A New Strategy for the Synthesis of 1,4-Benzodiazepine Derivatives Based on the Tandem N-Alkylation-Ring Opening-Cyclization Reactions of Methyl 1-Arylaziridine-2-carboxylates with N-[2-Bromomethyl(phenyl)]trifluoroacetamides
Jin-Yuan Wang; Xue-Fei Guo; De-Xiang Wang; Zhi-Tang Huang; Mei-Xiang Wang; Journal of Organic Chemistry 73 (2008) 1979–1982; doi:10.1021/jo7024306

data_4023319
_publ_section_title
;
 A New Strategy for the Synthesis of 1,4-Benzodiazepine Derivatives
 Based on the Tandem N-Alkylation-Ring Opening-Cyclization Reactions
 of Methyl 1-Arylaziridine-2-carboxylates with
 N-[2-Bromomethyl(phenyl)]trifluoroacetamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1979
_journal_page_last               1982
_journal_paper_doi               10.1021/jo7024306
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C20 H19 F3 N2 O3'
_chemical_formula_weight         392.37
_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                 94.06(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.100(3)
_cell_length_b                   7.9174(16)
_cell_length_c                   17.453(4)
_cell_measurement_reflns_used    4333
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.45
_cell_volume                     1943.5(7)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP'
_diffrn_measurement_method       "'\w oscillation"
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7161
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_correction_T_min  0.9564
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   abscor
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.2005
_refine_ls_R_factor_gt           0.1160
_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^)+(0.1141P)^2^+2.0835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2864
_refine_ls_wR_factor_ref         0.3314
_reflns_number_gt                2125
_reflns_number_total             4333
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7024306-File001.cif
_cod_data_source_block           a
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023319