#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:15:29 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179101 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/63/4306379.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_4306379
loop_
_publ_author_name
'Peter Nockemann'
'Ben Thijs'
'Tatjana N. Parac-Vogt'
'Kristof Van Hecke'
'Luc Van Meervelt'
'Bernard Tinant'
'Ingo Hartenbach'
'Thomas Schleid'
'Vu Thi Ngan'
'Minh Tho Nguyen'
'Koen Binnemans'
_publ_section_title
;
Carboxyl-Functionalized Task-Specific Ionic Liquids for Solubilizing Metal
Oxides
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9987
_journal_page_last               9999
_journal_paper_doi               10.1021/ic801213z
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         'C9 H18 N O3, C2 F6 N O4 S2'
_chemical_formula_sum            'C11 H18 F6 N2 O7 S2'
_chemical_formula_weight         468.41
_chemical_name_systematic
; 
 ? 
;
_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                 110.307(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0236(8)
_cell_length_b                   8.5641(7)
_cell_length_c                   17.3436(12)
_cell_measurement_temperature    100(2)
_cell_volume                     1814.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_publication_material  Platon
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'SMART 6000'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'crossed G\"obel mirrors'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16567
_diffrn_reflns_theta_full        70.61
_diffrn_reflns_theta_max         70.61
_diffrn_reflns_theta_min         3.62
_exptl_absorpt_coefficient_mu    3.617
_exptl_absorpt_correction_T_max  0.485
_exptl_absorpt_correction_T_min  0.309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0420
_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)+(0.0578P)²+0.5033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                2720
_reflns_number_total             3414
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801213z_si_006.cif
_cod_data_source_block           wg160
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4306379
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.87317(19) 0.7436(3) 0.16988(14) 0.0150(5) Uani 1 1 d . . .
H1A H 0.8429 0.8442 0.1803 0.018 Uiso 1 1 calc R . .
H1B H 0.8157 0.6630 0.1608 0.018 Uiso 1 1 calc R . .
C2 C 0.9716(2) 0.6998(3) 0.24449(14) 0.0168(5) Uani 1 1 d . . .
H2A H 1.0272 0.7837 0.2559 0.020 Uiso 1 1 calc R . .
H2B H 0.9487 0.6895 0.2931 0.020 Uiso 1 1 calc R . .
C3 C 1.0574(2) 0.5750(3) 0.16441(15) 0.0180(5) Uani 1 1 d . . .
H3A H 1.0945 0.4778 0.1575 0.022 Uiso 1 1 calc R . .
H3B H 1.1116 0.6608 0.1770 0.022 Uiso 1 1 calc R . .
C4 C 0.9648(2) 0.6111(3) 0.08539(14) 0.0163(5) Uani 1 1 d . . .
H4A H 0.9131 0.5221 0.0709 0.020 Uiso 1 1 calc R . .
H4B H 0.9946 0.6245 0.0405 0.020 Uiso 1 1 calc R . .
C5 C 0.79670(19) 0.7723(3) 0.02274(14) 0.0167(5) Uani 1 1 d . . .
H5A H 0.7579 0.8655 0.0325 0.020 Uiso 1 1 calc R . .
H5B H 0.7514 0.6800 0.0236 0.020 Uiso 1 1 calc R . .
C6 C 0.8037(2) 0.7856(3) -0.06287(15) 0.0162(5) Uani 1 1 d . . .
C7 C 0.97341(19) 0.9016(3) 0.09796(14) 0.0156(5) Uani 1 1 d . . .
H7A H 0.9995 0.9029 0.0513 0.023 Uiso 1 1 calc R . .
H7B H 1.0363 0.8995 0.1494 0.023 Uiso 1 1 calc R . .
H7C H 0.9296 0.9953 0.0965 0.023 Uiso 1 1 calc R . .
C8 C 0.6840(2) 0.8116(3) -0.20254(15) 0.0236(5) Uani 1 1 d . . .
H8A H 0.7501 0.8545 -0.2106 0.028 Uiso 1 1 calc R . .
H8B H 0.6220 0.8826 -0.2296 0.028 Uiso 1 1 calc R . .
C9 C 0.6596(2) 0.6517(3) -0.24089(16) 0.0257(6) Uani 1 1 d . . .
H9A H 0.7223 0.5828 -0.2154 0.039 Uiso 1 1 calc R . .
H9B H 0.6459 0.6596 -0.3000 0.039 Uiso 1 1 calc R . .
H9C H 0.5946 0.6089 -0.2322 0.039 Uiso 1 1 calc R . .
C10 C 0.3704(2) 0.7800(3) 1.10978(16) 0.0224(5) Uani 1 1 d . . .
C11 C 0.4329(2) 0.7365(3) 0.89710(17) 0.0234(5) Uani 1 1 d . . .
N1 N 0.90384(16) 0.7581(2) 0.09283(11) 0.0140(4) Uani 1 1 d . . .
N2 N 0.28256(18) 0.6434(2) 0.95870(13) 0.0191(4) Uani 1 1 d . . .
