Ruthenium-Catalyzed Remote C-H Sulfonylation of N-Aryl-2-aminopyridines with Aromatic Sulfonyl Chlorides.
Ramesh, Balu; Jeganmohan, Masilamani; Organic letters 19 (2017) 6000–6003; doi:10.1021/acs.orglett.7b03051

data_1547875
_publ_section_title
;
 Ruthenium-Catalyzed Remote C-H Sulfonylation of N-Aryl-2-aminopyridines
 with Aromatic Sulfonyl Chlorides.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              6000
_journal_page_last               6003
_journal_paper_doi               10.1021/acs.orglett.7b03051
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C20 H20 N2 O2 S'
_chemical_formula_weight         352.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.4759(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.8321(7)
_cell_length_b                   8.4143(3)
_cell_length_c                   29.8348(12)
_cell_measurement_reflns_used    3990
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.06
_cell_measurement_theta_min      2.75
_cell_volume                     3691.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            12265
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.754
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       Block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0575
_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^)+(0.0774P)^2^+5.5888P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2252
_reflns_number_total             3245
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b03051_si_003.cif
_cod_data_source_block           96
_cod_database_code               1547875
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              96540
_shelx_hkl_checksum              55652