Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700428X/bt2256sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680700428X/bt2256Isup2.hkl |
CCDC reference: 618046
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.037
- wR factor = 0.076
- Data-to-parameter ratio = 8.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.99 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C32 - C37 .. 5.71 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C38 - C40 .. 5.88 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT412_ALERT_2_C Short Intra XH3 .. XHn H22B .. H40B .. 1.87 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
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 25.02 From the CIF: _reflns_number_total 3389 Count of symmetry unique reflns 3401 Completeness (_total/calc) 99.65% 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 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: RAPID-AUTO (Rigaku, 2000); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.
C21H27NO | F(000) = 672 |
Mr = 309.44 | Dx = 1.114 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2697 (13) Å | Cell parameters from 10713 reflections |
b = 16.168 (3) Å | θ = 2.6–25.0° |
c = 18.260 (4) Å | µ = 0.07 mm−1 |
β = 94.60 (3)° | T = 293 K |
V = 1845.0 (6) Å3 | Block, colourless |
Z = 4 | 0.50 × 0.45 × 0.12 mm |
Rigaku R-AXIS RAPID image-plate diffractometer | 3389 independent reflections |
Radiation source: fine-focus sealed tube | 2089 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 10.00 pixels mm-1 | θmax = 25.0°, θmin = 2.6° |
Ω scans | h = −7→7 |
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995) | k = −19→19 |
Tmin = 0.967, Tmax = 0.992 | l = −21→21 |
10713 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom or difmap |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.027P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.001 |
3389 reflections | Δρmax = 0.16 e Å−3 |
424 parameters | Δρmin = −0.13 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.074 (2) |
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 | 0.4567 (3) | 0.9951 (2) | 0.90945 (11) | 0.0538 (6) | |
HO1 | 0.481 (6) | 1.055 (3) | 0.9099 (19) | 0.097 (14)* | |
O2 | 0.5526 (3) | 0.4558 (2) | 0.55357 (13) | 0.0549 (6) | |
HO2 | 0.559 (6) | 0.421 (2) | 0.515 (2) | 0.098 (16)* | |
N1 | 0.6059 (5) | 1.15110 (18) | 0.87459 (14) | 0.0621 (8) | |
N2 | 0.6158 (4) | 0.32346 (18) | 0.46635 (13) | 0.0563 (7) | |
C1 | 0.6550 (6) | 1.1077 (2) | 0.80766 (17) | 0.0635 (10) | |
H1A | 0.7009 | 1.1481 | 0.7729 | 0.076* | |
H1B | 0.5249 | 1.0823 | 0.7859 | 0.076* | |
