Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007824/qb0214sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007824/qb0214Isup2.hkl |
CCDC reference: 147687
A methanol solution of tris(N-methyl-1-benzimidazol-z-yl)amine (TMBMA; 100 mg, 0.222 mmol) and a methylene chloride solution of methylenebis(diphenylphosphine) (44 mg, 0.111 mmol) were mixed at room temperature. With stirring, the methanol solution of Ni(ClO4)·6H2O (81 mg, 0.222 mmol) was added to the mixture. After stirred for 12 h, the precipate was filtered, washed with methanol and ethanol in turn, then dried in vacuo to obtain a, green–yellow powder. Green–yellow monocrystals suitable for X-ray determination were formed by slowly evaporating the acetonitrile solution for a period of one month at room temperature.
All H atoms were located in difference Fourier maps and refined with isotropic displacement paramenters; the C—H range is 0.86 (3)–1.03 (4) Å.
Data collection: CAD-4 Operations Manual (Enraf-Nonius, 1977); cell refinement: CAD-4 Operations Manual; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1987); program(s) used to solve structure: MITHRIL (Gilmore, 1983); program(s) used to refine structure: LS in TEXSAN); software used to prepare material for publication: GCIF (local program).
[Ni(C25H22P2)2](ClO4)2 | F(000) = 1060 |
Mr = 1026.32 | Dx = 1.413 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
a = 11.226 (2) Å | Cell parameters from 25 reflections |
b = 17.836 (2) Å | θ = 14.2–14.8° |
c = 12.932 (2) Å | µ = 0.70 mm−1 |
β = 111.32 (1)° | T = 296 K |
V = 2412.0 (6) Å3 | Block, green yellow |
Z = 2 | 0.38 × 0.30 × 0.17 mm |
Enraf Nonius CAD-4 diffractometer | Rint = 0.033 |
ω/2θ scans | θmax = 25° |
Absorption correction: ψ scans (North et al., 1968) | h = 0→13 |
Tmin = 0.773, Tmax = 0.889 | k = 0→21 |
4624 measured reflections | l = −15→15 |
4431 independent reflections | 3 standard reflections every 300 reflections |
4340 reflections with I > 3σ(I) | intensity decay: 1.0% |
Refinement on F | All H-atom parameters refined |
Least-squares matrix: full | w = 1/[σ2(F)] |
R[F2 > 2σ(F2)] = 0.033 | (Δ/σ)max = 0.05 |
wR(F2) = 0.044 | Δρmax = 0.29 e Å−3 |
S = 1.22 | Δρmin = −0.25 e Å−3 |
3262 reflections | Extinction correction: ω/2θ |
323 parameters | Extinction coefficient: 0 |
[Ni(C25H22P2)2](ClO4)2 | V = 2412.0 (6) Å3 |
Mr = 1026.32 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.226 (2) Å | µ = 0.70 mm−1 |
b = 17.836 (2) Å | T = 296 K |
c = 12.932 (2) Å | 0.38 × 0.30 × 0.17 mm |
β = 111.32 (1)° |
Enraf Nonius CAD-4 diffractometer | 4340 reflections with I > 3σ(I) |
Absorption correction: ψ scans (North et al., 1968) | Rint = 0.033 |
Tmin = 0.773, Tmax = 0.889 | 3 standard reflections every 300 reflections |
