The title compound, C
38H
37NO
4, crystallizes with two molecules in the asymmetric unit. The molecules have similar geometric parameters and represent opposite enantiomers of the title compound. In both molecules, the pyrrolidine ring adopts an envelope conformation; the pyran ring in the chromanone moiety has a half-chair conformation. The molecular packing in the crystal is stabilized by C—H
O and C—H
π interactions, in addition to van der Waals forces.
Supporting information
CCDC reference: 225861
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.047
- wR factor = 0.137
- Data-to-parameter ratio = 10.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.09 Ratio
Alert level C
ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies
outside the range 0.99 <> 1.01
Calculated value of mu = 0.079
Value of mu given = 0.080
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.34 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.25 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.20 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O1B - C12B = 5.17 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 12
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C38 H37 N O4
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 28.30
From the CIF: _reflns_number_total 8348
Count of symmetry unique reflns 8422
Completeness (_total/calc) 99.12%
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
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
2-Benzoyl-3-cyclohexyl-4-(
p-methoxyphenyl)-5-phenylpyrrolidine-3-spiro-
3'-chroman-4'-one
top
Crystal data top
C38H37NO4 | F(000) = 2432 |
Mr = 571.69 | Dx = 1.226 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 24284 reflections |
a = 11.8945 (3) Å | θ = 2.0–28.2° |
b = 19.2698 (4) Å | µ = 0.08 mm−1 |
c = 27.0279 (6) Å | T = 293 K |
V = 6194.9 (2) Å3 | Block, yellow |
Z = 8 | 0.24 × 0.20 × 0.16 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 6500 reflections with I > \2s(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 28.3°, θmin = 1.8° |
ω scans | h = −10→15 |
42360 measured reflections | k = −25→23 |
8348 independent reflections | l = −35→32 |
Refinement top
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0668P)2 + 1.0304P] where P = (Fo2 + 2Fc2)/3 |
8348 reflections | (Δ/σ)max < 0.001 |
775 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1A | 0.69144 (18) | 0.99116 (11) | 0.14794 (8) | 0.0401 (5) | |
C2A | 0.7928 (2) | 0.97466 (14) | 0.17615 (9) | 0.0395 (5) | |
H2A | 0.8178 | 1.0154 | 0.1948 | 0.047* | |
C3A | 0.7509 (2) | 0.91714 (13) | 0.21220 (9) | 0.0389 (5) | |
H3A | 0.7606 | 0.8730 | 0.1947 | 0.047* | |
C4A | 0.6214 (2) | 0.92842 (13) | 0.21707 (9) | 0.0383 (5) | |
C5A | 0.5950 (2) | 0.99122 (13) | 0.18158 (9) | 0.0393 (5) | |
H5A | 0.5262 | 0.9815 | 0.1629 | 0.047* | |
C6A | 0.6995 (3) | 1.04323 (15) | 0.10778 (11) | 0.0498 (7) | |
H6A | 0.7442 | 1.0210 | 0.0818 | 0.060* | |
C7A | 0.7601 (4) | 1.1100 (2) | 0.11947 (16) | 0.0844 (13) | |
H7A1 | 0.8327 | 1.0997 | 0.1341 | 0.101* | |
H7A2 | 0.7167 | 1.1366 | 0.1432 | 0.101* | |
C8A | 0.7767 (5) | 1.1529 (2) | 0.07165 (18) | 0.0992 (16) | |
H8A1 | 0.8123 | 1.1968 | 0.0798 | 0.119* | |
H8A2 | 0.8260 | 1.1280 | 0.0493 | 0.119* | |
C9A | 0.6649 (5) | 1.1667 (2) | 0.04613 (19) | 0.0961 (15) | |
H9A1 | 0.6197 | 1.1971 | 0.0667 | 0.115* | |
H9A2 | 0.6785 | 1.1902 | 0.0150 | 0.115* | |
C10A | 0.6018 (4) | 1.1015 (2) | 0.03669 (15) | 0.0824 (12) | |
H10A | 0.6419 | 1.0740 | 0.0124 | 0.099* | |
H10B | 0.5285 | 1.1127 | 0.0231 | 0.099* | |
C11A | 0.5864 (3) | 1.05846 (18) | 0.08427 (12) | 0.0575 (8) | |
H11A | 0.5398 | 1.0839 | 0.1074 | 0.069* | |
H11B | 0.5488 | 1.0152 | 0.0764 | 0.069* | |
C12A | 0.5806 (2) | 1.05972 (14) | 0.21067 (10) | 0.0443 (6) | |
C13A | 0.4704 (3) | 1.09635 (14) | 0.21133 (10) | 0.0464 (6) | |
C14A | 0.3710 (3) | 1.06717 (18) | 0.19436 (14) | 0.0611 (8) | |
H14A | 0.3717 | 1.0226 | 0.1812 | 0.073* | |
C15A | 0.2704 (3) | 1.1035 (2) | 0.19676 (15) | 0.0702 (10) | |
H15A | 0.2044 | 1.0832 | 0.1853 | 0.084* | |
C16A | 0.2684 (3) | 1.1693 (2) | 0.21599 (15) | 0.0718 (10) | |
H16A | 0.2012 | 1.1939 | 0.2173 | 0.086* | |
C17A | 0.3655 (4) | 1.19866 (19) | 0.23321 (18) | 0.0825 (12) | |
H17A | 0.3640 | 1.2432 | 0.2464 | 0.099* | |
C18A | 0.4653 (3) | 1.16293 (16) | 0.23123 (14) | 0.0644 (9) | |
H18A | 0.5304 | 1.1835 | 0.2434 | 0.077* | |
C19A | 0.5572 (2) | 0.86495 (13) | 0.19690 (9) | 0.0407 (5) | |
C20A | 0.4405 (2) | 0.85702 (15) | 0.21468 (10) | 0.0458 (6) | |
C21A | 0.3974 (3) | 0.90207 (16) | 0.25034 (10) | 0.0490 (7) | |
C22A | 0.5806 (2) | 0.93863 (16) | 0.27049 (10) | 0.0453 (6) | |
H22A | 0.5981 | 0.8975 | 0.2897 | 0.054* | |
H22B | 0.6204 | 0.9774 | 0.2852 | 0.054* | |
C23A | 0.3698 (3) | 0.80547 (17) | 0.19469 (12) | 0.0574 (8) | |
