Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015020393/hb7516sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2056989015020393/hb7516Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015020393/hb7516Isup3.cml |
CCDC reference: 1433643
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.051
- wR factor = 0.124
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 30 % PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.956 Note PLAT410_ALERT_2_B Short Intra H...H Contact H4A .. H23 .. 1.84 Ang.
Alert level C CRYSC01_ALERT_1_C The word below has not been recognised as a standard identifier. broun CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour. GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.649 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) Range 3.6 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Uiso(max)/Uiso(min) ... 4.1 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 -- C3 .. 5.3 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 -- C10 .. 6.7 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 -- C20 .. 5.3 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C18 -- C27 .. 5.3 su PLAT241_ALERT_2_C High Ueq as Compared to Neighbors for ..... C39 Check PLAT241_ALERT_2_C High Ueq as Compared to Neighbors for ..... C40 Check PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... C23 Check PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... C31 Check PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... C38 Check PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... C41 Check PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C38 -C43 1.37 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0046 Ang. PLAT410_ALERT_2_C Short Intra H...H Contact H14 .. H28 .. 1.91 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 39.239 Check PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 7.116 Check PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.919 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 90 Report
Alert level G PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C5 -C10 1.43 Ang. PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C15 -C20 1.42 Ang. PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety ..... C26 Check PLAT606_ALERT_4_G VERY LARGE Solvent Accessible VOID(S) in Structure ! Info PLAT869_ALERT_4_G ALERTS Related to the use of SQUEEZE Suppressed ! Info PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 2 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 294 Note PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check
0 ALERT level A = Most likely a serious problem - resolve or explain 3 ALERT level B = A potentially serious problem, consider carefully 22 ALERT level C = Check. Ensure it is not caused by an omission or oversight 11 ALERT level G = General information/check it is not something unexpected 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 17 ALERT type 2 Indicator that the structure model may be wrong or deficient 9 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C44H44N2O8 | Z = 2 |
