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Acta Cryst. (2007). E63, m1975-m1976    [ doi:10.1107/S1600536807030073 ]

(3-Carboxypyridine-2-carboxylato-[kappa]2N,O)(4'-phenyl-2,2':6',2''-terpyridine-[kappa]3N,N',N'')copper(II) tetrafluoridoborate

S. Martínez-Vargas, R. A. Toscano and J. Valdés-Martínez

Abstract top

The title compound, [Cu(C7H4NO4)(C21H15N3)]BF4, was obtained from an attempt to use 3-carboxypyridine-2-carboxylate as an N,O-bidentate ligand with the carboxyl group as an intermolecular hydrogen-bond site to organize the molecules in the crystal structure. Unfortunately, instead of an intermolecular hydrogen bond, an intramolecular O-H...O hydrogen bond was observed, and the molecules are organized by van der Waals and [pi]-[pi] stacking interactions [3.770 (2) Å]. The metal center has a square-pyramidal geometry, with the 4'-phenyl-2,2':6',2''-terpyridine coordinated in a tridentate manner in basal positions and the 3-carboxypyridine-2-carboxylate ligand coordinated as a bidentate ligand with the pyridine N atom basal and the O atom of the carboxylate group apical. The F atoms are disordered over three sites with occupancies of approximately 2:1:1.

Comment top

Compounds with the 3-carboxylpyridine-2-carboxylato as ligand have been reported with the carboxyl group forming intermolecular (Turner et al., 2007), (Patrick et al., 2003), (Goher et al., 1993) or intramolecular (Xiang et al., 2006), (Sengupta et al., 2001), (Okabe et al., 1996), (Goher et al., 1993), (Drew et al., 1971), hydrogen bonds. In an attempt to use the carboxyl group in this ligand as an intermolecular H-bond site to organize the molecules in the crystal, the title compound, (I), was synthesized. Unfortunately, only an intramolecular O–H···O is observed.

In compound (I), the metal center has a square pyramidal geometry with the 4'-phenyl-2,2':6',2''-terpyridine coordinated as tridentate in equatorial position and the 3-carboxylpyridine-2-carboxylato coordinated as bidentate with the pyridine N atom in equatorial and the O atom of the carboxylate in axial position (Fig. 1). The 4-phenyl ring in the trpy (C26 - C31) forms an angle of 40.0 (2) Å with the central ring of the trpy (N14/C15—C19). The phenyl ring of the 3-carboxylpyridine-2-carboxylato is almost perpendicular to the trpy, the angle between the mean planes of N14/C15—C19 and N1/C2—C6 is 81.6 (2) Å.

The molecules intercalate with π - π stacking between N14/C15—C19 and N20/C21—C25 of a molecule generated by the symmetry code (1/2 + x,1/2 − y,1/2 + z), the rings are almost parallel (2.05 °) and have a centroid-centroid distance of 3.770 (2)Å an interplanar distance of 3.55 Å, and an offset angle of 19.7°.

Related literature top

For related structures see: Turner et al. (2007); Xiang et al. (2006); Patrick et al. (2003); Sengupta et al. (2001); Okabe et al. (1996); Goher et al. (1993); Drew et al. (1971). For related literature, see: Constable et al. (1990).

Experimental top

The 4'-Phenyl-2,2':6',2''-terpyridine was synthesized according to a published procedure (Constable et al., 1990). The 4'-phenyl-2,2':6',2''-terpyridine (15.4 mg, 0.05 mmol) was dissolved on warm ethanol (10 ml), solid copper(II) tetrafluoroborate hydrate (11.9 mg, 0.05 mmol) was added and then a warm aqueous solution (5 ml) of 2,3-pyridinedicarboxylic acid (8.36 mg, 0.05 mmol) was added to form a blue solution. Blue crystals suitable for X-ray structure determination were obtained by slow evaporation after three days at room temperature.

Refinement top

C-bound H atoms were placed in geometrically idealized positions and refined using a riding model with C–H = 0.93 Å, and Uiso(H) = 1.2Ueq(C). The O-bound H atom was located in a difference map and refined isotropically·The fluorine atoms of the tetrafluoroborate were refined with statistical disorder over three positions, with site occupancies of 0.54 (1) (for F1, F2 and F3), 0.25 (1) (for F1B, F2B and F3B) and 0.22 (1) (for F1C, F2C and F3C).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2007) and enCIFer (Allen et al., 2004).

