#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/35/4303535.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_4303535
loop_
_publ_author_name
'Stephen J. Geier'
'Austin L. Gille'
'Thomas M. Gilbert'
'Douglas W. Stephan'
_publ_section_title
;
From Classical Adducts to Frustrated Lewis Pairs: Steric Effects in the
Interactions of Pyridines and B(C6F5)3
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10466
_journal_page_last               10474
_journal_paper_doi               10.1021/ic901726b
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C28 H8 B F15 N2'
_chemical_formula_weight         668.17
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 91.27(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.706(2)
_cell_length_b                   16.332(3)
_cell_length_c                   14.368(3)
_cell_measurement_reflns_used    12019
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.7
_cell_volume                     2511.6(8)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0565
_diffrn_reflns_av_sigmaI/netI    0.0816
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12019
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         4389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0504
_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)+(0.0687P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                2499
_reflns_number_total             4389
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic901726b_si_002_05.cif
_cod_data_source_block           (((2-C5H4N)C5H4N)-B(C6F5)3)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4303535
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2371(2) 0.05683(16) 0.38193(19) 0.0256(7) Uani 1 1 d . . .
N2 N 0.0040(3) 0.18898(18) 0.4244(2) 0.0363(8) Uani 1 1 d . . .
B1 B 0.2700(4) 0.0970(2) 0.2800(3) 0.0278(10) Uani 1 1 d . . .
F2 F 0.18512(18) 0.02779(11) 0.08841(13) 0.0376(5) Uani 1 1 d . . .
F3 F 0.3211(2) -0.06344(12) -0.02082(13) 0.0460(6) Uani 1 1 d . . .
F4 F 0.5498(2) -0.12015(12) 0.03540(14) 0.0451(6) Uani 1 1 d . . .
F5 F 0.63760(19) -0.08343(12) 0.20989(15) 0.0435(6) Uani 1 1 d . . .
F6 F 0.50482(18) 0.01073(11) 0.32245(13) 0.0365(5) Uani 1 1 d . . .
F8 F 0.35190(17) 0.19299(11) 0.12659(12) 0.0320(5) Uani 1 1 d . . .
F9 F 0.54842(18) 0.29525(12) 0.12009(13) 0.0367(5) Uani 1 1 d . . .
F10 F 0.69868(17) 0.31751(11) 0.27346(13) 0.0348(5) Uani 1 1 d . . .
F11 F 0.64057(17) 0.24246(11) 0.43609(13) 0.0329(5) Uani 1 1 d . . .
F12 F 0.44423(17) 0.14275(11) 0.44597(12) 0.0314(5) Uani 1 1 d . . .
F14 F 0.05749(18) -0.00635(11) 0.25329(14) 0.0383(5) Uani 1 1 d . . .
F15 F -0.16972(18) 0.03442(12) 0.18983(15) 0.0461(6) Uani 1 1 d . . .
F16 F -0.22118(18) 0.19399(12) 0.13724(14) 0.0447(6) Uani 1 1 d . . .
F17 F -0.04101(18) 0.31181(11) 0.15737(14) 0.0388(5) Uani 1 1 d . . .
F18 F 0.18446(17) 0.27414(10) 0.22224(13) 0.0329(5) Uani 1 1 d . . .
C1 C 0.3366(3) 0.02571(19) 0.2130(2) 0.0269(8) Uani 1 1 d . . .
C2 C 0.2966(3) 0.00256(19) 0.1246(2) 0.0288(9) Uani 1 1 d . . .
C3 C 0.3658(3) -0.0453(2) 0.0648(2) 0.0320(9) Uani 1 1 d . . .
C4 C 0.4817(3) -0.07343(19) 0.0930(3) 0.0319(9) Uani 1 1 d . . .
C5 C 0.5259(3) -0.0543(2) 0.1802(3) 0.0327(9) Uani 1 1 d . . .
C6 C 0.4543(3) -0.0053(2) 0.2370(2) 0.0313(9) Uani 1 1 d . . .
C7 C 0.3826(3) 0.16616(19) 0.2877(2) 0.0237(8) Uani 1 1 d . . .
C8 C 0.4189(3) 0.2059(2) 0.2072(2) 0.0241(8) Uani 1 1 d . . .
C9 C 0.5211(3) 0.2569(2) 0.2006(2) 0.0272(8) Uani 1 1 d . . .
C10 C 0.5972(3) 0.26866(19) 0.2777(2) 0.0267(8) Uani 1 1 d . . .