4624 measured reflections | intensity decay: 1.0% |
4431 independent reflections |
R[F2 > 2σ(F2)] = 0.033 | 323 parameters |
wR(F2) = 0.044 | All H-atom parameters refined |
S = 1.22 | Δρmax = 0.29 e Å−3 |
3262 reflections | Δρmin = −0.25 e Å−3 |
Geometry. ——-Plane number 1——- 0 Atoms Defining Plane Distance e.s.d. P1 0.0000 0.0006 P2 0.0000 0.0006 P1 (3) 0.0000 0.0006 P2 (3) 0.0000 0.0006 Ni 0.0000 0.0010 0 Additional Atoms Distance C1 0.6647 C1 (3) −0.6647 0 Mean deviation from plane is 0.0000 angstroms Chi-squared: 1.9 0 —— Plane number 2 ——- 0 Atoms Defining Plane Distance e.s.d. C11 0.0031 0.0023 C12 − 0.0035 0.0035 C13 − 0.0065 0.0041 C14 0.0096 0.0037 C15 − 0.0040 0.0033 C16 − 0.0027 0.0030 0 Additional Atoms Distance P1 0.1016 C1 − 0.9283 0 Mean deviation from plane is 0.0049 angstroms Chi-squared: 15.1 0 Dihedral angles between least-squares planes plane plane angle 2 1 86.01 0 —— Plane number 3 —— 0 Atoms Defining Plane Distance e.s.d. C21 − 0.0039 0.0023 C22 0.0016 0.0029 C23 0.0048 0.0036 C24 − 0.0072 0.0041 C25 − 0.0030 0.0044 C26 0.0080 0.0034 0 Additional Atoms Distance P1 − 0.0030 C1 − 1.2643 0 Mean deviation from plane is 0.0047 angstroms Chi-squared: 14.1 0 Dihedral angles between least-squares planes plane plane angle 3 1 77.80 3 2 82.99 0 —— Plane number 4 ——- 0 Atoms Defining Plane Distance e.s.d. C31 0.0052 0.0022 C32 − 0.0041 0.0028 C33 − 0.0006 0.0035 C34 0.0010 0.0036 C35 0.0056 0.0036 C36 − 0.0085 0.0029 0 Additional Atoms Distance P2 0.1107 C1 − 0.1682 0 Mean deviation from plane is 0.0042 angstroms Chi-squared: 17.5 0 Dihedral angles between least-squares planes plane plane angle 4 1 63.49 4 2 27.72 4 3 63.94 0 ——– Plane number 5 ——- 0 Atoms Defining Plane Distance e.s.d. C41 0.0039 0.0023 C42 − 0.0026 0.0027 C43 − 0.0038 0.0033 C44 0.0087 0.0038 C45 − 0.0025 0.0041 C46 − 0.0046 0.0031 0 Additional Atoms Distance P2 0.1321 C1 1.6443 0 Mean deviation from plane is 0.0044 angstroms Chi-squared: 12.4 0 Dihedral angles between least-squares planes plane plane angle 5 1 92.85 5 2 104.04 5 3 25.10 5 4 88.58 0 ——- Plane number 6 ——— 0 Atoms Defining Plane Distance e.s.d. C11 (3) −0.0031 0.0023 C12 (3) 0.0035 0.0035 C13 (3) 0.0065 0.0041 C14 (3) −0.0096 0.0037 C15 (3) 0.0040 0.0033 C16 (3) 0.0027 0.0030 0 Additional Atoms Distance P1 (3) −0.1016 C1 (3) 0.9283 0 Mean deviation from plane is 0.0049 angstroms Chi-squared: 15.1 0 Dihedral angles between least-squares planes plane plane angle 6 1 86.01 6 2 0.00 6 3 82.99 6 4 27.72 6 5 104.04 0 ——- Plane number 7 ——– 0 Atoms Defining Plane Distance e.s.d. C21 (3) 0.0039 0.0023 C22 (3) −0.0016 0.0029 C23 (3) −0.0048 0.0036 C24 (3) 0.0072 0.0041 C25 (3) 0.0030 0.0044 C26 (3) −0.0080 0.0034 0 