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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2191.
Published online 2008 October 25. doi:  10.1107/S1600536808032078
PMCID: PMC2959779

(E)-3-(2-Chloro-3,3,3-trifluoro­prop-1-en­yl)-2,2-dimethyl-N-(2-naphth­yl)cyclo­propane­carboxamide

Abstract

The title compound, C19H17ClF3NO, was synthesized from 3-[(E)-2-chloro-3,3,3-trifluoro­prop-1-en­yl]-2,2-dimethyl­cyclopropane­carboxylic acid and 2-aminona­phthalene. There are two molecules in the asymmetric unit. The dihedral angle between the naphthalene and cyclo­propane units is 111.6 (5)°. Molecules are connected into chains by intermol­ecular N—H(...)O hydrogen bonds. One of the Cl atoms is disordered over two positions with occupancies 0.653 (15) and 0.347 (15).

Related literature

For general background, see: Punja (1981 [triangle]). For synthetic details, see: Liu & Yan (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2191-scheme1.jpg

Experimental

Crystal data

  • C19H17ClF3NO
  • M r = 367.79
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2191-efi1.jpg
  • a = 9.6310 (8) Å
  • b = 16.9090 (16) Å
  • c = 22.485 (2) Å
  • V = 3661.6 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 113 (2) K
  • 0.32 × 0.22 × 0.14 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.926, T max = 0.967
  • 34375 measured reflections
  • 8701 independent reflections
  • 8283 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.115
  • S = 1.14
  • 8701 reflections
  • 473 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.28 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3846 Friedel pairs
  • Flack parameter: −0.05 (6)

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 (Bruker, 1997 [triangle]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032078/bt2796sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032078/bt2796Isup2.hkl

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant No. 20376059) and Tianjin Polytechnic University

supplementary crystallographic information

Comment

3-[(E)-2-Chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylic acid is a very important intermediate for tefluthrin, an important insecticide controlling a wide range of soil insect pests in maize,sugar beet, and other crops (Punja, 1981). Naphthalene is also a good structure which has bioactivity. 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)-2,2-dimethyl-N-(naphthalen-2-yl)cyclopropanecarboxamide, (I), was synthesized and the structure of (I) was illustrated in Fig. 1. The dihedral angles between the naphthalene moiety and the cycloprapane group is 111.6 (5)°. The amide hydrogen is linking with the amide oxygen in another molecule by an intermolecular N—H···O···H—C hydrogen bond. The packing can be described as a dimeric arrangement of molecules linked through N—H···O···H—C hydrogen bond as shown in Fig. 2 and Table 1.

Experimental

The title compound was prepared according to the method of Liu & Yan (2007). The product was recrystallized from methanol and ethyl acetate (10:1) over 2 d at ambient temperature, gave colourless single crystals of (E)-3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N- (naphthalen-2-yl)cyclopropanecarboxamide, 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(carrier). H atom of N—H was located from difference map and refinded freely.

Figures

Fig. 1.
The molecular structure of (I), methanol, drawn with 30% probability ellipsoids. H atoms are drawn as spheres of arbitrary radius.
Fig. 2.
The crystal structure of (I), methanol, viewed along b axis

Crystal data

C19H17ClF3NODx = 1.334 Mg m3
Mr = 367.79Mo Kα radiation, λ = 0.71070 Å
Orthorhombic, P212121Cell parameters from 9431 reflections
a = 9.6310 (8) Åθ = 1.2–27.9°
b = 16.9090 (16) ŵ = 0.24 mm1
c = 22.485 (2) ÅT = 113 K
V = 3661.6 (6) Å3Block, colourless
Z = 80.32 × 0.22 × 0.14 mm
F(000) = 1520

Data collection

Rigaku Saturn diffractometer8701 independent reflections
Radiation source: rotating anode8283 reflections with I > 2σ(I)
confocalRint = 0.046
Detector resolution: 14.63 pixels mm-1θmax = 27.9°, θmin = 1.5°
ω scansh = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −22→21
Tmin = 0.926, Tmax = 0.967l = −29→29
34375 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115w = 1/[σ2(Fo2) + (0.0431P)2 + 0.7651P] where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.004
8701 reflectionsΔρmax = 0.23 e Å3
473 parametersΔρmin = −0.28 e Å3
0 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.05 (6)

