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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o451.
Published online 2008 January 16. doi:  10.1107/S160053680706816X
PMCID: PMC2960375

(E)-3-(2-Chloro-3,3,3-trifluoro­prop-1-en­yl)-2,2-dimethyl-N-p-tolyl­cyclo­propane­carboxamide

Abstract

There are two mol­ecules in the asymmetric unit of the title compound, C16H17ClF3NO. The benzene ring in each mol­ecule makes a dihedral angle of 66.6 (3)° [116.3 (4)° in the second mol­ecule] with the plane of the cyclo­propane ring. The F atoms of the CF3 groups are disordered equally over two positions. The amide hydrogen is linked with the amide oxygen in another mol­ecule by an inter­molecular N—H(...)O hydrogen bond. The packing can be described as a dimeric arrangement of mol­ecules linked through N—H(...)O hydrogen bonds.

Related literature

For related literature, see: Liu et al. (2006 [triangle]); Punja (1981 [triangle]); Zhang (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o451-scheme1.jpg

Experimental

Crystal data

  • C16H17ClF3NO
  • M r = 331.76
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o451-efi1.jpg
  • a = 9.400 (2) Å
  • b = 12.482 (3) Å
  • c = 16.201 (4) Å
  • α = 70.910 (4)°
  • β = 88.921 (5)°
  • γ = 72.517 (4)°
  • V = 1706.7 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 294 (2) K
  • 0.22 × 0.18 × 0.14 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick,1996 [triangle]) T min = 0.945, T max = 0.967
  • 8849 measured reflections
  • 5945 independent reflections
  • 3077 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.207
  • S = 1.09
  • 5945 reflections
  • 457 parameters
  • 137 restraints
  • H-atom parameters constrained
  • Δρmax = 0.60 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SMART; data reduction: SAINT (Bruker, 1997 [triangle]); program(s) used to solve structure: SHELXTL (Bruker, 2001 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; 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/S160053680706816X/bv2081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706816X/bv2081Isup2.hkl

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

Acknowledgments

This work was supported by the National Natural Science Foundation (No. 20376059)

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, a important insecticide controlling a wide range of soil insect pests in maize, sugar beet, and other crops (Punja 1981). p-Toluidine 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 is expected to show some insecticide activity. 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-p-tolylcyclopropane-carboxamide, (I), was synthesized and the structure of (I) is illustrated in Fig. 1. The dihedral angles between the benzene moiety and the cyclopropane group is 66.6 (3)°. The amide hydrogen is linked with the amide oxygen in an adjoining molecule by an intermolecular N—H···O hydrogen bond. The packing can be described as a dimeric arrangement of molecules linked through N—H···O hydrogen bonds (Table 1).

Experimental

The title compound 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 (15 ml), and a drop of anhydrous DMF was added in. The mixture was heated to reflux for 1 h. SOCl2 was removed by a rotoevaporator. The crude the product could be directly disolved in anhydrous toluene, already mixed with p-toluidine(0.44 g, 4.1 mmol). Triethylamine was dropped into the system, preventing the release of white fumes. After 5 h stirring at room temperature, the reaction mixture was treated with hexane. Recrystallization of the off-white product from methanol and a small amount of water (80:1) overnight at ambient temperature gave colorless single crystals of (E)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl -N-p-tolylcyclopropanecarboxamide, suitable for X-ray analysis.

Refinement

H atoms were positioned geometrically with C—H = 0.92–0.98 Å and refined using riding model with Uiso(H) = 1.2Ueq(carrier). The amine H atom was located from difference map and refined isotropically. The disordered CF3 was allowed to rotate about its C—C axis.

Figures

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

Crystal data

C16H17ClF3NOZ = 4
Mr = 331.76F000 = 688
Triclinic, P1Dx = 1.291 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.400 (2) ÅCell parameters from 2183 reflections
b = 12.482 (3) Åθ = 2.6–22.9º
c = 16.201 (4) ŵ = 0.25 mm1
α = 70.910 (4)ºT = 294 (2) K
β = 88.921 (5)ºPrism, colorless
γ = 72.517 (4)º0.22 × 0.18 × 0.14 mm
V = 1706.7 (7) Å3

Data collection

Bruker SMART CCD area-detector diffractometer5945 independent reflections
Radiation source: fine-focus sealed tube3077 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
T = 294(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick,1996)h = −11→9
Tmin = 0.945, Tmax = 0.967k = −14→14
8849 measured reflectionsl = −19→16

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.207  w = 1/[σ2(Fo2) + (0.0879P)2 + 0.5066P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
5945 reflectionsΔρmax = 0.60 e Å3
457 parametersΔρmin = −0.44 e Å3
137 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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)
Cl10.63184 (16)0.55693 (11)1.02621 (11)0.1052 (5)
Cl21.13400 (19)0.54200 (14)0.72738 (18)0.1836 (12)
F10.9100 (9)0.6078 (8)1.0169 (8)0.133 (3)0.50
F20.7921 (10)0.6990 (8)1.0952 (5)0.116 (3)0.50
F30.8242 (11)0.7991 (7)0.9530 (5)0.089 (3)0.50
F1'0.9073 (7)0.6378 (7)0.9589 (6)0.113 (2)0.50
F2'0.8042 (12)0.8127 (7)0.9874 (6)0.095 (3)0.50
F3'0.8598 (11)0.6504 (9)1.0803 (6)0.127 (3)0.50
F41.3243 (9)0.7790 (8)0.6310 (6)0.096 (2)0.50
F51.3304 (11)0.6367 (10)0.5804 (6)0.146 (3)0.50
F61.4122 (11)0.5960 (9)0.7020 (7)0.147 (4)0.50
F4'1.3120 (12)0.7716 (9)0.5891 (6)0.118 (3)0.50
F5'1.3672 (10)0.5822 (7)0.6257 (7)0.127 (3)0.50
F6'1.4006 (8)0.6447 (7)0.7274 (5)0.109 (2)0.50
O10.4629 (3)1.0115 (3)0.78523 (18)0.0712 (8)
O20.9714 (3)0.9971 (3)0.70315 (19)0.0708 (8)
N10.2560 (3)1.0571 (3)0.6969 (2)0.0580 (8)
H10.18291.03200.68980.070*
N20.7591 (3)1.0502 (3)0.7686 (2)0.0586 (9)
H20.68311.02770.78770.070*
C10.7972 (6)0.7010 (5)1.0040 (4)0.106 (2)
C20.6514 (4)0.6955 (4)0.9814 (3)0.0653 (11)
C30.5468 (4)0.7882 (4)0.9324 (3)0.0692 (12)
H30.56830.86010.91330.083*
C40.3983 (4)0.7911 (4)0.9041 (3)0.0726 (13)
H40.38700.71230.91470.087*
C50.3031 (4)0.8882 (4)0.8247 (3)0.0665 (12)
H50.24120.86080.79330.080*
C60.2592 (5)0.8832 (5)0.9160 (3)0.0831 (15)
C70.2734 (6)0.9764 (6)0.9514 (4)0.112 (2)
H7A0.18321.04300.93460.168*
H7B0.35661.00250.92810.168*
H7C0.28950.94361.01420.168*
