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IUCrData (2021). 6, x210428
https://doi.org/10.1107/S2414314621004284
Open access
D. Yan
In the title compound, C30H19IN2, two independent molecules (A and B) are present in the asymmetric unit, with different conformations. The dihedral angle between the mean planes of the carbazole systems for molecule A is 49.1 (2)° compared to 84.0 (1)° for molecule B. In the crystal, numerous aromatic π–π stacking interactions [shortest centroid–centroid separation = 3.7069 (19) Å] help to establish the three-dimensional supramolecular network.
Keywords: crystal structure; carbazole derivative; π–π stacking; supramolecular network.
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Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314621004284/hb4376sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2414314621004284/hb4376Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314621004284/hb4376Isup3.cml |
CCDC reference: 2079137
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.039
- wR factor = 0.088
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors foundAlert level CPLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.707 CheckPLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.596 18 Report
Alert level GPLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do !PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 5.83 Why ?PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL/ 2018 NotePLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still 59% NotePLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 3 NotePLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 NotePLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 Info 0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 7 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Computing details top
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
Crystal data
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C30H19IN2 | F(000) = 2128 |
Mr = 534.37 | Dx = 1.543 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5057 (4) Å | Cell parameters from 296(2) reflections |
b = 29.3757 (17) Å | θ = 2.3–25.0° |
c = 16.5679 (8) Å | µ = 1.41 mm−1 |
β = 96.127 (2)° | T = 296 K |
V = 4599.9 (4) Å3 | Block, colourless |
Z = 8 | 0.25 × 0.23 × 0.23 mm |
Data collection
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Bruker SMART APEX CCD diffractometer | 8124 independent reflections |
Radiation source: fine-focus sealed tube | 6636 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scan | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −11→11 |
Tmin = 0.719, Tmax = 0.737 | k = −34→34 |
27536 measured reflections | l = −19→19 |
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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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0331P)2 + 5.8326P] where P = (Fo2 + 2Fc2)/3 |
8124 reflections | (Δ/σ)max = 0.003 |
595 parameters | Δρmax = 0.78 e Å−3 |
0 restraints | Δρmin = −0.98 e Å−3 |
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Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
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x | y | z | Uiso*/Ueq | ||
C1 | 0.3030 (4) | 0.30347 (11) | 0.9652 (2) | 0.0357 (8) | |
C2 | 0.2194 (4) | 0.30625 (12) | 0.8916 (2) | 0.0377 (8) | |
