Synthesis of non-C<sub>2</sub> symmetrical NOBIN-type biaryls through a cascade N-arylation and [3,3]-sigmatropic rearrangement from O-arylhydroxylamines and diaryliodonium salts.
Liu, Fengting; Wang, Min; Qu, Jiatong; Lu, Haifeng; Gao, Hongyin; Organic & biomolecular chemistry 19 (2021) 7246–7251; doi:10.1039/d1ob00636c

data_7158213
_publ_section_title
;
 Synthesis of non-C<sub>2</sub> symmetrical NOBIN-type biaryls through a
 cascade N-arylation and [3,3]-sigmatropic rearrangement from
 O-arylhydroxylamines and diaryliodonium salts.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7246
_journal_page_last               7251
_journal_paper_doi               10.1039/d1ob00636c
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C24 H19 N O3'
_chemical_formula_sum            'C24 H19 N O3'
_chemical_formula_weight         369.40
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-12-12 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.796(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7971(5)
_cell_length_b                   10.5432(3)
_cell_length_c                   10.0972(3)
_cell_measurement_reflns_used    5715
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.0440
_cell_measurement_theta_min      4.2370
_cell_volume                     1894.44(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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     94.00 178.00   1.00    0.40    --  106.49  19.00 -60.00   84
  2  \w     95.00 132.00   1.00    0.40    --  106.49  21.00 -97.00   37
  3  \w     60.00 124.00   1.00    0.10    --   48.45  21.00 -97.00   64
  4  \w     35.00  61.00   1.00    0.40    --  106.49 -57.00-180.00   26
  5  \w    -22.00  22.00   1.00    0.10    --   48.45 -21.00  95.00   44
  6  \w     35.00  66.00   1.00    0.40    --  106.49 -57.00 150.00   31
  7  \w     40.00  66.00   1.00    0.40    --  106.49 -57.00 120.00   26
  8  \w     34.00 105.00   1.00    0.40    --  106.49 -77.00  30.00   71
  9  \w     34.00 106.00   1.00    0.40    --  106.49 -99.00   0.00   72
 10  \w     34.00  60.00   1.00    0.40    --  106.49-125.00   0.00   26
 11  \w     64.00 106.00   1.00    0.40    --  106.49-125.00   0.00   42
 12  \w     -7.00  26.00   1.00    0.10    --  -48.45  21.00 -97.00   33
 13  \w    -62.00 -16.00   1.00    0.40    --  -86.25  57.00  60.00   46
 14  \w    -25.00  27.00   1.00    0.10    --  -48.45  19.00  60.00   52
 15  \w   -120.00 -53.00   1.00    0.10    --  -48.45 -21.00  95.00   67
 16  \w   -109.00 -84.00   1.00    0.40    --  -86.25 -21.00  95.00   25
 17  \w   -151.00 -86.00   1.00    0.40    --  -86.25 -99.00-120.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0439627000
_diffrn_orient_matrix_UB_12      0.0409499000
_diffrn_orient_matrix_UB_13      0.1231780000
_diffrn_orient_matrix_UB_21      0.0732570000
_diffrn_orient_matrix_UB_22      -0.0009042000
_diffrn_orient_matrix_UB_23      0.0828458000
_diffrn_orient_matrix_UB_31      0.0132370000
_diffrn_orient_matrix_UB_32      0.1404418000
_diffrn_orient_matrix_UB_33      -0.0354071000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9973
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.875
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0770P)^2^+0.6736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1484
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2939
_reflns_number_total             3343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00636c2.cif
_cod_data_source_block           200919c
_cod_depositor_comments
'Adding full bibliography for 7158213--7158214.cif.'
_cod_database_code               7158213
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         OC
_reflns_odcompleteness_completeness 98.78
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 N17(H17), C9(H9), C16(H16), C14(H14), C13(H13), C15(H15), C6(H6), C3(H3),
 C8(H8), C4(H4), C7(H7), C27(H27), C23(H23), C26(H26), C25(H25), C24(H24)
2.c Idealised tetrahedral OH refined as rotating group:
 O28(H28)
;
_shelx_res_checksum              66491
_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 1.550
_oxdiff_exptl_absorpt_empirical_full_min 0.565