HCl-mediated cascade cyclocondensation of oxygenated arylacetic acids with arylaldehydes: one-pot synthesis of 1-arylisoquinolines.
Hsueh, Nai-Chen; Chen, Shin-Mei; Lin, Chun-Yi; Chang, Meng-Yang; Organic & biomolecular chemistry 19 (2021) 1047–1059; doi:10.1039/d0ob02431g

data_7157833
_publ_section_title
;
 HCl-mediated cascade cyclocondensation of oxygenated arylacetic acids
 with arylaldehydes: one-pot synthesis of 1-arylisoquinolines.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1047
_journal_page_last               1059
_journal_paper_doi               10.1039/d0ob02431g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C19 H18 N2 O6'
_chemical_formula_sum            'C19 H18 N2 O6'
_chemical_formula_weight         370.35
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-05-02 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.680(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5325(2)
_cell_length_b                   8.1523(2)
_cell_length_c                   19.8965(4)
_cell_measurement_reflns_used    7192
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.7850
_cell_measurement_theta_min      1.9380
_cell_volume                     1702.70(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.955
_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     10.00  40.00   0.50   10.87    --   10.60  77.00 -90.00   60
  2  \w    -77.00  17.00   0.50   10.87    --   10.60 -38.00  60.00  188
  3  \w    -13.00  48.00   0.50   10.87    --   10.60 -38.00  90.00  122
  4  \w     60.00 100.00   0.50   10.87    --   10.60  77.00 -90.00   80
  5  \w    -86.00 -52.00   0.50   10.87    --  -10.90 -57.00 -30.00   68
  6  \w    -34.00   7.00   0.50   10.87    --  -10.90 -57.00 -30.00   82
  7  \w    -38.00  -5.00   0.50   10.87    --  -10.90  82.00  60.00   66
  8  \w    -24.00  10.00   0.50   10.87    --  -10.90  77.00 -30.00   68
  9  \w     42.00  67.00   0.50   10.87    --  -10.90  82.00  60.00   50
 10  \w    -17.00  78.00   0.50   10.87    --  -10.90  77.00   0.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0422832000
_diffrn_orient_matrix_UB_12      -0.0662012000
_diffrn_orient_matrix_UB_13      -0.0079700000
_diffrn_orient_matrix_UB_21      0.0215807000
_diffrn_orient_matrix_UB_22      -0.0392618000
_diffrn_orient_matrix_UB_23      0.0306354000
_diffrn_orient_matrix_UB_31      -0.0480777000
_diffrn_orient_matrix_UB_32      0.0405979000
_diffrn_orient_matrix_UB_33      0.0166485000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13633
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.014
_diffrn_reflns_theta_min         1.940
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
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    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0074(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0431P)^2^+0.5305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2987
_reflns_number_total             3558
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02431g2.cif
_cod_data_source_block           sh0211-2
_cod_depositor_comments
'Adding full bibliography for 7157832--7157834.cif.'
_cod_database_code               7157833
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H19 N2 O6'
_diffrn_oxdiff_digest_frames
;
01093e50bc978df131db035efeec0c360400025243a
;
_diffrn_oxdiff_digest_hkl
;
01079d6a7905a75d102c6591f61e05c7e8a36f
;
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2), C4(H4), C7(H7), C15(H15), C16(H16), C18(H18)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C)
;
_shelx_res_checksum              86873
_shelx_hkl_checksum              71843
_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 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.719