Synergistic Effect of the TiCl4/p-TsOH Promoter System on the Aza-Prins Cyclization.
Durel, Vianney; Lalli, Claudia; Roisnel, Thierry; Weghe, Pierre van de; The Journal of organic chemistry 81 (2016) 849–859; doi:10.1021/acs.joc.5b02342

data_4031921
_publ_section_title
;
 Synergistic Effect of the TiCl4/p-TsOH Promoter System on the Aza-Prins
 Cyclization.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              849
_journal_page_last               859
_journal_paper_doi               10.1021/acs.joc.5b02342
_journal_volume                  81
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H13 Br Cl N'
_chemical_formula_sum            'C11 H13 Br Cl N'
_chemical_formula_weight         274.58
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2c'
_symmetry_space_group_name_H-M   'P c a n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2014-11-04T12:08:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.4944(6)
_cell_length_b                   17.8095(14)
_cell_length_c                   23.213(3)
_cell_measurement_reflns_used    1393
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.83
_cell_measurement_theta_min      3.51
_cell_measurement_wavelength     0.71073
_cell_volume                     2271.5(4)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
          WinGX publication routines (Farrugia, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10758
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.51
_exptl_absorpt_coefficient_mu    3.815
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_correction_T_min  0.523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0413P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                1623
_reflns_number_total             2592
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02342_si_002.cif
_cod_data_source_block           VD338
_cod_database_code               4031921