#------------------------------------------------------------------------------
#$Date: 2026-03-28 00:49:44 +0100 (Sat, 28 Mar 2026) $
#$Revision: 305202 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/25/18/7251834.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_7251834
loop_
_publ_author_name
'Gerasimova, Daria P.'
'Zakharychev, Dmitry V.'
'Saifina, Alina F.'
'Fayzullin, Robert R.'
'Lodochnikova, Olga'
_publ_section_title
;
 Solvent-controlled stereoselective supramolecular synthesis: a case of
 diastereomeric dimers of 16-S-dihydrosteviol
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D6CE00081A
_journal_year                    2026
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H32 O3'
_chemical_formula_sum            'C20 H32 O3'
_chemical_formula_weight         320.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-08-29 deposited with the CCDC.	2026-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.164(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.580(4)
_cell_length_b                   7.2369(13)
_cell_length_c                   22.829(4)
_cell_measurement_reflns_used    3781
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      16.65
_cell_measurement_theta_min      2.43
_cell_volume                     3529.1(11)
_computing_cell_refinement       'APEX4 v2021.10-0 (Bruker AXS)'
_computing_data_collection       'APEX4 v2021.10-0 (Bruker AXS)'
_computing_data_reduction        'APEX4 v2021.10-0 (Bruker AXS)'
_computing_molecular_graphics
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012);
PLATON (Spek, 2009); Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012);
PLATON (Spek, 2009); Olex2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      101(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3413
_diffrn_reflns_av_unetI/netI     0.2829
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            33546
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.862
_diffrn_reflns_theta_max         24.862
_diffrn_reflns_theta_min         1.402
_diffrn_source                   'microfocus Mo X-ray tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.4325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Stalke et al., 2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       plate
_exptl_crystal_F_000             1408
_exptl_crystal_recrystallization_method 'annealing of a solvate with tBuOH'
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.150
_refine_ls_abs_structure_details
;
 Flack x determined using 614 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -4.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6092
_refine_ls_number_restraints     1233
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.3270
_refine_ls_R_factor_gt           0.2315
_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)+(0.1641P)²+120.7618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4662
_refine_ls_wR_factor_ref         0.5163
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3163
_reflns_number_total             6092
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ce00081a2.cif
_cod_data_source_block           dp226i2
_cod_original_cell_volume        3529.1(12)
_cod_original_sg_symbol_H-M      'I 2'
_cod_database_code               7251834
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
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
O1A O 0.9180(8) 0.184(2) 0.0221(6) 0.031(4) Uani 1 1 d D U . . .
H1A H 0.934902 0.255697 0.000155 0.046 Uiso 1 1 calc R U . . .
O2A O 0.9242(8) 0.4383(18) 0.0808(7) 0.032(4) Uani 1 1 d D U . . .
O3A O 0.5814(7) 0.6051(18) 0.0777(6) 0.020(2) Uani 1 1 d D U . . .
H3A H 0.543869 0.591141 0.082677 0.030 Uiso 1 1 calc R U . . .
C1A C 0.7805(9) -0.064(2) 0.0902(9) 0.023(3) Uani 1 1 d D U . . .
H1AA H 0.778171 -0.132077 0.127399 0.027 Uiso 1 1 calc R U . . .
H1AB H 0.744256 -0.102351 0.061178 0.027 Uiso 1 1 calc R U . . .
C2A C 0.8374(9) -0.117(3) 0.0678(9) 0.028(4) Uani 1 1 d D U . . .
H2AA H 0.837100 -0.061632 0.028090 0.033 Uiso 1 1 calc R U . . .
H2AB H 0.837945 -0.252615 0.063342 0.033 Uiso 1 1 calc R U . . .
C3A C 0.8962(9) -0.058(3) 0.1065(9) 0.028(3) Uani 1 1 d D U . . .
H3AA H 0.932362 -0.084842 0.085543 0.034 Uiso 1 1 calc R U . . .
H3AB H 0.901099 -0.133548 0.143011 0.034 Uiso 1 1 calc R U . . .
C4A C 0.8983(9) 0.146(2) 0.1239(8) 0.027(3) Uani 1 1 d D U . . .
C5A C 0.8357(9) 0.203(2) 0.1440(8) 0.022(3) Uani 1 1 d D U . . .
H5A H 0.834155 0.128384 0.180600 0.027 Uiso 1 1 calc R U . . .
C6A C 0.8292(9) 0.402(2) 0.1645(9) 0.024(3) Uani 1 1 d D U . . .
H6AA H 0.820770 0.484875 0.129678 0.029 Uiso 1 1 calc R U . . .