C2 | 0.8257 (5) | 1.0418 (2) | 0.81882 (14) | 0.0552 (9) | |
H2 | 0.9710 | 1.0623 | 0.8140 | 0.066* | |
C3 | 0.8165 (5) | 0.96729 (19) | 0.87137 (14) | 0.0496 (8) | |
H3 | 0.9603 | 0.9509 | 0.8911 | 0.060* | |
C4 | 0.6514 (5) | 0.9497 (2) | 0.92625 (15) | 0.0454 (8) | |
C5 | 0.7349 (5) | 0.97082 (18) | 1.00602 (15) | 0.0484 (8) | |
C6 | 0.9350 (6) | 1.0016 (2) | 1.02677 (18) | 0.0659 (10) | |
H6 | 1.0308 | 1.0114 | 0.9914 | 0.079* | |
C7 | 0.9949 (7) | 1.0183 (2) | 1.0998 (2) | 0.0812 (13) | |
H7 | 1.1294 | 1.0405 | 1.1129 | 0.097* | |
C8 | 0.8591 (8) | 1.0026 (2) | 1.1529 (2) | 0.0803 (12) | |
H8 | 0.9018 | 1.0132 | 1.2020 | 0.096* | |
C9 | 0.6600 (8) | 0.9712 (2) | 1.13356 (18) | 0.0746 (11) | |
H9 | 0.5664 | 0.9607 | 1.1694 | 0.089* | |
C10 | 0.5980 (6) | 0.9551 (2) | 1.06044 (17) | 0.0608 (9) | |
H10 | 0.4627 | 0.9336 | 1.0476 | 0.073* | |
C11 | 0.5993 (5) | 0.85797 (19) | 0.92379 (15) | 0.0446 (8) | |
C12 | 0.3978 (6) | 0.8279 (2) | 0.90163 (17) | 0.0621 (9) | |
H12 | 0.2883 | 0.8648 | 0.8876 | 0.075* | |
C13 | 0.3566 (7) | 0.7438 (3) | 0.9000 (2) | 0.0742 (11) | |
H13 | 0.2198 | 0.7248 | 0.8852 | 0.089* | |
C14 | 0.5159 (8) | 0.6884 (2) | 0.9198 (2) | 0.0783 (13) | |
H14 | 0.4877 | 0.6319 | 0.9185 | 0.094* | |
C15 | 0.7172 (8) | 0.7166 (2) | 0.94171 (19) | 0.0735 (12) | |
H15 | 0.8257 | 0.6792 | 0.9557 | 0.088* | |
C16 | 0.7587 (6) | 0.8005 (2) | 0.94301 (16) | 0.0576 (9) | |
H16 | 0.8964 | 0.8189 | 0.9571 | 0.069* | |
C17 | 0.7876 (5) | 0.9540 (2) | 0.78896 (15) | 0.0509 (8) | |
C18 | 0.5734 (5) | 0.9311 (2) | 0.75188 (16) | 0.0690 (11) | |
H18A | 0.4626 | 0.9586 | 0.7758 | 0.103* | |
H18B | 0.5538 | 0.8723 | 0.7548 | 0.103* | |
H18C | 0.5669 | 0.9476 | 0.7012 | 0.103* | |
C19 | 0.9706 (6) | 0.9121 (2) | 0.75433 (17) | 0.0736 (11) | |
H19A | 1.1037 | 0.9279 | 0.7802 | 0.110* | |
H19B | 0.9702 | 0.9285 | 0.7038 | 0.110* | |
H19C | 0.9538 | 0.8531 | 0.7571 | 0.110* | |
C20 | 0.7942 (7) | 1.1954 (3) | 0.9070 (2) | 0.0894 (13) | |
H20A | 0.7590 | 1.2230 | 0.9510 | 0.134* | |
H20B | 0.8389 | 1.2355 | 0.8726 | 0.134* | |
H20C | 0.9082 | 1.1568 | 0.9187 | 0.134* | |
C21 | 0.4286 (7) | 1.2093 (2) | 0.8572 (2) | 0.0914 (13) | |
H21A | 0.3066 | 1.1797 | 0.8356 | 0.137* | |
H21B | 0.4717 | 1.2502 | 0.8233 | 0.137* | |
H21C | 0.3919 | 1.2359 | 0.9015 | 0.137* | |
C22 | 0.6997 (6) | 0.2854 (2) | 0.53611 (17) | 0.0652 (10) | |
H22A | 0.7317 | 0.2278 | 0.5271 | 0.078* | |
H22B | 0.5885 | 0.2869 | 0.5701 | 0.078* | |
C23 | 0.8972 (5) | 0.32602 (19) | 0.57201 (15) | 0.0517 (8) | |
H23 | 1.0298 | 0.2993 | 0.5595 | 0.062* | |
C24 | 0.9255 (5) | 0.41844 (18) | 0.58918 (15) | 0.0478 (8) | |
