Synthesis of fully-substituted 1,2,3-triazoles via copper(i)-catalyzed three-component coupling of sulfoximines, alkynes and azides
Xu, Jian; Song, Qiuling; Organic Chemistry Frontiers 4 (2017) 938–; doi:10.1039/C6QO00725B

data_1553608
_publ_section_title
;
 Synthesis of fully-substituted 1,2,3-triazoles via copper(i)-catalyzed
 three-component coupling of sulfoximines, alkynes and azides
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              938
_journal_paper_doi               10.1039/C6QO00725B
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C26 H31 F2 N O3'
_chemical_formula_sum            'C26 H31 F2 N O3'
_chemical_formula_weight         443.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2016-06-13 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                89.023(7)
_cell_angle_beta                 76.071(7)
_cell_angle_gamma                71.074(8)
_cell_formula_units_Z            2
_cell_length_a                   9.4574(7)
_cell_length_b                   9.9936(9)
_cell_length_c                   14.0156(13)
_cell_measurement_reflns_used    2528
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2290
_cell_measurement_theta_min      3.0890
_cell_volume                     1213.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0266851000
_diffrn_orient_matrix_UB_12      0.0520219000
_diffrn_orient_matrix_UB_13      -0.0262362000
_diffrn_orient_matrix_UB_21      0.0067391000
_diffrn_orient_matrix_UB_22      0.0275896000
_diffrn_orient_matrix_UB_23      0.0443684000
_diffrn_orient_matrix_UB_31      0.0770913000
_diffrn_orient_matrix_UB_32      -0.0467685000
_diffrn_orient_matrix_UB_33      -0.0085953000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9649
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.035
_diffrn_reflns_theta_min         3.088
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.048
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    0.424
_exptl_crystal_F_000             155
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         5470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0660P)^2^+0.2930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1560
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3753
_reflns_number_total             5470
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00725b2.cif
_cod_data_source_block           exp_1694
_cod_depositor_comments
;

2025-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C H F N O'
_cod_original_formula_weight         62.03
_cod_original_formula_moiety         '0.4(C26 H31 F2 N O3)'
_cod_original_formula_units_Z            5
_cod_original_cell_volume        1213.52(19)
_cod_database_code               1553608
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.68
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C16(H16), C18(H18), C22(H22), C25(H25), C39(H39)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C2(H2A,H2B,H2C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              21476
_shelx_hkl_checksum              69042
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.860
_oxdiff_exptl_absorpt_empirical_full_min 0.539