A facile metal-free one-pot synthesis of 3-aminoisoquinolines by intramolecular transannulation of 1-sulfonyl-4-(2-aminomethylphenyl)-1,2,3-triazoles
Shang, Hai; Li, Ling-Yu; Tian, Yu; Jia, Hong-Mei; Zou, Zhong-Mei; RSC Advances 10 (2020) 39067–39071; doi:10.1039/D0RA06563C

data_7241661
_publ_section_title
;
 A facile metal-free one-pot synthesis of 3-aminoisoquinolines by
 intramolecular transannulation of
 1-sulfonyl-4-(2-aminomethylphenyl)-1,2,3-triazoles
;
_journal_issue                   64
_journal_name_full               'RSC Advances'
_journal_page_first              39067
_journal_page_last               39071
_journal_paper_doi               10.1039/D0RA06563C
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C16 H14 N2 O2 S'
_chemical_formula_sum            'C16 H14 N2 O2 S'
_chemical_formula_weight         298.35
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-09-01
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  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2020-09-02 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.613(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8959(4)
_cell_length_b                   11.5231(4)
_cell_length_c                   10.6044(4)
_cell_measurement_reflns_used    2112
_cell_measurement_temperature    112.05(10)
_cell_measurement_theta_max      29.0070
_cell_measurement_theta_min      3.9390
_cell_volume                     1418.55(9)
_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
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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_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      112.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.8432
_diffrn_measurement_details
;
  1 omega  -45.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -37.0000  -30.0000 78

  2 omega   -1.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   37.0000  150.0000 69

  3 omega   41.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  178.0000    0.0000 46

  4 omega  -83.00  -44.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  152.0000 -122.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0491023000
_diffrn_orient_matrix_UB_12      -0.0328646000
_diffrn_orient_matrix_UB_13      0.0296116000
_diffrn_orient_matrix_UB_21      0.0357726000
_diffrn_orient_matrix_UB_22      0.0486294000
_diffrn_orient_matrix_UB_23      -0.0035900000
_diffrn_orient_matrix_UB_31      -0.0066467000
_diffrn_orient_matrix_UB_32      0.0185722000
_diffrn_orient_matrix_UB_33      0.0616899000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6321
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.51
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97758
_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_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.4807P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                2328
_reflns_number_total             2785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ra06563c2.cif
_cod_data_source_block           exp_6362
_cod_original_cell_volume        1418.54(9)
_cod_database_code               7241661
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32