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)
Cl10.67199 (8)0.75840 (5)0.01612 (3)0.05570 (19)
Cl20.2270 (3)0.5061 (5)0.02545 (13)0.0676 (12)0.653 (15)
Cl2'0.2403 (3)0.5502 (9)0.0412 (4)0.070 (3)0.347 (15)
F10.9051 (2)0.85834 (13)0.05947 (11)0.0915 (7)
F20.94983 (18)0.73920 (13)0.08421 (10)0.0805 (6)
F30.89532 (17)0.82357 (13)0.15124 (9)0.0722 (5)
F40.43674 (15)0.43635 (10)0.16241 (7)0.0552 (4)
F50.50212 (16)0.51978 (12)0.09630 (9)0.0693 (5)
F60.44470 (19)0.40315 (14)0.07147 (9)0.0872 (7)
O10.64390 (15)0.66486 (10)0.22636 (7)0.0378 (4)
O20.14813 (15)0.59263 (9)0.24189 (7)0.0329 (3)
N10.45095 (19)0.59688 (11)0.25494 (8)0.0291 (4)
N2−0.05216 (19)0.66161 (11)0.25605 (8)0.0283 (4)
C10.5205 (2)0.64882 (12)0.21976 (10)0.0277 (4)
C20.4298 (2)0.68560 (12)0.17359 (9)0.0264 (4)
H20.35940.64910.15580.032*
C30.3824 (2)0.77078 (13)0.17939 (9)0.0304 (5)
C40.4844 (2)0.74882 (13)0.13117 (9)0.0302 (5)
H40.44430.74680.09020.036*
C50.6308 (2)0.77356 (13)0.13406 (10)0.0324 (5)
H50.66640.78660.17220.039*
C60.7173 (2)0.77930 (14)0.08877 (11)0.0362 (5)
C70.8664 (3)0.80168 (18)0.09634 (14)0.0542 (7)
C80.4284 (3)0.81968 (14)0.23245 (11)0.0390 (5)
H8A0.52270.80420.24400.059*
H8B0.36490.81050.26580.059*
H8C0.42740.87590.22180.059*
C90.2351 (2)0.78755 (15)0.15899 (11)0.0387 (5)
H9A0.22800.84270.14600.058*
H9B0.17070.77830.19200.058*
H9C0.21160.75240.12580.058*
C100.5010 (2)0.55608 (12)0.30557 (9)0.0283 (4)
C110.4000 (2)0.51516 (13)0.33956 (10)0.0322 (5)
H110.30580.51500.32700.039*
C120.4372 (3)0.47600 (14)0.39024 (10)0.0358 (5)
H120.36830.44840.41230.043*
C130.5761 (3)0.47564 (13)0.41061 (10)0.0343 (5)
C140.6182 (3)0.43805 (14)0.46424 (11)0.0431 (6)
H140.55210.40970.48730.052*
C150.7531 (3)0.44237 (15)0.48295 (12)0.0470 (6)
H150.77970.41760.51910.056*
C160.8524 (3)0.48304 (15)0.44914 (11)0.0443 (6)
H160.94560.48590.46280.053*
C170.8165 (2)0.51854 (14)0.39682 (10)0.0374 (5)
H170.88540.54490.37400.045*
C180.6773 (2)0.51631 (13)0.37624 (10)0.0312 (4)
C190.6375 (2)0.55512 (12)0.32312 (9)0.0299 (4)
H190.70580.58070.29940.036*
C200.0286 (2)0.60868 (12)0.22699 (9)0.0254 (4)
C21−0.0453 (2)0.56913 (13)0.17712 (9)0.0277 (4)
H21−0.11680.60260.15700.033*
C22−0.0824 (2)0.48145 (13)0.18118 (9)0.0289 (4)
C230.0254 (2)0.50805 (13)0.13649 (9)0.0288 (4)
H23−0.00810.50880.09440.035*
C240.1721 (2)0.48659 (13)0.14322 (9)0.0298 (4)
H240.20220.47040.18160.036*