Additional Atoms Distance P1 (3) 0.0030 C1 (3) 1.2643 0 Mean deviation from plane is 0.0047 angstroms Chi-squared: 14.1 0 Dihedral angles between least-squares planes plane plane angle 7 1 77.80 7 2 82.99 7 3 0.00 7 4 63.94 7 5 25.10 7 6 82.99 0 ——– Plane number 8 ——– 0 Atoms Defining Plane Distance e.s.d. C31 (3) −0.0052 0.0022 C32 (3) 0.0041 0.0028 C33 (3) 0.0006 0.0035 C34 (3) −0.0010 0.0036 C35 (3) −0.0056 0.0036 C36 (3) 0.0085 0.0029 0 Additional Atoms Distance P2 (3) −0.1107 C1 (3) 0.1682 0 Mean deviation from plane is 0.0042 angstroms Chi-squared: 17.5 0 Dihedral angles between least-squares planes plane plane angle 8 1 63.49 8 2 27.72 8 3 63.94 8 4 0.00 8 5 88.58 8 6 27.72 8 7 63.94 0 ——- Plane number 9 ——– 0 Atoms Defining Plane Distance e.s.d. C41 (3) −0.0039 0.0023 C42 (3) 0.0026 0.0027 C43 (3) 0.0038 0.0033 C44 (3) −0.0087 0.0038 C45 (3) 0.0025 0.0041 C46 (3) 0.0046 0.0031 0 Additional Atoms Distance P2 (3) −0.1321 C1 (3) −1.6443 0 Mean deviation from plane is 0.0044 angstroms Chi-squared: 12.4 0 Dihedral angles between least-squares planes plane plane angle 9 1 92.85 9 2 104.04 9 3 25.10 9 4 88.58 9 5 0.00 9 6 104.04 9 7 25.10 9 8 88.58 |
x | y | z | Uiso*/Ueq | ||
Ni | 0.00000 (2) | 0.00000 (2) | 0.00000 (2) | 2.89 (2) | |
P1 | 0.00278 (6) | 0.06311 (4) | −0.14818 (5) | 2.92 (3) | |
P2 | −0.18977 (6) | 0.05440 (4) | −0.07613 (6) | 2.90 (3) | |
C1 | −0.1284 (3) | 0.12426 (16) | −0.1482 (2) | 3.1 (1) | |
C11 | 0.1363 (2) | 0.11841 (17) | −0.1532 (2) | 3.4 (1) | |
C12 | 0.1711 (4) | 0.1833 (2) | −0.0934 (3) | 5.9 (2) | |
C13 | 0.2779 (4) | 0.2231 (3) | −0.0931 (4) | 7.3 (2) | |
C14 | 0.3479 (4) | 0.1967 (3) | −0.1519 (3) | 6.6 (2) | |
C15 | 0.3130 (3) | 0.1337 (3) | −0.2120 (3) | 5.6 (2) | |
C16 | 0.2075 (3) | 0.0941 (2) | −0.2128 (3) | 4.5 (1) | |
C21 | −0.0539 (3) | 0.01166 (15) | −0.2768 (2) | 3.2 (1) | |
C22 | −0.1176 (3) | 0.0485 (2) | −0.3760 (3) | 4.5 (1) | |
C23 | −0.1603 (4) | 0.0087 (3) | −0.4739 (3) | 6.0 (2) | |
C24 | −0.1407 (5) | −0.0666 (3) | −0.4730 (4) | 6.6 (2) | |
C25 | −0.0780 (5) | −0.1030 (3) | −0.3770 (4) | 7.2 (2) | |
C26 | −0.0332 (4) | −0.0642 (2) | −0.2782 (3) | 5.2 (2) | |
C31 | −0.2759 (2) | 0.09965 (16) | 0.0001 (2) | 3.2 (1) | |
C32 | −0.2709 (3) | 0.1760 (2) | 0.0182 (3) | 4.3 (1) | |
C33 | −0.3327 (4) | 0.2065 (2) | 0.0834 (3) | 5.7 (2) | |
C34 | −0.3987 (4) | 0.1626 (3) | 0.1288 (3) | 6.1 (2) | |
C35 | −0.4050 (4) | 0.0863 (3) | 0.1112 (3) | 5.7 (2) | |
C36 | −0.3448 (3) | 0.0550 (2) | 0.0457 (3) | 4.4 (1) | |
C41 | −0.3027 (2) | −0.00250 (15) | −0.1822 (2) | 3.1 (1) | |
C42 | −0.4039 (3) | 0.0321 (2) | −0.2644 (3) | 4.1 (1) | |
C43 | −0.4859 (3) | −0.0090 (3) | −0.3504 (3) | 5.5 (2) | |
C44 | −0.4674 (4) | −0.0847 (3) | −0.3554 (3) | 6.4 (2) | |
