Synthesis of α-aminoketones from N-sulfonyl-1,2,3-triazoles via N-sulfinyl imines generated by intramolecular oxygen transfer
Xu, Ze-Feng; Shan, Lihong; Zhang, Wan; Cen, Mengjie; Li, Chuan-Ying; Organic Chemistry Frontiers 6 (2019) 1391–; doi:10.1039/C9QO00126C

data_1554739
_publ_section_title
;
 Synthesis of \a-aminoketones from N-sulfonyl-1,2,3-triazoles via
 N-sulfinyl imines generated by intramolecular oxygen transfer
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1391
_journal_paper_doi               10.1039/C9QO00126C
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C23 H19 Br N2 O3 S'
_chemical_formula_sum            'C23 H19 Br N2 O3 S'
_chemical_formula_weight         483.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-22
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
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_audit_update_record
;
2018-10-31 deposited with the CCDC.	2019-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.486(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1948(12)
_cell_length_b                   18.8246(10)
_cell_length_c                   10.1822(8)
_cell_measurement_reflns_used    4090
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3273
_cell_measurement_theta_min      3.1681
_cell_volume                     2252.6(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -70.00    2.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  126.0000  -76.0000 72

  2 omega  -56.00    1.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  -77.0000 -120.0000 57

  3 omega  -89.00  -63.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  154.0000 -171.0000 26

  4 omega  -64.00   38.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371  -38.0000 -150.0000 102

  5 omega  -14.00   73.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000   30.0000 87
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0602120000
_diffrn_orient_matrix_UB_12      0.0008544000
_diffrn_orient_matrix_UB_13      0.0142764000
_diffrn_orient_matrix_UB_21      -0.0042574000
_diffrn_orient_matrix_UB_22      -0.0015825000
_diffrn_orient_matrix_UB_23      -0.0707542000
_diffrn_orient_matrix_UB_31      -0.0015635000
_diffrn_orient_matrix_UB_32      0.0376364000
_diffrn_orient_matrix_UB_33      -0.0033461000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17026
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         3.174
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.944
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0418P)^2^+1.4923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3195
_reflns_number_total             4121
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00126c2.cif
_cod_data_source_block           180522_slh1
_cod_database_code               1554739
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o s br'
_shelx_estimated_absorpt_t_max   0.518
_shelx_estimated_absorpt_t_min   0.449
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2)
2.b Ternary CH refined with riding coordinates:
 C10(H10)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              54577
_shelx_hkl_checksum              75026
_olex2_submission_special_instructions 'No special instructions were received'