#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:37:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180088 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/34/7053401.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_7053401
loop_
_publ_author_name
'Dechambenoit, Pierre'
'Ferlay, Sylvie'
'Kyritsakas, Nathalie'
'Hosseini, Mir Wais'
_publ_section_title
;
 Amidinium based ionic liquids
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1184
_journal_paper_doi               10.1039/b9nj00625g
_journal_volume                  34
_journal_year                    2010
_chemical_formula_moiety         'C11 H15 N2, C F3 O3 S'
_chemical_formula_sum            'C12 H15 F3 N2 O3 S'
_chemical_formula_weight         324.32
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.0219(4)
_cell_length_b                   15.3857(5)
_cell_length_c                   16.9442(6)
_cell_measurement_reflns_used    5535
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.24
_cell_measurement_theta_min      2.40
_cell_volume                     2873.39(17)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            56466
_diffrn_reflns_theta_full        30.10
_diffrn_reflns_theta_max         30.10
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.9657
_exptl_absorpt_correction_T_min  0.9479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0364
_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)+(0.0445P)²+0.6296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                2950
_reflns_number_total             4217
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b9nj00625g.txt
_cod_data_source_block           e830a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7053401
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'
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
S1 S 0.25948(3) 0.15275(2) 0.37012(2) 0.02308(10) Uani 1 1 d .
O3 O 0.15929(9) 0.10981(7) 0.33165(6) 0.0329(3) Uani 1 1 d .
O1 O 0.22821(11) 0.23107(7) 0.41132(7) 0.0391(3) Uani 1 1 d .
O2 O 0.36859(9) 0.15499(7) 0.32430(6) 0.0337(3) Uani 1 1 d .
C5 C 0.48012(12) -0.06010(9) 0.13515(8) 0.0254(3) Uani 1 1 d .
H5 H 0.5114 -0.0361 0.0877 0.031 Uiso 1 1 calc R
C8 C 0.33597(12) 0.06369(9) 0.14223(8) 0.0213(3) Uani 1 1 d .
C6 C 0.38524(12) -0.01856(8) 0.17464(8) 0.0214(3) Uani 1 1 d .
C11 C 0.38174(13) 0.20594(10) 0.08408(9) 0.0307(3) Uani 1 1 d .
H11A H 0.3708 0.2007 0.0263 0.037 Uiso 1 1 calc R
H11B H 0.4462 0.2493 0.0943 0.037 Uiso 1 1 calc R
C7 C 0.34197(13) -0.05298(8) 0.24540(8) 0.0248(3) Uani 1 1 d .
H7 H 0.2787 -0.0243 0.2732 0.030 Uiso 1 1 calc R
C10 C 0.26425(13) 0.23450(10) 0.12234(10) 0.0320(3) Uani 1 1 d .
H10A H 0.2775 0.2453 0.1793 0.038 Uiso 1 1 calc R
H10B H 0.2355 0.2891 0.0978 0.038 Uiso 1 1 calc R
C1 C 0.29624(14) 0.07849(10) 0.45068(9) 0.0297(3) Uani 1 1 d .
C12 C 0.12403(13) 0.01345(10) 0.15156(9) 0.0299(3) Uani 1 1 d .
H12A H 0.1606 -0.0446 0.1525 0.045 Uiso 1 1 calc R
H12B H 0.0627 0.0161 0.1098 0.045 Uiso 1 1 calc R
H12C H 0.0857 0.0254 0.2026 0.045 Uiso 1 1 calc R
C2 C 0.39134(14) -0.12891(9) 0.27502(9) 0.0297(3) Uani 1 1 d .
H2 H 0.3616 -0.1525 0.3231 0.036 Uiso 1 1 calc R
C9 C 0.17074(13) 0.16404(10) 0.11149(10) 0.0337(4) Uani 1 1 d .
H9A H 0.0977 0.1783 0.1430 0.040 Uiso 1 1 calc R
H9B H 0.1466 0.1613 0.0553 0.040 Uiso 1 1 calc R
C3 C 0.48392(14) -0.17073(9) 0.23491(9) 0.0322(3) Uani 1 1 d .
