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_1558581
_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_absolute_configuration rmad
_chemical_formula_moiety         'C19 H14 O7'
_chemical_formula_sum            'C19 H14 O7'
_chemical_formula_weight         354.30
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   8.4122(5)
_cell_length_b                   20.1750(11)
_cell_length_c                   26.6799(16)
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    277(2)
_cell_measurement_theta_max      74.535
_cell_measurement_theta_min      3.973
_cell_volume                     4528.0(5)
_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      277.0
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.963
_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  0.0589
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            49200
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.528
_diffrn_reflns_theta_min         2.746
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.019
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1584 before and 0.0781 after correction. The Ratio of minimum to maximum transmission is 0.8492. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       plate
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details
;
 Flack x determined using 3359 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     712
_refine_ls_number_reflns         8932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0498
_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^)+(0.1441P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1775
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                8142
_reflns_number_total             8932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01052_si_004.cif
_cod_data_source_block           22019692_0m
_cod_depositor_comments
'Adding full bibliography for 1558578--1558581.cif.'
_cod_database_code               1558581
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.862
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C20(H20), C39(H39)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C17(H17A,H17B), C22(H22A,H22B), C41(H41A,H41B), C36(H36A,H36B),
 C21(H21A,H21B), C55(H55A,H55B), C2(H2A,H2B), C40(H40A,H40B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C25(H25), C44(H44), C53(H53), C15(H15), C34(H34)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C57(H57A,H57B,H57C), C37(H37A,H37B,H37C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O17(H17), O10(H10), O7(H7), O21(H21), O14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'