The structure of 8-oxo-5,10,15,20-tetraphenyl-7-oxaporphyrin N24-oxide, C43H28N4O3, (4B), shows that N-oxidation of the pyrrole opposite the oxazolidone group cants the pyrrole out of the mean plane of the chromophore. This also affects the oxazolidone group, which is also slightly canted out. This conformation is qualitatively similar to that of the parent meso-tetraphenylporphyrin N-oxide, but dissimilar to that of the porpholactone N-oxide isomer 8-oxo-5,10,15,20-tetraphenyl-7-oxaporphyrin N22-oxide, (4A), carrying the N-oxide at the oxazolidone group. While the degree of canting of the N-oxidized groups in both cases is comparable (and more pronounced than in the porphyrin N-oxide case), in (4A) the pyrrolic groups adjacent to the N-oxidized group are more affected than the opposing group. These differences in the conformational modes may contribute to rationalizing the distinctly different electronic properties of (4A) and (4B).
Supporting information
CCDC reference: 1008298
Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 (Bruker, 2009); data reduction: APEX2 (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2014) and SHELXLE (Hübschle et al.,
2011); molecular graphics: Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).
8-Oxo-5,10,15,20-tetraphenyl-7-oxaporphyrin
N24-oxide
top
Crystal data top
C43H28N4O3 | Z = 1 |
Mr = 648.69 | F(000) = 338 |
Triclinic, P1 | Dx = 1.358 Mg m−3 |
a = 6.3512 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.405 (2) Å | Cell parameters from 2036 reflections |
c = 12.464 (2) Å | θ = 2.4–30.3° |
α = 95.548 (3)° | µ = 0.09 mm−1 |
β = 99.348 (3)° | T = 100 K |
γ = 100.200 (3)° | Block, black |
V = 793.2 (3) Å3 | 0.32 × 0.17 × 0.11 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3185 independent reflections |
Radiation source: fine-focus sealed tube | 2371 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ω scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: multi-scan (APEX2; Bruker, 2009) | h = −7→7 |
Tmin = 0.469, Tmax = 0.746 | k = −12→12 |
6892 measured reflections | l = −15→15 |
Refinement top
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.052P)2 + 0.4642P] where P = (Fo2 + 2Fc2)/3 |
3185 reflections | (Δ/σ)max < 0.001 |
283 parameters | Δρmax = 0.28 e Å−3 |
152 restraints | Δρmin = −0.27 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | −0.3131 (3) | 0.4285 (2) | 0.66082 (19) | 0.0272 (5) | |
N1_a | −0.132 (2) | 0.5132 (16) | 0.6439 (7) | 0.0301 (18) | 0.3159 (16) |
H1A1_a | −0.0917 | 0.5218 | 0.5803 | 0.036* | 0.3159 (16) |
C2_a | −0.314 (2) | 0.4428 (17) | 0.7792 (9) | 0.0272 (5) | 0.3159 (16) |
H2_a | −0.4192 | 0.3959 | 0.8146 | 0.033* | 0.3159 (16) |
C3_a | −0.137 (3) | 0.535 (2) | 0.8287 (9) | 0.0262 (4) | 0.3159 (16) |
H3_a | −0.0944 | 0.5635 | 0.9052 | 0.031* | 0.3159 (16) |
N1A1_b | −0.132 (2) | 0.5132 (16) | 0.6439 (7) | 0.0301 (18) | 0.2905 (12) |
O2A1_b | −0.3357 (16) | 0.4401 (12) | 0.7628 (7) | 0.0272 (5) | 0.2905 (12) |
O3A1_b | −0.1305 (10) | 0.5544 (7) | 0.9180 (5) | 0.0424 (16) | 0.2905 (12) |
C3A1_b | −0.160 (2) | 0.5349 (17) | 0.8218 (11) | 0.0262 (4) | 0.2905 (12) |