Figures top
[Figure 1] Fig. 1. The molecular structure of the complex cation in (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radius.
(3-Carboxypyridine-2-carboxylato-κ2N,O)(4'-phenyl-2,2':6',2''-terpyridine- κ3N,N',N'')copper(II) tetrafluoridoborate top
Crystal data top
[Cu(C7H4NO4)(C21H15N3)]BF4F000 = 1268.3
Mr = 625.82Dx = 1.611 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5948 reflections
a = 9.7975 (5) Åθ = 2.3–30.9º
b = 25.1020 (10) ŵ = 0.92 mm−1
c = 11.0414 (6) ÅT = 298 (2) K
β = 108.1830 (10)ºPrism, blue
V = 2579.9 (2) Å30.24 × 0.16 × 0.06 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		4561 independent reflections
Radiation source: fine-focus sealed tube3122 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.058
Detector resolution: 0.661 pixels mm-1θmax = 25.0º
T = 298(2) Kθmin = 2.1º
ω scansh = −11→11
Absorption correction: analytical
(Sheldrick, 2000)		k = −29→29
Tmin = 0.797, Tmax = 0.946l = −13→13
21071 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.085  w = 1/[σ2(Fo2) + (0.036P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max = 0.001
4561 reflectionsΔρmax = 0.63 e Å−3
457 parametersΔρmin = −0.25 e Å−3
251 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Cu(C7H4NO4)(C21H15N3)]BF4V = 2579.9 (2) Å3
Mr = 625.82Z = 4
Monoclinic, P21/nMo Kα
a = 9.7975 (5) ŵ = 0.92 mm−1
b = 25.1020 (10) ÅT = 298 (2) K
c = 11.0414 (6) Å0.24 × 0.16 × 0.06 mm
β = 108.1830 (10)º
Data collection top
Bruker SMART APEX CCD
diffractometer		4561 independent reflections
Absorption correction: analytical
(Sheldrick, 2000)		3122 reflections with I > 2σ(I)
Tmin = 0.797, Tmax = 0.946Rint = 0.058
21071 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043251 restraints
wR(F2) = 0.085H atoms treated by a mixture of
independent and constrained refinement
S = 0.88Δρmax = 0.63 e Å−3
4561 reflectionsΔρmin = −0.25 e Å−3
457 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*/UeqOcc. (<1)
Cu10.93735 (4)0.164025 (14)0.23849 (4)0.03900 (14)
O10.8720 (2)0.14954 (8)0.4057 (2)0.0472 (6)
O20.7696 (3)0.08826 (9)0.4917 (2)0.0698 (8)
O30.7734 (3)−0.00739 (10)0.5131 (3)0.0752 (8)
H30.754 (4)0.0275 (5)0.501 (3)0.090*
O40.8507 (3)−0.07591 (9)0.4332 (2)0.0640 (7)
C10.8353 (3)0.10311 (13)0.4160 (3)0.0433 (8)
N10.8989 (3)0.08547 (9)0.2279 (2)0.0369 (6)
C20.8651 (3)0.06176 (11)0.3245 (3)0.0345 (8)
C30.8586 (3)0.00616 (12)0.3314 (3)0.0371 (8)
C40.8873 (3)−0.02276 (12)0.2352 (3)0.0469 (9)
H40.8897−0.05980.23970.056*