H6AB H 0.868642 0.442565 0.188568 0.029 Uiso 1 1 calc R U . . .
C7A C 0.7739(8) 0.415(3) 0.2022(8) 0.024(3) Uani 1 1 d D U . . .
H7AA H 0.782425 0.329399 0.236322 0.029 Uiso 1 1 calc R U . . .
H7AB H 0.772191 0.541727 0.218084 0.029 Uiso 1 1 calc R U . . .
C8A C 0.7129(9) 0.369(2) 0.1687(8) 0.023(3) Uani 1 1 d D U . . .
C9A C 0.7169(9) 0.178(2) 0.1355(8) 0.022(3) Uani 1 1 d D U . . .
H9A H 0.722465 0.085421 0.168249 0.027 Uiso 1 1 calc R U . . .
C10A C 0.7749(9) 0.145(2) 0.1022(8) 0.022(3) Uani 1 1 d D U . . .
C11A C 0.6530(9) 0.124(3) 0.0987(9) 0.021(3) Uani 1 1 d D U . . .
H11A H 0.661357 0.039249 0.066804 0.025 Uiso 1 1 calc R U . . .
H11B H 0.628289 0.055296 0.124819 0.025 Uiso 1 1 calc R U . . .
C12A C 0.6127(9) 0.284(2) 0.0705(8) 0.018(3) Uani 1 1 d D U . . .
H12A H 0.624920 0.309695 0.031088 0.022 Uiso 1 1 calc R U . . .
H12B H 0.568487 0.243716 0.064270 0.022 Uiso 1 1 calc R U . . .
C13A C 0.6170(9) 0.463(2) 0.1054(8) 0.020(2) Uani 1 1 d D U . . .
C14A C 0.6856(8) 0.519(3) 0.1227(8) 0.021(3) Uani 1 1 d D U . . .
H14A H 0.688932 0.643530 0.140570 0.026 Uiso 1 1 calc R U . . .
H14B H 0.708036 0.517709 0.087732 0.026 Uiso 1 1 calc R U . . .
C15A C 0.6611(8) 0.363(3) 0.2060(8) 0.023(3) Uani 1 1 d D U . . .
H15A H 0.672315 0.441936 0.241411 0.028 Uiso 1 1 calc R U . . .
H15B H 0.655628 0.235213 0.219417 0.028 Uiso 1 1 calc R U . . .
C16A C 0.6001(8) 0.432(3) 0.1710(8) 0.021(3) Uani 1 1 d D U . . .
H16A H 0.592099 0.556868 0.186986 0.025 Uiso 1 1 calc R U . . .
C17A C 0.5425(9) 0.319(3) 0.1743(9) 0.025(4) Uani 1 1 d D U . . .
H17A H 0.544591 0.204718 0.151875 0.038 Uiso 1 1 calc R U . . .
H17B H 0.505475 0.390210 0.157432 0.038 Uiso 1 1 calc R U . . .
H17C H 0.539600 0.289955 0.215721 0.038 Uiso 1 1 calc R U . . .
C18A C 0.9516(9) 0.171(3) 0.1744(9) 0.032(4) Uani 1 1 d D U . . .
H18A H 0.954719 0.061616 0.199795 0.048 Uiso 1 1 calc R U . . .
H18B H 0.943531 0.280262 0.197651 0.048 Uiso 1 1 calc R U . . .
H18C H 0.990957 0.188243 0.158258 0.048 Uiso 1 1 calc R U . . .
C19A C 0.9146(10) 0.268(2) 0.0744(7) 0.029(3) Uani 1 1 d D U . . .
C20A C 0.7677(10) 0.248(3) 0.0426(8) 0.022(4) Uani 1 1 d D U . . .
H20A H 0.727581 0.215042 0.019182 0.034 Uiso 1 1 calc R U . . .
H20B H 0.801968 0.213462 0.020858 0.034 Uiso 1 1 calc R U . . .
H20C H 0.768906 0.381739 0.049759 0.034 Uiso 1 1 calc R U . . .
O1B O 0.3716(8) 0.741(2) 0.0155(6) 0.030(4) Uani 1 1 d D U . . .
H1B H 0.385690 0.684243 -0.011807 0.045 Uiso 1 1 calc R U . . .
O2B O 0.4488(7) 0.579(2) 0.0706(6) 0.028(3) Uani 1 1 d D U . . .
O3B O 0.0539(7) 0.458(2) 0.0555(6) 0.037(4) Uani 1 1 d D U . . .
H3B H 0.018550 0.471031 0.066323 0.056 Uiso 1 1 calc DR U . . .
