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Acta Crystallogr Sect E Struct Rep Online. Mar 1, 2010; 66(Pt 3): o582–o583.
Published online Feb 10, 2010. doi:  10.1107/S1600536810004435
PMCID: PMC2983722
1-[3,5-Bis(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone
Hoong-Kun Fun,a* Madhukar Hemamalini,a S. Samshuddin,b B. Narayana,b and H. S. Yathirajanc
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
cDepartment of Studies in Chemistry, University of Mysore, Mysore 570 006, India
Correspondence e-mail: hkfun/at/usm.my
Thomson Reuters ResearcherID: A-3561-2009.
Received January 28, 2010; Accepted February 4, 2010.
In the asymmetric unit of the title compound, C17H14F2N2O, there are three independent mol­ecules (A, B and C) which differ slightly in the relative orientations of the two fluoro­phenyl rings. In mol­ecules A and C one of the fluoro­phenyl rings is disordered over two positions, with occupancy ratios of 0.72 (2):0.28 (2) for mol­ecule A and 0.67 (2):0.33 (2) for mol­ecule C. The dihedral angle between the two fluoro­phenyl rings in the independent mol­ecules lie in the range 70.3 (3)–84.0 (3)°. In the crystal structure, the mol­ecules are linked via inter­molecular C—H(...)O and C—H(...)F hydrogen bonds and π(...)π stacking inter­actions [centroid–centroid distance = 3.7508 (13) Å], forming a three-dimensional network.
Related literature
For the biological activity of pyrazoline derivatives, see: Amir et al. (2008 [triangle]); Garge et al. (1971 [triangle]); Hes et al. (1978 [triangle]); Manna et al. (2005 [triangle]); Regaila et al. (1979 [triangle]). For the role of pyrazolines in organic synthesis, see: Bhaskarreddy et al. (1997 [triangle]); Klimova et al. (1999 [triangle]). For related structures, see: Anuradha et al. (2008 [triangle]); Jian et al. (2006 [triangle]); Jian & Wang (2006 [triangle]); Lu et al. (2008 [triangle]); Wang et al. (2005 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).
An external file that holds a picture, illustration, etc.
Object name is e-66-0o582-scheme1.jpg Object name is e-66-0o582-scheme1.jpg
Crystal data
  • C17H14F2N2O
  • M r = 300.30
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o582-efi1.jpg
  • a = 7.1447 (1) Å
  • b = 17.2332 (3) Å
  • c = 18.4871 (4) Å
  • α = 102.880 (1)°
  • β = 97.941 (1)°
  • γ = 96.373 (1)°
  • V = 2173.86 (7) Å3
  • Z = 6
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 100 K
  • 0.40 × 0.27 × 0.21 mm
Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.960, T max = 0.978
  • 40717 measured reflections
  • 12544 independent reflections
  • 6078 reflections with I > 2σ(I)
  • R int = 0.039
Refinement
  • R[F 2 > 2σ(F 2)] = 0.078
  • wR(F 2) = 0.242
  • S = 1.03
  • 12544 reflections
  • 726 parameters
  • 510 restraints
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.22 e Å−3
Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004435/ci5026sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004435/ci5026Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH thanks Universiti Sains Malaysia for a post-doctoral research fellowship. SS thanks Mangalore University for the research facilities.
supplementary crystallographic information
Comment
Considerable attention has been focused on substituted pyrazoline compounds, due to their biological activity. In particular, they are used as antitumor, antibacterial, antifungal, antiviral, antiparasitic, anti-tubercular and insecticidal agents (Hes et al., 1978; Manna et al., 2005; Amir et al., 2008). Some of these compounds have also exhibit anti-inflammatory, anti-diabetic, anaesthetic and analgesic properties (Garge et al., 1971; Regaila et al., 1979). Among the pyrazoline derivatives, 1-acetyl-pyrazolines have been identified as one of the most promising scaffold. In the field of medicinal chemistry, 1-acetyl-pyrazoline derivatives have been found to display anticancer and anti-inflammatory activities. In addition, pyrazolines have played a crucial part in the development of the theory of heterocyclic chemistry and are also used extensively in organic synthesis (Klimova et al., 1999; Bhaskarreddy et al., 1997).
The crystal structures of 1-[5-(4-hydroxy-3-methoxyphenyl)-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone (Wang et al., 2005), 1-[4,5-dihydro-5-phenyl-3-(p-tolyl) pyrazol-1-yl]ethanone (Jian et al., 2006), 1-[3-(4-methoxyphenyl)- 5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone (Jian & Wang, 2006), 1-[3-(2,4-dichloro-5-fluorophenyl)-5-(3-methyl-2-thienyl)-4,5-dihydro-1H- pyrazol-1-yl]ethanone (Anuradha et al., 2008) and 1-[3-(2-naphthyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro- 1H-pyrazol-1-yl]ethanone (Lu et al., 2008) have been reported. Pyrazolines can be conveniently synthesized by the treatment of α,β-unsaturated carbonyl compounds with hydrazine reagents in basic and acidic media. In this method, hydrazones are formed as intermediates, which can be subsequently cyclized to 2-pyrazolines in the presence of acetic acid. In view of the biological importance of pyrazolines, we report here the crystal structure of a new pyrazoline derivative.
The asymmetric unit of the title compound consists of three crystallographically independent molecules, A, B and C (Fig. 1). In each independent molecule, the pyrazole ring adopts a flattened envelope conformation; the flap atoms C9A, C9B and C9C are displaced by 0.078 (3) and 0.099 (3) and 0.205 (3) Å from the planes of the other four atoms. The dihedral angle between the two fluorophenyl rings are: 70.3 (3) and 72.7 (9)° in the major and minor components of molecule A, 74.73 (10)° in molecule B and 84.0 (3) and 76.1 (9)° in the major and minor components of molecule C.
In the crystal structure (Fig. 2), the molecules are linked through intermolecular C—H···O and C—H···F hydrogen bonds (see Table 1) to form three-dimensional network. The crystal structure is further stabilized by weak π···π stacking interactions between C10A–C15A and C10B–C15B phenyl rings at (x, y, z), with a ring centroid-to-centroid distance of 3.7509 (13)Å.
Experimental
A mixture of (2E)-1,3-bis(4-fluorophenyl)prop-2-en-1-one (2.44 g, 0.01 mol) and hydrazine hydrate (0.5ml, 0.01 mol) in ethanol (25 ml) in presence of glacial acetic acid (2 ml) was refluxed for 5 h. The reaction mixture was cooled and poured into 50 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown by slow evaporation of a toluene solution (yield: 84%, m.p. 387 K). Analytical data: Found (Calculated): C 67.86 (67.99), H 4.62 (4.70), N 9.29 (9.33)%.
