#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:41:58 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179073 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/35/4303539.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_4303539
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            'C25 H9 B F15 N'
_chemical_formula_weight         619.14
_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                 100.156(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8108(4)
_cell_length_b                   13.4663(4)
_cell_length_c                   13.3937(4)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    150
_cell_measurement_theta_max      32.27
_cell_measurement_theta_min      2.21
_cell_volume                     2274.40(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            56522
_diffrn_reflns_theta_full        32.42
_diffrn_reflns_theta_max         32.42
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.9626
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         7942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0494
_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)+(0.0633P)²+2.2750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1475
_reflns_number_gt                6118
_reflns_number_total             7942
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic901726b_si_002_09.cif
_cod_data_source_block           (2,6-Me2C5H3N)B(C6F5)3
_cod_database_code               4303539
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 0.16210(11) 0.27685(10) 0.65126(10) 0.0186(2) Uani 1 1 d . . .
B1 B 0.25781(14) 0.26647(12) 0.58282(13) 0.0170(3) Uani 1 1 d . . .
F1 F 0.27747(8) 0.13566(8) 0.77784(8) 0.0248(2) Uani 1 1 d . . .
F2 F 0.43309(9) 0.01194(8) 0.84185(8) 0.0265(2) Uani 1 1 d . . .
F3 F 0.60183(9) -0.00383(9) 0.74410(10) 0.0364(3) Uani 1 1 d . . .
F4 F 0.60725(10) 0.10945(10) 0.57653(10) 0.0374(3) Uani 1 1 d . . .
F5 F 0.45041(9) 0.23521(8) 0.50948(8) 0.0258(2) Uani 1 1 d . . .
F6 F 0.11142(8) 0.40598(8) 0.47698(8) 0.0250(2) Uani 1 1 d . . .
F7 F 0.13960(10) 0.59759(8) 0.44449(9) 0.0311(2) Uani 1 1 d . . .
F8 F 0.33225(11) 0.68358(8) 0.50483(9) 0.0325(3) Uani 1 1 d . . .
F9 F 0.49562(9) 0.57200(8) 0.60319(10) 0.0329(3) Uani 1 1 d . . .
F10 F 0.46910(9) 0.38317(8) 0.64345(9) 0.0294(2) Uani 1 1 d . . .
F11 F 0.18866(9) 0.06185(8) 0.57784(9) 0.0286(2) Uani 1 1 d . . .
F12 F 0.15971(11) -0.06207(9) 0.42216(11) 0.0416(3) Uani 1 1 d . . .
F13 F 0.17435(11) 0.00384(11) 0.23186(10) 0.0430(3) Uani 1 1 d . . .
F14 F 0.22340(11) 0.19776(12) 0.20568(9) 0.0419(3) Uani 1 1 d . . .
F15 F 0.25767(11) 0.32130(8) 0.35890(8) 0.0322(3) Uani 1 1 d . . .
C1 C 0.35694(12) 0.19732(11) 0.64210(12) 0.0177(3) Uani 1 1 d . . .
C2 C 0.35847(12) 0.13594(11) 0.72571(12) 0.0184(3) Uani 1 1 d . . .
C3 C 0.43914(13) 0.06914(12) 0.76164(12) 0.0202(3) Uani 1 1 d . . .
C4 C 0.52437(13) 0.06074(13) 0.71214(14) 0.0244(3) Uani 1 1 d . . .
C5 C 0.52675(14) 0.11874(13) 0.62750(14) 0.0243(3) Uani 1 1 d . . .
C6 C 0.44467(13) 0.18410(12) 0.59507(12) 0.0200(3) Uani 1 1 d . . .
C7 C 0.28819(13) 0.38194(11) 0.56057(12) 0.0180(3) Uani 1 1 d . . .
C8 C 0.20869(13) 0.44380(11) 0.51057(12) 0.0187(3) Uani 1 1 d . . .
C9 C 0.22111(14) 0.54310(12) 0.49110(12) 0.0214(3) Uani 1 1 d . . .
C10 C 0.31845(15) 0.58710(12) 0.52192(12) 0.0226(3) Uani 1 1 d . . .