C250.2655 (2)0.48783 (16)0.10067 (10)0.0391 (5)
C260.4110 (3)0.46160 (17)0.10780 (12)0.0463 (6)
C27−0.0401 (2)0.43473 (14)0.23534 (10)0.0355 (5)
H27A−0.11380.43770.26530.053*
H27B0.04590.45680.25170.053*
H27C−0.02490.37940.22410.053*
C28−0.2230 (2)0.45972 (15)0.15708 (11)0.0395 (5)
H28A−0.22470.40320.14740.059*
H28B−0.24180.49060.12110.059*
H28C−0.29410.47110.18700.059*
C29−0.0231 (2)0.70345 (12)0.30899 (10)0.0282 (4)
C30−0.1384 (2)0.74173 (12)0.33609 (10)0.0333 (5)
H30−0.22760.73840.31820.040*
C31−0.1216 (3)0.78325 (14)0.38760 (11)0.0384 (5)
H31−0.19970.80830.40520.046*
C320.0095 (3)0.78970 (14)0.41532 (11)0.0384 (5)
C330.0309 (3)0.83374 (15)0.46851 (12)0.0491 (7)
H33−0.04500.86050.48650.059*
C340.1589 (3)0.83780 (15)0.49368 (11)0.0514 (7)
H340.17150.86710.52930.062*
C350.2722 (3)0.79948 (15)0.46779 (11)0.0479 (7)
H350.36110.80320.48590.057*
C360.2568 (3)0.75658 (14)0.41665 (11)0.0409 (6)
H360.33470.73050.39970.049*
C370.1248 (2)0.75090 (13)0.38880 (10)0.0338 (5)
C380.1057 (2)0.70761 (12)0.33494 (10)0.0312 (5)
H380.18240.68160.31700.037*
H2A−0.132 (3)0.6668 (13)0.2440 (9)0.022 (6)*
H10.365 (3)0.5892 (15)0.2472 (11)0.039 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0553 (4)0.0665 (4)0.0453 (3)−0.0042 (3)0.0152 (3)−0.0084 (3)
Cl20.0340 (7)0.136 (3)0.0327 (7)0.0050 (11)0.0050 (5)0.0149 (14)
Cl2'0.0385 (13)0.131 (6)0.040 (3)−0.0058 (19)−0.0029 (12)0.039 (3)
F10.0505 (11)0.0977 (14)0.1265 (18)−0.0318 (11)−0.0061 (12)0.0623 (14)
F20.0335 (9)0.0963 (15)0.1117 (16)0.0213 (10)0.0170 (10)0.0165 (13)
F30.0329 (9)0.0979 (14)0.0857 (13)−0.0179 (9)−0.0102 (9)0.0028 (11)
F40.0276 (7)0.0795 (11)0.0584 (9)0.0131 (7)−0.0018 (7)0.0173 (9)
F50.0238 (8)0.0884 (13)0.0956 (14)−0.0049 (8)0.0092 (8)0.0256 (11)
F60.0486 (11)0.1165 (17)0.0963 (15)0.0210 (11)0.0111 (10)−0.0522 (13)
O10.0180 (7)0.0449 (9)0.0506 (9)−0.0053 (7)−0.0075 (7)0.0136 (8)
O20.0172 (7)0.0385 (8)0.0431 (9)0.0025 (6)−0.0058 (6)−0.0056 (7)
N10.0168 (8)0.0326 (9)0.0380 (10)−0.0030 (7)−0.0057 (8)0.0016 (8)
N20.0169 (8)0.0321 (9)0.0359 (10)0.0001 (7)−0.0042 (7)−0.0027 (8)
C10.0196 (10)0.0286 (10)0.0351 (11)0.0003 (8)−0.0020 (8)−0.0005 (9)
C20.0166 (9)0.0311 (10)0.0315 (11)−0.0012 (8)−0.0027 (8)−0.0002 (8)
C30.0241 (10)0.0331 (11)0.0338 (11)0.0020 (9)−0.0005 (9)0.0052 (9)
C40.0232 (10)0.0389 (12)0.0283 (10)−0.0005 (9)−0.0021 (8)0.0029 (9)
