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_1573001
_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         '2(C21 H27 Cl N5 Ni P), C6 H6, H2 O'
_chemical_formula_sum            'C48 H62 Cl2 N10 Ni2 O P2'
_chemical_formula_weight         1045.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-05
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-06-13 deposited with the CCDC.	2024-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                85.707(4)
_cell_angle_beta                 85.978(4)
_cell_angle_gamma                74.077(4)
_cell_formula_units_Z            1
_cell_length_a                   7.8912(7)
_cell_length_b                   8.8336(10)
_cell_length_c                   18.4362(19)
_cell_measurement_reflns_used    9797
_cell_measurement_temperature    113.00
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      2.22
_cell_volume                     1230.7(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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      113.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0550
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            61201
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.534
_diffrn_reflns_theta_min         2.219
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1460 before and 0.0649 after correction.
The Ratio of minimum to maximum transmission is 0.8558.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.052
_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     311
_refine_ls_number_reflns         6249
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0220P)^2^+0.7931P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0647
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5592
_reflns_number_total             6249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cy00863d2.cif
_cod_data_source_block           comp_8
_cod_database_code               1573001
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.887
_shelx_estimated_absorpt_t_min   0.766
_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, All O(H,H) groups
2. Restrained distances
 C23-C24 \\sim C23A-C24A
 with sigma of 0.02
 C23-C22 \\sim C23A-C22A
 with sigma of 0.02
 C24-C22 \\sim C24A-C22A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C22) = Uanis(C23) = Uanis(C24)
Uanis(C22A) = Uanis(C23A) = Uanis(C24A)
4. Others
 Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=1-FVAR(1)
 Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C22)=Sof(H22)=FVAR(1)
 Fixed Sof: O2(0.5) H2A(0.5) H2B(0.5)
5.a Free rotating group:
 O2(H2A,H2B)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C13(H13), C4(H4), C11(H11), C3(H3), C2(H2), C12(H12),
 C10(H10), C23(H23), C24(H24), C22(H22), C22A(H22A), C23A(H23A), C24A(H24A)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C16(H16A,H16B,
 H16C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              83773
_olex2_submission_special_instructions 'No special instructions were received'