C11 C 0.40092(14) 0.53052(12) 0.57152(13) 0.0228(3) Uani 1 1 d . . .
C12 C 0.38425(13) 0.43060(12) 0.59019(13) 0.0210(3) Uani 1 1 d . . .
C13 C 0.22426(12) 0.19969(11) 0.47876(12) 0.0180(3) Uani 1 1 d . . .
C14 C 0.20043(13) 0.09910(12) 0.48653(13) 0.0216(3) Uani 1 1 d . . .
C15 C 0.18351(14) 0.03325(13) 0.40655(16) 0.0272(3) Uani 1 1 d . . .
C16 C 0.19001(14) 0.06605(15) 0.31051(15) 0.0285(4) Uani 1 1 d . . .
C17 C 0.21450(15) 0.16411(15) 0.29772(13) 0.0268(3) Uani 1 1 d . . .
C18 C 0.23172(14) 0.22815(12) 0.38037(12) 0.0217(3) Uani 1 1 d . . .
C19 C 0.18988(14) 0.31740(12) 0.74688(12) 0.0222(3) Uani 1 1 d . . .
C20 C 0.29648(16) 0.36272(14) 0.78402(13) 0.0274(3) Uani 1 1 d . . .
H20A H 0.3396 0.3567 0.7325 0.041 Uiso 1 1 calc R . .
H20B H 0.3301 0.3288 0.8442 0.041 Uiso 1 1 calc R . .
H20C H 0.2880 0.4316 0.7991 0.041 Uiso 1 1 calc R . .
C21 C 0.11823(17) 0.32020(14) 0.81339(14) 0.0293(4) Uani 1 1 d . . .
H21A H 0.1385 0.3479 0.8775 0.035 Uiso 1 1 calc R . .
C22 C 0.01768(18) 0.28254(16) 0.78569(16) 0.0341(4) Uani 1 1 d . . .
H22A H -0.0290 0.2804 0.8316 0.041 Uiso 1 1 calc R . .
C23 C -0.01192(15) 0.24829(14) 0.68855(15) 0.0285(4) Uani 1 1 d . . .
H23A H -0.0806 0.2251 0.6674 0.034 Uiso 1 1 calc R . .
C24 C 0.05888(13) 0.24760(12) 0.62096(13) 0.0211(3) Uani 1 1 d . . .
C25 C 0.01039(14) 0.21733(14) 0.51455(14) 0.0265(3) Uani 1 1 d . . .
H25A H 0.0637 0.2188 0.4724 0.040 Uiso 1 1 calc R . .
H25B H -0.0456 0.2626 0.4882 0.040 Uiso 1 1 calc R . .
H25C H -0.0178 0.1513 0.5153 0.040 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
C24 N1 C19 117.77(14) . . ?
C24 N1 B1 125.44(13) . . ?
C19 N1 B1 116.79(13) . . ?
C7 B1 C13 113.41(12) . . ?
C7 B1 C1 115.59(13) . . ?
C13 B1 C1 99.30(12) . . ?
C7 B1 N1 104.00(11) . . ?
C13 B1 N1 113.84(12) . . ?
C1 B1 N1 111.11(12) . . ?
C2 C1 C6 112.99(14) . . ?
C2 C1 B1 128.34(13) . . ?
C6 C1 B1 117.75(13) . . ?
F1 C2 C1 121.08(14) . . ?
F1 C2 C3 114.30(13) . . ?
C1 C2 C3 124.61(14) . . ?
F2 C3 C4 120.19(14) . . ?
F2 C3 C2 120.44(14) . . ?
C4 C3 C2 119.34(14) . . ?
F3 C4 C3 120.50(15) . . ?
F3 C4 C5 120.65(16) . . ?
C3 C4 C5 118.83(15) . . ?
F4 C5 C6 120.75(15) . . ?
F4 C5 C4 119.73(15) . . ?
C6 C5 C4 119.51(15) . . ?
F5 C6 C5 116.07(14) . . ?
F5 C6 C1 119.19(14) . . ?
