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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Pages o2783-o2784
https://doi.org/10.1107/S160053681103902X

4-[Bis(4-fluoro­phenyl)methyl]piperazin-1-ium 2-(2-phenylethyl)benzoate

Richard Betz,a* Thomas Gerber,a Eric Hosten,a Alaloor S. Dayanandab and Hemmige S. Yathirajanb

aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa, and bUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: richard.betz@webmail.co.za

(Received 21 September 2011; accepted 22 September 2011; online 30 September 2011)

The asymmetric unit of the title salt, C17H19F2N2+.C15H13O2−, derived from a 1,4-diaza­cyclo­hexane derivative and a carb­oxy­lic acid, contains two formula units. The cation is protonated at the secondary amine functionality. The six-membered heterocycles adopt chair conformations. The fluorophenyl rings in the two cations make dihedral angles of 77.21 (19) and 78.8 (2)° while the aromatic rings in the anions enclose angles of 69.5 (2) and 69.9 (2)°. In the crystal, classical N—H⋯O hydrogen bonds as well as C—H⋯F and C—H⋯O contacts connect the entities into layers parallel to ac.

Related literature

For the biological activity of piperazines, see: Brockunier et al. (2004[Brockunier, L. L., He, J., Colwell, L. F. Jr, Habulihaz, B., He, H., Leiting, B., Lyons, K. A., Marsilio, F., Patel, R. A., Teffera, Y., Wu, J. K., Thornberry, N. A., Weber, A. E. & Parmee, E. R. (2004). Bioorg. Med. Chem. Lett. 14, 4763-4766.]); Bogatcheva et al. (2006[Bogatcheva, E., Hanrahan, C., Nikonenko, B., Samala, R., Chen, P., Gearhart, J., Barbosa, F., Einck, L., Nacy, C. A. & Protopopova, M. (2006). J. Med. Chem. 49, 3045-3048.]). For related structures, see: Anilkumar et al. (2005[Anilkumar, H. G., Yathirajan, H. S., Narasimhamurthy, T., Vijay, T. & Rathore, R. S. (2005). Acta Cryst. E61, o2704-o2705.]); Betz et al. (2011[Betz, R., Gerber, T., Hosten, E., Dayananda, A. S., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o2587-o2588.]); Fun et al. (2011[Fun, H.-K., Hemamalini, M., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o1726.]); Jasinski et al. (2010[Jasinski, J. P., Butcher, R. J., Siddegowda, M. S., Yathirajan, H. S. & Ramesha, A. R. (2010). Acta Cryst. E66, o3167.], 2011[Jasinski, J. P., Butcher, R. J., Siddegowda, M. S., Yathirajan, H. S. & Chidan Kumar, C. S. (2011). Acta Cryst. E67, o500-o501.]); Dutkiewicz et al. (2011[Dutkiewicz, G., Samshuddin, S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2011). Acta Cryst. E67, o390-o391.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C17H19F2N2+·C15H13O2−

  • Mr = 514.60

  • Monoclinic, P 21

  • a = 8.2330 (2) Å

  • b = 35.5366 (10) Å

  • c = 10.1505 (3) Å

  • β = 112.925 (1)°

  • V = 2735.19 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 200 K

  • 0.52 × 0.34 × 0.31 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • 24852 measured reflections

  • 6889 independent reflections

  • 6401 reflections with I > 2σ(I)

  • Rint = 0.033
Refinement

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.129

  • S = 1.07

  • 6889 reflections

  • 701 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H721⋯O22 0.89 (4) 1.81 (4) 2.691 (3) 173 (4)
N2—H722⋯O12i 0.99 (4) 1.70 (4) 2.688 (3) 174 (4)
N4—H741⋯O21ii 0.94 (3) 1.75 (3) 2.683 (3) 174 (3)
N4—H742⋯O11iii 0.98 (4) 1.71 (4) 2.688 (3) 174 (3)
C23—H23⋯F1iv 0.95 2.41 3.281 (6) 153
C55—H55⋯F3iv 0.95 2.46 3.374 (5) 161
C3—H3A⋯O21iv 0.99 2.61 3.576 (3) 165
C5—H5B⋯O12v 0.99 2.60 3.564 (3) 164
Symmetry codes: (i) x+1, y, z; (ii) [-x+2, y+{\script{1\over 2}}, -z+1]; (iii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iv) x-1, y, z-1; (v) x+1, y, z+1.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT Bruker AXS Inc., Madison, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT Bruker AXS Inc., Madison, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681103902X/bt5651sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S160053681103902X/bt5651Isup2.cdx

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681103902X/bt5651Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681103902X/bt5651Isup4.cml

checkCIF report


Comment top

4,4'-Difluorobenzhydryl piperazine is an intermediate for the preparation of flunarizine which is a calcium channel blocker. Piperazines are among the most important building blocks in today's drug discovery. They are found in biologically active compounds across a number of different therapeutic areas such as antifungal, antibacterial, antimalarial, antipsychotic, antidepressant and antitumour activity against colon, prostate, breast, lung and leukemia tumors (Brockunier et al., 2004; Bogatcheva et al., 2006). The crystal structures of some related compounds, viz., 2-(2-phenylethyl)benzoic acid (Anilkumar et al., 2005), levocetirizinium dipicrate (Jasinski et al., 2010), cinnarizinium dipicrate (Jasinski et al., 2011), 1-methylpiperazine-1,4- diium dipicrate (Dutkiewicz et al., 2011) and 4-(4-chlorophenyl)-4-hydroxypipe ridinium 2-(2-phenylethyl)benzoate (Fun et al., 2011) have been reported. Recently, we have reported the crystal structure of 4-[bis(4-fluorophenyl) methyl]piperazin-1-ium picrate (Betz et al., 2011). In the course of our studies on the salts of piperazines and in view of the importance of piperazines, the paper reports the crystal and molecular structure of the title salt.

In both cations present in the asymmetric unit protonation occurred on the secondary amine functionality. According to a conformational analysis (Cremer & Pople, 1975), both diazacyclohexane moieties adopt a 4C1 chair conformation. The least-squares planes defined by the carbon atoms of the para-fluorophenyl moieties in the respective cations intersect at angles of 77.21 (19) ° and 78.8 (2) °. The aromatic systems in the anions enclose angles of 69.5 (2) ° and 69.9 (2) °, respectively (Fig. 1).