C45 | −0.3695 (4) | −0.1196 (3) | −0.2746 (4) | 6.6 (2) | |
C46 | −0.2858 (3) | −0.0784 (2) | −0.1867 (3) | 4.7 (1) | |
Cl | 0.06093 (7) | 0.26883 (4) | 0.13398 (6) | 4.1 (3) | |
O1 | 0.0351 (2) | 0.19307 (12) | 0.09475 (6) | 4.8 (1) | |
O2 | 0.0946 (3) | 0.27031 (16) | 0.2509 (2) | 7.1 (1) | |
O3 | −0.0507 (3) | 0.31392 (14) | 0.0838 (3) | 7.5 (1) | |
O4 | 0.1636 (2) | 0.29876 (16) | 0.1077 (2) | 6.9 (1) | |
H1 | −0.187 (3) | 0.1438 (14) | −0.217 (2) | 3.3 (6)* | |
H2 | −0.095 (3) | 0.1627 (16) | −0.098 (2) | 3.5 (6)* | |
H3 | 0.125 (4) | 0.205 (2) | −0.052 (3) | 7 (1)* | |
H4 | 0.292 (4) | 0.272 (2) | −0.051 (4) | 8 (1)* | |
H5 | 0.412 (4) | 0.226 (2) | −0.155 (3) | 7 (1)* | |
H6 | 0.365 (4) | 0.115 (2) | −0.257 (3) | 7 (1)* | |
H7 | 0.189 (3) | 0.0529 (18) | −0.249 (3) | 4.7 (8)* | |
H8 | −0.134 (3) | 0.1013 (19) | −0.375 (3) | 4.8 (8)* | |
H9 | −0.197 (4) | 0.036 (2) | −0.536 (3) | 6.0 (9)* | |
H10 | −0.174 (4) | −0.091 (2) | −0.541 (4) | 8 (1)* | |
H11 | −0.063 (5) | −0.155 (3) | −0.370 (4) | 11 (2)* | |
H12 | 0.004 (3) | −0.0904 (18) | −0.212 (3) | 5.0 (8)* | |
H13 | −0.229 (3) | 0.2060 (16) | −0.014 (2) | 3.8 (7)* | |
H14 | −0.325 (4) | 0.258 (2) | 0.099 (3) | 6 (1)* | |
H15 | −0.442 (4) | 0.181 (2) | 0.179 (3) | 8 (1)* | |
H16 | −0.445 (3) | 0.053 (2) | 0.139 (3) | 5.5 (8)* | |
H17 | −0.348 (3) | 0.0021 (18) | 0.033 (3) | 4.7 (8)* | |
H18 | −0.418 (3) | 0.082 (2) | −0.260 (3) | 4.7 (8)* | |
H19 | −0.561 (4) | 0.0172 (18) | −0.410 (3) | 5.8 (8)* | |
H20 | −0.522 (4) | −0.112 (2) | −0.415 (3) | 7 (1)* | |
H21 | −0.350 (4) | −0.168 (3) | −0.276 (3) | 8 (1)* | |
H22 | −0.221 (3) | −0.102 (2) | −0.134 (3) | 5.7 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.0250 (2) | 0.0554 (3) | 0.0304 (2) | 0.0019 (2) | 0.01144 (19) | 0.0068 (2) |
P1 | 0.0301 (3) | 0.0510 (4) | 0.0312 (4) | −0.0005 (3) | 0.0128 (3) | 0.0040 (3) |
P2 | 0.0261 (3) | 0.0496 (4) | 0.0346 (4) | 0.0004 (3) | 0.0114 (3) | 0.0036 (3) |
C1 | 0.0328 (14) | 0.0471 (17) | 0.0367 (15) | −0.0003 (12) | 0.0133 (12) | 0.0017 (13) |
C11 | 0.0337 (14) | 0.0621 (18) | 0.0333 (14) | −0.0059 (13) | 0.0127 (12) | 0.0069 (13) |
C12 | 0.069 (2) | 0.095 (3) | 0.078 (2) | −0.030 (2) | 0.047 (2) | −0.026 (2) |
C13 | 0.085 (3) | 0.110 (3) | 0.098 (3) | −0.056 (3) | 0.052 (3) | −0.039 (3) |
C14 | 0.054 (2) | 0.129 (4) | 0.072 (3) | −0.039 (2) | 0.028 (2) | −0.002 (3) |
C15 | 0.048 (2) | 0.107 (3) | 0.068 (2) | −0.009 (2) | 0.0347 (18) | 0.004 (2) |
C16 | 0.0448 (18) | 0.076 (2) | 0.057 (2) | −0.0041 (17) | 0.0284 (15) | −0.0007 (19) |
C21 | 0.0382 (14) | 0.0506 (18) | 0.0366 (14) | −0.0036 (12) | 0.0172 (12) | 0.0017 (12) |
C22 | 0.059 (2) | 0.066 (2) | 0.0395 (17) | 0.0040 (17) | 0.0107 (15) | 0.0013 (15) |
