Gold-catalyzed tandem synthesis of bioactive spiro-dipyrroloquinolines and its application in the one-step synthesis of incargranine B aglycone and seneciobipyrrolidine (I)
Ma, Can-Liang; Li, Xiao-Hua; Yu, Xiao-Long; Zhu, Xiao-Long; Hu, Yong-Zhou; Dong, Xiao-Wu; Tan, Bin; Liu, Xin-Yuan; Organic Chemistry Frontiers 3 (2016) 324–; doi:10.1039/C5QO00354G

data_1553211
_publ_section_title
;
 Gold-catalyzed tandem synthesis of bioactive spiro-dipyrroloquinolines
 and its application in the one-step synthesis of incargranine B aglycone
 and seneciobipyrrolidine (I)
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              324
_journal_paper_doi               10.1039/C5QO00354G
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C20 H22 N2'
_chemical_formula_sum            'C20 H22 N2'
_chemical_formula_weight         290.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-07-14 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                77.721(6)
_cell_angle_beta                 79.566(6)
_cell_angle_gamma                69.529(5)
_cell_formula_units_Z            2
_cell_length_a                   7.49870(10)
_cell_length_b                   7.90730(10)
_cell_length_c                   14.5997(10)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      6.70
_cell_volume                     787.06(6)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11432
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.220
_diffrn_reflns_theta_min         6.738
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.217
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0851P)^2^+0.1193P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1652
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2268
_reflns_number_total             2784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00354g2.cif
_cod_data_source_block           shelx
_cod_database_code               1553211
_shelx_estimated_absorpt_t_min   0.898
_shelx_estimated_absorpt_t_max   0.947
_shelxl_version_number           2013-2
_shelx_res_checksum              58539
_shelx_hkl_checksum              48350