In the crystal, classical hydrogen bonds as well as C–H···F contacts and C–H···O contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating are observed. The classical hydrogen bonds are apparent between the protonated amine functionality and both oxygen atoms of the carboxylic acid and give rise to the formation of cyclic patterns involving both symmetry-independent cations and anions of the asymmetric unit. While the C–H···F contacts exclusively involve hydrogen atoms in ortho-position to the fluorine atoms on the para-fluorophenyl moieties and connect only one of the cations with its symmetry-generated equivalents, the C–H···O contacts appear between hydrogen atoms of the methylene groups in the carboxylates and "dimerize" the two independent anions present in the asymmetric unit. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the classical hydrogen bonds is DDDD on the unitary level while a R44(12) descriptor on the quartenary level emphasizes the presence of the cyclic patterns illustrated in Figure 2. For the C–H···F contacts, a C11(10)C11(10) descriptor on the unitary level shows the presence of two homodromic chains as depicted in Figure 3 while a R22(12) descriptor on the binary level is indicative for the cyclization of the two anions present in the asymmetric unit on grounds of C–H···O contacts (Fig. 4). In total, the entities of the title compound are connected to planes parallel to ac. The shortest intercentroid distance between two centers of gravity was found at 4.615 (3) Å.

The packing of the title compound in the crystal is shown in Figure 5.

Related literature top

For the biological activity of piperazines, see: Brockunier et al. (2004); Bogatcheva et al. (2006). For related structures, see: Anilkumar et al. (2005); Betz et al. (2011); Fun et al. (2011); Jasinski et al. (2010, 2011); Dutkiewicz et al. (2011). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995). For puckering analysis, see: Cremer & Pople (1975).

Experimental top

4,4'-Difluorobenzhydryl piperazine was obtained from R. L. Fine Chem., Bengaluru, India. 4,4'-Difluorobenzhydryl piperazine (2.88 g, 0.01 mol) was dissolved in 10 ml of methanol and 2-(2-phenylethyl)benzoic acid (2.26 g, 0.01 mol) was also dissolved in 10 ml of methanol. Both the solutions were mixed and stirred in a beaker at 333 K for 60 minutes. The mixture was kept aside for a day at room temperature. The salt formed was filtered & dried in vaccum desiccator over phosphorous pentoxide. X-ray quality crystals of the title compound were obtained from ethanol by slow evaporation.

Refinement top

Carbon-bound H atoms were placed in calculated positions (C—H 0.95 Å for aromatic carbon atoms, C—H 0.99 Å for methylene groups and C—H 1.00 Å for methine groups) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). All nitrogen-bound H atoms were located on a difference Fourier map and refined freely. A search for higher or missed symmetry by means of PLATON (Spek, 2009) revealed the presence of a local center of symmetry which is not compatible with the reported space-group symmetry nor with another space group.

Structure description top

4,4'-Difluorobenzhydryl piperazine is an intermediate for the preparation of flunarizine which is a calcium channel blocker. Piperazines are among the most important building blocks in today's drug discovery. They are found in biologically active compounds across a number of different therapeutic areas such as antifungal, antibacterial, antimalarial, antipsychotic, antidepressant and antitumour activity against colon, prostate, breast, lung and leukemia tumors (Brockunier et al., 2004; Bogatcheva et al., 2006). The crystal structures of some related compounds, viz., 2-(2-phenylethyl)benzoic acid (Anilkumar et al., 2005), levocetirizinium dipicrate (Jasinski et al., 2010), cinnarizinium dipicrate (Jasinski et al., 2011), 1-methylpiperazine-1,4- diium dipicrate (Dutkiewicz et al., 2011) and 4-(4-chlorophenyl)-4-hydroxypipe ridinium 2-(2-phenylethyl)benzoate (Fun et al., 2011) have been reported. Recently, we have reported the crystal structure of 4-[bis(4-fluorophenyl) methyl]piperazin-1-ium picrate (Betz et al., 2011). In the course of our studies on the salts of piperazines and in view of the importance of piperazines, the paper reports the crystal and molecular structure of the title salt.

In both cations present in the asymmetric unit protonation occurred on the secondary amine functionality. According to a conformational analysis (Cremer & Pople, 1975), both diazacyclohexane moieties adopt a 4C1 chair conformation. The least-squares planes defined by the carbon atoms of the para-fluorophenyl moieties in the respective cations intersect at angles of 77.21 (19) ° and 78.8 (2) °. The aromatic systems in the anions enclose angles of 69.5 (2) ° and 69.9 (2) °, respectively (Fig. 1).

In the crystal, classical hydrogen bonds as well as C–H···F contacts and C–H···O contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating are observed. The classical hydrogen bonds are apparent between the protonated amine functionality and both oxygen atoms of the carboxylic acid and give rise to the formation of cyclic patterns involving both symmetry-independent cations and anions of the asymmetric unit. While the C–H···F contacts exclusively involve hydrogen atoms in ortho-position to the fluorine atoms on the para-fluorophenyl moieties and connect only one of the cations with its symmetry-generated equivalents, the C–H···O contacts appear between hydrogen atoms of the methylene groups in the carboxylates and "dimerize" the two independent anions present in the asymmetric unit. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the classical hydrogen bonds is DDDD on the unitary level while a R44(12) descriptor on the quartenary level emphasizes the presence of the cyclic patterns illustrated in Figure 2. For the C–H···F contacts, a C11(10)C11(10) descriptor on the unitary level shows the presence of two homodromic chains as depicted in Figure 3 while a R22(12) descriptor on the binary level is indicative for the cyclization of the two anions present in the asymmetric unit on grounds of C–H···O contacts (Fig. 4). In total, the entities of the title compound are connected to planes parallel to ac. The shortest intercentroid distance between two centers of gravity was found at 4.615 (3) Å.

The packing of the title compound in the crystal is shown in Figure 5.

For the biological activity of piperazines, see: Brockunier et al. (2004); Bogatcheva et al. (2006). For related structures, see: Anilkumar et al. (2005); Betz et al. (2011); Fun et al. (2011); Jasinski et al. (2010, 2011); Dutkiewicz et al. (2011). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995). For puckering analysis, see: Cremer & Pople (1975).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
[Figure 2] Fig. 2. Intermolecular hydrogen bonds, viewed along [0 0 - 1]. Symmetry operators: i x + 1, y, z; ii -x + 2, y - 1/2, -z + 1.
[Figure 3] Fig. 3. Intermolecular C–H···F contacts, viewed along [0 - 1 0]. Symmetry operators: i x + 1, y, z + 1; ii x - 1, y, z - 1.
[Figure 4] Fig. 4. Intermolecular C–H···O contacts, viewed along [0 - 1 0]. Symmetry operator: i x + 1, y, z + 1.
[Figure 5] Fig. 5. Molecular packing of the title compound, viewed along [-1 0 0] (anisotropic displacement ellipsoids drawn at 50% probability level).
1-(4,4'-Difluorobenzhydryl)piperazinium 2-(2-phenylethyl)benzoate top
Crystal data top
C17H19F2N2+·C15H13O2−F(000) = 1088
Mr = 514.60Dx = 1.250 Mg m−3
Monoclinic, P21Melting point = 421–423 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 8.2330 (2) ÅCell parameters from 9860 reflections
b = 35.5366 (10) Åθ = 2.7–28.4°
c = 10.1505 (3) ŵ = 0.09 mm−1
β = 112.925 (1)°T = 200 K
V = 2735.19 (13) Å3Block, colourless
Z = 40.52 × 0.34 × 0.31 mm
Data collection top
Bruker APEXII CCD
diffractometer		6401 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 28.4°, θmin = 2.2°
φ and ω scansh = −10→10
24852 measured reflectionsk = −47→47
6889 independent reflectionsl = −13→13
Refinement top
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) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0526P)2 + 1.0497P]
where P = (Fo2 + 2Fc2)/3
6889 reflections(Δ/σ)max < 0.001
701 parametersΔρmax = 0.29 e Å−3
1 restraintΔρmin = −0.21 e Å−3
Crystal data top
C17H19F2N2+·C15H13O2−V = 2735.19 (13) Å3
Mr = 514.60Z = 4
Monoclinic, P21Mo Kα radiation
a = 8.2330 (2) ŵ = 0.09 mm−1
b = 35.5366 (10) ÅT = 200 K
c = 10.1505 (3) Å0.52 × 0.34 × 0.31 mm
β = 112.925 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		6401 reflections with I > 2σ(I)
24852 measured reflectionsRint = 0.033
6889 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0501 restraint
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.29 e Å−3
6889 reflectionsΔρmin = −0.21 e Å−3
701 parameters
Special details top

