#------------------------------------------------------------------------------
#$Date: 2016-03-25 15:42:56 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179932 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/27/7022759.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_7022759
loop_
_publ_author_name
'Sabourin, Kyle J.'
'Malcolm, Adam C.'
'McDonald, Robert'
'Ferguson, Michael J.'
'Rivard, Eric'
_publ_section_title
;
 Metal-free dehydrogenation of amine-boranes by an N-heterocyclic carbene.
;
_journal_issue                   13
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4625
_journal_page_last               4632
_journal_paper_doi               10.1039/c3dt32988g
_journal_volume                  42
_journal_year                    2013
_chemical_formula_moiety         'C12 H22 B N'
_chemical_formula_sum            'C12 H22 B N'
_chemical_formula_weight         191.12
_chemical_name_common            6
_chemical_name_systematic
;
?
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   15.4951(12)
_cell_length_b                   15.4951(12)
_cell_length_c                   27.816(2)
_cell_measurement_reflns_used    5867
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.82
_cell_measurement_theta_min      2.63
_cell_volume                     5783.8(8)
_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    'SHELXD (Schneider & Sheldrick, 2002)'
_diffrn_ambient_temperature      173(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       '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  0.0301
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13920
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.988
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1908
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0406
_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)+(0.0548P)²+3.2448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1114
_reflns_number_gt                1921
_reflns_number_total             2343
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3dt32988g.txt
_cod_data_source_block           riv12c3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        5783.9(8)
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               7022759
#BEGIN Tags that were not found in dictionaries:
_diffrn_reflns_av_unetl/netl     0.0167
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
N N 0.78096(7) 0.88569(7) 0.05270(4) 0.0295(3) Uani 1 1 d .
H1NA H 0.7790(10) 0.8979(10) 0.0208(6) 0.041(4) Uiso 1 1 d .
H1NB H 0.8237(11) 0.9486(11) 0.0658(5) 0.045(4) Uiso 1 1 d .
C1 C 0.68173(8) 0.84862(8) 0.07336(4) 0.0279(3) Uani 1 1 d .
C2 C 0.67489(9) 0.87709(9) 0.12022(4) 0.0321(3) Uani 1 1 d .
C3 C 0.58013(10) 0.84713(10) 0.13811(5) 0.0413(3) Uani 1 1 d .
H3 H 0.5733 0.8672 0.1695 0.050 Uiso 1 1 calc R
C4 C 0.49660(10) 0.78918(11) 0.11128(5) 0.0473(4) Uani 1 1 d .
H4 H 0.4326 0.7708 0.1238 0.057 Uiso 1 1 calc R
C5 C 0.50536(10) 0.75765(10) 0.06626(5) 0.0427(3) Uani 1 1 d .
H5 H 0.4467 0.7153 0.0486 0.051 Uiso 1 1 calc R
C6 C 0.59773(9) 0.78613(8) 0.04596(4) 0.0323(3) Uani 1 1 d .
C7 C 0.76508(10) 0.93928(10) 0.15177(4) 0.0381(3) Uani 1 1 d .
H7 H 0.8253 0.9488 0.1339 0.046 Uiso 1 1 calc R
C8 C 0.75960(15) 0.88640(12) 0.19859(6) 0.0679(5) Uani 1 1 d .
H8A H 0.8180 0.9291 0.2183 0.082 Uiso 1 1 calc R
H8B H 0.7583 0.8238 0.1916 0.082 Uiso 1 1 calc R
H8C H 0.6989 0.8722 0.2160 0.082 Uiso 1 1 calc R
C9 C 0.77852(12) 1.04145(10) 0.16125(6) 0.0541(4) Uani 1 1 d .
H9A H 0.7877 1.0764 0.1307 0.065 Uiso 1 1 calc R
H9B H 0.8373 1.0797 0.1816 0.065 Uiso 1 1 calc R
H9C H 0.7193 1.0344 0.1776 0.065 Uiso 1 1 calc R
C10 C 0.60153(10) 0.74528(9) -0.00321(4) 0.0377(3) Uani 1 1 d .
H10 H 0.6726 0.7799 -0.0140 0.045 Uiso 1 1 calc R
C11 C 0.56536(12) 0.63395(10) 0.00015(6) 0.0535(4) Uani 1 1 d .