C80.1253 (5)0.8399 (6)0.9429 (4)0.136 (3)
H8A0.12120.82011.00520.203*
H8B0.13480.77060.92710.203*
H8C0.03520.90180.91360.203*
C90.3514 (4)0.9896 (3)0.7677 (3)0.0540 (10)
C100.2592 (4)1.1642 (4)0.6323 (3)0.0581 (10)
C110.3843 (5)1.2017 (4)0.6188 (3)0.0752 (13)
H110.47311.15560.65380.090*
C120.3780 (6)1.3067 (5)0.5542 (3)0.0825 (14)
H120.46331.33080.54690.099*
C130.2518 (6)1.3772 (4)0.5000 (3)0.0809 (14)
C140.1285 (6)1.3385 (5)0.5130 (3)0.0926 (16)
H140.04071.38460.47710.111*
C150.1306 (5)1.2333 (4)0.5776 (3)0.0738 (12)
H150.04551.20900.58420.089*
C160.2484 (7)1.4916 (5)0.4283 (4)0.126 (2)
H16A0.25621.54910.45400.190*
H16B0.15601.52240.39190.190*
H16C0.33091.47620.39350.190*
C171.3029 (6)0.6758 (5)0.6514 (4)0.1067 (19)
C181.1515 (5)0.6795 (4)0.6771 (3)0.0761 (13)
C191.0418 (4)0.7782 (4)0.6611 (3)0.0705 (12)
H191.06220.84860.63110.085*
C200.8898 (4)0.7886 (4)0.6857 (3)0.0694 (12)
H200.87120.71190.71220.083*
C210.7992 (4)0.8857 (4)0.7199 (3)0.0606 (11)
H210.73310.85980.76430.073*
C220.7560 (4)0.8877 (4)0.6299 (3)0.0690 (12)
C230.7770 (5)0.9826 (4)0.5517 (3)0.0881 (15)
H23A0.86660.99970.56230.132*
H23B0.69261.05330.54040.132*
H23C0.78540.95620.50190.132*
C240.6168 (5)0.8525 (5)0.6222 (4)0.1013 (18)
H24A0.53010.92200.60810.152*
H24B0.60780.79540.67690.152*
H24C0.62470.81800.57670.152*
C250.8538 (4)0.9809 (4)0.7301 (3)0.0549 (10)
C260.7657 (4)1.1539 (4)0.7823 (2)0.0551 (10)
C270.8957 (4)1.1829 (4)0.7839 (3)0.0685 (12)
H270.98581.13270.77510.082*
C280.8923 (5)1.2861 (4)0.7986 (3)0.0714 (12)
H280.98121.30410.79950.086*
C290.7633 (5)1.3630 (4)0.8118 (3)0.0742 (12)
C300.6350 (5)1.3321 (4)0.8109 (3)0.0843 (14)
H300.54531.38220.82020.101*
C310.6353 (5)1.2295 (4)0.7966 (3)0.0751 (13)
H310.54651.21110.79660.090*
C320.7605 (6)1.4761 (5)0.8269 (4)0.1064 (18)
H32A0.83761.45860.87180.160*
H32B0.66471.51050.84500.160*
H32C0.77761.53160.77360.160*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1007 (10)0.0663 (8)0.1359 (13)−0.0321 (7)−0.0128 (8)−0.0109 (8)
Cl20.0972 (12)0.0787 (10)0.283 (3)−0.0084 (9)0.0387 (14)0.0387 (13)
F10.095 (4)0.144 (5)0.139 (5)−0.027 (4)−0.006 (4)−0.025 (4)
F20.107 (5)0.117 (5)0.119 (4)−0.040 (4)−0.039 (3)−0.025 (3)
F30.067 (4)0.104 (4)0.099 (5)−0.049 (3)−0.002 (3)−0.019 (3)
F1'0.067 (3)0.124 (4)0.131 (5)−0.021 (3)0.011 (3)−0.030 (4)
F2'0.084 (4)0.106 (4)0.109 (5)−0.053 (3)−0.003 (4)−0.032 (3)
F3'0.108 (5)0.136 (5)0.128 (5)−0.040 (4)−0.033 (4)−0.028 (4)
F40.064 (3)0.113 (4)0.111 (5)−0.043 (3)0.025 (4)−0.023 (4)
F50.124 (5)0.161 (5)0.146 (5)−0.039 (4)0.049 (4)−0.048 (4)
