Visible-light photocatalyzed C–N bond activation of tertiary amines: a three-component approach to synthesize quinazolines
Arumugam, Ajithkumar; Senadi, Gopal Chandru; Organic & Biomolecular Chemistry 22 (2024) 1245–1253; doi:10.1039/D3OB02067C

data_7159769
_publ_section_title
;
 Visible-light photocatalyzed C--N bond activation of tertiary amines: a
 three-component approach to synthesize quinazolines
;
_journal_issue                   6
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1245
_journal_page_last               1253
_journal_paper_doi               10.1039/D3OB02067C
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C15 H12 N2 O'
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.275
_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'
_symmetry_Int_Tables_number      14
_audit_creation_date             2024-01-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-09 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.928(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0428(11)
_cell_length_b                   20.506(4)
_cell_length_c                   9.995(2)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.84
_cell_measurement_theta_min      2.40
_cell_volume                     1184.9(4)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.9995
_diffrn_reflns_Laue_measured_fraction_max 0.9982
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14983
_diffrn_reflns_point_group_measured_fraction_full 0.9995
_diffrn_reflns_point_group_measured_fraction_max 0.9982
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.70
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       needle
_exptl_crystal_F_000             496.305
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.1646
_refine_diff_density_min         -0.1892
_refine_diff_density_rms         0.0373
_refine_ls_d_res_high            0.8195
_refine_ls_d_res_low             10.2530
_refine_ls_goodness_of_fit_ref   1.0588
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0588
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          -0.0006
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+0.3337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1960
_reflns_number_total             2249
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3ob02067c2.cif
_cod_data_source_block           AK-1_a
_cod_depositor_comments          'Adding full bibliography for 7159769.cif.'
_cod_database_code               7159769
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1a), C2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'