Refinement
One of the 4-fluorophenyl rings (F1/C1-C6) in molecules A and C are each disordered over two positions with occupancies of 0.72 (2) and 0.28 (2) for molecule A, and 0.67 (2) and 0.33 (2) for molecule C. In all disorder components atoms closer than 1.7 Å were restrained to have the same Uij components and all bonds were subjected to a rigid bond restraint. The 1,2- and 1,3-distances in the major and minor disorder components were restrained to be the same. H atoms were positioned geometrically [C–H = 0.93–0.98 Å] and were refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was used for the methyl groups.
Figures
Fig. 1.
Fig. 1.
The three independent molecules of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Open bonds indicate minor disorder components. H atoms have been omitted for clarity.
Fig. 2.
Fig. 2.
The crystal packing of the title compound, showing a hydrogen-bonded (dashed lines) network.
Crystal data
C17H14F2N2OZ = 6
Mr = 300.30F(000) = 936
Triclinic, P1Dx = 1.376 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1447 (1) ÅCell parameters from 8334 reflections
b = 17.2332 (3) Åθ = 2.9–30.0°
c = 18.4871 (4) ŵ = 0.11 mm1
α = 102.880 (1)°T = 100 K
β = 97.941 (1)°Block, colourless
γ = 96.373 (1)°0.40 × 0.27 × 0.21 mm
V = 2173.86 (7) Å3
Data collection
Bruker SMART APEXII CCD area-detector diffractometer12544 independent reflections
Radiation source: fine-focus sealed tube6078 reflections with I > 2σ(I)
graphiteRint = 0.039
[var phi] and ω scansθmax = 30.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −10→10
Tmin = 0.960, Tmax = 0.978k = −22→24
40717 measured reflectionsl = −20→25
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)] = 0.078Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.242H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.1087P)2 + 0.1919P] where P = (Fo2 + 2Fc2)/3
12544 reflections(Δ/σ)max = 0.002
726 parametersΔρmax = 0.32 e Å3
510 restraintsΔρmin = −0.22 e Å3
Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) k.
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
F2A0.4613 (3)0.09609 (11)0.49187 (11)0.1240 (6)
O1A0.9145 (2)−0.05242 (8)0.25336 (9)0.0730 (5)
N1A0.9407 (2)0.11515 (8)0.17523 (8)0.0456 (4)
N2A0.9414 (2)0.06841 (9)0.22753 (8)0.0512 (4)
F1A1.1097 (13)0.42500 (19)0.0516 (2)0.0741 (14)0.72 (2)
C1A1.1010 (14)0.3317 (5)0.2059 (4)0.0436 (16)0.72 (2)
H1AA1.12660.34560.25830.052*0.72 (2)
C2A1.1175 (13)0.3910 (4)0.1671 (3)0.0483 (15)0.72 (2)
H2AA1.14740.44510.19220.058*0.72 (2)
C3A1.0883 (11)0.3676 (3)0.0906 (3)0.0477 (12)0.72 (2)
C4A1.0423 (10)0.2887 (3)0.0501 (3)0.0489 (11)0.72 (2)
H4AA1.02520.2754−0.00220.059*0.72 (2)
C5A1.0224 (9)0.2300 (4)0.0894 (4)0.0431 (11)0.72 (2)
H5AA0.99270.17610.06360.052*0.72 (2)
C6A1.0466 (13)0.2513 (4)0.1680 (4)0.0364 (12)0.72 (2)
F1X1.002 (4)0.4294 (6)0.0552 (7)0.097 (5)0.28 (2)
C1X1.055 (3)0.3297 (12)0.2090 (11)0.041 (4)0.28 (2)
H1XA1.08060.34440.26140.050*0.28 (2)
C2X1.062 (3)0.3898 (12)0.1703 (9)0.052 (4)0.28 (2)
H2XA1.10140.44320.19640.062*0.28 (2)
C3X1.011 (3)0.3712 (8)0.0948 (8)0.061 (4)0.28 (2)
C4X0.966 (4)0.2924 (8)0.0541 (9)0.071 (4)0.28 (2)
H4XA0.93970.27910.00180.086*0.28 (2)
C5X0.962 (4)0.2339 (10)0.0943 (10)0.066 (5)0.28 (2)
H5XA0.92260.18100.06710.079*0.28 (2)
C6X1.012 (4)0.2471 (11)0.1724 (11)0.054 (5)0.28 (2)
C7A1.0168 (3)0.18737 (10)0.21017 (10)0.0451 (4)
C8A1.0795 (3)0.19916 (12)0.29317 (11)0.0615 (6)
H8AA1.01700.23990.32180.074*
H8AB1.21680.21430.30710.074*
C9A1.0154 (3)0.11514 (11)0.30573 (10)0.0550 (5)
H9AA1.12760.09370.32580.066*
C10A0.8666 (3)0.11110 (11)0.35581 (10)0.0523 (5)