Refinement. Due to the absence of a strong anomalous scatterer, the Flack parameter is meaningless. Thus, Friedel opposites (6158 pairs) have been merged and the item was removed from the CIF.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F11.4107 (4)0.32440 (7)0.8569 (3)0.0889 (10)
F20.3726 (4)0.28909 (10)0.1502 (4)0.1198 (15)
N11.0316 (3)0.18603 (6)0.4512 (2)0.0314 (5)
N21.0636 (3)0.10540 (7)0.4518 (2)0.0305 (4)
H7211.043 (5)0.0832 (12)0.482 (4)0.044 (10)*
H7221.118 (5)0.1010 (11)0.382 (4)0.047 (10)*
C11.0484 (4)0.22471 (8)0.4080 (3)0.0355 (6)
H11.10650.22430.33800.043*
C111.1561 (4)0.24926 (9)0.5339 (3)0.0388 (6)
C121.1569 (4)0.24388 (9)0.6691 (3)0.0430 (7)
H121.09700.22280.68660.052*
C131.2436 (5)0.26877 (10)0.7796 (4)0.0517 (8)
H131.24470.26510.87260.062*
C141.3285 (5)0.29921 (10)0.7495 (4)0.0596 (10)
C151.3315 (5)0.30519 (11)0.6190 (5)0.0644 (11)
H151.39200.32630.60240.077*
C161.2453 (4)0.28013 (10)0.5099 (4)0.0498 (8)
H161.24680.28400.41780.060*
C210.8656 (4)0.24235 (9)0.3364 (3)0.0428 (7)
C220.8159 (6)0.26097 (11)0.2082 (4)0.0613 (10)
H220.89600.26250.16170.074*
C230.6517 (7)0.27755 (12)0.1455 (6)0.0815 (17)
H230.61900.29090.05790.098*
C240.5385 (7)0.27419 (12)0.2126 (6)0.0814 (17)
C250.5820 (6)0.25625 (17)0.3407 (5)0.0835 (17)
H250.50070.25470.38600.100*
C260.7489 (5)0.24032 (14)0.4030 (4)0.0634 (11)
H260.78270.22790.49260.076*
C310.9217 (4)0.16322 (8)0.3277 (3)0.0363 (6)
H31A0.98030.16100.25940.044*
H31B0.80660.17580.27790.044*
C320.8927 (4)0.12467 (9)0.3757 (3)0.0385 (6)
H32A0.82860.12690.44010.046*
H32B0.81940.10960.29160.046*
C331.1822 (4)0.12887 (8)0.5717 (3)0.0356 (6)
H33A1.29890.11650.61580.043*
H33B1.13220.13120.64570.043*
C341.2041 (4)0.16766 (8)0.5187 (3)0.0325 (5)
H34A1.28180.18310.60000.039*
H34B1.26010.16550.44870.039*
F30.9184 (4)0.30926 (7)0.8907 (3)0.0936 (11)
F4−0.1354 (4)0.35140 (9)0.2007 (4)0.0943 (10)
N30.5476 (3)0.44862 (6)0.4875 (2)0.0303 (4)
N40.5911 (3)0.52871 (6)0.4938 (2)0.0300 (4)
H7410.645 (4)0.5329 (9)0.429 (3)0.027 (7)*
H7420.573 (5)0.5529 (12)0.533 (4)0.047 (10)*
C20.5545 (4)0.40945 (8)0.4434 (3)0.0330 (5)
H20.60900.40900.37090.040*
C410.6616 (4)0.38422 (8)0.5681 (3)0.0363 (6)
C420.6641 (5)0.38961 (9)0.7039 (4)0.0444 (7)
H420.60530.41070.72250.053*
C430.7521 (6)0.36434 (10)0.8138 (4)0.0552 (9)
H430.75390.36790.90710.066*
C440.8353 (6)0.33440 (10)0.7838 (4)0.0635 (12)
C450.8376 (5)0.32788 (11)0.6516 (5)0.0617 (11)
H450.89710.30670.63450.074*
C460.7499 (4)0.35332 (10)0.5432 (4)0.0465 (7)
H460.75010.34960.45060.056*
C510.3684 (4)0.39346 (8)0.3756 (3)0.0378 (6)
C520.2507 (4)0.39973 (10)0.4405 (4)0.0462 (7)
H520.28670.41430.52560.055*
C530.0810 (5)0.38509 (12)0.3830 (4)0.0578 (9)
H530.00040.38930.42770.069*
C540.0338 (5)0.36447 (11)0.2600 (5)0.0622 (11)
C550.1451 (6)0.35709 (11)0.1942 (5)0.0675 (12)
H550.10830.34210.11010.081*
C560.3157 (5)0.37207 (10)0.2527 (4)0.0520 (8)
H560.39550.36750.20760.062*
C610.4425 (4)0.47188 (8)0.3648 (3)0.0343 (6)
H61A0.32650.45990.31310.041*
H61B0.50340.47400.29810.041*
C620.4163 (4)0.51067 (8)0.4146 (3)0.0355 (6)
H62A0.34630.52630.33110.043*
H62B0.35050.50870.47780.043*
C630.7059 (4)0.50441 (8)0.6112 (3)0.0347 (6)
H63A0.65580.50210.68510.042*
H63B0.82420.51600.65620.042*
C640.7228 (4)0.46568 (8)0.5556 (3)0.0344 (6)
H64A0.77860.46770.48530.041*
H64B0.79850.44960.63560.041*
O110.4801 (3)0.09313 (7)0.4005 (2)0.0450 (5)
O120.2001 (3)0.09716 (8)0.2522 (2)0.0479 (6)
C30.4593 (4)0.05677 (9)0.0815 (3)0.0387 (6)
H3A0.42310.0473−0.01770.046*
H3B0.37000.04830.11790.046*
C40.6352 (4)0.03940 (10)0.1726 (4)0.0432 (7)
H4A0.66300.04620.27370.052*
H4B0.72710.05080.14510.052*
C700.3612 (4)0.10230 (7)0.2842 (3)0.0303 (5)
C710.4142 (3)0.12085 (8)0.1735 (3)0.0286 (5)
C720.4604 (3)0.09921 (9)0.0786 (3)0.0328 (6)
C730.5049 (4)0.11850 (11)−0.0232 (3)0.0468 (8)
H730.53640.1044−0.08920.056*
