Sulfonamide-Directed Chemo- and Site-Selective Oxidative Halogenation/Amination Using Halogenating Reagents Generated in Situ from Cyclic Diacyl Peroxides.
Chang, Denghu; Zhao, Rong; Wei, Congyin; Yao, Yuan; Liu, Yang; Shi, Lei; The Journal of organic chemistry 83 (2018) 3305–3315; doi:10.1021/acs.joc.8b00243

data_4035176
_publ_section_title
;
 Sulfonamide-Directed Chemo- and Site-Selective Oxidative
 Halogenation/Amination Using Halogenating Reagents Generated in Situ from
 Cyclic Diacyl Peroxides.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3305
_journal_page_last               3315
_journal_paper_doi               10.1021/acs.joc.8b00243
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C8 H5 O4, C16 H36 N'
_chemical_formula_sum            'C24 H41 N O4'
_chemical_formula_weight         407.58
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.278(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2253(9)
_cell_length_b                   9.1994(6)
_cell_length_c                   17.8109(10)
_cell_measurement_reflns_used    2252
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.7110
_cell_measurement_theta_min      3.7650
_cell_volume                     2474.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     -7.00  40.00   1.00   20.00    --   18.81  37.00 -30.00   47
  2  \w    -44.00  46.00   1.00   20.00    --   18.81 -37.00 150.00   90
  3  \w    -19.00   7.00   1.00   20.00    --   18.81 -99.00  60.00   26
  4  \w    -40.00  -7.00   1.00   20.00    --   18.81 -57.00  90.00   33
  5  \w     15.00  40.00   1.00   20.00    --   18.81 -57.00  90.00   25
  6  \w     59.00  91.00   1.00   20.00    --   18.81  37.00 -30.00   32
  7  \w    -60.00 -35.00   1.00   20.00    --  -19.74 -37.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0365918000
_diffrn_orient_matrix_UB_12      0.0200638000
_diffrn_orient_matrix_UB_13      0.0266302000
_diffrn_orient_matrix_UB_21      -0.0293643000
_diffrn_orient_matrix_UB_22      0.0225526000
_diffrn_orient_matrix_UB_23      0.0255638000
_diffrn_orient_matrix_UB_31      0.0009801000
_diffrn_orient_matrix_UB_32      -0.0708535000
_diffrn_orient_matrix_UB_33      0.0156601000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10996
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.906
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0758
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0955P)^2^+0.6036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2066
_refine_ls_wR_factor_ref         0.2538
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2206
_reflns_number_total             4500
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00243_si_001.cif
_cod_data_source_block           161223
_cod_database_code               4035176
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'Br C H N O'
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Shared sites
{C22A, C22}
3. Rigid bond restraints
 C7, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C22A) = Uanis(C22)
5. Others
 Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23C)=
 Sof(H23D)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
6.a Riding coordinates:
 O3(H3)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B),
  C21(H21C,H21D), C22(H22A,H22B), C22A(H22C,H22D), C23(H23A,H23B), C23A(H23C,
 H23D)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6)
6.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C24(H24A,H24B,
 H24C), C24A(H24D,H24E,H24F)
;
_shelx_res_checksum              19704
_shelx_hkl_checksum              97039
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.723
_oxdiff_exptl_absorpt_empirical_full_min 0.620