#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:05:52 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179439 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/36/4333636.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_4333636
loop_
_publ_author_name
'Daniel P. Fagnant'
'George S. Goff'
'Brian L. Scott'
'Wolfgang Runde'
'Joan F. Brennecke'
_publ_section_title
;
 Switchable Phase Behavior of [HBet][Tf2N]-H2O upon Neodymium Loading:
 Implications for Lanthanide Separations
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              549
_journal_page_last               551
_journal_paper_doi               10.1021/ic302359d
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C28 H60 Cl2 F24 N8 Nd2 O32 S8'
_chemical_formula_weight         2092.70
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 117.251(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.2899(19)
_cell_length_b                   14.2978(17)
_cell_length_c                   16.912(2)
_cell_measurement_temperature    120(1)
_cell_volume                     3501.8(7)
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω 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  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33034
_diffrn_reflns_theta_full        25.28
_diffrn_reflns_theta_max         25.28
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.931
_exptl_absorpt_correction_T_max  0.9268
_exptl_absorpt_correction_T_min  0.8609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v. 1 (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.985
_exptl_crystal_description       block
_exptl_crystal_F_000             2076
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.104
_refine_diff_density_min         -1.049
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0335
_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)+(0.0439P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                5006
_reflns_number_total             6327
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302359d_si_002.cif
_cod_data_source_block           apx1217
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4333636
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Nd1 Nd 0.115902(15) -0.032819(16) 0.114880(15) 0.00980(8) Uani 1 1 d .
Cl1 Cl 0.15655(8) 0.63721(8) 0.15609(7) 0.0177(2) Uani 1 1 d .
S1 S 1.01501(8) 0.89658(8) 0.37115(7) 0.0148(2) Uani 1 1 d .
S2 S 0.92548(8) 0.74756(8) 0.25541(8) 0.0182(3) Uani 1 1 d .
S3 S 0.12662(8) 0.66231(8) 0.88033(8) 0.0160(3) Uani 1 1 d .
S4 S 0.01347(8) 0.64861(8) 0.69715(8) 0.0164(3) Uani 1 1 d .
F1 F 1.12835(18) 0.7907(2) 0.50128(19) 0.0312(7) Uani 1 1 d .
F2 F 0.98756(18) 0.78437(18) 0.47863(17) 0.0240(6) Uani 1 1 d .
F3 F 1.0702(2) 0.9055(2) 0.54019(18) 0.0334(7) Uani 1 1 d .
F4 F 0.9232(2) 0.56754(19) 0.2470(2) 0.0319(7) Uani 1 1 d .
F5 F 1.0008(2) 0.6208(2) 0.37988(19) 0.0342(7) Uani 1 1 d .
F6 F 1.0578(2) 0.6277(2) 0.2885(3) 0.0470(9) Uani 1 1 d .
F7 F 0.30088(19) 0.6429(2) 0.92127(19) 0.0367(8) Uani 1 1 d .
F8 F 0.2260(2) 0.5135(2) 0.8978(2) 0.0389(8) Uani 1 1 d .
F9 F 0.26052(18) 0.5905(2) 1.01752(18) 0.0263(7) Uani 1 1 d .
F10 F 0.0234(2) 0.8266(2) 0.6680(2) 0.0421(9) Uani 1 1 d .
F11 F -0.0495(2) 0.7943(2) 0.7426(2) 0.0476(9) Uani 1 1 d .
F12 F -0.1121(2) 0.7678(2) 0.6020(2) 0.0487(9) Uani 1 1 d .
N1 N 0.1315(2) 0.3290(2) 0.0563(2) 0.0136(8) Uani 1 1 d .
N2 N -0.2548(2) 0.0085(3) 0.1106(2) 0.0151(8) Uani 1 1 d .
N3 N 1.0102(2) 0.8150(3) 0.3060(2) 0.0151(8) Uani 1 1 d .
N4 N 0.1083(3) 0.6608(3) 0.7805(3) 0.0208(9) Uani 1 1 d .
O1 O 0.01091(19) 0.1018(2) 0.01225(19) 0.0134(7) Uani 1 1 d .
O2 O 0.1470(2) 0.1401(2) 0.11949(19) 0.0177(7) Uani 1 1 d .
O3 O -0.1496(2) 0.0094(2) 0.01106(19) 0.0140(7) Uani 1 1 d .
