# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2011
data_global
_journal_name_full 'Dalton Trans.'
#TrackingRef 'Crystal Structures.cif'
_journal_coden_Cambridge 0222
#==============================================================================
# TITLE AND AUTHOR LIST
_publ_section_title
;
Reversible Metal-Free Hydrogen Activation by Frustrated Lewis Pairs
;
loop_
_publ_author_name
_publ_author_address
C.Jiang
;
Anorganisch-Chemisches Institut der Universit\"at Z\"urich
Winterthurerstrasse 190
CH-8057 Z\"urich
;
O.Blacque
;
Anorganisch-Chemisches Institut der Universit\"at Z\"urich
Winterthurerstrasse 190
CH-8057 Z\"urich
;
T.Fox
;
Anorganisch-Chemisches Institut der Universit\"at Z\"urich
Winterthurerstrasse 190
CH-8057 Z\"urich
;
H.Berke
;
Anorganisch-Chemisches Institut der Universit\"at Z\"urich
Winterthurerstrasse 190
CH-8057 Z\"urich
;
#-----------REFINEMENT DETAILS-----------------------------------------#
_publ_section_exptl_refinement
;
The hydrogen atoms bound to the phosphorus, nitrogen and boron atoms were
located in the difference Fourier map and freely refined. All other hydrogen
positions were calculated after each cycle of refinement using a riding model
with C---H = 0.93 \%A and U~iso~(H) = 1.2U~eq~(C) for aromatic H
atoms, with C---H = 0.97 \%A and U~iso~(H) = 1.2U~eq~(C) for
methylene H atoms, with C---H = 0.98 \%A and U~iso~(H) =
1.2U~eq~(C) for methine H atoms, and with C---H = 0.96 \%A and
U~iso~(H) = 1.5U~eq~(C) for methyl H atoms.
In 4 b, the anion and the cation are oriented face-to-face to
each other with a non-bonding H1...H2 distance of 2.63 \%A. In 6, a
close B---H...H---N bonding contact of 1.88 \%A exists, consistent with a
strong dihydrogen bonding. Furthermore, the crystal structures are stabilized
by weak C---H...F intermolecular interactions.
;
_publ_contact_author_name 'Dr. Blacque, Olivier'
_publ_contact_author_email oblacque@aci.uzh.ch
#----------------------------------------------------------------------------#
data_4b
_database_code_depnum_ccdc_archive 'CCDC 793471'
#TrackingRef 'Crystal Structures.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
Tri-tert-butylphosphonium cyclohexylbis(pentafluorophenyl)hydridoborate
;
_chemical_name_common
;Tri-tert-butylphosphonium
cyclohexylbis(pentafluorophenyl)hydridoborate
;
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H28 P, C18 H12 B F10'
_chemical_formula_sum 'C30 H40 B F10 P'
_chemical_formula_weight 632.40
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P b c a'
_symmetry_space_group_name_Hall '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
_cell_length_a 18.3337(3)
_cell_length_b 16.1172(3)
_cell_length_c 20.7593(3)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 6134.12(18)
_cell_formula_units_Z 8
_cell_measurement_temperature 183(2)
_cell_measurement_reflns_used 11084
_cell_measurement_theta_min 2.5510
_cell_measurement_theta_max 32.8117
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.44
_exptl_crystal_size_mid 0.29
_exptl_crystal_size_min 0.24
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.370
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2640
_exptl_absorpt_coefficient_mu 0.170
_exptl_absorpt_correction_T_min 0.870
_exptl_absorpt_correction_T_max 0.960
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 183(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type
; Goniometer Xcalibur, detector: Ruby
Oxford Diffraction (2007). Oxford Diffraction Ltd.,
Xcalibur CCD system
;
_diffrn_measurement_method 'omega scans'
_diffrn_detector_area_resol_mean 10.4498
_diffrn_standards_number 2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time 60
_diffrn_standards_decay_% 0
_diffrn_reflns_number 43845
_diffrn_reflns_av_R_equivalents 0.0455
_diffrn_reflns_av_sigmaI/netI 0.0664
_diffrn_reflns_limit_h_min -26
_diffrn_reflns_limit_h_max 24
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_limit_l_max 29
_diffrn_reflns_theta_min 2.56
_diffrn_reflns_theta_max 30.51
_reflns_number_total 9356
_reflns_number_gt 5223
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41
;
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41
;
_computing_structure_solution
; SHELXS97. Program for Crystal Structure solution.
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_computing_structure_refinement
; SHELXL97. Program for crystal structure refinement.
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_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.
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0508P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 9356
_refine_ls_number_parameters 396
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0895
_refine_ls_R_factor_gt 0.0427
_refine_ls_wR_factor_ref 0.0999
_refine_ls_wR_factor_gt 0.0918
_refine_ls_goodness_of_fit_ref 0.864
_refine_ls_restrained_S_all 0.864
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
C1 C 0.34939(7) 0.33886(9) -0.01939(7) 0.0255(3) Uani 1 1 d . . .
C2 C 0.36951(8) 0.28384(9) -0.06780(7) 0.0310(3) Uani 1 1 d . . .
C3 C 0.38849(9) 0.20187(10) -0.05823(8) 0.0380(4) Uani 1 1 d . . .
C4 C 0.38785(9) 0.17001(9) 0.00284(9) 0.0395(4) Uani 1 1 d . . .
C5 C 0.37006(8) 0.22103(10) 0.05297(8) 0.0356(4) Uani 1 1 d . . .
C6 C 0.35196(8) 0.30273(9) 0.04122(7) 0.0291(3) Uani 1 1 d . . .
C7 C 0.23450(8) 0.42397(8) -0.05878(6) 0.0244(3) Uani 1 1 d . . .
C8 C 0.20804(8) 0.44157(9) -0.11953(7) 0.0287(3) Uani 1 1 d . . .