C50.9120 (4)0.00184 (13)0.1340 (4)0.0549 (10)
H50.9243−0.01790.06690.066*
C60.9182 (4)0.05619 (13)0.1337 (3)0.0507 (9)
H60.93650.07330.06570.061*
C70.8259 (4)−0.02882 (14)0.4319 (3)0.0480 (9)
N81.1567 (3)0.16328 (10)0.3086 (2)0.0370 (6)
C91.2439 (4)0.12160 (13)0.3443 (3)0.0454 (9)
H91.20340.08780.33800.055*
C101.3912 (4)0.12612 (14)0.3902 (3)0.0518 (9)
H101.44830.09600.41600.062*
C111.4525 (4)0.17548 (14)0.3974 (3)0.0537 (10)
H111.55180.17940.42590.064*
C121.3637 (3)0.21937 (13)0.3616 (3)0.0478 (9)
H121.40270.25340.36680.057*
C131.2169 (3)0.21217 (12)0.3179 (3)0.0363 (8)
N140.9758 (2)0.23913 (9)0.2358 (2)0.0340 (6)
C151.1114 (3)0.25650 (11)0.2800 (3)0.0352 (8)
C161.1407 (3)0.31016 (11)0.2911 (3)0.0388 (8)
H161.23520.32200.32120.047*
C171.0275 (3)0.34679 (11)0.2569 (3)0.0365 (8)
C180.8878 (3)0.32764 (11)0.2081 (3)0.0379 (8)
H180.81070.35110.18270.045*
C190.8651 (3)0.27295 (11)0.1976 (3)0.0343 (7)
N200.7350 (3)0.19182 (10)0.1475 (2)0.0381 (6)
C210.7243 (3)0.24570 (12)0.1464 (3)0.0348 (7)
C220.5939 (3)0.27147 (13)0.1016 (3)0.0432 (8)
H220.58920.30850.10080.052*
C230.4704 (3)0.24127 (14)0.0578 (3)0.0514 (9)
H230.38130.25780.02690.062*
C240.4804 (4)0.18665 (14)0.0600 (3)0.0524 (10)
H240.39830.16570.03160.063*
C250.6140 (3)0.16369 (13)0.1053 (3)0.0490 (9)
H250.62040.12670.10650.059*
C261.0554 (3)0.40427 (12)0.2780 (3)0.0384 (8)
C271.1720 (4)0.42823 (13)0.2552 (3)0.0536 (10)
H271.23380.40800.22460.064*
C281.1973 (4)0.48222 (14)0.2775 (4)0.0648 (11)
H281.27560.49790.26110.078*
C291.1096 (4)0.51244 (14)0.3230 (3)0.0614 (11)
H291.12830.54850.33850.074*
C300.9930 (4)0.48949 (13)0.3459 (3)0.0565 (10)
H300.93180.51010.37620.068*
C310.9662 (4)0.43578 (12)0.3240 (3)0.0483 (9)
H310.88730.42050.34030.058*
B11.0843 (4)0.15628 (14)−0.0468 (4)0.0564 (12)
F10.9637 (6)0.1576 (3)−0.0024 (8)0.048 (2)0.537 (14)
F21.1713 (14)0.1141 (4)0.0048 (14)0.087 (4)0.537 (14)
F31.1512 (9)0.2052 (2)−0.0138 (14)0.071 (4)0.537 (14)
F41.0292 (13)0.1520 (4)−0.1777 (5)0.097 (3)0.537 (14)
F1B0.9442 (8)0.1429 (7)−0.0690 (19)0.092 (5)0.250 (8)
F2B1.159 (3)0.1154 (10)0.031 (3)0.068 (5)0.250 (8)
F3B1.127 (2)0.2018 (6)0.0264 (18)0.067 (5)0.250 (8)
F4B1.1384 (18)0.1567 (6)−0.1481 (11)0.093 (4)0.250 (8)
F1C1.007 (2)0.1714 (9)0.0328 (17)0.070 (5)0.215 (12)
F2C1.186 (3)0.1190 (12)0.013 (4)0.080 (7)0.215 (12)
F3C1.1472 (17)0.1973 (7)−0.093 (2)0.080 (4)0.215 (12)
F4C0.9825 (19)0.1355 (9)−0.1543 (17)0.084 (5)0.215 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0377 (2)0.0258 (2)0.0521 (3)−0.00247 (19)0.01201 (19)0.0014 (2)
