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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614013953/gz3266sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614013953/gz3266Isup2.hkl
Contains datablock I

CCDC reference: 1008298

Computing details top

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
C43H28N4O3Z = 1
Mr = 648.69F(000) = 338
Triclinic, P1Dx = 1.358 Mg m3
a = 6.3512 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.405 (2) ÅCell parameters from 2036 reflections
c = 12.464 (2) Åθ = 2.4–30.3°
α = 95.548 (3)°µ = 0.09 mm1
β = 99.348 (3)°T = 100 K
γ = 100.200 (3)°Block, black
V = 793.2 (3) Å30.32 × 0.17 × 0.11 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3185 independent reflections
Radiation source: fine-focus sealed tube2371 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan
(APEX2; Bruker, 2009)
h = 77
Tmin = 0.469, Tmax = 0.746k = 1212
6892 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-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 parametersΔρmax = 0.28 e Å3
152 restraintsΔρmin = 0.27 e Å3
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
xyzUiso*/UeqOcc. (<1)
C10.3131 (3)0.4285 (2)0.66082 (19)0.0272 (5)
N1_a0.132 (2)0.5132 (16)0.6439 (7)0.0301 (18)0.3159 (16)
H1A1_a0.09170.52180.58030.036*0.3159 (16)
C2_a0.314 (2)0.4428 (17)0.7792 (9)0.0272 (5)0.3159 (16)
H2_a0.41920.39590.81460.033*0.3159 (16)
C3_a0.137 (3)0.535 (2)0.8287 (9)0.0262 (4)0.3159 (16)
H3_a0.09440.56350.90520.031*0.3159 (16)
N1A1_b0.132 (2)0.5132 (16)0.6439 (7)0.0301 (18)0.2905 (12)
O2A1_b0.3357 (16)0.4401 (12)0.7628 (7)0.0272 (5)0.2905 (12)
O3A1_b0.1305 (10)0.5544 (7)0.9180 (5)0.0424 (16)0.2905 (12)
C3A1_b0.160 (2)0.5349 (17)0.8218 (11)0.0262 (4)0.2905 (12)
N1A2_c0.132 (2)0.5132 (16)0.6439 (7)0.0301 (18)0.0515 (12)
O2A2_c0.156 (4)0.574 (2)0.8167 (17)0.0262 (4)0.0515 (12)
C2A2_c0.336 (3)0.475 (2)0.7706 (17)0.0272 (5)0.0515 (12)
O3A2_c0.468 (5)0.441 (3)0.821 (2)0.0272 (5)0.0515 (12)
N1A_d0.149 (5)0.524 (3)0.6446 (12)0.0301 (18)0.3421 (8)
O1A_d0.1322 (7)0.5743 (4)0.5521 (3)0.0239 (9)0.3421 (8)
C2A_d0.2990 (17)0.4309 (11)0.7796 (9)0.0272 (5)0.3421 (8)
H2A_d0.39300.37500.81510.033*0.3421 (8)
C3A_d0.129 (2)0.5267 (14)0.8297 (8)0.0262 (4)0.3421 (8)
H3A_d0.08470.55300.90640.031*0.3421 (8)
C40.0261 (3)0.5819 (2)0.74314 (18)0.0262 (4)
C50.1760 (3)0.6717 (2)0.76366 (19)0.0254 (5)
