Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035751/hb2475sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035751/hb2475Isup2.hkl |
CCDC reference: 657856
Key indicators
- Single-crystal X-ray study
- T = 141 K
- Mean (C-C) = 0.007 Å
- R factor = 0.049
- wR factor = 0.053
- Data-to-parameter ratio = 7.4
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.72 Deg.
Author Response: Data up to a theta max of 24.72 degrees was obtained. Beyond this angle, no diffraction was observed. This is attributed to the weak scattering factors of the low molecular weight elements carbon, nitrogen, oxygen and hydrogen that compose the title compound. |
PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 60
Author Response: Only oxygen, nitrogen and methoxy carbon atoms were refined anisotropically. This was due to the low data to parameter ratio obtained for this data set. |
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 2.161 REFNR01_ALERT_3_C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5884 Proportion of unique data used 0.6967 Ratio reflections to parameters 7.3805 THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5884 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.72 Deg. PLAT087_ALERT_2_C Unsatisfactory S value (Too High) .............. 2.16 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.38 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT414_ALERT_2_C Short Intra D-H..H-X H21 .. H56 .. 1.94 Ang. PLAT414_ALERT_2_C Short Intra D-H..H-X H22 .. H55 .. 1.95 Ang. PLAT414_ALERT_2_C Short Intra D-H..H-X H11 .. H53 .. 1.92 Ang. PLAT701_ALERT_1_C Bond Calc 0.95(4), Rep 0.87(4), Dev.. 2.00 Sigma N2 -H54 1.555 1.555 PLAT702_ALERT_1_C Angle Calc 115(3), Rep 119(2), Dev.. 1.33 Sigma C1 -N1 -H53 1.555 1.555 1.555 PLAT702_ALERT_1_C Angle Calc 116(3), Rep 111(2), Dev.. 1.67 Sigma C17 -N1 -H53 1.555 1.555 1.555 PLAT702_ALERT_1_C Angle Calc 117(2), Rep 114(2), Dev.. 1.50 Sigma C26 -N2 -H54 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 24.72 From the CIF: _reflns_number_total 5011 Count of symmetry unique reflns 5056 Completeness (_total/calc) 99.11% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared by condensation of 1,8-diaminopyrene with the appropriate acid chloride according to the method described by Vollman et al. (1937). X-ray quality crystals of (I) were obtained by vapor diffusion of petroleum ether into chloroform at room temperature.
Due to negligible anomalous dispersion, Friedel pairs were merged before refinement. Only the oxygen, nitrogen and methoxy carbon atoms were refined anisotropically due to the low data to parameter ratio. The C-bound H atoms were geometrically placed and refined as riding. The N-bound H atoms were located in difference maps and their positions were refined.
The title compound, (I), cyrstallizes in space group P212121 with a pseudo-inversion center that lies between the two molecules of the asymmetric unit. The pseudo-inversion center is not located at coordinates appropriate to generate a centrosymmetric space group. The structure exhibits C—N, C—C, and C—O bond lengths and angles typical for common organic molecules. There are intramolecular hydrogen bonds located between the amide NH groups and the methoxy oxygen atoms for both molecules (Table 1).
Intermolecular distances between pyrene and catechol-derived rings range between 3.753 (7) Å and 3.800 (7) Å. These can be attributed to weak π–π interactions (Janiak, 2000). Such intermolecular contacts are not unexpected in a molecule with many aromatic rings. The aromatic rings do not stack closer to one another because the methoxy groups are positioned between the ring systems. Interplanar angles between the pyrene and a catechol-derivative ring range from 7.85–12.25 degrees. The angle between the two pyrene rings in the asymmetric unit is 3.38 degrees. The angle between catechol-derivative rings of the same molecule ranges from 5.93 to 11.24 degrees. Deviations from planarity between rings within the same molecule are most likely a result of the molecule accomodating favorable π–π interactions.
For related literature, see: Janiak (2000); Vollman et al. (1937).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1999); molecular graphics: PLEASE PROVIDE; software used to prepare material for publication: TEXSAN.
