What Are the Radical Intermediates in Oxidative N-Heterocyclic Carbene Organocatalysis?
Regnier, Vianney; Romero, Erik A.; Molton, Florian; Jazzar, Rodolphe; Bertrand, Guy; Martin, David; Journal of the American Chemical Society 141 (2019) 1109–1117; doi:10.1021/jacs.8b11824

data_4133623
_publ_section_title
;
 What Are the Radical Intermediates in Oxidative N-Heterocyclic Carbene
 Organocatalysis?
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1109
_journal_page_last               1117
_journal_paper_doi               10.1021/jacs.8b11824
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C37 H46 N O'
_chemical_formula_sum            'C37 H46 N O'
_chemical_formula_weight         520.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-20
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.805(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.5873(11)
_cell_length_b                   9.0822(4)
_cell_length_c                   23.4041(8)
_cell_measurement_reflns_used    3812
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.08
_cell_volume                     6107.4(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19452
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.391
_diffrn_reflns_theta_min         3.076
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_T_max  0.5210
_exptl_absorpt_correction_T_min  0.4207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0678 before and 0.0428 after correction. The Ratio of minimum to maximum transmission is 0.8075. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       block
_exptl_crystal_F_000             2264
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0531P)^2^+4.5764P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5217
_reflns_number_total             5599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b11824_si_002.cif
_cod_data_source_block           2f_radical
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4133623
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.893
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C35(H35), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C18(H18A,H18B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C30(H30), C28(H28), C6(H6), C12(H12), C29(H29), C9(H9),
 C16(H16), C7(H7), C13(H13), C8(H8), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C33(H33A,H33B,H33C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C), C20(H20A,H20B,H20C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C34(H34A,
 H34B,H34C)
;
_shelx_res_checksum              19292
_shelx_hkl_checksum              84229
_olex2_submission_special_instructions 'No special instructions were received'