Scheme 1.
The synthetic pathway of the tetraphenylborate salt of clonidine (Catapres®) (3).
Scheme 1.
The synthetic pathway of the tetraphenylborate salt of clonidine (Catapres®) (3).
Figure 1.
UV spectrum of 1 clonidine, 2 NaTPB and 3 clonidine-TPB.
Figure 1.
UV spectrum of 1 clonidine, 2 NaTPB and 3 clonidine-TPB.
Figure 2.
Thermal gravimetric analysis of the titled compound 3.
Figure 2.
Thermal gravimetric analysis of the titled compound 3.
Figure 3.
Differential scanning calorimetry thermogram of the titled compound.
Figure 3.
Differential scanning calorimetry thermogram of the titled compound.
Figure 4.
ORTEP diagram of the titled compound 3 showing the cation and anion parts. Displacement ellipsoids are plotted at the 40% probability level for non-H atoms.
Figure 4.
ORTEP diagram of the titled compound 3 showing the cation and anion parts. Displacement ellipsoids are plotted at the 40% probability level for non-H atoms.
Figure 5.
Molecular packing of titled compound viewed hydrogen bonds which are drawn as dashed lines along c axis.
Figure 5.
Molecular packing of titled compound viewed hydrogen bonds which are drawn as dashed lines along c axis.
Figure 6.
(a) Non-covalent interaction (NCI) scatter diagram and (b) reduced density gradient (RDG) analysis of the clonidine–tetraphenylborate complex.
Figure 6.
(a) Non-covalent interaction (NCI) scatter diagram and (b) reduced density gradient (RDG) analysis of the clonidine–tetraphenylborate complex.
Figure 7.
Topological atoms in molecules (AIM) graph of the clonidine–tetraphenylborate complex.
Figure 7.
Topological atoms in molecules (AIM) graph of the clonidine–tetraphenylborate complex.
Figure 8.
Graphical representation of the Fukui descriptors.
Figure 8.
Graphical representation of the Fukui descriptors.
Figure 9.
MESP analysis of the electrophilic sites for: (A) clonidine, (E) tetraphenylborate; MESP analysis of the nucleophilic sites for:(B) clonidine, (D) tetraphenylborate; Electrostatic potential maps for: (C) clonidine, (F) tetraphenylborate, (G) complex, superimposed on the isodensity surface of the structures (isovalue 0.002), computed at B3LYP/6-311 G (d, p) level.
Figure 9.
MESP analysis of the electrophilic sites for: (A) clonidine, (E) tetraphenylborate; MESP analysis of the nucleophilic sites for:(B) clonidine, (D) tetraphenylborate; Electrostatic potential maps for: (C) clonidine, (F) tetraphenylborate, (G) complex, superimposed on the isodensity surface of the structures (isovalue 0.002), computed at B3LYP/6-311 G (d, p) level.
Table 1.
Crystallographic data and refinement information for compound 3.
Table 1.
Crystallographic data and refinement information for compound 3.
Crystal Data |
Chemical formula | C33H30BCl2N3 |
Mr | 550.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 9.151 (3), 12.522 (3), 25.493 (6) |
β (°) | 105.161 (13) |
V (Å3) | 2819.5 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.57 × 0.25 × 0.11 |
Data collection |
Diffractometer | Bruker APEX-II D8 venture diffractometer |
Absorption correction | Multi-scan SADABS Bruker 2014 |
Tmin, Tmax | 0.867, 0.971 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 32,394, 4958, 2969 |
Rint | 0.229 |
Refinement |
R [F2 > 2σ(F2)], wR(F2), S | 0.068, 0.164, 1.03 |
No. of reflections | 4958 |
No. of parameters | 355 |
No. of restraints | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.43, −0.36 |
Table 2.
Selected geometric parameters (Å, °).
Table 2.
Selected geometric parameters (Å, °).
