Aqua­(1,10-phenanthroline-κN,N′)bis­(2,3,4,5-tetra­fluoro­benzoato-κO)copper(II) 1,2,3,4-tetra­fluoro­benzene solvate

Sun, J.; Ma, C.; He, G.; Li, J.

doi:10.1107/S1600536807056887

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Aqua(1,10-phenanthroline-κN,N′)bis(2,3,4,5-tetrafluorobenzoato-κO)copper(II) 1,2,3,4-tetrafluorobenzene solvate

J. Sun, C. Ma, G. He and J. Li

In the title compound, [Cu(C₁₃H₆F₄O₂)₂(C₁₂H₈N₂)(H₂O)]·C₆H₂F₄, each Cu^II ion is coordinated by two N atoms [Cu—N = 1.985 (6) and 2.052 (6) Å] from a 1,10-phenanthroline ligand, and three O atoms [Cu—O = 1.922 (6)–2.243 (5) Å] from two 2,3,4,5-tetrafluorobenzoate ligands and a water molecule, respectively, in a distorted square-pyramidal geometry. Intermolecular O—H

O hydrogen bonds link the complex molecules into chains parallel to the a axis. The crystal packing exhibits weak C—H

O hydrogen bonds and π–π interactions, as evidenced by a short distance of 3.717 (13) Å between the centroids of the benzene rings of neighbouring solvent molecules. One F atom is disordered over two positions; the site occupancy factors are 0.57 and 0.43.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056887/cv2347sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056887/cv2347Isup2.hkl Contains datablock I

CCDC reference: 672681

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.015 Å
Disorder in main residue
R factor = 0.076
wR factor = 0.241
Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       3.12 Sigma
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) .....          8 Ang.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C30
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.56
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT334_ALERT_2_C Small Average Benzene C-C Dist.  C27    -C32           1.34 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         15
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            O1  -CU1 -N1  -C15  -172.20  1.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          5
            O1  -CU1 -N1  -C19     7.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            N1  -CU1 -O1  -C1     70.00  2.00   1.555   1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       4.40 Deg.
              F1   -C3   -H3      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       6.20 Deg.
              F1'  -C7   -H7      1.555   1.555   1.555

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        594

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  21 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Metal complexes with carboxylates are among the most investigated complexes in the field of coordination chemistry. Nevertheless, the crystal structures of metal complexes with fluorated carboxylic ligands have rarely been reported. In our work, we have reported the organotin(IV) carboxylates complexes with this ligand (Ma et al., 2006). In continuation of this study, we present here the crystal structure of the title compound.

In the title compound (Fig. 1), the Cu^II ion exhibits a five-coordinated square-pyramidal environment formed by three O atoms from two carboxylic ligands (Cu1—O1 1.922 (6) Å, Cu1—O3 1.948 (5) Å) and one water molecule (Cu1—O5 2.243 (5) Å), and two N atoms (Cu1—N1 1.985 (6) Å, Cu1—N2 2.052 (6) Å) from 1,10-phenanthroline ligand. Two N atoms and two O atoms form the basal plane and atom O5 occupies the apical site.

The intermolecular O—H···O hydrogen bonds (Table 1) link the main molecules related by translation along a axis into chains. The crystal packing exhibits also weak C—H···O hydrogen bonds (Table 1) and π···π interactions, proved by short distance of 3.717 (13) Å between the centroids of benzene rings of neighbouring solvent molecules.

Related literature top

For the crystal structures of related organotin(IV) carboxylate complexes, see: Ma et al. (2006).

Experimental top

The reaction was carried out by the solvothermal method. 2,3,4,5-tetrafluorobenzoic acid(0.386 g,2 mmol) and cupric acetate(0.199 g, 1 mmol) and 1,10-phenanthroline(0.180 g, 1 mmol) were added to the airtight vessel with 20 ml water. The resulting green solution was filtered. The filtrate was placed for sevaral days yielding green block-shaped crystals.

The yield is 81% and elemental analysis: calc. for C₃₂H₁₄CuF₁₂N₂O₅: C 48.16, H 1.77, N 3.51; found: C 48.45, H 3.39, N 3.22. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. View of the title compound with the atomic numbering and 30% probability displacement ellipsoids. H atoms omitted for clarity.