H23A | 0.3983 | 0.7741 | 0.1717 | 0.069* | |
C24A | 0.2591 (3) | 0.8012 (2) | 0.20887 (15) | 0.0725 (10) | |
H24A | 0.2127 | 0.7672 | 0.1955 | 0.087* | |
C25A | 0.2169 (3) | 0.8477 (2) | 0.24307 (15) | 0.0766 (11) | |
H25A | 0.1414 | 0.8453 | 0.2519 | 0.092* | |
C26A | 0.2845 (3) | 0.8977 (2) | 0.26441 (13) | 0.0667 (9) | |
H26A | 0.2553 | 0.9281 | 0.2879 | 0.080* | |
C27A | 0.8186 (2) | 0.91100 (14) | 0.25931 (9) | 0.0404 (5) | |
C28A | 0.8633 (2) | 0.84708 (14) | 0.27223 (10) | 0.0456 (6) | |
H28A | 0.8500 | 0.8091 | 0.2518 | 0.055* | |
C29A | 0.9277 (3) | 0.83801 (16) | 0.31491 (11) | 0.0541 (7) | |
H29A | 0.9571 | 0.7946 | 0.3226 | 0.065* | |
C30A | 0.9473 (3) | 0.89393 (16) | 0.34554 (11) | 0.0548 (7) | |
C31A | 0.9042 (3) | 0.95894 (16) | 0.33304 (11) | 0.0565 (8) | |
H31A | 0.9177 | 0.9969 | 0.3535 | 0.068* | |
C32A | 0.8417 (3) | 0.96717 (15) | 0.29055 (10) | 0.0486 (6) | |
H32A | 0.8142 | 1.0109 | 0.2825 | 0.058* | |
C33A | 1.0592 (5) | 0.8263 (3) | 0.4003 (2) | 0.128 (2) | |
H33A | 1.0981 | 0.8301 | 0.4313 | 0.192* | |
H33B | 1.1118 | 0.8145 | 0.3747 | 0.192* | |
H33C | 1.0029 | 0.7908 | 0.4027 | 0.192* | |
C34A | 0.8886 (2) | 0.94639 (14) | 0.14519 (10) | 0.0437 (6) | |
C35A | 0.9985 (3) | 0.95537 (19) | 0.16074 (13) | 0.0593 (8) | |
H35A | 1.0136 | 0.9837 | 0.1878 | 0.071* | |
C36A | 1.0871 (3) | 0.9223 (2) | 0.13616 (18) | 0.0801 (12) | |
H36A | 1.1607 | 0.9281 | 0.1471 | 0.096* | |
C37A | 1.0650 (4) | 0.8814 (2) | 0.09592 (18) | 0.0828 (13) | |
H37A | 1.1238 | 0.8589 | 0.0798 | 0.099* | |
C38A | 0.9573 (4) | 0.87315 (19) | 0.07915 (15) | 0.0735 (11) | |
H38A | 0.9434 | 0.8463 | 0.0512 | 0.088* | |
C39A | 0.8688 (3) | 0.90485 (16) | 0.10381 (12) | 0.0551 (7) | |
H39A | 0.7956 | 0.8983 | 0.0926 | 0.066* | |
O1A | 0.66158 (18) | 1.08332 (11) | 0.23288 (9) | 0.0604 (6) | |
O2A | 0.46192 (17) | 0.95149 (11) | 0.27278 (7) | 0.0526 (5) | |
O3A | 0.59905 (18) | 0.82430 (11) | 0.16769 (8) | 0.0554 (5) | |
O4A | 1.0073 (3) | 0.89056 (14) | 0.38889 (10) | 0.0876 (9) | |
N1B | 1.30653 (19) | 1.02866 (11) | 0.47633 (8) | 0.0411 (5) | |
C2B | 1.2027 (2) | 1.05236 (14) | 0.45270 (9) | 0.0410 (6) | |
H2B | 1.1747 | 1.0169 | 0.4298 | 0.049* | |
C3B | 1.2446 (2) | 1.11710 (14) | 0.42340 (9) | 0.0406 (6) | |
H3B | 1.2416 | 1.1562 | 0.4466 | 0.049* | |
C4B | 1.3722 (2) | 1.10313 (13) | 0.41338 (9) | 0.0403 (5) | |
C5B | 1.3963 (2) | 1.03185 (13) | 0.43930 (9) | 0.0412 (5) | |
H5B | 1.4697 | 1.0333 | 0.4558 | 0.049* | |
C6B | 1.3002 (3) | 0.97011 (15) | 0.51124 (11) | 0.0492 (6) | |
H6B | 1.2570 | 0.9873 | 0.5396 | 0.059* | |
C7B | 1.2396 (3) | 0.90557 (18) | 0.49401 (15) | 0.0676 (9) | |
H7B1 | 1.2820 | 0.8838 | 0.4675 | 0.081* | |
H7B2 | 1.1662 | 0.9181 | 0.4812 | 0.081* | |
C8B | 1.2257 (4) | 0.8541 (2) | 0.53706 (17) | 0.0794 (12) | |
H8B1 | 1.1782 | 0.8744 | 0.5624 | 0.095* | |
H8B2 | 1.1896 | 0.8121 | 0.5252 | 0.095* | |
C9B | 1.3402 (4) | 0.8360 (2) | 0.55918 (18) | 0.0821 (12) | |
H9B1 | 1.3296 | 0.8063 | 0.5877 | 0.098* | |
H9B2 | 1.3840 | 0.8106 | 0.5350 | 0.098* | |
C10B | 1.4037 (4) | 0.8999 (2) | 0.57453 (15) | 0.0755 (10) | |
H10C | 1.4778 | 0.8866 | 0.5862 | 0.091* | |
H10D | 1.3646 | 0.9222 | 0.6017 | 0.091* | |
C11B | 1.4158 (3) | 0.95120 (16) | 0.53183 (11) | 0.0533 (7) | |
H11C | 1.4613 | 0.9307 | 0.5059 | 0.064* | |
H11D | 1.4535 | 0.9928 | 0.5434 | 0.064* | |
C12B | 1.3925 (3) | 0.97044 (14) | 0.40265 (10) | 0.0493 (7) | |
C13B | 1.4897 (3) | 0.92064 (16) | 0.40035 (12) | 0.0599 (9) | |
C14B | 1.5980 (3) | 0.9382 (2) | 0.41412 (15) | 0.0757 (11) | |
H14B | 1.6130 | 0.9824 | 0.4263 | 0.091* | |
C15B | 1.6845 (4) | 0.8902 (3) | 0.4097 (2) | 0.1086 (19) | |
H15B | 1.7578 | 0.9024 | 0.4180 | 0.130* | |
C16B | 1.6604 (7) | 0.8242 (3) | 0.3930 (2) | 0.131 (3) | |
H16B | 1.7176 | 0.7915 | 0.3913 | 0.157* | |
C17B | 1.5523 (7) | 0.8057 (2) | 0.3785 (2) | 0.123 (2) | |
H17B | 1.5378 | 0.7614 | 0.3665 | 0.147* | |
C18B | 1.4664 (5) | 0.85387 (18) | 0.38200 (16) | 0.0852 (13) | |
H18B | 1.3938 | 0.8422 | 0.3723 | 0.102* | |
C19B | 1.4454 (2) | 1.15707 (13) | 0.44057 (10) | 0.0428 (6) | |
C20B | 1.5627 (2) | 1.16194 (14) | 0.42221 (11) | 0.0455 (6) | |
C21B | 1.5962 (3) | 1.12617 (15) | 0.38027 (11) | 0.0476 (6) | |
C22B | 1.4064 (2) | 1.10657 (16) | 0.35888 (9) | 0.0465 (6) | |
H22C | 1.3594 | 1.0754 | 0.3398 | 0.056* | |
H22D | 1.3946 | 1.1533 | 0.3466 | 0.056* | |
C23B | 1.6434 (3) | 1.20067 (16) | 0.44807 (13) | 0.0561 (7) | |
H23B | 1.6217 | 1.2259 | 0.4758 | 0.067* | |
C24B | 1.7540 (3) | 1.2022 (2) | 0.43330 (16) | 0.0698 (10) | |
H24B | 1.8067 | 1.2278 | 0.4510 | 0.084* | |
C25B | 1.7860 (3) | 1.1647 (2) | 0.39150 (15) | 0.0724 (10) | |
H25B | 1.8606 | 1.1652 | 0.3813 | 0.087* | |
C26B | 1.7083 (3) | 1.12717 (19) | 0.36528 (13) | 0.0632 (9) | |
