Crystal structure of bis­(μ-2,3,4,5-tetra­fluoro­benzoato-κ2O:O′)bis­[(1,10-phen­anthroline-κ2N:N′)(2,3,4,5-tetra­fluoro­benzoato-κO)copper(II)] dihydrate

Sun, J.

doi:10.1107/S1600536814022065

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages m365-m366

doi:10.1107/S1600536814022065

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Crystal structure of bis(μ-2,3,4,5-tetrafluorobenzoato-κ²O:O′)bis[(1,10-phenanthroline-κ²N:N′)(2,3,4,5-tetrafluorobenzoato-κO)copper(II)] dihydrate

Junshan Sun ^a ^*

^aBeijing Key Laboratory for Science and Application of Functional Molecular and Crystalline Materials, Department of Chemistry, University of Science and Technology Beijing, Beijing 100083, People's Republic of China
^*Correspondence e-mail: klsz79@163.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 12 September 2014; accepted 7 October 2014; online 11 October 2014)

In the title compound, [Cu₂(C₇HF₄O₂)₄(C₁₂H₈N₂)₂]·2H₂O, the Cu^II ion has a square-pyramidal coordination sphere. The basal plane consists of two N atoms [Cu—N = 2.008 (3) and 2.032 (3) Å] from the phenanthroline ligand, and of two carboxylate O atoms [Cu—O = 1.942 (3) and 1.948 (3) Å] from two 2,3,4,5-tetrafluorobenzoate anions. Another 2,3,4,5-tetrafluorobenzoate anion provides the apical carboxylate O atom [Cu—O = 2.262 (3) Å] and bridges two Cu^II ions into a binuclear centrosymmetric dimer. Intramolecular π–π interactions between one of the tetrafluorobenzene rings and the middle of the phenenanthroline rings [3.617 (3) Å] stabilize the molecular configuration. O—H⋯O hydrogen bonds between the lattice water molecules and the unbound carboxylate O atoms of the metal complexes leads to the formation of a chain structure parallel to [100].

Keywords: crystal structure; phenanthroline ligands; tetrafluorobenzoate ligands; copper(II) complex; hydrogen bonding.

CCDC reference: 1027857

1. Related literature

For metal complexes with phenanthroline ligands and their derivatives, see: Liu et al. (2006 ); Kaizer et al. (2006 ).

2. Experimental

2.1. Crystal data

[Cu₂(C₇HF₄O₂)₄(C₁₂H₈N₂)₂]·2H₂O
M_r = 1295.84
Monoclinic, P 2₁ /c
a = 7.1880 (8) Å
b = 22.611 (2) Å
c = 15.2343 (15) Å
β = 103.446 (2)°
V = 2408.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 298 K
0.34 × 0.29 × 0.26 mm

2.2. Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.725, T_max = 0.779
12157 measured reflections
4246 independent reflections
2683 reflections with I > 2σ(I)
R_int = 0.049

2.3. Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.116
S = 1.01
4246 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O3	0.85	2.08	2.918 (5)	168
O5—H5B⋯O4ⁱ	0.85	1.95	2.785 (5)	168
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1027857

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814022065/wm5062sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022065/wm5062Isup2.hkl

checkCIF report

Synthesis and crystallisation top

The reaction was carried out under solvothermal conditions. 2,3,4,5-tetrafluorobenzoic acid (0.388 g, 1 mmol), cupric acetate (0.199 g, 1 mmol) and phenanthroline (0.180 g, 2 mmol) were added into an air-tight vessel together with ethanol and water in a volume ratio of 1:2. The vessel was heated at 393 K for three days and was then cooled down to room temperature with a rate of 10 Kh^-. The resulting blue solution was filtered and the filtrate was left for sevaral days giving blue block-shaped crystals. Yield: 81%. Elemental analysis (performed with a Perkin Elmer Model 2400 Series II): calc. for C₂₆H₁₂CuF₈N₂O₅: C 48.26, H 1.61, N 4.40; found: C 48.20, H 1.87, N 4.32.

