Ortho Derivatization of Phenols through C‒H Nickelation: Synthesis, Characterization, and Reactivities of Ortho-Nickelated Phosphinite Complexes
Vabre, Boris; Deschamps, Félix; Zargarian, Davit; Organometallics 33 (2014) 6623–; doi:10.1021/om500938u

data_4084632
_publ_section_title
;
 Ortho Derivatization of Phenols through C--H Nickelation: Synthesis,
 Characterization, and Reactivities of Ortho-Nickelated Phosphinite
 Complexes
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              6623
_journal_paper_doi               10.1021/om500938u
_journal_volume                  33
_journal_year                    2014
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C26 H42 Br2 Ni O4 P2'
_chemical_formula_sum            'C26 H42 Br2 Ni O4 P2'
_chemical_formula_weight         699.06
_chemical_name_systematic
;
 ?
;
_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
_audit_creation_date             2014-07-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                102.066(1)
_cell_angle_beta                 96.868(1)
_cell_angle_gamma                96.906(1)
_cell_formula_units_Z            2
_cell_length_a                   9.0321(2)
_cell_length_b                   11.0400(3)
_cell_length_c                   15.7000(4)
_cell_measurement_reflns_used    9595
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.72
_cell_measurement_theta_min      4.14
_cell_volume                     1502.84(7)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, )'
_computing_data_collection       'APEX2 (Bruker AXS, 0)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, )'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            79263
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.175
_diffrn_reflns_theta_min         2.911
_exptl_absorpt_coefficient_mu    5.283
_exptl_absorpt_correction_T_max  0.1209
_exptl_absorpt_correction_T_min  0.1112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_refine_diff_density_max         1.808
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0403P)^2^+5.9162P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5606
_reflns_number_total             5630
_cod_data_source_file            om500938u_si_002.cif
_cod_data_source_block           BORS97
_cod_depositor_comments
'Adding full bibliography for 4084629--4084634.cif.'
_cod_database_code               4084632
_shelx_estimated_absorpt_t_max   0.226
_shelx_estimated_absorpt_t_min   0.087
_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:
 C213(H213), C210(H210), C110(H110), C113(H113)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C25(H25), C26(H26), C16(H16), C15(H15), C13(H13), C12(H12)
2.c Idealised Me refined as rotating group:
 C215(H21A,H21B,H21C), C214(H21D,H21E,H21F), C211(H21G,H21H,H21I), C212(H21J,
 H21K,H21L), C27(H27A,H27B,H27C), C111(H11A,H11B,H11C), C112(H11D,H11E,H11F),
 C115(H11G,H11H,H11I), C114(H11J,H11K,H11L), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'