#------------------------------------------------------------------------------
#$Date: 2019-03-05 09:52:05 +0100 (mar 05 de mar de 2019) $
#$Revision: 213973 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/23/7012322.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_7012322
loop_
_publ_author_name
'Vagedes, Dominik'
'Erker, Gerhard'
'Kehr, Gerald'
'Bergander, Klaus'
'Kataeva, Olga'
'Fröhlich, Roland'
'Grimme, Stefan'
'Mück-Lichtenfeld, Christian'
_publ_section_title
;
 Tris(pentafluorophenyl)borane adducts of substituted imidazoles:
 conformational features and chemical behavior upon deprotonation
;
_journal_issue                   7
_journal_name_full               'Dalton Transactions'
_journal_page_first              1337
_journal_paper_doi               10.1039/b210030b
_journal_year                    2003
_chemical_formula_sum            'C26 H23 B N2'
_chemical_formula_weight         374.27
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 123.12(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.155(2)
_cell_length_b                   14.400(1)
_cell_length_c                   17.119(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      44.70
_cell_measurement_theta_min      39.88
_cell_volume                     4161.2(8)
_computing_cell_refinement       'Express (Nonius B.V., 1994)'
_computing_data_collection       'Express (Nonius B.V., 1994)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8590
_diffrn_reflns_theta_full        74.20
_diffrn_reflns_theta_max         74.20
_diffrn_reflns_theta_min         4.04
_diffrn_standards_decay_%        0.7
_diffrn_standards_interval_count 250
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.527
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_correction_T_min  0.8796
_exptl_absorpt_correction_type   'empirical via \y scan data'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00051(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    'refined as ridign atoms'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0665P)²+0.9894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                2791
_reflns_number_total             4241
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b210030b.txt
_cod_data_source_block           erk1632
_cod_original_cell_volume        4161.2(7)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7012322
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.22359(7) 0.26214(9) 0.29290(9) 0.0438(3) Uani 1 1 d . . .
C2 C 0.28998(10) 0.21346(11) 0.33180(11) 0.0483(4) Uani 1 1 d . . .
H2 H 0.3265 0.2179 0.3141 0.058 Uiso 1 1 calc R . .
N3 N 0.29915(8) 0.15733(10) 0.39901(9) 0.0491(3) Uani 1 1 d . . .
C4 C 0.23409(9) 0.16877(11) 0.40527(10) 0.0452(4) Uani 1 1 d . . .
C5 C 0.18612(9) 0.23501(11) 0.33829(10) 0.0432(4) Uani 1 1 d . . .
C6 C 0.21375(11) 0.12596(13) 0.46203(11) 0.0556(4) Uani 1 1 d . . .
H6 H 0.2469 0.0817 0.5071 0.067 Uiso 1 1 calc R . .
C7 C 0.14285(11) 0.15164(14) 0.44877(12) 0.0598(5) Uani 1 1 d . . .
H7 H 0.1267 0.1242 0.4856 0.072 Uiso 1 1 calc R . .
C8 C 0.09395(11) 0.21758(14) 0.38190(13) 0.0579(4) Uani 1 1 d . . .
H8 H 0.0457 0.2332 0.3748 0.069 Uiso 1 1 calc R . .
C9 C 0.11443(9) 0.26046(13) 0.32599(11) 0.0510(4) Uani 1 1 d . . .
H9 H 0.0813 0.3050 0.2814 0.061 Uiso 1 1 calc R . .
C10 C 0.36449(11) 0.09348(14) 0.45527(14) 0.0671(5) Uani 1 1 d . . .
H10A H 0.4045 0.1016 0.4409 0.101 Uiso 1 1 calc R . .
H10B H 0.3450 0.0301 0.4415 0.101 Uiso 1 1 calc R . .
H10C H 0.3875 0.1062 0.5209 0.101 Uiso 1 1 calc R . .
B B 0.18631(11) 0.32669(13) 0.20043(12) 0.0449(4) Uani 1 1 d . . .
C11 C 0.15182(9) 0.41779(11) 0.22306(11) 0.0444(4) Uani 1 1 d . . .
C12 C 0.07515(10) 0.45202(12) 0.16412(12) 0.0529(4) Uani 1 1 d . . .
H12 H 0.0405 0.4206 0.1079 0.063 Uiso 1 1 calc R . .
C13 C 0.04804(11) 0.53031(14) 0.18514(14) 0.0634(5) Uani 1 1 d . . .
H13 H -0.0042 0.5509 0.1434 0.076 Uiso 1 1 calc R . .
C14 C 0.09688(13) 0.57829(14) 0.26668(14) 0.0656(5) Uani 1 1 d . . .
H14 H 0.0787 0.6322 0.2803 0.079 Uiso 1 1 calc R . .
C15 C 0.17283(12) 0.54644(13) 0.32823(13) 0.0599(5) Uani 1 1 d . . .
H15 H 0.2066 0.5778 0.3847 0.072 Uiso 1 1 calc R . .
