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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2535.
Published online 2009 September 26. doi:  10.1107/S160053680903801X
PMCID: PMC2970377

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

Abstract

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 π–π [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 [triangle]); Choudhury & Row (2004 [triangle]); Gdaniec et al. (2003 [triangle]); Kawahara et al. (2004 [triangle]); Mori & Matsumoo (2007 [triangle]); Reddy et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2535-scheme1.jpg

Experimental

Crystal data

  • C12H9N2 +·C7F5O2 ·2C7HF5O2
  • M r = 816.44
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2535-efi1.jpg
  • 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 [triangle]) T min = 0.934, T max = 0.952
  • 6444 measured reflections
  • 5387 independent reflections
  • 1611 reflections with I > 2σ(I)
  • R int = 0.075

Refinement

  • R[F 2 > 2σ(F 2)] = 0.078
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903801X/hb5105sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903801X/hb5105Isup2.hkl

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

Acknowledgments

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.

supplementary crystallographic information

Comment

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. π–π 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}.

Experimental

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

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).

Figures

Fig. 1.
The structure of (I). Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

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

Bruker SMART CCD diffractometer5387 independent reflections
Radiation source: fine-focus sealed tube1611 reflections with I > 2σ(I)
graphiteRint = 0.075
ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −11→1
Tmin = 0.934, Tmax = 0.952k = −13→13
6444 measured reflectionsl = −18→18

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) = 0.276H-atom parameters constrained
S = 0.86w = 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

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/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)
F4−0.0784 (5)0.1431 (5)0.0989 (4)0.0996 (17)
F5−0.0761 (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)
F11−0.0973 (5)0.3169 (5)0.7283 (4)0.115 (2)
F12−0.0313 (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*
O6−0.0504 (7)0.2012 (6)0.5975 (5)0.101 (2)

Atomic displacement parameters (Å2)

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, °)

