Synthesis of pyridino[2,1-<i>b</i>]quinazolinones <i>via</i> a visible light-induced functionalization of alkynes/nitrile insertion/cyclization tandem sequences in continuous-flow technology.
Wei, Minghui; Wang, Xujia; Zhang, Jintao; Chen, Jiankun; Liu, Chengkou; Yang, Zhao; Li, Yuguang; Qin, Hong; Fang, Zheng; Guo, Kai; Organic & biomolecular chemistry 23 (2025) 5203–5207; doi:10.1039/d5ob00368g

data_7160526
_publ_section_title
;
 Synthesis of pyridino[2,1-<i>b</i>]quinazolinones <i>via</i> a visible
 light-induced functionalization of alkynes/nitrile insertion/cyclization
 tandem sequences in continuous-flow technology.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5203
_journal_page_last               5207
_journal_paper_doi               10.1039/d5ob00368g
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H22 N2 O'
_chemical_formula_sum            'C26 H22 N2 O'
_chemical_formula_weight         378.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_Hall           'A 2 -2ab'
_space_group_name_H-M_alt        'A e a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2j43wp
_audit_creation_date             2024-01-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-23 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.6782(8)
_cell_length_b                   24.5075(17)
_cell_length_c                   12.7134(6)
_cell_measurement_reflns_used    4114
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      24.41
_cell_measurement_theta_min      2.31
_cell_volume                     3950.2(4)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0822
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36824
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         2.416
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0796 before and 0.0715 after correction.
The Ratio of minimum to maximum transmission is 0.4058.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4048
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0359P)^2^+1.9157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3412
_reflns_number_total             4048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00368g2.cif
_cod_data_source_block           mo_0109_7_0ma
_cod_depositor_comments          'Adding full bibliography for 7160526.cif.'
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               7160526
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1(3)
 0(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C008(H008)
3.b Aromatic/amide H refined with riding coordinates:
 C005(H005), C007(H007), C00A(H00A), C00C(H00C), C00E(H00E), C00G(H00G),
 C00H(H00H), C00J(H00J), C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00T(H00T)
3.c Idealised Me refined as rotating group:
 C00K(H00B,H00D,H00F), C00N(H00I,H00K,H00N)
;
_shelx_res_checksum              34531
_shelx_hkl_checksum              3075
_olex2_submission_special_instructions 'No special instructions were received'