Aqua(1,10-phenanthroline-κN,N')bis(2,3,4,5-tetrafluorobenzoato-κO)copper(II) 1,2,3,4-tetrafluorobenzene solvate top

Crystal data top

[Cu(C₁₃H₆F₄O₂)₂(C₁₂H₈N₂)(H₂O)]·C₆H₂F₄	F(000) = 1588
M_r = 797.99	D_x = 1.760 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.8150 (8) Å	Cell parameters from 2282 reflections
b = 28.9810 (16) Å	θ = 2.7–25.3°
c = 15.44800 (8) Å	µ = 0.85 mm⁻¹
β = 99.226 (2)°	T = 298 K
V = 3011.6 (4) Å³	Block, green
Z = 4	0.37 × 0.15 × 0.14 mm

Data collection top

CCD area detector diffractometer	5137 independent reflections
Radiation source: fine-focus sealed tube	2352 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→6
T_min = 0.745, T_max = 0.891	k = −26→34
14410 measured reflections	l = −18→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.076	H-atom parameters constrained
wR(F²) = 0.241	w = 1/[σ²(F_o²) + (0.1138P)² + 2.0328P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5137 reflections	Δρ_max = 0.77 e Å⁻³
450 parameters	Δρ_min = −0.68 e Å⁻³
594 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0025 (8)

Crystal data top

[Cu(C₁₃H₆F₄O₂)₂(C₁₂H₈N₂)(H₂O)]·C₆H₂F₄	V = 3011.6 (4) Å³
M_r = 797.99	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.8150 (8) Å	µ = 0.85 mm⁻¹
b = 28.9810 (16) Å	T = 298 K
c = 15.44800 (8) Å	0.37 × 0.15 × 0.14 mm
β = 99.226 (2)°