Cl1—C5 | 1.734 (4) | N3—C3 | 1.333 (5) |
Cl2—C9 | 1.724 (4) | N3—C4 | 1.416 (5) |
N1—C1 | 1.475 (5) | C10—B1 | 1.653 (5) |
N1—C3 | 1.311 (6) | C16—B1 | 1.661 (6) |
N2—C3 | 1.328 (5) | C22—B1 | 1.647 (6) |
N2—C2 | 1.467 (6) | C28—B1 | 1.655 (7) |
C1—N1—C3 | 110.3 (3) | N1—C3—N2 | 111.5 (4) |
C2—N2—C3 | 109.1 (4) | N1—C3—N3 | 125.9 (4) |
C3—N3—C4 | 123.6 (4) | N3—C4—C5 | 121.2 (4) |
C15—C10—B1 | 123.8 (3) | N3—C4—C9 | 120.9 (4) |
C11—C10—B1 | 122.3 (3) | Cl1—C5—C6 | 119.2 (3) |
C17—C16—B1 | 122.0 (3) | Cl1—C5—C4 | 119.8 (3) |
C21—C16—B1 | 122.7 (3) | Cl2—C9—C8 | 119.3 (3) |
C23—C22—B1 | 120.6 (3) | Cl2—C9—C4 | 119.5 (3) |
C27—C22—B1 | 123.9 (3) | C16—B1—C28 | 109.7 (3) |
C33—C28—B1 | 123.3 (4) | C22—B1—C28 | 107.2 (3) |
C29—C28—B1 | 122.9 (3) | C16—B1—C22 | 109.8 (3) |
N1—C1—C2 | 101.2 (3) | C10—B1—C16 | 107.6 (3) |
N2—C2—C1 | 102.1 (3) | C10—B1—C22 | 108.4 (3) |
N2—C3—N3 | 122.6 (4) | C10—B1—C28 | 114.0 (4) |
Table 3.
Hydrogen-bond geometry (Å, °).
Table 3.
Hydrogen-bond geometry (Å, °).
D—H···A | D—H | H···A | D···A | D—H···A |
---|
C2—H2A···Cl2i | 0.9700 | 2.7300 | 3.648 (4) | 159.00 |
Symmetry codes: (i) −x − 3, y + 1/2, −z − 3/2. |
Table 4.
Geometric parameters for the clonidine–tetraphenylborate complex obtained using DFT techniques and B3LYP functionals. Distances are measured in Å, and bond angles are measured in degrees.
Table 4.
Geometric parameters for the clonidine–tetraphenylborate complex obtained using DFT techniques and B3LYP functionals. Distances are measured in Å, and bond angles are measured in degrees.
Bond Distance | Exp. | DFT-B3LYP | Bond Distance | Exp. | DFT-B3LYP |
---|
Cl1—C5 | 1.734 (4) | 1.756 | N3—C3 | 1.333 (5) | 1.337 |
Cl2—C9 | 1.724 (4) | 1.739 | N3—C4 | 1.416 (5) | 1.419 |
N1—C1 | 1.475 (5) | 1.473 | C10—B1 | 1.653 (5) | 1.662 |
N1—C3 | 1.311 (6) | 1.326 | C16—B1 | 1.661 (6) | 1.655 |
N2—C3 | 1.328 (5) | 1.345 | C22—B1 | 1.647 (6) | 1.653 |
N2—C2 | 1.467 (6) | 1.474 | C28—B1 | 1.655 (7) | 1.666 |
Bond angle | | | | | |
C1—N1—C3 | 110.3 (3) | 110.539 | N1—C3—N2 | 111.5 (4) | 111.402 |
C2—N2—C3 | 109.1 (4) | 109.892 | N1—C3—N3 | 125.9 (4) | 123.444 |
C3—N3—C4 | 123.6 (4) | 125.239 | N3—C4—C5 | 121.2 (4) | 121.628 |
C15—C10—B1 | 123.8 (3) | 121.836 | N3—C4—C9 | 120.9 (4) | 120.495 |
C11—C10—B1 | 122.3 (3) | 123.0899 | Cl1—C5—C6 | 119.2 (3) | 119.213 |
C17—C16—B1 | 122.0 (3) | 119.0318 | Cl1—C5—C4 | 119.8 (3) | 119.851 |
C21—C16—B1 | 122.7 (3) | 125.277 | Cl2—C9—C8 | 119.3 (3) | 118.237 |
C23—C22—B1 | 120.6 (3) | 119.147 | Cl2—C9—C4 | 119.5 (3) | 120.234 |
C27—C22—B1 | 123.9 (3) | 125.431 | C16—B1—C28 | 109.7 (3) | 105.195 |
C33—C28—B1 | 123.3 (4) | 120.389 | C22—B1—C28 | 107.2 (3) | 105.913 |
C29—C28—B1 | 122.9 (3) | 124.664 | C16—B1—C22 | 109.8 (3) | 111.056 |
N1—C1—C2 | 101.2 (3) | 101.827 | C10—B1—C16 | 107.6 (3) | 110.477 |
N2—C2—C1 | 102.1 (3) | 101.843 | C10—B1—C22 | 108.4 (3) | 111.494 |
N2—C3—N3 | 122.6 (4) | 125.153 | C10—B1—C28 | 114.0 (4) | 112.802 |
Table 5.
