Sonogashira reactions of alkyl halides catalyzed by NHC [CNN] pincer nickel(ii) complexes
Wang, Zijing; Zheng, Tingting; Sun, Hongjian; Li, Xiaoyan; Fuhr, Olaf; Fenske, Dieter; New Journal of Chemistry 42 (2018) 11465–; doi:10.1039/C8NJ02138D

data_7057470
_publ_section_title
;
 Sonogashira reactions of alkyl halides catalyzed by NHC [CNN] pincer
 nickel(ii) complexes
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11465
_journal_paper_doi               10.1039/C8NJ02138D
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C28 H28 N4 Ni'
_chemical_formula_sum            'C28 H28 N4 Ni'
_chemical_formula_weight         479.25
_chemical_name_systematic        2018Li01
_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'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-16 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.637(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1930(1)
_cell_length_b                   8.6954(1)
_cell_length_c                   24.4859(4)
_cell_measurement_reflns_used    7064
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      73.4810
_cell_measurement_theta_min      3.9450
_cell_volume                     2375.35(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9831
_diffrn_measured_fraction_theta_max 0.9831
_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    -18.00  89.00   0.50    2.50    --    0.00  19.00 120.00  214
  2  \w    -17.00  78.00   0.50    2.50    --    0.00  37.00-180.00  190
  3  \w     33.00  89.00   0.50    2.50    --    0.00  57.00  30.00  112
  4  \w    -20.00  66.00   0.50    2.50    --    0.00  57.00   0.00  172
  5  \w     68.00 168.00   0.50   27.00    --   94.60  77.00-120.00  200
  6  \w     88.00 167.00   0.50   27.00    --   94.60  45.00   0.00  158
  7  \w     12.00 116.00   0.50   27.00    --   94.60 -61.00 150.00  208
  8  \w     83.00 128.00   0.50   27.00    --   94.60  45.00  60.00   90
  9  \w     91.00 117.00   0.50   27.00    --   94.60  30.00-150.00   52
 10  \w     76.00 171.00   0.50   27.00    --   94.60  45.00  30.00  190
 11  \w     72.00 184.00   0.50   27.00    --   94.60  61.00 -60.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0674073000
_diffrn_orient_matrix_UB_12      -0.1188608000
_diffrn_orient_matrix_UB_13      0.0325098000
_diffrn_orient_matrix_UB_21      -0.0540663000
_diffrn_orient_matrix_UB_22      -0.0713135000
_diffrn_orient_matrix_UB_23      -0.0540539000
_diffrn_orient_matrix_UB_31      0.1077348000
_diffrn_orient_matrix_UB_32      -0.1104891000
_diffrn_orient_matrix_UB_33      -0.0003175000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1210
_diffrn_reflns_av_unetI/netI     0.0887
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13102
_diffrn_reflns_theta_full        66.5958
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         3.62
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.345
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.3400
_exptl_crystal_description       block
_exptl_crystal_F_000             998.5406
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.1407
_refine_diff_density_min         -1.1761
_refine_diff_density_rms         0.1341
_refine_ls_d_res_high            0.8400
_refine_ls_d_res_low             12.2029
_refine_ls_goodness_of_fit_ref   0.9755
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9755
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0833
_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^)+(0.1875P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2237
_refine_ls_wR_factor_ref         0.2359
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                3213
_reflns_number_total             4133
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8nj02138d2.cif
_cod_data_source_block           complex9
_cod_depositor_comments          'Adding full bibliography for 7057470.cif.'
_cod_database_code               7057470
_chemical_oxdiff_formula         'C12 H12 N3 O1 Ni1'
_reflns_odcompleteness_completeness 99.19
_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 Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C14(H14a,H14b,H14c), C27(H27a,H27b,H27c), C28(H28a,H28b,
 H28c)
;
_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 6.449
_oxdiff_exptl_absorpt_empirical_full_min 0.245