C16 C 0.19890(10) 0.46764(12) 0.30608(12) 0.0516(4) Uani 1 1 d . . .
H16 H 0.2508 0.4467 0.3489 0.062 Uiso 1 1 calc R . .
C21 C 0.11870(9) 0.26404(11) 0.11397(11) 0.0470(4) Uani 1 1 d . . .
C22 C 0.09949(12) 0.17323(12) 0.12225(12) 0.0586(5) Uani 1 1 d . . .
H22 H 0.1264 0.1456 0.1817 0.070 Uiso 1 1 calc R . .
C23 C 0.04232(14) 0.12173(15) 0.04657(14) 0.0730(6) Uani 1 1 d . . .
H23 H 0.0311 0.0608 0.0557 0.088 Uiso 1 1 calc R . .
C24 C 0.00216(12) 0.15889(15) -0.04117(14) 0.0699(6) Uani 1 1 d . . .
H24 H -0.0368 0.1242 -0.0925 0.084 Uiso 1 1 calc R . .
C25 C 0.01960(11) 0.24746(15) -0.05303(13) 0.0653(5) Uani 1 1 d . . .
H25 H -0.0073 0.2737 -0.1130 0.078 Uiso 1 1 calc R . .
C26 C 0.07674(11) 0.29895(13) 0.02292(12) 0.0570(4) Uani 1 1 d . . .
H26 H 0.0876 0.3596 0.0127 0.068 Uiso 1 1 calc R . .
C31 C 0.25746(10) 0.35267(11) 0.18503(11) 0.0469(4) Uani 1 1 d . . .
C32 C 0.30520(10) 0.43170(13) 0.22062(12) 0.0556(4) Uani 1 1 d . . .
H32 H 0.2960 0.4740 0.2555 0.067 Uiso 1 1 calc R . .
C33 C 0.36538(11) 0.45069(15) 0.20690(14) 0.0648(5) Uani 1 1 d . . .
H33 H 0.3961 0.5046 0.2327 0.078 Uiso 1 1 calc R . .
C34 C 0.38032(12) 0.39127(16) 0.15590(15) 0.0691(6) Uani 1 1 d . . .
H34 H 0.4214 0.4038 0.1467 0.083 Uiso 1 1 calc R . .
C35 C 0.33449(14) 0.31319(17) 0.11844(16) 0.0784(6) Uani 1 1 d . . .
H35 H 0.3438 0.2721 0.0828 0.094 Uiso 1 1 calc R . .
C36 C 0.27440(12) 0.29451(14) 0.13288(15) 0.0667(5) Uani 1 1 d . . .
H36 H 0.2439 0.2405 0.1065 0.080 Uiso 1 1 calc R . .
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'
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
_geom_angle_publ_flag
C2 N1 C5 106.04(13) . . ?
C2 N1 B 126.57(13) . . ?
C5 N1 B 126.67(12) . . ?
N1 C2 N3 112.36(15) . . ?
C2 N3 C4 107.72(13) . . ?
C2 N3 C10 127.02(14) . . ?
C4 N3 C10 125.25(14) . . ?
N3 C4 C6 131.04(15) . . ?
N3 C4 C5 106.17(14) . . ?
C6 C4 C5 122.79(16) . . ?
C9 C5 C4 120.04(15) . . ?
C9 C5 N1 132.23(15) . . ?
C4 C5 N1 107.72(13) . . ?
C7 C6 C4 116.39(16) . . ?
C6 C7 C8 121.63(17) . . ?
C9 C8 C7 121.93(17) . . ?
C8 C9 C5 117.22(16) . . ?
N1 B C11 105.05(12) . . ?
N1 B C21 106.29(13) . . ?
C11 B C21 114.10(13) . . ?
N1 B C31 107.97(12) . . ?
C11 B C31 112.33(13) . . ?
C21 B C31 110.58(13) . . ?
C12 C11 C16 114.93(15) . . ?
C12 C11 B 124.14(15) . . ?
C16 C11 B 120.93(14) . . ?
C13 C12 C11 122.60(17) . . ?
C14 C13 C12 120.52(18) . . ?
C13 C14 C15 119.23(18) . . ?
C14 C15 C16 119.42(18) . . ?
C15 C16 C11 123.27(17) . . ?
C22 C21 C26 114.73(16) . . ?
C22 C21 B 124.62(15) . . ?
C26 C21 B 120.62(15) . . ?
C23 C22 C21 122.82(18) . . ?
C24 C23 C22 120.5(2) . . ?
C23 C24 C25 118.83(18) . . ?
C24 C25 C26 120.52(19) . . ?
C25 C26 C21 122.57(18) . . ?
C36 C31 C32 114.65(16) . . ?
C36 C31 B 120.52(15) . . ?
C32 C31 B 124.83(15) . . ?
C33 C32 C31 123.09(17) . . ?
C34 C33 C32 120.26(19) . . ?
C33 C34 C35 118.95(18) . . ?
C34 C35 C36 120.39(19) . . ?
C35 C36 C31 122.66(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.324(2) . ?