Data collection top

CCD area detector diffractometer	5137 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2352 reflections with I > 2σ(I)
T_min = 0.745, T_max = 0.891	R_int = 0.067
14410 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	594 restraints
wR(F²) = 0.241	H-atom parameters constrained
S = 1.03	Δρ_max = 0.77 e Å⁻³
5137 reflections	Δρ_min = −0.68 e Å⁻³
450 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	Occ. (<1)
Cu1	0.78922 (12)	0.40017 (3)	0.82641 (6)	0.0500 (4)
F1	1.3110 (12)	0.4545 (3)	0.6146 (6)	0.092 (2)	0.572 (7)
F1'	0.6297 (16)	0.4035 (4)	0.5423 (8)	0.092 (2)	0.428 (7)
F2	1.3111 (7)	0.46696 (19)	0.4451 (3)	0.0910 (16)
F3	0.9875 (8)	0.45009 (19)	0.3259 (3)	0.0962 (17)
F4	0.6523 (8)	0.4203 (2)	0.3754 (3)	0.0969 (17)
F5	1.4666 (8)	0.2934 (2)	0.9151 (5)	0.136 (3)
F6	1.5600 (9)	0.2049 (2)	0.9159 (6)	0.160 (3)
F7	1.2794 (10)	0.14033 (18)	0.8663 (5)	0.146 (3)
F8	0.8983 (9)	0.16610 (18)	0.8170 (5)	0.129 (2)
F9	0.5918 (14)	0.2803 (3)	0.2011 (7)	0.188 (2)
F10	0.2495 (13)	0.3180 (2)	0.1405 (6)	0.173 (3)
F11	−0.0500 (14)	0.2650 (3)	0.0694 (7)	0.188 (2)
F12	−0.0109 (15)	0.1768 (3)	0.0570 (8)	0.225 (5)
N1	0.7820 (8)	0.40042 (19)	0.9543 (4)	0.0516 (15)
N2	0.7463 (8)	0.4693 (2)	0.8454 (4)	0.0520 (16)
O1	0.7985 (8)	0.40807 (18)	0.7036 (4)	0.0688 (15)
O2	1.1109 (8)	0.4300 (2)	0.7359 (4)	0.0768 (17)
O3	0.8838 (8)	0.33670 (17)	0.8284 (3)	0.0617 (14)
O4	1.1788 (8)	0.35633 (18)	0.9038 (4)	0.0701 (16)
O5	0.4629 (7)	0.38446 (19)	0.7994 (4)	0.0707 (16)
H5A	0.3958	0.4073	0.7765	0.085*
H5B	0.4205	0.3765	0.8460	0.085*
C1	0.9584 (12)	0.4212 (3)	0.6839 (5)	0.0525 (17)
C2	0.9670 (11)	0.4291 (2)	0.5874 (5)	0.0507 (17)
C3	1.1382 (11)	0.4449 (2)	0.5596 (5)	0.0561 (18)
H3	1.2503	0.4513	0.6006	0.067*	0.428 (7)
C4	1.1439 (12)	0.4510 (3)	0.4727 (6)	0.0600 (19)
C5	0.9808 (13)	0.4434 (3)	0.4121 (5)	0.063 (2)
C6	0.8114 (12)	0.4276 (3)	0.4375 (6)	0.0628 (19)
C7	0.8020 (11)	0.4210 (3)	0.5250 (5)	0.0573 (18)
H7	0.6841	0.4111	0.5421	0.069*	0.572 (7)
C8	1.0611 (12)	0.3282 (3)	0.8664 (6)	0.0578 (19)
C9	1.1242 (11)	0.2780 (3)	0.8655 (6)	0.065 (2)
C10	1.3182 (13)	0.2639 (3)	0.8900 (7)	0.076 (2)
C11	1.3644 (14)	0.2171 (3)	0.8885 (7)	0.088 (3)
C12	1.2302 (15)	0.1857 (3)	0.8678 (7)	0.084 (2)
C13	1.0365 (15)	0.1984 (3)	0.8409 (7)	0.086 (2)
C14	0.9808 (14)	0.2456 (3)	0.8398 (6)	0.077 (2)
H14	0.8493	0.2544	0.8218	0.093*