C11A0.8752 (3)0.06103 (12)0.40491 (12)0.0629 (6)
H11A0.97470.03070.40760.075*
C12A0.7375 (4)0.05556 (14)0.45006 (14)0.0797 (7)
H12A0.74320.02150.48270.096*
C13A0.5947 (4)0.10047 (15)0.44597 (15)0.0770 (7)
C14A0.5789 (3)0.15065 (14)0.39909 (13)0.0708 (6)
H14A0.47830.18050.39730.085*
C15A0.7175 (3)0.15619 (12)0.35381 (11)0.0613 (6)
H15A0.71020.19070.32170.074*
C16A0.8997 (3)−0.01320 (11)0.20599 (11)0.0527 (5)
C17A0.8353 (3)−0.04987 (11)0.12432 (12)0.0621 (6)
H17A0.8408−0.10660.11420.093*
H17B0.9171−0.02550.09600.093*
H17C0.7064−0.04120.11000.093*
F1B0.6346 (2)−0.09751 (7)0.94366 (8)0.0912 (5)
F2B1.2124 (3)0.23406 (10)0.50335 (11)0.1207 (6)
O1B0.7863 (3)0.38636 (8)0.74826 (9)0.0774 (5)
N1B0.7612 (2)0.21708 (8)0.82439 (8)0.0474 (4)
N2B0.7549 (2)0.26485 (9)0.77306 (9)0.0544 (4)
C1B0.5996 (3)0.00176 (11)0.79147 (11)0.0512 (5)
H1BA0.5638−0.01100.73940.061*
C2B0.5897 (3)−0.05886 (11)0.82958 (12)0.0572 (5)
H2BA0.5488−0.11220.80380.069*
C3B0.6414 (3)−0.03835 (11)0.90579 (12)0.0575 (5)
C4B0.6973 (3)0.03970 (11)0.94695 (12)0.0590 (5)
H4BA0.72710.05180.99920.071*
C5B0.7078 (3)0.09941 (11)0.90838 (11)0.0516 (5)
H5BA0.74580.15260.93510.062*
C6B0.6628 (2)0.08176 (10)0.83014 (10)0.0437 (4)
C7B0.6789 (3)0.14553 (11)0.78974 (10)0.0458 (4)
C8B0.6035 (3)0.13564 (12)0.70780 (11)0.0644 (6)
H8BA0.46530.12290.69730.077*
H8BB0.65760.09380.67650.077*
C9B0.6710 (3)0.21961 (12)0.69536 (11)0.0564 (5)
H9BA0.55990.24300.67730.068*
C10B0.8155 (3)0.22149 (11)0.64289 (10)0.0517 (5)
C11B0.8024 (3)0.27024 (12)0.59256 (11)0.0616 (5)
H11B0.70220.30020.59000.074*
C12B0.9375 (4)0.27470 (14)0.54602 (13)0.0791 (7)
H12B0.92950.30770.51250.095*
C13B1.0813 (4)0.23014 (14)0.55029 (14)0.0749 (7)
C14B1.1007 (3)0.18113 (13)0.59823 (13)0.0694 (6)
H14B1.20150.15140.59980.083*
C15B0.9645 (3)0.17688 (12)0.64496 (11)0.0596 (5)
H15B0.97410.14350.67810.071*
C16B0.8064 (3)0.34635 (11)0.79500 (12)0.0595 (5)
C17B0.8895 (4)0.38121 (11)0.87589 (12)0.0752 (7)
H17D0.93140.43780.88370.113*
H17E0.99640.35510.88960.113*
H17F0.79440.37310.90650.113*
F2C0.1119 (3)0.42973 (11)0.48513 (12)0.1249 (6)
O1C0.6321 (3)0.28974 (9)0.26097 (9)0.0863 (6)
N1C0.6015 (2)0.45434 (8)0.18017 (8)0.0458 (4)
N2C0.6263 (2)0.40862 (9)0.23277 (9)0.0518 (4)
F1C0.6000 (10)0.7682 (4)0.0556 (5)0.0767 (13)0.67 (2)
C1C0.712 (2)0.6756 (5)0.2086 (5)0.0469 (16)0.67 (2)
H1CA0.77130.68960.25880.056*0.67 (2)
C2C0.6924 (16)0.7348 (5)0.1691 (4)0.0506 (17)0.67 (2)
H2CA0.73180.78890.19260.061*0.67 (2)
C3C0.6135 (11)0.7112 (4)0.0953 (4)0.0487 (13)0.67 (2)
C4C0.5451 (11)0.6328 (3)0.0575 (4)0.0527 (12)0.67 (2)
H4CA0.49240.61960.00670.063*0.67 (2)
C5C0.5571 (12)0.5745 (4)0.0975 (4)0.0461 (12)0.67 (2)
H5CA0.50680.52120.07410.055*0.67 (2)
C6C0.6446 (13)0.5950 (5)0.1731 (4)0.0395 (14)0.67 (2)
F1Y0.671 (5)0.7647 (9)0.0556 (10)0.123 (6)0.33 (2)
C1Y0.718 (5)0.6637 (12)0.2093 (10)0.057 (4)0.33 (2)
H1YA0.74730.67760.26150.068*0.33 (2)
C2Y0.733 (3)0.7245 (11)0.1713 (9)0.056 (4)0.33 (2)
H2YA0.78200.77710.19760.068*0.33 (2)
C3Y0.676 (3)0.7066 (8)0.0951 (9)0.064 (4)0.33 (2)
C4Y0.623 (4)0.6273 (7)0.0549 (8)0.075 (4)0.33 (2)
H4YA0.58640.61450.00290.090*0.33 (2)
C5Y0.626 (3)0.5680 (8)0.0937 (8)0.056 (3)0.33 (2)
H5YA0.60510.51480.06600.068*0.33 (2)
C6Y0.660 (3)0.5826 (11)0.1730 (8)0.057 (4)0.33 (2)
C7C0.6597 (2)0.52828 (10)0.21396 (10)0.0450 (4)
C8C0.7417 (3)0.54173 (12)0.29583 (11)0.0606 (5)
H8CA0.68400.58230.32700.073*
H8CB0.87910.55770.30490.073*
C9C0.6887 (3)0.45806 (11)0.31055 (11)0.0552 (5)
H9CA0.80330.44050.33370.066*
C10C0.5332 (3)0.45217 (11)0.35786 (10)0.0506 (5)
C11C0.5377 (3)0.40019 (12)0.40562 (11)0.0615 (5)
