Generation of 1-amino-isoquinoline-N-oxides via a tandem reaction of 2-alkynylbenzaldoxime with secondary amines in the presence of silver(i) and copper(i)
Song, Junjie; Fan, Congbin; Liu, Gang; Qiu, Guanyinsheng; Org. Chem. Front. 1 (2014) 1045–; doi:10.1039/C4QO00209A

data_1553032
_publ_section_title
;
 Generation of 1-amino-isoquinoline-N-oxides via a tandem reaction of
 2-alkynylbenzaldoxime with secondary amines in the presence of silver(i)
 and copper(i)
;
_journal_issue                   9
_journal_name_full               'Org. Chem. Front.'
_journal_page_first              1045
_journal_paper_doi               10.1039/C4QO00209A
_journal_volume                  1
_journal_year                    2014
_chemical_formula_sum            'C20 H20 N2 O'
_chemical_formula_weight         304.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 100.618(8)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   11.245(6)
_cell_length_b                   22.954(12)
_cell_length_c                   26.071(13)
_cell_measurement_reflns_used    1017
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.514
_cell_measurement_theta_min      2.373
_cell_volume                     6614(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.1399
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27066
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         1.589
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            corlorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.00023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.698
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     830
_refine_ls_number_reflns         11651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.698
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0230P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4288
_reflns_number_total             11651
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4qo00209a2.cif
_cod_data_source_block           a40519a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1553032
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2013-2
_shelx_res_checksum              37892
_shelx_hkl_checksum              53461