Intramolecular 1,5-C(sp3)-H Radical Amination via Co(II)-Based Metalloradical Catalysis for Five-Membered Cyclic Sulfamides
Lu, Hongjian; lang, kai; Jiang, Huiling; Wojtas, Lukasz; Zhang, Peter; Chem. Sci.  (2016) –; doi:10.1039/C6SC02231F

data_1543744
_publ_section_title
;
 Intramolecular 1,5-C(sp3)-H Radical Amination via Co(II)-Based
 Metalloradical Catalysis for Five-Membered Cyclic Sulfamides
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C6SC02231F
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H17 N3 O4 S'
_chemical_formula_sum            'C15 H17 N3 O4 S'
_chemical_formula_weight         335.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2016-05-19 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0617(2)
_cell_length_b                   7.1812(2)
_cell_length_c                   35.5229(10)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.02
_cell_measurement_theta_min      4.98
_cell_volume                     1546.32(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            19967
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.325
_diffrn_reflns_theta_min         4.980
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.086
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.4798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1620 before and 0.0935 after correction.
The Ratio of minimum to maximum transmission is 0.6370.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.086(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0524P)^2^+0.4201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0849
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2715
_reflns_number_total             2863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc02231f3.cif
_cod_data_source_block           lk_4_36_0m
_cod_database_code               1543744
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.624
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_shelx_res_checksum              88154
_olex2_submission_special_instructions 'No special instructions were received'