#------------------------------------------------------------------------------
#$Date: 2019-11-23 12:26:05 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233278 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/30/1553091.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1553091
loop_
_publ_author_name
'Farrell, Jeffrey M.'
'Posaratnanathan, Roy T.'
'Stephan, Douglas W.'
_publ_section_title
;
 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_sum            'C11 H24 B P'
_chemical_formula_weight         198.08
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
;
2014-11-23 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.038(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0408(11)
_cell_length_b                   6.6868(6)
_cell_length_c                   16.9825(15)
_cell_measurement_reflns_used    4157
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.42
_cell_volume                     1244.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9241
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_correction_T_min  0.9481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.057
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0373P)²+0.3394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                1785
_reflns_number_total             2187
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc03675a2.cif
_cod_data_source_block           jf053_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1553091
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.30414(4) 1.02667(7) 0.80027(2) 0.01700(14) Uani 1 1 d .
C3 C 0.25749(17) 0.9124(3) 0.51183(10) 0.0257(4) Uani 1 1 d .
H3A H 0.1706 0.8818 0.4945 0.031 Uiso 1 1 calc R
H3B H 0.3011 0.9086 0.4643 0.031 Uiso 1 1 calc R
C4 C 0.26657(17) 1.1254(3) 0.54649(10) 0.0235(4) Uani 1 1 d .
H4A H 0.2136 1.2146 0.5107 0.028 Uiso 1 1 calc R
H4B H 0.3516 1.1728 0.5470 0.028 Uiso 1 1 calc R
C5 C 0.23033(15) 1.1454(2) 0.63111(10) 0.0197(4) Uani 1 1 d .
H5 H 0.2523 1.2830 0.6511 0.024 Uiso 1 1 calc R
C10 C 0.32421(18) 1.2889(3) 0.82471(11) 0.0282(5) Uani 1 1 d .
H10A H 0.3307 1.3059 0.8824 0.042 Uiso 1 1 calc R
H10B H 0.2540 1.3648 0.7995 0.042 Uiso 1 1 calc R
H10C H 0.3988 1.3381 0.8054 0.042 Uiso 1 1 calc R
C9 C 0.17191(15) 0.9516(3) 0.84723(10) 0.0253(4) Uani 1 1 d .
H9A H 0.1645 0.8056 0.8458 0.038 Uiso 1 1 calc R
H9B H 0.0982 1.0115 0.8187 0.038 Uiso 1 1 calc R
H9C H 0.1817 0.9973 0.9025 0.038 Uiso 1 1 calc R
C11 C 0.42933(16) 0.8999(3) 0.85850(10) 0.0252(4) Uani 1 1 d .
H11A H 0.5069 0.9501 0.8438 0.038 Uiso 1 1 calc R
H11B H 0.4234 0.7558 0.8482 0.038 Uiso 1 1 calc R
H11C H 0.4255 0.9251 0.9150 0.038 Uiso 1 1 calc R
C6 C 0.09299(16) 1.1127(3) 0.63493(11) 0.0249(4) Uani 1 1 d .
H6A H 0.0466 1.2030 0.5960 0.030 Uiso 1 1 calc R
H6B H 0.0743 1.1520 0.6883 0.030 Uiso 1 1 calc R
C7 C 0.04745(16) 0.8971(3) 0.61824(11) 0.0286(4) Uani 1 1 d .
H7A H 0.0339 0.8774 0.5601 0.034 Uiso 1 1 calc R
H7B H -0.0325 0.8823 0.6384 0.034 Uiso 1 1 calc R
C8 C 0.13272(16) 0.7297(3) 0.65476(11) 0.0247(4) Uani 1 1 d .
H8A H 0.1102 0.6039 0.6258 0.030 Uiso 1 1 calc R
H8B H 0.1174 0.7099 0.7105 0.030 Uiso 1 1 calc R
C1 C 0.27096(15) 0.7652(2) 0.65391(9) 0.0181(4) Uani 1 1 d .
H1 H 0.3170 0.6631 0.6887 0.022 Uiso 1 1 calc R
C2 C 0.31008(17) 0.7492(3) 0.56972(10) 0.0230(4) Uani 1 1 d .
H2A H 0.4003 0.7550 0.5741 0.028 Uiso 1 1 calc R
H2B H 0.2844 0.6171 0.5472 0.028 Uiso 1 1 calc R
B1 B 0.31131(17) 0.9855(3) 0.68666(11) 0.0162(4) Uani 1 1 d .
