TFA-Mediated DMSO-Participant Sequential Oxidation/1,3-Dipolar Cycloaddition Cascade of Pyridinium Ylides for the Assembly of Indolizines.
Shu, Wen-Ming; He, Jian-Xin; Zhang, Xun-Fang; Wang, Shuai; Wu, An-Xin; The Journal of organic chemistry 84 (2019) 2962–2968; doi:10.1021/acs.joc.8b02755

data_4033734
_publ_section_title
;
 TFA-Mediated DMSO-Participant Sequential Oxidation/1,3-Dipolar
 Cycloaddition Cascade of Pyridinium Ylides for the Assembly of
 Indolizines.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2962
_journal_page_last               2968
_journal_paper_doi               10.1021/acs.joc.8b02755
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C24 H19 N O2'
_chemical_formula_weight         353.40
_space_group_crystal_system      triclinic
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_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                106.563(4)
_cell_angle_beta                 92.469(4)
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_cell_length_b                   9.882(3)
_cell_length_c                   13.685(4)
_cell_measurement_reflns_used    2688
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      29.77
_cell_measurement_theta_min      2.95
_cell_volume                     894.4(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9083
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.283
_diffrn_reflns_theta_min         1.569
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         5172
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0562
_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^)+(0.1170P)^2^+0.0015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3509
_reflns_number_total             5172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02755_si_002.cif
_cod_data_source_block           1_a
_cod_original_cell_volume        894.4(4)
_cod_database_code               4033734
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              45310
_shelx_hkl_checksum              13942