#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/96/7019696.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_7019696
loop_
_publ_author_name
'Palomas, David'
'Holle, Sigrid'
'Inés, Blanca'
'Bruns, Hans'
'Goddard, Richard'
'Alcarazo, Manuel'
_publ_section_title
;
 Synthesis and reactivity of electron poor allenes: formation of
 completely organic frustrated Lewis pairs.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9073
_journal_page_last               9082
_journal_paper_doi               10.1039/c2dt30195d
_journal_volume                  41
_journal_year                    2012
_chemical_compound_source        pentane
_chemical_formula_moiety         'C14 H12 F12 N2'
_chemical_formula_sum            'C14 H12 F12 N2'
_chemical_formula_weight         436.26
_chemical_name_systematic
;
2-(1,2,3,4-(tetramethyl)imidazol-3-ium-2-yl)-
1,1,3,3-tetra(trifluoromethyl)-propan-2-ide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_block_code                BHC-BB-024-02
_audit_creation_date             2012-01-18
_cell_angle_alpha                90.00
_cell_angle_beta                 111.802(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.0303(8)
_cell_length_b                   8.0790(8)
_cell_length_c                   15.6424(12)
_cell_measurement_reflns_used    36858
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.0996
_cell_measurement_theta_min      2.6488
_cell_volume                     1646.3(2)
_computing_cell_refinement       'DENZO (Bruker AXS, 2006)'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'DENZO (Bruker AXS, 2006)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33671
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         33.23
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.97398
_exptl_absorpt_correction_T_min  0.95608
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         6308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0927P)²+1.0104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1772
_reflns_number_gt                4676
_reflns_number_total             6308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt30195d.txt
_cod_data_source_block           6946_17
_cod_original_sg_symbol_Hall     '-p 2yn'
_cod_original_sg_symbol_H-M      'p 21/n'
_cod_database_code               7019696
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
C1 C 0.08563(10) 0.45608(17) 0.33228(9) 0.0172(2) Uani 1 1 d .
C2 C 0.20435(11) 0.33197(18) 0.45171(10) 0.0195(3) Uani 1 1 d .
C3 C 0.12574(12) 0.22288(18) 0.41371(10) 0.0210(3) Uani 1 1 d .
C4 C 0.23908(12) 0.6280(2) 0.41896(12) 0.0255(3) Uani 1 1 d .
H4C H 0.2427 0.6726 0.4783 0.038 Uiso 1 1 calc R
H4A H 0.2066 0.7094 0.3704 0.038 Uiso 1 1 calc R
H4B H 0.3086 0.6040 0.4215 0.038 Uiso 1 1 calc R
C5 C 0.30023(13) 0.3171(2) 0.53490(11) 0.0267(3) Uani 1 1 d .
H5A H 0.3592 0.3486 0.5192 0.040 Uiso 1 1 calc R
H5B H 0.3084 0.2025 0.5569 0.040 Uiso 1 1 calc R
H5C H 0.2961 0.3906 0.5833 0.040 Uiso 1 1 calc R
C6 C 0.11223(15) 0.0477(2) 0.43762(13) 0.0307(3) Uani 1 1 d .
H6A H 0.1056 -0.0242 0.3852 0.046 Uiso 1 1 calc R
H6B H 0.0502 0.0388 0.4521 0.046 Uiso 1 1 calc R
H6C H 0.1720 0.0135 0.4912 0.046 Uiso 1 1 calc R
C7 C -0.04243(13) 0.2276(2) 0.27716(13) 0.0301(3) Uani 1 1 d .
H7A H -0.0256 0.1411 0.2412 0.045 Uiso 1 1 calc R
H7B H -0.0850 0.3123 0.2355 0.045 Uiso 1 1 calc R
H7C H -0.0801 0.1788 0.3126 0.045 Uiso 1 1 calc R
C8 C 0.02728(10) 0.58005(17) 0.26112(9) 0.0178(2) Uani 1 1 d .
C9 C -0.06082(11) 0.64432(18) 0.27239(10) 0.0201(3) Uani 1 1 d .
C10 C -0.07018(13) 0.6488(2) 0.36370(12) 0.0285(3) Uani 1 1 d .
C11 C -0.15553(13) 0.6876(3) 0.19437(13) 0.0314(4) Uani 1 1 d .
C12 C 0.06375(11) 0.61379(18) 0.19156(10) 0.0201(3) Uani 1 1 d .
C13 C 0.04363(14) 0.7703(2) 0.13792(13) 0.0292(3) Uani 1 1 d .
C14 C 0.13759(14) 0.5022(2) 0.17146(11) 0.0292(3) Uani 1 1 d .
F1 F 0.01898(9) 0.66601(14) 0.43438(7) 0.0326(2) Uani 1 1 d .
F2 F -0.11257(11) 0.50867(18) 0.38589(9) 0.0447(3) Uani 1 1 d .
F3 F -0.13230(11) 0.77018(18) 0.36997(9) 0.0485(4) Uani 1 1 d .
F4 F -0.23874(9) 0.6211(2) 0.20322(11) 0.0561(4) Uani 1 1 d .
F5 F -0.18027(12) 0.85517(19) 0.18823(12) 0.0541(4) Uani 1 1 d .
F6 F -0.15618(9) 0.64462(16) 0.11241(8) 0.0368(3) Uani 1 1 d .
F7 F 0.00029(11) 0.88776(14) 0.17127(9) 0.0394(3) Uani 1 1 d .
F8 F -0.01584(10) 0.75572(17) 0.04607(8) 0.0408(3) Uani 1 1 d .