H11A H 0.6044 0.6227 0.0245 0.064 Uiso 1 1 calc R
H11B H 0.5736 0.6098 -0.0311 0.064 Uiso 1 1 calc R
H11C H 0.4948 0.5980 0.0092 0.064 Uiso 1 1 calc R
C12 C 0.54102(12) 0.76449(11) -0.04077(5) 0.0523(4) Uani 1 1 d .
H12A H 0.5633 0.8358 -0.0417 0.063 Uiso 1 1 calc R
H12B H 0.4702 0.7271 -0.0322 0.063 Uiso 1 1 calc R
H12C H 0.5507 0.7429 -0.0724 0.063 Uiso 1 1 calc R
B B 0.83132(12) 0.81704(12) 0.06095(6) 0.0399(4) Uani 1 1 d .
H1BA H 0.9094(10) 0.8602(10) 0.0455(5) 0.047(4) Uiso 1 1 d .
H1BB H 0.7842(11) 0.7466(10) 0.0404(5) 0.047(4) Uiso 1 1 d .
H1BC H 0.8352(11) 0.8065(11) 0.0993(5) 0.053(4) 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'
N N 0.0061 0.0033 '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
C1 N B 116.31(10)
C1 N H1NA 109.0(9)
B N H1NA 110.6(9)
C1 N H1NB 108.3(8)
B N H1NB 107.8(9)
H1NA N H1NB 104.1(12)
C2 C1 C6 122.43(11)
C2 C1 N 118.25(10)
C6 C1 N 119.32(10)
C3 C2 C1 117.53(11)
C3 C2 C7 119.19(11)
C1 C2 C7 123.28(11)
C4 C3 C2 121.15(12)
C3 C4 C5 120.02(12)
C4 C5 C6 121.74(12)
C5 C6 C1 116.95(11)
C5 C6 C10 118.78(11)
C1 C6 C10 124.24(11)
C9 C7 C8 110.88(12)
C9 C7 C2 111.49(11)
C8 C7 C2 111.59(12)
C6 C10 C11 110.27(11)
C6 C10 C12 112.23(11)
C11 C10 C12 110.33(11)
N B H1BA 106.4(7)
N B H1BB 106.0(7)
H1BA B H1BB 111.4(10)
N B H1BC 108.6(8)
H1BA B H1BC 109.7(10)
H1BB B H1BC 114.4(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C1 1.4633(14)
N B 1.6197(17)
N H1NA 0.911(15)
N H1NB 0.936(15)
C1 C2 1.3970(16)
C1 C6 1.3971(16)
C2 C3 1.3920(18)
C2 C7 1.5183(17)
C3 C4 1.3697(19)
C4 C5 1.375(2)
C5 C6 1.3895(18)
C6 C10 1.5207(17)
C7 C9 1.5131(18)
C7 C8 1.518(2)
C10 C11 1.5269(18)
C10 C12 1.5293(19)
B H1BA 1.134(14)
B H1BB 1.120(14)
B H1BC 1.085(15)
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
B N C1 C2 90.20(13)
B N C1 C6 -89.48(14)
C6 C1 C2 C3 -4.84(17)
N C1 C2 C3 175.49(10)
C6 C1 C2 C7 175.83(11)
N C1 C2 C7 -3.83(17)
C1 C2 C3 C4 2.06(19)
C7 C2 C3 C4 -178.58(12)
C2 C3 C4 C5 1.5(2)
C3 C4 C5 C6 -2.5(2)
C4 C5 C6 C1 -0.11(19)
C4 C5 C6 C10 177.79(12)
C2 C1 C6 C5 3.87(17)
N C1 C6 C5 -176.46(11)
C2 C1 C6 C10 -173.90(11)
N C1 C6 C10 5.76(17)
C3 C2 C7 C9 -66.67(15)
C1 C2 C7 C9 112.65(14)
C3 C2 C7 C8 57.92(16)
C1 C2 C7 C8 -122.76(14)
C5 C6 C10 C11 -69.46(16)
C1 C6 C10 C11 108.27(14)
C5 C6 C10 C12 53.97(16)
C1 C6 C10 C12 -128.29(13)
