Transition metal/Brønsted acid cooperative catalysis enabled facile synthesis of 8-hydroxyquinolines through one-pot reactions of ortho-aminophenol, aldehydes and alkynes
Yu, Shuyan; Wu, Jingxin; Lan, Hongbing; Xu, Hanwen; Shi, Xiaofei; Zhu, Xuewen; Yin, Zhigang; RSC Advances 8 (2018) 33968–; doi:10.1039/C8RA07212D

data_7231606
_publ_section_title
;
 Transition metal/Br\/onsted acid cooperative catalysis enabled facile
 synthesis of 8-hydroxyquinolines through one-pot reactions of
 ortho-aminophenol, aldehydes and alkynes
;
_journal_issue                   59
_journal_name_full               'RSC Advances'
_journal_page_first              33968
_journal_paper_doi               10.1039/C8RA07212D
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         '2(C22 H17 N O2)'
_chemical_formula_sum            'C44 H34 N2 O4'
_chemical_formula_weight         654.73
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc20l3k9
_audit_creation_date             2017-10-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-08-29 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                67.800(3)
_cell_angle_beta                 87.298(3)
_cell_angle_gamma                81.654(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0073(4)
_cell_length_b                   12.1668(5)
_cell_length_c                   15.4066(5)
_cell_measurement_reflns_used    5368
_cell_measurement_temperature    293
_cell_measurement_theta_max      73.3300
_cell_measurement_theta_min      3.9280
_cell_volume                     1718.35(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.966
_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    -65.00  -3.00   1.00    1.96    --  -40.80  57.00   0.00   62
  2  \w    -65.00  30.00   1.00    1.96    --  -40.80  38.00 150.00   95
  3  \w   -109.00 -19.00   1.00    1.96    --  -40.80 -38.00 -30.00   90
  4  \w   -104.00 -19.00   1.00    1.96    --  -40.80 -57.00-150.00   85
  5  \w     50.00  92.00   1.00    1.96    --   40.80-125.00-180.00   42
  6  \w     90.00 118.00   1.00    7.85    --  107.14-125.00-180.00   28
  7  \w     77.00 121.00   1.00    7.85    --  107.14-125.00 -60.00   44
  8  \w     89.00 121.00   1.00    7.85    --  107.14 -77.00 -30.00   32
  9  \w     60.00 108.00   1.00    7.85    --  107.14 -95.00   0.00   48
 10  \w     38.00 135.00   1.00    7.85    --  107.14 -30.00 -60.00   97
 11  \w     80.00 171.00   1.00    7.85    --  107.14  30.00 -30.00   91
 12  \w    104.00 136.00   1.00    7.85    --  107.14 125.00 -90.00   32
 13  \w     57.00 175.00   1.00    7.85    --  107.14  15.00 -90.00  118
 14  \w     36.00  64.00   1.00    7.85    --  107.14-125.00-180.00   28
 15  \w     34.00  73.00   1.00    7.85    --  107.14 -77.00 -60.00   39
 16  \w     33.00  64.00   1.00    7.85    --  107.14 -77.00 -30.00   31
 17  \w     31.00 108.00   1.00    7.85    --  107.14 -77.00  90.00   77
 18  \w     35.00 135.00   1.00    7.85    --  107.14 -61.00 150.00  100
;
_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      -0.0770224000
_diffrn_orient_matrix_UB_12      -0.0914296000
_diffrn_orient_matrix_UB_13      -0.0163195000
_diffrn_orient_matrix_UB_21      0.1345159000
_diffrn_orient_matrix_UB_22      -0.0808417000
_diffrn_orient_matrix_UB_23      0.0024486000
_diffrn_orient_matrix_UB_31      -0.0135393000
_diffrn_orient_matrix_UB_32      -0.0645715000
_diffrn_orient_matrix_UB_33      0.1067352000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11762
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.735
_diffrn_reflns_theta_min         3.962
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         6711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0624P)^2^+0.1084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5494
_reflns_number_total             6711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra07212d2.cif
_cod_data_source_block           su-dy-20171002-1
_cod_database_code               7231606
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C H O N Dy '
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.850
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C3(H3), C19(H19), C25(H25), C44(H44), C22(H22), C16(H16), C21(H21),
 C7(H7), C5(H5), C6(H6), C29(H29), C40(H40), C12(H12), C43(H43), C41(H41),
 C28(H28), C38(H38), C27(H27), C15(H15), C14(H14), C13(H13), C37(H37), C34(H34),
  C36(H36), C35(H35)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C45(H45A,H45B,H45C)
;
_shelx_res_checksum              28572
_shelx_hkl_checksum              18895
_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 1.774
_oxdiff_exptl_absorpt_empirical_full_min 0.800