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_7129144
_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         'C9 H9 N O3 S'
_chemical_formula_sum            'C9 H9 N O3 S'
_chemical_formula_weight         211.24
_chemical_name_systematic
5,5-Dimethyl-3-(3-thiophenyl)-2,4-oxazolidinedione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-07-13
_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                90
_cell_formula_units_Z            8
_cell_length_a                   13.5471(10)
_cell_length_b                   7.5236(5)
_cell_length_c                   18.4113(14)
_cell_measurement_reflns_used    8689
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      2.68
_cell_volume                     1876.5(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 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 0.9830
_diffrn_measured_fraction_theta_max 0.9830
_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           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18385
_diffrn_reflns_theta_full        30.5675
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         2.68
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0824 before and 0.0444 after correction. The Ratio of minimum to maximum transmission is 0.9425. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4953
_exptl_crystal_description       block
_exptl_crystal_F_000             881.4544
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.5089
_refine_diff_density_min         -0.3274
_refine_diff_density_rms         0.0835
_refine_ls_d_res_high            0.6988
_refine_ls_d_res_low             7.6141
_refine_ls_goodness_of_fit_ref   1.0526
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0526
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.7002P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0804
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              0
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                2348
_reflns_number_total             2826
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1cc04356k2.cif
_cod_data_source_block           TNS4_14
_cod_database_code               7129144
_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. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(S1A)
Uanis(S1) = Uanis(C1A)
3. Others
 Sof(H4b)=Sof(S1A)=Sof(C1A)=Sof(H1A)=Sof(H2b)=Sof(H4b)=Sof(H1A)=1-FVAR(1)
 Sof(S1)=Sof(C1)=Sof(H1)=Sof(H4a)=Sof(H2)=Sof(H2a)=Sof(H1)=Sof(H4a)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2a), C2(H2b), C1(H1), C4(H4a), C4(H4b), C1A(H1A)
4.b Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c)
;
_olex2_date_sample_completion    2021-07-08
_olex2_date_sample_data_collection 2021-07-08
_olex2_exptl_crystal_mounting_method
'Frozen on Mitegen cryoloop with Paretone oil'
_olex2_submission_special_instructions 'No special instructions were received'