Selective remote C-H sulfonylation of aminoquinolines with arylsulfonyl chlorides via copper catalysis
Hong-Wen Liang; Kun Jiang; Wei Ding; Yi Yuan; Li Shuai; Ying-Chun Chen; Ye Wei; Chem.Commun. 51 (2015) 16928–; doi:10.1039/C5cc05527J

data_7118088
_publ_section_title
;
 Selective remote C-H sulfonylation of aminoquinolines with arylsulfonyl
 chlorides via copper catalysis
;
_journal_name_full               Chem.Commun.
_journal_page_first              16928
_journal_paper_doi               10.1039/C5cc05527J
_journal_volume                  51
_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'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-07-08
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_audit_update_record
;
2014-11-10 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                102.651(4)
_cell_angle_beta                 93.971(5)
_cell_angle_gamma                114.471(5)
_cell_formula_units_Z            2
_cell_length_a                   9.4496(6)
_cell_length_b                   10.2550(5)
_cell_length_c                   11.2370(6)
_cell_measurement_reflns_used    4151
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      72.4540
_cell_measurement_theta_min      4.9120
_cell_volume                     951.23(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9670
_diffrn_measurement_details
;
  1 omega  -50.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3992   38.0000   90.0000 78

  2 omega  -50.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3992   38.0000  -60.0000 85

  3 omega  -81.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3992   19.0000 -120.0000 100

  4 omega   25.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3992 -125.0000    0.0000 58

  5 omega   51.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -94.0000  120.0000 54

  6 omega   91.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122 -125.0000   60.0000 27

  7 omega   39.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -45.0000   90.0000 57

  8 omega  119.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122   30.0000  150.0000 57

  9 omega   93.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122   30.0000   90.0000 85

 10 omega  138.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  125.0000  -30.0000 40

 11 omega   97.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  125.0000  -30.0000 26

 12 omega   77.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122   30.0000  150.0000 26

 13 omega   30.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -30.0000  150.0000 61

 14 omega   39.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -77.0000  -30.0000 102

 15 omega   40.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3992 -125.0000 -180.0000 47

 16 omega   25.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -94.0000  -90.0000 45

 17 omega   39.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122 -125.0000  -30.0000 74

 18 omega   32.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -30.0000  -90.0000 26

 19 omega   29.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -30.0000  -30.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1240947000
_diffrn_orient_matrix_UB_12      0.0550931000
_diffrn_orient_matrix_UB_13      0.0361147000
_diffrn_orient_matrix_UB_21      0.0936896000
_diffrn_orient_matrix_UB_22      0.0734843000
_diffrn_orient_matrix_UB_23      0.1336079000
_diffrn_orient_matrix_UB_31      0.0947771000
_diffrn_orient_matrix_UB_32      0.1449042000
_diffrn_orient_matrix_UB_33      -0.0353497000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6105
_diffrn_reflns_theta_full        73.32
_diffrn_reflns_theta_max         73.32
_diffrn_reflns_theta_min         4.10
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           n/a
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    1.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.200
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.152
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.7470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                3536
_reflns_number_total             3694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05527j2.cif
_cod_data_source_block           exp_7336
_cod_original_cell_volume        951.22(9)
_cod_database_code               7118088
_chemical_oxdiff_formula         'C H N O S'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97