N1A2_c | −0.132 (2) | 0.5132 (16) | 0.6439 (7) | 0.0301 (18) | 0.0515 (12) |
O2A2_c | −0.156 (4) | 0.574 (2) | 0.8167 (17) | 0.0262 (4) | 0.0515 (12) |
C2A2_c | −0.336 (3) | 0.475 (2) | 0.7706 (17) | 0.0272 (5) | 0.0515 (12) |
O3A2_c | −0.468 (5) | 0.441 (3) | 0.821 (2) | 0.0272 (5) | 0.0515 (12) |
N1A_d | −0.149 (5) | 0.524 (3) | 0.6446 (12) | 0.0301 (18) | 0.3421 (8) |
O1A_d | −0.1322 (7) | 0.5743 (4) | 0.5521 (3) | 0.0239 (9) | 0.3421 (8) |
C2A_d | −0.2990 (17) | 0.4309 (11) | 0.7796 (9) | 0.0272 (5) | 0.3421 (8) |
H2A_d | −0.3930 | 0.3750 | 0.8151 | 0.033* | 0.3421 (8) |
C3A_d | −0.129 (2) | 0.5267 (14) | 0.8297 (8) | 0.0262 (4) | 0.3421 (8) |
H3A_d | −0.0847 | 0.5530 | 0.9064 | 0.031* | 0.3421 (8) |
C4 | −0.0261 (3) | 0.5819 (2) | 0.74314 (18) | 0.0262 (4) | |
C5 | 0.1760 (3) | 0.6717 (2) | 0.76366 (19) | 0.0254 (5) | |
C6 | 0.3127 (3) | 0.6980 (2) | 0.68682 (19) | 0.0261 (5) | |
N2_e | 0.2750 (5) | 0.6423 (3) | 0.5795 (3) | 0.0248 (8) | 0.6841 (16) |
H2A1_e | 0.1601 | 0.5825 | 0.5475 | 0.030* | 0.6841 (16) |
C7_e | 0.5221 (9) | 0.7860 (6) | 0.7068 (4) | 0.0281 (9) | 0.6841 (16) |
H7_e | 0.5910 | 0.8389 | 0.7740 | 0.034* | 0.6841 (16) |
C8_e | 0.6032 (11) | 0.7794 (10) | 0.6122 (5) | 0.0311 (11) | 0.6841 (16) |
H8_e | 0.7417 | 0.8238 | 0.6026 | 0.037* | 0.6841 (16) |
N2B1_f | 0.2750 (5) | 0.6423 (3) | 0.5795 (3) | 0.0248 (8) | 0.1204 (12) |
C7B1_f | 0.517 (4) | 0.790 (2) | 0.6983 (17) | 0.0281 (9) | 0.1204 (12) |
O2B1_f | 0.589 (4) | 0.786 (3) | 0.5993 (18) | 0.0311 (11) | 0.1204 (12) |
O3B1_f | 0.630 (2) | 0.8609 (12) | 0.7705 (11) | 0.0281 (9) | 0.1204 (12) |
N2B2_g | 0.2750 (5) | 0.6423 (3) | 0.5795 (3) | 0.0248 (8) | 0.0375 (12) |
O2B2_g | 0.517 (4) | 0.771 (3) | 0.7143 (17) | 0.0281 (9) | 0.0375 (12) |
C8B2_g | 0.605 (4) | 0.766 (4) | 0.6199 (18) | 0.0311 (11) | 0.0375 (12) |
O3B2_g | 0.786 (6) | 0.815 (4) | 0.619 (4) | 0.0311 (11) | 0.0375 (12) |
N2B_h | 0.254 (3) | 0.673 (2) | 0.574 (2) | 0.0248 (8) | 0.1579 (8) |
O1B_h | 0.0475 (14) | 0.6399 (9) | 0.5187 (8) | 0.0239 (9) | 0.1579 (8) |
C7B_h | 0.541 (2) | 0.759 (2) | 0.7114 (11) | 0.0281 (9) | 0.1579 (8) |
H7B_h | 0.6258 | 0.7881 | 0.7826 | 0.034* | 0.1579 (8) |
C8B_h | 0.613 (3) | 0.769 (4) | 0.6156 (14) | 0.0311 (11) | 0.1579 (8) |
H8B_h | 0.7497 | 0.8157 | 0.6064 | 0.037* | 0.1579 (8) |
C9 | 0.4418 (3) | 0.6931 (2) | 0.52916 (18) | 0.0269 (5) | |
C10 | 0.4587 (3) | 0.6664 (2) | 0.41797 (19) | 0.0257 (5) | |
C11 | 0.2558 (4) | 0.7396 (2) | 0.87888 (19) | 0.0284 (5) | |
C12 | 0.1378 (4) | 0.8249 (3) | 0.9251 (2) | 0.0394 (6) | |
H12 | 0.0059 | 0.8387 | 0.8840 | 0.047* | |
C13 | 0.2131 (5) | 0.8894 (3) | 1.0309 (2) | 0.0501 (8) | |
H13 | 0.1313 | 0.9464 | 1.0620 | 0.060* | |
C14 | 0.4048 (5) | 0.8716 (3) | 1.0910 (2) | 0.0535 (8) | |
H14 | 0.4563 | 0.9171 | 1.1629 | 0.064* | |
C15 | 0.5222 (5) | 0.7875 (3) | 1.0464 (2) | 0.0540 (8) | |
H15 | 0.6549 | 0.7753 | 1.0878 | 0.065* | |
C16 | 0.4476 (4) | 0.7206 (3) | 0.9414 (2) | 0.0419 (7) | |
H16 | 0.5281 | 0.6615 | 0.9121 | 0.050* | |
C17 | 0.6396 (3) | 0.7525 (2) | 0.37954 (18) | 0.0235 (5) | |
