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_7158214
_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         'C30 H23 N O3'
_chemical_formula_sum            'C30 H23 N O3'
_chemical_formula_weight         445.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-15
_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                97.174(3)
_cell_angle_beta                 111.174(3)
_cell_angle_gamma                92.350(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4667(4)
_cell_length_b                   10.6302(4)
_cell_length_c                   12.2360(4)
_cell_measurement_reflns_used    7540
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      75.9300
_cell_measurement_theta_min      3.9160
_cell_volume                     1134.28(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.973
_diffrn_measured_fraction_theta_max 0.986
_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    137.00 178.00   1.00    0.60    --  106.49  19.00 -90.00   41
  2  \w     89.00 126.00   1.00    0.60    --  106.49  77.00 120.00   37
  3  \w    136.00 178.00   1.00    0.60    --  106.49  77.00 120.00   42
  4  \w     95.00 174.00   1.00    0.60    --  106.49  62.00 170.00   79
  5  \w     32.00 114.00   1.00    0.10    --   48.45  62.00 170.00   82
  6  \w    111.00 176.00   1.00    0.60    --  106.49  19.00  60.00   65
  7  \w     95.00 134.00   1.00    0.60    --  106.49  19.00 -90.00   39
  8  \w     41.00  66.00   1.00    0.60    --  106.49 -57.00-120.00   25
  9  \w    145.00 178.00   1.00    0.60    --  106.49 125.00  90.00   33
 10  \w    102.00 134.00   1.00    0.60    --  106.49 125.00  90.00   32
 11  \w     34.00  59.00   1.00    0.60    --  106.49 -62.00  33.00   25
 12  \w    -23.00  43.00   1.00    0.10    --   48.45 -62.00  33.00   66
 13  \w     34.00 102.00   1.00    0.60    --  106.49 -99.00-120.00   68
 14  \w     83.00 109.00   1.00    0.60    --  106.49-125.00-120.00   26
 15  \w     65.00 106.00   1.00    0.60    --  106.49-125.00-150.00   41
 16  \w     40.00  81.00   1.00    0.60    --  106.49-125.00-120.00   41
 17  \w     34.00  60.00   1.00    0.60    --  106.49-125.00-150.00   26
 18  \w     35.00  96.00   1.00    0.10    --   48.45-125.00-120.00   61
 19  \w     73.00 104.00   1.00    0.60    --  106.49 -99.00 -30.00   31
 20  \w     43.00 105.00   1.00    0.60    --  106.49 -99.00 -90.00   62
 21  \w     34.00  64.00   1.00    0.60    --  106.49 -99.00 -30.00   30
 22  \w     36.00 106.00   1.00    0.60    --  106.49 -99.00  30.00   70
 23  \w     37.00  99.00   1.00    0.60    --  106.49 -99.00  90.00   62
 24  \w     40.00  80.00   1.00    0.60    --  106.49-125.00 150.00   40
 25  \w     86.00 111.00   1.00    0.60    --  106.49-125.00 150.00   25
 26  \w    -72.00 -34.00   1.00    0.60    --  -86.25  62.00 170.00   38
 27  \w    -64.00   9.00   1.00    0.10    --  -48.45  62.00 170.00   73
 28  \w    -66.00 -15.00   1.00    0.60    --  -86.25  57.00   0.00   51
 29  \w    -43.00 -17.00   1.00    0.60    --  -86.25  38.00 -30.00   26
 30  \w    -43.00 -18.00   1.00    0.60    --  -86.25  38.00-180.00   25
 31  \w   -119.00 -94.00   1.00    0.10    --  -48.45 -62.00  33.00   25
 32  \w    -87.00 -32.00   1.00    0.10    --  -48.45 -62.00  33.00   55
 33  \w   -109.00 -84.00   1.00    0.60    --  -86.25 -62.00  33.00   25
 34  \w   -143.00-114.00   1.00    0.60    --  -86.25 -62.00  33.00   29
;
_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      0.1382470000
_diffrn_orient_matrix_UB_12      -0.0544656000
_diffrn_orient_matrix_UB_13      -0.0204602000
_diffrn_orient_matrix_UB_21      0.0172152000
_diffrn_orient_matrix_UB_22      -0.0843674000
_diffrn_orient_matrix_UB_23      0.0968551000
_diffrn_orient_matrix_UB_31      -0.1063676000
_diffrn_orient_matrix_UB_32      -0.1069458000
_diffrn_orient_matrix_UB_33      -0.0940744000
_diffrn_radiation_collimation    0.3
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11182
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.919
_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    0.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0439P)^2^+0.2193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3565
_reflns_number_total             4003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00636c2.cif
_cod_data_source_block           200912c
_cod_depositor_comments
'Adding full bibliography for 7158213--7158214.cif.'
_cod_original_cell_volume        1134.28(7)
_cod_database_code               7158214
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CN
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.980
_diffrn_oxdiff_digest_frames
;
0124cea257839cf4f32f8bbb631c3f184a01496e42f
;
_diffrn_oxdiff_digest_hkl
;
0128a54342d866389c40f9221648549278ec34
;
_reflns_odcompleteness_completeness 98.67
_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
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 N17(H17), C8(H8), C3(H3), C16(H16), C15(H15), C33(H33), C9(H9), C34(H34),
 C32(H32), C13(H13), C30(H30), C31(H31), C14(H14), C23(H23), C6(H6), C4(H4),
 C7(H7), C25(H25), C27(H27), C26(H26), C24(H24)
;
_shelx_res_checksum              33729
_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 1.535
_oxdiff_exptl_absorpt_empirical_full_min 0.717