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_4084629
_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_formula_moiety         'C24 H36 Br2 Ni2 O2 P2'
_chemical_formula_sum            'C24 H36 Br2 Ni2 O2 P2'
_chemical_formula_weight         695.71
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.5970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.89710(10)
_cell_length_b                   11.02090(10)
_cell_length_c                   12.80450(10)
_cell_measurement_temperature    100(2)
_cell_volume                     1351.57(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0070
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            50716
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.018
_diffrn_reflns_theta_min         6.475
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.462
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.043
_refine_diff_density_min         -1.274
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0853P)^2^+7.0839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2591
_reflns_number_total             2592
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om500938u_si_002.cif
_cod_data_source_block           bor134
_cod_depositor_comments
'Adding full bibliography for 4084629--4084634.cif.'
_cod_database_code               4084629
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.626
_shelx_estimated_absorpt_t_min   0.511
_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:
 C10(H10), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              47402
_shelx_hkl_checksum              78542
_olex2_submission_special_instructions 'No special instructions were received'