#------------------------------------------------------------------------------
#$Date: 2021-01-27 00:25:56 +0200 (Wed, 27 Jan 2021) $
#$Revision: 261236 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/84/4518421.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4518421
loop_
_publ_author_name
'Ghouilem, Juba'
'Tran, Christine'
'Grimblat, Nicolas'
'Retailleau, Pascal'
'Alami, Mouad'
'Gandon, Vincent'
'Messaoudi, Samir'
_publ_section_title
;
 Diastereoselective Pd-Catalyzed Anomeric C(sp3)--H Activation: Synthesis
 of α-(Hetero)aryl C-Glycosides
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              1818
_journal_page_last               1826
_journal_paper_doi               10.1021/acscatal.0c05052
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H30 N2 O6'
_chemical_formula_sum            'C25 H30 N2 O6'
_chemical_formula_weight         454.51
_chemical_name_systematic
;
'((2R,3S,4S,6S)-3-acetoxy-6-(4-isopropylphenyl)-
4-(picolinamido)tetrahydro-2H-pyran-2-yl)methyl acetate'
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0246(4)
_cell_length_b                   11.6273(4)
_cell_length_c                   21.2713(8)
_cell_measurement_reflns_used    11532
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1060
_cell_measurement_theta_min      4.0500
_cell_volume                     2479.36(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32915
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.265
_diffrn_reflns_theta_min         3.633
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         6014
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0813P)²+0.3736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                5077
_reflns_number_total             6017
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c05052_si_003.cif
_cod_data_source_block           JG757
_cod_original_cell_volume        2479.35(16)
_cod_database_code               4518421
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4911(2) 0.5168(2) 0.45177(11) 0.0402(5) Uani 1 1 d . . . . .
H1 H 0.546411 0.580481 0.436522 0.048 Uiso 1 1 calc R U . . .
N8 N 0.2024(2) 0.54624(19) 0.56772(10) 0.0457(5) Uani 1 1 d . . . . .
H8N H 0.168(3) 0.613(3) 0.5601(15) 0.055 Uiso 1 1 d . U . . .
C2 C 0.4060(2) 0.56534(19) 0.50521(11) 0.0407(5) Uani 1 1 d . . . . .
H2 H 0.461805 0.578941 0.542315 0.049 Uiso 1 1 calc R U . . .
C3 C 0.2886(2) 0.4882(2) 0.52260(11) 0.0420(5) Uani 1 1 d . . . . .
H3 H 0.324335 0.419071 0.542889 0.050 Uiso 1 1 calc R U . . .
C4 C 0.2131(3) 0.4504(2) 0.46365(12) 0.0473(5) Uani 1 1 d . . . . .
H4A H 0.169608 0.516282 0.444569 0.057 Uiso 1 1 calc R U . . .
H4AB H 0.145068 0.394730 0.474802 0.057 Uiso 1 1 calc R U . . .
O6 O 0.41153(17) 0.48096(15) 0.40007(8) 0.0433(4) Uani 1 1 d . . . . .
C5 C 0.3113(2) 0.3969(2) 0.41705(11) 0.0445(5) Uani 1 1 d . . . . .
H5 H 0.355123 0.331075 0.437075 0.053 Uiso 1 1 calc R U . . .
C7 C 0.2464(3) 0.3575(3) 0.35714(13) 0.0517(6) Uani 1 1 d . . . . .
O9 O 0.34690(16) 0.67241(13) 0.48450(9) 0.0459(4) Uani 1 1 d . . . . .
C10 C 0.5869(2) 0.4238(2) 0.47399(12) 0.0450(5) Uani 1 1 d . . . . .
H10A H 0.638124 0.450316 0.509858 0.054 Uiso 1 1 calc R U . . .
H10B H 0.538478 0.354940 0.485935 0.054 Uiso 1 1 calc R U . . .
O11 O 0.67334(18) 0.40086(17) 0.42133(9) 0.0524(4) Uani 1 1 d . . . . .
C12 C 0.1605(3) 0.4991(3) 0.62083(14) 0.0610(7) Uani 1 1 d . . . . .
O13 O 0.1902(4) 0.4021(3) 0.63701(17) 0.1327(17) Uani 1 1 d . . . . .
C14 C 0.0738(3) 0.5742(3) 0.66185(12) 0.0541(6) Uani 1 1 d . . . . .
C15 C 0.0208(5) 0.5296(4) 0.7157(2) 0.1042(18) Uani 1 1 d . . . . .
