#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:07:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180412 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/81/7208152.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_7208152
loop_
_publ_author_name
'Sánchez, Ignacio'
'Campo, José Antonio'
'Heras, José Vicente'
'Rosario Torres, M.'
'Cano, Mercedes'
_publ_section_title
;
 Pyrazolium salts as a new class of ionic liquid crystals
;
_journal_issue                   26
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              13239
_journal_paper_doi               10.1039/c2jm31939j
_journal_volume                  22
_journal_year                    2012
_chemical_formula_sum            'C11 H11 F3 N2 O4 S'
_chemical_formula_weight         324.28
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.910(10)
_cell_angle_beta                 83.266(12)
_cell_angle_gamma                89.319(12)
_cell_formula_units_Z            2
_cell_length_a                   6.344(4)
_cell_length_b                   10.275(6)
_cell_length_c                   11.844(7)
_cell_measurement_reflns_used    830
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.30
_cell_measurement_theta_min      3.21
_cell_volume                     724.3(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0959
_diffrn_reflns_av_sigmaI/netI    0.1272
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5594
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1514
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1681
_reflns_number_gt                1029
_reflns_number_total             2489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2jm31939j.txt
_cod_data_source_block           C11H11F3N2O4S
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        724.3(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7208152
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O2 O 0.4991(5) 0.4967(4) 0.8560(4) 0.1043(13) Uani 1 1 d .
N1 N 0.3738(6) 0.7333(4) 0.9095(3) 0.0637(11) Uani 1 1 d .
H1 H 0.4378 0.6434 0.8979 0.116(18) Uiso 1 1 d R
N2 N 0.1897(6) 0.7237(4) 0.9819(4) 0.0689(12) Uani 1 1 d .
H2 H 0.1254 0.6286 1.0361 0.17(3) Uiso 1 1 d R
C3 C 0.1511(7) 0.8460(5) 0.9940(5) 0.0745(15) Uani 1 1 d .
H3 H 0.0339 0.8670 1.0393 0.089 Uiso 1 1 calc R
C4 C 0.3133(7) 0.9362(5) 0.9284(4) 0.0690(15) Uani 1 1 d .
H4 H 0.3260 1.0288 0.9210 0.083 Uiso 1 1 calc R
C5 C 0.4546(7) 0.8631(5) 0.8754(4) 0.0560(12) Uani 1 1 d .
C6 C 0.6582(7) 0.9041(5) 0.8014(4) 0.0595(13) Uani 1 1 d .
C7 C 0.7244(7) 1.0413(5) 0.7557(4) 0.0756(15) Uani 1 1 d .
H7 H 0.6370 1.1077 0.7723 0.091 Uiso 1 1 calc R
C8 C 0.9189(9) 1.0819(6) 0.6853(5) 0.0872(17) Uani 1 1 d .
H8 H 0.9619 1.1743 0.6557 0.105 Uiso 1 1 calc R
C9 C 1.0467(8) 0.9833(8) 0.6604(5) 0.0846(18) Uani 1 1 d .
C10 C 0.9859(8) 0.8461(7) 0.7051(5) 0.0932(19) Uani 1 1 d .
H10 H 1.0744 0.7804 0.6882 0.112 Uiso 1 1 calc R
C11 C 0.7955(8) 0.8069(5) 0.7743(5) 0.0790(16) Uani 1 1 d .
H11 H 0.7554 0.7140 0.8043 0.095 Uiso 1 1 calc R
C12 C 1.3227(10) 1.1423(8) 0.5475(6) 0.136(3) Uani 1 1 d .
H12A H 1.2262 1.1983 0.4965 0.204 Uiso 1 1 calc R
H12B H 1.4592 1.1460 0.5018 0.204 Uiso 1 1 calc R
H12C H 1.3361 1.1760 0.6130 0.204 Uiso 1 1 calc R
C13 C 0.3242(16) 0.4784(8) 0.6781(7) 0.126(3) Uani 1 1 d .
F1 F 0.1628(13) 0.4332(6) 0.6466(5) 0.222(3) Uani 1 1 d .
F2 F 0.5026(9) 0.4317(5) 0.6336(4) 0.199(2) Uani 1 1 d .
F3 F 0.3390(9) 0.6140(5) 0.6304(4) 0.187(2) Uani 1 1 d .
O1 O 1.2457(6) 1.0076(5) 0.5925(4) 0.1165(15) Uani 1 1 d .
O3 O 0.1214(5) 0.4766(3) 0.8804(3) 0.0897(12) Uani 1 1 d .
O4 O 0.3288(5) 0.2801(3) 0.8738(3) 0.0913(12) Uani 1 1 d .
