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_4037693
_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 O3 S'
_chemical_formula_sum            'C18 H14 N2 O3 S'
_chemical_formula_weight         338.39
_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_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             13-12-09
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2013-12-09 - Report on C18 H14 N2 O3 S 
             by Anthony C. Willis
             for   Benoit Bolte and Martin Banwell

2013-12-09 - passes checkcif tests with no warnings  
;
_cell_angle_alpha                82.5503(12)
_cell_angle_beta                 87.7791(10)
_cell_angle_gamma                67.7136(12)
_cell_formula_units_Z            2
_cell_length_a                   8.0748(2)
_cell_length_b                   8.08420(10)
_cell_length_c                   12.4871(3)
_cell_measurement_reflns_used    14160
_cell_measurement_temperature    200
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     747.83(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.036
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22771
_diffrn_reflns_theta_full        30.041
_diffrn_reflns_theta_max         30.041
_diffrn_reflns_theta_min         2.726
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.925
_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    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9890
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4380
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.0134204
_refine_ls_shift/su_mean         0.0004520
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.32P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0999
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0999
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3938
_reflns_number_total             4382
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.88
_oxford_diffrn_Wilson_scale      0.15
_oxford_refine_ls_r_factor_ref   0.0397
_oxford_refine_ls_scale          2.212(16)
_oxford_reflns_number_all        4380
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1368 At 12:31 on 9/12'
_cod_data_source_file            jo9b02725_si_009.cif
_cod_data_source_block           ban1368
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4037693
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (   24 ) 
CONT H    (   31 ,X'S)  UNTIL H    (  243 ) 
END                                                                             
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_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 24) TO H(241) 
CONT C ( 24) TO H(242) 
CONT C ( 24) TO H(243) 
REST 0.066, 0.002 = H(241,U[ISO]) 
REST 0.066, 0.002 = H(242,U[ISO]) 
REST 0.066, 0.002 = H(243,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(21) TO C ( 24) TO H(241) 
CONT C(21) TO C ( 24) TO H(242) 
CONT C(21) TO C ( 24) TO H(243) 
ANGLE 0.0, 2.0 = MEAN H(241) TO C ( 24) TO H(242) 
CONT H(241) TO C ( 24) TO H(243) 
CONT H(242) TO C ( 24) TO H(243) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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