C60.3127 (3)0.6980 (2)0.68682 (19)0.0261 (5)
N2_e0.2750 (5)0.6423 (3)0.5795 (3)0.0248 (8)0.6841 (16)
H2A1_e0.16010.58250.54750.030*0.6841 (16)
C7_e0.5221 (9)0.7860 (6)0.7068 (4)0.0281 (9)0.6841 (16)
H7_e0.59100.83890.77400.034*0.6841 (16)
C8_e0.6032 (11)0.7794 (10)0.6122 (5)0.0311 (11)0.6841 (16)
H8_e0.74170.82380.60260.037*0.6841 (16)
N2B1_f0.2750 (5)0.6423 (3)0.5795 (3)0.0248 (8)0.1204 (12)
C7B1_f0.517 (4)0.790 (2)0.6983 (17)0.0281 (9)0.1204 (12)
O2B1_f0.589 (4)0.786 (3)0.5993 (18)0.0311 (11)0.1204 (12)
O3B1_f0.630 (2)0.8609 (12)0.7705 (11)0.0281 (9)0.1204 (12)
N2B2_g0.2750 (5)0.6423 (3)0.5795 (3)0.0248 (8)0.0375 (12)
O2B2_g0.517 (4)0.771 (3)0.7143 (17)0.0281 (9)0.0375 (12)
C8B2_g0.605 (4)0.766 (4)0.6199 (18)0.0311 (11)0.0375 (12)
O3B2_g0.786 (6)0.815 (4)0.619 (4)0.0311 (11)0.0375 (12)
N2B_h0.254 (3)0.673 (2)0.574 (2)0.0248 (8)0.1579 (8)
O1B_h0.0475 (14)0.6399 (9)0.5187 (8)0.0239 (9)0.1579 (8)
C7B_h0.541 (2)0.759 (2)0.7114 (11)0.0281 (9)0.1579 (8)
H7B_h0.62580.78810.78260.034*0.1579 (8)
C8B_h0.613 (3)0.769 (4)0.6156 (14)0.0311 (11)0.1579 (8)
H8B_h0.74970.81570.60640.037*0.1579 (8)
C90.4418 (3)0.6931 (2)0.52916 (18)0.0269 (5)
C100.4587 (3)0.6664 (2)0.41797 (19)0.0257 (5)
C110.2558 (4)0.7396 (2)0.87888 (19)0.0284 (5)
C120.1378 (4)0.8249 (3)0.9251 (2)0.0394 (6)
H120.00590.83870.88400.047*
C130.2131 (5)0.8894 (3)1.0309 (2)0.0501 (8)
H130.13130.94641.06200.060*
C140.4048 (5)0.8716 (3)1.0910 (2)0.0535 (8)
H140.45630.91711.16290.064*
C150.5222 (5)0.7875 (3)1.0464 (2)0.0540 (8)
H150.65490.77531.08780.065*
C160.4476 (4)0.7206 (3)0.9414 (2)0.0419 (7)
H160.52810.66150.91210.050*
C170.6396 (3)0.7525 (2)0.37954 (18)0.0235 (5)
C180.6600 (4)0.8896 (2)0.39499 (19)0.0290 (5)
H180.55910.92740.43000.035*
C190.8262 (4)0.9711 (2)0.3597 (2)0.0335 (6)
H190.83901.06400.37100.040*
C200.9736 (4)0.9164 (2)0.3079 (2)0.0325 (6)
H201.08750.97190.28390.039*
C210.9545 (4)0.7808 (2)0.2912 (2)0.0333 (6)
H211.05460.74350.25520.040*
C220.7888 (4)0.6994 (2)0.3272 (2)0.0296 (5)
H220.77720.60660.31600.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0187 (10)0.0220 (9)0.0384 (11)0.0010 (7)0.0035 (8)0.0002 (8)
N1_a0.022 (2)0.029 (3)0.0343 (11)0.002 (2)0.0022 (10)0.0058 (10)
C2_a0.0187 (10)0.0220 (9)0.0384 (11)0.0010 (7)0.0035 (8)0.0002 (8)
C3_a0.0205 (10)0.0227 (9)0.0333 (10)0.0042 (7)0.0010 (7)0.0000 (7)