C15	0.7900 (11)	0.3644 (3)	1.0091 (5)	0.0626 (19)
H15	0.7997	0.3347	0.9872	0.075*
C16	0.7840 (12)	0.3702 (3)	1.0981 (6)	0.072 (2)
H16	0.7858	0.3441	1.1334	0.086*
C17	0.7758 (12)	0.4119 (3)	1.1349 (6)	0.068 (2)
H17	0.7750	0.4151	1.1947	0.082*
C18	0.7686 (10)	0.4502 (3)	1.0802 (5)	0.0543 (17)
C19	0.7699 (10)	0.4428 (3)	0.9901 (5)	0.0529 (17)
C20	0.7507 (10)	0.4802 (3)	0.9295 (6)	0.0531 (17)
C21	0.7379 (10)	0.5253 (3)	0.9603 (6)	0.0590 (18)
C22	0.7192 (11)	0.5600 (3)	0.8973 (7)	0.067 (2)
H22	0.7150	0.5907	0.9142	0.081*
C23	0.7073 (12)	0.5493 (3)	0.8130 (7)	0.071 (2)
H23	0.6892	0.5724	0.7708	0.086*
C24	0.7222 (11)	0.5028 (3)	0.7875 (6)	0.064 (2)
H24	0.7148	0.4957	0.7284	0.077*
C25	0.7577 (11)	0.4964 (3)	1.1095 (6)	0.066 (2)
H25	0.7590	0.5020	1.1689	0.079*
C26	0.7457 (10)	0.5319 (3)	1.0539 (6)	0.0634 (19)
H26	0.7423	0.5617	1.0758	0.076*
C27	0.451 (3)	0.2499 (7)	0.1628 (13)	0.188 (2)
C28	0.278 (3)	0.2712 (5)	0.1346 (12)	0.173 (3)
C29	0.132 (3)	0.2465 (7)	0.1038 (13)	0.188 (2)
C30	0.151 (3)	0.1996 (5)	0.0959 (11)	0.163 (4)
C31	0.328 (3)	0.1800 (5)	0.1200 (11)	0.165 (4)
H31	0.3432	0.1487	0.1101	0.198*
C32	0.486 (2)	0.2046 (5)	0.1583 (11)	0.162 (4)
H32	0.6083	0.1913	0.1796	0.195*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0465 (6)	0.0506 (6)	0.0529 (6)	0.0004 (4)	0.0082 (4)	−0.0032 (4)
F1	0.061 (4)	0.131 (6)	0.082 (5)	−0.011 (4)	0.007 (4)	0.000 (5)
F1'	0.061 (4)	0.131 (6)	0.082 (5)	−0.011 (4)	0.007 (4)	0.000 (5)
F2	0.085 (3)	0.111 (4)	0.086 (4)	−0.003 (3)	0.040 (3)	0.016 (3)
F3	0.109 (4)	0.128 (5)	0.057 (3)	0.007 (3)	0.028 (3)	0.008 (3)
F4	0.085 (4)	0.138 (5)	0.059 (3)	−0.011 (3)	−0.014 (3)	−0.002 (3)
F5	0.062 (3)	0.079 (4)	0.264 (9)	−0.010 (3)	0.015 (4)	0.010 (4)
F6	0.082 (4)	0.106 (5)	0.293 (10)	0.041 (4)	0.035 (5)	0.038 (5)
F7	0.157 (6)	0.056 (3)	0.238 (9)	0.043 (4)	0.070 (6)	0.008 (4)
F8	0.123 (5)	0.053 (3)	0.201 (7)	−0.014 (3)	−0.005 (5)	−0.028 (4)
F9	0.184 (5)	0.148 (4)	0.213 (5)	−0.018 (4)	−0.025 (4)	0.040 (4)
F10	0.218 (6)	0.085 (4)	0.200 (6)	0.006 (4)	−0.014 (5)	0.017 (4)
F11	0.184 (5)	0.148 (4)	0.213 (5)	−0.018 (4)	−0.025 (4)	0.040 (4)
F12	0.206 (9)	0.136 (7)	0.302 (14)	−0.052 (6)	−0.055 (9)	0.038 (7)
N1	0.040 (3)	0.035 (3)	0.079 (5)	0.006 (3)	0.007 (3)	0.001 (3)
N2	0.037 (3)	0.059 (4)	0.061 (4)	−0.002 (3)	0.012 (3)	0.017 (3)
O1	0.053 (3)	0.082 (4)	0.075 (4)	−0.005 (3)	0.020 (3)	−0.007 (3)
O2	0.066 (4)	0.108 (5)	0.052 (4)	0.007 (3)	−0.006 (3)	−0.005 (3)
O3	0.059 (3)	0.062 (3)	0.065 (4)	−0.001 (3)	0.013 (3)	−0.005 (3)
O4	0.060 (3)	0.053 (3)	0.097 (5)	−0.008 (3)	0.011 (3)	−0.009 (3)
O5	0.044 (3)	0.084 (4)	0.086 (4)	−0.004 (3)	0.014 (3)	0.001 (3)
C1	0.052 (4)	0.058 (4)	0.047 (4)	0.011 (3)	0.006 (4)	0.002 (3)
C2	0.051 (4)	0.056 (4)	0.047 (4)	0.003 (3)	0.011 (3)	0.000 (3)
C3	0.050 (4)	0.058 (4)	0.059 (4)	0.005 (3)	0.006 (4)	−0.001 (4)
C4	0.056 (4)	0.064 (4)	0.063 (5)	0.001 (4)	0.020 (4)	0.002 (4)
C5	0.073 (5)	0.076 (5)	0.042 (4)	0.000 (4)	0.014 (4)	0.000 (4)
C6	0.063 (4)	0.071 (5)	0.054 (4)	−0.005 (4)	0.008 (4)	−0.001 (4)
C7	0.053 (4)	0.070 (4)	0.051 (4)	−0.007 (4)	0.016 (4)	−0.001 (4)
C8	0.055 (4)	0.048 (4)	0.075 (5)	−0.007 (4)	0.021 (4)	0.001 (4)
C9	0.050 (4)	0.051 (4)	0.097 (6)	−0.001 (3)	0.023 (4)	0.000 (4)
C10	0.059 (5)	0.058 (4)	0.112 (6)	0.001 (4)	0.016 (4)	0.001 (4)
C11	0.070 (5)	0.076 (5)	0.120 (7)	0.014 (5)	0.021 (5)	0.009 (5)
C12	0.083 (5)	0.049 (5)	0.121 (6)	0.006 (4)	0.025 (5)	0.004 (5)
C13	0.084 (5)	0.059 (5)	0.113 (6)	−0.002 (5)	0.008 (5)	−0.004 (5)
C14	0.075 (5)	0.053 (4)	0.104 (6)	−0.004 (4)	0.012 (4)	−0.012 (4)
C15	0.056 (4)	0.062 (4)	0.070 (5)	0.006 (4)	0.012 (4)	−0.004 (4)
C16	0.062 (4)	0.089 (5)	0.063 (5)	0.001 (4)	0.010 (4)	0.017 (4)
C17	0.058 (4)	0.086 (5)	0.059 (4)	−0.004 (4)	0.001 (4)	−0.007 (4)
C18	0.033 (3)	0.068 (4)	0.061 (4)	−0.004 (3)	0.007 (3)	−0.012 (4)
C19	0.032 (3)	0.061 (4)	0.065 (4)	−0.005 (3)	0.005 (3)	−0.008 (3)
C20	0.033 (3)	0.055 (4)	0.074 (4)	−0.003 (3)	0.017 (3)	−0.013 (3)
C21	0.033 (3)	0.061 (4)	0.084 (5)	−0.008 (3)	0.013 (3)	−0.015 (4)
C22	0.048 (4)	0.055 (4)	0.100 (5)	0.002 (3)	0.015 (4)	−0.001 (4)
C23	0.055 (4)	0.061 (5)	0.101 (6)	−0.001 (4)	0.021 (4)	0.012 (4)
C24	0.056 (4)	0.063 (4)	0.076 (5)	0.001 (4)	0.019 (4)	0.008 (4)
C25	0.042 (4)	0.081 (5)	0.073 (5)	−0.003 (4)	0.007 (4)	−0.020 (4)
C26	0.039 (4)	0.065 (4)	0.085 (5)	−0.004 (3)	0.008 (4)	−0.027 (4)
C27	0.184 (5)	0.148 (4)	0.213 (5)	−0.018 (4)	−0.025 (4)	0.040 (4)
C28	0.218 (6)	0.085 (4)	0.200 (6)	0.006 (4)	−0.014 (5)	0.017 (4)
C29	0.184 (5)	0.148 (4)	0.213 (5)	−0.018 (4)	−0.025 (4)	0.040 (4)
C30	0.174 (9)	0.105 (7)	0.195 (9)	−0.017 (7)	−0.017 (8)	0.043 (7)
C31	0.179 (9)	0.105 (7)	0.195 (9)	0.000 (7)	−0.021 (8)	0.040 (7)
C32	0.170 (8)	0.110 (7)	0.191 (9)	0.004 (7)	−0.021 (8)	0.043 (7)

