#------------------------------------------------------------------------------
#$Date: 2017-07-04 04:33:08 +0300 (Tue, 04 Jul 2017) $
#$Revision: 198352 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/64/1546447.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_1546447
loop_
_publ_author_name
'Böser, Richard'
'Haufe, Lisa Cathrin'
'Freytag, Matthias'
'Jones, P. G.'
'Hörner, Gerald'
'René, Frank'
_publ_section_title
;
 Completing the series of boron-nucleophilic cyanoborates: Boryl anions of
 type (NHC)−B(CN)2−
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC02238G
_journal_year                    2017
_chemical_formula_sum            'C14 H20 B N3 S2'
_chemical_formula_weight         305.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-05-17 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.764(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4737(2)
_cell_length_b                   12.0926(2)
_cell_length_c                   13.1679(3)
_cell_measurement_reflns_used    32313
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.9250
_cell_measurement_theta_min      2.3220
_cell_volume                     1612.71(6)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            120276
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         31.38
_diffrn_reflns_theta_min         2.23
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut prism'
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         5120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0364
_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)+(0.0349P)²+0.7616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                4528
_reflns_number_total             5120
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7sc02238g2.cif
_cod_data_source_block           rf13mf
_cod_original_cell_volume        1612.71(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1546447
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S1 S 0.44342(3) 0.11552(2) 0.62347(3) 0.02571(8) Uani 1 1 d .
S2 S 0.14428(3) 0.14806(2) 0.61599(2) 0.02247(8) Uani 1 1 d .
B1 B 0.27827(12) 0.17011(10) 0.54146(9) 0.0163(2) Uani 1 1 d .
N1 N 0.33387(9) 0.37546(7) 0.60330(7) 0.01498(17) Uani 1 1 d .
N2 N 0.29614(9) 0.35633(7) 0.43372(7) 0.01460(17) Uani 1 1 d .
N3 N 0.19977(12) 0.03964(9) 0.36730(8) 0.0280(2) Uani 1 1 d .
C1 C 0.30306(10) 0.30047(9) 0.52424(8) 0.01431(18) Uani 1 1 d .
C2 C 0.34526(10) 0.47992(9) 0.56318(8) 0.01491(19) Uani 1 1 d .
C3 C 0.37636(11) 0.58159(9) 0.61275(9) 0.0193(2) Uani 1 1 d .
H3 H 0.3940 0.5893 0.6868 0.023 Uiso 1 1 calc R
C4 C 0.38000(11) 0.67091(9) 0.54767(10) 0.0223(2) Uani 1 1 d .
H4 H 0.4001 0.7421 0.5780 0.027 Uiso 1 1 calc R
C5 C 0.35495(11) 0.65934(9) 0.43866(10) 0.0222(2) Uani 1 1 d .
H5 H 0.3581 0.7229 0.3970 0.027 Uiso 1 1 calc R
C6 C 0.32576(11) 0.55778(9) 0.38981(9) 0.0191(2) Uani 1 1 d .
H6 H 0.3100 0.5497 0.3159 0.023 Uiso 1 1 calc R
C7 C 0.32083(10) 0.46805(9) 0.45512(8) 0.01515(19) Uani 1 1 d .
C8 C 0.36075(12) 0.35566(10) 0.71643(8) 0.0208(2) Uani 1 1 d .
H8A H 0.3307 0.2813 0.7288 0.031 Uiso 1 1 calc R
H8B H 0.3137 0.4106 0.7480 0.031 Uiso 1 1 calc R
H8C H 0.4558 0.3618 0.7482 0.031 Uiso 1 1 calc R
C9 C 0.26915(12) 0.31141(10) 0.32714(8) 0.0203(2) Uani 1 1 d .
H9A H 0.3219 0.2444 0.3273 0.031 Uiso 1 1 calc R
H9B H 0.2923 0.3665 0.2803 0.031 Uiso 1 1 calc R
H9C H 0.1751 0.2932 0.3025 0.031 Uiso 1 1 calc R
C10 C 0.41193(14) -0.03191(9) 0.63242(10) 0.0255(2) Uani 1 1 d .
H10A H 0.3155 -0.0454 0.6133 0.031 Uiso 1 1 calc R
H10B H 0.4504 -0.0728 0.5822 0.031 Uiso 1 1 calc R
C11 C 0.47088(16) -0.07339(13) 0.74134(13) 0.0401(4) Uani 1 1 d .
H11A H 0.5668 -0.0629 0.7591 0.060 Uiso 1 1 calc R
H11B H 0.4509 -0.1522 0.7451 0.060 Uiso 1 1 calc R
H11C H 0.4336 -0.0322 0.7911 0.060 Uiso 1 1 calc R
C12 C -0.01138(12) 0.16622(12) 0.51683(11) 0.0300(3) Uani 1 1 d .
