#------------------------------------------------------------------------------
#$Date: 2022-05-05 04:45:47 +0300 (Thu, 05 May 2022) $
#$Revision: 274909 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/89/2108966.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2108966
loop_
_publ_author_name
'Langer, Dominik'
'Wicher, Barbara'
'Tykarska, Ewa'
_publ_section_title
;
 Single-crystal-to-single-crystal phase transition of 18β-glycyrrhetinic
 acid isopropyl ester
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520622002517
_journal_volume                  78
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C36 H57 N O5'
_chemical_formula_sum            'C36 H57 N O5'
_chemical_formula_weight         583.82
_chemical_melting_point          478.5(5)
_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   geom
_audit_creation_date             2021-10-29
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9136(2)
_cell_length_b                   13.7752(3)
_cell_length_c                   18.7441(4)
_cell_measurement_reflns_used    20546
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      76.243
_cell_measurement_theta_min      3.929
_cell_volume                     3334.34(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 10.3991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            64824
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         6.426
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2381 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         6099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0586P)²+0.3153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5635
_reflns_number_total             6099
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            rm5058sup1.cif
_cod_data_source_block           2-morpholinoethyl-GE
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '478-479' was changed to
'478.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        3334.32(10)
_cod_database_code               2108966
_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_max   0.971
_shelx_estimated_absorpt_t_min   0.797
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3A), C5(H5), C9(H9), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C15(H15A,H15B), C16(H16A,
 H16B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B), C31(H31A,H31B),
 C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
O1 O 0.7062(3) 0.8231(2) 0.59577(15) 0.1175(10) Uani 1 1 d . . . . .
O3 O 0.65538(14) -0.16260(16) 0.82993(12) 0.0767(6) Uani 1 1 d . . . . .
H3 H 0.594289 -0.178572 0.832028 0.115 Uiso 1 1 calc R U . . .
O11 O 0.54649(12) 0.26207(13) 0.67561(11) 0.0661(5) Uani 1 1 d . . . . .
O30 O 0.56759(12) 0.51704(12) 0.41328(11) 0.0620(4) Uani 1 1 d . . . . .
O31 O 0.67744(17) 0.62505(13) 0.36652(11) 0.0734(5) Uani 1 1 d . . . . .
N1 N 0.59458(18) 0.67050(17) 0.52685(12) 0.0643(5) Uani 1 1 d . . . . .
C1 C 0.59157(15) 0.06282(16) 0.72346(12) 0.0478(5) Uani 1 1 d . . . . .
H1A H 0.533638 0.107420 0.726690 0.057 Uiso 1 1 calc R U . . .
H1B H 0.589673 0.032984 0.676605 0.057 Uiso 1 1 calc R U . . .
C2 C 0.57905(17) -0.01595(18) 0.78003(13) 0.0535(5) Uani 1 1 d . . . . .
H2A H 0.575484 0.014021 0.826799 0.064 Uiso 1 1 calc R U . . .
H2B H 0.514580 -0.050381 0.771969 0.064 Uiso 1 1 calc R U . . .
C3 C 0.66748(17) -0.08698(17) 0.77847(13) 0.0516(5) Uani 1 1 d . . . . .
H3A H 0.667977 -0.117343 0.731191 0.062 Uiso 1 1 calc R U . . .
C4 C 0.77382(17) -0.03905(18) 0.78962(12) 0.0520(5) Uani 1 1 d . . . . .
C5 C 0.78324(15) 0.04489(15) 0.73409(11) 0.0424(4) Uani 1 1 d . . . . .
H5 H 0.780454 0.012259 0.687676 0.051 Uiso 1 1 calc R U . . .
C6 C 0.88865(16) 0.09568(19) 0.73474(14) 0.0551(6) Uani 1 1 d . . . . .
H6A H 0.891987 0.140364 0.774672 0.066 Uiso 1 1 calc R U . . .
H6B H 0.943136 0.047865 0.740603 0.066 Uiso 1 1 calc R U . . .
C7 C 0.90501(15) 0.15092(18) 0.66539(13) 0.0524(5) Uani 1 1 d . . . . .