Geometric parameters (Å, º) top

Cu1—O1	1.922 (6)	C8—C9	1.517 (10)
Cu1—O3	1.948 (5)	C9—C14	1.367 (11)
Cu1—N1	1.985 (6)	C9—C10	1.378 (11)
Cu1—N2	2.052 (6)	C10—C11	1.393 (12)
Cu1—O5	2.243 (5)	C11—C12	1.294 (12)
F1—C3	1.366 (11)	C12—C13	1.369 (12)
F1'—C7	1.345 (13)	C13—C14	1.421 (11)
F2—C4	1.360 (8)	C14—H14	0.9300
F3—C5	1.354 (8)	C15—C16	1.391 (11)
F4—C6	1.345 (9)	C15—H15	0.9300
F5—C10	1.332 (9)	C16—C17	1.341 (11)
F6—C11	1.379 (10)	C16—H16	0.9300
F7—C12	1.358 (9)	C17—C18	1.391 (11)
F8—C13	1.336 (10)	C17—H17	0.9300
F9—C27	1.368 (17)	C18—C19	1.410 (10)
F10—C28	1.373 (15)	C18—C25	1.418 (10)
F11—C29	1.378 (18)	C19—C20	1.425 (10)
F12—C30	1.343 (17)	C20—C21	1.399 (10)
N1—C15	1.340 (9)	C21—C22	1.390 (11)
N1—C19	1.354 (9)	C21—C26	1.450 (11)
N2—C24	1.312 (9)	C22—C23	1.329 (11)
N2—C20	1.333 (9)	C22—H22	0.9300
O1—C1	1.238 (9)	C23—C24	1.412 (11)
O2—C1	1.234 (9)	C23—H23	0.9300
O3—C8	1.280 (9)	C24—H24	0.9300
O4—C8	1.222 (9)	C25—C26	1.335 (11)
O5—H5A	0.8501	C25—H25	0.9300
O5—H5B	0.8499	C26—H26	0.9300
C1—C2	1.520 (10)	C27—C32	1.34 (2)
C2—C7	1.378 (10)	C27—C28	1.34 (2)
C2—C3	1.384 (10)	C28—C29	1.25 (2)
C3—C4	1.361 (10)	C29—C30	1.37 (2)
C3—H3	0.9300	C30—C31	1.334 (19)
C4—C5	1.352 (11)	C31—C32	1.344 (18)
C5—C6	1.357 (11)	C31—H31	0.9300
C6—C7	1.377 (10)	C32—H32	0.9300
C7—H7	0.9300