H26B | 1.7304 | 1.1023 | 0.3374 | 0.076* | |
C27B | 1.1724 (2) | 1.13755 (14) | 0.37954 (10) | 0.0419 (6) | |
C28B | 1.1315 (3) | 1.09111 (14) | 0.34479 (11) | 0.0491 (6) | |
H28B | 1.1494 | 1.0443 | 0.3479 | 0.059* | |
C29B | 1.0641 (3) | 1.11233 (14) | 0.30530 (11) | 0.0484 (6) | |
H29B | 1.0370 | 1.0801 | 0.2826 | 0.058* | |
C30B | 1.0380 (2) | 1.18193 (14) | 0.30027 (10) | 0.0458 (6) | |
C31B | 1.0770 (3) | 1.22945 (14) | 0.33451 (11) | 0.0508 (7) | |
H31B | 1.0587 | 1.2762 | 0.3314 | 0.061* | |
C32B | 1.1436 (3) | 1.20712 (14) | 0.37356 (11) | 0.0486 (6) | |
H32B | 1.1696 | 1.2395 | 0.3964 | 0.058* | |
C33B | 0.9203 (4) | 1.1636 (2) | 0.22940 (15) | 0.0794 (11) | |
H33D | 0.8799 | 1.1896 | 0.2049 | 0.119* | |
H33E | 0.8687 | 1.1350 | 0.2476 | 0.119* | |
H33F | 0.9751 | 1.1347 | 0.2134 | 0.119* | |
C34B | 1.1109 (2) | 1.07349 (14) | 0.48838 (10) | 0.0439 (6) | |
C35B | 0.9988 (3) | 1.06271 (19) | 0.47594 (12) | 0.0601 (8) | |
H35B | 0.9805 | 1.0374 | 0.4478 | 0.072* | |
C36B | 0.9135 (3) | 1.0899 (3) | 0.50581 (17) | 0.0833 (13) | |
H36B | 0.8388 | 1.0842 | 0.4966 | 0.100* | |
C37B | 0.9389 (4) | 1.1248 (2) | 0.54860 (17) | 0.0781 (11) | |
H37B | 0.8817 | 1.1423 | 0.5685 | 0.094* | |
C38B | 1.0491 (4) | 1.13354 (19) | 0.56187 (15) | 0.0742 (11) | |
H38B | 1.0667 | 1.1561 | 0.5913 | 0.089* | |
C39B | 1.1346 (3) | 1.10894 (17) | 0.53168 (12) | 0.0578 (8) | |
H39B | 1.2090 | 1.1164 | 0.5407 | 0.069* | |
O1B | 1.3088 (2) | 0.96044 (12) | 0.37793 (8) | 0.0629 (6) | |
O2B | 1.52243 (18) | 1.08770 (11) | 0.35236 (8) | 0.0535 (5) | |
O3B | 1.41214 (19) | 1.19051 (12) | 0.47564 (8) | 0.0594 (6) | |
O4B | 0.97510 (19) | 1.20964 (11) | 0.26213 (9) | 0.0608 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0377 (11) | 0.0463 (11) | 0.0362 (10) | 0.0019 (9) | 0.0020 (9) | 0.0033 (9) |
C2A | 0.0361 (13) | 0.0434 (13) | 0.0392 (12) | −0.0002 (11) | 0.0013 (10) | 0.0010 (10) |
C3A | 0.0400 (13) | 0.0397 (13) | 0.0370 (12) | −0.0021 (11) | 0.0026 (10) | −0.0011 (10) |
C4A | 0.0387 (13) | 0.0429 (12) | 0.0332 (11) | −0.0018 (11) | 0.0021 (10) | −0.0014 (10) |
C5A | 0.0380 (13) | 0.0400 (12) | 0.0398 (12) | 0.0006 (10) | −0.0011 (11) | −0.0027 (10) |
C6A | 0.0495 (16) | 0.0527 (15) | 0.0473 (14) | −0.0001 (13) | 0.0021 (12) | 0.0098 (12) |
C7A | 0.102 (3) | 0.074 (2) | 0.078 (2) | −0.033 (2) | −0.019 (2) | 0.018 (2) |
C8A | 0.122 (4) | 0.080 (3) | 0.095 (3) | −0.042 (3) | −0.020 (3) | 0.036 (2) |
C9A | 0.120 (4) | 0.069 (2) | 0.100 (3) | 0.002 (3) | −0.004 (3) | 0.038 (2) |
C10A | 0.076 (3) | 0.100 (3) | 0.071 (2) | 0.004 (2) | −0.009 (2) | 0.038 (2) |
C11A | 0.0540 (18) | 0.0644 (18) | 0.0541 (16) | 0.0036 (15) | −0.0022 (14) | 0.0150 (14) |
C12A | 0.0440 (14) | 0.0442 (14) | 0.0446 (13) | −0.0022 (12) | 0.0039 (12) | −0.0053 (11) |
C13A | 0.0521 (16) | 0.0437 (14) | 0.0435 (13) | 0.0016 (12) | 0.0064 (12) | −0.0010 (11) |
C14A | 0.0474 (17) | 0.0582 (17) | 0.078 (2) | 0.0075 (15) | 0.0003 (16) | −0.0174 (16) |
C15A | 0.0504 (18) | 0.080 (2) | 0.080 (2) | 0.0106 (17) | 0.0036 (17) | −0.015 (2) |
C16A | 0.066 (2) | 0.071 (2) | 0.079 (2) | 0.0239 (19) | 0.0114 (19) | −0.0036 (19) |
C17A | 0.088 (3) | 0.0534 (19) | 0.106 (3) | 0.024 (2) | 0.008 (3) | −0.019 (2) |
C18A | 0.072 (2) | 0.0465 (16) | 0.075 (2) | 0.0035 (16) | 0.0011 (18) | −0.0139 (15) |
C19A | 0.0438 (14) | 0.0422 (13) | 0.0362 (12) | −0.0052 (11) | −0.0017 (11) | 0.0039 (10) |
C20A | 0.0461 (15) | 0.0482 (14) | 0.0430 (13) | −0.0070 (12) | −0.0013 (12) | 0.0034 (11) |
C21A | 0.0463 (15) | 0.0612 (17) | 0.0396 (13) | −0.0101 (14) | 0.0002 (12) | 0.0008 (12) |
C22A | 0.0401 (14) | 0.0593 (16) | 0.0367 (12) | −0.0067 (12) | 0.0018 (11) | −0.0066 (12) |
C23A | 0.0539 (18) | 0.0590 (17) | 0.0593 (18) | −0.0157 (15) | −0.0010 (15) | −0.0030 (14) |
C24A | 0.059 (2) | 0.086 (3) | 0.073 (2) | −0.0295 (19) | 0.0004 (18) | −0.005 (2) |
C25A | 0.0447 (18) | 0.111 (3) | 0.074 (2) | −0.022 (2) | 0.0043 (17) | −0.003 (2) |
C26A | 0.0447 (17) | 0.098 (3) | 0.0577 (18) | −0.0078 (18) | 0.0111 (15) | −0.0060 (19) |
C27A | 0.0381 (13) | 0.0452 (13) | 0.0377 (12) | −0.0039 (11) | 0.0003 (10) | −0.0003 (10) |
C28A | 0.0455 (15) | 0.0445 (13) | 0.0467 (14) | −0.0007 (12) | −0.0012 (12) | −0.0020 (11) |
C29A | 0.0552 (17) | 0.0505 (15) | 0.0566 (16) | 0.0059 (14) | −0.0099 (14) | 0.0026 (13) |
C30A | 0.0527 (17) | 0.0607 (17) | 0.0509 (15) | −0.0045 (14) | −0.0153 (14) | 0.0045 (14) |
C31A | 0.068 (2) | 0.0510 (15) | 0.0504 (15) | −0.0132 (15) | −0.0120 (15) | −0.0071 (13) |
C32A | 0.0578 (17) | 0.0395 (13) | 0.0484 (14) | −0.0020 (12) | −0.0071 (13) | 0.0001 (11) |
C33A | 0.169 (6) | 0.090 (3) | 0.125 (4) | 0.014 (3) | −0.101 (4) | 0.008 (3) |
C34A | 0.0417 (14) | 0.0460 (14) | 0.0434 (13) | 0.0004 (12) | 0.0087 (11) | 0.0077 (11) |
