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

Zhang, X.; Men, Y.; Yan, X.; Ge, C.; Kong, Y.

doi:10.1107/S160053680903801X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2535

doi:10.1107/S160053680903801X

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

Xiangdong Zhang,^a ^* Yanmei Men,^a Xianghua Yan,^a Chunhua Ge ^a and Yuxia Kong ^a

^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 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 ); Choudhury & Row (2004 ); Gdaniec et al. (2003 ); Kawahara et al. (2004 ); Mori & Matsumoo (2007 ); Reddy et al. (2004 ).

Experimental

Crystal data

C₁₂H₉N₂⁺·C₇F₅O₂⁻·2C₇HF₅O₂
M_r = 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 ) 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[F² > 2σ(F²)] = 0.078
wR(F²) = 0.276
S = 0.86
5387 reflections
508 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯F7^iv	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); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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.

Supporting information

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

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

checkCIF report

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. 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}.

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.

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

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⁻·2C₇HF₅O₂	Z = 2
M_r = 816.44	F(000) = 812
Triclinic, P1	D_x = 1.754 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.288 (2) Å	Cell parameters from 76 reflections
b = 11.099 (3) Å	θ = 2.1–22.2°
c = 15.723 (6) Å	µ = 0.18 mm⁻¹
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 tube	1611 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→1
T_min = 0.934, T_max = 0.952	k = −13→13
6444 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.276	H-atom parameters constrained
S = 0.86	w = 1/[σ²(F_o²) + (0.1316P)²] where P = (F_o² + 2F_c²)/3
5387 reflections	(Δ/σ)_max = 0.001
508 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₂H₉N₂⁺·C₇F₅O₂⁻·2C₇HF₅O₂	γ = 87.14 (2)°
M_r = 816.44	V = 1545.6 (8) Å³
Triclinic, P1	Z = 2
a = 9.288 (2) Å	Mo Kα radiation
b = 11.099 (3) Å	µ = 0.18 mm⁻¹
c = 15.723 (6) Å	T = 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)
T_min = 0.934, T_max = 0.952	R_int = 0.075
6444 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	0 restraints
wR(F²) = 0.276	H-atom parameters constrained
S = 0.86	Δρ_max = 0.33 e Å⁻³
5387 reflections	Δρ_min = −0.39 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	0.4878 (9)	0.2131 (7)	0.3967 (6)	0.074 (2)
H1	0.4624	0.1972	0.3460	0.088*
C2	0.6122 (9)	0.1593 (7)	0.4257 (6)	0.070 (2)
H2	0.6686	0.1063	0.3952	0.084*
C3	0.6539 (9)	0.1832 (7)	0.4993 (7)	0.080 (3)
H3	0.7385	0.1477	0.5187	0.096*
C4	0.5663 (7)	0.2620 (6)	0.5443 (5)	0.0533 (19)
C5	0.4400 (7)	0.3161 (6)	0.5110 (5)	0.0462 (17)
C6	0.3436 (8)	0.3972 (6)	0.5566 (5)	0.054 (2)
C7	0.5997 (9)	0.2977 (7)	0.6186 (7)	0.080 (3)
H7	0.6849	0.2665	0.6394	0.096*