O1—Cu1—O3	93.7 (2)	F7—C12—C13	118.9 (9)
O1—Cu1—N1	172.9 (2)	F8—C13—C12	119.9 (8)
O3—Cu1—N1	92.8 (2)	F8—C13—C14	119.7 (8)
O1—Cu1—N2	93.0 (2)	C12—C13—C14	120.3 (9)
O3—Cu1—N2	166.9 (2)	C9—C14—C13	118.8 (9)
N1—Cu1—N2	80.0 (2)	C9—C14—H14	120.6
O1—Cu1—O5	91.7 (2)	C13—C14—H14	120.6
O3—Cu1—O5	97.3 (2)	N1—C15—C16	121.6 (8)
N1—Cu1—O5	90.2 (2)	N1—C15—H15	119.2
N2—Cu1—O5	93.7 (2)	C16—C15—H15	119.2
C15—N1—C19	116.6 (7)	C17—C16—C15	122.5 (8)
C15—N1—Cu1	128.4 (5)	C17—C16—H16	118.7
C19—N1—Cu1	115.0 (5)	C15—C16—H16	118.7
C24—N2—C20	117.9 (7)	C16—C17—C18	117.5 (8)
C24—N2—Cu1	129.0 (6)	C16—C17—H17	121.3
C20—N2—Cu1	113.0 (5)	C18—C17—H17	121.3
C1—O1—Cu1	116.7 (5)	C17—C18—C19	118.2 (7)
C8—O3—Cu1	118.3 (5)	C17—C18—C25	123.8 (8)
Cu1—O5—H5A	111.7	C19—C18—C25	117.9 (8)
Cu1—O5—H5B	111.0	N1—C19—C18	123.5 (7)
H5A—O5—H5B	109.3	N1—C19—C20	115.3 (7)
O2—C1—O1	125.9 (8)	C18—C19—C20	121.2 (7)
O2—C1—C2	116.5 (7)	N2—C20—C21	124.2 (8)
O1—C1—C2	117.5 (7)	N2—C20—C19	116.4 (7)
C7—C2—C3	118.2 (7)	C21—C20—C19	119.5 (8)
C7—C2—C1	120.3 (7)	C22—C21—C20	116.1 (8)
C3—C2—C1	121.4 (7)	C22—C21—C26	126.0 (8)
C4—C3—F1	115.4 (8)	C20—C21—C26	117.9 (8)
C4—C3—C2	120.5 (8)	C23—C22—C21	120.1 (8)
F1—C3—C2	124.0 (8)	C23—C22—H22	119.9
C4—C3—H3	119.7	C21—C22—H22	119.9
F1—C3—H3	4.4	C22—C23—C24	120.0 (9)
C2—C3—H3	119.7	C22—C23—H23	120.0
C5—C4—F2	118.4 (7)	C24—C23—H23	120.0
C5—C4—C3	120.8 (7)	N2—C24—C23	121.5 (9)
F2—C4—C3	120.8 (8)	N2—C24—H24	119.2
C4—C5—F3	120.3 (7)	C23—C24—H24	119.2
C4—C5—C6	119.8 (8)	C26—C25—C18	121.5 (8)
F3—C5—C6	119.8 (8)	C26—C25—H25	119.3
F4—C6—C5	118.3 (8)	C18—C25—H25	119.3
F4—C6—C7	121.2 (7)	C25—C26—C21	121.9 (8)
C5—C6—C7	120.5 (8)	C25—C26—H26	119.0
F1'—C7—C6	115.2 (9)	C21—C26—H26	119.0
F1'—C7—C2	124.5 (8)	C32—C27—C28	126.3 (19)
C6—C7—C2	120.1 (7)	C32—C27—F9	122.4 (18)
F1'—C7—H7	6.2	C28—C27—F9	111.3 (19)
C6—C7—H7	120.0	C29—C28—C27	117.3 (18)
C2—C7—H7	120.0	C29—C28—F10	119 (2)
O4—C8—O3	126.1 (7)	C27—C28—F10	124.0 (19)
O4—C8—C9	118.6 (8)	C28—C29—C30	121 (2)
O3—C8—C9	115.4 (7)	C28—C29—F11	122.2 (19)
C14—C9—C10	119.1 (8)	C30—C29—F11	116.1 (17)
C14—C9—C8	118.1 (7)	C31—C30—F12	123.8 (16)
C10—C9—C8	122.8 (7)	C31—C30—C29	119.3 (18)
F5—C10—C9	122.7 (7)	F12—C30—C29	116.6 (17)
F5—C10—C11	117.7 (8)	C30—C31—C32	121.4 (17)
C9—C10—C11	119.5 (8)	C30—C31—H31	119.3
C12—C11—F6	120.3 (9)	C32—C31—H31	119.3
C12—C11—C10	122.5 (9)	C27—C32—C31	113.9 (17)
F6—C11—C10	117.1 (9)	C27—C32—H32	123.1
C11—C12—F7	121.3 (9)	C31—C32—H32	123.1
C11—C12—C13	119.7 (9)