Refinement top

H atoms of the phenanthroline ring and the anion were placed geometrically (C—H = 0.93 Å) and refined with U_iso(H) = 1.2U_eq(C). H atoms of the water molecule were found from a Fourier difference map and refined with a fixed O—H distance of 0.85 Å and with U_iso(H) = 1.5U_eq(O).

Related literature top

For metal complexes with phenanthroline ligands and their derivatives, see: Liu et al. (2006); Kaizer et al. (2006).

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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: publCIF (Westrip, 2010).

Figures top

The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level for non-H atoms. The non-labelled atoms are generated by symmetry code –x + 1, –y + 1, –z + 2.

The packing of the molecular entities of the title compound. O—H···O hydrogen-bonding interactions are indicated by dashed lines.

Bis(µ-2,3,4,5-tetrafluorobenzoato-κ²O:O')bis[(1,10-phenanthroline-κ²N:N')(2,3,4,5-tetrafluorobenzoato-κO)copper(II)] dihydrate top

Crystal data top

[Cu₂(C₇HF₄O₂)₄(C₁₂H₈N₂)₂]·2H₂O	F(000) = 1292
M_r = 1295.84	D_x = 1.787 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2862 reflections
a = 7.1880 (8) Å	θ = 2.3–25.3°
b = 22.611 (2) Å	µ = 1.01 mm⁻¹
c = 15.2343 (15) Å	T = 298 K
β = 103.446 (2)°	Block, blue
V = 2408.1 (4) Å³	0.34 × 0.29 × 0.26 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	4246 independent reflections
Radiation source: fine-focus sealed tube	2683 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→8
T_min = 0.725, T_max = 0.779	k = −25→26
12157 measured reflections	l = −18→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.043P)² + 2.2045P] where P = (F_o² + 2F_c²)/3
4246 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Cu₂(C₇HF₄O₂)₄(C₁₂H₈N₂)₂]·2H₂O	V = 2408.1 (4) Å³
M_r = 1295.84	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1880 (8) Å	µ = 1.01 mm⁻¹
b = 22.611 (2) Å	T = 298 K
c = 15.2343 (15) Å	0.34 × 0.29 × 0.26 mm
β = 103.446 (2)°