H3 H 0.5170 -0.2232 0.2553 0.039 Uiso 1 1 calc R
C4 C 0.52854(13) -0.13619(10) 0.16502(9) 0.0306(3) Uani 1 1 d .
H4 H 0.5923 -0.1648 0.1377 0.037 Uiso 1 1 calc R
N1 N 0.21817(10) 0.07842(8) 0.13630(7) 0.0236(2) Uani 1 1 d .
N2 N 0.41588(10) 0.12171(8) 0.11773(7) 0.0258(3) Uani 1 1 d .
H2A H 0.4935 0.1091 0.1218 0.031 Uiso 1 1 calc R
F1 F 0.20314(10) 0.07005(7) 0.49994(6) 0.0492(3) Uani 1 1 d .
F3 F 0.39018(10) 0.10774(7) 0.49241(6) 0.0478(3) Uani 1 1 d .
F2 F 0.32499(10) -0.00071(6) 0.42530(6) 0.0464(3) 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
O2 S1 O1 116.45(7)
O2 S1 O3 114.14(6)
O1 S1 O3 114.87(7)
O2 S1 C1 103.54(7)
O1 S1 C1 102.42(7)
O3 S1 C1 102.78(7)
C4 C5 C6 120.09(14)
C4 C5 H5 120.0
C6 C5 H5 120.0
N2 C8 N1 121.01(12)
N2 C8 C6 116.67(11)
N1 C8 C6 122.30(12)
C7 C6 C5 119.61(12)
C7 C6 C8 121.15(12)
C5 C6 C8 119.18(12)
N2 C11 C10 108.05(12)
N2 C11 H11A 110.1
C10 C11 H11A 110.1
N2 C11 H11B 110.1
C10 C11 H11B 110.1
H11A C11 H11B 108.4
C2 C7 C6 119.88(13)
C2 C7 H7 120.1
C6 C7 H7 120.1
C9 C10 C11 108.91(13)
C9 C10 H10A 109.9
C11 C10 H10A 109.9
C9 C10 H10B 109.9
C11 C10 H10B 109.9
H10A C10 H10B 108.3
F1 C1 F2 107.29(12)
F1 C1 F3 107.44(12)
F2 C1 F3 107.21(13)
F1 C1 S1 111.06(11)
F2 C1 S1 112.60(10)
F3 C1 S1 110.98(10)
N1 C12 H12A 109.5
N1 C12 H12B 109.5
H12A C12 H12B 109.5
N1 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C7 C2 C3 120.29(14)
C7 C2 H2 119.9
C3 C2 H2 119.9
N1 C9 C10 111.37(12)
N1 C9 H9A 109.4
C10 C9 H9A 109.4
N1 C9 H9B 109.4
C10 C9 H9B 109.4
H9A C9 H9B 108.0
C2 C3 C4 120.13(14)
C2 C3 H3 119.9
C4 C3 H3 119.9
C5 C4 C3 119.98(14)
C5 C4 H4 120.0
C3 C4 H4 120.0
C8 N1 C12 124.45(12)
C8 N1 C9 121.45(12)
C12 N1 C9 114.09(11)
C8 N2 C11 123.28(11)
C8 N2 H2A 118.4
C11 N2 H2A 118.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4318(10)
S1 O1 1.4347(11)
S1 O3 1.4426(10)
S1 C1 1.8255(15)
C5 C4 1.383(2)
C5 C6 1.3963(19)
C5 H5 0.9500
C8 N2 1.3210(17)
C8 N1 1.3218(17)
C8 C6 1.4825(19)
C6 C7 1.395(2)
C11 N2 1.4651(18)
C11 C10 1.513(2)
C11 H11A 0.9900
C11 H11B 0.9900
C7 C2 1.383(2)
C7 H7 0.9500
C10 C9 1.507(2)
C10 H10A 0.9900
C10 H10B 0.9900
C1 F1 1.3291(17)
C1 F2 1.3305(17)
C1 F3 1.3320(18)
C12 N1 1.4639(18)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C2 C3 1.385(2)
C2 H2 0.9500
C9 N1 1.4783(19)
C9 H9A 0.9900
C9 H9B 0.9900
C3 C4 1.388(2)
C3 H3 0.9500
C4 H4 0.9500
N2 H2A 0.8800
