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_7229030
_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        4b
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-07
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_audit_update_record
;
2017-05-07 deposited with the CCDC.
2017-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.6800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.1622(3)
_cell_length_b                   3.82800(10)
_cell_length_c                   31.4881(3)
_cell_measurement_reflns_used    14387
_cell_measurement_temperature    293.3(3)
_cell_measurement_theta_max      76.3830
_cell_measurement_theta_min      2.8410
_cell_volume                     2752.14(8)
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.3(3)
_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 0.9952
_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   -106.00 -30.00   1.00    1.10    --  -41.49 -38.00 -60.00   76
  2  \w   -112.00 -17.00   1.00    1.10    --  -41.49 -38.00-150.00   95
  3  \w     18.00  44.00   1.00    1.10    --   41.49  38.00 -90.00   26
  4  \w     68.00  95.00   1.00    1.10    --   41.49-129.00-114.00   27
  5  \w     41.00  94.00   1.00    5.00    --  112.00 -94.00   0.00   53
  6  \w     86.00 166.00   1.00    5.00    --  112.00  45.00 -30.00   80
  7  \w     76.00 114.00   1.00    5.00    --  112.00 -30.00 120.00   38
  8  \w     48.00 145.00   1.00    5.00    --  112.00 -77.00  60.00   97
  9  \w    147.00 173.00   1.00    5.00    --  112.00  30.00-120.00   26
 10  \w    103.00 130.00   1.00    5.00    --  112.00 111.00-120.00   27
 11  \w     86.00 178.00   1.00    5.00    --  112.00  45.00-150.00   92
 12  \w     93.00 178.00   1.00    5.00    --  112.00  30.00 -60.00   85
 13  \w     37.00  91.00   1.00    5.00    --  112.00 -77.00  30.00   54
 14  \w    -87.00 -50.00   1.00    1.10    --  -41.49 -57.00   0.00   37
 15  \w    -38.00 -13.00   1.00    1.10    --  -41.49 -57.00   0.00   25
 16  \w      1.00  62.00   1.00    1.10    --   41.49 -99.00-180.00   61
 17  \w      7.00  34.00   1.00    1.10    --   41.49  87.00 173.01   27
 18  \w    -31.00  66.00   1.00    1.10    --   41.49 -38.00-150.00   97
 19  \w     42.00  74.00   1.00    1.10    --   41.49-140.00  72.00   32
 20  \w     38.00  64.00   1.00    1.10    --   41.49-125.00 120.00   26
 21  \w     13.00  40.00   1.00    1.10    --   46.00  83.00   5.01   27
 22  \w     17.00  49.00   1.00    1.10    --   50.00  78.00  56.45   32
 23  \w     18.00  46.00   1.00    1.10    --   50.00  80.00 -48.20   28
 24  \w     76.00 125.00   1.00    1.10    --   54.00  77.00 121.44   49
 25  \w     21.00  63.00   1.00    1.10    --   54.00  77.00-101.08   42
 26  \w     21.00  58.00   1.00    1.10    --   54.00  77.00 121.44   37
 27  \w    105.00 130.00   1.00    1.10    --   54.00  77.00-101.08   25
 28  \w     27.00  59.00   1.00    1.10    --   58.00  76.00 162.68   32
 29  \w     31.00  61.00   1.00    1.10    --   58.00  76.00-154.04   30
 30  \w    102.00 127.00   1.00    1.10    --   58.00  76.00-154.04   25
 31  \w    100.00 125.00   1.00    1.10    --   58.00  76.00 162.68   25
 32  \w     37.00  63.00   1.00    1.10    --   62.00  34.00  60.77   26
 33  \w     38.00  77.00   1.00    1.10    --   66.00  57.00  67.81   39
 34  \w     57.00 101.00   1.00    5.00    --  112.00-111.00 -90.00   44
 35  \w     80.00 107.00   1.00    5.00    --  112.00  77.00  30.00   27
 36  \w     79.00 105.00   1.00    5.00    --  112.00  77.00 120.00   26
 37  \w    141.00 172.00   1.00    5.00    --  112.00  77.00 -30.00   31
 38  \w     83.00 109.00   1.00    5.00    --  112.00  61.00-150.00   26
 39  \w     79.00 132.00   1.00    5.00    --  112.00  77.00 -30.00   53
 40  \w    111.00 138.00   1.00    5.00    --  112.00 -61.00  90.00   27
 41  \w    119.00 177.00   1.00    5.00    --  112.00  77.00  30.00   58
