A Formal Total Synthesis of (±)-Kopsihainanine A Using a Raney-Cobalt Mediated Reductive Cyclization Route to Polyhydroquinolines.
Tan, Shen H.; Banwell, Martin G.; Willis, Anthony C.; The Journal of organic chemistry 81 (2016) 8022–8028; doi:10.1021/acs.joc.6b01400

data_4037065
_publ_section_title
;
 A Formal Total Synthesis of (+-)-Kopsihainanine A Using a Raney-Cobalt
 Mediated Reductive Cyclization Route to Polyhydroquinolines.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8022
_journal_page_last               8028
_journal_paper_doi               10.1021/acs.joc.6b01400
_journal_volume                  81
_journal_year                    2016
_chemical_compound_source        local
_chemical_formula_moiety         'C19 H23 N3 O, C H4 O'
_chemical_formula_sum            'C20 H27 N3 O2'
_chemical_formula_weight         341.45
_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_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             12-10-09
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-10-09 - Report on C20 H27 N3 O2
             by Anthony C. Willis
             for  Shen H. Tan and Martin Banwell

2012-10-09 - passes most checkcif tests 

;
_cell_angle_alpha                90
_cell_angle_beta                 94.8955(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3982(1)
_cell_length_b                   10.5143(2)
_cell_length_c                   20.8016(4)
_cell_measurement_reflns_used    21056
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1830.11(5)
_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  0.035
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            34123
_diffrn_reflns_theta_full        27.441
_diffrn_reflns_theta_max         27.441
_diffrn_reflns_theta_min         2.760
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.27
_refine_ls_extinction_coef       420(40)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9581
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.0061929
_refine_ls_shift/su_mean         0.0005878
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.55P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1028
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1028
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                3240
_reflns_number_total             4173
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.16
_oxford_diffrn_Wilson_scale      1.46
_oxford_refine_ls_r_factor_ref   0.0554
_oxford_refine_ls_scale          0.791(2)
_oxford_reflns_number_all        4172
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '10041623 ban1237'
_cod_data_source_file            jo6b01400_si_002.cif
_cod_data_source_block           ban1237
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4037065
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S H(11,X'S) UNTIL H(182) 
CONT H(241,X'S) UNTIL H(253) EXTPARAM 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 223,X'S) H   ( 222,X'S) 
CONT H(224,X'S) H(225,X'S) H(226,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 233,X'S) H   ( 232,X'S) 
CONT H(234,X'S) H(235,X'S) H(236,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;