Rhodium(III)-catalyzed mild and regioselective dearomative spirocyclization of 2-aryl-3-nitrosoindoles with alkynes.
Li, Cheng; Zhao, Bin; Mao, Guojiang; Deng, Guo-Jun; Chemical communications (Cambridge, England) 59 (2023) 7044–7047; doi:10.1039/d3cc01940c

data_7131630
_publ_section_title
;
 Rhodium(III)-catalyzed mild and regioselective dearomative
 spirocyclization of 2-aryl-3-nitrosoindoles with alkynes.
;
_journal_issue                   46
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7044
_journal_page_last               7047
_journal_paper_doi               10.1039/d3cc01940c
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C24 H19 Cl N2 O'
_chemical_formula_sum            'C24 H19 Cl N2 O'
_chemical_formula_weight         386.86
_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.cc2fglj1
_audit_creation_date             2023-01-06
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-03-13 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.930(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2188(4)
_cell_length_b                   20.7777(7)
_cell_length_c                   8.8300(3)
_cell_measurement_reflns_used    4340
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      73.2190
_cell_measurement_theta_min      2.0850
_cell_volume                     1935.01(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL n/a (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_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     30.00  57.00   1.00    1.00    --   40.92  37.00  30.00   27
  2  \w     39.00 131.00   1.00    1.00    --  107.58 -45.00 -60.00   92
  3  \w     71.00 109.00   1.00    1.00    --  107.58 -94.00-150.00   38
  4  \w     60.00  97.00   1.00    1.00    --  107.58 -94.00 -60.00   37
  5  \w     52.00 128.00   1.00    1.00    --  107.58 -61.00  30.00   76
  6  \w     82.00 175.00   1.00    1.00    --  107.58  30.00 120.00   93
  7  \w    140.00 177.00   1.00    1.00    --  107.58 126.00 -62.00   37
  8  \w     95.00 125.00   1.00    1.00    --  107.58 126.00 -62.00   30
  9  \w      2.00  60.00   1.00    1.00    --   40.92 -99.00 150.00   58
 10  \w     35.00  88.00   1.00    1.00    --   40.92-125.00 -30.00   53
 11  \w     27.00  52.00   1.00    1.00    --  107.58 -94.00-150.00   25
 12  \w   -113.00 -20.00   1.00    1.00    --  -40.92 -37.00 -90.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1431740000
_diffrn_orient_matrix_UB_12      0.0142735000
_diffrn_orient_matrix_UB_13      -0.0535211000
_diffrn_orient_matrix_UB_21      0.0285427000
_diffrn_orient_matrix_UB_22      0.0725702000
_diffrn_orient_matrix_UB_23      0.0227677000
_diffrn_orient_matrix_UB_31      -0.0052729000
_diffrn_orient_matrix_UB_32      0.0050566000
_diffrn_orient_matrix_UB_33      -0.1762453000
_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  0.0305
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7351
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.813
_diffrn_reflns_theta_min         4.192
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.873
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0017(3)
_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   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0806P)^2^+0.5660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3352
_reflns_number_total             3811
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01940c2.cif
_cod_data_source_block           553
_cod_depositor_comments
'Adding full bibliography for 7131630--7131631.cif.'
_cod_original_cell_volume        1935.01(12)
_cod_database_code               7131630
_shelx_shelxl_version_number     2018/3
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C23(H23)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C24(H24A,H24B,H24C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              71245
_shelx_hkl_checksum              83624
_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 1.537
_oxdiff_exptl_absorpt_empirical_full_min 0.527