#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/42/7214290.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_7214290
loop_
_publ_author_name
'Xuan, Xiao-Peng'
'Chang, Liang-Liang'
'Zhang, Heng'
'Wang, Na'
'Zhao, Yang'
_publ_section_title
;
 Hydrogen bonds in the crystal structure of hydrophobic and hydrophilic
 COOH-functionalized imidazolium ionic liquids
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              3040
_journal_paper_doi               10.1039/c3ce42492h
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C9 H11 F6 N3 O6 S2'
_chemical_formula_weight         435.35
_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                 127.51(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.898(5)
_cell_length_b                   16.937(8)
_cell_length_c                   12.581(5)
_cell_measurement_reflns_used    3170
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.34
_cell_measurement_theta_min      2.43
_cell_volume                     1673.0(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9096
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.9365
_exptl_absorpt_correction_T_min  0.9253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0447
_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)+(0.0445P)²+1.4393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1143
_reflns_number_gt                2571
_reflns_number_total             3280
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce42492h2.cif
_cod_data_source_block           a2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1673.0(13)
_cod_original_sg_symbol_H-M      'P2(1)/c '
_cod_database_code               7214290
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_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
O1 O -0.3389(2) -0.03933(11) 0.51157(19) 0.0560(5) Uani 1 1 d .
O2 O -0.5328(2) 0.04336(12) 0.35362(19) 0.0597(5) Uani 1 1 d .
H2 H -0.5723 0.0395 0.3949 0.089 Uiso 1 1 d R
N1 N -0.3082(3) -0.26330(13) 0.3779(2) 0.0483(5) Uani 1 1 d .
N2 N -0.2590(2) -0.14317(12) 0.35431(19) 0.0418(5) Uani 1 1 d .
C1 C -0.3036(5) -0.33743(18) 0.4394(3) 0.0710(9) Uani 1 1 d .
H1A H -0.2110 -0.3362 0.5336 0.107 Uiso 1 1 calc R
H1B H -0.2876 -0.3806 0.3985 0.107 Uiso 1 1 calc R
H1C H -0.4090 -0.3443 0.4265 0.107 Uiso 1 1 calc R
C2 C -0.4130(4) -0.24671(19) 0.2437(3) 0.0591(8) Uani 1 1 d .
H2A H -0.4913 -0.2810 0.1754 0.071 Uiso 1 1 calc R
C3 C -0.3824(4) -0.17260(19) 0.2285(3) 0.0567(7) Uani 1 1 d .
H3A H -0.4348 -0.1457 0.1478 0.068 Uiso 1 1 calc R
C4 C -0.2172(3) -0.19924(15) 0.4419(2) 0.0446(6) Uani 1 1 d .
H4A H -0.1364 -0.1946 0.5343 0.054 Uiso 1 1 calc R
C5 C -0.1870(3) -0.06353(16) 0.3854(3) 0.0498(6) Uani 1 1 d .
H5A H -0.1331 -0.0553 0.3427 0.060 Uiso 1 1 calc R
H5B H -0.1000 -0.0588 0.4814 0.060 Uiso 1 1 calc R
C6 C -0.3203(4) -0.00037(16) 0.3388(3) 0.0509(6) Uani 1 1 d .
H6A H -0.2687 0.0509 0.3515 0.061 Uiso 1 1 calc R
H6B H -0.4100 -0.0071 0.2436 0.061 Uiso 1 1 calc R
C7 C -0.3979(3) -0.00120(14) 0.4100(3) 0.0439(6) Uani 1 1 d .
S1 S 0.20353(8) -0.38254(4) 0.36241(6) 0.04586(19) Uani 1 1 d .
S2 S 0.14100(9) -0.22279(4) 0.37006(7) 0.0495(2) Uani 1 1 d .
F1 F -0.0586(5) -0.4038(2) 0.3563(4) 0.1713(15) Uani 1 1 d .
F2 F 0.0557(5) -0.50893(17) 0.3536(3) 0.1591(14) Uani 1 1 d .
F3 F 0.1769(5) -0.44625(18) 0.5356(3) 0.1555(14) Uani 1 1 d .
F4 F 0.2284(4) -0.22133(15) 0.2130(3) 0.1195(10) Uani 1 1 d .
F5 F 0.2115(4) -0.10775(14) 0.2767(3) 0.1339(11) Uani 1 1 d .
F6 F 0.4205(3) -0.18054(17) 0.4093(3) 0.1178(9) Uani 1 1 d .
O3 O 0.3594(3) -0.42492(14) 0.4289(2) 0.0785(7) Uani 1 1 d .
O4 O 0.0959(3) -0.38093(12) 0.22062(18) 0.0636(6) Uani 1 1 d .
O5 O 0.1784(3) -0.17069(13) 0.4735(2) 0.0772(7) Uani 1 1 d .
O6 O -0.0298(3) -0.22990(14) 0.2536(2) 0.0768(7) Uani 1 1 d .
N3 N 0.2389(3) -0.30231(13) 0.4361(2) 0.0520(6) Uani 1 1 d .
C8 C 0.0852(7) -0.4374(3) 0.4045(5) 0.0972(13) Uani 1 1 d .
