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_7157834
_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         'C20 H21 N O5'
_chemical_formula_sum            'C20 H21 N O5'
_chemical_formula_weight         355.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-02 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.235(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6565(2)
_cell_length_b                   9.9527(2)
_cell_length_c                   20.7506(5)
_cell_measurement_reflns_used    13673
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9150
_cell_measurement_theta_min      2.2690
_cell_volume                     1777.20(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -40.00 -14.00   0.50    8.60    --   10.60 -52.00 132.00   52
  2  \w      3.00  29.00   0.50    8.60    --  -10.90  52.00 -82.00   52
  3  \w    -64.00 -39.00   0.50    8.60    --  -10.90 -52.00 132.00   50
  4  \w    -15.00  40.00   0.50    8.60    --   10.60  82.00  60.00  110
  5  \w     43.00  73.00   0.50    8.60    --   10.60  19.00 120.00   60
  6  \w     21.00  87.00   0.50    8.60    --   10.60  82.00 150.00  132
  7  \w    -79.00  -8.00   0.50    8.60    --   10.60 -82.00 -90.00  142
  8  \w    -10.00  96.00   0.50    8.60    --   10.60  82.00 -30.00  212
  9  \w    -15.00 100.00   0.50    8.60    --   10.60  77.00 -90.00  230
 10  \w     22.00  49.00   0.50    8.60    --   10.60  77.00  30.00   54
 11  \w    -13.00  15.00   0.50    8.60    --   10.60  77.00  30.00   56
 12  \w    -15.00  12.00   0.50    8.60    --   10.60  82.00 150.00   54
 13  \w      5.00  31.00   0.50    8.60    --   10.60 -82.00 -90.00   52
 14  \w    -27.00  18.00   0.50    8.60    --   10.60  19.00 120.00   90
 15  \w    -84.00 -59.00   0.50    8.60    --  -10.90 -82.00 -30.00   50
 16  \w    -72.00 -18.00   0.50    8.60    --  -10.90 -82.00-150.00  108
 17  \w    -97.00  17.00   0.50    8.60    --  -10.90 -82.00 120.00  228
 18  \w    -49.00 -24.00   0.50    8.60    --  -10.90 -82.00  60.00   50
 19  \w    -18.00   7.00   0.50    8.60    --  -10.90 -82.00  90.00   50
 20  \w    -96.00 -69.00   0.50    8.60    --  -10.90 -82.00  60.00   54
 21  \w     -9.00  16.00   0.50    8.60    --  -10.90 -82.00 -30.00   50
 22  \w    -69.00 -28.00   0.50    8.60    --  -10.90 -82.00  90.00   82
;
_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      -0.0594768000
_diffrn_orient_matrix_UB_12      -0.0155805000
_diffrn_orient_matrix_UB_13      0.0197595000
_diffrn_orient_matrix_UB_21      0.0375976000
_diffrn_orient_matrix_UB_22      -0.0615148000
_diffrn_orient_matrix_UB_23      0.0090496000
_diffrn_orient_matrix_UB_31      0.0428949000
_diffrn_orient_matrix_UB_32      0.0323950000
_diffrn_orient_matrix_UB_33      0.0266701000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28695
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.27
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
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    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0048(12)
_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   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+2.3008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1550
_reflns_number_gt                2942
_reflns_number_total             3493
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob02431g2.cif
_cod_data_source_block           sh0205down
_cod_depositor_comments
'Adding full bibliography for 7157832--7157834.cif.'
_cod_database_code               7157834
_chemical_oxdiff_formula         'C20 H20 N1 O5'
_diffrn_oxdiff_digest_frames
;
0126b3a205291ef699f7e1abb21f8374d4000253e04
;
_diffrn_oxdiff_digest_hkl
;
019a516f6cf94014a8a4bb4453f8688049f96f
;
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C20(H20A,H20B,H20C)
;
_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 1.319
_oxdiff_exptl_absorpt_empirical_full_min 0.754