Cytotoxic Tigliane Diterpenoids from Croton damayeshu.
Cui, Jiao-Jiao; Ji, Kai-Long; Liu, Hong-Chun; Zhou, Bin; Liu, Qun-Fang; Xu, Cheng-Hui; Ding, Jian; Zhao, Jin-Xin; Yue, Jian-Min; Journal of natural products 82 (2019) 1550–1557; doi:10.1021/acs.jnatprod.9b00042

data_1552653
_publ_section_title
;
 Cytotoxic Tigliane Diterpenoids from Croton damayeshu.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1550
_journal_page_last               1557
_journal_paper_doi               10.1021/acs.jnatprod.9b00042
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C25 H34 O6'
_chemical_formula_sum            'C25 H34 O6'
_chemical_formula_weight         430.52
_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             2018-08-17
_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            4
_cell_length_a                   9.4458(2)
_cell_length_b                   9.5339(2)
_cell_length_c                   24.4990(5)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.946
_cell_measurement_theta_min      4.073
_cell_volume                     2206.27(8)
_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      169.97
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.983
_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  0.0323
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            23672
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.921
_diffrn_reflns_theta_min         7.433
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.477
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1171 before and 0.0487 after correction. The Ratio of minimum to maximum transmission is 0.8470. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1735 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+1.0035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4089
_reflns_number_total             4139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00042_si_004.cif
_cod_data_source_block           mjl18377_0m
_cod_database_code               1552653
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.945
_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:
 C2"(H2"), C4(H4), C8(H8), C10(H10), C11(H11), C12(H12), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C3"(H3"A,H3"B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C20(H20)
2.d Idealised Me refined as rotating group:
 C4"(H4"A,H4"B,H4"C), C5"(H5"A,H5"B,H5"C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_shelx_res_checksum              29542
_shelx_hkl_checksum              91744
_olex2_submission_special_instructions 'No special instructions were received'