Nickel(i)-catalyzed (de)hydrogenative coupling of amines and alkyl heteroarenes with alcohols
Zhang, Chunyan; Liang, Qianqian; Yang, Wei; Zhang, Guohui; Hu, Maolin; Zhang, Guoying; Green Chemistry 24 (2022) 7368–7375; doi:10.1039/D2GC02206K

data_7245467
_publ_section_title
;
 Nickel(i)-catalyzed (de)hydrogenative coupling of amines and alkyl
 heteroarenes with alcohols
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              7368
_journal_page_last               7375
_journal_paper_doi               10.1039/D2GC02206K
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         '2(Br), C36 H30 N10 Ni O2'
_chemical_formula_sum            'C36 H30 Br2 N10 Ni O2'
_chemical_formula_weight         853.23
_space_group_crystal_system      tetragonal
_space_group_IT_number           142
_space_group_name_Hall           '-I 4bd 2c'
_space_group_name_H-M_alt        'I 41/a c d :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2022-06-06 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   17.2287(5)
_cell_length_b                   17.2287(5)
_cell_length_c                   50.201(3)
_cell_measurement_reflns_used    5182
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      24.3380
_cell_measurement_theta_min      2.3600
_cell_volume                     14901.1(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -84.00 -15.00   0.75    5.00    --  -11.59 -37.00 -30.00   92
  2  \w     51.00  87.00   0.75    5.00    --   11.74-178.00-180.00   48
;
_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      -0.0398750000
_diffrn_orient_matrix_UB_12      0.0074210000
_diffrn_orient_matrix_UB_13      0.0024493000
_diffrn_orient_matrix_UB_21      0.0025863000
_diffrn_orient_matrix_UB_22      0.0345907000
_diffrn_orient_matrix_UB_23      -0.0075876000
_diffrn_orient_matrix_UB_31      -0.0099750000
_diffrn_orient_matrix_UB_32      -0.0209730000
_diffrn_orient_matrix_UB_33      -0.0116701000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            16361
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.364
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       block
_exptl_crystal_F_000             6880
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.588
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0713
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1104P)^2^+85.2121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1898
_refine_ls_wR_factor_ref         0.2181
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2300
_reflns_number_total             3292
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02206k2.cif
_cod_data_source_block           zgy-1-1
_cod_depositor_comments          'Adding full bibliography for 7245467.cif.'
_cod_original_cell_volume        14901.0(12)
_cod_original_sg_symbol_H-M      'I 41/a c d'
_cod_database_code               7245467
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H,H) groups
2. Others
 Fixed Sof: Br1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C14(H14), C2(H2), C18(H18), C3(H3), C17(H17), C16(H16),
 C15(H15), C9(H9), C10(H10), C12(H12), C11(H11)
3.b X=CH2 refined with riding coordinates:
 O1(H1A,H1B)
;
_shelx_res_checksum              16329
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.423
_oxdiff_exptl_absorpt_empirical_full_min 0.688