F60.113 (5)0.147 (5)0.159 (5)−0.014 (4)0.007 (4)−0.046 (4)
F4'0.091 (4)0.126 (5)0.117 (5)−0.038 (3)0.034 (4)−0.013 (4)
F5'0.104 (4)0.125 (5)0.133 (5)−0.018 (3)0.033 (4)−0.038 (4)
F6'0.058 (3)0.120 (4)0.139 (5)−0.014 (3)−0.016 (3)−0.042 (4)
O10.0452 (15)0.090 (2)0.0752 (19)−0.0406 (14)−0.0030 (13)−0.0050 (16)
O20.0466 (15)0.095 (2)0.091 (2)−0.0404 (15)0.0181 (14)−0.0415 (18)
N10.0428 (17)0.073 (2)0.059 (2)−0.0291 (16)0.0015 (15)−0.0140 (18)
N20.0421 (18)0.072 (2)0.068 (2)−0.0311 (16)0.0106 (15)−0.0206 (18)
C10.071 (4)0.086 (4)0.134 (6)−0.019 (3)−0.020 (4)−0.004 (4)
C20.051 (2)0.069 (3)0.074 (3)−0.028 (2)−0.001 (2)−0.013 (2)
C30.049 (2)0.069 (3)0.082 (3)−0.031 (2)−0.004 (2)−0.004 (2)
C40.052 (2)0.069 (3)0.088 (3)−0.034 (2)−0.007 (2)−0.001 (2)
C50.047 (2)0.082 (3)0.069 (3)−0.036 (2)−0.0034 (19)−0.008 (2)
C60.047 (2)0.108 (4)0.068 (3)−0.029 (2)0.008 (2)0.009 (3)
C70.097 (4)0.136 (5)0.077 (4)−0.008 (4)0.016 (3)−0.028 (4)
C80.055 (3)0.173 (6)0.116 (5)−0.047 (3)0.009 (3)0.043 (4)
C90.038 (2)0.071 (3)0.054 (2)−0.0223 (19)0.0057 (17)−0.017 (2)
C100.050 (2)0.075 (3)0.053 (2)−0.023 (2)0.0093 (18)−0.022 (2)
C110.063 (3)0.090 (3)0.068 (3)−0.039 (2)0.004 (2)−0.008 (3)
C120.084 (3)0.096 (4)0.066 (3)−0.047 (3)0.015 (3)−0.009 (3)
C130.085 (3)0.078 (3)0.066 (3)−0.021 (3)0.025 (3)−0.011 (3)
C140.068 (3)0.093 (4)0.079 (4)0.003 (3)0.008 (3)−0.007 (3)
C150.050 (2)0.084 (3)0.073 (3)−0.016 (2)0.004 (2)−0.013 (3)
C160.124 (5)0.099 (4)0.103 (5)−0.014 (4)0.032 (4)0.015 (4)
C170.066 (4)0.095 (5)0.127 (6)−0.004 (3)0.002 (3)−0.015 (4)
C180.049 (3)0.071 (3)0.087 (3)−0.015 (2)0.002 (2)−0.002 (2)
C190.047 (2)0.066 (3)0.094 (3)−0.022 (2)0.007 (2)−0.017 (2)
C200.051 (2)0.060 (3)0.098 (3)−0.026 (2)0.011 (2)−0.021 (2)
C210.042 (2)0.069 (3)0.076 (3)−0.0286 (19)0.0094 (19)−0.022 (2)
C220.044 (2)0.073 (3)0.098 (4)−0.016 (2)−0.006 (2)−0.040 (3)
C230.084 (3)0.092 (4)0.082 (4)−0.016 (3)−0.014 (3)−0.031 (3)
C240.054 (3)0.122 (4)0.156 (5)−0.029 (3)−0.004 (3)−0.081 (4)
C250.037 (2)0.070 (3)0.057 (2)−0.0222 (19)−0.0018 (17)−0.014 (2)
C260.045 (2)0.066 (3)0.053 (2)−0.0225 (19)0.0024 (17)−0.014 (2)
C270.051 (2)0.090 (3)0.077 (3)−0.031 (2)0.008 (2)−0.035 (3)
C280.061 (3)0.088 (3)0.075 (3)−0.035 (3)0.003 (2)−0.030 (3)
C290.077 (3)0.075 (3)0.069 (3)−0.028 (3)−0.006 (2)−0.017 (2)
C300.066 (3)0.079 (3)0.102 (4)−0.014 (3)0.002 (3)−0.032 (3)
C310.052 (3)0.085 (3)0.091 (3)−0.026 (2)0.009 (2)−0.029 (3)
C320.106 (4)0.091 (4)0.132 (5)−0.030 (3)−0.003 (3)−0.049 (4)