C35A | 0.0417 (16) | 0.075 (2) | 0.0608 (18) | −0.0027 (15) | 0.0030 (14) | 0.0071 (16) |
C36A | 0.0390 (17) | 0.095 (3) | 0.106 (3) | 0.0087 (18) | 0.0188 (19) | 0.030 (3) |
C37A | 0.075 (3) | 0.072 (2) | 0.102 (3) | 0.016 (2) | 0.051 (2) | 0.015 (2) |
C38A | 0.086 (3) | 0.0608 (19) | 0.074 (2) | 0.0000 (19) | 0.039 (2) | −0.0066 (17) |
C39A | 0.0575 (18) | 0.0524 (16) | 0.0553 (16) | −0.0015 (14) | 0.0131 (14) | −0.0018 (13) |
O1A | 0.0511 (12) | 0.0581 (12) | 0.0721 (14) | −0.0056 (10) | −0.0037 (11) | −0.0215 (11) |
O2A | 0.0447 (11) | 0.0684 (13) | 0.0448 (10) | −0.0054 (10) | 0.0084 (9) | −0.0113 (9) |
O3A | 0.0545 (12) | 0.0530 (11) | 0.0586 (12) | −0.0043 (10) | 0.0015 (10) | −0.0169 (10) |
O4A | 0.110 (2) | 0.0744 (16) | 0.0781 (17) | −0.0002 (16) | −0.0525 (17) | −0.0017 (13) |
N1B | 0.0407 (11) | 0.0430 (11) | 0.0396 (11) | 0.0020 (10) | 0.0048 (9) | 0.0043 (9) |
C2B | 0.0397 (13) | 0.0442 (13) | 0.0390 (12) | 0.0012 (11) | 0.0007 (11) | 0.0015 (11) |
C3B | 0.0432 (14) | 0.0395 (13) | 0.0390 (12) | 0.0005 (11) | 0.0031 (11) | −0.0038 (10) |
C4B | 0.0445 (14) | 0.0388 (12) | 0.0375 (12) | −0.0005 (11) | 0.0027 (11) | −0.0008 (10) |
C5B | 0.0399 (13) | 0.0416 (12) | 0.0422 (13) | 0.0022 (11) | 0.0031 (11) | −0.0006 (10) |
C6B | 0.0483 (16) | 0.0486 (15) | 0.0507 (15) | −0.0010 (13) | 0.0046 (13) | 0.0097 (12) |
C7B | 0.066 (2) | 0.0563 (18) | 0.080 (2) | −0.0134 (17) | −0.0106 (18) | 0.0125 (17) |
C8B | 0.077 (2) | 0.061 (2) | 0.100 (3) | −0.0229 (19) | −0.012 (2) | 0.028 (2) |
C9B | 0.086 (3) | 0.055 (2) | 0.105 (3) | −0.0069 (19) | −0.013 (2) | 0.030 (2) |
C10B | 0.079 (2) | 0.076 (2) | 0.071 (2) | −0.001 (2) | −0.007 (2) | 0.0282 (19) |
C11B | 0.0545 (17) | 0.0523 (16) | 0.0531 (16) | −0.0014 (14) | −0.0039 (14) | 0.0102 (13) |
C12B | 0.0582 (18) | 0.0449 (14) | 0.0449 (14) | 0.0018 (13) | 0.0168 (14) | −0.0011 (12) |
C13B | 0.078 (2) | 0.0494 (16) | 0.0525 (17) | 0.0167 (16) | 0.0263 (16) | 0.0097 (13) |
C14B | 0.071 (2) | 0.084 (2) | 0.072 (2) | 0.029 (2) | 0.021 (2) | 0.0170 (19) |
C15B | 0.088 (3) | 0.132 (4) | 0.106 (3) | 0.062 (3) | 0.038 (3) | 0.042 (3) |
C16B | 0.161 (6) | 0.100 (4) | 0.132 (5) | 0.082 (4) | 0.065 (5) | 0.047 (4) |
C17B | 0.193 (7) | 0.055 (2) | 0.120 (4) | 0.041 (4) | 0.071 (5) | 0.016 (2) |
C18B | 0.123 (4) | 0.0505 (18) | 0.082 (2) | 0.015 (2) | 0.042 (3) | 0.0035 (17) |
C19B | 0.0500 (15) | 0.0390 (12) | 0.0394 (13) | −0.0016 (12) | 0.0004 (12) | 0.0007 (10) |
C20B | 0.0447 (14) | 0.0416 (13) | 0.0502 (14) | −0.0037 (12) | 0.0015 (12) | 0.0080 (12) |
C21B | 0.0459 (15) | 0.0467 (14) | 0.0503 (14) | −0.0036 (12) | 0.0059 (13) | 0.0066 (12) |
C22B | 0.0481 (15) | 0.0543 (15) | 0.0372 (13) | 0.0017 (13) | 0.0049 (12) | 0.0011 (11) |
C23B | 0.0562 (18) | 0.0485 (15) | 0.0636 (18) | −0.0069 (14) | −0.0018 (15) | 0.0032 (14) |
C24B | 0.055 (2) | 0.066 (2) | 0.088 (3) | −0.0140 (17) | −0.0058 (19) | 0.0114 (19) |
C25B | 0.0469 (19) | 0.082 (2) | 0.088 (3) | −0.0049 (18) | 0.0104 (18) | 0.014 (2) |
C26B | 0.0528 (19) | 0.069 (2) | 0.067 (2) | −0.0014 (16) | 0.0147 (16) | 0.0083 (17) |
C27B | 0.0423 (14) | 0.0422 (13) | 0.0411 (13) | 0.0027 (11) | 0.0021 (11) | 0.0012 (11) |
C28B | 0.0574 (17) | 0.0376 (13) | 0.0523 (15) | 0.0021 (13) | −0.0062 (14) | 0.0003 (11) |
C29B | 0.0536 (16) | 0.0440 (13) | 0.0475 (14) | −0.0044 (13) | −0.0058 (13) | −0.0008 (11) |
C30B | 0.0415 (14) | 0.0484 (14) | 0.0476 (14) | −0.0017 (12) | 0.0001 (12) | 0.0081 (12) |
C31B | 0.0563 (17) | 0.0409 (13) | 0.0552 (16) | 0.0043 (13) | −0.0010 (14) | 0.0056 (12) |
C32B | 0.0546 (17) | 0.0426 (13) | 0.0486 (15) | 0.0005 (13) | −0.0031 (13) | −0.0023 (12) |
C33B | 0.081 (3) | 0.072 (2) | 0.086 (3) | −0.008 (2) | −0.041 (2) | 0.007 (2) |
C34B | 0.0413 (14) | 0.0459 (14) | 0.0445 (13) | 0.0005 (12) | 0.0032 (12) | 0.0069 (11) |
C35B | 0.0438 (16) | 0.083 (2) | 0.0537 (17) | −0.0022 (16) | −0.0021 (13) | 0.0080 (16) |
C36B | 0.0428 (18) | 0.121 (3) | 0.086 (3) | 0.009 (2) | 0.0101 (18) | 0.031 (3) |
C37B | 0.067 (2) | 0.079 (2) | 0.089 (3) | 0.014 (2) | 0.034 (2) | 0.007 (2) |
C38B | 0.082 (3) | 0.064 (2) | 0.077 (2) | −0.0068 (19) | 0.032 (2) | −0.0167 (18) |
C39B | 0.0539 (18) | 0.0593 (18) | 0.0603 (17) | −0.0066 (15) | 0.0119 (15) | −0.0123 (15) |
O1B | 0.0643 (14) | 0.0648 (13) | 0.0597 (12) | −0.0014 (12) | 0.0001 (12) | −0.0213 (11) |
O2B | 0.0506 (11) | 0.0616 (12) | 0.0482 (11) | 0.0004 (10) | 0.0100 (9) | −0.0051 (9) |
O3B | 0.0608 (13) | 0.0628 (13) | 0.0546 (12) | −0.0050 (11) | 0.0037 (10) | −0.0177 (10) |
O4B | 0.0610 (13) | 0.0547 (11) | 0.0668 (13) | −0.0026 (11) | −0.0219 (11) | 0.0105 (10) |
Geometric parameters (Å, º) top
N1A—C2A | 1.461 (3) | N1B—C2B | 1.464 (3) |
N1A—C5A | 1.464 (3) | N1B—C5B | 1.465 (3) |
N1A—C6A | 1.481 (3) | N1B—C6B | 1.473 (3) |
