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_4037682
_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         'C17 H15 N7 2+, (Cl -)2, 2(H2 O)'
_chemical_formula_sum            'C17 H19 Cl2 N7 O2'
_chemical_formula_weight         424.29
_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             15-01-28
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2015-01-28 - Report on C17 H19 Cl2 N7 O2 
             by Anthony C. Willis
             for   Benoit Bolte and Martin Banwell

2015-01-28 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                81.329(6)
_cell_angle_beta                 88.911(5)
_cell_angle_gamma                79.292(6)
_cell_formula_units_Z            2
_cell_length_a                   7.1854(5)
_cell_length_b                   10.7930(8)
_cell_length_c                   12.3568(7)
_cell_measurement_reflns_used    4595
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     930.81(11)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.958
_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  0.030
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9721
_diffrn_reflns_theta_full        66.906
_diffrn_reflns_theta_max         72.218
_diffrn_reflns_theta_min         4.216
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.403
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.92
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3520
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0750
_refine_ls_shift/su_max          0.0200797
_refine_ls_shift/su_mean         0.0007029
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 5.25P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2009
_refine_ls_wR_factor_gt          0.1905
_refine_ls_wR_factor_ref         0.2009
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2838
_reflns_number_total             3523
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.74
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0880
_oxford_refine_ls_scale          4.95(17)
_oxford_reflns_number_all        3520
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\ban1502SN\Tony_ban1502SN_data At 10:32 on'
_cod_data_source_file            jo9b02725_si_010.cif
_cod_data_source_block           ban1502SN
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4037682
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT H(11,X'S) UNTIL H(922) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
ANGLE 110 2 = H(911) TO O(1) TO H(912) 
ANGLE 110 2 = H(921) TO O(2) TO H(922) 
DIST 0.82 .03 = O(1) TO H(911), O(1) TO H(912) 
DIST 0.82 .03 = O(2) TO H(921), O(2) TO H(922) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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