metal-organic compounds
[5-(Pyridin-2-yl)-1H-tetrazole-κ2N4,N5]bis(triphenylphosphane-κP)copper(I) tetrafluoridoborate
aCollege of Sciences, Zhejiang A & F University, Hangzhou 311300, People's Republic of China
*Correspondence e-mail: lfshi2003@163.com
In the title CuI compound, [Cu(C6H5N5)(C18H15P)2]BF4, the CuI cation is N,N′-chelated by a 5-(pyridin-2-yl)-1H-tetrazole ligand and coordinated by two triphenylphosphane ligands in a distorted tetrahedral geometry. The tetrazole and pyridine rings are essentially coplanar [dihedral angle = 4.1 (3)°]. The tetrafluoridoborate anion links to the complex cation via an N—H⋯F hydrogen bond.
Related literature
For applications of CuI complexes, see: Jia et al. (2005); Tsuboyama et al. (2007); Zhang et al. (2004). For the synthesis, see: Kuang et al. (2002); Demko & Sharpless (2001).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536812047605/xu5633sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047605/xu5633Isup2.hkl
The 5-(2-Pyridyl)tetrazole ligand was synthesized according to the literature method (Demko & Sharpless, 2001) with some minor modification. The specific synthetic procedure is as follows: (i) To a 100 ml round-bottomed flask was added 2-cyanopyridine (0.52 g, 5 mmol), sodium azide (0.36 g, 5.5 mmol), zinc bromide (1.15 g, 5 mmol), and water (30 ml). The reaction mixture was refluxed for 5 h, cooled to room temperature. Then the mixture was basified by addition of 2.5 equiv of NaOH, filtered, acidified to pH = 1, and filtered, and the solid was washed with water then 5-(2-Pyridyl)tetrazole (0.58 g, 78%) was obtained.
[Cu(PPh3)2(L)]BF4 was synthesized according to the following procedure (Kuang et al., 2002): To a 100 ml flask was added [Cu(CH3CN)4]BF4 0.314 g (1 mmol), triphenylphosphane 0.522 g(2 mmol) and 10 ml dichioromethane, kept stirring for 1 h. Then 0.148 g 5-(2-Pyridyl)tetrazole was added and stirred for another hour. After the evaporation of solvent, the product was obtained as a light green powder. Single crystals of complex [Cu(PPh3)2(L)]BF4 suitable for X-ray diffraction studies were grown from slow evaporation of a CH2Cl2 solution.
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The asymmetric unit of [Cu(PPh3)2(L)]BF4, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level (arbitrary spheres for the H atoms). |
[Cu(C6H5N5)(C18H15P)2]BF4 | Z = 2 |
Mr = 822.05 | F(000) = 844 |
Triclinic, P1 | Dx = 1.367 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6640 (19) Å | Cell parameters from 6566 reflections |
b = 13.052 (3) Å | θ = 3.0–26.0° |
c = 15.947 (3) Å | µ = 0.68 mm−1 |
α = 88.66 (3)° | T = 293 K |
β = 84.80 (3)° | Block, light green |
γ = 85.72 (3)° | 0.29 × 0.17 × 0.16 mm |
V = 1997.3 (7) Å3 |