C2A—C34A | 1.515 (4) | C2B—C34B | 1.513 (4) |
C2A—C3A | 1.557 (4) | C2B—C3B | 1.559 (4) |
C2A—H2A | 0.9800 | C2B—H2B | 0.9800 |
C3A—C27A | 1.511 (4) | C3B—C27B | 1.516 (4) |
C3A—C4A | 1.562 (4) | C3B—C4B | 1.564 (4) |
C3A—H3A | 0.9800 | C3B—H3B | 0.9800 |
C4A—C5A | 1.576 (4) | C4B—C5B | 1.568 (4) |
C4A—C22A | 1.536 (3) | C4B—C22B | 1.530 (3) |
C4A—C19A | 1.541 (4) | C4B—C19B | 1.543 (4) |
C5A—C12A | 1.546 (4) | C5B—C12B | 1.544 (4) |
C5A—H5A | 0.9800 | C5B—H5B | 0.9800 |
C6A—C7A | 1.508 (5) | C6B—C7B | 1.511 (4) |
C6A—C11A | 1.516 (4) | C6B—C11B | 1.528 (4) |
C6A—H6A | 0.9800 | C6B—H6B | 0.9800 |
C7A—C8A | 1.548 (5) | C7B—C8B | 1.538 (5) |
C7A—H7A1 | 0.9700 | C7B—H7B1 | 0.9700 |
C7A—H7A2 | 0.9700 | C7B—H7B2 | 0.9700 |
C8A—C9A | 1.522 (7) | C8B—C9B | 1.527 (6) |
C8A—H8A1 | 0.9700 | C8B—H8B1 | 0.9700 |
C8A—H8A2 | 0.9700 | C8B—H8B2 | 0.9700 |
C9A—C10A | 1.486 (6) | C9B—C10B | 1.502 (6) |
C9A—H9A1 | 0.9700 | C9B—H9B1 | 0.9700 |
C9A—H9A2 | 0.9700 | C9B—H9B2 | 0.9700 |
C10A—C11A | 1.541 (5) | C10B—C11B | 1.527 (4) |
C10A—H10A | 0.9700 | C10B—H10C | 0.9700 |
C10A—H10B | 0.9700 | C10B—H10D | 0.9700 |
C11A—H11A | 0.9700 | C11B—H11C | 0.9700 |
C11A—H11B | 0.9700 | C11B—H11D | 0.9700 |
C12A—O1A | 1.223 (3) | C12B—O1B | 1.214 (4) |
C12A—C13A | 1.488 (4) | C12B—C13B | 1.504 (4) |
C13A—C14A | 1.388 (4) | C13B—C14B | 1.383 (6) |
C13A—C18A | 1.393 (4) | C13B—C18B | 1.407 (5) |
C14A—C15A | 1.387 (5) | C14B—C15B | 1.389 (5) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.371 (6) | C15B—C16B | 1.379 (10) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—C17A | 1.368 (6) | C16B—C17B | 1.391 (10) |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C17A—C18A | 1.373 (5) | C17B—C18B | 1.383 (7) |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
C18A—H18A | 0.9300 | C18B—H18B | 0.9300 |
C19A—O3A | 1.219 (3) | C19B—O3B | 1.212 (3) |
C19A—C20A | 1.477 (4) | C19B—C20B | 1.484 (4) |
C20A—C21A | 1.395 (4) | C20B—C21B | 1.385 (4) |
C20A—C23A | 1.409 (4) | C20B—C23B | 1.403 (4) |
C21A—O2A | 1.365 (3) | C21B—O2B | 1.374 (4) |
C21A—C26A | 1.398 (4) | C21B—C26B | 1.393 (4) |
C22A—O2A | 1.435 (3) | C22B—O2B | 1.438 (4) |
C22A—H22A | 0.9700 | C22B—H22C | 0.9700 |
C22A—H22B | 0.9700 | C22B—H22D | 0.9700 |
C23A—C24A | 1.375 (5) | C23B—C24B | 1.375 (5) |
C23A—H23A | 0.9300 | C23B—H23B | 0.9300 |
C24A—C25A | 1.381 (6) | C24B—C25B | 1.393 (6) |
C24A—H24A | 0.9300 | C24B—H24B | 0.9300 |
C25A—C26A | 1.382 (5) | C25B—C26B | 1.371 (5) |
C25A—H25A | 0.9300 | C25B—H25B | 0.9300 |
C26A—H26A | 0.9300 | C26B—H26B | 0.9300 |
C27A—C28A | 1.386 (4) | C27B—C28B | 1.386 (4) |
C27A—C32A | 1.400 (4) | C27B—C32B | 1.393 (4) |
C28A—C29A | 1.396 (4) | C28B—C29B | 1.396 (4) |
C28A—H28A | 0.9300 | C28B—H28B | 0.9300 |
C29A—C30A | 1.379 (4) | C29B—C30B | 1.383 (4) |
C29A—H29A | 0.9300 | C29B—H29B | 0.9300 |
C30A—O4A | 1.373 (4) | C30B—O4B | 1.381 (3) |
C30A—C31A | 1.395 (4) | C30B—C31B | 1.382 (4) |
C31A—C32A | 1.377 (4) | C31B—C32B | 1.388 (4) |
C31A—H31A | 0.9300 | C31B—H31B | 0.9300 |
C32A—H32A | 0.9300 | C32B—H32B | 0.9300 |
C33A—O4A | 1.418 (5) | C33B—O4B | 1.413 (4) |
C33A—H33A | 0.9600 | C33B—H33D | 0.9600 |
C33A—H33B | 0.9600 | C33B—H33E | 0.9600 |
C33A—H33C | 0.9600 | C33B—H33F | 0.9600 |
C34A—C35A | 1.384 (4) | C34B—C39B | 1.384 (4) |
C34A—C39A | 1.396 (4) | C34B—C35B | 1.391 (4) |
C35A—C36A | 1.399 (5) | C35B—C36B | 1.398 (5) |
C35A—H35A | 0.9300 | C35B—H35B | 0.9300 |
C36A—C37A | 1.369 (6) | C36B—C37B | 1.372 (6) |
C36A—H36A | 0.9300 | C36B—H36B | 0.9300 |
C37A—C38A | 1.369 (6) | C37B—C38B | 1.369 (6) |
C37A—H37A | 0.9300 | C37B—H37B | 0.9300 |
C38A—C39A | 1.388 (5) | C38B—C39B | 1.387 (5) |
C38A—H38A | 0.9300 | C38B—H38B | 0.9300 |
C39A—H39A | 0.9300 | C39B—H39B | 0.9300 |
| | | |
C2A—N1A—C5A | 108.84 (19) | C2B—N1B—C5B | 107.69 (19) |
C2A—N1A—C6A | 118.4 (2) | C2B—N1B—C6B | 118.4 (2) |
C5A—N1A—C6A | 120.4 (2) | C5B—N1B—C6B | 120.5 (2) |
N1A—C2A—C34A | 114.2 (2) | N1B—C2B—C34B | 114.5 (2) |
N1A—C2A—C3A | 102.6 (2) | N1B—C2B—C3B | 101.6 (2) |
C34A—C2A—C3A | 109.3 (2) | C34B—C2B—C3B | 109.8 (2) |
N1A—C2A—H2A | 110.2 | N1B—C2B—H2B | 110.2 |
C34A—C2A—H2A | 110.2 | C34B—C2B—H2B | 110.2 |
C3A—C2A—H2A | 110.2 | C3B—C2B—H2B | 110.2 |
C27A—C3A—C2A | 114.4 (2) | C27B—C3B—C2B | 115.1 (2) |
C27A—C3A—C4A | 117.7 (2) | C27B—C3B—C4B | 117.3 (2) |
C2A—C3A—C4A | 105.6 (2) | C2B—C3B—C4B | 105.1 (2) |
C27A—C3A—H3A | 106.1 | C27B—C3B—H3B | 106.2 |
C2A—C3A—H3A | 106.1 | C2B—C3B—H3B | 106.2 |
C4A—C3A—H3A | 106.1 | C4B—C3B—H3B | 106.2 |
C22A—C4A—C19A | 106.1 (2) | C22B—C4B—C19B | 106.2 (2) |
C22A—C4A—C3A | 114.1 (2) | C22B—C4B—C3B | 114.7 (2) |
C19A—C4A—C3A | 110.4 (2) | C19B—C4B—C3B | 110.4 (2) |
C22A—C4A—C5A | 114.3 (2) | C22B—C4B—C5B | 114.8 (2) |
C19A—C4A—C5A | 107.17 (19) | C19B—C4B—C5B | 105.9 (2) |
