Cu-catalyzed C(sp2)-N-bond coupling of boronic acids and cyclic imides
Berntsen, Linn Neerbye; Nordbø Solvi, Thomas; Sørnes, Kristian; Wragg, David S.; Sandtorv, Alexander Harald H.; Chemical Communications  (2021) –; doi:10.1039/D1CC04356K

data_7129141
_publ_section_title
;
 Cu-catalyzed C(sp2)-N-bond coupling of boronic acids and cyclic imides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC04356K
_journal_year                    2021
_chemical_formula_moiety         'C26 H19 Br N2 O2'
_chemical_formula_sum            'C26 H19 Br N2 O2'
_chemical_formula_weight         471.34
_chemical_name_systematic
(Z)-(5-(2-bromobenzylidene))-(E,E)-1,3-distyrylhydantoin
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-27 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                77.804(3)
_cell_angle_beta                 72.890(3)
_cell_angle_gamma                73.581(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2065(11)
_cell_length_b                   10.3700(13)
_cell_length_c                   12.0590(15)
_cell_measurement_reflns_used    5140
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      2.38
_cell_volume                     1045.1(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3678
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.134
_diffrn_reflns_theta_max         25.134
_diffrn_reflns_theta_min         2.068
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.993
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 20573 reflections, Rint = 0.0739
 (14415 with I > 3sig(I), Rint = 0.0630)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          1.1
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0784P)^2^+1.0318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3024
_reflns_number_total             3678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04356k2.cif
_cod_data_source_block           LNB387_bis_twin
_cod_database_code               7129141
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.218
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.700(3)
 0.300(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C23(H23), C19(H19), C7(H7), C12(H12), C11(H11), C14(H14), C4(H4),
 C25(H25), C9(H9), C24(H24), C26(H26), C16(H16), C8(H8), C22(H22), C18(H18),
 C10(H10), C15(H15), C17(H17)
;
_shelx_res_checksum              96511
_olex2_date_sample_data_collection 2021-04-15
_olex2_date_sample_submission    2021-04-15
_olex2_exptl_crystal_mounting_method
'Frozen on a Mitegen cryoloop in Paretone oil.'
_olex2_submission_original_sample_id LNB387_bis
_olex2_submission_special_instructions 'No special instructions were received'