Selective formation of heterocyclic trans-cycloalkenes by alkyne addition to a biphenylene-based phosphane/borane frustrated Lewis pair.
Li, Jun; Daniliuc, Constantin G.; Kehr, Gerald; Erker, Gerhard; Chemical communications (Cambridge, England) 54 (2018) 6344–6347; doi:10.1039/c8cc03369b

data_7121681
_publ_section_title
;
 Selective formation of heterocyclic trans-cycloalkenes by alkyne addition
 to a biphenylene-based phosphane/borane frustrated Lewis pair.
;
_journal_issue                   49
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6344
_journal_page_last               6347
_journal_paper_doi               10.1039/c8cc03369b
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C50 H34 B F10 P'
_chemical_formula_weight         866.55
_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   geom
_audit_update_record
;
2017-11-28 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                75.9580(10)
_cell_angle_beta                 83.4140(10)
_cell_angle_gamma                65.3740(10)
_cell_formula_units_Z            4
_cell_length_a                   13.3724(3)
_cell_length_b                   14.8949(3)
_cell_length_c                   23.4627(5)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.7272
_cell_measurement_theta_min      3.3428
_cell_volume                     4120.83(16)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX2 v.2014.1-----1 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'APEX2 v.2014.1-----1 (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 v.2014.1-----1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'KappaCCD APEXII'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'CuK\a '
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            60594
_diffrn_reflns_theta_full        66.87
_diffrn_reflns_theta_max         66.87
_diffrn_reflns_theta_min         3.34
_diffrn_source                   'fine--focus sealed tube'
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison,
Wisconsin, USA.'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.030
_platon_squeeze_details
;
A disordered solvent molecule (possible half hexane molecule) was found 
in the asymmetrical unit and could not be satisfactorily refined. The 
program SQUEEZE (Spek, A.L. (2015). Acta Cryst. C71, 9-18) was therefore
used to remove mathematically the effect of the solvent. 
The quoted formula and derived parameters are not included the squeezed
solvent molecule. 
;
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.365
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1129
_refine_ls_number_reflns         14488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+0.5624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                11039
_reflns_number_total             14488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03369b2.cif
_cod_data_source_block           erk8598
_cod_depositor_comments
'Adding full bibliography for 7121673--7121682.cif.'
_cod_database_code               7121681
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              84684
_shelx_fab_checksum              78026