Copper(I)-Catalyzed Sulfonylation of 8-Aminoquinoline Amides with Sulfonyl Chlorides in Air.
Qiao, Huijie; Sun, Suyan; Yang, Fan; Zhu, Yu; Zhu, Weiguo; Dong, Yaxi; Wu, Yusheng; Kong, Xiangtao; Jiang, Ling; Wu, Yangjie; Organic letters 17 (2015) 6086–6089; doi:10.1021/acs.orglett.5b03114

data_1555457
_publ_section_title
;
 Copper(I)-Catalyzed Sulfonylation of 8-Aminoquinoline Amides with
 Sulfonyl Chlorides in Air.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6086
_journal_page_last               6089
_journal_paper_doi               10.1021/acs.orglett.5b03114
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C23 H18 N2 O3 S'
_chemical_formula_sum            'C23 H18 N2 O3 S'
_chemical_formula_weight         402.45
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                103.653(5)
_cell_angle_beta                 93.612(5)
_cell_angle_gamma                114.414(6)
_cell_formula_units_Z            2
_cell_length_a                   9.5468(5)
_cell_length_b                   10.4076(6)
_cell_length_c                   11.3179(7)
_cell_measurement_reflns_used    3303
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.3650
_cell_measurement_theta_min      4.8690
_cell_volume                     978.53(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -77.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -120.0000 25

  2 omega  -64.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 29

  3 omega  -58.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 26

  4 omega  -73.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 40

  5 omega   -3.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -150.0000 32

  6 omega   -4.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -30.0000 25

  7 omega  -13.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000   60.0000 82

  8 omega  -12.00   73.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000    0.0000 85

  9 omega   41.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -120.0000 26

 10 omega   41.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -60.0000 84

 11 omega   -2.00   24.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -120.0000 26

 12 omega   64.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -150.0000 61

 13 omega   49.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -180.0000 48

 14 omega  -11.00   39.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  150.0000 50

 15 omega   47.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 42

 16 omega   40.00  157.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000   90.0000 117

 17 omega   70.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  150.0000 26

 18 omega   43.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 53

 19 omega   39.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 49

 20 omega  111.00  173.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   90.0000 62

 21 omega   85.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 29

 22 omega   58.00  127.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -150.0000 69

 23 omega   47.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 39

 24 omega   39.00   73.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 34

 25 omega   50.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 57

 26 omega  145.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  150.0000 31

 27 omega   43.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  150.0000 65

 28 omega   90.00  125.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  150.0000 35

 29 omega   41.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 57

 30 omega   45.00   79.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 34

 31 omega  -70.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000   60.0000 100

 32 omega  -55.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  121.0000  130.0000 61

 33 omega  -21.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 90

 34 omega   35.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   30.0000 90

 35 omega   35.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  120.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1383018000
_diffrn_orient_matrix_UB_12      0.1458237000
_diffrn_orient_matrix_UB_13      0.0017234000
_diffrn_orient_matrix_UB_21      0.0428293000
_diffrn_orient_matrix_UB_22      0.0390654000
_diffrn_orient_matrix_UB_23      0.1416015000
_diffrn_orient_matrix_UB_31      0.1072964000
_diffrn_orient_matrix_UB_32      -0.0776637000
_diffrn_orient_matrix_UB_33      -0.0153345000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6846
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.087
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.698
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description
;
;
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0761P)^2^+0.3093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1513
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2978
_reflns_number_total             3491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03114_si_002.cif
_cod_data_source_block           20150355
_cod_original_cell_volume        978.54(11)
_cod_database_code               1555457
_chemical_oxdiff_formula         C20H20N4O4S1
_shelx_estimated_absorpt_t_max   0.728
_shelx_estimated_absorpt_t_min   0.706
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 N1-H1A
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
3.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              74186
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'