Total synthesis of (+)-iresin.
Wang, Bian-Lin; Gao, Hai-Tao; Li, Wei-Dong Z; The Journal of organic chemistry 80 (2015) 5296–5301; doi:10.1021/acs.joc.5b00365

data_4030957
_publ_section_title
;
 Total synthesis of (+)-iresin.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5296
_journal_page_last               5301
_journal_paper_doi               10.1021/acs.joc.5b00365
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C29 H28 Br2 O6'
_chemical_formula_sum            'C29 H28 Br2 O6'
_chemical_formula_weight         632.33
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.047(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2860(12)
_cell_length_b                   7.3672(15)
_cell_length_c                   28.272(6)
_cell_measurement_reflns_used    3760
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.20
_cell_volume                     1308.4(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_sigmaI/netI    0.1684
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            10197
_diffrn_reflns_theta_full        27.91
_diffrn_reflns_theta_max         27.91
_diffrn_reflns_theta_min         1.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.141
_exptl_absorpt_correction_T_max  0.8847
_exptl_absorpt_correction_T_min  0.5194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.020(13)
_refine_ls_extinction_coef       0.0033(10)
_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   0.840
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5551
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.840
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0536P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                2728
_reflns_number_total             5551
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00365_si_003.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 4030957.cif.'
_cod_database_code               4030957