Green light-mediated dual eosin Y/Pd<sup>II</sup>-catalyzed C(sp<sup>2</sup>)-H arylation of N-H unprotected 2-arylquinazolinones.
Mondal, Shuvam; Jana, Ranjan; Organic & biomolecular chemistry 22 (2024) 5540–5545; doi:10.1039/d4ob00779d

data_7159992
_publ_section_title
;
 Green light-mediated dual eosin Y/Pd<sup>II</sup>-catalyzed
 C(sp<sup>2</sup>)-H arylation of N-H unprotected 2-arylquinazolinones.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5540
_journal_page_last               5545
_journal_paper_doi               10.1039/d4ob00779d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C21 H15 F N2 O2'
_chemical_formula_sum            'C21 H15 F N2 O2'
_chemical_formula_weight         446.35
_chemical_name_systematic        QUINAZOLINONE
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-05-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-05-06 deposited with the CCDC.	2024-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.812(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4997(6)
_cell_length_b                   13.6212(11)
_cell_length_c                   16.1797(12)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      67.00
_cell_measurement_theta_min      4.25
_cell_volume                     1649.2(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24330
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.661
_diffrn_reflns_theta_min         4.247
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  0.5842
_exptl_absorpt_correction_T_min  0.3909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1442 before and 0.1001 after correction.
The Ratio of minimum to maximum transmission is 0.6691.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             720
_exptl_crystal_preparation       'chloroform and hexane'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0080(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0682
_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^)+(0.0331P)^2^+3.3167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1533
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2766
_reflns_number_total             2914
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00779d2.cif
_cod_data_source_block           shm_420_0m_a
_cod_depositor_comments
;
Adding full bibliography for 7159991--7159992.cif.

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C84 H60 F4 N8 O8'
_cod_original_formula_weight         1385.40
_cod_original_formula_moiety         '4(C21 H15 F N2 O2)'
_cod_original_formula_units_Z            1
_cod_database_code               7159992
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.854
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q)
1.b Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C)
;
_shelx_res_checksum              14643
_olex2_submission_original_sample_id SHM-420
_olex2_submission_special_instructions 'No special instructions were received'