Bruker SMART 1000 CCD area-detector diffractometer | 8838 independent reflections |
Radiation source: fine-focus sealed tube | 4984 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
phi and ω scans | θmax = 27.4°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −12→12 |
Tmin = 0.908, Tmax = 0.947 | k = −16→16 |
19069 measured reflections | l = −18→20 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.166 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0409P)2 + 3.0232P] where P = (Fo2 + 2Fc2)/3 |
8838 reflections | (Δ/σ)max = 0.001 |
496 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −1.12 e Å−3 |
[Cu(C6H5N5)(C18H15P)2]BF4 | γ = 85.72 (3)° |
Mr = 822.05 | V = 1997.3 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.6640 (19) Å | Mo Kα radiation |
b = 13.052 (3) Å | µ = 0.68 mm−1 |
c = 15.947 (3) Å | T = 293 K |
α = 88.66 (3)° | 0.29 × 0.17 × 0.16 mm |
β = 84.80 (3)° |
Bruker SMART 1000 CCD area-detector diffractometer | 8838 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 4984 reflections with I > 2σ(I) |
Tmin = 0.908, Tmax = 0.947 | Rint = 0.036 |
19069 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.166 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.70 e Å−3 |
8838 reflections | Δρmin = −1.12 e Å−3 |
496 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cu | 0.58602 (5) | 0.22693 (4) | 0.77067 (3) | 0.04916 (17) | |
P1 | 0.57823 (11) | 0.05451 (8) | 0.77005 (7) | 0.0470 (3) | |
P2 | 0.54981 (11) | 0.33726 (8) | 0.66269 (7) | 0.0453 (3) | |
N1 | 0.5096 (4) | 0.2971 (3) | 0.8908 (2) | 0.0528 (9) | |
N2 | 0.7728 (4) | 0.2473 (3) | 0.8243 (2) | 0.0524 (9) | |
N3 | 0.9126 (4) | 0.2261 (3) | 0.8087 (3) | 0.0661 (11) | |
N4 | 0.9758 (4) | 0.2553 (4) | 0.8710 (3) | 0.0777 (13) | |
N5 | 0.8761 (5) | 0.2956 (3) | 0.9278 (3) | 0.0731 (12) | |
H55 | 0.8905 | 0.3207 | 0.9754 | 0.088* | |
B1 | 1.0728 (9) | 0.5802 (7) | 0.8609 (5) | 0.094 (3) | |
F1 | 1.1936 (6) | 0.5302 (6) | 0.8667 (4) | 0.235 (4) | |
F2 | 0.9726 (7) | 0.5127 (4) | 0.8631 (3) | 0.168 (2) | |
F3 | 1.0651 (6) | 0.6349 (5) | 0.7899 (3) | 0.171 (2) | |
F4 | 1.0472 (6) | 0.6438 (4) | 0.9270 (3) | 0.167 (2) | |
C1 | 0.6524 (5) | 0.0373 (4) | 0.9330 (3) | 0.0623 (12) | |
H1 | 0.5935 | 0.0966 | 0.9411 | 0.075* | |
C2 | 0.6681 (4) | −0.0088 (3) | 0.8555 (3) | 0.0478 (10) | |
C3 | 0.7541 (5) | −0.0988 (4) | 0.8461 (3) | 0.0653 (13) | |
H3 | 0.7650 | −0.1320 | 0.7947 | 0.078* | |
C4 | 0.8237 (6) | −0.1392 (5) | 0.9129 (4) | 0.0845 (18) | |
H4 | 0.8814 | −0.1992 | 0.9060 | 0.101* | |
C5 | 0.8083 (6) | −0.0915 (5) | 0.9885 (4) | 0.0898 (19) | |
H5 | 0.8557 | −0.1189 | 1.0331 | 0.108* | |
C6 | 0.7236 (6) | −0.0037 (5) | 0.9990 (3) | 0.0853 (17) | |
H6 | 0.7134 | 0.0288 | 1.0507 | 0.102* | |