H7A H 0.907496 0.104756 0.626354 0.063 Uiso 1 1 calc R U . . .
H7B H 0.971556 0.183477 0.667396 0.063 Uiso 1 1 calc R U . . .
C8 C 0.82074(14) 0.22662(15) 0.64940(10) 0.0392(4) Uani 1 1 d . . . . .
C9 C 0.71135(13) 0.18155(14) 0.66164(10) 0.0361(4) Uani 1 1 d . . . . .
H9 H 0.703412 0.134508 0.622796 0.043 Uiso 1 1 calc R U . . .
C10 C 0.69357(14) 0.12058(15) 0.73126(10) 0.0401(4) Uani 1 1 d . . . . .
C11 C 0.63064(15) 0.25939(15) 0.64578(12) 0.0445(5) Uani 1 1 d . . . . .
C12 C 0.65543(15) 0.33144(16) 0.59114(12) 0.0466(5) Uani 1 1 d . . . . .
H12 H 0.604905 0.377239 0.580314 0.056 Uiso 1 1 calc R U . . .
C13 C 0.74495(14) 0.33679(14) 0.55544(10) 0.0385(4) Uani 1 1 d . . . . .
C14 C 0.82834(14) 0.26033(14) 0.56862(10) 0.0391(4) Uani 1 1 d . . . . .
C15 C 0.93900(16) 0.29807(17) 0.55156(13) 0.0512(5) Uani 1 1 d . . . . .
H15A H 0.965704 0.331375 0.593284 0.061 Uiso 1 1 calc R U . . .
H15B H 0.983591 0.242772 0.542474 0.061 Uiso 1 1 calc R U . . .
C16 C 0.94506(16) 0.36686(18) 0.48779(13) 0.0527(5) Uani 1 1 d . . . . .
H16A H 0.927957 0.331343 0.444686 0.063 Uiso 1 1 calc R U . . .
H16B H 1.015505 0.390442 0.483064 0.063 Uiso 1 1 calc R U . . .
C17 C 0.87162(16) 0.45368(16) 0.49510(12) 0.0483(5) Uani 1 1 d . . . . .
C18 C 0.75897(15) 0.41470(15) 0.49886(11) 0.0419(4) Uani 1 1 d . . . . .
H18 H 0.714941 0.469484 0.512734 0.050 Uiso 1 1 calc R U . . .
C19 C 0.71886(16) 0.37844(16) 0.42613(11) 0.0453(5) Uani 1 1 d . . . . .
H19A H 0.758778 0.322070 0.411781 0.054 Uiso 1 1 calc R U . . .
H19B H 0.647239 0.358370 0.431200 0.054 Uiso 1 1 calc R U . . .
C20 C 0.72606(17) 0.45589(17) 0.36755(12) 0.0491(5) Uani 1 1 d . . . . .
C21 C 0.83911(19) 0.4884(2) 0.36162(14) 0.0600(6) Uani 1 1 d . . . . .
H21A H 0.880701 0.434324 0.344933 0.072 Uiso 1 1 calc R U . . .
H21B H 0.844124 0.539922 0.326524 0.072 Uiso 1 1 calc R U . . .
C22 C 0.88237(19) 0.52428(18) 0.43201(14) 0.0592(6) Uani 1 1 d . . . . .
H22A H 0.847703 0.584454 0.444333 0.071 Uiso 1 1 calc R U . . .
H22B H 0.955238 0.538911 0.425505 0.071 Uiso 1 1 calc R U . . .
C24 C 0.7874(2) -0.0069(2) 0.86750(13) 0.0747(9) Uani 1 1 d . . . . .
H24A H 0.727201 0.028516 0.882545 0.112 Uiso 1 1 calc R U . . .
H24B H 0.847372 0.033969 0.871382 0.112 Uiso 1 1 calc R U . . .
H24C H 0.796125 -0.063002 0.897262 0.112 Uiso 1 1 calc R U . . .
C23 C 0.8562(2) -0.1163(2) 0.7728(2) 0.0793(9) Uani 1 1 d . . . . .
