#------------------------------------------------------------------------------
#$Date: 2017-07-04 04:33:08 +0300 (Tue, 04 Jul 2017) $
#$Revision: 198352 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/64/1546456.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_1546456
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            'C12.5 H14 B Cl N4'
_chemical_formula_weight         266.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.3418(3)
_cell_length_b                   18.4372(5)
_cell_length_c                   12.9532(3)
_cell_measurement_reflns_used    19537
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9740
_cell_measurement_theta_min      4.5550
_cell_volume                     2708.66(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_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 10.3543
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27441
_diffrn_reflns_theta_full        75.00
_diffrn_reflns_theta_max         76.21
_diffrn_reflns_theta_min         4.58
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.   
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut needle'
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.019(17)
_refine_ls_extinction_coef       0.00070(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0327
_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)+(0.0479P)²+1.5380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                2733
_reflns_number_total             2795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7sc02238g2.cif
_cod_data_source_block           rf17fr
_cod_original_cell_volume        2708.64(12)
_cod_original_formula_sum        'C12.50 H14 B Cl N4'
_cod_database_code               1546456
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
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
B1 B 0.5000 0.63642(13) 0.9324(2) 0.0225(5) Uani 1 2 d S
N1 N 0.40422(10) 0.50659(7) 0.96985(10) 0.0201(3) Uani 1 1 d .
N2 N 0.68929(14) 0.70823(9) 1.01636(13) 0.0363(4) Uani 1 1 d .
C1 C 0.5000 0.54959(12) 0.95899(16) 0.0201(4) Uani 1 2 d S
C2 C 0.43864(13) 0.43544(8) 0.98898(12) 0.0203(3) Uani 1 1 d .
C3 C 0.37377(13) 0.37217(8) 1.00466(13) 0.0229(3) Uani 1 1 d .
H3 H 0.2900 0.3722 1.0047 0.027 Uiso 1 1 calc R
C4 C 0.43787(14) 0.30940(8) 1.02013(12) 0.0249(3) Uani 1 1 d .
H4 H 0.3971 0.2650 1.0311 0.030 Uiso 1 1 calc R
C5 C 0.28032(13) 0.52767(8) 0.95934(14) 0.0260(3) Uani 1 1 d .
H5A H 0.2727 0.5641 0.9046 0.039 Uiso 1 1 calc R
H5B H 0.2523 0.5481 1.0247 0.039 Uiso 1 1 calc R
H5C H 0.2330 0.4849 0.9417 0.039 Uiso 1 1 calc R
C6 C 0.61125(14) 0.67633(8) 0.98334(13) 0.0267(3) Uani 1 1 d .
C7 C 0.5000 0.65013(12) 0.80849(19) 0.0246(4) Uani 1 2 d S
H7A H 0.5000 0.7013 0.7949 0.037 Uiso 1 2 d SR
H7B H 0.5691 0.6286 0.7787 0.037 Uiso 1 1 d R
B1' B 0.5000 0.86411(13) 0.2797(2) 0.0219(5) Uani 1 2 d S
N1' N 0.59575(11) 0.73387(7) 0.25355(11) 0.0213(3) Uani 1 1 d .
N2' N 0.68559(13) 0.93714(8) 0.19042(13) 0.0337(3) Uani 1 1 d .
C1' C 0.5000 0.77709(11) 0.25973(18) 0.0211(4) Uani 1 2 d S
C2' C 0.56113(13) 0.66211(8) 0.24173(11) 0.0209(3) Uani 1 1 d .
C3' C 0.62613(14) 0.59847(8) 0.22948(12) 0.0239(3) Uani 1 1 d .
H3' H 0.7099 0.5986 0.2291 0.029 Uiso 1 1 calc R
C4' C 0.56187(15) 0.53490(8) 0.21788(13) 0.0252(3) Uani 1 1 d .
H4' H 0.6027 0.4903 0.2097 0.030 Uiso 1 1 calc R
C5' C 0.71968(13) 0.75545(9) 0.26308(14) 0.0276(3) Uani 1 1 d .
H5'1 H 0.7251 0.7999 0.3044 0.041 Uiso 1 1 calc R
H5'2 H 0.7525 0.7643 0.1943 0.041 Uiso 1 1 calc R
H5'3 H 0.7642 0.7166 0.2970 0.041 Uiso 1 1 calc R
C6' C 0.61066(14) 0.90319(8) 0.22545(13) 0.0248(3) Uani 1 1 d .
C7' C 0.5000 0.88051(12) 0.4033(2) 0.0259(5) Uani 1 2 d S
H7'1 H 0.5000 0.9320 0.4146 0.039 Uiso 1 2 d SR
H7'2 H 0.5691 0.8596 0.4340 0.039 Uiso 1 1 d R
C99 C 0.5000 0.92182(14) 0.7880(3) 0.0411(6) Uani 1 2 d S
H99 H 0.4294 0.9533 0.7849 0.049 Uiso 1 1 d R
Cl1 Cl 0.5000 0.86370(5) 0.68202(8) 0.0642(3) Uani 1 2 d S
Cl2 Cl 0.5000 0.87422(6) 0.90481(8) 0.0786(3) Uani 1 2 d S
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 B1 C6 103.84(18) . 4_655
C6 B1 C7 109.60(13) . .