N1 C5 1.403(2) . ?
N1 B 1.623(2) . ?
C2 N3 1.334(2) . ?
N3 C4 1.383(2) . ?
N3 C10 1.456(2) . ?
C4 C6 1.388(2) . ?
C4 C5 1.396(2) . ?
C5 C9 1.391(2) . ?
C6 C7 1.370(3) . ?
C7 C8 1.397(3) . ?
C8 C9 1.378(2) . ?
B C11 1.627(2) . ?
B C21 1.630(2) . ?
B C31 1.637(2) . ?
C11 C12 1.395(2) . ?
C11 C16 1.401(2) . ?
C12 C13 1.383(2) . ?
C13 C14 1.376(3) . ?
C14 C15 1.379(3) . ?
C15 C16 1.388(2) . ?
C21 C22 1.393(2) . ?
C21 C26 1.399(2) . ?
C22 C23 1.387(3) . ?
C23 C24 1.367(3) . ?
C24 C25 1.367(3) . ?
C25 C26 1.389(3) . ?
C31 C36 1.396(2) . ?
C31 C32 1.397(2) . ?
C32 C33 1.383(2) . ?
C33 C34 1.368(3) . ?
C34 C35 1.372(3) . ?
C35 C36 1.388(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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 -0.35(18) . . . . ?
B N1 C2 N3 -171.13(14) . . . . ?
N1 C2 N3 C4 0.37(19) . . . . ?
N1 C2 N3 C10 179.18(16) . . . . ?
C2 N3 C4 C6 178.56(17) . . . . ?
C10 N3 C4 C6 -0.3(3) . . . . ?
C2 N3 C4 C5 -0.22(17) . . . . ?
C10 N3 C4 C5 -179.06(16) . . . . ?
N3 C4 C5 C9 178.67(14) . . . . ?
C6 C4 C5 C9 -0.2(2) . . . . ?
N3 C4 C5 N1 0.01(17) . . . . ?
C6 C4 C5 N1 -178.89(14) . . . . ?
C2 N1 C5 C9 -178.24(17) . . . . ?
B N1 C5 C9 -7.5(3) . . . . ?
C2 N1 C5 C4 0.20(17) . . . . ?
B N1 C5 C4 170.96(14) . . . . ?
N3 C4 C6 C7 -178.19(17) . . . . ?
C5 C4 C6 C7 0.4(3) . . . . ?
C4 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C5 0.4(3) . . . . ?
C4 C5 C9 C8 -0.2(2) . . . . ?
N1 C5 C9 C8 178.11(16) . . . . ?
C2 N1 B C11 -140.49(15) . . . . ?
C5 N1 B C11 50.58(19) . . . . ?
C2 N1 B C21 98.24(17) . . . . ?
C5 N1 B C21 -70.68(18) . . . . ?
C2 N1 B C31 -20.4(2) . . . . ?
C5 N1 B C31 170.64(14) . . . . ?
N1 B C11 C12 -128.87(15) . . . . ?
C21 B C11 C12 -12.9(2) . . . . ?
C31 B C11 C12 114.01(17) . . . . ?
N1 B C11 C16 50.63(19) . . . . ?
C21 B C11 C16 166.63(14) . . . . ?
C31 B C11 C16 -66.49(18) . . . . ?
C16 C11 C12 C13 1.2(2) . . . . ?
B C11 C12 C13 -179.29(16) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C12 C11 C16 C15 -1.4(2) . . . . ?
B C11 C16 C15 179.08(15) . . . . ?
N1 B C21 C22 -0.1(2) . . . . ?
C11 B C21 C22 -115.38(18) . . . . ?
C31 B C21 C22 116.85(18) . . . . ?
N1 B C21 C26 -177.90(14) . . . . ?
C11 B C21 C26 66.8(2) . . . . ?
C31 B C21 C26 -61.0(2) . . . . ?
C26 C21 C22 C23 -1.1(3) . . . . ?
B C21 C22 C23 -178.97(18) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
C22 C23 C24 C25 0.3(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C21 -0.1(3) . . . . ?
C22 C21 C26 C25 0.9(3) . . . . ?
B C21 C26 C25 178.89(17) . . . . ?
N1 B C31 C36 88.52(18) . . . . ?
C11 B C31 C36 -156.12(16) . . . . ?
C21 B C31 C36 -27.4(2) . . . . ?
N1 B C31 C32 -91.72(18) . . . . ?
C11 B C31 C32 23.6(2) . . . . ?
C21 B C31 C32 152.38(16) . . . . ?
C36 C31 C32 C33 -1.0(3) . . . . ?
B C31 C32 C33 179.27(17) . . . . ?
C31 C32 C33 C34 0.5(3) . . . . ?
C32 C33 C34 C35 0.3(3) . . . . ?
C33 C34 C35 C36 -0.6(3) . . . . ?
C34 C35 C36 C31 0.0(3) . . . . ?
C32 C31 C36 C35 0.7(3) . . . . ?
B C31 C36 C35 -179.52(18) . . . . ?
