#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/35/4303534.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_4303534
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            'C32.5 H13 B F15 N'
_chemical_formula_weight         713.25
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 101.05(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0823(18)
_cell_length_b                   15.684(3)
_cell_length_c                   20.242(4)
_cell_measurement_reflns_used    6440
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.60
_cell_volume                     2830.0(10)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker P4'
_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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18764
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.919
_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    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1420
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         6440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0522
_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)+(0.0759P)²+0.7980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1506
_reflns_number_gt                4163
_reflns_number_total             6440
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic901726b_si_002_04.cif
_cod_data_source_block           ((2-Ph)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_original_formula_sum        'C32.50 H13 B F15 N'
_cod_database_code               4303534
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.11677(19) 0.69368(11) 0.16187(8) 0.0270(4) Uani 1 1 d . . .
F2 F 1.08687(14) 0.87443(8) 0.22222(6) 0.0377(3) Uani 1 1 d . . .
F3 F 0.97319(16) 1.02936(8) 0.19639(7) 0.0442(4) Uani 1 1 d . . .
F4 F 0.70061(17) 1.05063(8) 0.11261(7) 0.0462(4) Uani 1 1 d . . .
F5 F 0.55251(15) 0.91176(9) 0.05293(7) 0.0420(3) Uani 1 1 d . . .
F6 F 0.66134(14) 0.75793(8) 0.07704(6) 0.0350(3) Uani 1 1 d . . .
F8 F 1.21523(16) 0.73249(9) 0.29678(7) 0.0475(4) Uani 1 1 d . . .
F9 F 1.1915(2) 0.75639(12) 0.42420(8) 0.0728(6) Uani 1 1 d . . .
F10 F 0.9169(2) 0.75400(12) 0.46111(7) 0.0768(6) Uani 1 1 d . . .
F11 F 0.6657(2) 0.73632(11) 0.36505(8) 0.0683(5) Uani 1 1 d . . .
F12 F 0.68636(15) 0.72046(9) 0.23619(6) 0.0408(3) Uani 1 1 d . . .
F14 F 0.78549(14) 0.56313(8) 0.23738(6) 0.0357(3) Uani 1 1 d . . .
F15 F 0.62756(16) 0.44275(9) 0.16658(8) 0.0507(4) Uani 1 1 d . . .
F16 F 0.60868(19) 0.43321(10) 0.03068(8) 0.0628(5) Uani 1 1 d . . .
F17 F 0.7514(2) 0.55180(11) -0.03242(7) 0.0596(5) Uani 1 1 d . . .
F18 F 0.90696(15) 0.67756(9) 0.03785(6) 0.0400(3) Uani 1 1 d . . .
C1 C 0.8837(2) 0.80569(14) 0.15089(10) 0.0266(5) Uani 1 1 d . . .
C2 C 0.9529(2) 0.88033(14) 0.17923(10) 0.0296(5) Uani 1 1 d . . .
C3 C 0.8963(3) 0.96161(14) 0.16728(11) 0.0323(5) Uani 1 1 d . . .
C4 C 0.7603(3) 0.97254(14) 0.12502(11) 0.0334(5) Uani 1 1 d . . .
C5 C 0.6859(2) 0.90242(15) 0.09521(11) 0.0315(5) Uani 1 1 d . . .
C6 C 0.7471(2) 0.82229(14) 0.10833(10) 0.0273(5) Uani 1 1 d . . .
C7 C 0.9519(3) 0.71919(14) 0.25975(10) 0.0305(5) Uani 1 1 d . . .
C8 C 1.0758(3) 0.73185(15) 0.31055(12) 0.0379(6) Uani 1 1 d . . .
C9 C 1.0659(3) 0.74511(16) 0.37792(12) 0.0498(7) Uani 1 1 d . . .
C10 C 0.9279(4) 0.74475(17) 0.39593(12) 0.0519(7) Uani 1 1 d . . .