H15 H 0.033892 0.452623 0.725938 0.125 Uiso 1 1 calc R U . . .
C16 C -0.0531(4) 0.6006(4) 0.75497(18) 0.0938(14) Uani 1 1 d . . . . .
H16 H -0.088689 0.572491 0.792303 0.113 Uiso 1 1 calc R U . . .
C20 C 0.2292(4) 0.2418(3) 0.34595(17) 0.0723(9) Uani 1 1 d . . . . .
H20 H 0.257828 0.188056 0.375390 0.087 Uiso 1 1 calc R U . . .
N19 N 0.0561(3) 0.6811(2) 0.64460(12) 0.0631(7) Uani 1 1 d . . . . .
C18 C -0.0170(5) 0.7479(3) 0.68262(18) 0.0836(12) Uani 1 1 d . . . . .
H18 H -0.031296 0.823896 0.670773 0.100 Uiso 1 1 calc R U . . .
C17 C -0.0721(4) 0.7106(3) 0.73805(16) 0.0726(9) Uani 1 1 d . . . . .
H17 H -0.121373 0.760227 0.763252 0.087 Uiso 1 1 calc R U . . .
C21 C 0.1685(5) 0.2053(4) 0.2901(2) 0.0933(13) Uani 1 1 d . . . . .
H21 H 0.156500 0.127053 0.282945 0.112 Uiso 1 1 calc R U . . .
C22 C 0.1263(4) 0.2832(4) 0.24553(18) 0.0861(12) Uani 1 1 d . . . . .
C23 C 0.1404(4) 0.3967(4) 0.25796(17) 0.0814(11) Uani 1 1 d . . . . .
H23 H 0.108964 0.450548 0.229240 0.098 Uiso 1 1 calc R U . . .
C24 C 0.2009(4) 0.4337(3) 0.31292(15) 0.0701(8) Uani 1 1 d . . . . .
H24 H 0.210958 0.512123 0.319960 0.084 Uiso 1 1 calc R U . . .
C25 C 0.0624(5) 0.2478(6) 0.1836(3) 0.131(2) Uani 1 1 d D . . . .
H25 H 0.096037 0.307099 0.154892 0.157 Uiso 1 1 calc R U . . .
C26 C 0.1167(6) 0.1435(4) 0.1557(2) 0.1130(18) Uani 1 1 d D . . . .
H26A H 0.091518 0.078392 0.180779 0.169 Uiso 1 1 calc R U . . .
H26B H 0.212193 0.148906 0.154103 0.169 Uiso 1 1 calc R U . . .
H26C H 0.082173 0.134520 0.113914 0.169 Uiso 1 1 calc R U . . .
C27 C -0.0812(5) 0.2685(6) 0.1814(3) 0.134(2) Uani 1 1 d D . . . .
H27A H -0.113337 0.255494 0.139529 0.202 Uiso 1 1 calc R U . . .
H27B H -0.099300 0.346517 0.193495 0.202 Uiso 1 1 calc R U . . .
H27C H -0.125442 0.217034 0.209936 0.202 Uiso 1 1 calc R U . . .
C28 C 0.4210(3) 0.7682(2) 0.49090(13) 0.0498(6) Uani 1 1 d . . . . .
C29 C 0.3421(3) 0.8716(2) 0.4727(2) 0.0722(9) Uani 1 1 d . . . . .
H29A H 0.393514 0.939622 0.480776 0.108 Uiso 1 1 calc R U . . .
H29B H 0.261241 0.874014 0.496886 0.108 Uiso 1 1 calc R U . . .
H29C H 0.320599 0.867635 0.428792 0.108 Uiso 1 1 calc R U . . .
C31 C 0.7882(3) 0.3463(2) 0.43346(14) 0.0503(6) Uani 1 1 d . . . . .
C32 C 0.8661(3) 0.3251(3) 0.37505(17) 0.0668(8) Uani 1 1 d . . . . .
H32A H 0.959421 0.334627 0.383649 0.100 Uiso 1 1 calc R U . . .
H32B H 0.839158 0.378906 0.343232 0.100 Uiso 1 1 calc R U . . .
H32C H 0.849842 0.248190 0.360578 0.100 Uiso 1 1 calc R U . . .
O33 O 0.8216(2) 0.3201(2) 0.48475(12) 0.0807(7) Uani 1 1 d . . . . .
O30 O 0.53399(19) 0.76749(18) 0.50989(12) 0.0639(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 C1 C10 112.7(2) . . ?
