Transition metal free oxygenation of 8-aminoquinoline amides in water
Yao, Xinghui; Weng, Xin; Wang, Kaixuan; Xiang, Haifeng; Zhou, Xiangge; Green Chemistry 20 (2018) 2472–; doi:10.1039/C8GC00191J

data_7230471
_publ_section_title
;
 Transition metal free oxygenation of 8-aminoquinoline amides in water
;
_journal_issue                   11
_journal_name_full               'Green Chemistry'
_journal_page_first              2472
_journal_paper_doi               10.1039/C8GC00191J
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C23 H18 N2 O5 S'
_chemical_formula_sum            'C23 H18 N2 O5 S'
_chemical_formula_weight         434.45
_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     iterative
_audit_creation_date             2017-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-10-30 deposited with the CCDC.
2018-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                68.418(7)
_cell_angle_beta                 81.041(7)
_cell_angle_gamma                68.191(7)
_cell_formula_units_Z            2
_cell_length_a                   9.1495(7)
_cell_length_b                   11.0385(8)
_cell_length_c                   11.7750(10)
_cell_measurement_reflns_used    2746
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1610
_cell_measurement_theta_min      3.8150
_cell_volume                     1026.46(16)
_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      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -42.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000  150.0000 95

  2 omega  -34.00   54.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   38.0000  -60.0000 88

  3 omega  -25.00   20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -90.0000 45

  4 omega  -87.00  -37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000  120.0000 50

  5 omega  -80.00   12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -77.0000   30.0000 92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0766850000
_diffrn_orient_matrix_UB_12      0.0110840000
_diffrn_orient_matrix_UB_13      -0.0159886000
_diffrn_orient_matrix_UB_21      0.0095887000
_diffrn_orient_matrix_UB_22      -0.0703843000
_diffrn_orient_matrix_UB_23      0.0340094000
_diffrn_orient_matrix_UB_31      -0.0316713000
_diffrn_orient_matrix_UB_32      0.0181952000
_diffrn_orient_matrix_UB_33      0.0527839000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0376
_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       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8234
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         3.003
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80480
_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_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0504P)^2^+0.2602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3151
_reflns_number_total             4187
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc00191j2.cif
_cod_data_source_block           171023_s4_yxh-178
_cod_depositor_comments          'Adding full bibliography for 7230471.cif.'
_cod_database_code               7230471
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3s1
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.934
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C19(H19), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'