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_4131709
_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         'C33 H34 N2 O4 S'
_chemical_formula_sum            'C33 H34 N2 O4 S'
_chemical_formula_weight         554.68
_chemical_name_common            MH127B
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                78.028(1)
_cell_angle_beta                 74.768(2)
_cell_angle_gamma                83.519(2)
_cell_formula_units_Z            4
_cell_length_a                   10.3202(5)
_cell_length_b                   15.5911(6)
_cell_length_c                   19.1946(8)
_cell_measurement_reflns_used    9758
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4754
_cell_measurement_theta_min      2.3770
_cell_volume                     2909.6(2)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_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 7.9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            176522
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.588
_diffrn_reflns_theta_min         2.238
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       nugget
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
 Flack x determined using 10263 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.002(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1461
_refine_ls_number_reflns         25501
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0471P)^2^+1.0740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.913
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                23537
_reflns_number_total             25501
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b09152_si_003.cif
_cod_data_source_block           MH127B_0m
_cod_database_code               4131709
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              91455
_shelx_hkl_checksum              56506