H2 | 0.1401 | 0.2878 | 0.8809 | 0.045* | |
C3 | 0.2562 (4) | 0.33710 (12) | 0.83435 (19) | 0.0354 (8) | |
C4 | 0.3751 (4) | 0.36416 (12) | 0.8498 (2) | 0.0364 (8) | |
H4 | 0.4006 | 0.3842 | 0.8104 | 0.044* | |
C5 | 0.4564 (3) | 0.36128 (11) | 0.9248 (2) | 0.0332 (8) | |
C6 | 0.4186 (3) | 0.33118 (11) | 0.9835 (2) | 0.0355 (8) | |
H6 | 0.4706 | 0.3298 | 1.0343 | 0.043* | |
C7 | 0.2157 (4) | 0.32577 (11) | 0.6837 (2) | 0.0353 (8) | |
C8 | 0.3480 (4) | 0.31137 (13) | 0.6656 (2) | 0.0477 (9) | |
H8 | 0.4250 | 0.3100 | 0.7051 | 0.057* | |
C9 | 0.3598 (5) | 0.29915 (14) | 0.5863 (3) | 0.0535 (10) | |
H9 | 0.4471 | 0.2894 | 0.5724 | 0.064* | |
C10 | 0.2464 (4) | 0.30083 (14) | 0.5265 (2) | 0.0517 (10) | |
H10 | 0.2590 | 0.2924 | 0.4737 | 0.062* | |
C11 | 0.1152 (4) | 0.31491 (12) | 0.5448 (2) | 0.0438 (9) | |
H11 | 0.0388 | 0.3157 | 0.5047 | 0.053* | |
C12 | 0.0987 (4) | 0.32798 (11) | 0.62428 (19) | 0.0337 (8) | |
C13 | −0.0203 (4) | 0.34428 (10) | 0.66338 (19) | 0.0308 (7) | |
C14 | −0.1601 (4) | 0.35443 (11) | 0.6368 (2) | 0.0369 (8) | |
H14 | −0.1938 | 0.3509 | 0.5823 | 0.044* | |
C15 | −0.2492 (4) | 0.36993 (12) | 0.6918 (2) | 0.0413 (9) | |
H15 | −0.3433 | 0.3765 | 0.6744 | 0.050* | |
C16 | −0.1982 (4) | 0.37567 (12) | 0.7729 (2) | 0.0439 (9) | |
H16 | −0.2594 | 0.3860 | 0.8091 | 0.053* | |
C17 | −0.0594 (4) | 0.36652 (12) | 0.8015 (2) | 0.0417 (9) | |
H17 | −0.0262 | 0.3709 | 0.8558 | 0.050* | |
C18 | 0.0293 (4) | 0.35050 (11) | 0.74595 (19) | 0.0329 (7) | |
C19 | 0.5865 (3) | 0.43534 (11) | 0.92762 (19) | 0.0328 (7) | |
C20 | 0.4833 (4) | 0.46598 (13) | 0.8984 (2) | 0.0441 (9) | |
H20 | 0.3915 | 0.4561 | 0.8825 | 0.053* | |
C21 | 0.5176 (4) | 0.51059 (14) | 0.8933 (2) | 0.0512 (10) | |
H21 | 0.4480 | 0.5315 | 0.8748 | 0.061* | |
C22 | 0.6547 (4) | 0.52566 (13) | 0.9149 (2) | 0.0504 (10) | |
H22 | 0.6761 | 0.5563 | 0.9097 | 0.060* | |
C23 | 0.7595 (4) | 0.49572 (13) | 0.9441 (2) | 0.0460 (9) | |
H23 | 0.8513 | 0.5060 | 0.9586 | 0.055* | |
C24 | 0.7261 (4) | 0.45019 (12) | 0.95148 (19) | 0.0353 (8) | |
C25 | 0.8049 (3) | 0.41074 (11) | 0.98263 (19) | 0.0341 (8) | |
C26 | 0.9457 (4) | 0.40398 (13) | 1.0141 (2) | 0.0447 (9) | |
H26 | 1.0089 | 0.4282 | 1.0185 | 0.054* | |
C27 | 0.9894 (4) | 0.36122 (14) | 1.0382 (2) | 0.0515 (10) | |
H27 | 1.0825 | 0.3566 | 1.0602 | 0.062* | |
C28 | 0.8964 (4) | 0.32481 (14) | 1.0304 (2) | 0.0509 (10) | |
H28 | 0.9287 | 0.2960 | 1.0469 | 0.061* | |
C29 | 0.7569 (4) | 0.33008 (12) | 0.9987 (2) | 0.0426 (9) | |
H29 | 0.6954 | 0.3054 | 0.9928 | 0.051* | |
C30 | 0.7121 (3) | 0.37348 (11) | 0.97597 (19) | 0.0338 (8) | |
C31 | 0.9320 (4) | 0.52604 (12) | 0.7581 (2) | 0.0379 (8) | |
C32 | 0.8601 (4) | 0.49528 (11) | 0.7056 (2) | 0.0377 (8) | |
H32 | 0.8932 | 0.4657 | 0.7011 | 0.045* | |
C33 | 0.7369 (4) | 0.50968 (11) | 0.65984 (19) | 0.0337 (8) | |
C34 | 0.6863 (4) | 0.55340 (11) | 0.6678 (2) | 0.0343 (8) | |
H34 | 0.6029 | 0.5625 | 0.6377 | 0.041* | |
C35 | 0.7604 (4) | 0.58358 (11) | 0.7210 (2) | 0.0344 (8) | |
C36 | 0.8849 (4) | 0.57009 (12) | 0.7663 (2) | 0.0395 (8) | |
H36 | 0.9354 | 0.5903 | 0.8016 | 0.047* | |
C37 | 0.7209 (4) | 0.45443 (11) | 0.54364 (19) | 0.0338 (8) | |
C38 | 0.8564 (4) | 0.45616 (13) | 0.5199 (2) | 0.0451 (9) | |
H38 | 0.9251 | 0.4753 | 0.5457 | 0.054* | |
C39 | 0.8854 (5) | 0.42831 (15) | 0.4566 (2) | 0.0577 (11) | |
H39 | 0.9750 | 0.4290 | 0.4389 | 0.069* | |