C11 C 0.8027(3) 0.73562(16) 0.34794(13) 0.0468(7) Uani 1 1 d . . .
C12 C 0.8162(3) 0.72533(15) 0.28169(11) 0.0341(5) Uani 1 1 d . . .
C13 C 0.8490(2) 0.63071(14) 0.14106(10) 0.0269(5) Uani 1 1 d . . .
C14 C 0.7765(2) 0.56732(14) 0.17022(11) 0.0298(5) Uani 1 1 d . . .
C15 C 0.6956(2) 0.50198(15) 0.13432(12) 0.0362(5) Uani 1 1 d . . .
C16 C 0.6864(3) 0.49655(16) 0.06641(13) 0.0425(6) Uani 1 1 d . . .
C17 C 0.7587(3) 0.55616(17) 0.03471(12) 0.0412(6) Uani 1 1 d . . .
C18 C 0.8381(2) 0.62058(15) 0.07209(11) 0.0321(5) Uani 1 1 d . . .
C19 C 1.1776(2) 0.75309(14) 0.12688(11) 0.0312(5) Uani 1 1 d . . .
H19A H 1.1244 0.8049 0.1158 0.037 Uiso 1 1 calc R . .
C20 C 1.3128(3) 0.74262(15) 0.10640(12) 0.0353(5) Uani 1 1 d . . .
H20A H 1.3509 0.7862 0.0817 0.042 Uiso 1 1 calc R . .
C21 C 1.3914(3) 0.66850(16) 0.12218(12) 0.0395(6) Uani 1 1 d . . .
H21A H 1.4852 0.6597 0.1090 0.047 Uiso 1 1 calc R . .
C22 C 1.3308(3) 0.60695(16) 0.15762(12) 0.0387(6) Uani 1 1 d . . .
H22A H 1.3841 0.5552 0.1691 0.046 Uiso 1 1 calc R . .
C23 C 1.1939(2) 0.61884(14) 0.17690(11) 0.0305(5) Uani 1 1 d . . .
C24 C 1.1335(2) 0.54414(14) 0.20913(12) 0.0340(5) Uani 1 1 d . . .
C25 C 1.0853(3) 0.47473(16) 0.16772(13) 0.0420(6) Uani 1 1 d . . .
H25A H 1.0846 0.4783 0.1208 0.050 Uiso 1 1 calc R . .
C26 C 1.0382(3) 0.40040(17) 0.19440(17) 0.0541(8) Uani 1 1 d . . .
H26A H 1.0043 0.3535 0.1658 0.065 Uiso 1 1 calc R . .
C27 C 1.0407(3) 0.39465(18) 0.26255(17) 0.0552(8) Uani 1 1 d . . .
H27A H 1.0057 0.3444 0.2807 0.066 Uiso 1 1 calc R . .
C28 C 1.0941(3) 0.46167(18) 0.30428(15) 0.0486(7) Uani 1 1 d . . .
H28A H 1.0988 0.4567 0.3514 0.058 Uiso 1 1 calc R . .
C29 C 1.1408(3) 0.53596(16) 0.27808(13) 0.0398(6) Uani 1 1 d . . .
H29A H 1.1782 0.5817 0.3073 0.048 Uiso 1 1 calc R . .
B1 B 0.9485(3) 0.71077(16) 0.17866(12) 0.0265(5) Uani 1 1 d . . .
