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_7154654
_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            'C16 H8 B F10 N O'
_chemical_formula_weight         431.04
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-07-07 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.102(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.6260(5)
_cell_length_b                   18.2872(12)
_cell_length_c                   21.3911(14)
_cell_measurement_reflns_used    5163
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      4.08
_cell_volume                     3373.7(4)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.128
_diffrn_reflns_av_sigmaI/netI    0.1694
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17034
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         4.09
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.247
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         5714
_refine_ls_number_restraints     129
_refine_ls_restrained_S_all      1.247
_refine_ls_R_factor_all          0.3246
_refine_ls_R_factor_gt           0.1902
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+32.8256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2615
_refine_ls_wR_factor_ref         0.3268
_reflns_number_gt                2608
_reflns_number_total             5714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01602a2.cif
_cod_data_source_block           erk7693
_cod_depositor_comments
'Adding full bibliography for 7154649--7154656.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7154654