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_7231607
_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         'C23 H17 N O3'
_chemical_formula_sum            'C23 H17 N O3'
_chemical_formula_weight         355.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_block_doi                 10.5517/ccdc.csd.cc20l3mc
_audit_creation_date             2018-08-29
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
;
2018-08-29 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.7396(11)
_cell_length_b                   12.3042(9)
_cell_length_c                   19.6197(12)
_cell_measurement_reflns_used    3219
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8130
_cell_measurement_theta_min      3.4620
_cell_volume                     3558.2(4)
_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
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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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2542
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9959
_diffrn_measured_fraction_theta_max 0.9959
_diffrn_measurement_details
;
  1 omega  -11.00   47.00   1.0000   14.5400
omega____ theta____ kappa____ phi______ frames
    -       16.6207   19.0000   30.0000 58

  2 omega  -18.00   36.00   1.0000   14.5400
omega____ theta____ kappa____ phi______ frames
    -       16.6207  -99.0000   30.0000 54

  3 omega  -17.00   19.00   1.0000   14.5400
omega____ theta____ kappa____ phi______ frames
    -      -16.8550  -99.0000  150.0000 36

  4 omega  -25.00    0.00   1.0000   14.5400
omega____ theta____ kappa____ phi______ frames
    -      -16.8550  -99.0000   90.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12148
_diffrn_reflns_theta_full        26.4949
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87907
_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_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3267
_exptl_crystal_description       block
_exptl_crystal_F_000             1488.7569
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.3550
_refine_diff_density_min         -0.3591
_refine_diff_density_rms         0.1019
_refine_ls_d_res_high            0.7966
_refine_ls_d_res_low             5.8703
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0422
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0422
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0910P)^2^+0.1340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              0
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                2668
_reflns_number_total             3671
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ra07212d2.cif
_cod_data_source_block           wjx-20180704
_cod_database_code               7231607
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'