Data collection top

Bruker SMART CCD diffractometer	4246 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2683 reflections with I > 2σ(I)
T_min = 0.725, T_max = 0.779	R_int = 0.049
12157 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.01	Δρ_max = 0.42 e Å⁻³
4246 reflections	Δρ_min = −0.48 e Å⁻³
379 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
Cu1	0.26351 (7)	0.42966 (2)	0.96727 (3)	0.03433 (17)
F1	0.1254 (4)	0.56914 (13)	0.76852 (17)	0.0710 (8)
F2	−0.0108 (5)	0.67144 (15)	0.6908 (2)	0.0943 (11)
F3	−0.0237 (5)	0.76847 (14)	0.7904 (3)	0.0997 (12)
F4	0.1064 (5)	0.76414 (13)	0.9711 (2)	0.0947 (11)
F5	−0.2468 (5)	0.37774 (16)	0.6457 (2)	0.0933 (11)
F6	−0.2536 (6)	0.39045 (19)	0.4738 (2)	0.1363 (17)
F7	0.0539 (8)	0.43382 (19)	0.4210 (2)	0.1446 (19)
F8	0.3701 (7)	0.4633 (2)	0.5452 (3)	0.1405 (17)
N1	0.2919 (5)	0.43593 (14)	1.1012 (2)	0.0332 (8)
N2	0.3007 (5)	0.34263 (15)	0.9999 (2)	0.0369 (8)
O1	0.1742 (4)	0.50970 (13)	0.93618 (18)	0.0414 (7)
O2	0.4181 (4)	0.56062 (12)	1.01997 (18)	0.0405 (7)
O3	0.2454 (4)	0.41553 (13)	0.83942 (18)	0.0444 (8)
O4	−0.0627 (4)	0.39979 (14)	0.8205 (2)	0.0528 (8)
O5	0.5762 (5)	0.35119 (16)	0.8084 (3)	0.0868 (13)
H5A	0.4904	0.3742	0.8189	0.104*
H5B	0.6795	0.3706	0.8140	0.104*
C1	0.2693 (6)	0.55631 (18)	0.9608 (3)	0.0350 (10)
C2	0.1864 (5)	0.61257 (18)	0.9132 (3)	0.0370 (10)
C3	0.1176 (6)	0.6160 (2)	0.8215 (3)	0.0465 (12)
C4	0.0502 (7)	0.6682 (2)	0.7804 (4)	0.0586 (14)
C5	0.0448 (7)	0.7175 (2)	0.8309 (4)	0.0636 (15)
C6	0.1115 (7)	0.7149 (2)	0.9221 (4)	0.0594 (14)
C7	0.1842 (6)	0.6634 (2)	0.9644 (3)	0.0466 (11)
H7	0.2315	0.6625	1.0266	0.056*
C8	0.0790 (7)	0.40866 (18)	0.7915 (3)	0.0377 (10)
C9	0.0673 (7)	0.41365 (19)	0.6907 (3)	0.0443 (11)
C10	−0.0898 (8)	0.3995 (2)	0.6260 (3)	0.0610 (14)
C11	−0.0961 (11)	0.4054 (3)	0.5346 (4)	0.080 (2)
C12	0.0596 (13)	0.4274 (3)	0.5097 (4)	0.090 (2)
C13	0.2181 (11)	0.4413 (3)	0.5731 (4)	0.0830 (19)
C14	0.2248 (8)	0.4351 (2)	0.6621 (3)	0.0648 (15)
H14	0.3356	0.4452	0.7045	0.078*
C15	0.2727 (6)	0.48237 (19)	1.1508 (3)	0.0403 (10)
H15	0.2219	0.5170	1.1220	0.048*
C16	0.3258 (6)	0.4814 (2)	1.2446 (3)	0.0492 (12)
H16	0.3102	0.5149	1.2774	0.059*
C17	0.4000 (7)	0.4316 (2)	1.2880 (3)	0.0522 (12)
H17	0.4380	0.4310	1.3507	0.063*
C18	0.4194 (6)	0.3809 (2)	1.2385 (3)	0.0427 (11)
C19	0.3594 (5)	0.38506 (18)	1.1446 (3)	0.0341 (10)
C20	0.3611 (6)	0.33451 (18)	1.0892 (3)	0.0360 (10)
C21	0.4190 (6)	0.2798 (2)	1.1298 (3)	0.0471 (12)
C22	0.4042 (7)	0.2311 (2)	1.0711 (4)	0.0628 (15)
H22	0.4401	0.1936	1.0938	0.075*
C23	0.3376 (8)	0.2392 (2)	0.9815 (4)	0.0663 (15)
H23	0.3239	0.2069	0.9427	0.080*
C24	0.2888 (7)	0.2959 (2)	0.9466 (3)	0.0523 (13)
H24	0.2472	0.3009	0.8845	0.063*
C25	0.4879 (7)	0.3249 (2)	1.2765 (3)	0.0589 (14)
H25	0.5346	0.3220	1.3386	0.071*
C26	0.4871 (7)	0.2767 (2)	1.2254 (3)	0.0592 (14)