O4 O -0.0195(2) -0.0095(2) 0.1393(2) 0.0160(7) Uani 1 1 d .
O5W O 0.1075(2) -0.1695(2) 0.2010(2) 0.0164(7) Uani 1 1 d .
O6W O 0.1672(2) 0.0190(2) 0.2715(2) 0.0176(7) Uani 1 1 d .
O7W O 0.1921(2) -0.1745(2) 0.0888(2) 0.0152(7) Uani 1 1 d .
O8W O 0.2846(2) -0.0039(2) 0.1860(2) 0.0159(7) Uani 1 1 d .
O9 O 0.9030(2) 0.7465(2) 0.1631(2) 0.0297(9) Uani 1 1 d .
O10 O 0.8521(2) 0.7529(2) 0.2793(2) 0.0250(8) Uani 1 1 d .
O11 O 0.9284(2) 0.9388(2) 0.3509(2) 0.0211(8) Uani 1 1 d .
O12 O 1.0913(2) 0.9544(2) 0.3837(2) 0.0209(7) Uani 1 1 d .
O13 O 0.1506(2) 0.7547(2) 0.9175(2) 0.0288(8) Uani 1 1 d .
O14 O 0.0646(2) 0.6105(2) 0.9014(2) 0.0237(8) Uani 1 1 d .
O15 O 0.0284(2) 0.6263(2) 0.6227(2) 0.0233(8) Uani 1 1 d .
O16 O -0.0545(2) 0.5961(2) 0.7096(2) 0.0272(8) Uani 1 1 d .
C1 C 0.0748(3) 0.1611(3) 0.0528(3) 0.0123(9) Uani 1 1 d .
C2 C 0.0566(3) 0.2579(3) 0.0124(3) 0.0124(9) Uani 1 1 d .
H2A H 0.0442 0.2522 -0.0492 0.015 Uiso 1 1 calc R
H2B H 0.0009 0.2817 0.0126 0.015 Uiso 1 1 calc R
C3 C 0.0973(3) 0.4176(3) 0.0044(3) 0.0225(11) Uani 1 1 d .
H3A H 0.0927 0.4096 -0.0538 0.034 Uiso 1 1 calc R
H3B H 0.1396 0.4675 0.0346 0.034 Uiso 1 1 calc R
H3C H 0.0376 0.4327 -0.0008 0.034 Uiso 1 1 calc R
C4 C 0.2192(3) 0.3002(3) 0.0536(3) 0.0192(11) Uani 1 1 d .
H4A H 0.2434 0.2448 0.0887 0.029 Uiso 1 1 calc R
H4B H 0.2637 0.3498 0.0771 0.029 Uiso 1 1 calc R
H4C H 0.2062 0.2878 -0.0068 0.029 Uiso 1 1 calc R
C5 C 0.1519(3) 0.3469(3) 0.1508(3) 0.0201(11) Uani 1 1 d .
H5A H 0.0962 0.3652 0.1528 0.030 Uiso 1 1 calc R
H5B H 0.1968 0.3960 0.1750 0.030 Uiso 1 1 calc R
H5C H 0.1757 0.2909 0.1851 0.030 Uiso 1 1 calc R
C6 C -0.1038(3) 0.0062(3) 0.0944(3) 0.0125(10) Uani 1 1 d .
C7 C -0.1526(3) 0.0261(3) 0.1507(3) 0.0183(10) Uani 1 1 d .
H7A H -0.1229 -0.0112 0.2044 0.022 Uiso 1 1 calc R
H7B H -0.1419 0.0913 0.1686 0.022 Uiso 1 1 calc R
C8 C -0.3095(3) 0.0779(4) 0.0397(3) 0.0247(12) Uani 1 1 d .
H8A H -0.3742 0.0658 0.0182 0.037 Uiso 1 1 calc R
H8B H -0.2939 0.0724 -0.0084 0.037 Uiso 1 1 calc R
H8C H -0.2954 0.1399 0.0639 0.037 Uiso 1 1 calc R
C9 C -0.2791(3) -0.0886(3) 0.0726(4) 0.0311(13) Uani 1 1 d .