H24 | 1.0736 | 0.4364 | 0.5857 | 0.057* | |
C25 | 0.7665 (5) | 0.48670 (18) | 0.56599 (15) | 0.0445 (8) | |
C26 | 0.7655 (5) | 0.55076 (19) | 0.62732 (15) | 0.0473 (8) | |
C27 | 0.9439 (6) | 0.5995 (2) | 0.64531 (17) | 0.0579 (9) | |
H27 | 1.0637 | 0.5941 | 0.6187 | 0.070* | |
C28 | 0.9467 (7) | 0.6563 (2) | 0.70243 (19) | 0.0689 (11) | |
H28 | 1.0685 | 0.6880 | 0.7141 | 0.083* | |
C29 | 0.7714 (8) | 0.6661 (2) | 0.74170 (19) | 0.0735 (11) | |
H29 | 0.7737 | 0.7040 | 0.7801 | 0.088* | |
C30 | 0.5910 (7) | 0.6190 (3) | 0.7237 (2) | 0.0769 (11) | |
H30 | 0.4705 | 0.6258 | 0.7497 | 0.092* | |
C31 | 0.5882 (6) | 0.5619 (2) | 0.66747 (18) | 0.0639 (10) | |
H31 | 0.4659 | 0.5305 | 0.6562 | 0.077* | |
C32 | 0.8254 (5) | 0.52993 (18) | 0.49466 (16) | 0.0463 (8) | |
C33 | 1.0225 (6) | 0.5258 (2) | 0.46656 (18) | 0.0657 (10) | |
H33 | 1.1318 | 0.4952 | 0.4911 | 0.079* | |
C34 | 1.0599 (7) | 0.5669 (2) | 0.4016 (2) | 0.0775 (11) | |
H34 | 1.1945 | 0.5640 | 0.3837 | 0.093* | |
C35 | 0.9025 (9) | 0.6109 (2) | 0.3643 (2) | 0.0819 (12) | |
H35 | 0.9271 | 0.6365 | 0.3201 | 0.098* | |
C36 | 0.7087 (8) | 0.6173 (3) | 0.3919 (2) | 0.0832 (12) | |
H36 | 0.6015 | 0.6490 | 0.3675 | 0.100* | |
C37 | 0.6699 (6) | 0.5769 (2) | 0.45641 (19) | 0.0672 (10) | |
H37 | 0.5357 | 0.5815 | 0.4744 | 0.081* | |
C38 | 0.9078 (5) | 0.35643 (19) | 0.65091 (17) | 0.0507 (8) | |
C39 | 1.1132 (6) | 0.3378 (2) | 0.69741 (19) | 0.0777 (11) | |
H39A | 1.2316 | 0.3399 | 0.6672 | 0.116* | |
H39B | 1.1045 | 0.2836 | 0.7185 | 0.116* | |
H39C | 1.1336 | 0.3781 | 0.7360 | 0.116* | |
C40 | 0.7142 (6) | 0.3532 (2) | 0.69333 (18) | 0.0746 (11) | |
H40A | 0.7318 | 0.3105 | 0.7299 | 0.112* | |
H40B | 0.5905 | 0.3414 | 0.6606 | 0.112* | |
H40C | 0.6958 | 0.4055 | 0.7169 | 0.112* | |
C41 | 0.4150 (6) | 0.2827 (3) | 0.43890 (19) | 0.0861 (13) | |
H41A | 0.3139 | 0.2858 | 0.4756 | 0.129* | |
H41B | 0.4429 | 0.2258 | 0.4282 | 0.129* | |
H41C | 0.3573 | 0.3100 | 0.3950 | 0.129* | |
C42 | 0.7733 (6) | 0.3204 (3) | 0.41183 (18) | 0.0894 (13) | |
H42A | 0.7149 | 0.3459 | 0.3671 | 0.134* | |
H42B | 0.8086 | 0.2639 | 0.4024 | 0.134* | |
H42C | 0.9000 | 0.3496 | 0.4301 | 0.134* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0441 (15) | 0.0572 (16) | 0.0609 (14) | 0.0073 (12) | 0.0087 (11) | 0.0137 (12) |
O2 | 0.0414 (15) | 0.0559 (14) | 0.0673 (15) | −0.0030 (12) | 0.0043 (11) | −0.0010 (13) |
N1 | 0.074 (2) | 0.0601 (18) | 0.0533 (17) | 0.0034 (17) | 0.0127 (16) | 0.0062 (15) |
N2 | 0.0567 (19) | 0.0626 (18) | 0.0491 (15) | −0.0036 (16) | 0.0016 (14) | 0.0005 (15) |