C18 | 0.6600 (4) | 0.8896 (2) | 0.39499 (19) | 0.0290 (5) | |
H18 | 0.5591 | 0.9274 | 0.4300 | 0.035* | |
C19 | 0.8262 (4) | 0.9711 (2) | 0.3597 (2) | 0.0335 (6) | |
H19 | 0.8390 | 1.0640 | 0.3710 | 0.040* | |
C20 | 0.9736 (4) | 0.9164 (2) | 0.3079 (2) | 0.0325 (6) | |
H20 | 1.0875 | 0.9719 | 0.2839 | 0.039* | |
C21 | 0.9545 (4) | 0.7808 (2) | 0.2912 (2) | 0.0333 (6) | |
H21 | 1.0546 | 0.7435 | 0.2552 | 0.040* | |
C22 | 0.7888 (4) | 0.6994 (2) | 0.3272 (2) | 0.0296 (5) | |
H22 | 0.7772 | 0.6066 | 0.3160 | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0187 (10) | 0.0220 (9) | 0.0384 (11) | 0.0010 (7) | 0.0035 (8) | −0.0002 (8) |
N1_a | 0.022 (2) | 0.029 (3) | 0.0343 (11) | −0.002 (2) | −0.0022 (10) | 0.0058 (10) |
C2_a | 0.0187 (10) | 0.0220 (9) | 0.0384 (11) | 0.0010 (7) | 0.0035 (8) | −0.0002 (8) |
C3_a | 0.0205 (10) | 0.0227 (9) | 0.0333 (10) | 0.0042 (7) | 0.0010 (7) | 0.0000 (7) |
N1A1_b | 0.022 (2) | 0.029 (3) | 0.0343 (11) | −0.002 (2) | −0.0022 (10) | 0.0058 (10) |
O2A1_b | 0.0187 (10) | 0.0220 (9) | 0.0384 (11) | 0.0010 (7) | 0.0035 (8) | −0.0002 (8) |
O3A1_b | 0.035 (3) | 0.052 (4) | 0.030 (3) | −0.012 (3) | 0.005 (3) | −0.007 (3) |
C3A1_b | 0.0205 (10) | 0.0227 (9) | 0.0333 (10) | 0.0042 (7) | 0.0010 (7) | 0.0000 (7) |
N1A2_c | 0.022 (2) | 0.029 (3) | 0.0343 (11) | −0.002 (2) | −0.0022 (10) | 0.0058 (10) |
O2A2_c | 0.0205 (10) | 0.0227 (9) | 0.0333 (10) | 0.0042 (7) | 0.0010 (7) | 0.0000 (7) |
C2A2_c | 0.0187 (10) | 0.0220 (9) | 0.0384 (11) | 0.0010 (7) | 0.0035 (8) | −0.0002 (8) |
O3A2_c | 0.0187 (10) | 0.0220 (9) | 0.0384 (11) | 0.0010 (7) | 0.0035 (8) | −0.0002 (8) |
N1A_d | 0.022 (2) | 0.029 (3) | 0.0343 (11) | −0.002 (2) | −0.0022 (10) | 0.0058 (10) |
O1A_d | 0.022 (2) | 0.021 (2) | 0.026 (2) | 0.0011 (15) | 0.0004 (16) | 0.0029 (16) |
C2A_d | 0.0187 (10) | 0.0220 (9) | 0.0384 (11) | 0.0010 (7) | 0.0035 (8) | −0.0002 (8) |
C3A_d | 0.0205 (10) | 0.0227 (9) | 0.0333 (10) | 0.0042 (7) | 0.0010 (7) | 0.0000 (7) |
C4 | 0.0205 (10) | 0.0227 (9) | 0.0333 (10) | 0.0042 (7) | 0.0010 (7) | 0.0000 (7) |
C5 | 0.0227 (11) | 0.0199 (11) | 0.0318 (12) | 0.0035 (8) | 0.0000 (9) | 0.0033 (9) |
C6 | 0.0198 (11) | 0.0199 (11) | 0.0352 (13) | 0.0013 (8) | −0.0010 (9) | 0.0019 (9) |
N2_e | 0.0191 (11) | 0.021 (2) | 0.0311 (12) | −0.0013 (10) | 0.0014 (10) | 0.0032 (13) |
C7_e | 0.0206 (13) | 0.023 (2) | 0.0361 (15) | 0.0006 (11) | −0.0011 (10) | −0.0024 (12) |
C8_e | 0.0191 (14) | 0.0258 (19) | 0.0453 (19) | −0.0026 (13) | 0.0074 (13) | −0.0010 (15) |
N2B1_f | 0.0191 (11) | 0.021 (2) | 0.0311 (12) | −0.0013 (10) | 0.0014 (10) | 0.0032 (13) |
C7B1_f | 0.0206 (13) | 0.023 (2) | 0.0361 (15) | 0.0006 (11) | −0.0011 (10) | −0.0024 (12) |
O2B1_f | 0.0191 (14) | 0.0258 (19) | 0.0453 (19) | −0.0026 (13) | 0.0074 (13) | −0.0010 (15) |
O3B1_f | 0.0206 (13) | 0.023 (2) | 0.0361 (15) | 0.0006 (11) | −0.0011 (10) | −0.0024 (12) |
N2B2_g | 0.0191 (11) | 0.021 (2) | 0.0311 (12) | −0.0013 (10) | 0.0014 (10) | 0.0032 (13) |
O2B2_g | 0.0206 (13) | 0.023 (2) | 0.0361 (15) | 0.0006 (11) | −0.0011 (10) | −0.0024 (12) |