H26	0.5312	0.2409	1.2525	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0356 (3)	0.0364 (3)	0.0293 (3)	−0.0019 (2)	0.0041 (2)	0.0010 (2)
F1	0.095 (2)	0.063 (2)	0.0478 (16)	0.0002 (17)	0.0018 (15)	0.0055 (15)
F2	0.113 (3)	0.091 (3)	0.066 (2)	0.003 (2)	−0.0062 (19)	0.0388 (18)
F3	0.095 (3)	0.055 (2)	0.140 (3)	0.0138 (18)	0.009 (2)	0.045 (2)
F4	0.114 (3)	0.048 (2)	0.126 (3)	0.0141 (19)	0.038 (2)	−0.0052 (19)
F5	0.071 (2)	0.116 (3)	0.077 (2)	−0.016 (2)	−0.0150 (18)	−0.025 (2)
F6	0.158 (4)	0.136 (4)	0.070 (2)	0.022 (3)	−0.063 (2)	−0.034 (2)
F7	0.255 (6)	0.141 (4)	0.0347 (18)	0.034 (4)	0.027 (3)	0.005 (2)
F8	0.178 (4)	0.178 (4)	0.087 (3)	−0.033 (4)	0.073 (3)	0.023 (3)
N1	0.037 (2)	0.031 (2)	0.0311 (17)	0.0036 (16)	0.0072 (15)	0.0034 (15)
N2	0.034 (2)	0.036 (2)	0.041 (2)	−0.0038 (16)	0.0092 (17)	−0.0027 (16)
O1	0.0372 (17)	0.0368 (18)	0.0440 (17)	−0.0052 (14)	−0.0033 (14)	0.0069 (14)
O2	0.0276 (16)	0.0471 (19)	0.0430 (16)	−0.0006 (14)	0.0003 (14)	0.0011 (13)
O3	0.0356 (18)	0.063 (2)	0.0315 (15)	−0.0012 (15)	0.0023 (14)	−0.0011 (14)
O4	0.042 (2)	0.063 (2)	0.053 (2)	−0.0077 (17)	0.0102 (16)	−0.0065 (16)
O5	0.061 (2)	0.072 (3)	0.137 (4)	−0.018 (2)	0.042 (2)	−0.044 (2)
C1	0.028 (2)	0.042 (3)	0.037 (2)	0.004 (2)	0.0105 (19)	0.004 (2)
C2	0.025 (2)	0.037 (3)	0.048 (3)	−0.0019 (19)	0.005 (2)	0.007 (2)
C3	0.041 (3)	0.045 (3)	0.052 (3)	−0.006 (2)	0.007 (2)	0.008 (2)
C4	0.048 (3)	0.060 (4)	0.064 (3)	−0.002 (3)	0.005 (3)	0.027 (3)
C5	0.049 (3)	0.048 (3)	0.093 (4)	0.007 (3)	0.014 (3)	0.029 (3)
C6	0.050 (3)	0.035 (3)	0.097 (4)	0.002 (2)	0.023 (3)	−0.001 (3)
C7	0.040 (3)	0.042 (3)	0.058 (3)	0.000 (2)	0.012 (2)	0.002 (2)
C8	0.041 (3)	0.033 (2)	0.037 (2)	0.003 (2)	0.004 (2)	−0.0046 (19)
C9	0.053 (3)	0.040 (3)	0.036 (2)	0.006 (2)	0.003 (2)	−0.006 (2)
C10	0.064 (4)	0.052 (3)	0.057 (3)	0.002 (3)	−0.007 (3)	−0.013 (3)
C11	0.110 (6)	0.066 (4)	0.042 (3)	0.020 (4)	−0.031 (4)	−0.014 (3)
C12	0.154 (7)	0.072 (5)	0.035 (3)	0.024 (5)	0.006 (4)	−0.001 (3)
C13	0.116 (6)	0.079 (5)	0.059 (4)	0.000 (4)	0.031 (4)	0.011 (3)
C14	0.087 (4)	0.071 (4)	0.037 (3)	−0.002 (3)	0.016 (3)	0.009 (3)
C15	0.039 (3)	0.038 (3)	0.046 (3)	0.002 (2)	0.014 (2)	0.003 (2)
C16	0.054 (3)	0.059 (3)	0.037 (3)	−0.001 (3)	0.015 (2)	−0.011 (2)
C17	0.051 (3)	0.074 (4)	0.032 (2)	−0.005 (3)	0.009 (2)	0.003 (3)
C18	0.037 (3)	0.049 (3)	0.041 (3)	−0.003 (2)	0.008 (2)	0.010 (2)
C19	0.027 (2)	0.041 (3)	0.034 (2)	−0.0019 (19)	0.0068 (18)	0.0064 (19)
C20	0.028 (2)	0.038 (3)	0.043 (3)	−0.0009 (19)	0.0113 (19)	0.007 (2)
C21	0.041 (3)	0.037 (3)	0.066 (3)	0.002 (2)	0.018 (2)	0.011 (2)
C22	0.063 (4)	0.035 (3)	0.093 (4)	0.003 (3)	0.024 (3)	0.011 (3)
C23	0.078 (4)	0.039 (3)	0.088 (4)	−0.007 (3)	0.031 (3)	−0.013 (3)
C24	0.063 (3)	0.045 (3)	0.051 (3)	−0.010 (2)	0.016 (3)	−0.008 (2)
C25	0.058 (3)	0.067 (4)	0.050 (3)	0.003 (3)	0.008 (3)	0.024 (3)
C26	0.060 (3)	0.050 (3)	0.067 (4)	0.010 (3)	0.015 (3)	0.033 (3)

