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ISSN: 2056-9890

1,10-Phenanthrolinium 2,3,4,5,6-penta­fluoro­benzoate–2,3,4,5,6-penta­fluoro­benzoic acid (1/2)

aCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China
*Correspondence e-mail: xdzhang@lnu.edu.cn

(Received 17 September 2009; accepted 20 September 2009; online 26 September 2009)

In the title compound, C12H9N2+·C7F5O2·2C7HF5O2, the cation and anion are linked by an N—H⋯O hydrogen bond. The neutral mol­ecules bond to the anion via O—H⋯O hydrogen bonds to form associations of one cation, one anion and two neutral mol­ecules. Inter­molecular C—H⋯O, C—H⋯F, F⋯F [shortest contact = 2.768 (8) Å], F⋯π [shortest contact = 3.148 (13) Å] and ππ [shortest centroid–centroid separation = 3.689 (5) Å] inter­actions further link the components to form a three-dimensional network.

Related literature

For recent developments in the supra­molecular chemistry of fluorine-containing compounds, see: Chopra & Row (2008[Chopra, D. & Row, T. N. G. (2008). CrystEngComm, 10, 54-67.]); Choudhury & Row (2004[Choudhury, A. R. & Row, T. N. G. (2004). Cryst. Growth Des. 4, 47-52.]); Gdaniec et al. (2003[Gdaniec, M., Jankowski, W., Milewska, M. J. & Połoñski, T. (2003). Angew. Chem. Int. Ed. 42, 3903-3906.]); Kawahara et al. (2004[Kawahara, S.-i., Tsuzuki, S. & Uchimaru, T. (2004). J. Phys. Chem. A, 108, 6744-6749.]); Mori & Matsumoo (2007[Mori, Y. & Matsumoo, A. (2007). Cryst. Growth Des. 7, 377-385.]); Reddy et al. (2004[Reddy, L. S., Nangia, A. & Lynch, V. M. (2004). Cryst. Growth Des. 4, 89-94.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9N2+·C7F5O2·2C7HF5O2

  • Mr = 816.44

  • Triclinic, [P \overline 1]

  • a = 9.288 (2) Å

  • b = 11.099 (3) Å

  • c = 15.723 (6) Å

  • α = 75.93 (3)°

  • β = 79.45 (2)°

  • γ = 87.14 (2)°

  • V = 1545.6 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 293 K

  • 0.30 × 0.25 × 0.25 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.934, Tmax = 0.952

  • 6444 measured reflections

  • 5387 independent reflections

  • 1611 reflections with I > 2σ(I)

  • Rint = 0.075

Refinement
  • R[F2 > 2σ(F2)] = 0.078

  • wR(F2) = 0.276

  • S = 0.86

  • 5387 reflections

  • 508 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O1 0.86 2.17 2.876 (8) 139
O3—H3A⋯O1 0.82 1.72 2.526 (8) 166
O5—H5⋯O2 0.82 1.80 2.572 (10) 157
C7—H7⋯O6i 0.93 2.54 3.353 (12) 146
C8—H8⋯O4ii 0.93 2.57 3.391 (11) 147
C2—H2⋯F15iii 0.93 2.51 3.357 (10) 151
C10—H10⋯F7iv 0.93 2.54 3.375 (11) 149
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1; (iv) x, y, z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The research of supramolecular interaction based on the fluorine containing organic compound has been an area of explosive growth in recent years (Chopra & Row, 2008; Choudhury & Row, 2004; Gdaniec, et al., 2003; Kawahara, Tsuzuki & Uchimaru, 2004; Mori & Matsumoo, 2007; Reddy et al., 2004). Recent studies unravel the importance of weak but important of fluorine involving interactions in many crystal structures. The structure of the title complex is shown in Fig. 1. N—H···O and O—H···O bond one 1,10-phenanthrolinium 2,3,4,5,6-pentafluorobenzoate and two 2,3,4,5,6-pentafluorobenzoic acid molecules form a organic cluster. Additional nonclassical hydrogen bond of C—H···O, C—H···F (Table 1), F···F [F2···F14(1 - x, -y,1 - z), 2.768 (8) Å; F3···F13(x, y, -1 + z), 2.867 (8) Å; F5···F7(-x, 1 - y, -z), 2.935 (8) Å; F6···F13(x, y, -1 + z), 2.861 (8) Å] and F···π[F4···C24(-x, 1 - y, -z), 3.148 (13) Å; F9···C16 (1 - x, 1 - y, -z), 3.103 (11) Å; F12···C21(-x, 1 - y, 1 - z), 3.078 (10) Å; F13···C17(x, y, 1 + z), 3.101 (11) Å] are involved in the construction of the supramolecular three-dimensional network. ππ stacking also strengthen the stability of the structure {[Cg1···Cg2 (1 - x,1 - y,1 - z) 3.700 (5) Å; Cg2···Cg3 (1 - x,1 - y,1 - z) 3.689 (5) Å; Cg2···Cg5 3.786 (5) Å; Cg4···Cg4 (1 - x,1 - y,-z) 3.763 (6) Å; Cg5···Cg6 (-x, -y, 1 - z) 3.891 (5) Å], Cg1 is the centroid of the N1/C1–C5 ring, Cg2 is the centroid of the N2/C6/C9—C12 ring, Cg3 is the centroid of the C4—C9 ring, Cg4 is the centroid of the C21—C16 ring, Cg5 is the centroid of the C28—C33 ring, Cg6 is the centroid of the C14—C19 ring, respectively}.

