A family of N-heterocyclic carbene-stabilized borenium ions for metal-free imine hydrogenation catalysis.
Farrell, Jeffrey M.; Posaratnanathan, Roy T.; Stephan, Douglas W.; Chemical science 6 (2015) 2010–2015; doi:10.1039/c4sc03675a

data_1553084
_publ_section_title
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 A family of N-heterocyclic carbene-stabilized borenium ions for
 metal-free imine hydrogenation catalysis.
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_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              2010
_journal_page_last               2015
_journal_paper_doi               10.1039/c4sc03675a
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C23 H18.71 B F10 N2'
_chemical_formula_sum            'C23 H18.711 B F10 N2'
_chemical_formula_weight         523.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-11-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_audit_update_record
;
2014-11-23 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.409(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5423(18)
_cell_length_b                   12.863(2)
_cell_length_c                   15.801(2)
_cell_measurement_temperature    150(2)
_cell_volume                     2341.8(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      149.7
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9783
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19692
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0581 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.9225.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.4860
_exptl_crystal_description       block
_exptl_crystal_F_000             1063.7835
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.2215
_refine_diff_density_min         -1.1698
_refine_diff_density_rms         0.1128
_refine_ls_d_res_high            0.7673
_refine_ls_d_res_low             9.9683
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0563
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    11
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0563
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0754
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+4.9380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1836
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -14
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -11
_reflns_number_gt                3100
_reflns_number_total             5311
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4sc03675a2.cif
_cod_data_source_block           jf034_0m
_cod_original_cell_volume        2341.7(6)
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               1553084
_olex2_refinement_description
;
1. Others
 Sof(C7A)=Sof(H7Aa)=Sof(H7Ab)=Sof(H7Ac)=Sof(C11)=Sof(H11a)=Sof(H11b)=Sof(H11c)=
 Sof(B2)=1-FVAR(1)
 Sof(C7)=Sof(H7a)=Sof(H7b)=Sof(C11A)=Sof(H11d)=Sof(H11e)=Sof(B1)=FVAR(1)
 Fixed Uiso: H1(0.06) H2(0.06) H5a(0.06) H5b(0.06) H5c(0.06) H6a(0.06)
 H6b(0.06) H6c(0.06) H7a(0.06) H7b(0.06) H7Aa(0.06) H7Ab(0.06) H7Ac(0.06)
 H9a(0.06) H9b(0.06) H9c(0.06) H10a(0.06) H10b(0.06) H10c(0.06) H11a(0.06)
 H11b(0.06) H11c(0.06) H11d(0.06) H11e(0.06)
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C11A(H11d,H11e)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
2.c Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c), C6(H6a,H6b,H6c), C7A(H7Aa,H7Ab,H7Ac), C9(H9a,H9b,H9c),
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c)
;
_olex2_submission_special_instructions 'No special instructions were received'