H9A H -0.3433 -0.1004 0.0546 0.047 Uiso 1 1 calc R
H9B H -0.2421 -0.1334 0.1170 0.047 Uiso 1 1 calc R
H9C H -0.2675 -0.0940 0.0220 0.047 Uiso 1 1 calc R
C10 C -0.2808(4) 0.0176(4) 0.1848(3) 0.0309(13) Uani 1 1 d .
H10A H -0.2669 0.0797 0.2089 0.046 Uiso 1 1 calc R
H10B H -0.2464 -0.0269 0.2306 0.046 Uiso 1 1 calc R
H10C H -0.3456 0.0058 0.1622 0.046 Uiso 1 1 calc R
C11 C 1.0525(3) 0.8414(3) 0.4797(3) 0.0186(11) Uani 1 1 d .
C12 C 0.9808(3) 0.6345(3) 0.2953(3) 0.0233(11) Uani 1 1 d .
C13 C 0.2353(3) 0.5984(4) 0.9319(3) 0.0230(11) Uani 1 1 d .
C14 C -0.0338(4) 0.7666(4) 0.6755(4) 0.0296(13) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 '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'
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'
Cl Cl 0.1484 0.1585 '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
O1 Nd1 O4 74.63(10) 3 .
O1 Nd1 O3 73.88(10) 3 3
O4 Nd1 O3 134.86(10) . 3
O1 Nd1 O8W 144.00(10) 3 .
O4 Nd1 O8W 141.34(10) . .
O3 Nd1 O8W 76.08(10) 3 .
O1 Nd1 O5W 86.91(10) 3 .
O4 Nd1 O5W 73.23(10) . .
O3 Nd1 O5W 135.45(10) 3 .
O8W Nd1 O5W 101.15(10) . .
O1 Nd1 O6W 143.35(10) 3 .
O4 Nd1 O6W 70.75(10) . .
O3 Nd1 O6W 141.36(10) 3 .
O8W Nd1 O6W 71.20(10) . .
O5W Nd1 O6W 72.05(10) . .
O1 Nd1 O2 120.55(10) 3 .
O4 Nd1 O2 92.58(10) . .
O3 Nd1 O2 76.76(10) 3 .
O8W Nd1 O2 70.05(10) . .
O5W Nd1 O2 145.12(10) . .
O6W Nd1 O2 73.21(10) . .
O1 Nd1 O7W 78.68(9) 3 .
O4 Nd1 O7W 133.95(10) . .
O3 Nd1 O7W 68.51(10) 3 .
O8W Nd1 O7W 72.14(10) . .
O5W Nd1 O7W 68.47(10) . .
O6W Nd1 O7W 118.18(10) . .
O2 Nd1 O7W 133.42(10) . .
O1 Nd1 O1 71.23(10) 3 .
O4 Nd1 O1 69.37(9) . .
O3 Nd1 O1 70.34(9) 3 .
O8W Nd1 O1 116.06(9) . .
O5W Nd1 O1 140.40(9) . .
O6W Nd1 O1 106.46(9) . .
O2 Nd1 O1 50.41(9) . .
O7W Nd1 O1 134.15(9) . .
O1 Nd1 C1 96.10(11) 3 .
O4 Nd1 C1 81.71(11) . .
O3 Nd1 C1 70.44(11) 3 .
O8W Nd1 C1 92.10(11) . .
O5W Nd1 C1 153.02(11) . .
O6W Nd1 C1 90.56(11) . .
O2 Nd1 C1 24.76(10) . .
O7W Nd1 C1 138.44(11) . .
O1 Nd1 C1 25.72(10) . .
O1 Nd1 Nd1 37.44(7) 3 3
O4 Nd1 Nd1 67.55(7) . 3
O3 Nd1 Nd1 67.72(7) 3 3
O8W Nd1 Nd1 139.23(7) . 3
O5W Nd1 Nd1 117.59(7) . 3
O6W Nd1 Nd1 130.78(7) . 3
O2 Nd1 Nd1 83.65(7) . 3
O7W Nd1 Nd1 109.39(7) . 3
O1 Nd1 Nd1 33.79(6) . 3
C1 Nd1 Nd1 58.93(8) . 3
O11 S1 O12 119.4(2) . .
O11 S1 N3 114.7(2) . .
O12 S1 N3 107.01(19) . .
O11 S1 C11 105.3(2) . .
O12 S1 C11 103.5(2) . .
