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_4037691
_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         'C24 H19 N7 O5 S'
_chemical_formula_sum            'C24 H19 N7 O5 S'
_chemical_formula_weight         517.52
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             14-10-15
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2014-10-16 - Report on C24 H19 N7 O5 S 
             by Anthony C. Willis
             for   Benoit Bolte and Martin Banwell

2014-10-16 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 129.298(6)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   63.464(2)
_cell_length_b                   6.8824(1)
_cell_length_c                   30.4144(12)
_cell_measurement_reflns_used    16395
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     10280.4(10)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement
;
CRYSTALS (Betteridge et al., 2003),
PLATON (Spek, 2008)

;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Supernova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_max       78
_diffrn_reflns_limit_h_min       -75
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            57418
_diffrn_reflns_theta_full        70.373
_diffrn_reflns_theta_max         71.997
_diffrn_reflns_theta_min         3.152
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.536
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4288
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.028
_platon_squeeze_details
;
PLATON (Spek, 2008)

;
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9816
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     731
_refine_ls_number_reflns         10055
_refine_ls_number_restraints     93
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.0773438
_refine_ls_shift/su_mean         0.0013081
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ +14.80P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1048
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1048
_reflns_limit_h_max              60
_reflns_limit_h_min              -78
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              37
_reflns_limit_l_min              0
_reflns_number_gt                8743
_reflns_number_total             10061
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.25
_oxford_diffrn_Wilson_scale      0.44
_oxford_refine_ls_r_factor_ref   0.0472
_oxford_refine_ls_scale          1.555(5)
_oxford_reflns_number_all        10055
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\ban1450SN\Tony_ban1450SN_data At 17:18 on'
_cod_data_source_file            jo9b02725_si_016.cif
_cod_data_source_block           ban1450SN
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_database_code               4037691
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, N(1,U'S) UNTIL N(110) 
CONT C(111,U'S,OCC) UNTIL N(117) 
CONT C(118,U'S) UNTIL O(137) 
CONT C(211,U'S,OCC) UNTIL N(217) 
EQUIV C(111,OCC) UNTIL N(117) C(211,OCC) UNTIL N(217) 
WEIGHT -1 C(211,OCC) UNTIL N(217) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) H   ( 343,X'S) 
RIDE C   ( 104,X'S) H   (1041,X'S) 
RIDE C   ( 105,X'S) H   (1051,X'S) 
RIDE C   ( 107,X'S) H   (1071,X'S) H   (1072,X'S) 
RIDE C   ( 109,X'S) H   (1091,X'S) 
RIDE C   ( 114,X'S) H   (1141,X'S) 
RIDE C   ( 120,X'S) H   (1201,X'S) 
RIDE C   ( 121,X'S) H   (1211,X'S) 
RIDE C   ( 122,X'S) H   (1221,X'S) 
RIDE C   ( 123,X'S) H   (1231,X'S) 
RIDE C   ( 129,X'S) H   (1291,X'S) 
RIDE C   ( 130,X'S) H   (1301,X'S) 
RIDE C   ( 132,X'S) H   (1321,X'S) 
RIDE C   ( 133,X'S) H   (1331,X'S) 
RIDE C   ( 134,X'S) H   (1341,X'S) H   (1342,X'S) H   (1343,X'S) 
RIDE N(17,X'S) H(171,X'S) H(172,X'S) 
RIDE N(117,X'S) H(1171,X'S) H(1172,X'S) 
RIDE N(217,X'S) H(2171,X'S) H(2172,X'S) 
RIDE C   ( 214,X'S) H   (2141,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
PLANAR C(111) UNTIL N(117) 
PLANAR C(211) UNTIL N(217) 
DIST 0.0, .02 = MEAN N(110) TO C(111), N(110) TO C(211) 
DIST 0.0, .02 = MEAN N(108) TO C(112), N(108) TO C(212) 
DIST 0.0, .02 = MEAN C(111) TO C(112), C(211) TO C(212) 
DIST 0.0, .02 = MEAN C(112) TO N(113), C(212) TO N(213) 
DIST 0.0, .02 = MEAN N(113) TO C(114), N(213) TO C(214) 
DIST 0.0, .02 = MEAN C(114) TO N(115), C(214) TO N(215) 
DIST 0.0, .02 = MEAN N(115) TO C(116), N(215) TO C(216) 
DIST 0.0, .02 = MEAN C(111) TO C(116), C(211) TO C(216) 
DIST 0.0, .02 = MEAN C(116) TO N(117), C(216) TO N(217) 
REM 
ANGLE 0.0, 2 = MEAN C(116) TO C(111) TO C(112), C(216) TO C(211) TO C(212) 
ANGLE 0.0, 2 = MEAN C(111) TO C(112) TO N(113), C(211) TO C(212) TO N(213) 
ANGLE 0.0, 2 = MEAN C(112) TO N(113) TO C(114), C(212) TO N(213) TO C(214) 
ANGLE 0.0, 2 = MEAN N(113) TO C(114) TO N(115), N(213) TO C(214) TO N(215) 
ANGLE 0.0, 2 = MEAN C(114) TO N(115) TO C(116), C(214) TO N(215) TO C(216) 
ANGLE 0.0, 2 = MEAN N(115) TO C(116) TO C(111), N(215) TO C(216) TO C(211) 
ANGLE 0.0, 2 = MEAN N(115) TO C(116) TO N(117), N(215) TO C(216) TO N(217) 
ANGLE 0.0, 2 = MEAN C(111) TO C(116) TO N(117), C(211) TO C(216) TO N(217) 
REM 
U(IJ) 0.0, .01 = C(111) TO C(211) 
U(IJ) 0.0, .01 = C(112) TO C(212) 
U(IJ) 0.0, .01 = N(113) TO N(213) 
U(IJ) 0.0, .01 = C(114) TO C(214) 
U(IJ) 0.0, .01 = N(115) TO N(215) 
U(IJ) 0.0, .01 = C(116) TO C(216) 
U(IJ) 0.0, .01 = N(117) TO N(217) 
REM 
LIMIT .0002 C(211,Z) 
LIMIT .0001 C(211,Y) 
LIMIT .0001 C(211,X) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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