#------------------------------------------------------------------------------
#$Date: 2016-03-26 04:00:09 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180205 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/99/7109928.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_7109928
loop_
_publ_author_name
'Hikaru Yanai'
'Yoichi Takahashi'
'Haruhiko Fukaya'
'Yasuo Dobashi'
'Takashi Matsumoto'
_publ_section_title
;
 2-(Pyridinium-1-yl)-1,1-bis(triflyl)ethanides: structural behaviour and
 availability as bis(triflyl)ethylating reagents
;
_journal_name_full               Chem.Commun.
_journal_page_first              10091
_journal_paper_doi               10.1039/c3cc46171h
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C12 H13 F6 N O4 S2'
_chemical_formula_sum            'C12 H13 F6 N O4 S2'
_chemical_formula_weight         413.35
_chemical_melting_point          458
_chemical_name_systematic
; 
2-(2-Isopropylpyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide
;
_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_date             '10 January 2013'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.8640(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5646(8)
_cell_length_b                   12.1042(11)
_cell_length_c                   16.0084(14)
_cell_measurement_reflns_used    4335
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.51
_cell_volume                     1624.1(3)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7745
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.9187
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0263
_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)+(0.0341P)²+0.8839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0698
_reflns_number_gt                2610
_reflns_number_total             2865
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc46171h.txt
_cod_data_source_block           CBA09-2e
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7109928
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 0.38738(19) 0.31484(13) 0.80822(10) 0.0124(3) Uani 1 1 d .
C2 C 0.5150(2) 0.26902(14) 0.77869(10) 0.0156(4) Uani 1 1 d .
H2 H 0.5073 0.2603 0.7190 0.019 Uiso 1 1 calc R
C3 C 0.6531(2) 0.23585(14) 0.83430(11) 0.0167(4) Uani 1 1 d .
H3 H 0.7384 0.2038 0.8130 0.020 Uiso 1 1 calc R
C4 C 0.6653(2) 0.24993(14) 0.92145(10) 0.0148(3) Uani 1 1 d .
H4 H 0.7584 0.2273 0.9609 0.018 Uiso 1 1 calc R
C5 C 0.54007(19) 0.29716(13) 0.94900(10) 0.0134(3) Uani 1 1 d .
H5 H 0.5485 0.3091 1.0084 0.016 Uiso 1 1 calc R
C6 C 0.23590(19) 0.35271(13) 0.74843(10) 0.0139(3) Uani 1 1 d .
H6 H 0.1435 0.3323 0.7746 0.017 Uiso 1 1 calc R
C7 C 0.2360(2) 0.47904(14) 0.73820(11) 0.0201(4) Uani 1 1 d .
H7A H 0.2504 0.5139 0.7945 0.030 Uiso 1 1 calc R
H7B H 0.1342 0.5028 0.7029 0.030 Uiso 1 1 calc R
H7C H 0.3235 0.5009 0.7107 0.030 Uiso 1 1 calc R
C8 C 0.2117(2) 0.29772(15) 0.66051(11) 0.0201(4) Uani 1 1 d .
H8A H 0.2957 0.3221 0.6313 0.030 Uiso 1 1 calc R
H8B H 0.1072 0.3186 0.6265 0.030 Uiso 1 1 calc R
H8C H 0.2167 0.2173 0.6674 0.030 Uiso 1 1 calc R
C9 C 0.27710(19) 0.38090(13) 0.93409(10) 0.0124(3) Uani 1 1 d .
H9A H 0.3094 0.4578 0.9501 0.015 Uiso 1 1 calc R
H9B H 0.1762 0.3839 0.8909 0.015 Uiso 1 1 calc R
C10 C 0.24771(19) 0.32154(13) 1.01131(10) 0.0114(3) Uani 1 1 d .
C11 C 0.1531(2) 0.47292(14) 1.12761(11) 0.0179(4) Uani 1 1 d .
C12 C 0.2562(2) 0.08577(14) 1.01610(11) 0.0178(4) Uani 1 1 d .
F1 F 0.01634(12) 0.42084(8) 1.12857(7) 0.0248(2) Uani 1 1 d .
F2 F 0.19987(14) 0.52406(9) 1.20220(7) 0.0309(3) Uani 1 1 d .
F3 F 0.12344(12) 0.54953(8) 1.06626(6) 0.0224(2) Uani 1 1 d .
