Total synthesis of natural derivatives and artificial analogs of 13-oxyingenol and their biological evaluation.
Ohyoshi, Takayuki; Tamura, Yuki; Hayakawa, Ichiro; Hirai, Go; Miyazawa, Yamato; Funakubo, Shota; Sodeoka, Mikiko; Kigoshi, Hideo; Organic & biomolecular chemistry 14 (2016) 11426–11437; doi:10.1039/c6ob02268e

data_7155362
_publ_section_title
;
 Total synthesis of natural derivatives and artificial analogs of
 13-oxyingenol and their biological evaluation.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              11426
_journal_page_last               11437
_journal_paper_doi               10.1039/c6ob02268e
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C39 H59 Br O7 Si2'
_chemical_formula_weight         775.95
_chemical_name_systematic
; 
 epoxy_ingenol derivative 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-10-06 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                87.071(2)
_cell_angle_beta                 81.557(2)
_cell_angle_gamma                64.601(2)
_cell_formula_units_Z            4
_cell_length_a                   14.369(2)
_cell_length_b                   15.522(3)
_cell_length_c                   20.704(4)
_cell_measurement_reflns_used    2698
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.37
_cell_volume                     4125.8(13)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120.0(1)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.6766
_diffrn_reflns_av_sigmaI/netI    0.3083
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            86050
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    1.099
_exptl_absorpt_correction_T_max  0.8632
_exptl_absorpt_correction_T_min  0.7981
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.947
_refine_diff_density_min         -1.104
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       0.0073(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     884
_refine_ls_number_reflns         18685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.2126
_refine_ls_R_factor_gt           0.1423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1272P)^2^+13.8341P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3578
_refine_ls_wR_factor_ref         0.4093
_reflns_number_gt                9337
_reflns_number_total             18685
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02268e2.cif
_cod_data_source_block           epoxy_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155362.cif.
;
_cod_original_cell_volume        4126.0(12)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               7155362