C1B C 0.3309(9) 0.541(3) 0.2005(8) 0.033(4) Uani 1 1 d D U . . .
H1BA H 0.324656 0.620155 0.234527 0.039 Uiso 1 1 calc R U . . .
H1BB H 0.316668 0.415024 0.208913 0.039 Uiso 1 1 calc R U . . .
C2B C 0.3971(9) 0.534(3) 0.1967(10) 0.035(4) Uani 1 1 d D U . . .
H2BA H 0.404532 0.437359 0.167684 0.041 Uiso 1 1 calc R U . . .
H2BB H 0.419679 0.495989 0.235700 0.041 Uiso 1 1 calc R U . . .
C3B C 0.4242(10) 0.713(3) 0.1789(9) 0.035(4) Uani 1 1 d D U . . .
H3BA H 0.468408 0.692568 0.173515 0.042 Uiso 1 1 calc R U . . .
H3BB H 0.423679 0.803546 0.211299 0.042 Uiso 1 1 calc R U . . .
C4B C 0.3888(8) 0.794(2) 0.1218(8) 0.032(3) Uani 1 1 d D U . . .
C5B C 0.3183(9) 0.799(2) 0.1265(9) 0.031(3) Uani 1 1 d D U . . .
H5B H 0.315881 0.882536 0.161039 0.037 Uiso 1 1 calc R U . . .
C6B C 0.2742(9) 0.891(3) 0.0766(9) 0.035(4) Uani 1 1 d D U . . .
H6BA H 0.265544 0.804333 0.042763 0.042 Uiso 1 1 calc R U . . .
H6BB H 0.294084 1.002756 0.062921 0.042 Uiso 1 1 calc R U . . .
C7B C 0.2112(9) 0.944(3) 0.0994(9) 0.033(3) Uani 1 1 d D U . . .
H7BA H 0.220478 1.030263 0.133110 0.040 Uiso 1 1 calc R U . . .
H7BB H 0.184061 1.009705 0.067389 0.040 Uiso 1 1 calc R U . . .
C8B C 0.1768(9) 0.785(3) 0.1181(8) 0.034(3) Uani 1 1 d D U . . .
C9B C 0.2222(9) 0.660(3) 0.1620(8) 0.032(3) Uani 1 1 d D U . . .
H9B H 0.231571 0.737696 0.198371 0.039 Uiso 1 1 calc R U . . .
C10B C 0.2889(9) 0.614(2) 0.1452(8) 0.030(3) Uani 1 1 d D U . . .
C11B C 0.1877(9) 0.489(3) 0.1833(9) 0.036(4) Uani 1 1 d D U . . .
H11C H 0.219200 0.391250 0.195159 0.043 Uiso 1 1 calc R U . . .
H11D H 0.169542 0.524613 0.219101 0.043 Uiso 1 1 calc R U . . .
C12B C 0.1355(10) 0.406(3) 0.1386(9) 0.037(4) Uani 1 1 d D U . . .
H12C H 0.154345 0.311290 0.115090 0.044 Uiso 1 1 calc R U . . .
H12D H 0.105800 0.340988 0.160850 0.044 Uiso 1 1 calc R U . . .
C13B C 0.0989(9) 0.540(3) 0.0962(8) 0.036(3) Uani 1 1 d D U . . .
C14B C 0.1437(9) 0.662(3) 0.0668(8) 0.036(3) Uani 1 1 d D U . . .
H14C H 0.120399 0.738680 0.035157 0.043 Uiso 1 1 calc R U . . .
H14D H 0.174522 0.585271 0.049500 0.043 Uiso 1 1 calc R U . . .
C15B C 0.1209(9) 0.840(3) 0.1463(9) 0.034(3) Uani 1 1 d D U . . .
H15C H 0.106470 0.963843 0.132125 0.041 Uiso 1 1 calc R U . . .
H15D H 0.132693 0.845902 0.189761 0.041 Uiso 1 1 calc R U . . .
C16B C 0.0681(9) 0.701(3) 0.1312(9) 0.035(3) Uani 1 1 d D U . . .
H16B H 0.036091 0.762720 0.101636 0.042 Uiso 1 1 calc R U . . .
C17B C 0.0342(11) 0.636(3) 0.1803(10) 0.041(5) Uani 1 1 d D U . . .
H17D H 0.064637 0.604330 0.214837 0.062 Uiso 1 1 calc R U . . .
H17E H 0.009023 0.527301 0.167248 0.062 Uiso 1 1 calc R U . . .
H17F H 0.006743 0.735050 0.190867 0.062 Uiso 1 1 calc R U . . .
