Ring-opening and cyclization of aziridines with aryl azides: metal-free synthesis of 6-(triflyloxy)quinolines
Yi, Ruxia; Li, Xincheng; Wan, Boshun; Organic Chemistry Frontiers 5 (2018) 3488–; doi:10.1039/C8QO00984H

data_1554483
_publ_section_title
;
 Ring-opening and cyclization of aziridines with aryl azides: metal-free
 synthesis of 6-(triflyloxy)quinolines
;
_journal_issue                   23
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3488
_journal_paper_doi               10.1039/C8QO00984H
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C16 H9 Cl F3 N O3 S'
_chemical_formula_sum            'C16 H9 Cl F3 N O3 S'
_chemical_formula_weight         387.75
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_Hall           'I 2 -2c'
_space_group_name_H-M_alt        'I b a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-18 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.569(2)
_cell_length_b                   29.973(4)
_cell_length_c                   7.0564(10)
_cell_measurement_reflns_used    2015
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.488
_cell_measurement_theta_min      2.949
_cell_volume                     3292.9(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4604
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.488
_diffrn_reflns_theta_max         25.488
_diffrn_reflns_theta_min         2.949
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details
;
 Flack x determined using 584 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2015
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0730P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    0.747
_reflns_Friedel_fraction_max     0.747
_reflns_number_gt                1721
_reflns_number_total             2015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00984h2.cif
_cod_data_source_block           yrx-74c
_cod_database_code               1554483
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C3(H3), C10(H10), C5(H5), C13(H13), C16(H16), C14(H14),
 C15(H15)
;