Selective Removal of Aminoquinoline Auxiliary by IBX Oxidation.
Zhang, Zhiguo; Li, Xiang; Song, Mengmeng; Wan, Yameng; Zheng, Dan; Zhang, Guisheng; Chen, Gong; The Journal of organic chemistry 84 (2019) 12792–12799; doi:10.1021/acs.joc.9b01362

data_4034079
_publ_section_title
;
 Selective Removal of Aminoquinoline Auxiliary by IBX Oxidation.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12792
_journal_page_last               12799
_journal_paper_doi               10.1021/acs.joc.9b01362
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C35 H24 N4 O6 S'
_chemical_formula_sum            'C35 H24 N4 O6 S'
_chemical_formula_weight         628.64
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                72.864(5)
_cell_angle_beta                 76.772(6)
_cell_angle_gamma                80.111(6)
_cell_formula_units_Z            2
_cell_length_a                   9.1900(9)
_cell_length_b                   10.8639(6)
_cell_length_c                   17.9645(9)
_cell_measurement_reflns_used    3479
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5540
_cell_measurement_theta_min      4.2690
_cell_volume                     1657.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega -108.00  -32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   30.0000 76

  2 omega  -49.00   37.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -150.0000 86

  3 omega -106.00  -45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   90.0000 61

  4 omega    1.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -77.0000  -60.0000 27

  5 omega  -31.00   52.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -57.0000  -30.0000 83

  6 omega   42.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015   57.0000 -120.0000 48

  7 omega   43.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015   57.0000 -150.0000 61

  8 omega   34.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -99.0000 -120.0000 43

  9 omega   31.00   58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -77.0000  -60.0000 27

 10 omega   42.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -99.0000    0.0000 35

 11 omega   11.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -57.0000   60.0000 27

 12 omega  -29.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -19.0000   60.0000 95

 13 omega   81.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015  178.0000  120.0000 25

 14 omega  -13.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -77.0000   90.0000 76

 15 omega   19.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015   57.0000  -60.0000 85

 16 omega  -32.00    4.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -57.0000   60.0000 36

 17 omega   40.00   67.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 27

 18 omega   39.00   96.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 57

 19 omega   38.00   91.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 53

 20 omega   90.00  177.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 87

 21 omega   41.00   85.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 44

 22 omega   96.00  153.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 57

 23 omega   40.00   99.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 59

 24 omega   54.00  115.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 61

 25 omega   44.00   76.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 32

 26 omega   52.00   98.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 46

 27 omega   47.00   88.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 41

 28 omega   57.00   88.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 31

 29 omega   38.00   88.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 50

 30 omega  145.00  175.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 30

 31 omega  119.00  178.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 59

 32 omega   77.00  109.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 32

 33 omega   58.00  109.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 51

 34 omega   55.00  110.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 55

 35 omega   50.00   91.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 41

 36 omega  -14.00   12.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   22.0000   39.0000 26

 37 omega  -65.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 83

 38 omega  -30.00   -5.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   90.0000 25

 39 omega  -93.00  -50.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   90.0000 43

 40 omega   -4.00   21.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   99.0000  -44.6881 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1220063000
_diffrn_orient_matrix_UB_12      -0.1087876000
_diffrn_orient_matrix_UB_13      -0.0187074000
_diffrn_orient_matrix_UB_21      0.1188139000
_diffrn_orient_matrix_UB_22      0.0662281000
_diffrn_orient_matrix_UB_23      0.0176548000
_diffrn_orient_matrix_UB_31      -0.0320832000
_diffrn_orient_matrix_UB_32      -0.0779748000
_diffrn_orient_matrix_UB_33      0.0876974000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12488
_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         4.286
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.285
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       prism
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0685
_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^)+(0.0973P)^2^+0.7037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1886
_refine_ls_wR_factor_ref         0.2026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4070
_reflns_number_total             5901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01362_si_002.cif
_cod_data_source_block           201811478a
_cod_original_cell_volume        1658.0(2)
_cod_database_code               4034079
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N1S1
_shelx_estimated_absorpt_t_max   0.861
_shelx_estimated_absorpt_t_min   0.802
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C33(H33),
  C34(H34)
2.d Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C)
;
_olex2_submission_special_instructions 'No special instructions were received'