C18B C 0.4132(10) 0.988(3) 0.1142(10) 0.033(4) Uani 1 1 d D U . . .
H18D H 0.398461 1.031968 0.074058 0.050 Uiso 1 1 calc R U . . .
H18E H 0.459095 0.986828 0.120803 0.050 Uiso 1 1 calc R U . . .
H18F H 0.397886 1.070852 0.142989 0.050 Uiso 1 1 calc R U . . .
C19B C 0.4029(8) 0.687(3) 0.0683(7) 0.029(3) Uani 1 1 d D U . . .
C20B C 0.2847(11) 0.466(3) 0.0962(9) 0.032(4) Uani 1 1 d D U . . .
H20D H 0.322395 0.389291 0.102141 0.048 Uiso 1 1 calc R U . . .
H20E H 0.281292 0.526821 0.057454 0.048 Uiso 1 1 calc R U . . .
H20F H 0.247730 0.388952 0.097869 0.048 Uiso 1 1 calc R U . . .
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'
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
C19A O1A H1A 109.5 . . ?
C13A O3A H3A 109.5 . . ?
C2A C1A C10A 114.4(15) . . ?
C2A C1A H1AA 108.7 . . ?
C10A C1A H1AA 108.7 . . ?
C2A C1A H1AB 108.7 . . ?
C10A C1A H1AB 108.7 . . ?
H1AA C1A H1AB 107.6 . . ?
C1A C2A C3A 114.1(16) . . ?
C1A C2A H2AA 108.7 . . ?
C3A C2A H2AA 108.7 . . ?
C1A C2A H2AB 108.7 . . ?
C3A C2A H2AB 108.7 . . ?
H2AA C2A H2AB 107.6 . . ?
C2A C3A C4A 114.6(16) . . ?
C2A C3A H3AA 108.6 . . ?
C4A C3A H3AA 108.6 . . ?
C2A C3A H3AB 108.6 . . ?
C4A C3A H3AB 108.6 . . ?
H3AA C3A H3AB 107.6 . . ?
C19A C4A C18A 105.4(14) . . ?
C19A C4A C3A 111.6(11) . . ?
C18A C4A C3A 107.6(15) . . ?
C19A C4A C5A 112.0(14) . . ?
C18A C4A C5A 110.1(13) . . ?
C3A C4A C5A 109.9(14) . . ?
C6A C5A C4A 117.7(14) . . ?
C6A C5A C10A 109.5(15) . . ?
C4A C5A C10A 116.1(14) . . ?
C6A C5A H5A 103.8 . . ?
C4A C5A H5A 103.8 . . ?
C10A C5A H5A 103.8 . . ?
C5A C6A C7A 109.4(14) . . ?
C5A C6A H6AA 109.8 . . ?
C7A C6A H6AA 109.8 . . ?
C5A C6A H6AB 109.8 . . ?
C7A C6A H6AB 109.8 . . ?
H6AA C6A H6AB 108.2 . . ?
C8A C7A C6A 113.4(15) . . ?
C8A C7A H7AA 108.9 . . ?
C6A C7A H7AA 108.9 . . ?
C8A C7A H7AB 108.9 . . ?
C6A C7A H7AB 108.9 . . ?
H7AA C7A H7AB 107.7 . . ?
C7A C8A C15A 113.4(15) . . ?
C7A C8A C14A 114.8(15) . . ?
C15A C8A C14A 99.3(14) . . ?
C7A C8A C9A 109.9(15) . . ?
C15A C8A C9A 110.1(15) . . ?
C14A C8A C9A 108.8(14) . . ?
C11A C9A C10A 113.9(14) . . ?
C11A C9A C8A 111.8(14) . . ?
C10A C9A C8A 117.8(14) . . ?
C11A C9A H9A 103.8 . . ?
C10A C9A H9A 103.8 . . ?
C8A C9A H9A 103.8 . . ?
C20A C10A C1A 108.5(15) . . ?
C20A C10A C5A 112.2(14) . . ?
C1A C10A C5A 107.0(14) . . ?
C20A C10A C9A 111.4(15) . . ?
C1A C10A C9A 108.9(14) . . ?
C5A C10A C9A 108.7(14) . . ?
C12A C11A C9A 116.3(15) . . ?
C12A C11A H11A 108.2 . . ?
C9A C11A H11A 108.2 . . ?
C12A C11A H11B 108.2 . . ?
C9A C11A H11B 108.2 . . ?
H11A C11A H11B 107.4 . . ?
C13A C12A C11A 115.8(15) . . ?
C13A C12A H12A 108.3 . . ?
