Construction of Unique Eight- or Nine-Membered Polyheterocyclic Systems via Multicomponent Reaction of l-Proline, Alkyl Propiolate, and Isatin.
Cao, Jun; Yang, Fan; Sun, Jing; Huang, Ying; Yan, Chao-Guo; The Journal of organic chemistry 84 (2019) 622–635; doi:10.1021/acs.joc.8b02457

data_4035985
_publ_section_title
;
 Construction of Unique Eight- or Nine-Membered Polyheterocyclic Systems
 via Multicomponent Reaction of l-Proline, Alkyl Propiolate, and Isatin.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              622
_journal_page_last               635
_journal_paper_doi               10.1021/acs.joc.8b02457
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C24 H27 Cl N2 O5'
_chemical_formula_sum            'C24 H27 Cl N2 O5'
_chemical_formula_weight         458.92
_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                 105.72
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.806(4)
_cell_length_b                   9.349(4)
_cell_length_c                   21.788(7)
_cell_measurement_reflns_used    3689
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.09
_cell_measurement_theta_min      2.26
_cell_volume                     2314.9(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.853
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1036
_diffrn_reflns_av_unetI/netI     0.1716
_diffrn_reflns_Laue_measured_fraction_full 0.853
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13229
_diffrn_reflns_point_group_measured_fraction_full 0.853
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        24.712
_diffrn_reflns_theta_max         24.712
_diffrn_reflns_theta_min         2.385
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0020(18)
_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   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3354
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.2016
_refine_ls_R_factor_gt           0.0717
_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^)+(0.0780P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1951
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1404
_reflns_number_total             3354
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02457_si_002.cif
_cod_data_source_block           1h
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035985
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.964
_shelx_res_checksum              97525
_shelx_hkl_checksum              20484