C8B2_g | 0.0191 (14) | 0.0258 (19) | 0.0453 (19) | −0.0026 (13) | 0.0074 (13) | −0.0010 (15) |
O3B2_g | 0.0191 (14) | 0.0258 (19) | 0.0453 (19) | −0.0026 (13) | 0.0074 (13) | −0.0010 (15) |
N2B_h | 0.0191 (11) | 0.021 (2) | 0.0311 (12) | −0.0013 (10) | 0.0014 (10) | 0.0032 (13) |
O1B_h | 0.022 (2) | 0.021 (2) | 0.026 (2) | 0.0011 (15) | 0.0004 (16) | 0.0029 (16) |
C7B_h | 0.0206 (13) | 0.023 (2) | 0.0361 (15) | 0.0006 (11) | −0.0011 (10) | −0.0024 (12) |
C8B_h | 0.0191 (14) | 0.0258 (19) | 0.0453 (19) | −0.0026 (13) | 0.0074 (13) | −0.0010 (15) |
C9 | 0.0207 (11) | 0.0228 (11) | 0.0347 (13) | 0.0015 (9) | 0.0032 (9) | 0.0008 (9) |
C10 | 0.0182 (11) | 0.0238 (11) | 0.0332 (13) | 0.0019 (8) | 0.0027 (9) | 0.0013 (9) |
C11 | 0.0252 (12) | 0.0240 (12) | 0.0304 (12) | −0.0060 (9) | −0.0001 (9) | 0.0040 (9) |
C12 | 0.0404 (15) | 0.0329 (14) | 0.0399 (15) | 0.0054 (11) | −0.0009 (12) | −0.0022 (11) |
C13 | 0.067 (2) | 0.0376 (16) | 0.0386 (16) | 0.0069 (14) | 0.0004 (14) | −0.0074 (12) |
C14 | 0.065 (2) | 0.0484 (18) | 0.0303 (15) | −0.0127 (15) | −0.0096 (13) | −0.0040 (13) |
C15 | 0.0420 (17) | 0.068 (2) | 0.0434 (17) | 0.0029 (15) | −0.0105 (13) | 0.0093 (15) |
C16 | 0.0351 (14) | 0.0480 (16) | 0.0376 (15) | 0.0052 (12) | −0.0050 (11) | 0.0056 (12) |
C17 | 0.0158 (10) | 0.0247 (11) | 0.0264 (11) | −0.0003 (8) | −0.0004 (8) | 0.0003 (9) |
C18 | 0.0243 (12) | 0.0250 (12) | 0.0356 (13) | 0.0033 (9) | 0.0036 (10) | 0.0000 (10) |
C19 | 0.0297 (13) | 0.0212 (12) | 0.0446 (15) | −0.0025 (9) | 0.0016 (11) | 0.0027 (10) |
C20 | 0.0220 (12) | 0.0325 (13) | 0.0387 (14) | −0.0046 (9) | 0.0030 (10) | 0.0066 (11) |
C21 | 0.0220 (12) | 0.0348 (14) | 0.0430 (15) | 0.0031 (10) | 0.0093 (10) | 0.0037 (11) |
C22 | 0.0252 (12) | 0.0218 (11) | 0.0401 (14) | 0.0028 (9) | 0.0048 (10) | 0.0001 (10) |
Geometric parameters (Å, º) top
C1—O2A1_b | 1.299 (10) | C8_e—H8_e | 0.9500 |
C1—N1A_d | 1.36 (2) | C7B1_f—O3B1_f | 1.16 (2) |
C1—N1_a | 1.377 (11) | C7B1_f—O2B1_f | 1.384 (17) |
C1—C10i | 1.410 (3) | O2B1_f—C9 | 1.349 (18) |
C1—C2A2_c | 1.448 (19) | O2B2_g—C8B2_g | 1.383 (18) |
C1—C2A_d | 1.466 (11) | C8B2_g—O3B2_g | 1.18 (4) |
C1—C2_a | 1.470 (12) | C8B2_g—C9 | 1.45 (2) |
N1_a—C4 | 1.372 (7) | N2B_h—O1B_h | 1.35 (2) |
N1_a—H1A1_a | 0.8800 | N2B_h—C9 | 1.386 (14) |
C2_a—C3_a | 1.357 (12) | C7B_h—C8B_h | 1.352 (14) |
C2_a—H2_a | 0.9500 | C7B_h—H7B_h | 0.9500 |
C3_a—C4 | 1.448 (12) | C8B_h—C9 | 1.452 (15) |
C3_a—H3_a | 0.9500 | C8B_h—H8B_h | 0.9500 |
O2A1_b—C3A1_b | 1.400 (12) | C9—C10 | 1.412 (3) |
O3A1_b—C3A1_b | 1.176 (14) | C10—C1i | 1.410 (3) |
C3A1_b—C4 | 1.463 (14) | C10—C17 | 1.500 (3) |
O2A2_c—C4 | 1.330 (18) | C11—C16 | 1.392 (3) |
O2A2_c—C2A2_c | 1.395 (17) | C11—C12 | 1.399 (4) |
C2A2_c—O3A2_c | 1.15 (4) | C12—C13 | 1.389 (4) |
N1A_d—O1A_d | 1.32 (2) | C12—H12 | 0.9500 |
N1A_d—C4 | 1.364 (11) | C13—C14 | 1.374 (4) |
C2A_d—C3A_d | 1.353 (11) | C13—H13 | 0.9500 |
C2A_d—H2A_d | 0.9500 | C14—C15 | 1.379 (5) |
C3A_d—C4 | 1.462 (11) | C14—H14 | 0.9500 |
C3A_d—H3A_d | 0.9500 | C15—C16 | 1.387 (4) |
C4—C5 | 1.417 (3) | C15—H15 | 0.9500 |
C5—C6 | 1.408 (3) | C16—H16 | 0.9500 |