C40 | 0.7834 (5) | 0.39940 (16) | 0.4188 (3) | 0.0638 (13) | |
H40 | 0.8065 | 0.3807 | 0.3769 | 0.077* | |
C41 | 0.6489 (4) | 0.39783 (14) | 0.4420 (2) | 0.0518 (10) | |
H41 | 0.5813 | 0.3784 | 0.4161 | 0.062* | |
C42 | 0.6154 (4) | 0.42606 (11) | 0.5053 (2) | 0.0360 (8) | |
C43 | 0.4876 (4) | 0.43387 (11) | 0.5432 (2) | 0.0361 (8) | |
C44 | 0.3517 (4) | 0.41591 (12) | 0.5316 (2) | 0.0441 (9) | |
H44 | 0.3286 | 0.3942 | 0.4915 | 0.053* | |
C45 | 0.2528 (4) | 0.43036 (15) | 0.5793 (3) | 0.0569 (11) | |
H45 | 0.1617 | 0.4185 | 0.5717 | 0.068* | |
C46 | 0.2868 (5) | 0.46268 (15) | 0.6394 (3) | 0.0600 (11) | |
H46 | 0.2175 | 0.4721 | 0.6713 | 0.072* | |
C47 | 0.4207 (4) | 0.48124 (14) | 0.6530 (2) | 0.0501 (10) | |
H47 | 0.4430 | 0.5027 | 0.6936 | 0.060* | |
C48 | 0.5203 (4) | 0.46660 (11) | 0.6036 (2) | 0.0351 (8) | |
C49 | 0.5797 (4) | 0.64261 (12) | 0.7489 (2) | 0.0372 (8) | |
C50 | 0.4706 (4) | 0.61640 (14) | 0.7728 (2) | 0.0479 (9) | |
H50 | 0.4767 | 0.5848 | 0.7741 | 0.057* | |
C51 | 0.3520 (5) | 0.63869 (16) | 0.7946 (3) | 0.0589 (11) | |
H51 | 0.2773 | 0.6218 | 0.8109 | 0.071* | |
C52 | 0.3425 (5) | 0.68580 (18) | 0.7925 (3) | 0.0673 (13) | |
H52 | 0.2621 | 0.7000 | 0.8077 | 0.081* | |
C53 | 0.4507 (5) | 0.71163 (15) | 0.7682 (3) | 0.0585 (12) | |
H53 | 0.4435 | 0.7432 | 0.7668 | 0.070* | |
C54 | 0.5713 (4) | 0.69033 (12) | 0.7456 (2) | 0.0424 (9) | |
C55 | 0.7041 (4) | 0.70643 (12) | 0.7205 (2) | 0.0439 (9) | |
C56 | 0.7564 (6) | 0.74945 (13) | 0.7061 (3) | 0.0603 (12) | |
H56 | 0.7023 | 0.7753 | 0.7128 | 0.072* | |
C57 | 0.8889 (6) | 0.75312 (16) | 0.6819 (3) | 0.0731 (15) | |
H57 | 0.9240 | 0.7818 | 0.6712 | 0.088* | |
C58 | 0.9727 (5) | 0.71487 (18) | 0.6729 (3) | 0.0677 (13) | |
H58 | 1.0634 | 0.7185 | 0.6576 | 0.081* | |
C59 | 0.9224 (5) | 0.67159 (15) | 0.6865 (2) | 0.0552 (10) | |
H59 | 0.9769 | 0.6459 | 0.6796 | 0.066* | |
C60 | 0.7879 (4) | 0.66813 (12) | 0.7107 (2) | 0.0397 (8) | |
I1 | 0.25530 (3) | 0.255028 (10) | 1.050844 (18) | 0.05953 (10) | |
I2 | 1.11186 (3) | 0.504351 (11) | 0.831782 (18) | 0.06639 (11) | |
N1 | 0.1724 (3) | 0.33975 (10) | 0.75786 (16) | 0.0364 (7) | |
N2 | 0.5786 (3) | 0.38871 (9) | 0.94166 (17) | 0.0349 (6) | |
N3 | 0.6627 (3) | 0.47903 (9) | 0.60422 (16) | 0.0359 (7) | |
N4 | 0.7111 (3) | 0.62920 (9) | 0.72709 (18) | 0.0387 (7) |
Atomic displacement parameters (Å2)
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U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0306 (19) | 0.0364 (19) | 0.0402 (19) | 0.0020 (15) | 0.0044 (15) | 0.0111 (15) |
C2 | 0.0299 (19) | 0.041 (2) | 0.0405 (19) | −0.0051 (16) | −0.0025 (15) | 0.0032 (16) |
C3 | 0.0311 (18) | 0.041 (2) | 0.0318 (17) | 0.0011 (16) | −0.0065 (14) | −0.0006 (15) |
C4 | 0.037 (2) | 0.0379 (19) | 0.0339 (18) | −0.0025 (16) | 0.0014 (15) | 0.0036 (15) |
C5 | 0.0272 (18) | 0.0363 (19) | 0.0351 (18) | −0.0006 (15) | −0.0019 (14) | −0.0021 (14) |
C6 | 0.0283 (18) | 0.043 (2) | 0.0337 (18) | −0.0001 (15) | −0.0047 (14) | 0.0050 (15) |
C7 | 0.037 (2) | 0.0332 (18) | 0.0357 (18) | −0.0018 (15) | 0.0020 (15) | 0.0002 (14) |
C8 | 0.037 (2) | 0.050 (2) | 0.055 (2) | 0.0056 (18) | −0.0007 (18) | 0.0003 (18) |
C9 | 0.049 (3) | 0.054 (2) | 0.060 (3) | 0.011 (2) | 0.017 (2) | −0.005 (2) |
C10 | 0.058 (3) | 0.053 (2) | 0.045 (2) | 0.001 (2) | 0.014 (2) | −0.0149 (19) |
