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#$Date: 2023-04-05 11:47:10 +0300 (Wed, 05 Apr 2023) $
#$Revision: 282394 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107039.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_8107039
loop_
_publ_author_name
'Liu, Ya-Hua'
'Zhang, Jing-Jie'
'Ye, Jiang-Hai'
'Zhao, Chen-Liang'
'Pan, Lu-Tai'
_publ_section_title
;
 Crystal structure of
 1α,7β-dihydroxy-11β-acetoxy-ent-7β,20-epoxykaur-16-en-15-one,
 C22H30O6
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              891
_journal_page_last               892
_journal_paper_doi               10.1515/ncrs-2015-0306
_journal_volume                  231
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C22 H30 O6'
_chemical_formula_weight         390.46
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.979(4)
_cell_length_b                   16.735(12)
_cell_length_c                   20.323(15)
_cell_measurement_reflns_used    1650
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      1.58
_cell_volume                     2033(2)
_computing_cell_refinement       'APEX2 (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX II CCD Area Detector'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13551
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(15)
_refine_ls_extinction_coef       0.0066(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                2294
_reflns_number_total             3524
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0306_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        2034(3)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               8107039
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3989(5) 0.32832(15) 0.71942(14) 0.0470(8) Uani 1 1 d . . .
H1 H 0.2356 0.3320 0.7225 0.056 Uiso 1 1 calc R . .
C2 C 0.4671(6) 0.34966(16) 0.64969(14) 0.0592(9) Uani 1 1 d . . .
H2A H 0.6290 0.3521 0.6471 0.071 Uiso 1 1 calc R . .
H2B H 0.4090 0.4022 0.6389 0.071 Uiso 1 1 calc R . .
C3 C 0.3811(7) 0.28935(18) 0.59987(15) 0.0651(10) Uani 1 1 d . . .
H3A H 0.4278 0.3055 0.5561 0.078 Uiso 1 1 calc R . .
H3B H 0.2189 0.2891 0.6008 0.078 Uiso 1 1 calc R . .
C4 C 0.4674(6) 0.20423(17) 0.61361(15) 0.0535(9) Uani 1 1 d . . .
C5 C 0.4048(5) 0.18244(15) 0.68570(13) 0.0433(7) Uani 1 1 d . . .
H5 H 0.2412 0.1793 0.6865 0.052 Uiso 1 1 calc R . .
C6 C 0.4890(6) 0.09792(16) 0.70632(15) 0.0489(8) Uani 1 1 d . . .
H6A H 0.3627 0.0621 0.7116 0.059 Uiso 1 1 calc R . .
H6B H 0.5857 0.0764 0.6724 0.059 Uiso 1 1 calc R . .
C7 C 0.6161(5) 0.10403(15) 0.77040(15) 0.0453(8) Uani 1 1 d . . .
C8 C 0.4710(5) 0.13261(16) 0.82733(14) 0.0424(7) Uani 1 1 d . . .
C9 C 0.3483(5) 0.21273(14) 0.80550(13) 0.0409(7) Uani 1 1 d . . .
H9 H 0.1951 0.1984 0.7930 0.049 Uiso 1 1 calc R . .
C10 C 0.4700(5) 0.24357(15) 0.74142(14) 0.0401(7) Uani 1 1 d . . .
C11 C 0.3328(6) 0.27121(15) 0.86359(14) 0.0471(8) Uani 1 1 d . . .
H11 H 0.4723 0.3017 0.8666 0.057 Uiso 1 1 calc R . .
C12 C 0.2828(7) 0.23253(18) 0.93073(15) 0.0643(10) Uani 1 1 d . . .
H12A H 0.1229 0.2238 0.9344 0.077 Uiso 1 1 calc R . .
H12B H 0.3261 0.2694 0.9653 0.077 Uiso 1 1 calc R . .
C13 C 0.4041(6) 0.15225(19) 0.94194(15) 0.0635(10) Uani 1 1 d . . .
H13 H 0.4555 0.1466 0.9875 0.076 Uiso 1 1 calc R . .
C14 C 0.5972(6) 0.14528(18) 0.89298(15) 0.0562(9) Uani 1 1 d . . .
H14A H 0.6928 0.1001 0.9032 0.067 Uiso 1 1 calc R . .
H14B H 0.6865 0.1937 0.8920 0.067 Uiso 1 1 calc R . .
C15 C 0.2886(6) 0.07363(16) 0.84821(16) 0.0478(8) Uani 1 1 d . . .
C16 C 0.2554(6) 0.08279(19) 0.92121(17) 0.0592(9) Uani 1 1 d . . .