C50.0251 (11)0.0345 (11)0.0375 (11)0.0006 (9)−0.0051 (9)0.0047 (9)
C60.0268 (11)0.0375 (12)0.0443 (13)0.0023 (9)0.0036 (10)0.0052 (10)
C70.0314 (14)0.0605 (17)0.0706 (19)−0.0041 (13)0.0048 (13)0.0268 (15)
C80.0375 (13)0.0362 (12)0.0434 (13)0.0041 (10)0.0015 (10)−0.0019 (10)
C90.0244 (11)0.0462 (13)0.0455 (13)0.0066 (10)0.0006 (10)0.0105 (11)
C100.0256 (10)0.0256 (10)0.0336 (11)−0.0017 (8)−0.0030 (8)0.0002 (8)
C110.0264 (10)0.0332 (11)0.0372 (11)−0.0040 (9)−0.0008 (9)−0.0022 (9)
C120.0372 (13)0.0338 (11)0.0365 (12)−0.0045 (10)0.0023 (10)−0.0004 (10)
C130.0405 (13)0.0285 (10)0.0337 (11)0.0042 (10)−0.0016 (10)−0.0047 (9)
C140.0549 (16)0.0376 (12)0.0369 (12)0.0071 (12)−0.0002 (11)−0.0007 (10)
C150.0618 (18)0.0434 (14)0.0359 (12)0.0157 (13)−0.0104 (12)−0.0018 (11)
C160.0430 (14)0.0435 (13)0.0465 (13)0.0150 (12)−0.0140 (12)−0.0067 (11)
C170.0328 (12)0.0372 (11)0.0421 (12)0.0097 (10)−0.0086 (10)−0.0051 (10)
C180.0300 (11)0.0275 (10)0.0360 (11)0.0062 (9)−0.0050 (9)−0.0051 (9)
C190.0233 (10)0.0292 (10)0.0372 (11)0.0000 (8)−0.0023 (9)0.0001 (9)
C200.0193 (10)0.0244 (9)0.0324 (11)−0.0038 (8)−0.0019 (8)0.0028 (8)
C210.0168 (9)0.0337 (10)0.0327 (11)0.0026 (8)−0.0031 (8)0.0011 (9)
C220.0195 (10)0.0333 (10)0.0340 (11)−0.0045 (8)0.0011 (8)−0.0026 (9)
C230.0203 (10)0.0375 (11)0.0288 (10)−0.0013 (9)−0.0019 (8)−0.0043 (9)
C240.0228 (10)0.0358 (11)0.0309 (10)−0.0016 (9)−0.0019 (8)−0.0010 (9)
C250.0253 (11)0.0556 (15)0.0365 (12)0.0023 (11)0.0034 (9)0.0058 (11)
C260.0276 (12)0.0649 (17)0.0463 (14)0.0038 (12)0.0086 (11)−0.0043 (13)
C270.0314 (12)0.0349 (11)0.0401 (12)−0.0040 (10)0.0051 (10)0.0034 (10)
C280.0231 (11)0.0473 (13)0.0480 (13)−0.0086 (10)−0.0025 (10)−0.0111 (11)
C290.0255 (10)0.0261 (10)0.0331 (11)−0.0047 (8)−0.0008 (9)−0.0004 (8)
C300.0266 (11)0.0290 (10)0.0444 (12)−0.0013 (9)0.0028 (9)−0.0007 (9)
C310.0342 (13)0.0323 (11)0.0488 (14)−0.0008 (10)0.0067 (11)−0.0032 (10)
C320.0468 (14)0.0323 (11)0.0360 (12)−0.0070 (10)0.0018 (10)−0.0020 (10)
C330.0654 (19)0.0384 (13)0.0434 (14)−0.0113 (13)0.0072 (13)−0.0069 (11)
C340.075 (2)0.0415 (14)0.0380 (13)−0.0180 (14)−0.0051 (14)−0.0040 (11)
C350.0603 (18)0.0410 (13)0.0422 (14)−0.0143 (13)−0.0188 (13)0.0032 (11)
C360.0441 (14)0.0369 (12)0.0417 (12)−0.0079 (11)−0.0108 (11)0.0018 (10)
C370.0379 (13)0.0294 (11)0.0342 (11)−0.0051 (9)−0.0049 (10)0.0027 (9)
C380.0253 (10)0.0304 (10)0.0379 (12)−0.0001 (8)−0.0027 (9)−0.0026 (9)