C11 | 0.048 (2) | 0.049 (2) | 0.0335 (19) | −0.0040 (18) | −0.0010 (17) | −0.0045 (16) |
C12 | 0.0361 (19) | 0.0297 (17) | 0.0342 (18) | −0.0021 (15) | −0.0006 (15) | −0.0014 (14) |
C13 | 0.0371 (19) | 0.0250 (16) | 0.0291 (16) | −0.0031 (14) | −0.0014 (14) | −0.0020 (13) |
C14 | 0.039 (2) | 0.0333 (18) | 0.0352 (18) | 0.0008 (16) | −0.0092 (16) | 0.0016 (15) |
C15 | 0.034 (2) | 0.042 (2) | 0.047 (2) | 0.0066 (16) | −0.0041 (17) | 0.0064 (17) |
C16 | 0.047 (2) | 0.045 (2) | 0.040 (2) | 0.0063 (18) | 0.0074 (17) | −0.0005 (17) |
C17 | 0.046 (2) | 0.048 (2) | 0.0313 (18) | 0.0015 (18) | 0.0013 (16) | −0.0034 (16) |
C18 | 0.0337 (19) | 0.0303 (17) | 0.0332 (18) | −0.0029 (15) | −0.0035 (14) | 0.0029 (14) |
C19 | 0.0303 (18) | 0.0366 (19) | 0.0311 (17) | −0.0018 (15) | 0.0016 (14) | 0.0007 (14) |
C20 | 0.039 (2) | 0.047 (2) | 0.044 (2) | 0.0016 (18) | −0.0062 (16) | 0.0031 (17) |
C21 | 0.047 (2) | 0.049 (2) | 0.056 (2) | 0.0006 (19) | −0.0011 (19) | 0.0136 (19) |
C22 | 0.057 (3) | 0.036 (2) | 0.059 (2) | −0.0054 (19) | 0.009 (2) | 0.0081 (18) |
C23 | 0.041 (2) | 0.047 (2) | 0.051 (2) | −0.0162 (18) | 0.0053 (18) | −0.0042 (18) |
C24 | 0.0320 (19) | 0.041 (2) | 0.0330 (18) | −0.0032 (16) | 0.0047 (15) | −0.0036 (15) |
C25 | 0.0291 (18) | 0.0397 (19) | 0.0331 (18) | −0.0022 (15) | 0.0025 (14) | −0.0091 (15) |
C26 | 0.0311 (19) | 0.049 (2) | 0.053 (2) | −0.0046 (17) | −0.0019 (17) | −0.0168 (18) |
C27 | 0.032 (2) | 0.060 (3) | 0.059 (2) | 0.0094 (19) | −0.0087 (18) | −0.014 (2) |
C28 | 0.042 (2) | 0.046 (2) | 0.064 (3) | 0.0111 (19) | −0.0024 (19) | 0.0010 (19) |
C29 | 0.038 (2) | 0.039 (2) | 0.049 (2) | −0.0008 (17) | −0.0030 (17) | 0.0001 (17) |
C30 | 0.0293 (18) | 0.041 (2) | 0.0300 (17) | 0.0010 (15) | −0.0005 (14) | −0.0046 (14) |
C31 | 0.0313 (19) | 0.045 (2) | 0.0359 (18) | 0.0098 (16) | −0.0033 (15) | −0.0034 (16) |
C32 | 0.041 (2) | 0.0325 (18) | 0.0393 (19) | 0.0104 (16) | 0.0004 (16) | −0.0026 (15) |
C33 | 0.0370 (19) | 0.0305 (18) | 0.0333 (17) | 0.0005 (15) | 0.0025 (15) | −0.0028 (14) |
C34 | 0.0343 (19) | 0.0325 (18) | 0.0353 (18) | 0.0055 (15) | −0.0006 (15) | −0.0012 (14) |
C35 | 0.037 (2) | 0.0288 (17) | 0.0372 (18) | 0.0052 (15) | 0.0050 (15) | −0.0027 (14) |
C36 | 0.041 (2) | 0.038 (2) | 0.0392 (19) | 0.0017 (17) | 0.0008 (16) | −0.0110 (16) |
C37 | 0.035 (2) | 0.0308 (18) | 0.0341 (18) | 0.0088 (15) | −0.0027 (15) | −0.0019 (14) |
C38 | 0.040 (2) | 0.051 (2) | 0.043 (2) | 0.0032 (18) | 0.0002 (17) | −0.0061 (17) |
C39 | 0.045 (2) | 0.079 (3) | 0.050 (2) | 0.018 (2) | 0.008 (2) | −0.008 (2) |
C40 | 0.060 (3) | 0.083 (3) | 0.046 (2) | 0.027 (3) | −0.004 (2) | −0.024 (2) |
C41 | 0.054 (3) | 0.053 (2) | 0.044 (2) | 0.016 (2) | −0.0134 (19) | −0.0175 (18) |
C42 | 0.040 (2) | 0.0324 (18) | 0.0335 (18) | 0.0088 (16) | −0.0053 (15) | −0.0007 (14) |
C43 | 0.037 (2) | 0.0295 (18) | 0.0390 (19) | 0.0020 (15) | −0.0068 (15) | 0.0037 (15) |
C44 | 0.046 (2) | 0.035 (2) | 0.048 (2) | −0.0024 (17) | −0.0076 (18) | 0.0064 (16) |
C45 | 0.039 (2) | 0.061 (3) | 0.070 (3) | −0.009 (2) | 0.003 (2) | 0.009 (2) |
C46 | 0.047 (3) | 0.072 (3) | 0.064 (3) | 0.002 (2) | 0.020 (2) | −0.001 (2) |
C47 | 0.045 (2) | 0.059 (2) | 0.048 (2) | −0.005 (2) | 0.0119 (18) | −0.0120 (19) |
C48 | 0.0336 (19) | 0.0356 (19) | 0.0351 (18) | 0.0023 (15) | −0.0006 (15) | 0.0025 (15) |
C49 | 0.044 (2) | 0.0368 (19) | 0.0302 (17) | 0.0061 (17) | 0.0013 (15) | −0.0052 (15) |