C23 | 0.076 (3) | 0.103 (4) | 0.0365 (19) | −0.003 (2) | 0.0058 (18) | 0.000 (2) |
C24 | 0.104 (3) | 0.092 (3) | 0.058 (2) | −0.024 (3) | 0.032 (2) | −0.028 (2) |
C25 | 0.146 (4) | 0.060 (3) | 0.076 (3) | −0.004 (3) | 0.049 (3) | −0.013 (2) |
C26 | 0.093 (3) | 0.057 (2) | 0.053 (2) | 0.006 (2) | 0.032 (2) | 0.0028 (17) |
C31 | 0.0294 (13) | 0.0566 (18) | 0.0336 (14) | 0.0009 (12) | 0.0106 (11) | −0.0029 (12) |
C32 | 0.0434 (17) | 0.063 (2) | 0.061 (2) | −0.0082 (15) | 0.0258 (15) | −0.0101 (16) |
C33 | 0.075 (2) | 0.073 (3) | 0.079 (3) | −0.007 (2) | 0.042 (2) | −0.023 (2) |
C34 | 0.076 (3) | 0.102 (3) | 0.073 (2) | −0.004 (2) | 0.048 (2) | −0.019 (2) |
C35 | 0.072 (2) | 0.090 (3) | 0.076 (2) | −0.011 (2) | 0.051 (2) | −0.001 (2) |
C36 | 0.0546 (19) | 0.065 (2) | 0.057 (2) | −0.0033 (16) | 0.0318 (16) | −0.0001 (16) |
C41 | 0.0302 (13) | 0.0495 (16) | 0.0407 (14) | −0.0011 (12) | 0.0166 (11) | 0.0021 (12) |
C42 | 0.0370 (16) | 0.062 (2) | 0.0494 (18) | −0.0061 (15) | 0.0086 (14) | 0.0070 (16) |
C43 | 0.050 (2) | 0.103 (3) | 0.048 (2) | −0.017 (2) | 0.0088 (17) | 0.000 (2) |
C44 | 0.063 (3) | 0.116 (4) | 0.066 (3) | −0.030 (3) | 0.027 (2) | −0.040 (3) |
C45 | 0.075 (3) | 0.063 (3) | 0.118 (4) | −0.010 (2) | 0.042 (3) | −0.037 (3) |
C46 | 0.0473 (19) | 0.054 (2) | 0.073 (2) | 0.0042 (16) | 0.0173 (17) | −0.0056 (18) |
Cl | 0.0511 (4) | 0.0580 (5) | 0.0479 (4) | −0.0087 (3) | 0.0185 (3) | −0.0067 (3) |
O1 | 0.0602 (13) | 0.0585 (14) | 0.0643 (14) | −0.0058 (11) | 0.0221 (11) | −0.0099 (11) |
O2 | 0.121 (2) | 0.102 (2) | 0.0509 (15) | −0.0165 (17) | 0.0357 (15) | −0.0113 (14) |
O3 | 0.0703 (16) | 0.0653 (16) | 0.125 (2) | 0.0097 (14) | 0.0051 (16) | 0.0106 (16) |
O4 | 0.0798 (18) | 0.106 (2) | 0.095 (2) | −0.0428 (16) | 0.0544 (16) | −0.0359 (16) |
Ni—P2 | 2.2188 (5) | C42—C43 | 1.370 (5) |
Ni—P2i | 2.2188 (5) | C43—C44 | 1.371 (6) |
Ni—P1 | 2.2322 (5) | C44—C45 | 1.360 (6) |
Ni—P1i | 2.2322 (5) | C45—C46 | 1.392 (5) |
P1—C21 | 1.802 (3) | Cl—O4 | 1.419 (2) |
P1—C11 | 1.815 (3) | Cl—O2 | 1.420 (3) |
P1—C1 | 1.832 (3) | Cl—O3 | 1.430 (3) |
P2—C31 | 1.803 (3) | Cl—O1 | 1.435 (2) |
P2—C41 | 1.805 (3) | C1—H2 | 0.92 (3) |
P2—C1 | 1.834 (3) | C1—H1 | 0.96 (3) |
C11—C12 | 1.367 (5) | C12—H3 | 0.95 (4) |
C11—C16 | 1.368 (4) | C13—H4 | 1.01 (4) |
C12—C13 | 1.393 (5) | C14—H5 | 0.90 (4) |
C13—C14 | 1.362 (6) | C15—H6 | 1.02 (4) |
C14—C15 | 1.341 (6) | C16—H7 | 0.86 (3) |
C15—C16 | 1.377 (5) | C22—H8 | 0.96 (3) |
C21—C26 | 1.374 (4) | C23—H9 | 0.90 (4) |
C21—C22 | 1.385 (4) | C24—H10 | 0.93 (4) |
C22—C23 | 1.377 (5) | C25—H11 | 0.94 (5) |
C23—C24 | 1.361 (6) | C26—H12 | 0.93 (3) |
C24—C25 | 1.350 (6) | C32—H13 | 0.91 (3) |
C25—C26 | 1.378 (5) | C33—H14 | 0.94 (4) |
C31—C32 | 1.380 (4) | C34—H15 | 1.00 (4) |
