#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:15:29 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179101 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/63/4306382.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_4306382
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         'C7 H14 N O2, C2 F6 N O4 S2'
_chemical_formula_sum            'C9 H14 F6 N2 O6 S2'
_chemical_formula_weight         424.36
_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                 108.721(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.6959(16)
_cell_length_b                   7.0808(8)
_cell_length_c                   15.3090(13)
_cell_measurement_temperature    100(2)
_cell_volume                     1611.4(3)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0668
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15225
_diffrn_reflns_theta_full        71.29
_diffrn_reflns_theta_max         71.29
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    3.951
_exptl_absorpt_correction_T_max  0.674
_exptl_absorpt_correction_T_min  0.463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0374
_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)+(0.0474P)²+0.4327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                2689
_reflns_number_total             3106
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801213z_si_009.cif
_cod_data_source_block           wg162
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4306382
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 0.07541(15) 0.3194(3) 0.30411(15) 0.0231(5) Uani 1 1 d . . .
C2 C 0.40758(14) 0.2064(3) 0.46383(15) 0.0198(4) Uani 1 1 d . . .
C3 C 0.70351(14) 0.5014(3) 0.35117(15) 0.0190(4) Uani 1 1 d . . .
H3A H 0.7124(2) 0.5672(12) 0.4091(10) 0.023 Uiso 1 1 calc R . .
H3B H 0.7173(3) 0.5870(16) 0.3080(8) 0.023 Uiso 1 1 calc R . .
C4 C 0.60733(15) 0.4276(3) 0.31215(16) 0.0256(5) Uani 1 1 d . . .
H4A H 0.5865(5) 0.4376(4) 0.2471(13) 0.031 Uiso 1 1 calc R . .
H4B H 0.5684(8) 0.4972(15) 0.3361(5) 0.031 Uiso 1 1 calc R . .
C5 C 0.61091(15) 0.2191(3) 0.34197(17) 0.0275(5) Uani 1 1 d . . .
H5A H 0.5727(8) 0.1982(6) 0.3766(7) 0.033 Uiso 1 1 calc R . .
H5B H 0.5938(4) 0.1402(17) 0.2906(11) 0.033 Uiso 1 1 calc R . .
C6 C 0.70842(15) 0.1823(3) 0.39987(15) 0.0201(4) Uani 1 1 d . . .
H6A H 0.7169(2) 0.2008(4) 0.4643(12) 0.024 Uiso 1 1 calc R . .
H6B H 0.7259(4) 0.056(2) 0.3908(2) 0.024 Uiso 1 1 calc R . .
C7 C 0.85171(13) 0.3672(3) 0.43536(14) 0.0183(4) Uani 1 1 d . . .
H7A H 0.8420(2) 0.4139(9) 0.4915(10) 0.022 Uiso 1 1 calc R . .
H7B H 0.8800(5) 0.4688(18) 0.4113(4) 0.022 Uiso 1 1 calc R . .
C8 C 0.91604(13) 0.2021(3) 0.46053(13) 0.0154(4) Uani 1 1 d . . .
C9 C 0.77154(14) 0.2651(3) 0.27519(14) 0.0195(4) Uani 1 1 d . . .
H9A H 0.8060(11) 0.3606(18) 0.2545(7) 0.029 Uiso 1 1 calc R . .
H9B H 0.7117(9) 0.252(2) 0.2292(7) 0.029 Uiso 1 1 calc R . .
H9C H 0.8030(11) 0.144(2) 0.2827(3) 0.029 Uiso 1 1 calc R . .
N1 N 0.24338(12) 0.1999(3) 0.34155(12) 0.0188(4) Uani 1 1 d . . .
N2 N 0.76209(11) 0.3245(2) 0.36576(11) 0.0145(4) Uani 1 1 d . . .
O1 O 0.17687(10) 0.2511(2) 0.47194(10) 0.0192(3) Uani 1 1 d . . .
O2 O 0.13017(11) -0.0160(2) 0.36447(11) 0.0252(4) Uani 1 1 d . . .
O3 O 0.30581(10) 0.5057(2) 0.42869(10) 0.0221(3) Uani 1 1 d . . .
O4 O 0.36198(10) 0.3778(2) 0.30726(11) 0.0247(4) Uani 1 1 d . . .
O5 O 0.89917(9) 0.0438(2) 0.42844(9) 0.0171(3) Uani 1 1 d . . .
O6 O 0.99197(10) 0.2554(2) 0.52190(10) 0.0188(3) Uani 1 1 d . . .
H6 H 1.025(2) 0.164(4) 0.5380(19) 0.028 Uiso 1 1 d . . .
F1 F 0.09903(9) 0.5003(2) 0.31273(11) 0.0341(3) Uani 1 1 d . . .