C34H28N2O6 | Dx = 1.400 Mg m−3 |
Mr = 560.60 | Mo Kα radiation, λ = 0.7107 Å |
Orthorhombic, P212121 | Cell parameters from 4595 reflections |
a = 12.5065 (9) Å | θ = 3.3–23.5° |
b = 15.074 (1) Å | µ = 0.10 mm−1 |
c = 28.223 (2) Å | T = 141 K |
V = 5320.8 (6) Å3 | Slab, green |
Z = 8 | 0.24 × 0.18 × 0.07 mm |
F(000) = 2352.00 |
Bruker SMART 1000 diffractometer | 3491 reflections with F2 > 3σ(F2) |
ω scans | Rint = 0.025 |
Absorption correction: multi-scan (Blessing, 1995) | θmax = 24.7° |
Tmin = 0.914, Tmax = 0.993 | h = 0→14 |
23940 measured reflections | k = 0→17 |
5011 independent reflections | l = 0→33 |
Refinement on F | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo) + 0.00022|Fo|2] |
wR(F2) = 0.053 | (Δ/σ)max = 0.001 |
S = 2.16 | Δρmax = 0.29 e Å−3 |
3491 reflections | Δρmin = −0.30 e Å−3 |
473 parameters |
C34H28N2O6 | V = 5320.8 (6) Å3 |
Mr = 560.60 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 12.5065 (9) Å | µ = 0.10 mm−1 |
b = 15.074 (1) Å | T = 141 K |
c = 28.223 (2) Å | 0.24 × 0.18 × 0.07 mm |
Bruker SMART 1000 diffractometer | 5011 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 3491 reflections with F2 > 3σ(F2) |
Tmin = 0.914, Tmax = 0.993 | Rint = 0.025 |
23940 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 473 parameters |
wR(F2) = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
S = 2.16 | Δρmax = 0.29 e Å−3 |
3491 reflections | Δρmin = −0.30 e Å−3 |
Refinement. Refinement using reflections with F2 > 3.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 3.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1497 (3) | −0.3210 (2) | 0.1913 (1) | 0.051 (1) | |
O2 | 0.1194 (3) | −0.1567 (2) | 0.1632 (1) | 0.0335 (10) | |
O3 | 0.0472 (4) | −0.1003 (3) | 0.0231 (1) | 0.077 (2) | |
O4 | 0.1354 (3) | 0.3934 (2) | 0.3115 (1) | 0.057 (1) | |
O5 | 0.1516 (3) | 0.1158 (2) | 0.3304 (1) | 0.0324 (9) | |
O6 | 0.2436 (3) | 0.0517 (2) | 0.4074 (1) | 0.043 (1) | |
O7 | 0.2627 (3) | 0.3786 (2) | 0.0847 (1) | 0.050 (1) | |
O8 | 0.3468 (3) | 0.3176 (2) | 0.1643 (1) | 0.0333 (10) | |
O9 | 0.3531 (3) | 0.0418 (2) | 0.1885 (1) | 0.059 (1) | |
O10 | 0.4824 (4) | 0.5331 (3) | 0.4771 (1) | 0.066 (1) | |
O11 | 0.3775 (3) | 0.5875 (2) | 0.3402 (1) | 0.037 (1) | |
O12 | 0.3409 (3) | 0.7512 (2) | 0.3127 (1) | 0.051 (1) | |
N1 | 0.4875 (3) | 0.4834 (3) | 0.4009 (2) | 0.034 (1) | |
N2 | 0.4193 (3) | 0.1729 (3) | 0.2139 (1) | 0.033 (1) | |
N3 | 0.0788 (3) | 0.2612 (3) | 0.2831 (1) | 0.030 (1) | |
N4 | 0.0194 (4) | −0.0517 (3) | 0.0982 (1) | 0.035 (1) | |
C1 | 0.5229 (4) | 0.3959 (3) | 0.4064 (2) | 0.032 (1)* | |
C2 | 0.5754 (4) | 0.3684 (3) | 0.4475 (2) | 0.037 (1)* | |
C3 | 0.6079 (4) | 0.2809 (3) | 0.4523 (2) | 0.044 (1)* | |
C4 | 0.5879 (4) | 0.2174 (3) | 0.4179 (2) | 0.035 (1)* | |
C5 | 0.6150 (4) | 0.1261 (4) | 0.4237 (2) | 0.045 (1)* | |
C6 | 0.5947 (4) | 0.0663 (4) | 0.3903 (2) | 0.046 (1)* | |
C7 | 0.5499 (4) | 0.0913 (3) | 0.3452 (2) | 0.035 (1)* | |
C8 | 0.5340 (4) | 0.0315 (3) | 0.3082 (2) | 0.040 (1)* | |
C9 | 0.4940 (4) | 0.0579 (3) | 0.2656 (2) | 0.037 (1)* | |
C10 | 0.4659 (4) | 0.1460 (3) | 0.2572 (2) | 0.030 (1)* | |
C11 | 0.4792 (4) | 0.2093 (3) | 0.2933 (2) | 0.029 (1)* | |
C12 | 0.4477 (4) | 0.3005 (3) | 0.2889 (2) | 0.035 (1)* | |
C13 | 0.4592 (4) | 0.3589 (3) | 0.3248 (2) | 0.033 (1)* | |
C14 | 0.5073 (4) | 0.3355 (3) | 0.3689 (2) | 0.028 (1)* | |
C15 | 0.5397 (4) | 0.2457 (3) | 0.3748 (2) | 0.031 (1)* | |
C16 | 0.5231 (4) | 0.1836 (3) | 0.3376 (2) | 0.032 (1)* | |
C17 | 0.4704 (4) | 0.5460 (3) | 0.4347 (2) | 0.035 (1)* | |
C18 | 0.4411 (4) | 0.6363 (3) | 0.4165 (2) | 0.033 (1)* | |
C19 | 0.4602 (4) | 0.7072 (3) | 0.4470 (2) | 0.044 (1)* | |
C20 | 0.4406 (5) | 0.7924 (4) | 0.4327 (2) | 0.051 (2)* | |
C21 | 0.4011 (4) | 0.8114 (4) | 0.3881 (2) | 0.045 (1)* | |
C22 | 0.3791 (4) | 0.7425 (4) | 0.3574 (2) | 0.039 (1)* | |
C23 | 0.3985 (4) | 0.6547 (3) | 0.3718 (2) | 0.031 (1)* | |
C24 | 0.2656 (5) | 0.5666 (4) | 0.3378 (2) | 0.054 (2) | |
C25 | 0.3139 (5) | 0.8375 (4) | 0.2961 (2) | 0.065 (2) | |
C26 | 0.3647 (4) | 0.1219 (3) | 0.1828 (2) | 0.034 (1)* | |
C27 | 0.3196 (4) | 0.1662 (3) | 0.1390 (2) | 0.032 (1)* | |
C28 | 0.2814 (4) | 0.1075 (3) | 0.1042 (2) | 0.038 (1)* | |
C29 | 0.2360 (4) | 0.1399 (3) | 0.0634 (2) | 0.042 (1)* | |
C30 | 0.2268 (4) | 0.2297 (3) | 0.0551 (2) | 0.042 (1)* | |
