Three-Component Cycloaddition To Synthesize Aziridines and 1,2,3-Triazolines.
Chen, Shuqi; Yao, Yongqi; Yang, Wen; Lin, Qifu; Wang, Lin; Li, Huanyong; Chen, Donghan; Tan, Yun; Yang, Dingqiao; The Journal of organic chemistry 84 (2019) 11863–11872; doi:10.1021/acs.joc.9b01713

data_4034429
_publ_section_title
;
 Three-Component Cycloaddition To Synthesize Aziridines and
 1,2,3-Triazolines.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11863
_journal_page_last               11872
_journal_paper_doi               10.1021/acs.joc.9b01713
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C19 H19 N O6 S'
_chemical_formula_sum            'C19 H19 N O6 S'
_chemical_formula_weight         389.43
_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_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-08
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                67.889(8)
_cell_angle_beta                 81.813(8)
_cell_angle_gamma                89.110(8)
_cell_formula_units_Z            2
_cell_length_a                   9.2602(9)
_cell_length_b                   9.6004(9)
_cell_length_c                   11.0248(8)
_cell_measurement_reflns_used    1651
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.2640
_cell_measurement_theta_min      3.5710
_cell_volume                     898.01(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9611
_diffrn_measured_fraction_theta_max 0.8110
_diffrn_measurement_details
;
  1 omega  -25.00   31.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       12.6335   91.0000   97.0000 56

  2 omega  -54.00   58.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.5085   19.0000  150.0000 112

  3 omega    1.00   51.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       12.6335  -99.0000  -90.0000 50

  4 omega  -86.00  -36.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.5085 -178.0000   90.0000 50

  5 omega  -83.00   -5.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.5085  -57.0000  -30.0000 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0175874000
_diffrn_orient_matrix_UB_12      -0.0330974000
_diffrn_orient_matrix_UB_13      -0.0476470000
_diffrn_orient_matrix_UB_21      0.0394063000
_diffrn_orient_matrix_UB_22      0.0670087000
_diffrn_orient_matrix_UB_23      -0.0437171000
_diffrn_orient_matrix_UB_31      0.0643163000
_diffrn_orient_matrix_UB_32      -0.0280165000
_diffrn_orient_matrix_UB_33      0.0273515000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5594
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         27.21
_diffrn_reflns_theta_min         3.22
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4401
_exptl_crystal_description       block
_exptl_crystal_F_000             408.4818
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.6689
_refine_diff_density_min         -0.4297
_refine_diff_density_rms         0.0657
_refine_ls_d_res_high            0.7771
_refine_ls_d_res_low             6.3361
_refine_ls_goodness_of_fit_ref   1.0707
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0707
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.5158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2407
_reflns_number_total             3245
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b01713_si_001.cif
_cod_data_source_block           wl-0508
_cod_database_code               4034429
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     23.77
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10), C12(H12), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C15(H15), C14(H14), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C6(H6a,H6b,H6c), C1(H1a,H1b,H1c)
;
_olex2_submission_special_instructions 'No special instructions were received'