Enantioselective Synthesis of Azamerone.
Landry, Matthew L.; McKenna, Grace M.; Burns, Noah Z.; Journal of the American Chemical Society 141 (2019) 2867–2871; doi:10.1021/jacs.8b12566

data_4128455
_publ_section_title
;
 Enantioselective Synthesis of Azamerone.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2867
_journal_page_last               2871
_journal_paper_doi               10.1021/jacs.8b12566
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C23 H31 Cl3 O4'
_chemical_formula_sum            'C23 H31 Cl3 O4'
_chemical_formula_weight         477.83
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 99.171(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.9120(5)
_cell_length_b                   9.4971(5)
_cell_length_c                   11.5555(6)
_cell_measurement_reflns_used    9841
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.33
_cell_measurement_theta_min      3.87
_cell_volume                     1182.22(10)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19514
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.443
_diffrn_reflns_theta_min         3.875
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    3.726
_exptl_absorpt_correction_T_max  0.7149
_exptl_absorpt_correction_T_min  0.6056
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.139
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0460P)^2^+0.2505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0764
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                4526
_reflns_number_total             4561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b12566_si_003.cif
_cod_data_source_block           su1811
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4128455
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.580
_shelx_estimated_absorpt_t_max   0.625
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelx_res_checksum              71162
_shelx_hkl_checksum              68925