C740.5045 (5)0.15704 (12)−0.0306 (4)0.0528 (9)
H740.53620.1692−0.10050.063*
C750.4583 (5)0.17797 (10)0.0633 (4)0.0476 (8)
H750.45740.20470.05830.057*
C760.4130 (4)0.15991 (9)0.1651 (3)0.0384 (6)
H760.38080.17440.22990.046*
C810.6466 (4)−0.00298 (10)0.1627 (4)0.0436 (7)
C820.7804 (4)−0.02184 (11)0.2695 (4)0.0459 (7)
H820.8586−0.00820.34980.055*
C830.8023 (5)−0.06030 (12)0.2611 (5)0.0567 (9)
H830.8960−0.07280.33480.068*
C840.6894 (6)−0.08038 (12)0.1471 (5)0.0645 (11)
H840.7046−0.10670.14120.077*
C850.5545 (7)−0.06220 (13)0.0419 (6)0.0752 (13)
H850.4742−0.0762−0.03600.090*
C860.5335 (6)−0.02363 (12)0.0474 (5)0.0658 (11)
H860.4414−0.0113−0.02800.079*
O211.2741 (3)0.03769 (8)0.7060 (2)0.0476 (6)
O220.9933 (3)0.04102 (7)0.5589 (2)0.0474 (6)
C51.0165 (4)0.07915 (9)0.8772 (3)0.0372 (6)
H5A1.10550.08740.84010.045*
H5B1.05310.08890.97600.045*
C60.8398 (4)0.09635 (10)0.7856 (4)0.0454 (7)
H6A0.81110.08910.68480.054*
H6B0.74850.08520.81460.054*
C901.1135 (4)0.03262 (7)0.6758 (3)0.0290 (5)
C911.0624 (3)0.01466 (8)0.7887 (3)0.0284 (5)
C921.0155 (3)0.03688 (8)0.8817 (3)0.0318 (5)
C930.9734 (4)0.01861 (11)0.9856 (3)0.0435 (7)
H930.94300.03311.05120.052*
C940.9748 (5)−0.02027 (12)0.9953 (4)0.0505 (8)
H940.9443−0.03211.06650.061*
C951.0202 (5)−0.04179 (10)0.9028 (4)0.0479 (8)
H951.0210−0.06850.90930.057*
C961.0649 (4)−0.02419 (9)0.7995 (3)0.0394 (6)
H961.0975−0.03890.73560.047*
C1010.8281 (4)0.13874 (10)0.7924 (4)0.0438 (7)
C1020.9426 (6)0.16027 (12)0.9050 (5)0.0647 (11)
H1021.03620.14840.98100.078*
C1030.9205 (7)0.19880 (13)0.9066 (6)0.0736 (13)
H1031.00120.21320.98280.088*
C1040.7849 (6)0.21651 (11)0.8007 (6)0.0662 (11)
H1040.76930.24290.80340.079*
C1050.6722 (5)0.19542 (11)0.6909 (5)0.0555 (9)
H1050.57690.20750.61710.067*
C1060.6932 (4)0.15714 (11)0.6844 (4)0.0476 (7)
H1060.61450.14330.60520.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.096 (2)0.0387 (12)0.0827 (17)−0.0108 (13)−0.0189 (15)−0.0037 (12)
F20.0812 (19)0.090 (2)0.120 (2)0.0560 (17)−0.0348 (17)−0.0352 (19)
N10.0293 (11)0.0271 (11)0.0342 (11)0.0013 (9)0.0084 (9)0.0027 (8)
N20.0326 (11)0.0275 (11)0.0334 (11)0.0002 (9)0.0150 (9)0.0045 (9)
C10.0360 (14)0.0322 (14)0.0376 (14)0.0025 (11)0.0136 (11)0.0054 (11)
C110.0347 (14)0.0318 (14)0.0455 (15)0.0053 (11)0.0107 (12)0.0092 (11)
C120.0468 (17)0.0325 (15)0.0447 (16)−0.0021 (13)0.0125 (13)0.0031 (12)
C130.056 (2)0.0381 (17)0.0487 (18)0.0050 (15)0.0068 (15)−0.0011 (13)
C140.056 (2)0.0283 (16)0.066 (2)−0.0024 (15)−0.0074 (17)0.0033 (15)
C150.051 (2)0.0377 (18)0.076 (3)−0.0085 (15)−0.0063 (18)0.0159 (17)
C160.0392 (16)0.0417 (18)0.062 (2)−0.0010 (14)0.0121 (14)0.0167 (15)
C210.0471 (17)0.0314 (15)0.0397 (15)0.0084 (12)0.0056 (13)0.0010 (11)
C220.061 (2)0.0430 (19)0.055 (2)−0.0063 (16)−0.0035 (17)0.0135 (16)
C230.073 (3)0.042 (2)0.079 (3)−0.002 (2)−0.025 (2)0.018 (2)
C240.061 (3)0.045 (2)0.088 (3)0.028 (2)−0.026 (2)−0.024 (2)
C250.057 (2)0.113 (4)0.064 (3)0.044 (3)0.006 (2)−0.025 (3)
C260.053 (2)0.084 (3)0.0454 (18)0.032 (2)0.0104 (15)−0.0022 (18)
C310.0302 (13)0.0332 (14)0.0374 (14)0.0011 (11)0.0043 (11)0.0010 (11)
C320.0271 (12)0.0391 (16)0.0472 (16)0.0001 (11)0.0122 (12)−0.0001 (12)
C330.0349 (13)0.0359 (15)0.0315 (13)0.0036 (11)0.0081 (11)0.0043 (10)
C340.0263 (12)0.0303 (13)0.0368 (13)0.0011 (10)0.0077 (10)0.0031 (10)
F30.117 (2)0.0433 (13)0.0669 (15)0.0117 (14)−0.0221 (15)0.0043 (11)
F40.0596 (14)0.0745 (18)0.112 (2)−0.0370 (13)−0.0065 (14)−0.0032 (16)
N30.0278 (11)0.0243 (10)0.0350 (11)−0.0013 (8)0.0081 (9)−0.0030 (8)
N40.0299 (11)0.0287 (11)0.0342 (11)−0.0016 (9)0.0155 (9)−0.0035 (8)
C20.0388 (14)0.0272 (13)0.0341 (13)−0.0006 (11)0.0153 (11)−0.0034 (10)
C410.0360 (14)0.0269 (13)0.0436 (15)−0.0009 (11)0.0129 (12)−0.0039 (11)
C420.0516 (18)0.0336 (16)0.0454 (16)0.0010 (13)0.0159 (14)−0.0008 (12)
C430.069 (2)0.0392 (18)0.0427 (17)−0.0043 (16)0.0053 (16)0.0003 (13)
