Nickel-Catalyzed Heteroarenes Cross Coupling via Tandem C‒H/C‒O Activation
Wang, Ting-Hsuan; Ambre, Ram; Wang, Qing; Lee, Wei-Chih; Wang, Pen-Cheng; Liu, Yuhua; Zhao, Lili; Ong, Tiow-Gan; ACS Catalysis 8 (2018) 11368–; doi:10.1021/acscatal.8b03436

data_4515800
_publ_section_title
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 Nickel-Catalyzed Heteroarenes Cross Coupling via Tandem C--H/C--O
 Activation
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_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              11368
_journal_paper_doi               10.1021/acscatal.8b03436
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C41 H43 Cl N4 Ni P, C4 H8 O'
_chemical_formula_sum            'C45 H51 Cl N4 Ni O P'
_chemical_formula_weight         789.02
_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     dual
_audit_creation_date             2017-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.361(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8919(6)
_cell_length_b                   12.6768(4)
_cell_length_c                   19.8115(7)
_cell_measurement_reflns_used    9281
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      2.26
_cell_volume                     4093.4(2)
_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_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1224
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            133407
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.161
_diffrn_reflns_theta_min         1.963
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1516 before and 0.0767 after correction.
The Ratio of minimum to maximum transmission is 0.8398.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       plate
_exptl_crystal_F_000             1668
_exptl_crystal_recrystallization_method
'Concentrated THF solution laid with Hexane'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         9058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0161P)^2^+4.0933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6270
_reflns_number_total             9058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03436_si_002.cif
_cod_data_source_block           i16705
_cod_database_code               4515800
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.790
_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.a Ternary CH refined with riding coordinates:
 C3(H3), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C20(H20), C21(H21),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32),
  C33(H33), C34(H34), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C),
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_olex2_exptl_crystal_mounting_method
;
The data was collected under N2 stream at 100 K 
;
_olex2_submission_special_instructions 'No special instructions were received'