H23A H 0.923397 -0.092004 0.785311 0.119 Uiso 1 1 calc R U . . .
H23B H 0.854562 -0.131166 0.722719 0.119 Uiso 1 1 calc R U . . .
H23C H 0.841941 -0.174087 0.799689 0.119 Uiso 1 1 calc R U . . .
C25 C 0.6853(2) 0.18551(19) 0.79811(12) 0.0573(6) Uani 1 1 d . . . . .
H25A H 0.647095 0.243213 0.786617 0.086 Uiso 1 1 calc R U . . .
H25B H 0.753471 0.202965 0.813986 0.086 Uiso 1 1 calc R U . . .
H25C H 0.650153 0.150732 0.835312 0.086 Uiso 1 1 calc R U . . .
C26 C 0.83772(19) 0.31309(18) 0.70015(12) 0.0529(5) Uani 1 1 d . . . . .
H26A H 0.845566 0.289683 0.748089 0.079 Uiso 1 1 calc R U . . .
H26B H 0.779116 0.355851 0.697745 0.079 Uiso 1 1 calc R U . . .
H26C H 0.899045 0.347646 0.686259 0.079 Uiso 1 1 calc R U . . .
C27 C 0.8064(2) 0.17643(16) 0.51518(11) 0.0521(5) Uani 1 1 d . . . . .
H27A H 0.733685 0.161792 0.515267 0.078 Uiso 1 1 calc R U . . .
H27B H 0.844712 0.119837 0.529173 0.078 Uiso 1 1 calc R U . . .
H27C H 0.827144 0.195867 0.468128 0.078 Uiso 1 1 calc R U . . .
C28 C 0.8962(2) 0.51063(19) 0.56308(15) 0.0654(7) Uani 1 1 d . . . . .
H28A H 0.881997 0.470873 0.603991 0.098 Uiso 1 1 calc R U . . .
H28B H 0.854010 0.567968 0.564857 0.098 Uiso 1 1 calc R U . . .
H28C H 0.967955 0.528786 0.563045 0.098 Uiso 1 1 calc R U . . .
C29 C 0.6914(2) 0.4131(2) 0.29565(13) 0.0634(6) Uani 1 1 d . . . . .
H29A H 0.621299 0.390575 0.299437 0.095 Uiso 1 1 calc R U . . .
H29B H 0.735756 0.359756 0.283192 0.095 Uiso 1 1 calc R U . . .
H29C H 0.695652 0.462185 0.259421 0.095 Uiso 1 1 calc R U . . .
C30 C 0.65707(18) 0.54289(18) 0.38234(12) 0.0519(5) Uani 1 1 d . . . . .
C31 C 0.4942(2) 0.5932(2) 0.4296(2) 0.0784(9) Uani 1 1 d . . . . .
H31A H 0.424716 0.571298 0.418487 0.094 Uiso 1 1 calc R U . . .
H31B H 0.508991 0.649759 0.400514 0.094 Uiso 1 1 calc R U . . .
C32 C 0.5003(2) 0.6204(2) 0.5070(2) 0.0842(9) Uani 1 1 d . . . . .
H32A H 0.441635 0.661488 0.518575 0.101 Uiso 1 1 calc R U . . .
H32B H 0.494448 0.561802 0.535496 0.101 Uiso 1 1 calc R U . . .
C33 C 0.6052(4) 0.6770(3) 0.60412(18) 0.1010(13) Uani 1 1 d . . . . .
H33A H 0.606160 0.612222 0.624346 0.121 Uiso 1 1 calc R U . . .
H33B H 0.546068 0.711282 0.623743 0.121 Uiso 1 1 calc R U . . .
C34 C 0.7019(5) 0.7288(3) 0.6241(2) 0.1235(18) Uani 1 1 d . . . . .
H34A H 0.706528 0.732339 0.675636 0.148 Uiso 1 1 calc R U . . .
H34B H 0.760924 0.692014 0.606974 0.148 Uiso 1 1 calc R U . . .
C35 C 0.6959(4) 0.8180(3) 0.5211(2) 0.1120(14) Uani 1 1 d . . . . .
