Environmentally friendly Nafion-catalyzed synthesis of 3-substituted isoquinoline by using hexamethyldisilazane as a nitrogen source under microwave irradiation.
Lin, Tzu-Chun; Chan, Chieh-Kai; Chung, Yi-Hsiu; Wang, Cheng-Chung; Organic & biomolecular chemistry 21 (2023) 7316–7326; doi:10.1039/d3ob01032e

data_7159492
_publ_section_title
;
 Environmentally friendly Nafion-catalyzed synthesis of 3-substituted
 isoquinoline by using hexamethyldisilazane as a nitrogen source under
 microwave irradiation.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7316
_journal_page_last               7326
_journal_paper_doi               10.1039/d3ob01032e
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H13 N'
_chemical_formula_sum            'C16 H13 N'
_chemical_formula_weight         219.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-26 deposited with the CCDC.	2023-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.6020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.07430(10)
_cell_length_b                   7.29170(10)
_cell_length_c                   12.6835(2)
_cell_measurement_reflns_used    7487
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      72.5
_cell_measurement_theta_min      3.55
_cell_volume                     552.187(15)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonIII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8632
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.608
_diffrn_reflns_theta_min         3.545
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8369
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.165
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 894 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2104
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.0996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                2083
_reflns_number_total             2104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01032e2.cif
_cod_data_source_block           i18487
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159492--7159494.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159492
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.892
_shelx_estimated_absorpt_t_max   0.909
_shelx_res_checksum              33831