An environmentally benign cascade reaction of chromone-3-carboxaldehydes with ethyl 2-(pyridine-2-yl)acetate derivatives for highly site-selective synthesis of quinolizines and quinolizinium salts in water
Chen, Li; Huang, Rong; Li, Kun; Yun, Xing-Han; Yang, Chang-Long; Yan, Sheng-Jiao; Green Chemistry 22 (2020) 6943–6953; doi:10.1039/D0GC02460K

data_7241185
_publ_section_title
;
 An environmentally benign cascade reaction of chromone-3-carboxaldehydes
 with ethyl 2-(pyridine-2-yl)acetate derivatives for highly site-selective
 synthesis of quinolizines and quinolizinium salts in water
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              6943
_journal_page_last               6953
_journal_paper_doi               10.1039/D0GC02460K
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'Cl O4, C19 H15 F N O4'
_chemical_formula_sum            'C19 H15 Cl F N O8'
_chemical_formula_weight         439.77
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-02 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.194(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1097(12)
_cell_length_b                   14.3670(19)
_cell_length_c                   16.622(2)
_cell_measurement_reflns_used    4083
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.093
_cell_measurement_theta_min      2.660
_cell_volume                     1916.9(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11596
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.867
_diffrn_reflns_theta_min         2.660
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0906 before and 0.0323 after correction. The Ratio of minimum to maximum transmission is 0.9218. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0532P)^2^+0.7741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1193
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3315
_reflns_number_total             4491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc02460k2.cif
_cod_data_source_block           191219ysjd1_0m
_cod_depositor_comments          'Adding full bibliography for 7241185.cif.'
_cod_database_code               7241185
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_shelx_res_checksum              77774
_olex2_submission_special_instructions 'No special instructions were received'