C50 | 0.049 (2) | 0.046 (2) | 0.048 (2) | 0.0064 (19) | 0.0062 (18) | 0.0021 (18) |
C51 | 0.050 (3) | 0.074 (3) | 0.053 (3) | 0.007 (2) | 0.008 (2) | 0.000 (2) |
C52 | 0.058 (3) | 0.083 (4) | 0.061 (3) | 0.033 (3) | 0.007 (2) | −0.006 (2) |
C53 | 0.074 (3) | 0.045 (2) | 0.055 (3) | 0.029 (2) | 0.000 (2) | −0.0056 (19) |
C54 | 0.058 (2) | 0.0323 (19) | 0.0357 (19) | 0.0090 (18) | −0.0021 (17) | −0.0060 (15) |
C55 | 0.063 (3) | 0.0319 (19) | 0.0348 (19) | −0.0008 (18) | −0.0060 (18) | −0.0047 (15) |
C56 | 0.088 (4) | 0.034 (2) | 0.055 (3) | −0.007 (2) | −0.009 (2) | −0.0021 (18) |
C57 | 0.105 (4) | 0.052 (3) | 0.057 (3) | −0.036 (3) | −0.015 (3) | 0.008 (2) |
C58 | 0.065 (3) | 0.079 (3) | 0.058 (3) | −0.029 (3) | 0.001 (2) | 0.005 (2) |
C59 | 0.052 (3) | 0.057 (3) | 0.057 (3) | −0.008 (2) | 0.008 (2) | −0.005 (2) |
C60 | 0.051 (2) | 0.0346 (19) | 0.0326 (18) | −0.0030 (17) | 0.0012 (16) | −0.0043 (15) |
I1 | 0.04082 (16) | 0.0682 (2) | 0.06848 (19) | −0.00388 (13) | 0.00070 (13) | 0.03549 (15) |
I2 | 0.04937 (18) | 0.0874 (2) | 0.05720 (18) | 0.03071 (15) | −0.01822 (13) | −0.01873 (15) |
N1 | 0.0299 (16) | 0.0466 (17) | 0.0309 (15) | 0.0000 (13) | −0.0049 (12) | −0.0020 (13) |
N2 | 0.0271 (15) | 0.0352 (16) | 0.0404 (16) | −0.0023 (12) | −0.0052 (12) | 0.0023 (12) |
N3 | 0.0360 (16) | 0.0330 (15) | 0.0376 (15) | 0.0012 (13) | −0.0016 (13) | −0.0087 (12) |
N4 | 0.0417 (18) | 0.0266 (15) | 0.0483 (17) | 0.0016 (13) | 0.0068 (14) | −0.0051 (13) |
top
C1—C6 | 1.375 (5) | C31—C36 | 1.381 (5) |
C1—C2 | 1.385 (5) | C31—C32 | 1.383 (5) |
C1—I1 | 2.093 (3) | C31—I2 | 2.091 (3) |
C2—C3 | 1.383 (5) | C32—C33 | 1.391 (5) |
C2—H2 | 0.9300 | C32—H32 | 0.9300 |
C3—C4 | 1.383 (5) | C33—C34 | 1.383 (5) |
C3—N1 | 1.425 (4) | C33—N3 | 1.421 (4) |
C4—C5 | 1.393 (5) | C34—C35 | 1.387 (5) |
C4—H4 | 0.9300 | C34—H34 | 0.9300 |
C5—C6 | 1.391 (5) | C35—C36 | 1.390 (5) |
C5—N2 | 1.417 (4) | C35—N4 | 1.427 (4) |
C6—H6 | 0.9300 | C36—H36 | 0.9300 |
C7—C8 | 1.390 (5) | C37—C38 | 1.387 (5) |
C7—N1 | 1.398 (4) | C37—N3 | 1.398 (4) |
C7—C12 | 1.406 (5) | C37—C42 | 1.403 (5) |
C8—C9 | 1.377 (5) | C38—C39 | 1.382 (5) |
C8—H8 | 0.9300 | C38—H38 | 0.9300 |
C9—C10 | 1.384 (6) | C39—C40 | 1.387 (6) |
C9—H9 | 0.9300 | C39—H39 | 0.9300 |
C10—C11 | 1.378 (5) | C40—C41 | 1.375 (6) |
C10—H10 | 0.9300 | C40—H40 | 0.9300 |
C11—C12 | 1.397 (5) | C41—C42 | 1.401 (5) |
C11—H11 | 0.9300 | C41—H41 | 0.9300 |
C12—C13 | 1.444 (5) | C42—C43 | 1.445 (5) |
C13—C14 | 1.387 (5) | C43—C44 | 1.389 (5) |
C13—C18 | 1.411 (4) | C43—C48 | 1.398 (5) |
C14—C15 | 1.386 (5) | C44—C45 | 1.360 (6) |
C14—H14 | 0.9300 | C44—H44 | 0.9300 |
C15—C16 | 1.390 (5) | C45—C46 | 1.388 (6) |
C15—H15 | 0.9300 | C45—H45 | 0.9300 |
C16—C17 | 1.380 (5) | C46—C47 | 1.380 (6) |
C16—H16 | 0.9300 | C46—H46 | 0.9300 |
C17—C18 | 1.394 (5) | C47—C48 | 1.385 (5) |
C17—H17 | 0.9300 | C47—H47 | 0.9300 |
C18—N1 | 1.390 (4) | C48—N3 | 1.400 (4) |
C19—C20 | 1.380 (5) | C49—C50 | 1.382 (5) |
C19—N2 | 1.393 (4) | C49—N4 | 1.394 (4) |
C19—C24 | 1.413 (5) | C49—C54 | 1.405 (5) |
C20—C21 | 1.356 (5) | C50—C51 | 1.385 (6) |
C20—H20 | 0.9300 | C50—H50 | 0.9300 |
C21—C22 | 1.387 (6) | C51—C52 | 1.387 (6) |
C21—H21 | 0.9300 | C51—H51 | 0.9300 |
C22—C23 | 1.377 (5) | C52—C53 | 1.372 (7) |
C22—H22 | 0.9300 | C52—H52 | 0.9300 |
C23—C24 | 1.383 (5) | C53—C54 | 1.393 (6) |
C23—H23 | 0.9300 | C53—H53 | 0.9300 |
