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_7126729
_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_formula_moiety         'C24 H16 F3 N O2'
_chemical_formula_sum            'C24 H16 F3 N O2'
_chemical_formula_weight         407.38
_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   geom
_audit_creation_date             2018-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2020-03-09 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.910(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0044(8)
_cell_length_b                   8.2203(3)
_cell_length_c                   19.4734(10)
_cell_measurement_reflns_used    3629
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      76.4970
_cell_measurement_theta_min      4.7410
_cell_volume                     2272.2(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.992
_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    -48.00  26.00   1.00    0.70    --  -48.45  15.00  44.00   74
  2  \w   -123.00 -38.00   1.00    0.70    --  -48.45 -15.00-126.00   85
  3  \w     55.00  81.00   1.00    0.70    --   48.45  15.00  44.00   26
  4  \w    -19.00   7.00   1.00    0.70    --   48.45 -15.00-126.00   26
  5  \w    -80.00 -55.00   1.00    6.00    --  -86.25  15.00  44.00   25
  6  \w   -142.00-101.00   1.00    6.00    --  -86.25 -15.00-126.00   41
  7  \w     97.00 176.00   1.00    6.00    --  107.75  15.00  44.00   79
  8  \w     34.00 108.00   1.00    6.00    --  107.75 -15.00-126.00   74
  9  \w    -24.00  61.00   1.00    0.70    --   48.45 -37.00 120.00   85
 10  \w     35.00 120.00   1.00    6.00    --  107.75 -37.00-150.00   85
 11  \w     35.00 117.00   1.00    6.00    --  107.75-125.00-120.00   82
 12  \w     49.00 108.00   1.00    6.00    --  107.75 -99.00   0.00   59
 13  \w     35.00 109.00   1.00    6.00    --  107.75 -99.00-120.00   74
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0003964000
_diffrn_orient_matrix_UB_12      0.0281041000
_diffrn_orient_matrix_UB_13      0.0783227000
_diffrn_orient_matrix_UB_21      -0.1076527000
_diffrn_orient_matrix_UB_22      -0.0237017000
_diffrn_orient_matrix_UB_23      -0.0251212000
_diffrn_orient_matrix_UB_31      0.0140803000
_diffrn_orient_matrix_UB_32      -0.1836957000
_diffrn_orient_matrix_UB_33      0.0152125000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12336
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         3.257
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (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    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0666
_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^)+(0.1121P)^2^+0.7710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1903
_refine_ls_wR_factor_ref         0.2101
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2986
_reflns_number_total             4025
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02919j2.cif
_cod_data_source_block           181016a_sq_s
_cod_depositor_comments
'Adding full bibliography for 7126729--7126730.cif.'
_cod_database_code               7126729
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CNOF
_reflns_odcompleteness_completeness 99.18
_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), C23(H23), C4(H4), C20(H20), C17(H17), C8(H8), C1(H1B), C3(H3),
 C13(H13), C21(H21), C2(H2), C7(H7), C14(H14), C16(H16), C15(H15)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              49297
_shelx_fab_checksum              85284
_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 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.642