H11C0.63780.37030.40900.074*
C12C0.3949 (4)0.39252 (14)0.44809 (14)0.0780 (7)
H12C0.39760.35770.47990.094*
C13C0.2514 (4)0.43678 (15)0.44227 (15)0.0762 (7)
C14C0.2400 (3)0.48843 (13)0.39656 (13)0.0682 (6)
H14C0.13890.51790.39390.082*
C15C0.3827 (3)0.49603 (12)0.35406 (11)0.0572 (5)
H15C0.37750.53110.32250.069*
C16C0.6052 (3)0.32713 (11)0.21266 (12)0.0598 (5)
C17C0.5497 (4)0.28828 (11)0.13118 (12)0.0732 (7)
H17G0.56670.23270.12240.110*
H17H0.62850.31490.10330.110*
H17I0.41820.29210.11510.110*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
F2A0.1377 (15)0.1098 (12)0.1409 (15)0.0033 (11)0.0792 (13)0.0377 (11)
O1A0.1061 (12)0.0531 (8)0.0716 (10)0.0171 (8)0.0127 (9)0.0381 (8)
N1A0.0561 (9)0.0378 (8)0.0454 (9)0.0016 (6)0.0047 (7)0.0202 (7)
N2A0.0690 (10)0.0413 (8)0.0442 (9)−0.0003 (7)0.0014 (7)0.0215 (7)
F1A0.123 (4)0.0429 (10)0.0600 (13)−0.0076 (16)0.0184 (17)0.0272 (9)
C1A0.044 (4)0.042 (2)0.039 (2)−0.0108 (19)0.005 (2)0.0067 (15)
C2A0.058 (4)0.0319 (16)0.051 (2)−0.010 (2)0.0107 (19)0.0091 (14)
C3A0.060 (3)0.0363 (15)0.0505 (18)−0.0030 (17)0.0139 (19)0.0195 (13)
C4A0.066 (3)0.0417 (16)0.0386 (17)−0.0042 (17)0.0114 (18)0.0132 (13)
C5A0.055 (3)0.0323 (15)0.0397 (18)−0.0034 (15)0.0084 (17)0.0088 (13)
C6A0.034 (2)0.0368 (19)0.040 (2)−0.0050 (15)0.0039 (14)0.0207 (17)
F1X0.151 (13)0.049 (3)0.090 (5)−0.012 (5)0.008 (6)0.037 (3)
C1X0.041 (9)0.035 (4)0.051 (5)−0.006 (4)0.024 (5)0.014 (3)
C2X0.056 (9)0.037 (4)0.059 (5)−0.011 (5)0.020 (5)0.008 (4)
C3X0.073 (9)0.043 (4)0.065 (5)−0.013 (5)0.012 (6)0.022 (4)
C4X0.104 (12)0.051 (5)0.056 (5)−0.017 (7)0.016 (7)0.019 (4)
C5X0.099 (12)0.039 (5)0.055 (5)−0.012 (7)0.016 (7)0.013 (4)
C6X0.064 (11)0.041 (5)0.044 (5)−0.018 (5)0.007 (6)−0.003 (5)
C7A0.0499 (10)0.0398 (9)0.0447 (11)−0.0031 (8)0.0025 (8)0.0165 (8)
C8A0.0758 (14)0.0540 (12)0.0491 (12)−0.0158 (10)−0.0053 (10)0.0227 (10)
C9A0.0645 (12)0.0543 (11)0.0447 (11)−0.0010 (9)−0.0061 (9)0.0230 (9)
C10A0.0677 (13)0.0455 (10)0.0398 (10)−0.0049 (9)−0.0070 (9)0.0182 (9)
C11A0.0840 (15)0.0545 (12)0.0549 (13)0.0068 (10)0.0051 (11)0.0287 (10)
C12A0.117 (2)0.0615 (14)0.0678 (16)−0.0007 (14)0.0212 (15)0.0347 (12)
C13A0.0909 (18)0.0617 (14)0.0769 (17)−0.0080 (13)0.0264 (14)0.0155 (13)
C14A0.0716 (15)0.0642 (14)0.0698 (15)0.0057 (11)0.0023 (12)0.0099 (12)
C15A0.0786 (15)0.0510 (11)0.0498 (12)0.0030 (10)−0.0097 (11)0.0187 (10)
C16A0.0621 (12)0.0418 (10)0.0611 (13)0.0092 (8)0.0108 (10)0.0258 (10)
C17A0.0827 (15)0.0387 (10)0.0664 (14)0.0049 (9)0.0156 (11)0.0160 (10)
F1B0.1521 (14)0.0463 (7)0.0769 (9)−0.0046 (7)0.0106 (9)0.0329 (7)
F2B0.1402 (15)0.1065 (12)0.1281 (14)−0.0002 (10)0.0764 (12)0.0311 (11)
O1B0.1182 (13)0.0545 (8)0.0744 (10)0.0239 (8)0.0208 (9)0.0383 (8)
N1B0.0634 (10)0.0389 (8)0.0458 (9)0.0084 (7)0.0122 (7)0.0200 (7)
N2B0.0790 (11)0.0437 (9)0.0444 (9)0.0061 (8)0.0083 (8)0.0216 (7)
C1B0.0632 (12)0.0436 (10)0.0438 (11)−0.0027 (8)0.0104 (9)0.0083 (9)
C2B0.0758 (14)0.0340 (9)0.0596 (13)−0.0017 (9)0.0122 (10)0.0108 (9)
C3B0.0749 (14)0.0400 (10)0.0610 (14)0.0002 (9)0.0114 (11)0.0235 (10)
C4B0.0797 (14)0.0458 (11)0.0491 (12)−0.0032 (9)0.0018 (10)0.0181 (9)
C5B0.0676 (12)0.0363 (9)0.0467 (11)−0.0037 (8)0.0010 (9)0.0119 (8)
C6B0.0463 (10)0.0387 (9)0.0468 (11)0.0009 (7)0.0074 (8)0.0146 (8)
C7B0.0499 (10)0.0434 (10)0.0445 (11)0.0005 (8)0.0066 (8)0.0157 (8)
C8B0.0770 (14)0.0614 (13)0.0510 (12)−0.0118 (10)−0.0034 (10)0.0255 (10)
C9B0.0654 (13)0.0566 (11)0.0477 (12)0.0016 (9)−0.0025 (9)0.0247 (10)
C10B0.0679 (12)0.0462 (10)0.0371 (10)−0.0036 (9)−0.0063 (9)0.0170 (8)
C11B0.0828 (15)0.0537 (12)0.0518 (12)0.0065 (10)0.0032 (11)0.0271 (10)
