Organocopper(ii) complexes: new catalysts for carbon–carbon bond formation via electrochemical atom transfer radical addition (eATRA)
Gonzálvez, Miguel A.; Su, Chuyi; Williams, Craig M.; Bernhardt, Paul V.; Chemical Science  (2022) –; doi:10.1039/D2SC03418B

data_1567527
_publ_section_title
;
 Organocopper(ii) complexes: new catalysts for carbon--carbon bond
 formation via electrochemical atom transfer radical addition (eATRA)
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC03418B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H12 Br N'
_chemical_formula_weight         274.16
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2022-05-30T14:50:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2022-06-01 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5971(6)
_cell_length_b                   17.1790(10)
_cell_length_c                   5.9922(3)
_cell_measurement_reflns_used    1171
_cell_measurement_temperature    194(2)
_cell_measurement_theta_max      61.34
_cell_measurement_theta_min      4.6
_cell_measurement_wavelength     1.54184
_cell_volume                     1193.81(11)
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      194(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.091467
_diffrn_orient_matrix_UB_12      0.064391
_diffrn_orient_matrix_UB_13      0.026688
_diffrn_orient_matrix_UB_21      -0.090944
_diffrn_orient_matrix_UB_22      0.061894
_diffrn_orient_matrix_UB_23      -0.060112
_diffrn_orient_matrix_UB_31      -0.031806
_diffrn_orient_matrix_UB_32      0.008157
_diffrn_orient_matrix_UB_33      0.248495
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            2736
_diffrn_reflns_point_group_measured_fraction_full 0.745
_diffrn_reflns_point_group_measured_fraction_max 0.745
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        61.486
_diffrn_reflns_theta_max         61.486
_diffrn_reflns_theta_min         4.6
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.436
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate and petroleum ether'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.27
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1382
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0380P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.346
_reflns_Friedel_fraction_full    0.43
_reflns_Friedel_fraction_max     0.43
_reflns_number_gt                1246
_reflns_number_total             1382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03418b2.cif
_cod_data_source_block           2214mg14
_cod_database_code               1567527
_shelx_estimated_absorpt_t_min   0.471
_shelx_estimated_absorpt_t_max   0.917
_shelx_shelxl_version_number     2018/1