Frustrated Lewis pair behavior of monomeric (boryl)iminomethanes accessed from isocyanide 1,1-hydroboration
Brandon R. Barnett; Curtis E. Moore; Arnold L. Rheingold; Joshua S. Figuero; Chem.Commun. 51 (2015) 541–; doi:10.1039/C4cc08037H

data_7116374
_publ_section_title
;
 Frustrated Lewis pair behavior of monomeric (boryl)iminomethanes accessed
 from isocyanide 1,1-hydroboration
;
_journal_name_full               Chem.Commun.
_journal_page_first              541
_journal_paper_doi               10.1039/C4cc08037H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C44 H60 B N O2'
_chemical_formula_sum            'C44 H60 B N O2'
_chemical_formula_weight         645.74
_chemical_name_common            Cy2BIM_CO2
_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_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
_audit_creation_date             2014-10-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 116.965(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4420(17)
_cell_length_b                   11.9605(12)
_cell_length_c                   19.592(2)
_cell_measurement_reflns_used    2798
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.584
_cell_measurement_theta_min      2.518
_cell_volume                     3851.7(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II TXS'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.1025
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17810
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.410
_diffrn_reflns_theta_min         2.064
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0581 before and 0.0401 after correction.
The Ratio of minimum to maximum transmission is 0.8811.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         7152
_refine_ls_number_restraints     139
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1409
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.9391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3930
_reflns_number_total             7152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc08037h2.cif
_cod_data_source_block           JFig899
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to the built-in table from CIF Core dictionary named 'cif_core.dic'
version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_database_code               7116374
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.992
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C40C-C39C = C41C-C40C = C42C-C41C = C43C-C42C = C44C-C43C = C44C-C39C
 1.54 with sigma of 0.02
 C40B-C39B = C41B-C40B = C42B-C41B = C43B-C42B = C44B-C43B = C44B-C39B
 1.54 with sigma of 0.02
 C40-C39 = C41-C40 = C42-C41 = C43-C42 = C44-C43 = C44-C39
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C42) = Uanis(C42B)
Uanis(C42B) = Uanis(C42) = Uanis(C42C)
Uanis(C39) = Uanis(C39C) = Uanis(C39B)
Uanis(C43C) = Uanis(C43B)
Uanis(C44C) = Uanis(C44)
Uanis(C43C) = Uanis(C44B)
Uanis(C40B) = Uanis(C40C) = Uanis(C40)
Uanis(C41C) = Uanis(C41)
4. Rigid body (RIGU) restrains
 C39, C42, C44B, C40, C40B, C44, C43B, C41B, C41, C43, C39B, C42B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C39C, C40C, C41C, C42C, C44C, C43C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C39, C40, C41, C42, C43, C44}
as
{C39C, C40C, C41C, C42C, C43C, C44C}
6. Others
 1*[Sof(C39C)+Sof(H39C)+Sof(C40C)+Sof(H40E)+Sof(H40F)+Sof(C41C)+Sof(H41E)+
 Sof(H41F)+Sof(C42C)+Sof(H42E)+Sof(H42F)+Sof(C43C)+Sof(H43E)+Sof(H43F)+
 Sof(C44C)+Sof(H44E)+Sof(H44F)]+1*[Sof(C39)+Sof(H39)+Sof(C40)+Sof(H40A)+
 Sof(H40B)+Sof(C41)+Sof(H41A)+Sof(H41B)+Sof(C42)+Sof(H42A)+Sof(H42B)+Sof(C43)+
 Sof(H43A)+Sof(H43B)+Sof(C44)+Sof(H44A)+Sof(H44B)]+1*[Sof(C39B)+Sof(H39B)+
 Sof(C40B)+Sof(H40C)+Sof(H40D)+Sof(C41B)+Sof(H41C)+Sof(H41D)+Sof(C42B)+
 Sof(H42C)+Sof(H42D)+Sof(C43B)+Sof(H43C)+Sof(H43D)+Sof(C44B)+Sof(H44C)+
 Sof(H44D)]=1 with esd of 0.00001
 Sof(C39C)=Sof(H39C)=Sof(C40C)=Sof(H40E)=Sof(H40F)=Sof(C41C)=Sof(H41E)=
 Sof(H41F)=Sof(C42C)=Sof(H42E)=Sof(H42F)=Sof(C43C)=Sof(H43E)=Sof(H43F)=
 Sof(C44C)=Sof(H44E)=Sof(H44F)=FVAR(1)
 Sof(C39)=Sof(H39)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(C41)=Sof(H41A)=Sof(H41B)=
 Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=
 Sof(H44B)=FVAR(2)
 Sof(C39B)=Sof(H39B)=Sof(C40B)=Sof(H40C)=Sof(H40D)=Sof(C41B)=Sof(H41C)=
 Sof(H41D)=Sof(C42B)=Sof(H42C)=Sof(H42D)=Sof(C43B)=Sof(H43C)=Sof(H43D)=
 Sof(C44B)=Sof(H44C)=Sof(H44D)=FVAR(3)
7.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C21(H21), C24(H24), C33(H33), C36(H36), C39(H39), C39B(H39B),
 C39C(H39C)
7.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C40(H40A,
 H40B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B),
 C40B(H40C,H40D), C41B(H41C,H41D), C42B(H42C,H42D), C43B(H43C,H43D), C44B(H44C,
 H44D), C40C(H40E,H40F), C41C(H41E,H41F), C42C(H42E,H42F), C43C(H43E,H43F),
 C44C(H44E,H44F)
7.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C17(H17), C18(H18), C19(H19), C29(H29),
 C30(H30), C31(H31)
7.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C37(H37A,H37B,H37C), C38(H38A,
 H38B,H38C)
;
_shelx_res_checksum              12575
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'