C12B0.119 (2)0.0616 (14)0.0610 (15)−0.0049 (14)0.0171 (14)0.0315 (12)
C13B0.0900 (18)0.0596 (14)0.0729 (16)−0.0089 (12)0.0261 (14)0.0135 (12)
C14B0.0735 (15)0.0636 (14)0.0647 (15)0.0058 (11)0.0044 (12)0.0089 (12)
C15B0.0762 (14)0.0528 (11)0.0470 (12)0.0067 (10)−0.0060 (10)0.0178 (9)
C16B0.0845 (15)0.0431 (11)0.0626 (14)0.0166 (10)0.0238 (11)0.0265 (10)
C17B0.130 (2)0.0381 (10)0.0620 (14)0.0134 (12)0.0289 (14)0.0122 (10)
F2C0.1355 (15)0.1059 (12)0.1501 (16)0.0022 (10)0.0853 (13)0.0360 (11)
O1C0.1375 (16)0.0627 (9)0.0793 (11)0.0351 (10)0.0268 (10)0.0446 (9)
N1C0.0557 (9)0.0376 (8)0.0477 (9)0.0036 (6)0.0081 (7)0.0195 (7)
N2C0.0712 (11)0.0433 (8)0.0447 (9)0.0048 (7)0.0063 (8)0.0222 (7)
F1C0.117 (3)0.0422 (15)0.081 (2)0.0150 (16)0.021 (2)0.0325 (15)
C1C0.059 (3)0.030 (3)0.046 (3)−0.006 (2)0.006 (2)0.005 (2)
C2C0.072 (4)0.025 (2)0.060 (3)0.007 (2)0.022 (2)0.0142 (17)
C3C0.059 (3)0.0343 (18)0.060 (2)0.0096 (17)0.020 (2)0.0203 (16)
C4C0.072 (3)0.0406 (18)0.047 (2)0.011 (2)0.006 (2)0.0161 (15)
C5C0.059 (3)0.0294 (17)0.0475 (19)0.0037 (18)0.004 (2)0.0092 (14)
C6C0.055 (3)0.025 (2)0.044 (2)0.0003 (18)0.018 (2)0.0181 (19)
F1Y0.238 (17)0.042 (4)0.075 (6)−0.013 (7)−0.019 (9)0.031 (4)
C1Y0.093 (9)0.035 (6)0.050 (6)−0.001 (6)0.027 (6)0.023 (4)
C2Y0.078 (9)0.023 (5)0.059 (5)0.007 (5)−0.004 (5)0.001 (4)
C3Y0.098 (11)0.035 (4)0.058 (5)−0.002 (5)0.003 (6)0.020 (4)
C4Y0.119 (11)0.036 (4)0.054 (5)−0.002 (6)−0.022 (7)0.007 (3)
C5Y0.081 (9)0.033 (4)0.051 (4)0.001 (5)−0.007 (5)0.015 (3)
C6Y0.073 (7)0.030 (5)0.053 (5)−0.002 (5)−0.019 (5)−0.003 (4)
C7C0.0490 (10)0.0410 (10)0.0445 (11)−0.0046 (8)0.0043 (8)0.0166 (8)
C8C0.0690 (13)0.0567 (12)0.0504 (12)−0.0149 (9)−0.0031 (10)0.0211 (10)
C9C0.0603 (12)0.0562 (12)0.0493 (12)−0.0026 (9)−0.0034 (9)0.0260 (10)
C10C0.0608 (12)0.0488 (10)0.0387 (10)−0.0041 (9)−0.0053 (8)0.0174 (8)
C11C0.0801 (15)0.0575 (12)0.0516 (12)0.0080 (10)0.0051 (11)0.0277 (10)
C12C0.111 (2)0.0615 (14)0.0675 (16)−0.0037 (14)0.0241 (14)0.0316 (12)
C13C0.0844 (17)0.0630 (14)0.0797 (17)−0.0094 (12)0.0307 (14)0.0134 (13)
C14C0.0655 (14)0.0614 (13)0.0707 (15)0.0018 (10)0.0034 (12)0.0099 (12)
C15C0.0665 (13)0.0533 (11)0.0484 (12)0.0012 (9)−0.0063 (10)0.0187 (9)
C16C0.0784 (14)0.0439 (11)0.0679 (14)0.0164 (10)0.0197 (11)0.0281 (10)
C17C0.1102 (19)0.0383 (10)0.0728 (16)0.0099 (11)0.0195 (14)0.0147 (11)
Geometric parameters (Å, °)
F2A—C13A1.368 (3)C8B—C9B1.550 (3)
O1A—C16A1.220 (2)C8B—H8BA0.97
N1A—C7A1.287 (2)C8B—H8BB0.97
N1A—N2A1.3895 (18)C9B—C10B1.514 (3)
N2A—C16A1.360 (2)C9B—H9BA0.98
N2A—C9A1.481 (2)C10B—C15B1.382 (3)
F1A—C3A1.355 (4)C10B—C11B1.386 (2)
C1A—C2A1.379 (6)C11B—C12B1.386 (3)
C1A—C6A1.390 (6)C11B—H11B0.93
C1A—H1AA0.93C12B—C13B1.353 (4)
C2A—C3A1.360 (5)C12B—H12B0.93
C2A—H2AA0.93C13B—C14B1.358 (3)
C3A—C4A1.377 (5)C14B—C15B1.394 (3)
C4A—C5A1.376 (5)C14B—H14B0.93
C4A—H4AA0.93C15B—H15B0.93
C5A—C6A1.399 (6)C16B—C17B1.492 (3)
C5A—H5AA0.93C17B—H17D0.96
C6A—C7A1.497 (6)C17B—H17E0.96
F1X—C3X1.369 (11)C17B—H17F0.96
C1X—C2X1.385 (13)F2C—C13C1.368 (3)
C1X—C6X1.413 (13)O1C—C16C1.219 (2)
C1X—H1XA0.93N1C—C7C1.282 (2)
C2X—C3X1.348 (13)N1C—N2C1.3867 (18)
C2X—H2XA0.93N2C—C16C1.356 (2)
C3X—C4X1.377 (12)N2C—C9C1.478 (2)
C4X—C5X1.379 (13)F1C—C3C1.355 (6)
C4X—H4XA0.93C1C—C2C1.390 (7)
C5X—C6X1.399 (14)C1C—C6C1.396 (6)
C5X—H5XA0.93C1C—H1CA0.93
C6X—C7A1.367 (18)C2C—C3C1.354 (7)
C7A—C8A1.499 (2)C2C—H2CA0.93
C8A—C9A1.547 (2)C3C—C4C1.375 (6)
C8A—H8AA0.97C4C—C5C1.376 (6)
C8A—H8AB0.97C4C—H4CA0.93
C9A—C10A1.509 (3)C5C—C6C1.400 (7)
C9A—H9AA0.98C5C—H5CA0.93
C10A—C11A1.385 (2)C6C—C7C1.516 (7)
C10A—C15A1.388 (3)F1Y—C3Y1.365 (11)
C11A—C12A1.384 (3)C1Y—C2Y1.388 (13)
