#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/35/4303537.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_4303537
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 H9 B F15 N3'
_chemical_formula_weight         683.19
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.830(3)
_cell_angle_beta                 102.077(4)
_cell_angle_gamma                98.166(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6501(10)
_cell_length_b                   9.7264(8)
_cell_length_c                   14.9925(11)
_cell_measurement_reflns_used    5042
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.34
_cell_measurement_theta_min      1.48
_cell_volume                     1277.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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 0.997
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19690
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.34
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6838
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         6580
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0427
_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)+(0.0418P)²+0.2211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                4247
_reflns_number_total             6580
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic901726b_si_002_07.cif
_cod_data_source_block           ((2-C5H4N)NH(2-C5H4N)B(C6F5)3)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        1277.46(19)
_cod_database_code               4303537
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B -0.0954(2) 0.5784(2) 0.21927(14) 0.0190(4) Uani 1 1 d . . .
N1 N -0.21745(15) 0.44229(16) 0.13455(10) 0.0180(3) Uani 1 1 d . . .
N2 N -0.24376(16) 0.32456(16) 0.24580(10) 0.0208(3) Uani 1 1 d . . .
H2A H -0.1693 0.3962 0.2845 0.025 Uiso 1 1 calc R . .
N3 N -0.36704(18) 0.09059(17) 0.23718(11) 0.0260(4) Uani 1 1 d . . .
F2 F -0.29942(11) 0.72153(12) 0.12831(8) 0.0285(3) Uani 1 1 d . . .
F3 F -0.23871(13) 0.94720(13) 0.06655(8) 0.0355(3) Uani 1 1 d . . .
F4 F 0.04079(14) 1.08768(13) 0.10048(9) 0.0428(3) Uani 1 1 d . . .
F5 F 0.26022(13) 0.98593(14) 0.18722(10) 0.0465(3) Uani 1 1 d . . .
F6 F 0.20668(11) 0.75435(12) 0.23992(8) 0.0334(3) Uani 1 1 d . . .
F8 F -0.41376(11) 0.55618(12) 0.23023(7) 0.0278(3) Uani 1 1 d . . .
F9 F -0.49741(13) 0.70120(13) 0.38141(9) 0.0389(3) Uani 1 1 d . . .
F10 F -0.29874(14) 0.88173(13) 0.54998(8) 0.0419(3) Uani 1 1 d . . .
F11 F -0.01054(13) 0.91156(12) 0.56145(7) 0.0361(3) Uani 1 1 d . . .
F12 F 0.07728(11) 0.78123(12) 0.40525(7) 0.0285(3) Uani 1 1 d . . .
F14 F 0.03845(11) 0.50174(12) 0.40133(7) 0.0264(3) Uani 1 1 d . . .
F15 F 0.27673(12) 0.39794(13) 0.42577(8) 0.0360(3) Uani 1 1 d . . .
F16 F 0.40858(12) 0.31780(13) 0.27986(9) 0.0373(3) Uani 1 1 d . . .
F17 F 0.29409(12) 0.35020(13) 0.10651(8) 0.0331(3) Uani 1 1 d . . .
F18 F 0.06218(11) 0.46622(12) 0.08310(7) 0.0277(3) Uani 1 1 d . . .
C1 C -0.05096(19) 0.7179(2) 0.18231(12) 0.0202(4) Uani 1 1 d . . .
C2 C -0.1575(2) 0.7808(2) 0.14146(13) 0.0223(4) Uani 1 1 d . . .
C3 C -0.1302(2) 0.8995(2) 0.11114(13) 0.0259(4) Uani 1 1 d . . .
C4 C 0.0108(2) 0.9690(2) 0.12686(14) 0.0301(5) Uani 1 1 d . . .
C5 C 0.1212(2) 0.9179(2) 0.17081(14) 0.0310(5) Uani 1 1 d . . .
C6 C 0.0893(2) 0.7947(2) 0.19704(13) 0.0249(4) Uani 1 1 d . . .
C7 C -0.16151(19) 0.65372(19) 0.31118(12) 0.0201(4) Uani 1 1 d . . .
C8 C -0.3067(2) 0.6429(2) 0.31016(13) 0.0222(4) Uani 1 1 d . . .
C9 C -0.3540(2) 0.7173(2) 0.38869(14) 0.0275(4) Uani 1 1 d . . .
C10 C -0.2545(2) 0.8081(2) 0.47330(14) 0.0287(5) Uani 1 1 d . . .