C9 C 0.13579(9) 0.43612(9) -0.13763(7) 0.0324(3) Uani 1 1 d . . .
C10 C 0.08548(8) 0.40873(9) -0.09404(7) 0.0295(3) Uani 1 1 d . . .
C11 C 0.10731(8) 0.38915(9) -0.03297(7) 0.0288(3) Uani 1 1 d . . .
C12 C 0.17984(8) 0.39757(8) -0.01683(6) 0.0258(3) Uani 1 1 d . . .
C13 C 0.33108(8) 0.50446(9) 0.01745(6) 0.0263(3) Uani 1 1 d . . .
H13 H 0.3026 0.4877 0.0564 0.032 Uiso 1 1 calc R . .
C14 C 0.41105(8) 0.51388(9) 0.03650(7) 0.0326(3) Uani 1 1 d . . .
H14A H 0.4278 0.4614 0.0563 0.039 Uiso 1 1 calc R . .
H14B H 0.4403 0.5231 -0.0029 0.039 Uiso 1 1 calc R . .
C15 C 0.42543(9) 0.58452(10) 0.08322(8) 0.0431(4) Uani 1 1 d . . .
H15A H 0.4010 0.5726 0.1247 0.052 Uiso 1 1 calc R . .
H15B H 0.4785 0.5888 0.0914 0.052 Uiso 1 1 calc R . .
C16 C 0.39779(10) 0.66589(10) 0.05703(8) 0.0451(4) Uani 1 1 d . . .
H16A H 0.4262 0.6812 0.0182 0.054 Uiso 1 1 calc R . .
H16B H 0.4047 0.7100 0.0897 0.054 Uiso 1 1 calc R . .
C17 C 0.31686(10) 0.65939(10) 0.03962(9) 0.0469(4) Uani 1 1 d . . .
H17A H 0.2880 0.6513 0.0794 0.056 Uiso 1 1 calc R . .
H17B H 0.3008 0.7119 0.0194 0.056 Uiso 1 1 calc R . .
C18 C 0.30233(9) 0.58798(9) -0.00622(8) 0.0357(4) Uani 1 1 d . . .
H18A H 0.3251 0.6008 -0.0483 0.043 Uiso 1 1 calc R . .
H18B H 0.2491 0.5834 -0.0132 0.043 Uiso 1 1 calc R . .
C19 C 0.37771(8) 0.52994(9) -0.29082(6) 0.0292(3) Uani 1 1 d . . .
C20 C 0.42421(9) 0.56371(10) -0.34669(7) 0.0392(4) Uani 1 1 d . . .
H20A H 0.4245 0.5234 -0.3821 0.059 Uiso 1 1 calc R . .
H20B H 0.4742 0.5730 -0.3317 0.059 Uiso 1 1 calc R . .
H20C H 0.4035 0.6162 -0.3619 0.059 Uiso 1 1 calc R . .
C21 C 0.41107(9) 0.45066(9) -0.26187(7) 0.0381(4) Uani 1 1 d . . .
H21A H 0.3829 0.4339 -0.2240 0.057 Uiso 1 1 calc R . .
H21B H 0.4617 0.4615 -0.2492 0.057 Uiso 1 1 calc R . .
H21C H 0.4099 0.4061 -0.2940 0.057 Uiso 1 1 calc R . .
C22 C 0.30225(9) 0.50634(10) -0.31743(7) 0.0372(4) Uani 1 1 d . . .
H22A H 0.2787 0.5557 -0.3356 0.056 Uiso 1 1 calc R . .
H22B H 0.2721 0.4840 -0.2825 0.056 Uiso 1 1 calc R . .
H22C H 0.3079 0.4642 -0.3511 0.056 Uiso 1 1 calc R . .
C23 C 0.45958(8) 0.65569(10) -0.20091(7) 0.0341(4) Uani 1 1 d . . .
C24 C 0.52013(9) 0.59023(11) -0.20262(9) 0.0473(4) Uani 1 1 d . . .
H24A H 0.5282 0.5723 -0.2472 0.071 Uiso 1 1 calc R . .
H24B H 0.5057 0.5424 -0.1764 0.071 Uiso 1 1 calc R . .
H24C H 0.5653 0.6141 -0.1854 0.071 Uiso 1 1 calc R . .
C25 C 0.48146(10) 0.72936(11) -0.24343(9) 0.0524(5) Uani 1 1 d . . .
H25A H 0.5291 0.7505 -0.2296 0.079 Uiso 1 1 calc R . .
H25B H 0.4449 0.7734 -0.2395 0.079 Uiso 1 1 calc R . .
H25C H 0.4844 0.7113 -0.2884 0.079 Uiso 1 1 calc R . .
C26 C 0.45349(10) 0.68249(11) -0.12948(7) 0.0469(4) Uani 1 1 d . . .
H26A H 0.4386 0.6348 -0.1033 0.070 Uiso 1 1 calc R . .
H26B H 0.4171 0.7267 -0.1255 0.070 Uiso 1 1 calc R . .
H26C H 0.5009 0.7029 -0.1145 0.070 Uiso 1 1 calc R . .
C27 C 0.29510(8) 0.68587(9) -0.23683(7) 0.0332(4) Uani 1 1 d . . .
C28 C 0.29962(10) 0.72860(10) -0.30273(8) 0.0474(4) Uani 1 1 d . . .
H28A H 0.2602 0.7693 -0.3066 0.071 Uiso 1 1 calc R . .
H28B H 0.2948 0.6870 -0.3369 0.071 Uiso 1 1 calc R . .
H28C H 0.3468 0.7568 -0.3068 0.071 Uiso 1 1 calc R . .
C29 C 0.29875(10) 0.75225(11) -0.18403(9) 0.0505(5) Uani 1 1 d . . .
H29A H 0.3437 0.7845 -0.1889 0.076 Uiso 1 1 calc R . .
H29B H 0.2983 0.7254 -0.1417 0.076 Uiso 1 1 calc R . .
H29C H 0.2565 0.7892 -0.1878 0.076 Uiso 1 1 calc R . .
C30 C 0.22053(9) 0.64266(11) -0.22855(9) 0.0451(4) Uani 1 1 d . . .
H30A H 0.1816 0.6842 -0.2303 0.068 Uiso 1 1 calc R . .
H30B H 0.2191 0.6142 -0.1869 0.068 Uiso 1 1 calc R . .
H30C H 0.2136 0.6022 -0.2632 0.068 Uiso 1 1 calc R . .
B1 B 0.32103(9) 0.43321(10) -0.03758(8) 0.0250(3) Uani 1 1 d . . .
H1 H 0.3555(6) 0.4537(7) -0.0844(5) 0.013(3) Uiso 1 1 d . . .
F1 F 0.37016(5) 0.30925(6) -0.13022(4) 0.0444(2) Uani 1 1 d . . .
F2 F 0.40645(6) 0.15254(6) -0.10826(5) 0.0603(3) Uani 1 1 d . . .
F3 F 0.40303(6) 0.08923(6) 0.01327(6) 0.0585(3) Uani 1 1 d . . .
F4 F 0.36907(5) 0.19105(6) 0.11379(5) 0.0521(3) Uani 1 1 d . . .
F5 F 0.33518(5) 0.34788(5) 0.09459(4) 0.0391(2) Uani 1 1 d . . .
F6 F 0.25478(5) 0.46388(6) -0.16748(4) 0.0451(2) Uani 1 1 d . . .
F7 F 0.11517(5) 0.45292(7) -0.19882(4) 0.0544(3) Uani 1 1 d . . .
F8 F 0.01532(5) 0.39835(6) -0.11196(4) 0.0459(2) Uani 1 1 d . . .
F9 F 0.05813(5) 0.36159(6) 0.01015(4) 0.0459(2) Uani 1 1 d . . .
F10 F 0.19770(5) 0.37712(6) 0.04455(4) 0.0381(2) Uani 1 1 d . . .
P1 P 0.37009(2) 0.60898(2) -0.225326(17) 0.02427(9) Uani 1 1 d . . .
H2 H 0.3498(7) 0.5686(8) -0.1743(6) 0.025(4) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0162(7) 0.0277(7) 0.0325(8) 0.0009(6) -0.0043(6) -0.0012(6)
C2 0.0271(8) 0.0337(8) 0.0322(8) -0.0014(6) -0.0064(7) 0.0002(7)
C3 0.0290(9) 0.0345(9) 0.0505(10) -0.0127(8) -0.0087(8) 0.0054(7)
C4 0.0262(9) 0.0254(8) 0.0670(12) 0.0023(8) -0.0119(8) 0.0010(7)
C5 0.0241(8) 0.0363(9) 0.0465(9) 0.0169(7) -0.0088(7) -0.0031(7)
C6 0.0200(8) 0.0346(8) 0.0327(8) -0.0012(6) -0.0019(6) -0.0004(6)
C7 0.0256(8) 0.0195(7) 0.0279(7) -0.0010(5) -0.0021(6) 0.0020(6)
C8 0.0301(9) 0.0270(8) 0.0290(7) 0.0053(6) 0.0016(7) -0.0017(7)
C9 0.0348(9) 0.0316(8) 0.0309(8) 0.0059(6) -0.0111(7) 0.0025(7)
C10 0.0203(7) 0.0282(8) 0.0401(8) -0.0026(6) -0.0081(7) 0.0020(6)
C11 0.0225(7) 0.0324(8) 0.0316(7) -0.0020(6) 0.0035(6) 0.0007(6)
C12 0.0276(8) 0.0271(8) 0.0228(7) -0.0018(6) -0.0040(6) 0.0048(6)
C13 0.0211(8) 0.0289(7) 0.0290(7) -0.0007(6) 0.0005(6) -0.0013(6)
C14 0.0246(8) 0.0353(8) 0.0379(8) 0.0005(7) -0.0021(7) -0.0013(7)
C15 0.0377(10) 0.0488(10) 0.0428(9) -0.0090(8) -0.0079(8) -0.0091(8)
C16 0.0489(11) 0.0357(9) 0.0506(10) -0.0146(8) 0.0033(9) -0.0101(8)
C17 0.0443(11) 0.0340(9) 0.0625(11) -0.0118(8) 0.0013(9) 0.0035(8)
C18 0.0282(8) 0.0301(8) 0.0489(9) -0.0029(7) -0.0009(7) 0.0028(7)
C19 0.0362(9) 0.0286(8) 0.0229(7) -0.0038(6) 0.0010(6) 0.0038(7)
C20 0.0458(10) 0.0458(10) 0.0261(8) -0.0004(7) 0.0073(7) 0.0054(8)
C21 0.0464(10) 0.0311(9) 0.0368(9) -0.0030(7) 0.0009(8) 0.0073(8)
C22 0.0446(10) 0.0372(9) 0.0299(8) -0.0084(7) -0.0039(7) -0.0025(8)
C23 0.0264(8) 0.0423(9) 0.0338(8) -0.0030(7) -0.0017(7) -0.0073(7)
C24 0.0287(9) 0.0635(12) 0.0496(10) -0.0070(9) -0.0071(8) 0.0025(9)
C25 0.0443(11) 0.0516(11) 0.0613(11) 0.0027(9) 0.0010(9) -0.0198(9)
C26 0.0375(10) 0.0604(11) 0.0429(9) -0.0141(8) -0.0081(8) -0.0084(9)
C27 0.0309(9) 0.0328(8) 0.0360(8) -0.0045(6) -0.0009(7) 0.0056(7)
C28 0.0527(12) 0.0411(10) 0.0485(10) 0.0094(8) -0.0059(9) 0.0103(9)
C29 0.0481(11) 0.0449(10) 0.0584(11) -0.0199(8) -0.0024(9) 0.0096(9)
C30 0.0274(9) 0.0467(10) 0.0612(11) -0.0088(8) 0.0010(8) 0.0047(8)
B1 0.0232(9) 0.0253(8) 0.0265(8) 0.0014(7) 0.0008(7) 0.0005(7)
F1 0.0542(7) 0.0460(6) 0.0331(5) -0.0058(4) -0.0014(4) 0.0078(5)
F2 0.0653(7) 0.0452(6) 0.0703(7) -0.0255(5) -0.0104(6) 0.0186(5)
F3 0.0487(6) 0.0272(5) 0.0996(8) 0.0064(5) -0.0210(6) 0.0056(5)
F4 0.0467(6) 0.0522(6) 0.0574(6) 0.0272(5) -0.0064(5) 0.0008(5)
F5 0.0396(5) 0.0473(5) 0.0303(5) 0.0044(4) 0.0001(4) 0.0043(4)
F6 0.0413(6) 0.0617(6) 0.0322(5) 0.0173(4) -0.0013(4) -0.0111(5)
F7 0.0499(6) 0.0741(7) 0.0391(5) 0.0205(5) -0.0185(5) -0.0030(5)
F8 0.0239(5) 0.0600(6) 0.0538(6) 0.0014(5) -0.0131(4) 0.0004(5)
F9 0.0253(5) 0.0714(7) 0.0411(5) 0.0050(5) 0.0048(4) -0.0053(5)
F10 0.0308(5) 0.0590(6) 0.0245(4) 0.0053(4) -0.0020(4) -0.0025(4)
P1 0.02414(19) 0.02733(19) 0.02133(16) -0.00124(15) 0.00057(15) -0.00080(16)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 C6 1.3871(19) . ?
C1 C2 1.390(2) . ?
C1 B1 1.651(2) . ?
C2 F1 1.3590(16) . ?
C2 C3 1.381(2) . ?
C3 F2 1.3487(18) . ?
C3 C4 1.368(2) . ?
C4 F3 1.3488(17) . ?
C4 C5 1.366(2) . ?
C5 F4 1.3520(17) . ?
C5 C6 1.380(2) . ?
C6 F5 1.3607(16) . ?
C7 C8 1.3805(19) . ?
C7 C12 1.3941(19) . ?
C7 B1 1.653(2) . ?
C8 F6 1.3617(16) . ?
C8 C9 1.380(2) . ?
C9 F7 1.3528(16) . ?
C9 C10 1.365(2) . ?
C10 F8 1.3495(16) . ?
C10 C11 1.366(2) . ?
C11 F9 1.3459(16) . ?
C11 C12 1.378(2) . ?
C12 F10 1.3563(15) . ?
C13 C14 1.526(2) . ?
C13 C18 1.527(2) . ?
C13 B1 1.630(2) . ?
C13 H13 1.0000 . ?
C14 C15 1.519(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.507(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.531(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.517(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C22 1.537(2) . ?
C19 C20 1.539(2) . ?
C19 C21 1.539(2) . ?
C19 P1 1.8684(14) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.532(2) . ?
C23 C25 1.533(2) . ?
C23 C26 1.549(2) . ?
C23 P1 1.8748(15) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C29 1.533(2) . ?
C27 C28 1.534(2) . ?
C27 C30 1.544(2) . ?
C27 P1 1.8663(15) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
B1 H1 1.205(12) . ?
P1 H2 1.298(13) . ?
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
C6 C1 C2 112.27(13) . . ?
C6 C1 B1 127.22(12) . . ?
C2 C1 B1 120.38(12) . . ?
F1 C2 C3 115.04(13) . . ?
F1 C2 C1 119.96(13) . . ?
C3 C2 C1 124.98(14) . . ?
F2 C3 C4 119.64(14) . . ?
F2 C3 C2 120.99(15) . . ?
C4 C3 C2 119.36(14) . . ?
F3 C4 C5 120.54(15) . . ?
F3 C4 C3 120.61(15) . . ?
C5 C4 C3 118.83(14) . . ?
F4 C5 C4 119.97(14) . . ?
F4 C5 C6 120.19(14) . . ?
C4 C5 C6 119.82(14) . . ?
F5 C6 C5 114.88(13) . . ?
F5 C6 C1 120.42(12) . . ?
C5 C6 C1 124.69(13) . . ?
C8 C7 C12 112.39(13) . . ?
C8 C7 B1 124.18(12) . . ?
C12 C7 B1 123.43(12) . . ?
F6 C8 C9 114.95(12) . . ?
F6 C8 C7 120.06(13) . . ?
C9 C8 C7 124.96(13) . . ?
F7 C9 C10 119.88(13) . . ?
F7 C9 C8 120.75(14) . . ?
C10 C9 C8 119.25(13) . . ?
F8 C10 C9 120.09(13) . . ?
F8 C10 C11 120.42(14) . . ?
C9 C10 C11 119.46(13) . . ?
F9 C11 C10 119.81(13) . . ?
F9 C11 C12 121.15(13) . . ?
C10 C11 C12 119.04(13) . . ?
F10 C12 C11 115.94(12) . . ?
F10 C12 C7 119.18(12) . . ?
C11 C12 C7 124.87(13) . . ?
C14 C13 C18 109.11(12) . . ?
C14 C13 B1 111.12(12) . . ?
C18 C13 B1 110.89(11) . . ?
C14 C13 H13 108.6 . . ?
C18 C13 H13 108.6 . . ?
B1 C13 H13 108.6 . . ?
C15 C14 C13 114.01(13) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 111.32(13) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 110.58(14) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 111.73(14) . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C13 113.98(13) . . ?
C17 C18 H18A 108.8 . . ?
C13 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C13 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C22 C19 C20 108.38(12) . . ?
C22 C19 C21 107.00(12) . . ?
C20 C19 C21 111.59(12) . . ?
C22 C19 P1 111.28(10) . . ?
C20 C19 P1 110.41(10) . . ?
C21 C19 P1 108.16(9) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C25 109.30(14) . . ?
C24 C23 C26 105.45(13) . . ?
C25 C23 C26 110.75(14) . . ?
C24 C23 P1 110.56(11) . . ?
C25 C23 P1 112.61(11) . . ?
C26 C23 P1 107.93(11) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 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 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C29 C27 C28 108.78(14) . . ?
C29 C27 C30 105.89(13) . . ?
C28 C27 C30 110.46(13) . . ?
C29 C27 P1 109.86(11) . . ?
C28 C27 P1 111.87(11) . . ?
C30 C27 P1 109.79(11) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C13 B1 C1 116.93(12) . . ?
C13 B1 C7 111.01(12) . . ?
C1 B1 C7 106.27(11) . . ?
C13 B1 H1 108.2(6) . . ?
C1 B1 H1 105.7(6) . . ?
C7 B1 H1 108.3(6) . . ?
C27 P1 C19 114.50(7) . . ?
C27 P1 C23 114.37(7) . . ?
C19 P1 C23 113.90(7) . . ?
C27 P1 H2 103.1(6) . . ?
C19 P1 H2 105.8(6) . . ?
C23 P1 H2 103.4(6) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
P1 H2 F6 1.298(13) 2.429(13) 3.3735(9) 127.0(8) .
C13 H13 F5 1.00 2.46 2.9898(16) 112.4 .
C22 H22B F6 0.98 2.43 3.3040(17) 148.1 .
C30 H30B F6 0.98 2.54 3.210(2) 125.4 .
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 30.51
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.317
_refine_diff_density_min -0.277
_refine_diff_density_rms 0.043
#===END
data_6
_database_code_depnum_ccdc_archive 'CCDC 793472'
#TrackingRef 'Crystal Structures.cif'
_vrf_PLAT415_6
;
PROBLEM: Short Inter D-H..H-X H1.. H2.. 1.88 \%A.
RESPONSE: A close B-H...H-N bonding contact of 1.88 \%A exists, consistent with
a strong dihydrogen bonding.
;
# end Validation Reply Form
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
2,2,6,6-Tetramethylpiperidinium phenethylbis(pentafluorophenyl)hydridoborate
;
_chemical_name_common
;2,2,6,6-Tetramethylpiperidinium
phenethylbis(pentafluorophenyl)hydridoborate
;
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H10 B F10, C9 H20 N'
_chemical_formula_sum 'C29 H30 B F10 N'
_chemical_formula_weight 593.35
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'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.4346(2)
_cell_length_b 11.4068(3)
_cell_length_c 14.4546(3)
_cell_angle_alpha 74.034(2)
_cell_angle_beta 87.133(2)
_cell_angle_gamma 68.809(2)
_cell_volume 1392.33(6)
_cell_formula_units_Z 2
_cell_measurement_temperature 183(2)
_cell_measurement_reflns_used 12086
_cell_measurement_theta_min 2.62
_cell_measurement_theta_max 32.74
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.27
_exptl_crystal_size_min 0.19
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.415
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 612
_exptl_absorpt_coefficient_mu 0.128
_exptl_absorpt_correction_T_min 0.969
_exptl_absorpt_correction_T_max 0.981
_exptl_absorpt_correction_type analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 183(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type
; Goniometer Xcalibur, detector: Ruby
Oxford Diffraction (2007). Oxford Diffraction Ltd.,
Xcalibur CCD system
;
_diffrn_measurement_method 'omega scans'
_diffrn_detector_area_resol_mean 10.4498
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 28610
_diffrn_reflns_av_R_equivalents 0.0257
_diffrn_reflns_av_sigmaI/netI 0.0251
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.63
_diffrn_reflns_theta_max 29.12
_reflns_number_total 7497
_reflns_number_gt 5114
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41
;
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41
;
_computing_structure_solution
; SHELXS97. Program for Crystal Structure solution.
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_computing_structure_refinement
; SHELXL97. Program for crystal structure refinement.
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_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.
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1095P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 7497
_refine_ls_number_parameters 385
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0781
_refine_ls_R_factor_gt 0.0562
_refine_ls_wR_factor_ref 0.1814
_refine_ls_wR_factor_gt 0.1720
_refine_ls_goodness_of_fit_ref 1.094
_refine_ls_restrained_S_all 1.094
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
C1 C 0.06874(17) 0.29081(14) 0.28019(10) 0.0329(3) Uani 1 1 d . . .
C2 C 0.15133(18) 0.32551(16) 0.33781(13) 0.0396(4) Uani 1 1 d . . .
C3 C 0.3080(2) 0.27816(18) 0.34950(15) 0.0508(4) Uani 1 1 d . . .
C4 C 0.39214(19) 0.18965(17) 0.30133(15) 0.0505(5) Uani 1 1 d . . .
C5 C 0.3178(2) 0.15258(15) 0.24286(14) 0.0464(4) Uani 1 1 d . . .
C6 C 0.1607(2) 0.20146(15) 0.23349(12) 0.0402(4) Uani 1 1 d . . .
C7 C -0.17592(16) 0.28516(14) 0.37875(10) 0.0313(3) Uani 1 1 d . . .
C8 C -0.15597(18) 0.15347(15) 0.40691(11) 0.0372(3) Uani 1 1 d . . .
C9 C -0.2148(2) 0.09464(18) 0.48794(13) 0.0481(4) Uani 1 1 d . . .
C10 C -0.2951(2) 0.1686(2) 0.54684(13) 0.0552(5) Uani 1 1 d . . .
C11 C -0.31544(19) 0.2985(2) 0.52440(12) 0.0492(4) Uani 1 1 d . . .
C12 C -0.25566(17) 0.35329(16) 0.44203(11) 0.0379(3) Uani 1 1 d . . .
C13 C -0.20576(19) 0.33757(15) 0.18751(11) 0.0388(4) Uani 1 1 d . . .
H13A H -0.1663 0.3721 0.1271 0.047 Uiso 1 1 calc R . .
H13B H -0.1839 0.2455 0.1950 0.047 Uiso 1 1 calc R . .
C14 C -0.3785(2) 0.40886(17) 0.18294(12) 0.0423(4) Uani 1 1 d . . .
H14A H -0.4257 0.3747 0.1438 0.051 Uiso 1 1 calc R . .
H14B H -0.4140 0.3891 0.2475 0.051 Uiso 1 1 calc R . .
C15 C -0.43172(17) 0.55558(16) 0.14240(11) 0.0365(3) Uani 1 1 d . . .
C16 C -0.4382(2) 0.61210(19) 0.04322(13) 0.0510(4) Uani 1 1 d . . .
H16 H -0.4065 0.5584 0.0023 0.061 Uiso 1 1 calc R . .
C17 C -0.4904(3) 0.7458(2) 0.00476(17) 0.0677(6) Uani 1 1 d . . .
H17 H -0.4955 0.7817 -0.0616 0.081 Uiso 1 1 calc R . .
C18 C -0.5351(3) 0.8260(2) 0.0648(2) 0.0714(7) Uani 1 1 d . . .
H18 H -0.5701 0.9164 0.0391 0.086 Uiso 1 1 calc R . .
C19 C -0.5281(2) 0.7730(2) 0.1622(2) 0.0663(6) Uani 1 1 d . . .
H19 H -0.5575 0.8273 0.2028 0.080 Uiso 1 1 calc R . .
C20 C -0.4774(2) 0.63918(19) 0.20033(14) 0.0498(4) Uani 1 1 d . . .
H20 H -0.4740 0.6044 0.2668 0.060 Uiso 1 1 calc R . .
C21 C -0.02208(19) 0.70474(17) 0.12674(13) 0.0423(4) Uani 1 1 d . . .
C22 C -0.0888(3) 0.8471(2) 0.06668(16) 0.0632(5) Uani 1 1 d . . .
H22A H -0.1905 0.8649 0.0422 0.076 Uiso 1 1 calc R . .
H22B H -0.0272 0.8599 0.0118 0.076 Uiso 1 1 calc R . .
C23 C -0.0970(3) 0.9448(2) 0.12309(19) 0.0740(7) Uani 1 1 d . . .
H23A H -0.1422 1.0332 0.0815 0.089 Uiso 1 1 calc R . .
H23B H 0.0051 0.9320 0.1436 0.089 Uiso 1 1 calc R . .
C24 C -0.1923(3) 0.92738(19) 0.21204(17) 0.0602(5) Uani 1 1 d . . .
H24A H -0.1928 0.9888 0.2471 0.072 Uiso 1 1 calc R . .
H24B H -0.2966 0.9480 0.1908 0.072 Uiso 1 1 calc R . .
C25 C -0.1317(2) 0.78840(16) 0.28006(13) 0.0428(4) Uani 1 1 d . . .
C26 C -0.0547(3) 0.6169(2) 0.07542(16) 0.0662(6) Uani 1 1 d . . .
H26A H -0.0120 0.6273 0.0133 0.099 Uiso 1 1 calc R . .
H26B H -0.1628 0.6405 0.0675 0.099 Uiso 1 1 calc R . .
H26C H -0.0101 0.5274 0.1130 0.099 Uiso 1 1 calc R . .
C27 C 0.1455(2) 0.6584(3) 0.1526(2) 0.0789(7) Uani 1 1 d . . .
H27A H 0.1757 0.5763 0.2016 0.118 Uiso 1 1 calc R . .
H27B H 0.1659 0.7219 0.1763 0.118 Uiso 1 1 calc R . .
H27C H 0.2019 0.6475 0.0965 0.118 Uiso 1 1 calc R . .
C28 C -0.2471(3) 0.7655(3) 0.35254(17) 0.0702(6) Uani 1 1 d . . .
H28A H -0.2052 0.6788 0.3952 0.105 Uiso 1 1 calc R . .
H28B H -0.3378 0.7750 0.3192 0.105 Uiso 1 1 calc R . .
H28C H -0.2714 0.8283 0.3891 0.105 Uiso 1 1 calc R . .
C29 C 0.0170(3) 0.7583(2) 0.33302(18) 0.0694(6) Uani 1 1 d . . .
H29A H 0.0611 0.6662 0.3638 0.104 Uiso 1 1 calc R . .
H29B H -0.0015 0.8056 0.3808 0.104 Uiso 1 1 calc R . .
H29C H 0.0858 0.7842 0.2881 0.104 Uiso 1 1 calc R . .
N1 N -0.11245(18) 0.69454(14) 0.21862(11) 0.0395(3) Uani 1 1 d . . .
H2 H -0.065(2) 0.603(2) 0.2574(16) 0.058(6) Uiso 1 1 d . . .
H3 H -0.207(2) 0.705(2) 0.2031(14) 0.051(5) Uiso 1 1 d . . .
F1 F 0.07548(11) 0.41397(11) 0.38661(8) 0.0545(3) Uani 1 1 d . . .
F2 F 0.37839(13) 0.31795(14) 0.40667(11) 0.0774(4) Uani 1 1 d . . .
F3 F 0.54475(12) 0.13977(12) 0.31241(11) 0.0747(4) Uani 1 1 d . . .
F4 F 0.39938(13) 0.06421(11) 0.19553(9) 0.0633(3) Uani 1 1 d . . .
F5 F 0.09848(13) 0.15580(11) 0.17559(8) 0.0564(3) Uani 1 1 d . . .
F6 F -0.07632(13) 0.07497(9) 0.35239(7) 0.0497(3) Uani 1 1 d . . .
F7 F -0.19473(15) -0.03335(12) 0.50937(10) 0.0712(4) Uani 1 1 d . . .
F8 F -0.35345(16) 0.11397(15) 0.62717(10) 0.0865(5) Uani 1 1 d . . .
F9 F -0.38971(14) 0.37055(14) 0.58389(8) 0.0782(4) Uani 1 1 d . . .
F10 F -0.27985(12) 0.48183(10) 0.42566(7) 0.0513(3) Uani 1 1 d . . .
B1 B -0.11821(19) 0.35239(16) 0.27592(12) 0.0311(3) Uani 1 1 d . . .
H1 H -0.150(2) 0.4748(18) 0.2654(13) 0.047 Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0370(8) 0.0293(7) 0.0312(7) -0.0053(6) 0.0064(6) -0.0134(6)
C2 0.0361(8) 0.0360(8) 0.0477(9) -0.0132(7) 0.0057(7) -0.0133(7)
C3 0.0401(9) 0.0481(10) 0.0670(12) -0.0147(9) 0.0010(8) -0.0197(8)
C4 0.0342(8) 0.0392(9) 0.0724(13) -0.0072(9) 0.0109(8) -0.0137(7)
C5 0.0475(10) 0.0294(8) 0.0556(11) -0.0088(7) 0.0228(8) -0.0110(7)
C6 0.0504(9) 0.0332(8) 0.0374(8) -0.0086(6) 0.0096(7) -0.0174(7)
C7 0.0300(7) 0.0355(7) 0.0293(7) -0.0051(6) -0.0033(6) -0.0151(6)
C8 0.0380(8) 0.0386(8) 0.0348(8) -0.0037(6) -0.0030(6) -0.0176(6)
C9 0.0465(10) 0.0486(10) 0.0435(10) 0.0086(8) -0.0075(8) -0.0251(8)
C10 0.0408(9) 0.0719(13) 0.0369(9) 0.0129(9) 0.0027(7) -0.0227(9)
C11 0.0331(8) 0.0680(12) 0.0318(8) -0.0063(8) 0.0035(7) -0.0071(8)
C12 0.0330(8) 0.0431(8) 0.0311(8) -0.0052(6) -0.0026(6) -0.0095(7)
C13 0.0534(9) 0.0350(8) 0.0299(8) -0.0067(6) -0.0008(7) -0.0195(7)
C14 0.0486(9) 0.0478(9) 0.0334(8) 0.0003(7) -0.0085(7) -0.0279(8)
C15 0.0346(8) 0.0426(8) 0.0329(8) -0.0033(6) -0.0055(6) -0.0192(7)
C16 0.0658(12) 0.0527(10) 0.0335(9) -0.0042(8) -0.0024(8) -0.0253(9)
C17 0.0799(15) 0.0589(13) 0.0538(12) 0.0146(10) -0.0118(11) -0.0332(11)
C18 0.0613(13) 0.0422(11) 0.1027(19) 0.0016(12) -0.0238(13) -0.0216(10)
C19 0.0535(12) 0.0581(12) 0.0882(17) -0.0305(12) -0.0156(11) -0.0111(10)
C20 0.0436(9) 0.0609(11) 0.0445(10) -0.0162(9) -0.0057(7) -0.0162(8)
C21 0.0458(9) 0.0439(9) 0.0450(9) -0.0143(7) 0.0135(7) -0.0251(7)
C22 0.0744(14) 0.0549(12) 0.0584(12) -0.0030(10) 0.0096(10) -0.0314(10)
C23 0.0914(17) 0.0490(11) 0.0827(17) -0.0065(11) 0.0060(13) -0.0354(12)
C24 0.0632(12) 0.0421(10) 0.0754(14) -0.0207(10) -0.0083(10) -0.0142(9)
C25 0.0491(9) 0.0394(8) 0.0469(9) -0.0193(7) 0.0008(7) -0.0184(7)
C26 0.0994(17) 0.0752(14) 0.0508(12) -0.0314(11) 0.0330(11) -0.0560(13)
C27 0.0437(11) 0.0863(17) 0.104(2) -0.0296(15) 0.0160(12) -0.0201(11)
C28 0.0820(16) 0.0848(16) 0.0657(14) -0.0447(13) 0.0276(12) -0.0409(13)
C29 0.0648(13) 0.0628(13) 0.0800(16) -0.0283(12) -0.0235(11) -0.0126(11)
N1 0.0425(8) 0.0391(7) 0.0439(8) -0.0157(6) 0.0080(6) -0.0206(6)
F1 0.0426(5) 0.0623(7) 0.0699(7) -0.0394(6) 0.0008(5) -0.0162(5)
F2 0.0436(6) 0.0896(9) 0.1132(11) -0.0462(8) -0.0099(7) -0.0254(6)
F3 0.0335(6) 0.0615(7) 0.1211(12) -0.0213(7) 0.0122(6) -0.0119(5)
F4 0.0616(7) 0.0450(6) 0.0767(8) -0.0216(6) 0.0341(6) -0.0122(5)
F5 0.0658(7) 0.0563(6) 0.0551(7) -0.0323(5) 0.0108(5) -0.0199(5)
F6 0.0714(7) 0.0340(5) 0.0464(6) -0.0106(4) 0.0023(5) -0.0225(5)
F7 0.0845(9) 0.0557(7) 0.0699(8) 0.0155(6) -0.0045(6) -0.0445(6)
F8 0.0732(9) 0.1020(11) 0.0561(8) 0.0203(7) 0.0225(6) -0.0329(8)
F9 0.0660(8) 0.0926(10) 0.0444(7) -0.0138(7) 0.0211(6) 0.0017(7)
F10 0.0591(6) 0.0435(6) 0.0442(6) -0.0164(5) 0.0068(5) -0.0078(5)
B1 0.0356(8) 0.0301(8) 0.0284(8) -0.0069(6) 0.0012(6) -0.0138(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 C2 1.388(2) . ?
C1 C6 1.389(2) . ?
C1 B1 1.643(2) . ?
C2 F1 1.3589(18) . ?
C2 C3 1.379(2) . ?
C3 F2 1.345(2) . ?
C3 C4 1.373(3) . ?
C4 F3 1.343(2) . ?
C4 C5 1.362(3) . ?
C5 F4 1.3572(19) . ?
C5 C6 1.381(2) . ?
C6 F5 1.3518(19) . ?
C7 C12 1.381(2) . ?
C7 C8 1.387(2) . ?
C7 B1 1.639(2) . ?
C8 F6 1.3527(19) . ?
C8 C9 1.379(2) . ?
C9 F7 1.349(2) . ?
C9 C10 1.371(3) . ?
C10 F8 1.351(2) . ?
C10 C11 1.369(3) . ?
C11 F9 1.348(2) . ?
C11 C12 1.380(2) . ?
C12 F10 1.3530(19) . ?
C13 C14 1.532(2) . ?
C13 B1 1.634(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.510(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.379(2) . ?
C15 C16 1.395(2) . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C27 1.505(3) . ?
C21 C26 1.518(2) . ?
C21 C22 1.525(3) . ?
C21 N1 1.542(2) . ?
C22 C23 1.531(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.541(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.533(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C29 1.513(3) . ?
C25 C28 1.514(3) . ?
C25 N1 1.528(2) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
N1 H2 0.98(2) . ?
N1 H3 0.89(2) . ?
B1 H1 1.283(18) . ?
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
C2 C1 C6 112.87(14) . . ?
C2 C1 B1 119.53(13) . . ?
C6 C1 B1 127.58(14) . . ?
F1 C2 C3 115.83(14) . . ?
F1 C2 C1 119.07(14) . . ?
C3 C2 C1 125.10(16) . . ?
F2 C3 C4 120.05(16) . . ?
F2 C3 C2 120.94(17) . . ?
C4 C3 C2 119.00(17) . . ?
F3 C4 C5 120.66(17) . . ?
F3 C4 C3 120.57(18) . . ?
C5 C4 C3 118.76(16) . . ?
F4 C5 C4 119.44(16) . . ?
F4 C5 C6 119.97(17) . . ?
C4 C5 C6 120.56(16) . . ?
F5 C6 C5 115.76(15) . . ?
F5 C6 C1 120.54(15) . . ?
C5 C6 C1 123.70(16) . . ?
C12 C7 C8 113.80(14) . . ?
C12 C7 B1 124.21(13) . . ?
C8 C7 B1 121.87(13) . . ?
F6 C8 C9 116.04(14) . . ?
F6 C8 C7 119.71(13) . . ?
C9 C8 C7 124.24(16) . . ?
F7 C9 C10 120.10(16) . . ?
F7 C9 C8 121.03(18) . . ?
C10 C9 C8 118.87(17) . . ?
F8 C10 C11 119.83(19) . . ?
F8 C10 C9 120.44(19) . . ?
C11 C10 C9 119.73(16) . . ?
F9 C11 C10 119.93(17) . . ?
F9 C11 C12 120.74(18) . . ?
C10 C11 C12 119.30(17) . . ?
F10 C12 C11 115.47(15) . . ?
F10 C12 C7 120.53(14) . . ?
C11 C12 C7 124.01(16) . . ?
C14 C13 B1 112.92(13) . . ?
C14 C13 H13A 109.0 . . ?
B1 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
B1 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 114.86(13) . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.5 . . ?
C20 C15 C16 117.22(16) . . ?
C20 C15 C14 122.26(15) . . ?
C16 C15 C14 120.52(16) . . ?
C17 C16 C15 121.33(19) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 121.63(19) . . ?
C19 C20 H20 119.2 . . ?
C15 C20 H20 119.2 . . ?
C27 C21 C26 110.74(17) . . ?
C27 C21 C22 113.55(17) . . ?
C26 C21 C22 110.12(17) . . ?
C27 C21 N1 110.42(17) . . ?
C26 C21 N1 105.24(13) . . ?
C22 C21 N1 106.37(15) . . ?
C21 C22 C23 113.38(18) . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C22 C23 C24 111.06(17) . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C25 C24 C23 112.87(17) . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C29 C25 C28 109.26(18) . . ?
C29 C25 N1 110.79(15) . . ?
C28 C25 N1 105.86(13) . . ?
C29 C25 C24 112.50(16) . . ?
C28 C25 C24 111.24(17) . . ?
N1 C25 C24 106.98(14) . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 C27 H27A 109.5 . . ?
C21 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C21 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C25 N1 C21 120.63(12) . . ?
C25 N1 H2 110.7(12) . . ?
C21 N1 H2 104.9(12) . . ?
C25 N1 H3 104.6(13) . . ?
C21 N1 H3 109.1(13) . . ?
H2 N1 H3 106.1(18) . . ?
C13 B1 C7 109.27(12) . . ?
C13 B1 C1 116.23(13) . . ?
C7 B1 C1 108.43(12) . . ?
C13 B1 H1 108.0(8) . . ?
C7 B1 H1 110.6(8) . . ?
C1 B1 H1 104.3(8) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H2 F1 0.98(2) 2.42(2) 3.367(2) 161.2(16) .
C13 H13B F5 0.97 2.52 2.900(2) 103.4 .
C13 H13B F6 0.97 2.52 3.1406(18) 121.6 .
C20 H20 F9 0.93 2.49 3.291(2) 144.6 2_466
C28 H28A F10 0.96 2.51 3.239(3) 132.6 .
C24 H24A F6 0.97 2.50 3.403(2) 154.5 1_565
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 29.12
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.540
_refine_diff_density_min -0.319
_refine_diff_density_rms 0.053
#===END