F9 F 0.13170(10) 0.83433(16) 0.13606(9) 0.0385(3) Uani 1 1 d .
F10 F 0.13092(10) 0.51351(16) 0.08378(8) 0.0392(3) Uani 1 1 d .
F11 F 0.23837(9) 0.5381(2) 0.22118(9) 0.0505(4) Uani 1 1 d .
F12 F 0.12654(12) 0.34313(15) 0.18838(10) 0.0450(3) Uani 1 1 d .
N1 N 0.17840(9) 0.47545(15) 0.39894(8) 0.0179(2) Uani 1 1 d .
N2 N 0.05233(9) 0.30352(15) 0.34023(9) 0.0193(2) 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 0.0000 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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 1.00 0.0700
1.00 0.00 -1.00 0.0700
-1.00 0.00 -3.00 0.1300
1.00 0.00 1.00 0.1400
-1.00 3.00 -1.00 0.0700
1.00 -1.00 1.00 0.1400
1.00 1.00 1.00 0.1500
-1.00 -3.00 -1.00 0.1100
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N1 107.84(12) y
N2 C1 C8 124.88(12) y
N1 C1 C8 127.28(12) y
C3 C2 N1 106.79(12) y
C3 C2 C5 130.61(14) y
N1 C2 C5 122.56(14) y
C2 C3 N2 106.79(13) y
C2 C3 C6 131.34(15) y
N2 C3 C6 121.86(14) y
N1 C4 H4C 109.5 n
N1 C4 H4A 109.5 n
H4C C4 H4A 109.5 n
N1 C4 H4B 109.5 n
H4C C4 H4B 109.5 n
H4A C4 H4B 109.5 n
C2 C5 H5A 109.5 n
C2 C5 H5B 109.5 n
H5A C5 H5B 109.5 n
C2 C5 H5C 109.5 n
H5A C5 H5C 109.5 n
H5B C5 H5C 109.5 n
C3 C6 H6A 109.5 n
C3 C6 H6B 109.5 n
H6A C6 H6B 109.5 n
C3 C6 H6C 109.5 n
H6A C6 H6C 109.5 n
H6B C6 H6C 109.5 n
N2 C7 H7A 109.5 n
N2 C7 H7B 109.5 n
H7A C7 H7B 109.5 n
N2 C7 H7C 109.5 n
H7A C7 H7C 109.5 n
H7B C7 H7C 109.5 n
C12 C8 C9 128.29(13) y
C12 C8 C1 117.07(12) y
C9 C8 C1 114.61(12) y
C8 C9 C11 123.11(14) y
C8 C9 C10 121.64(13) y
C11 C9 C10 114.61(13) y
F1 C10 F3 107.37(15) y
F1 C10 F2 103.63(14) y
F3 C10 F2 103.24(14) y
F1 C10 C9 114.19(14) y
F3 C10 C9 112.42(14) y
F2 C10 C9 114.97(15) y
F6 C11 F4 107.57(17) y
F6 C11 F5 106.05(15) y
F4 C11 F5 101.13(15) y
F6 C11 C9 114.76(14) y
F4 C11 C9 111.82(14) y
F5 C11 C9 114.40(17) y
C8 C12 C13 124.12(13) y
C8 C12 C14 122.16(13) y
C13 C12 C14 113.35(13) y
F7 C13 F9 106.83(15) y
F7 C13 F8 106.39(15) y
F9 C13 F8 102.46(14) y
F7 C13 C12 113.79(14) y
F9 C13 C12 110.80(14) y
F8 C13 C12 115.63(15) y
F12 C14 F10 107.42(15) y
F12 C14 F11 105.28(15) y
F10 C14 F11 103.38(15) y
F12 C14 C12 113.56(15) y
F10 C14 C12 112.56(14) y
F11 C14 C12 113.82(15) y
C1 N1 C2 109.20(12) y
C1 N1 C4 125.74(13) y
C2 N1 C4 124.84(12) y
C1 N2 C3 109.36(12) y
C1 N2 C7 125.68(13) y
C3 N2 C7 124.78(13) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 1.3402(18) y
C1 N1 1.3409(17) y
C1 C8 1.4951(19) y
C2 C3 1.364(2) y
C2 N1 1.3909(19) y
C2 C5 1.489(2) y
C3 N2 1.3882(19) y
C3 C6 1.494(2) y
C4 N1 1.4640(19) y
C4 H4C 0.9800 n
C4 H4A 0.9800 n
C4 H4B 0.9800 n
C5 H5A 0.9800 n
C5 H5B 0.9800 n
C5 H5C 0.9800 n
C6 H6A 0.9800 n
C6 H6B 0.9800 n
C6 H6C 0.9800 n
C7 N2 1.464(2) y
C7 H7A 0.9800 n
C7 H7B 0.9800 n
C7 H7C 0.9800 n
C8 C12 1.391(2) y
C8 C9 1.4108(19) y
C9 C11 1.474(2) y
C9 C10 1.483(2) y
C10 F1 1.334(2) y
C10 F3 1.3393(19) y
C10 F2 1.382(2) y
C11 F6 1.325(2) y
C11 F4 1.338(2) y
C11 F5 1.392(2) y
C12 C13 1.485(2) y
C12 C14 1.492(2) y
C13 F7 1.334(2) y
C13 F9 1.350(2) y
C13 F8 1.372(2) y
C14 F12 1.333(2) y
C14 F10 1.3428(19) y
C14 F11 1.368(2) y
