Total Syntheses of the 3H-Pyrrolo[2,3-c]quinolone-containing Alkaloids Marinoquinolines A-F, K and Aplidiopsamine A Using a Palladium-catalysed Ullmann Cross-coupling/Reductive Cyclization Pathway.
Bolte, Benoit; Bryan, Christopher S.; Sharp, Phillip P.; Sayyahi, Soheil; Rihouey, Charly; Kendrick, Amy; Lan, Ping; Banwell, Martin G.; Jackson, Colin J.; Fraser, Nicholas J.; Willis, Anthony C.; Ward, James S.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02725

data_4037684
_publ_section_title
;
 Total Syntheses of the 3H-Pyrrolo[2,3-c]quinolone-containing Alkaloids
 Marinoquinolines A-F, K and Aplidiopsamine A Using a Palladium-catalysed
 Ullmann Cross-coupling/Reductive Cyclization Pathway.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02725
_journal_year                    2019
_chemical_compound_source        'Research School of Chemistry'
_chemical_formula_moiety         'C20 H13 N3 O1'
_chemical_formula_sum            'C20 H13 N3 O'
_chemical_formula_weight         311.34
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-02
_audit_creation_method           CRYSTALS_ver_14.43
_cell_angle_alpha                90
_cell_angle_beta                 109.2474(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4569(2)
_cell_length_b                   6.52690(10)
_cell_length_c                   17.6639(2)
_cell_measurement_reflns_used    6443
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      3
_cell_volume                     1464.73(4)
_computing_cell_refinement       'CrysAlis PRO, (Agilent Technologies, 2013)'
_computing_data_collection       'SuperNova, (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlis PRO, (Agilent Technologies, 2013)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10101
_diffrn_reflns_theta_full        70.844
_diffrn_reflns_theta_max         72.290
_diffrn_reflns_theta_min         3.479
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.20
_refine_ls_extinction_coef       22(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9931
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.0003790
_refine_ls_shift/su_mean         0.0000347
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.58P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0812
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0812
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                2678
_reflns_number_total             2875
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.81
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0345
_oxford_refine_ls_scale          5.76(12)
_oxford_reflns_number_all        2875
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'C:\Users\Hill Group\Desktop\Jas At 14:31 on '
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
CONT H(111, X,Y,Z) 
CONT H(181, X,Y,Z) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            jo9b02725_si_014.cif
_cod_data_source_block           BB_B132_2
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C20 H13 N3 O1'
_cod_database_code               4037684