N1A1_b0.022 (2)0.029 (3)0.0343 (11)0.002 (2)0.0022 (10)0.0058 (10)
O2A1_b0.0187 (10)0.0220 (9)0.0384 (11)0.0010 (7)0.0035 (8)0.0002 (8)
O3A1_b0.035 (3)0.052 (4)0.030 (3)0.012 (3)0.005 (3)0.007 (3)
C3A1_b0.0205 (10)0.0227 (9)0.0333 (10)0.0042 (7)0.0010 (7)0.0000 (7)
N1A2_c0.022 (2)0.029 (3)0.0343 (11)0.002 (2)0.0022 (10)0.0058 (10)
O2A2_c0.0205 (10)0.0227 (9)0.0333 (10)0.0042 (7)0.0010 (7)0.0000 (7)
C2A2_c0.0187 (10)0.0220 (9)0.0384 (11)0.0010 (7)0.0035 (8)0.0002 (8)
O3A2_c0.0187 (10)0.0220 (9)0.0384 (11)0.0010 (7)0.0035 (8)0.0002 (8)
N1A_d0.022 (2)0.029 (3)0.0343 (11)0.002 (2)0.0022 (10)0.0058 (10)
O1A_d0.022 (2)0.021 (2)0.026 (2)0.0011 (15)0.0004 (16)0.0029 (16)
C2A_d0.0187 (10)0.0220 (9)0.0384 (11)0.0010 (7)0.0035 (8)0.0002 (8)
C3A_d0.0205 (10)0.0227 (9)0.0333 (10)0.0042 (7)0.0010 (7)0.0000 (7)
C40.0205 (10)0.0227 (9)0.0333 (10)0.0042 (7)0.0010 (7)0.0000 (7)
C50.0227 (11)0.0199 (11)0.0318 (12)0.0035 (8)0.0000 (9)0.0033 (9)
C60.0198 (11)0.0199 (11)0.0352 (13)0.0013 (8)0.0010 (9)0.0019 (9)
N2_e0.0191 (11)0.021 (2)0.0311 (12)0.0013 (10)0.0014 (10)0.0032 (13)
C7_e0.0206 (13)0.023 (2)0.0361 (15)0.0006 (11)0.0011 (10)0.0024 (12)
C8_e0.0191 (14)0.0258 (19)0.0453 (19)0.0026 (13)0.0074 (13)0.0010 (15)
N2B1_f0.0191 (11)0.021 (2)0.0311 (12)0.0013 (10)0.0014 (10)0.0032 (13)
C7B1_f0.0206 (13)0.023 (2)0.0361 (15)0.0006 (11)0.0011 (10)0.0024 (12)
O2B1_f0.0191 (14)0.0258 (19)0.0453 (19)0.0026 (13)0.0074 (13)0.0010 (15)
O3B1_f0.0206 (13)0.023 (2)0.0361 (15)0.0006 (11)0.0011 (10)0.0024 (12)
N2B2_g0.0191 (11)0.021 (2)0.0311 (12)0.0013 (10)0.0014 (10)0.0032 (13)
O2B2_g0.0206 (13)0.023 (2)0.0361 (15)0.0006 (11)0.0011 (10)0.0024 (12)
C8B2_g0.0191 (14)0.0258 (19)0.0453 (19)0.0026 (13)0.0074 (13)0.0010 (15)
O3B2_g0.0191 (14)0.0258 (19)0.0453 (19)0.0026 (13)0.0074 (13)0.0010 (15)
N2B_h0.0191 (11)0.021 (2)0.0311 (12)0.0013 (10)0.0014 (10)0.0032 (13)
O1B_h0.022 (2)0.021 (2)0.026 (2)0.0011 (15)0.0004 (16)0.0029 (16)
C7B_h0.0206 (13)0.023 (2)0.0361 (15)0.0006 (11)0.0011 (10)0.0024 (12)
C8B_h0.0191 (14)0.0258 (19)0.0453 (19)0.0026 (13)0.0074 (13)0.0010 (15)
C90.0207 (11)0.0228 (11)0.0347 (13)0.0015 (9)0.0032 (9)0.0008 (9)
C100.0182 (11)0.0238 (11)0.0332 (13)0.0019 (8)0.0027 (9)0.0013 (9)
C110.0252 (12)0.0240 (12)0.0304 (12)0.0060 (9)0.0001 (9)0.0040 (9)
C120.0404 (15)0.0329 (14)0.0399 (15)0.0054 (11)0.0009 (12)0.0022 (11)
