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
Kumpaty, Hephzibah J.; Van Linn, Michael L.; Kabir, M. Shahjahan; Försterling, F. Holger; Deschamps, Jeffrey R.; Cook, James M.; The Journal of Organic Chemistry 74 (2009) 2771–2779; doi:10.1021/jo8028168

data_4028950
_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_issue                   7
_journal_name_full               'The 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_formula_moiety         'C21 H22 N2 O3'
_chemical_formula_sum            'C21 H22 N2 O3'
_chemical_formula_weight         350.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 99.4450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2561(6)
_cell_length_b                   9.8431(5)
_cell_length_c                   14.5414(7)
_cell_measurement_reflns_used    3671
_cell_measurement_temperature    103(1)
_cell_measurement_theta_max      29.16
_cell_measurement_theta_min      2.67
_cell_volume                     1730.46(15)
_computing_cell_refinement       'Bruker APEX2  v2.0-2(Bruker, 2006)'
_computing_data_collection       'Bruker APEX2  v2.0-2(Bruker, 2006)'
_computing_data_reduction
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000)'
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000)'
_diffrn_ambient_temperature      103(1)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19229
_diffrn_reflns_theta_full        29.95
_diffrn_reflns_theta_max         29.95
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS v1.05 (Bruker, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.4257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1151
_reflns_number_gt                3587
_reflns_number_total             4946
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo8028168sup2.cif
_cod_data_source_block           cook55a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c  '
_cod_database_code               4028950