Related literature top

For recent developments in the supramolecular chemistry of fluorine-containing compounds, see Chopra & Row (2008); Choudhury & Row (2004); Gdaniec et al. (2003); Kawahara et al. (2004); Mori & Matsumoo (2007); Reddy et al. (2004).

Experimental top

A solution of 1,10-phenanthroline (5 mmol) in ethanol (10 ml) was added into 2,3,4,5,6-pentafluorobenzoic acid (15 mmol) in ethanol (25 ml). The mixture was filtered. Colourless blocks of (I) were formed after one week by evaporation of the solvent at room temperature.

Refinement top

All H atoms were placed in calculated positions and included in a riding-model approximation, with C—H = 0.93 Å, O—H = 0.82 Å, N—H = 0.86 Å and Uiso(H)= 1.2Ueq(C), Uiso(H)= 1.2Ueq(N) or 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
1,10-Phenanthrolinium 2,3,4,5,6-pentafluorobenzoate–2,3,4,5,6-pentafluorobenzoic acid (1/2) top
Crystal data top
C12H9N2+·C7F5O2·2C7HF5O2Z = 2
Mr = 816.44F(000) = 812
Triclinic, P1Dx = 1.754 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.288 (2) ÅCell parameters from 76 reflections
b = 11.099 (3) Åθ = 2.1–22.2°
c = 15.723 (6) ŵ = 0.18 mm1
α = 75.93 (3)°T = 293 K
β = 79.45 (2)°Block, colourless
γ = 87.14 (2)°0.30 × 0.25 × 0.25 mm
V = 1545.6 (8) Å3
Data collection top
Bruker SMART CCD
diffractometer
5387 independent reflections
Radiation source: fine-focus sealed tube1611 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 111
Tmin = 0.934, Tmax = 0.952k = 1313
6444 measured reflectionsl = 1818
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)] = 0.078Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.276H-atom parameters constrained
S = 0.86 w = 1/[σ2(Fo2) + (0.1316P)2]
where P = (Fo2 + 2Fc2)/3
5387 reflections(Δ/σ)max = 0.001
508 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.39 e Å3
Crystal data top
C12H9N2+·C7F5O2·2C7HF5O2γ = 87.14 (2)°
Mr = 816.44V = 1545.6 (8) Å3
Triclinic, P1Z = 2
a = 9.288 (2) ÅMo Kα radiation
b = 11.099 (3) ŵ = 0.18 mm1
c = 15.723 (6) ÅT = 293 K
α = 75.93 (3)°0.30 × 0.25 × 0.25 mm
β = 79.45 (2)°
Data collection top
Bruker SMART CCD
diffractometer
5387 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1611 reflections with I > 2σ(I)
Tmin = 0.934, Tmax = 0.952Rint = 0.075
6444 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0780 restraints
wR(F2) = 0.276H-atom parameters constrained
S = 0.86Δρmax = 0.33 e Å3
5387 reflectionsΔρmin = 0.39 e Å3
508 parameters
Special details top