Geometric parameters (Å, °)

Cl1—C61.727 (3)C14—H140.9500
Cl2—Cl2'0.836 (9)C15—C161.402 (4)
Cl2—C251.759 (3)C15—H150.9500
Cl2'—C251.721 (4)C16—C171.365 (3)
F1—C71.321 (3)C16—H160.9500
F2—C71.355 (3)C17—C181.419 (3)
F3—C71.318 (4)C17—H170.9500
F4—C261.324 (3)C18—C191.416 (3)
F5—C261.344 (3)C19—H190.9500
F6—C261.323 (3)C20—C211.487 (3)
O1—C11.228 (2)C21—C221.528 (3)
O2—C201.230 (2)C21—C231.538 (3)
N1—C11.358 (3)C21—H211.0000
N1—C101.416 (3)C22—C281.504 (3)
N1—H10.86 (3)C22—C271.508 (3)
N2—C201.354 (3)C22—C231.513 (3)
N2—C291.413 (3)C23—C241.467 (3)
N2—H2A0.82 (2)C23—H231.0000
C1—C21.492 (3)C24—C251.313 (3)
C2—C31.517 (3)C24—H240.9500
C2—C41.526 (3)C25—C261.478 (3)
C2—H21.0000C27—H27A0.9800
C3—C41.509 (3)C27—H27B0.9800
C3—C81.518 (3)C27—H27C0.9800
C3—C91.518 (3)C28—H28A0.9800
C4—C51.472 (3)C28—H28B0.9800
C4—H41.0000C28—H28C0.9800
C5—C61.319 (3)C29—C381.373 (3)
C5—H50.9500C29—C301.422 (3)
C6—C71.495 (4)C30—C311.364 (3)
C8—H8A0.9800C30—H300.9500
C8—H8B0.9800C31—C321.413 (4)
C8—H8C0.9800C31—H310.9500
C9—H9A0.9800C32—C371.421 (3)
C9—H9B0.9800C32—C331.424 (3)
C9—H9C0.9800C33—C341.359 (4)
C10—C191.373 (3)C33—H330.9500
C10—C111.417 (3)C34—C351.397 (4)
C11—C121.366 (3)C34—H340.9500
C11—H110.9500C35—C361.368 (3)
C12—C131.414 (3)C35—H350.9500
C12—H120.9500C36—C371.421 (3)
C13—C181.421 (3)C36—H360.9500
C13—C141.422 (3)C37—C381.427 (3)
C14—C151.368 (4)C38—H380.9500
Cl2'—Cl2—C2573.6 (3)C10—C19—H19119.8
Cl2—Cl2'—C2578.6 (5)C18—C19—H19119.8
C1—N1—C10128.00 (18)O2—C20—N2123.53 (19)
C1—N1—H1117.1 (17)O2—C20—C21123.67 (19)
C10—N1—H1114.8 (17)N2—C20—C21112.74 (17)
C20—N2—C29128.63 (18)C20—C21—C22120.22 (18)
C20—N2—H2A116.8 (15)C20—C21—C23122.55 (17)
C29—N2—H2A114.2 (15)C22—C21—C2359.16 (14)
O1—C1—N1123.3 (2)C20—C21—H21114.6
O1—C1—C2123.93 (19)C22—C21—H21114.6
N1—C1—C2112.73 (17)C23—C21—H21114.6
C1—C2—C3120.80 (18)C28—C22—C27113.99 (19)
C1—C2—C4121.70 (17)C28—C22—C23116.81 (18)
C3—C2—C459.48 (14)C27—C22—C23120.43 (18)
C1—C2—H2114.6C28—C22—C21115.22 (19)
C3—C2—H2114.6C27—C22—C21119.57 (18)
C4—C2—H2114.6C23—C22—C2160.75 (14)
C4—C3—C260.57 (14)C24—C23—C22121.26 (19)
C4—C3—C8120.59 (19)C24—C23—C21122.10 (18)
C2—C3—C8119.82 (18)C22—C23—C2160.09 (13)
C4—C3—C9115.91 (18)C24—C23—H23114.3
C2—C3—C9115.64 (19)C22—C23—H23114.3
C8—C3—C9114.12 (19)C21—C23—H23114.3
C5—C4—C3121.43 (19)C25—C24—C23125.5 (2)
C5—C4—C2120.08 (18)C25—C24—H24117.3
C3—C4—C259.95 (14)C23—C24—H24117.3
C5—C4—H4114.8C24—C25—C26124.4 (2)
C3—C4—H4114.8C24—C25—Cl2'118.7 (3)
C2—C4—H4114.8C26—C25—Cl2'113.7 (2)