C31—C36 | 1.382 (4) | C35—H16 | 0.89 (3) |
C32—C33 | 1.383 (5) | C36—H17 | 0.96 (3) |
C33—C34 | 1.352 (5) | C42—H18 | 0.91 (3) |
C34—C35 | 1.376 (6) | C43—H19 | 1.02 (4) |
C35—C36 | 1.379 (5) | C44—H20 | 0.93 (4) |
C41—C46 | 1.371 (4) | C45—H21 | 0.89 (4) |
C41—C42 | 1.386 (4) | C46—H22 | 0.90 (3) |
C1···O1 | 3.248 (4) | C32···O1 | 3.224 (4) |
C1···O4ii | 3.456 (4) | C32···O2ii | 3.369 (4) |
C1···O2ii | 3.459 (4) | C32···O3 | 3.370 (4) |
C12···O1 | 3.314 (4) | C42···O3ii | 3.429 (4) |
C12···O4 | 3.343 (5) | C42···O2ii | 3.531 (5) |
C13···O4 | 3.554 (5) | C43···O3ii | 3.594 (5) |
C14···O2iii | 3.481 (5) | C44···O3iv | 3.532 (5) |
C25···O2i | 3.438 (6) | C46···O1i | 3.329 (4) |
C26···O1i | 3.308 (4) | ||
P2—Ni—P2 | 180.00 (3) | O4—Cl—O2 | 108.9 (2) |
P2—Ni—P1 | 73.12 (3) | O4—Cl—O3 | 109.5 (2) |
P2—Ni—P1 | 106.88 (3) | O4—Cl—O1 | 110.3 (1) |
P2i—Ni—P1 | 106.88 (3) | O2—Cl—O3 | 108.8 (2) |
P2i—Ni—P1 | 73.12 (3) | O2—Cl—O1 | 109.6 (2) |
P1—Ni—P1 | 180.00 (2) | O3—Cl—O1 | 109.7 (1) |
C21—P1—C11 | 105.3 (1) | H2—C1—H1 | 110.0 (2) |
C21—P1—C1 | 106.8 (1) | H2—C1—P1 | 109.0 (2) |
C21—P1—Ni | 115.2 (1) | H2—C1—P2 | 106.0 (2) |
C11—P1—C1 | 110.5 (1) | H1—C1—P1 | 120.0 (2) |
C11—P1—Ni | 125.03 (9) | H1—C1—P2 | 117.0 (2) |
C1—P1—Ni | 92.2 (1) | H3—C12—C11 | 124.0 (2) |
C31—P2—C41 | 107.4 (1) | H3—C12—C13 | 115.0 (2) |
C31—P2—C1 | 110.4 (1) | H4—C13—C14 | 127.0 (2) |
C31—P2—Ni | 124.91 (9) | H4—C13—C12 | 114.0 (3) |
C41—P2—C1 | 106.6 (1) | H5—C14—C15 | 122.0 (3) |
C41—P2—Ni | 112.8 (1) | H5—C14—C13 | 117.0 (3) |
C1—P2—Ni | 92.57 (9) | H6—C15—C14 | 120.0 (2) |
P1—C1—P2 | 92.6 (1) | H6—C15—C16 | 120.0 (2) |
C12—C11—C16 | 118.8 (3) | H7—C16—C11 | 120.0 (2) |
C12—C11—P1 | 120.62 (7) | H7—C16—C15 | 119.0 (2) |
C16—C11—P1 | 120.5 (2) | H8—C22—C23 | 121.0 (2) |
C11—C12—C13 | 120.1 (4) | H8—C22—C21 | 119.0 (2) |
C14—C13—C12 | 119.6 (4) | H9—C23—C24 | 124.0 (2) |
C15—C14—C13 | 120.5 (4) | H9—C23—C22 | 116.0 (2) |
C14—C15—C16 | 120.3 (4) | H10—C24—C25 | 123.0 (3) |
C11—C16—C15 | 120.7 (4) | H10—C24—C23 | 116.0 (3) |
C26—C21—C22 | 119.2 (3) | H11—C25—C24 | 126.0 (3) |
C26—C21—P1 | 120.6 (2) | H11—C25—C26 | 114.0 (3) |
C22—C21—P1 | 120.2 (2) | H12—C26—C21 | 120.0 (5) |
C23—C22—C21 | 119.8 (4) | H12—C26—C25 | 119.0 (5) |
C24—C23—C22 | 120.0 (4) | H13—C32—C31 | 120.0 (5) |
C25—C24—C23 | 120.8 (4) | H13—C32—C33 | 120.4 (5) |
C24—C25—C26 | 120.3 (4) | H14—C33—C34 | 120.0 (5) |
C21—C26—C25 | 120.0 (4) | H14—C33—C32 | 119.0 (5) |
C32—C31—C36 | 119.3 (3) | H15—C34—C33 | 125.0 (5) |
C32—C31—P2 | 122.6 (2) | H15—C34—C35 | 115.0 (5) |
C36—C31—P2 | 118.0 (2) | H16—C35—C34 | 126.0 (5) |
C31—C32—C33 | 119.6 (3) | H16—C35—C36 | 114.0 (5) |
C34—C33—C32 | 120.8 (4) | H17—C36—C35 | 121.0 (5) |