C7 | 0.8132 (5) | 0.0060 (4) | 0.6619 (3) | 0.0669 (13) | |
H7 | 0.8582 | 0.0419 | 0.6997 | 0.080* | |
C8 | 0.8880 (6) | −0.0373 (5) | 0.5923 (4) | 0.0832 (17) | |
H8 | 0.9837 | −0.0320 | 0.5842 | 0.100* | |
C9 | 0.8223 (7) | −0.0880 (5) | 0.5349 (4) | 0.0889 (18) | |
H9 | 0.8734 | −0.1177 | 0.4883 | 0.107* | |
C10 | 0.6813 (7) | −0.0948 (4) | 0.5462 (4) | 0.0823 (17) | |
H10 | 0.6363 | −0.1272 | 0.5063 | 0.099* | |
C11 | 0.6053 (5) | −0.0540 (4) | 0.6167 (3) | 0.0614 (12) | |
H11 | 0.5098 | −0.0601 | 0.6246 | 0.074* | |
C12 | 0.6713 (4) | −0.0038 (3) | 0.6757 (3) | 0.0507 (10) | |
C13 | 0.4103 (4) | 0.0003 (4) | 0.7760 (3) | 0.0536 (11) | |
C14 | 0.3943 (5) | −0.1031 (4) | 0.7932 (3) | 0.0640 (13) | |
H14 | 0.4715 | −0.1464 | 0.8045 | 0.077* | |
C15 | 0.2646 (6) | −0.1428 (5) | 0.7937 (4) | 0.0849 (18) | |
H15 | 0.2548 | −0.2122 | 0.8052 | 0.102* | |
C16 | 0.1518 (6) | −0.0788 (7) | 0.7772 (5) | 0.105 (2) | |
H16 | 0.0648 | −0.1049 | 0.7775 | 0.125* | |
C17 | 0.1653 (6) | 0.0231 (6) | 0.7603 (5) | 0.106 (2) | |
H17 | 0.0876 | 0.0661 | 0.7493 | 0.128* | |
C18 | 0.2942 (5) | 0.0625 (4) | 0.7594 (4) | 0.0750 (16) | |
H18 | 0.3026 | 0.1319 | 0.7475 | 0.090* | |
C19 | 0.6554 (4) | 0.3099 (3) | 0.5644 (3) | 0.0454 (10) | |
C20 | 0.6671 (5) | 0.2101 (4) | 0.5339 (3) | 0.0629 (12) | |
H20 | 0.6228 | 0.1588 | 0.5650 | 0.076* | |
C21 | 0.7436 (6) | 0.1857 (4) | 0.4581 (3) | 0.0749 (15) | |
H21 | 0.7480 | 0.1191 | 0.4380 | 0.090* | |
C22 | 0.8129 (5) | 0.2602 (5) | 0.4129 (3) | 0.0721 (14) | |
H22 | 0.8659 | 0.2437 | 0.3628 | 0.087* | |
C23 | 0.8038 (5) | 0.3585 (4) | 0.4416 (3) | 0.0673 (13) | |
H23 | 0.8504 | 0.4089 | 0.4110 | 0.081* | |
C24 | 0.7246 (5) | 0.3833 (4) | 0.5170 (3) | 0.0569 (11) | |
H24 | 0.7184 | 0.4506 | 0.5356 | 0.068* | |
C25 | 0.5866 (4) | 0.4693 (3) | 0.6838 (3) | 0.0493 (10) | |
C26 | 0.7149 (5) | 0.4857 (4) | 0.7118 (3) | 0.0629 (13) | |
H26 | 0.7758 | 0.4298 | 0.7238 | 0.076* | |
C27 | 0.7529 (6) | 0.5842 (4) | 0.7220 (3) | 0.0759 (15) | |
H27 | 0.8396 | 0.5947 | 0.7400 | 0.091* | |
C28 | 0.6622 (7) | 0.6666 (4) | 0.7055 (4) | 0.0820 (17) | |
H28 | 0.6879 | 0.7331 | 0.7117 | 0.098* | |
C29 | 0.5351 (6) | 0.6514 (4) | 0.6802 (4) | 0.0786 (16) | |
H29 | 0.4735 | 0.7076 | 0.6701 | 0.094* | |
C30 | 0.4964 (5) | 0.5533 (4) | 0.6692 (3) | 0.0622 (13) | |
H30 | 0.4090 | 0.5438 | 0.6519 | 0.075* | |
C31 | 0.3718 (4) | 0.3494 (3) | 0.6329 (3) | 0.0456 (9) | |
C32 | 0.3376 (5) | 0.3416 (3) | 0.5508 (3) | 0.0558 (11) | |
H32 | 0.4079 | 0.3320 | 0.5072 | 0.067* | |
C33 | 0.1983 (5) | 0.3481 (4) | 0.5333 (4) | 0.0720 (15) | |
H33 | 0.1759 | 0.3415 | 0.4782 | 0.086* | |
C34 | 0.0941 (5) | 0.3641 (4) | 0.5973 (4) | 0.0784 (16) | |
H34 | 0.0013 | 0.3671 | 0.5856 | 0.094* | |
C35 | 0.1268 (5) | 0.3756 (5) | 0.6780 (4) | 0.0801 (16) | |