C31 | 0.2651 (4) | 0.2891 (3) | 0.0890 (2) | 0.040 (1)* | |
C32 | 0.3103 (4) | 0.2562 (3) | 0.1311 (2) | 0.032 (1)* | |
C33 | 0.2590 (4) | 0.3556 (3) | 0.1908 (2) | 0.047 (2) | |
C34 | 0.1973 (4) | 0.4145 (4) | 0.0483 (2) | 0.052 (2) | |
C35 | 0.0323 (4) | 0.2886 (3) | 0.2398 (2) | 0.031 (1)* | |
C36 | 0.0046 (4) | 0.3761 (3) | 0.2310 (2) | 0.036 (1)* | |
C37 | −0.0330 (4) | 0.4011 (3) | 0.1870 (2) | 0.037 (1)* | |
C38 | −0.0470 (4) | 0.3411 (3) | 0.1501 (2) | 0.034 (1)* | |
C39 | −0.0869 (4) | 0.3666 (3) | 0.1044 (2) | 0.040 (1)* | |
C40 | −0.1005 (4) | 0.3069 (3) | 0.0701 (2) | 0.038 (1)* | |
C41 | −0.0720 (4) | 0.2155 (3) | 0.0767 (2) | 0.036 (1)* | |
C42 | −0.0829 (4) | 0.1524 (3) | 0.0411 (2) | 0.040 (1)* | |
C43 | −0.0519 (4) | 0.0656 (3) | 0.0468 (2) | 0.039 (1)* | |
C44 | −0.0105 (4) | 0.0371 (3) | 0.0901 (2) | 0.032 (1)* | |
C45 | −0.0010 (4) | 0.0974 (3) | 0.1281 (2) | 0.028 (1)* | |
C46 | 0.0395 (4) | 0.0738 (3) | 0.1738 (2) | 0.034 (1)* | |
C47 | 0.0487 (4) | 0.1326 (3) | 0.2093 (2) | 0.034 (1)* | |
C48 | 0.0189 (4) | 0.2238 (3) | 0.2037 (2) | 0.029 (1)* | |
C49 | −0.0200 (4) | 0.2510 (3) | 0.1587 (2) | 0.028 (1)* | |
C50 | −0.0306 (4) | 0.1878 (3) | 0.1212 (2) | 0.028 (1)* | |
C51 | 0.1290 (4) | 0.3131 (3) | 0.3153 (2) | 0.034 (1)* | |
C52 | 0.1779 (4) | 0.2675 (3) | 0.3578 (2) | 0.031 (1)* | |
C53 | 0.2180 (4) | 0.3227 (3) | 0.3934 (2) | 0.039 (1)* | |
C54 | 0.2678 (4) | 0.2896 (3) | 0.4324 (2) | 0.038 (1)* | |
C55 | 0.2798 (4) | 0.1990 (3) | 0.4387 (2) | 0.040 (1)* | |
C56 | 0.2395 (4) | 0.1418 (3) | 0.4049 (2) | 0.036 (1)* | |
C57 | 0.1883 (4) | 0.1765 (3) | 0.3639 (2) | 0.031 (1)* | |
C58 | 0.2379 (4) | 0.0788 (3) | 0.3031 (2) | 0.044 (2) | |
C59 | 0.2925 (5) | 0.0143 (4) | 0.4484 (2) | 0.056 (2) | |
C60 | 0.0461 (4) | −0.1147 (4) | 0.0659 (2) | 0.040 (1)* | |
C61 | 0.0686 (4) | −0.2063 (3) | 0.0849 (2) | 0.035 (1)* | |
C62 | 0.0519 (4) | −0.2768 (3) | 0.0538 (2) | 0.042 (1)* | |
C63 | 0.0648 (5) | −0.3622 (4) | 0.0687 (2) | 0.049 (2)* | |
C64 | 0.0973 (4) | −0.3808 (3) | 0.1144 (2) | 0.045 (1)* | |
C65 | 0.1173 (4) | −0.3115 (3) | 0.1455 (2) | 0.036 (1)* | |
C66 | 0.1015 (4) | −0.2243 (3) | 0.1306 (2) | 0.032 (1)* | |
C67 | 0.2306 (5) | −0.1351 (4) | 0.1675 (2) | 0.050 (2) | |
C68 | 0.1803 (5) | −0.4063 (4) | 0.2073 (2) | 0.064 (2) | |
H1 | 0.3892 | 0.8711 | 0.3787 | 0.0543* | |
H2 | 0.4870 | 0.6963 | 0.4779 | 0.0529* | |
H3 | 0.4545 | 0.8398 | 0.4540 | 0.0615* | |
H4 | 0.5890 | 0.4096 | 0.4722 | 0.0440* | |
H5 | 0.6451 | 0.2639 | 0.4801 | 0.0524* | |
H6 | 0.6484 | 0.1076 | 0.4523 | 0.0542* | |
H7 | 0.6101 | 0.0056 | 0.3963 | 0.0552* | |
H8 | 0.5515 | −0.0293 | 0.3129 | 0.0483* | |
H9 | 0.4850 | 0.0154 | 0.2410 | 0.0439* | |
H10 | 0.4179 | 0.3204 | 0.2598 | 0.0420* | |
H11 | 0.4344 | 0.4179 | 0.3206 | 0.0400* | |
H12 | 0.2870 | 0.0453 | 0.1090 | 0.0456* | |
H13 | 0.2104 | 0.0993 | 0.0402 | 0.0501* | |
H14 | 0.1947 | 0.2508 | 0.0268 | 0.0505* | |
H15 | 0.0115 | 0.4191 | 0.2554 | 0.0433* | |
H16 | −0.0500 | 0.4618 | 0.1817 | 0.0438* | |
H17 | −0.1039 | 0.4271 | 0.0985 | 0.0476* | |
H18 | −0.1297 | 0.3253 | 0.0406 | 0.0459* | |
H19 | −0.1131 | 0.1699 | 0.0116 | 0.0476* | |
H20 | −0.0585 | 0.0250 | 0.0212 | 0.0469* | |
H21 | 0.0606 | 0.0141 | 0.1792 | 0.0407* | |
H22 | 0.0758 | 0.1131 | 0.2390 | 0.0408* | |
H23 | 0.0314 | −0.2653 | 0.0220 | 0.0503* | |
H24 | 0.0512 | −0.4096 | 0.0473 | 0.0586* | |
H25 | 0.1060 | −0.4405 | 0.1244 | 0.0546* | |
H26 | 0.2103 | 0.3851 | 0.3902 | 0.0463* | |
H27 | 0.2947 | 0.3292 | 0.4557 | 0.0455* | |
H28 | 0.3152 | 0.1765 | 0.4659 | 0.0477* | |
H29 | 0.2269 | 0.6177 | 0.3280 | 0.0652* | |
H30 | 0.2547 | 0.5201 | 0.3156 | 0.0652* | |
H31 | 0.2412 | 0.5484 | 0.3681 | 0.0652* | |
H32 | 0.3755 | 0.8744 | 0.2972 | 0.0782* | |
H33 | 0.2886 | 0.8338 | 0.2645 | 0.0782* | |
H34 | 0.2597 | 0.8620 | 0.3158 | 0.0782* | |
H35 | 0.2691 | −0.1860 | 0.1777 | 0.0594* | |
H36 | 0.2573 | −0.1162 | 0.1376 | 0.0594* | |
H37 | 0.2393 | −0.0888 | 0.1900 | 0.0594* | |
H38 | 0.1216 | −0.4460 | 0.2041 | 0.0765* | |
H39 | 0.2387 | −0.4272 | 0.1889 | 0.0765* | |
H40 | 0.2009 | −0.4031 | 0.2397 | 0.0765* | |
H41 | 0.2861 | 0.3967 | 0.2133 | 0.0560* | |
H42 | 0.2120 | 0.3854 | 0.1696 | 0.0560* | |
H43 | 0.2213 | 0.3098 | 0.2067 | 0.0560* | |
H44 | 0.2855 | 0.0480 | 0.3236 | 0.0527* | |
H45 | 0.2100 | 0.0388 | 0.2803 | 0.0527* | |
H46 | 0.2754 | 0.1252 | 0.2875 | 0.0527* | |