H12 H 0.4139(15) 1.018(3) 0.6891(10) 0.025(5) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 P1 C10 105.36(9)
C11 P1 C9 103.40(8)
C10 P1 C9 104.44(9)
C11 P1 B1 110.61(8)
C10 P1 B1 110.08(8)
C9 P1 B1 121.63(8)
C2 C3 C4 114.27(14)
C2 C3 H3A 108.7
C4 C3 H3A 108.7
C2 C3 H3B 108.7
C4 C3 H3B 108.7
H3A C3 H3B 107.6
C3 C4 C5 115.10(14)
C3 C4 H4A 108.5
C5 C4 H4A 108.5
C3 C4 H4B 108.5
C5 C4 H4B 108.5
H4A C4 H4B 107.5
C6 C5 C4 113.28(14)
C6 C5 B1 110.93(14)
C4 C5 B1 107.27(13)
C6 C5 H5 108.4
C4 C5 H5 108.4
B1 C5 H5 108.4
P1 C10 H10A 109.5
P1 C10 H10B 109.5
H10A C10 H10B 109.5
P1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
P1 C9 H9A 109.5
P1 C9 H9B 109.5
H9A C9 H9B 109.5
P1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
P1 C11 H11A 109.5
P1 C11 H11B 109.5
H11A C11 H11B 109.5
P1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C5 C6 C7 115.18(14)
C5 C6 H6A 108.5
C7 C6 H6A 108.5
C5 C6 H6B 108.5
C7 C6 H6B 108.5
H6A C6 H6B 107.5
C6 C7 C8 115.81(14)
C6 C7 H7A 108.3
C8 C7 H7A 108.3
C6 C7 H7B 108.3
C8 C7 H7B 108.3
H7A C7 H7B 107.4
C7 C8 C1 116.05(14)
C7 C8 H8A 108.3
C1 C8 H8A 108.3
C7 C8 H8B 108.3
C1 C8 H8B 108.3
H8A C8 H8B 107.4
C8 C1 C2 112.68(14)
C8 C1 B1 111.54(14)
C2 C1 B1 106.52(13)
C8 C1 H1 108.7
C2 C1 H1 108.7
B1 C1 H1 108.7
C3 C2 C1 114.61(14)
C3 C2 H2A 108.6
C1 C2 H2A 108.6
C3 C2 H2B 108.6
C1 C2 H2B 108.6
H2A C2 H2B 107.6
C1 B1 C5 106.96(13)
C1 B1 P1 115.07(12)
C5 B1 P1 113.22(12)
C1 B1 H12 114.3(9)
C5 B1 H12 111.6(9)
P1 B1 H12 95.5(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C11 1.8089(17)
P1 C10 1.8093(18)
P1 C9 1.8179(17)
P1 B1 1.9601(19)
C3 C2 1.534(2)
C3 C4 1.539(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.544(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.541(2)
C5 B1 1.621(2)
C5 H5 1.0000
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C6 C7 1.541(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.543(2)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C1 1.546(2)
C8 H8A 0.9900
C8 H8B 0.9900
C1 C2 1.547(2)
C1 B1 1.618(3)
C1 H1 1.0000
C2 H2A 0.9900
C2 H2B 0.9900
B1 H12 1.149(17)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 C3 C4 C5 -44.6(2)
C3 C4 C5 C6 -68.77(19)
C3 C4 C5 B1 53.99(19)
C4 C5 C6 C7 68.50(19)
B1 C5 C6 C7 -52.21(19)
C5 C6 C7 C8 40.4(2)
C6 C7 C8 C1 -38.5(2)
C7 C8 C1 C2 -71.36(19)
C7 C8 C1 B1 48.4(2)
C4 C3 C2 C1 46.0(2)
C8 C1 C2 C3 65.95(19)
B1 C1 C2 C3 -56.66(18)
C8 C1 B1 C5 -57.72(17)
C2 C1 B1 C5 65.60(16)
C8 C1 B1 P1 68.99(16)
C2 C1 B1 P1 -167.68(11)
C6 C5 B1 C1 59.75(17)
C4 C5 B1 C1 -64.45(17)
C6 C5 B1 P1 -68.05(16)
C4 C5 B1 P1 167.75(11)
C11 P1 B1 C1 74.39(14)
C10 P1 B1 C1 -169.58(12)
C9 P1 B1 C1 -47.10(16)
C11 P1 B1 C5 -162.16(12)
C10 P1 B1 C5 -46.13(14)
C9 P1 B1 C5 76.35(15)