H35 | 0.0563 | 0.3895 | 0.7208 | 0.096* | |
C36 | 0.2637 (5) | 0.3666 (4) | 0.6959 (3) | 0.0695 (14) | |
H36 | 0.2846 | 0.3722 | 0.7514 | 0.083* | |
C37 | 0.3794 (5) | 0.3180 (4) | 0.9229 (3) | 0.0710 (14) | |
H37 | 0.3071 | 0.3033 | 0.8913 | 0.085* | |
C38 | 0.3466 (7) | 0.3612 (5) | 1.0023 (4) | 0.0869 (18) | |
H38 | 0.2542 | 0.3763 | 1.0225 | 0.104* | |
C39 | 0.4517 (8) | 0.3807 (5) | 1.0494 (4) | 0.0923 (19) | |
H39 | 0.4319 | 0.4080 | 1.1029 | 0.111* | |
C40 | 0.5873 (7) | 0.3598 (4) | 1.0173 (3) | 0.0787 (16) | |
H40 | 0.6606 | 0.3735 | 1.0483 | 0.094* | |
C41 | 0.6128 (5) | 0.3183 (3) | 0.9383 (3) | 0.0539 (11) | |
C42 | 0.7515 (5) | 0.2904 (3) | 0.8988 (3) | 0.0533 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.0538 (3) | 0.0448 (3) | 0.0488 (3) | 0.0032 (2) | −0.0101 (2) | 0.0002 (2) |
P1 | 0.0445 (6) | 0.0425 (6) | 0.0540 (7) | 0.0010 (4) | −0.0083 (5) | −0.0014 (5) |
P2 | 0.0472 (6) | 0.0423 (6) | 0.0463 (6) | 0.0039 (4) | −0.0101 (5) | 0.0008 (5) |
N1 | 0.058 (2) | 0.052 (2) | 0.047 (2) | 0.0029 (17) | 0.0012 (17) | 0.0002 (17) |
N2 | 0.052 (2) | 0.051 (2) | 0.052 (2) | 0.0000 (16) | −0.0021 (17) | 0.0046 (17) |
N3 | 0.049 (2) | 0.070 (3) | 0.079 (3) | 0.0067 (19) | −0.008 (2) | 0.001 (2) |
N4 | 0.057 (3) | 0.085 (3) | 0.094 (4) | 0.002 (2) | −0.023 (3) | −0.006 (3) |
N5 | 0.073 (3) | 0.075 (3) | 0.075 (3) | −0.002 (2) | −0.032 (2) | −0.009 (2) |
B1 | 0.101 (6) | 0.097 (6) | 0.091 (6) | 0.010 (5) | −0.057 (5) | −0.029 (5) |
F1 | 0.174 (5) | 0.282 (8) | 0.247 (7) | 0.130 (5) | −0.103 (5) | −0.132 (6) |
F2 | 0.234 (6) | 0.144 (4) | 0.143 (4) | −0.071 (4) | −0.069 (4) | 0.022 (3) |
F3 | 0.189 (5) | 0.211 (6) | 0.134 (4) | −0.100 (4) | −0.066 (4) | 0.044 (4) |
F4 | 0.192 (5) | 0.168 (4) | 0.145 (4) | 0.061 (4) | −0.079 (4) | −0.090 (4) |
C1 | 0.069 (3) | 0.062 (3) | 0.054 (3) | −0.001 (2) | −0.001 (2) | 0.006 (2) |
C2 | 0.042 (2) | 0.046 (2) | 0.055 (3) | −0.0010 (18) | −0.0031 (18) | 0.004 (2) |
C3 | 0.068 (3) | 0.056 (3) | 0.070 (3) | 0.010 (2) | −0.009 (3) | 0.005 (2) |
C4 | 0.077 (4) | 0.081 (4) | 0.090 (4) | 0.022 (3) | −0.007 (3) | 0.029 (3) |
C5 | 0.085 (4) | 0.116 (5) | 0.067 (4) | 0.007 (4) | −0.019 (3) | 0.038 (4) |
C6 | 0.104 (5) | 0.099 (5) | 0.052 (3) | 0.004 (4) | −0.015 (3) | 0.012 (3) |
C7 | 0.052 (3) | 0.082 (4) | 0.066 (3) | −0.003 (2) | −0.003 (2) | −0.002 (3) |
C8 | 0.064 (3) | 0.095 (5) | 0.084 (4) | 0.008 (3) | 0.019 (3) | −0.003 (3) |
C9 | 0.108 (5) | 0.070 (4) | 0.082 (4) | −0.003 (3) | 0.032 (4) | −0.013 (3) |
C10 | 0.112 (5) | 0.068 (4) | 0.066 (4) | −0.023 (3) | 0.011 (3) | −0.023 (3) |
C11 | 0.065 (3) | 0.056 (3) | 0.063 (3) | −0.009 (2) | 0.003 (2) | −0.010 (2) |
C12 | 0.052 (2) | 0.042 (2) | 0.058 (3) | −0.0024 (18) | −0.006 (2) | 0.005 (2) |