C5—C11 | 1.503 (3) | C17—C22 | 1.395 (3) |
C6—O2B2_g | 1.35 (2) | C17—C18 | 1.401 (3) |
C6—N2_e | 1.371 (5) | C18—C19 | 1.390 (3) |
C6—N2B_h | 1.38 (3) | C18—H18 | 0.9500 |
C6—C7_e | 1.444 (6) | C19—C20 | 1.389 (4) |
C6—C7B1_f | 1.45 (2) | C19—H19 | 0.9500 |
C6—C7B_h | 1.447 (14) | C20—C21 | 1.387 (3) |
N2_e—C9 | 1.370 (4) | C20—H20 | 0.9500 |
N2_e—H2A1_e | 0.8800 | C21—C22 | 1.392 (3) |
C7_e—C8_e | 1.362 (6) | C21—H21 | 0.9500 |
C7_e—H7_e | 0.9500 | C22—H22 | 0.9500 |
C8_e—C9 | 1.441 (6) | | |
| | | |
O2A1_b—C1—C10i | 120.9 (4) | O3B1_f—C7B1_f—C6 | 134.5 (18) |
N1A_d—C1—C10i | 128.3 (7) | O2B1_f—C7B1_f—C6 | 109.7 (15) |
N1_a—C1—C10i | 126.9 (4) | C9—O2B1_f—C7B1_f | 106.2 (14) |
C10i—C1—C2A2_c | 128.7 (8) | C6—O2B2_g—C8B2_g | 106.2 (15) |
N1A_d—C1—C2A_d | 107.2 (7) | O3B2_g—C8B2_g—O2B2_g | 122 (3) |
C10i—C1—C2A_d | 124.2 (4) | O3B2_g—C8B2_g—C9 | 128 (3) |
N1_a—C1—C2_a | 107.6 (6) | O2B2_g—C8B2_g—C9 | 109.6 (15) |
C10i—C1—C2_a | 125.1 (5) | O1B_h—N2B_h—C6 | 124.5 (12) |
C4—N1_a—C1 | 108.4 (8) | O1B_h—N2B_h—C9 | 126.8 (19) |
C4—N1_a—H1A1_a | 125.8 | C6—N2B_h—C9 | 108.6 (14) |
C1—N1_a—H1A1_a | 125.8 | C8B_h—C7B_h—C6 | 108.1 (10) |
C3_a—C2_a—C1 | 107.6 (8) | C8B_h—C7B_h—H7B_h | 125.9 |
C3_a—C2_a—H2_a | 126.2 | C6—C7B_h—H7B_h | 125.9 |
C1—C2_a—H2_a | 126.2 | C7B_h—C8B_h—C9 | 107.4 (10) |
C2_a—C3_a—C4 | 107.1 (8) | C7B_h—C8B_h—H8B_h | 126.3 |
C2_a—C3_a—H3_a | 126.4 | C9—C8B_h—H8B_h | 126.3 |
C4—C3_a—H3_a | 126.4 | O2B1_f—C9—C10 | 121.8 (8) |
C1—O2A1_b—C3A1_b | 107.7 (9) | N2_e—C9—C10 | 127.6 (3) |
O3A1_b—C3A1_b—O2A1_b | 121.1 (11) | N2B_h—C9—C10 | 127.3 (11) |
O3A1_b—C3A1_b—C4 | 131.4 (10) | N2_e—C9—C8_e | 106.9 (3) |
O2A1_b—C3A1_b—C4 | 107.1 (10) | C10—C9—C8_e | 125.4 (3) |
C4—O2A2_c—C2A2_c | 106.2 (14) | C10—C9—C8B2_g | 128.9 (9) |
O3A2_c—C2A2_c—O2A2_c | 121 (2) | N2B_h—C9—C8B_h | 106.3 (13) |
O3A2_c—C2A2_c—C1 | 131 (2) | C10—C9—C8B_h | 125.7 (6) |
O2A2_c—C2A2_c—C1 | 108.6 (15) | C1i—C10—C9 | 125.6 (2) |
O1A_d—N1A_d—C1 | 126.3 (12) | C1i—C10—C17 | 117.6 (2) |
O1A_d—N1A_d—C4 | 122.4 (15) | C9—C10—C17 | 116.69 (19) |
C1—N1A_d—C4 | 109.8 (13) | C16—C11—C12 | 118.6 (2) |
C3A_d—C2A_d—C1 | 108.0 (8) | C16—C11—C5 | 121.4 (2) |
C3A_d—C2A_d—H2A_d | 126.0 | C12—C11—C5 | 120.1 (2) |
C1—C2A_d—H2A_d | 126.0 | C13—C12—C11 | 120.1 (3) |
C2A_d—C3A_d—C4 | 106.8 (8) | C13—C12—H12 | 119.9 |
C2A_d—C3A_d—H3A_d | 126.6 | C11—C12—H12 | 119.9 |
C4—C3A_d—H3A_d | 126.6 | C14—C13—C12 | 120.6 (3) |
O2A2_c—C4—C5 | 121.6 (8) | C14—C13—H13 | 119.7 |
N1A_d—C4—C5 | 128.3 (10) | C12—C13—H13 | 119.7 |
N1_a—C4—C5 | 126.6 (6) | C13—C14—C15 | 119.7 (3) |
N1_a—C4—C3_a | 109.1 (7) | C13—C14—H14 | 120.2 |
C5—C4—C3_a | 123.7 (5) | C15—C14—H14 | 120.2 |
N1A_d—C4—C3A_d | 108.0 (11) | C14—C15—C16 | 120.4 (3) |
C5—C4—C3A_d | 123.4 (5) | C14—C15—H15 | 119.8 |
C5—C4—C3A1_b | 128.6 (5) | C16—C15—H15 | 119.8 |
C6—C5—C4 | 125.6 (2) | C15—C16—C11 | 120.5 (3) |
C6—C5—C11 | 117.33 (19) | C15—C16—H16 | 119.8 |
C4—C5—C11 | 117.0 (2) | C11—C16—H16 | 119.8 |
O2B2_g—C6—C5 | 123.1 (9) | C22—C17—C18 | 118.5 (2) |
N2_e—C6—C5 | 126.5 (2) | C22—C17—C10 | 121.5 (2) |
N2B_h—C6—C5 | 126.8 (6) | C18—C17—C10 | 119.9 (2) |