Geometric parameters (Å, º) top

Cu1—O1	1.942 (3)	C6—C7	1.374 (6)
Cu1—O3	1.948 (3)	C7—H7	0.9300
Cu1—N1	2.008 (3)	C8—C9	1.523 (6)
Cu1—N2	2.032 (3)	C9—C10	1.353 (6)
Cu1—O2ⁱ	2.262 (3)	C9—C14	1.392 (7)
F1—C3	1.341 (5)	C10—C11	1.389 (8)
F2—C4	1.336 (6)	C11—C12	1.357 (9)
F3—C5	1.346 (5)	C12—C13	1.348 (9)
F4—C6	1.345 (6)	C13—C14	1.352 (7)
F5—C10	1.327 (6)	C14—H14	0.9300
F6—C11	1.329 (6)	C15—C16	1.391 (6)
F7—C12	1.349 (6)	C15—H15	0.9300
F8—C13	1.356 (7)	C16—C17	1.351 (6)
N1—C15	1.319 (5)	C16—H16	0.9300
N1—C19	1.359 (5)	C17—C18	1.396 (6)
N2—C24	1.323 (5)	C17—H17	0.9300
N2—C20	1.340 (5)	C18—C19	1.398 (5)
O1—C1	1.265 (5)	C18—C25	1.430 (6)
O2—C1	1.232 (5)	C19—C20	1.423 (6)
O2—Cu1ⁱ	2.262 (3)	C20—C21	1.402 (6)
O3—C8	1.257 (5)	C21—C22	1.407 (6)
O4—C8	1.218 (5)	C21—C26	1.427 (6)
O5—H5A	0.8500	C22—C23	1.350 (7)
O5—H5B	0.8499	C22—H22	0.9300
C1—C2	1.516 (5)	C23—C24	1.402 (7)
C2—C3	1.371 (6)	C23—H23	0.9300
C2—C7	1.391 (6)	C24—H24	0.9300
C3—C4	1.369 (6)	C25—C26	1.339 (7)
C4—C5	1.361 (7)	C25—H25	0.9300
C5—C6	1.362 (7)	C26—H26	0.9300

