Metal-Free Synthesis of 2-Substituted 3-(2-Hydroxyaryl)quinolines and 4-(2-Hydroxyaryl)acridines via Benzyne Chemistry.
Dhiman, Ankit Kumar; Kumar, Rakesh; Kumar, Rakesh; Sharma, Upendra; The Journal of organic chemistry 82 (2017) 12307–12317; doi:10.1021/acs.joc.7b02149

data_4033174
_publ_section_title
;
 Metal-Free Synthesis of 2-Substituted 3-(2-Hydroxyaryl)quinolines and
 4-(2-Hydroxyaryl)acridines via Benzyne Chemistry.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12307
_journal_page_last               12317
_journal_paper_doi               10.1021/acs.joc.7b02149
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C19 H13 N O'
_chemical_formula_sum            'C19 H13 N O'
_chemical_formula_weight         271.30
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-08-09
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.111(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1335(7)
_cell_length_b                   9.0731(4)
_cell_length_c                   13.4839(7)
_cell_measurement_reflns_used    2087
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.8710
_cell_measurement_theta_min      3.8610
_cell_volume                     1402.61(14)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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     -8.00  70.00   1.00    1.00    --   25.69  57.00 -30.00   78
  2  \w     73.00  99.00   1.00    1.00    --   25.69  57.00 -30.00   26
  3  \w    100.00 150.00   1.00    1.00    --   66.85 111.00 -60.00   50
  4  \w    111.00 150.00   1.00    1.00    --   66.85 111.00   0.00   39
  5  \w    113.00 146.00   1.00    2.50    --  108.00 104.00 -90.00   33
  6  \w    121.00 170.00   1.00    2.50    --  108.00 104.00-120.00   49
  7  \w    135.00 170.00   1.00    2.50    --  108.00  54.00-150.00   35
  8  \w    139.00 176.00   1.00    2.50    --  108.00  54.00-180.00   37
  9  \w    100.00 147.00   1.00    1.00    --   66.85 111.00-150.00   47
 10  \w     90.00 119.00   1.00    2.50    --  108.00  54.00-150.00   29
 11  \w     79.00 124.00   1.00    2.50    --  108.00  54.00-180.00   45
 12  \w     33.00 153.00   1.00    2.50    --  108.00 -43.00-180.00  120
 13  \w     50.00  79.00   1.00    1.00    --   25.69 -99.00 -60.00   29
 14  \w     12.00 113.00   1.00    1.00    --   66.85-111.00  30.00  101
 15  \w     34.00 149.00   1.00    2.50    --  108.00 -89.00  30.00  115
 16  \w     30.00 100.00   1.00    2.50    --  108.00-104.00 -60.00   70
 17  \w     22.00 135.00   1.00    1.00    --   66.85  45.00 -30.00  113
 18  \w    137.00 167.00   1.00    2.50    --  108.00 138.00 120.00   30
 19  \w     90.00 123.00   1.00    2.50    --  108.00 138.00 120.00   33
 20  \w    -13.00  34.00   1.00    1.00    --   25.69  57.00-120.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1321955000
_diffrn_orient_matrix_UB_12      0.0104001000
_diffrn_orient_matrix_UB_13      0.0197099000
_diffrn_orient_matrix_UB_21      0.0012811000
_diffrn_orient_matrix_UB_22      -0.1623138000
_diffrn_orient_matrix_UB_23      -0.0327603000
_diffrn_orient_matrix_UB_31      -0.0240207000
_diffrn_orient_matrix_UB_32      0.0482850000
_diffrn_orient_matrix_UB_33      -0.1148127000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4309
_diffrn_reflns_theta_full        66.88
_diffrn_reflns_theta_max         66.88
_diffrn_reflns_theta_min         3.86
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0907P)^2^+0.0664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                2105
_reflns_number_total             2453
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02149_si_002.cif
_cod_data_source_block           drk_01_29_rt_cu
_cod_depositor_comments          'Adding full bibliography for 4033174.cif.'
_cod_original_cell_volume        1402.61(13)
_cod_database_code               4033174
_chemical_oxdiff_formula         'C76 H52 N4 O4'
_reflns_odcompleteness_completeness 98.28
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C6(H6), C10(H10), C4(H4), C16(H16), C5(H5), C11(H11),
 C12(H12), C19(H19), C17(H17), C18(H18)
2.b Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_olex2_date_sample_data_collection 2016-06-24
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.804