C6—C5—C4126.3 (2)C24—C25—Cl2124.02 (19)
C6—C5—H5116.9C26—C25—Cl2110.87 (18)
C4—C5—H5116.9Cl2'—C25—Cl227.8 (3)
C5—C6—C7122.5 (2)F6—C26—F4106.6 (2)
C5—C6—Cl1123.73 (19)F6—C26—F5105.5 (2)
C7—C6—Cl1113.73 (19)F4—C26—F5107.0 (2)
F3—C7—F1108.9 (3)F6—C26—C25113.0 (2)
F3—C7—F2106.4 (2)F4—C26—C25112.0 (2)
F1—C7—F2105.8 (2)F5—C26—C25112.3 (2)
F3—C7—C6112.4 (2)C22—C27—H27A109.5
F1—C7—C6112.5 (2)C22—C27—H27B109.5
F2—C7—C6110.4 (3)H27A—C27—H27B109.5
C3—C8—H8A109.5C22—C27—H27C109.5
C3—C8—H8B109.5H27A—C27—H27C109.5
H8A—C8—H8B109.5H27B—C27—H27C109.5
C3—C8—H8C109.5C22—C28—H28A109.5
H8A—C8—H8C109.5C22—C28—H28B109.5
H8B—C8—H8C109.5H28A—C28—H28B109.5
C3—C9—H9A109.5C22—C28—H28C109.5
C3—C9—H9B109.5H28A—C28—H28C109.5
H9A—C9—H9B109.5H28B—C28—H28C109.5
C3—C9—H9C109.5C38—C29—N2124.2 (2)
H9A—C9—H9C109.5C38—C29—C30120.0 (2)
H9B—C9—H9C109.5N2—C29—C30115.76 (19)
C19—C10—N1124.25 (19)C31—C30—C29120.4 (2)
C19—C10—C11119.77 (19)C31—C30—H30119.8
N1—C10—C11115.98 (19)C29—C30—H30119.8
C12—C11—C10120.4 (2)C30—C31—C32121.4 (2)
C12—C11—H11119.8C30—C31—H31119.3
C10—C11—H11119.8C32—C31—H31119.3
C11—C12—C13121.4 (2)C31—C32—C37118.5 (2)
C11—C12—H12119.3C31—C32—C33122.7 (3)
C13—C12—H12119.3C37—C32—C33118.8 (2)
C12—C13—C18118.1 (2)C34—C33—C32120.5 (3)
C12—C13—C14123.1 (2)C34—C33—H33119.7
C18—C13—C14118.8 (2)C32—C33—H33119.7
C15—C14—C13120.5 (3)C33—C34—C35120.8 (2)
C15—C14—H14119.7C33—C34—H34119.6
C13—C14—H14119.7C35—C34—H34119.6
C14—C15—C16120.5 (2)C36—C35—C34120.8 (3)
C14—C15—H15119.8C36—C35—H35119.6
C16—C15—H15119.8C34—C35—H35119.6
C17—C16—C15120.7 (2)C35—C36—C37120.2 (3)
C17—C16—H16119.7C35—C36—H36119.9
C15—C16—H16119.7C37—C36—H36119.9
C16—C17—C18120.6 (2)C32—C37—C36118.9 (2)
C16—C17—H17119.7C32—C37—C38119.5 (2)
C18—C17—H17119.7C36—C37—C38121.6 (2)
C19—C18—C17121.2 (2)C29—C38—C37120.2 (2)
C19—C18—C13119.8 (2)C29—C38—H38119.9
C17—C18—C13118.9 (2)C37—C38—H38119.9
C10—C19—C18120.5 (2)
C10—N1—C1—O13.6 (4)O2—C20—C21—C23−4.4 (3)
C10—N1—C1—C2−174.8 (2)N2—C20—C21—C23178.52 (18)
O1—C1—C2—C3−72.5 (3)C20—C21—C22—C28139.9 (2)
N1—C1—C2—C3106.0 (2)C23—C21—C22—C28−107.9 (2)
O1—C1—C2—C4−1.6 (3)C20—C21—C22—C27−1.7 (3)
N1—C1—C2—C4176.88 (19)C23—C21—C22—C27110.5 (2)
C1—C2—C3—C4111.0 (2)C20—C21—C22—C23−112.2 (2)
C1—C2—C3—C80.5 (3)C28—C22—C23—C24−143.1 (2)
C4—C2—C3—C8−110.5 (2)C27—C22—C23—C242.5 (3)
C1—C2—C3—C9−142.4 (2)C21—C22—C23—C24111.6 (2)
C4—C2—C3—C9106.6 (2)C28—C22—C23—C21105.3 (2)
C2—C3—C4—C5−109.0 (2)C27—C22—C23—C21−109.1 (2)
C8—C3—C4—C50.3 (3)C20—C21—C23—C24−1.9 (3)