O10.0622 (16)0.0309 (13)0.0509 (15)−0.0032 (11)0.0214 (12)−0.0050 (11)
O20.105 (2)0.0463 (15)0.083 (2)−0.0069 (14)0.0654 (18)−0.0038 (14)
O30.119 (2)0.0430 (16)0.080 (2)−0.0027 (17)0.0537 (19)0.0127 (15)
O40.087 (2)0.0342 (14)0.0670 (18)−0.0035 (13)0.0185 (15)0.0097 (13)
C10.046 (2)0.039 (2)0.044 (2)−0.0005 (17)0.0123 (18)−0.0020 (17)
N10.0406 (16)0.0258 (14)0.0457 (17)−0.0039 (12)0.0156 (14)−0.0030 (13)
C20.0277 (17)0.0314 (18)0.042 (2)−0.0031 (14)0.0075 (15)0.0001 (15)
C30.0304 (18)0.0299 (18)0.047 (2)−0.0034 (14)0.0062 (16)0.0011 (16)
C40.046 (2)0.0252 (18)0.070 (3)−0.0041 (16)0.0203 (19)−0.0049 (18)
C50.071 (3)0.034 (2)0.072 (3)−0.0080 (18)0.041 (2)−0.0120 (19)
C60.064 (2)0.038 (2)0.059 (3)−0.0078 (18)0.033 (2)−0.0015 (18)
C70.051 (2)0.041 (2)0.049 (2)−0.0081 (18)0.0099 (19)0.0021 (19)
N80.0393 (15)0.0281 (14)0.0433 (16)0.0033 (13)0.0123 (13)0.0023 (13)
C90.049 (2)0.036 (2)0.052 (2)0.0038 (18)0.0171 (18)0.0042 (17)
C100.048 (2)0.044 (2)0.062 (3)0.0175 (19)0.0144 (19)0.0061 (18)
C110.037 (2)0.055 (2)0.065 (3)0.0059 (19)0.0096 (18)−0.005 (2)
C120.037 (2)0.037 (2)0.066 (3)−0.0050 (17)0.0115 (18)−0.0077 (17)
C130.0365 (19)0.0322 (19)0.040 (2)−0.0007 (15)0.0117 (16)−0.0020 (15)
N140.0296 (15)0.0266 (14)0.0431 (16)−0.0004 (12)0.0074 (13)0.0011 (12)
C150.0361 (19)0.0285 (18)0.041 (2)−0.0026 (15)0.0128 (16)0.0004 (15)
C160.0324 (18)0.0340 (18)0.047 (2)−0.0033 (15)0.0081 (16)−0.0012 (15)
C170.038 (2)0.0319 (18)0.0393 (19)−0.0027 (15)0.0122 (16)−0.0002 (15)
C180.0367 (18)0.0282 (18)0.046 (2)0.0024 (15)0.0084 (15)0.0032 (15)
C190.0338 (18)0.0306 (17)0.038 (2)0.0002 (15)0.0101 (15)0.0013 (15)
N200.0351 (16)0.0297 (15)0.0472 (17)−0.0035 (12)0.0095 (13)−0.0002 (12)
C210.0331 (18)0.0354 (19)0.0360 (19)−0.0003 (15)0.0108 (15)0.0009 (15)
C220.040 (2)0.0361 (19)0.051 (2)0.0006 (16)0.0101 (17)0.0036 (17)
C230.033 (2)0.055 (2)0.061 (3)0.0025 (18)0.0076 (18)0.0060 (19)
C240.032 (2)0.052 (2)0.067 (3)−0.0107 (18)0.0065 (18)0.0030 (19)
C250.043 (2)0.038 (2)0.063 (2)−0.0076 (18)0.0122 (18)−0.0006 (18)
C260.0376 (19)0.0323 (18)0.042 (2)−0.0031 (16)0.0080 (16)0.0003 (16)
C270.061 (2)0.039 (2)0.065 (3)−0.0039 (19)0.027 (2)0.0024 (19)
C280.069 (3)0.042 (2)0.085 (3)−0.020 (2)0.027 (2)0.003 (2)
C290.077 (3)0.031 (2)0.067 (3)−0.010 (2)0.008 (2)−0.0044 (19)
C300.056 (2)0.039 (2)0.068 (3)0.0030 (19)0.010 (2)−0.0080 (19)
C310.045 (2)0.034 (2)0.061 (2)−0.0051 (17)0.0107 (18)−0.0014 (17)