C8	0.5155 (9)	0.3739 (8)	0.6606 (6)	0.074 (2)
H8	0.5416	0.3937	0.7099	0.089*
C9	0.3853 (8)	0.4250 (7)	0.6296 (5)	0.058 (2)
C10	0.2887 (10)	0.5029 (7)	0.6736 (6)	0.076 (3)
H10	0.3065	0.5211	0.7255	0.091*
C11	0.1699 (11)	0.5500 (8)	0.6380 (7)	0.087 (3)
H11	0.1080	0.6044	0.6642	0.105*
C12	0.1388 (8)	0.5189 (7)	0.5633 (7)	0.077 (3)
H12	0.0551	0.5521	0.5415	0.092*
C13	0.1394 (9)	0.1546 (7)	0.3570 (7)	0.075 (3)
C14	0.1375 (8)	0.1115 (6)	0.2753 (5)	0.056 (2)
C15	0.2427 (8)	0.0300 (7)	0.2470 (6)	0.060 (2)
C16	0.2420 (8)	−0.0126 (7)	0.1718 (6)	0.065 (2)
C17	0.1343 (9)	0.0258 (7)	0.1219 (6)	0.070 (2)
C18	0.0268 (8)	0.1056 (7)	0.1491 (5)	0.060 (2)
C19	0.0311 (8)	0.1477 (7)	0.2225 (6)	0.059 (2)
C20	0.3200 (10)	0.4593 (7)	0.1686 (7)	0.069 (2)
C21	0.3384 (8)	0.5419 (7)	0.0810 (6)	0.064 (2)
C22	0.2675 (9)	0.5264 (8)	0.0133 (7)	0.074 (2)
C23	0.2855 (12)	0.6078 (11)	−0.0694 (8)	0.090 (3)
C24	0.3716 (13)	0.7039 (10)	−0.0867 (8)	0.095 (4)
C25	0.4436 (11)	0.7280 (10)	−0.0227 (8)	0.087 (3)
C26	0.4280 (9)	0.6450 (8)	0.0577 (7)	0.074 (2)
C27	0.0622 (10)	0.1652 (7)	0.6233 (6)	0.065 (2)
C28	0.1027 (8)	0.1805 (6)	0.7065 (5)	0.0546 (19)
C29	0.0191 (8)	0.2546 (7)	0.7561 (6)	0.064 (2)
C30	0.0509 (9)	0.2739 (8)	0.8310 (7)	0.078 (3)
C31	0.1650 (9)	0.2107 (7)	0.8679 (6)	0.070 (2)
C32	0.2517 (8)	0.1351 (7)	0.8192 (5)	0.0565 (19)
C33	0.2195 (7)	0.1205 (6)	0.7433 (5)	0.0541 (19)
F1	0.3534 (5)	−0.0062 (4)	0.2915 (4)	0.0929 (16)
F2	0.3421 (5)	−0.0938 (5)	0.1470 (4)	0.1060 (19)
F3	0.1284 (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)
F6	0.1787 (6)	0.4264 (5)	0.0310 (4)	0.1046 (18)
F7	0.2095 (7)	0.5766 (6)	−0.1270 (4)	0.126 (2)
F8	0.3868 (7)	0.7807 (6)	−0.1671 (5)	0.134 (2)
F9	0.5289 (7)	0.8267 (6)	−0.0453 (5)	0.137 (3)
F10	0.5005 (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)
F13	0.1964 (5)	0.2264 (5)	0.9440 (4)	0.0971 (17)
F14	0.3613 (6)	0.0731 (5)	0.8556 (4)	0.112 (2)
F15	0.3053 (5)	0.0431 (5)	0.7037 (4)	0.1061 (19)
N1	0.4050 (6)	0.2857 (5)	0.4388 (4)	0.0610 (17)
H1A	0.3259	0.3152	0.4203	0.073*
N2	0.2233 (6)	0.4436 (5)	0.5217 (4)	0.0642 (18)
O1	0.1633 (6)	0.2656 (4)	0.3520 (4)	0.0755 (16)
O2	0.1327 (8)	0.0702 (6)	0.4259 (5)	0.103 (2)
O3	0.1898 (6)	0.4156 (5)	0.2009 (4)	0.0847 (18)
H3A	0.1870	0.3755	0.2524	0.127*
O4	0.4205 (6)	0.4356 (5)	0.2115 (4)	0.0821 (18)
O5	0.1662 (6)	0.1127 (6)	0.5748 (4)	0.0879 (18)
H5	0.1327	0.0928	0.5354	0.132*
O6	−0.0504 (7)	0.2012 (6)	0.5975 (5)	0.101 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.066 (6)	0.074 (5)	0.091 (7)	0.006 (5)	−0.007 (5)	−0.046 (5)
C2	0.067 (6)	0.062 (5)	0.083 (7)	0.005 (4)	−0.001 (5)	−0.032 (5)
C3	0.056 (5)	0.062 (5)	0.128 (9)	0.013 (4)	−0.018 (5)	−0.035 (6)
C4	0.049 (4)	0.055 (4)	0.059 (5)	0.002 (4)	−0.021 (4)	−0.012 (4)
C5	0.046 (4)	0.039 (4)	0.058 (5)	−0.007 (3)	−0.007 (4)	−0.021 (4)
C6	0.049 (4)	0.037 (4)	0.071 (6)	−0.008 (3)	0.002 (4)	−0.011 (4)
C7	0.070 (6)	0.059 (5)	0.116 (8)	−0.002 (4)	−0.022 (6)	−0.024 (5)
C8	0.081 (6)	0.079 (6)	0.076 (7)	−0.010 (5)	−0.033 (5)	−0.028 (5)
C9	0.057 (5)	0.064 (5)	0.059 (5)	−0.010 (4)	−0.004 (4)	−0.029 (4)
