Study of the Cis to Trans Isomerization of 1-Phenyl-2,3-disubstituted Tetrahydro-β-carbolines at C(1). Evidence for the Carbocation-Mediated Mechanism
Hephzibah J. Kumpaty; Michael L. Van Linn; M. Shahjahan Kabir; F. Holger Försterling; Jeffrey R. Deschamps; James M. Cook; Journal of Organic Chemistry 74 (2009) 2771–2779; doi:10.1021/jo8028168

data_4024439
_publ_section_title
;
Study of the Cis to Trans Isomerization of 1-Phenyl-2,3-disubstituted
Tetrahydro-\b-carbolines at C(1). Evidence for the Carbocation-Mediated
Mechanism
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2771
_journal_page_last               2779
_journal_paper_doi               10.1021/jo8028168
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H22 N2 O3'
_chemical_formula_sum            'C21 H22 N2 O3'
_chemical_formula_weight         350.41
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9054(5)
_cell_length_b                   12.2932(8)
_cell_length_c                   16.4551(9)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.47
_cell_volume                     1801.44(18)
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_reduction
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19021
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  variable
_diffrn_standards_number         'not reported'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisim
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.765
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.2727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0825
_reflns_number_gt                4332
_reflns_number_total             4485
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo8028168_si_004.cif
_cod_data_source_block           cook61
_cod_database_code               4024439