Topological parameters found by QTAIM analysis of the interactions in the atomic unit (u.a).
Table 5.
Topological parameters found by QTAIM analysis of the interactions in the atomic unit (u.a).
BCP | Bond | ρ(r) (a.u.) | K(r) (a.u.) | V(r) (a.u.) | H(r) (a.u.) | ∇2ρ(r) (a.u.) | G(r) (a.u.) | |V(r)|/G(r) |
---|
147 | Cl(19)-H(54) ··· C(50) | 0.00567 | −0.00103 | −0.00262 | 0.00104 | 0.0188 | 0.00366 | 0.71658 |
140 | Cl(19) ··· H(8)-N(7) | 0.0151 | −0.00269 | −0.00961 | 0.00269 | 0.06 | 0.01230 | 0.78120 |
131 | N(7)-H(8) ··· C(50) | 0.00831 | −0.000929 | −0.00348 | 0.000929 | 0.0213 | 0.00441 | 0.78934 |
108 | N(7)-H(24) ··· C(63) | 0.0213 | −0.000864 | −0.011 | 0.000864 | 0.0508 | 0.01183 | 0.92994 |
84 | N(21)-H(22) ··· C(49) | 0.0101 | −0.00122 | −0.00444 | 0.00122 | 0.0275 | 0.00566 | 0.78479 |
77 | C(2)-H(5) ··· C(55) | 0.00668 | −0.000683 | −0.00306 | 0.000683 | 0.0177 | 0.0037 | 0.81746 |
Table 6.
Calculated 𝜀HOMO, 𝜀LUMO, energy band gap (𝜀LUMO- 𝜀HOMO), chemical potential (𝜇), electronegativity (𝜒), global hardness (𝜂), global softness (𝑆), and global electrophilicity index (𝜔) for tetrahydrofuran and its derivatives at B3LYP/6-311 G (d, p) level.
Table 6.
Calculated 𝜀HOMO, 𝜀LUMO, energy band gap (𝜀LUMO- 𝜀HOMO), chemical potential (𝜇), electronegativity (𝜒), global hardness (𝜂), global softness (𝑆), and global electrophilicity index (𝜔) for tetrahydrofuran and its derivatives at B3LYP/6-311 G (d, p) level.
Compounds | 𝜀𝐻 | 𝜀𝐿 | 𝜀𝐿-𝜀𝐻 | 𝜒 | 𝜇 | 𝜂 | 𝑆 | 𝜔 |
Tetraphenylborate | −0.284 | −0.145 | 0.139 | 0.214 | −0.214 | 0.07 | 7.191 | 0.165 |
clonidine | −0.111 | 0.056 | 0.166 | 0.028 | −0.028 | 0.083 | 6.012 | 0.002 |
Table 7.
Fukui functions ( , ), local softness (, ), and local electrophilicity indices (, ) for selected atomic sites of tetraphenylborate, using Mulliken population analysis at B3LYP/6-311 G (d, p) level.
Table 7.