C10	0.086 (7)	0.071 (6)	0.072 (6)	−0.011 (5)	0.010 (5)	−0.032 (5)
C11	0.080 (7)	0.069 (6)	0.115 (9)	0.000 (5)	0.005 (6)	−0.044 (6)
C12	0.045 (5)	0.069 (5)	0.119 (8)	0.009 (4)	−0.003 (5)	−0.038 (6)
C13	0.092 (7)	0.039 (5)	0.108 (8)	0.004 (4)	−0.048 (6)	−0.023 (5)
C14	0.048 (4)	0.042 (4)	0.074 (6)	−0.017 (4)	−0.008 (4)	−0.004 (4)
C15	0.058 (5)	0.054 (5)	0.065 (6)	−0.005 (4)	−0.017 (4)	−0.006 (4)
C16	0.050 (5)	0.069 (5)	0.084 (7)	0.003 (4)	−0.009 (5)	−0.040 (5)
C17	0.065 (5)	0.059 (5)	0.093 (7)	−0.017 (4)	−0.003 (5)	−0.037 (5)
C18	0.061 (5)	0.060 (5)	0.062 (6)	−0.001 (4)	−0.016 (4)	−0.016 (4)
C19	0.056 (5)	0.055 (5)	0.070 (6)	0.003 (4)	−0.005 (4)	−0.026 (4)
C20	0.065 (6)	0.054 (5)	0.089 (8)	0.012 (5)	−0.007 (6)	−0.024 (5)
C21	0.056 (5)	0.056 (5)	0.082 (7)	0.016 (4)	−0.017 (5)	−0.016 (5)
C22	0.071 (6)	0.054 (5)	0.103 (8)	0.026 (5)	−0.026 (6)	−0.029 (6)
C23	0.099 (8)	0.085 (7)	0.098 (9)	0.049 (6)	−0.052 (7)	−0.028 (7)
C24	0.105 (9)	0.057 (6)	0.094 (9)	0.031 (6)	0.010 (7)	0.009 (6)
C25	0.072 (7)	0.079 (7)	0.095 (9)	0.010 (6)	−0.006 (6)	−0.003 (7)
C26	0.058 (5)	0.069 (6)	0.088 (8)	0.005 (5)	−0.009 (5)	−0.012 (6)
C27	0.064 (6)	0.050 (5)	0.082 (7)	−0.009 (4)	−0.017 (5)	−0.011 (4)
C28	0.060 (5)	0.047 (4)	0.063 (5)	−0.010 (4)	−0.015 (4)	−0.020 (4)
C29	0.050 (5)	0.061 (5)	0.082 (7)	0.006 (4)	−0.016 (5)	−0.017 (5)
C30	0.062 (6)	0.066 (5)	0.113 (9)	0.016 (4)	−0.008 (6)	−0.040 (6)
C31	0.063 (5)	0.065 (5)	0.092 (7)	−0.017 (4)	−0.005 (5)	−0.040 (5)
C32	0.052 (4)	0.076 (5)	0.048 (5)	0.011 (4)	−0.019 (4)	−0.022 (4)
C33	0.048 (4)	0.057 (4)	0.067 (6)	0.015 (4)	−0.023 (4)	−0.027 (4)
F1	0.076 (3)	0.093 (3)	0.123 (5)	0.017 (3)	−0.041 (3)	−0.038 (3)
F2	0.079 (3)	0.103 (4)	0.145 (5)	0.027 (3)	−0.007 (3)	−0.063 (4)
F3	0.088 (3)	0.091 (3)	0.107 (4)	−0.009 (3)	−0.008 (3)	−0.057 (3)
F4	0.087 (3)	0.110 (4)	0.124 (5)	0.021 (3)	−0.061 (3)	−0.041 (3)
F5	0.077 (3)	0.089 (3)	0.114 (4)	0.032 (3)	−0.026 (3)	−0.051 (3)
F6	0.124 (4)	0.093 (4)	0.115 (5)	0.002 (3)	−0.044 (4)	−0.043 (3)
F7	0.136 (5)	0.149 (5)	0.096 (5)	0.039 (4)	−0.041 (4)	−0.030 (4)
F8	0.129 (5)	0.119 (5)	0.120 (5)	0.052 (4)	−0.002 (4)	0.009 (4)
F9	0.113 (5)	0.102 (4)	0.166 (7)	−0.026 (4)	−0.003 (4)	0.015 (4)
F10	0.086 (4)	0.089 (4)	0.125 (5)	−0.023 (3)	−0.020 (3)	−0.015 (3)
F11	0.081 (4)	0.099 (4)	0.181 (6)	0.046 (3)	−0.055 (4)	−0.050 (4)
F12	0.109 (4)	0.134 (5)	0.132 (5)	0.053 (4)	−0.014 (4)	−0.086 (4)
F13	0.097 (4)	0.096 (4)	0.113 (5)	−0.003 (3)	−0.016 (3)	−0.053 (3)
F14	0.091 (4)	0.132 (4)	0.143 (5)	0.055 (3)	−0.066 (4)	−0.069 (4)
F15	0.088 (3)	0.132 (4)	0.129 (5)	0.057 (3)	−0.039 (3)	−0.087 (4)
N1	0.053 (4)	0.064 (4)	0.074 (5)	0.003 (3)	−0.013 (3)	−0.030 (4)
N2	0.054 (4)	0.061 (4)	0.091 (5)	0.012 (3)	−0.023 (4)	−0.038 (4)
O1	0.076 (4)	0.048 (3)	0.103 (5)	−0.004 (3)	−0.018 (3)	−0.018 (3)
O2	0.148 (6)	0.071 (4)	0.093 (6)	−0.012 (4)	−0.025 (5)	−0.020 (4)
O3	0.070 (4)	0.074 (4)	0.101 (6)	−0.013 (3)	−0.014 (4)	−0.002 (4)
O4	0.073 (4)	0.097 (4)	0.077 (4)	0.010 (3)	−0.023 (3)	−0.017 (3)
O5	0.085 (4)	0.105 (5)	0.086 (5)	0.012 (4)	−0.025 (4)	−0.041 (4)
O6	0.082 (4)	0.111 (5)	0.126 (6)	0.020 (4)	−0.056 (4)	−0.033 (4)