C24—C25 | 1.445 (5) | C54—C55 | 1.449 (6) |
C25—C26 | 1.397 (5) | C55—C56 | 1.388 (5) |
C25—C30 | 1.403 (5) | C55—C60 | 1.398 (5) |
C26—C27 | 1.369 (5) | C56—C57 | 1.365 (7) |
C26—H26 | 0.9300 | C56—H56 | 0.9300 |
C27—C28 | 1.385 (6) | C57—C58 | 1.395 (7) |
C27—H27 | 0.9300 | C57—H57 | 0.9300 |
C28—C29 | 1.382 (5) | C58—C59 | 1.385 (6) |
C28—H28 | 0.9300 | C58—H58 | 0.9300 |
C29—C30 | 1.384 (5) | C59—C60 | 1.385 (5) |
C29—H29 | 0.9300 | C59—H59 | 0.9300 |
C30—N2 | 1.407 (4) | C60—N4 | 1.399 (4) |
C6—C1—C2 | 122.0 (3) | C34—C33—C32 | 120.8 (3) |
C6—C1—I1 | 118.6 (2) | C34—C33—N3 | 119.8 (3) |
C2—C1—I1 | 119.4 (3) | C32—C33—N3 | 119.5 (3) |
C3—C2—C1 | 118.6 (3) | C33—C34—C35 | 119.7 (3) |
C3—C2—H2 | 120.7 | C33—C34—H34 | 120.1 |
C1—C2—H2 | 120.7 | C35—C34—H34 | 120.1 |
C4—C3—C2 | 120.7 (3) | C34—C35—C36 | 120.4 (3) |
C4—C3—N1 | 120.1 (3) | C34—C35—N4 | 119.8 (3) |
C2—C3—N1 | 119.1 (3) | C36—C35—N4 | 119.8 (3) |
C3—C4—C5 | 119.7 (3) | C31—C36—C35 | 118.7 (3) |
C3—C4—H4 | 120.2 | C31—C36—H36 | 120.7 |
C5—C4—H4 | 120.2 | C35—C36—H36 | 120.7 |
C6—C5—C4 | 120.2 (3) | C38—C37—N3 | 129.4 (3) |
C6—C5—N2 | 119.4 (3) | C38—C37—C42 | 122.3 (3) |
C4—C5—N2 | 120.4 (3) | N3—C37—C42 | 108.3 (3) |
C1—C6—C5 | 118.8 (3) | C39—C38—C37 | 117.4 (4) |
C1—C6—H6 | 120.6 | C39—C38—H38 | 121.3 |
C5—C6—H6 | 120.6 | C37—C38—H38 | 121.3 |
C8—C7—N1 | 129.6 (3) | C38—C39—C40 | 121.3 (4) |
C8—C7—C12 | 121.9 (3) | C38—C39—H39 | 119.4 |
N1—C7—C12 | 108.5 (3) | C40—C39—H39 | 119.4 |
C9—C8—C7 | 116.9 (4) | C41—C40—C39 | 121.4 (4) |
C9—C8—H8 | 121.5 | C41—C40—H40 | 119.3 |
C7—C8—H8 | 121.5 | C39—C40—H40 | 119.3 |
C8—C9—C10 | 122.4 (4) | C40—C41—C42 | 118.8 (4) |
C8—C9—H9 | 118.8 | C40—C41—H41 | 120.6 |
C10—C9—H9 | 118.8 | C42—C41—H41 | 120.6 |
C11—C10—C9 | 120.5 (4) | C41—C42—C37 | 118.8 (3) |
C11—C10—H10 | 119.7 | C41—C42—C43 | 133.5 (3) |
C9—C10—H10 | 119.7 | C37—C42—C43 | 107.6 (3) |
C10—C11—C12 | 119.0 (3) | C44—C43—C48 | 119.6 (3) |
C10—C11—H11 | 120.5 | C44—C43—C42 | 133.8 (3) |
C12—C11—H11 | 120.5 | C48—C43—C42 | 106.6 (3) |
C11—C12—C7 | 119.2 (3) | C45—C44—C43 | 119.4 (4) |
C11—C12—C13 | 133.4 (3) | C45—C44—H44 | 120.3 |
C7—C12—C13 | 107.5 (3) | C43—C44—H44 | 120.3 |
C14—C13—C18 | 119.4 (3) | C44—C45—C46 | 120.5 (4) |
C14—C13—C12 | 134.3 (3) | C44—C45—H45 | 119.7 |
C18—C13—C12 | 106.3 (3) | C46—C45—H45 | 119.7 |
C15—C14—C13 | 119.6 (3) | C47—C46—C45 | 121.8 (4) |
C15—C14—H14 | 120.2 | C47—C46—H46 | 119.1 |
C13—C14—H14 | 120.2 | C45—C46—H46 | 119.1 |
C14—C15—C16 | 120.1 (3) | C46—C47—C48 | 117.2 (4) |
C14—C15—H15 | 120.0 | C46—C47—H47 | 121.4 |
C16—C15—H15 | 120.0 | C48—C47—H47 | 121.4 |
C17—C16—C15 | 122.1 (3) | C47—C48—C43 | 121.4 (3) |
C17—C16—H16 | 119.0 | C47—C48—N3 | 129.5 (3) |
C15—C16—H16 | 119.0 | C43—C48—N3 | 109.0 (3) |
C16—C17—C18 | 117.6 (3) | C50—C49—N4 | 129.6 (3) |
C16—C17—H17 | 121.2 | C50—C49—C54 | 121.7 (3) |
C18—C17—H17 | 121.2 | N4—C49—C54 | 108.7 (3) |
N1—C18—C17 | 129.4 (3) | C49—C50—C51 | 117.9 (4) |
N1—C18—C13 | 109.2 (3) | C49—C50—H50 | 121.1 |
C17—C18—C13 | 121.3 (3) | C51—C50—H50 | 121.1 |
C20—C19—N2 | 130.6 (3) | C50—C51—C52 | 121.2 (4) |
C20—C19—C24 | 120.5 (3) | C50—C51—H51 | 119.4 |
N2—C19—C24 | 108.8 (3) | C52—C51—H51 | 119.4 |
C21—C20—C19 | 119.0 (4) | C53—C52—C51 | 120.7 (4) |
C21—C20—H20 | 120.5 | C53—C52—H52 | 119.7 |
C19—C20—H20 | 120.5 | C51—C52—H52 | 119.7 |