C1 | 0.080 (3) | 0.056 (2) | 0.055 (2) | 0.010 (2) | 0.0128 (19) | 0.0132 (18) |
C2 | 0.052 (2) | 0.067 (2) | 0.0475 (18) | −0.0064 (19) | 0.0055 (16) | 0.0105 (18) |
C3 | 0.0388 (19) | 0.062 (2) | 0.0487 (17) | 0.0012 (17) | 0.0071 (14) | 0.0104 (17) |
C4 | 0.038 (2) | 0.0494 (18) | 0.0488 (18) | 0.0008 (17) | 0.0044 (15) | 0.0077 (16) |
C5 | 0.060 (2) | 0.0406 (18) | 0.0450 (17) | −0.0001 (17) | 0.0051 (16) | 0.0051 (16) |
C6 | 0.073 (3) | 0.070 (2) | 0.054 (2) | −0.015 (2) | −0.0005 (18) | 0.0041 (18) |
C7 | 0.103 (3) | 0.074 (3) | 0.063 (2) | −0.030 (3) | −0.013 (2) | 0.004 (2) |
C8 | 0.123 (4) | 0.063 (2) | 0.052 (2) | −0.010 (3) | −0.007 (3) | −0.0036 (19) |
C9 | 0.112 (4) | 0.064 (2) | 0.050 (2) | −0.001 (3) | 0.015 (2) | 0.001 (2) |
C10 | 0.071 (3) | 0.062 (2) | 0.0504 (19) | 0.002 (2) | 0.0104 (18) | −0.0005 (18) |
C11 | 0.045 (2) | 0.050 (2) | 0.0389 (16) | 0.0017 (18) | 0.0066 (15) | 0.0007 (16) |
C12 | 0.056 (3) | 0.068 (3) | 0.062 (2) | −0.007 (2) | 0.0055 (19) | 0.006 (2) |
C13 | 0.073 (3) | 0.075 (3) | 0.077 (3) | −0.021 (3) | 0.015 (2) | −0.006 (2) |
C14 | 0.116 (4) | 0.054 (2) | 0.068 (3) | −0.014 (3) | 0.028 (3) | −0.012 (2) |
C15 | 0.101 (4) | 0.049 (2) | 0.071 (3) | 0.010 (3) | 0.010 (2) | −0.006 (2) |
C16 | 0.063 (3) | 0.053 (2) | 0.057 (2) | 0.006 (2) | 0.0021 (18) | −0.0016 (17) |
C17 | 0.046 (2) | 0.064 (2) | 0.0439 (17) | −0.0024 (19) | 0.0092 (15) | 0.0009 (17) |
C18 | 0.065 (3) | 0.092 (3) | 0.0494 (18) | −0.008 (2) | 0.0006 (17) | −0.0035 (19) |
C19 | 0.069 (3) | 0.090 (3) | 0.065 (2) | 0.013 (2) | 0.023 (2) | 0.004 (2) |
C20 | 0.111 (4) | 0.078 (3) | 0.080 (3) | −0.014 (3) | 0.015 (3) | −0.014 (2) |
C21 | 0.119 (4) | 0.075 (3) | 0.083 (3) | 0.036 (3) | 0.030 (2) | 0.018 (2) |
C22 | 0.087 (3) | 0.049 (2) | 0.057 (2) | −0.009 (2) | −0.0048 (19) | −0.0002 (18) |
C23 | 0.053 (2) | 0.048 (2) | 0.0535 (19) | 0.0044 (18) | 0.0021 (16) | −0.0003 (16) |
C24 | 0.036 (2) | 0.052 (2) | 0.0557 (19) | 0.0012 (17) | 0.0053 (16) | 0.0060 (17) |
C25 | 0.035 (2) | 0.0447 (18) | 0.0537 (19) | 0.0005 (16) | 0.0030 (15) | −0.0008 (16) |
C26 | 0.050 (2) | 0.0462 (19) | 0.0465 (17) | 0.0053 (18) | 0.0081 (16) | 0.0062 (15) |
C27 | 0.060 (2) | 0.062 (2) | 0.052 (2) | −0.006 (2) | 0.0089 (18) | 0.0011 (18) |
C28 | 0.084 (3) | 0.066 (2) | 0.056 (2) | −0.009 (2) | 0.000 (2) | 0.000 (2) |
C29 | 0.116 (4) | 0.055 (2) | 0.052 (2) | 0.007 (3) | 0.018 (2) | −0.0008 (18) |
C30 | 0.088 (3) | 0.074 (3) | 0.072 (3) | 0.015 (3) | 0.030 (2) | −0.003 (2) |
C31 | 0.060 (3) | 0.061 (2) | 0.072 (2) | 0.003 (2) | 0.015 (2) | −0.005 (2) |
C32 | 0.048 (2) | 0.0415 (18) | 0.0499 (18) | 0.0016 (17) | 0.0042 (17) | −0.0002 (16) |