Geometric parameters (Å, º) top

C1—N1	1.299 (9)	C18—C19	1.354 (10)
C1—C2	1.376 (11)	C18—F4	1.354 (8)
C1—H1	0.9300	C19—F5	1.336 (8)
C2—C3	1.371 (12)	C20—O4	1.231 (10)
C2—H2	0.9300	C20—O3	1.292 (9)
C3—C4	1.394 (10)	C20—C21	1.442 (11)
C3—H3	0.9300	C21—C26	1.384 (11)
C4—C7	1.411 (11)	C21—C22	1.399 (11)
C4—C5	1.419 (9)	C22—F6	1.359 (9)
C5—N1	1.357 (9)	C22—C23	1.377 (13)
C5—C6	1.457 (9)	C23—C24	1.310 (13)
C6—N2	1.358 (9)	C23—F7	1.359 (11)
C6—C9	1.382 (10)	C24—F8	1.329 (11)
C7—C8	1.334 (11)	C24—C25	1.389 (14)
C7—H7	0.9300	C25—F9	1.322 (11)
C8—C9	1.427 (10)	C25—C26	1.359 (12)
C8—H8	0.9300	C26—F10	1.333 (10)
C9—C10	1.421 (10)	C27—O6	1.206 (9)
C10—C11	1.353 (12)	C27—O5	1.320 (9)
C10—H10	0.9300	C27—C28	1.476 (11)
C11—C12	1.382 (13)	C28—C29	1.385 (10)
C11—H11	0.9300	C28—C33	1.387 (9)
C12—N2	1.324 (9)	C29—C30	1.332 (11)
C12—H12	0.9300	C29—F11	1.338 (8)
C13—O2	1.242 (10)	C30—F12	1.336 (9)
C13—O1	1.244 (8)	C30—C31	1.381 (11)
C13—C14	1.479 (12)	C31—F13	1.333 (10)
C14—C15	1.386 (10)	C31—C32	1.400 (10)
C14—C19	1.388 (10)	C32—C33	1.328 (10)
C15—F1	1.340 (8)	C32—F14	1.338 (8)
C15—C16	1.376 (11)	C33—F15	1.331 (7)
C16—F2	1.336 (8)	N1—H1A	0.8600
C16—C17	1.372 (11)	O3—H3A	0.8200
C17—F3	1.340 (9)	O5—H5	0.8200
C17—C18	1.379 (10)