C13 | 0.047 (2) | 0.057 (3) | 0.056 (3) | 0.008 (2) | −0.005 (2) | −0.014 (2) |
C14 | 0.054 (3) | 0.065 (3) | 0.073 (3) | −0.008 (2) | 0.003 (2) | −0.010 (3) |
C15 | 0.070 (4) | 0.092 (4) | 0.095 (4) | −0.035 (3) | 0.011 (3) | −0.022 (3) |
C16 | 0.050 (3) | 0.145 (7) | 0.121 (6) | −0.023 (4) | 0.006 (3) | −0.055 (5) |
C17 | 0.046 (3) | 0.123 (6) | 0.151 (7) | 0.013 (3) | −0.022 (3) | −0.056 (5) |
C18 | 0.052 (3) | 0.069 (3) | 0.107 (4) | 0.006 (2) | −0.021 (3) | −0.024 (3) |
C19 | 0.041 (2) | 0.046 (2) | 0.049 (2) | 0.0042 (17) | −0.0122 (18) | 0.0079 (19) |
C20 | 0.074 (3) | 0.047 (3) | 0.065 (3) | 0.007 (2) | −0.001 (2) | 0.000 (2) |
C21 | 0.096 (4) | 0.060 (3) | 0.064 (3) | 0.014 (3) | 0.001 (3) | −0.009 (3) |
C22 | 0.070 (3) | 0.084 (4) | 0.059 (3) | 0.015 (3) | 0.000 (3) | −0.005 (3) |
C23 | 0.063 (3) | 0.077 (4) | 0.060 (3) | −0.001 (3) | −0.003 (2) | 0.007 (3) |
C24 | 0.064 (3) | 0.057 (3) | 0.049 (3) | 0.002 (2) | −0.005 (2) | −0.002 (2) |
C25 | 0.052 (2) | 0.050 (3) | 0.047 (2) | 0.0005 (19) | −0.0151 (19) | −0.0027 (19) |
C26 | 0.060 (3) | 0.062 (3) | 0.070 (3) | −0.003 (2) | −0.023 (2) | 0.005 (2) |
C27 | 0.080 (4) | 0.079 (4) | 0.074 (4) | −0.022 (3) | −0.027 (3) | −0.002 (3) |
C28 | 0.104 (5) | 0.059 (3) | 0.089 (4) | −0.014 (3) | −0.029 (3) | −0.020 (3) |
C29 | 0.097 (4) | 0.046 (3) | 0.094 (4) | 0.011 (3) | −0.026 (3) | −0.017 (3) |
C30 | 0.065 (3) | 0.052 (3) | 0.071 (3) | 0.007 (2) | −0.023 (2) | −0.011 (2) |
C31 | 0.048 (2) | 0.036 (2) | 0.051 (2) | 0.0021 (17) | −0.0053 (19) | 0.0008 (18) |
C32 | 0.060 (3) | 0.056 (3) | 0.052 (3) | 0.001 (2) | −0.009 (2) | −0.010 (2) |
C33 | 0.060 (3) | 0.080 (4) | 0.081 (4) | −0.001 (3) | −0.032 (3) | −0.017 (3) |
C34 | 0.048 (3) | 0.086 (4) | 0.105 (5) | −0.009 (3) | −0.023 (3) | 0.000 (3) |
C35 | 0.048 (3) | 0.102 (5) | 0.087 (4) | 0.002 (3) | 0.001 (3) | 0.015 (3) |
C36 | 0.055 (3) | 0.095 (4) | 0.057 (3) | 0.006 (3) | −0.005 (2) | 0.008 (3) |
C37 | 0.056 (3) | 0.081 (4) | 0.071 (3) | 0.003 (3) | 0.011 (2) | 0.000 (3) |
C38 | 0.087 (4) | 0.080 (4) | 0.085 (4) | 0.011 (3) | 0.027 (3) | 0.002 (3) |
C39 | 0.124 (6) | 0.085 (5) | 0.063 (4) | 0.006 (4) | 0.013 (4) | −0.014 (3) |
C40 | 0.103 (4) | 0.076 (4) | 0.056 (3) | 0.000 (3) | −0.004 (3) | −0.013 (3) |
C41 | 0.071 (3) | 0.044 (3) | 0.046 (2) | 0.002 (2) | −0.009 (2) | −0.0014 (19) |
C42 | 0.059 (3) | 0.045 (3) | 0.057 (3) | 0.000 (2) | −0.014 (2) | 0.001 (2) |
Cu—P1 | 2.2575 (13) | C15—H15 | 0.9300 |
Cu—P2 | 2.2538 (14) | C16—C17 | 1.364 (10) |
Cu—N1 | 2.185 (4) | C16—H16 | 0.9300 |
Cu—N2 | 2.103 (4) | C17—C18 | 1.381 (8) |
P1—C13 | 1.812 (5) | C17—H17 | 0.9300 |
P1—C2 | 1.831 (4) | C18—H18 | 0.9300 |
P1—C12 | 1.832 (5) | C19—C24 | 1.381 (6) |
P2—C19 | 1.819 (4) | C19—C20 | 1.394 (6) |
