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#$Date: 2022-12-05 11:44:17 +0200 (Mon, 05 Dec 2022) $
#$Revision: 279688 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106312.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_8106312
loop_
_publ_author_name
'Ye, Jiang-Hai'
'Zhao, Chen-Liang'
'Zou, Juan'
'He, Kang'
'Teng, Chao-Jie'
'Pan, Lu-Tai'
_publ_section_title
;
 Crystal structure of
 Ent-7β,20-epoxy-kaur-16-en-1β,6α,7α,14α,15α-pentaol-20-one,
 C20H30O8
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              827
_journal_page_last               828
_journal_paper_doi               10.1515/ncrs-2018-0038
_journal_volume                  233
_journal_year                    2018
_chemical_absolute_configuration .
_chemical_formula_moiety         'C20 H28 O7, H2 O'
_chemical_formula_sum            'C20 H30 O8'
_chemical_formula_weight         398.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 118.975(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.684(13)
_cell_length_b                   7.275(4)
_cell_length_c                   14.320(9)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.15
_cell_volume                     1976(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_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       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6731
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.626
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7859
_exptl_absorpt_correction_T_min  0.5786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;SADABS;2012
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(13)
_refine_ls_extinction_coef       0.0054(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0362
_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)+(0.0500P)²+0.0303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2782
_reflns_number_total             3180
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0038_suppl.cif
_cod_data_source_block           m
_cod_database_code               8106312
_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   0.988
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(13)
 -0.0(13)
2. 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, All O(H,H) groups
3.a Free rotating group:
 O1W(H1WA,H1WB)
3.b Ternary CH refined with riding coordinates:
 C13(H13), C5(H5A), C1(H1A), C9(H9), C6(H6), C15(H15), C14(H14)
3.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C2(H2A,H2B), C3(H3A,H3B)
3.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
3.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
3.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2), O5(H5), O3(H3), O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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
O6 O 0.82004(10) 0.1521(3) 0.83061(14) 0.0431(5) Uani 1 1 d . . . . .
O4 O 0.70911(11) 0.2527(3) 0.54417(16) 0.0513(5) Uani 1 1 d . . . . .
H4 H 0.6972 0.1516 0.5156 0.077 Uiso 1 1 calc GR . . . .
O2 O 0.94759(11) 0.0481(3) 0.77058(18) 0.0552(6) Uani 1 1 d . . . . .
H2 H 0.9854 0.0062 0.8160 0.083 Uiso 1 1 calc GR . . . .
O5 O 0.81147(10) -0.0093(3) 0.68756(16) 0.0491(5) Uani 1 1 d . . . . .
H5 H 0.8528 -0.0352 0.7077 0.074 Uiso 1 1 calc GR . . . .
O3 O 0.81428(10) 0.4196(3) 0.53502(16) 0.0568(6) Uani 1 1 d . . . . .
H3 H 0.7749 0.3795 0.5180 0.085 Uiso 1 1 calc GR . . . .
O1 O 0.84642(11) 0.6845(3) 0.95572(17) 0.0595(6) Uani 1 1 d . . . . .
H1 H 0.8487 0.6006 0.9956 0.089 Uiso 1 1 calc GR . . . .
O7 O 0.83642(12) 0.3135(3) 0.97054(17) 0.0562(6) Uani 1 1 d . . . . .
C7 C 0.80727(14) 0.1664(4) 0.7188(2) 0.0386(6) Uani 1 1 d . . . . .
C8 C 0.86364(13) 0.2984(4) 0.7232(2) 0.0354(6) Uani 1 1 d . . . . .
C10 C 0.79511(13) 0.4740(4) 0.8000(2) 0.0381(6) Uani 1 1 d . . . . .
C13 C 0.98124(15) 0.3701(4) 0.7687(2) 0.0471(7) Uani 1 1 d . . . . .
H13 H 1.0294 0.3269 0.7922 0.057 Uiso 1 1 calc R . . . .
C5 C 0.72399(13) 0.4222(4) 0.6981(2) 0.0424(7) Uani 1 1 d . . . . .
H5A H 0.7180 0.5125 0.6436 0.051 Uiso 1 1 calc R . . . .
C20 C 0.81831(14) 0.3115(4) 0.8752(2) 0.0408(7) Uani 1 1 d . . . . .
C1 C 0.78786(14) 0.6534(5) 0.8511(2) 0.0472(7) Uani 1 1 d . . . . .
H1A H 0.7873 0.7548 0.8057 0.057 Uiso 1 1 calc R . . . .
C9 C 0.85221(13) 0.4900(4) 0.7619(2) 0.0362(6) Uani 1 1 d . . . . .
H9 H 0.8327 0.5719 0.6998 0.043 Uiso 1 1 calc R . . . .
C6 C 0.73157(13) 0.2358(4) 0.6551(2) 0.0410(7) Uani 1 1 d . . . . .
H6 H 0.7005 0.1477 0.6638 0.049 Uiso 1 1 calc R . . . .
C11 C 0.92205(14) 0.5767(4) 0.8466(2) 0.0453(7) Uani 1 1 d . . . . .