C17 C 0.1250(7) 0.0360(2) 0.9560(2) 0.0911(14) Uani 1 1 d . . .
H17A H 0.0474 -0.0053 0.9356 0.109 Uiso 1 1 calc R . .
H17B H 0.1100 0.0442 1.0010 0.109 Uiso 1 1 calc R . .
C18 C 0.7181(7) 0.1992(2) 0.59837(17) 0.0738(11) Uani 1 1 d . . .
H18A H 0.7982 0.2354 0.6264 0.111 Uiso 1 1 calc R . .
H18B H 0.7433 0.2133 0.5532 0.111 Uiso 1 1 calc R . .
H18C H 0.7697 0.1456 0.6060 0.111 Uiso 1 1 calc R . .
C19 C 0.3456(7) 0.14544(19) 0.56715(15) 0.0708(11) Uani 1 1 d . . .
H19A H 0.3969 0.0920 0.5755 0.106 Uiso 1 1 calc R . .
H19B H 0.3769 0.1594 0.5223 0.106 Uiso 1 1 calc R . .
H19C H 0.1874 0.1483 0.5748 0.106 Uiso 1 1 calc R . .
C20 C 0.7199(5) 0.24097(15) 0.75545(16) 0.0497(8) Uani 1 1 d . . .
H20A H 0.7999 0.2673 0.7201 0.060 Uiso 1 1 calc R . .
H20B H 0.7509 0.2697 0.7959 0.060 Uiso 1 1 calc R . .
C21 C 0.1591(7) 0.39984(18) 0.87589(16) 0.0552(9) Uani 1 1 d . . .
C22 C -0.0352(6) 0.44923(18) 0.85350(19) 0.0712(11) Uani 1 1 d . . .
H22A H -0.1238 0.4190 0.8230 0.107 Uiso 1 1 calc R . .
H22B H 0.0186 0.4968 0.8324 0.107 Uiso 1 1 calc R . .
H22C H -0.1252 0.4636 0.8908 0.107 Uiso 1 1 calc R . .
O1 O 0.1487(4) 0.32576(11) 0.84910(9) 0.0518(6) Uani 1 1 d . . .
O2 O 0.3029(5) 0.42087(13) 0.91317(13) 0.0809(8) Uani 1 1 d . . .
O3 O 0.4943(4) 0.38429(11) 0.76532(11) 0.0586(7) Uani 1 1 d D . .
O4 O 0.7149(4) 0.02883(12) 0.78496(12) 0.0589(7) Uani 1 1 d . . .
O5 O 0.1796(4) 0.02973(12) 0.81295(11) 0.0588(6) Uani 1 1 d . . .
O6 O 0.7988(3) 0.15896(10) 0.76159(10) 0.0551(6) Uani 1 1 d . . .
H3 H 0.430(5) 0.4293(12) 0.7612(16) 0.066 Uiso 1 1 d D . .
H4 H 0.852(6) 0.0332(19) 0.7942(17) 0.066 Uiso 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'
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
O3 C1 C2 110.2(2) . .
O3 C1 C10 107.5(2) . .
C2 C1 C10 114.3(2) . .
O3 C1 H1 108.2 . .
C2 C1 H1 108.2 . .
C10 C1 H1 108.2 . .
C1 C2 C3 112.0(2) . .
C1 C2 H2A 109.2 . .
C3 C2 H2A 109.2 . .
C1 C2 H2B 109.2 . .
C3 C2 H2B 109.2 . .
H2A C2 H2B 107.9 . .
C2 C3 C4 112.3(3) . .
C2 C3 H3A 109.1 . .
C4 C3 H3A 109.1 . .
C2 C3 H3B 109.1 . .
C4 C3 H3B 109.1 . .
H3A C3 H3B 107.9 . .
C18 C4 C3 110.0(3) . .
C18 C4 C19 107.6(3) . .
C3 C4 C19 108.7(3) . .
C18 C4 C5 114.4(3) . .
C3 C4 C5 107.9(2) . .
C19 C4 C5 108.2(2) . .
C4 C5 C6 112.8(2) . .
C4 C5 C10 117.7(2) . .
C6 C5 C10 108.4(2) . .
C4 C5 H5 105.6 . .
C6 C5 H5 105.6 . .
C10 C5 H5 105.6 . .
C7 C6 C5 109.4(2) . .
C7 C6 H6A 109.8 . .
C5 C6 H6A 109.8 . .
C7 C6 H6B 109.8 . .
C5 C6 H6B 109.8 . .
H6A C6 H6B 108.2 . .
O4 C7 O6 106.0(2) . .
O4 C7 C6 109.2(2) . .
