Copper-Catalyzed Tandem Reaction of Terminal Alkynes and Sulfonyl Azides for the Assembly of Substituted Aminotriazoles.
Zheng, Xuchun; Wan, Yanjun; Ling, Fei; Ma, Cheng; Organic letters 19 (2017) 3859–3862; doi:10.1021/acs.orglett.7b01729

data_1547108
_publ_section_title
;
 Copper-Catalyzed Tandem Reaction of Terminal Alkynes and Sulfonyl Azides
 for the Assembly of Substituted Aminotriazoles.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3859
_journal_page_last               3862
_journal_paper_doi               10.1021/acs.orglett.7b01729
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C23 H22 N4 O5 S2'
_chemical_formula_sum            'C23 H22 N4 O5 S2'
_chemical_formula_weight         498.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-11
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.964(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6611(5)
_cell_length_b                   11.0315(6)
_cell_length_c                   24.1732(12)
_cell_measurement_reflns_used    2383
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4070
_cell_measurement_theta_min      3.1317
_cell_volume                     2281.4(2)
_computing_cell_refinement
;
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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0393466000
_diffrn_orient_matrix_UB_12      -0.0034967000
_diffrn_orient_matrix_UB_13      -0.0235770000
_diffrn_orient_matrix_UB_21      -0.0179887000
_diffrn_orient_matrix_UB_22      -0.0626520000
_diffrn_orient_matrix_UB_23      -0.0026649000
_diffrn_orient_matrix_UB_31      -0.0707410000
_diffrn_orient_matrix_UB_32      0.0140041000
_diffrn_orient_matrix_UB_33      -0.0178689000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9557
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1375
_reflns_number_gt                3003
_reflns_number_total             4165
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b01729_si_002.cif
_cod_data_source_block           160411_wyj20160407_(A)
_cod_database_code               1547108
_chemical_oxdiff_formula         'c10 h10 o10 n2 F1 S1'
_reflns_odcompleteness_completeness 99.53
_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:
 N4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4A), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;