O1—Cu1—O3	88.14 (12)	C9—C10—C11	122.3 (6)
O1—Cu1—N1	97.58 (13)	F6—C11—C12	121.5 (6)
O3—Cu1—N1	174.29 (13)	F6—C11—C10	119.8 (7)
O1—Cu1—N2	168.38 (13)	C12—C11—C10	118.6 (6)
O3—Cu1—N2	93.47 (13)	C13—C12—F7	121.1 (8)
N1—Cu1—N2	80.97 (13)	C13—C12—C11	119.9 (6)
O1—Cu1—O2ⁱ	101.59 (11)	F7—C12—C11	119.0 (7)
O3—Cu1—O2ⁱ	86.16 (11)	C12—C13—C14	121.5 (7)
N1—Cu1—O2ⁱ	92.52 (12)	C12—C13—F8	117.9 (6)
N2—Cu1—O2ⁱ	90.01 (12)	C14—C13—F8	120.6 (6)
C15—N1—C19	117.9 (3)	C13—C14—C9	120.5 (6)
C15—N1—Cu1	129.7 (3)	C13—C14—H14	119.7
C19—N1—Cu1	112.0 (3)	C9—C14—H14	119.7
C24—N2—C20	118.2 (4)	N1—C15—C16	122.3 (4)
C24—N2—Cu1	129.5 (3)	N1—C15—H15	118.8
C20—N2—Cu1	112.0 (3)	C16—C15—H15	118.8
C1—O1—Cu1	125.4 (3)	C17—C16—C15	119.9 (4)
C1—O2—Cu1ⁱ	139.4 (3)	C17—C16—H16	120.0
C8—O3—Cu1	115.7 (3)	C15—C16—H16	120.0
H5A—O5—H5B	108.7	C16—C17—C18	119.8 (4)
O2—C1—O1	126.9 (4)	C16—C17—H17	120.1
O2—C1—C2	117.5 (4)	C18—C17—H17	120.1
O1—C1—C2	115.6 (4)	C17—C18—C19	116.8 (4)
C3—C2—C7	118.4 (4)	C17—C18—C25	125.2 (4)
C3—C2—C1	122.9 (4)	C19—C18—C25	118.0 (4)
C7—C2—C1	118.7 (4)	N1—C19—C18	123.0 (4)
F1—C3—C4	117.7 (4)	N1—C19—C20	116.3 (3)
F1—C3—C2	120.8 (4)	C18—C19—C20	120.7 (4)
C4—C3—C2	121.3 (5)	N2—C20—C21	124.1 (4)
F2—C4—C5	119.1 (5)	N2—C20—C19	116.5 (4)
F2—C4—C3	120.8 (5)	C21—C20—C19	119.3 (4)
C5—C4—C3	120.1 (5)	C20—C21—C22	116.0 (4)
F3—C5—C4	119.9 (5)	C20—C21—C26	119.3 (4)
F3—C5—C6	120.6 (5)	C22—C21—C26	124.6 (5)
C4—C5—C6	119.5 (5)	C23—C22—C21	119.6 (5)
F4—C6—C5	118.9 (5)	C23—C22—H22	120.2
F4—C6—C7	119.9 (5)	C21—C22—H22	120.2
C5—C6—C7	121.2 (5)	C22—C23—C24	120.3 (5)
C6—C7—C2	119.4 (5)	C22—C23—H23	119.8
C6—C7—H7	120.3	C24—C23—H23	119.8
C2—C7—H7	120.3	N2—C24—C23	121.6 (5)
O4—C8—O3	124.9 (4)	N2—C24—H24	119.2
O4—C8—C9	121.6 (4)	C23—C24—H24	119.2
O3—C8—C9	113.5 (4)	C26—C25—C18	122.1 (5)
C10—C9—C14	117.1 (5)	C26—C25—H25	118.9
C10—C9—C8	123.9 (5)	C18—C25—H25	118.9
C14—C9—C8	118.9 (4)	C25—C26—C21	120.5 (4)
F5—C10—C9	122.2 (5)	C25—C26—H26	119.8
F5—C10—C11	115.5 (5)	C21—C26—H26	119.8

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3	0.85	2.08	2.918 (5)	168
O5—H5B···O4ⁱⁱ	0.85	1.95	2.785 (5)	168

Symmetry code: (ii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3	0.85	2.08	2.918 (5)	168.4
O5—H5B···O4ⁱ	0.85	1.95	2.785 (5)	168.3

Symmetry code: (i) x+1, y, z.

References

Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kaizer, J., Csay, T., Speier, G., Réglier, M. & Giorgi, M. (2006). Inorg. Chem. Commun. 9, 1037–1039. Web of Science CSD CrossRef CAS Google Scholar
Liu, J.-W., Zhu, B., Tian, Y. & Gu, C.-S. (2006). Acta Cryst. E62, m2030–m2032. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 11| November 2014| Pages m365-m366

doi:10.1107/S1600536814022065

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