Fukui functions ( , ), local softness (, ), and local electrophilicity indices (, ) for selected atomic sites of tetraphenylborate, using Mulliken population analysis at B3LYP/6-311 G (d, p) level.
| N − 1 | N + 1 | N | f+ | f− | fo | Df | s+ | S− | ω+ | ω− |
---|
B1 | 0.839456 | 0.836684 | 0.836112 | −0.00057 | 0.003344 | 0.001386 | −0.00392 | −0.00411 | 0.024046 | −0.00009 | 0.00055 |
C2 | −0.2508 | −0.25196 | −0.25421 | −0.00226 | 0.003416 | 0.000579 | −0.00567 | −0.01623 | 0.024564 | −0.00037 | 0.00056 |
C3 | −0.06902 | −0.10923 | −0.08563 | 0.023596 | 0.01661 | 0.020103 | 0.006986 | 0.169674 | 0.119439 | 0.00389 | 0.00274 |
C4 | −0.07577 | −0.10353 | −0.09281 | 0.010722 | 0.017038 | 0.01388 | −0.00632 | 0.077099 | 0.122516 | 0.00177 | 0.00281 |
C5 | −0.0487 | −0.11404 | −0.08427 | 0.029772 | 0.035572 | 0.032672 | −0.0058 | 0.214084 | 0.25579 | 0.0049 | 0.00586 |
C6 | −0.0711 | −0.10162 | −0.08696 | 0.014663 | 0.015857 | 0.01526 | −0.00119 | 0.105438 | 0.114024 | 0.00242 | 0.00261 |
C7 | −0.09032 | −0.09647 | −0.09426 | 0.002212 | 0.003942 | 0.003077 | −0.00173 | 0.015906 | 0.028346 | 0.00036 | 0.00065 |
C8 | −0.24004 | −0.25191 | −0.24535 | 0.006559 | 0.005314 | 0.005937 | 0.001245 | 0.047164 | 0.038212 | 0.00108 | 0.00088 |
C9 | −0.08348 | −0.1094 | −0.09278 | 0.016622 | 0.009298 | 0.01296 | 0.007324 | 0.119525 | 0.06686 | 0.00274 | 0.00153 |
C10 | −0.06628 | −0.10348 | −0.08932 | 0.014161 | 0.023037 | 0.018599 | −0.00888 | 0.101829 | 0.165654 | 0.00233 | 0.00379 |
C11 | −0.05648 | −0.11405 | −0.08681 | 0.027237 | 0.030339 | 0.028788 | −0.0031 | 0.195855 | 0.218161 | 0.00449 | 0.005 |
C12 | −0.07361 | −0.10163 | −0.08875 | 0.012874 | 0.015143 | 0.014009 | −0.00227 | 0.092574 | 0.10889 | 0.00212 | 0.00249 |
C13 | −0.08866 | −0.09674 | −0.09423 | 0.002509 | 0.005568 | 0.004039 | −0.00306 | 0.018042 | 0.040038 | 0.00041 | 0.00092 |
C14 | −0.24005 | −0.25192 | −0.24534 | 0.006583 | 0.005291 | 0.005937 | 0.001292 | 0.047337 | 0.038046 | 0.00108 | 0.00087 |
C15 | −0.08324 | −0.1092 | −0.09252 | 0.016683 | 0.009275 | 0.012979 | 0.007408 | 0.119964 | 0.066694 | 0.00275 | 0.00153 |
C16 | −0.06643 | −0.1036 | −0.08944 | 0.014157 | 0.023013 | 0.018585 | −0.00886 | 0.1018 | 0.165481 | 0.00233 | 0.00379 |
C17 | −0.05636 | −0.114 | −0.08669 | 0.027305 | 0.030331 | 0.028818 | −0.00303 | 0.196344 | 0.218103 | 0.0045 | 0.005 |
C18 | −0.07361 | −0.10161 | −0.08875 | 0.012866 | 0.015134 | 0.014 | −0.00227 | 0.092516 | 0.108825 | 0.00212 | 0.00249 |
C19 | −0.0886 | −0.09679 | −0.09419 | 0.002603 | 0.005588 | 0.004096 | −0.00299 | 0.018718 | 0.040182 | 0.00043 | 0.00092 |
C20 | −0.25035 | −0.25162 | −0.25378 | −0.00216 | 0.003429 | 0.000635 | −0.00559 | −0.01552 | 0.024657 | −0.00036 | 0.00056 |
C21 | −0.06924 | −0.10939 | −0.08581 | 0.023573 | 0.016578 | 0.020076 | 0.006995 | 0.169508 | 0.119209 | 0.00388 | 0.00273 |
C22 | −0.07585 | −0.1036 | −0.09287 | 0.010725 | 0.017023 | 0.013874 | −0.0063 | 0.077121 | 0.122409 | 0.00177 | 0.0028 |
C23 | −0.04866 | −0.114 | −0.08421 | 0.029785 | 0.035552 | 0.032669 | −0.00577 | 0.214177 | 0.255646 | 0.00491 | 0.00586 |
C24 | −0.07098 | −0.10158 | −0.08687 | 0.014709 | 0.015891 | 0.0153 | −0.00118 | 0.105769 | 0.114269 | 0.00242 | 0.0034 |
C25 | −0.09101 | −0.09715 | −0.09492 | 0.002233 | 0.003907 | 0.00307 | −0.00167 | 0.016057 | 0.028094 | 0.00048 | 0.00084 |
Table 8.
Fukui functions ( , ), local softness (, ), and local electrophilicity indices (, ) for selected atomic sites of clonidine, using Mulliken population analysis at B3LYP/6-311 G (d, p) level.
Table 8.
Fukui functions ( , ), local softness (, ), and local electrophilicity indices (, ) for selected atomic sites of clonidine, using Mulliken population analysis at B3LYP/6-311 G (d, p) level.
| N − 1 | N + 1 | N | f+ | f− | fo | Df | s+ | S− | ω+ | ω− |
---|
C1 | −0.02712 | −0.08481 | −0.07787 | 0.006941 | 0.050748 | 0.028845 | −0.04381 | 0.041733 | 0.305121 | 0.00002 | 0.00012 |
C2 | −0.00889 | −0.09302 | −0.08584 | 0.00718 | 0.076947 | 0.042064 | −0.06977 | 0.04317 | 0.462642 | 0.00002 | 0.00018 |
N7 | −0.41227 | −0.44987 | −0.43231 | 0.017552 | 0.020048 | 0.0188 | −0.0025 | 0.105531 | 0.120538 | 0.00004 | 0.00005 |
C9 | 0.097191 | 0.161876 | 0.102019 | −0.05986 | −0.00483 | −0.03234 | −0.05503 | −0.35989 | −0.02903 | −0.00014 | −0.00001 |
C10 | −0.20574 | −0.20295 | −0.22272 | −0.01977 | 0.016981 | −0.00139 | −0.03675 | −0.11887 | 0.102098 | −0.00005 | 0.00004 |
C11 | −0.22565 | −0.18438 | −0.21974 | −0.03536 | −0.00591 | −0.02063 | −0.02945 | −0.21259 | −0.03554 | −0.00008 | −0.00001 |
C12 | −0.00928 | 0.035943 | 0.008042 | −0.0279 | −0.01732 | −0.02261 | −0.01058 | −0.16775 | −0.10416 | −0.00006 | −0.00004 |
C13 | 0.011457 | 0.03894 | 0.019476 | −0.01946 | −0.00802 | −0.01374 | −0.01145 | −0.11703 | −0.04821 | −0.00004 | −0.00002 |
C14 | −0.20549 | −0.05483 | −0.1533 | −0.09848 | −0.05219 | −0.07533 | −0.04629 | −0.59208 | −0.31379 | −0.00023 | −0.00012 |
Cl18 | −0.17184 | −0.00223 | −0.12117 | −0.11894 | −0.05067 | −0.08481 | −0.06827 | −0.71512 | −0.30468 | −0.00027 | −0.00012 |
Cl19 | −0.17958 | −0.00233 | −0.12537 | −0.12304 | −0.05421 | −0.08863 | −0.06883 | −0.7398 | −0.32595 | −0.00028 | −0.00012 |
N20 | −0.39893 | −0.43217 | −0.43143 | 0.00074 | 0.032494 | 0.016617 | −0.03175 | 0.004449 | 0.195369 | 0.000002 | 0.00007 |
N21 | −0.39135 | −0.44454 | −0.44651 | −0.00197 | 0.055164 | 0.026596 | −0.05714 | −0.01186 | 0.331672 | −0.000005 | 0.00013 |
C23 | 0.728694 | 0.741153 | 0.720165 | −0.02099 | 0.008529 | −0.00623 | −0.02952 | −0.12619 | 0.05128 | −0.00005 | 0.00002 |
Table 9.