C11A C12A H12A 108.3 . . ?
C13A C12A H12B 108.3 . . ?
C11A C12A H12B 108.3 . . ?
H12A C12A H12B 107.4 . . ?
O3A C13A C12A 114.0(14) . . ?
O3A C13A C14A 112.2(14) . . ?
C12A C13A C14A 110.1(15) . . ?
O3A C13A C16A 110.3(14) . . ?
C12A C13A C16A 111.3(14) . . ?
C14A C13A C16A 97.8(13) . . ?
C13A C14A C8A 104.5(13) . . ?
C13A C14A H14A 110.9 . . ?
C8A C14A H14A 110.9 . . ?
C13A C14A H14B 110.9 . . ?
C8A C14A H14B 110.9 . . ?
H14A C14A H14B 108.9 . . ?
C8A C15A C16A 110.7(14) . . ?
C8A C15A H15A 109.5 . . ?
C16A C15A H15A 109.5 . . ?
C8A C15A H15B 109.5 . . ?
C16A C15A H15B 109.5 . . ?
H15A C15A H15B 108.1 . . ?
C17A C16A C15A 117.4(15) . . ?
C17A C16A C13A 115.1(15) . . ?
C15A C16A C13A 103.9(14) . . ?
C17A C16A H16A 106.6 . . ?
C15A C16A H16A 106.6 . . ?
C13A C16A H16A 106.6 . . ?
C16A C17A H17A 109.5 . . ?
C16A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C16A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C4A C18A H18A 109.5 . . ?
C4A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C4A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
O2A C19A O1A 121.0(15) . . ?
O2A C19A C4A 122.4(11) . . ?
O1A C19A C4A 116.6(10) . . ?
C10A C20A H20A 109.5 . . ?
C10A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C10A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C19B O1B H1B 109.5 . . ?
C13B O3B H3B 109.5 . . ?
C2B C1B C10B 115.9(16) . . ?
C2B C1B H1BA 108.3 . . ?
C10B C1B H1BA 108.3 . . ?
C2B C1B H1BB 108.3 . . ?
C10B C1B H1BB 108.3 . . ?
H1BA C1B H1BB 107.4 . . ?
C1B C2B C3B 114.2(17) . . ?
C1B C2B H2BA 108.7 . . ?
C3B C2B H2BA 108.7 . . ?
C1B C2B H2BB 108.7 . . ?
C3B C2B H2BB 108.7 . . ?
H2BA C2B H2BB 107.6 . . ?
C2B C3B C4B 113.3(16) . . ?
C2B C3B H3BA 108.9 . . ?
C4B C3B H3BA 108.9 . . ?
C2B C3B H3BB 108.9 . . ?
C4B C3B H3BB 108.9 . . ?
H3BA C3B H3BB 107.7 . . ?
C19B C4B C18B 105.6(14) . . ?
C19B C4B C3B 110.9(11) . . ?
C18B C4B C3B 108.2(15) . . ?
C19B C4B C5B 112.5(14) . . ?
C18B C4B C5B 110.4(14) . . ?
C3B C4B C5B 109.1(15) . . ?
C6B C5B C4B 118.4(14) . . ?
C6B C5B C10B 109.8(15) . . ?
C4B C5B C10B 116.2(14) . . ?
C6B C5B H5B 103.4 . . ?
C4B C5B H5B 103.4 . . ?
C10B C5B H5B 103.4 . . ?
C5B C6B C7B 109.7(15) . . ?
C5B C6B H6BA 109.7 . . ?
C7B C6B H6BA 109.7 . . ?
C5B C6B H6BB 109.7 . . ?
C7B C6B H6BB 109.7 . . ?
H6BA C6B H6BB 108.2 . . ?
C8B C7B C6B 113.7(15) . . ?
C8B C7B H7BA 108.8 . . ?
C6B C7B H7BA 108.8 . . ?
C8B C7B H7BB 108.8 . . ?
C6B C7B H7BB 108.8 . . ?
H7BA C7B H7BB 107.7 . . ?
C7B C8B C15B 113.0(15) . . ?
C7B C8B C14B 115.2(15) . . ?
C15B C8B C14B 99.3(14) . . ?
C7B C8B C9B 110.0(15) . . ?
C15B C8B C9B 110.1(15) . . ?
C14B C8B C9B 108.8(14) . . ?
C11B C9B C10B 113.8(14) . . ?
C11B C9B C8B 111.9(15) . . ?
C10B C9B C8B 118.0(14) . . ?
C11B C9B H9B 103.7 . . ?
C10B C9B H9B 103.7 . . ?
