Regioselective <i>ortho</i> C-H insertion of <i>N</i>-nitrosoanilines with naphthoquinone carbenes.
Peng, Rui-Jun; Chen, Yuan; Zhang, Xue-Jing; Yan, Ming; Organic & biomolecular chemistry 21 (2023) 7525–7529; doi:10.1039/d3ob01104f

data_7159547
_publ_section_title
;
 Regioselective <i>ortho</i> C-H insertion of <i>N</i>-nitrosoanilines
 with naphthoquinone carbenes.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7525
_journal_page_last               7529
_journal_paper_doi               10.1039/d3ob01104f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C17 H14 N2 O2'
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30
_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     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2gw99z
_audit_creation_date             2023-08-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-08-23 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.324(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3559(4)
_cell_length_b                   8.1137(2)
_cell_length_c                   16.0334(4)
_cell_measurement_reflns_used    6131
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3330
_cell_measurement_theta_min      3.9370
_cell_volume                     1448.53(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.949
_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     83.00 176.00   0.50    0.05    --  105.85  15.00 150.00  186
  2  \w     91.00 135.00   0.50    0.05    --  105.85  45.00 -60.00   88
  3  \w     93.00 157.00   0.50    0.05    --  105.85  19.00-140.00  128
  4  \w     51.00  77.00   0.50    0.05    --   44.84  19.00-140.00   52
  5  \w     41.00  70.00   0.50    0.05    --  105.85 -77.00 -60.00   58
  6  \w     33.00  63.00   0.50    0.05    --  105.85 -61.00 120.00   60
  7  \w     38.00  73.00   0.50    0.05    --  105.85 -61.00  60.00   70
  8  \w     36.00  70.00   0.50    0.05    --  105.85 -61.00  30.00   68
  9  \w     38.00  68.00   0.50    0.05    --  105.85 -61.00-180.00   60
 10  \w     71.00 110.00   0.50    0.05    --  105.85-125.00 -90.00   78
 11  \w    -16.00  13.00   0.50    0.05    --  -44.84  19.00-140.00   58
 12  \w    -39.00  30.00   0.50    0.05    --  -44.84  38.00 -60.00  138
 13  \w     34.00 101.00   0.50    0.05    --  105.85 -94.00-120.00  134
 14  \w    -29.00  28.00   0.50    0.05    --   44.84 -19.00 -90.00  114
 15  \w   -141.00 -79.00   0.50    0.05    -- -100.00 -19.00  52.00  124
 16  \w    -30.00  16.00   0.50    0.05    --   44.84 -19.00  52.00   92
 17  \w    -31.00  26.00   0.50    0.05    --   44.84 -19.00 -30.00  114
 18  \w    -98.00 -73.00   0.50    0.05    --  -44.84 -19.00  52.00   50
 19  \w    -63.00 -30.00   0.50    0.05    -- -100.00  61.00   0.00   66
 20  \w    -59.00 -28.00   0.50    0.05    -- -100.00  77.00   0.00   62
 21  \w    -60.00 -34.00   0.50    0.05    -- -100.00  61.00  60.00   52
 22  \w    -98.00 -72.00   0.50    0.05    -- -100.00  77.00   0.00   52
 23  \w    -66.00 -32.00   0.50    0.05    -- -100.00  61.00 -60.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1356691000
_diffrn_orient_matrix_UB_12      0.0345293000
_diffrn_orient_matrix_UB_13      -0.0249710000
_diffrn_orient_matrix_UB_21      -0.0131942000
_diffrn_orient_matrix_UB_22      -0.0336554000
_diffrn_orient_matrix_UB_23      0.0922965000
_diffrn_orient_matrix_UB_31      0.0235466000
_diffrn_orient_matrix_UB_32      0.1836334000
_diffrn_orient_matrix_UB_33      0.0217002000
_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  0.0272
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8568
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.594
_diffrn_reflns_theta_min         3.970
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0670P)^2^+0.4587P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2496
_reflns_number_total             2857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01104f2.cif
_cod_data_source_block           cheny_230823_auto
_cod_depositor_comments          'Adding full bibliography for 7159547.cif.'
_cod_original_cell_volume        1448.52(7)
_cod_database_code               7159547
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     CHON
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.820
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C12(H12), C9(H9), C4(H4), C3(H3), C13(H13), C6(H6),
 C7(H7), C8(H8)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
2.c Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_shelx_res_checksum              65949
_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 2.390
_oxdiff_exptl_absorpt_empirical_full_min 0.578