Synthesis of pyrano[3,2-c]quinolones and furo[3,2-c]quinolones via acid-catalyzed tandem reaction of 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols
Yin, Haiting; Wu, Yunjun; Gu, Xiaoxia; Feng, Zhijun; Wang, Meifang; Feng, Dexiang; Wang, Ming; Cheng, Ziyang; Wang, Shaoyin; RSC Advances 12 (2022) 21066–21078; doi:10.1039/D2RA03416F

data_7245209
_publ_section_title
;
 Synthesis of pyrano[3,2-c]quinolones and furo[3,2-c]quinolones via
 acid-catalyzed tandem reaction of 4-hydroxy-1-methylquinolin-2(1H)-one
 and propargylic alcohols
;
_journal_issue                   33
_journal_name_full               'RSC Advances'
_journal_page_first              21066
_journal_page_last               21078
_journal_paper_doi               10.1039/D2RA03416F
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C55 H45 N O3'
_chemical_formula_sum            'C55 H45 N O3'
_chemical_formula_weight         767.92
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-09 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                72.580(15)
_cell_angle_beta                 78.270(15)
_cell_angle_gamma                74.539(15)
_cell_formula_units_Z            2
_cell_length_a                   12.978(6)
_cell_length_b                   13.234(6)
_cell_length_c                   13.515(6)
_cell_measurement_reflns_used    9273
_cell_measurement_temperature    300
_cell_measurement_theta_max      25.410
_cell_measurement_theta_min      2.575
_cell_volume                     2115.3(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 0.999
_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  0.0904
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            71040
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         2.575
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0770 before and 0.0614 after correction. The Ratio of minimum to maximum transmission is 0.8794. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0138(13)
_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   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         9697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0607P)^2^+0.3211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1416
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5401
_reflns_number_total             9697
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra03416f2.cif
_cod_data_source_block           20211227a
_cod_original_cell_volume        2115.3(16)
_cod_database_code               7245209
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.991
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28),
  C30(H30), C31(H31), C34(H34), C37(H37), C38(H38), C39(H39), C40(H40),
 C41(H41), C43(H43), C44(H44), C46(H46), C47(H47), C50(H50), C51(H51), C53(H53),
  C54(H54)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C32(H32A,H32B,H32C), C48(H48A,H48B,H48C), C55(H55A,H55B,
 H55C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              2516
_olex2_submission_special_instructions 'No special instructions were received'