N2_e—C6—C7_e | 106.9 (3) | C19—C18—C17 | 120.8 (2) |
C5—C6—C7_e | 126.6 (3) | C19—C18—H18 | 119.6 |
C5—C6—C7B1_f | 129.9 (8) | C17—C18—H18 | 119.6 |
N2B_h—C6—C7B_h | 106.9 (8) | C20—C19—C18 | 119.8 (2) |
C5—C6—C7B_h | 126.2 (6) | C20—C19—H19 | 120.1 |
C9—N2_e—C6 | 110.2 (3) | C18—C19—H19 | 120.1 |
C9—N2_e—H2A1_e | 124.9 | C21—C20—C19 | 120.1 (2) |
C6—N2_e—H2A1_e | 124.9 | C21—C20—H20 | 120.0 |
C8_e—C7_e—C6 | 107.8 (4) | C19—C20—H20 | 120.0 |
C8_e—C7_e—H7_e | 126.1 | C20—C21—C22 | 120.0 (2) |
C6—C7_e—H7_e | 126.1 | C20—C21—H21 | 120.0 |
C7_e—C8_e—C9 | 107.9 (4) | C22—C21—H21 | 120.0 |
C7_e—C8_e—H8_e | 126.0 | C21—C22—C17 | 120.8 (2) |
C9—C8_e—H8_e | 126.0 | C21—C22—H22 | 119.6 |
O3B1_f—C7B1_f—O2B1_f | 115.7 (18) | C17—C22—H22 | 119.6 |
| | | |
O2A1_b—C1—N1_a—C4 | 2.0 (18) | O2B2_g—C6—C7_e—C8_e | 116 (10) |
N1A_d—C1—N1_a—C4 | 80 (7) | N2_e—C6—C7_e—C8_e | −0.5 (5) |
C10i—C1—N1_a—C4 | −175.3 (6) | N2B_h—C6—C7_e—C8_e | −16.5 (10) |
C2A2_c—C1—N1_a—C4 | 14.0 (18) | C5—C6—C7_e—C8_e | 177.9 (5) |
C2A_d—C1—N1_a—C4 | −9.0 (17) | C7B1_f—C6—C7_e—C8_e | −45 (14) |
C2_a—C1—N1_a—C4 | −2.1 (18) | C7B_h—C6—C7_e—C8_e | 84 (3) |
O2A1_b—C1—C2_a—C3_a | −140 (12) | C6—C7_e—C8_e—C9 | 3.2 (7) |
N1A_d—C1—C2_a—C3_a | −7 (2) | O2B2_g—C6—C7B1_f—O3B1_f | −52 (8) |
N1_a—C1—C2_a—C3_a | 0.5 (15) | N2_e—C6—C7B1_f—O3B1_f | −177 (3) |
C10i—C1—C2_a—C3_a | 173.8 (10) | N2B_h—C6—C7B1_f—O3B1_f | 167 (3) |
C2A2_c—C1—C2_a—C3_a | −77 (3) | C5—C6—C7B1_f—O3B1_f | 5 (4) |
C2A_d—C1—C2_a—C3_a | 90 (6) | C7_e—C6—C7B1_f—O3B1_f | −41 (12) |
C1—C2_a—C3_a—C4 | 1.2 (16) | C7B_h—C6—C7B1_f—O3B1_f | −79 (4) |
N1A_d—C1—O2A1_b—C3A1_b | −9 (2) | O2B2_g—C6—C7B1_f—O2B1_f | 126 (8) |
N1_a—C1—O2A1_b—C3A1_b | −1.5 (14) | N2_e—C6—C7B1_f—O2B1_f | 0.3 (12) |
C10i—C1—O2A1_b—C3A1_b | 175.9 (8) | N2B_h—C6—C7B1_f—O2B1_f | −15.2 (15) |
C2A2_c—C1—O2A1_b—C3A1_b | −57 (4) | C5—C6—C7B1_f—O2B1_f | −177.7 (13) |
C2A_d—C1—O2A1_b—C3A1_b | 66 (3) | C7_e—C6—C7B1_f—O2B1_f | 136 (14) |
C2_a—C1—O2A1_b—C3A1_b | 39 (11) | C7B_h—C6—C7B1_f—O2B1_f | 99 (4) |
C1—O2A1_b—C3A1_b—O3A1_b | −172.4 (15) | O3B1_f—C7B1_f—O2B1_f—C9 | 177 (3) |
C1—O2A1_b—C3A1_b—C4 | 0.6 (12) | C6—C7B1_f—O2B1_f—C9 | −1.5 (18) |
C4—O2A2_c—C2A2_c—O3A2_c | 174 (3) | N2_e—C6—O2B2_g—C8B2_g | 2.9 (18) |
C4—O2A2_c—C2A2_c—C1 | −3.2 (18) | N2B_h—C6—O2B2_g—C8B2_g | −13 (2) |
O2A1_b—C1—C2A2_c—O3A2_c | −55 (4) | C5—C6—O2B2_g—C8B2_g | 175.2 (12) |
N1A_d—C1—C2A2_c—O3A2_c | 170 (3) | C7_e—C6—O2B2_g—C8B2_g | −62 (9) |
N1_a—C1—C2A2_c—O3A2_c | 176 (3) | C7B1_f—C6—O2B2_g—C8B2_g | −55 (8) |
C10i—C1—C2A2_c—O3A2_c | 6 (3) | C7B_h—C6—O2B2_g—C8B2_g | 59 (9) |
C2A_d—C1—C2A2_c—O3A2_c | −81 (3) | C6—O2B2_g—C8B2_g—O3B2_g | −176 (3) |
C2_a—C1—C2A2_c—O3A2_c | −77 (4) | C6—O2B2_g—C8B2_g—C9 | 3.8 (19) |
O2A1_b—C1—C2A2_c—O2A2_c | 122 (5) | O2B2_g—C6—N2B_h—O1B_h | −158 (2) |
N1A_d—C1—C2A2_c—O2A2_c | −13 (2) | N2_e—C6—N2B_h—O1B_h | 107 (4) |
N1_a—C1—C2A2_c—O2A2_c | −6.8 (16) | C5—C6—N2B_h—O1B_h | 13 (3) |
C10i—C1—C2A2_c—O2A2_c | −177.2 (11) | C7_e—C6—N2B_h—O1B_h | −153.0 (17) |
C2A_d—C1—C2A2_c—O2A2_c | 96 (3) | C7B1_f—C6—N2B_h—O1B_h | −151 (2) |
C2_a—C1—C2A2_c—O2A2_c | 100 (3) | C7B_h—C6—N2B_h—O1B_h | −166.4 (19) |