O6 C1 C2 111.73(18) . . ?
C10 C1 C2 112.55(19) . . ?
O6 C1 H1 106.4 . . ?
C10 C1 H1 106.4 . . ?
C2 C1 H1 106.4 . . ?
C12 N8 C3 123.9(2) . . ?
C12 N8 H8N 114(2) . . ?
C3 N8 H8N 122(2) . . ?
O9 C2 C3 105.28(18) . . ?
O9 C2 C1 108.63(18) . . ?
C3 C2 C1 113.19(19) . . ?
O9 C2 H2 109.9 . . ?
C3 C2 H2 109.9 . . ?
C1 C2 H2 109.9 . . ?
N8 C3 C2 110.17(18) . . ?
N8 C3 C4 112.3(2) . . ?
C2 C3 C4 110.60(19) . . ?
N8 C3 H3 107.9 . . ?
C2 C3 H3 107.9 . . ?
C4 C3 H3 107.9 . . ?
C3 C4 C5 109.3(2) . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4AB 109.8 . . ?
C5 C4 H4AB 109.8 . . ?
H4A C4 H4AB 108.3 . . ?
C1 O6 C5 113.25(17) . . ?
O6 C5 C7 107.2(2) . . ?
O6 C5 C4 109.49(19) . . ?
C7 C5 C4 113.3(2) . . ?
O6 C5 H5 108.9 . . ?
C7 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
C24 C7 C20 118.1(3) . . ?
C24 C7 C5 122.0(3) . . ?
C20 C7 C5 119.9(3) . . ?
C28 O9 C2 117.05(19) . . ?
O11 C10 C1 105.63(19) . . ?
O11 C10 H10A 110.6 . . ?
C1 C10 H10A 110.6 . . ?
O11 C10 H10B 110.6 . . ?
C1 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C31 O11 C10 117.0(2) . . ?
O13 C12 N8 123.2(3) . . ?
O13 C12 C14 120.9(3) . . ?
N8 C12 C14 115.9(2) . . ?
N19 C14 C15 122.9(3) . . ?
N19 C14 C12 117.8(2) . . ?
C15 C14 C12 119.3(3) . . ?
C14 C15 C16 119.1(4) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 118.8(3) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C7 C20 C21 119.8(4) . . ?
C7 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C14 N19 C18 117.1(3) . . ?
N19 C18 C17 123.7(3) . . ?
N19 C18 H18 118.1 . . ?
C17 C18 H18 118.1 . . ?
C16 C17 C18 118.3(3) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C22 C21 C20 121.2(4) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C21 118.4(3) . . ?
C23 C22 C25 118.5(4) . . ?
C21 C22 C25 123.2(5) . . ?
C22 C23 C24 120.9(4) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C7 C24 C23 121.6(4) . . ?
C7 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C26 C25 C27 119.5(5) . . ?
C26 C25 C22 114.9(4) . . ?
C27 C25 C22 113.4(4) . . ?
C26 C25 H25 101.8 . . ?
C27 C25 H25 101.8 . . ?
C22 C25 H25 101.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O30 C28 O9 123.3(2) . . ?
O30 C28 C29 126.4(3) . . ?
O9 C28 C29 110.4(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O33 C31 O11 123.0(3) . . ?
O33 C31 C32 125.4(3) . . ?
O11 C31 C32 111.6(3) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O6 1.421(3) . ?
C1 C10 1.522(3) . ?
C1 C2 1.529(3) . ?
C1 H1 0.9800 . ?
N8 C12 1.324(3) . ?
N8 C3 1.457(3) . ?
N8 H8N 0.87(3) . ?
C2 O9 1.448(3) . ?
C2 C3 1.526(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.529(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.530(3) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
O6 C5 1.447(3) . ?
C5 C7 1.503(3) . ?
C5 H5 0.9800 . ?
C7 C24 1.370(4) . ?
C7 C20 1.377(5) . ?
O9 C28 1.346(3) . ?
C10 O11 1.441(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
O11 C31 1.339(3) . ?
C12 O13 1.216(4) . ?
C12 C14 1.510(4) . ?
C14 N19 1.307(4) . ?
C14 C15 1.366(4) . ?
C15 C16 1.388(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.342(6) . ?
C16 H16 0.9300 . ?
C20 C21 1.401(5) . ?
C20 H20 0.9300 . ?
N19 C18 1.340(4) . ?
