Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.
Landry, Matthew L.; Hu, Dennis X.; McKenna, Grace M.; Burns, Noah Z.; Journal of the American Chemical Society 138 (2016) 5150–5158; doi:10.1021/jacs.6b01643

data_4130262
_publ_section_title
;
 Catalytic Enantioselective Dihalogenation and the Selective Synthesis of
 (-)-Deschloromytilipin A and (-)-Danicalipin A.
;
_journal_issue                   15
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5150
_journal_page_last               5158
_journal_paper_doi               10.1021/jacs.6b01643
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H16 Br Cl5 O3'
_chemical_formula_sum            'C15 H16 Br Cl5 O3'
_chemical_formula_weight         501.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.710(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.3275(10)
_cell_length_b                   5.0556(2)
_cell_length_c                   18.7396(11)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.32
_cell_volume                     1890.00(16)
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_collection       'Bruker APEX-II v2014-11.0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28629
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.346
_diffrn_reflns_theta_min         1.960
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.893
_exptl_absorpt_correction_T_max  0.9072
_exptl_absorpt_correction_T_min  0.3809
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5 (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_description       blade
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1865 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4715
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0204
_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^)+(0.0141P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0446
_refine_ls_wR_factor_ref         0.0455
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                4405
_reflns_number_total             4715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b01643_si_004.cif
_cod_data_source_block           su1504
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4130262
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.342
_shelx_estimated_absorpt_t_max   0.859
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_shelx_res_checksum              40594
_shelx_hkl_checksum              36551