A Synthetic Route to Chiral 1,4-Disubstituted Tetrahydro-β-Carbolines via Domino Ring-Opening Cyclization of Activated Aziridines with 2-Vinylindoles.
Sayyad, Masthanvali; Wani, Imtiyaz Ahmad; Babu, Raja; Nanaji, Yerramsetti; Ghorai, Manas K.; The Journal of organic chemistry 82 (2017) 2364–2374; doi:10.1021/acs.joc.6b02719

data_4032194
_publ_section_title
;
 A Synthetic Route to Chiral 1,4-Disubstituted Tetrahydro-\b-Carbolines
 via Domino Ring-Opening Cyclization of Activated Aziridines with
 2-Vinylindoles.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2364
_journal_page_last               2374
_journal_paper_doi               10.1021/acs.joc.6b02719
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C29 H30 N2 O4 S'
_chemical_formula_sum            'C29 H30 N2 O4 S'
_chemical_formula_weight         502.61
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 110.754(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4759(9)
_cell_length_b                   9.5223(5)
_cell_length_c                   18.2158(9)
_cell_measurement_reflns_used    3582
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.6
_cell_volume                     2510.2(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX'
_computing_data_reduction        'Bruker SAINT PLUS'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97(Altomare, et. al. 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1039
_diffrn_reflns_av_sigmaI/netI    0.1248
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24887
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0648
_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^)+(0.0648P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1480
_reflns_number_gt                3582
_reflns_number_total             6250
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02719_si_002.cif
_cod_data_source_block           4decd_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032193--4032194.cif.
;
_cod_original_sg_symbol_H-M      p21/n
_cod_database_code               4032194