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_4037683
_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         'C20 H13 N3 O'
_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_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             14-06-10
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2014-06-10 - Report on C20 H13 N3 O 
             by Anthony C. Willis
             for   Benoit Bolte and Martin Banwell

2014-06-10 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 91.612(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.83600(10)
_cell_length_b                   11.6306(4)
_cell_length_c                   32.4071(11)
_cell_measurement_reflns_used    6658
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     1445.27(8)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.21t (release 24-10-2013 CrysAlis171 .NET)
(compiled Oct 24 2013,16:12:21)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Sapphire3'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            16466
_diffrn_reflns_theta_full        72.290
_diffrn_reflns_theta_max         72.290
_diffrn_reflns_theta_min         4.038
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.21t (release 24-10-2013 CrysAlis171 .NET)
(compiled Oct 24 2013,16:12:21)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0021
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2852
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.0044702
_refine_ls_shift/su_mean         0.0006769
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 0.96P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1353
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1353
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              40
_reflns_limit_l_min              0
_reflns_number_gt                2601
_reflns_number_total             2852
_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   0.0516
_oxford_refine_ls_scale          5.71(19)
_oxford_reflns_number_all        2852
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\ban1426SN\Tony_ban1426ASN_dat At 16:52 on'
_cod_data_source_file            jo9b02725_si_006.cif
_cod_data_source_block           ban1426SN
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4037683
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (   24 ) 
CONT H    (   61 ,X'S)  UNTIL H    (  111 ) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;