H35A H 0.754869 0.783387 0.501587 0.134 Uiso 1 1 calc R U . . .
H35B H 0.696711 0.883257 0.501709 0.134 Uiso 1 1 calc R U . . .
C36 C 0.5989(3) 0.7684(2) 0.49816(18) 0.0813(9) Uani 1 1 d . . . . .
H36A H 0.539449 0.805062 0.514704 0.098 Uiso 1 1 calc R U . . .
H36B H 0.596289 0.765834 0.446476 0.098 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C34 O1 C35 109.0(3) . . ?
C3 O3 H3 109.5 . . ?
C30 O30 C31 117.6(2) . . ?
C32 N1 C33 111.3(3) . . ?
C32 N1 C36 112.3(3) . . ?
C36 N1 C33 107.9(3) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C2 C1 C10 113.00(17) . . ?
C10 C1 H1A 109.0 . . ?
C10 C1 H1B 109.0 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 C1 111.63(19) . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
O3 C3 C2 112.2(2) . . ?
O3 C3 H3A 107.5 . . ?
O3 C3 C4 108.61(17) . . ?
C2 C3 H3A 107.5 . . ?
C2 C3 C4 113.33(19) . . ?
C4 C3 H3A 107.5 . . ?
C3 C4 C5 107.28(16) . . ?
C24 C4 C3 110.8(2) . . ?
C24 C4 C5 114.3(2) . . ?
C24 C4 C23 108.4(2) . . ?
C23 C4 C3 107.0(2) . . ?
C23 C4 C5 108.8(2) . . ?
C4 C5 H5 104.4 . . ?
C6 C5 C4 113.75(17) . . ?
C6 C5 H5 104.4 . . ?
C6 C5 C10 110.80(17) . . ?
C10 C5 C4 117.41(17) . . ?
C10 C5 H5 104.4 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 C5 110.21(17) . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C6 C7 C8 114.07(18) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C7 C8 C9 110.03(16) . . ?
C7 C8 C14 109.93(16) . . ?
C7 C8 C26 107.67(17) . . ?
C9 C8 C14 108.22(14) . . ?
C26 C8 C9 110.24(16) . . ?
C26 C8 C14 110.75(17) . . ?
C8 C9 H9 104.4 . . ?
C8 C9 C10 117.89(15) . . ?
C10 C9 H9 104.4 . . ?
C11 C9 C8 108.09(15) . . ?
C11 C9 H9 104.4 . . ?
C11 C9 C10 116.02(15) . . ?
C1 C10 C5 106.97(16) . . ?
C1 C10 C9 108.76(15) . . ?
C5 C10 C9 106.12(15) . . ?
C25 C10 C1 108.43(17) . . ?
C25 C10 C5 114.29(18) . . ?
C25 C10 C9 112.04(16) . . ?
O11 C11 C9 122.66(19) . . ?
O11 C11 C12 119.65(19) . . ?
C12 C11 C9 117.68(16) . . ?
C11 C12 H12 117.4 . . ?
C13 C12 C11 125.25(18) . . ?
C13 C12 H12 117.4 . . ?
C12 C13 C14 119.39(18) . . ?
C12 C13 C18 119.40(18) . . ?
C18 C13 C14 121.07(16) . . ?
C13 C14 C8 108.22(15) . . ?
C13 C14 C15 112.62(16) . . ?
C13 C14 C27 106.25(16) . . ?
C15 C14 C8 110.56(15) . . ?
C15 C14 C27 106.49(17) . . ?
C27 C14 C8 112.69(16) . . ?
C14 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.57(17) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C15 C16 C17 112.48(18) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 C18 108.31(17) . . ?
C16 C17 C22 111.65(19) . . ?
C22 C17 C18 109.78(17) . . ?
C28 C17 C16 110.3(2) . . ?
C28 C17 C18 109.51(19) . . ?
C28 C17 C22 107.31(19) . . ?
C13 C18 C17 112.80(16) . . ?
C13 C18 H18 106.8 . . ?
C13 C18 C19 110.38(16) . . ?
