Iron-Catalyzed α-C–H functionalization of π-Bonds: Cross-Dehydrogenative Coupling and Mechanistic Insights
Wang, Yidong; Zhu, Jin; Guo, Rui; Lindberg, Haley; Wang, Yiming; Chemical Science  (2020) –; doi:10.1039/D0SC05091A

data_1559368
_publ_section_title
;
 Iron-Catalyzed \a-C--H functionalization of \p-Bonds:
 Cross-Dehydrogenative Coupling and Mechanistic Insights
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC05091A
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H23 N O4'
_chemical_formula_weight         365.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-04-12 deposited with the CCDC.	2020-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.511(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0265(10)
_cell_length_b                   14.1187(8)
_cell_length_c                   8.9890(5)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      70.063
_cell_measurement_theta_min      4.305
_cell_volume                     1898.82(19)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15496
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.057
_diffrn_reflns_theta_min         4.305
_diffrn_source                   'Bruker AXS X8 Prospector Ultra IMuS'
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1693 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3528
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0257
_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^)+(0.0680P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                3509
_reflns_number_total             3528
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05091a2.cif
_cod_data_source_block           wyd2_282
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'direct methods' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1559368
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.859
_shelx_estimated_absorpt_t_max   0.919
_shelx_res_checksum              15749