H47 | 0.2023 | 0.4774 | 0.0488 | 0.0620* | |
H48 | 0.2207 | 0.3930 | 0.0184 | 0.0620* | |
H49 | 0.1252 | 0.3973 | 0.0534 | 0.0620* | |
H50 | 0.2535 | 0.0315 | 0.4758 | 0.0668* | |
H51 | 0.2926 | −0.0486 | 0.4459 | 0.0668* | |
H52 | 0.3640 | 0.0350 | 0.4509 | 0.0668* | |
H53 | 0.473 (4) | 0.501 (3) | 0.369 (2) | 0.04 (1)* | |
H54 | 0.427 (4) | 0.234 (3) | 0.206 (1) | 0.04 (1)* | |
H55 | 0.074 (5) | 0.200 (4) | 0.290 (2) | 0.04 (2)* | |
H56 | 0.021 (4) | −0.070 (3) | 0.130 (2) | 0.04 (1)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.071 (3) | 0.038 (2) | 0.042 (2) | 0.014 (2) | 0.003 (2) | 0.005 (2) |
O2 | 0.036 (2) | 0.030 (2) | 0.034 (2) | −0.002 (2) | −0.002 (2) | −0.004 (2) |
O3 | 0.134 (4) | 0.066 (3) | 0.031 (2) | 0.042 (3) | 0.016 (2) | 0.004 (2) |
O4 | 0.075 (3) | 0.028 (2) | 0.066 (3) | −0.006 (2) | −0.024 (2) | 0.002 (2) |
O5 | 0.037 (2) | 0.029 (2) | 0.031 (2) | −0.001 (2) | 0.002 (2) | −0.005 (1) |
O6 | 0.060 (3) | 0.032 (2) | 0.039 (2) | −0.001 (2) | −0.009 (2) | 0.005 (2) |
O7 | 0.057 (3) | 0.037 (2) | 0.056 (2) | −0.001 (2) | −0.019 (2) | 0.007 (2) |
O8 | 0.029 (2) | 0.031 (2) | 0.039 (2) | −0.003 (2) | 0.000 (2) | −0.009 (2) |
O9 | 0.081 (3) | 0.031 (2) | 0.065 (3) | −0.014 (2) | −0.025 (2) | 0.004 (2) |
O10 | 0.109 (4) | 0.060 (2) | 0.028 (2) | 0.023 (3) | 0.004 (2) | −0.002 (2) |
O11 | 0.038 (2) | 0.035 (2) | 0.036 (2) | −0.003 (2) | −0.003 (2) | −0.005 (2) |
O12 | 0.069 (3) | 0.042 (2) | 0.043 (2) | 0.014 (2) | −0.004 (2) | 0.006 (2) |
N1 | 0.045 (3) | 0.029 (2) | 0.028 (2) | 0.002 (2) | −0.000 (2) | −0.005 (2) |
N2 | 0.040 (3) | 0.024 (3) | 0.035 (3) | −0.004 (2) | 0.001 (2) | −0.002 (2) |
N3 | 0.038 (3) | 0.025 (2) | 0.028 (2) | −0.001 (2) | 0.002 (2) | −0.002 (2) |
N4 | 0.051 (3) | 0.029 (2) | 0.026 (2) | −0.003 (2) | 0.002 (2) | −0.001 (2) |
C24 | 0.053 (4) | 0.045 (3) | 0.065 (4) | −0.008 (3) | −0.017 (3) | −0.003 (3) |
C25 | 0.081 (5) | 0.057 (4) | 0.058 (4) | 0.025 (4) | 0.007 (4) | 0.015 (3) |
C33 | 0.039 (3) | 0.040 (3) | 0.060 (4) | 0.001 (3) | 0.005 (3) | −0.011 (3) |
C34 | 0.052 (4) | 0.050 (4) | 0.053 (4) | 0.011 (3) | −0.002 (3) | 0.004 (3) |
C58 | 0.037 (3) | 0.041 (3) | 0.054 (3) | 0.005 (3) | 0.011 (3) | −0.010 (3) |
C59 | 0.073 (5) | 0.044 (4) | 0.050 (3) | 0.005 (3) | −0.007 (3) | 0.005 (3) |
C67 | 0.044 (4) | 0.048 (3) | 0.056 (4) | −0.007 (3) | −0.008 (3) | −0.009 (3) |
C68 | 0.078 (5) | 0.046 (4) | 0.067 (4) | 0.019 (4) | 0.009 (4) | 0.017 (3) |
O1—C65 | 1.363 (5) | C45—C50 | 1.425 (6) |
O1—C68 | 1.417 (6) | C46—C47 | 1.344 (6) |
O2—C66 | 1.391 (6) | C47—C48 | 1.434 (7) |
O2—C67 | 1.434 (6) | C48—C49 | 1.420 (6) |
O3—C60 | 1.228 (6) | C49—C50 | 1.430 (6) |
O4—C51 | 1.217 (6) | C51—C52 | 1.514 (6) |
O5—C57 | 1.393 (5) | C52—C53 | 1.396 (7) |
O5—C58 | 1.438 (5) | C52—C57 | 1.388 (7) |
O6—C56 | 1.361 (6) | C53—C54 | 1.361 (7) |
O6—C59 | 1.426 (6) | C54—C55 | 1.384 (7) |
O7—C31 | 1.355 (6) | C55—C56 | 1.382 (7) |
O7—C34 | 1.419 (6) | C56—C57 | 1.421 (6) |
O8—C32 | 1.393 (5) | C60—C61 | 1.506 (7) |
O8—C33 | 1.446 (6) | C61—C62 | 1.394 (6) |
O9—C26 | 1.225 (6) | C61—C66 | 1.382 (6) |
O10—C17 | 1.222 (5) | C62—C63 | 1.364 (7) |
O11—C23 | 1.375 (5) | C63—C64 | 1.380 (7) |
O11—C24 | 1.436 (6) | C64—C65 | 1.387 (7) |
O12—C22 | 1.357 (6) | C65—C66 | 1.394 (7) |
O12—C25 | 1.422 (6) | N1—H53 | 0.93 (5) |
N1—C1 | 1.401 (6) | N2—H54 | 0.87 (4) |
N1—C17 | 1.358 (6) | N3—H55 | 0.91 (6) |
N2—C10 | 1.413 (6) | N4—H56 | 0.95 (5) |
N2—C26 | 1.354 (6) | C2—H4 | 0.950 |
N3—C35 | 1.413 (6) | C3—H5 | 0.950 |
N3—C51 | 1.354 (6) | C5—H6 | 0.950 |
N4—C44 | 1.408 (6) | C6—H7 | 0.950 |
N4—C60 | 1.359 (6) | C8—H8 | 0.950 |
C1—C2 | 1.396 (6) | C9—H9 | 0.950 |
C1—C14 | 1.409 (6) | C12—H10 | 0.950 |
C2—C3 | 1.385 (7) | C13—H11 | 0.950 |
C3—C4 | 1.386 (7) | C19—H2 | 0.950 |
C4—C5 | 1.427 (7) | C20—H3 | 0.950 |
C4—C15 | 1.422 (6) | C21—H1 | 0.950 |
C5—C6 | 1.330 (7) | C24—H29 | 0.950 |
C6—C7 | 1.441 (7) | C24—H30 | 0.950 |
C7—C8 | 1.392 (6) | C24—H31 | 0.950 |
C7—C16 | 1.447 (7) | C25—H32 | 0.950 |
C8—C9 | 1.364 (6) | C25—H33 | 0.950 |
C9—C10 | 1.395 (7) | C25—H34 | 0.950 |
C10—C11 | 1.405 (6) | C28—H12 | 0.950 |
C11—C12 | 1.436 (7) | C29—H13 | 0.950 |
C11—C16 | 1.420 (6) | C30—H14 | 0.950 |
C12—C13 | 1.351 (6) | C33—H41 | 0.950 |
C13—C14 | 1.427 (6) | C33—H42 | 0.950 |
C14—C15 | 1.422 (7) | C33—H43 | 0.950 |
C15—C16 | 1.423 (6) | C34—H47 | 0.950 |
