#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/28/2222812.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222812
loop_
_publ_author_name
'Chen, Gang'
'Xu, Wei'
'Yang, Zhen'
'Fan, Zheng'
_publ_section_title
;
 Pyridinium 4-(trifluoromethyl)benzenesulfonate
;
_journal_coeditor_code           NG2593
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1797
_journal_paper_doi               10.1107/S1600536809025835
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C5 H6 N +, C7 H4 F3 O3 S -'
_chemical_formula_moiety         'C5 H6 N +, C7 H4 F3 O3 S -'
_chemical_formula_sum            'C12 H10 F3 N O3 S'
_chemical_formula_weight         305.27
_chemical_name_systematic
;
Pyridinium 4-(trifluoromethyl)benzenesulfonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 90.8220(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7905(5)
_cell_length_b                   9.0294(7)
_cell_length_c                   24.988(2)
_cell_measurement_reflns_used    2733
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.96
_cell_measurement_theta_min      2.38
_cell_volume                     1306.36(18)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6394
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.9310
_exptl_absorpt_correction_T_min  0.8709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.534
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2291
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0877
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1117P)²+3.3401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2319
_refine_ls_wR_factor_ref         0.2418
_reflns_number_gt                1880
_reflns_number_total             2291
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2593.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1306.35(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222812
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 1.1078(2) 0.88952(12) 0.32068(5) 0.0451(4) Uani d . 1 A .
O O1 1.3546(6) 0.8891(4) 0.32268(15) 0.0603(10) Uani d . 1 . .
O O2 1.0094(6) 1.0326(4) 0.30758(14) 0.0595(10) Uani d . 1 . .
O O3 1.0162(7) 0.7709(4) 0.28780(15) 0.0629(10) Uani d . 1 . .
C C1 0.7591(12) 0.7361(7) 0.5413(3) 0.086(2) Uani d D 1 . .
C C2 0.8504(10) 0.7742(7) 0.4880(2) 0.0598(14) Uani d . 1 A .
C C3 0.7200(11) 0.8601(8) 0.4550(3) 0.0756(18) Uani d . 1 . .
H H3 0.5780 0.8954 0.4664 0.091 Uiso calc R 1 A .
C C4 0.7974(10) 0.8958(7) 0.4043(2) 0.0679(16) Uani d . 1 A .
H H4 0.7050 0.9535 0.3818 0.082 Uiso calc R 1 . .
C C5 1.0090(8) 0.8472(5) 0.38668(19) 0.0444(11) Uani d . 1 . .
C C6 1.1354(10) 0.7576(8) 0.4195(2) 0.0730(18) Uani d . 1 A .
H H6 1.2761 0.7203 0.4080 0.088 Uiso calc R 1 . .
C C7 1.0565(12) 0.7217(8) 0.4696(3) 0.081(2) Uani d . 1 . .
H H7 1.1455 0.6602 0.4915 0.098 Uiso calc R 1 A .
F F1' 0.9025(16) 0.6547(13) 0.5717(3) 0.1146(16) Uani d PD 0.584(9) A 2
F F2' 0.5792(17) 0.6419(11) 0.5388(4) 0.1146(16) Uani d PD 0.584(9) A 2
F F3' 0.700(2) 0.8521(9) 0.5715(3) 0.1146(16) Uani d PD 0.584(9) A 2
F F1 0.921(2) 0.7454(19) 0.5793(4) 0.1146(16) Uani d PD 0.416(9) A 1
F F2 0.672(3) 0.5995(12) 0.5458(5) 0.1146(16) Uani d PD 0.416(9) A 1
F F3 0.577(2) 0.8166(15) 0.5579(5) 0.1146(16) Uani d PD 0.416(9) A 1
N N1 0.6745(8) 0.8321(6) 0.21165(18) 0.0650(13) Uani d . 1 . .
H H1 0.7923 0.7923 0.2273 0.078 Uiso calc R 1 . .
C C8 0.6591(10) 0.9796(7) 0.2096(2) 0.0610(15) Uani d . 1 . .
H H8 0.7754 1.0376 0.2248 0.073 Uiso calc R 1 . .
C C9 0.4777(10) 1.0437(6) 0.1859(2) 0.0613(14) Uani d . 1 . .