P2—C31 | 1.820 (4) | C20—C21 | 1.389 (7) |
P2—C25 | 1.830 (4) | C20—H20 | 0.9300 |
N1—C37 | 1.326 (6) | C21—C22 | 1.375 (7) |
N1—C41 | 1.355 (5) | C21—H21 | 0.9300 |
N2—C42 | 1.320 (5) | C22—C23 | 1.366 (7) |
N2—N3 | 1.360 (5) | C22—H22 | 0.9300 |
N3—N4 | 1.292 (6) | C23—C24 | 1.396 (6) |
N4—N5 | 1.346 (6) | C23—H23 | 0.9300 |
N5—C42 | 1.336 (6) | C24—H24 | 0.9300 |
N5—H55 | 0.8600 | C25—C30 | 1.378 (6) |
B1—F1 | 1.304 (8) | C25—C26 | 1.388 (6) |
B1—F3 | 1.329 (9) | C26—C27 | 1.381 (7) |
B1—F4 | 1.351 (8) | C26—H26 | 0.9300 |
B1—F2 | 1.355 (9) | C27—C28 | 1.371 (7) |
C1—C2 | 1.378 (6) | C27—H27 | 0.9300 |
C1—C6 | 1.384 (7) | C28—C29 | 1.357 (7) |
C1—H1 | 0.9300 | C28—H28 | 0.9300 |
C2—C3 | 1.390 (6) | C29—C30 | 1.380 (7) |
C3—C4 | 1.384 (7) | C29—H29 | 0.9300 |
C3—H3 | 0.9300 | C30—H30 | 0.9300 |
C4—C5 | 1.361 (8) | C31—C32 | 1.387 (6) |
C4—H4 | 0.9300 | C31—C36 | 1.391 (6) |
C5—C6 | 1.362 (8) | C32—C33 | 1.396 (6) |
C5—H5 | 0.9300 | C32—H32 | 0.9300 |
C6—H6 | 0.9300 | C33—C34 | 1.375 (7) |
C7—C8 | 1.377 (7) | C33—H33 | 0.9300 |
C7—C12 | 1.384 (6) | C34—C35 | 1.367 (8) |
C7—H7 | 0.9300 | C34—H34 | 0.9300 |
C8—C9 | 1.370 (8) | C35—C36 | 1.375 (7) |
C8—H8 | 0.9300 | C35—H35 | 0.9300 |
C9—C10 | 1.367 (8) | C36—H36 | 0.9300 |
C9—H9 | 0.9300 | C37—C38 | 1.399 (8) |
C10—C11 | 1.381 (7) | C37—H37 | 0.9300 |
C10—H10 | 0.9300 | C38—C39 | 1.360 (9) |
C11—C12 | 1.385 (6) | C38—H38 | 0.9300 |
C11—H11 | 0.9300 | C39—C40 | 1.373 (8) |
C13—C18 | 1.377 (6) | C39—H39 | 0.9300 |
C13—C14 | 1.388 (6) | C40—C41 | 1.378 (6) |
C14—C15 | 1.391 (7) | C40—H40 | 0.9300 |
C14—H14 | 0.9300 | C41—C42 | 1.452 (6) |
C15—C16 | 1.364 (9) | ||
N2—Cu—N1 | 78.18 (14) | C17—C16—H16 | 119.6 |
N2—Cu—P2 | 112.66 (11) | C15—C16—H16 | 119.6 |
N1—Cu—P2 | 110.72 (10) | C16—C17—C18 | 120.0 (6) |
N2—Cu—P1 | 103.38 (11) | C16—C17—H17 | 120.0 |
N1—Cu—P1 | 114.14 (11) | C18—C17—H17 | 120.0 |
P2—Cu—P1 | 126.75 (5) | C13—C18—C17 | 120.9 (6) |
C13—P1—C2 | 105.0 (2) | C13—C18—H18 | 119.5 |
C13—P1—C12 | 103.4 (2) | C17—C18—H18 | 119.5 |
C2—P1—C12 | 102.91 (19) | C24—C19—C20 | 117.5 (4) |
C13—P1—Cu | 119.03 (15) | C24—C19—P2 | 123.5 (3) |
C2—P1—Cu | 112.17 (15) | C20—C19—P2 | 119.0 (3) |
C12—P1—Cu | 112.77 (15) | C21—C20—C19 | 121.3 (5) |
C19—P2—C31 | 104.20 (18) | C21—C20—H20 | 119.4 |
C19—P2—C25 | 102.9 (2) | C19—C20—H20 | 119.4 |
C31—P2—C25 | 103.88 (18) | C22—C21—C20 | 119.9 (5) |
C19—P2—Cu | 116.03 (13) | C22—C21—H21 | 120.1 |
C31—P2—Cu | 114.80 (14) | C20—C21—H21 | 120.1 |
C25—P2—Cu | 113.54 (14) | C23—C22—C21 | 120.0 (5) |
C37—N1—C41 | 117.5 (4) | C23—C22—H22 | 120.0 |
C37—N1—Cu | 129.1 (3) | C21—C22—H22 | 120.0 |
C41—N1—Cu | 113.3 (3) | C22—C23—C24 | 120.1 (5) |
C42—N2—N3 | 107.1 (4) | C22—C23—H23 | 120.0 |