C17 C18 H18 106.8 . . ?
C19 C18 C17 112.76(17) . . ?
C19 C18 H18 106.8 . . ?
C18 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 C18 112.78(17) . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C19 C20 C29 110.07(19) . . ?
C21 C20 C19 108.25(18) . . ?
C21 C20 C29 109.0(2) . . ?
C30 C20 C19 112.50(18) . . ?
C30 C20 C21 110.0(2) . . ?
C30 C20 C29 107.0(2) . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 C20 112.6(2) . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C17 C22 H22A 108.4 . . ?
C17 C22 H22B 108.4 . . ?
C21 C22 C17 115.5(2) . . ?
C21 C22 H22A 108.4 . . ?
C21 C22 H22B 108.4 . . ?
H22A C22 H22B 107.5 . . ?
C4 C24 H24A 109.5 . . ?
C4 C24 H24B 109.5 . . ?
C4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C4 C23 H23A 109.5 . . ?
C4 C23 H23B 109.5 . . ?
C4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C10 C25 H25A 109.5 . . ?
C10 C25 H25B 109.5 . . ?
C10 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8 C26 H26A 109.5 . . ?
C8 C26 H26B 109.5 . . ?
C8 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C14 C27 H27A 109.5 . . ?
C14 C27 H27B 109.5 . . ?
C14 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C17 C28 H28A 109.5 . . ?
C17 C28 H28B 109.5 . . ?
C17 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C20 C29 H29A 109.5 . . ?
C20 C29 H29B 109.5 . . ?
C20 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O30 C30 C20 112.01(19) . . ?
O31 C30 O30 123.1(2) . . ?
O31 C30 C20 124.8(2) . . ?
O30 C31 H31A 109.5 . . ?
O30 C31 H31B 109.5 . . ?
O30 C31 C32 110.6(3) . . ?
H31A C31 H31B 108.1 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
N1 C32 C31 114.2(2) . . ?
N1 C32 H32A 108.7 . . ?
N1 C32 H32B 108.7 . . ?
C31 C32 H32A 108.7 . . ?
C31 C32 H32B 108.7 . . ?
H32A C32 H32B 107.6 . . ?
N1 C33 H33A 109.4 . . ?
N1 C33 H33B 109.4 . . ?
N1 C33 C34 111.0(3) . . ?
H33A C33 H33B 108.0 . . ?
C34 C33 H33A 109.4 . . ?
C34 C33 H33B 109.4 . . ?
O1 C34 C33 112.5(4) . . ?
O1 C34 H34A 109.1 . . ?
O1 C34 H34B 109.1 . . ?
C33 C34 H34A 109.1 . . ?
C33 C34 H34B 109.1 . . ?
H34A C34 H34B 107.8 . . ?
O1 C35 H35A 109.0 . . ?
O1 C35 H35B 109.0 . . ?
O1 C35 C36 112.9(3) . . ?
H35A C35 H35B 107.8 . . ?
C36 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
N1 C36 C35 110.5(3) . . ?
N1 C36 H36A 109.5 . . ?
N1 C36 H36B 109.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 108.1 . . ?
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
O1 C34 1.404(5) . ?
O1 C35 1.407(5) . ?
O3 H3 0.8200 . ?
O3 C3 1.428(3) . ?
O11 C11 1.223(3) . ?
O30 C30 1.341(3) . ?
O30 C31 1.447(3) . ?
O31 C30 1.199(3) . ?
N1 C32 1.449(4) . ?
N1 C33 1.458(4) . ?
N1 C36 1.453(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.526(3) . ?
C1 C10 1.546(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.504(3) . ?
C3 H3A 0.9800 . ?
C3 C4 1.538(3) . ?
C4 C5 1.560(3) . ?
C4 C24 1.536(4) . ?
C4 C23 1.537(4) . ?
C5 H5 0.9800 . ?
C5 C6 1.531(3) . ?
C5 C10 1.559(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.521(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.537(3) . ?
C8 C9 1.560(2) . ?
C8 C14 1.587(3) . ?
C8 C26 1.540(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.569(3) . ?
