Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone.
Bucher, Cyril; Deans, Richard M.; Burns, Noah Z.; Journal of the American Chemical Society 137 (2015) 12784–12787; doi:10.1021/jacs.5b08398

data_4129571
_publ_section_title
;
 Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12784
_journal_page_last               12787
_journal_paper_doi               10.1021/jacs.5b08398
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H17 Br Cl2 Fe O2'
_chemical_formula_sum            'C16 H17 Br Cl2 Fe O2'
_chemical_formula_weight         447.95
_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   geom
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.9070(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4370(6)
_cell_length_b                   9.6628(8)
_cell_length_c                   11.6887(10)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.74
_cell_volume                     833.88(12)
_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, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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  0.0245
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22494
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_min         1.755
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.623
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.5493
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_description       tablet
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1794 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4128
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0187
_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^)+(0.0244P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0478
_refine_ls_wR_factor_ref         0.0480
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3993
_reflns_number_total             4128
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b08398_si_004.cif
_cod_data_source_block           su1515a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4129571
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.443
_shelx_estimated_absorpt_t_max   0.755
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_shelx_res_checksum              54669
_shelx_hkl_checksum              15076