S1 S 0.3167(2) 0.42614(13) 0.83967(12) 0.0675(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 0.0000 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
N2 N1 C5 109.3(4)
N2 N1 H1 118.9
C5 N1 H1 131.3
C3 N2 N1 108.6(4)
C3 N2 H2 128.0
N1 N2 H2 120.7
N2 C3 C4 108.5(4)
N2 C3 H3 125.8
C4 C3 H3 125.8
C3 C4 C5 107.0(4)
C3 C4 H4 126.5
C5 C4 H4 126.5
N1 C5 C4 106.6(4)
N1 C5 C6 122.3(4)
C4 C5 C6 131.1(4)
C7 C6 C11 117.5(4)
C7 C6 C5 120.8(4)
C11 C6 C5 121.8(4)
C6 C7 C8 121.4(5)
C6 C7 H7 119.3
C8 C7 H7 119.3
C9 C8 C7 119.0(5)
C9 C8 H8 120.5
C7 C8 H8 120.5
C10 C9 O1 113.3(6)
C10 C9 C8 121.0(5)
O1 C9 C8 125.7(6)
C9 C10 C11 119.8(5)
C9 C10 H10 120.1
C11 C10 H10 120.1
C10 C11 C6 121.4(5)
C10 C11 H11 119.3
C6 C11 H11 119.3
O1 C12 H12A 109.5
O1 C12 H12B 109.5
H12A C12 H12B 109.5
O1 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
F1 C13 F3 109.9(8)
F1 C13 F2 110.1(8)
F3 C13 F2 105.7(7)
F1 C13 S1 112.0(6)
F3 C13 S1 110.6(6)
F2 C13 S1 108.3(6)
C12 O1 C9 117.2(5)
O4 S1 O2 115.6(2)
O4 S1 O3 115.5(2)
O2 S1 O3 112.4(2)
O4 S1 C13 103.1(3)
O2 S1 C13 103.3(4)
O3 S1 C13 105.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 S1 1.437(3)
N1 N2 1.350(5)
N1 C5 1.349(5)
N1 H1 1.0477
N2 C3 1.327(5)
N2 H2 1.0352
C3 C4 1.374(6)
C3 H3 0.9300
C4 C5 1.387(6)
C4 H4 0.9300
C5 C6 1.456(6)
C6 C7 1.385(6)
C6 C11 1.408(6)
C7 C8 1.391(6)
C7 H7 0.9300
C8 C9 1.375(7)
C8 H8 0.9300
C9 C10 1.376(7)
C9 O1 1.393(6)
C10 C11 1.363(6)
C10 H10 0.9300
C11 H11 0.9300
C12 O1 1.382(6)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 F1 1.272(9)
C13 F3 1.320(7)
C13 F2 1.342(8)
C13 S1 1.805(8)
O3 S1 1.430(3)
O4 S1 1.424(3)
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 H1 O2 1.05 1.76 2.791(5) 166.6 .
N2 H2 O3 1.04 1.89 2.817(5) 147.2 2_567
C4 H4 O4 0.93 2.46 3.378(6) 171.0 1_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 N1 N2 C3 0.3(5)
N1 N2 C3 C4 -0.1(6)
N2 C3 C4 C5 -0.2(6)
N2 N1 C5 C4 -0.4(5)
N2 N1 C5 C6 177.0(4)
C3 C4 C5 N1 0.4(5)
C3 C4 C5 C6 -176.8(5)
N1 C5 C6 C7 171.9(4)
C4 C5 C6 C7 -11.3(8)
N1 C5 C6 C11 -8.5(7)
C4 C5 C6 C11 168.2(5)
C11 C6 C7 C8 0.1(7)
C5 C6 C7 C8 179.7(5)
C6 C7 C8 C9 0.5(8)
C7 C8 C9 C10 -0.9(9)
C7 C8 C9 O1 -179.4(5)
O1 C9 C10 C11 179.3(5)
C8 C9 C10 C11 0.6(9)
C9 C10 C11 C6 0.0(9)
C7 C6 C11 C10 -0.4(8)
C5 C6 C11 C10 -179.9(5)
C10 C9 O1 C12 -177.8(6)
C8 C9 O1 C12 0.9(8)
F1 C13 S1 O4 64.3(7)
F3 C13 S1 O4 -172.8(6)
F2 C13 S1 O4 -57.4(7)
F1 C13 S1 O2 -175.1(6)
F3 C13 S1 O2 -52.1(7)
F2 C13 S1 O2 63.3(7)
F1 C13 S1 O3 -57.1(7)
F3 C13 S1 O3 65.9(7)
F2 C13 S1 O3 -178.7(6)