C9 C11 1.525(3) . ?
C10 C25 1.543(3) . ?
C11 C12 1.462(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.338(3) . ?
C13 C14 1.527(3) . ?
C13 C18 1.520(3) . ?
C14 C15 1.554(3) . ?
C14 C27 1.556(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.527(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.532(3) . ?
C17 C18 1.552(3) . ?
C17 C22 1.537(3) . ?
C17 C28 1.530(3) . ?
C18 H18 0.9800 . ?
C18 C19 1.541(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.534(3) . ?
C20 C21 1.531(3) . ?
C20 C29 1.538(3) . ?
C20 C30 1.519(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.516(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
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 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.500(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.485(7) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.490(5) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
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
O3 H3 O11 0.82 2.00 2.808(2) 169.0 4_646 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
O1 C35 C36 N1 -58.2(5) . . . . ?
O3 C3 C4 C5 -178.4(2) . . . . ?
O3 C3 C4 C24 -53.1(3) . . . . ?
O3 C3 C4 C23 64.9(3) . . . . ?
O11 C11 C12 C13 179.2(2) . . . . ?
O30 C31 C32 N1 69.8(3) . . . . ?
N1 C33 C34 O1 58.4(5) . . . . ?
C1 C2 C3 O3 -178.46(19) . . . . ?
C1 C2 C3 C4 58.1(2) . . . . ?
C2 C1 C10 C5 52.6(2) . . . . ?
C2 C1 C10 C9 166.84(18) . . . . ?
C2 C1 C10 C25 -71.1(2) . . . . ?
C2 C3 C4 C5 -53.0(3) . . . . ?
C2 C3 C4 C24 72.4(3) . . . . ?
C2 C3 C4 C23 -169.6(2) . . . . ?
C3 C4 C5 C6 -175.9(2) . . . . ?
C3 C4 C5 C10 52.4(3) . . . . ?
C4 C5 C6 C7 161.1(2) . . . . ?
C4 C5 C10 C1 -52.3(2) . . . . ?
C4 C5 C10 C9 -168.29(16) . . . . ?
C4 C5 C10 C25 67.7(2) . . . . ?
C5 C6 C7 C8 57.4(3) . . . . ?
C6 C5 C10 C1 174.67(17) . . . . ?
C6 C5 C10 C9 58.7(2) . . . . ?
C6 C5 C10 C25 -65.3(2) . . . . ?
C6 C7 C8 C9 -46.5(3) . . . . ?
C6 C7 C8 C14 -165.62(19) . . . . ?
C6 C7 C8 C26 73.6(2) . . . . ?
C7 C8 C9 C10 45.5(2) . . . . ?
C7 C8 C9 C11 179.52(17) . . . . ?
C7 C8 C14 C13 -178.86(16) . . . . ?
C7 C8 C14 C15 -55.1(2) . . . . ?
C7 C8 C14 C27 64.0(2) . . . . ?
C8 C9 C10 C1 -166.04(16) . . . . ?
C8 C9 C10 C5 -51.3(2) . . . . ?
C8 C9 C10 C25 74.1(2) . . . . ?
C8 C9 C11 O11 -149.9(2) . . . . ?
C8 C9 C11 C12 31.8(2) . . . . ?
C8 C14 C15 C16 -157.29(19) . . . . ?
C9 C8 C14 C13 60.9(2) . . . . ?
C9 C8 C14 C15 -175.29(16) . . . . ?
C9 C8 C14 C27 -56.2(2) . . . . ?
C9 C11 C12 C13 -2.5(3) . . . . ?
C10 C1 C2 C3 -57.9(2) . . . . ?
C10 C5 C6 C7 -64.1(2) . . . . ?
C10 C9 C11 O11 -14.9(3) . . . . ?
C10 C9 C11 C12 166.76(18) . . . . ?
C11 C9 C10 C1 63.5(2) . . . . ?
C11 C9 C10 C5 178.25(16) . . . . ?
C11 C9 C10 C25 -56.4(2) . . . . ?
C11 C12 C13 C14 3.0(3) . . . . ?
