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_1553210
_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         'C22 H24 Br2 N2'
_chemical_formula_sum            'C22 H24 Br2 N2'
_chemical_formula_weight         476.25
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-07-14 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                78.194(6)
_cell_angle_beta                 82.379(6)
_cell_angle_gamma                72.418(5)
_cell_formula_units_Z            2
_cell_length_a                   9.1241(2)
_cell_length_b                   10.2171(2)
_cell_length_c                   11.3635(8)
_cell_measurement_reflns_used    12173
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      6.6
_cell_volume                     985.63(8)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM Auto 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  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12869
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         6.61
_exptl_absorpt_coefficient_mu    5.264
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.463
_refine_diff_density_min         -1.141
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0612P)^2^+1.0667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                3023
_reflns_number_total             3484
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c5qo00354g2.cif
_cod_data_source_block           b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1553210