C5 C6 C1 124.70(15) . . ?
C12 C7 C8 113.04(14) . . ?
C12 C7 B1 128.39(14) . . ?
C8 C7 B1 118.48(14) . . ?
F6 C8 C9 115.76(14) . . ?
F6 C8 C7 119.29(13) . . ?
C9 C8 C7 124.95(15) . . ?
F7 C9 C10 119.69(15) . . ?
F7 C9 C8 120.96(16) . . ?
C10 C9 C8 119.34(15) . . ?
F8 C10 C11 120.52(16) . . ?
F8 C10 C9 120.48(16) . . ?
C11 C10 C9 118.99(15) . . ?
F9 C11 C10 119.96(15) . . ?
F9 C11 C12 120.46(16) . . ?
C10 C11 C12 119.56(16) . . ?
F10 C12 C7 121.18(14) . . ?
F10 C12 C11 114.66(15) . . ?
C7 C12 C11 124.12(15) . . ?
C18 C13 C14 112.96(14) . . ?
C18 C13 B1 126.75(14) . . ?
C14 C13 B1 119.56(14) . . ?
F11 C14 C15 115.86(15) . . ?
F11 C14 C13 119.14(14) . . ?
C15 C14 C13 124.95(16) . . ?
F12 C15 C16 120.30(17) . . ?
F12 C15 C14 120.16(18) . . ?
C16 C15 C14 119.53(16) . . ?
F13 C16 C17 120.73(18) . . ?
F13 C16 C15 120.75(18) . . ?
C17 C16 C15 118.51(16) . . ?
F14 C17 C16 119.92(16) . . ?
F14 C17 C18 119.78(17) . . ?
C16 C17 C18 120.29(17) . . ?
F15 C18 C17 114.83(15) . . ?
F15 C18 C13 121.42(14) . . ?
C17 C18 C13 123.74(16) . . ?
N1 C19 C21 120.99(17) . . ?
N1 C19 C20 122.69(15) . . ?
C21 C19 C20 116.31(16) . . ?
C22 C21 C19 120.78(18) . . ?
C23 C22 C21 118.07(17) . . ?
C22 C23 C24 121.19(19) . . ?
N1 C24 C23 120.77(16) . . ?
N1 C24 C25 124.96(14) . . ?
C23 C24 C25 114.22(16) . . ?
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 C24 1.371(2) . ?
N1 C19 1.380(2) . ?
N1 B1 1.661(2) . ?
B1 C7 1.643(2) . ?
B1 C13 1.651(2) . ?
B1 C1 1.660(2) . ?
F1 C2 1.3490(18) . ?
F2 C3 1.3351(18) . ?
F3 C4 1.3319(19) . ?
F4 C5 1.3392(19) . ?
F5 C6 1.3502(18) . ?
F6 C8 1.3479(19) . ?
F7 C9 1.3374(19) . ?
F8 C10 1.3364(18) . ?
F9 C11 1.335(2) . ?
F10 C12 1.3508(19) . ?
F11 C14 1.355(2) . ?
F12 C15 1.344(2) . ?
F13 C16 1.333(2) . ?
F14 C17 1.337(2) . ?
F15 C18 1.342(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.393(2) . ?
C2 C3 1.391(2) . ?
C3 C4 1.378(2) . ?
C4 C5 1.382(2) . ?
C5 C6 1.381(2) . ?
C7 C12 1.389(2) . ?
C7 C8 1.393(2) . ?
C8 C9 1.377(2) . ?
C9 C10 1.377(2) . ?
C10 C11 1.375(2) . ?
C11 C12 1.392(2) . ?
C13 C18 1.392(2) . ?
C13 C14 1.396(2) . ?
C14 C15 1.378(2) . ?
C15 C16 1.376(3) . ?
C16 C17 1.375(3) . ?
C17 C18 1.390(2) . ?
C19 C21 1.388(2) . ?
C19 C20 1.498(3) . ?
C21 C22 1.373(3) . ?
C22 C23 1.369(3) . ?
C23 C24 1.390(2) . ?
C24 C25 1.507(3) . ?