H11A H 0.9143 0.7059 0.8541 0.054 Uiso 1 1 calc R . . . .
H11B H 0.9365 0.5177 0.9148 0.054 Uiso 1 1 calc R . . . .
C15 C 0.86578(14) 0.3079(4) 0.6163(2) 0.0423(7) Uani 1 1 d . . . . .
H15 H 0.8615 0.1827 0.5885 0.051 Uiso 1 1 calc R . . . .
C14 C 0.93987(14) 0.2325(4) 0.7985(2) 0.0423(7) Uani 1 1 d . . . . .
H14 H 0.9521 0.2427 0.8738 0.051 Uiso 1 1 calc R . . . .
C4 C 0.65640(15) 0.4365(5) 0.7094(3) 0.0600(9) Uani 1 1 d . . . . .
C16 C 0.93917(16) 0.3777(5) 0.6494(3) 0.0522(8) Uani 1 1 d . . . . .
C12 C 0.98131(16) 0.5588(4) 0.8184(3) 0.0527(8) Uani 1 1 d . . . . .
H12A H 1.0262 0.5761 0.8825 0.063 Uiso 1 1 calc R . . . .
H12B H 0.9763 0.6552 0.7684 0.063 Uiso 1 1 calc R . . . .
C2 C 0.72062(17) 0.6673(6) 0.8585(3) 0.0668(9) Uani 1 1 d . . . . .
H2A H 0.7226 0.5801 0.9111 0.080 Uiso 1 1 calc R . . . .
H2B H 0.7171 0.7897 0.8825 0.080 Uiso 1 1 calc R . . . .
C3 C 0.65578(18) 0.6292(6) 0.7524(3) 0.0732(11) Uani 1 1 d . . . . .
H3A H 0.6529 0.7199 0.7007 0.088 Uiso 1 1 calc R . . . .
H3B H 0.6141 0.6420 0.7606 0.088 Uiso 1 1 calc R . . . .
C18 C 0.6521(2) 0.2901(6) 0.7828(3) 0.0810(12) Uani 1 1 d . . . . .
H18A H 0.6485 0.1707 0.7520 0.122 Uiso 1 1 calc GR . . . .
H18B H 0.6114 0.3123 0.7910 0.122 Uiso 1 1 calc GR . . . .
H18C H 0.6937 0.2954 0.8513 0.122 Uiso 1 1 calc GR . . . .
C19 C 0.59212(17) 0.4185(7) 0.5972(3) 0.0851(13) Uani 1 1 d . . . . .
H19A H 0.5932 0.5150 0.5523 0.128 Uiso 1 1 calc GR . . . .
H19B H 0.5496 0.4279 0.6020 0.128 Uiso 1 1 calc GR . . . .
H19C H 0.5935 0.3015 0.5672 0.128 Uiso 1 1 calc GR . . . .
C17 C 0.9603(2) 0.4375(8) 0.5836(3) 0.0886(14) Uani 1 1 d . . . . .
H17A H 1.0060 0.4816 0.6099 0.106 Uiso 1 1 calc R . . . .
H17B H 0.9296 0.4360 0.5105 0.106 Uiso 1 1 calc R . . . .
O1W O 0.42572(14) 0.4888(4) 0.0620(2) 0.0963(10) Uani 1 1 d . . . . .
H1WA H 0.3991 0.5821 0.0283 0.144 Uiso 1 1 d G . . . .
H1WB H 0.4037 0.3941 0.0229 0.144 Uiso 1 1 d G . . . .
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
C20 O6 C7 114.8(2) . .
C6 O4 H4 109.5 . .
C14 O2 H2 109.5 . .
C7 O5 H5 109.5 . .
C15 O3 H3 109.5 . .
C1 O1 H1 109.5 . .
O6 C7 C8 105.71(19) . .
O6 C7 C6 104.6(2) . .
O5 C7 O6 106.2(2) . .
O5 C7 C8 114.8(2) . .
O5 C7 C6 109.6(2) . .
C6 C7 C8 115.0(2) . .
C7 C8 C9 108.2(2) . .
C7 C8 C15 113.1(2) . .
C7 C8 C14 113.3(2) . .
C15 C8 C9 113.3(2) . .
C14 C8 C9 109.1(2) . .
C14 C8 C15 99.7(2) . .
C5 C10 C9 106.1(2) . .
C20 C10 C5 108.2(2) . .
C20 C10 C1 113.6(2) . .
C20 C10 C9 104.9(2) . .
C1 C10 C5 111.3(2) . .
C1 C10 C9 112.2(2) . .
C14 C13 H13 111.3 . .
C14 C13 C12 108.7(2) . .
C16 C13 H13 111.3 . .
C16 C13 C14 103.1(3) . .
C16 C13 C12 110.9(3) . .
C12 C13 H13 111.3 . .
C10 C5 H5A 105.7 . .
C6 C5 C10 109.7(2) . .
C6 C5 H5A 105.7 . .
C6 C5 C4 113.1(2) . .
C4 C5 C10 116.0(2) . .