C8B C9B H9B 103.7 . . ?
C1B C10B C20B 108.8(15) . . ?
C1B C10B C5B 107.7(14) . . ?
C20B C10B C5B 112.4(14) . . ?
C1B C10B C9B 108.9(14) . . ?
C20B C10B C9B 111.1(15) . . ?
C5B C10B C9B 107.9(14) . . ?
C12B C11B C9B 116.3(15) . . ?
C12B C11B H11C 108.2 . . ?
C9B C11B H11C 108.2 . . ?
C12B C11B H11D 108.2 . . ?
C9B C11B H11D 108.2 . . ?
H11C C11B H11D 107.4 . . ?
C13B C12B C11B 116.1(15) . . ?
C13B C12B H12C 108.3 . . ?
C11B C12B H12C 108.3 . . ?
C13B C12B H12D 108.3 . . ?
C11B C12B H12D 108.3 . . ?
H12C C12B H12D 107.4 . . ?
O3B C13B C12B 113.8(15) . . ?
O3B C13B C14B 112.4(15) . . ?
C12B C13B C14B 110.2(15) . . ?
O3B C13B C16B 110.3(14) . . ?
C12B C13B C16B 111.3(14) . . ?
C14B C13B C16B 97.7(13) . . ?
C13B C14B C8B 104.5(13) . . ?
C13B C14B H14C 110.9 . . ?
C8B C14B H14C 110.9 . . ?
C13B C14B H14D 110.9 . . ?
C8B C14B H14D 110.9 . . ?
H14C C14B H14D 108.9 . . ?
C8B C15B C16B 110.7(15) . . ?
C8B C15B H15C 109.5 . . ?
C16B C15B H15C 109.5 . . ?
C8B C15B H15D 109.5 . . ?
C16B C15B H15D 109.5 . . ?
H15C C15B H15D 108.1 . . ?
C17B C16B C15B 117.9(16) . . ?
C17B C16B C13B 115.2(16) . . ?
C15B C16B C13B 103.9(14) . . ?
C17B C16B H16B 106.3 . . ?
C15B C16B H16B 106.3 . . ?
C13B C16B H16B 106.3 . . ?
C16B C17B H17D 109.5 . . ?
C16B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C16B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C4B C18B H18D 109.5 . . ?
C4B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C4B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
O2B C19B O1B 120.5(15) . . ?
O2B C19B C4B 122.1(11) . . ?
O1B C19B C4B 116.1(10) . . ?
C10B C20B H20D 109.5 . . ?
C10B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C10B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 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
O1A C19A 1.350(14) . ?
O1A H1A 0.8400 . ?
O2A C19A 1.257(14) . ?
O3A C13A 1.38(2) . ?
O3A H3A 0.8400 . ?
C1A C2A 1.45(2) . ?
C1A C10A 1.54(2) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C2A C3A 1.50(2) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3A C4A 1.53(2) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A C19A 1.51(2) . ?
C4A C18A 1.52(2) . ?
C4A C5A 1.54(2) . ?
C5A C6A 1.53(2) . ?
C5A C10A 1.57(2) . ?
C5A H5A 1.0000 . ?
C6A C7A 1.57(2) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A C8A 1.46(2) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C15A 1.50(2) . ?
C8A C14A 1.56(2) . ?
C8A C9A 1.58(2) . ?
C9A C11A 1.56(2) . ?
C9A C10A 1.57(2) . ?
C9A H9A 1.0000 . ?
C10A C20A 1.54(2) . ?
C11A C12A 1.53(2) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A C13A 1.52(2) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A C14A 1.53(2) . ?
C13A C16A 1.61(2) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A C16A 1.52(2) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A C17A 1.50(2) . ?
C16A H16A 1.0000 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
O1B C19B 1.352(13) . ?
O1B H1B 0.8400 . ?
O2B C19B 1.258(14) . ?
O3B C13B 1.38(2) . ?
O3B H3B 0.8400 . ?
C1B C2B 1.45(2) . ?
C1B C10B 1.54(2) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C2B C3B 1.50(3) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C3B C4B 1.53(2) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C4B C19B 1.51(2) . ?
C4B C18B 1.52(2) . ?
C4B C5B 1.54(2) . ?
C5B C6B 1.53(2) . ?
C5B C10B 1.57(2) . ?
C5B H5B 1.0000 . ?
C6B C7B 1.57(2) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C8B 1.46(2) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C15B 1.50(2) . ?
C8B C14B 1.56(2) . ?
C8B C9B 1.58(2) . ?
C9B C11B 1.56(2) . ?
C9B C10B 1.58(2) . ?
