Stereoselective Construction of Pyrazinoindoles and Oxazinoindoles via Ring-Opening/Pictet-Spengler Reaction of Aziridines and Epoxides with 3-Methylindoles and Carbonyls.
Wani, Imtiyaz Ahmad; Das, Subhomoy; Mondal, Shobhan; Ghorai, Manas K.; The Journal of organic chemistry 83 (2018) 14553–14567; doi:10.1021/acs.joc.8b02339

data_4035710
_publ_section_title
;
 Stereoselective Construction of Pyrazinoindoles and Oxazinoindoles via
 Ring-Opening/Pictet-Spengler Reaction of Aziridines and Epoxides with
 3-Methylindoles and Carbonyls.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14553
_journal_page_last               14567
_journal_paper_doi               10.1021/acs.joc.8b02339
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C31.5 H27 Br Cl N3 O4 S'
_chemical_formula_sum            'C31.5 H27 Br Cl N3 O4 S'
_chemical_formula_weight         658.98
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.6160(10)
_cell_angle_beta                 90.5890(10)
_cell_angle_gamma                102.6200(10)
_cell_formula_units_Z            4
_cell_length_a                   9.7286(5)
_cell_length_b                   17.3772(8)
_cell_length_c                   17.4481(8)
_cell_measurement_reflns_used    14012
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.2
_cell_volume                     2814.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX'
_computing_data_reduction        'Bruker SAINT PLUS'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WingX publication routine (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 scan'
_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  0.0740
_diffrn_reflns_av_sigmaI/netI    0.1077
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            43295
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    1.674
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1348
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.265
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     752
_refine_ls_number_reflns         14012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0698P)^2^+0.5897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1476
_reflns_number_gt                8818
_reflns_number_total             14012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02339_si_004.cif
_cod_data_source_block           11june_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Empirical' was
changed to 'empirical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/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 

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_moiety     'C63 H54 Br2 Cl2 N6 O8 S2'
_cod_original_formula_sum        'C63 H54 Br2 Cl2 N6 O8 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1317.96
_cod_database_code               4035710