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) top
xyzUiso*/Ueq
C10.4878 (9)0.2131 (7)0.3967 (6)0.074 (2)
H10.46240.19720.34600.088*
C20.6122 (9)0.1593 (7)0.4257 (6)0.070 (2)
H20.66860.10630.39520.084*
C30.6539 (9)0.1832 (7)0.4993 (7)0.080 (3)
H30.73850.14770.51870.096*
C40.5663 (7)0.2620 (6)0.5443 (5)0.0533 (19)
C50.4400 (7)0.3161 (6)0.5110 (5)0.0462 (17)
C60.3436 (8)0.3972 (6)0.5566 (5)0.054 (2)
C70.5997 (9)0.2977 (7)0.6186 (7)0.080 (3)
H70.68490.26650.63940.096*
C80.5155 (9)0.3739 (8)0.6606 (6)0.074 (2)
H80.54160.39370.70990.089*
C90.3853 (8)0.4250 (7)0.6296 (5)0.058 (2)
C100.2887 (10)0.5029 (7)0.6736 (6)0.076 (3)
H100.30650.52110.72550.091*
C110.1699 (11)0.5500 (8)0.6380 (7)0.087 (3)
H110.10800.60440.66420.105*
C120.1388 (8)0.5189 (7)0.5633 (7)0.077 (3)
H120.05510.55210.54150.092*
C130.1394 (9)0.1546 (7)0.3570 (7)0.075 (3)
C140.1375 (8)0.1115 (6)0.2753 (5)0.056 (2)
C150.2427 (8)0.0300 (7)0.2470 (6)0.060 (2)
C160.2420 (8)0.0126 (7)0.1718 (6)0.065 (2)
C170.1343 (9)0.0258 (7)0.1219 (6)0.070 (2)
C180.0268 (8)0.1056 (7)0.1491 (5)0.060 (2)
C190.0311 (8)0.1477 (7)0.2225 (6)0.059 (2)
C200.3200 (10)0.4593 (7)0.1686 (7)0.069 (2)
C210.3384 (8)0.5419 (7)0.0810 (6)0.064 (2)
C220.2675 (9)0.5264 (8)0.0133 (7)0.074 (2)
C230.2855 (12)0.6078 (11)0.0694 (8)0.090 (3)
C240.3716 (13)0.7039 (10)0.0867 (8)0.095 (4)
C250.4436 (11)0.7280 (10)0.0227 (8)0.087 (3)
C260.4280 (9)0.6450 (8)0.0577 (7)0.074 (2)
C270.0622 (10)0.1652 (7)0.6233 (6)0.065 (2)
C280.1027 (8)0.1805 (6)0.7065 (5)0.0546 (19)
C290.0191 (8)0.2546 (7)0.7561 (6)0.064 (2)
C300.0509 (9)0.2739 (8)0.8310 (7)0.078 (3)
C310.1650 (9)0.2107 (7)0.8679 (6)0.070 (2)
C320.2517 (8)0.1351 (7)0.8192 (5)0.0565 (19)
C330.2195 (7)0.1205 (6)0.7433 (5)0.0541 (19)
F10.3534 (5)0.0062 (4)0.2915 (4)0.0929 (16)
F20.3421 (5)0.0938 (5)0.1470 (4)0.1060 (19)
F30.1284 (5)0.0194 (4)0.0509 (4)0.0906 (16)
F40.0784 (5)0.1431 (5)0.0989 (4)0.0996 (17)
F50.0761 (5)0.2232 (4)0.2477 (3)0.0887 (16)
F60.1787 (6)0.4264 (5)0.0310 (4)0.1046 (18)
F70.2095 (7)0.5766 (6)0.1270 (4)0.126 (2)
F80.3868 (7)0.7807 (6)0.1671 (5)0.134 (2)
F90.5289 (7)0.8267 (6)0.0453 (5)0.137 (3)
F100.5005 (6)0.6728 (4)0.1161 (4)0.1004 (18)
F110.0973 (5)0.3169 (5)0.7283 (4)0.115 (2)
F120.0313 (6)0.3457 (5)0.8780 (4)0.118 (2)
F130.1964 (5)0.2264 (5)0.9440 (4)0.0971 (17)
F140.3613 (6)0.0731 (5)0.8556 (4)0.112 (2)
F150.3053 (5)0.0431 (5)0.7037 (4)0.1061 (19)
N10.4050 (6)0.2857 (5)0.4388 (4)0.0610 (17)
H1A0.32590.31520.42030.073*
N20.2233 (6)0.4436 (5)0.5217 (4)0.0642 (18)
O10.1633 (6)0.2656 (4)0.3520 (4)0.0755 (16)