O6 C7 C6 108.5(2) . .
O4 C7 C8 110.9(2) . .
O6 C7 C8 109.1(2) . .
C6 C7 C8 112.9(3) . .
C7 C8 C15 114.5(2) . .
C7 C8 C14 114.8(3) . .
C15 C8 C14 101.3(2) . .
C7 C8 C9 108.4(2) . .
C15 C8 C9 107.0(2) . .
C14 C8 C9 110.5(2) . .
C11 C9 C10 117.0(2) . .
C11 C9 C8 110.5(2) . .
C10 C9 C8 107.0(2) . .
C11 C9 H9 107.3 . .
C10 C9 H9 107.3 . .
C8 C9 H9 107.3 . .
C20 C10 C1 110.5(2) . .
C20 C10 C5 111.0(2) . .
C1 C10 C5 108.7(2) . .
C20 C10 C9 106.8(2) . .
C1 C10 C9 114.3(2) . .
C5 C10 C9 105.5(2) . .
O1 C11 C9 106.8(2) . .
O1 C11 C12 107.2(2) . .
C9 C11 C12 115.1(2) . .
O1 C11 H11 109.2 . .
C9 C11 H11 109.2 . .
C12 C11 H11 109.2 . .
C11 C12 C13 113.9(3) . .
C11 C12 H12A 108.8 . .
C13 C12 H12A 108.8 . .
C11 C12 H12B 108.8 . .
C13 C12 H12B 108.8 . .
H12A C12 H12B 107.7 . .
C16 C13 C14 101.7(3) . .
C16 C13 C12 110.4(3) . .
C14 C13 C12 109.0(3) . .
C16 C13 H13 111.8 . .
C14 C13 H13 111.8 . .
C12 C13 H13 111.8 . .
C13 C14 C8 101.7(3) . .
C13 C14 H14A 111.4 . .
C8 C14 H14A 111.4 . .
C13 C14 H14B 111.4 . .
C8 C14 H14B 111.4 . .
H14A C14 H14B 109.3 . .
O5 C15 C16 124.9(3) . .
O5 C15 C8 127.5(3) . .
C16 C15 C8 107.6(3) . .
C17 C16 C15 123.3(4) . .
C17 C16 C13 130.8(4) . .
C15 C16 C13 105.9(3) . .
C16 C17 H17A 120.0 . .
C16 C17 H17B 120.0 . .
H17A C17 H17B 120.0 . .
C4 C18 H18A 109.5 . .
C4 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C4 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C4 C19 H19A 109.5 . .
C4 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C4 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
O6 C20 C10 111.1(2) . .
O6 C20 H20A 109.4 . .
C10 C20 H20A 109.4 . .
O6 C20 H20B 109.4 . .
C10 C20 H20B 109.4 . .
H20A C20 H20B 108.0 . .
O2 C21 O1 123.7(3) . .
O2 C21 C22 125.9(3) . .
O1 C21 C22 110.3(3) . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C21 O1 C11 117.1(2) . .
C1 O3 H3 110(2) . .
C7 O4 H4 112(2) . .
C7 O6 C20 111.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O3 1.440(3) .
C1 C2 1.517(4) .
C1 C10 1.547(4) .
C1 H1 0.9800 .
C2 C3 1.519(4) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.541(4) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C18 1.533(5) .
C4 C19 1.546(4) .
C4 C5 1.555(4) .
C5 C6 1.559(4) .
C5 C10 1.575(4) .
C5 H5 0.9800 .
C6 C7 1.511(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 O4 1.421(3) .
C7 O6 1.439(3) .
C7 C8 1.523(4) .
C8 C15 1.531(4) .
C8 C14 1.547(4) .
C8 C9 1.591(4) .
C9 C11 1.536(4) .
C9 C10 1.578(4) .
C9 H9 0.9800 .
C10 C20 1.522(5) .
C11 O1 1.460(3) .
C11 C12 1.539(4) .
C11 H11 0.9800 .
C12 C13 1.544(4) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C16 1.523(5) .
C13 C14 1.529(5) .
C13 H13 0.9800 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 O5 1.216(3) .
C15 C16 1.505(5) .
C16 C17 1.311(5) .
C17 H17A 0.9300 .
C17 H17B 0.9300 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 O6 1.457(3) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 O2 1.199(4) .
C21 O1 1.355(4) .
C21 C22 1.497(5) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
O3 H3 0.849(17) .
O4 H4 0.84(3) .
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
O3 H3 O4 0.849(17) 2.10(2) 2.909(3) 159(3) 4_656
O4 H4 O5 0.84(3) 2.00(4) 2.836(4) 173(3) 1_655
