Diastereomeric Reissert Compounds of Isoquinoline and 6,7-Dimethoxy-3,4-dihydroisoquinoline in Stereoselective Synthesis
Harry W. Gibson; Michael A. G. Berg; Jennifer Clifton Dickson; Pierre R. Lecavalier; Hong Wang; Joseph S. Merola; Journal of Organic Chemistry 72 (2007) 5759–5770; doi:10.1021/jo070786k

data_4024071
_publ_contact_author             'Berg, Michael A. G.'
_publ_contact_author_email       bergm@vt.edu
_publ_section_title
;
 Diastereomeric Reissert Compounds of Isoquinoline and
 6,7-Dimethoxy-3,4-dihydroisoquinoline in Stereoselective Synthesis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5759
_journal_page_last               5770
_journal_paper_doi               10.1021/jo070786k
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C38 H52 N2 O2'
_chemical_formula_sum            'C38 H52 N2 O2'
_chemical_formula_weight         568.82
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-09-15T17:33:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90(0)
_cell_angle_beta                 92.86(4)
_cell_angle_gamma                90(0)
_cell_formula_units_Z            2
_cell_length_a                   10.224(5)
_cell_length_b                   9.366(5)
_cell_length_c                   16.942(9)
_cell_measurement_reflns_used    4125
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.75
_cell_measurement_wavelength     0.71073
_cell_volume                     1620.4(14)
_computing_cell_refinement       'Siemens SHELXTL PLUS (VMS) (Sheldrick, 1990)'
_computing_data_collection       'Siemens SHELXTL PLUS (VMS) (Sheldrick, 1990)'
_computing_data_reduction        'Siemens SHELXTL PLUS (VMS) (Sheldrick, 1990)'
_computing_molecular_graphics    'Ortep 3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Siemens SHELXTL PLUS (VMS) (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'scintillation counter'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'four circle'
_diffrn_measurement_device_type  'Siemens R3m/V four-circle defractometer'
_diffrn_measurement_method       'Wyckoff scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4120
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.41
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 300
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       0.099(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.1
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         3912
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.1
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0677
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1533P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.186
_refine_ls_wR_factor_ref         0.2183
_reflns_number_gt                2742
_reflns_number_total             3912
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070786krom20070415_124357.cif
_cod_data_source_block           newchol
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024071