O20.1327 (8)0.0702 (6)0.4259 (5)0.103 (2)
O30.1898 (6)0.4156 (5)0.2009 (4)0.0847 (18)
H3A0.18700.37550.25240.127*
O40.4205 (6)0.4356 (5)0.2115 (4)0.0821 (18)
O50.1662 (6)0.1127 (6)0.5748 (4)0.0879 (18)
H50.13270.09280.53540.132*
O60.0504 (7)0.2012 (6)0.5975 (5)0.101 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.066 (6)0.074 (5)0.091 (7)0.006 (5)0.007 (5)0.046 (5)
C20.067 (6)0.062 (5)0.083 (7)0.005 (4)0.001 (5)0.032 (5)
C30.056 (5)0.062 (5)0.128 (9)0.013 (4)0.018 (5)0.035 (6)
C40.049 (4)0.055 (4)0.059 (5)0.002 (4)0.021 (4)0.012 (4)
C50.046 (4)0.039 (4)0.058 (5)0.007 (3)0.007 (4)0.021 (4)
C60.049 (4)0.037 (4)0.071 (6)0.008 (3)0.002 (4)0.011 (4)
C70.070 (6)0.059 (5)0.116 (8)0.002 (4)0.022 (6)0.024 (5)
C80.081 (6)0.079 (6)0.076 (7)0.010 (5)0.033 (5)0.028 (5)
C90.057 (5)0.064 (5)0.059 (5)0.010 (4)0.004 (4)0.029 (4)
C100.086 (7)0.071 (6)0.072 (6)0.011 (5)0.010 (5)0.032 (5)
C110.080 (7)0.069 (6)0.115 (9)0.000 (5)0.005 (6)0.044 (6)
C120.045 (5)0.069 (5)0.119 (8)0.009 (4)0.003 (5)0.038 (6)
C130.092 (7)0.039 (5)0.108 (8)0.004 (4)0.048 (6)0.023 (5)
C140.048 (4)0.042 (4)0.074 (6)0.017 (4)0.008 (4)0.004 (4)
C150.058 (5)0.054 (5)0.065 (6)0.005 (4)0.017 (4)0.006 (4)
C160.050 (5)0.069 (5)0.084 (7)0.003 (4)0.009 (5)0.040 (5)
C170.065 (5)0.059 (5)0.093 (7)0.017 (4)0.003 (5)0.037 (5)
C180.061 (5)0.060 (5)0.062 (6)0.001 (4)0.016 (4)0.016 (4)
C190.056 (5)0.055 (5)0.070 (6)0.003 (4)0.005 (4)0.026 (4)
C200.065 (6)0.054 (5)0.089 (8)0.012 (5)0.007 (6)0.024 (5)
C210.056 (5)0.056 (5)0.082 (7)0.016 (4)0.017 (5)0.016 (5)
C220.071 (6)0.054 (5)0.103 (8)0.026 (5)0.026 (6)0.029 (6)
C230.099 (8)0.085 (7)0.098 (9)0.049 (6)0.052 (7)0.028 (7)
C240.105 (9)0.057 (6)0.094 (9)0.031 (6)0.010 (7)0.009 (6)
C250.072 (7)0.079 (7)0.095 (9)0.010 (6)0.006 (6)0.003 (7)
C260.058 (5)0.069 (6)0.088 (8)0.005 (5)0.009 (5)0.012 (6)
C270.064 (6)0.050 (5)0.082 (7)0.009 (4)0.017 (5)0.011 (4)
C280.060 (5)0.047 (4)0.063 (5)0.010 (4)0.015 (4)0.020 (4)
C290.050 (5)0.061 (5)0.082 (7)0.006 (4)0.016 (5)0.017 (5)
C300.062 (6)0.066 (5)0.113 (9)0.016 (4)0.008 (6)0.040 (6)
C310.063 (5)0.065 (5)0.092 (7)0.017 (4)0.005 (5)0.040 (5)
C320.052 (4)0.076 (5)0.048 (5)0.011 (4)0.019 (4)0.022 (4)
C330.048 (4)0.057 (4)0.067 (6)0.015 (4)0.023 (4)0.027 (4)
F10.076 (3)0.093 (3)0.123 (5)0.017 (3)0.041 (3)0.038 (3)
F20.079 (3)0.103 (4)0.145 (5)0.027 (3)0.007 (3)0.063 (4)
F30.088 (3)0.091 (3)0.107 (4)0.009 (3)0.008 (3)0.057 (3)
F40.087 (3)0.110 (4)0.124 (5)0.021 (3)0.061 (3)0.041 (3)
F50.077 (3)0.089 (3)0.114 (4)0.032 (3)0.026 (3)0.051 (3)
F60.124 (4)0.093 (4)0.115 (5)0.002 (3)0.044 (4)0.043 (3)
