Visible-Light-Activated Asymmetric β-C-H Functionalization of Acceptor-Substituted Ketones with 1,2-Dicarbonyl Compounds.
Ma, Jiajia; Rosales, Anthony R.; Huang, Xiaoqiang; Harms, Klaus; Riedel, Radostan; Wiest, Olaf; Meggers, Eric; Journal of the American Chemical Society 139 (2017) 17245–17248; doi:10.1021/jacs.7b09152

data_4131708
_publ_section_title
;
 Visible-Light-Activated Asymmetric \b-C-H Functionalization of
 Acceptor-Substituted Ketones with 1,2-Dicarbonyl Compounds.
;
_journal_issue                   48
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17245
_journal_page_last               17248
_journal_paper_doi               10.1021/jacs.7b09152
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C49 H41 Br2 F N3 O2 Rh S2'
_chemical_formula_sum            'C49 H41 Br2 F N3 O2 Rh S2'
_chemical_formula_weight         1049.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.86140(10)
_cell_length_b                   17.9146(2)
_cell_length_c                   18.8871(2)
_cell_measurement_reflns_used    79289
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.89
_cell_measurement_theta_min      2.34
_cell_volume                     4351.72(8)
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.127.0 (STOE, 2016)'
_computing_data_reduction
'X-Area Integrate 1.71.0.0 (STOE, 2016) X-Area LANA 1.68.2.0 (STOE, 2016)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  'X-Area 1.77'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            77982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.137
_diffrn_reflns_theta_min         3.400
_diffrn_source                   'GeniX 3D HF Cu'
_exptl_absorpt_coefficient_mu    6.609
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.2381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'STOE LANA, absorption correction by scaling of reflection intensities.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
; 
 Flack x determined using 3696 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.006(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         8981
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0265
_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^)+(0.0459P)^2^+1.5670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                8638
_reflns_number_total             8981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b09152_si_002.cif
_cod_data_source_block           MH139B
_cod_database_code               4131708
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.194
_shelx_estimated_absorpt_t_max   0.558
_shelx_res_checksum              26036
_shelx_hkl_checksum              47745