N1—C1—C2	121.3 (8)	F4—C18—C17	118.3 (8)
N1—C1—H1	119.3	F5—C19—C18	118.4 (7)
C2—C1—H1	119.3	F5—C19—C14	118.3 (7)
C3—C2—C1	120.6 (8)	C18—C19—C14	123.2 (7)
C3—C2—H2	119.7	O4—C20—O3	121.9 (9)
C1—C2—H2	119.7	O4—C20—C21	122.1 (9)
C2—C3—C4	118.4 (8)	O3—C20—C21	115.9 (8)
C2—C3—H3	120.8	C26—C21—C22	114.3 (9)
C4—C3—H3	120.8	C26—C21—C20	122.0 (9)
C3—C4—C7	124.0 (8)	C22—C21—C20	123.6 (9)
C3—C4—C5	118.8 (7)	F6—C22—C23	119.9 (9)
C7—C4—C5	117.1 (7)	F6—C22—C21	117.7 (9)
N1—C5—C4	119.0 (6)	C23—C22—C21	122.4 (10)
N1—C5—C6	120.0 (6)	C24—C23—F7	126.0 (12)
C4—C5—C6	120.9 (7)	C24—C23—C22	119.9 (10)
N2—C6—C9	125.2 (7)	F7—C23—C22	114.1 (11)
N2—C6—C5	117.5 (7)	C23—C24—F8	118.5 (13)
C9—C6—C5	117.3 (7)	C23—C24—C25	121.5 (11)
C8—C7—C4	123.4 (8)	F8—C24—C25	119.9 (12)
C8—C7—H7	118.3	F9—C25—C26	124.2 (11)
C4—C7—H7	118.3	F9—C25—C24	117.9 (11)
C7—C8—C9	119.7 (8)	C26—C25—C24	117.8 (11)
C7—C8—H8	120.1	F10—C26—C25	115.0 (9)
C9—C8—H8	120.1	F10—C26—C21	121.0 (9)
C6—C9—C10	116.3 (8)	C25—C26—C21	123.9 (10)
C6—C9—C8	121.4 (7)	O6—C27—O5	121.3 (9)
C10—C9—C8	122.2 (8)	O6—C27—C28	125.2 (9)
C11—C10—C9	118.1 (9)	O5—C27—C28	113.4 (7)
C11—C10—H10	121.0	C29—C28—C33	114.8 (7)
C9—C10—H10	121.0	C29—C28—C27	120.6 (7)
C10—C11—C12	121.4 (8)	C33—C28—C27	124.6 (7)
C10—C11—H11	119.3	C30—C29—F11	115.6 (8)
C12—C11—H11	119.3	C30—C29—C28	123.6 (7)
N2—C12—C11	122.6 (8)	F11—C29—C28	120.8 (8)
N2—C12—H12	118.7	C29—C30—F12	122.7 (9)
C11—C12—H12	118.7	C29—C30—C31	120.6 (8)
O2—C13—O1	124.7 (9)	F12—C30—C31	116.4 (9)
O2—C13—C14	114.5 (7)	F13—C31—C30	121.6 (8)
O1—C13—C14	120.3 (9)	F13—C31—C32	121.5 (8)
C15—C14—C19	115.4 (7)	C30—C31—C32	116.8 (8)
C15—C14—C13	121.5 (7)	C33—C32—F14	122.3 (7)
C19—C14—C13	123.1 (7)	C33—C32—C31	120.9 (7)
F1—C15—C16	117.7 (7)	F14—C32—C31	116.7 (7)
F1—C15—C14	119.7 (7)	C32—C33—F15	116.3 (6)
C16—C15—C14	122.5 (8)	C32—C33—C28	123.0 (7)
F2—C16—C17	118.5 (7)	F15—C33—C28	120.7 (7)
F2—C16—C15	121.5 (8)	C1—N1—C5	121.8 (7)
C17—C16—C15	119.9 (7)	C1—N1—H1A	119.1
F3—C17—C16	120.5 (7)	C5—N1—H1A	119.1
F3—C17—C18	120.4 (8)	C12—N2—C6	116.4 (7)
C16—C17—C18	118.9 (8)	C20—O3—H3A	109.5
C19—C18—F4	121.7 (7)	C27—O5—H5	109.5
C19—C18—C17	120.0 (8)