C440.069 (2)0.0320 (17)0.057 (2)−0.0004 (16)−0.0104 (18)0.0013 (14)
C450.058 (2)0.0330 (17)0.071 (2)0.0139 (15)−0.0001 (18)−0.0100 (16)
C460.0436 (17)0.0359 (16)0.0530 (18)0.0030 (13)0.0111 (14)−0.0089 (13)
C510.0432 (15)0.0249 (13)0.0375 (14)−0.0049 (11)0.0073 (12)−0.0025 (10)
C520.0448 (17)0.0463 (17)0.0464 (17)−0.0168 (14)0.0163 (14)−0.0050 (13)
C530.0496 (19)0.054 (2)0.065 (2)−0.0190 (16)0.0168 (17)0.0047 (17)
C540.049 (2)0.0357 (17)0.075 (3)−0.0171 (15)−0.0046 (18)0.0060 (16)
C550.067 (3)0.0378 (18)0.065 (2)−0.0010 (17)−0.0110 (19)−0.0186 (16)
C560.057 (2)0.0368 (16)0.0480 (18)0.0038 (14)0.0049 (15)−0.0126 (14)
C610.0306 (13)0.0311 (14)0.0347 (13)−0.0041 (11)0.0056 (10)−0.0033 (10)
C620.0271 (12)0.0307 (14)0.0467 (15)0.0003 (10)0.0122 (11)−0.0012 (11)
C630.0355 (13)0.0293 (13)0.0345 (13)−0.0031 (11)0.0084 (11)−0.0036 (10)
C640.0255 (12)0.0326 (14)0.0402 (14)−0.0008 (10)0.0074 (10)−0.0027 (11)
O110.0446 (12)0.0491 (13)0.0376 (11)−0.0035 (10)0.0119 (9)0.0152 (9)
O120.0352 (11)0.0733 (17)0.0412 (11)−0.0098 (11)0.0214 (9)0.0006 (11)
C30.0359 (14)0.0436 (17)0.0376 (14)0.0001 (12)0.0155 (12)−0.0065 (12)
C40.0326 (14)0.0419 (16)0.0501 (17)−0.0010 (12)0.0106 (12)−0.0086 (13)
C700.0397 (14)0.0266 (12)0.0292 (12)−0.0022 (10)0.0185 (10)−0.0040 (9)
C710.0241 (11)0.0342 (13)0.0268 (11)−0.0040 (10)0.0092 (9)0.0023 (9)
C720.0271 (12)0.0427 (16)0.0286 (12)0.0007 (11)0.0108 (10)0.0007 (10)
C730.0440 (16)0.066 (2)0.0367 (15)−0.0039 (15)0.0229 (13)−0.0004 (14)
C740.0529 (19)0.064 (2)0.0466 (18)−0.0066 (17)0.0246 (15)0.0187 (16)
C750.0478 (18)0.0401 (17)0.0538 (19)−0.0073 (14)0.0187 (15)0.0123 (14)
C760.0427 (15)0.0318 (14)0.0426 (15)−0.0044 (12)0.0185 (12)0.0010 (11)
C810.0313 (14)0.0442 (17)0.0551 (18)−0.0005 (13)0.0166 (13)−0.0083 (14)
C820.0386 (16)0.055 (2)0.0481 (17)−0.0031 (14)0.0215 (13)0.0008 (14)
C830.052 (2)0.059 (2)0.069 (2)0.0083 (18)0.0354 (18)0.0204 (19)
C840.069 (3)0.0378 (19)0.099 (3)0.0017 (18)0.047 (2)0.0075 (19)
C850.076 (3)0.045 (2)0.089 (3)−0.007 (2)0.014 (2)−0.018 (2)
C860.055 (2)0.045 (2)0.075 (3)0.0003 (17)0.0012 (19)−0.0105 (18)
O210.0380 (11)0.0722 (17)0.0379 (11)−0.0064 (11)0.0206 (9)0.0020 (10)
O220.0448 (12)0.0552 (14)0.0382 (11)−0.0088 (11)0.0118 (9)0.0152 (10)
C50.0346 (14)0.0375 (15)0.0431 (15)−0.0010 (11)0.0190 (12)−0.0079 (12)
C60.0341 (14)0.0447 (18)0.0513 (18)−0.0007 (13)0.0100 (13)−0.0109 (14)
C900.0355 (13)0.0249 (12)0.0297 (12)−0.0029 (10)0.0162 (10)−0.0013 (9)
C910.0232 (11)0.0329 (13)0.0284 (12)−0.0018 (9)0.0094 (9)0.0014 (9)
C920.0266 (12)0.0402 (15)0.0299 (12)−0.0030 (11)0.0123 (10)−0.0012 (10)
C930.0464 (17)0.057 (2)0.0341 (14)−0.0012 (15)0.0226 (13)0.0005 (13)
C940.056 (2)0.060 (2)0.0409 (16)−0.0091 (17)0.0245 (14)0.0137 (14)
C950.0498 (19)0.0427 (18)0.0494 (18)−0.0071 (14)0.0174 (15)0.0115 (13)
C960.0395 (15)0.0380 (16)0.0436 (15)−0.0032 (12)0.0194 (12)0.0009 (12)
C1010.0344 (14)0.0357 (15)0.0619 (19)−0.0020 (12)0.0195 (14)−0.0098 (14)
C1020.050 (2)0.049 (2)0.072 (3)−0.0002 (17)−0.0006 (18)−0.0118 (19)
C1030.071 (3)0.047 (2)0.091 (3)−0.011 (2)0.019 (2)−0.023 (2)
C1040.067 (3)0.0350 (19)0.109 (4)−0.0043 (17)0.047 (3)−0.0024 (19)
C1050.0471 (18)0.049 (2)0.077 (2)0.0017 (16)0.0314 (18)0.0175 (18)
C1060.0366 (15)0.054 (2)0.0567 (19)−0.0030 (14)0.0226 (14)−0.0064 (15)
Geometric parameters (Å, º) top
F1—C141.369 (4)C56—H560.9500
F2—C241.369 (5)C61—C621.512 (4)
N1—C11.466 (4)C61—H61A0.9900
N1—C341.468 (3)C61—H61B0.9900
N1—C311.471 (3)C62—H62A0.9900
N2—C321.483 (4)C62—H62B0.9900
N2—C331.485 (4)C63—C641.514 (4)
N2—H7210.89 (4)C63—H63A0.9900
N2—H7220.99 (4)C63—H63B0.9900
C1—C111.515 (4)C64—H64A0.9900
C1—C211.528 (4)C64—H64B0.9900
C1—H11.0000O11—C701.248 (3)
C11—C121.383 (5)O12—C701.250 (3)
C11—C161.393 (4)C3—C721.508 (4)
C12—C131.388 (5)C3—C41.513 (4)
C12—H120.9500C3—H3A0.9900
C13—C141.385 (6)C3—H3B0.9900
C13—H130.9500C4—C811.515 (5)