C11 C -0.1093(2) 0.8244(2) 0.47883(13) 0.0260(4) Uani 1 1 d . . .
C12 C -0.0668(2) 0.7519(2) 0.39810(13) 0.0230(4) Uani 1 1 d . . .
C13 C 0.04190(18) 0.49946(19) 0.24233(12) 0.0184(4) Uani 1 1 d . . .
C14 C 0.10143(19) 0.4724(2) 0.32610(12) 0.0208(4) Uani 1 1 d . . .
C15 C 0.2228(2) 0.4142(2) 0.34027(13) 0.0239(4) Uani 1 1 d . . .
C16 C 0.2905(2) 0.3740(2) 0.26712(14) 0.0243(4) Uani 1 1 d . . .
C17 C 0.2328(2) 0.3913(2) 0.18021(13) 0.0231(4) Uani 1 1 d . . .
C18 C 0.11201(19) 0.4511(2) 0.17020(12) 0.0204(4) Uani 1 1 d . . .
C19 C -0.24997(19) 0.4401(2) 0.04103(12) 0.0212(4) Uani 1 1 d . . .
H19A H -0.2010 0.5202 0.0276 0.025 Uiso 1 1 calc R . .
C20 C -0.3482(2) 0.3299(2) -0.03364(13) 0.0252(4) Uani 1 1 d . . .
H20A H -0.3674 0.3330 -0.0977 0.030 Uiso 1 1 calc R . .
C21 C -0.4205(2) 0.2124(2) -0.01469(13) 0.0250(4) Uani 1 1 d . . .
H21A H -0.4918 0.1351 -0.0655 0.030 Uiso 1 1 calc R . .
C22 C -0.3883(2) 0.2089(2) 0.07775(13) 0.0220(4) Uani 1 1 d . . .
H22A H -0.4369 0.1286 0.0912 0.026 Uiso 1 1 calc R . .
C23 C -0.28410(19) 0.32294(19) 0.15239(12) 0.0183(4) Uani 1 1 d . . .
C24 C -0.30205(19) 0.2301(2) 0.29009(12) 0.0190(4) Uani 1 1 d . . .
C25 C -0.2853(2) 0.2915(2) 0.38948(12) 0.0237(4) Uani 1 1 d . . .
H25A H -0.2355 0.3915 0.4248 0.028 Uiso 1 1 calc R . .
C26 C -0.3426(2) 0.2041(2) 0.43524(13) 0.0270(4) Uani 1 1 d . . .
H26A H -0.3338 0.2429 0.5030 0.032 Uiso 1 1 calc R . .
C27 C -0.4131(2) 0.0592(2) 0.38161(13) 0.0275(4) Uani 1 1 d . . .
H27A H -0.4551 -0.0034 0.4112 0.033 Uiso 1 1 calc R . .
C28 C -0.4210(2) 0.0082(2) 0.28456(14) 0.0303(5) Uani 1 1 d . . .
H28A H -0.4677 -0.0924 0.2482 0.036 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
N1 B1 C13 102.54(14) . . ?
N1 B1 C7 110.77(14) . . ?
C13 B1 C7 116.80(14) . . ?
N1 B1 C1 112.04(13) . . ?
C13 B1 C1 112.06(15) . . ?
C7 B1 C1 102.95(14) . . ?
C19 N1 C23 117.69(15) . . ?
C19 N1 B1 120.00(14) . . ?
C23 N1 B1 122.20(13) . . ?
C23 N2 C24 130.46(15) . . ?
C24 N3 C28 116.23(16) . . ?
C6 C1 C2 113.01(16) . . ?
C6 C1 B1 125.73(15) . . ?
C2 C1 B1 120.88(16) . . ?
F2 C2 C3 116.07(16) . . ?
F2 C2 C1 119.07(15) . . ?
C3 C2 C1 124.85(17) . . ?
F3 C3 C4 119.83(16) . . ?
F3 C3 C2 121.27(17) . . ?
C4 C3 C2 118.90(17) . . ?
F4 C4 C3 120.27(17) . . ?
F4 C4 C5 120.22(18) . . ?
C3 C4 C5 119.51(17) . . ?
F5 C5 C4 120.00(17) . . ?
F5 C5 C6 120.18(18) . . ?
C4 C5 C6 119.81(18) . . ?
F6 C6 C1 121.58(16) . . ?
F6 C6 C5 114.66(16) . . ?
C1 C6 C5 123.76(17) . . ?
C8 C7 C12 113.37(16) . . ?
