Photoredox synthesis of functionalized quinazolines via copper-catalyzed aerobic oxidative Csp2‒H annulation of amidines with terminal alkynes
Charpe, Vaibhav Pramod; Ragupathi, Ayyakkannu; Sagadevan, Arunachalam; Hwang, Kuo Chu; Green Chemistry 23 (2021) 5024–5030; doi:10.1039/D1GC01493E

data_7243062
_publ_section_title
;
 Photoredox synthesis of functionalized quinazolines via copper-catalyzed
 aerobic oxidative Csp2--H annulation of amidines with terminal alkynes
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              5024
_journal_page_last               5030
_journal_paper_doi               10.1039/D1GC01493E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C20 H14 N2 O S'
_chemical_formula_weight         330.39
_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
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2020-05-12 deposited with the CCDC.	2021-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.934(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8618(3)
_cell_length_b                   33.708(3)
_cell_length_c                   11.8039(12)
_cell_measurement_reflns_used    2766
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3557
_cell_measurement_theta_min      2.4168
_cell_volume                     1517.9(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_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  0.0329
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.992
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_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10411
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_min         1.208
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             688
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_exptl_crystal_size_mid          0.05
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_refine_diff_density_max         0.263
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3072
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.5640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0856
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2575
_reflns_number_total             3072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc01493e2.cif
_cod_data_source_block           190416lt_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7243062--7243064.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7243062
_shelxl_version_number           2014/6
_shelx_res_checksum              72370
_shelx_hkl_checksum              38038