C33 | 0.062 (3) | 0.070 (3) | 0.067 (2) | 0.002 (2) | 0.013 (2) | 0.011 (2) |
C34 | 0.087 (3) | 0.077 (3) | 0.073 (2) | −0.012 (3) | 0.032 (2) | 0.007 (2) |
C35 | 0.129 (4) | 0.062 (2) | 0.057 (2) | 0.003 (3) | 0.019 (3) | 0.008 (2) |
C36 | 0.110 (4) | 0.084 (3) | 0.056 (2) | 0.024 (3) | 0.008 (2) | 0.010 (2) |
C37 | 0.074 (3) | 0.070 (2) | 0.058 (2) | 0.012 (2) | 0.010 (2) | 0.001 (2) |
C38 | 0.048 (2) | 0.053 (2) | 0.0508 (18) | 0.0012 (18) | 0.0020 (17) | 0.0034 (17) |
C39 | 0.076 (3) | 0.069 (2) | 0.082 (2) | 0.012 (2) | −0.025 (2) | −0.002 (2) |
C40 | 0.080 (3) | 0.083 (3) | 0.062 (2) | −0.008 (2) | 0.009 (2) | 0.014 (2) |
C41 | 0.088 (3) | 0.101 (3) | 0.067 (2) | −0.023 (3) | −0.007 (2) | −0.006 (2) |
C42 | 0.086 (3) | 0.126 (4) | 0.058 (2) | 0.016 (3) | 0.018 (2) | −0.002 (2) |
O1—C4 | 1.436 (4) | C20—H20B | 0.9600 |
O1—HO1 | 0.98 (4) | C20—H20C | 0.9600 |
O2—C25 | 1.432 (4) | C21—H21A | 0.9600 |
O2—HO2 | 0.90 (4) | C21—H21B | 0.9600 |
N1—C1 | 1.463 (4) | C21—H21C | 0.9600 |
N1—C20 | 1.466 (4) | C22—C23 | 1.505 (4) |
N1—C21 | 1.471 (4) | C22—H22A | 0.9700 |
N2—C42 | 1.458 (4) | C22—H22B | 0.9700 |
N2—C41 | 1.473 (4) | C23—C38 | 1.519 (4) |
N2—C22 | 1.473 (4) | C23—C24 | 1.534 (4) |
C1—C2 | 1.513 (4) | C23—H23 | 0.9800 |
C1—H1A | 0.9700 | C24—C38 | 1.519 (4) |
C1—H1B | 0.9700 | C24—C25 | 1.524 (4) |
C2—C17 | 1.532 (4) | C24—H24 | 0.9800 |
C2—C3 | 1.544 (4) | C25—C26 | 1.526 (4) |
C2—H2 | 0.9800 | C25—C32 | 1.549 (4) |
C3—C17 | 1.516 (4) | C26—C27 | 1.386 (4) |
C3—C4 | 1.524 (4) | C26—C31 | 1.392 (4) |
C3—H3 | 0.9800 | C27—C28 | 1.389 (5) |
C4—C11 | 1.518 (4) | C27—H27 | 0.9300 |
C4—C5 | 1.546 (4) | C28—C29 | 1.368 (5) |
C5—C6 | 1.374 (4) | C28—H28 | 0.9300 |
C5—C10 | 1.388 (4) | C29—C30 | 1.382 (5) |
C6—C7 | 1.383 (4) | C29—H29 | 0.9300 |
C6—H6 | 0.9300 | C30—C31 | 1.379 (5) |
C7—C8 | 1.365 (5) | C30—H30 | 0.9300 |
C7—H7 | 0.9300 | C31—H31 | 0.9300 |
C8—C9 | 1.368 (5) | C32—C33 | 1.377 (4) |
C8—H8 | 0.9300 | C32—C37 | 1.380 (4) |
C9—C10 | 1.385 (4) | C33—C34 | 1.397 (5) |
C9—H9 | 0.9300 | C33—H33 | 0.9300 |
C10—H10 | 0.9300 | C34—C35 | 1.355 (5) |
C11—C12 | 1.383 (4) | C34—H34 | 0.9300 |
C11—C16 | 1.389 (4) | C35—C36 | 1.357 (5) |
C12—C13 | 1.384 (5) | C35—H35 | 0.9300 |
C12—H12 | 0.9300 | C36—C37 | 1.385 (5) |
C13—C14 | 1.368 (5) | C36—H36 | 0.9300 |
C13—H13 | 0.9300 | C37—H37 | 0.9300 |
C14—C15 | 1.371 (5) | C38—C40 | 1.492 (4) |
C14—H14 | 0.9300 | C38—C39 | 1.515 (4) |
C15—C16 | 1.382 (5) | C39—H39A | 0.9600 |
C15—H15 | 0.9300 | C39—H39B | 0.9600 |
C16—H16 | 0.9300 | C39—H39C | 0.9600 |