C6 B1 C7 109.60(13) 4_655 .
C6 B1 C1 111.22(13) . .
C6 B1 C1 111.22(13) 4_655 .
C7 B1 C1 111.11(18) . .
C1 N1 C2 110.24(13) . .
C1 N1 C5 127.28(13) . .
C2 N1 C5 122.43(12) . .
N1 C1 N1 106.91(18) 4_655 .
N1 C1 B1 126.52(9) 4_655 .
N1 C1 B1 126.52(9) . .
N1 C2 C2 106.30(8) . 4_655
N1 C2 C3 131.84(13) . .
C2 C2 C3 121.85(9) 4_655 .
C4 C3 C2 116.39(14) . .
C3 C4 C4 121.76(9) . 4_655
N2 C6 B1 176.09(19) . .
C6' B1' C6' 102.55(18) . 4_655
C6' B1' C1' 111.88(13) . .
C6' B1' C1' 111.88(13) 4_655 .
C6' B1' C7' 110.25(13) . .
C6' B1' C7' 110.25(13) 4_655 .
C1' B1' C7' 109.86(19) . .
C1' N1' C2' 109.97(13) . .
C1' N1' C5' 127.32(13) . .
C2' N1' C5' 122.62(12) . .
N1' C1' N1' 107.19(17) 4_655 .
N1' C1' B1' 126.33(9) 4_655 .
N1' C1' B1' 126.33(9) . .
C2' C2' N1' 106.43(8) 4_655 .
C2' C2' C3' 121.91(9) 4_655 .
N1' C2' C3' 131.65(14) . .
C4' C3' C2' 116.43(15) . .
C3' C4' C4' 121.67(10) . 4_655
N2' C6' B1' 173.52(17) . .
Cl1 C99 Cl2 111.91(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 C6 1.603(2) .
B1 C6 1.603(2) 4_655
B1 C7 1.624(4) .
B1 C1 1.638(3) .
N1 C1 1.3522(17) .
N1 C2 1.3910(18) .
N1 C5 1.4643(18) .
N2 C6 1.146(2) .
C1 N1 1.3522(17) 4_655
C2 C2 1.392(3) 4_655
C2 C3 1.394(2) .
C3 C4 1.381(2) .
C4 C4 1.409(3) 4_655
B1' C6' 1.609(2) .
B1' C6' 1.609(2) 4_655
B1' C1' 1.625(3) .
B1' C7' 1.629(4) .
N1' C1' 1.3494(17) .
N1' C2' 1.3884(18) .
N1' C5' 1.4660(19) .
N2' C6' 1.149(2) .
C1' N1' 1.3494(17) 4_655
C2' C2' 1.387(3) 4_655
C2' C3' 1.395(2) .
C3' C4' 1.388(2) .
C4' C4' 1.403(3) 4_655
C99 Cl1 1.741(3) .
C99 Cl2 1.749(3) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 N1 C1 N1 0.7(2) . 4_655
C5 N1 C1 N1 -176.75(10) . 4_655
C2 N1 C1 B1 178.04(19) . .
C5 N1 C1 B1 0.6(3) . .
C6 B1 C1 N1 -34.0(3) . 4_655
C6 B1 C1 N1 -149.17(18) 4_655 4_655
C7 B1 C1 N1 88.44(19) . 4_655
C6 B1 C1 N1 149.17(18) . .
C6 B1 C1 N1 34.0(3) 4_655 .
C7 B1 C1 N1 -88.44(19) . .
C1 N1 C2 C2 -0.41(14) . 4_655
C5 N1 C2 C2 177.15(12) . 4_655
C1 N1 C2 C3 -179.47(18) . .
C5 N1 C2 C3 -1.9(3) . .
N1 C2 C3 C4 178.89(15) . .
C2 C2 C3 C4 -0.05(19) 4_655 .
C2 C3 C4 C4 0.05(19) . 4_655
C2' N1' C1' N1' 0.9(2) . 4_655
C5' N1' C1' N1' -175.92(11) . 4_655
C2' N1' C1' B1' 176.6(2) . .
C5' N1' C1' B1' -0.2(3) . .
C6' B1' C1' N1' -149.74(18) . 4_655
C6' B1' C1' N1' -35.3(3) 4_655 4_655
C7' B1' C1' N1' 87.5(2) . 4_655
C6' B1' C1' N1' 35.3(3) . .
C6' B1' C1' N1' 149.74(18) 4_655 .
C7' B1' C1' N1' -87.5(2) . .
C1' N1' C2' C2' -0.55(15) . 4_655
C5' N1' C2' C2' 176.43(13) . 4_655
C1' N1' C2' C3' 178.20(18) . .
C5' N1' C2' C3' -4.8(3) . .
C2' C2' C3' C4' -0.38(18) 4_655 .
N1' C2' C3' C4' -178.97(16) . .
C2' C3' C4' C4' 0.37(18) . 4_655