C130.067 (2)0.0376 (16)0.0386 (16)0.0069 (14)0.0004 (14)0.0074 (12)
C140.065 (2)0.0484 (18)0.0303 (15)0.0127 (15)0.0096 (13)0.0040 (13)
C150.0420 (17)0.068 (2)0.0434 (17)0.0029 (15)0.0105 (13)0.0093 (15)
C160.0351 (14)0.0480 (16)0.0376 (15)0.0052 (12)0.0050 (11)0.0056 (12)
C170.0158 (10)0.0247 (11)0.0264 (11)0.0003 (8)0.0004 (8)0.0003 (9)
C180.0243 (12)0.0250 (12)0.0356 (13)0.0033 (9)0.0036 (10)0.0000 (10)
C190.0297 (13)0.0212 (12)0.0446 (15)0.0025 (9)0.0016 (11)0.0027 (10)
C200.0220 (12)0.0325 (13)0.0387 (14)0.0046 (9)0.0030 (10)0.0066 (11)
C210.0220 (12)0.0348 (14)0.0430 (15)0.0031 (10)0.0093 (10)0.0037 (11)
C220.0252 (12)0.0218 (11)0.0401 (14)0.0028 (9)0.0048 (10)0.0001 (10)
Geometric parameters (Å, º) top
C1—O2A1_b1.299 (10)C8_e—H8_e0.9500
C1—N1A_d1.36 (2)C7B1_f—O3B1_f1.16 (2)
C1—N1_a1.377 (11)C7B1_f—O2B1_f1.384 (17)
C1—C10i1.410 (3)O2B1_f—C91.349 (18)
C1—C2A2_c1.448 (19)O2B2_g—C8B2_g1.383 (18)
C1—C2A_d1.466 (11)C8B2_g—O3B2_g1.18 (4)
C1—C2_a1.470 (12)C8B2_g—C91.45 (2)
N1_a—C41.372 (7)N2B_h—O1B_h1.35 (2)
N1_a—H1A1_a0.8800N2B_h—C91.386 (14)
C2_a—C3_a1.357 (12)C7B_h—C8B_h1.352 (14)
C2_a—H2_a0.9500C7B_h—H7B_h0.9500
C3_a—C41.448 (12)C8B_h—C91.452 (15)
C3_a—H3_a0.9500C8B_h—H8B_h0.9500
O2A1_b—C3A1_b1.400 (12)C9—C101.412 (3)
O3A1_b—C3A1_b1.176 (14)C10—C1i1.410 (3)
C3A1_b—C41.463 (14)C10—C171.500 (3)
O2A2_c—C41.330 (18)C11—C161.392 (3)
O2A2_c—C2A2_c1.395 (17)C11—C121.399 (4)
C2A2_c—O3A2_c1.15 (4)C12—C131.389 (4)
N1A_d—O1A_d1.32 (2)C12—H120.9500
N1A_d—C41.364 (11)C13—C141.374 (4)
C2A_d—C3A_d1.353 (11)C13—H130.9500
C2A_d—H2A_d0.9500C14—C151.379 (5)
C3A_d—C41.462 (11)C14—H140.9500
C3A_d—H3A_d0.9500C15—C161.387 (4)
C4—C51.417 (3)C15—H150.9500
C5—C61.408 (3)C16—H160.9500
C5—C111.503 (3)C17—C221.395 (3)
C6—O2B2_g1.35 (2)C17—C181.401 (3)
C6—N2_e1.371 (5)C18—C191.390 (3)
C6—N2B_h1.38 (3)C18—H180.9500
C6—C7_e1.444 (6)C19—C201.389 (4)
C6—C7B1_f1.45 (2)C19—H190.9500
C6—C7B_h1.447 (14)C20—C211.387 (3)
N2_e—C91.370 (4)C20—H200.9500
N2_e—H2A1_e0.8800C21—C221.392 (3)
C7_e—C8_e1.362 (6)C21—H210.9500
C7_e—H7_e0.9500C22—H220.9500
C8_e—C91.441 (6)
O2A1_b—C1—C10i120.9 (4)O3B1_f—C7B1_f—C6134.5 (18)
N1A_d—C1—C10i128.3 (7)O2B1_f—C7B1_f—C6109.7 (15)
N1_a—C1—C10i126.9 (4)C9—O2B1_f—C7B1_f106.2 (14)
C10i—C1—C2A2_c128.7 (8)C6—O2B2_g—C8B2_g106.2 (15)
N1A_d—C1—C2A_d107.2 (7)O3B2_g—C8B2_g—O2B2_g122 (3)
C10i—C1—C2A_d124.2 (4)O3B2_g—C8B2_g—C9128 (3)
