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_7157832
_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         'C H Cl3, 2(C26 H21 N O3)'
_chemical_formula_sum            'C53 H43 Cl3 N2 O6'
_chemical_formula_weight         910.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-03-05
_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                83.0810(10)
_cell_angle_beta                 83.3180(10)
_cell_angle_gamma                79.1050(10)
_cell_formula_units_Z            2
_cell_length_a                   9.82420(10)
_cell_length_b                   13.6944(2)
_cell_length_c                   17.0549(3)
_cell_measurement_reflns_used    22767
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.8650
_cell_measurement_theta_min      1.8440
_cell_volume                     2226.41(6)
_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    '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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -17.00 100.00   0.50   22.14    --   10.60  82.00-120.00  234
  2  \w    -17.00 100.00   0.50   22.14    --   10.60  82.00 -60.00  234
  3  \w    -15.00 100.00   0.50   22.14    --   10.60  77.00 -60.00  230
  4  \w    -79.00  38.00   0.50   22.14    --   10.60 -82.00  60.00  234
  5  \w    -15.00 100.00   0.50   22.14    --   10.60  77.00 -30.00  230
  6  \w    -16.00  29.00   0.50   22.14    --   10.60  82.00 150.00   90
  7  \w    -20.00 100.00   0.50   22.14    --   10.60  57.00-120.00  240
  8  \w    -60.00 -24.00   0.50   22.14    --   10.60 -57.00-180.00   72
  9  \w    -13.00  17.00   0.50   22.14    --   10.60  57.00 120.00   60
 10  \w     32.00  59.00   0.50   22.14    --   10.60  57.00 120.00   54
 11  \w     61.00  87.00   0.50   22.14    --   10.60  57.00 120.00   52
 12  \w    -79.00  18.00   0.50   22.14    --   10.60 -38.00 120.00  194
 13  \w    -17.00   9.00   0.50   22.14    --   10.60  82.00   0.00   52
 14  \w     38.00  92.00   0.50   22.14    --   10.60  82.00   0.00  108
 15  \w     34.00  93.00   0.50   22.14    --   10.60  77.00-120.00  118
 16  \w    -97.00 -72.00   0.50   22.14    --  -10.90 -82.00 -60.00   50
 17  \w     -8.00  17.00   0.50   22.14    --  -10.90 -82.00  90.00   50
 18  \w    -82.00   4.00   0.50   22.14    --  -10.90 -82.00   0.00  172
 19  \w    -90.00 -64.00   0.50   22.14    --  -10.90 -82.00  90.00   52
 20  \w    -31.00  17.00   0.50   22.14    --  -10.90 -82.00 -60.00   96
;
_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      -0.0137704000
_diffrn_orient_matrix_UB_12      -0.0373826000
_diffrn_orient_matrix_UB_13      0.0309271000
_diffrn_orient_matrix_UB_21      0.0135905000
_diffrn_orient_matrix_UB_22      0.0299773000
_diffrn_orient_matrix_UB_23      0.0283183000
_diffrn_orient_matrix_UB_31      -0.0712869000
_diffrn_orient_matrix_UB_32      0.0226864000
_diffrn_orient_matrix_UB_33      0.0036115000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            49820
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.04
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64568
_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    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.420
_refine_diff_density_min         -1.269
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         8704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0963P)^2^+3.0166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.1861
_reflns_number_gt                7076
_reflns_number_total             8704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob02431g2.cif
_cod_data_source_block           sh0227-1
_cod_depositor_comments
'Adding full bibliography for 7157832--7157834.cif.'
_cod_database_code               7157832
_diffrn_oxdiff_digest_frames
;
01158603f32e28b6ec1a96e8701814ca40000258219
;
_diffrn_oxdiff_digest_hkl
;
01c179d4427678c9a692e448c57aea4bfa4ca3
;
_reflns_odcompleteness_completeness 99.37
_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. Others
 Sof(Cl4)=Sof(Cl5)=Sof(H53A)=1-FVAR(1)
 Sof(Cl2)=Sof(Cl3)=Sof(H53)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C53(H53), C53(H53A)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C28(H28), C32(H32), C34(H34), C39(H39),
  C40(H40), C41(H41), C42(H42), C44(H44), C46(H46), C47(H47), C48(H48), C49(H49)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C36(H36A,H36B,
 H36C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C)
;
_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.761