C17—C18 | 1.501 (4) | C40—H40A | 0.9600 |
C17—C19 | 1.514 (4) | C40—H40B | 0.9600 |
C18—H18A | 0.9600 | C40—H40C | 0.9600 |
C18—H18B | 0.9600 | C41—H41A | 0.9600 |
C18—H18C | 0.9600 | C41—H41B | 0.9600 |
C19—H19A | 0.9600 | C41—H41C | 0.9600 |
C19—H19B | 0.9600 | C42—H42A | 0.9600 |
C19—H19C | 0.9600 | C42—H42B | 0.9600 |
C20—H20A | 0.9600 | C42—H42C | 0.9600 |
C4—O1—HO1 | 112 (2) | H21A—C21—H21B | 109.5 |
C25—O2—HO2 | 104 (3) | N1—C21—H21C | 109.5 |
C1—N1—C20 | 110.8 (3) | H21A—C21—H21C | 109.5 |
C1—N1—C21 | 109.4 (3) | H21B—C21—H21C | 109.5 |
C20—N1—C21 | 110.2 (3) | N2—C22—C23 | 114.8 (3) |
C42—N2—C41 | 111.1 (3) | N2—C22—H22A | 108.6 |
C42—N2—C22 | 111.3 (3) | C23—C22—H22A | 108.6 |
C41—N2—C22 | 110.1 (3) | N2—C22—H22B | 108.6 |
N1—C1—C2 | 114.8 (3) | C23—C22—H22B | 108.6 |
N1—C1—H1A | 108.6 | H22A—C22—H22B | 107.6 |
C2—C1—H1A | 108.6 | C22—C23—C38 | 121.8 (3) |
N1—C1—H1B | 108.6 | C22—C23—C24 | 126.2 (3) |
C2—C1—H1B | 108.6 | C38—C23—C24 | 59.69 (19) |
H1A—C1—H1B | 107.5 | C22—C23—H23 | 113.0 |
C1—C2—C17 | 121.1 (3) | C38—C23—H23 | 113.0 |
C1—C2—C3 | 124.9 (3) | C24—C23—H23 | 113.0 |
C17—C2—C3 | 59.09 (19) | C38—C24—C25 | 126.8 (3) |
C1—C2—H2 | 113.7 | C38—C24—C23 | 59.65 (19) |
C17—C2—H2 | 113.7 | C25—C24—C23 | 125.9 (3) |
C3—C2—H2 | 113.7 | C38—C24—H24 | 111.7 |
C17—C3—C4 | 126.3 (3) | C25—C24—H24 | 111.7 |
C17—C3—C2 | 60.05 (19) | C23—C24—H24 | 111.7 |
C4—C3—C2 | 128.0 (3) | O2—C25—C24 | 112.0 (3) |
C17—C3—H3 | 111.1 | O2—C25—C26 | 107.1 (3) |
C4—C3—H3 | 111.1 | C24—C25—C26 | 109.2 (2) |
C2—C3—H3 | 111.1 | O2—C25—C32 | 107.9 (2) |
O1—C4—C11 | 108.4 (3) | C24—C25—C32 | 111.5 (2) |
O1—C4—C3 | 112.0 (2) | C26—C25—C32 | 109.0 (2) |
C11—C4—C3 | 108.6 (3) | C27—C26—C31 | 117.7 (3) |
O1—C4—C5 | 107.8 (2) | C27—C26—C25 | 120.6 (3) |
C11—C4—C5 | 107.4 (2) | C31—C26—C25 | 121.7 (3) |
C3—C4—C5 | 112.4 (3) | C26—C27—C28 | 121.0 (3) |
C6—C5—C10 | 118.2 (3) | C26—C27—H27 | 119.5 |
C6—C5—C4 | 124.9 (3) | C28—C27—H27 | 119.5 |
C10—C5—C4 | 116.9 (3) | C29—C28—C27 | 120.5 (4) |
C5—C6—C7 | 120.5 (3) | C29—C28—H28 | 119.7 |
C5—C6—H6 | 119.7 | C27—C28—H28 | 119.7 |
C7—C6—H6 | 119.7 | C28—C29—C30 | 119.2 (3) |
C8—C7—C6 | 120.9 (4) | C28—C29—H29 | 120.4 |
C8—C7—H7 | 119.6 | C30—C29—H29 | 120.4 |
C6—C7—H7 | 119.6 | C31—C30—C29 | 120.5 (4) |
C7—C8—C9 | 119.6 (3) | C31—C30—H30 | 119.8 |
C7—C8—H8 | 120.2 | C29—C30—H30 | 119.8 |
C9—C8—H8 | 120.2 | C30—C31—C26 | 121.1 (4) |
C8—C9—C10 | 119.9 (4) | C30—C31—H31 | 119.5 |
C8—C9—H9 | 120.0 | C26—C31—H31 | 119.5 |
C10—C9—H9 | 120.0 | C33—C32—C37 | 117.2 (3) |
C9—C10—C5 | 120.9 (4) | C33—C32—C25 | 124.9 (3) |
C9—C10—H10 | 119.5 | C37—C32—C25 | 117.9 (3) |