C4 C5 H5A 105.7 . .
O6 C20 C10 114.6(2) . .
O7 C20 O6 118.4(3) . .
O7 C20 C10 127.0(3) . .
O1 C1 C10 112.7(2) . .
O1 C1 H1A 107.1 . .
O1 C1 C2 108.1(2) . .
C10 C1 H1A 107.1 . .
C2 C1 C10 114.4(3) . .
C2 C1 H1A 107.1 . .
C8 C9 C10 110.0(2) . .
C8 C9 H9 107.0 . .
C10 C9 H9 107.0 . .
C11 C9 C8 112.3(2) . .
C11 C9 C10 113.2(2) . .
C11 C9 H9 107.0 . .
O4 C6 C7 112.6(2) . .
O4 C6 C5 109.1(2) . .
O4 C6 H6 108.3 . .
C7 C6 C5 110.2(2) . .
C7 C6 H6 108.3 . .
C5 C6 H6 108.3 . .
C9 C11 H11A 109.0 . .
C9 C11 H11B 109.0 . .
H11A C11 H11B 107.8 . .
C12 C11 C9 112.9(2) . .
C12 C11 H11A 109.0 . .
C12 C11 H11B 109.0 . .
O3 C15 C8 116.5(2) . .
O3 C15 H15 108.5 . .
O3 C15 C16 110.9(2) . .
C8 C15 H15 108.5 . .
C16 C15 C8 103.6(2) . .
C16 C15 H15 108.5 . .
O2 C14 C8 109.0(2) . .
O2 C14 C13 111.7(2) . .
O2 C14 H14 111.9 . .
C8 C14 H14 111.9 . .
C13 C14 C8 100.0(2) . .
C13 C14 H14 111.9 . .
C3 C4 C5 107.2(3) . .
C3 C4 C19 108.5(3) . .
C18 C4 C5 113.5(3) . .
C18 C4 C3 110.2(3) . .
C18 C4 C19 109.4(3) . .
C19 C4 C5 107.9(3) . .
C13 C16 C15 108.2(2) . .
C17 C16 C13 127.0(3) . .
C17 C16 C15 124.7(3) . .
C13 C12 H12A 109.1 . .
C13 C12 H12B 109.1 . .
C11 C12 C13 112.6(2) . .
C11 C12 H12A 109.1 . .
C11 C12 H12B 109.1 . .
H12A C12 H12B 107.8 . .
C1 C2 H2A 109.2 . .
C1 C2 H2B 109.2 . .
H2A C2 H2B 107.9 . .
C3 C2 C1 112.0(3) . .
C3 C2 H2A 109.2 . .
C3 C2 H2B 109.2 . .
C4 C3 H3A 109.1 . .
C4 C3 H3B 109.1 . .
C2 C3 C4 112.7(3) . .
C2 C3 H3A 109.1 . .
C2 C3 H3B 109.1 . .
H3A C3 H3B 107.8 . .
C4 C18 H18A 109.5 . .
C4 C18 H18B 109.5 . .
C4 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C4 C19 H19A 109.5 . .
C4 C19 H19B 109.5 . .
C4 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C16 C17 H17A 120.0 . .
C16 C17 H17B 120.0 . .
H17A C17 H17B 120.0 . .
H1WA O1W H1WB 104.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O6 C7 1.490(3) .
O6 C20 1.333(3) .
O4 H4 0.8200 .
O4 C6 1.423(3) .
O2 H2 0.8200 .
O2 C14 1.433(4) .
O5 H5 0.8200 .
O5 C7 1.372(4) .
O3 H3 0.8200 .
O3 C15 1.415(3) .
O1 H1 0.8200 .
O1 C1 1.437(4) .
O7 C20 1.224(3) .
C7 C8 1.532(4) .
C7 C6 1.527(4) .
C8 C9 1.564(4) .
C8 C15 1.555(4) .
C8 C14 1.549(4) .
C10 C5 1.571(4) .
C10 C20 1.511(4) .
C10 C1 1.541(4) .
C10 C9 1.581(3) .
C13 H13 0.9800 .
C13 C14 1.537(4) .
C13 C16 1.497(4) .
C13 C12 1.546(4) .
C5 H5A 0.9800 .
C5 C6 1.531(4) .
C5 C4 1.554(4) .
C1 H1A 0.9800 .
C1 C2 1.516(4) .
C9 H9 0.9800 .
C9 C11 1.544(4) .
C6 H6 0.9800 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.528(4) .
C15 H15 0.9800 .
C15 C16 1.511(4) .
C14 H14 0.9800 .
C4 C3 1.533(5) .
C4 C18 1.530(5) .
C4 C19 1.541(5) .
C16 C17 1.305(5) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 C3 1.515(5) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C17 H17A 0.9300 .
C17 H17B 0.9300 .
O1W H1WA 0.8698 .
O1W H1WB 0.8699 .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.0(13)
2 -0.0(13)
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{ce38c5ec-447b-4635-92a2-3cf77e4530d5} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{ce38c5ec-447b-4635-92a2-3cf77e4530d5} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
CB