C11 C 0.5677(3) 0.23032(19) 0.3592(2) 0.0275(8) Uani 1 1 d . . .
C12 C 0.4634(3) 0.18030(19) 0.3631(2) 0.0253(8) Uani 1 1 d . . .
C13 C 0.1356(3) 0.12957(19) 0.2394(2) 0.0251(8) Uani 1 1 d . . .
C14 C 0.0374(3) 0.0743(2) 0.2298(2) 0.0298(9) Uani 1 1 d . . .
C15 C -0.0803(3) 0.0936(2) 0.1968(2) 0.0329(9) Uani 1 1 d . . .
C16 C -0.1068(3) 0.1736(2) 0.1705(2) 0.0301(9) Uani 1 1 d . . .
C17 C -0.0147(3) 0.23228(19) 0.1799(2) 0.0280(8) Uani 1 1 d . . .
C18 C 0.1023(3) 0.2101(2) 0.2132(2) 0.0271(8) Uani 1 1 d . . .
C19 C 0.2627(3) -0.0235(2) 0.3992(2) 0.0327(9) Uani 1 1 d . . .
H19A H 0.2989 -0.0540 0.3522 0.039 Uiso 1 1 calc R . .
C20 C 0.2385(4) -0.0623(2) 0.4815(3) 0.0390(10) Uani 1 1 d . . .
H20A H 0.2575 -0.1175 0.4895 0.047 Uiso 1 1 calc R . .
C21 C 0.1858(4) -0.0185(2) 0.5514(3) 0.0460(11) Uani 1 1 d . . .
H21A H 0.1710 -0.0425 0.6088 0.055 Uiso 1 1 calc R . .
C22 C 0.1546(4) 0.0635(2) 0.5345(3) 0.0389(10) Uani 1 1 d . . .
H22A H 0.1171 0.0938 0.5811 0.047 Uiso 1 1 calc R . .
C23 C 0.1781(3) 0.1003(2) 0.4504(2) 0.0278(8) Uani 1 1 d . . .
C24 C 0.1293(3) 0.1868(2) 0.4358(2) 0.0284(8) Uani 1 1 d . . .
C25 C 0.2018(3) 0.2570(2) 0.4434(2) 0.0318(9) Uani 1 1 d . . .
H25A H 0.2875 0.2531 0.4546 0.038 Uiso 1 1 calc R . .
C26 C 0.1448(4) 0.3336(2) 0.4342(3) 0.0378(9) Uani 1 1 d . . .
H26A H 0.1922 0.3813 0.4376 0.045 Uiso 1 1 calc R . .
C27 C 0.0182(4) 0.3372(2) 0.4201(3) 0.0418(10) Uani 1 1 d . . .
H27A H -0.0225 0.3872 0.4130 0.050 Uiso 1 1 calc R . .
C28 C -0.0480(4) 0.2640(2) 0.4165(3) 0.0411(10) Uani 1 1 d . . .
H28A H -0.1343 0.2669 0.4082 0.049 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 0.0033 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'
F F 0.0171 0.0103 '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
C19 N1 C23 117.4(3) . . ?
C19 N1 B1 119.9(3) . . ?
C23 N1 B1 122.6(3) . . ?
C24 N2 C28 116.3(3) . . ?
C13 B1 N1 104.1(3) . . ?
C13 B1 C7 115.9(3) . . ?
N1 B1 C7 112.5(3) . . ?
C13 B1 C1 113.8(3) . . ?
N1 B1 C1 109.6(3) . . ?
C7 B1 C1 101.2(3) . . ?
C2 C1 C6 112.8(3) . . ?
C2 C1 B1 126.1(3) . . ?
C6 C1 B1 120.1(3) . . ?
F2 C2 C1 121.3(3) . . ?
F2 C2 C3 114.3(3) . . ?
C1 C2 C3 124.3(3) . . ?
F3 C3 C4 119.8(3) . . ?
F3 C3 C2 120.5(3) . . ?
C4 C3 C2 119.8(3) . . ?
F4 C4 C5 120.7(3) . . ?
F4 C4 C3 120.2(3) . . ?
C5 C4 C3 119.1(3) . . ?
F5 C5 C4 119.8(3) . . ?
F5 C5 C6 121.1(3) . . ?
C4 C5 C6 119.1(3) . . ?
F6 C6 C5 115.4(3) . . ?
F6 C6 C1 119.7(3) . . ?
C5 C6 C1 124.9(3) . . ?
C8 C7 C12 113.0(3) . . ?
