#------------------------------------------------------------------------------
#$Date: 2023-01-06 10:27:38 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280149 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106420.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_8106420
loop_
_publ_author_name
'Zhao, Neng-Wu'
'Ye, Jiang-Hai'
'Zhao, Chen-Liang'
'Zhang, Jing-Jie'
'Pan, Lu-Tai'
_publ_section_title
;
 Crystal constructure of 16(S)-methyl-6α-carboxy-1, 15-dioxo-6,
 7-seco-ent-kaur-2-en-7, 20-olide, C20H24O6
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              27
_journal_page_last               28
_journal_paper_doi               10.1515/ncrs-2016-0112
_journal_volume                  232
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C20 H24 O6'
_chemical_formula_weight         360.39
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.697(14)
_cell_length_b                   13.91(2)
_cell_length_c                   16.75(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1793(5)
_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 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12305
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(12)
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0541P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                2512
_reflns_number_total             3327
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0112_suppl.cif
_cod_data_source_block           o
_cod_original_cell_volume        1794(6)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               8106420
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
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 0.2181(3) 0.20318(17) 0.20048(13) 0.0484(6) Uani 1 1 d . . .
C2 C 0.0937(4) 0.1500(2) 0.24967(15) 0.0645(8) Uani 1 1 d . . .
H2 H 0.0493 0.0924 0.2303 0.077 Uiso 1 1 calc R . .
C3 C 0.0426(4) 0.1804(2) 0.31994(15) 0.0653(8) Uani 1 1 d . . .
H3 H -0.0314 0.1401 0.3483 0.078 Uiso 1 1 calc R . .
C4 C 0.0909(3) 0.27313(18) 0.35911(13) 0.0503(6) Uani 1 1 d . . .
C5 C 0.1925(3) 0.33691(15) 0.29904(12) 0.0403(5) Uani 1 1 d . . .
H5 H 0.1037 0.3665 0.2651 0.048 Uiso 1 1 calc R . .
C6 C 0.2808(3) 0.41966(17) 0.34100(13) 0.0466(6) Uani 1 1 d . . .
C7 C 0.6013(3) 0.21400(18) 0.15093(15) 0.0514(6) Uani 1 1 d . . .
C8 C 0.5430(3) 0.31356(16) 0.12817(13) 0.0436(6) Uani 1 1 d . . .
C9 C 0.3919(3) 0.35780(16) 0.17948(12) 0.0408(5) Uani 1 1 d . . .
H9 H 0.4449 0.4093 0.2111 0.049 Uiso 1 1 calc R . .
C10 C 0.3190(3) 0.28497(15) 0.24043(12) 0.0399(5) Uani 1 1 d . . .
C11 C 0.2579(3) 0.40658(18) 0.12593(14) 0.0520(6) Uani 1 1 d . . .
H11A H 0.1925 0.3578 0.0975 0.062 Uiso 1 1 calc R . .
H11B H 0.1771 0.4426 0.1588 0.062 Uiso 1 1 calc R . .
C12 C 0.3424(3) 0.47436(19) 0.06578(15) 0.0551(7) Uani 1 1 d . . .
H12A H 0.3690 0.5347 0.0920 0.066 Uiso 1 1 calc R . .
H12B H 0.2604 0.4877 0.0233 0.066 Uiso 1 1 calc R . .
C13 C 0.5102(3) 0.43320(17) 0.02926(14) 0.0472(6) Uani 1 1 d . . .
H13 H 0.5198 0.4510 -0.0272 0.057 Uiso 1 1 calc R . .
C14 C 0.5083(3) 0.32376(17) 0.03875(13) 0.0490(6) Uani 1 1 d . . .
H14A H 0.3966 0.2968 0.0241 0.059 Uiso 1 1 calc R . .
H14B H 0.5989 0.2936 0.0073 0.059 Uiso 1 1 calc R . .
C15 C 0.6958(3) 0.38373(18) 0.13675(13) 0.0475(6) Uani 1 1 d . . .
C16 C 0.6755(3) 0.46194(17) 0.07494(14) 0.0492(6) Uani 1 1 d . . .
H16 H 0.6560 0.5235 0.1019 0.059 Uiso 1 1 calc R . .
C17 C 0.8374(3) 0.4690(2) 0.02353(16) 0.0636(7) Uani 1 1 d . . .
H17A H 0.8226 0.5192 -0.0152 0.095 Uiso 1 1 calc R . .
H17B H 0.8560 0.4090 -0.0034 0.095 Uiso 1 1 calc R . .
H17C H 0.9358 0.4832 0.0566 0.095 Uiso 1 1 calc R . .
C18 C -0.0779(4) 0.3264(2) 0.38106(16) 0.0664(8) Uani 1 1 d . . .
H18A H -0.0498 0.3867 0.4058 0.100 Uiso 1 1 calc R . .
H18B H -0.1445 0.2879 0.4174 0.100 Uiso 1 1 calc R . .
H18C H -0.1446 0.3379 0.3336 0.100 Uiso 1 1 calc R . .
C19 C 0.1867(4) 0.2507(2) 0.43728(14) 0.0699(8) Uani 1 1 d . . .