C11A—H11A0.93C1Y—C6Y1.396 (12)
C12A—C13A1.351 (4)C1Y—H1YA0.93
C12A—H12A0.93C2Y—C3Y1.367 (12)
C13A—C14A1.357 (3)C2Y—H2YA0.93
C14A—C15A1.391 (3)C3Y—C4Y1.384 (11)
C14A—H14A0.93C4Y—C5Y1.373 (11)
C15A—H15A0.93C4Y—H4YA0.93
C16A—C17A1.486 (3)C5Y—C6Y1.412 (12)
C17A—H17A0.96C5Y—H5YA0.93
C17A—H17B0.96C6Y—C7C1.329 (16)
C17A—H17C0.96C7C—C8C1.502 (2)
F1B—C3B1.360 (2)C8C—C9C1.542 (2)
F2B—C13B1.368 (3)C8C—H8CA0.97
O1B—C16B1.223 (2)C8C—H8CB0.97
N1B—C7B1.288 (2)C9C—C10C1.514 (3)
N1B—N2B1.3873 (18)C9C—H9CA0.98
N2B—C16B1.365 (2)C10C—C15C1.384 (3)
N2B—C9B1.480 (2)C10C—C11C1.391 (2)
C1B—C2B1.385 (2)C11C—C12C1.383 (3)
C1B—C6B1.396 (2)C11C—H11C0.93
C1B—H1BA0.93C12C—C13C1.351 (4)
C2B—C3B1.361 (3)C12C—H12C0.93
C2B—H2BA0.93C13C—C14C1.358 (3)
C3B—C4B1.374 (3)C14C—C15C1.383 (3)
C4B—C5B1.377 (2)C14C—H14C0.93
C4B—H4BA0.93C15C—H15C0.93
C5B—C6B1.394 (3)C16C—C17C1.483 (3)
C5B—H5BA0.93C17C—H17G0.96
C6B—C7B1.463 (2)C17C—H17H0.96
C7B—C8B1.501 (3)C17C—H17I0.96
C7A—N1A—N2A108.01 (14)N2B—C9B—C8B101.28 (14)
C16A—N2A—N1A121.67 (15)C10B—C9B—C8B115.55 (17)
C16A—N2A—C9A124.59 (15)N2B—C9B—H9BA109.5
N1A—N2A—C9A113.27 (13)C10B—C9B—H9BA109.5
C2A—C1A—C6A121.0 (5)C8B—C9B—H9BA109.5
C2A—C1A—H1AA119.5C15B—C10B—C11B118.6 (2)
C6A—C1A—H1AA119.5C15B—C10B—C9B121.48 (16)
C3A—C2A—C1A117.5 (5)C11B—C10B—C9B119.88 (18)
C3A—C2A—H2AA121.2C12B—C11B—C10B120.5 (2)
C1A—C2A—H2AA121.2C12B—C11B—H11B119.7
F1A—C3A—C2A118.2 (4)C10B—C11B—H11B119.7
F1A—C3A—C4A117.7 (4)C13B—C12B—C11B118.7 (2)
C2A—C3A—C4A124.1 (4)C13B—C12B—H12B120.6
C5A—C4A—C3A117.9 (5)C11B—C12B—H12B120.6
C5A—C4A—H4AA121.0C12B—C13B—C14B123.3 (2)
C3A—C4A—H4AA121.0C12B—C13B—F2B118.3 (2)
C4A—C5A—C6A120.1 (5)C14B—C13B—F2B118.4 (2)
C4A—C5A—H5AA119.9C13B—C14B—C15B117.8 (2)
C6A—C5A—H5AA119.9C13B—C14B—H14B121.1
C1A—C6A—C5A119.2 (5)C15B—C14B—H14B121.1
C1A—C6A—C7A121.0 (5)C10B—C15B—C14B121.08 (19)
C5A—C6A—C7A119.8 (5)C10B—C15B—H15B119.5
C2X—C1X—C6X122.8 (15)C14B—C15B—H15B119.5
C2X—C1X—H1XA118.6O1B—C16B—N2B119.4 (2)
C6X—C1X—H1XA118.6O1B—C16B—C17B123.72 (18)
C3X—C2X—C1X120.2 (15)N2B—C16B—C17B116.87 (16)
C3X—C2X—H2XA119.9C16B—C17B—H17D109.5
C1X—C2X—H2XA119.9C16B—C17B—H17E109.5
C2X—C3X—F1X121.8 (12)H17D—C17B—H17E109.5
C2X—C3X—C4X121.1 (12)C16B—C17B—H17F109.5
F1X—C3X—C4X117.1 (12)H17D—C17B—H17F109.5
C3X—C4X—C5X117.1 (13)H17E—C17B—H17F109.5
C3X—C4X—H4XA121.4C7C—N1C—N2C108.00 (14)
C5X—C4X—H4XA121.4C16C—N2C—N1C122.17 (16)
C4X—C5X—C6X125.9 (14)C16C—N2C—C9C124.71 (15)
C4X—C5X—H5XA117.1N1C—N2C—C9C113.01 (13)
C6X—C5X—H5XA117.1C2C—C1C—C6C120.1 (6)
C7A—C6X—C5X124.4 (15)C2C—C1C—H1CA119.9
C7A—C6X—C1X123.0 (14)C6C—C1C—H1CA119.9
C5X—C6X—C1X112.6 (14)C3C—C2C—C1C117.9 (6)
N1A—C7A—C6X119.1 (8)C3C—C2C—H2CA121.1
N1A—C7A—C6A120.7 (3)C1C—C2C—H2CA121.1
N1A—C7A—C8A114.60 (15)C2C—C3C—F1C118.3 (6)
C6X—C7A—C8A125.8 (8)C2C—C3C—C4C124.4 (6)
C6A—C7A—C8A124.6 (3)F1C—C3C—C4C117.4 (6)
C7A—C8A—C9A102.63 (15)C3C—C4C—C5C117.8 (6)
C7A—C8A—H8AA111.2C3C—C4C—H4CA121.1
C9A—C8A—H8AA111.2C5C—C4C—H4CA121.1
C7A—C8A—H8AB111.2C4C—C5C—C6C120.3 (5)
C9A—C8A—H8AB111.2C4C—C5C—H5CA119.9
H8AA—C8A—H8AB109.2C6C—C5C—H5CA119.9
N2A—C9A—C10A111.54 (15)C1C—C6C—C5C119.5 (6)
N2A—C9A—C8A101.25 (13)C1C—C6C—C7C122.2 (6)
C10A—C9A—C8A116.02 (17)C5C—C6C—C7C118.2 (5)
N2A—C9A—H9AA109.2C2Y—C1Y—C6Y123.4 (14)
C10A—C9A—H9AA109.2C2Y—C1Y—H1YA118.3
C8A—C9A—H9AA109.2C6Y—C1Y—H1YA118.3
C11A—C10A—C15A118.2 (2)C3Y—C2Y—C1Y119.5 (13)
C11A—C10A—C9A120.21 (18)C3Y—C2Y—H2YA120.2
C15A—C10A—C9A121.60 (17)C1Y—C2Y—H2YA120.2
C12A—C11A—C10A120.8 (2)F1Y—C3Y—C2Y122.2 (13)
C12A—C11A—H11A119.6F1Y—C3Y—C4Y117.5 (12)
C10A—C11A—H11A119.6C2Y—C3Y—C4Y120.2 (11)
C13A—C12A—C11A118.9 (2)C5Y—C4Y—C3Y118.4 (11)
C13A—C12A—H12A120.6C5Y—C4Y—H4YA120.8
