C–H bond chlorination using nickel(ii) complexes of tetradentate amido-quinoline ligands
Adhikari, Sanjay; Sarkar, Aniruddha; Dhar, Basab Bijayi; Chemical Communications  (2022) –; doi:10.1039/D2CC00639A

data_7129798
_publ_section_title
;
 C--H bond chlorination using nickel(ii) complexes of tetradentate
 amido-quinoline ligands
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00639A
_journal_year                    2022
_chemical_formula_moiety         'C23 H18 N4 Ni O2'
_chemical_formula_sum            'C23 H18 N4 Ni O2'
_chemical_formula_weight         441.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-07 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.232(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.456(3)
_cell_length_b                   14.261(3)
_cell_length_c                   13.237(3)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.80
_cell_volume                     1953.5(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29713
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.702
_diffrn_reflns_theta_min         2.432
_exptl_absorpt_coefficient_mu    1.022
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       Block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0300P)^2^+0.8744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3965
_reflns_number_total             5029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00639a2.cif
_cod_data_source_block           sa-1
_cod_database_code               7129798
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.799
_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 Aromatic/amide H refined with riding coordinates:
 C17(H17), C14(H14), C13(H13), C22(H22), C15(H15), C7(H7), C16(H16), C20(H20),
 C12(H12), C9(H9), C8(H8), C21(H21)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              35969
_olex2_submission_special_instructions 'No special instructions were received'