Copper-catalyzed C5-selective thio/selenocyanation of 8-aminoquinolines
Chen, Jichao; Wang, Tianyu; Wang, Tong; Lin, Aijun; Yao, Hequan; Xu, Jinyi; Organic Chemistry Frontiers 4 (2017) 130–; doi:10.1039/C6QO00590J

data_1553573
_publ_section_title
;
 Copper-catalyzed C5-selective thio/selenocyanation of 8-aminoquinolines
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              130
_journal_paper_doi               10.1039/C6QO00590J
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C14 H13 N3 O S'
_chemical_formula_weight         271.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-06-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                85.960(7)
_cell_angle_beta                 77.314(7)
_cell_angle_gamma                66.467(7)
_cell_formula_units_Z            2
_cell_length_a                   7.680(5)
_cell_length_b                   8.494(5)
_cell_length_c                   11.449(7)
_cell_measurement_reflns_used    1593
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.619
_cell_volume                     667.9(7)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_device_type  'Bruker Smart Aepex CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5029
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.766
_diffrn_reflns_theta_min         1.823
_exptl_absorpt_coefficient_mu    0.237
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.017(8)
_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   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2544
_refine_ls_number_restraints     280
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.172
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1184P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1661
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1906
_reflns_number_total             2544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00590j2.cif
_cod_data_source_block           A
_cod_database_code               1553573
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.986
_shelxl_version_number           2013-2
_shelx_res_checksum              4172
_shelx_hkl_checksum              32033