C−H Nickellation of Phenol-Derived Phosphinites: Regioselectivity and Structures of Cyclonickellated Complexes
Mangin, Loïc P; Zargarian, Davit; Dalton Transactions  (2017) –; doi:10.1039/C7DT03403B

data_7044635
_publ_section_title
;
 C&#x2212;H Nickellation of Phenol-Derived Phosphinites: Regioselectivity
 and Structures of Cyclonickellated Complexes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/C7DT03403B
_journal_year                    2017
_chemical_formula_moiety         'C14 H21 Br N Ni O P'
_chemical_formula_sum            'C14 H21 Br N Ni O P'
_chemical_formula_weight         388.91
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-10-24 deposited with the CCDC.
2017-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                97.074(2)
_cell_angle_beta                 101.279(2)
_cell_angle_gamma                111.252(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4137(4)
_cell_length_b                   9.6993(5)
_cell_length_c                   12.7577(7)
_cell_measurement_reflns_used    9081
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.611
_cell_measurement_theta_min      3.146
_cell_volume                     819.36(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19653
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.638
_diffrn_reflns_theta_min         3.145
_exptl_absorpt_coefficient_mu    9.146
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1288 before and 0.0726 after correction. The Ratio of minimum to maximum transmission is 0.7766. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_preparation       'Slow evap Et2O'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.630
_refine_diff_density_min         -1.540
_refine_diff_density_rms         0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.251
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0682P)^2^+0.1205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3695
_reflns_number_total             3772
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt03403b2.cif
_cod_data_source_block           loic94
_cod_database_code               7044635
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.711
_shelx_estimated_absorpt_t_min   0.528
_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:
 C7(H7), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              12856
_olex2_submission_special_instructions 'No special instructions were received'