Tandem approach to NOBIN analogues from arylhydroxylamines and diaryliodonium salts via [3,3]-sigmatropic rearrangement.
Yuan, Hairui; Du, Yuanbo; Liu, Fengting; Guo, Lirong; Sun, Qianyu; Feng, Lei; Gao, Hongyin; Chemical communications (Cambridge, England) 56 (2020) 8226–8229; doi:10.1039/d0cc02919j

data_7126730
_publ_section_title
;
 Tandem approach to NOBIN analogues from arylhydroxylamines and
 diaryliodonium salts via [3,3]-sigmatropic rearrangement.
;
_journal_issue                   59
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8226
_journal_page_last               8229
_journal_paper_doi               10.1039/d0cc02919j
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C23 H15 Br2 N O2'
_chemical_formula_sum            'C23 H15 Br2 N O2'
_chemical_formula_weight         497.18
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-30 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.98050(10)
_cell_length_b                   11.7542(2)
_cell_length_c                   18.4054(3)
_cell_measurement_reflns_used    10629
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.6820
_cell_measurement_theta_min      4.4240
_cell_volume                     1942.85(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.999
_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   -118.00 -65.00   1.00    0.12    --  -48.45-137.00 -58.00   53
  2  \w   -102.00 -67.00   1.00    0.12    --  -48.45-132.00 118.00   35
  3  \w    -92.00 -39.00   1.00    0.12    --  -48.45 137.00   4.00   53
  4  \w     43.00  68.00   1.00    0.12    --   48.45-132.00 118.00   25
  5  \w     46.00  71.00   1.00    0.12    --   48.45-137.00 -58.00   25
  6  \w   -101.00 -75.00   1.00    0.60    --  -86.25-137.00 -58.00   26
  7  \w    -97.00 -17.00   1.00    0.60    --  -86.25 132.00-171.00   80
  8  \w     72.00  98.00   1.00    0.60    --  106.49-137.00 -58.00   26
  9  \w     35.00  88.00   1.00    0.60    --  106.49-132.00 118.00   53
 10  \w     92.00 170.00   1.00    0.60    --  106.49 137.00   4.00   78
 11  \w     91.00 176.00   1.00    0.60    --  106.49 132.00-171.00   85
 12  \w     91.00 122.00   1.00    0.60    --  106.49-132.00 118.00   31
 13  \w    -61.00  26.00   1.00    0.12    --  -48.45  19.00  30.00   87
 14  \w    -49.00 -22.00   1.00    0.12    --  -48.45 132.00-171.00   27
 15  \w     27.00 120.00   1.00    0.12    --   48.45  77.00 -90.00   93
 16  \w   -158.00 -74.00   1.00    0.60    --  -86.25 -38.00 -60.00   84
 17  \w     34.00 106.00   1.00    0.60    --  106.49 -99.00 -30.00   72
 18  \w     92.00 177.00   1.00    0.60    --  106.49 125.00-120.00   85
 19  \w     34.00  64.00   1.00    0.60    --  106.49 -38.00-120.00   30
 20  \w    139.00 175.00   1.00    0.60    --  106.49 125.00 120.00   36
 21  \w     98.00 134.00   1.00    0.60    --  106.49 125.00 120.00   36
 22  \w     36.00 101.00   1.00    0.60    --  106.49 -99.00-150.00   65
 23  \w     76.00 118.00   1.00    0.60    --  106.49 -38.00-120.00   42
 24  \w     84.00 178.00   1.00    0.60    --  106.49  77.00  90.00   94
 25  \w     34.00 120.00   1.00    0.60    --  106.49 -38.00  60.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0240420000
_diffrn_orient_matrix_UB_12      0.1162621000
_diffrn_orient_matrix_UB_13      0.0367600000
_diffrn_orient_matrix_UB_21      -0.0410298000
_diffrn_orient_matrix_UB_22      -0.0604601000
_diffrn_orient_matrix_UB_23      0.0715415000
_diffrn_orient_matrix_UB_31      0.1648358000
_diffrn_orient_matrix_UB_32      0.0019251000
_diffrn_orient_matrix_UB_33      0.0231566000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18763
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         4.463
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    5.447
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1286 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.083(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0343P)^2^+1.1482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3194
_reflns_number_total             3460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02919j2.cif
_cod_data_source_block           191227b
_cod_depositor_comments
'Adding full bibliography for 7126729--7126730.cif.'
_cod_database_code               7126730
_shelxl_version_number           2013-4
_chemical_oxdiff_usercomment     BrCNO
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              81048
_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 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.740