Maoeriocalysins A–D, four novel ent-kaurane diterpenoids from Isodon eriocalyx and their structure determination utilizing quantum chemical calculation in conjunction with quantitative interproton distance analysis
Yang, Qian; Hu, Kun; Yan, Bing-Chao; Liu, Miao; Li, Xiao-Nian; Sun, Han-Dong; Puno, Pema-Tenzin; Organic Chemistry Frontiers 6 (2019) 45–; doi:10.1039/C8QO01007B

data_1554485
_publ_section_title
;
 Maoeriocalysins A--D, four novel ent-kaurane diterpenoids from Isodon
 eriocalyx and their structure determination utilizing quantum chemical
 calculation in conjunction with quantitative interproton distance
 analysis
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              45
_journal_paper_doi               10.1039/C8QO01007B
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H24 O5'
_chemical_formula_sum            'C20 H24 O5'
_chemical_formula_weight         344.39
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-08-03 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1036(4)
_cell_length_b                   12.5506(7)
_cell_length_c                   21.9760(13)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.21
_cell_measurement_theta_min      4.02
_cell_volume                     1683.45(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18010
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.204
_diffrn_reflns_theta_min         4.023
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.850
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.010
_exptl_transmission_factor_max   0.4685
_exptl_transmission_factor_min   0.3438
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1270 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0353
_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/[\s^2^(Fo^2^)+(0.0575P)^2^+0.3714P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3118
_reflns_number_total             3157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01007b2.cif
_cod_data_source_block           cu_sie140_0m
_cod_database_code               1554485
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.552
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              1256
_shelx_hkl_checksum              31372