Pd-Catalyzed C–H Annulation of Five-Membered Heteroaryl Halides with Norbornene Derivatives
Padhi, Birakishore; Kang, Geunhee; Kim, Eunmin; Ha, Jeongmin; Kim, Hyun Tae; Lim, Jeewoo; Joo, Jung Min; ACS Catalysis  (2020) 1792–1798; doi:10.1021/acscatal.9b05177

data_4517310
_publ_section_title
;
 Pd-Catalyzed C--H Annulation of Five-Membered Heteroaryl Halides with
 Norbornene Derivatives
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              1792
_journal_page_last               1798
_journal_paper_doi               10.1021/acscatal.9b05177
_journal_year                    2020
_chemical_formula_sum            'C18 H20 N2'
_chemical_formula_weight         264.36
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
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_cell_angle_beta                 91.977(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   5.9745(7)
_cell_length_c                   24.769(3)
_cell_measurement_reflns_used    3557
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.21
_cell_volume                     1361.6(3)
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_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
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_diffrn_reflns_limit_l_max       29
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_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         1.645
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
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_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
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_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     181
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0894P)^2^+0.4961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1700
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2043
_reflns_number_total             2664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b05177_si_002.cif
_cod_data_source_block           ss
_cod_depositor_comments          'Adding full bibliography for 4517310.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4517310
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              99475
_shelx_hkl_checksum              88438