Cobalt(ii)-catalyzed remote C5-selective C–H sulfonylation of quinolines via insertion of sulfur dioxide
Wang, Kai; Wang, Guodong; Duan, Guiyun; Xia, Chengcai; RSC Advances 7 (2017) 51313–; doi:10.1039/C7RA11363C

data_7229499
_publ_section_title
;
 Cobalt(ii)-catalyzed remote C5-selective C--H sulfonylation of quinolines
 via insertion of sulfur dioxide
;
_journal_issue                   81
_journal_name_full               'RSC Advances'
_journal_page_first              51313
_journal_paper_doi               10.1039/C7RA11363C
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C23 H18 N2 O4 S'
_chemical_formula_sum            'C23 H18 N2 O4 S'
_chemical_formula_weight         418.45
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-27 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                104.003(3)
_cell_angle_beta                 97.178(3)
_cell_angle_gamma                111.781(3)
_cell_formula_units_Z            2
_cell_length_a                   10.136(3)
_cell_length_b                   10.173(3)
_cell_length_c                   11.012(3)
_cell_measurement_reflns_used    4417
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      2.23
_cell_volume                     993.6(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7906
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.801
_diffrn_reflns_theta_min         2.228
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.1640 before and 0.0640 after correction. The Ratio of minimum to maximum transmission is 0.5471. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0731P)^2^+0.2596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3560
_reflns_number_total             4238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra11363c2.cif
_cod_data_source_block           xjk2
_cod_database_code               7229499
_shelx_shelxl_version_number     2014/7
_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 Riding coordinates:
 N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              28880
_olex2_submission_special_instructions 'No special instructions were received'