Gold(I)/Gold(III)-Catalyzed Selective Synthesis of N-Sulfonyl Enaminone Isomers from Sulfonamides and Ynones via Two Distinct Reaction Pathways.
Lee, Dabon; Kim, Sang Min; Hirao, Hajime; Hong, Soon Hyeok; Organic letters 19 (2017) 4734–4737; doi:10.1021/acs.orglett.7b02022

data_1547558
_publ_section_title
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 Gold(I)/Gold(III)-Catalyzed Selective Synthesis of N-Sulfonyl Enaminone
 Isomers from Sulfonamides and Ynones via Two Distinct Reaction Pathways.
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_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4734
_journal_page_last               4737
_journal_paper_doi               10.1021/acs.orglett.7b02022
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C17 H17 N O3 S'
_chemical_formula_sum            'C17 H17 N O3 S'
_chemical_formula_weight         315.37
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-05-22 deposited with the CCDC.
2017-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.150(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8615(8)
_cell_length_b                   12.1461(10)
_cell_length_c                   14.1071(12)
_cell_measurement_reflns_used    7765
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.90
_cell_measurement_theta_min      2.26
_cell_volume                     1614.6(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      223.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1092
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            52632
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.364
_diffrn_reflns_theta_min         2.161
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1063 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.9297.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       Block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         4030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0410P)^2^+1.0970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2538
_reflns_number_total             4030
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02022_si_002.cif
_cod_data_source_block           no1
_cod_database_code               1547558
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H6(0.047) H10(0.056) H11(0.06) H12(0.051) H13(0.061) H14(0.057)
 H18(0.062) H19(0.057) H20(0.062) H21A(0.124) H21B(0.124) H21C(0.124)
 H0AA(0.048) H1A(0.093) H1B(0.093) H1C(0.093)
 Fixed X: H6(0.3847) H10(0.9276) H11(0.2139) H12(0.4551) H13(0.0599)
 H14(0.5343) H18(0.9485) H19(0.145) H20(0.5588) H21A(0.746) H21B(0.6992)
 H21C(0.862) H0AA(0.561) H1A(0.7776) H1B(0.7374) H1C(0.8976)
 Fixed Y: H6(0.574) H10(0.654) H11(0.9303) H12(0.897) H13(0.7875) H14(0.6907)
 H18(0.4868) H19(0.6095) H20(0.5246) H21A(0.318) H21B(0.3688) H21C(0.3644)
 H0AA(0.579) H1A(0.502) H1B(0.4303) H1C(0.4633)
 Fixed Z: H6(-0.0456) H10(0.1866) H11(-0.1065) H12(-0.0738) H13(-0.105)
 H14(0.2137) H18(0.2677) H19(-0.0733) H20(0.2972) H21A(0.2861) H21B(0.375)
 H21C(0.3808) H0AA(-0.1346) H1A(-0.2093) H1B(-0.1278) H1C(-0.1134)
;
_olex2_submission_special_instructions 'No special instructions were received'