H H9 0.4666 1.1464 0.1840 0.074 Uiso calc R 1 . .
C C10 0.3107(10) 0.9570(7) 0.1649(2) 0.0628(14) Uani d . 1 . .
H H10 0.1821 1.0001 0.1485 0.075 Uiso calc R 1 . .
C C11 0.3284(10) 0.8056(6) 0.1673(2) 0.0619(14) Uani d . 1 . .
H H11 0.2120 0.7459 0.1531 0.074 Uiso calc R 1 . .
C C12 0.5144(10) 0.7456(6) 0.1903(2) 0.0581(14) Uani d . 1 . .
H H12 0.5314 0.6432 0.1914 0.070 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O3 . . 112.1(2) ?
O1 S1 O2 . . 113.6(2) ?
O3 S1 O2 . . 113.1(2) ?
O1 S1 C5 . . 107.4(2) ?
O3 S1 C5 . . 104.2(2) ?
O2 S1 C5 . . 105.6(2) ?
F1 C1 F2 . . 105.1(9) ?
F1' C1 F3' . . 105.7(7) ?
F1 C1 F2' . . 127.7(9) ?
F1' C1 F2' . . 98.8(7) ?
F3' C1 F2' . . 108.6(8) ?
F1 C1 F3 . . 107.1(9) ?
F2 C1 F3 . . 100.0(10) ?
F1 C1 C2 . . 111.7(8) ?
F2 C1 C2 . . 115.5(8) ?
F1' C1 C2 . . 114.3(6) ?
F3' C1 C2 . . 115.0(6) ?
F2' C1 C2 . . 113.1(6) ?
F3 C1 C2 . . 116.2(7) ?
C3 C2 C7 . . 118.3(5) ?
C3 C2 C1 . . 118.5(5) ?
C7 C2 C1 . . 123.1(5) ?
C2 C3 C4 . . 120.3(5) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C5 C4 C3 . . 121.2(5) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C6 C5 C4 . . 118.0(5) ?
C6 C5 S1 . . 120.3(4) ?
C4 C5 S1 . . 121.5(4) ?
C5 C6 C7 . . 120.4(5) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C2 C7 C6 . . 121.7(5) ?
C2 C7 H7 . . 119.1 ?
C6 C7 H7 . . 119.1 ?
C12 N1 C8 . . 122.0(5) ?
C12 N1 H1 . . 119.0 ?
C8 N1 H1 . . 119.0 ?
C9 C8 N1 . . 120.2(5) ?
C9 C8 H8 . . 119.9 ?
N1 C8 H8 . . 119.9 ?
C8 C9 C10 . . 118.6(5) ?
C8 C9 H9 . . 120.7 ?
C10 C9 H9 . . 120.7 ?
C9 C10 C11 . . 120.6(6) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C12 C11 C10 . . 119.0(5) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
N1 C12 C11 . . 119.6(5) ?
N1 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.429(4) ?
S1 O3 . 1.446(4) ?
S1 O2 . 1.447(3) ?
S1 C5 . 1.795(5) ?
C1 F1 . 1.330(8) ?
C1 F2 . 1.337(8) ?
C1 F1' . 1.338(7) ?
C1 F3' . 1.339(7) ?
C1 F2' . 1.345(7) ?
C1 F3 . 1.353(8) ?
C1 C2 . 1.479(9) ?
C2 C3 . 1.354(8) ?
C2 C7 . 1.370(9) ?
C3 C4 . 1.388(8) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.379(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.358(7) ?
C6 C7 . 1.378(9) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
N1 C12 . 1.319(7) ?
N1 C8 . 1.336(8) ?
N1 H1 . 0.8600 ?
C8 C9 . 1.331(8) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.346(8) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.372(8) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.329(8) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O3 . 0.86 1.99 2.781(6) 153 yes
C4 H4 O1 1_455 0.93 2.56 3.255(7) 132 no
C8 H8 O2 . 0.93 2.47 3.192(7) 136 no
C8 H8 O3 2_755 0.93 2.45 3.233(8) 142 no
C9 H9 O1 2_755 0.93 2.43 3.274(6) 151 no
C11 H11 O2 2_645 0.93 2.52 3.214(8) 132 no
C12 H12 O1 2_745 0.93 2.42 3.324(7) 166 no