F2 F -0.00102(8) 0.3021(2) 0.32387(9) 0.0300(3) Uani 1 1 d . . .
F3 F 0.06014(10) 0.2670(3) 0.21722(9) 0.0382(4) Uani 1 1 d . . .
F4 F 0.42465(9) 0.04793(19) 0.42581(10) 0.0306(3) Uani 1 1 d . . .
F5 F 0.48360(9) 0.3037(2) 0.49658(10) 0.0304(3) Uani 1 1 d . . .
F6 F 0.38019(9) 0.16011(19) 0.53483(9) 0.0291(3) Uani 1 1 d . . .
S1 S 0.16336(3) 0.17310(7) 0.38228(3) 0.01562(14) Uani 1 1 d . . .
S2 S 0.32255(3) 0.34647(7) 0.37846(3) 0.01651(15) 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
F3 C1 F1 108.91(18) . . ?
F3 C1 F2 108.40(18) . . ?
F1 C1 F2 107.98(19) . . ?
F3 C1 S1 110.66(16) . . ?
F1 C1 S1 110.67(15) . . ?
F2 C1 S1 110.14(15) . . ?
F5 C2 F4 108.65(17) . . ?
F5 C2 F6 107.80(18) . . ?
F4 C2 F6 108.21(17) . . ?
F5 C2 S2 110.42(15) . . ?
F4 C2 S2 110.34(15) . . ?
F6 C2 S2 111.32(14) . . ?
C4 C3 N2 104.46(17) . . ?
C4 C3 H3A 110.9 . . ?
N2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
N2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 C5 105.94(18) . . ?
C3 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C6 C5 C4 105.69(18) . . ?
C6 C5 H5A 110.6 . . ?
C4 C5 H5A 110.6 . . ?
C6 C5 H5B 110.6 . . ?
C4 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
N2 C6 C5 104.61(17) . . ?
N2 C6 H6A 110.8 . . ?
C5 C6 H6A 110.8 . . ?
N2 C6 H6B 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
N2 C7 C8 115.04(17) . . ?
N2 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
N2 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
O5 C8 O6 125.60(19) . . ?
O5 C8 C7 124.60(18) . . ?
O6 C8 C7 109.80(17) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S2 N1 S1 124.82(11) . . ?
C7 N2 C9 111.41(15) . . ?
C7 N2 C6 112.92(16) . . ?
C9 N2 C6 111.33(16) . . ?
C7 N2 C3 108.81(15) . . ?
C9 N2 C3 109.16(15) . . ?
C6 N2 C3 102.79(16) . . ?
C8 O6 H6 110(2) . . ?
O2 S1 O1 118.48(9) . . ?
O2 S1 N1 108.88(9) . . ?
O1 S1 N1 116.08(9) . . ?
O2 S1 C1 104.65(10) . . ?
O1 S1 C1 104.90(10) . . ?
N1 S1 C1 101.66(10) . . ?
O4 S2 O3 118.95(9) . . ?
O4 S2 N1 108.18(10) . . ?
O3 S2 N1 116.73(9) . . ?
O4 S2 C2 103.47(10) . . ?
O3 S2 C2 105.06(10) . . ?
N1 S2 C2 102.07(10) . . ?
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 F3 1.327(3) . ?
C1 F1 1.329(3) . ?
C1 F2 1.333(2) . ?
C1 S1 1.830(2) . ?
C2 F5 1.329(3) . ?
C2 F4 1.330(3) . ?
C2 F6 1.332(3) . ?
C2 S2 1.831(2) . ?
C3 C4 1.527(3) . ?
C3 N2 1.527(2) . ?
C3 H3A 0.9706 . ?
C3 H3B 0.9706 . ?
C4 C5 1.541(3) . ?
C4 H4A 0.9457 . ?
C4 H4B 0.9457 . ?
C5 C6 1.525(3) . ?
C5 H5A 0.9308 . ?
C5 H5B 0.9308 . ?
C6 N2 1.510(3) . ?
C6 H6A 0.9613 . ?
C6 H6B 0.9613 . ?
C7 N2 1.498(2) . ?
C7 C8 1.512(3) . ?
C7 H7A 0.9778 . ?
C7 H7B 0.9778 . ?
C8 O5 1.219(2) . ?
C8 O6 1.314(3) . ?
C9 N2 1.501(2) . ?
C9 H9A 0.9805 . ?
C9 H9B 0.9805 . ?
C9 H9C 0.9805 . ?
N1 S2 1.5780(18) . ?
N1 S1 1.5827(18) . ?
O1 S1 1.4308(15) . ?
O2 S1 1.4309(16) . ?
O3 S2 1.4356(16) . ?
O4 S2 1.4330(15) . ?
O6 H6 0.82(3) . ?