Mr = 728.81 | F(000) = 772 |
Triclinic, P1 | Dx = 0.983 Mg m−3 |
a = 11.6622 (9) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 14.0738 (11) Å | Cell parameters from 2564 reflections |
c = 15.6906 (10) Å | θ = 3.9–70.6° |
α = 82.472 (6)° | µ = 0.55 mm−1 |
β = 84.831 (6)° | T = 293 K |
γ = 75.009 (7)° | Prism, broun |
V = 2462.0 (3) Å3 | 0.40 × 0.32 × 0.27 mm |
Oxford Diffraction Xcalibur Ruby diffractometer | 9019 independent reflections |
Radiation source: fine-focus sealed tube | 2706 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
Detector resolution: 10.2576 pixels mm-1 | θmax = 70.6°, θmin = 3.9° |
ω scans | h = −14→13 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | k = −16→16 |
Tmin = 0.811, Tmax = 0.862 | l = −18→16 |
18952 measured reflections |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.65 | w = 1/[σ2(Fo2) + (0.0542P)2] where P = (Fo2 + 2Fc2)/3 |
9019 reflections | (Δ/σ)max < 0.001 |
519 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Experimental. Absorption correction: CrysAlisPro, Oxford Diffraction (2009), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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. |
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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.06997 (18) | 0.40724 (17) | 0.33397 (13) | 0.0668 (6) | |
O2 | −0.6101 (2) | 0.2359 (2) | 0.58343 (19) | 0.1250 (10) | |
O3 | −0.23580 (18) | 0.62089 (16) | 0.58330 (12) | 0.0774 (6) | |
O4 | −0.1425 (2) | 0.7699 (2) | 0.55783 (17) | 0.0923 (8) | |
O5 | 0.27695 (17) | 0.35008 (18) | 0.24986 (14) | 0.0741 (7) | |
O6 | 0.97592 (18) | 0.21416 (17) | 0.27160 (14) | 0.0886 (7) | |
O7 | 0.46897 (19) | 0.06734 (18) | 0.07019 (15) | 0.1002 (9) | |
O8 | 0.3149 (2) | 0.06336 (18) | −0.03842 (14) | 0.0887 (8) | |
N1 | −0.2902 (2) | 0.4750 (2) | 0.53257 (17) | 0.0736 (8) | |
N2 | 0.5550 (2) | 0.1627 (2) | 0.16491 (18) | 0.0824 (9) | |
C1 | −0.0203 (2) | 0.4872 (2) | 0.32283 (17) | 0.0543 (7) | |
C2 | 0.0593 (2) | 0.4959 (2) | 0.25382 (17) | 0.0546 (8) | |
C3 | 0.1135 (3) | 0.5752 (2) | 0.24359 (18) | 0.0657 (9) | |
C4 | 0.0827 (3) | 0.6422 (2) | 0.30335 (19) | 0.0677 (9) | |
H4A | 0.1188 | 0.6946 | 0.2968 | 0.081* | |
C5 | −0.0267 (3) | 0.7112 (2) | 0.43314 (19) | 0.0680 (9) | |
C6 | −0.1066 (3) | 0.7018 (2) | 0.4998 (2) | 0.0681 (9) | |
C7 | −0.1641 (3) | 0.6211 (2) | 0.51583 (18) | 0.0627 (9) | |
C8 | −0.1427 (2) | 0.5498 (2) | 0.45576 (17) | 0.0570 (8) | |
C9 | −0.0561 (2) | 0.5568 (2) | 0.38381 (17) | 0.0537 (8) | |
C10 | 0.0002 (2) | 0.6367 (2) | 0.37361 (18) | 0.0600 (8) | |
C11 | 0.1982 (2) | 0.3535 (2) | 0.18905 (16) | 0.0563 (8) | |
C12 | 0.0890 (2) | 0.4206 (2) | 0.19037 (17) | 0.0587 (8) | |
C13 | 0.0074 (2) | 0.4204 (2) | 0.12890 (17) | 0.0615 (8) | |
C14 | 0.0405 (3) | 0.3496 (2) | 0.07254 (17) | 0.0688 (9) | |
H14 | −0.0149 | 0.3470 | 0.0344 | 0.083* | |
C15 | 0.1802 (2) | 0.2079 (2) | 0.00811 (18) | 0.0623 (8) | |
C16 | 0.2827 (3) | 0.1384 (2) | 0.01332 (18) | 0.0677 (9) | |
C17 | 0.3742 (3) | 0.1370 (3) | 0.07291 (19) | 0.0730 (10) | |
C18 | 0.3505 (2) | 0.2143 (2) | 0.12572 (17) | 0.0601 (8) | |
C19 | 0.2357 (2) | 0.2845 (2) | 0.12808 (17) | 0.0571 (8) | |
C20 | 0.1511 (2) | 0.2814 (2) | 0.06846 (17) | 0.0591 (8) | |
C21 | 0.1981 (3) | 0.5900 (2) | 0.16700 (19) | 0.0862 (11) | |
H21A | 0.2164 | 0.6529 | 0.1662 | 0.129* | |
H21B | 0.1616 | 0.5886 | 0.1149 | 0.129* | |
H21C | 0.2700 | 0.5381 | 0.1713 | 0.129* | |
C22 | −0.2114 (3) | 0.4812 (2) | 0.46653 (19) | 0.0642 (8) | |
H22 | −0.2017 | 0.4374 | 0.4254 | 0.077* | |
C23 | 0.0276 (4) | 0.7993 (3) | 0.4206 (2) | 0.0993 (13) | |
H23 | 0.0914 | 0.7849 | 0.3755 | 0.119* | |
C24 | 0.0868 (4) | 0.8144 (3) | 0.4976 (3) | 0.1269 (15) | |
H24A | 0.1543 | 0.8405 | 0.4785 | 0.190* | |
H24B | 0.1126 | 0.7522 | 0.5323 | 0.190* | |
H24C | 0.0313 | 0.8601 | 0.5312 | 0.190* | |
C25 | −0.0552 (5) | 0.8930 (4) | 0.3869 (3) | 0.192 (3) | |
H25A | −0.0664 | 0.8912 | 0.3274 | 0.288* | |
H25B | −0.0226 | 0.9478 | 0.3925 | 0.288* | |
H25C | −0.1304 | 0.9008 | 0.4192 | 0.288* | |
C26 | −0.1129 (3) | 0.4922 (2) | 0.12655 (19) | 0.0819 (10) | |
H26A | −0.1553 | 0.4803 | 0.0810 | 0.123* | |
H26B | −0.1035 | 0.5586 | 0.1166 | 0.123* | |
H26C | −0.1567 | 0.4836 | 0.1806 | 0.123* | |
C27 | 0.4492 (3) | 0.2255 (2) | 0.16703 (18) | 0.0742 (10) | |
H27 | 0.4385 | 0.2801 | 0.1972 | 0.089* | |
C28 | 0.0952 (3) | 0.2073 (3) | −0.0607 (2) | 0.0935 (13) | |
H28 | 0.0313 | 0.2681 | −0.0592 | 0.112* | |
C29 | 0.1528 (3) | 0.2089 (3) | −0.1511 (2) | 0.1217 (16) | |
H29A | 0.1918 | 0.2619 | −0.1618 | 0.183* | |
H29B | 0.0930 | 0.2187 | −0.1919 | 0.183* | |
H29C | 0.2101 | 0.1471 | −0.1571 | 0.183* | |
C30 | 0.0377 (4) | 0.1211 (4) | −0.0378 (3) | 0.1432 (19) | |
H30A | −0.0126 | 0.1310 | 0.0138 | 0.215* | |
H30B | 0.0985 | 0.0606 | −0.0287 | 0.215* | |
H30C | −0.0089 | 0.1174 | −0.0841 | 0.215* | |
C31 | −0.3701 (3) | 0.4116 (3) | 0.5449 (2) | 0.0736 (9) | |
C32 | −0.4309 (3) | 0.4051 (3) | 0.6236 (2) | 0.1032 (13) | |
H32 | −0.4178 | 0.4399 | 0.6668 | 0.124* | |
C33 | −0.5130 (3) | 0.3461 (3) | 0.6395 (3) | 0.1062 (13) | |
H33 | −0.5537 | 0.3408 | 0.6930 | 0.127* | |
C34 | −0.5315 (3) | 0.2971 (3) | 0.5753 (3) | 0.0971 (12) | |
C35 | −0.4745 (3) | 0.3059 (3) | 0.4958 (3) | 0.1026 (12) | |
H35 | −0.4903 | 0.2730 | 0.4523 | 0.123* | |
C36 | −0.3941 (3) | 0.3627 (3) | 0.4797 (2) | 0.0961 (12) | |
H36 | −0.3558 | 0.3686 | 0.4254 | 0.115* | |
C37 | −0.6735 (3) | 0.2272 (4) | 0.6640 (3) | 0.1379 (18) | |
H37A | −0.7292 | 0.1883 | 0.6609 | 0.207* | |
H37B | −0.7155 | 0.2919 | 0.6782 | 0.207* | |
H37C | −0.6188 | 0.1956 | 0.7074 | 0.207* | |
C38 | 0.6624 (3) | 0.1761 (3) | 0.1948 (2) | 0.0750 (10) | |
C39 | 0.6640 (3) | 0.2563 (3) | 0.2352 (2) | 0.1141 (15) | |
H39 | 0.5938 | 0.3032 | 0.2470 | 0.137* | |
C40 | 0.7716 (3) | 0.2665 (3) | 0.2581 (2) | 0.1103 (14) | |
H40 | 0.7740 | 0.3230 | 0.2821 | 0.132* | |
C41 | 0.8741 (3) | 0.1953 (3) | 0.24610 (19) | 0.0739 (10) | |
C42 | 0.8717 (3) | 0.1150 (3) | 0.2073 (2) | 0.0886 (11) | |
H42 | 0.9415 | 0.0669 | 0.1976 | 0.106* | |
C43 | 0.7637 (3) | 0.1053 (3) | 0.1821 (2) | 0.0935 (12) | |
H43 | 0.7616 | 0.0499 | 0.1565 | 0.112* | |
C44 | 1.0825 (3) | 0.1378 (2) | 0.2661 (2) | 0.0842 (10) | |
H44A | 1.1459 | 0.1576 | 0.2882 | 0.126* | |
H44B | 1.1024 | 0.1261 | 0.2070 | 0.126* | |
H44C | 1.0713 | 0.0783 | 0.2993 | 0.126* | |
H1A | −0.302 (4) | 0.518 (4) | 0.577 (3) | 0.20 (2)* | |
H2 | 0.571 (3) | 0.109 (2) | 0.1344 (19) | 0.095 (11)* | |
H1 | −0.023 (3) | 0.352 (3) | 0.313 (2) | 0.133 (16)* | |
H4 | −0.184 (3) | 0.745 (3) | 0.598 (2) | 0.122 (18)* | |
H5 | 0.243 (2) | 0.381 (2) | 0.2898 (17) | 0.071 (10)* | |
H8 | 0.397 (3) | 0.023 (3) | −0.037 (2) | 0.124 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0682 (13) | 0.0589 (16) | 0.0781 (14) | −0.0206 (12) | 0.0069 (11) | −0.0238 (12) |
O2 | 0.099 (2) | 0.146 (3) | 0.140 (3) | −0.063 (2) | −0.0104 (18) | 0.017 (2) |
O3 | 0.0750 (14) | 0.0936 (19) | 0.0625 (13) | −0.0130 (12) | 0.0044 (11) | −0.0264 (12) |
O4 | 0.0997 (19) | 0.099 (2) | 0.0850 (18) | −0.0209 (16) | 0.0106 (15) | −0.0536 (16) |
O5 | 0.0574 (13) | 0.0986 (19) | 0.0710 (14) | −0.0096 (12) | −0.0063 (11) | −0.0454 (14) |
O6 | 0.0646 (14) | 0.0966 (19) | 0.1167 (18) | −0.0211 (14) | −0.0188 (13) | −0.0442 (15) |
O7 | 0.0664 (14) | 0.106 (2) | 0.130 (2) | 0.0146 (14) | −0.0295 (13) | −0.0754 (16) |
O8 | 0.0720 (15) | 0.0960 (19) | 0.1022 (17) | 0.0015 (14) | −0.0224 (13) | −0.0600 (15) |
N1 | 0.0690 (18) | 0.085 (2) | 0.0626 (18) | −0.0132 (16) | 0.0030 (15) | −0.0088 (16) |
N2 | 0.0558 (17) | 0.091 (2) | 0.106 (2) | −0.0032 (16) | −0.0107 (14) | −0.0588 (19) |
C1 | 0.0517 (17) | 0.050 (2) | 0.0596 (19) | −0.0086 (15) | −0.0007 (15) | −0.0118 (15) |
C2 | 0.0550 (17) | 0.055 (2) | 0.0539 (18) | −0.0107 (16) | 0.0007 (15) | −0.0152 (15) |
C3 | 0.0634 (19) | 0.074 (2) | 0.0596 (19) | −0.0141 (18) | 0.0024 (15) | −0.0169 (17) |
C4 | 0.072 (2) | 0.056 (2) | 0.080 (2) | −0.0191 (17) | −0.0099 (18) | −0.0172 (18) |
C5 | 0.083 (2) | 0.063 (2) | 0.061 (2) | −0.0160 (18) | −0.0017 (17) | −0.0223 (17) |
C6 | 0.067 (2) | 0.070 (2) | 0.067 (2) | −0.0036 (18) | −0.0080 (17) | −0.0309 (18) |
C7 | 0.0558 (19) | 0.068 (2) | 0.056 (2) | 0.0051 (17) | −0.0085 (16) | −0.0172 (17) |
C8 | 0.0521 (17) | 0.060 (2) | 0.0576 (18) | −0.0088 (16) | −0.0031 (15) | −0.0136 (16) |
C9 | 0.0474 (16) | 0.054 (2) | 0.0570 (18) | −0.0038 (15) | −0.0039 (14) | −0.0151 (15) |
C10 | 0.0609 (19) | 0.057 (2) | 0.063 (2) | −0.0113 (16) | −0.0017 (16) | −0.0186 (16) |
C11 | 0.0543 (18) | 0.067 (2) | 0.0513 (17) | −0.0173 (16) | 0.0010 (14) | −0.0202 (15) |
C12 | 0.0559 (19) | 0.065 (2) | 0.0545 (18) | −0.0082 (16) | 0.0002 (15) | −0.0191 (16) |
C13 | 0.0612 (19) | 0.061 (2) | 0.0595 (18) | −0.0050 (16) | −0.0022 (15) | −0.0184 (16) |
C14 | 0.064 (2) | 0.085 (3) | 0.0593 (19) | −0.0121 (18) | −0.0081 (15) | −0.0252 (18) |
C15 | 0.0551 (18) | 0.066 (2) | 0.067 (2) | −0.0084 (17) | −0.0084 (15) | −0.0228 (17) |
C16 | 0.062 (2) | 0.074 (2) | 0.074 (2) | −0.0143 (18) | −0.0047 (16) | −0.0385 (18) |
C17 | 0.061 (2) | 0.080 (3) | 0.082 (2) | −0.0069 (19) | −0.0089 (17) | −0.040 (2) |
C18 | 0.0492 (17) | 0.070 (2) | 0.0641 (19) | −0.0088 (16) | −0.0069 (14) | −0.0295 (17) |
C19 | 0.0486 (17) | 0.066 (2) | 0.0601 (18) | −0.0123 (15) | 0.0012 (14) | −0.0242 (16) |
C20 | 0.0532 (18) | 0.064 (2) | 0.0594 (18) | −0.0062 (16) | −0.0010 (14) | −0.0234 (16) |
C21 | 0.086 (2) | 0.088 (3) | 0.090 (2) | −0.034 (2) | 0.026 (2) | −0.028 (2) |
C22 | 0.0582 (18) | 0.066 (2) | 0.066 (2) | −0.0066 (17) | 0.0035 (16) | −0.0186 (16) |
C23 | 0.133 (3) | 0.092 (3) | 0.091 (3) | −0.053 (3) | 0.019 (2) | −0.043 (2) |
C24 | 0.125 (3) | 0.111 (4) | 0.168 (4) | −0.061 (3) | −0.048 (3) | −0.013 (3) |
C25 | 0.273 (7) | 0.104 (4) | 0.234 (6) | −0.104 (5) | −0.152 (5) | 0.065 (4) |
C26 | 0.068 (2) | 0.094 (3) | 0.079 (2) | −0.0016 (19) | −0.0089 (17) | −0.026 (2) |
C27 | 0.058 (2) | 0.083 (3) | 0.085 (2) | −0.0089 (18) | −0.0003 (17) | −0.0433 (19) |
C28 | 0.076 (2) | 0.118 (3) | 0.086 (3) | 0.005 (2) | −0.026 (2) | −0.052 (2) |
C29 | 0.148 (4) | 0.126 (4) | 0.082 (3) | 0.007 (3) | −0.035 (3) | −0.042 (2) |
C30 | 0.101 (3) | 0.199 (5) | 0.166 (4) | −0.074 (3) | −0.020 (3) | −0.070 (4) |
C31 | 0.060 (2) | 0.085 (3) | 0.073 (2) | −0.0167 (19) | 0.0062 (18) | −0.0060 (19) |
C32 | 0.099 (3) | 0.129 (4) | 0.080 (3) | −0.035 (3) | 0.005 (2) | −0.002 (2) |
C33 | 0.094 (3) | 0.134 (4) | 0.093 (3) | −0.046 (3) | 0.010 (2) | 0.006 (3) |
C34 | 0.074 (2) | 0.105 (4) | 0.109 (3) | −0.032 (2) | 0.002 (2) | 0.012 (3) |
C35 | 0.085 (3) | 0.112 (4) | 0.121 (3) | −0.045 (3) | 0.003 (2) | −0.015 (3) |
C36 | 0.086 (3) | 0.114 (3) | 0.094 (3) | −0.036 (2) | 0.014 (2) | −0.025 (2) |
C37 | 0.094 (3) | 0.185 (5) | 0.128 (4) | −0.057 (3) | −0.009 (3) | 0.054 (3) |
C38 | 0.0506 (18) | 0.088 (3) | 0.093 (2) | −0.0087 (18) | −0.0132 (16) | −0.047 (2) |
C39 | 0.069 (2) | 0.121 (3) | 0.164 (4) | −0.003 (2) | −0.015 (2) | −0.097 (3) |
C40 | 0.071 (2) | 0.118 (3) | 0.161 (4) | −0.016 (2) | −0.021 (2) | −0.088 (3) |
C41 | 0.061 (2) | 0.084 (3) | 0.084 (2) | −0.0150 (19) | −0.0073 (17) | −0.037 (2) |
C42 | 0.056 (2) | 0.090 (3) | 0.125 (3) | −0.0051 (19) | −0.0157 (19) | −0.051 (2) |
C43 | 0.063 (2) | 0.087 (3) | 0.140 (3) | −0.007 (2) | −0.015 (2) | −0.068 (2) |
C44 | 0.064 (2) | 0.089 (3) | 0.105 (3) | −0.020 (2) | −0.0120 (19) | −0.023 (2) |
O1—C1 | 1.379 (3) | C21—H21B | 0.9600 |
O1—H1 | 0.91 (4) | C21—H21C | 0.9600 |
O2—C34 | 1.398 (4) | C22—H22 | 0.9300 |
O2—C37 | 1.413 (4) | C23—H23 | 0.9800 |
O3—C7 | 1.289 (3) | C23—C24 | 1.508 (4) |
O4—C6 | 1.371 (3) | C23—C25 | 1.484 (5) |
O4—H4 | 0.86 (3) | C24—H24A | 0.9600 |
O5—C11 | 1.371 (3) | C24—H24B | 0.9600 |
O5—H5 | 0.82 (3) | C24—H24C | 0.9600 |
O6—C41 | 1.384 (3) | C25—H25A | 0.9600 |
O6—C44 | 1.422 (3) | C25—H25B | 0.9600 |
O7—C17 | 1.275 (3) | C25—H25C | 0.9600 |
O8—C16 | 1.371 (3) | C26—H26A | 0.9600 |
O8—H8 | 0.98 (3) | C26—H26B | 0.9600 |
N1—C22 | 1.332 (4) | C26—H26C | 0.9600 |
N1—C31 | 1.433 (4) | C27—H27 | 0.9300 |
N1—H1A | 0.95 (5) | C28—H28 | 0.9800 |
N2—C27 | 1.319 (4) | C28—C29 | 1.514 (4) |
N2—C38 | 1.441 (4) | C28—C30 | 1.521 (5) |
N2—H2 | 0.92 (3) | C29—H29A | 0.9600 |
C1—C2 | 1.376 (3) | C29—H29B | 0.9600 |
C1—C9 | 1.417 (3) | C29—H29C | 0.9600 |
C2—C3 | 1.403 (4) | C30—H30A | 0.9600 |
C2—C12 | 1.502 (4) | C30—H30B | 0.9600 |
C3—C4 | 1.376 (4) | C30—H30C | 0.9600 |
C3—C21 | 1.513 (4) | C31—C32 | 1.373 (4) |
C4—H4A | 0.9300 | C31—C36 | 1.391 (4) |
C4—C10 | 1.404 (4) | C32—H32 | 0.9300 |
C5—C6 | 1.353 (4) | C32—C33 | 1.409 (5) |
C5—C10 | 1.450 (4) | C33—H33 | 0.9300 |
C5—C23 | 1.516 (5) | C33—C34 | 1.354 (5) |
C6—C7 | 1.446 (4) | C34—C35 | 1.367 (5) |
C7—C8 | 1.426 (4) | C35—H35 | 0.9300 |
C8—C9 | 1.456 (4) | C35—C36 | 1.368 (5) |
C8—C22 | 1.390 (4) | C36—H36 | 0.9300 |
C9—C10 | 1.428 (4) | C37—H37A | 0.9600 |
C11—C12 | 1.376 (4) | C37—H37B | 0.9600 |
C11—C19 | 1.414 (3) | C37—H37C | 0.9600 |
C12—C13 | 1.415 (4) | C38—C39 | 1.369 (4) |
C13—C14 | 1.376 (3) | C38—C43 | 1.353 (4) |
C13—C26 | 1.502 (4) | C39—H39 | 0.9300 |
C14—H14 | 0.9300 | C39—C40 | 1.383 (4) |
C14—C20 | 1.397 (4) | C40—H40 | 0.9300 |
C15—C16 | 1.336 (4) | C40—C41 | 1.364 (4) |
C15—C20 | 1.449 (3) | C41—C42 | 1.359 (4) |
C15—C28 | 1.532 (4) | C42—H42 | 0.9300 |
C16—C17 | 1.476 (4) | C42—C43 | 1.398 (4) |
C17—C18 | 1.409 (4) | C43—H43 | 0.9300 |
C18—C19 | 1.445 (4) | C44—H44A | 0.9600 |
C18—C27 | 1.423 (4) | C44—H44B | 0.9600 |
C19—C20 | 1.431 (4) | C44—H44C | 0.9600 |
C21—H21A | 0.9600 | ||
C1—O1—H1 | 114 (2) | C23—C24—H24A | 109.5 |
C34—O2—C37 | 116.4 (4) | C23—C24—H24B | 109.5 |
C6—O4—H4 | 107 (3) | C23—C24—H24C | 109.5 |
C11—O5—H5 | 110 (2) | H24A—C24—H24B | 109.5 |
C41—O6—C44 | 116.8 (2) | H24A—C24—H24C | 109.5 |
C16—O8—H8 | 117 (2) | H24B—C24—H24C | 109.5 |
C22—N1—C31 | 126.7 (3) | C23—C25—H25A | 109.5 |
C22—N1—H1A | 121 (3) | C23—C25—H25B | 109.5 |
C31—N1—H1A | 112 (3) | C23—C25—H25C | 109.5 |
C27—N2—C38 | 126.5 (3) | H25A—C25—H25B | 109.5 |
C27—N2—H2 | 122 (2) | H25A—C25—H25C | 109.5 |
C38—N2—H2 | 111 (2) | H25B—C25—H25C | 109.5 |
O1—C1—C9 | 117.2 (3) | C13—C26—H26A | 109.5 |
C2—C1—O1 | 119.0 (2) | C13—C26—H26B | 109.5 |
C2—C1—C9 | 123.8 (3) | C13—C26—H26C | 109.5 |
C1—C2—C3 | 119.4 (3) | H26A—C26—H26B | 109.5 |
C1—C2—C12 | 120.3 (3) | H26A—C26—H26C | 109.5 |
C3—C2—C12 | 120.2 (3) | H26B—C26—H26C | 109.5 |
C2—C3—C21 | 121.4 (3) | N2—C27—C18 | 123.6 (3) |
C4—C3—C2 | 117.8 (3) | N2—C27—H27 | 118.2 |
C4—C3—C21 | 120.7 (3) | C18—C27—H27 | 118.2 |
C3—C4—H4A | 117.8 | C15—C28—H28 | 106.9 |
C3—C4—C10 | 124.3 (3) | C29—C28—C15 | 113.3 (3) |
C10—C4—H4A | 117.8 | C29—C28—H28 | 106.9 |
C6—C5—C10 | 117.5 (3) | C29—C28—C30 | 112.2 (3) |
C6—C5—C23 | 120.2 (3) | C30—C28—C15 | 110.2 (3) |
C10—C5—C23 | 122.3 (3) | C30—C28—H28 | 106.9 |
O4—C6—C7 | 113.5 (3) | C28—C29—H29A | 109.5 |
C5—C6—O4 | 122.6 (3) | C28—C29—H29B | 109.5 |
C5—C6—C7 | 123.9 (3) | C28—C29—H29C | 109.5 |
O3—C7—C6 | 116.7 (3) | H29A—C29—H29B | 109.5 |
O3—C7—C8 | 124.1 (3) | H29A—C29—H29C | 109.5 |
C8—C7—C6 | 119.2 (3) | H29B—C29—H29C | 109.5 |
C7—C8—C9 | 118.4 (3) | C28—C30—H30A | 109.5 |
C22—C8—C7 | 117.8 (3) | C28—C30—H30B | 109.5 |
C22—C8—C9 | 123.8 (3) | C28—C30—H30C | 109.5 |
C1—C9—C8 | 124.3 (3) | H30A—C30—H30B | 109.5 |
C1—C9—C10 | 116.4 (3) | H30A—C30—H30C | 109.5 |
C10—C9—C8 | 119.2 (2) | H30B—C30—H30C | 109.5 |
C4—C10—C5 | 120.2 (3) | C32—C31—N1 | 117.3 (3) |
C4—C10—C9 | 118.1 (3) | C32—C31—C36 | 119.3 (4) |
C9—C10—C5 | 121.7 (3) | C36—C31—N1 | 123.2 (3) |
O5—C11—C12 | 120.1 (2) | C31—C32—H32 | 119.8 |
O5—C11—C19 | 116.3 (2) | C31—C32—C33 | 120.4 (4) |
C12—C11—C19 | 123.6 (2) | C33—C32—H32 | 119.8 |
C11—C12—C2 | 120.2 (2) | C32—C33—H33 | 120.6 |
C11—C12—C13 | 119.1 (2) | C34—C33—C32 | 118.7 (4) |
C13—C12—C2 | 120.7 (2) | C34—C33—H33 | 120.6 |
C12—C13—C26 | 121.7 (2) | C33—C34—O2 | 124.0 (4) |
C14—C13—C12 | 117.6 (3) | C33—C34—C35 | 121.3 (4) |
C14—C13—C26 | 120.7 (3) | C35—C34—O2 | 114.7 (4) |
C13—C14—H14 | 117.6 | C34—C35—H35 | 119.7 |
C13—C14—C20 | 124.8 (3) | C34—C35—C36 | 120.5 (4) |
C20—C14—H14 | 117.6 | C36—C35—H35 | 119.7 |
C16—C15—C20 | 119.2 (3) | C31—C36—H36 | 120.1 |
C16—C15—C28 | 119.3 (3) | C35—C36—C31 | 119.7 (4) |
C20—C15—C28 | 121.4 (3) | C35—C36—H36 | 120.1 |
O8—C16—C17 | 113.5 (3) | O2—C37—H37A | 109.5 |
C15—C16—O8 | 123.2 (3) | O2—C37—H37B | 109.5 |
C15—C16—C17 | 123.4 (3) | O2—C37—H37C | 109.5 |
O7—C17—C16 | 116.9 (3) | H37A—C37—H37B | 109.5 |
O7—C17—C18 | 126.0 (3) | H37A—C37—H37C | 109.5 |
C18—C17—C16 | 117.1 (3) | H37B—C37—H37C | 109.5 |
C17—C18—C19 | 120.7 (2) | C39—C38—N2 | 122.5 (3) |
C17—C18—C27 | 116.1 (2) | C43—C38—N2 | 117.3 (3) |
C27—C18—C19 | 122.7 (2) | C43—C38—C39 | 120.2 (3) |
C11—C19—C18 | 124.1 (2) | C38—C39—H39 | 120.5 |
C11—C19—C20 | 117.1 (2) | C38—C39—C40 | 119.0 (3) |
C20—C19—C18 | 118.7 (2) | C40—C39—H39 | 120.5 |
C14—C20—C15 | 122.2 (3) | C39—C40—H40 | 119.5 |
C14—C20—C19 | 117.6 (2) | C41—C40—C39 | 121.1 (3) |
C19—C20—C15 | 120.2 (2) | C41—C40—H40 | 119.5 |
C3—C21—H21A | 109.5 | C40—C41—O6 | 115.6 (3) |
C3—C21—H21B | 109.5 | C42—C41—O6 | 124.7 (3) |
C3—C21—H21C | 109.5 | C42—C41—C40 | 119.5 (3) |
H21A—C21—H21B | 109.5 | C41—C42—H42 | 120.2 |
H21A—C21—H21C | 109.5 | C41—C42—C43 | 119.6 (3) |
H21B—C21—H21C | 109.5 | C43—C42—H42 | 120.2 |
N1—C22—C8 | 123.5 (3) | C38—C43—C42 | 120.3 (3) |
N1—C22—H22 | 118.3 | C38—C43—H43 | 119.8 |
C8—C22—H22 | 118.3 | C42—C43—H43 | 119.8 |
C5—C23—H23 | 105.6 | O6—C44—H44A | 109.5 |
C24—C23—C5 | 115.0 (3) | O6—C44—H44B | 109.5 |
C24—C23—H23 | 105.6 | O6—C44—H44C | 109.5 |
C25—C23—C5 | 113.6 (4) | H44A—C44—H44B | 109.5 |
C25—C23—H23 | 105.6 | H44A—C44—H44C | 109.5 |
C25—C23—C24 | 110.6 (3) | H44B—C44—H44C | 109.5 |
O1—C1—C2—C3 | −177.8 (3) | C12—C11—C19—C18 | 179.5 (3) |
O1—C1—C2—C12 | 1.6 (4) | C12—C11—C19—C20 | −4.0 (5) |
O1—C1—C9—C8 | −1.1 (4) | C12—C13—C14—C20 | −3.7 (5) |
O1—C1—C9—C10 | 177.2 (2) | C13—C14—C20—C15 | 179.4 (3) |
O2—C34—C35—C36 | −179.2 (4) | C13—C14—C20—C19 | 1.0 (5) |
O3—C7—C8—C9 | −177.9 (2) | C15—C16—C17—O7 | −178.8 (3) |
O3—C7—C8—C22 | 6.1 (4) | C15—C16—C17—C18 | −0.6 (5) |
O4—C6—C7—O3 | −3.1 (4) | C16—C15—C20—C14 | −173.1 (3) |
O4—C6—C7—C8 | 174.5 (3) | C16—C15—C20—C19 | 5.2 (5) |
O5—C11—C12—C2 | 5.0 (4) | C16—C15—C28—C29 | −55.0 (5) |
O5—C11—C12—C13 | −177.7 (3) | C16—C15—C28—C30 | 71.5 (4) |
O5—C11—C19—C18 | −1.5 (5) | C16—C17—C18—C19 | 7.1 (5) |
O5—C11—C19—C20 | 175.0 (3) | C16—C17—C18—C27 | −165.5 (3) |
O6—C41—C42—C43 | −178.1 (3) | C17—C18—C19—C11 | 169.1 (3) |
O7—C17—C18—C19 | −174.9 (3) | C17—C18—C19—C20 | −7.3 (5) |
O7—C17—C18—C27 | 12.5 (5) | C17—C18—C27—N2 | −6.9 (5) |
O8—C16—C17—O7 | −1.0 (5) | C18—C19—C20—C14 | 179.5 (3) |
O8—C16—C17—C18 | 177.2 (3) | C18—C19—C20—C15 | 1.1 (5) |
N1—C31—C32—C33 | 178.5 (3) | C19—C11—C12—C2 | −176.0 (3) |
N1—C31—C36—C35 | −177.9 (3) | C19—C11—C12—C13 | 1.3 (5) |
N2—C38—C39—C40 | −176.7 (4) | C19—C18—C27—N2 | −179.3 (3) |
N2—C38—C43—C42 | 178.2 (3) | C20—C15—C16—O8 | 176.9 (3) |
C1—C2—C3—C4 | −0.9 (4) | C20—C15—C16—C17 | −5.5 (5) |
C1—C2—C3—C21 | −177.7 (3) | C20—C15—C28—C29 | 125.8 (3) |
C1—C2—C12—C11 | −107.7 (3) | C20—C15—C28—C30 | −107.6 (4) |
C1—C2—C12—C13 | 75.0 (4) | C21—C3—C4—C10 | 176.5 (3) |
C1—C9—C10—C4 | 2.1 (4) | C22—N1—C31—C32 | 169.9 (3) |
C1—C9—C10—C5 | −178.4 (3) | C22—N1—C31—C36 | −14.6 (5) |
C2—C1—C9—C8 | 178.3 (3) | C22—C8—C9—C1 | −8.7 (4) |
C2—C1—C9—C10 | −3.4 (4) | C22—C8—C9—C10 | 173.1 (3) |
C2—C3—C4—C10 | −0.3 (5) | C23—C5—C6—O4 | 0.4 (5) |
C2—C12—C13—C14 | 179.8 (3) | C23—C5—C6—C7 | 179.0 (3) |
C2—C12—C13—C26 | −2.3 (5) | C23—C5—C10—C4 | 2.7 (5) |
C3—C2—C12—C11 | 71.7 (4) | C23—C5—C10—C9 | −176.8 (3) |
C3—C2—C12—C13 | −105.6 (3) | C26—C13—C14—C20 | 178.4 (3) |
C3—C4—C10—C5 | −179.9 (3) | C27—N2—C38—C39 | 4.3 (6) |
C3—C4—C10—C9 | −0.3 (4) | C27—N2—C38—C43 | −176.1 (3) |
C5—C6—C7—O3 | 178.2 (3) | C27—C18—C19—C11 | −18.8 (5) |
C5—C6—C7—C8 | −4.3 (5) | C27—C18—C19—C20 | 164.8 (3) |
C6—C5—C10—C4 | −179.8 (3) | C28—C15—C16—O8 | −2.3 (5) |
C6—C5—C10—C9 | 0.7 (4) | C28—C15—C16—C17 | 175.3 (3) |
C6—C5—C23—C24 | 54.8 (5) | C28—C15—C20—C14 | 6.0 (5) |
C6—C5—C23—C25 | −74.1 (4) | C28—C15—C20—C19 | −175.6 (3) |
C6—C7—C8—C9 | 4.7 (4) | C31—N1—C22—C8 | 175.1 (3) |
C6—C7—C8—C22 | −171.3 (3) | C31—C32—C33—C34 | −0.8 (6) |
C7—C8—C9—C1 | 175.5 (3) | C32—C31—C36—C35 | −2.5 (6) |
C7—C8—C9—C10 | −2.7 (4) | C32—C33—C34—O2 | 179.6 (4) |
C7—C8—C22—N1 | −4.3 (4) | C32—C33—C34—C35 | −1.5 (7) |
C8—C9—C10—C4 | −179.5 (3) | C33—C34—C35—C36 | 1.8 (6) |
C8—C9—C10—C5 | 0.0 (4) | C34—C35—C36—C31 | 0.2 (6) |
C9—C1—C2—C3 | 2.9 (4) | C36—C31—C32—C33 | 2.8 (6) |
C9—C1—C2—C12 | −177.7 (3) | C37—O2—C34—C33 | 0.8 (6) |
C9—C8—C22—N1 | 179.9 (3) | C37—O2—C34—C35 | −178.2 (3) |
C10—C5—C6—O4 | −177.2 (3) | C38—N2—C27—C18 | 170.9 (3) |
C10—C5—C6—C7 | 1.5 (5) | C38—C39—C40—C41 | −4.2 (7) |
C10—C5—C23—C24 | −127.8 (3) | C39—C38—C43—C42 | −2.2 (6) |
C10—C5—C23—C25 | 103.3 (4) | C39—C40—C41—O6 | 180.0 (4) |
C11—C12—C13—C14 | 2.5 (5) | C39—C40—C41—C42 | 3.1 (6) |
C11—C12—C13—C26 | −179.6 (3) | C40—C41—C42—C43 | −1.6 (6) |
C11—C19—C20—C14 | 2.8 (4) | C41—C42—C43—C38 | 1.1 (6) |
C11—C19—C20—C15 | −175.6 (3) | C43—C38—C39—C40 | 3.7 (6) |
C12—C2—C3—C4 | 179.7 (3) | C44—O6—C41—C40 | 175.3 (3) |
C12—C2—C3—C21 | 2.9 (4) | C44—O6—C41—C42 | −8.1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3 | 0.95 (5) | 1.83 (5) | 2.538 (4) | 129 (4) |
N2—H2···O7 | 0.92 (3) | 1.87 (3) | 2.550 (3) | 129 (3) |
O1—H1···O6i | 0.91 (4) | 2.13 (4) | 2.912 (3) | 144 (3) |
O4—H4···O3 | 0.86 (3) | 2.04 (4) | 2.574 (4) | 119 (3) |
O5—H5···O3ii | 0.82 (3) | 1.98 (3) | 2.684 (3) | 143 (3) |
O8—H8···O7 | 0.98 (3) | 2.17 (3) | 2.601 (3) | 105 (2) |
O8—H8···O7iii | 0.98 (3) | 1.83 (3) | 2.757 (3) | 158 (3) |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y, −z. |