C14—C151.351 (6)C4—H4A0.9900
C15—C161.382 (6)C4—H4B0.9900
C15—H150.9500C70—C711.506 (3)
C16—H160.9500C71—C761.391 (4)
C21—C221.373 (5)C71—C721.396 (4)
C21—C261.375 (6)C72—C731.402 (4)
C22—C231.382 (6)C73—C741.372 (6)
C22—H220.9500C73—H730.9500
C23—C241.358 (8)C74—C751.375 (6)
C23—H230.9500C74—H740.9500
C24—C251.365 (8)C75—C761.385 (4)
C25—C261.390 (5)C75—H750.9500
C25—H250.9500C76—H760.9500
C26—H260.9500C81—C821.381 (5)
C31—C321.504 (4)C81—C861.388 (5)
C31—H31A0.9900C82—C831.386 (6)
C31—H31B0.9900C82—H820.9500
C32—H32A0.9900C83—C841.369 (6)
C32—H32B0.9900C83—H830.9500
C33—C341.515 (4)C84—C851.366 (7)
C33—H33A0.9900C84—H840.9500
C33—H33B0.9900C85—C861.386 (6)
C34—H34A0.9900C85—H850.9500
C34—H34B0.9900C86—H860.9500
F3—C441.365 (4)O21—C901.249 (3)
F4—C541.366 (4)O22—C901.250 (3)
N3—C611.464 (3)C5—C921.503 (4)
N3—C641.466 (3)C5—C61.517 (4)
N3—C21.470 (3)C5—H5A0.9900
N4—C631.477 (4)C5—H5B0.9900
N4—C621.492 (3)C6—C1011.513 (5)
N4—H7410.94 (3)C6—H6A0.9900
N4—H7420.98 (4)C6—H6B0.9900
C2—C411.521 (4)C90—C911.508 (3)
C2—C511.524 (4)C91—C961.384 (4)
C2—H21.0000C91—C921.396 (4)
C41—C421.384 (5)C92—C931.393 (4)
C41—C461.393 (4)C93—C941.385 (5)
C42—C431.395 (5)C93—H930.9500
C42—H420.9500C94—C951.371 (6)
C43—C441.362 (6)C94—H940.9500
C43—H430.9500C95—C961.388 (4)
C44—C451.370 (7)C95—H950.9500
C45—C461.389 (5)C96—H960.9500
C45—H450.9500C101—C1061.383 (5)
C46—H460.9500C101—C1021.393 (5)
C51—C561.378 (4)C102—C1031.383 (6)
C51—C521.386 (5)C102—H1020.9500
C52—C531.388 (5)C103—C1041.365 (7)
C52—H520.9500C103—H1030.9500
C53—C541.368 (6)C104—C1051.363 (6)
C53—H530.9500C104—H1040.9500
C54—C551.353 (7)C105—C1061.376 (6)
C55—C561.399 (6)C105—H1050.9500
C55—H550.9500C106—H1060.9500
C1—N1—C34111.7 (2)N3—C61—C62110.1 (2)
C1—N1—C31111.1 (2)N3—C61—H61A109.6
C34—N1—C31108.4 (2)C62—C61—H61A109.6
C32—N2—C33110.8 (2)N3—C61—H61B109.6
C32—N2—H721109 (2)C62—C61—H61B109.6
C33—N2—H721111 (2)H61A—C61—H61B108.1
C32—N2—H722108 (2)N4—C62—C61109.8 (2)
C33—N2—H722110 (2)N4—C62—H62A109.7
H721—N2—H722108 (3)C61—C62—H62A109.7
N1—C1—C11112.4 (2)N4—C62—H62B109.7
N1—C1—C21109.7 (2)C61—C62—H62B109.7
C11—C1—C21108.0 (2)H62A—C62—H62B108.2
N1—C1—H1108.9N4—C63—C64110.7 (2)
C11—C1—H1108.9N4—C63—H63A109.5
C21—C1—H1108.9C64—C63—H63A109.5
C12—C11—C16118.9 (3)N4—C63—H63B109.5
C12—C11—C1122.1 (3)C64—C63—H63B109.5
C16—C11—C1118.8 (3)H63A—C63—H63B108.1
C11—C12—C13121.0 (3)N3—C64—C63109.6 (2)
C11—C12—H12119.5N3—C64—H64A109.7
C13—C12—H12119.5C63—C64—H64A109.7
C14—C13—C12117.7 (4)N3—C64—H64B109.7
C14—C13—H13121.2C63—C64—H64B109.7
C12—C13—H13121.2H64A—C64—H64B108.2
C15—C14—F1119.1 (4)C72—C3—C4114.1 (3)
C15—C14—C13122.8 (3)C72—C3—H3A108.7
F1—C14—C13118.1 (4)C4—C3—H3A108.7
C14—C15—C16118.9 (4)C72—C3—H3B108.7
C14—C15—H15120.5C4—C3—H3B108.7
C16—C15—H15120.5H3A—C3—H3B107.6
C15—C16—C11120.6 (4)C3—C4—C81115.7 (3)
C15—C16—H16119.7C3—C4—H4A108.3
C11—C16—H16119.7C81—C4—H4A108.3
C22—C21—C26119.0 (4)C3—C4—H4B108.3
C22—C21—C1121.5 (4)C81—C4—H4B108.3
C26—C21—C1119.5 (3)H4A—C4—H4B107.4
C21—C22—C23121.2 (5)O11—C70—O12124.7 (3)
C21—C22—H22119.4O11—C70—C71118.1 (2)
C23—C22—H22119.4O12—C70—C71117.2 (2)
C24—C23—C22118.1 (4)C76—C71—C72120.3 (2)
C24—C23—H23120.9C76—C71—C70119.1 (2)
C22—C23—H23120.9C72—C71—C70120.6 (2)
C23—C24—C25122.9 (4)C71—C72—C73117.3 (3)
C23—C24—F2119.3 (5)C71—C72—C3122.1 (2)
C25—C24—F2117.8 (6)C73—C72—C3120.5 (3)
C24—C25—C26118.0 (5)C74—C73—C72122.2 (3)
C24—C25—H25121.0C74—C73—H73118.9
C26—C25—H25121.0C72—C73—H73118.9
C21—C26—C25120.7 (4)C73—C74—C75119.8 (3)
C21—C26—H26119.6C73—C74—H74120.1
C25—C26—H26119.6C75—C74—H74120.1
N1—C31—C32110.4 (2)C74—C75—C76119.6 (3)
N1—C31—H31A109.6C74—C75—H75120.2
C32—C31—H31A109.6C76—C75—H75120.2
N1—C31—H31B109.6C75—C76—C71120.7 (3)
C32—C31—H31B109.6C75—C76—H76119.6
H31A—C31—H31B108.1C71—C76—H76119.6
N2—C32—C31110.5 (2)C82—C81—C86118.3 (3)
N2—C32—H32A109.5C82—C81—C4118.8 (3)