C11 C12 C13 C18 178.79(19) . . . . ?
C12 C13 C14 C8 -32.2(2) . . . . ?
C12 C13 C14 C15 -154.7(2) . . . . ?
C12 C13 C14 C27 89.0(2) . . . . ?
C12 C13 C18 C17 145.4(2) . . . . ?
C12 C13 C18 C19 -87.4(2) . . . . ?
C13 C14 C15 C16 -36.1(3) . . . . ?
C13 C18 C19 C20 177.17(16) . . . . ?
C14 C8 C9 C10 165.62(15) . . . . ?
C14 C8 C9 C11 -60.35(19) . . . . ?
C14 C13 C18 C17 -38.8(2) . . . . ?
C14 C13 C18 C19 88.3(2) . . . . ?
C14 C15 C16 C17 54.7(3) . . . . ?
C15 C16 C17 C18 -61.5(2) . . . . ?
C15 C16 C17 C22 177.49(19) . . . . ?
C15 C16 C17 C28 58.3(3) . . . . ?
C16 C17 C18 C13 52.2(2) . . . . ?
C16 C17 C18 C19 -73.7(2) . . . . ?
C16 C17 C22 C21 71.7(3) . . . . ?
C17 C18 C19 C20 -55.7(2) . . . . ?
C18 C13 C14 C8 152.04(17) . . . . ?
C18 C13 C14 C15 29.5(3) . . . . ?
C18 C13 C14 C27 -86.7(2) . . . . ?
C18 C17 C22 C21 -48.4(3) . . . . ?
C18 C19 C20 C21 57.4(2) . . . . ?
C18 C19 C20 C29 176.42(19) . . . . ?
C18 C19 C20 C30 -64.4(2) . . . . ?
C19 C20 C21 C22 -55.7(3) . . . . ?
C19 C20 C30 O30 -36.3(3) . . . . ?
C19 C20 C30 O31 145.9(2) . . . . ?
C20 C21 C22 C17 53.8(3) . . . . ?
C21 C20 C30 O30 -157.1(2) . . . . ?
C21 C20 C30 O31 25.2(3) . . . . ?
C22 C17 C18 C13 174.32(18) . . . . ?
C22 C17 C18 C19 48.4(2) . . . . ?
C24 C4 C5 C6 60.8(3) . . . . ?
C24 C4 C5 C10 -70.9(3) . . . . ?
C23 C4 C5 C6 -60.5(3) . . . . ?
C23 C4 C5 C10 167.8(2) . . . . ?
C26 C8 C9 C10 -73.1(2) . . . . ?
C26 C8 C9 C11 60.9(2) . . . . ?
C26 C8 C14 C13 -60.0(2) . . . . ?
C26 C8 C14 C15 63.8(2) . . . . ?
C26 C8 C14 C27 -177.19(17) . . . . ?
C27 C14 C15 C16 80.0(2) . . . . ?
C28 C17 C18 C13 -68.1(2) . . . . ?
C28 C17 C18 C19 166.00(19) . . . . ?
C28 C17 C22 C21 -167.3(2) . . . . ?
C29 C20 C21 C22 -175.4(2) . . . . ?
C29 C20 C30 O30 84.6(2) . . . . ?
C29 C20 C30 O31 -93.1(3) . . . . ?
C30 O30 C31 C32 -100.0(3) . . . . ?
C30 C20 C21 C22 67.6(3) . . . . ?
C31 O30 C30 O31 -1.7(4) . . . . ?
C31 O30 C30 C20 -179.4(2) . . . . ?
C32 N1 C33 C34 -179.8(3) . . . . ?
C32 N1 C36 C35 178.7(3) . . . . ?
C33 N1 C32 C31 -168.4(3) . . . . ?
C33 N1 C36 C35 55.7(4) . . . . ?
C34 O1 C35 C36 56.9(6) . . . . ?
C35 O1 C34 C33 -56.8(5) . . . . ?
C36 N1 C32 C31 70.6(3) . . . . ?
C36 N1 C33 C34 -56.2(4) . . . . ?

_cod_database_fobs_code 2108966