C9B H9B 1.0000 . ?
C10B C20B 1.54(2) . ?
C11B C12B 1.53(2) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B C13B 1.52(2) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B C14B 1.53(2) . ?
C13B C16B 1.61(2) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B C16B 1.52(2) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B C17B 1.50(2) . ?
C16B H16B 1.0000 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
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
O1A H1A O3B 0.84 1.97 2.78(2) 160.9 2_655 yes
O3A H3A O2B 0.84 2.03 2.85(2) 164.0 . yes
O1B H1B O3A 0.84 1.84 2.67(2) 168.8 2_655 yes
O3B H3B O2A 0.84 2.12 2.94(2) 164.7 1_455 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
C10A C1A C2A C3A 56(2) . . . . ?
C1A C2A C3A C4A -51(2) . . . . ?
C2A C3A C4A C19A -79(2) . . . . ?
C2A C3A C4A C18A 165.8(16) . . . . ?
C2A C3A C4A C5A 46(2) . . . . ?
C19A C4A C5A C6A -56.6(19) . . . . ?
C18A C4A C5A C6A 60(2) . . . . ?
C3A C4A C5A C6A 178.7(16) . . . . ?
C19A C4A C5A C10A 76.1(17) . . . . ?
C18A C4A C5A C10A -166.9(15) . . . . ?
C3A C4A C5A C10A -49(2) . . . . ?
C4A C5A C6A C7A -161.0(15) . . . . ?
C10A C5A C6A C7A 63.4(18) . . . . ?
C5A C6A C7A C8A -63(2) . . . . ?
C6A C7A C8A C15A 174.5(15) . . . . ?
C6A C7A C8A C14A -72(2) . . . . ?
C6A C7A C8A C9A 51(2) . . . . ?
C7A C8A C9A C11A -179.6(15) . . . . ?
C15A C8A C9A C11A 54.8(19) . . . . ?
C14A C8A C9A C11A -53.0(18) . . . . ?
C7A C8A C9A C10A -45(2) . . . . ?
C15A C8A C9A C10A -170.4(15) . . . . ?
C14A C8A C9A C10A 81.8(18) . . . . ?
C2A C1A C10A C20A 68(2) . . . . ?
C2A C1A C10A C5A -54(2) . . . . ?
C2A C1A C10A C9A -171.1(16) . . . . ?
C6A C5A C10A C20A 68.8(19) . . . . ?
C4A C5A C10A C20A -68(2) . . . . ?
C6A C5A C10A C1A -172.3(14) . . . . ?
C4A C5A C10A C1A 51.4(19) . . . . ?
C6A C5A C10A C9A -54.8(17) . . . . ?
C4A C5A C10A C9A 168.8(14) . . . . ?
C11A C9A C10A C20A 56.3(19) . . . . ?
C8A C9A C10A C20A -77.7(19) . . . . ?
C11A C9A C10A C1A -63.4(19) . . . . ?
C8A C9A C10A C1A 162.6(15) . . . . ?
C11A C9A C10A C5A -179.6(15) . . . . ?
C8A C9A C10A C5A 46.4(19) . . . . ?
C10A C9A C11A C12A -102.5(18) . . . . ?
C8A C9A C11A C12A 34(2) . . . . ?
C9A C11A C12A C13A -34(2) . . . . ?
C11A C12A C13A O3A 178.3(15) . . . . ?
C11A C12A C13A C14A 51(2) . . . . ?
C11A C12A C13A C16A -56(2) . . . . ?
O3A C13A C14A C8A 163.5(14) . . . . ?
C12A C13A C14A C8A -68.4(17) . . . . ?
C16A C13A C14A C8A 47.8(16) . . . . ?
C7A C8A C14A C13A -166.5(15) . . . . ?
C15A C8A C14A C13A -45.2(17) . . . . ?
C9A C8A C14A C13A 69.8(17) . . . . ?
C7A C8A C15A C16A 145.5(16) . . . . ?
C14A C8A C15A C16A 23.2(19) . . . . ?
C9A C8A C15A C16A -90.9(18) . . . . ?
C8A C15A C16A C17A 133.6(18) . . . . ?
C8A C15A C16A C13A 5(2) . . . . ?
O3A C13A C16A C17A 81(2) . . . . ?
C12A C13A C16A C17A -47(2) . . . . ?
C14A C13A C16A C17A -161.7(16) . . . . ?
O3A C13A C16A C15A -149.2(15) . . . . ?
C12A C13A C16A C15A 83.2(18) . . . . ?
C14A C13A C16A C15A -31.9(17) . . . . ?