N1—C1—C2—C3	−1.3 (13)	C20—C21—C22—F6	−1.3 (11)
C1—C2—C3—C4	0.7 (13)	C26—C21—C22—C23	−0.3 (11)
C2—C3—C4—C7	−177.5 (8)	C20—C21—C22—C23	179.1 (7)
C2—C3—C4—C5	−1.4 (12)	F6—C22—C23—C24	−179.7 (8)
C3—C4—C5—N1	2.6 (10)	C21—C22—C23—C24	0.0 (13)
C7—C4—C5—N1	179.1 (7)	F6—C22—C23—F7	−0.6 (11)
C3—C4—C5—C6	178.8 (7)	C21—C22—C23—F7	179.1 (7)
C7—C4—C5—C6	−4.7 (10)	F7—C23—C24—F8	1.0 (14)
N1—C5—C6—N2	−2.6 (9)	C22—C23—C24—F8	180.0 (7)
C4—C5—C6—N2	−178.8 (6)	F7—C23—C24—C25	179.5 (8)
N1—C5—C6—C9	−179.9 (7)	C22—C23—C24—C25	−1.5 (14)
C4—C5—C6—C9	4.0 (10)	C23—C24—C25—F9	179.9 (8)
C3—C4—C7—C8	179.5 (8)	F8—C24—C25—F9	−1.7 (13)
C5—C4—C7—C8	3.3 (12)	C23—C24—C25—C26	3.3 (14)
C4—C7—C8—C9	−0.9 (13)	F8—C24—C25—C26	−178.2 (7)
N2—C6—C9—C10	3.7 (11)	F9—C25—C26—F10	3.3 (13)
C5—C6—C9—C10	−179.2 (6)	C24—C25—C26—F10	179.6 (8)
N2—C6—C9—C8	−178.6 (7)	F9—C25—C26—C21	179.9 (8)
C5—C6—C9—C8	−1.5 (11)	C24—C25—C26—C21	−3.8 (13)
C7—C8—C9—C6	0.1 (12)	C22—C21—C26—F10	178.7 (7)
C7—C8—C9—C10	177.6 (8)	C20—C21—C26—F10	−0.7 (11)
C6—C9—C10—C11	−4.2 (11)	C22—C21—C26—C25	2.3 (12)
C8—C9—C10—C11	178.1 (8)	C20—C21—C26—C25	−177.1 (8)
C9—C10—C11—C12	3.1 (13)	O6—C27—C28—C29	−9.0 (12)
C10—C11—C12—N2	−1.1 (15)	O5—C27—C28—C29	167.5 (7)
O2—C13—C14—C15	−58.5 (11)	O6—C27—C28—C33	168.2 (8)
O1—C13—C14—C15	113.5 (8)	O5—C27—C28—C33	−15.3 (11)
O2—C13—C14—C19	120.7 (9)	C33—C28—C29—C30	3.6 (12)
O1—C13—C14—C19	−67.2 (11)	C27—C28—C29—C30	−178.9 (8)
C19—C14—C15—F1	177.2 (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—F12	3.1 (13)
C13—C14—C15—C16	179.1 (8)	C28—C29—C30—F12	−179.9 (7)
F1—C15—C16—F2	4.5 (12)	F11—C29—C30—C31	177.3 (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—C17	0.1 (12)	F12—C30—C31—F13	−3.8 (12)
F2—C16—C17—F3	1.4 (12)	C29—C30—C31—C32	5.4 (13)
C15—C16—C17—F3	−176.9 (7)	F12—C30—C31—C32	179.9 (7)
F2—C16—C17—C18	177.3 (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—C19	177.9 (7)	F13—C31—C32—F14	4.3 (11)
C16—C17—C18—C19	2.0 (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—F4	179.7 (7)	C31—C32—C33—F15	−177.5 (7)
F4—C18—C19—F5	3.4 (11)	F14—C32—C33—C28	177.4 (7)
C17—C18—C19—F5	−178.9 (7)	C31—C32—C33—C28	1.8 (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—F5	178.0 (6)	C29—C28—C33—F15	177.6 (7)
C13—C14—C19—F5	−1.3 (11)	C27—C28—C33—F15	0.3 (11)
C15—C14—C19—C18	1.2 (11)	C2—C1—N1—C5	2.7 (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—C26	142.3 (8)	C11—C12—N2—C6	0.4 (12)
O4—C20—C21—C22	145.8 (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—F6	179.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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···F7^iv	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.

Experimental details

Crystal data
Chemical formula	C₁₂H₉N₂⁺·C₇F₅O₂⁻·2C₇HF₅O₂
M_r	816.44
Crystal system, space group	Triclinic, 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)
V (Å³)	1545.6 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.934, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	6444, 5387, 1611
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.276, 0.86
No. of reflections	5387
No. of parameters	508
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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···F7^iv	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.

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

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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