C17—C18 | 1.500 (6) | C34—H48 | 0.950 |
C18—C19 | 1.393 (7) | C34—H49 | 0.950 |
C18—C23 | 1.398 (6) | C36—H15 | 0.950 |
C19—C20 | 1.368 (7) | C37—H16 | 0.950 |
C20—C21 | 1.383 (7) | C39—H17 | 0.950 |
C21—C22 | 1.380 (7) | C40—H18 | 0.950 |
C22—C23 | 1.404 (7) | C42—H19 | 0.950 |
C26—C27 | 1.514 (6) | C43—H20 | 0.950 |
C27—C28 | 1.405 (6) | C46—H21 | 0.950 |
C27—C32 | 1.380 (6) | C47—H22 | 0.950 |
C28—C29 | 1.375 (7) | C53—H26 | 0.950 |
C29—C30 | 1.379 (7) | C54—H27 | 0.950 |
C30—C31 | 1.394 (7) | C55—H28 | 0.950 |
C31—C32 | 1.407 (7) | C58—H44 | 0.950 |
C35—C36 | 1.386 (7) | C58—H45 | 0.950 |
C35—C48 | 1.423 (6) | C58—H46 | 0.950 |
C36—C37 | 1.380 (6) | C59—H50 | 0.950 |
C37—C38 | 1.391 (6) | C59—H51 | 0.950 |
C38—C39 | 1.435 (6) | C59—H52 | 0.950 |
C38—C49 | 1.421 (6) | C62—H23 | 0.950 |
C39—C40 | 1.334 (7) | C63—H24 | 0.950 |
C40—C41 | 1.435 (7) | C64—H25 | 0.950 |
C41—C42 | 1.391 (7) | C67—H35 | 0.950 |
C41—C50 | 1.423 (6) | C67—H36 | 0.950 |
C42—C43 | 1.374 (7) | C67—H37 | 0.950 |
C43—C44 | 1.397 (6) | C68—H38 | 0.950 |
C44—C45 | 1.410 (6) | C68—H39 | 0.950 |
C45—C46 | 1.431 (6) | C68—H40 | 0.950 |
O1···N3i | 3.198 (6) | O12···C10iv | 3.499 (6) |
O1···C35i | 3.419 (6) | N1···C28iv | 3.446 (7) |
O2···N3i | 3.159 (5) | N2···C23v | 3.335 (6) |
O2···C51i | 3.198 (6) | N2···C22v | 3.393 (7) |
O2···O4i | 3.351 (5) | N3···C66iii | 3.328 (6) |
O2···C36i | 3.401 (6) | N3···C65iii | 3.360 (6) |
O2···C35i | 3.431 (6) | N4···C53i | 3.529 (7) |
O3···C59ii | 3.185 (7) | C3···C62vii | 3.494 (7) |
O3···C5ii | 3.483 (7) | C9···C58 | 3.388 (7) |
O3···C55ii | 3.546 (6) | C10···C58 | 3.291 (7) |
O4···C24 | 3.166 (7) | C14···C67iv | 3.463 (7) |
O4···N4iii | 3.305 (6) | C14···C54 | 3.559 (7) |
O4···C46iii | 3.514 (6) | C15···C67iv | 3.591 (7) |
O5···C64iii | 3.482 (6) | C17···C28iv | 3.420 (7) |
O5···C37i | 3.593 (6) | C18···C27iv | 3.408 (7) |
O6···C39i | 3.425 (6) | C18···C28iv | 3.546 (7) |
O7···C6iv | 3.419 (6) | C23···C26iv | 3.375 (7) |
O8···C21v | 3.484 (6) | C23···C27iv | 3.542 (7) |
O9···C67 | 3.132 (6) | C24···C45iii | 3.478 (8) |
O9···N1v | 3.334 (6) | C28···C45 | 3.599 (7) |
O9···O11v | 3.533 (6) | C29···C44 | 3.533 (7) |
O9···C58 | 3.586 (6) | C29···C45 | 3.540 (7) |
O10···C34vi | 3.118 (7) | C33···C35 | 3.313 (7) |
O11···N2iv | 3.233 (5) | C33···C36 | 3.393 (7) |
O11···C26iv | 3.330 (6) | C51···C66iii | 3.311 (7) |
O11···C9iv | 3.420 (6) | C52···C61iii | 3.505 (7) |
O11···C10iv | 3.490 (6) | C52···C66iii | 3.512 (7) |
O12···N2iv | 3.310 (6) | ||
C65—O1—C68 | 118.6 (4) | C60—C61—C62 | 116.6 (4) |
C66—O2—C67 | 112.2 (4) | C60—C61—C66 | 124.6 (5) |
C57—O5—C58 | 111.7 (4) | C62—C61—C66 | 118.8 (5) |
C56—O6—C59 | 116.9 (4) | C61—C62—C63 | 120.6 (5) |
C31—O7—C34 | 117.3 (4) | C62—C63—C64 | 121.0 (5) |
C32—O8—C33 | 111.2 (4) | C63—C64—C65 | 119.4 (5) |
C23—O11—C24 | 112.2 (4) | O1—C65—C64 | 125.1 (5) |
C22—O12—C25 | 118.5 (4) | O1—C65—C66 | 115.2 (4) |
C1—N1—C17 | 128.8 (4) | C64—C65—C66 | 119.6 (5) |
C10—N2—C26 | 127.3 (4) | O2—C66—C61 | 121.4 (4) |
C35—N3—C51 | 127.0 (4) | O2—C66—C65 | 118.0 (4) |
C44—N4—C60 | 128.4 (4) | C61—C66—C65 | 120.6 (5) |
N1—C1—C2 | 121.4 (4) | C1—N1—H53 | 119 (2) |
N1—C1—C14 | 118.8 (4) | C17—N1—H53 | 111 (2) |
C2—C1—C14 | 119.8 (4) | C10—N2—H54 | 117 (2) |
C1—C2—C3 | 120.1 (5) | C26—N2—H54 | 114 (2) |
C2—C3—C4 | 122.4 (5) | C35—N3—H55 | 114 (3) |
C3—C4—C5 | 122.9 (5) | C51—N3—H55 | 119 (3) |
C3—C4—C15 | 117.9 (5) | C44—N4—H56 | 116 (2) |
C5—C4—C15 | 119.3 (4) | C60—N4—H56 | 115 (3) |
C4—C5—C6 | 121.8 (5) | C1—C2—H4 | 119.949 |
C5—C6—C7 | 121.6 (5) | C3—C2—H4 | 119.940 |
C6—C7—C8 | 123.2 (5) | C2—C3—H5 | 118.796 |
C6—C7—C16 | 118.1 (4) | C4—C3—H5 | 118.790 |
C8—C7—C16 | 118.7 (4) | C4—C5—H6 | 119.115 |
C7—C8—C9 | 121.6 (5) | C6—C5—H6 | 119.117 |
C8—C9—C10 | 121.3 (5) | C5—C6—H7 | 119.191 |
N2—C10—C9 | 121.6 (4) | C7—C6—H7 | 119.187 |
N2—C10—C11 | 118.7 (4) | C7—C8—H8 | 119.189 |
C9—C10—C11 | 119.6 (4) | C9—C8—H8 | 119.193 |
C10—C11—C12 | 123.6 (4) | C8—C9—H9 | 119.327 |
C10—C11—C16 | 119.9 (4) | C10—C9—H9 | 119.330 |
C12—C11—C16 | 116.4 (4) | C11—C12—H10 | 119.031 |
C11—C12—C13 | 121.9 (4) | C13—C12—H10 | 119.040 |
C12—C13—C14 | 122.6 (4) | C12—C13—H11 | 118.676 |
C1—C14—C13 | 123.6 (4) | C14—C13—H11 | 118.679 |
C1—C14—C15 | 119.2 (4) | C18—C19—H2 | 119.750 |
C13—C14—C15 | 117.2 (4) | C20—C19—H2 | 119.755 |
