Aerobic oxidation-functionalization of the aryl moiety in van Koten's pincer complex (NCN)Ni(ii)Br: relevance to carbon–heteroatom coupling reactions promoted by high-valent nickel species
Cloutier, Jean-Philippe; Zamani, Fahimeh; Zargarian, Davit; New Journal of Chemistry 46 (2022) 1800–1807; doi:10.1039/D1NJ05162H

data_7061169
_publ_section_title
;
 Aerobic oxidation-functionalization of the aryl moiety in van Koten's
 pincer complex (NCN)Ni(ii)Br: relevance to carbon--heteroatom coupling
 reactions promoted by high-valent nickel species
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1800
_journal_page_last               1807
_journal_paper_doi               10.1039/D1NJ05162H
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C15 H28 N2 Ni O Si'
_chemical_formula_sum            'C15 H28 N2 Ni O Si'
_chemical_formula_weight         339.19
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2021-10-25 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 121.2275(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3810(7)
_cell_length_b                   13.9962(8)
_cell_length_c                   11.9361(7)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.609
_cell_measurement_theta_min      5.502
_cell_volume                     1768.70(18)
_computing_cell_refinement
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23724
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         67.132
_diffrn_reflns_theta_min         3.768
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    6.525
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.3912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1576 before and 0.1030 after correction.
The Ratio of minimum to maximum transmission is 0.5196.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       chunk
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.239
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 1607 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.476(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4033
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0605
_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^)+(0.1041P)^2^+5.7470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1644
_reflns_Friedel_coverage         0.970
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3989
_reflns_number_total             4033
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05162h2.cif
_cod_data_source_block           jeanp91
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_colour_primary' value 'Yellow' was changed
to 'yellow' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7061169.cif.
;
_cod_original_cell_volume        1768.69(18)
_cod_database_code               7061169
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1(10) 0.44(9) 0(10) 0.05(9)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'