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_1553083
_publ_section_title
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 A family of N-heterocyclic carbene-stabilized borenium ions for
 metal-free imine hydrogenation catalysis.
;
_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 H21 B F10 N2'
_chemical_formula_sum            'C23 H21 B F10 N2'
_chemical_formula_weight         526.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_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                 101.938(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6299(9)
_cell_length_b                   19.4566(9)
_cell_length_c                   12.2650(6)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.291
_cell_measurement_theta_min      2.418
_cell_volume                     4583.1(4)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.02
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            77613
_diffrn_reflns_theta_full        27.5805
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         1.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0669 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.8873.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5252
_exptl_crystal_description       block
_exptl_crystal_F_000             2145.8804
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.4438
_refine_diff_density_min         -0.4090
_refine_diff_density_rms         0.1035
_refine_ls_d_res_high            0.7675
_refine_ls_d_res_low             13.6682
_refine_ls_goodness_of_fit_ref   1.0948
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     660
_refine_ls_number_reflns         10567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0948
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+6.2019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              25
_reflns_limit_h_min              -25
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                7086
_reflns_number_total             10567
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4sc03675a2.cif
_cod_data_source_block           JF024
_cod_database_code               1553083
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H14(0.06) H15(0.06) H17a(0.06) H17b(0.06) H17c(0.06) H18a(0.06)
 H18b(0.06) H18c(0.06) H19a(0.06) H19b(0.06) H19c(0.06) H21a(0.06) H21b(0.06)
 H21c(0.06) H22a(0.06) H22b(0.06) H22c(0.06) H23a(0.06) H23b(0.06) H23c(0.06)
 H1(0.06) H37(0.06) H38(0.06) H40a(0.06) H40b(0.06) H40c(0.06) H41a(0.06)
 H41b(0.06) H41c(0.06) H42a(0.06) H42b(0.06) H42c(0.06) H44a(0.06) H44b(0.06)
 H44c(0.06) H45a(0.06) H45b(0.06) H45c(0.06) H46a(0.06) H46b(0.06) H46c(0.06)
 H2(0.06)
2.a Ternary CH refined with riding coordinates:
 B1(H1), B2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C37(H37), C38(H38)
2.c Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C19(H19a,H19b,H19c), C21(H21a,H21b,
 H21c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c), C40(H40a,H40b,H40c), C41(H41a,
 H41b,H41c), C42(H42a,H42b,H42c), C44(H44a,H44b,H44c), C45(H45a,H45b,H45c),
 C46(H46a,H46b,H46c)
;
_olex2_submission_special_instructions 'No special instructions were received'