Palladium catalyzed annulation of 2-iodobiphenyl with a non-terminal alkene enabled by neighboring group assistance.
Tang, Bo-Cheng; He, Cai; Chen, Xiang-Long; Ma, Jin-Tian; Wang, Miao; Wu, Yan-Dong; Wu, An-Xin; Chemical communications (Cambridge, England) 57 (2021) 121–124; doi:10.1039/d0cc07133a

data_7127471
_publ_section_title
;
 Palladium catalyzed annulation of 2-iodobiphenyl with a non-terminal
 alkene enabled by neighboring group assistance.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              121
_journal_page_last               124
_journal_paper_doi               10.1039/d0cc07133a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C27 H17 F O2'
_chemical_formula_sum            'C27 H17 F O2'
_chemical_formula_weight         392.40
_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     direct
_audit_creation_date             2019-09-26
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2020-08-24 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                95.856(2)
_cell_angle_beta                 112.392(2)
_cell_angle_gamma                103.122(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1584(13)
_cell_length_b                   10.6273(15)
_cell_length_c                   11.0747(16)
_cell_measurement_reflns_used    6488
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      31.73
_cell_measurement_theta_min      2.49
_cell_volume                     949.1(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      210(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            6806
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.012
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.056(6)
_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   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0706P)^2^+0.2617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3053
_reflns_number_total             3491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07133a2.cif
_cod_data_source_block           mo_190926b_0m
_cod_depositor_comments          'Adding full bibliography for 7127471.cif.'
_cod_database_code               7127471
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All O(H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), 
 C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27) 
2.b Idealised tetrahedral OH refined as rotating group: 
 O1(H1) 
;
_shelx_res_checksum              61369
_olex2_submission_special_instructions 'No special instructions were received'