8
F2'—C1—C2110.6 (6)C30—C29—H29119.8
C3—C2—C1124.7 (3)C29—C30—C31118.3 (2)
C3—C2—Cl1'114.3 (3)C29—C30—C34120.7 (3)
C1—C2—Cl1'116.7 (2)C31—C30—C34121.0 (3)
C3—C2—Cl1124.4 (2)C30—C31—C32123.1 (2)
C1—C2—Cl1110.2 (2)C30—C31—H31118.5
Cl1'—C2—Cl132.3 (3)C32—C31—H31118.5
C2—C3—C4125.0 (2)C31—C32—C27117.3 (2)
C2—C3—H3117.5C31—C32—C33121.1 (2)
C4—C3—H3117.5C27—C32—C33121.65 (19)
C3—C4—C6122.1 (2)C32—C33—H33A109.5
C3—C4—C5119.69 (19)C32—C33—H33B109.5
C6—C4—C559.57 (14)H33A—C33—H33B109.5
C3—C4—H4114.8C32—C33—H33C109.5
C6—C4—H4114.8H33A—C33—H33C109.5
C5—C4—H4114.8H33B—C33—H33C109.5
C9—C5—C6124.1 (2)C30—C34—H34A109.5
C9—C5—C4120.18 (18)C30—C34—H34B109.5
C6—C5—C459.09 (15)H34A—C34—H34B109.5
C9—C5—H5114.2C30—C34—H34C109.5
C6—C5—H5114.2H34A—C34—H34C109.5
C4—C5—H5114.2H34B—C34—H34C109.5
C7—C6—C4119.8 (2)F8—C35—F9106.8 (2)
C7—C6—C8114.0 (2)F8—C35—F7106.5 (2)
C4—C6—C8116.0 (2)F9—C35—F7106.4 (2)
C7—C6—C5120.94 (19)F8—C35—C36112.3 (2)
C4—C6—C561.34 (15)F9—C35—C36112.2 (2)
C8—C6—C5114.9 (2)F7—C35—C36112.2 (2)
C6—C7—H7A109.5C37—C36—C35124.3 (2)
C6—C7—H7B109.5C37—C36—Cl3123.44 (19)
H7A—C7—H7B109.5C35—C36—Cl3112.24 (17)
C6—C7—H7C109.5C36—C37—C38125.0 (2)
H7A—C7—H7C109.5C36—C37—H37117.5
H7B—C7—H7C109.5C38—C37—H37117.5
C6—C8—H8A109.5C37—C38—C40122.90 (19)
C6—C8—H8B109.5C37—C38—C39121.05 (18)
H8A—C8—H8B109.5C40—C38—C3959.66 (14)
C6—C8—H8C109.5C37—C38—H38114.2
H8A—C8—H8C109.5C40—C38—H38114.2
H8B—C8—H8C109.5C39—C38—H38114.2
O1—C9—N1122.2 (2)C43—C39—C40121.59 (18)
O1—C9—C5124.4 (2)C43—C39—C38123.25 (19)
N1—C9—C5113.4 (2)C40—C39—C3859.84 (14)
C11—C10—C15120.8 (2)C43—C39—H39113.9
C11—C10—N1119.1 (2)C40—C39—H39113.9
C15—C10—N1120.1 (2)C38—C39—H39113.9
C12—C11—C10120.3 (2)C41—C40—C39121.13 (18)
C12—C11—H11119.8C41—C40—C42113.58 (19)
C10—C11—H11119.8C39—C40—C42115.55 (19)
C11—C12—C13120.6 (2)C41—C40—C38119.7 (2)
C11—C12—H12119.7C39—C40—C3860.50 (14)
C13—C12—H12119.7C42—C40—C38116.51 (18)
C14—C13—C12118.0 (2)C40—C41—H41A109.5
C14—C13—C17121.0 (2)C40—C41—H41B109.5
C12—C13—C17121.0 (2)H41A—C41—H41B109.5
C13—C14—C15123.0 (2)C40—C41—H41C109.5
C13—C14—H14118.5H41A—C41—H41C109.5
C15—C14—H14118.5H41B—C41—H41C109.5
C14—C15—C10117.1 (2)C40—C42—H42A109.5
C14—C15—C16120.9 (2)C40—C42—H42B109.5
C10—C15—C16122.0 (2)H42A—C42—H42B109.5
C15—C16—H16A109.5C40—C42—H42C109.5
C15—C16—H16B109.5H42A—C42—H42C109.5
H16A—C16—H16B109.5H42B—C42—H42C109.5
C15—C16—H16C109.5O3—C43—N3123.50 (19)
H16A—C16—H16C109.5O3—C43—C39123.32 (19)
H16B—C16—H16C109.5N3—C43—C39113.15 (19)
C13—C17—H17A109.5C45—C44—C49120.8 (2)