N1_a—C1—C2_a107.6 (6)O2B2_g—C8B2_g—C9109.6 (15)
C10i—C1—C2_a125.1 (5)O1B_h—N2B_h—C6124.5 (12)
C4—N1_a—C1108.4 (8)O1B_h—N2B_h—C9126.8 (19)
C4—N1_a—H1A1_a125.8C6—N2B_h—C9108.6 (14)
C1—N1_a—H1A1_a125.8C8B_h—C7B_h—C6108.1 (10)
C3_a—C2_a—C1107.6 (8)C8B_h—C7B_h—H7B_h125.9
C3_a—C2_a—H2_a126.2C6—C7B_h—H7B_h125.9
C1—C2_a—H2_a126.2C7B_h—C8B_h—C9107.4 (10)
C2_a—C3_a—C4107.1 (8)C7B_h—C8B_h—H8B_h126.3
C2_a—C3_a—H3_a126.4C9—C8B_h—H8B_h126.3
C4—C3_a—H3_a126.4O2B1_f—C9—C10121.8 (8)
C1—O2A1_b—C3A1_b107.7 (9)N2_e—C9—C10127.6 (3)
O3A1_b—C3A1_b—O2A1_b121.1 (11)N2B_h—C9—C10127.3 (11)
O3A1_b—C3A1_b—C4131.4 (10)N2_e—C9—C8_e106.9 (3)
O2A1_b—C3A1_b—C4107.1 (10)C10—C9—C8_e125.4 (3)
C4—O2A2_c—C2A2_c106.2 (14)C10—C9—C8B2_g128.9 (9)
O3A2_c—C2A2_c—O2A2_c121 (2)N2B_h—C9—C8B_h106.3 (13)
O3A2_c—C2A2_c—C1131 (2)C10—C9—C8B_h125.7 (6)
O2A2_c—C2A2_c—C1108.6 (15)C1i—C10—C9125.6 (2)
O1A_d—N1A_d—C1126.3 (12)C1i—C10—C17117.6 (2)
O1A_d—N1A_d—C4122.4 (15)C9—C10—C17116.69 (19)
C1—N1A_d—C4109.8 (13)C16—C11—C12118.6 (2)
C3A_d—C2A_d—C1108.0 (8)C16—C11—C5121.4 (2)
C3A_d—C2A_d—H2A_d126.0C12—C11—C5120.1 (2)
C1—C2A_d—H2A_d126.0C13—C12—C11120.1 (3)
C2A_d—C3A_d—C4106.8 (8)C13—C12—H12119.9
C2A_d—C3A_d—H3A_d126.6C11—C12—H12119.9
C4—C3A_d—H3A_d126.6C14—C13—C12120.6 (3)
O2A2_c—C4—C5121.6 (8)C14—C13—H13119.7
N1A_d—C4—C5128.3 (10)C12—C13—H13119.7
N1_a—C4—C5126.6 (6)C13—C14—C15119.7 (3)
N1_a—C4—C3_a109.1 (7)C13—C14—H14120.2
C5—C4—C3_a123.7 (5)C15—C14—H14120.2
N1A_d—C4—C3A_d108.0 (11)C14—C15—C16120.4 (3)
C5—C4—C3A_d123.4 (5)C14—C15—H15119.8
C5—C4—C3A1_b128.6 (5)C16—C15—H15119.8
C6—C5—C4125.6 (2)C15—C16—C11120.5 (3)
C6—C5—C11117.33 (19)C15—C16—H16119.8
C4—C5—C11117.0 (2)C11—C16—H16119.8
O2B2_g—C6—C5123.1 (9)C22—C17—C18118.5 (2)
N2_e—C6—C5126.5 (2)C22—C17—C10121.5 (2)
N2B_h—C6—C5126.8 (6)C18—C17—C10119.9 (2)
N2_e—C6—C7_e106.9 (3)C19—C18—C17120.8 (2)
C5—C6—C7_e126.6 (3)C19—C18—H18119.6
C5—C6—C7B1_f129.9 (8)C17—C18—H18119.6
N2B_h—C6—C7B_h106.9 (8)C20—C19—C18119.8 (2)
C5—C6—C7B_h126.2 (6)C20—C19—H19120.1
C9—N2_e—C6110.2 (3)C18—C19—H19120.1
C9—N2_e—H2A1_e124.9C21—C20—C19120.1 (2)
C6—N2_e—H2A1_e124.9C21—C20—H20120.0
C8_e—C7_e—C6107.8 (4)C19—C20—H20120.0
C8_e—C7_e—H7_e126.1C20—C21—C22120.0 (2)
C6—C7_e—H7_e126.1C20—C21—H21120.0
C7_e—C8_e—C9107.9 (4)C22—C21—H21120.0
C7_e—C8_e—H8_e126.0C21—C22—C17120.8 (2)
C9—C8_e—H8_e126.0C21—C22—H22119.6