Fukui functions ( , ), local softness (, ), and local electrophilicity indices (, ) for selected atomic sites of complex, using Mulliken population analysis at B3LYP/6-311 G (d, p) level.
Table 9.
Fukui functions ( , ), local softness (, ), and local electrophilicity indices (, ) for selected atomic sites of complex, using Mulliken population analysis at B3LYP/6-311 G (d, p) level.
Atom | N | N + 1 | N − 1 | f− | f+ | fo | Df | s+ | S− | ω+ | ω− |
---|
1C | 0.003 | −0.0058 | 0.0083 | 0.0052 | 0.0088 | 0.007 | 0.0036 | 0.005 | 0.0084 | 0.000062 | 0.000036 |
2C | 0.007 | −0.0038 | 0.0083 | 0.0012 | 0.0108 | 0.006 | 0.0096 | 0.0012 | 0.0104 | 0.000076 | 0.000008 |
7N | 0.054 | 0.0405 | 0.0538 | −0.0002 | 0.0134 | 0.0066 | 0.0136 | −0.0002 | 0.0128 | 0.000094 | −1×10−6 |
9C | 0.0397 | −0.0597 | 0.035 | −0.0047 | 0.0995 | 0.0474 | 0.1042 | −0.0045 | 0.095 | 0.000697 | −3.3×10−6 |
10C | 0.0353 | −0.0295 | 0.0357 | 0.0005 | 0.0648 | 0.0326 | 0.0643 | 0.0004 | 0.0619 | 0.000454 | 0.000004 |
11C | 0.0334 | −0.0189 | 0.0327 | −0.0007 | 0.0523 | 0.0258 | 0.0529 | −0.0006 | 0.0499 | 0.000366 | −5×10−6 |
12C | −0.0286 | −0.0806 | −0.0225 | 0.0062 | 0.052 | 0.0291 | 0.0459 | 0.0059 | 0.0497 | 0.000364 | 0.000043 |
13C | −0.0285 | −0.0932 | −0.0244 | 0.0041 | 0.0646 | 0.0344 | 0.0606 | 0.0039 | 0.0618 | 0.000453 | 0.000029 |
14C | −0.009 | −0.1338 | −0.0021 | 0.0069 | 0.1248 | 0.0658 | 0.1179 | 0.0066 | 0.1192 | 0.000874 | 0.000048 |
18Cl | 0.0134 | −0.0926 | 0.0105 | −0.0028 | 0.106 | 0.0516 | 0.1088 | −0.0027 | 0.1013 | 0.000743 | −0.00002 |
19Cl | 0.0326 | −0.0644 | 0.0185 | −0.0141 | 0.097 | 0.0415 | 0.1111 | −0.0134 | 0.0927 | 0.000679 | −9.9×10−5 |
20N | −0.1986 | −0.2022 | −0.1918 | 0.0067 | 0.0036 | 0.0052 | −0.0031 | 0.0064 | 0.0034 | 0.000025 | 0.000047 |
21N | −0.108 | −0.1278 | −0.1193 | −0.0113 | 0.0197 | 0.0042 | 0.031 | −0.0108 | 0.0189 | 0.000138 | −7.6×10−5 |
23C | 0.1434 | 0.1376 | 0.1418 | −0.0016 | 0.0058 | 0.0021 | 0.0073 | −0.0015 | 0.0055 | 0.000041 | −1.1×10−5 |
25B | −0.0134 | −0.0105 | −0.0016 | 0.0118 | −0.0029 | 0.0045 | −0.0148 | 0.0113 | −0.0028 | −0.00002 | 0.000083 |
26C | −0.0527 | −0.0486 | −0.0008 | 0.0519 | −0.004 | 0.0239 | −0.0559 | 0.0496 | −0.0038 | −2.8×10−5 | 0.000364 |
27C | −0.0557 | −0.0565 | −0.0208 | 0.0348 | 0.0008 | 0.0178 | −0.034 | 0.0333 | 0.0008 | 0.000006 | 0.000244 |
28C | −0.046 | −0.0467 | −0.007 | 0.039 | 0.0008 | 0.0199 | −0.0382 | 0.0372 | 0.0007 | 0.000006 | 0.000273 |