C20—C21—C22 | 121.2 (4) | C52—C53—C54 | 119.7 (4) |
C20—C21—H21 | 119.4 | C52—C53—H53 | 120.2 |
C22—C21—H21 | 119.4 | C54—C53—H53 | 120.2 |
C23—C22—C21 | 120.8 (4) | C53—C54—C49 | 118.8 (4) |
C23—C22—H22 | 119.6 | C53—C54—C55 | 134.2 (4) |
C21—C22—H22 | 119.6 | C49—C54—C55 | 106.8 (3) |
C22—C23—C24 | 119.0 (4) | C56—C55—C60 | 119.6 (4) |
C22—C23—H23 | 120.5 | C56—C55—C54 | 133.3 (4) |
C24—C23—H23 | 120.5 | C60—C55—C54 | 107.1 (3) |
C23—C24—C19 | 119.4 (3) | C57—C56—C55 | 118.7 (4) |
C23—C24—C25 | 133.8 (3) | C57—C56—H56 | 120.6 |
C19—C24—C25 | 106.7 (3) | C55—C56—H56 | 120.6 |
C26—C25—C30 | 119.2 (3) | C56—C57—C58 | 121.5 (4) |
C26—C25—C24 | 133.3 (3) | C56—C57—H57 | 119.2 |
C30—C25—C24 | 107.4 (3) | C58—C57—H57 | 119.2 |
C27—C26—C25 | 119.2 (3) | C59—C58—C57 | 120.7 (5) |
C27—C26—H26 | 120.4 | C59—C58—H58 | 119.6 |
C25—C26—H26 | 120.4 | C57—C58—H58 | 119.6 |
C26—C27—C28 | 120.7 (4) | C60—C59—C58 | 117.4 (4) |
C26—C27—H27 | 119.6 | C60—C59—H59 | 121.3 |
C28—C27—H27 | 119.6 | C58—C59—H59 | 121.3 |
C29—C28—C27 | 121.7 (4) | C59—C60—C55 | 122.0 (4) |
C29—C28—H28 | 119.1 | C59—C60—N4 | 129.3 (3) |
C27—C28—H28 | 119.1 | C55—C60—N4 | 108.7 (3) |
C28—C29—C30 | 117.5 (3) | C18—N1—C7 | 108.5 (3) |
C28—C29—H29 | 121.3 | C18—N1—C3 | 125.8 (3) |
C30—C29—H29 | 121.3 | C7—N1—C3 | 125.2 (3) |
C29—C30—C25 | 121.7 (3) | C19—N2—C30 | 108.5 (3) |
C29—C30—N2 | 129.8 (3) | C19—N2—C5 | 125.7 (3) |
C25—C30—N2 | 108.4 (3) | C30—N2—C5 | 125.7 (3) |
C36—C31—C32 | 122.0 (3) | C37—N3—C48 | 108.4 (3) |
C36—C31—I2 | 118.8 (3) | C37—N3—C33 | 125.9 (3) |
C32—C31—I2 | 119.1 (2) | C48—N3—C33 | 125.7 (3) |
C31—C32—C33 | 118.3 (3) | C49—N4—C60 | 108.7 (3) |
C31—C32—H32 | 120.8 | C49—N4—C35 | 126.5 (3) |
C33—C32—H32 | 120.8 | C60—N4—C35 | 124.9 (3) |
C6—C1—C2—C3 | 1.7 (5) | C37—C42—C43—C44 | −179.7 (4) |
I1—C1—C2—C3 | −177.2 (3) | C41—C42—C43—C48 | −179.6 (4) |
C1—C2—C3—C4 | 0.9 (5) | C37—C42—C43—C48 | −0.3 (4) |
C1—C2—C3—N1 | 178.9 (3) | C48—C43—C44—C45 | −0.3 (5) |
C2—C3—C4—C5 | −1.9 (5) | C42—C43—C44—C45 | 179.1 (4) |
N1—C3—C4—C5 | −179.9 (3) | C43—C44—C45—C46 | −0.1 (6) |
C3—C4—C5—C6 | 0.3 (5) | C44—C45—C46—C47 | 0.0 (7) |
C3—C4—C5—N2 | 179.9 (3) | C45—C46—C47—C48 | 0.6 (6) |
C2—C1—C6—C5 | −3.2 (5) | C46—C47—C48—C43 | −1.0 (6) |
I1—C1—C6—C5 | 175.7 (3) | C46—C47—C48—N3 | −179.2 (4) |
C4—C5—C6—C1 | 2.2 (5) | C44—C43—C48—C47 | 0.8 (5) |
N2—C5—C6—C1 | −177.4 (3) | C42—C43—C48—C47 | −178.7 (3) |
N1—C7—C8—C9 | 179.5 (4) | C44—C43—C48—N3 | 179.4 (3) |
C12—C7—C8—C9 | −0.1 (5) | C42—C43—C48—N3 | −0.1 (4) |
C7—C8—C9—C10 | −0.1 (6) | N4—C49—C50—C51 | 177.4 (4) |
C8—C9—C10—C11 | −0.3 (7) | C54—C49—C50—C51 | −0.8 (5) |
C9—C10—C11—C12 | 0.8 (6) | C49—C50—C51—C52 | 0.1 (6) |
C10—C11—C12—C7 | −1.0 (5) | C50—C51—C52—C53 | 0.4 (7) |
C10—C11—C12—C13 | 179.7 (4) | C51—C52—C53—C54 | −0.1 (7) |
C8—C7—C12—C11 | 0.7 (5) | C52—C53—C54—C49 | −0.6 (6) |
N1—C7—C12—C11 | −179.1 (3) | C52—C53—C54—C55 | −177.2 (4) |
C8—C7—C12—C13 | −179.8 (3) | C50—C49—C54—C53 | 1.0 (5) |
N1—C7—C12—C13 | 0.5 (4) | N4—C49—C54—C53 | −177.5 (3) |
C11—C12—C13—C14 | −2.6 (7) | C50—C49—C54—C55 | 178.6 (3) |
C7—C12—C13—C14 | 178.0 (4) | N4—C49—C54—C55 | 0.0 (4) |
C11—C12—C13—C18 | 178.4 (4) | C53—C54—C55—C56 | −3.7 (7) |
C7—C12—C13—C18 | −1.1 (4) | C49—C54—C55—C56 | 179.3 (4) |
C18—C13—C14—C15 | −0.9 (5) | C53—C54—C55—C60 | 176.2 (4) |
C12—C13—C14—C15 | −179.9 (3) | C49—C54—C55—C60 | −0.7 (4) |