F70.136 (5)0.149 (5)0.096 (5)0.039 (4)0.041 (4)0.030 (4)
F80.129 (5)0.119 (5)0.120 (5)0.052 (4)0.002 (4)0.009 (4)
F90.113 (5)0.102 (4)0.166 (7)0.026 (4)0.003 (4)0.015 (4)
F100.086 (4)0.089 (4)0.125 (5)0.023 (3)0.020 (3)0.015 (3)
F110.081 (4)0.099 (4)0.181 (6)0.046 (3)0.055 (4)0.050 (4)
F120.109 (4)0.134 (5)0.132 (5)0.053 (4)0.014 (4)0.086 (4)
F130.097 (4)0.096 (4)0.113 (5)0.003 (3)0.016 (3)0.053 (3)
F140.091 (4)0.132 (4)0.143 (5)0.055 (3)0.066 (4)0.069 (4)
F150.088 (3)0.132 (4)0.129 (5)0.057 (3)0.039 (3)0.087 (4)
N10.053 (4)0.064 (4)0.074 (5)0.003 (3)0.013 (3)0.030 (4)
N20.054 (4)0.061 (4)0.091 (5)0.012 (3)0.023 (4)0.038 (4)
O10.076 (4)0.048 (3)0.103 (5)0.004 (3)0.018 (3)0.018 (3)
O20.148 (6)0.071 (4)0.093 (6)0.012 (4)0.025 (5)0.020 (4)
O30.070 (4)0.074 (4)0.101 (6)0.013 (3)0.014 (4)0.002 (4)
O40.073 (4)0.097 (4)0.077 (4)0.010 (3)0.023 (3)0.017 (3)
O50.085 (4)0.105 (5)0.086 (5)0.012 (4)0.025 (4)0.041 (4)
O60.082 (4)0.111 (5)0.126 (6)0.020 (4)0.056 (4)0.033 (4)
Geometric parameters (Å, º) top
C1—N11.299 (9)C18—C191.354 (10)
C1—C21.376 (11)C18—F41.354 (8)
C1—H10.9300C19—F51.336 (8)
C2—C31.371 (12)C20—O41.231 (10)
C2—H20.9300C20—O31.292 (9)
C3—C41.394 (10)C20—C211.442 (11)
C3—H30.9300C21—C261.384 (11)
C4—C71.411 (11)C21—C221.399 (11)
C4—C51.419 (9)C22—F61.359 (9)
C5—N11.357 (9)C22—C231.377 (13)
C5—C61.457 (9)C23—C241.310 (13)
C6—N21.358 (9)C23—F71.359 (11)
C6—C91.382 (10)C24—F81.329 (11)
C7—C81.334 (11)C24—C251.389 (14)
C7—H70.9300C25—F91.322 (11)
C8—C91.427 (10)C25—C261.359 (12)
C8—H80.9300C26—F101.333 (10)
C9—C101.421 (10)C27—O61.206 (9)
C10—C111.353 (12)C27—O51.320 (9)
C10—H100.9300C27—C281.476 (11)
C11—C121.382 (13)C28—C291.385 (10)
C11—H110.9300C28—C331.387 (9)
C12—N21.324 (9)C29—C301.332 (11)
C12—H120.9300C29—F111.338 (8)
C13—O21.242 (10)C30—F121.336 (9)
C13—O11.244 (8)C30—C311.381 (11)
C13—C141.479 (12)C31—F131.333 (10)
C14—C151.386 (10)C31—C321.400 (10)
C14—C191.388 (10)C32—C331.328 (10)
C15—F11.340 (8)C32—F141.338 (8)
C15—C161.376 (11)C33—F151.331 (7)
C16—F21.336 (8)N1—H1A0.8600
C16—C171.372 (11)O3—H3A0.8200
C17—F31.340 (9)O5—H50.8200
C17—C181.379 (10)
N1—C1—C2121.3 (8)F4—C18—C17118.3 (8)
N1—C1—H1119.3F5—C19—C18118.4 (7)
C2—C1—H1119.3F5—C19—C14118.3 (7)
C3—C2—C1120.6 (8)C18—C19—C14123.2 (7)
C3—C2—H2119.7O4—C20—O3121.9 (9)
C1—C2—H2119.7O4—C20—C21122.1 (9)
C2—C3—C4118.4 (8)O3—C20—C21115.9 (8)
C2—C3—H3120.8C26—C21—C22114.3 (9)
C4—C3—H3120.8C26—C21—C20122.0 (9)
C3—C4—C7124.0 (8)C22—C21—C20123.6 (9)
C3—C4—C5118.8 (7)F6—C22—C23119.9 (9)
C7—C4—C5117.1 (7)F6—C22—C21117.7 (9)
N1—C5—C4119.0 (6)C23—C22—C21122.4 (10)
