Synthesis of indene-fused spiro-dibenz(ox)azepines <i>via</i> Rh(III)-catalyzed cascade regioselective C-H activation/annulation.
Naskar, Koushik; Karmakar, Sudip; Mondal, Imtiaj; Sarkar, Writhabrata; Roy, Shantonu; Roy, Anupam; Deb, Indubhusan; Chemical communications (Cambridge, England) 59 (2023) 7751–7754; doi:10.1039/d3cc01416a

data_7131572
_publ_section_title
;
 Synthesis of indene-fused spiro-dibenz(ox)azepines <i>via</i>
 Rh(III)-catalyzed cascade regioselective C-H activation/annulation.
;
_journal_issue                   50
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7751
_journal_page_last               7754
_journal_paper_doi               10.1039/d3cc01416a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C34 H22 Br N O2'
_chemical_formula_sum            'C34 H22 Br N O2'
_chemical_formula_weight         556.43
_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             2022-11-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-12-14 deposited with the CCDC.	2023-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.2500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7008(2)
_cell_length_b                   13.1668(3)
_cell_length_c                   17.7959(3)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      64.97
_cell_measurement_theta_min      3.94
_cell_volume                     2632.14(9)
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III (1)'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            45439
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        65.051
_diffrn_reflns_theta_max         65.051
_diffrn_reflns_theta_min         3.935
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.379
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1237 before and 0.0621 after correction.
The Ratio of minimum to maximum transmission is 0.7258.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+1.8978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0853
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4365
_reflns_number_total             4432
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01416a2.cif
_cod_data_source_block           kn_01_260_0m_a
_cod_depositor_comments
'Adding full bibliography for 7131569--7131574.cif.'
_cod_database_code               7131572
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.648
_shelx_estimated_absorpt_t_min   0.490
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C20(H20), C18(H18), C34(H34), C12(H12), C30(H30), C17(H17), C28(H28),
 C3(H3), C9(H9), C27(H27), C33(H33), C4(H4), C2(H2), C24(H24), C31(H31),
 C32(H32), C5(H5), C11(H11), C10(H10), C26(H26), C25(H25)
;
_shelx_res_checksum              4241
_shelx_hkl_checksum              92704
_olex2_submission_original_sample_id KN_01_260
_olex2_submission_special_instructions 'No special instructions were received'