Cytotoxic Diterpenoids from <i>Caryopteris aureoglandulosa</i>.
Mao, Xu-Dong; Zhang, Cheng-Gang; Chen, Ting; Zhao, Sen-Miao; Chou, Gui-Xin; Journal of natural products 83 (2020) 2093–2101; doi:10.1021/acs.jnatprod.9b01052

data_1558579
_publ_section_title
;
 Cytotoxic Diterpenoids from <i>Caryopteris aureoglandulosa</i>.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              2093
_journal_page_last               2101
_journal_paper_doi               10.1021/acs.jnatprod.9b01052
_journal_volume                  83
_journal_year                    2020
_chemical_formula_moiety         'C19 H14 O6, 0.5(O)'
_chemical_formula_sum            'C19 H14 O6.5'
_chemical_formula_weight         346.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.713(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7598(12)
_cell_length_b                   6.7923(5)
_cell_length_c                   19.840(2)
_cell_measurement_reflns_used    1636
_cell_measurement_temperature    297
_cell_measurement_theta_max      66.613
_cell_measurement_theta_min      3.772
_cell_volume                     1579.4(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      297.0
_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       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_unetI/netI     0.1013
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8911
_diffrn_reflns_point_group_measured_fraction_full 0.823
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        66.881
_diffrn_reflns_theta_max         66.881
_diffrn_reflns_theta_min         3.771
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1364 before and 0.0787 after correction. The Ratio of minimum to maximum transmission is 0.8065. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         4607
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1371
_refine_ls_R_factor_gt           0.0816
_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^)+(0.1164P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2089
_refine_ls_wR_factor_ref         0.2450
_reflns_Friedel_coverage         0.521
_reflns_Friedel_fraction_full    0.622
_reflns_Friedel_fraction_max     0.622
_reflns_number_gt                2525
_reflns_number_total             4607
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01052_si_005.cif
_cod_data_source_block           22019728_0m
_cod_depositor_comments
;
Adding full bibliography for 1558578--1558581.cif.

2022-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C38 H28 O13'
_cod_original_formula_weight         692.60
_cod_original_formula_moiety         '2(C19 H14 O6), O'
_cod_original_formula_units_Z            2
_cod_database_code               1558579
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: -0.2(8)
 1.2(8)
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
3.a Ternary CH refined with riding coordinates:
 C20(H20), C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C21(H21A,H21B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C25(H25), C34(H34), C15(H15)
3.d Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C)
3.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O6(H6A)
;
_olex2_submission_special_instructions 'No special instructions were received'