H12A H -0.0146 0.1130 0.4591 0.036 Uiso 1 1 calc R
H12B H -0.0849 0.1481 0.5486 0.036 Uiso 1 1 calc R
C13 C -0.03278(13) 0.28144(13) 0.47098(11) 0.0336(3) Uani 1 1 d .
H13A H -0.0236 0.3355 0.5279 0.050 Uiso 1 1 calc R
H13B H -0.1216 0.2867 0.4238 0.050 Uiso 1 1 calc R
H13C H 0.0329 0.2968 0.4315 0.050 Uiso 1 1 calc R
C14 C 0.23387(11) 0.09928(9) 0.43668(9) 0.0193(2) Uani 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'
S S 0.1246 0.1234 '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
C10 S1 B1 102.83(6)
C12 S2 B1 104.66(6)
C14 B1 C1 115.08(9)
C14 B1 S1 109.10(8)
C1 B1 S1 105.12(7)
C14 B1 S2 106.14(7)
C1 B1 S2 111.66(8)
S1 B1 S2 109.70(6)
C1 N1 C2 110.09(9)
C1 N1 C8 128.20(9)
C2 N1 C8 121.61(9)
C1 N2 C7 109.90(9)
C1 N2 C9 127.74(9)
C7 N2 C9 122.36(9)
N2 C1 N1 106.90(9)
N2 C1 B1 129.21(9)
N1 C1 B1 123.88(9)
N1 C2 C7 106.58(9)
N1 C2 C3 131.23(10)
C7 C2 C3 122.18(10)
C4 C3 C2 116.03(10)
C3 C4 C5 121.95(11)
C6 C5 C4 121.82(10)
C5 C6 C7 116.27(10)
C2 C7 N2 106.52(9)
C2 C7 C6 121.75(10)
N2 C7 C6 131.72(10)
C11 C10 S1 110.65(9)
C13 C12 S2 114.28(9)
N3 C14 B1 173.16(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C10 1.8223(12)
S1 B1 1.9084(13)
S2 C12 1.8238(14)
S2 B1 1.9250(12)
B1 C14 1.5895(16)
B1 C1 1.6229(16)
N1 C1 1.3562(13)
N1 C2 1.3861(13)
N1 C8 1.4635(14)
N2 C1 1.3558(13)
N2 C7 1.3908(13)
N2 C9 1.4637(14)
N3 C14 1.1472(15)
C2 C7 1.3875(15)
C2 C3 1.3912(15)
C3 C4 1.3853(16)
C4 C5 1.3990(18)
C5 C6 1.3839(16)
C6 C7 1.3937(15)
C10 C11 1.4962(19)
C12 C13 1.512(2)
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
C10 S1 B1 C14 -52.46(9)
C10 S1 B1 C1 -176.39(7)
C10 S1 B1 S2 63.42(7)
C12 S2 B1 C14 -46.70(9)
C12 S2 B1 C1 79.44(9)
C12 S2 B1 S1 -164.44(6)
C7 N2 C1 N1 -0.87(11)
C9 N2 C1 N1 178.32(10)
C7 N2 C1 B1 178.12(10)
C9 N2 C1 B1 -2.69(17)
C2 N1 C1 N2 0.67(11)
C8 N1 C1 N2 -175.79(10)
C2 N1 C1 B1 -178.39(9)
C8 N1 C1 B1 5.16(17)
C14 B1 C1 N2 -2.79(16)
S1 B1 C1 N2 117.26(10)
S2 B1 C1 N2 -123.86(10)
C14 B1 C1 N1 176.05(10)
S1 B1 C1 N1 -63.91(11)
S2 B1 C1 N1 54.98(12)
C1 N1 C2 C7 -0.22(12)
C8 N1 C2 C7 176.52(9)
C1 N1 C2 C3 -179.20(11)
C8 N1 C2 C3 -2.47(17)
N1 C2 C3 C4 179.60(11)
C7 C2 C3 C4 0.75(16)
C2 C3 C4 C5 -0.51(16)
C3 C4 C5 C6 -0.33(18)
C4 C5 C6 C7 0.91(16)
N1 C2 C7 N2 -0.32(11)
C3 C2 C7 N2 178.78(9)
N1 C2 C7 C6 -179.26(10)
C3 C2 C7 C6 -0.16(16)
C1 N2 C7 C2 0.74(11)
C9 N2 C7 C2 -178.50(9)
C1 N2 C7 C6 179.54(11)
C9 N2 C7 C6 0.30(17)
C5 C6 C7 C2 -0.67(15)
C5 C6 C7 N2 -179.32(11)
B1 S1 C10 C11 -137.55(11)
B1 S2 C12 C13 -64.32(11)
C1 B1 C14 N3 -172.1(10)
S1 B1 C14 N3 70.1(11)
S2 B1 C14 N3 -48.1(11)
