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_1558580
_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         'C20 H18 O5'
_chemical_formula_sum            'C20 H18 O5'
_chemical_formula_weight         338.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.7600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5220(3)
_cell_length_b                   13.0651(2)
_cell_length_c                   7.04120(10)
_cell_measurement_reflns_used    5063
_cell_measurement_temperature    296
_cell_measurement_theta_max      54.545
_cell_measurement_theta_min      7.071
_cell_volume                     1655.01(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      296.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9333
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.863
_diffrn_reflns_theta_min         7.069
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1423 before and 0.0586 after correction. The Ratio of minimum to maximum transmission is 0.8290. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1088 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0570P)^2^+0.1192P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                2641
_reflns_number_total             2945
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01052_si_002.cif
_cod_data_source_block           mjr18011_0m
_cod_depositor_comments
'Adding full bibliography for 1558578--1558581.cif.'
_cod_database_code               1558580
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.904
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C15(H15)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'