Regio- and Stereoselective Electrophilic Cyclization Approach for the Protecting-Group-Free Synthesis of Alkaloids Lennoxamine, Chilenine, Fumaridine, 8-Oxypseudoplamatine, and 2- O-(Methyloxy)fagaronine.
Yao, Tuanli; Guo, Zhen; Liang, Xiujuan; Qi, Lihan; The Journal of organic chemistry 83 (2018) 13370–13380; doi:10.1021/acs.joc.8b02154

data_4035761
_publ_section_title
;
 Regio- and Stereoselective Electrophilic Cyclization Approach for the
 Protecting-Group-Free Synthesis of Alkaloids Lennoxamine, Chilenine,
 Fumaridine, 8-Oxypseudoplamatine, and 2- O-(Methyloxy)fagaronine.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13370
_journal_page_last               13380
_journal_paper_doi               10.1021/acs.joc.8b02154
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C22 H21 N O7'
_chemical_formula_weight         411.40
_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                 128.512(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4582(6)
_cell_length_b                   7.4973(3)
_cell_length_c                   23.2194(7)
_cell_measurement_reflns_used    3404
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.58
_cell_measurement_theta_min      2.82
_cell_volume                     1969.44(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.818
_diffrn_measured_fraction_theta_max 0.867
_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  0.1219
_diffrn_reflns_av_unetI/netI     0.1882
_diffrn_reflns_Laue_measured_fraction_full 0.818
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17425
_diffrn_reflns_point_group_measured_fraction_full 0.818
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_min         2.818
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.2153
_refine_ls_R_factor_gt           0.0661
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1614
_reflns_number_total             4243
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02154_si_002.cif
_cod_data_source_block           SUST_1386_0ma
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035761
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              68703
_shelx_hkl_checksum              69716