C42—N2—Cu | 112.5 (3) | C24—C23—H23 | 120.0 |
N3—N2—Cu | 140.3 (3) | C19—C24—C23 | 121.3 (5) |
N4—N3—N2 | 110.0 (4) | C19—C24—H24 | 119.3 |
N3—N4—N5 | 106.4 (4) | C23—C24—H24 | 119.3 |
C42—N5—N4 | 109.5 (4) | C30—C25—C26 | 118.5 (4) |
C42—N5—H55 | 125.3 | C30—C25—P2 | 123.3 (3) |
N4—N5—H55 | 125.3 | C26—C25—P2 | 118.1 (3) |
F1—B1—F3 | 113.6 (9) | C27—C26—C25 | 120.6 (5) |
F1—B1—F4 | 108.3 (5) | C27—C26—H26 | 119.7 |
F3—B1—F4 | 109.1 (7) | C25—C26—H26 | 119.7 |
F1—B1—F2 | 109.4 (8) | C28—C27—C26 | 119.7 (5) |
F3—B1—F2 | 106.8 (5) | C28—C27—H27 | 120.2 |
F4—B1—F2 | 109.5 (8) | C26—C27—H27 | 120.2 |
C2—C1—C6 | 120.7 (5) | C29—C28—C27 | 120.2 (5) |
C2—C1—H1 | 119.7 | C29—C28—H28 | 119.9 |
C6—C1—H1 | 119.7 | C27—C28—H28 | 119.9 |
C1—C2—C3 | 118.3 (4) | C28—C29—C30 | 120.5 (5) |
C1—C2—P1 | 117.8 (3) | C28—C29—H29 | 119.7 |
C3—C2—P1 | 123.8 (4) | C30—C29—H29 | 119.7 |
C4—C3—C2 | 120.3 (5) | C25—C30—C29 | 120.4 (5) |
C4—C3—H3 | 119.9 | C25—C30—H30 | 119.8 |
C2—C3—H3 | 119.9 | C29—C30—H30 | 119.8 |
C5—C4—C3 | 120.4 (5) | C32—C31—C36 | 118.0 (4) |
C5—C4—H4 | 119.8 | C32—C31—P2 | 123.6 (3) |
C3—C4—H4 | 119.8 | C36—C31—P2 | 118.4 (3) |
C4—C5—C6 | 120.0 (5) | C31—C32—C33 | 120.3 (5) |
C4—C5—H5 | 120.0 | C31—C32—H32 | 119.9 |
C6—C5—H5 | 120.0 | C33—C32—H32 | 119.9 |
C5—C6—C1 | 120.3 (6) | C34—C33—C32 | 120.1 (5) |
C5—C6—H6 | 119.9 | C34—C33—H33 | 120.0 |
C1—C6—H6 | 119.9 | C32—C33—H33 | 120.0 |
C8—C7—C12 | 120.2 (5) | C35—C34—C33 | 120.1 (5) |
C8—C7—H7 | 119.9 | C35—C34—H34 | 119.9 |
C12—C7—H7 | 119.9 | C33—C34—H34 | 119.9 |
C9—C8—C7 | 120.4 (5) | C34—C35—C36 | 120.0 (5) |
C9—C8—H8 | 119.8 | C34—C35—H35 | 120.0 |
C7—C8—H8 | 119.8 | C36—C35—H35 | 120.0 |
C10—C9—C8 | 119.8 (5) | C35—C36—C31 | 121.4 (5) |
C10—C9—H9 | 120.1 | C35—C36—H36 | 119.3 |
C8—C9—H9 | 120.1 | C31—C36—H36 | 119.3 |
C9—C10—C11 | 120.4 (5) | N1—C37—C38 | 122.5 (5) |
C9—C10—H10 | 119.8 | N1—C37—H37 | 118.7 |
C11—C10—H10 | 119.8 | C38—C37—H37 | 118.7 |
C10—C11—C12 | 120.1 (5) | C39—C38—C37 | 119.1 (6) |
C10—C11—H11 | 120.0 | C39—C38—H38 | 120.5 |
C12—C11—H11 | 120.0 | C37—C38—H38 | 120.5 |
C7—C12—C11 | 118.9 (4) | C38—C39—C40 | 119.3 (6) |
C7—C12—P1 | 118.1 (4) | C38—C39—H39 | 120.3 |
C11—C12—P1 | 123.0 (3) | C40—C39—H39 | 120.3 |
C18—C13—C14 | 118.1 (4) | C39—C40—C41 | 118.8 (6) |
C18—C13—P1 | 119.2 (4) | C39—C40—H40 | 120.6 |
C14—C13—P1 | 122.6 (3) | C41—C40—H40 | 120.6 |
C13—C14—C15 | 120.9 (5) | N1—C41—C40 | 122.7 (5) |
C13—C14—H14 | 119.5 | N1—C41—C42 | 113.5 (4) |
C15—C14—H14 | 119.5 | C40—C41—C42 | 123.8 (5) |
C16—C15—C14 | 119.3 (6) | N2—C42—N5 | 107.1 (4) |
C16—C15—H15 | 120.4 | N2—C42—C41 | 122.5 (4) |
C14—C15—H15 | 120.4 | N5—C42—C41 | 130.3 (4) |
C17—C16—C15 | 120.7 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H55···F4i | 0.86 | 1.80 | 2.650 (7) | 168 |