C13—C14—C15—C16 | 0.7 (5) | C60—C55—C56—C57 | 0.5 (6) |
C14—C15—C16—C17 | 0.2 (6) | C54—C55—C56—C57 | −179.5 (4) |
C15—C16—C17—C18 | −0.8 (6) | C55—C56—C57—C58 | −1.1 (7) |
C16—C17—C18—N1 | 178.4 (3) | C56—C57—C58—C59 | 1.5 (7) |
C16—C17—C18—C13 | 0.6 (5) | C57—C58—C59—C60 | −1.2 (6) |
C14—C13—C18—N1 | −178.0 (3) | C58—C59—C60—C55 | 0.6 (6) |
C12—C13—C18—N1 | 1.3 (4) | C58—C59—C60—N4 | 178.9 (4) |
C14—C13—C18—C17 | 0.2 (5) | C56—C55—C60—C59 | −0.3 (5) |
C12—C13—C18—C17 | 179.5 (3) | C54—C55—C60—C59 | 179.7 (3) |
N2—C19—C20—C21 | 177.4 (4) | C56—C55—C60—N4 | −178.9 (3) |
C24—C19—C20—C21 | −0.3 (5) | C54—C55—C60—N4 | 1.2 (4) |
C19—C20—C21—C22 | 1.5 (6) | C17—C18—N1—C7 | −179.0 (3) |
C20—C21—C22—C23 | −1.4 (6) | C13—C18—N1—C7 | −1.0 (4) |
C21—C22—C23—C24 | 0.0 (6) | C17—C18—N1—C3 | 9.2 (6) |
C22—C23—C24—C19 | 1.2 (5) | C13—C18—N1—C3 | −172.8 (3) |
C22—C23—C24—C25 | −176.4 (4) | C8—C7—N1—C18 | −179.4 (4) |
C20—C19—C24—C23 | −1.1 (5) | C12—C7—N1—C18 | 0.3 (4) |
N2—C19—C24—C23 | −179.2 (3) | C8—C7—N1—C3 | −7.5 (6) |
C20—C19—C24—C25 | 177.1 (3) | C12—C7—N1—C3 | 172.2 (3) |
N2—C19—C24—C25 | −1.0 (4) | C4—C3—N1—C18 | −121.8 (4) |
C23—C24—C25—C26 | −2.8 (7) | C2—C3—N1—C18 | 60.1 (5) |
C19—C24—C25—C26 | 179.4 (4) | C4—C3—N1—C7 | 67.7 (5) |
C23—C24—C25—C30 | 178.4 (4) | C2—C3—N1—C7 | −110.4 (4) |
C19—C24—C25—C30 | 0.6 (4) | C20—C19—N2—C30 | −176.8 (4) |
C30—C25—C26—C27 | −0.6 (5) | C24—C19—N2—C30 | 1.1 (4) |
C24—C25—C26—C27 | −179.2 (4) | C20—C19—N2—C5 | 2.8 (6) |
C25—C26—C27—C28 | 1.2 (6) | C24—C19—N2—C5 | −179.3 (3) |
C26—C27—C28—C29 | −0.5 (6) | C29—C30—N2—C19 | −178.5 (4) |
C27—C28—C29—C30 | −1.0 (6) | C25—C30—N2—C19 | −0.7 (4) |
C28—C29—C30—C25 | 1.6 (5) | C29—C30—N2—C5 | 1.9 (6) |
C28—C29—C30—N2 | 179.2 (3) | C25—C30—N2—C5 | 179.7 (3) |
C26—C25—C30—C29 | −0.9 (5) | C6—C5—N2—C19 | −132.6 (3) |
C24—C25—C30—C29 | 178.1 (3) | C4—C5—N2—C19 | 47.8 (5) |
C26—C25—C30—N2 | −179.0 (3) | C6—C5—N2—C30 | 47.0 (5) |
C24—C25—C30—N2 | 0.0 (4) | C4—C5—N2—C30 | −132.6 (3) |
C36—C31—C32—C33 | 0.3 (5) | C38—C37—N3—C48 | 178.0 (3) |
I2—C31—C32—C33 | 177.0 (3) | C42—C37—N3—C48 | −0.6 (4) |
C31—C32—C33—C34 | −1.3 (5) | C38—C37—N3—C33 | −5.0 (6) |
C31—C32—C33—N3 | 178.7 (3) | C42—C37—N3—C33 | 176.4 (3) |
C32—C33—C34—C35 | 1.2 (5) | C47—C48—N3—C37 | 178.9 (4) |
N3—C33—C34—C35 | −178.7 (3) | C43—C48—N3—C37 | 0.5 (4) |
C33—C34—C35—C36 | −0.2 (5) | C47—C48—N3—C33 | 1.8 (6) |
C33—C34—C35—N4 | 177.7 (3) | C43—C48—N3—C33 | −176.5 (3) |
C32—C31—C36—C35 | 0.7 (6) | C34—C33—N3—C37 | 127.3 (4) |
I2—C31—C36—C35 | −176.1 (3) | C32—C33—N3—C37 | −52.6 (5) |
C34—C35—C36—C31 | −0.7 (5) | C34—C33—N3—C48 | −56.2 (5) |
N4—C35—C36—C31 | −178.7 (3) | C32—C33—N3—C48 | 123.9 (4) |
N3—C37—C38—C39 | −178.9 (3) | C50—C49—N4—C60 | −177.7 (4) |
C42—C37—C38—C39 | −0.5 (5) | C54—C49—N4—C60 | 0.7 (4) |
C37—C38—C39—C40 | −0.7 (6) | C50—C49—N4—C35 | 3.2 (6) |
C38—C39—C40—C41 | 1.1 (7) | C54—C49—N4—C35 | −178.4 (3) |
C39—C40—C41—C42 | −0.2 (6) | C59—C60—N4—C49 | −179.6 (4) |
C40—C41—C42—C37 | −0.9 (5) | C55—C60—N4—C49 | −1.2 (4) |
C40—C41—C42—C43 | 178.4 (4) | C59—C60—N4—C35 | −0.4 (6) |
C38—C37—C42—C41 | 1.3 (5) | C55—C60—N4—C35 | 178.0 (3) |
N3—C37—C42—C41 | −180.0 (3) | C34—C35—N4—C49 | 59.1 (5) |
C38—C37—C42—C43 | −178.2 (3) | C36—C35—N4—C49 | −123.0 (4) |
N3—C37—C42—C43 | 0.6 (4) | C34—C35—N4—C60 | −119.9 (4) |
C41—C42—C43—C44 | 1.0 (7) | C36—C35—N4—C60 | 58.0 (5) |