C33—C34—C35 | 120.3 (4) | H17—C36—C31 | 119.0 (5) |
C34—C35—C36 | 119.6 (4) | H18—C42—C43 | 120.0 (5) |
C35—C36—C31 | 120.3 (4) | H18—C42—C41 | 120.0 (5) |
C46—C41—C42 | 119.6 (3) | H19—C43—C42 | 119.5 (5) |
C46—C41—P2 | 121.2 (2) | H19—C43—C44 | 120.7 (5) |
C42—C41—P2 | 119.1 (2) | H20—C44—C45 | 120.0 (5) |
C43—C42—C41 | 120.4 (4) | H20—C44—C43 | 119.0 (5) |
C42—C43—C44 | 119.8 (4) | H21—C45—C44 | 124.0 (5) |
C45—C44—C43 | 120.5 (4) | H21—C45—C46 | 115.0 (5) |
C44—C45—C46 | 120.2 (4) | H22—C46—C41 | 121.0 (5) |
C41—C46—C45 | 119.5 (4) | H22—C46—C45 | 119.0 (5) |
Ni—P2—C41—C46 | 20.5 (3) | C1—P1—C21—C26 | −134.6 (3) |
Ni—P2—C41—C42 | −155.5 (2) | C1—P1—C21—C22 | 46.3 (3) |
Ni—P2—C1—P1 | 25.1 (1) | C11—C12—C13—C14 | −0.6 (7) |
Ni—P2—C31—C32 | 96.3 (3) | C11—C16—C15—C14 | 0.5 (6) |
Ni—P2—C31—C36 | −80.9 (2) | C11—P1—C21—C26 | 107.9 (3) |
Ni—P2—C41—C46 | 20.5 (3) | C11—P1—C21—C22 | −71.2 (3) |
Ni—P2—C41—C42 | −155.5 (2) | C12—C11—C16—C15 | 0.5 (6) |
Ni—P2—C1—P1 | 25.03 (9) | C12—C11—P1—C21 | 154.9 (3) |
Ni—P1—C21—C26 | −33.9 (3) | C12—C13—C14—C15 | 1.6 (8) |
Ni—P1—C21—C22 | 147.0 (2) | C13—C14—C15—C16 | −1.5 (7) |
Ni—P1—C11—C12 | −68.2 (3) | C13—C12—C11—C16 | −0.5 (6) |
Ni—P1—C11—C16 | 108.7 (2) | C16—C11—P1—C21 | −28.2 (3) |
Ni—P1—C1—P2 | −24.9 (1) | C21—C26—C25—C24 | 0.9 (7) |
Ni—P1—C21—C26 | −33.9 (4) | C21—C22—C23—C24 | 0.5 (7) |
Ni—P1—C21—C22 | 147.0 (3) | C22—C23—C24—C25 | −1.0 (7) |
Ni—P1—C11—C12 | −68.3 (3) | C22—C21—C26—C25 | −1.4 (6) |
Ni—P1—C11—C16 | 108.7 (2) | C23—C24—C25—C26 | 0.3 (9) |
Ni—P1—C1—P2 | −24.86 (9) | C23—C22—C21—C26 | 0.7 (5) |
P1—C21—C26—C25 | 179.5 (4) | C31—C32—C33—C34 | −0.5 (6) |
P1—C21—C22—C23 | 179.8 (8) | C31—C36—C35—C34 | 1.6 (6) |
P1—C11—C16—C15 | −176.5 (3) | C31—P2—C41—C46 | −121.0 (3) |
P1—C1—P2—C31 | 154.0 (1) | C31—P2—C41—C42 | 63.0 (3) |
P1—C1—P2—C41 | −89.68 (13) | C32—C31—C36—C35 | −1.8 (5) |
P1—Ni—P2—C31 | −138.48 (12) | C32—C31—P2—C41 | −128.2 (2) |
P1—Ni—P2—C41 | 88.0 (1) | C32—C33—C34—C35 | 0.3 (7) |
P1—Ni—P2—C1 | −21.3 (1) | C33—C34—C35—C36 | −0.8 (7) |
P1—Ni—P2—C31 | −138.48 (12) | C33—C32—C31—C36 | 1.3 (5) |
P1—Ni—P2—C41 | 87.97 (9) | C36—C31—P2—C41 | 54.6 (3) |
P1—Ni—P2—C1 | −21.26 (9) | C1—P1—C11—C12 | 39.9 (3) |
P2—C31—C32—C33 | −175.9 (3) | C1—P1—C11—C16 | −143.1 (2) |
P2—C31—C36—C35 | 175.5 (3) | C1—P2—C31—C32 | −12.3 (3) |
P2—C41—C46—C45 | −175.2 (3) | C1—P2—C31—C36 | 170.5 (2) |
P2—C41—C42—C43 | 175.4 (3) | C1—P2—C41—C46 | 120.6 (3) |
P2—C1—P1—C21 | 92.3 (1) | C1—P2—C41—C42 | −55.3 (3) |
P2—C1—P1—C11 | −153.7 (1) | C41—C46—C45—C44 | 0.0 (3) |
P2—Ni—P1—C21 | −88.5 (1) | C41—C42—C43—C44 | −0.4 (6) |
P2—Ni—P1—C11 | 138.3 (1) | C42—C43—C44—C45 | 1.2 (6) |
P2—Ni—P1—C1 | 21.3 (1) | C42—C41—C46—C45 | 0.8 (5) |
P2—Ni—P1—C21 | −88.46 (13) | C43—C42—C41—C46 | −0.7 (5) |