O2A1_b—C1—N1A_d—O1A_d | −152 (3) | O2B2_g—C6—N2B_h—C9 | 19 (2) |
N1_a—C1—N1A_d—O1A_d | 104 (8) | N2_e—C6—N2B_h—C9 | −76 (2) |
C10i—C1—N1A_d—O1A_d | 23 (5) | C5—C6—N2B_h—C9 | −170.5 (7) |
C2A2_c—C1—N1A_d—O1A_d | −141 (4) | C7_e—C6—N2B_h—C9 | 23.9 (16) |
C2A_d—C1—N1A_d—O1A_d | −163 (3) | C7B1_f—C6—N2B_h—C9 | 26.2 (18) |
C2_a—C1—N1A_d—O1A_d | −157 (3) | C7B_h—C6—N2B_h—C9 | 10.6 (18) |
O2A1_b—C1—N1A_d—C4 | 14 (4) | O2B2_g—C6—C7B_h—C8B_h | −110 (9) |
N1_a—C1—N1A_d—C4 | −90 (8) | N2_e—C6—C7B_h—C8B_h | 15.7 (11) |
C10i—C1—N1A_d—C4 | −170.9 (13) | N2B_h—C6—C7B_h—C8B_h | −0.3 (13) |
C2A2_c—C1—N1A_d—C4 | 25 (3) | C5—C6—C7B_h—C8B_h | −179.2 (14) |
C2A_d—C1—N1A_d—C4 | 3 (3) | C7_e—C6—C7B_h—C8B_h | −83 (3) |
C2_a—C1—N1A_d—C4 | 9 (3) | C7B1_f—C6—C7B_h—C8B_h | −70 (4) |
O2A1_b—C1—C2A_d—C3A_d | −109 (4) | C6—C7B_h—C8B_h—C9 | −9.6 (18) |
N1A_d—C1—C2A_d—C3A_d | 0 (2) | C7B1_f—O2B1_f—C9—N2_e | 2 (2) |
N1_a—C1—C2A_d—C3A_d | 7.3 (14) | C7B1_f—O2B1_f—C9—N2B_h | 18 (2) |
C10i—C1—C2A_d—C3A_d | 174.1 (7) | C7B1_f—O2B1_f—C9—C10 | 177.0 (8) |
C2A2_c—C1—C2A_d—C3A_d | −76 (2) | C7B1_f—O2B1_f—C9—C8_e | −59 (10) |
C2_a—C1—C2A_d—C3A_d | −86 (6) | C7B1_f—O2B1_f—C9—C8B2_g | −58 (6) |
C1—C2A_d—C3A_d—C4 | −2.7 (10) | C7B1_f—O2B1_f—C9—C8B_h | −71 (5) |
C2A2_c—O2A2_c—C4—N1A_d | 19 (2) | C6—N2_e—C9—O2B1_f | −1.9 (19) |
C2A2_c—O2A2_c—C4—N1_a | 12 (2) | C6—N2_e—C9—N2B_h | −82 (5) |
C2A2_c—O2A2_c—C4—C5 | −179.0 (9) | C6—N2_e—C9—C10 | −176.6 (2) |
C2A2_c—O2A2_c—C4—C3_a | −77 (3) | C6—N2_e—C9—C8_e | 4.4 (5) |
C2A2_c—O2A2_c—C4—C3A_d | −77 (2) | C6—N2_e—C9—C8B2_g | 10.6 (17) |
C2A2_c—O2A2_c—C4—C3A1_b | −58 (4) | C6—N2_e—C9—C8B_h | 10.3 (17) |
O1A_d—N1A_d—C4—O2A2_c | 138 (3) | O1B_h—N2B_h—C9—O2B1_f | 148 (2) |
C1—N1A_d—C4—O2A2_c | −29 (4) | C6—N2B_h—C9—O2B1_f | −29 (2) |
O1A_d—N1A_d—C4—N1_a | −101 (12) | O1B_h—N2B_h—C9—N2_e | −107 (6) |
C1—N1A_d—C4—N1_a | 92 (12) | C6—N2B_h—C9—N2_e | 76 (4) |
O1A_d—N1A_d—C4—C5 | −23 (5) | O1B_h—N2B_h—C9—C10 | −10 (3) |
C1—N1A_d—C4—C5 | 170.3 (13) | C6—N2B_h—C9—C10 | 173.3 (6) |
O1A_d—N1A_d—C4—C3_a | 158 (3) | O1B_h—N2B_h—C9—C8_e | 154.8 (18) |
C1—N1A_d—C4—C3_a | −9 (3) | C6—N2B_h—C9—C8_e | −22.1 (16) |
O1A_d—N1A_d—C4—C3A_d | 162 (3) | O1B_h—N2B_h—C9—C8B2_g | 162 (2) |
C1—N1A_d—C4—C3A_d | −4 (4) | C6—N2B_h—C9—C8B2_g | −15 (2) |
O1A_d—N1A_d—C4—C3A1_b | 154 (3) | O1B_h—N2B_h—C9—C8B_h | 161 (2) |
C1—N1A_d—C4—C3A1_b | −13 (3) | C6—N2B_h—C9—C8B_h | −16 (2) |
C1—N1_a—C4—O2A2_c | −17 (2) | C7_e—C8_e—C9—O2B1_f | 116 (12) |
C1—N1_a—C4—N1A_d | −78 (12) | C7_e—C8_e—C9—N2_e | −4.7 (7) |
C1—N1_a—C4—C5 | 174.8 (6) | C7_e—C8_e—C9—N2B_h | 11.3 (11) |
C1—N1_a—C4—C3_a | 3 (2) | C7_e—C8_e—C9—C10 | 176.3 (3) |
C1—N1_a—C4—C3A_d | 7.4 (17) | C7_e—C8_e—C9—C8B2_g | −62 (9) |
C1—N1_a—C4—C3A1_b | −1.5 (17) | C7_e—C8_e—C9—C8B_h | −89 (7) |
C2_a—C3_a—C4—O2A2_c | 95 (3) | O3B2_g—C8B2_g—C9—O2B1_f | −66 (6) |
C2_a—C3_a—C4—N1A_d | 4 (2) | O2B2_g—C8B2_g—C9—O2B1_f | 115 (7) |
C2_a—C3_a—C4—N1_a | −2.6 (19) | O3B2_g—C8B2_g—C9—N2_e | 171 (3) |
C2_a—C3_a—C4—C5 | −174.8 (8) | O2B2_g—C8B2_g—C9—N2_e | −8.8 (19) |
C2_a—C3_a—C4—C3A_d | −87 (10) | O3B2_g—C8B2_g—C9—N2B_h | −173 (3) |