H19A H 0.2192 0.3097 0.4629 0.105 Uiso 1 1 calc R . .
H19B H 0.2890 0.2137 0.4259 0.105 Uiso 1 1 calc R . .
H19C H 0.1117 0.2146 0.4719 0.105 Uiso 1 1 calc R . .
C20 C 0.4757(3) 0.23948(18) 0.28090(13) 0.0492(6) Uani 1 1 d . . .
H20A H 0.5497 0.2895 0.3025 0.059 Uiso 1 1 calc R . .
H20B H 0.4369 0.1995 0.3248 0.059 Uiso 1 1 calc R . .
O1 O 0.2457(3) 0.18088(13) 0.13163(10) 0.0695(6) Uani 1 1 d . . .
O2 O 0.1920(2) 0.49999(13) 0.33388(12) 0.0660(5) Uani 1 1 d . . .
H2A H 0.2433 0.5434 0.3571 0.099 Uiso 1 1 calc R . .
O3 O 0.4139(3) 0.41425(14) 0.37736(12) 0.0813(7) Uani 1 1 d . . .
O4 O 0.6800(3) 0.16234(13) 0.10546(11) 0.0695(5) Uani 1 1 d . . .
O5 O 0.5744(2) 0.18158(12) 0.22487(10) 0.0572(5) Uani 1 1 d . . .
O6 O 0.8116(2) 0.37705(15) 0.18469(11) 0.0726(6) 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'
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
O1 C1 C2 121.4(2) . .
O1 C1 C10 121.1(2) . .
C2 C1 C10 117.4(2) . .
C3 C2 C1 122.6(3) . .
C2 C3 C4 126.7(2) . .
C3 C4 C19 108.6(2) . .
C3 C4 C18 108.1(2) . .
C19 C4 C18 107.4(2) . .
C3 C4 C5 109.5(2) . .
C19 C4 C5 115.3(2) . .
C18 C4 C5 107.7(2) . .
C6 C5 C4 111.1(2) . .
C6 C5 C10 111.4(2) . .
C4 C5 C10 117.2(2) . .
O3 C6 O2 123.0(2) . .
O3 C6 C5 125.1(2) . .
O2 C6 C5 111.8(2) . .
O4 C7 O5 117.5(2) . .
O4 C7 C8 122.4(2) . .
O5 C7 C8 120.0(2) . .
C7 C8 C14 112.7(2) . .
C7 C8 C15 109.5(2) . .
C14 C8 C15 99.58(18) . .
C7 C8 C9 116.3(2) . .
C14 C8 C9 111.7(2) . .
C15 C8 C9 105.5(2) . .
C11 C9 C10 115.8(2) . .
C11 C9 C8 110.6(2) . .
C10 C9 C8 111.9(2) . .
C20 C10 C1 106.7(2) . .
C20 C10 C9 106.2(2) . .
C1 C10 C9 112.5(2) . .
C20 C10 C5 114.0(2) . .
C1 C10 C5 107.6(2) . .
C9 C10 C5 109.8(2) . .
C12 C11 C9 112.0(2) . .
C11 C12 C13 113.0(2) . .
C14 C13 C16 102.4(2) . .
C14 C13 C12 108.7(2) . .
C16 C13 C12 113.6(2) . .
C8 C14 C13 101.10(18) . .
O6 C15 C16 126.2(2) . .
O6 C15 C8 125.5(2) . .
C16 C15 C8 108.3(2) . .
C15 C16 C17 110.5(2) . .
C15 C16 C13 103.9(2) . .
C17 C16 C13 114.4(2) . .
O5 C20 C10 110.9(2) . .
C7 O5 C20 119.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.213(3) .
C1 C2 1.464(4) .
C1 C10 1.532(3) .
C2 C3 1.311(4) .
C3 C4 1.495(4) .
C4 C19 1.535(4) .
C4 C18 1.541(4) .
C4 C5 1.553(3) .
C5 C6 1.511(4) .
C5 C10 1.560(3) .
C6 O3 1.194(3) .
C6 O2 1.316(3) .
C7 O4 1.210(3) .
C7 O5 1.335(3) .
C7 C8 1.505(4) .
C8 C14 1.528(4) .
C8 C15 1.535(4) .
C8 C9 1.572(3) .
C9 C11 1.526(3) .
C9 C10 1.544(3) .
C10 C20 1.522(4) .
C11 C12 1.526(4) .
C12 C13 1.540(4) .
C13 C14 1.531(4) .
C13 C16 1.537(4) .
C15 O6 1.203(3) .
C15 C16 1.510(4) .
C16 C17 1.518(4) .
C20 O5 1.452(3) .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{24eef63c-c0d8-45ca-95f7-be3dbbb5a2dc} ? ? ?
{51c3a4b6-a1b0-4842-8492-8a47089b3985} ? ? ?
{884b93c8-4692-4669-bd5e-e6d44b6bac7c} 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
{24eef63c-c0d8-45ca-95f7-be3dbbb5a2dc} '_publcif_info_datablock.publ_exptl'