Geometric parameters (Å, °)

Cl1—C21.708 (4)C11—H110.9300
Cl2—C181.699 (5)C12—C131.363 (7)
F1—C11.276 (8)C12—H120.9300
F2—C11.468 (8)C13—C141.372 (7)
F3—C11.328 (8)C13—C161.510 (7)
F1'—C11.444 (8)C14—C151.380 (6)
F2'—C11.352 (8)C14—H140.9300
F3'—C11.251 (8)C15—H150.9300
F4—C171.297 (10)C16—H16A0.9600
F5—C171.382 (8)C16—H16B0.9600
F6—C171.265 (8)C16—H16C0.9600
F4'—C171.313 (8)C17—C181.467 (7)
F5'—C171.338 (8)C18—C191.298 (6)
F6'—C171.423 (8)C19—C201.456 (5)
O1—C91.219 (4)C19—H190.9300
O2—C251.230 (4)C20—C211.517 (6)
N1—C91.335 (5)C20—C221.519 (6)
N1—C101.411 (5)C20—H200.9800
N1—H10.8600C21—C251.484 (5)
N2—C251.341 (5)C21—C221.511 (6)
N2—C261.403 (5)C21—H210.9800
N2—H20.8600C22—C231.481 (7)
C1—C21.453 (6)C22—C241.519 (6)
C2—C31.297 (5)C23—H23A0.9600
C3—C41.464 (5)C23—H23B0.9600
C3—H30.9300C23—H23C0.9600
C4—C51.515 (6)C24—H24A0.9600
C4—C61.516 (7)C24—H24B0.9600
C4—H40.9800C24—H24C0.9600
C5—C91.492 (5)C26—C311.372 (6)
C5—C61.514 (7)C26—C271.377 (5)
C5—H50.9800C27—C281.376 (6)
C6—C71.495 (8)C27—H270.9300
C6—C81.516 (6)C28—C291.365 (6)
C7—H7A0.9600C28—H280.9300
C7—H7B0.9600C29—C301.374 (6)
C7—H7C0.9600C29—C321.502 (7)
C8—H8A0.9600C30—C311.374 (6)
C8—H8B0.9600C30—H300.9300
C8—H8C0.9600C31—H310.9300
C10—C151.380 (6)C32—H32A0.9600
C10—C111.380 (5)C32—H32B0.9600
C11—C121.369 (6)C32—H32C0.9600
C9—N1—C10128.6 (3)F4—C17—F4'32.5 (6)
C9—N1—H1115.7F6—C17—F5'64.6 (7)
C10—N1—H1115.7F4—C17—F5'130.9 (7)
C25—N2—C26129.5 (3)F4'—C17—F5'107.5 (8)
C25—N2—H2115.2F6—C17—F596.3 (8)
C26—N2—H2115.2F4—C17—F5108.3 (8)
F1—C1—F3112.4 (7)F4'—C17—F577.7 (7)
F3'—C1—F2'101.0 (8)F5'—C17—F534.8 (5)
F3'—C1—F1'99.0 (7)F6—C17—F6'35.0 (5)
F2'—C1—F1'110.7 (7)F4—C17—F6'84.8 (7)
F3'—C1—C2121.7 (6)F4'—C17—F6'112.5 (8)
F1—C1—C2118.0 (6)F5'—C17—F6'99.3 (7)
F3—C1—C2112.8 (6)F5—C17—F6'128.3 (7)
F2'—C1—C2114.6 (6)F6—C17—C18117.7 (7)
F1'—C1—C2108.6 (5)F4—C17—C18112.6 (6)
F3—C1—F2110.4 (7)F4'—C17—C18115.2 (6)
C2—C1—F2104.4 (5)F5'—C17—C18111.8 (6)
C3—C2—C1122.4 (4)F5—C17—C18110.4 (6)
C3—C2—Cl1124.0 (3)F6'—C17—C18109.4 (6)
C1—C2—Cl1113.6 (3)C19—C18—C17123.0 (4)
C2—C3—C4126.5 (4)C19—C18—Cl2123.8 (3)
C2—C3—H3116.8C17—C18—Cl2113.2 (4)
C4—C3—H3116.8C18—C19—C20126.0 (4)
C3—C4—C5123.0 (3)C18—C19—H19117.0
C3—C4—C6120.3 (4)C20—C19—H19117.0
C5—C4—C659.9 (3)C19—C20—C21123.0 (4)
C3—C4—H4114.3C19—C20—C22121.5 (4)
C5—C4—H4114.3C21—C20—C2259.7 (3)
C6—C4—H4114.3C19—C20—H20114.0
C9—C5—C6120.5 (4)C21—C20—H20114.0
C9—C5—C4123.5 (3)C22—C20—H20114.0
