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_4037688
_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        local
_chemical_formula_moiety         'C18 H14 N2 O, C H4 O'
_chemical_formula_sum            'C19 H18 N2 O2'
_chemical_formula_weight         306.36
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             13-05-29
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2013-05-29 - Report on C19 H18 N2 O2 
             by Anthony C. Willis
             for   Benoit Bolte and Martin Banwell

2013-05-29 - passes checkcif tests with few warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 96.7633(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5218(2)
_cell_length_b                   8.2073(2)
_cell_length_c                   20.3649(3)
_cell_measurement_reflns_used    23999
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1580.41(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_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      200
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            34908
_diffrn_reflns_theta_full        27.491
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         2.678
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9467
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.0070421
_refine_ls_shift/su_mean         0.0003143
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.38P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1156
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1156
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                2616
_reflns_number_total             3631
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.95
_oxford_diffrn_Wilson_scale      3.17
_oxford_refine_ls_r_factor_ref   0.0693
_oxford_refine_ls_scale          0.5713(14)
_oxford_reflns_number_all        3630
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1333 At 9:53 on 29/ 5/13'
_cod_data_source_file            jo9b02725_si_004.cif
_cod_data_source_block           ban1333
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4037688
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (   23 ) 
CONT H    (   31 ,X'S)  UNTIL H    (  233 ) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;