Ni(II)-catalyzed C–H hydroarylation of diarylacetylenes with imidazolium salts
Wang, Tianbao; Zheng, Xuesong; Zheng, Qinze; Zhou, Fulin; Wang, Linhua; Gao, Ge; Chemical Communications  (2022) –; doi:10.1039/D1CC07309E

data_7129624
_publ_section_title
;
 Ni(II)-catalyzed C--H hydroarylation of diarylacetylenes with imidazolium
 salts
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07309E
_journal_year                    2022
_chemical_formula_moiety         'I, C23 H21 N2'
_chemical_formula_sum            'C23 H21 I N2'
_chemical_formula_weight         452.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2021-10-06 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.336(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5543(4)
_cell_length_b                   8.6038(2)
_cell_length_c                   14.9273(4)
_cell_measurement_reflns_used    4651
_cell_measurement_temperature    292.2(6)
_cell_measurement_theta_max      71.4600
_cell_measurement_theta_min      4.6030
_cell_volume                     2050.39(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.2(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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   -103.00 -16.00   1.00    2.42    --  -34.98 -57.00-180.00   87
  2  \w      1.00  75.00   1.00    2.42    --   34.98 -99.00-150.00   74
  3  \w     23.00  90.00   1.00    2.42    --   34.98-125.00-150.00   67
  4  \w      1.00  75.00   1.00    2.42    --   34.98 -99.00   0.00   74
  5  \w     13.00 106.00   1.00    2.42    --   34.98  38.00-180.00   93
  6  \w    -33.00  53.00   1.00    2.42    --   34.98 -57.00  30.00   86
  7  \w     -3.00 107.00   1.00    2.42    --   34.98  19.00  30.00  110
  8  \w     35.00 133.00   1.00    9.67    --  106.90 -30.00-180.00   98
  9  \w     36.00 113.00   1.00    9.67    --  106.90-111.00-120.00   77
 10  \w     57.00 151.00   1.00    9.67    --  106.90 178.00 -90.00   94
 11  \w     87.00 175.00   1.00    9.67    --  106.90  61.00 120.00   88
 12  \w     37.00 110.00   1.00    9.67    --  106.90 -94.00-120.00   73
 13  \w     39.00 127.00   1.00    9.67    --  106.90 -61.00   0.00   88
 14  \w     87.00 175.00   1.00    9.67    --  106.90  61.00   0.00   88
 15  \w     38.00 136.00   1.00    9.67    --  106.90 -77.00-120.00   98
 16  \w      6.00  82.00   1.00    2.42    --   34.98  77.00  60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0790366000
_diffrn_orient_matrix_UB_12      -0.0781801000
_diffrn_orient_matrix_UB_13      0.0152905000
_diffrn_orient_matrix_UB_21      0.0541079000
_diffrn_orient_matrix_UB_22      -0.1336135000
_diffrn_orient_matrix_UB_23      0.0528521000
_diffrn_orient_matrix_UB_31      0.0117456000
_diffrn_orient_matrix_UB_32      0.0898497000
_diffrn_orient_matrix_UB_33      0.0918199000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11549
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.363
_diffrn_reflns_theta_min         5.542
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.345
_refine_diff_density_min         -2.032
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0618
_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^)+(0.1127P)^2^+2.1006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1795
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3451
_reflns_number_total             3936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc07309e2.cif
_cod_data_source_block           wtb-1
_cod_original_cell_volume        2050.41(10)
_cod_database_code               7129624
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C009(H009), C00D(H00D), C00E(H00E), C00G(H00G),
 C00H(H00H), C00I(H00I), C00K(H00L), C00L(H00M), C00M(H00N), C00N(H00O),
 C00O(H00P), C00P(H00Q), C00Q(H00R)
2.b Idealised Me refined as rotating group:
 C00B(H00A,H00B,H00C), C00J(H00F,H00J,H00K)
;
_shelx_res_checksum              92556
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-10-20
_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 2.210
_oxdiff_exptl_absorpt_empirical_full_min 0.571