 42  \w     80.00 105.00   1.00    5.00    --  112.00  77.00-150.00   25
 43  \w    151.00 176.00   1.00    5.00    --  112.00  77.00-150.00   25
 44  \w     79.00 105.00   1.00    5.00    --  112.00  77.00 -90.00   26
 45  \w    143.00 176.00   1.00    5.00    --  112.00  61.00-180.00   33
 46  \w     83.00 113.00   1.00    5.00    --  112.00  61.00-180.00   30
 47  \w    133.00 174.00   1.00    5.00    --  112.00  77.00  90.00   41
 48  \w     79.00 106.00   1.00    5.00    --  112.00  77.00  90.00   27
 49  \w     84.00 109.00   1.00    5.00    --  112.00  61.00 -30.00   25
 50  \w     79.00 147.00   1.00    5.00    --  112.00  77.00   0.00   68
 51  \w    152.00 178.00   1.00    5.00    --  112.00  61.00-120.00   26
 52  \w     54.00 140.00   1.00    5.00    --  112.00 -61.00-120.00   86
 53  \w     84.00 109.00   1.00    5.00    --  112.00  61.00 -60.00   25
 54  \w     83.00 125.00   1.00    5.00    --  112.00  61.00-120.00   42
 55  \w     83.00 178.00   1.00    5.00    --  112.00  61.00 150.00   95
 56  \w     80.00 105.00   1.00    5.00    --  112.00  77.00-180.00   25
 57  \w     86.00 151.00   1.00    5.00    --  112.00  61.00  90.00   65
 58  \w     83.00 122.00   1.00    5.00    --  112.00  61.00 120.00   39
 59  \w    129.00 178.00   1.00    5.00    --  112.00  61.00 120.00   49
 60  \w    115.00 175.00   1.00    5.00    --  112.00  77.00  60.00   60
 61  \w     79.00 105.00   1.00    5.00    --  112.00  77.00 150.00   26
 62  \w     84.00 110.00   1.00    5.00    --  112.00  61.00 -90.00   26
 63  \w    148.00 177.00   1.00    5.00    --  112.00  61.00 -90.00   29
 64  \w     80.00 105.00   1.00    5.00    --  112.00  77.00  60.00   25
 65  \w     79.00 105.00   1.00    5.00    --  112.00  77.00 -60.00   26
 66  \w    149.00 175.00   1.00    5.00    --  112.00  77.00 -60.00   26
 67  \w     45.00  71.00   1.00    5.00    --  112.00 -61.00  90.00   26
 68  \w     79.00 108.00   1.00    5.00    --  112.00  77.00-120.00   29
 69  \w     43.00  69.00   1.00    5.00    --  112.00-111.00-180.00   26
 70  \w     89.00 115.00   1.00    5.00    --  112.00-111.00-180.00   26
 71  \w     83.00 126.00   1.00    5.00    --  112.00  61.00  60.00   43
;
_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      0.0671134000
_diffrn_orient_matrix_UB_12      0.0366808000
_diffrn_orient_matrix_UB_13      0.0107427000
_diffrn_orient_matrix_UB_21      0.0034786000
_diffrn_orient_matrix_UB_22      -0.0067493000
_diffrn_orient_matrix_UB_23      -0.0484222000
_diffrn_orient_matrix_UB_31      -0.0060777000
_diffrn_orient_matrix_UB_32      0.4006932000
_diffrn_orient_matrix_UB_33      -0.0017826000
_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  0.0194
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            25095
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.61
_diffrn_reflns_theta_min         2.20
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.511
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80762
_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    1.442
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00166(14)
_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   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0676P)^2^+1.9139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2753
_reflns_number_total             2882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra05287a2.cif
_cod_data_source_block           exp_588
_cod_database_code               7229030
_chemical_oxdiff_formula         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
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C9(H9), C10(H10), C13(H13), C15(H15), C16(H16)
2.b Idealised tetrahedral OH refined as rotating group:
 O12(H12)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-12-06
_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 1.197
_oxdiff_exptl_absorpt_empirical_full_min 0.863