C18 C17 1.372(5) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C21 C22 1.378(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.353(6) . ?
C22 C25 1.522(5) . ?
C23 C24 1.386(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.455(5) . ?
C25 C27 1.461(5) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 O30 1.202(3) . ?
C28 C29 1.490(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 O33 1.181(4) . ?
C31 C32 1.488(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N8 H8N N19 0.87(3) 2.26(3) 2.699(3) 111(3) . yes
N8 H8N O30 0.87(3) 2.44(3) 3.204(3) 148(3) 4_466 yes
C5 H5 O33 0.98 2.44 3.277(4) 142.8 4_456 yes
C32 H32C O13 0.96 2.37 3.187(4) 142.6 4_556 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 C1 C2 O9 -67.9(2) . . . . ?
C10 C1 C2 O9 164.13(19) . . . . ?
O6 C1 C2 C3 48.7(3) . . . . ?
C10 C1 C2 C3 -79.3(2) . . . . ?
C12 N8 C3 C2 -130.2(3) . . . . ?
C12 N8 C3 C4 106.0(3) . . . . ?
O9 C2 C3 N8 -54.1(2) . . . . ?
C1 C2 C3 N8 -172.56(19) . . . . ?
O9 C2 C3 C4 70.7(2) . . . . ?
C1 C2 C3 C4 -47.8(3) . . . . ?
N8 C3 C4 C5 176.6(2) . . . . ?
C2 C3 C4 C5 53.1(3) . . . . ?
C10 C1 O6 C5 71.3(2) . . . . ?
C2 C1 O6 C5 -56.6(2) . . . . ?
C1 O6 C5 C7 -173.6(2) . . . . ?
C1 O6 C5 C4 63.1(2) . . . . ?
C3 C4 C5 O6 -60.2(3) . . . . ?
C3 C4 C5 C7 -179.7(2) . . . . ?
O6 C5 C7 C24 -48.9(3) . . . . ?
C4 C5 C7 C24 72.0(3) . . . . ?
O6 C5 C7 C20 132.2(3) . . . . ?
C4 C5 C7 C20 -106.9(3) . . . . ?
C3 C2 O9 C28 153.4(2) . . . . ?
C1 C2 O9 C28 -85.0(2) . . . . ?
O6 C1 C10 O11 61.6(2) . . . . ?
C2 C1 C10 O11 -170.91(19) . . . . ?
C1 C10 O11 C31 162.1(2) . . . . ?
C3 N8 C12 O13 0.0(6) . . . . ?
C3 N8 C12 C14 178.9(2) . . . . ?
O13 C12 C14 N19 173.6(4) . . . . ?
N8 C12 C14 N19 -5.3(4) . . . . ?
O13 C12 C14 C15 -4.6(6) . . . . ?
N8 C12 C14 C15 176.4(4) . . . . ?
N19 C14 C15 C16 -1.5(7) . . . . ?
C12 C14 C15 C16 176.7(4) . . . . ?
C14 C15 C16 C17 1.3(8) . . . . ?
C24 C7 C20 C21 1.0(5) . . . . ?
C5 C7 C20 C21 179.9(3) . . . . ?
C15 C14 N19 C18 0.5(6) . . . . ?
C12 C14 N19 C18 -177.6(3) . . . . ?
C14 N19 C18 C17 0.6(6) . . . . ?
C15 C16 C17 C18 -0.2(7) . . . . ?
N19 C18 C17 C16 -0.8(7) . . . . ?
C7 C20 C21 C22 0.5(6) . . . . ?
C20 C21 C22 C23 -2.4(7) . . . . ?
C20 C21 C22 C25 178.7(4) . . . . ?
C21 C22 C23 C24 2.8(6) . . . . ?
C25 C22 C23 C24 -178.3(4) . . . . ?
C20 C7 C24 C23 -0.6(5) . . . . ?
C5 C7 C24 C23 -179.6(3) . . . . ?
C22 C23 C24 C7 -1.3(6) . . . . ?
C23 C22 C25 C26 144.9(5) . . . . ?
C21 C22 C25 C26 -36.2(8) . . . . ?
C23 C22 C25 C27 -72.6(8) . . . . ?
C21 C22 C25 C27 106.2(6) . . . . ?
C2 O9 C28 O30 3.6(4) . . . . ?
C2 O9 C28 C29 -175.1(2) . . . . ?
C10 O11 C31 O33 -2.1(4) . . . . ?
C10 O11 C31 C32 178.4(2) . . . . ?
