One-Pot Acid-Catalyzed Ring-Opening/Cyclization/Oxidation of Aziridines with N-Tosylhydrazones: Access to 1,2,4-Triazines.
Crespin, Lorène; Biancalana, Lorenzo; Morack, Tobias; Blakemore, David C.; Ley, Steven V.; Organic letters 19 (2017) 1084–1087; doi:10.1021/acs.orglett.7b00101

data_1545440
_publ_section_title
;
 One-Pot Acid-Catalyzed Ring-Opening/Cyclization/Oxidation of Aziridines
 with N-Tosylhydrazones: Access to 1,2,4-Triazines.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1084
_journal_page_last               1087
_journal_paper_doi               10.1021/acs.orglett.7b00101
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C29 H28 Br N3 O4 S2, 0.5(C6 H14)'
_chemical_formula_sum            'C32 H35 Br N3 O4 S2'
_chemical_formula_weight         669.66
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                103.583(2)
_cell_angle_beta                 97.723(2)
_cell_angle_gamma                92.687(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6338(3)
_cell_length_b                   11.7849(4)
_cell_length_c                   14.3792(4)
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      66.73
_cell_measurement_theta_min      3.20
_cell_volume                     1567.24(9)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            38636
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.918
_diffrn_reflns_theta_max         66.918
_diffrn_reflns_theta_min         3.198
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    3.366
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             694
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.934
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5548
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+2.6869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4388
_reflns_number_total             5548
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00101_si_001.cif
_cod_data_source_block           SL_B2_0005
_cod_database_code               1545440
_cambridge_user_name             'Lorene Crespin'
_cambridge_user_crsid            lc667
_cambridge_supervisor_name       'Steven Ley'
_cambridge_supervisor_crsid      svl1000
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             LB1_56
_cambridge_data_id               SL_B2_0005
_ccdc_publ_extra_info
;
_cambridge_sample_id LB1_56
_cambridge_data_id SL_B2_0005
;
_shelx_estimated_absorpt_t_min   0.730
_shelx_estimated_absorpt_t_max   0.799
_shelx_res_checksum              3962
_shelx_hkl_checksum              47608