C31—C32—H32A109.5C86—C81—C4122.9 (3)
N2—C32—H32B109.5C81—C82—C83120.9 (3)
C31—C32—H32B109.5C81—C82—H82119.6
H32A—C32—H32B108.1C83—C82—H82119.6
N2—C33—C34110.5 (2)C84—C83—C82120.3 (4)
N2—C33—H33A109.5C84—C83—H83119.9
C34—C33—H33A109.5C82—C83—H83119.9
N2—C33—H33B109.5C85—C84—C83119.5 (4)
C34—C33—H33B109.5C85—C84—H84120.3
H33A—C33—H33B108.1C83—C84—H84120.3
N1—C34—C33110.1 (2)C84—C85—C86120.8 (4)
N1—C34—H34A109.6C84—C85—H85119.6
C33—C34—H34A109.6C86—C85—H85119.6
N1—C34—H34B109.6C85—C86—C81120.3 (4)
C33—C34—H34B109.6C85—C86—H86119.9
H34A—C34—H34B108.2C81—C86—H86119.9
C61—N3—C64108.3 (2)C92—C5—C6114.0 (3)
C61—N3—C2110.8 (2)C92—C5—H5A108.8
C64—N3—C2112.8 (2)C6—C5—H5A108.8
C63—N4—C62111.3 (2)C92—C5—H5B108.8
C63—N4—H741109 (2)C6—C5—H5B108.8
C62—N4—H741108.0 (19)H5A—C5—H5B107.7
C63—N4—H742110 (2)C101—C6—C5115.9 (3)
C62—N4—H742109 (2)C101—C6—H6A108.3
H741—N4—H742109 (3)C5—C6—H6A108.3
N3—C2—C41112.5 (2)C101—C6—H6B108.3
N3—C2—C51109.8 (2)C5—C6—H6B108.3
C41—C2—C51108.1 (2)H6A—C6—H6B107.4
N3—C2—H2108.8O21—C90—O22124.7 (2)
C41—C2—H2108.8O21—C90—C91117.2 (2)
C51—C2—H2108.8O22—C90—C91118.1 (2)
C42—C41—C46118.9 (3)C96—C91—C92120.7 (2)
C42—C41—C2121.7 (3)C96—C91—C90118.8 (2)
C46—C41—C2119.2 (3)C92—C91—C90120.5 (2)
C41—C42—C43120.6 (3)C93—C92—C91117.7 (3)
C41—C42—H42119.7C93—C92—C5119.6 (3)
C43—C42—H42119.7C91—C92—C5122.6 (2)
C44—C43—C42118.3 (4)C94—C93—C92121.4 (3)
C44—C43—H43120.9C94—C93—H93119.3
C42—C43—H43120.9C92—C93—H93119.3
C43—C44—F3118.3 (4)C95—C94—C93120.3 (3)
C43—C44—C45123.4 (3)C95—C94—H94119.8
F3—C44—C45118.3 (4)C93—C94—H94119.8
C44—C45—C46117.7 (3)C94—C95—C96119.3 (3)
C44—C45—H45121.2C94—C95—H95120.4
C46—C45—H45121.2C96—C95—H95120.4
C45—C46—C41121.1 (3)C91—C96—C95120.6 (3)
C45—C46—H46119.5C91—C96—H96119.7
C41—C46—H46119.5C95—C96—H96119.7
C56—C51—C52119.1 (3)C106—C101—C102117.9 (3)
C56—C51—C2121.4 (3)C106—C101—C6118.7 (3)
C52—C51—C2119.4 (3)C102—C101—C6123.3 (3)
C51—C52—C53121.1 (3)C103—C102—C101120.2 (4)
C51—C52—H52119.5C103—C102—H102119.9
C53—C52—H52119.5C101—C102—H102119.9
C54—C53—C52117.7 (4)C104—C103—C102121.2 (4)
C54—C53—H53121.1C104—C103—H103119.4
C52—C53—H53121.1C102—C103—H103119.4
C55—C54—F4119.2 (4)C105—C104—C103118.5 (4)
C55—C54—C53123.3 (4)C105—C104—H104120.7
F4—C54—C53117.5 (5)C103—C104—H104120.7
C54—C55—C56118.5 (4)C104—C105—C106121.6 (4)
C54—C55—H55120.7C104—C105—H105119.2
C56—C55—H55120.7C106—C105—H105119.2
C51—C56—C55120.3 (4)C105—C106—C101120.4 (3)
C51—C56—H56119.9C105—C106—H106119.8
C55—C56—H56119.9C101—C106—H106119.8
C34—N1—C1—C11−60.7 (3)C53—C54—C55—C56−1.7 (6)
C31—N1—C1—C11178.1 (2)C52—C51—C56—C550.4 (5)
C34—N1—C1—C21179.2 (2)C2—C51—C56—C55178.7 (3)
C31—N1—C1—C2158.0 (3)C54—C55—C56—C510.7 (6)
N1—C1—C11—C12−32.0 (4)C64—N3—C61—C62−63.3 (3)
C21—C1—C11—C1289.1 (3)C2—N3—C61—C62172.4 (2)
N1—C1—C11—C16153.4 (3)C63—N4—C62—C61−53.9 (3)
C21—C1—C11—C16−85.5 (3)N3—C61—C62—N458.7 (3)
C16—C11—C12—C130.4 (5)C62—N4—C63—C6454.1 (3)
C1—C11—C12—C13−174.1 (3)C61—N3—C64—C6362.6 (3)
C11—C12—C13—C140.3 (5)C2—N3—C64—C63−174.3 (2)
C12—C13—C14—C15−0.8 (6)N4—C63—C64—N3−58.5 (3)
C12—C13—C14—F1178.4 (3)C72—C3—C4—C81−172.1 (3)
F1—C14—C15—C16−178.7 (4)O11—C70—C71—C76−95.5 (3)
C13—C14—C15—C160.5 (6)O12—C70—C71—C7684.6 (3)
C14—C15—C16—C110.2 (6)O11—C70—C71—C7285.8 (3)
C12—C11—C16—C15−0.7 (5)O12—C70—C71—C72−94.1 (3)
C1—C11—C16—C15174.0 (3)C76—C71—C72—C730.2 (4)
N1—C1—C21—C22−131.5 (3)C70—C71—C72—C73178.8 (3)
C11—C1—C21—C22105.8 (4)C76—C71—C72—C3−178.5 (3)
N1—C1—C21—C2650.0 (4)C70—C71—C72—C30.1 (4)
C11—C1—C21—C26−72.8 (4)C4—C3—C72—C71−92.8 (3)
C26—C21—C22—C230.0 (6)C4—C3—C72—C7388.6 (3)
C1—C21—C22—C23−178.6 (3)C71—C72—C73—C740.2 (5)
C21—C22—C23—C24−1.5 (6)C3—C72—C73—C74178.9 (3)
C22—C23—C24—C252.1 (7)C72—C73—C74—C75−0.4 (6)
C22—C23—C24—F2−177.5 (4)C73—C74—C75—C760.2 (5)
C23—C24—C25—C26−1.1 (8)C74—C75—C76—C710.1 (5)
F2—C24—C25—C26178.6 (4)C72—C71—C76—C75−0.3 (5)
C22—C21—C26—C251.1 (6)C70—C71—C76—C75−179.0 (3)
C1—C21—C26—C25179.7 (4)C3—C4—C81—C82−161.7 (3)
C24—C25—C26—C21−0.6 (7)C3—C4—C81—C8621.6 (5)
C1—N1—C31—C32−175.0 (2)C86—C81—C82—C830.6 (5)
C34—N1—C31—C3261.9 (3)C4—C81—C82—C83−176.3 (3)
C33—N2—C32—C3154.6 (3)C81—C82—C83—C84−0.9 (5)
N1—C31—C32—N2−58.7 (3)C82—C83—C84—C85−0.2 (6)
C32—N2—C33—C34−54.4 (3)C83—C84—C85—C861.7 (8)
C1—N1—C34—C33175.7 (2)C84—C85—C86—C81−2.0 (8)
C31—N1—C34—C33−61.5 (3)C82—C81—C86—C850.8 (6)
N2—C33—C34—N158.4 (3)C4—C81—C86—C85177.6 (4)
C61—N3—C2—C41−179.6 (2)C92—C5—C6—C101172.6 (3)
C64—N3—C2—C4158.7 (3)O21—C90—C91—C96−84.3 (3)
C61—N3—C2—C51−59.1 (3)O22—C90—C91—C9695.1 (3)
C64—N3—C2—C51179.2 (2)O21—C90—C91—C9294.9 (3)
N3—C2—C41—C4234.3 (4)O22—C90—C91—C92−85.7 (3)
C51—C2—C41—C42−87.2 (3)C96—C91—C92—C930.6 (4)
N3—C2—C41—C46−150.2 (3)C90—C91—C92—C93−178.6 (3)
C51—C2—C41—C4688.4 (3)C96—C91—C92—C5178.0 (3)
C46—C41—C42—C43−0.6 (5)C90—C91—C92—C5−1.3 (4)
C2—C41—C42—C43174.9 (3)C6—C5—C92—C93−89.2 (3)
C41—C42—C43—C440.1 (6)C6—C5—C92—C9193.4 (3)
C42—C43—C44—F3−178.7 (4)C91—C92—C93—C94−1.1 (5)
C42—C43—C44—C450.2 (7)C5—C92—C93—C94−178.5 (3)
C43—C44—C45—C460.0 (7)C92—C93—C94—C950.7 (6)
F3—C44—C45—C46178.9 (4)C93—C94—C95—C960.1 (5)
C44—C45—C46—C41−0.5 (6)C92—C91—C96—C950.2 (4)
C42—C41—C46—C450.8 (5)C90—C91—C96—C95179.5 (3)
C2—C41—C46—C45−174.9 (3)C94—C95—C96—C91−0.6 (5)
N3—C2—C51—C56136.8 (3)C5—C6—C101—C106161.6 (3)
C41—C2—C51—C56−100.1 (3)C5—C6—C101—C102−20.9 (5)
N3—C2—C51—C52−44.8 (4)C106—C101—C102—C103−0.3 (7)
C41—C2—C51—C5278.3 (3)C6—C101—C102—C103−177.8 (4)
C56—C51—C52—C53−0.6 (5)C101—C102—C103—C1041.5 (8)
C2—C51—C52—C53−179.0 (3)C102—C103—C104—C105−1.1 (8)
C51—C52—C53—C54−0.3 (6)C103—C104—C105—C106−0.5 (6)
C52—C53—C54—C551.5 (6)C104—C105—C106—C1011.7 (6)
C52—C53—C54—F4−177.4 (3)C102—C101—C106—C105−1.3 (5)
F4—C54—C55—C56177.2 (4)C6—C101—C106—C105176.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H721···O220.89 (4)1.81 (4)2.691 (3)173 (4)
N2—H722···O12i0.99 (4)1.70 (4)2.688 (3)174 (4)
N4—H741···O21ii0.94 (3)1.75 (3)2.683 (3)174 (3)
N4—H742···O11iii0.98 (4)1.71 (4)2.688 (3)174 (3)
C23—H23···F1iv0.952.413.281 (6)153
C55—H55···F3iv0.952.463.374 (5)161
C3—H3A···O21iv0.992.613.576 (3)165
C5—H5B···O12v0.992.603.564 (3)164
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y+1/2, −z+1; (iii) −x+1, y+1/2, −z+1; (iv) x−1, y, z−1; (v) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC17H19F2N2+·C15H13O2−
Mr514.60
Crystal system, space groupMonoclinic, P21
Temperature (K)200
a, b, c (Å)8.2330 (2), 35.5366 (10), 10.1505 (3)
β (°) 112.925 (1)
V (Å3)2735.19 (13)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.52 × 0.34 × 0.31
Data collection
DiffractometerBruker APEXII CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		24852, 6889, 6401
Rint0.033
(sin θ/λ)max (Å−1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.129, 1.07
No. of reflections6889
No. of parameters701
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.29, −0.21

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H721···O220.89 (4)1.81 (4)2.691 (3)173 (4)
N2—H722···O12i0.99 (4)1.70 (4)2.688 (3)174 (4)
N4—H741···O21ii0.94 (3)1.75 (3)2.683 (3)174 (3)
N4—H742···O11iii0.98 (4)1.71 (4)2.688 (3)174 (3)
C23—H23···F1iv0.952.413.281 (6)153
C55—H55···F3iv0.952.463.374 (5)161
C3—H3A···O21iv0.992.613.576 (3)165
C5—H5B···O12v0.992.603.564 (3)164
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y+1/2, −z+1; (iii) −x+1, y+1/2, −z+1; (iv) x−1, y, z−1; (v) x+1, y, z+1.
 

Acknowledgements

ASD thanks the University of Mysore for research facilities. HSY thanks R. L. Fine Chem., Bengaluru, for the gift sample of the title compound.

References

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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Pages o2783-o2784
https://doi.org/10.1107/S160053681103902X
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