O3B1_f—C7B1_f—O2B1_f115.7 (18)C17—C22—H22119.6
O2A1_b—C1—N1_a—C42.0 (18)O2B2_g—C6—C7_e—C8_e116 (10)
N1A_d—C1—N1_a—C480 (7)N2_e—C6—C7_e—C8_e0.5 (5)
C10i—C1—N1_a—C4175.3 (6)N2B_h—C6—C7_e—C8_e16.5 (10)
C2A2_c—C1—N1_a—C414.0 (18)C5—C6—C7_e—C8_e177.9 (5)
C2A_d—C1—N1_a—C49.0 (17)C7B1_f—C6—C7_e—C8_e45 (14)
C2_a—C1—N1_a—C42.1 (18)C7B_h—C6—C7_e—C8_e84 (3)
O2A1_b—C1—C2_a—C3_a140 (12)C6—C7_e—C8_e—C93.2 (7)
N1A_d—C1—C2_a—C3_a7 (2)O2B2_g—C6—C7B1_f—O3B1_f52 (8)
N1_a—C1—C2_a—C3_a0.5 (15)N2_e—C6—C7B1_f—O3B1_f177 (3)
C10i—C1—C2_a—C3_a173.8 (10)N2B_h—C6—C7B1_f—O3B1_f167 (3)
C2A2_c—C1—C2_a—C3_a77 (3)C5—C6—C7B1_f—O3B1_f5 (4)
C2A_d—C1—C2_a—C3_a90 (6)C7_e—C6—C7B1_f—O3B1_f41 (12)
C1—C2_a—C3_a—C41.2 (16)C7B_h—C6—C7B1_f—O3B1_f79 (4)
N1A_d—C1—O2A1_b—C3A1_b9 (2)O2B2_g—C6—C7B1_f—O2B1_f126 (8)
N1_a—C1—O2A1_b—C3A1_b1.5 (14)N2_e—C6—C7B1_f—O2B1_f0.3 (12)
C10i—C1—O2A1_b—C3A1_b175.9 (8)N2B_h—C6—C7B1_f—O2B1_f15.2 (15)
C2A2_c—C1—O2A1_b—C3A1_b57 (4)C5—C6—C7B1_f—O2B1_f177.7 (13)
C2A_d—C1—O2A1_b—C3A1_b66 (3)C7_e—C6—C7B1_f—O2B1_f136 (14)
C2_a—C1—O2A1_b—C3A1_b39 (11)C7B_h—C6—C7B1_f—O2B1_f99 (4)
C1—O2A1_b—C3A1_b—O3A1_b172.4 (15)O3B1_f—C7B1_f—O2B1_f—C9177 (3)
C1—O2A1_b—C3A1_b—C40.6 (12)C6—C7B1_f—O2B1_f—C91.5 (18)
C4—O2A2_c—C2A2_c—O3A2_c174 (3)N2_e—C6—O2B2_g—C8B2_g2.9 (18)
C4—O2A2_c—C2A2_c—C13.2 (18)N2B_h—C6—O2B2_g—C8B2_g13 (2)
O2A1_b—C1—C2A2_c—O3A2_c55 (4)C5—C6—O2B2_g—C8B2_g175.2 (12)
N1A_d—C1—C2A2_c—O3A2_c170 (3)C7_e—C6—O2B2_g—C8B2_g62 (9)
N1_a—C1—C2A2_c—O3A2_c176 (3)C7B1_f—C6—O2B2_g—C8B2_g55 (8)
C10i—C1—C2A2_c—O3A2_c6 (3)C7B_h—C6—O2B2_g—C8B2_g59 (9)
C2A_d—C1—C2A2_c—O3A2_c81 (3)C6—O2B2_g—C8B2_g—O3B2_g176 (3)
C2_a—C1—C2A2_c—O3A2_c77 (4)C6—O2B2_g—C8B2_g—C93.8 (19)
O2A1_b—C1—C2A2_c—O2A2_c122 (5)O2B2_g—C6—N2B_h—O1B_h158 (2)
N1A_d—C1—C2A2_c—O2A2_c13 (2)N2_e—C6—N2B_h—O1B_h107 (4)
N1_a—C1—C2A2_c—O2A2_c6.8 (16)C5—C6—N2B_h—O1B_h13 (3)
C10i—C1—C2A2_c—O2A2_c177.2 (11)C7_e—C6—N2B_h—O1B_h153.0 (17)
C2A_d—C1—C2A2_c—O2A2_c96 (3)C7B1_f—C6—N2B_h—O1B_h151 (2)
C2_a—C1—C2A2_c—O2A2_c100 (3)C7B_h—C6—N2B_h—O1B_h166.4 (19)
O2A1_b—C1—N1A_d—O1A_d152 (3)O2B2_g—C6—N2B_h—C919 (2)
N1_a—C1—N1A_d—O1A_d104 (8)N2_e—C6—N2B_h—C976 (2)
C10i—C1—N1A_d—O1A_d23 (5)C5—C6—N2B_h—C9170.5 (7)
C2A2_c—C1—N1A_d—O1A_d141 (4)C7_e—C6—N2B_h—C923.9 (16)
C2A_d—C1—N1A_d—O1A_d163 (3)C7B1_f—C6—N2B_h—C926.2 (18)
C2_a—C1—N1A_d—O1A_d157 (3)C7B_h—C6—N2B_h—C910.6 (18)
O2A1_b—C1—N1A_d—C414 (4)O2B2_g—C6—C7B_h—C8B_h110 (9)