C13—C17—H17B109.5C45—C44—N3119.6 (2)
H17A—C17—H17B109.5C49—C44—N3119.5 (2)
C13—C17—H17C109.5C46—C45—C44119.8 (2)
H17A—C17—H17C109.5C46—C45—H45120.1
H17B—C17—H17C109.5C44—C45—H45120.1
F6—C18—F5107.1 (2)C47—C46—C45121.2 (3)
F6—C18—F4106.2 (2)C47—C46—H46119.4
F5—C18—F4105.6 (2)C45—C46—H46119.4
F6—C18—C19112.3 (2)C46—C47—C48118.0 (2)
F5—C18—C19112.8 (2)C46—C47—C51121.5 (3)
F4—C18—C19112.3 (2)C48—C47—C51120.6 (3)
C20—C19—C18123.9 (2)C47—C48—C49123.1 (2)
C20—C19—Cl2123.72 (18)C47—C48—H48118.5
C18—C19—Cl2112.34 (18)C49—C48—H48118.5
C19—C20—C21125.4 (2)C44—C49—C48117.1 (2)
C19—C20—H20117.3C44—C49—C50122.1 (2)
C21—C20—H20117.3C48—C49—C50120.8 (2)
C20—C21—C23121.1 (2)C49—C50—H50A109.5
C20—C21—C22123.12 (17)C49—C50—H50B109.5
C23—C21—C2259.62 (14)H50A—C50—H50B109.5
C20—C21—H21114.1C49—C50—H50C109.5
C23—C21—H21114.1H50A—C50—H50C109.5
C22—C21—H21114.1H50B—C50—H50C109.5
C26—C22—C23123.0 (2)C47—C51—H51A109.5
C26—C22—C21120.64 (17)C47—C51—H51B109.5
C23—C22—C2159.53 (14)H51A—C51—H51B109.5
C26—C22—H22114.3C47—C51—H51C109.5
C23—C22—H22114.3H51A—C51—H51C109.5
C21—C22—H22114.3H51B—C51—H51C109.5
F3'—C1—C2—C3−137.2 (10)C20—C21—C23—C24−140.0 (2)
F1'—C1—C2—C3−14.5 (11)C22—C21—C23—C24107.3 (2)
F2—C1—C2—C3132.1 (7)C26—C22—C23—C251.2 (3)
F1—C1—C2—C310.0 (7)C21—C22—C23—C25110.1 (2)
F3—C1—C2—C3−109.1 (8)C26—C22—C23—C21−108.8 (2)
F2'—C1—C2—C3103.8 (11)C26—C22—C23—C24146.1 (2)
F3'—C1—C2—Cl1'67.7 (11)C21—C22—C23—C24−105.1 (2)
F1'—C1—C2—Cl1'−169.6 (11)C27—N2—C26—O25.7 (4)
F2—C1—C2—Cl1'−23.0 (8)C27—N2—C26—C22−174.6 (2)
F1—C1—C2—Cl1'−145.1 (8)C23—C22—C26—O244.6 (3)
F3—C1—C2—Cl1'95.8 (9)C21—C22—C26—O2−26.9 (3)
F2'—C1—C2—Cl1'−51.4 (12)C23—C22—C26—N2−135.1 (2)
F3'—C1—C2—Cl133.0 (10)C21—C22—C26—N2153.5 (2)
F1'—C1—C2—Cl1155.8 (10)C26—N2—C27—C2846.4 (3)
F2—C1—C2—Cl1−57.7 (7)C26—N2—C27—C32−136.8 (2)
F1—C1—C2—Cl1−179.7 (6)C32—C27—C28—C290.5 (4)
F3—C1—C2—Cl161.2 (8)N2—C27—C28—C29177.3 (2)
F2'—C1—C2—Cl1−86.0 (11)C27—C28—C29—C30−0.2 (4)
C1—C2—C3—C4−179.3 (2)C28—C29—C30—C31−0.7 (4)
Cl1'—C2—C3—C4−23.7 (5)C28—C29—C30—C34179.7 (3)
Cl1—C2—C3—C411.8 (5)C29—C30—C31—C321.3 (4)
C2—C3—C4—C6−168.2 (3)C34—C30—C31—C32−179.1 (3)
C2—C3—C4—C5121.1 (3)C30—C31—C32—C27−1.0 (4)
C3—C4—C5—C9−2.0 (3)C30—C31—C32—C33179.3 (3)
C6—C4—C5—C9−114.0 (2)C28—C27—C32—C310.0 (3)
C3—C4—C5—C6112.0 (3)N2—C27—C32—C31−176.8 (2)
C3—C4—C6—C73.2 (3)C28—C27—C32—C33179.8 (2)
C5—C4—C6—C7111.2 (2)N2—C27—C32—C333.0 (3)
C3—C4—C6—C8146.5 (2)F8—C35—C36—C37−119.2 (2)
C5—C4—C6—C8−105.5 (2)F9—C35—C36—C371.1 (3)
C3—C4—C6—C5−108.0 (2)F7—C35—C36—C37120.9 (2)
C9—C5—C6—C7−1.9 (3)F8—C35—C36—Cl360.5 (2)