C3A—C4A—C5A | 104.6 (2) | C3B—C4B—C5B | 104.5 (2) |
N1A—C5A—C12A | 113.8 (2) | N1B—C5B—C12B | 112.6 (2) |
N1A—C5A—C4A | 102.8 (2) | N1B—C5B—C4B | 102.0 (2) |
C12A—C5A—C4A | 111.6 (2) | C12B—C5B—C4B | 112.3 (2) |
N1A—C5A—H5A | 109.5 | N1B—C5B—H5B | 109.9 |
C12A—C5A—H5A | 109.5 | C12B—C5B—H5B | 109.9 |
C4A—C5A—H5A | 109.5 | C4B—C5B—H5B | 109.9 |
N1A—C6A—C7A | 117.1 (3) | N1B—C6B—C7B | 117.2 (3) |
N1A—C6A—C11A | 112.4 (2) | N1B—C6B—C11B | 111.7 (2) |
C7A—C6A—C11A | 110.3 (3) | C7B—C6B—C11B | 110.2 (3) |
N1A—C6A—H6A | 105.4 | N1B—C6B—H6B | 105.6 |
C7A—C6A—H6A | 105.4 | C7B—C6B—H6B | 105.6 |
C11A—C6A—H6A | 105.4 | C11B—C6B—H6B | 105.6 |
C6A—C7A—C8A | 110.0 (3) | C6B—C7B—C8B | 110.4 (3) |
C6A—C7A—H7A1 | 109.7 | C6B—C7B—H7B1 | 109.6 |
C8A—C7A—H7A1 | 109.7 | C8B—C7B—H7B1 | 109.6 |
C6A—C7A—H7A2 | 109.7 | C6B—C7B—H7B2 | 109.6 |
C8A—C7A—H7A2 | 109.7 | C8B—C7B—H7B2 | 109.6 |
H7A1—C7A—H7A2 | 108.2 | H7B1—C7B—H7B2 | 108.1 |
C9A—C8A—C7A | 111.1 (4) | C9B—C8B—C7B | 110.3 (3) |
C9A—C8A—H8A1 | 109.4 | C9B—C8B—H8B1 | 109.6 |
C7A—C8A—H8A1 | 109.4 | C7B—C8B—H8B1 | 109.6 |
C9A—C8A—H8A2 | 109.4 | C9B—C8B—H8B2 | 109.6 |
C7A—C8A—H8A2 | 109.4 | C7B—C8B—H8B2 | 109.6 |
H8A1—C8A—H8A2 | 108.0 | H8B1—C8B—H8B2 | 108.1 |
C10A—C9A—C8A | 111.9 (4) | C10B—C9B—C8B | 111.7 (3) |
C10A—C9A—H9A1 | 109.2 | C10B—C9B—H9B1 | 109.3 |
C8A—C9A—H9A1 | 109.2 | C8B—C9B—H9B1 | 109.3 |
C10A—C9A—H9A2 | 109.2 | C10B—C9B—H9B2 | 109.3 |
C8A—C9A—H9A2 | 109.2 | C8B—C9B—H9B2 | 109.3 |
H9A1—C9A—H9A2 | 107.9 | H9B1—C9B—H9B2 | 107.9 |
C9A—C10A—C11A | 111.8 (4) | C9B—C10B—C11B | 111.7 (3) |
C9A—C10A—H10A | 109.3 | C9B—C10B—H10C | 109.3 |
C11A—C10A—H10A | 109.3 | C11B—C10B—H10C | 109.3 |
C9A—C10A—H10B | 109.3 | C9B—C10B—H10D | 109.3 |
C11A—C10A—H10B | 109.3 | C11B—C10B—H10D | 109.3 |
H10A—C10A—H10B | 107.9 | H10C—C10B—H10D | 107.9 |
C6A—C11A—C10A | 110.4 (3) | C10B—C11B—C6B | 110.2 (3) |
C6A—C11A—H11A | 109.6 | C10B—C11B—H11C | 109.6 |
C10A—C11A—H11A | 109.6 | C6B—C11B—H11C | 109.6 |
C6A—C11A—H11B | 109.6 | C10B—C11B—H11D | 109.6 |
C10A—C11A—H11B | 109.6 | C6B—C11B—H11D | 109.6 |
H11A—C11A—H11B | 108.1 | H11C—C11B—H11D | 108.1 |
O1A—C12A—C13A | 120.8 (2) | O1B—C12B—C13B | 120.4 (3) |
O1A—C12A—C5A | 118.7 (2) | O1B—C12B—C5B | 119.9 (3) |
C13A—C12A—C5A | 120.6 (2) | C13B—C12B—C5B | 119.5 (3) |
C14A—C13A—C18A | 117.6 (3) | C14B—C13B—C18B | 120.2 (4) |
C14A—C13A—C12A | 123.7 (2) | C14B—C13B—C12B | 123.3 (3) |
C18A—C13A—C12A | 118.7 (3) | C18B—C13B—C12B | 116.5 (4) |
C15A—C14A—C13A | 121.0 (3) | C13B—C14B—C15B | 120.3 (5) |
C15A—C14A—H14A | 119.5 | C13B—C14B—H14B | 119.9 |
C13A—C14A—H14A | 119.5 | C15B—C14B—H14B | 119.9 |
C16A—C15A—C14A | 120.0 (4) | C16B—C15B—C14B | 119.2 (6) |
C16A—C15A—H15A | 120.0 | C16B—C15B—H15B | 120.4 |
C14A—C15A—H15A | 120.0 | C14B—C15B—H15B | 120.4 |
C17A—C16A—C15A | 119.7 (3) | C15B—C16B—C17B | 121.4 (5) |
C17A—C16A—H16A | 120.1 | C15B—C16B—H16B | 119.3 |
C15A—C16A—H16A | 120.1 | C17B—C16B—H16B | 119.3 |
C16A—C17A—C18A | 120.6 (3) | C18B—C17B—C16B | 119.5 (5) |
C16A—C17A—H17A | 119.7 | C18B—C17B—H17B | 120.3 |
C18A—C17A—H17A | 119.7 | C16B—C17B—H17B | 120.3 |
C17A—C18A—C13A | 121.0 (4) | C17B—C18B—C13B | 119.5 (5) |
C17A—C18A—H18A | 119.5 | C17B—C18B—H18B | 120.3 |
C13A—C18A—H18A | 119.5 | C13B—C18B—H18B | 120.3 |
O3A—C19A—C20A | 121.9 (2) | O3B—C19B—C20B | 122.3 (3) |
O3A—C19A—C4A | 122.5 (2) | O3B—C19B—C4B | 123.1 (3) |
C20A—C19A—C4A | 115.6 (2) | C20B—C19B—C4B | 114.5 (2) |
C21A—C20A—C23A | 119.0 (3) | C21B—C20B—C23B | 118.4 (3) |
C21A—C20A—C19A | 120.4 (3) | C21B—C20B—C19B | 120.8 (3) |
C23A—C20A—C19A | 120.6 (3) | C23B—C20B—C19B | 120.7 (3) |
O2A—C21A—C20A | 122.3 (3) | O2B—C21B—C20B | 122.3 (3) |
O2A—C21A—C26A | 117.5 (3) | O2B—C21B—C26B | 117.3 (3) |
C20A—C21A—C26A | 120.2 (3) | C20B—C21B—C26B | 120.4 (3) |
O2A—C22A—C4A | 111.9 (2) | O2B—C22B—C4B | 111.3 (2) |
O2A—C22A—H22A | 109.2 | O2B—C22B—H22C | 109.4 |
C4A—C22A—H22A | 109.2 | C4B—C22B—H22C | 109.4 |
O2A—C22A—H22B | 109.2 | O2B—C22B—H22D | 109.4 |
C4A—C22A—H22B | 109.2 | C4B—C22B—H22D | 109.4 |
H22A—C22A—H22B | 107.9 | H22C—C22B—H22D | 108.0 |
C24A—C23A—C20A | 120.5 (3) | C24B—C23B—C20B | 121.4 (3) |
C24A—C23A—H23A | 119.8 | C24B—C23B—H23B | 119.3 |
C20A—C23A—H23A | 119.8 | C20B—C23B—H23B | 119.3 |
C23A—C24A—C25A | 119.7 (3) | C23B—C24B—C25B | 119.1 (3) |
C23A—C24A—H24A | 120.1 | C23B—C24B—H24B | 120.5 |
C25A—C24A—H24A | 120.1 | C25B—C24B—H24B | 120.5 |
C24A—C25A—C26A | 121.3 (3) | C26B—C25B—C24B | 120.6 (3) |
C24A—C25A—H25A | 119.3 | C26B—C25B—H25B | 119.7 |
C26A—C25A—H25A | 119.3 | C24B—C25B—H25B | 119.7 |
C25A—C26A—C21A | 119.2 (4) | C25B—C26B—C21B | 120.1 (3) |
C25A—C26A—H26A | 120.4 | C25B—C26B—H26B | 119.9 |
C21A—C26A—H26A | 120.4 | C21B—C26B—H26B | 119.9 |
C28A—C27A—C32A | 117.4 (2) | C28B—C27B—C32B | 117.1 (3) |