N1—C5—C6120.0 (6)C24—C23—F7126.0 (12)
C4—C5—C6120.9 (7)C24—C23—C22119.9 (10)
N2—C6—C9125.2 (7)F7—C23—C22114.1 (11)
N2—C6—C5117.5 (7)C23—C24—F8118.5 (13)
C9—C6—C5117.3 (7)C23—C24—C25121.5 (11)
C8—C7—C4123.4 (8)F8—C24—C25119.9 (12)
C8—C7—H7118.3F9—C25—C26124.2 (11)
C4—C7—H7118.3F9—C25—C24117.9 (11)
C7—C8—C9119.7 (8)C26—C25—C24117.8 (11)
C7—C8—H8120.1F10—C26—C25115.0 (9)
C9—C8—H8120.1F10—C26—C21121.0 (9)
C6—C9—C10116.3 (8)C25—C26—C21123.9 (10)
C6—C9—C8121.4 (7)O6—C27—O5121.3 (9)
C10—C9—C8122.2 (8)O6—C27—C28125.2 (9)
C11—C10—C9118.1 (9)O5—C27—C28113.4 (7)
C11—C10—H10121.0C29—C28—C33114.8 (7)
C9—C10—H10121.0C29—C28—C27120.6 (7)
C10—C11—C12121.4 (8)C33—C28—C27124.6 (7)
C10—C11—H11119.3C30—C29—F11115.6 (8)
C12—C11—H11119.3C30—C29—C28123.6 (7)
N2—C12—C11122.6 (8)F11—C29—C28120.8 (8)
N2—C12—H12118.7C29—C30—F12122.7 (9)
C11—C12—H12118.7C29—C30—C31120.6 (8)
O2—C13—O1124.7 (9)F12—C30—C31116.4 (9)
O2—C13—C14114.5 (7)F13—C31—C30121.6 (8)
O1—C13—C14120.3 (9)F13—C31—C32121.5 (8)
C15—C14—C19115.4 (7)C30—C31—C32116.8 (8)
C15—C14—C13121.5 (7)C33—C32—F14122.3 (7)
C19—C14—C13123.1 (7)C33—C32—C31120.9 (7)
F1—C15—C16117.7 (7)F14—C32—C31116.7 (7)
F1—C15—C14119.7 (7)C32—C33—F15116.3 (6)
C16—C15—C14122.5 (8)C32—C33—C28123.0 (7)
F2—C16—C17118.5 (7)F15—C33—C28120.7 (7)
F2—C16—C15121.5 (8)C1—N1—C5121.8 (7)
C17—C16—C15119.9 (7)C1—N1—H1A119.1
F3—C17—C16120.5 (7)C5—N1—H1A119.1
F3—C17—C18120.4 (8)C12—N2—C6116.4 (7)
C16—C17—C18118.9 (8)C20—O3—H3A109.5
C19—C18—F4121.7 (7)C27—O5—H5109.5
C19—C18—C17120.0 (8)
N1—C1—C2—C31.3 (13)C20—C21—C22—F61.3 (11)
C1—C2—C3—C40.7 (13)C26—C21—C22—C230.3 (11)
C2—C3—C4—C7177.5 (8)C20—C21—C22—C23179.1 (7)
C2—C3—C4—C51.4 (12)F6—C22—C23—C24179.7 (8)
C3—C4—C5—N12.6 (10)C21—C22—C23—C240.0 (13)
C7—C4—C5—N1179.1 (7)F6—C22—C23—F70.6 (11)
C3—C4—C5—C6178.8 (7)C21—C22—C23—F7179.1 (7)
C7—C4—C5—C64.7 (10)F7—C23—C24—F81.0 (14)
N1—C5—C6—N22.6 (9)C22—C23—C24—F8180.0 (7)
C4—C5—C6—N2178.8 (6)F7—C23—C24—C25179.5 (8)
N1—C5—C6—C9179.9 (7)C22—C23—C24—C251.5 (14)
C4—C5—C6—C94.0 (10)C23—C24—C25—F9179.9 (8)
C3—C4—C7—C8179.5 (8)F8—C24—C25—F91.7 (13)
C5—C4—C7—C83.3 (12)C23—C24—C25—C263.3 (14)
C4—C7—C8—C90.9 (13)F8—C24—C25—C26178.2 (7)
N2—C6—C9—C103.7 (11)F9—C25—C26—F103.3 (13)
C5—C6—C9—C10179.2 (6)C24—C25—C26—F10179.6 (8)
N2—C6—C9—C8178.6 (7)F9—C25—C26—C21179.9 (8)
C5—C6—C9—C81.5 (11)C24—C25—C26—C213.8 (13)
C7—C8—C9—C60.1 (12)C22—C21—C26—F10178.7 (7)
C7—C8—C9—C10177.6 (8)C20—C21—C26—F100.7 (11)
C6—C9—C10—C114.2 (11)C22—C21—C26—C252.3 (12)
C8—C9—C10—C11178.1 (8)C20—C21—C26—C25177.1 (8)
C9—C10—C11—C123.1 (13)O6—C27—C28—C299.0 (12)