O1 O 1.01814(14) 0.55656(19) 0.23102(10) 0.0187(4) Uani 1 1 d . . .
O2 O 0.70185(15) 0.8024(2) -0.11449(10) 0.0206(4) Uani 1 1 d . . .
O3 O 0.88487(14) 0.7807(2) -0.08061(10) 0.0196(4) Uani 1 1 d . . .
O4 O 0.21897(17) 0.5704(2) 1.06970(11) 0.0256(4) Uani 1 1 d . . .
O5 O 0.17318(16) 0.8344(2) 1.01310(11) 0.0268(4) Uani 1 1 d . . .
O6 O 0.23446(16) 0.6602(2) 0.80872(11) 0.0276(4) Uani 1 1 d . . .
O7 O 0.26262(16) 0.9074(2) 0.88547(12) 0.0261(4) Uani 1 1 d . . .
F1 F 0.40810(14) 0.90439(18) 1.08284(10) 0.0293(4) Uani 1 1 d . . .
F2 F 0.34661(16) 0.82077(19) 1.17572(10) 0.0348(4) Uani 1 1 d . . .
F3 F 0.44819(15) 0.6728(2) 1.13156(11) 0.0401(5) Uani 1 1 d . . .
F4 F 0.49415(14) 0.7974(2) 0.96789(10) 0.0389(4) Uani 1 1 d . . .
F5 F 0.46367(16) 0.5914(2) 0.89288(14) 0.0476(5) Uani 1 1 d . . .
F6 F 0.44875(14) 0.8175(2) 0.83672(10) 0.0326(4) Uani 1 1 d . . .
S1 S 0.24646(5) 0.70446(7) 1.03143(3) 0.01701(16) Uani 1 1 d . . .
S2 S 0.28632(5) 0.74475(7) 0.88328(4) 0.01749(16) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 111.47(19) . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N1 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
O1 C2 C1 110.77(19) . . ?
O1 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
O1 C3 C4 111.1(2) . . ?
O1 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
O1 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 N1 111.66(18) . . ?
C3 C4 H4A 109.3 . . ?
N1 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
N1 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
N1 C5 C6 116.18(19) . . ?
N1 C5 H5A 108.2 . . ?
C6 C5 H5A 108.2 . . ?
N1 C5 H5B 108.2 . . ?
C6 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
O3 C6 O2 126.5(2) . . ?
O3 C6 C5 127.1(2) . . ?
O2 C6 C5 106.4(2) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C9 110.1(2) . . ?
O2 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
O2 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F3 C10 F1 108.6(2) . . ?
F3 C10 F2 108.7(2) . . ?
F1 C10 F2 108.5(2) . . ?
F3 C10 S1 110.95(17) . . ?
F1 C10 S1 111.23(18) . . ?
F2 C10 S1 108.81(19) . . ?
F5 C11 F4 109.1(2) . . ?
F5 C11 F6 108.4(2) . . ?
F4 C11 F6 108.5(2) . . ?
F5 C11 S2 110.60(18) . . ?
F4 C11 S2 111.81(18) . . ?
F6 C11 S2 108.34(18) . . ?
C5 N1 C7 110.52(17) . . ?
C5 N1 C4 111.39(17) . . ?
C7 N1 C4 111.03(18) . . ?
C5 N1 C1 105.23(17) . . ?
C7 N1 C1 110.37(17) . . ?
C4 N1 C1 108.11(17) . . ?
S1 N2 S2 125.49(13) . . ?
C2 O1 C3 109.32(17) . . ?
C6 O2 C8 118.0(2) . . ?
O5 S1 O4 118.19(12) . . ?
O5 S1 N2 116.17(11) . . ?
O4 S1 N2 107.23(11) . . ?
O5 S1 C10 103.82(12) . . ?
O4 S1 C10 103.73(12) . . ?
N2 S1 C10 106.24(12) . . ?
O7 S2 O6 118.60(12) . . ?
O7 S2 N2 116.28(11) . . ?
O6 S2 N2 109.18(12) . . ?
O7 S2 C11 104.94(12) . . ?
O6 S2 C11 103.95(12) . . ?
N2 S2 C11 101.48(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.519(3) . ?
C1 N1 1.527(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O1 1.424(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O1 1.425(3) . ?
C3 C4 1.510(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.518(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.504(3) . ?
C5 C6 1.523(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O3 1.200(3) . ?
C6 O2 1.326(3) . ?
C7 N1 1.511(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O2 1.465(3) . ?
C8 C9 1.507(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 F3 1.322(3) . ?
C10 F1 1.324(3) . ?
C10 F2 1.331(3) . ?
C10 S1 1.830(3) . ?
C11 F5 1.315(3) . ?
C11 F4 1.318(3) . ?
C11 F6 1.331(3) . ?
C11 S2 1.840(3) . ?
N2 S1 1.580(2) . ?
N2 S2 1.585(2) . ?
O4 S1 1.4323(18) . ?
O5 S1 1.4279(19) . ?
O6 S2 1.4307(19) . ?
O7 S2 1.4298(19) . ?
