Enamine/butadienylborane cycloaddition in the frustrated Lewis pair regime.
Chen, Guo-Qiang; Türkyilmaz, Fatma; Daniliuc, Constantin G.; Bannwarth, Christoph; Grimme, Stefan; Kehr, Gerald; Erker, Gerhard; Organic & biomolecular chemistry 13 (2015) 10477–10486; doi:10.1039/c5ob01602a

data_7154656
_publ_section_title
;
 Enamine/butadienylborane cycloaddition in the frustrated Lewis pair
 regime.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10477
_journal_page_last               10486
_journal_paper_doi               10.1039/c5ob01602a
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C17 H10 B F10 N'
_chemical_formula_weight         429.07
_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
;
2015-07-07 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                70.278(2)
_cell_angle_beta                 74.540(2)
_cell_angle_gamma                65.394(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0935(5)
_cell_length_b                   9.5304(5)
_cell_length_c                   11.4509(7)
_cell_measurement_reflns_used    6710
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.4180
_cell_measurement_theta_min      2.4906
_cell_volume                     840.08(8)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14380
_diffrn_reflns_theta_full        26.46
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         2.43
_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.91
_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    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.173
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0379P)^2^+0.4930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                2806
_reflns_number_total             3450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01602a2.cif
_cod_data_source_block           erk7963
_cod_depositor_comments
'Adding full bibliography for 7154649--7154656.cif.'
_cod_database_code               7154656
_shelx_res_checksum              10824