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_1552651
_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         'C29 H42 O7'
_chemical_formula_sum            'C29 H42 O7'
_chemical_formula_weight         502.62
_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             2018-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.2480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2498(2)
_cell_length_b                   12.1481(3)
_cell_length_c                   15.2910(3)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.89
_cell_measurement_theta_min      5.353
_cell_volume                     1335.94(6)
_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      170.01
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0357
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16571
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.935
_diffrn_reflns_theta_min         5.351
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1034 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.8424. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.344
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 2026 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5052
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0951P)^2^+0.6311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4724
_reflns_number_total             5052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00042_si_002.cif
_cod_data_source_block           mjl18200_0m
_cod_database_code               1552651
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.934
_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:
 C4(H4), C8(H8), C10(H10), C11(H11), C12(H12), C14(H14), C2"(H2"), C2'(H2')
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C20(H20A,H20B), C3'(H3'A,H3'B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7)
2.d Tetrahedral OH refined with riding coordinates:
 O2(H2)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C3"(H3"A,H3"B,H3"C), C4"(H4"A,H4"B,H4"C), C4'(H4'A,H4'B,H4'C), C5'(H5'A,
 H5'B,H5'C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              40660
_shelx_hkl_checksum              55921
_olex2_submission_special_instructions 'No special instructions were received'