C1S C 1.4952(8) 0.4436(3) 0.5147(3) 0.063(3) Uani 0.50 1 d PG A -1
C2S C 1.6243(6) 0.4931(6) 0.5225(3) 0.072(4) Uani 0.50 1 d PG A -1
H2SA H 1.7178 0.4702 0.5444 0.086 Uiso 0.50 1 calc PR A -1
C3S C 1.6166(9) 0.5763(5) 0.4984(4) 0.098(4) Uani 0.50 1 d PG A -1
H3SA H 1.7048 0.6102 0.5038 0.117 Uiso 0.50 1 calc PR A -1
C4S C 1.4798(13) 0.6099(3) 0.4664(4) 0.117(8) Uani 0.50 1 d PG A -1
H4SA H 1.4745 0.6668 0.4499 0.141 Uiso 0.50 1 calc PR A -1
C5S C 1.3507(9) 0.5604(4) 0.4586(3) 0.073(3) Uani 0.50 1 d PG A -1
H5SA H 1.2573 0.5833 0.4367 0.088 Uiso 0.50 1 calc PR A -1
C6S C 1.3585(6) 0.4772(4) 0.4827(3) 0.055(2) Uani 0.50 1 d PG A -1
H6SA H 1.2702 0.4433 0.4773 0.067 Uiso 0.50 1 calc PR A -1
C7S C 1.5124(17) 0.3596(12) 0.5375(6) 0.120(6) Uani 0.50 1 d P A -1
H7SA H 1.6179 0.3492 0.5575 0.181 Uiso 0.50 1 calc PR A -1
H7SB H 1.4810 0.3206 0.4996 0.181 Uiso 0.50 1 calc PR A -1
H7SC H 1.4503 0.3501 0.5714 0.181 Uiso 0.50 1 calc PR A -1
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 117.63(18) . . ?
C19 N1 B1 118.96(18) . . ?
C23 N1 B1 123.19(17) . . ?
C6 C1 C2 111.98(19) . . ?
C6 C1 B1 126.41(19) . . ?
C2 C1 B1 120.65(18) . . ?
F2 C2 C3 115.72(19) . . ?
F2 C2 C1 118.91(19) . . ?
C3 C2 C1 125.4(2) . . ?
F3 C3 C4 120.3(2) . . ?
F3 C3 C2 120.6(2) . . ?
C4 C3 C2 119.1(2) . . ?
F4 C4 C5 120.2(2) . . ?
F4 C4 C3 120.9(2) . . ?
C5 C4 C3 118.9(2) . . ?
F5 C5 C4 119.9(2) . . ?
F5 C5 C6 120.0(2) . . ?
C4 C5 C6 120.0(2) . . ?
F6 C6 C5 114.47(18) . . ?
F6 C6 C1 120.91(19) . . ?
C5 C6 C1 124.6(2) . . ?
C8 C7 C12 113.4(2) . . ?
C8 C7 B1 127.6(2) . . ?
C12 C7 B1 118.47(19) . . ?
F8 C8 C7 120.6(2) . . ?
F8 C8 C9 116.0(2) . . ?
C7 C8 C9 123.4(2) . . ?
F9 C9 C10 120.9(2) . . ?
F9 C9 C8 119.7(3) . . ?
C10 C9 C8 119.4(2) . . ?
F10 C10 C11 120.2(3) . . ?
F10 C10 C9 120.1(3) . . ?
C11 C10 C9 119.6(2) . . ?
C10 C11 F11 120.1(2) . . ?
C10 C11 C12 119.4(3) . . ?
F11 C11 C12 120.4(3) . . ?
F12 C12 C11 116.2(2) . . ?
F12 C12 C7 119.27(19) . . ?
C11 C12 C7 124.6(2) . . ?
C14 C13 C18 113.4(2) . . ?
C14 C13 B1 127.89(18) . . ?
C18 C13 B1 118.62(18) . . ?
F14 C14 C15 114.66(19) . . ?
F14 C14 C13 121.52(19) . . ?
C15 C14 C13 123.8(2) . . ?
F15 C15 C16 119.9(2) . . ?
F15 C15 C14 120.1(2) . . ?
C16 C15 C14 120.0(2) . . ?
F16 C16 C15 120.8(2) . . ?
F16 C16 C17 120.0(2) . . ?
C15 C16 C17 119.1(2) . . ?
F17 C17 C16 120.1(2) . . ?
F17 C17 C18 120.6(2) . . ?