C4—C15—C14 | 120.4 (4) | C19—C20—H3 | 119.120 |
C4—C15—C16 | 119.6 (4) | C21—C20—H3 | 119.112 |
C14—C15—C16 | 120.0 (4) | C20—C21—H1 | 120.424 |
C7—C16—C11 | 118.8 (4) | C22—C21—H1 | 120.419 |
C7—C16—C15 | 119.4 (4) | O11—C24—H29 | 109.457 |
C11—C16—C15 | 121.7 (4) | O11—C24—H30 | 109.465 |
O10—C17—N1 | 123.9 (5) | O11—C24—H31 | 109.467 |
O10—C17—C18 | 120.7 (5) | H29—C24—H30 | 109.476 |
N1—C17—C18 | 115.4 (4) | H29—C24—H31 | 109.477 |
C17—C18—C19 | 116.3 (4) | H30—C24—H31 | 109.486 |
C17—C18—C23 | 125.6 (4) | O12—C25—H32 | 109.478 |
C19—C18—C23 | 118.1 (5) | O12—C25—H33 | 109.478 |
C18—C19—C20 | 120.5 (5) | O12—C25—H34 | 109.472 |
C19—C20—C21 | 121.8 (5) | H32—C25—H33 | 109.475 |
C20—C21—C22 | 119.2 (5) | H32—C25—H34 | 109.465 |
O12—C22—C21 | 125.5 (5) | H33—C25—H34 | 109.460 |
O12—C22—C23 | 114.9 (5) | C27—C28—H12 | 119.915 |
C21—C22—C23 | 119.5 (5) | C29—C28—H12 | 119.924 |
O11—C23—C18 | 120.7 (4) | C28—C29—H13 | 119.199 |
O11—C23—C22 | 118.3 (4) | C30—C29—H13 | 119.191 |
C18—C23—C22 | 120.9 (5) | C29—C30—H14 | 120.437 |
O9—C26—N2 | 122.3 (5) | C31—C30—H14 | 120.427 |
O9—C26—C27 | 119.9 (5) | O8—C33—H41 | 109.476 |
N2—C26—C27 | 117.8 (4) | O8—C33—H42 | 109.466 |
C26—C27—C28 | 114.7 (4) | O8—C33—H43 | 109.470 |
C26—C27—C32 | 126.7 (5) | H41—C33—H42 | 109.473 |
C28—C27—C32 | 118.6 (5) | H41—C33—H43 | 109.479 |
C27—C28—C29 | 120.2 (5) | H42—C33—H43 | 109.464 |
C28—C29—C30 | 121.6 (5) | O7—C34—H47 | 109.474 |
C29—C30—C31 | 119.1 (5) | O7—C34—H48 | 109.468 |
O7—C31—C30 | 124.8 (5) | O7—C34—H49 | 109.471 |
O7—C31—C32 | 115.8 (5) | H47—C34—H48 | 109.472 |
C30—C31—C32 | 119.4 (5) | H47—C34—H49 | 109.474 |
O8—C32—C27 | 121.1 (4) | H48—C34—H49 | 109.468 |
O8—C32—C31 | 117.8 (4) | C35—C36—H15 | 119.766 |
C27—C32—C31 | 121.1 (5) | C37—C36—H15 | 119.759 |
N3—C35—C36 | 122.4 (4) | C36—C37—H16 | 118.701 |
N3—C35—C48 | 117.8 (4) | C38—C37—H16 | 118.703 |
C36—C35—C48 | 119.7 (4) | C38—C39—H17 | 119.453 |
C35—C36—C37 | 120.5 (5) | C40—C39—H17 | 119.455 |
C36—C37—C38 | 122.6 (5) | C39—C40—H18 | 119.272 |
C37—C38—C39 | 122.9 (4) | C41—C40—H18 | 119.285 |
C37—C38—C49 | 117.6 (4) | C41—C42—H19 | 118.690 |
C39—C38—C49 | 119.5 (4) | C43—C42—H19 | 118.680 |
C38—C39—C40 | 121.1 (5) | C42—C43—H20 | 119.993 |
C39—C40—C41 | 121.4 (5) | C44—C43—H20 | 119.988 |
C40—C41—C42 | 122.6 (5) | C45—C46—H21 | 118.664 |
C40—C41—C50 | 119.2 (4) | C47—C46—H21 | 118.660 |
C42—C41—C50 | 118.2 (4) | C46—C47—H22 | 119.110 |
C41—C42—C43 | 122.6 (5) | C48—C47—H22 | 119.111 |
C42—C43—C44 | 120.0 (5) | C52—C53—H26 | 119.085 |
N4—C44—C43 | 122.2 (4) | C54—C53—H26 | 119.065 |
N4—C44—C45 | 117.9 (4) | C53—C54—H27 | 119.532 |
C43—C44—C45 | 119.9 (4) | C55—C54—H27 | 119.532 |
C44—C45—C46 | 123.7 (4) | C54—C55—H28 | 120.381 |
C44—C45—C50 | 119.4 (4) | C56—C55—H28 | 120.392 |
C46—C45—C50 | 116.9 (4) | O5—C58—H44 | 109.471 |
C45—C46—C47 | 122.7 (4) | O5—C58—H45 | 109.473 |
C46—C47—C48 | 121.8 (4) | O5—C58—H46 | 109.466 |
C35—C48—C47 | 123.2 (4) | H44—C58—H45 | 109.476 |
C35—C48—C49 | 118.9 (4) | H44—C58—H46 | 109.469 |
C47—C48—C49 | 117.8 (4) | H45—C58—H46 | 109.472 |
C38—C49—C48 | 120.7 (4) | O6—C59—H50 | 109.474 |
C38—C49—C50 | 119.2 (4) | O6—C59—H51 | 109.470 |
C48—C49—C50 | 120.0 (4) | O6—C59—H52 | 109.470 |
C41—C50—C45 | 119.7 (4) | H50—C59—H51 | 109.471 |
C41—C50—C49 | 119.5 (4) | H50—C59—H52 | 109.472 |
C45—C50—C49 | 120.8 (4) | H51—C59—H52 | 109.469 |
O4—C51—N3 | 123.2 (5) | C61—C62—H23 | 119.719 |
O4—C51—C52 | 119.6 (5) | C63—C62—H23 | 119.715 |
N3—C51—C52 | 117.2 (4) | C62—C63—H24 | 119.521 |
C51—C52—C53 | 116.4 (4) | C64—C63—H24 | 119.516 |
C51—C52—C57 | 125.8 (5) | C63—C64—H25 | 120.297 |
C53—C52—C57 | 117.8 (4) | C65—C64—H25 | 120.306 |
C52—C53—C54 | 121.8 (5) | O2—C67—H35 | 109.469 |
C53—C54—C55 | 120.9 (5) | O2—C67—H36 | 109.468 |
C54—C55—C56 | 119.2 (5) | O2—C67—H37 | 109.468 |
O6—C56—C55 | 125.0 (5) | H35—C67—H36 | 109.475 |
O6—C56—C57 | 115.3 (4) | H35—C67—H37 | 109.474 |
C55—C56—C57 | 119.7 (5) | H36—C67—H37 | 109.474 |
O5—C57—C52 | 122.3 (4) | O1—C68—H38 | 109.465 |
O5—C57—C56 | 117.3 (4) | O1—C68—H39 | 109.467 |
C52—C57—C56 | 120.5 (4) | O1—C68—H40 | 109.473 |
O3—C60—N4 | 122.6 (5) | H38—C68—H39 | 109.468 |
O3—C60—C61 | 120.6 (5) | H38—C68—H40 | 109.475 |
N4—C60—C61 | 116.7 (4) | H39—C68—H40 | 109.479 |
O1—C65—C64—C63 | −180.0 (5) | C12—C13—C14—C15 | −2.5 (7) |
O1—C65—C66—O2 | −0.3 (7) | C13—C12—C11—C16 | 0.1 (7) |
O1—C65—C66—C61 | 180.0 (4) | C13—C14—C15—C16 | −0.3 (7) |
O2—C66—C61—C60 | −1.7 (8) | C14—C1—N1—C17 | 162.7 (5) |
O2—C66—C61—C62 | −180.0 (4) | C17—C18—C19—C20 | 177.0 (5) |
O2—C66—C65—C64 | 178.2 (4) | C17—C18—C23—C22 | −176.6 (5) |
O3—C60—N4—C44 | −0.1 (9) | C18—C19—C20—C21 | 0.3 (9) |
O3—C60—C61—C62 | −22.6 (8) | C18—C23—O11—C24 | 102.9 (5) |
O3—C60—C61—C66 | 159.1 (6) | C18—C23—C22—C21 | −0.8 (8) |
O4—C51—N3—C35 | 3.8 (8) | C19—C18—C23—C22 | 2.2 (7) |
O4—C51—C52—C53 | 6.9 (7) | C19—C20—C21—C22 | 1.1 (9) |
O4—C51—C52—C57 | −171.6 (5) | C20—C19—C18—C23 | −1.9 (8) |
O5—C57—C52—C51 | −1.1 (7) | C20—C21—C22—C23 | −0.9 (8) |
O5—C57—C52—C53 | −179.6 (4) | C21—C22—O12—C25 | −4.4 (8) |
O5—C57—C56—O6 | −2.1 (6) | C22—C23—O11—C24 | −79.0 (5) |
O5—C57—C56—C55 | 178.4 (4) | C23—C22—O12—C25 | 176.9 (5) |
O6—C56—C55—C54 | −178.3 (5) | C26—C27—C28—C29 | 178.3 (4) |
O6—C56—C57—C52 | 179.1 (4) | C26—C27—C32—C31 | −178.9 (5) |
O7—C31—C30—C29 | 178.6 (5) | C27—C28—C29—C30 | 0.1 (8) |
O7—C31—C32—O8 | 0.8 (7) | C27—C32—O8—C33 | −103.3 (5) |
O7—C31—C32—C27 | −178.3 (4) | C27—C32—C31—C30 | 1.5 (8) |
O8—C32—C27—C26 | 2.1 (8) | C28—C27—C32—C31 | −0.9 (7) |
O8—C32—C27—C28 | −180.0 (4) | C28—C29—C30—C31 | 0.5 (8) |
O8—C32—C31—C30 | −179.4 (4) | C29—C28—C27—C32 | 0.1 (8) |
O9—C26—N2—C10 | −3.0 (8) | C29—C30—C31—C32 | −1.3 (8) |
O9—C26—C27—C28 | −9.5 (7) | C30—C31—O7—C34 | 13.9 (7) |
O9—C26—C27—C32 | 168.5 (5) | C31—C32—O8—C33 | 77.6 (5) |
O10—C17—N1—C1 | −1.6 (9) | C32—C31—O7—C34 | −166.3 (4) |
O10—C17—C18—C19 | 18.9 (7) | C35—N3—C51—C52 | −176.7 (4) |
O10—C17—C18—C23 | −162.2 (5) | C35—C36—C37—C38 | 1.3 (8) |
O11—C23—C18—C17 | 1.5 (7) | C35—C48—C47—C46 | −177.0 (5) |
O11—C23—C18—C19 | −179.7 (4) | C35—C48—C49—C38 | −1.1 (7) |
O11—C23—C22—O12 | −0.2 (7) | C35—C48—C49—C50 | 177.8 (4) |
O11—C23—C22—C21 | −178.9 (5) | C36—C35—N3—C51 | −19.4 (8) |
O12—C22—C21—C20 | −179.5 (5) | C36—C35—C48—C47 | 177.9 (5) |
O12—C22—C23—C18 | 178.0 (4) | C36—C35—C48—C49 | 1.7 (7) |
N1—C1—C2—C3 | 178.8 (5) | C36—C37—C38—C39 | 179.5 (5) |
N1—C1—C14—C13 | 1.5 (8) | C36—C37—C38—C49 | −0.6 (8) |
N1—C1—C14—C15 | −177.9 (4) | C37—C36—C35—C48 | −1.9 (7) |
N1—C17—C18—C19 | −157.8 (5) | C37—C38—C39—C40 | −179.1 (5) |
N1—C17—C18—C23 | 21.0 (7) | C37—C38—C49—C48 | 0.5 (7) |
N2—C10—C9—C8 | −176.7 (5) | C37—C38—C49—C50 | −178.3 (5) |
N2—C10—C11—C12 | 0.2 (7) | C38—C39—C40—C41 | −2.5 (8) |
N2—C10—C11—C16 | 178.3 (4) | C38—C49—C48—C47 | −177.5 (4) |
N2—C26—C27—C28 | 168.9 (4) | C38—C49—C50—C41 | −2.5 (7) |
N2—C26—C27—C32 | −13.1 (7) | C38—C49—C50—C45 | 177.9 (4) |
N3—C35—C36—C37 | 175.0 (5) | C39—C38—C49—C48 | −179.6 (5) |
N3—C35—C48—C47 | 1.0 (7) | C39—C38—C49—C50 | 1.6 (7) |
N3—C35—C48—C49 | −175.2 (4) | C39—C40—C41—C42 | −178.4 (5) |
N3—C51—C52—C53 | −172.6 (4) | C39—C40—C41—C50 | 1.4 (8) |
N3—C51—C52—C57 | 8.9 (7) | C40—C39—C38—C49 | 1.0 (8) |
N4—C44—C43—C42 | 178.0 (5) | C40—C41—C42—C43 | 177.4 (5) |
N4—C44—C45—C46 | 1.4 (7) | C40—C41—C50—C45 | −179.3 (5) |
N4—C44—C45—C50 | −179.9 (4) | C40—C41—C50—C49 | 1.1 (7) |
N4—C60—C61—C62 | 153.9 (5) | C41—C42—C43—C44 | 2.1 (8) |
N4—C60—C61—C66 | −24.4 (8) | C41—C50—C45—C44 | 1.6 (7) |
C1—N1—C17—C18 | 175.0 (5) | C41—C50—C45—C46 | −179.6 (4) |
C1—C2—C3—C4 | −1.6 (8) | C41—C50—C49—C48 | 178.6 (4) |
C1—C14—C13—C12 | 178.1 (5) | C42—C41—C50—C45 | 0.5 (7) |
C1—C14—C15—C4 | −0.4 (7) | C42—C41—C50—C49 | −179.1 (5) |
C1—C14—C15—C16 | 179.1 (4) | C42—C43—C44—C45 | 0.1 (8) |
C2—C1—N1—C17 | −19.0 (8) | C43—C42—C41—C50 | −2.4 (8) |
C2—C1—C14—C13 | −176.8 (4) | C43—C44—N4—C60 | 22.4 (8) |
C2—C1—C14—C15 | 3.8 (7) | C43—C44—C45—C46 | 179.4 (5) |
C2—C3—C4—C5 | −176.0 (5) | C43—C44—C45—C50 | −2.0 (7) |
C2—C3—C4—C15 | 5.0 (8) | C44—N4—C60—C61 | −176.5 (5) |
C3—C2—C1—C14 | −2.9 (7) | C44—C45—C46—C47 | 179.4 (5) |
C3—C4—C5—C6 | 179.8 (5) | C44—C45—C50—C49 | −178.8 (5) |
C3—C4—C15—C14 | −3.9 (7) | C45—C44—N4—C60 | −159.6 (5) |
C3—C4—C15—C16 | 176.6 (5) | C45—C46—C47—C48 | −0.3 (8) |
C4—C5—C6—C7 | 3.7 (9) | C45—C50—C49—C48 | −1.0 (7) |
C4—C15—C14—C13 | −179.8 (4) | C46—C45—C50—C49 | −0.1 (7) |
C4—C15—C16—C7 | 3.5 (7) | C46—C47—C48—C49 | −0.7 (7) |
C4—C15—C16—C11 | −177.5 (4) | C47—C46—C45—C50 | 0.7 (7) |
C5—C4—C15—C14 | 177.0 (5) | C47—C48—C49—C50 | 1.4 (7) |
C5—C4—C15—C16 | −2.4 (7) | C48—C35—N3—C51 | 157.5 (5) |
C5—C6—C7—C8 | 175.7 (5) | C51—C52—C53—C54 | −177.3 (5) |
C5—C6—C7—C16 | −2.5 (8) | C51—C52—C57—C56 | 177.6 (5) |
C6—C5—C4—C15 | −1.2 (8) | C52—C53—C54—C55 | −0.7 (8) |
C6—C7—C8—C9 | −178.3 (5) | C52—C57—O5—C58 | 103.9 (5) |
C6—C7—C16—C11 | 179.8 (5) | C52—C57—C56—C55 | −0.4 (7) |
C6—C7—C16—C15 | −1.2 (7) | C53—C52—C57—C56 | −0.8 (7) |
C7—C8—C9—C10 | −0.8 (8) | C53—C54—C55—C56 | −0.6 (8) |
C7—C16—C11—C10 | −2.1 (7) | C54—C53—C52—C57 | 1.4 (8) |
C7—C16—C11—C12 | 176.1 (4) | C54—C55—C56—C57 | 1.1 (8) |
C7—C16—C15—C14 | −175.9 (4) | C55—C56—O6—C59 | 0.6 (7) |
C8—C7—C16—C11 | 1.5 (7) | C56—C57—O5—C58 | −74.9 (5) |
C8—C7—C16—C15 | −179.5 (5) | C57—C56—O6—C59 | −178.8 (4) |
C8—C9—C10—C11 | 0.2 (8) | C60—C61—C62—C63 | −176.5 (5) |
C9—C8—C7—C16 | −0.1 (8) | C60—C61—C66—C65 | 178.0 (5) |
C9—C10—N2—C26 | 23.2 (7) | C61—C62—C63—C64 | −1.7 (9) |
C9—C10—C11—C12 | −176.8 (5) | C61—C66—O2—C67 | −99.2 (5) |
C9—C10—C11—C16 | 1.3 (7) | C61—C66—C65—C64 | −1.6 (8) |
C10—N2—C26—C27 | 178.6 (4) | C62—C61—C66—C65 | −0.2 (8) |
C10—C11—C12—C13 | 178.2 (5) | C62—C63—C64—C65 | −0.1 (9) |
C10—C11—C16—C15 | 178.9 (4) | C63—C62—C61—C66 | 1.9 (8) |
C11—C10—N2—C26 | −153.7 (5) | C63—C64—C65—C66 | 1.7 (8) |
C11—C12—C13—C14 | 2.7 (8) | C64—C65—O1—C68 | 9.4 (8) |
C11—C16—C15—C14 | 3.1 (7) | C65—C66—O2—C67 | 81.1 (5) |
C12—C11—C16—C15 | −2.9 (7) | C66—C65—O1—C68 | −172.3 (5) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1/2, −y, z−1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) −x+1, y−1/2, −z+1/2; (vi) −x+1/2, −y+1, z+1/2; (vii) −x+1/2, −y, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H53···O11 | 0.96 (6) | 1.95 (5) | 2.700 (6) | 134 (4) |
N2—H54···O8 | 0.95 (4) | 2.00 (4) | 2.746 (5) | 134 (4) |
N3—H55···O5 | 0.95 (6) | 1.96 (6) | 2.723 (5) | 136 (5) |
N4—H56···O2 | 0.94 (6) | 2.03 (5) | 2.727 (5) | 130 (4) |
Experimental details
Crystal data | |
Chemical formula | C34H28N2O6 |
Mr | 560.60 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 141 |
a, b, c (Å) | 12.5065 (9), 15.074 (1), 28.223 (2) |
V (Å3) | 5320.8 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.24 × 0.18 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART 1000 |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.914, 0.993 |
No. of measured, independent and observed [F2 > 3σ(F2)] reflections | 23940, 5011, 3491 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.588 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.053, 2.16 |
No. of reflections | 3491 |
No. of parameters | 473 |
No. of restraints | ? |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.30 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SIR97 (Altomare et al., 1999), TEXSAN (Molecular Structure Corporation, 1999), PLEASE PROVIDE, TEXSAN.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H53···O11 | 0.96 (6) | 1.95 (5) | 2.700 (6) | 134 (4) |
N2—H54···O8 | 0.95 (4) | 2.00 (4) | 2.746 (5) | 134 (4) |
N3—H55···O5 | 0.95 (6) | 1.96 (6) | 2.723 (5) | 136 (5) |
N4—H56···O2 | 0.94 (6) | 2.03 (5) | 2.727 (5) | 130 (4) |
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The title compound, (I), cyrstallizes in space group P212121 with a pseudo-inversion center that lies between the two molecules of the asymmetric unit. The pseudo-inversion center is not located at coordinates appropriate to generate a centrosymmetric space group. The structure exhibits C—N, C—C, and C—O bond lengths and angles typical for common organic molecules. There are intramolecular hydrogen bonds located between the amide NH groups and the methoxy oxygen atoms for both molecules (Table 1).
Intermolecular distances between pyrene and catechol-derived rings range between 3.753 (7) Å and 3.800 (7) Å. These can be attributed to weak π–π interactions (Janiak, 2000). Such intermolecular contacts are not unexpected in a molecule with many aromatic rings. The aromatic rings do not stack closer to one another because the methoxy groups are positioned between the ring systems. Interplanar angles between the pyrene and a catechol-derivative ring range from 7.85–12.25 degrees. The angle between the two pyrene rings in the asymmetric unit is 3.38 degrees. The angle between catechol-derivative rings of the same molecule ranges from 5.93 to 11.24 degrees. Deviations from planarity between rings within the same molecule are most likely a result of the molecule accomodating favorable π–π interactions.