BiCl3-catalyzed green synthesis of 4-hydroxy-2-quinolone analogues under microwave irradiation
Bouone, Yousra Ouafa; Bouzina, Abdeslem; Sayad, Rayene; Djemel, Abdelhak; Benaceur, Farouk; Zoukel, Abdelhalim; Ibrahim-Ouali, Malika; Aouf, Nour-Eddine; Bouchareb, Fouzia; RSC Advances 13 (2023) 28030–28041; doi:10.1039/D3RA05289C

data_7247428
_publ_section_title
;
 BiCl3-catalyzed green synthesis of 4-hydroxy-2-quinolone analogues under
 microwave irradiation
;
_journal_issue                   40
_journal_name_full               'RSC Advances'
_journal_page_first              28030
_journal_page_last               28041
_journal_paper_doi               10.1039/D3RA05289C
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C18 H19 N O3'
_chemical_formula_sum            'C18 H19 N O3'
_chemical_formula_weight         297.34
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2frhxm
_audit_creation_date             2022-06-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-27 deposited with the CCDC.	2023-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                102.588(4)
_cell_angle_beta                 102.906(4)
_cell_angle_gamma                91.799(3)
_cell_formula_units_Z            2
_cell_length_a                   6.4370(3)
_cell_length_b                   10.9513(4)
_cell_length_c                   11.3400(6)
_cell_measurement_reflns_used    5848
_cell_measurement_temperature    295
_cell_measurement_theta_max      31.3890
_cell_measurement_theta_min      2.9990
_cell_volume                     757.77(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -57.00  11.00   1.00   25.00    --  -19.88  90.00  26.00   68
  2  \w    -23.00  12.00   1.00   25.00    --  -19.88 -90.00 -88.00   35
  3  \w    -32.00  57.00   1.00   25.00    --   20.34 -90.00 -88.00   89
  4  \w    -90.00   4.00   1.00   25.00    --  -19.88 -38.00  90.00   94
  5  \w    -93.00   5.00   1.00   25.00    --  -19.88 -57.00   0.00   98
  6  \w    -44.00  -4.00   1.00   25.00    --  -19.88  38.00 150.00   40
  7  \w      8.00  54.00   1.00   25.00    --  -19.88  38.00 150.00   46
  8  \w    -94.00  -2.00   1.00   25.00    --  -19.88 -38.00-150.00   92
  9  \w     36.00 106.00   1.00   25.00    --   20.34-178.00  60.00   70
 10  \w     -8.00  81.00   1.00   25.00    --   20.34  57.00-120.00   89
 11  \w     35.00  74.00   1.00   25.00    --   20.34 178.00 -90.00   39
 12  \w     -4.00  74.00   1.00   25.00    --   22.00-118.00-174.02   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0369776000
_diffrn_orient_matrix_UB_12      0.0313510000
_diffrn_orient_matrix_UB_13      0.0520987000
_diffrn_orient_matrix_UB_21      -0.0286316000
_diffrn_orient_matrix_UB_22      0.0498129000
_diffrn_orient_matrix_UB_23      -0.0296412000
_diffrn_orient_matrix_UB_31      -0.1033613000
_diffrn_orient_matrix_UB_32      -0.0311670000
_diffrn_orient_matrix_UB_33      -0.0275092000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19501
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.343
_diffrn_reflns_theta_min         2.360
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         5272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0579P)^2^+0.1794P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1579
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3672
_reflns_number_total             5272
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra05289c2.cif
_cod_data_source_block           db
_cod_database_code               7247428
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. 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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              64643
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.460