F4 F 0.32850(13) 0.07613(9) 1.09726(7) 0.0291(3) Uani 1 1 d .
F5 F 0.16909(13) -0.00390(8) 0.99335(7) 0.0294(3) Uani 1 1 d .
F6 F 0.36832(12) 0.09025(8) 0.96928(7) 0.0277(3) Uani 1 1 d .
N1 N 0.40443(16) 0.32745(11) 0.89437(8) 0.0107(3) Uani 1 1 d .
O1 O 0.44132(14) 0.45074(9) 1.10609(7) 0.0168(3) Uani 1 1 d .
O2 O 0.32037(14) 0.29778(10) 1.17607(7) 0.0173(3) Uani 1 1 d .
O3 O 0.03053(14) 0.19921(10) 1.06004(8) 0.0182(3) Uani 1 1 d .
O4 O 0.05599(14) 0.20115(10) 0.90787(7) 0.0201(3) Uani 1 1 d .
S1 S 0.31004(5) 0.37688(3) 1.10870(2) 0.01163(11) Uani 1 1 d .
S2 S 0.12669(5) 0.20953(3) 0.99715(3) 0.01262(11) 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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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
N1 C1 C2 117.33(14)
N1 C1 C6 120.26(14)
C2 C1 C6 122.40(14)
C3 C2 C1 121.55(15)
C3 C2 H2 119.2
C1 C2 H2 119.2
C2 C3 C4 119.24(15)
C2 C3 H3 120.4
C4 C3 H3 120.4
C5 C4 C3 118.29(15)
C5 C4 H4 120.9
C3 C4 H4 120.9
N1 C5 C4 122.10(15)
N1 C5 H5 118.9
C4 C5 H5 118.9
C1 C6 C8 112.66(14)
C1 C6 C7 110.41(14)
C8 C6 C7 109.70(13)
C1 C6 H6 108.0
C8 C6 H6 108.0
C7 C6 H6 108.0
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 N1 113.55(13)
C10 C9 H9A 108.9
N1 C9 H9A 108.9
C10 C9 H9B 108.9
N1 C9 H9B 108.9
H9A C9 H9B 107.7
C9 C10 S1 120.02(12)
C9 C10 S2 118.46(11)
S1 C10 S2 120.83(9)
F2 C11 F1 108.21(13)
F2 C11 F3 108.25(14)
F1 C11 F3 107.56(14)
F2 C11 S1 110.15(12)
F1 C11 S1 112.01(11)
F3 C11 S1 110.54(11)
F5 C12 F4 108.71(14)
F5 C12 F6 107.95(14)
F4 C12 F6 108.00(14)
F5 C12 S2 109.47(12)
F4 C12 S2 112.06(12)
F6 C12 S2 110.55(12)
C5 N1 C1 121.46(13)
C5 N1 C9 116.15(12)
C1 N1 C9 122.32(13)
O2 S1 O1 120.54(7)
O2 S1 C10 113.03(8)
O1 S1 C10 108.71(7)
O2 S1 C11 103.40(7)
O1 S1 C11 102.25(7)
C10 S1 C11 107.44(8)
O3 S2 O4 120.52(7)
O3 S2 C10 113.62(7)
O4 S2 C10 108.12(8)
O3 S2 C12 103.07(8)
O4 S2 C12 102.81(8)
C10 S2 C12 107.24(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.365(2)
C1 C2 1.392(2)
C1 C6 1.516(2)
C2 C3 1.385(2)
C2 H2 0.9500
C3 C4 1.388(2)
C3 H3 0.9500
C4 C5 1.366(2)
C4 H4 0.9500
C5 N1 1.353(2)
C5 H5 0.9500
C6 C8 1.532(2)
C6 C7 1.538(2)
C6 H6 1.0000
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.495(2)
C9 N1 1.5156(19)
C9 H9A 0.9900
C9 H9B 0.9900
C10 S1 1.6799(15)
C10 S2 1.6933(16)
C11 F2 1.3314(19)
C11 F1 1.333(2)
C11 F3 1.336(2)
C11 S1 1.8484(17)
C12 F5 1.325(2)
C12 F4 1.325(2)
C12 F6 1.335(2)
C12 S2 1.8515(18)
O1 S1 1.4438(12)
O2 S1 1.4313(12)
O3 S2 1.4313(12)
O4 S2 1.4365(12)