C5—C10—H10 | 119.5 | C32—C33—C34 | 120.7 (4) |
C12—C11—C16 | 117.4 (3) | C32—C33—H33 | 119.7 |
C12—C11—C4 | 122.7 (3) | C34—C33—H33 | 119.7 |
C16—C11—C4 | 119.8 (3) | C35—C34—C33 | 120.8 (4) |
C11—C12—C13 | 121.1 (4) | C35—C34—H34 | 119.6 |
C11—C12—H12 | 119.5 | C33—C34—H34 | 119.6 |
C13—C12—H12 | 119.5 | C34—C35—C36 | 119.4 (4) |
C14—C13—C12 | 120.4 (4) | C34—C35—H35 | 120.3 |
C14—C13—H13 | 119.8 | C36—C35—H35 | 120.3 |
C12—C13—H13 | 119.8 | C35—C36—C37 | 120.3 (4) |
C13—C14—C15 | 119.7 (4) | C35—C36—H36 | 119.9 |
C13—C14—H14 | 120.2 | C37—C36—H36 | 119.9 |
C15—C14—H14 | 120.2 | C32—C37—C36 | 121.6 (4) |
C14—C15—C16 | 120.0 (4) | C32—C37—H37 | 119.2 |
C14—C15—H15 | 120.0 | C36—C37—H37 | 119.2 |
C16—C15—H15 | 120.0 | C40—C38—C39 | 113.1 (3) |
C15—C16—C11 | 121.5 (4) | C40—C38—C23 | 120.4 (3) |
C15—C16—H16 | 119.3 | C39—C38—C23 | 116.0 (3) |
C11—C16—H16 | 119.3 | C40—C38—C24 | 121.3 (3) |
C18—C17—C19 | 112.4 (3) | C39—C38—C24 | 116.0 (3) |
C18—C17—C3 | 120.9 (3) | C23—C38—C24 | 60.66 (19) |
C19—C17—C3 | 116.3 (3) | C38—C39—H39A | 109.5 |
C18—C17—C2 | 119.9 (3) | C38—C39—H39B | 109.5 |
C19—C17—C2 | 117.5 (3) | H39A—C39—H39B | 109.5 |
C3—C17—C2 | 60.86 (19) | C38—C39—H39C | 109.5 |
C17—C18—H18A | 109.5 | H39A—C39—H39C | 109.5 |
C17—C18—H18B | 109.5 | H39B—C39—H39C | 109.5 |
H18A—C18—H18B | 109.5 | C38—C40—H40A | 109.5 |
C17—C18—H18C | 109.5 | C38—C40—H40B | 109.5 |
H18A—C18—H18C | 109.5 | H40A—C40—H40B | 109.5 |
H18B—C18—H18C | 109.5 | C38—C40—H40C | 109.5 |
C17—C19—H19A | 109.5 | H40A—C40—H40C | 109.5 |
C17—C19—H19B | 109.5 | H40B—C40—H40C | 109.5 |
H19A—C19—H19B | 109.5 | N2—C41—H41A | 109.5 |
C17—C19—H19C | 109.5 | N2—C41—H41B | 109.5 |
H19A—C19—H19C | 109.5 | H41A—C41—H41B | 109.5 |
H19B—C19—H19C | 109.5 | N2—C41—H41C | 109.5 |
N1—C20—H20A | 109.5 | H41A—C41—H41C | 109.5 |
N1—C20—H20B | 109.5 | H41B—C41—H41C | 109.5 |
H20A—C20—H20B | 109.5 | N2—C42—H42A | 109.5 |
N1—C20—H20C | 109.5 | N2—C42—H42B | 109.5 |
H20A—C20—H20C | 109.5 | H42A—C42—H42B | 109.5 |
H20B—C20—H20C | 109.5 | N2—C42—H42C | 109.5 |
N1—C21—H21A | 109.5 | H42A—C42—H42C | 109.5 |
N1—C21—H21B | 109.5 | H42B—C42—H42C | 109.5 |
C20—N1—C1—C2 | 62.1 (4) | C42—N2—C22—C23 | 60.4 (4) |
C21—N1—C1—C2 | −176.2 (3) | C41—N2—C22—C23 | −176.0 (3) |
N1—C1—C2—C17 | 128.8 (3) | N2—C22—C23—C38 | 125.7 (3) |
N1—C1—C2—C3 | 56.9 (4) | N2—C22—C23—C24 | 52.1 (4) |
C1—C2—C3—C17 | 108.4 (3) | C22—C23—C24—C38 | 109.1 (3) |
C1—C2—C3—C4 | −6.3 (5) | C22—C23—C24—C25 | −6.6 (5) |
C17—C2—C3—C4 | −114.7 (3) | C38—C23—C24—C25 | −115.7 (3) |
C17—C3—C4—O1 | −58.2 (4) | C38—C24—C25—O2 | −51.7 (4) |