C2_a—C3_a—C4—C3A1_b | 41 (12) | O2B2_g—C8B2_g—C9—N2B_h | 7 (2) |
C2A_d—C3A_d—C4—O2A2_c | 96 (3) | O3B2_g—C8B2_g—C9—C10 | −2 (4) |
C2A_d—C3A_d—C4—N1A_d | 4 (2) | O2B2_g—C8B2_g—C9—C10 | 178.4 (11) |
C2A_d—C3A_d—C4—N1_a | −2.8 (13) | O3B2_g—C8B2_g—C9—C8_e | −65 (8) |
C2A_d—C3A_d—C4—C5 | −170.6 (6) | O2B2_g—C8B2_g—C9—C8_e | 116 (10) |
C2A_d—C3A_d—C4—C3_a | 94 (10) | O3B2_g—C8B2_g—C9—C8B_h | −13 (42) |
C2A_d—C3A_d—C4—C3A1_b | 64 (5) | O2B2_g—C8B2_g—C9—C8B_h | 167 (44) |
O3A1_b—C3A1_b—C4—O2A2_c | −73 (4) | C7B_h—C8B_h—C9—O2B1_f | 111 (7) |
O2A1_b—C3A1_b—C4—O2A2_c | 115 (5) | C7B_h—C8B_h—C9—N2_e | 0 (2) |
O3A1_b—C3A1_b—C4—N1A_d | 179 (3) | C7B_h—C8B_h—C9—N2B_h | 16 (2) |
O2A1_b—C3A1_b—C4—N1A_d | 7 (2) | C7B_h—C8B_h—C9—C10 | −173.3 (7) |
O3A1_b—C3A1_b—C4—N1_a | 173 (2) | C7B_h—C8B_h—C9—C8_e | 97 (7) |
O2A1_b—C3A1_b—C4—N1_a | 0.6 (15) | C7B_h—C8B_h—C9—C8B2_g | −4 (42) |
O3A1_b—C3A1_b—C4—C5 | −4 (2) | O2B1_f—C9—C10—C1i | 180 (2) |
O2A1_b—C3A1_b—C4—C5 | −175.6 (6) | N2_e—C9—C10—C1i | −6.2 (4) |
O3A1_b—C3A1_b—C4—C3_a | 35 (12) | N2B_h—C9—C10—C1i | −25.7 (12) |
O2A1_b—C3A1_b—C4—C3_a | −137 (14) | C8_e—C9—C10—C1i | 172.6 (6) |
O3A1_b—C3A1_b—C4—C3A_d | 56 (4) | C8B2_g—C9—C10—C1i | 165 (2) |
O2A1_b—C3A1_b—C4—C3A_d | −116 (5) | C8B_h—C9—C10—C1i | 166 (2) |
O2A2_c—C4—C5—C6 | −172.3 (16) | O2B1_f—C9—C10—C17 | −4 (2) |
N1A_d—C4—C5—C6 | −14 (2) | N2_e—C9—C10—C17 | 169.7 (2) |
N1_a—C4—C5—C6 | −5.5 (12) | N2B_h—C9—C10—C17 | 150.2 (12) |
C3_a—C4—C5—C6 | 165.2 (13) | C8_e—C9—C10—C17 | −11.5 (6) |
C3A_d—C4—C5—C6 | 160.1 (8) | C8B2_g—C9—C10—C17 | −19 (2) |
C3A1_b—C4—C5—C6 | 169.8 (10) | C8B_h—C9—C10—C17 | −18 (2) |
O2A2_c—C4—C5—C11 | 10.8 (16) | C6—C5—C11—C16 | −60.3 (3) |
N1A_d—C4—C5—C11 | 169 (2) | C4—C5—C11—C16 | 116.9 (3) |
N1_a—C4—C5—C11 | 177.5 (11) | C6—C5—C11—C12 | 119.1 (2) |
C3_a—C4—C5—C11 | −11.7 (13) | C4—C5—C11—C12 | −63.7 (3) |
C3A_d—C4—C5—C11 | −16.8 (9) | C16—C11—C12—C13 | 0.5 (4) |
C3A1_b—C4—C5—C11 | −7.1 (10) | C5—C11—C12—C13 | −178.9 (2) |
C4—C5—C6—O2B2_g | −171 (2) | C11—C12—C13—C14 | 0.7 (4) |
C11—C5—C6—O2B2_g | 6 (2) | C12—C13—C14—C15 | −0.9 (5) |
C4—C5—C6—N2_e | 0.1 (4) | C13—C14—C15—C16 | −0.1 (5) |
C11—C5—C6—N2_e | 177.0 (2) | C14—C15—C16—C11 | 1.3 (5) |
C4—C5—C6—N2B_h | 19.4 (12) | C12—C11—C16—C15 | −1.5 (4) |
C11—C5—C6—N2B_h | −163.7 (12) | C5—C11—C16—C15 | 177.9 (2) |
C4—C5—C6—C7_e | −178.0 (4) | C1i—C10—C17—C22 | −57.5 (3) |
C11—C5—C6—C7_e | −1.1 (4) | C9—C10—C17—C22 | 126.3 (2) |
C4—C5—C6—C7B1_f | 177.7 (15) | C1i—C10—C17—C18 | 121.9 (2) |
C11—C5—C6—C7B1_f | −5.4 (15) | C9—C10—C17—C18 | −54.4 (3) |
C4—C5—C6—C7B_h | −161.8 (12) | C22—C17—C18—C19 | −0.5 (3) |
C11—C5—C6—C7B_h | 15.1 (12) | C10—C17—C18—C19 | −179.8 (2) |
O2B2_g—C6—N2_e—C9 | −9.0 (17) | C17—C18—C19—C20 | 0.3 (4) |
N2B_h—C6—N2_e—C9 | 82 (3) | C18—C19—C20—C21 | 0.2 (4) |
C5—C6—N2_e—C9 | 179.1 (2) | C19—C20—C21—C22 | −0.6 (4) |
C7_e—C6—N2_e—C9 | −2.5 (4) | C20—C21—C22—C17 | 0.5 (4) |
C7B1_f—C6—N2_e—C9 | 0.9 (12) | C18—C17—C22—C21 | 0.1 (3) |
C7B_h—C6—N2_e—C9 | −15.9 (10) | C10—C17—C22—C21 | 179.4 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |