#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:46:16 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178533 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/38/4063802.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_4063802
loop_
_publ_author_name
'Jiang, Chunfang'
'Blacque, Olivier'
'Fox, Thomas'
'Berke, Heinz'
_publ_section_title
;
 Heterolytic Cleavage of H2by Frustrated B/N Lewis Pairs
;
_journal_issue                   8
_journal_name_full               Organometallics
_journal_page_first              2117
_journal_paper_doi               10.1021/om100951a
_journal_volume                  30
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H15 B F15 N'
_chemical_formula_sum            'C25 H15 B F15 N'
_chemical_formula_weight         625.19
_chemical_name_systematic
;
2,6-Dimethylpiperidinium tris(perfluorophenyl)borohydride
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2008-08-15T10:56:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8991(4)
_cell_length_b                   9.0917(2)
_cell_length_c                   14.4468(3)
_cell_measurement_reflns_used    8821
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      37.5064
_cell_measurement_theta_min      2.5066
_cell_volume                     2350.97(9)
_computing_cell_refinement
' CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.32.4'
_computing_data_collection
' CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.32.4'
_computing_data_reduction
' CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.32.4'
_computing_molecular_graphics
; ORTEP-3 for Windows, Version 2.01.
  Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
;
_computing_publication_material
; WinGX -- An integrated system of Windows programs for the solution,
 refinment and analysis of single crystal X-ray diffraction data,
 Version 1.80.00.
 Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
 SHELXL97. Program for crystal structure refinement.
 Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
 PLATON for Windows, Version 1.12.
 Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
;
_computing_structure_refinement
; SHELXL97. Program for crystal structure refinement.
  Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_computing_structure_solution
; SHELXS97. Program for Crystal Structure solution.
  Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.  
;
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 10.4498
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
; Oxford Diffraction (2007). Oxford Diffraction Ltd.,
        Xcalibur CCD system
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.071
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23274
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  20
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        R.C. Clark and J.S. Reid, Acta Cryst. 1995, A51, 887-897
implemented in the CrysAlis Software system, Oxford Diffraction Ltd.,
        Version 1.171.32.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0566P)²+1.0792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1172
_reflns_number_gt                2972
_reflns_number_total             3713
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100951a_si_003.cif
_cod_data_source_block           1a
_cod_database_code               4063802
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
B1 B 0.56707(18) 0.8208(4) 0.0569(2) 0.0236(6) Uani 1 1 d .
N1 N 0.55767(14) 0.7094(3) -0.03285(16) 0.0229(4) Uani 1 1 d .
H1 H 0.604(2) 0.700(4) -0.054(3) 0.022(8) Uiso 1 1 d .
C1 C 0.62022(16) 0.7442(3) 0.1376(2) 0.0245(5) Uani 1 1 d .
C2 C 0.61467(17) 0.7708(3) 0.2329(2) 0.0279(6) Uani 1 1 d .
C3 C 0.66446(18) 0.7191(4) 0.2983(2) 0.0296(6) Uani 1 1 d .
C4 C 0.72471(18) 0.6359(4) 0.2712(2) 0.0300(6) Uani 1 1 d .
C5 C 0.73577(16) 0.6100(3) 0.1783(2) 0.0273(6) Uani 1 1 d .
C6 C 0.68436(17) 0.6630(3) 0.1152(2) 0.0266(6) Uani 1 1 d .
C7 C 0.48263(15) 0.8656(3) 0.0933(2) 0.0243(5) Uani 1 1 d .
C8 C 0.44258(16) 0.7840(3) 0.1574(2) 0.0263(6) Uani 1 1 d .
C9 C 0.37426(17) 0.8253(4) 0.1937(2) 0.0306(6) Uani 1 1 d .
C10 C 0.34200(17) 0.9556(4) 0.1648(2) 0.0326(6) Uani 1 1 d .
C11 C 0.37786(18) 1.0386(4) 0.0992(2) 0.0309(6) Uani 1 1 d .
C12 C 0.44611(17) 0.9933(3) 0.0651(2) 0.0287(6) Uani 1 1 d .
C13 C 0.61940(15) 0.9651(3) 0.0297(2) 0.0249(5) Uani 1 1 d .
C14 C 0.67389(17) 0.9737(3) -0.0390(2) 0.0279(6) Uani 1 1 d .
C15 C 0.72451(17) 1.0874(4) -0.0492(2) 0.0304(6) Uani 1 1 d .
C16 C 0.72177(17) 1.2048(4) 0.0109(3) 0.0341(7) Uani 1 1 d .
C17 C 0.66961(19) 1.2039(3) 0.0797(3) 0.0355(7) Uani 1 1 d .
C18 C 0.62103(17) 1.0863(3) 0.0888(2) 0.0297(6) Uani 1 1 d .
C19 C 0.52999(17) 0.5540(3) -0.0095(2) 0.0275(6) Uani 1 1 d .
H19 H 0.5427 0.535 0.0554 0.036 Uiso 1 1 calc R
C20 C 0.44490(18) 0.5371(4) -0.0191(3) 0.0351(7) Uani 1 1 d .
H20A H 0.4319 0.434 -0.0129 0.046 Uiso 1 1 calc R
H20B H 0.4207 0.5903 0.0308 0.046 Uiso 1 1 calc R
C21 C 0.41582(19) 0.5935(4) -0.1104(3) 0.0373(7) Uani 1 1 d .
H21A H 0.362 0.5812 -0.1133 0.049 Uiso 1 1 calc R
H21B H 0.4381 0.5387 -0.1609 0.049 Uiso 1 1 calc R
C22 C 0.43576(17) 0.7555(4) -0.1188(3) 0.0339(7) Uani 1 1 d .
H22A H 0.4131 0.8092 -0.068 0.044 Uiso 1 1 calc R
H22B H 0.4154 0.7939 -0.1761 0.044 Uiso 1 1 calc R
C23 C 0.51994(16) 0.7808(3) -0.1174(2) 0.0270(5) Uani 1 1 d .
H23 H 0.528 0.8871 -0.1126 0.035 Uiso 1 1 calc R
C24 C 0.5707(2) 0.4384(4) -0.0684(3) 0.0363(7) Uani 1 1 d .
H24A H 0.5534 0.444 -0.1312 0.047 Uiso 1 1 calc R
H24B H 0.5607 0.3421 -0.0441 0.047 Uiso 1 1 calc R
H24C H 0.6235 0.4568 -0.0667 0.047 Uiso 1 1 calc R
C25 C 0.55503(19) 0.7308(4) -0.2087(2) 0.0355(7) Uani 1 1 d .
H25A H 0.5425 0.6297 -0.2199 0.046 Uiso 1 1 calc R
H25B H 0.6083 0.7409 -0.2051 0.046 Uiso 1 1 calc R
H25C H 0.5363 0.7905 -0.2584 0.046 Uiso 1 1 calc R
F1 F 0.55863(11) 0.8528(2) 0.26798(14) 0.0380(5) Uani 1 1 d .
F2 F 0.65400(12) 0.7469(3) 0.38797(14) 0.0415(5) Uani 1 1 d .
F3 F 0.77222(11) 0.5797(2) 0.33382(15) 0.0404(5) Uani 1 1 d .
F4 F 0.79535(11) 0.5341(2) 0.14936(16) 0.0379(4) Uani 1 1 d .
F5 F 0.70022(10) 0.6359(2) 0.02509(13) 0.0349(4) Uani 1 1 d .
F6 F 0.47000(10) 0.65469(19) 0.18864(14) 0.0334(4) Uani 1 1 d .
F7 F 0.34005(12) 0.7417(2) 0.25754(16) 0.0439(5) Uani 1 1 d .
F8 F 0.27632(11) 0.9994(3) 0.19982(17) 0.0444(5) Uani 1 1 d .
F9 F 0.34660(12) 1.1655(2) 0.07110(16) 0.0451(5) Uani 1 1 d .
F10 F 0.47664(11) 1.0823(2) 0.00048(15) 0.0371(4) Uani 1 1 d .
F11 F 0.68129(11) 0.8625(2) -0.10115(15) 0.0369(4) Uani 1 1 d .
F12 F 0.77525(11) 1.0838(3) -0.11674(16) 0.0442(5) Uani 1 1 d .
F13 F 0.76987(12) 1.3167(2) 0.00189(19) 0.0506(6) Uani 1 1 d .
F14 F 0.66575(14) 1.3171(2) 0.1395(2) 0.0543(7) Uani 1 1 d .
F15 F 0.57338(12) 1.0949(2) 0.16038(16) 0.0439(5) Uani 1 1 d .
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 0 '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
C7 B1 N1 107.9(2)
C7 B1 C1 113.8(2)
N1 B1 C1 110.6(2)
C7 B1 C13 113.4(2)
N1 B1 C13 110.9(2)
C1 B1 C13 100.1(2)
C19 N1 C23 114.9(2)
C19 N1 B1 115.1(2)
C23 N1 B1 114.1(2)
C19 N1 H1 107(2)
C23 N1 H1 101(2)
B1 N1 H1 103(2)
C2 C1 C6 112.1(3)
C2 C1 B1 125.3(3)
C6 C1 B1 121.9(3)
F1 C2 C3 114.3(3)
F1 C2 C1 121.1(3)
C3 C2 C1 124.5(3)
F2 C3 C4 119.4(3)
F2 C3 C2 120.6(3)
C4 C3 C2 119.9(3)
F3 C4 C3 121.0(3)
F3 C4 C5 120.1(3)
C3 C4 C5 119.0(3)
F4 C5 C4 120.5(3)
F4 C5 C6 120.3(3)
C4 C5 C6 119.2(3)
F5 C6 C5 115.5(3)
F5 C6 C1 119.3(3)
C5 C6 C1 125.2(3)
C8 C7 C12 113.5(3)
C8 C7 B1 123.7(3)
C12 C7 B1 122.7(3)
F6 C8 C9 115.6(3)
F6 C8 C7 120.0(3)
C9 C8 C7 124.4(3)
F7 C9 C10 120.1(3)
F7 C9 C8 120.6(3)
C10 C9 C8 119.2(3)
F8 C10 C11 120.5(3)
F8 C10 C9 120.5(3)
C11 C10 C9 119.0(3)
F9 C11 C10 119.1(3)
F9 C11 C12 121.1(3)
C10 C11 C12 119.8(3)
F10 C12 C11 115.3(3)
F10 C12 C7 120.8(3)
C11 C12 C7 124.0(3)
C18 C13 C14 112.2(3)
C18 C13 B1 119.5(3)
C14 C13 B1 127.4(3)
F11 C14 C15 115.0(3)
F11 C14 C13 119.8(3)
C15 C14 C13 125.2(3)
F12 C15 C16 120.3(3)
F12 C15 C14 120.4(3)
C16 C15 C14 119.3(3)
F13 C16 C17 121.1(3)
F13 C16 C15 120.3(3)
C17 C16 C15 118.6(3)
F14 C17 C16 119.9(3)
F14 C17 C18 119.8(3)
C16 C17 C18 120.3(3)
F15 C18 C17 115.3(3)
F15 C18 C13 120.3(3)
C17 C18 C13 124.4(3)
N1 C19 C20 113.1(2)
N1 C19 C24 110.8(3)
C20 C19 C24 110.6(3)
N1 C19 H19 107.4
C20 C19 H19 107.4
C24 C19 H19 107.4
C21 C20 C19 112.8(3)
C21 C20 H20A 109
C19 C20 H20A 109
C21 C20 H20B 109
C19 C20 H20B 109
H20A C20 H20B 107.8
C20 C21 C22 108.6(3)
C20 C21 H21A 110
C22 C21 H21A 110
C20 C21 H21B 110
C22 C21 H21B 110
H21A C21 H21B 108.4
C21 C22 C23 112.2(3)
C21 C22 H22A 109.2
C23 C22 H22A 109.2
C21 C22 H22B 109.2
C23 C22 H22B 109.2
H22A C22 H22B 107.9
C22 C23 C25 110.5(3)
C22 C23 N1 112.4(3)
C25 C23 N1 112.3(2)
C22 C23 H23 107.1
C25 C23 H23 107.1
N1 C23 H23 107.1
C19 C24 H24A 109.5
C19 C24 H24B 109.5
H24A C24 H24B 109.5
C19 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C23 C25 H25A 109.5
C23 C25 H25B 109.5
H25A C25 H25B 109.5
C23 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 C7 1.651(4)
B1 N1 1.654(4)
B1 C1 1.659(4)
B1 C13 1.659(4)
N1 C19 1.535(4)
N1 C23 1.539(4)
N1 H1 0.89(4)
C1 C2 1.402(4)
C1 C6 1.403(4)
C2 F1 1.349(4)
C2 C3 1.381(4)
C3 F2 1.333(4)
C3 C4 1.374(5)
C4 F3 1.342(3)
C4 C5 1.377(4)
C5 F4 1.337(4)
C5 C6 1.382(4)
C6 F5 1.355(3)
C7 C8 1.386(4)
C7 C12 1.394(4)
C8 F6 1.351(3)
C8 C9 1.382(4)
C9 F7 1.343(4)
C9 C10 1.382(5)
C10 F8 1.340(4)
C10 C11 1.371(5)
C11 F9 1.345(4)
C11 C12 1.380(4)
C12 F10 1.350(4)
C13 C18 1.394(4)
C13 C14 1.394(4)
C14 F11 1.358(4)
C14 C15 1.383(4)
C15 F12 1.333(4)
C15 C16 1.377(5)
C16 F13 1.339(3)
C16 C17 1.363(5)
C17 F14 1.346(4)
C17 C18 1.384(4)
C18 F15 1.343(4)
C19 C20 1.537(4)
C19 C24 1.537(5)
C19 H19 0.98
C20 C21 1.508(5)
C20 H20A 0.97
C20 H20B 0.97
C21 C22 1.520(5)
C21 H21A 0.97
C21 H21B 0.97
C22 C23 1.524(4)
C22 H22A 0.97
C22 H22B 0.97
C23 C25 1.529(4)
C23 H23 0.98
C24 H24A 0.96
C24 H24B 0.96
C24 H24C 0.96
C25 H25A 0.96
C25 H25B 0.96
C25 H25C 0.96
