Palladium/norbornene-catalyzed C-H/N-H cycloaddition of carbazoles with 2-halobenzoic acid derivatives.
Liu, Shilei; Nan, Jiang; An, Nan; Cao, Rui; Zhu, Lanxin; Yan, Qiang; Zhang, Hanqing; Liang, Chengyuan; Chemical communications (Cambridge, England) 60 (2024) 11746–11749; doi:10.1039/d4cc03720k

data_7133717
_publ_section_title
;
 Palladium/norbornene-catalyzed C-H/N-H cycloaddition of carbazoles with
 2-halobenzoic acid derivatives.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11746
_journal_page_last               11749
_journal_paper_doi               10.1039/d4cc03720k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C27 H27 N O'
_chemical_formula_sum            'C27 H27 N O'
_chemical_formula_weight         381.49
_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             2023-09-22
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-06-27 deposited with the CCDC.	2024-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                76.338(13)
_cell_angle_beta                 79.786(14)
_cell_angle_gamma                78.458(14)
_cell_formula_units_Z            2
_cell_length_a                   7.057(3)
_cell_length_b                   12.282(4)
_cell_length_c                   13.493(5)
_cell_measurement_reflns_used    2375
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      20.72
_cell_measurement_theta_min      2.57
_cell_volume                     1103.0(7)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 V2022.08-RC130 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1207
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32354
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.598
_diffrn_reflns_theta_min         2.974
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms DIAMOND'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1217 before and 0.0784 after correction.
The Ratio of minimum to maximum transmission is 0.8448.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5054
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.0746
_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^)+(0.1183P)^2^+0.2349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2036
_refine_ls_wR_factor_ref         0.2676
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2495
_reflns_number_total             5054
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03720k2.cif
_cod_data_source_block           mo_230921lu_lgpz180396_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7133717.cif.
;
_cod_original_cell_volume        1103.0(8)
_cod_database_code               7133717
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.991
_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
2. Restrained distances
 C24-C21 \\sim C23A-C21 \\sim C23-C21 \\sim C22A-C21 \\sim C22-C21 \\sim
C24A-C21
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C21 \\sim C24 \\sim C23 \\sim C22 \\sim C22A \\sim C23A \\sim C24A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C23A)=Sof(H23D)=Sof(H23E)=
 Sof(H23F)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C9(H9), C19(H19), C6(H6), C3(H3), C26(H26), C4(H4), C5(H5), C25(H25)
5.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C24(H24A,H24B,
 H24C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F),
 C23A(H23D,H23E,H23F), C24A(H24D,H24E,H24F)
;
_shelx_res_checksum              75032
_shelx_hkl_checksum              93016
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU