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_7245736
_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         'C15 H11 N O'
_chemical_formula_sum            'C15 H11 N O'
_chemical_formula_weight         221.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-15 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.583(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.473(2)
_cell_length_b                   6.0831(6)
_cell_length_c                   19.451(2)
_cell_measurement_reflns_used    1593
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      2.80
_cell_volume                     2148.6(4)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9320
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.515
_diffrn_reflns_theta_min         2.130
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0664 before and 0.0552 after correction. The Ratio of minimum to maximum transmission is 0.8193. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0617
_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^)+(0.0781P)^2^+0.6741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1769
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1208
_reflns_number_total             2200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra06097c3.cif
_cod_data_source_block           zz
_cod_original_cell_volume        2148.5(4)
_cod_database_code               7245736
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.990
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C15(H15), C11(H11), C1(H1), C3(H3), C14(H14), C12(H12),
 C13(H13), C5(H5), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'