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_4084631
_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         'C28 H42 Br2 Ni O6 P2, C7 H8'
_chemical_formula_sum            'C35 H50 Br2 Ni O6 P2'
_chemical_formula_weight         847.22
_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                99.459(2)
_cell_angle_beta                 106.577(2)
_cell_angle_gamma                95.334(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4323(6)
_cell_length_b                   12.5239(7)
_cell_length_c                   15.3754(9)
_cell_measurement_reflns_used    9402
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.56
_cell_measurement_theta_min      4.47
_cell_volume                     1878.28(19)
_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      100.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            100396
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.828
_diffrn_reflns_theta_min         3.061
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.379
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         7027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0554P)^2^+1.3372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                6608
_reflns_number_total             7027
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om500938u_si_002.cif
_cod_data_source_block           bors95
_cod_depositor_comments
'Adding full bibliography for 4084629--4084634.cif.'
_cod_database_code               4084631
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.721
_shelx_estimated_absorpt_t_min   0.669
_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), C13(H13), C30(H30), C33(H33)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C22(H22), C23(H23), C25(H25), C26(H26),
 C41(H41), C42(H42), C43(H43), C44(H44), C45(H45)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C28(H28A,H28B,H28C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              89335
_shelx_hkl_checksum              85435
_olex2_submission_special_instructions 'No special instructions were received'