P2—Ni—P1—C11 | 138.35 (12) | C43—C44—C45—C46 | −1.1 (6) |
P2—Ni—P1—C1 | 21.27 (9) |
Symmetry codes: (i) −x, −y, −z; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x−1/2, y−1/2, −z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C25H22P2)2](ClO4)2 |
Mr | 1026.32 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 11.226 (2), 17.836 (2), 12.932 (2) |
β (°) | 111.32 (1) |
V (Å3) | 2412.0 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.70 |
Crystal size (mm) | 0.38 × 0.30 × 0.17 |
Data collection | |
Diffractometer | Enraf Nonius CAD-4 diffractometer |
Absorption correction | ψ scans (North et al., 1968) |
Tmin, Tmax | 0.773, 0.889 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 4624, 4431, 4340 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.044, 1.22 |
No. of reflections | 3262 |
No. of parameters | 323 |
No. of restraints | ? |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.29, −0.25 |
Computer programs: CAD-4 Operations Manual (Enraf-Nonius, 1977), CAD-4 Operations Manual, PROCESS in TEXSAN (Molecular Structure Corporation, 1987), MITHRIL (Gilmore, 1983), LS in TEXSAN), GCIF (local program).
Ni—P2 | 2.2188 (5) | P1—C1 | 1.832 (3) |
Ni—P1 | 2.2322 (5) | P2—C31 | 1.803 (3) |
P1—C21 | 1.802 (3) | P2—C41 | 1.805 (3) |
P1—C11 | 1.815 (3) | P2—C1 | 1.834 (3) |
P2—Ni—P1 | 73.12 (3) |
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Much interest has been given to metal–phosphine complexes because they not only have special geometrical and electronical structures, but also serve as catalysts in industry. In order to understand the microstructures of these complexes and research their catalytical mechanisms to provide more information for the development of catalysts, we now report the crystal structure of the title compound, (I). The four P atoms and the NiII atom are coplanar. At the same time, the two diphenylphosphine groups are linked by a methylene group. The NiII ion lies in the center of the square formed by atoms of P1, P2, P1' and P2'. The dihedral angles between the plane which these four P atoms are sited in and each of the eight benzene rings fall in the range 63–93°. It can be inferred that a negtively charged area is formed around the NiII ion, while the center of the positively charged NiII ion is completely exposed and easily coordinated by some gas or solid molecules along the axis vertical to the plane formed by four P atoms. Perhaps that is the reason that the title complex has high catalytical activities. The Ni—P bond lengths are 2.2322 (5), 2.2322 (5), 2.2188 (5) and 2.2188 (5) Å; the average length is 2.2255 (5) Å, which is in the normal range of Ni—P bond lengths. The Ni atom lies on an inversion centre.