N1_a—C1—N1A_d—C490 (8)N2_e—C6—C7B_h—C8B_h15.7 (11)
C10i—C1—N1A_d—C4170.9 (13)N2B_h—C6—C7B_h—C8B_h0.3 (13)
C2A2_c—C1—N1A_d—C425 (3)C5—C6—C7B_h—C8B_h179.2 (14)
C2A_d—C1—N1A_d—C43 (3)C7_e—C6—C7B_h—C8B_h83 (3)
C2_a—C1—N1A_d—C49 (3)C7B1_f—C6—C7B_h—C8B_h70 (4)
O2A1_b—C1—C2A_d—C3A_d109 (4)C6—C7B_h—C8B_h—C99.6 (18)
N1A_d—C1—C2A_d—C3A_d0 (2)C7B1_f—O2B1_f—C9—N2_e2 (2)
N1_a—C1—C2A_d—C3A_d7.3 (14)C7B1_f—O2B1_f—C9—N2B_h18 (2)
C10i—C1—C2A_d—C3A_d174.1 (7)C7B1_f—O2B1_f—C9—C10177.0 (8)
C2A2_c—C1—C2A_d—C3A_d76 (2)C7B1_f—O2B1_f—C9—C8_e59 (10)
C2_a—C1—C2A_d—C3A_d86 (6)C7B1_f—O2B1_f—C9—C8B2_g58 (6)
C1—C2A_d—C3A_d—C42.7 (10)C7B1_f—O2B1_f—C9—C8B_h71 (5)
C2A2_c—O2A2_c—C4—N1A_d19 (2)C6—N2_e—C9—O2B1_f1.9 (19)
C2A2_c—O2A2_c—C4—N1_a12 (2)C6—N2_e—C9—N2B_h82 (5)
C2A2_c—O2A2_c—C4—C5179.0 (9)C6—N2_e—C9—C10176.6 (2)
C2A2_c—O2A2_c—C4—C3_a77 (3)C6—N2_e—C9—C8_e4.4 (5)
C2A2_c—O2A2_c—C4—C3A_d77 (2)C6—N2_e—C9—C8B2_g10.6 (17)
C2A2_c—O2A2_c—C4—C3A1_b58 (4)C6—N2_e—C9—C8B_h10.3 (17)
O1A_d—N1A_d—C4—O2A2_c138 (3)O1B_h—N2B_h—C9—O2B1_f148 (2)
C1—N1A_d—C4—O2A2_c29 (4)C6—N2B_h—C9—O2B1_f29 (2)
O1A_d—N1A_d—C4—N1_a101 (12)O1B_h—N2B_h—C9—N2_e107 (6)
C1—N1A_d—C4—N1_a92 (12)C6—N2B_h—C9—N2_e76 (4)
O1A_d—N1A_d—C4—C523 (5)O1B_h—N2B_h—C9—C1010 (3)
C1—N1A_d—C4—C5170.3 (13)C6—N2B_h—C9—C10173.3 (6)
O1A_d—N1A_d—C4—C3_a158 (3)O1B_h—N2B_h—C9—C8_e154.8 (18)
C1—N1A_d—C4—C3_a9 (3)C6—N2B_h—C9—C8_e22.1 (16)
O1A_d—N1A_d—C4—C3A_d162 (3)O1B_h—N2B_h—C9—C8B2_g162 (2)
C1—N1A_d—C4—C3A_d4 (4)C6—N2B_h—C9—C8B2_g15 (2)
O1A_d—N1A_d—C4—C3A1_b154 (3)O1B_h—N2B_h—C9—C8B_h161 (2)
C1—N1A_d—C4—C3A1_b13 (3)C6—N2B_h—C9—C8B_h16 (2)
C1—N1_a—C4—O2A2_c17 (2)C7_e—C8_e—C9—O2B1_f116 (12)
C1—N1_a—C4—N1A_d78 (12)C7_e—C8_e—C9—N2_e4.7 (7)
C1—N1_a—C4—C5174.8 (6)C7_e—C8_e—C9—N2B_h11.3 (11)
C1—N1_a—C4—C3_a3 (2)C7_e—C8_e—C9—C10176.3 (3)
C1—N1_a—C4—C3A_d7.4 (17)C7_e—C8_e—C9—C8B2_g62 (9)
C1—N1_a—C4—C3A1_b1.5 (17)C7_e—C8_e—C9—C8B_h89 (7)
C2_a—C3_a—C4—O2A2_c95 (3)O3B2_g—C8B2_g—C9—O2B1_f66 (6)
C2_a—C3_a—C4—N1A_d4 (2)O2B2_g—C8B2_g—C9—O2B1_f115 (7)
C2_a—C3_a—C4—N1_a2.6 (19)O3B2_g—C8B2_g—C9—N2_e171 (3)
C2_a—C3_a—C4—C5174.8 (8)O2B2_g—C8B2_g—C9—N2_e8.8 (19)
C2_a—C3_a—C4—C3A_d87 (10)O3B2_g—C8B2_g—C9—N2B_h173 (3)
C2_a—C3_a—C4—C3A1_b41 (12)O2B2_g—C8B2_g—C9—N2B_h7 (2)
C2A_d—C3A_d—C4—O2A2_c96 (3)O3B2_g—C8B2_g—C9—C102 (4)
C2A_d—C3A_d—C4—N1A_d4 (2)O2B2_g—C8B2_g—C9—C10178.4 (11)