C2—C3—C4—O1 | 19.6 (4) | C23—C24—C25—O2 | 24.6 (4) |
C17—C3—C4—C11 | 61.5 (4) | C38—C24—C25—C26 | 66.8 (4) |
C2—C3—C4—C11 | 139.3 (3) | C23—C24—C25—C26 | 143.0 (3) |
C17—C3—C4—C5 | −179.8 (3) | C38—C24—C25—C32 | −172.7 (3) |
C2—C3—C4—C5 | −102.0 (3) | C23—C24—C25—C32 | −96.4 (3) |
O1—C4—C5—C6 | −124.3 (3) | O2—C25—C26—C27 | −171.6 (3) |
C11—C4—C5—C6 | 119.1 (3) | C24—C25—C26—C27 | 66.9 (3) |
C3—C4—C5—C6 | −0.3 (4) | C32—C25—C26—C27 | −55.1 (4) |
O1—C4—C5—C10 | 57.5 (4) | O2—C25—C26—C31 | 9.0 (4) |
C11—C4—C5—C10 | −59.2 (4) | C24—C25—C26—C31 | −112.5 (3) |
C3—C4—C5—C10 | −178.5 (3) | C32—C25—C26—C31 | 125.5 (3) |
C10—C5—C6—C7 | −1.6 (5) | C31—C26—C27—C28 | 1.2 (5) |
C4—C5—C6—C7 | −179.8 (3) | C25—C26—C27—C28 | −178.2 (3) |
C5—C6—C7—C8 | 1.7 (5) | C26—C27—C28—C29 | −0.8 (5) |
C6—C7—C8—C9 | −1.1 (6) | C27—C28—C29—C30 | −0.3 (5) |
C7—C8—C9—C10 | 0.4 (6) | C28—C29—C30—C31 | 0.9 (5) |
C8—C9—C10—C5 | −0.3 (6) | C29—C30—C31—C26 | −0.4 (5) |
C6—C5—C10—C9 | 0.9 (5) | C27—C26—C31—C30 | −0.7 (5) |
C4—C5—C10—C9 | 179.2 (3) | C25—C26—C31—C30 | 178.7 (3) |
O1—C4—C11—C12 | 5.6 (4) | O2—C25—C32—C33 | −140.8 (3) |
C3—C4—C11—C12 | −116.3 (3) | C24—C25—C32—C33 | −17.5 (4) |
C5—C4—C11—C12 | 121.9 (3) | C26—C25—C32—C33 | 103.1 (3) |
O1—C4—C11—C16 | −175.6 (2) | O2—C25—C32—C37 | 39.8 (4) |
C3—C4—C11—C16 | 62.5 (4) | C24—C25—C32—C37 | 163.1 (3) |
C5—C4—C11—C16 | −59.3 (4) | C26—C25—C32—C37 | −76.3 (3) |
C16—C11—C12—C13 | 1.1 (5) | C37—C32—C33—C34 | −0.7 (5) |
C4—C11—C12—C13 | 179.9 (3) | C25—C32—C33—C34 | 179.9 (3) |
C11—C12—C13—C14 | −0.5 (5) | C32—C33—C34—C35 | −0.8 (6) |
C12—C13—C14—C15 | 0.2 (6) | C33—C34—C35—C36 | 2.3 (6) |
C13—C14—C15—C16 | −0.5 (6) | C34—C35—C36—C37 | −2.2 (6) |
C14—C15—C16—C11 | 1.2 (5) | C33—C32—C37—C36 | 0.8 (5) |
C12—C11—C16—C15 | −1.4 (5) | C25—C32—C37—C36 | −179.7 (3) |
C4—C11—C16—C15 | 179.7 (3) | C35—C36—C37—C32 | 0.6 (6) |
C4—C3—C17—C18 | 7.9 (5) | C22—C23—C38—C40 | −5.2 (5) |
C2—C3—C17—C18 | −109.3 (4) | C24—C23—C38—C40 | 111.2 (3) |
C4—C3—C17—C19 | −134.4 (3) | C22—C23—C38—C39 | 137.1 (3) |
C2—C3—C17—C19 | 108.3 (3) | C24—C23—C38—C39 | −106.6 (3) |
C4—C3—C17—C2 | 117.3 (4) | C22—C23—C38—C24 | −116.3 (3) |
C1—C2—C17—C18 | −3.7 (4) | C25—C24—C38—C40 | 4.5 (5) |
C3—C2—C17—C18 | 111.0 (3) | C23—C24—C38—C40 | −109.7 (3) |
C1—C2—C17—C19 | 138.9 (3) | C25—C24—C38—C39 | −139.2 (3) |
C3—C2—C17—C19 | −106.4 (3) | C23—C24—C38—C39 | 106.6 (3) |
C1—C2—C17—C3 | −114.7 (3) | C25—C24—C38—C23 | 114.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—HO1···N1 | 0.98 (4) | 1.88 (4) | 2.782 (4) | 152 (3) |
O2—HO2···N2 | 0.90 (4) | 1.86 (4) | 2.716 (4) | 157 (3) |