A copper-catalyzed oxidative coupling reaction of arylboronic acids, amines and carbon dioxide using molecular oxygen as the oxidant
Xiong, Wenfang; Qi, Chaorong; Guo, Tianzuo; Zhang, Min; Chen, Kai; Jiang, Huanfeng; Green Chem. 19 (2017) 1642–; doi:10.1039/C6GC03465A

data_7227708
_publ_section_title
;
 A copper-catalyzed oxidative coupling reaction of arylboronic acids,
 amines and carbon dioxide using molecular oxygen as the oxidant
;
_journal_issue                   7
_journal_name_full               'Green Chem.'
_journal_page_first              1642
_journal_paper_doi               10.1039/C6GC03465A
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C27 H23 N O2'
_chemical_formula_sum            'C27 H23 N O2'
_chemical_formula_weight         393.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2016-07-06 deposited with the CCDC.
2017-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                63.221(7)
_cell_angle_beta                 63.896(5)
_cell_angle_gamma                74.519(5)
_cell_formula_units_Z            2
_cell_length_a                   10.4147(5)
_cell_length_b                   10.8221(8)
_cell_length_c                   11.4326(7)
_cell_measurement_reflns_used    5159
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.7650
_cell_measurement_theta_min      4.7540
_cell_volume                     1029.22(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      3.00  29.00   1.00    1.00    --   41.89 -99.00 -30.00   26
  2  \w     65.00 120.00   1.00    1.00    --  101.33-125.00-150.00   55
  3  \w     83.00 109.00   1.00    1.00    --  101.33 -94.00-150.00   26
  4  \w     42.00 125.00   1.00    1.00    --  101.33 -61.00-180.00   83
  5  \w     74.00 178.00   1.00    1.00    --  101.33  30.00 -90.00  104
  6  \w    109.00 136.00   1.00    1.00    --  101.33 125.00-150.00   27
  7  \w    149.00 175.00   1.00    1.00    --  101.33 125.00-150.00   26
  8  \w     75.00 151.00   1.00    1.00    --  101.33  45.00-180.00   76
  9  \w     75.00 142.00   1.00    1.00    --  101.33  61.00  30.00   67
 10  \w    124.00 150.00   1.00    1.00    --  101.33  45.00 120.00   26
 11  \w     29.00  90.00   1.00    1.00    --  101.33 -30.00 -90.00   61
 12  \w     30.00 118.00   1.00    1.00    --  101.33 -61.00  30.00   88
 13  \w     22.00  48.00   1.00    1.00    --  101.33 -94.00-150.00   26
 14  \w     19.00 107.00   1.00    1.00    --  101.33 -94.00 -30.00   88
 15  \w    -94.00  -3.00   1.00    1.00    --  -41.89 125.00 -30.00   91
 16  \w   -115.00 -28.00   1.00    1.00    --  -41.89 -38.00  90.00   87
 17  \w   -103.00  -9.00   1.00    1.00    --  -41.89 -77.00-150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0005519000
_diffrn_orient_matrix_UB_12      -0.0988679000
_diffrn_orient_matrix_UB_13      -0.0638072000
_diffrn_orient_matrix_UB_21      0.0487127000
_diffrn_orient_matrix_UB_22      0.1156423000
_diffrn_orient_matrix_UB_23      -0.1485469000
_diffrn_orient_matrix_UB_31      0.1579927000
_diffrn_orient_matrix_UB_32      -0.0496564000
_diffrn_orient_matrix_UB_33      -0.0172066000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6952
_diffrn_reflns_theta_full        70.94
_diffrn_reflns_theta_max         70.94
_diffrn_reflns_theta_min         4.59
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Petroleumether/Ethylacetate'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.2102P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                3557
_reflns_number_total             3823
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc03465a2.cif
_cod_data_source_block           1605301
_cod_depositor_comments          'Adding full bibliography for 7227708.cif.'
_cod_original_cell_volume        1029.22(11)
_cod_database_code               7227708
_chemical_oxdiff_formula         'C20 H20 O6'
_chemical_oxdiff_usercomment     'XWF '
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H4A(0.031) H4B(0.031) H6(0.039) H7(0.035) H8(0.034) H10A(0.035)
 H10B(0.035) H11(0.039) H12(0.034) H13(0.033) H14(0.036) H15(0.053) H16(0.037)
 H17(0.043) H18(0.041) H20(0.049) H21(0.035) H22(0.042) H25(0.043) H26(0.041)
 H28(0.04) H29(0.051) H30(0.044)
 Fixed X: H4A(0.473) H4B(0.4267) H6(0.3388) H7(0.558) H8(0.2115) H10A(0.2115)
 H10B(0.1293) H11(0.1673) H12(-0.0331) H13(0.1018) H14(-0.2153) H15(0.5697)
 H16(0.0877) H17(-0.3251) H18(0.5174) H20(0.4912) H21(0.0852) H22(-0.0232)
 H25(0.126) H26(0.3001) H28(0.3462) H29(0.4972) H30(-0.2301)
 Fixed Y: H4A(1.0985) H4B(0.9644) H6(1.0668) H7(1.2223) H8(0.7132)
 H10A(1.2658) H10B(1.19) H11(1.0842) H12(0.5111) H13(0.5126) H14(0.3972)
 H15(1.3608) H16(0.2771) H17(0.1957) H18(1.3447) H20(1.1408) H21(0.7063)
 H22(0.0766) H25(1.209) H26(1.3405) H28(1.4324) H29(1.5063) H30(0.0354)
 Fixed Z: H4A(0.246) H4B(0.3831) H6(0.0381) H7(0.3204) H8(0.7188) H10A(0.2536)
 H10B(0.2218) H11(0.5591) H12(0.6064) H13(0.8843) H14(0.8068) H15(-0.3116)
 H16(0.9725) H17(0.9705) H18(0.4572) H20(-0.1957) H21(0.4366) H22(1.1368)
 H25(0.693) H26(0.6422) H28(0.0434) H29(-0.1915) H30(1.1366)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.047
_oxdiff_exptl_absorpt_empirical_full_min 0.553