C28A—C27A—C3A | 119.1 (2) | C28B—C27B—C3B | 124.1 (2) |
C32A—C27A—C3A | 123.5 (2) | C32B—C27B—C3B | 118.7 (2) |
C27A—C28A—C29A | 122.0 (3) | C27B—C28B—C29B | 122.1 (3) |
C27A—C28A—H28A | 119.0 | C27B—C28B—H28B | 119.0 |
C29A—C28A—H28A | 119.0 | C29B—C28B—H28B | 119.0 |
C30A—C29A—C28A | 119.4 (3) | C30B—C29B—C28B | 119.2 (3) |
C30A—C29A—H29A | 120.3 | C30B—C29B—H29B | 120.4 |
C28A—C29A—H29A | 120.3 | C28B—C29B—H29B | 120.4 |
O4A—C30A—C29A | 124.3 (3) | O4B—C30B—C31B | 115.2 (2) |
O4A—C30A—C31A | 116.1 (3) | O4B—C30B—C29B | 124.7 (3) |
C29A—C30A—C31A | 119.6 (3) | C31B—C30B—C29B | 120.1 (3) |
C32A—C31A—C30A | 120.3 (3) | C30B—C31B—C32B | 119.7 (3) |
C32A—C31A—H31A | 119.9 | C30B—C31B—H31B | 120.2 |
C30A—C31A—H31A | 119.9 | C32B—C31B—H31B | 120.2 |
C31A—C32A—C27A | 121.3 (3) | C31B—C32B—C27B | 121.8 (3) |
C31A—C32A—H32A | 119.3 | C31B—C32B—H32B | 119.1 |
C27A—C32A—H32A | 119.3 | C27B—C32B—H32B | 119.1 |
O4A—C33A—H33A | 109.5 | O4B—C33B—H33D | 109.5 |
O4A—C33A—H33B | 109.5 | O4B—C33B—H33E | 109.5 |
H33A—C33A—H33B | 109.5 | H33D—C33B—H33E | 109.5 |
O4A—C33A—H33C | 109.5 | O4B—C33B—H33F | 109.5 |
H33A—C33A—H33C | 109.5 | H33D—C33B—H33F | 109.5 |
H33B—C33A—H33C | 109.5 | H33E—C33B—H33F | 109.5 |
C35A—C34A—C39A | 118.3 (3) | C39B—C34B—C35B | 118.2 (3) |
C35A—C34A—C2A | 119.9 (3) | C39B—C34B—C2B | 121.7 (3) |
C39A—C34A—C2A | 121.5 (3) | C35B—C34B—C2B | 119.9 (3) |
C34A—C35A—C36A | 120.7 (3) | C34B—C35B—C36B | 120.0 (3) |
C34A—C35A—H35A | 119.7 | C34B—C35B—H35B | 120.0 |
C36A—C35A—H35A | 119.7 | C36B—C35B—H35B | 120.0 |
C37A—C36A—C35A | 119.7 (4) | C37B—C36B—C35B | 120.7 (4) |
C37A—C36A—H36A | 120.2 | C37B—C36B—H36B | 119.6 |
C35A—C36A—H36A | 120.2 | C35B—C36B—H36B | 119.6 |
C38A—C37A—C36A | 120.6 (3) | C38B—C37B—C36B | 119.5 (3) |
C38A—C37A—H37A | 119.7 | C38B—C37B—H37B | 120.3 |
C36A—C37A—H37A | 119.7 | C36B—C37B—H37B | 120.3 |
C37A—C38A—C39A | 120.0 (4) | C37B—C38B—C39B | 120.4 (4) |
C37A—C38A—H38A | 120.0 | C37B—C38B—H38B | 119.8 |
C39A—C38A—H38A | 120.0 | C39B—C38B—H38B | 119.8 |
C38A—C39A—C34A | 120.6 (3) | C34B—C39B—C38B | 121.1 (3) |
C38A—C39A—H39A | 119.7 | C34B—C39B—H39B | 119.4 |
C34A—C39A—H39A | 119.7 | C38B—C39B—H39B | 119.4 |
C21A—O2A—C22A | 114.4 (2) | C21B—O2B—C22B | 114.2 (2) |
C30A—O4A—C33A | 117.0 (3) | C30B—O4B—C33B | 118.3 (2) |
| | | |
C5A—N1A—C2A—C34A | 158.0 (2) | C5B—N1B—C2B—C34B | −162.0 (2) |
C6A—N1A—C2A—C34A | −59.6 (3) | C6B—N1B—C2B—C34B | 57.0 (3) |
C5A—N1A—C2A—C3A | 39.9 (2) | C5B—N1B—C2B—C3B | −43.7 (2) |
C6A—N1A—C2A—C3A | −177.7 (2) | C6B—N1B—C2B—C3B | 175.3 (2) |
N1A—C2A—C3A—C27A | −155.1 (2) | N1B—C2B—C3B—C27B | 156.8 (2) |
C34A—C2A—C3A—C27A | 83.3 (3) | C34B—C2B—C3B—C27B | −81.6 (3) |
N1A—C2A—C3A—C4A | −24.0 (2) | N1B—C2B—C3B—C4B | 26.2 (2) |
C34A—C2A—C3A—C4A | −145.6 (2) | C34B—C2B—C3B—C4B | 147.8 (2) |
C27A—C3A—C4A—C22A | 5.4 (3) | C27B—C3B—C4B—C22B | −4.5 (3) |
C2A—C3A—C4A—C22A | −123.7 (2) | C2B—C3B—C4B—C22B | 124.8 (2) |
C27A—C3A—C4A—C19A | −114.0 (2) | C27B—C3B—C4B—C19B | 115.4 (2) |
C2A—C3A—C4A—C19A | 116.9 (2) | C2B—C3B—C4B—C19B | −115.3 (2) |
C27A—C3A—C4A—C5A | 131.0 (2) | C27B—C3B—C4B—C5B | −131.1 (2) |
C2A—C3A—C4A—C5A | 1.9 (3) | C2B—C3B—C4B—C5B | −1.8 (2) |
C2A—N1A—C5A—C12A | 82.1 (3) | C2B—N1B—C5B—C12B | −78.0 (3) |
C6A—N1A—C5A—C12A | −59.4 (3) | C6B—N1B—C5B—C12B | 62.1 (3) |
C2A—N1A—C5A—C4A | −38.7 (2) | C2B—N1B—C5B—C4B | 42.6 (3) |
C6A—N1A—C5A—C4A | 179.8 (2) | C6B—N1B—C5B—C4B | −177.4 (2) |
C22A—C4A—C5A—N1A | 146.4 (2) | C22B—C4B—C5B—N1B | −149.7 (2) |
C19A—C4A—C5A—N1A | −96.3 (2) | C19B—C4B—C5B—N1B | 93.5 (2) |
C3A—C4A—C5A—N1A | 20.9 (2) | C3B—C4B—C5B—N1B | −23.2 (2) |
C22A—C4A—C5A—C12A | 24.1 (3) | C22B—C4B—C5B—C12B | −28.9 (3) |
C19A—C4A—C5A—C12A | 141.4 (2) | C19B—C4B—C5B—C12B | −145.7 (2) |
C3A—C4A—C5A—C12A | −101.4 (2) | C3B—C4B—C5B—C12B | 97.6 (2) |
C2A—N1A—C6A—C7A | −46.9 (4) | C2B—N1B—C6B—C7B | 50.5 (4) |
C5A—N1A—C6A—C7A | 91.0 (4) | C5B—N1B—C6B—C7B | −85.5 (3) |
C2A—N1A—C6A—C11A | −176.1 (2) | C2B—N1B—C6B—C11B | 179.0 (2) |
C5A—N1A—C6A—C11A | −38.1 (3) | C5B—N1B—C6B—C11B | 43.1 (3) |
N1A—C6A—C7A—C8A | 171.2 (4) | N1B—C6B—C7B—C8B | −171.8 (3) |
C11A—C6A—C7A—C8A | −58.6 (5) | C11B—C6B—C7B—C8B | 58.9 (4) |
C6A—C7A—C8A—C9A | 56.2 (6) | C6B—C7B—C8B—C9B | −56.9 (5) |
C7A—C8A—C9A—C10A | −54.1 (6) | C7B—C8B—C9B—C10B | 54.8 (5) |
C8A—C9A—C10A—C11A | 54.0 (6) | C8B—C9B—C10B—C11B | −54.9 (5) |
N1A—C6A—C11A—C10A | −169.1 (3) | C9B—C10B—C11B—C6B | 56.2 (4) |
C7A—C6A—C11A—C10A | 58.3 (4) | N1B—C6B—C11B—C10B | 169.6 (3) |
C9A—C10A—C11A—C6A | −56.0 (5) | C7B—C6B—C11B—C10B | −58.2 (4) |
N1A—C5A—C12A—O1A | −50.9 (3) | N1B—C5B—C12B—O1B | 58.3 (3) |
C4A—C5A—C12A—O1A | 64.8 (3) | C4B—C5B—C12B—O1B | −56.2 (3) |
N1A—C5A—C12A—C13A | 128.7 (3) | N1B—C5B—C12B—C13B | −117.6 (3) |
C4A—C5A—C12A—C13A | −115.6 (3) | C4B—C5B—C12B—C13B | 127.9 (3) |