C8 C7 B1 127.13(15) . . ?
C12 C7 B1 119.16(16) . . ?
F8 C8 C7 121.27(16) . . ?
F8 C8 C9 114.92(16) . . ?
C7 C8 C9 123.80(17) . . ?
F9 C9 C10 120.28(17) . . ?
F9 C9 C8 120.01(18) . . ?
C10 C9 C8 119.71(18) . . ?
F10 C10 C11 120.21(18) . . ?
F10 C10 C9 120.41(19) . . ?
C11 C10 C9 119.38(17) . . ?
F11 C11 C10 120.11(17) . . ?
F11 C11 C12 120.78(18) . . ?
C10 C11 C12 119.10(17) . . ?
F12 C12 C11 116.53(16) . . ?
F12 C12 C7 118.97(16) . . ?
C11 C12 C7 124.49(18) . . ?
C14 C13 C18 112.46(16) . . ?
C14 C13 B1 129.12(16) . . ?
C18 C13 B1 118.42(14) . . ?
F14 C14 C15 115.31(15) . . ?
F14 C14 C13 120.20(15) . . ?
C15 C14 C13 124.49(16) . . ?
F15 C15 C16 119.69(16) . . ?
F15 C15 C14 120.33(17) . . ?
C16 C15 C14 119.97(16) . . ?
F16 C16 C15 120.67(16) . . ?
F16 C16 C17 120.79(17) . . ?
C15 C16 C17 118.53(17) . . ?
F17 C17 C18 120.73(16) . . ?
F17 C17 C16 120.15(16) . . ?
C18 C17 C16 119.11(17) . . ?
F18 C18 C17 115.85(15) . . ?
F18 C18 C13 118.85(15) . . ?
C17 C18 C13 125.28(15) . . ?
C20 C19 N1 123.55(17) . . ?
C19 C20 C21 118.68(16) . . ?
C22 C21 C20 119.46(17) . . ?
C21 C22 C23 120.18(17) . . ?
N2 C23 N1 116.41(15) . . ?
N2 C23 C22 123.25(15) . . ?
N1 C23 C22 120.33(15) . . ?
N3 C24 C25 123.78(16) . . ?
N3 C24 N2 119.86(15) . . ?
C25 C24 N2 116.35(16) . . ?
C26 C25 C24 118.27(18) . . ?
C27 C26 C25 119.16(17) . . ?
C28 C27 C26 118.10(17) . . ?
N3 C28 C27 124.42(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
B1 N1 1.629(2) . ?
B1 C13 1.651(3) . ?
B1 C7 1.650(3) . ?
B1 C1 1.651(3) . ?
N1 C19 1.364(2) . ?
N1 C23 1.372(2) . ?
N2 C23 1.367(2) . ?
N2 C24 1.409(2) . ?
N3 C24 1.325(2) . ?
N3 C28 1.343(2) . ?
F2 C2 1.357(2) . ?
F3 C3 1.339(2) . ?
F4 C4 1.343(2) . ?
F5 C5 1.345(2) . ?
F6 C6 1.352(2) . ?
F8 C8 1.353(2) . ?
F9 C9 1.348(2) . ?
F10 C10 1.343(2) . ?
F11 C11 1.339(2) . ?
F12 C12 1.354(2) . ?
F14 C14 1.3646(19) . ?
F15 C15 1.3445(19) . ?
F16 C16 1.336(2) . ?
F17 C17 1.342(2) . ?
F18 C18 1.3536(18) . ?
C1 C6 1.388(3) . ?
C1 C2 1.397(2) . ?
C2 C3 1.376(2) . ?
C3 C4 1.368(3) . ?
C4 C5 1.369(3) . ?
C5 C6 1.385(3) . ?
C7 C8 1.387(2) . ?
C7 C12 1.392(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.369(3) . ?
C10 C11 1.370(3) . ?
C11 C12 1.377(3) . ?
C13 C14 1.386(2) . ?
C13 C18 1.391(2) . ?
C14 C15 1.376(3) . ?
C15 C16 1.375(3) . ?
C16 C17 1.376(2) . ?
C17 C18 1.376(3) . ?
C19 C20 1.354(3) . ?
C20 C21 1.389(3) . ?
C21 C22 1.367(2) . ?
C22 C23 1.395(2) . ?
C24 C25 1.389(2) . ?
C25 C26 1.372(3) . ?
C26 C27 1.378(3) . ?
C27 C28 1.368(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139127251
