Rhodium-catalyzed intramolecular cascade sequence for the formation of fused carbazole-annulated medium-sized rings by cleavage of C(sp<sup>2</sup>)-H/C(sp<sup>3</sup>)-H bonds.
Li, Qiuyun; Li, Bin; Wang, Baiquan; Chemical communications (Cambridge, England) 54 (2018) 9147–9150; doi:10.1039/c8cc04428g

data_7122014
_publ_section_title
;
 Rhodium-catalyzed intramolecular cascade sequence for the formation of
 fused carbazole-annulated medium-sized rings by cleavage of
 C(sp<sup>2</sup>)-H/C(sp<sup>3</sup>)-H bonds.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9147
_journal_page_last               9150
_journal_paper_doi               10.1039/c8cc04428g
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C23 H18 N2 O'
_chemical_formula_sum            'C23 H18 N2 O'
_chemical_formula_weight         338.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-04-04 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                68.543(3)
_cell_angle_beta                 62.333(3)
_cell_angle_gamma                65.904(3)
_cell_formula_units_Z            2
_cell_length_a                   10.0747(3)
_cell_length_b                   10.1323(3)
_cell_length_c                   10.7896(3)
_cell_measurement_reflns_used    23429
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      78.9300
_cell_measurement_theta_min      4.7180
_cell_volume                     869.06(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.964
_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   -115.00 -21.00   1.00    5.00    --  -35.00 -72.00 -36.00   94
  2  \w   -125.00 -21.00   1.00    5.00    --  -35.00 -72.00-180.00  104
  3  \w    -50.00  40.00   1.00    5.00    --  -35.00  72.00  72.00   90
  4  \w   -115.00 -22.00   1.00    5.00    --  -35.00 -44.00-180.00   93
  5  \w    -50.00  40.00   1.00    5.00    --  -35.00  72.00-144.00   90
  6  \w    -50.00  40.00   1.00    5.00    --  -35.00  72.00   0.00   90
  7  \w   -114.00 -21.00   1.00    5.00    --  -35.00 -72.00-108.00   93
  8  \w   -115.00 -24.00   1.00    5.00    --  -35.00 -72.00-144.00   91
  9  \w   -112.00 -21.00   1.00    5.00    --  -35.00 -72.00 108.00   91
 10  \w   -115.00 -24.00   1.00    5.00    --  -35.00 -72.00  72.00   91
 11  \w   -115.00 -22.00   1.00    5.00    --  -35.00 -72.00   0.00   93
 12  \w    -50.00  40.00   1.00    5.00    --  -35.00  72.00-180.00   90
 13  \w    -50.00  40.00   1.00    5.00    --  -35.00  72.00 -72.00   90
 14  \w   -115.00 -25.00   1.00    5.00    --  -35.00 -44.00 108.00   90
 15  \w   -115.00 -24.00   1.00    5.00    --  -35.00 -72.00 -72.00   91
 16  \w    -50.00  40.00   1.00    5.00    --  -35.00  14.00 -72.00   90
 17  \w   -125.00 -33.00   1.00    5.00    --  -35.00 -44.00   0.00   92
 18  \w    -50.00  40.00   1.00    5.00    --  -35.00  72.00 108.00   90
 19  \w   -115.00 -25.00   1.00    5.00    --  -35.00 -72.00 144.00   90
 20  \w   -112.00 -21.00   1.00    5.00    --  -35.00 -72.00  36.00   91
 21  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00-108.00   91
 22  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -44.00  72.00   90
 23  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -15.00 -36.00   90
 24  \w   -125.00 -32.00   1.00    5.00    -- -110.00  72.00  72.00   93
 25  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00 108.00   91
 26  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00 144.00   91
 27  \w   -123.00 -33.00   1.00    5.00    -- -110.00  72.00 -72.00   90
 28  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -44.00 -36.00   90
 29  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00  36.00   91
 30  \w   -200.00 -96.00   1.00    5.00    -- -110.00 -72.00-108.00  104
 31  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00   0.00   91
 32  \w   -123.00 -33.00   1.00    5.00    -- -110.00  72.00   0.00   90
 33  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00 108.00   91
 34  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -72.00  72.00   90
 35  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -15.00 144.00   90
 36  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00  36.00   91
 37  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -44.00   0.00   90
 38  \w   -125.00 -33.00   1.00    5.00    -- -110.00  72.00-108.00   92
 39  \w   -125.00 -33.00   1.00    5.00    -- -110.00  72.00 108.00   92
 40  \w   -200.00-110.00   1.00    5.00    -- -110.00 -15.00-144.00   90
 41  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00-180.00   91
 42  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -72.00 144.00   90
 43  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00 -72.00   91
 44  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00 -72.00   91
 45  \w   -125.00 -32.00   1.00    5.00    -- -110.00  72.00 -36.00   93
 46  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00-144.00   91
 47  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -15.00 -72.00   90
 48  \w   -200.00-110.00   1.00    5.00    -- -110.00 -15.00-180.00   90
 49  \w   -115.00 -25.00   1.00    5.00    -- -110.00  72.00-180.00   90
 50  \w   -200.00-110.00   1.00    5.00    -- -110.00 -15.00   0.00   90
 51  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -44.00-144.00   90
 52  \w   -125.00 -31.00   1.00    5.00    -- -110.00  72.00 144.00   94
 53  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -15.00-108.00   90
 54  \w   -200.00-110.00   1.00    5.00    -- -110.00 -15.00  36.00   90
 55  \w   -200.00-110.00   1.00    5.00    -- -110.00 -15.00 108.00   90
 56  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00-180.00   91
 57  \w   -124.00 -33.00   1.00    5.00    -- -110.00  72.00-144.00   91
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1460124000
_diffrn_orient_matrix_UB_12      0.0529898000
_diffrn_orient_matrix_UB_13      -0.0608527000
_diffrn_orient_matrix_UB_21      0.0125054000
_diffrn_orient_matrix_UB_22      0.0214177000
_diffrn_orient_matrix_UB_23      -0.1535534000
_diffrn_orient_matrix_UB_31      -0.1051465000
_diffrn_orient_matrix_UB_32      0.1608078000
_diffrn_orient_matrix_UB_33      0.0022898000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0078
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28855
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.143
_diffrn_reflns_theta_min         4.742
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.067(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0710P)^2^+0.1300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1268
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3483
_reflns_number_total             3627
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04428g2.cif
_cod_data_source_block           p20171020a
_cod_depositor_comments          'Adding full bibliography for 7122014.cif.'
_cod_database_code               7122014
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C23H18N2O
_shelx_estimated_absorpt_t_max   0.864
_shelx_estimated_absorpt_t_min   0.805
_reflns_odcompleteness_completeness 96.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.90
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20),
 C21(H21)
;
_shelx_res_checksum              95237
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.347
_oxdiff_exptl_absorpt_empirical_full_min 0.723