B10.047 (3)0.046 (3)0.075 (4)−0.006 (2)0.016 (3)0.008 (3)
F10.034 (3)0.053 (4)0.044 (5)−0.013 (3)−0.008 (3)−0.005 (3)
F20.057 (7)0.043 (5)0.146 (8)0.011 (5)0.012 (6)0.000 (5)
F30.040 (3)0.042 (3)0.137 (10)−0.006 (2)0.036 (5)0.004 (4)
F40.121 (7)0.118 (6)0.064 (4)0.007 (5)0.045 (4)0.012 (3)
F1B0.049 (6)0.096 (8)0.092 (10)−0.024 (6)−0.032 (7)0.024 (8)
F2B0.059 (9)0.058 (9)0.100 (9)0.019 (8)0.041 (7)0.035 (7)
F3B0.059 (9)0.068 (7)0.083 (8)−0.005 (6)0.035 (6)−0.019 (6)
F4B0.111 (9)0.109 (8)0.067 (7)−0.029 (8)0.036 (7)−0.006 (6)
F1C0.078 (10)0.072 (10)0.052 (8)0.011 (8)0.009 (8)−0.020 (6)
F2C0.046 (10)0.063 (11)0.132 (13)0.005 (9)0.028 (11)0.028 (11)
F3C0.078 (7)0.084 (8)0.085 (9)0.001 (7)0.035 (7)0.027 (7)
F4C0.070 (9)0.112 (10)0.072 (9)−0.006 (7)0.023 (8)−0.020 (8)
Geometric parameters (Å, °) top
Cu1—N141.925 (2)C17—C181.390 (4)
Cu1—N12.004 (2)C17—C261.474 (4)
Cu1—N82.045 (2)C18—C191.390 (4)
Cu1—N202.045 (2)C18—H180.9300
Cu1—O12.165 (2)C19—C211.485 (4)
Cu1—F12.756 (7)N20—C251.333 (4)
O1—C11.236 (3)N20—C211.356 (3)
O2—C11.260 (4)C21—C221.378 (4)
O3—C71.283 (4)C22—C231.381 (4)
O3—H30.897 (11)C22—H220.9300
O4—C71.206 (4)C23—C241.374 (4)
C1—C21.539 (4)C23—H230.9300
N1—C61.334 (4)C24—C251.374 (4)
N1—C21.350 (3)C24—H240.9300
C2—C31.400 (4)C25—H250.9300
C3—C41.386 (4)C26—C271.382 (4)
C3—C71.526 (4)C26—C311.387 (4)
C4—C51.362 (4)C27—C281.386 (4)
C4—H40.9300C27—H270.9300
C5—C61.366 (4)C28—C291.354 (5)
C5—H50.9300C28—H280.9300
C6—H60.9300C29—C301.372 (5)
N8—C91.330 (4)C29—H290.9300
N8—C131.351 (3)C30—C311.380 (4)
C9—C101.377 (4)C30—H300.9300
C9—H90.9300C31—H310.9300
C10—C111.368 (4)B1—F1B1.360 (6)
C10—H100.9300B1—F21.366 (6)
C11—C121.383 (4)B1—F3C1.376 (7)
C11—H110.9300B1—F2C1.379 (7)
C12—C131.379 (4)B1—F4B1.379 (6)
C12—H120.9300B1—F41.380 (5)
C13—C151.487 (4)B1—F1C1.382 (7)
N14—C151.337 (3)B1—F31.385 (5)
N14—C191.338 (3)B1—F3B1.385 (7)
C15—C161.375 (4)B1—F2B1.390 (7)
C16—C171.399 (4)B1—F4C1.392 (7)
C16—H160.9300B1—F11.414 (5)
N14—Cu1—N1175.58 (10)C15—C16—H16120.2
N14—Cu1—N880.04 (10)C17—C16—H16120.2
N1—Cu1—N899.75 (10)C18—C17—C16118.6 (3)
N14—Cu1—N2079.78 (10)C18—C17—C26120.8 (3)
N1—Cu1—N2099.86 (10)C16—C17—C26120.5 (3)
N8—Cu1—N20158.79 (10)C19—C18—C17119.1 (3)
N14—Cu1—O1106.81 (9)C19—C18—H18120.4
N1—Cu1—O177.56 (9)C17—C18—H18120.4
N8—Cu1—O1103.36 (9)N14—C19—C18120.5 (3)
N20—Cu1—O188.70 (9)N14—C19—C21113.2 (3)
N14—Cu1—F187.96 (17)C18—C19—C21126.3 (3)
N1—Cu1—F187.62 (17)C25—N20—C21117.8 (3)