C6—C5—C460.1 (3)C25—C21—C22120.6 (4)
C9—C5—H5114.1C25—C21—C20124.1 (3)
C6—C5—H5114.1C22—C21—C2060.2 (3)
C4—C5—H5114.1C25—C21—H21113.9
C7—C6—C5119.8 (4)C22—C21—H21113.9
C7—C6—C8114.9 (5)C20—C21—H21113.9
C5—C6—C8115.3 (5)C23—C22—C21118.9 (4)
C7—C6—C4120.1 (4)C23—C22—C20120.8 (4)
C5—C6—C460.0 (3)C21—C22—C2060.1 (3)
C8—C6—C4115.8 (5)C23—C22—C24114.9 (4)
C6—C7—H7A109.5C21—C22—C24115.6 (4)
C6—C7—H7B109.5C20—C22—C24115.7 (4)
H7A—C7—H7B109.5C22—C23—H23A109.5
C6—C7—H7C109.5C22—C23—H23B109.5
H7A—C7—H7C109.5H23A—C23—H23B109.5
H7B—C7—H7C109.5C22—C23—H23C109.5
C6—C8—H8A109.5H23A—C23—H23C109.5
C6—C8—H8B109.5H23B—C23—H23C109.5
H8A—C8—H8B109.5C22—C24—H24A109.5
C6—C8—H8C109.5C22—C24—H24B109.5
H8A—C8—H8C109.5H24A—C24—H24B109.5
H8B—C8—H8C109.5C22—C24—H24C109.5
O1—C9—N1123.4 (3)H24A—C24—H24C109.5
O1—C9—C5123.9 (3)H24B—C24—H24C109.5
N1—C9—C5112.7 (3)O2—C25—N2123.5 (4)
C15—C10—C11118.2 (4)O2—C25—C21123.3 (4)
C15—C10—N1117.8 (3)N2—C25—C21113.2 (3)
C11—C10—N1123.9 (4)C31—C26—C27118.4 (4)
C12—C11—C10120.2 (4)C31—C26—N2117.8 (3)
C12—C11—H11119.9C27—C26—N2123.8 (4)
C10—C11—H11119.9C28—C27—C26120.0 (4)
C13—C12—C11122.6 (4)C28—C27—H27120.0
C13—C12—H12118.7C26—C27—H27120.0
C11—C12—H12118.7C29—C28—C27122.5 (4)
C12—C13—C14116.9 (5)C29—C28—H28118.8
C12—C13—C16121.6 (5)C27—C28—H28118.8
C14—C13—C16121.5 (5)C28—C29—C30116.8 (4)
C13—C14—C15122.1 (5)C28—C29—C32122.0 (4)
C13—C14—H14118.9C30—C29—C32121.2 (5)
C15—C14—H14118.9C31—C30—C29122.0 (4)
C10—C15—C14120.0 (4)C31—C30—H30119.0
C10—C15—H15120.0C29—C30—H30119.0
C14—C15—H15120.0C26—C31—C30120.4 (4)
C13—C16—H16A109.5C26—C31—H31119.8
C13—C16—H16B109.5C30—C31—H31119.8
H16A—C16—H16B109.5C29—C32—H32A109.5
C13—C16—H16C109.5C29—C32—H32B109.5
H16A—C16—H16C109.5H32A—C32—H32B109.5
H16B—C16—H16C109.5C29—C32—H32C109.5
F6—C17—F4110.0 (8)H32A—C32—H32C109.5
F6—C17—F4'125.2 (9)H32B—C32—H32C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.152.978 (4)161
N2—H2···O10.862.142.959 (4)158

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2081).

References

  • Bruker (1997). SADABS, SMART, and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2001). SHELXTL Bruker AXS Inc., Madison, Wisconsin, USA.
  • Liu, D.-Q., Feng, Y.-Q., Liu, D.-W. & Zhang, S.-S. (2006). Acta Cryst. E62, o1747–o1748.
  • Punja, N. (1981). European Patent EP 0 031 199.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Zhang, M. H. (2005). Fine Spec. Chem.13, 1–4.

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