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_1543745
_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_formula_moiety         'C22 H22 N2 O2 S'
_chemical_formula_sum            'C22 H22 N2 O2 S'
_chemical_formula_weight         378.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-08-04
_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                 90.2280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1061(3)
_cell_length_b                   18.1581(5)
_cell_length_c                   20.5423(6)
_cell_measurement_reflns_used    9737
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.98
_cell_measurement_theta_min      3.25
_cell_volume                     3769.64(19)
_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 0.988
_diffrn_measured_fraction_theta_max 0.980
_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  0.0432
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            49569
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.410
_diffrn_reflns_theta_min         3.248
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.680
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0713 before and 0.0576 after correction.
The Ratio of minimum to maximum transmission is 0.8858.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         6932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0457P)^2^+1.2559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5982
_reflns_number_total             6932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc02231f3.cif
_cod_data_source_block           lk_3_287a_0m_a
_cod_database_code               1543745
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.824
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C15(H15), C19(H19), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C21(H21A,H21B), C30(H30A,H30B), C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C6(H6), C8(H8), C9(H9), C10(H10), C12(H12), C14(H14), C16(H16),
 C17(H17), C18(H18), C20(H20), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28),
  C29(H29), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36),
 C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44)
;
_shelx_res_checksum              5930
_olex2_submission_special_instructions 'No special instructions were received'