N8—Cu1—F187.76 (15)C25—N20—Cu1127.7 (2)
N20—Cu1—F185.07 (14)C21—N20—Cu1113.92 (19)
O1—Cu1—F1162.70 (17)N20—C21—C22122.1 (3)
C1—O1—Cu1114.2 (2)N20—C21—C19113.3 (3)
C7—O3—H3114 (2)C22—C21—C19124.6 (3)
O1—C1—O2124.3 (3)C21—C22—C23118.7 (3)
O1—C1—C2117.1 (3)C21—C22—H22120.6
O2—C1—C2118.5 (3)C23—C22—H22120.6
C6—N1—C2120.2 (3)C24—C23—C22119.5 (3)
C6—N1—Cu1121.2 (2)C24—C23—H23120.3
C2—N1—Cu1118.4 (2)C22—C23—H23120.3
N1—C2—C3120.6 (3)C25—C24—C23118.6 (3)
N1—C2—C1111.4 (3)C25—C24—H24120.7
C3—C2—C1128.0 (3)C23—C24—H24120.7
C4—C3—C2117.2 (3)N20—C25—C24123.2 (3)
C4—C3—C7113.3 (3)N20—C25—H25118.4
C2—C3—C7129.5 (3)C24—C25—H25118.4
C5—C4—C3121.4 (3)C27—C26—C31118.0 (3)
C5—C4—H4119.3C27—C26—C17121.4 (3)
C3—C4—H4119.3C31—C26—C17120.6 (3)
C4—C5—C6118.3 (3)C26—C27—C28120.3 (3)
C4—C5—H5120.8C26—C27—H27119.8
C6—C5—H5120.8C28—C27—H27119.8
N1—C6—C5122.1 (3)C29—C28—C27121.0 (3)
N1—C6—H6119.0C29—C28—H28119.5
C5—C6—H6119.0C27—C28—H28119.5
O4—C7—O3121.7 (3)C28—C29—C30119.6 (3)
O4—C7—C3119.0 (3)C28—C29—H29120.2
O3—C7—C3119.2 (3)C30—C29—H29120.2
C9—N8—C13117.9 (3)C29—C30—C31120.1 (3)
C9—N8—Cu1128.4 (2)C29—C30—H30119.9
C13—N8—Cu1113.7 (2)C31—C30—H30119.9
N8—C9—C10123.1 (3)C30—C31—C26120.9 (3)
N8—C9—H9118.4C30—C31—H31119.5
C10—C9—H9118.4C26—C31—H31119.5
C11—C10—C9119.1 (3)F3C—B1—F2C110.2 (15)
C11—C10—H10120.4F1B—B1—F4B118.5 (9)
C9—C10—H10120.4F2—B1—F4111.5 (7)
C10—C11—C12118.7 (3)F3C—B1—F1C115.4 (11)
C10—C11—H11120.7F2C—B1—F1C109.8 (16)
C12—C11—H11120.7F2—B1—F3113.2 (7)
C13—C12—C11119.3 (3)F4—B1—F3110.0 (5)
C13—C12—H12120.3F1B—B1—F3B114.3 (11)
C11—C12—H12120.3F4B—B1—F3B110.3 (9)
N8—C13—C12121.9 (3)F1B—B1—F2B103.6 (14)
N8—C13—C15114.2 (3)F4B—B1—F2B104.3 (13)
C12—C13—C15123.9 (3)F3B—B1—F2B104.0 (15)
C15—N14—C19121.6 (2)F3C—B1—F4C104.4 (10)
C15—N14—Cu1119.39 (19)F2C—B1—F4C112.1 (17)
C19—N14—Cu1118.89 (19)F1C—B1—F4C104.8 (10)
N14—C15—C16120.5 (3)F2—B1—F1110.7 (7)
N14—C15—C13112.5 (2)F4—B1—F1105.6 (5)
C16—C15—C13126.9 (3)F3—B1—F1105.4 (5)
C15—C16—C17119.6 (3)B1—F1—Cu1132.5 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.897 (11)1.539 (15)2.412 (3)163 (4)
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.897 (11)1.539 (15)2.412 (3)163 (4)
Acknowledgements top

SM—V would like to thank CONACYT for a PhD scholarship. The authors are grateful to CONACYT (40332-Q) and DGAPA-UNAM (IN216806) for financial support, and to the CSCI, Spain, for a license to use the Cambridge Structural Database.

references
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