C10—C11—C12—N21.1 (15)O5—C27—C28—C29167.5 (7)
O2—C13—C14—C1558.5 (11)O6—C27—C28—C33168.2 (8)
O1—C13—C14—C15113.5 (8)O5—C27—C28—C3315.3 (11)
O2—C13—C14—C19120.7 (9)C33—C28—C29—C303.6 (12)
O1—C13—C14—C1967.2 (11)C27—C28—C29—C30178.9 (8)
C19—C14—C15—F1177.2 (7)C33—C28—C29—F11179.6 (7)
C13—C14—C15—F13.5 (11)C27—C28—C29—F112.1 (11)
C19—C14—C15—C160.1 (11)F11—C29—C30—F123.1 (13)
C13—C14—C15—C16179.1 (8)C28—C29—C30—F12179.9 (7)
F1—C15—C16—F24.5 (12)F11—C29—C30—C31177.3 (7)
C14—C15—C16—F2178.1 (7)C28—C29—C30—C315.7 (14)
F1—C15—C16—C17177.3 (7)C29—C30—C31—F13178.3 (8)
C14—C15—C16—C170.1 (12)F12—C30—C31—F133.8 (12)
F2—C16—C17—F31.4 (12)C29—C30—C31—C325.4 (13)
C15—C16—C17—F3176.9 (7)F12—C30—C31—C32179.9 (7)
F2—C16—C17—C18177.3 (7)F13—C31—C32—C33179.8 (8)
C15—C16—C17—C181.0 (12)C30—C31—C32—C333.5 (12)
F3—C17—C18—C19177.9 (7)F13—C31—C32—F144.3 (11)
C16—C17—C18—C192.0 (12)C30—C31—C32—F14179.4 (7)
F3—C17—C18—F44.4 (11)F14—C32—C33—F151.9 (12)
C16—C17—C18—F4179.7 (7)C31—C32—C33—F15177.5 (7)
F4—C18—C19—F53.4 (11)F14—C32—C33—C28177.4 (7)
C17—C18—C19—F5178.9 (7)C31—C32—C33—C281.8 (12)
F4—C18—C19—C14179.8 (7)C29—C28—C33—C321.6 (11)
C17—C18—C19—C142.2 (12)C27—C28—C33—C32179.0 (8)
C15—C14—C19—F5178.0 (6)C29—C28—C33—F15177.6 (7)
C13—C14—C19—F51.3 (11)C27—C28—C33—F150.3 (11)
C15—C14—C19—C181.2 (11)C2—C1—N1—C52.7 (12)
C13—C14—C19—C18178.1 (8)C4—C5—N1—C13.4 (10)
O4—C20—C21—C2634.9 (11)C6—C5—N1—C1179.6 (7)
O3—C20—C21—C26142.3 (8)C11—C12—N2—C60.4 (12)
O4—C20—C21—C22145.8 (8)C9—C6—N2—C121.8 (11)
O3—C20—C21—C2237.0 (11)C5—C6—N2—C12178.8 (6)
C26—C21—C22—F6179.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.862.172.876 (8)139
O3—H3A···O10.821.722.526 (8)166
O5—H5···O20.821.802.572 (10)157
C7—H7···O6i0.932.543.353 (12)146
C8—H8···O4ii0.932.573.391 (11)147
C2—H2···F15iii0.932.513.357 (10)151
C10—H10···F7iv0.932.543.375 (11)149
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+1; (iii) x+1, y, z+1; (iv) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC12H9N2+·C7F5O2·2C7HF5O2
Mr816.44
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.288 (2), 11.099 (3), 15.723 (6)
α, β, γ (°)75.93 (3), 79.45 (2), 87.14 (2)
V3)1545.6 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.30 × 0.25 × 0.25
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.934, 0.952
No. of measured, independent and
observed [I > 2σ(I)] reflections
6444, 5387, 1611
Rint0.075
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.078, 0.276, 0.86
No. of reflections5387
No. of parameters508
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.39