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—C3−1.3 (13)C20—C21—C22—F6−1.3 (11)
C1—C2—C3—C40.7 (13)C26—C21—C22—C23−0.3 (11)
C2—C3—C4—C7−177.5 (8)C20—C21—C22—C23179.1 (7)
C2—C3—C4—C5−1.4 (12)F6—C22—C23—C24−179.7 (8)
C3—C4—C5—N12.6 (10)C21—C22—C23—C240.0 (13)
C7—C4—C5—N1179.1 (7)F6—C22—C23—F7−0.6 (11)
C3—C4—C5—C6178.8 (7)C21—C22—C23—F7179.1 (7)
C7—C4—C5—C6−4.7 (10)F7—C23—C24—F81.0 (14)
N1—C5—C6—N2−2.6 (9)C22—C23—C24—F8180.0 (7)
C4—C5—C6—N2−178.8 (6)F7—C23—C24—C25179.5 (8)
N1—C5—C6—C9−179.9 (7)C22—C23—C24—C25−1.5 (14)
C4—C5—C6—C94.0 (10)C23—C24—C25—F9179.9 (8)
C3—C4—C7—C8179.5 (8)F8—C24—C25—F9−1.7 (13)
C5—C4—C7—C83.3 (12)C23—C24—C25—C263.3 (14)
C4—C7—C8—C9−0.9 (13)F8—C24—C25—C26−178.2 (7)
N2—C6—C9—C103.7 (11)F9—C25—C26—F103.3 (13)
C5—C6—C9—C10−179.2 (6)C24—C25—C26—F10179.6 (8)
N2—C6—C9—C8−178.6 (7)F9—C25—C26—C21179.9 (8)
C5—C6—C9—C8−1.5 (11)C24—C25—C26—C21−3.8 (13)
C7—C8—C9—C60.1 (12)C22—C21—C26—F10178.7 (7)
C7—C8—C9—C10177.6 (8)C20—C21—C26—F10−0.7 (11)
C6—C9—C10—C11−4.2 (11)C22—C21—C26—C252.3 (12)
C8—C9—C10—C11178.1 (8)C20—C21—C26—C25−177.1 (8)
C9—C10—C11—C123.1 (13)O6—C27—C28—C29−9.0 (12)
C10—C11—C12—N2−1.1 (15)O5—C27—C28—C29167.5 (7)
O2—C13—C14—C15−58.5 (11)O6—C27—C28—C33168.2 (8)
O1—C13—C14—C15113.5 (8)O5—C27—C28—C33−15.3 (11)
O2—C13—C14—C19120.7 (9)C33—C28—C29—C303.6 (12)
O1—C13—C14—C19−67.2 (11)C27—C28—C29—C30−178.9 (8)
C19—C14—C15—F1177.2 (7)C33—C28—C29—F11−179.6 (7)
C13—C14—C15—F1−3.5 (11)C27—C28—C29—F11−2.1 (11)
C19—C14—C15—C16−0.1 (11)F11—C29—C30—F123.1 (13)
C13—C14—C15—C16179.1 (8)C28—C29—C30—F12−179.9 (7)
F1—C15—C16—F24.5 (12)F11—C29—C30—C31177.3 (7)
C14—C15—C16—F2−178.1 (7)C28—C29—C30—C31−5.7 (14)
F1—C15—C16—C17−177.3 (7)C29—C30—C31—F13−178.3 (8)
C14—C15—C16—C170.1 (12)F12—C30—C31—F13−3.8 (12)
F2—C16—C17—F31.4 (12)C29—C30—C31—C325.4 (13)
C15—C16—C17—F3−176.9 (7)F12—C30—C31—C32179.9 (7)
F2—C16—C17—C18177.3 (7)F13—C31—C32—C33−179.8 (8)
C15—C16—C17—C18−1.0 (12)C30—C31—C32—C33−3.5 (12)
F3—C17—C18—C19177.9 (7)F13—C31—C32—F144.3 (11)
C16—C17—C18—C192.0 (12)C30—C31—C32—F14−179.4 (7)
F3—C17—C18—F4−4.4 (11)F14—C32—C33—F15−1.9 (12)
C16—C17—C18—F4179.7 (7)C31—C32—C33—F15−177.5 (7)
F4—C18—C19—F53.4 (11)F14—C32—C33—C28177.4 (7)
C17—C18—C19—F5−178.9 (7)C31—C32—C33—C281.8 (12)
F4—C18—C19—C14−179.8 (7)C29—C28—C33—C32−1.6 (11)
C17—C18—C19—C14−2.2 (12)C27—C28—C33—C32−179.0 (8)
C15—C14—C19—F5178.0 (6)C29—C28—C33—F15177.6 (7)
C13—C14—C19—F5−1.3 (11)C27—C28—C33—F150.3 (11)
C15—C14—C19—C181.2 (11)C2—C1—N1—C52.7 (12)
C13—C14—C19—C18−178.1 (8)C4—C5—N1—C1−3.4 (10)
O4—C20—C21—C26−34.9 (11)C6—C5—N1—C1−179.6 (7)
O3—C20—C21—C26142.3 (8)C11—C12—N2—C60.4 (12)
O4—C20—C21—C22145.8 (8)C9—C6—N2—C12−1.8 (11)
O3—C20—C21—C22−37.0 (11)C5—C6—N2—C12−178.8 (6)
C26—C21—C22—F6179.3 (6)

Hydrogen-bond geometry (Å, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5105).

References

  • Bruker (2001). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chopra, D. & Row, T. N. G. (2008). CrystEngComm, 10, 54–67.
  • Choudhury, A. R. & Row, T. N. G. (2004). Cryst. Growth Des.4, 47–52.
  • Gdaniec, M., Jankowski, W., Milewska, M. J. & Połoñski, T. (2003). Angew. Chem. Int. Ed.42, 3903–3906. [PubMed]
  • Kawahara, S.-i., Tsuzuki, S. & Uchimaru, T. (2004). J. Phys. Chem. A, 108, 6744–6749.
  • Mori, Y. & Matsumoo, A. (2007). Cryst. Growth Des. 7, 377–385.
  • Reddy, L. S., Nangia, A. & Lynch, V. M. (2004). Cryst. Growth Des.4, 89–94.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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