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_7129143
_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         'C20 H15 F N2 O2'
_chemical_formula_sum            'C20 H15 F N2 O2'
_chemical_formula_weight         334.34
_chemical_name_systematic        (E,E)-1,3-distyryl-5-fluorouracil
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-27 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   33.8915(10)
_cell_length_b                   33.8915(10)
_cell_length_c                   7.0535(13)
_cell_measurement_reflns_used    1455
_cell_measurement_temperature    99.9
_cell_measurement_theta_max      24.69
_cell_measurement_theta_min      2.40
_cell_volume                     7016.4(13)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.9
_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 0.999
_diffrn_measured_fraction_theta_max 0.996
_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     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5543
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_min         2.082
_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    0.101
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.700
_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 31204 reflections, Rint = 0.0562
 (21115 with I > 3sig(I), Rint = 0.0420)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       needle
_exptl_crystal_F_000             3132
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 982 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         5543
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0537
_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^)+(0.0410P)^2^+4.9561P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                4523
_reflns_number_total             5543
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04356k2.cif
_cod_data_source_block           LNB381_twin
_cod_original_cell_volume        7016.4(14)
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               7129143
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.34163
 0.26796 0.39041
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C6(H6), C5(H5), C13(H13), C12(H12), C11(H11), C14(H14),
 C00J(H00J), C19(H19), C18(H18), C4(H4), C8(H8), C9(H9), C10(H10)
;
_olex2_date_sample_data_collection 2021-04-16
_olex2_date_sample_submission    2021-04-16
_olex2_submission_original_sample_id LNB381
_olex2_submission_special_instructions 'No special instructions were received'