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.862.172.876 (8)139
O3—H3A···O10.821.722.526 (8)166
O5—H5···O20.821.802.572 (10)157
C7—H7···O6i0.932.543.353 (12)146
C8—H8···O4ii0.932.573.391 (11)147
C2—H2···F15iii0.932.513.357 (10)151
C10—H10···F7iv0.932.543.375 (11)149
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+1; (iii) x+1, y, z+1; (iv) x, y, z+1.
 

Acknowledgements

This work was supported by the Project for Innovation Team of Liaoning Province, China (grant No. 2007T052), the Project for Provincial Key Laboratory of Liaoning Province, China (grant No. 2008S104) and the Startup Project of Doctor, Liaoning University, China.

References

First citationBruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChopra, D. & Row, T. N. G. (2008). CrystEngComm, 10, 54–67.  Web of Science CSD CrossRef CAS Google Scholar
First citationChoudhury, A. R. & Row, T. N. G. (2004). Cryst. Growth Des. 4, 47–52.  Web of Science CSD CrossRef CAS Google Scholar
First citationGdaniec, M., Jankowski, W., Milewska, M. J. & Połoñski, T. (2003). Angew. Chem. Int. Ed. 42, 3903–3906.  Web of Science CSD CrossRef CAS Google Scholar
First citationKawahara, S.-i., Tsuzuki, S. & Uchimaru, T. (2004). J. Phys. Chem. A, 108, 6744–6749.  Web of Science CrossRef CAS Google Scholar
First citationMori, Y. & Matsumoo, A. (2007). Cryst. Growth Des. 7, 377–385.  Web of Science CSD CrossRef CAS Google Scholar
First citationReddy, L. S., Nangia, A. & Lynch, V. M. (2004). Cryst. Growth Des. 4, 89–94.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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