C18A C4A C19A O2A -57(2) . . . . ?
C3A C4A C19A O2A -174(2) . . . . ?
C5A C4A C19A O2A 63(2) . . . . ?
C18A C4A C19A O1A 123.4(19) . . . . ?
C3A C4A C19A O1A 7(2) . . . . ?
C5A C4A C19A O1A -116.9(19) . . . . ?
C10B C1B C2B C3B 53(2) . . . . ?
C1B C2B C3B C4B -53(2) . . . . ?
C2B C3B C4B C19B -74(2) . . . . ?
C2B C3B C4B C18B 170.5(17) . . . . ?
C2B C3B C4B C5B 50(2) . . . . ?
C19B C4B C5B C6B -62(2) . . . . ?
C18B C4B C5B C6B 56(2) . . . . ?
C3B C4B C5B C6B 174.9(16) . . . . ?
C19B C4B C5B C10B 72.4(17) . . . . ?
C18B C4B C5B C10B -169.9(15) . . . . ?
C3B C4B C5B C10B -51(2) . . . . ?
C4B C5B C6B C7B -160.0(16) . . . . ?
C10B C5B C6B C7B 63.3(19) . . . . ?
C5B C6B C7B C8B -62(2) . . . . ?
C6B C7B C8B C15B 173.2(16) . . . . ?
C6B C7B C8B C14B -74(2) . . . . ?
C6B C7B C8B C9B 50(2) . . . . ?
C7B C8B C9B C11B 180.0(16) . . . . ?
C15B C8B C9B C11B 54.8(19) . . . . ?
C14B C8B C9B C11B -53.0(19) . . . . ?
C7B C8B C9B C10B -45(2) . . . . ?
C15B C8B C9B C10B -170.3(15) . . . . ?
C14B C8B C9B C10B 81.9(19) . . . . ?
C2B C1B C10B C20B 73(2) . . . . ?
C2B C1B C10B C5B -49(2) . . . . ?
C2B C1B C10B C9B -166.0(17) . . . . ?
C6B C5B C10B C1B -172.9(15) . . . . ?
C4B C5B C10B C1B 49(2) . . . . ?
C6B C5B C10B C20B 67(2) . . . . ?
C4B C5B C10B C20B -70(2) . . . . ?
C6B C5B C10B C9B -55.5(18) . . . . ?
C4B C5B C10B C9B 166.7(15) . . . . ?
C11B C9B C10B C1B -61.8(19) . . . . ?
C8B C9B C10B C1B 164.1(16) . . . . ?
C11B C9B C10B C20B 58(2) . . . . ?
C8B C9B C10B C20B -76.2(19) . . . . ?
C11B C9B C10B C5B -178.4(15) . . . . ?
C8B C9B C10B C5B 47(2) . . . . ?
C10B C9B C11B C12B -103.2(19) . . . . ?
C8B C9B C11B C12B 34(2) . . . . ?
C9B C11B C12B C13B -33(3) . . . . ?
C11B C12B C13B O3B 177.8(17) . . . . ?
C11B C12B C13B C14B 50(2) . . . . ?
C11B C12B C13B C16B -57(2) . . . . ?
O3B C13B C14B C8B 163.8(14) . . . . ?
C12B C13B C14B C8B -68.1(17) . . . . ?
C16B C13B C14B C8B 48.0(16) . . . . ?
C7B C8B C14B C13B -166.1(15) . . . . ?
C15B C8B C14B C13B -45.1(17) . . . . ?
C9B C8B C14B C13B 69.9(17) . . . . ?
C7B C8B C15B C16B 145.3(17) . . . . ?
C14B C8B C15B C16B 23(2) . . . . ?
C9B C8B C15B C16B -91.3(19) . . . . ?
C8B C15B C16B C17B 134.8(18) . . . . ?
C8B C15B C16B C13B 6(2) . . . . ?
O3B C13B C16B C17B 80(2) . . . . ?
C12B C13B C16B C17B -48(2) . . . . ?
C14B C13B C16B C17B -162.9(17) . . . . ?
O3B C13B C16B C15B -149.9(16) . . . . ?
C12B C13B C16B C15B 82.8(18) . . . . ?
C14B C13B C16B C15B -32.4(18) . . . . ?
C18B C4B C19B O2B 101(2) . . . . ?
C3B C4B C19B O2B -16(3) . . . . ?
C5B C4B C19B O2B -138.7(19) . . . . ?
C18B C4B C19B O1B -66(2) . . . . ?
C3B C4B C19B O1B 176.6(17) . . . . ?
C5B C4B C19B O1B 54(2) . . . . ?