C9—C3—C4—C5144.9 (2)C22—C21—C23—C24−110.2 (2)
C8—C3—C4—C2109.3 (2)C20—C21—C23—C22108.3 (2)
C9—C3—C4—C2−106.2 (2)C22—C23—C24—C25160.7 (2)
C1—C2—C4—C51.6 (3)C21—C23—C24—C25−127.2 (3)
C3—C2—C4—C5111.2 (2)C23—C24—C25—C26−176.4 (2)
C1—C2—C4—C3−109.5 (2)C23—C24—C25—Cl2'25.3 (7)
C3—C4—C5—C6−158.2 (2)C23—C24—C25—Cl2−6.8 (5)
C2—C4—C5—C6130.7 (2)Cl2—Cl2'—C25—C24−109.3 (6)
C4—C5—C6—C7−177.3 (2)Cl2—Cl2'—C25—C2690.1 (4)
C4—C5—C6—Cl10.2 (4)Cl2'—Cl2—C25—C2487.8 (6)
C5—C6—C7—F3−7.5 (4)Cl2'—Cl2—C25—C26−101.4 (4)
Cl1—C6—C7—F3174.77 (19)C24—C25—C26—F6120.5 (3)
C5—C6—C7—F1−130.9 (3)Cl2'—C25—C26—F6−80.2 (7)
Cl1—C6—C7—F151.3 (3)Cl2—C25—C26—F6−50.2 (4)
C5—C6—C7—F2111.1 (3)C24—C25—C26—F40.1 (4)
Cl1—C6—C7—F2−66.6 (3)Cl2'—C25—C26—F4159.4 (7)
C1—N1—C10—C19−8.9 (4)Cl2—C25—C26—F4−170.7 (4)
C1—N1—C10—C11170.2 (2)C24—C25—C26—F5−120.3 (3)
C19—C10—C11—C121.2 (3)Cl2'—C25—C26—F539.0 (7)
N1—C10—C11—C12−178.0 (2)Cl2—C25—C26—F568.9 (4)
C10—C11—C12—C130.6 (3)C20—N2—C29—C3812.2 (3)
C11—C12—C13—C18−1.0 (3)C20—N2—C29—C30−166.7 (2)
C11—C12—C13—C14177.7 (2)C38—C29—C30—C310.6 (3)
C12—C13—C14—C15−177.3 (2)N2—C29—C30—C31179.5 (2)
C18—C13—C14—C151.3 (3)C29—C30—C31—C320.2 (3)
C13—C14—C15—C16−0.8 (4)C30—C31—C32—C37−0.8 (4)
C14—C15—C16—C17−0.5 (4)C30—C31—C32—C33178.9 (2)
C15—C16—C17—C181.3 (4)C31—C32—C33—C34179.6 (2)
C16—C17—C18—C19177.8 (2)C37—C32—C33—C34−0.7 (4)
C16—C17—C18—C13−0.8 (3)C32—C33—C34—C350.5 (4)
C12—C13—C18—C19−0.4 (3)C33—C34—C35—C36−0.4 (4)
C14—C13—C18—C19−179.1 (2)C34—C35—C36—C370.5 (4)
C12—C13—C18—C17178.2 (2)C31—C32—C37—C36−179.5 (2)
C14—C13—C18—C17−0.5 (3)C33—C32—C37—C360.8 (3)
N1—C10—C19—C18176.51 (19)C31—C32—C37—C380.8 (3)
C11—C10—C19—C18−2.6 (3)C33—C32—C37—C38−179.0 (2)
C17—C18—C19—C10−176.4 (2)C35—C36—C37—C32−0.7 (3)
C13—C18—C19—C102.2 (3)C35—C36—C37—C38179.0 (2)
C29—N2—C20—O2−4.7 (3)N2—C29—C38—C37−179.50 (19)
C29—N2—C20—C21172.35 (19)C30—C29—C38—C37−0.6 (3)
O2—C20—C21—C2266.2 (3)C32—C37—C38—C29−0.1 (3)
N2—C20—C21—C22−110.9 (2)C36—C37—C38—C29−179.8 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O20.86 (3)2.09 (3)2.932 (2)167 (2)
N2—H2A···O1i0.82 (2)2.19 (3)3.003 (2)169 (2)

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2796).

References

  • Bruker (1997). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Liu, D.-Q. & Yan, F.-Y. (2007). Acta Cryst. E63, o4202.
  • Punja, N. (1981). Eur. Patent EP 0031199.
  • Rigaku/MSC (2005). CrystalClear and CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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