29C | −0.0573 | −0.0647 | −0.019 | 0.0383 | 0.0074 | 0.0229 | −0.0309 | 0.0366 | 0.0071 | 0.000052 | 0.000268 |
31C | −0.0548 | −0.0633 | −0.0272 | 0.0276 | 0.0085 | 0.0181 | −0.0191 | 0.0264 | 0.0081 | 0.00006 | 0.000193 |
33C | −0.0611 | −0.0713 | 0.01 | 0.0711 | 0.0102 | 0.0406 | −0.061 | 0.068 | 0.0097 | 0.000071 | 0.000498 |
37C | −0.0528 | −0.0493 | −0.0003 | 0.0524 | −0.0035 | 0.0245 | −0.0559 | 0.0501 | −0.0033 | −2.5×10−5 | 0.000367 |
38C | −0.056 | −0.0561 | −0.0211 | 0.0349 | 0.0001 | 0.0175 | −0.0348 | 0.0334 | 0.0001 | 0.000001 | 0.000244 |
39C | −0.0452 | −0.048 | −0.0057 | 0.0395 | 0.0028 | 0.0212 | −0.0367 | 0.0378 | 0.0027 | 0.00002 | 0.000277 |
40C | −0.0572 | −0.0652 | −0.0183 | 0.0389 | 0.0079 | 0.0234 | −0.031 | 0.0372 | 0.0076 | 0.000055 | 0.000272 |
42C | −0.0544 | −0.0647 | −0.0267 | 0.0278 | 0.0103 | 0.019 | −0.0175 | 0.0265 | 0.0098 | 0.000072 | 0.000195 |
44C | −0.0608 | −0.0724 | 0.0109 | 0.0717 | 0.0116 | 0.0417 | −0.0601 | 0.0685 | 0.0111 | 0.000081 | 0.000502 |
48C | −0.0411 | −0.045 | −0.054 | −0.0129 | 0.0038 | −0.0045 | 0.0167 | −0.0123 | 0.0036 | 0.000027 | −0.00009 |
49C | −0.0448 | −0.054 | −0.0488 | −0.0041 | 0.0092 | 0.0026 | 0.0133 | −0.0039 | 0.0088 | 0.000064 | −2.9×10−5 |
50C | −0.0583 | −0.0531 | −0.0606 | −0.0023 | −0.0052 | −0.0037 | −0.0028 | −0.0022 | −0.0049 | −3.6×10−5 | −1.6×10−5 |
51C | −0.0463 | −0.0582 | −0.0373 | 0.0089 | 0.0119 | 0.0104 | 0.003 | 0.0085 | 0.0114 | 0.000083 | 0.000062 |
53C | −0.0579 | −0.0565 | −0.047 | 0.0109 | −0.0014 | 0.0048 | −0.0123 | 0.0104 | −0.0014 | −0.00001 | 0.000076 |
55C | −0.0587 | −0.0662 | −0.0439 | 0.0149 | 0.0075 | 0.0112 | −0.0074 | 0.0142 | 0.0071 | 0.000053 | 0.000104 |
59C | −0.0546 | −0.0507 | −0.0452 | 0.0094 | −0.004 | 0.0027 | −0.0134 | 0.009 | −0.0038 | −2.8×10−5 | 0.000066 |
60C | −0.0457 | −0.0522 | −0.05 | −0.0042 | 0.0065 | 0.0011 | 0.0107 | −0.004 | 0.0062 | 0.000046 | −2.9×10−5 |
61C | −0.0409 | −0.0513 | −0.0541 | −0.0132 | 0.0104 | −0.0014 | 0.0236 | −0.0126 | 0.01 | 0.000073 | −9.2×10−5 |
62C | −0.0435 | −0.054 | −0.0474 | −0.0039 | 0.0105 | 0.0033 | 0.0144 | −0.0037 | 0.01 | 0.000074 | −2.7×10−5 |
63C | −0.056 | −0.0592 | −0.0459 | 0.0101 | 0.0032 | 0.0066 | −0.0068 | 0.0096 | 0.0031 | 0.000022 | 0.000071 |
64C | −0.0641 | −0.0572 | −0.049 | 0.0151 | −0.0069 | 0.0041 | −0.022 | 0.0144 | −0.0066 | −4.8×10−5 | 0.000106 |