Changing stereoselectivity and regioselectivity in copper(i)-catalyzed 5-exo cyclization by chelation and rigidity in aminoalkyl radicals: synthesis towards diverse bioactive N-heterocycles
Sadanandan, Sandhya; Gupta, Dharmendra Kumar; New Journal of Chemistry 44 (2020) 3350–3365; doi:10.1039/C9NJ05166J

data_7059232
_publ_section_title
;
 Changing stereoselectivity and regioselectivity in copper(i)-catalyzed
 5-exo cyclization by chelation and rigidity in aminoalkyl radicals:
 synthesis towards diverse bioactive N-heterocycles
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3350
_journal_page_last               3365
_journal_paper_doi               10.1039/C9NJ05166J
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C13 H12 Cl3 N O2'
_chemical_formula_sum            'C13 H12 Cl3 N O2'
_chemical_formula_weight         320.59
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-12-08 deposited with the CCDC.	2020-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.188(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.302(3)
_cell_length_b                   13.884(3)
_cell_length_c                   8.368(2)
_cell_measurement_reflns_used    2237
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      0.923
_cell_measurement_theta_min      0.895
_cell_volume                     1402.1(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13072
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.275
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.275
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0861
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+3.0422P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1667
_refine_ls_wR_factor_ref         0.1723
_reflns_number_gt                2237
_reflns_number_total             2462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9nj05166j2.cif
_cod_data_source_block           dkg1m
_cod_depositor_comments
;Adding full bibliography for 7059231--7059232.cif.

 Adding full bibliography for 7059231--7059232.cif.
;
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7059232