Total synthesis of cynaropicrin.
Nakamura, Tenma; Pitna, Dinda B.; Kimura, Kogaku; Yoshimoto, Yukiko; Uchiyama, Tomoya; Mori, Takaya; Kondo, Ryosuke; Hara, Shihori; Egoshi, Yuki; Yamaguchi, Shoya; Suzuki, Noriyuki; Suzuki, Yumiko; Usuki, Toyonobu; Organic & biomolecular chemistry 19 (2021) 6038–6044; doi:10.1039/d1ob00657f

data_7158044
_publ_section_title
;
 Total synthesis of cynaropicrin.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6038
_journal_page_last               6044
_journal_paper_doi               10.1039/d1ob00657f
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C24 H31 Br O5'
_chemical_formula_sum            'C24 H31 Br O5'
_chemical_formula_weight         479.41
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-10-15 deposited with the CCDC.	2021-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                94.13(3)
_cell_angle_beta                 91.26(3)
_cell_angle_gamma                90.13(2)
_cell_formula_units_Z            2
_cell_length_a                   8.703(13)
_cell_length_b                   9.329(14)
_cell_length_c                   14.17(2)
_cell_measurement_reflns_used    3025
_cell_measurement_temperature    223
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.71
_cell_volume                     1147(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10727
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.706
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.828
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             500.00
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.73
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  3296 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.032(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7316
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0737
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1206P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.2234
_reflns_d_resolution_high        0.8410
_reflns_number_gt                3598
_reflns_number_total             7316
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d1ob00657f2.cif
_cod_data_source_block           mori160121a
_cod_depositor_comments          'Adding full bibliography for 7158044.cif.'
_cod_database_code               7158044
_shelx_title                     ' mori160121a'
_shelx_refln_list_code           4
_shelx_f_calc_maximum            126.81
_shelx_f_squared_multiplier      1.000