Facile synthesis of functionalized quinolinones in a green reaction medium and their photophysical properties.
Keerthana, Pari; Suresh, Sundararajan; Nawaz Khan, Fazlur Rahman; Organic & biomolecular chemistry 23 (2024) 126–137; doi:10.1039/d4ob01390e

data_7160194
_publ_section_title
;
 Facile synthesis of functionalized quinolinones in a green reaction
 medium and their photophysical properties.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              126
_journal_page_last               137
_journal_paper_doi               10.1039/d4ob01390e
_journal_volume                  23
_journal_year                    2024
_chemical_formula_moiety         'C25 H18 Cl N O3'
_chemical_formula_sum            'C25 H18 Cl N O3'
_chemical_formula_weight         415.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-29
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-29 deposited with the CCDC.	2024-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.602(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.624(2)
_cell_length_b                   5.2910(8)
_cell_length_c                   23.770(3)
_cell_measurement_reflns_used    7401
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.35
_cell_measurement_theta_min      2.51
_cell_volume                     2040.4(5)
_computing_cell_refinement       SHELXL
_computing_data_collection       APEX
_computing_data_reduction        SAINT
_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      298.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            28713
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         1.681
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0880 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.9225.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0700P)^2^+0.7098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1742
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2796
_reflns_number_total             5037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01390e2.cif
_cod_data_source_block           acpb9_070324_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160194--7160195.cif.'
_cod_database_code               7160194
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.964
_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
2. Others
 Sof(Cl1B)=1-FVAR(1)
 Sof(Cl1A)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C24(H24), C25(H25)
3.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_shelx_res_checksum              27013
_olex2_submission_special_instructions 'No special instructions were received'