Nickel–PNN catalysed sustainable synthesis of polysubstituted quinolines under microwave irradiation
Mohite, Manali A.; Sheokand, Sonu; Balakrishna, Maravanji S.; Catalysis Science & Technology 14 (2024) 5959–5969; doi:10.1039/D4CY00863D

data_1573000
_publ_section_title
;
 Nickel--PNN catalysed sustainable synthesis of polysubstituted quinolines
 under microwave irradiation
;
_journal_issue                   20
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              5959
_journal_page_last               5969
_journal_paper_doi               10.1039/D4CY00863D
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C21 H28 Cl N5 Ni P, C F3 O3 S'
_chemical_formula_sum            'C22 H28 Cl F3 N5 Ni O3 P S'
_chemical_formula_weight         624.68
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-03-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-06-13 deposited with the CCDC.	2024-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3501(8)
_cell_length_b                   10.6515(5)
_cell_length_c                   14.9182(6)
_cell_measurement_reflns_used    9414
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.24
_cell_volume                     2757.0(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15439
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.627
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4744
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1039 before and 0.0883 after correction.
The Ratio of minimum to maximum transmission is 0.6362.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.093
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1580 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.027(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4632
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0263P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                3946
_reflns_number_total             4632
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cy00863d2.cif
_cod_data_source_block           comp_6
_cod_database_code               1573000
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.914
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2A), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
1.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C20(H20A,H20B,
 H20C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              78227
_olex2_submission_special_instructions 'No special instructions were received'