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_7229029
_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         'C37 H30 N2 O5'
_chemical_formula_sum            'C37 H30 N2 O5'
_chemical_formula_weight         582.63
_chemical_name_common            3f
_chemical_name_systematic        SG-HQ1
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90
_cell_angle_beta                 94.309(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.841(4)
_cell_length_b                   8.9458(16)
_cell_length_c                   18.773(3)
_cell_measurement_reflns_used    6479
_cell_measurement_temperature    297.0(3)
_cell_measurement_theta_max      68.6580
_cell_measurement_theta_min      4.6830
_cell_volume                     2987.7(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9234
_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   -115.00 -13.00   1.00    5.90    --  -41.49 -57.00  90.00  102
  2  \w   -116.00 -17.00   1.00    5.90    --  -41.49 -38.00 120.00   99
  3  \w    -96.00  -2.00   1.00    5.90    --  -41.49 125.00-180.00   94
  4  \w    -35.00  74.00   1.00    5.90    --   41.49 -77.00 -60.00  109
  5  \w     36.00 116.00   1.00   28.00    --  112.00-111.00 150.00   80
  6  \w     57.00 151.00   1.00   28.00    --  112.00 178.00   0.00   94
  7  \w     40.00 141.00   1.00   28.00    --  112.00 -61.00  90.00  101
  8  \w     86.00 178.00   1.00   28.00    --  112.00  45.00-150.00   92
  9  \w     86.00 178.00   1.00   28.00    --  112.00  45.00-180.00   92
 10  \w    100.00 178.00   1.00   28.00    --  112.00 111.00  60.00   78
 11  \w     36.00 116.00   1.00   28.00    --  112.00-111.00-180.00   80
 12  \w     29.00 109.00   1.00   28.00    --  112.00 -94.00-150.00   80
 13  \w     84.00 178.00   1.00   28.00    --  112.00  30.00 150.00   94
 14  \w     86.00 178.00   1.00   28.00    --  112.00  45.00-120.00   92
 15  \w     36.00 116.00   1.00   28.00    --  112.00-111.00 -30.00   80
 16  \w   -115.00 -34.00   1.00    5.90    --  -41.49 -57.00 -30.00   81
 17  \w     98.00 132.00   1.00   28.00    --  112.00 -77.00 120.00   34
 18  \w   -116.00 -17.00   1.00    9.00    --  -41.49 -38.00-150.00   99
 19  \w   -118.00  -9.00   1.00    9.00    --  -41.49 -77.00  26.00  109
 20  \w      1.00  82.00   1.00    9.00    --   41.49 -99.00  90.00   81
 21  \w      9.00  99.00   1.00    9.00    --   41.49  77.00 -90.00   90
 22  \w    153.00 178.00   1.00   28.00    --  112.00 111.00-150.00   25
 23  \w   -115.00 -13.00   1.00   10.00    --  -41.49 -57.00  30.00  102
 24  \w      9.00 118.00   1.00   10.00    --   41.49  77.00-180.00  109
 25  \w      9.00 118.00   1.00   10.00    --   41.49  77.00 120.00  109
 26  \w      1.00  82.00   1.00   10.00    --   41.49 -99.00   0.00   81
 27  \w      9.00 118.00   1.00   10.00    --   41.49  77.00  60.00  109
 28  \w      9.00 118.00   1.00   10.00    --   41.49  77.00 -60.00  109
 29  \w      9.00 118.00   1.00   10.00    --   41.49  77.00   0.00  109
 30  \w     17.00  58.00   1.00   10.00    --   41.49  38.00   0.00   41
 31  \w    -33.00  66.00   1.00   10.00    --   41.49 -38.00  90.00   99
 32  \w    149.00 175.00   1.00   28.00    --  112.00 111.00 -60.00   26
 33  \w    153.00 178.00   1.00   28.00    --  112.00  30.00 -90.00   25
 34  \w     17.00  42.00   1.00    8.64    --   50.00  79.00 130.39   25
 35  \w     20.00  45.00   1.00    8.64    --   54.00  81.00  17.27   25
 36  \w     21.00  46.00   1.00    8.64    --   54.00  79.00-177.41   25
 37  \w     20.00  45.00   1.00    8.64    --   54.00  81.00 -73.43   25
 38  \w     20.00  45.00   1.00    8.64    --   54.00  81.00-119.04   25
 39  \w     33.00  66.00   1.00    8.64    --   66.00  77.00 -46.53   33
 40  \w     34.00  59.00   1.00    8.64    --   66.00  76.00-121.99   25
 41  \w     34.00  60.00   1.00    8.64    --   66.00  76.00  13.20   26
 42  \w     34.00  64.00   1.00    8.64    --   66.00  76.00  95.10   30
 43  \w     34.00  60.00   1.00    8.64    --   66.00  75.00  54.99   26
 44  \w     33.00  59.00   1.00    8.64    --   66.00  77.00 -85.13   26
 45  \w     34.00  63.00   1.00    8.64    --   66.00  76.00 143.19   29
 46  \w     41.00  80.00   1.00    8.64    --   74.00  77.00 179.34   39
 47  \w    134.00 178.00   1.00   28.00    --  112.00  77.00   0.00   44
 48  \w     79.00 104.00   1.00   28.00    --  112.00  77.00  60.00   25
 49  \w     79.00 104.00   1.00   28.00    --  112.00  77.00   0.00   25
 50  \w    140.00 166.00   1.00   28.00    --  112.00  77.00 -90.00   26
 51  \w     79.00 104.00   1.00   28.00    --  112.00  77.00  30.00   25
 52  \w     54.00  85.00   1.00   28.00    --  112.00 -94.00  30.00   31
 53  \w     79.00 106.00   1.00   28.00    --  112.00  77.00 -90.00   27
 54  \w     79.00 111.00   1.00   28.00    --  112.00  77.00 120.00   32
 55  \w    144.00 171.00   1.00   28.00    --  112.00  77.00 -60.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       '/w scans with narrow frames'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0008284000
_diffrn_orient_matrix_UB_12      -0.1677588000
_diffrn_orient_matrix_UB_13      0.0172262000
_diffrn_orient_matrix_UB_21      -0.0726332000
_diffrn_orient_matrix_UB_22      -0.0200196000
_diffrn_orient_matrix_UB_23      -0.0492274000
_diffrn_orient_matrix_UB_31      0.0474948000
_diffrn_orient_matrix_UB_32      -0.0303170000
_diffrn_orient_matrix_UB_33      -0.0637713000
_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  0.1276
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            49427
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.39
_diffrn_reflns_theta_min         2.36
_diffrn_source
;
Advanced Light Source, station 11.3.1
;
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       plate
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1821
_refine_ls_R_factor_gt           0.1176
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3203
_refine_ls_wR_factor_ref         0.3937
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2556
_reflns_number_total             6241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra05287a2.cif
_cod_data_source_block           exp_559
_cod_original_cell_volume        2987.7(9)
_cod_database_code               7229029
_chemical_oxdiff_formula         C37H30N2O5
_reflns_odcompleteness_completeness 99.82
_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 C(H,H) groups, All N(H,H) groups
2.a Rotating group:
 N15(H15a,H15b)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28a,H28b), C36(H36a,H36b), C44(H44a,H44b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C31(H31), C32(H32), C33(H33), C34(H34),
  C35(H35), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43)
;
_shelx_shelxl_version_number     2014/7
_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 5.190
_oxdiff_exptl_absorpt_empirical_full_min 0.328