C16 C17 C18 119.3(2) . . ?
F18 C18 C17 116.51(19) . . ?
F18 C18 C13 119.16(19) . . ?
C17 C18 C13 124.3(2) . . ?
N1 C19 C20 123.6(2) . . ?
C21 C20 C19 119.0(2) . . ?
C20 C21 C22 118.2(2) . . ?
C21 C22 C23 121.5(2) . . ?
N1 C23 C22 120.0(2) . . ?
N1 C23 C24 123.58(18) . . ?
C22 C23 C24 116.2(2) . . ?
C29 C24 C25 118.8(2) . . ?
C29 C24 C23 124.0(2) . . ?
C25 C24 C23 116.7(2) . . ?
C26 C25 C24 120.5(3) . . ?
C27 C26 C25 119.9(3) . . ?
C28 C27 C26 120.0(3) . . ?
C27 C28 C29 120.4(3) . . ?
C28 C29 C24 120.3(3) . . ?
C7 B1 C13 115.30(18) . . ?
C7 B1 N1 112.23(17) . . ?
C13 B1 N1 103.23(16) . . ?
C7 B1 C1 101.78(17) . . ?
C13 B1 C1 113.60(17) . . ?
N1 B1 C1 111.01(16) . . ?
C2S C1S C6S 120.0 . . ?
C2S C1S C7S 116.9(10) . . ?
C6S C1S C7S 123.1(10) . . ?
C3S C2S C1S 120.0 . . ?
C2S C3S C4S 120.0 . . ?
C5S C4S C3S 120.0 . . ?
C4S C5S C6S 120.0 . . ?
C5S C6S C1S 120.0 . . ?
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 1.351(3) . ?
N1 C23 1.371(3) . ?
N1 B1 1.650(3) . ?
F2 C2 1.356(2) . ?
F3 C3 1.344(3) . ?
F4 C4 1.343(3) . ?
F5 C5 1.350(3) . ?
F6 C6 1.356(2) . ?
F8 C8 1.348(3) . ?
F9 C9 1.342(3) . ?
F10 C10 1.350(3) . ?
F11 C11 1.354(3) . ?
F12 C12 1.352(3) . ?
F14 C14 1.348(2) . ?
F15 C15 1.351(3) . ?
F16 C16 1.346(3) . ?
F17 C17 1.349(3) . ?
F18 C18 1.355(3) . ?
C1 C6 1.393(3) . ?
C1 C2 1.399(3) . ?
C1 B1 1.659(3) . ?
C2 C3 1.378(3) . ?
C3 C4 1.372(3) . ?
C4 C5 1.369(3) . ?
C5 C6 1.379(3) . ?
C7 C8 1.385(3) . ?
C7 C12 1.391(3) . ?
C7 B1 1.641(3) . ?
C8 C9 1.399(4) . ?
C9 C10 1.371(4) . ?
C10 C11 1.354(4) . ?
C11 C12 1.379(3) . ?
C13 C14 1.386(3) . ?
C13 C18 1.390(3) . ?
C13 B1 1.646(3) . ?
C14 C15 1.383(3) . ?
C15 C16 1.364(3) . ?
C16 C17 1.371(4) . ?
C17 C18 1.380(3) . ?
C19 C20 1.379(3) . ?
C20 C21 1.370(3) . ?
C21 C22 1.379(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.495(3) . ?
C24 C29 1.390(3) . ?
C24 C25 1.392(3) . ?
C25 C26 1.386(4) . ?
C26 C27 1.378(4) . ?
C27 C28 1.377(4) . ?
C28 C29 1.380(3) . ?
C1S C2S 1.3900 . ?
C1S C6S 1.3900 . ?
C1S C7S 1.394(18) . ?
C2S C3S 1.3900 . ?
C3S C4S 1.3900 . ?
C4S C5S 1.3900 . ?
C5S C6S 1.3900 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139127247