Symmetry code: (i) −x+2, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C6H5N5)(C18H15P)2]BF4 |
Mr | 822.05 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.6640 (19), 13.052 (3), 15.947 (3) |
α, β, γ (°) | 88.66 (3), 84.80 (3), 85.72 (3) |
V (Å3) | 1997.3 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.68 |
Crystal size (mm) | 0.29 × 0.17 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.908, 0.947 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19069, 8838, 4984 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.166, 1.14 |
No. of reflections | 8838 |
No. of parameters | 496 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −1.12 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H55···F4i | 0.86 | 1.80 | 2.650 (7) | 168 |
Symmetry code: (i) −x+2, −y+1, −z+2. |
Acknowledgements
This work was supported by the Natural Science Foundation of Zhejiang Province (grant No. LY12B02013), the Foundation of Zhejiang Education Committee (Y201119787), the National Natural Science Foundation of China (No. 51103136) and the National Natural Science Foundation of China (No. 21207117).
References
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Demko, Z. P. & Sharpless, K. B. (2001). J. Org. Chem. 66, 7945–7950. Web of Science CrossRef PubMed CAS Google Scholar
Jia, W., McCormick, T., Tao, Y., Liu, J. & Wang, S. (2005). Inorg. Chem. 44, 5706–5712. Web of Science CSD CrossRef PubMed CAS Google Scholar
Kuang, S., Cuttell, D. G., McMillin, D. R., Fanwick, P. E. & Walton, R. A. (2002). Inorg. Chem. 41, 3313–3322. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tsuboyama, A., Kuge, K., Furugori, M., Okada, S., Hoshino, M. & Ueno, K. (2007). Inorg. Chem. 46, 1992–2001. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhang, Q.-S., Zhou, Q.-G., Cheng, Y., Wang, L.-X., Ma, D.-G., Jing, X.-B. & Wang, F.-S. (2004). Adv. Mater. 16, 432–436. Web of Science CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Many copper(I) complexes have been utilized in solar energy conversion, biological probing, and organic light-emitting devices (Jia et al., 2005; Tsuboyama et al., 2007; Zhang et al., 2004). Therefore, it is pressing to explore new Cu(I) complexes served as luminescent materials. In this article, we have successfully synthesized a novel mixed ligand Cu(I) complex.
Scheme 1 and Figure 1 display the four-coordinated environment of complex [Cu(PPh3)2(L)]BF4, the coordination geometry at the Cu atom is a distorted tetrahedron. The distances of N1 and N2 to Cu1 are 2.185 (4), and 2.103 (4) Å, respectively, and the Cu—P bond lengths are 2.2575 (13) and 2.2538 (14) Å. The counter tetrafluoroboronate ion links with the complex cation via N—H···F hydrogen bonds (Table 1).