C11A—C12A—H12A120.6C3Y—C4Y—H4YA120.8
C12A—C13A—C14A123.0 (2)C4Y—C5Y—C6Y124.3 (12)
C12A—C13A—F2A118.6 (2)C4Y—C5Y—H5YA117.9
C14A—C13A—F2A118.4 (3)C6Y—C5Y—H5YA117.9
C13A—C14A—C15A118.1 (2)C7C—C6Y—C1Y118.9 (13)
C13A—C14A—H14A121.0C7C—C6Y—C5Y127.3 (13)
C15A—C14A—H14A121.0C1Y—C6Y—C5Y113.4 (13)
C10A—C15A—C14A121.08 (19)N1C—C7C—C6Y118.2 (7)
C10A—C15A—H15A119.5N1C—C7C—C8C114.27 (15)
C14A—C15A—H15A119.5C6Y—C7C—C8C127.2 (7)
O1A—C16A—N2A119.64 (18)N1C—C7C—C6C121.6 (3)
O1A—C16A—C17A123.35 (17)C8C—C7C—C6C124.1 (3)
N2A—C16A—C17A117.00 (15)C7C—C8C—C9C102.18 (15)
C16A—C17A—H17A109.5C7C—C8C—H8CA111.3
C16A—C17A—H17B109.5C9C—C8C—H8CA111.3
H17A—C17A—H17B109.5C7C—C8C—H8CB111.3
C16A—C17A—H17C109.5C9C—C8C—H8CB111.3
H17A—C17A—H17C109.5H8CA—C8C—H8CB109.2
H17B—C17A—H17C109.5N2C—C9C—C10C111.47 (15)
C7B—N1B—N2B108.18 (15)N2C—C9C—C8C100.87 (13)
C16B—N2B—N1B121.94 (16)C10C—C9C—C8C115.30 (17)
C16B—N2B—C9B124.58 (15)N2C—C9C—H9CA109.6
N1B—N2B—C9B113.25 (14)C10C—C9C—H9CA109.6
C2B—C1B—C6B120.88 (18)C8C—C9C—H9CA109.6
C2B—C1B—H1BA119.6C15C—C10C—C11C118.38 (19)
C6B—C1B—H1BA119.6C15C—C10C—C9C121.91 (16)
C3B—C2B—C1B118.29 (17)C11C—C10C—C9C119.70 (18)
C3B—C2B—H2BA120.9C12C—C11C—C10C120.7 (2)
C1B—C2B—H2BA120.9C12C—C11C—H11C119.7
F1B—C3B—C2B118.77 (17)C10C—C11C—H11C119.7
F1B—C3B—C4B117.96 (18)C13C—C12C—C11C118.5 (2)
C2B—C3B—C4B123.26 (17)C13C—C12C—H12C120.7
C3B—C4B—C5B117.89 (18)C11C—C12C—H12C120.7
C3B—C4B—H4BA121.1C12C—C13C—C14C123.2 (2)
C5B—C4B—H4BA121.1C12C—C13C—F2C118.2 (2)
C4B—C5B—C6B121.40 (17)C14C—C13C—F2C118.5 (2)
C4B—C5B—H5BA119.3C13C—C14C—C15C118.2 (2)
C6B—C5B—H5BA119.3C13C—C14C—H14C120.9
C5B—C6B—C1B118.20 (16)C15C—C14C—H14C120.9
C5B—C6B—C7B120.86 (16)C14C—C15C—C10C120.96 (19)
C1B—C6B—C7B120.94 (17)C14C—C15C—H15C119.5
N1B—C7B—C6B120.47 (16)C10C—C15C—H15C119.5
N1B—C7B—C8B114.47 (15)O1C—C16C—N2C119.7 (2)
C6B—C7B—C8B125.06 (16)O1C—C16C—C17C123.49 (18)
C7B—C8B—C9B102.45 (15)N2C—C16C—C17C116.85 (16)
C7B—C8B—H8BA111.3C16C—C17C—H17G109.5
C9B—C8B—H8BA111.3C16C—C17C—H17H109.5
C7B—C8B—H8BB111.3H17G—C17C—H17H109.5
C9B—C8B—H8BB111.3C16C—C17C—H17I109.5
H8BA—C8B—H8BB109.2H17G—C17C—H17I109.5
N2B—C9B—C10B111.14 (16)H17H—C17C—H17I109.5
C7A—N1A—N2A—C16A−168.87 (17)C16B—N2B—C9B—C8B−168.37 (19)
C7A—N1A—N2A—C9A3.5 (2)N1B—N2B—C9B—C8B6.1 (2)
C6A—C1A—C2A—C3A−3.3 (11)C7B—C8B—C9B—N2B−5.5 (2)
C1A—C2A—C3A—F1A−178.0 (6)C7B—C8B—C9B—C10B114.70 (18)
C1A—C2A—C3A—C4A0.5 (9)N2B—C9B—C10B—C15B73.5 (2)
F1A—C3A—C4A—C5A179.3 (4)C8B—C9B—C10B—C15B−41.2 (2)
C2A—C3A—C4A—C5A0.8 (7)N2B—C9B—C10B—C11B−104.97 (19)
C3A—C4A—C5A—C6A0.7 (7)C8B—C9B—C10B—C11B140.37 (18)
C2A—C1A—C6A—C5A4.8 (12)C15B—C10B—C11B—C12B−0.8 (3)
C2A—C1A—C6A—C7A−176.1 (7)C9B—C10B—C11B—C12B177.75 (19)
C4A—C5A—C6A—C1A−3.4 (11)C10B—C11B—C12B—C13B0.5 (3)
C4A—C5A—C6A—C7A177.5 (5)C11B—C12B—C13B—C14B−0.2 (4)
C6X—C1X—C2X—C3X5(3)C11B—C12B—C13B—F2B179.1 (2)
C1X—C2X—C3X—F1X175.1 (15)C12B—C13B—C14B—C15B0.2 (4)
C1X—C2X—C3X—C4X−5(2)F2B—C13B—C14B—C15B−179.1 (2)
C2X—C3X—C4X—C5X5(2)C11B—C10B—C15B—C14B0.7 (3)
F1X—C3X—C4X—C5X−175.6 (12)C9B—C10B—C15B—C14B−177.75 (18)
C3X—C4X—C5X—C6X−5(2)C13B—C14B—C15B—C10B−0.4 (3)
C4X—C5X—C6X—C7A−176.1 (18)N1B—N2B—C16B—O1B−175.16 (17)
C4X—C5X—C6X—C1X5(3)C9B—N2B—C16B—O1B−1.1 (3)
C2X—C1X—C6X—C7A176 (2)N1B—N2B—C16B—C17B6.2 (3)
C2X—C1X—C6X—C5X−5(3)C9B—N2B—C16B—C17B−179.76 (19)
N2A—N1A—C7A—C6X−172.3 (15)C7C—N1C—N2C—C16C−169.85 (17)
N2A—N1A—C7A—C6A176.6 (4)C7C—N1C—N2C—C9C6.5 (2)
N2A—N1A—C7A—C8A−0.3 (2)C6C—C1C—C2C—C3C−2.9 (18)
C5X—C6X—C7A—N1A−12 (3)C1C—C2C—C3C—F1C−177.5 (10)
C1X—C6X—C7A—N1A166.6 (18)C1C—C2C—C3C—C4C2.7 (14)
C5X—C6X—C7A—C6A90 (7)C2C—C3C—C4C—C5C0.2 (9)
C1X—C6X—C7A—C6A−91 (7)F1C—C3C—C4C—C5C−179.6 (5)
