Chemoselective acylation of 2-amino-8-quinolinol in the generation of C2-amides or C8-esters
Park, Yongseok; Fei, Xiang; Yuan, Yue; Lee, Sanha; Hur, Joonseong; Park, Sung Jean; Jung, Jae-Kyung; Seo, Seung-Yong; RSC Adv. 7 (2017) 41955–; doi:10.1039/C7RA05287A

data_7229028
_publ_section_title
;
 Chemoselective acylation of 2-amino-8-quinolinol in the generation of
 C2-amides or C8-esters
;
_journal_issue                   67
_journal_name_full               'RSC Adv.'
_journal_page_first              41955
_journal_paper_doi               10.1039/C7RA05287A
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C16 H11 Cl N2 O2'
_chemical_formula_sum            'C16 H11 Cl N2 O2'
_chemical_formula_weight         298.72
_chemical_name_systematic        3b
_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     direct
_audit_creation_date             2017-01-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-05-07 deposited with the CCDC.
2017-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                112.293(2)
_cell_angle_beta                 92.6647(18)
_cell_angle_gamma                104.094(2)
_cell_formula_units_Z            4
_cell_length_a                   10.2425(2)
_cell_length_b                   11.2220(3)
_cell_length_c                   13.7847(3)
_cell_measurement_reflns_used    21206
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      76.2550
_cell_measurement_theta_min      3.5020
_cell_volume                     1404.75(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_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_environment      air
_diffrn_ambient_temperature      294(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9944
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -70.00  32.00   1.00    2.12    --  -41.49  57.00  90.00  102
  2  \w    -66.00  33.00   1.00    2.12    --  -41.49  38.00   0.00   99
  3  \w    -74.00  35.00   1.00    2.12    --  -41.49  77.00-150.00  109
  4  \w     13.00 115.00   1.00    2.12    --   41.49  57.00-180.00  102
  5  \w     23.00  98.00   1.00    2.12    --   41.49-125.00   0.00   75
  6  \w     57.00 151.00   1.00    8.50    --  112.00 178.00-120.00   94
  7  \w     29.00 109.00   1.00    8.50    --  112.00 -94.00 -90.00   80
  8  \w    100.00 178.00   1.00    8.50    --  112.00 111.00 150.00   78
  9  \w     83.00 178.00   1.00    8.50    --  112.00  61.00 -30.00   95
 10  \w     36.00 116.00   1.00    8.50    --  112.00-111.00  90.00   80
 11  \w    100.00 178.00   1.00    8.50    --  112.00 111.00  30.00   78
 12  \w     29.00 109.00   1.00    8.50    --  112.00 -94.00 -30.00   80
 13  \w     36.00 116.00   1.00    8.50    --  112.00-111.00 150.00   80
 14  \w     83.00 178.00   1.00    8.50    --  112.00  61.00-150.00   95
 15  \w     36.00 116.00   1.00    8.50    --  112.00-111.00 -90.00   80
 16  \w     29.00 109.00   1.00    8.50    --  112.00 -94.00-180.00   80
 17  \w     39.00 138.00   1.00    8.50    --  112.00 -45.00-120.00   99
 18  \w     36.00 116.00   1.00    8.50    --  112.00-111.00  60.00   80
 19  \w     29.00 109.00   1.00    8.50    --  112.00 -94.00-150.00   80
 20  \w     86.00 178.00   1.00    8.50    --  112.00  45.00 120.00   92
 21  \w     36.00 116.00   1.00    8.50    --  112.00-111.00 120.00   80
 22  \w     57.00 151.00   1.00    8.50    --  112.00 178.00 120.00   94
 23  \w     36.00 116.00   1.00    8.50    --  112.00-111.00 -30.00   80
 24  \w     57.00 151.00   1.00    8.50    --  112.00 178.00 -90.00   94
 25  \w     83.00 178.00   1.00    8.50    --  112.00  61.00  90.00   95
 26  \w      9.00 118.00   1.00    2.12    --   41.49  77.00 -30.00  109
 27  \w      9.00 118.00   1.00    2.12    --   41.49  77.00  90.00  109
 28  \w      9.00 118.00   1.00    2.12    --   41.49  77.00 -60.00  109
 29  \w     17.00 116.00   1.00    2.12    --   41.49  38.00 -30.00   99
 30  \w      9.00 118.00   1.00    2.12    --   41.49  77.00-150.00  109
 31  \w     13.00 115.00   1.00    2.12    --   41.49  57.00  60.00  102
 32  \w     86.00 178.00   1.00    8.50    --  112.00  45.00 -90.00   92
 33  \w     83.00 161.00   1.00    8.50    --  112.00  61.00  60.00   78
 34  \w     83.00 178.00   1.00    8.50    --  112.00  61.00   0.00   95
 35  \w     83.00 178.00   1.00    8.50    --  112.00  61.00 -60.00   95
 36  \w     79.00 178.00   1.00    8.50    --  112.00  77.00 150.00   99
 37  \w     83.00 178.00   1.00    8.50    --  112.00  61.00  30.00   95
 38  \w      9.00 118.00   1.00    2.12    --   41.49  77.00-180.00  109
 39  \w     17.00 116.00   1.00    2.12    --   41.49  38.00 150.00   99
 40  \w      9.00 118.00   1.00    2.12    --   41.49  77.00-120.00  109
 41  \w     23.00  98.00   1.00    2.12    --   41.49-125.00-180.00   75
 42  \w     13.00 115.00   1.00    2.12    --   41.49  57.00 -90.00  102
 43  \w      9.00 118.00   1.00    2.12    --   41.49  77.00  60.00  109
 44  \w     13.00 115.00   1.00    2.12    --   41.49  57.00 120.00  102
 45  \w    -47.00 130.00   1.00    2.12    --   41.49   0.00-180.00  177
 46  \w    -47.00 130.00   1.00    2.12    --   41.49   0.00-150.00  177
 47  \w     16.00 115.00   1.00    2.12    --   41.49  41.00  52.00   99
 48  \w     83.00 123.00   1.00    8.50    --  112.00  61.00 -90.00   40
 49  \w     79.00 178.00   1.00    8.50    --  112.00  77.00-180.00   99
 50  \w     83.00 178.00   1.00    8.50    --  112.00  61.00-120.00   95
 51  \w     79.00 178.00   1.00    8.50    --  112.00  77.00 120.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0222092000
_diffrn_orient_matrix_UB_12      -0.0952743000
_diffrn_orient_matrix_UB_13      0.0577690000
_diffrn_orient_matrix_UB_21      -0.1553698000
_diffrn_orient_matrix_UB_22      -0.0287269000
_diffrn_orient_matrix_UB_23      -0.0257748000
_diffrn_orient_matrix_UB_31      -0.0023699000
_diffrn_orient_matrix_UB_32      -0.1184111000
_diffrn_orient_matrix_UB_33      -0.1046221000
_diffrn_radiation_collimation    '0.2 mm sinlge-pinhole'
_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  0.0255
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.63
_diffrn_reflns_theta_min         3.51
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.44a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0575P)^2^+0.2605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5200
_reflns_number_total             5881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra05287a2.cif
_cod_data_source_block           exp_582
_cod_database_code               7229028
_chemical_oxdiff_formula         2(C16H11ClN2O2)
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C9(H9), C10(H10), C16(H16), C17(H17), C19(H19),
 C20(H20)
2.b X=CH2 refined with riding coordinates:
 N11(H11A,H11B)
;
_shelx_fab_checksum              84640
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-12-01
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.767