Facile synthesis of isoquinolines and isoquinoline N-oxides via a copper-catalyzed intramolecular cyclization in water
Zhang, Lujun; Xiong, Wenfang; Yao, Biao; Liu, Haitao; Li, Meng; Qin, Yu; Yu, Yujian; Li, Xu; Chen, Meng; Wu, Wanqing; Li, Jianxiao; Wang, Jinliang; Jiang, Huanfeng; RSC Advances 12 (2022) 30248–30252; doi:10.1039/D2RA06097C

data_7245737
_publ_section_title
;
 Facile synthesis of isoquinolines and isoquinoline N-oxides via a
 copper-catalyzed intramolecular cyclization in water
;
_journal_issue                   47
_journal_name_full               'RSC Advances'
_journal_page_first              30248
_journal_page_last               30252
_journal_paper_doi               10.1039/D2RA06097C
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C22 H28 N2 O2'
_chemical_formula_sum            'C22 H28 N2 O2'
_chemical_formula_weight         352.46
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-16 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   22.8147(12)
_cell_length_b                   22.8147(12)
_cell_length_c                   10.5217(7)
_cell_measurement_reflns_used    2460
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.947
_cell_measurement_theta_min      2.193
_cell_volume                     4742.9(5)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13322
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.459
_diffrn_reflns_theta_min         2.193
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0903 before and 0.0576 after correction. The Ratio of minimum to maximum transmission is 0.9109. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_description       block
_exptl_crystal_F_000             1710
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_platon_squeeze_details
;
TITL 04_a.res in R-3
CELL   22.8147   22.8147   10.5217     90.00     90.00    120.00
SPGR R-3
C101 0.030 0.086 0.024 !       4.62 eA-3
C102 1.000 0.998 0.063 !       2.32 eA-3
Q103 0.015 0.695 0.247 !       0.88 eA-3
Q104 0.766 0.609 0.375 !       0.83 eA-3
Q105 0.860 0.450 0.468 !       0.81 eA-3
Q106 0.719 0.935 0.846 !       0.79 eA-3
Q107 0.086 0.724 0.436 !       0.76 eA-3
Q108 0.718 0.227 0.025 !       0.67 eA-3
Q109 0.564 0.068 0.523 !       0.65 eA-3
Q110 0.845 0.532 0.218 !       0.64 eA-3
Q111 0.236 0.085 0.373 !       0.58 eA-3
Q112 0.234 0.195 0.371 !       0.57 eA-3
Q113 0.384 0.859 0.179 !       0.50 eA-3
;
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0586P)^2^+8.1661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1559
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1361
_reflns_number_total             2167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra06097c3.cif
_cod_data_source_block           04_sq
_cod_original_cell_volume        4742.9(6)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7245737
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.989
_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 Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C9(H9)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'