C5X—C6X—C7A—C8A176.6 (16)C3C—C4C—C5C—C6C−2.9 (8)
C1X—C6X—C7A—C8A−4(3)C2C—C1C—C6C—C5C0.3 (18)
C1A—C6A—C7A—N1A170.0 (6)C2C—C1C—C6C—C7C−178.9 (10)
C5A—C6A—C7A—N1A−10.9 (9)C4C—C5C—C6C—C1C2.7 (12)
C1A—C6A—C7A—C6X87 (6)C4C—C5C—C6C—C7C−178.1 (5)
C5A—C6A—C7A—C6X−94 (6)C6Y—C1Y—C2Y—C3Y5(4)
C1A—C6A—C7A—C8A−13.4 (10)C1Y—C2Y—C3Y—F1Y174 (2)
C5A—C6A—C7A—C8A165.7 (5)C1Y—C2Y—C3Y—C4Y−7(3)
N1A—C7A—C8A—C9A−2.7 (2)F1Y—C3Y—C4Y—C5Y−179.6 (12)
C6X—C7A—C8A—C9A168.6 (16)C2Y—C3Y—C4Y—C5Y1(2)
C6A—C7A—C8A—C9A−179.4 (5)C3Y—C4Y—C5Y—C6Y7(2)
C16A—N2A—C9A—C10A−68.8 (2)C2Y—C1Y—C6Y—C7C176 (3)
N1A—N2A—C9A—C10A119.06 (16)C2Y—C1Y—C6Y—C5Y3(4)
C16A—N2A—C9A—C8A167.22 (18)C4Y—C5Y—C6Y—C7C178.1 (15)
N1A—N2A—C9A—C8A−4.9 (2)C4Y—C5Y—C6Y—C1Y−9(3)
C7A—C8A—C9A—N2A4.23 (19)N2C—N1C—C7C—C6Y176.0 (12)
C7A—C8A—C9A—C10A−116.68 (18)N2C—N1C—C7C—C8C2.6 (2)
N2A—C9A—C10A—C11A102.35 (19)N2C—N1C—C7C—C6C−177.3 (4)
C8A—C9A—C10A—C11A−142.43 (18)C1Y—C6Y—C7C—N1C178 (2)
N2A—C9A—C10A—C15A−77.0 (2)C5Y—C6Y—C7C—N1C−9(3)
C8A—C9A—C10A—C15A38.2 (2)C1Y—C6Y—C7C—C8C−9(3)
C15A—C10A—C11A—C12A0.7 (3)C5Y—C6Y—C7C—C8C163.3 (15)
C9A—C10A—C11A—C12A−178.70 (19)C1Y—C6Y—C7C—C6C56 (8)
C10A—C11A—C12A—C13A−0.5 (4)C5Y—C6Y—C7C—C6C−131 (10)
C11A—C12A—C13A—C14A0.4 (4)C1C—C6C—C7C—N1C−178.1 (9)
C11A—C12A—C13A—F2A−178.6 (2)C5C—C6C—C7C—N1C2.8 (9)
C12A—C13A—C14A—C15A−0.5 (4)C1C—C6C—C7C—C6Y−117 (9)
F2A—C13A—C14A—C15A178.6 (2)C5C—C6C—C7C—C6Y64 (8)
C11A—C10A—C15A—C14A−0.8 (3)C1C—C6C—C7C—C8C2.0 (12)
C9A—C10A—C15A—C14A178.59 (18)C5C—C6C—C7C—C8C−177.1 (5)
C13A—C14A—C15A—C10A0.7 (3)N1C—C7C—C8C—C9C−9.8 (2)
N1A—N2A—C16A—O1A175.02 (16)C6Y—C7C—C8C—C9C177.4 (13)
C9A—N2A—C16A—O1A3.5 (3)C6C—C7C—C8C—C9C170.1 (4)
N1A—N2A—C16A—C17A−5.7 (3)C16C—N2C—C9C—C10C−72.8 (2)
C9A—N2A—C16A—C17A−177.21 (18)N1C—N2C—C9C—C10C110.90 (16)
C7B—N1B—N2B—C16B170.59 (18)C16C—N2C—C9C—C8C164.28 (18)
C7B—N1B—N2B—C9B−4.1 (2)N1C—N2C—C9C—C8C−12.0 (2)
C6B—C1B—C2B—C3B0.6 (3)C7C—C8C—C9C—N2C11.94 (19)
C1B—C2B—C3B—F1B−179.15 (18)C7C—C8C—C9C—C10C−108.26 (18)
C1B—C2B—C3B—C4B2.1 (3)N2C—C9C—C10C—C15C−80.1 (2)
F1B—C3B—C4B—C5B178.73 (18)C8C—C9C—C10C—C15C34.1 (2)
C2B—C3B—C4B—C5B−2.5 (3)N2C—C9C—C10C—C11C98.58 (19)
C3B—C4B—C5B—C6B0.2 (3)C8C—C9C—C10C—C11C−147.21 (17)
C4B—C5B—C6B—C1B2.3 (3)C15C—C10C—C11C—C12C0.1 (3)
C4B—C5B—C6B—C7B−178.54 (18)C9C—C10C—C11C—C12C−178.56 (19)
C2B—C1B—C6B—C5B−2.7 (3)C10C—C11C—C12C—C13C−0.2 (4)
C2B—C1B—C6B—C7B178.12 (17)C11C—C12C—C13C—C14C0.2 (4)
N2B—N1B—C7B—C6B−179.56 (15)C11C—C12C—C13C—F2C−179.2 (2)
N2B—N1B—C7B—C8B−0.1 (2)C12C—C13C—C14C—C15C−0.1 (4)
C5B—C6B—C7B—N1B10.3 (3)F2C—C13C—C14C—C15C179.2 (2)
C1B—C6B—C7B—N1B−170.53 (17)C13C—C14C—C15C—C10C0.1 (3)
C5B—C6B—C7B—C8B−169.09 (19)C11C—C10C—C15C—C14C−0.1 (3)
C1B—C6B—C7B—C8B10.1 (3)C9C—C10C—C15C—C14C178.58 (18)
N1B—C7B—C8B—C9B3.8 (2)N1C—N2C—C16C—O1C178.61 (17)
C6B—C7B—C8B—C9B−176.74 (18)C9C—N2C—C16C—O1C2.7 (3)
C16B—N2B—C9B—C10B68.4 (2)N1C—N2C—C16C—C17C−1.3 (3)
N1B—N2B—C9B—C10B−117.15 (16)C9C—N2C—C16C—C17C−177.25 (19)
Hydrogen-bond geometry (Å, °)
D—H···AD—HH···AD···AD—H···A
C12A—H12A···F2Ai0.932.533.294 (3)139
C12B—H12B···F2Cii0.932.533.309 (3)141
C12C—H12C···F2Biii0.932.533.320 (3)143
C17A—H17A···F1Civ0.962.533.276 (8)134
C17B—H17D···F1Av0.962.473.309 (4)146
C17C—H17G···F1Bi0.962.553.311 (2)137
C15A—H15A···O1C0.932.323.225 (3)165
C15B—H15B···O1Avi0.932.363.262 (3)162
C15C—H15C···O1Bvii0.932.423.281 (3)153
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z; (iii) x−1, y, z; (iv) x, y−1, z; (v) −x+2, −y+1, −z+1; (vi) −x+2, −y, −z+1; (vii) −x+1, −y+1, −z+1.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5026).
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