O1A—C12A—C13A—C14A | −168.6 (3) | O1B—C12B—C13B—C14B | 158.9 (3) |
C5A—C12A—C13A—C14A | 11.8 (4) | C5B—C12B—C13B—C14B | −25.2 (4) |
O1A—C12A—C13A—C18A | 9.6 (4) | O1B—C12B—C13B—C18B | −19.6 (4) |
C5A—C12A—C13A—C18A | −170.0 (3) | C5B—C12B—C13B—C18B | 156.3 (3) |
C18A—C13A—C14A—C15A | 0.7 (5) | C18B—C13B—C14B—C15B | 0.3 (6) |
C12A—C13A—C14A—C15A | 178.8 (3) | C12B—C13B—C14B—C15B | −178.2 (3) |
C13A—C14A—C15A—C16A | 0.1 (6) | C13B—C14B—C15B—C16B | −2.0 (7) |
C14A—C15A—C16A—C17A | −0.6 (6) | C14B—C15B—C16B—C17B | 2.7 (8) |
C15A—C16A—C17A—C18A | 0.3 (7) | C15B—C16B—C17B—C18B | −1.6 (9) |
C16A—C17A—C18A—C13A | 0.6 (7) | C16B—C17B—C18B—C13B | −0.2 (7) |
C14A—C13A—C18A—C17A | −1.0 (5) | C14B—C13B—C18B—C17B | 0.8 (6) |
C12A—C13A—C18A—C17A | −179.3 (4) | C12B—C13B—C18B—C17B | 179.4 (4) |
C22A—C4A—C19A—O3A | −145.9 (3) | C22B—C4B—C19B—O3B | 145.7 (3) |
C3A—C4A—C19A—O3A | −21.8 (3) | C3B—C4B—C19B—O3B | 20.7 (4) |
C5A—C4A—C19A—O3A | 91.6 (3) | C5B—C4B—C19B—O3B | −91.9 (3) |
C22A—C4A—C19A—C20A | 35.0 (3) | C22B—C4B—C19B—C20B | −37.8 (3) |
C3A—C4A—C19A—C20A | 159.1 (2) | C3B—C4B—C19B—C20B | −162.7 (2) |
C5A—C4A—C19A—C20A | −87.5 (3) | C5B—C4B—C19B—C20B | 84.7 (3) |
O3A—C19A—C20A—C21A | 176.2 (3) | O3B—C19B—C20B—C21B | −176.1 (3) |
C4A—C19A—C20A—C21A | −4.7 (4) | C4B—C19B—C20B—C21B | 7.3 (4) |
O3A—C19A—C20A—C23A | −6.1 (4) | O3B—C19B—C20B—C23B | 6.5 (4) |
C4A—C19A—C20A—C23A | 173.0 (3) | C4B—C19B—C20B—C23B | −170.1 (2) |
C23A—C20A—C21A—O2A | 177.4 (3) | C23B—C20B—C21B—O2B | −179.1 (3) |
C19A—C20A—C21A—O2A | −4.8 (4) | C19B—C20B—C21B—O2B | 3.4 (4) |
C23A—C20A—C21A—C26A | −2.6 (4) | C23B—C20B—C21B—C26B | 2.0 (4) |
C19A—C20A—C21A—C26A | 175.2 (3) | C19B—C20B—C21B—C26B | −175.5 (3) |
C19A—C4A—C22A—O2A | −60.5 (3) | C19B—C4B—C22B—O2B | 62.4 (3) |
C3A—C4A—C22A—O2A | 177.7 (2) | C3B—C4B—C22B—O2B | −175.3 (2) |
C5A—C4A—C22A—O2A | 57.4 (3) | C5B—C4B—C22B—O2B | −54.2 (3) |
C21A—C20A—C23A—C24A | 2.2 (5) | C21B—C20B—C23B—C24B | −1.6 (5) |
C19A—C20A—C23A—C24A | −175.6 (3) | C19B—C20B—C23B—C24B | 175.8 (3) |
C20A—C23A—C24A—C25A | −0.2 (6) | C20B—C23B—C24B—C25B | 0.5 (5) |
C23A—C24A—C25A—C26A | −1.6 (6) | C23B—C24B—C25B—C26B | 0.3 (6) |
C24A—C25A—C26A—C21A | 1.2 (6) | C24B—C25B—C26B—C21B | 0.1 (6) |
O2A—C21A—C26A—C25A | −179.1 (3) | O2B—C21B—C26B—C25B | 179.8 (3) |
C20A—C21A—C26A—C25A | 0.9 (5) | C20B—C21B—C26B—C25B | −1.2 (5) |
C2A—C3A—C27A—C28A | −125.9 (3) | C2B—C3B—C27B—C28B | −45.8 (4) |
C4A—C3A—C27A—C28A | 109.2 (3) | C4B—C3B—C27B—C28B | 78.6 (4) |
C2A—C3A—C27A—C32A | 52.4 (3) | C2B—C3B—C27B—C32B | 133.4 (3) |
C4A—C3A—C27A—C32A | −72.5 (3) | C4B—C3B—C27B—C32B | −102.1 (3) |
C32A—C27A—C28A—C29A | 0.8 (4) | C32B—C27B—C28B—C29B | 0.0 (5) |
C3A—C27A—C28A—C29A | 179.2 (3) | C3B—C27B—C28B—C29B | 179.2 (3) |
C27A—C28A—C29A—C30A | 0.4 (5) | C27B—C28B—C29B—C30B | 0.6 (5) |
C28A—C29A—C30A—O4A | 178.6 (3) | C28B—C29B—C30B—O4B | 178.0 (3) |
C28A—C29A—C30A—C31A | −1.1 (5) | C28B—C29B—C30B—C31B | −1.0 (5) |
O4A—C30A—C31A—C32A | −179.2 (3) | O4B—C30B—C31B—C32B | −178.3 (3) |
C29A—C30A—C31A—C32A | 0.5 (5) | C29B—C30B—C31B—C32B | 0.8 (5) |
C30A—C31A—C32A—C27A | 0.8 (5) | C30B—C31B—C32B—C27B | −0.2 (5) |
C28A—C27A—C32A—C31A | −1.4 (4) | C28B—C27B—C32B—C31B | −0.2 (5) |
C3A—C27A—C32A—C31A | −179.7 (3) | C3B—C27B—C32B—C31B | −179.5 (3) |
N1A—C2A—C34A—C35A | 153.2 (3) | N1B—C2B—C34B—C39B | 38.7 (4) |
C3A—C2A—C34A—C35A | −92.6 (3) | C3B—C2B—C34B—C39B | −74.9 (3) |
N1A—C2A—C34A—C39A | −33.7 (4) | N1B—C2B—C34B—C35B | −147.0 (3) |
C3A—C2A—C34A—C39A | 80.5 (3) | C3B—C2B—C34B—C35B | 99.5 (3) |
C39A—C34A—C35A—C36A | −1.4 (5) | C39B—C34B—C35B—C36B | 2.6 (5) |
C2A—C34A—C35A—C36A | 171.9 (3) | C2B—C34B—C35B—C36B | −172.0 (3) |
C34A—C35A—C36A—C37A | 0.9 (6) | C34B—C35B—C36B—C37B | −2.8 (6) |
C35A—C36A—C37A—C38A | 0.8 (6) | C35B—C36B—C37B—C38B | 0.6 (7) |
C36A—C37A—C38A—C39A | −1.8 (6) | C36B—C37B—C38B—C39B | 1.7 (6) |
C37A—C38A—C39A—C34A | 1.3 (5) | C35B—C34B—C39B—C38B | −0.4 (5) |
C35A—C34A—C39A—C38A | 0.3 (5) | C2B—C34B—C39B—C38B | 174.1 (3) |
C2A—C34A—C39A—C38A | −172.8 (3) | C37B—C38B—C39B—C34B | −1.8 (6) |
C20A—C21A—O2A—C22A | −20.7 (4) | C20B—C21B—O2B—C22B | 20.9 (4) |
C26A—C21A—O2A—C22A | 159.3 (3) | C26B—C21B—O2B—C22B | −160.1 (3) |
C4A—C22A—O2A—C21A | 55.1 (3) | C4B—C22B—O2B—C21B | −55.4 (3) |
C29A—C30A—O4A—C33A | 5.1 (6) | C31B—C30B—O4B—C33B | −171.9 (3) |
C31A—C30A—O4A—C33A | −175.3 (4) | C29B—C30B—O4B—C33B | 9.0 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3A—H3A···O3A | 0.98 | 2.26 | 2.813 (3) | 115 |
C3B—H3B···O3B | 0.98 | 2.27 | 2.822 (3) | 114 |
C2A—H2A···O1A | 0.98 | 2.49 | 3.028 (3) | 114 |
C2B—H2B···O1B | 0.98 | 2.39 | 2.969 (3) | 118 |
C22A—H22B···O1A | 0.97 | 2.53 | 3.120 (4) | 119 |
C22B—H22C···O1B | 0.97 | 2.52 | 3.089 (4) | 118 |
C26A—H26A···O1Bi | 0.93 | 2.59 | 3.310 (4) | 134 |
Symmetry code: (i) x−1, y, z. |