C4—C5—C6—C7−109.5 (2)F9—C35—C36—Cl3−179.19 (16)
C9—C5—C6—C4107.6 (2)F7—C35—C36—Cl3−59.5 (2)
C9—C5—C6—C8−145.1 (2)C35—C36—C37—C38−176.9 (2)
C4—C5—C6—C8107.3 (2)Cl3—C36—C37—C383.5 (3)
C10—N1—C9—O1−5.1 (3)C36—C37—C38—C40−125.4 (2)
C10—N1—C9—C5173.88 (19)C36—C37—C38—C39162.8 (2)
C6—C5—C9—O1−37.7 (3)C37—C38—C39—C432.4 (3)
C4—C5—C9—O133.3 (3)C40—C38—C39—C43−110.1 (2)
C6—C5—C9—N1143.3 (2)C37—C38—C39—C40112.5 (2)
C4—C5—C9—N1−145.6 (2)C43—C39—C40—C413.9 (3)
C9—N1—C10—C11111.4 (3)C38—C39—C40—C41−108.9 (2)
C9—N1—C10—C15−71.4 (3)C43—C39—C40—C42−139.9 (2)
C15—C10—C11—C12−1.2 (4)C38—C39—C40—C42107.3 (2)
N1—C10—C11—C12176.0 (2)C43—C39—C40—C38112.8 (2)
C10—C11—C12—C13−0.2 (4)C37—C38—C40—C411.7 (3)
C11—C12—C13—C141.7 (4)C39—C38—C40—C41111.2 (2)
C11—C12—C13—C17−177.0 (2)C37—C38—C40—C39−109.5 (2)
C12—C13—C14—C15−1.8 (4)C37—C38—C40—C42144.8 (2)
C17—C13—C14—C15176.9 (2)C39—C38—C40—C42−105.8 (2)
C13—C14—C15—C100.4 (4)C44—N3—C43—O39.0 (4)
C13—C14—C15—C16−179.8 (2)C44—N3—C43—C39−169.05 (19)
C11—C10—C15—C141.1 (4)C40—C39—C43—O3−43.1 (3)
N1—C10—C15—C14−176.1 (2)C38—C39—C43—O329.3 (3)
C11—C10—C15—C16−178.7 (2)C40—C39—C43—N3134.9 (2)
N1—C10—C15—C164.1 (4)C38—C39—C43—N3−152.7 (2)
F6—C18—C19—C20−2.9 (4)C43—N3—C44—C4545.3 (3)
F5—C18—C19—C20118.3 (3)C43—N3—C44—C49−138.2 (2)
F4—C18—C19—C20−122.5 (3)C49—C44—C45—C460.4 (4)
F6—C18—C19—Cl2178.17 (18)N3—C44—C45—C46176.9 (2)
F5—C18—C19—Cl2−60.7 (3)C44—C45—C46—C47−1.4 (4)
F4—C18—C19—Cl258.5 (2)C45—C46—C47—C481.6 (4)
C18—C19—C20—C21−175.4 (2)C45—C46—C47—C51−178.3 (3)
Cl2—C19—C20—C213.4 (3)C46—C47—C48—C49−0.8 (4)
C19—C20—C21—C23143.6 (2)C51—C47—C48—C49179.1 (3)
C19—C20—C21—C22−144.6 (2)C45—C44—C49—C480.4 (4)
C20—C21—C22—C263.2 (3)N3—C44—C49—C48−176.2 (2)
C23—C21—C22—C26112.7 (2)C45—C44—C49—C50−178.5 (2)
C20—C21—C22—C23−109.5 (3)N3—C44—C49—C505.0 (4)
C20—C21—C23—C252.0 (3)C47—C48—C49—C44−0.2 (4)
C22—C21—C23—C25−110.7 (2)C47—C48—C49—C50178.7 (3)
C20—C21—C23—C22112.7 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.90 (1)1.95 (1)2.840 (2)171 (2)
N2—H2A···O30.911.992.893 (2)174
N3—H3A···O1i0.902.102.980 (2)167

Symmetry codes: (i) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2966).

References

  • Liu, D.-Q., Feng, Y.-Q., Liu, D.-W. & Zhang, S.-S. (2006). Acta Cryst. E62, o1747–o1748.
  • Punja, N. (1981). Eur. Patent No. EP 0031199.
  • Rigaku/MSC (2005). CrystalClear and CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, M. H. (2005). Fine Specialty Chem 13, 1–4.

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