C2A_d—C3A_d—C4—N1_a2.8 (13)O3B2_g—C8B2_g—C9—C8_e65 (8)
C2A_d—C3A_d—C4—C5170.6 (6)O2B2_g—C8B2_g—C9—C8_e116 (10)
C2A_d—C3A_d—C4—C3_a94 (10)O3B2_g—C8B2_g—C9—C8B_h13 (42)
C2A_d—C3A_d—C4—C3A1_b64 (5)O2B2_g—C8B2_g—C9—C8B_h167 (44)
O3A1_b—C3A1_b—C4—O2A2_c73 (4)C7B_h—C8B_h—C9—O2B1_f111 (7)
O2A1_b—C3A1_b—C4—O2A2_c115 (5)C7B_h—C8B_h—C9—N2_e0 (2)
O3A1_b—C3A1_b—C4—N1A_d179 (3)C7B_h—C8B_h—C9—N2B_h16 (2)
O2A1_b—C3A1_b—C4—N1A_d7 (2)C7B_h—C8B_h—C9—C10173.3 (7)
O3A1_b—C3A1_b—C4—N1_a173 (2)C7B_h—C8B_h—C9—C8_e97 (7)
O2A1_b—C3A1_b—C4—N1_a0.6 (15)C7B_h—C8B_h—C9—C8B2_g4 (42)
O3A1_b—C3A1_b—C4—C54 (2)O2B1_f—C9—C10—C1i180 (2)
O2A1_b—C3A1_b—C4—C5175.6 (6)N2_e—C9—C10—C1i6.2 (4)
O3A1_b—C3A1_b—C4—C3_a35 (12)N2B_h—C9—C10—C1i25.7 (12)
O2A1_b—C3A1_b—C4—C3_a137 (14)C8_e—C9—C10—C1i172.6 (6)
O3A1_b—C3A1_b—C4—C3A_d56 (4)C8B2_g—C9—C10—C1i165 (2)
O2A1_b—C3A1_b—C4—C3A_d116 (5)C8B_h—C9—C10—C1i166 (2)
O2A2_c—C4—C5—C6172.3 (16)O2B1_f—C9—C10—C174 (2)
N1A_d—C4—C5—C614 (2)N2_e—C9—C10—C17169.7 (2)
N1_a—C4—C5—C65.5 (12)N2B_h—C9—C10—C17150.2 (12)
C3_a—C4—C5—C6165.2 (13)C8_e—C9—C10—C1711.5 (6)
C3A_d—C4—C5—C6160.1 (8)C8B2_g—C9—C10—C1719 (2)
C3A1_b—C4—C5—C6169.8 (10)C8B_h—C9—C10—C1718 (2)
O2A2_c—C4—C5—C1110.8 (16)C6—C5—C11—C1660.3 (3)
N1A_d—C4—C5—C11169 (2)C4—C5—C11—C16116.9 (3)
N1_a—C4—C5—C11177.5 (11)C6—C5—C11—C12119.1 (2)
C3_a—C4—C5—C1111.7 (13)C4—C5—C11—C1263.7 (3)
C3A_d—C4—C5—C1116.8 (9)C16—C11—C12—C130.5 (4)
C3A1_b—C4—C5—C117.1 (10)C5—C11—C12—C13178.9 (2)
C4—C5—C6—O2B2_g171 (2)C11—C12—C13—C140.7 (4)
C11—C5—C6—O2B2_g6 (2)C12—C13—C14—C150.9 (5)
C4—C5—C6—N2_e0.1 (4)C13—C14—C15—C160.1 (5)
C11—C5—C6—N2_e177.0 (2)C14—C15—C16—C111.3 (5)
C4—C5—C6—N2B_h19.4 (12)C12—C11—C16—C151.5 (4)
C11—C5—C6—N2B_h163.7 (12)C5—C11—C16—C15177.9 (2)
C4—C5—C6—C7_e178.0 (4)C1i—C10—C17—C2257.5 (3)
C11—C5—C6—C7_e1.1 (4)C9—C10—C17—C22126.3 (2)
C4—C5—C6—C7B1_f177.7 (15)C1i—C10—C17—C18121.9 (2)
C11—C5—C6—C7B1_f5.4 (15)C9—C10—C17—C1854.4 (3)
C4—C5—C6—C7B_h161.8 (12)C22—C17—C18—C190.5 (3)
C11—C5—C6—C7B_h15.1 (12)C10—C17—C18—C19179.8 (2)
O2B2_g—C6—N2_e—C99.0 (17)C17—C18—C19—C200.3 (4)
N2B_h—C6—N2_e—C982 (3)C18—C19—C20—C210.2 (4)
C5—C6—N2_e—C9179.1 (2)C19—C20—C21—C220.6 (4)
C7_e—C6—N2_e—C92.5 (4)C20—C21—C22—C170.5 (4)
C7B1_f—C6—N2_e—C90.9 (12)C18—C17—C22—C210.1 (3)
C7B_h—C6—N2_e—C915.9 (10)C10—C17—C22—C21179.4 (2)
Symmetry code: (i) x, y+1, z+1.
 

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