C8 C7 B1 118.8(3) . . ?
C12 C7 B1 127.2(3) . . ?
F8 C8 C9 116.0(3) . . ?
F8 C8 C7 118.8(3) . . ?
C9 C8 C7 125.2(3) . . ?
F9 C9 C10 119.3(3) . . ?
F9 C9 C8 121.6(3) . . ?
C10 C9 C8 119.1(3) . . ?
F10 C10 C11 120.7(3) . . ?
F10 C10 C9 120.6(3) . . ?
C11 C10 C9 118.7(3) . . ?
F11 C11 C10 119.4(3) . . ?
F11 C11 C12 120.2(3) . . ?
C10 C11 C12 120.4(3) . . ?
F12 C12 C11 116.1(3) . . ?
F12 C12 C7 120.3(3) . . ?
C11 C12 C7 123.6(3) . . ?
C14 C13 C18 113.1(3) . . ?
C14 C13 B1 118.9(3) . . ?
C18 C13 B1 128.0(3) . . ?
C15 C14 F14 116.2(3) . . ?
C15 C14 C13 124.9(3) . . ?
F14 C14 C13 118.9(3) . . ?
F15 C15 C14 120.1(3) . . ?
F15 C15 C16 120.5(3) . . ?
C14 C15 C16 119.4(3) . . ?
F16 C16 C17 120.4(3) . . ?
F16 C16 C15 120.6(3) . . ?
C17 C16 C15 119.1(3) . . ?
F17 C17 C18 120.8(3) . . ?
F17 C17 C16 119.6(3) . . ?
C18 C17 C16 119.6(3) . . ?
F18 C18 C17 114.1(3) . . ?
F18 C18 C13 121.9(3) . . ?
C17 C18 C13 124.0(3) . . ?
N1 C19 C20 124.1(3) . . ?
C21 C20 C19 118.7(3) . . ?
C20 C21 C22 118.4(3) . . ?
C23 C22 C21 121.4(3) . . ?
N1 C23 C22 119.8(3) . . ?
N1 C23 C24 122.9(3) . . ?
C22 C23 C24 117.3(3) . . ?
N2 C24 C25 122.7(3) . . ?
N2 C24 C23 112.3(3) . . ?
C25 C24 C23 124.6(3) . . ?
C24 C25 C26 119.4(3) . . ?
C27 C26 C25 118.8(4) . . ?
C26 C27 C28 118.1(4) . . ?
N2 C28 C27 124.6(4) . . ?
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 C19 1.362(4) . ?
N1 C23 1.378(4) . ?
N1 B1 1.649(5) . ?
N2 C24 1.348(4) . ?
N2 C28 1.349(4) . ?
B1 C13 1.631(5) . ?
B1 C7 1.654(5) . ?
B1 C1 1.680(5) . ?
F2 C2 1.356(4) . ?
F3 C3 1.344(4) . ?
F4 C4 1.351(4) . ?
F5 C5 1.347(4) . ?
F6 C6 1.356(4) . ?
F8 C8 1.365(3) . ?
F9 C9 1.354(4) . ?
F10 C10 1.350(4) . ?
F11 C11 1.354(4) . ?
F12 C12 1.359(3) . ?
F14 C14 1.376(4) . ?
F15 C15 1.362(4) . ?
F16 C16 1.346(4) . ?
F17 C17 1.367(4) . ?
F18 C18 1.370(4) . ?
C1 C2 1.384(4) . ?
C1 C6 1.394(5) . ?
C2 C3 1.387(5) . ?
C3 C4 1.376(5) . ?
C4 C5 1.366(5) . ?
C5 C6 1.387(5) . ?
C7 C8 1.389(4) . ?
C7 C12 1.391(4) . ?
C8 C9 1.379(5) . ?
C9 C10 1.374(4) . ?
C10 C11 1.370(5) . ?
C11 C12 1.385(4) . ?
C13 C14 1.390(5) . ?
C13 C18 1.412(4) . ?
C14 C15 1.373(5) . ?
C15 C16 1.389(5) . ?
C16 C17 1.380(5) . ?
C17 C18 1.379(5) . ?
C19 C20 1.371(5) . ?
C20 C21 1.365(5) . ?
C21 C22 1.400(5) . ?
C22 C23 1.379(5) . ?
C23 C24 1.518(5) . ?
C24 C25 1.388(5) . ?
C25 C26 1.397(5) . ?
C26 C27 1.368(5) . ?
C27 C28 1.391(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139127249
