Three-Component Site-Selective Synthesis of Highly Substituted 5 H-Chromeno-[4,3- b]pyridines.
Zhang, Cong-Hai; Huang, Rong; Hu, Xing-Mei; Lin, Jun; Yan, Sheng-Jiao; The Journal of organic chemistry 83 (2018) 4981–4989; doi:10.1021/acs.joc.8b00099

data_4035518
_publ_section_title
;
 Three-Component Site-Selective Synthesis of Highly Substituted 5
 H-Chromeno-[4,3- b]pyridines.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4981
_journal_page_last               4989
_journal_paper_doi               10.1021/acs.joc.8b00099
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C21 H17 F2 N3 O4'
_chemical_formula_weight         413.38
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.963(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.4590(17)
_cell_length_b                   17.667(7)
_cell_length_c                   24.108(9)
_cell_measurement_reflns_used    963
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.3703
_cell_measurement_theta_min      2.3055
_cell_volume                     1894.6(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0741
_diffrn_reflns_av_unetI/netI     0.0956
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10635
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.148
_diffrn_reflns_theta_max         25.148
_diffrn_reflns_theta_min         1.430
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            PINK
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0092(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0534
_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^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1497
_reflns_number_total             3402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00099_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035518
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.935
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              81970
_shelx_hkl_checksum              10658