O1—Cu1—N1—C15	−172.2 (16)	C9—C10—C11—F6	−178.3 (9)
O3—Cu1—N1—C15	−15.0 (6)	F6—C11—C12—F7	−4.8 (17)
N2—Cu1—N1—C15	176.1 (6)	C10—C11—C12—F7	179.6 (10)
O5—Cu1—N1—C15	82.3 (6)	F6—C11—C12—C13	179.8 (10)
O1—Cu1—N1—C19	7 (2)	C10—C11—C12—C13	4.2 (17)
O3—Cu1—N1—C19	164.1 (5)	C11—C12—C13—F8	178.0 (10)
N2—Cu1—N1—C19	−4.8 (4)	F7—C12—C13—F8	2.5 (16)
O5—Cu1—N1—C19	−98.6 (5)	C11—C12—C13—C14	−3.1 (17)
O1—Cu1—N2—C24	4.0 (6)	F7—C12—C13—C14	−178.6 (9)
O3—Cu1—N2—C24	124.9 (10)	C10—C9—C14—C13	1.3 (14)
N1—Cu1—N2—C24	−177.4 (6)	C8—C9—C14—C13	−178.3 (8)
O5—Cu1—N2—C24	−87.8 (6)	F8—C13—C14—C9	179.2 (9)
O1—Cu1—N2—C20	−173.7 (5)	C12—C13—C14—C9	0.3 (15)
O3—Cu1—N2—C20	−52.8 (11)	C19—N1—C15—C16	0.6 (10)
N1—Cu1—N2—C20	4.9 (4)	Cu1—N1—C15—C16	179.7 (5)
O5—Cu1—N2—C20	94.4 (5)	N1—C15—C16—C17	−2.0 (12)
O3—Cu1—O1—C1	−87.6 (5)	C15—C16—C17—C18	1.5 (12)
N1—Cu1—O1—C1	70 (2)	C16—C17—C18—C19	0.1 (11)
N2—Cu1—O1—C1	81.1 (5)	C16—C17—C18—C25	179.4 (7)
O5—Cu1—O1—C1	174.9 (5)	C15—N1—C19—C18	1.0 (10)
O1—Cu1—O3—C8	107.7 (5)	Cu1—N1—C19—C18	−178.2 (5)
N1—Cu1—O3—C8	−69.6 (6)	C15—N1—C19—C20	−176.7 (6)
N2—Cu1—O3—C8	−13.1 (13)	Cu1—N1—C19—C20	4.1 (7)
O5—Cu1—O3—C8	−160.1 (5)	C17—C18—C19—N1	−1.4 (10)
Cu1—O1—C1—O2	−0.6 (10)	C25—C18—C19—N1	179.2 (6)
Cu1—O1—C1—C2	−178.2 (5)	C17—C18—C19—C20	176.2 (6)
O2—C1—C2—C7	−178.7 (7)	C25—C18—C19—C20	−3.1 (10)
O1—C1—C2—C7	−0.9 (11)	C24—N2—C20—C21	−2.2 (10)
O2—C1—C2—C3	0.6 (10)	Cu1—N2—C20—C21	175.8 (5)
O1—C1—C2—C3	178.4 (7)	C24—N2—C20—C19	177.8 (6)
C7—C2—C3—C4	−1.7 (11)	Cu1—N2—C20—C19	−4.2 (7)
C1—C2—C3—C4	179.0 (7)	N1—C19—C20—N2	0.2 (9)
C7—C2—C3—F1	179.5 (8)	C18—C19—C20—N2	−177.6 (6)
C1—C2—C3—F1	0.2 (12)	N1—C19—C20—C21	−179.8 (6)
F1—C3—C4—C5	−178.8 (8)	C18—C19—C20—C21	2.4 (10)
C2—C3—C4—C5	2.3 (12)	N2—C20—C21—C22	0.1 (10)
F1—C3—C4—F2	−1.8 (11)	C19—C20—C21—C22	−179.9 (6)
C2—C3—C4—F2	179.4 (7)	N2—C20—C21—C26	−179.7 (6)
F2—C4—C5—F3	2.2 (12)	C19—C20—C21—C26	0.3 (9)
C3—C4—C5—F3	179.3 (7)	C20—C21—C22—C23	2.4 (11)
F2—C4—C5—C6	−179.8 (7)	C26—C21—C22—C23	−177.8 (7)
C3—C4—C5—C6	−2.7 (12)	C21—C22—C23—C24	−2.7 (12)
C4—C5—C6—F4	−179.7 (7)	C20—N2—C24—C23	1.9 (10)
F3—C5—C6—F4	−1.7 (12)	Cu1—N2—C24—C23	−175.8 (5)
C4—C5—C6—C7	2.5 (13)	C22—C23—C24—N2	0.5 (12)
F3—C5—C6—C7	−179.5 (7)	C17—C18—C25—C26	−178.2 (7)
F4—C6—C7—F1'	5.0 (13)	C19—C18—C25—C26	1.1 (11)
C5—C6—C7—F1'	−177.3 (9)	C18—C25—C26—C21	1.6 (11)
F4—C6—C7—C2	−179.7 (7)	C22—C21—C26—C25	177.9 (7)
C5—C6—C7—C2	−2.0 (12)	C20—C21—C26—C25	−2.3 (10)
C3—C2—C7—F1'	176.5 (9)	C32—C27—C28—C29	3 (4)
C1—C2—C7—F1'	−4.2 (13)	F9—C27—C28—C29	−175.1 (18)
C3—C2—C7—C6	1.5 (11)	C32—C27—C28—F10	−179.7 (16)
C1—C2—C7—C6	−179.2 (7)	F9—C27—C28—F10	2 (3)
Cu1—O3—C8—O4	1.4 (11)	C27—C28—C29—C30	−3 (3)
Cu1—O3—C8—C9	179.8 (5)	F10—C28—C29—C30	179.8 (16)
O4—C8—C9—C14	166.9 (8)	C27—C28—C29—F11	−177.1 (17)
O3—C8—C9—C14	−11.6 (12)	F10—C28—C29—F11	5 (3)
O4—C8—C9—C10	−12.7 (13)	C28—C29—C30—C31	−1 (3)
O3—C8—C9—C10	168.8 (8)	F11—C29—C30—C31	173.7 (17)
C14—C9—C10—F5	179.3 (9)	C28—C29—C30—F12	−176 (2)
C8—C9—C10—F5	−1.1 (15)	F11—C29—C30—F12	−1 (3)
C14—C9—C10—C11	−0.4 (15)	F12—C30—C31—C32	179.6 (16)
C8—C9—C10—C11	179.2 (9)	C29—C30—C31—C32	5 (3)
F5—C10—C11—C12	177.8 (10)	C28—C27—C32—C31	1 (3)
C9—C10—C11—C12	−2.5 (17)	F9—C27—C32—C31	178.7 (17)
F5—C10—C11—F6	2.1 (14)	C30—C31—C32—C27	−5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	0.85	2.05	2.776 (8)	143
O5—H5B···O4ⁱ	0.85	2.08	2.831 (7)	147
C25—H25···O2ⁱⁱ	0.93	2.53	3.221 (10)	131
C26—H26···O4ⁱⁱ	0.93	2.44	3.329 (10)	159

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₃H₆F₄O₂)₂(C₁₂H₈N₂)(H₂O)]·C₆H₂F₄
M_r	797.99
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	6.8150 (8), 28.9810 (16), 15.44800 (8)
β (°)	99.226 (2)
V (Å³)	3011.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.37 × 0.15 × 0.14

Data collection
Diffractometer	CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.745, 0.891
No. of measured, independent and observed [I > 2σ(I)] reflections	14410, 5137, 2352
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.241, 1.03
No. of reflections	5137
No. of parameters	450
No. of restraints	594
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.68

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	0.85	2.05	2.776 (8)	142.9
O5—H5B···O4ⁱ	0.85	2.08	2.831 (7)	147.2
C25—H25···O2ⁱⁱ	0.93	2.53	3.221 (10)	131.1
C26—H26···O4ⁱⁱ	0.93	2.44	3.329 (10)	158.8

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+2.

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