Copper-catalyzed three-component cascade reaction of alkynes, sulfonyl azides and simple aldehydes/ketones.
Hu, Yuanyuan; Zhou, Bingwei; Wang, Congyang; Organic & biomolecular chemistry 14 (2016) 3022–3026; doi:10.1039/c6ob00146g

data_7154975
_publ_section_title
;
 Copper-catalyzed three-component cascade reaction of alkynes, sulfonyl
 azides and simple aldehydes/ketones.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3022
_journal_page_last               3026
_journal_paper_doi               10.1039/c6ob00146g
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C23 H21 N O3 S'
_chemical_formula_sum            'C23 H21 N O3 S'
_chemical_formula_weight         391.47
_chemical_name_systematic        (E)-2,3-diphenyl-N-tosylbut-2-enamide
_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
_audit_creation_date             2014-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2015-12-27 deposited with the CCDC.
2016-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.104(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.710(3)
_cell_length_b                   19.200(5)
_cell_length_c                   22.065(6)
_cell_measurement_reflns_used    11764
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4846
_cell_measurement_theta_min      0.9300
_cell_volume                     4082(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0341
_diffrn_orient_matrix_UB_12      0.0884
_diffrn_orient_matrix_UB_13      -0.0423
_diffrn_orient_matrix_UB_21      0.0183
_diffrn_orient_matrix_UB_22      0.0151
_diffrn_orient_matrix_UB_23      0.0464
_diffrn_orient_matrix_UB_31      0.0416
_diffrn_orient_matrix_UB_32      -0.0150
_diffrn_orient_matrix_UB_33      -0.0116
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            29405
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         1.860
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       rod
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         9326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0870
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0135P)^2^+3.8809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7541
_reflns_number_total             9326
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00146g2.cif
_cod_data_source_block           mx3220
_cod_depositor_comments
'Adding full bibliography for 7154975--7154976.cif.'
_cod_original_cell_volume        4082.2(19)
_cod_database_code               7154975
_shelxl_version_number           2013-4
_diffrn_number_total             9621
_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 Aromatic/amide H refined with riding coordinates:
 N1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C11A(H11A),
 C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C18A(H18A), C19A(H19A),
 C21A(H21A), C22A(H22A), N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6),
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C21(H21),
  C22(H22)
2.b Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C23A(H23A,H23B,H23C), C8(H8A,H8B,H8C), C23(H23D,H23E,H23F)
;
_shelx_res_checksum              55340