C9 C 0.2550(5) -0.1809(2) 0.3123(4) 0.0723(9) 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'
F F 0.0171 0.0103 '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'
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
C7 O2 H2 109.5
C4 N1 C2 107.8(2)
C4 N1 C1 126.3(2)
C2 N1 C1 125.9(2)
C4 N2 C3 107.9(2)
C4 N2 C5 126.0(2)
C3 N2 C5 126.0(2)
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 N1 107.6(2)
C3 C2 H2A 126.2
N1 C2 H2A 126.2
C2 C3 N2 107.2(2)
C2 C3 H3A 126.4
N2 C3 H3A 126.4
N2 C4 N1 109.4(2)
N2 C4 H4A 125.3
N1 C4 H4A 125.3
N2 C5 C6 112.4(2)
N2 C5 H5A 109.1
C6 C5 H5A 109.1
N2 C5 H5B 109.1
C6 C5 H5B 109.1
H5A C5 H5B 107.9
C7 C6 C5 114.0(2)
C7 C6 H6A 108.8
C5 C6 H6A 108.8
C7 C6 H6B 108.8
C5 C6 H6B 108.8
H6A C6 H6B 107.6
O1 C7 O2 123.7(2)
O1 C7 C6 122.8(2)
O2 C7 C6 113.5(2)
O4 S1 O3 117.74(14)
O4 S1 N3 117.17(12)
O3 S1 N3 108.64(13)
O4 S1 C8 104.72(19)
O3 S1 C8 103.5(2)
N3 S1 C8 102.94(18)
O6 S2 O5 118.76(15)
O6 S2 N3 116.00(14)
O5 S2 N3 108.37(13)
O6 S2 C9 105.13(17)
O5 S2 C9 104.16(17)
N3 S2 C9 102.31(16)
S1 N3 S2 126.16(14)
F1 C8 F2 108.8(4)
F1 C8 F3 111.1(4)
F2 C8 F3 106.4(4)
F1 C8 S1 111.2(3)
F2 C8 S1 108.8(3)
F3 C8 S1 110.4(3)
F5 C9 F4 109.9(3)
F5 C9 F6 106.2(3)
F4 C9 F6 107.6(3)
F5 C9 S2 110.7(3)
F4 C9 S2 111.5(3)
F6 C9 S2 110.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.217(3)
O2 C7 1.305(3)
O2 H2 0.8201
N1 C4 1.324(3)
N1 C2 1.369(3)
N1 C1 1.461(4)
N2 C4 1.316(3)
N2 C3 1.376(3)
N2 C5 1.463(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.332(4)
C2 H2A 0.9300
C3 H3A 0.9300
C4 H4A 0.9300
C5 C6 1.512(4)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.493(4)
C6 H6A 0.9700
C6 H6B 0.9700
S1 O4 1.415(2)
S1 O3 1.423(2)
S1 N3 1.560(2)
S1 C8 1.809(4)
S2 O6 1.415(2)
S2 O5 1.422(2)
S2 N3 1.569(2)
S2 C9 1.818(4)
F1 C8 1.291(6)
F2 C8 1.318(5)
F3 C8 1.320(5)
F4 C9 1.303(4)
F5 C9 1.299(4)
F6 C9 1.318(4)
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
C4 N1 C2 C3 0.5(3)
C1 N1 C2 C3 178.1(3)
N1 C2 C3 N2 -0.5(3)
C4 N2 C3 C2 0.3(3)
C5 N2 C3 C2 -179.6(2)
C3 N2 C4 N1 0.0(3)
C5 N2 C4 N1 179.9(2)
C2 N1 C4 N2 -0.3(3)
C1 N1 C4 N2 -177.9(3)
C4 N2 C5 C6 -119.3(3)
C3 N2 C5 C6 60.5(3)
N2 C5 C6 C7 65.7(3)
C5 C6 C7 O1 12.4(4)
C5 C6 C7 O2 -168.2(2)
O4 S1 N3 S2 12.3(3)
O3 S1 N3 S2 148.8(2)
C8 S1 N3 S2 -101.9(3)
O6 S2 N3 S1 27.8(3)
O5 S2 N3 S1 164.32(19)
C9 S2 N3 S1 -86.0(2)
O4 S1 C8 F1 -59.3(4)
O3 S1 C8 F1 176.8(3)
N3 S1 C8 F1 63.8(4)
O4 S1 C8 F2 60.6(4)
O3 S1 C8 F2 -63.3(4)
N3 S1 C8 F2 -176.4(3)
O4 S1 C8 F3 177.0(3)
O3 S1 C8 F3 53.1(4)
N3 S1 C8 F3 -60.0(4)
O6 S2 C9 F5 70.3(3)
O5 S2 C9 F5 -55.3(3)
N3 S2 C9 F5 -168.1(3)
O6 S2 C9 F4 -52.3(3)
O5 S2 C9 F4 -177.9(3)
N3 S2 C9 F4 69.3(3)
O6 S2 C9 F6 -172.1(2)
O5 S2 C9 F6 62.2(3)
N3 S2 C9 F6 -50.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 87556464