N3 S1 C11 105.6(2) . .
O10 S2 O9 118.7(2) . .
O10 S2 N3 116.9(2) . .
O9 S2 N3 108.8(2) . .
O10 S2 C12 106.1(2) . .
O9 S2 C12 103.4(2) . .
N3 S2 C12 100.4(2) . .
O14 S3 O13 116.8(2) . .
O14 S3 N4 117.0(2) . .
O13 S3 N4 111.2(2) . .
O14 S3 C13 105.3(2) . .
O13 S3 C13 104.0(2) . .
N4 S3 C13 99.9(2) . .
O15 S4 O16 118.0(2) . .
O15 S4 N4 109.0(2) . .
O16 S4 N4 116.1(2) . .
O15 S4 C14 104.9(2) . .
O16 S4 C14 103.4(2) . .
N4 S4 C14 103.4(2) . .
C3 N1 C2 106.6(3) . .
C3 N1 C5 108.8(4) . .
C2 N1 C5 112.1(3) . .
C3 N1 C4 108.5(3) . .
C2 N1 C4 111.6(3) . .
C5 N1 C4 109.2(3) . .
C8 N2 C10 108.6(4) . .
C8 N2 C9 109.0(4) . .
C10 N2 C9 108.4(4) . .
C8 N2 C7 112.4(4) . .
C10 N2 C7 106.6(3) . .
C9 N2 C7 111.6(4) . .
S2 N3 S1 125.5(2) . .
S4 N4 S3 126.6(2) . .
C1 O1 Nd1 155.6(3) . 3
C1 O1 Nd1 90.4(2) . .
Nd1 O1 Nd1 108.77(10) 3 .
C1 O2 Nd1 96.7(3) . .
C6 O3 Nd1 136.4(3) . 3
C6 O4 Nd1 138.4(3) . .
O2 C1 O1 122.1(4) . .
O2 C1 C2 122.8(4) . .
O1 C1 C2 115.0(4) . .
O2 C1 Nd1 58.5(2) . .
O1 C1 Nd1 63.9(2) . .
C2 C1 Nd1 173.3(3) . .
N1 C2 C1 116.8(3) . .
O4 C6 O3 127.6(4) . .
O4 C6 C7 113.4(4) . .
O3 C6 C7 118.9(4) . .
N2 C7 C6 118.3(4) . .
F3 C11 F2 109.3(4) . .
F3 C11 F1 108.9(4) . .
F2 C11 F1 107.6(4) . .
F3 C11 S1 109.7(3) . .
F2 C11 S1 110.7(3) . .
F1 C11 S1 110.6(3) . .
F6 C12 F5 108.1(4) . .
F6 C12 F4 109.0(4) . .
F5 C12 F4 108.3(4) . .
F6 C12 S2 111.3(3) . .
F5 C12 S2 111.5(3) . .
F4 C12 S2 108.8(3) . .
F9 C13 F8 108.5(4) . .
F9 C13 F7 109.1(4) . .
F8 C13 F7 108.7(4) . .
F9 C13 S3 108.4(3) . .
F8 C13 S3 111.0(3) . .
F7 C13 S3 111.2(3) . .
F12 C14 F10 108.9(4) . .
F12 C14 F11 108.8(4) . .
F10 C14 F11 108.0(4) . .
F12 C14 S4 109.9(4) . .
F10 C14 S4 111.7(4) . .
F11 C14 S4 109.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Nd1 O1 2.408(3) 3
Nd1 O4 2.445(3) .
Nd1 O3 2.454(3) 3
Nd1 O8W 2.478(3) .
Nd1 O5W 2.478(3) .
Nd1 O6W 2.497(3) .
Nd1 O2 2.517(3) .
Nd1 O7W 2.519(3) .
Nd1 O1 2.632(3) .
Nd1 C1 2.931(4) .
Nd1 Nd1 4.0989(6) 3
S1 O11 1.424(3) .
S1 O12 1.426(3) .
S1 N3 1.581(4) .
S1 C11 1.827(5) .
S2 O10 1.428(3) .
S2 O9 1.431(3) .
S2 N3 1.577(4) .
S2 C12 1.823(5) .
S3 O14 1.423(3) .
S3 O13 1.438(3) .
S3 N4 1.574(4) .
S3 C13 1.821(5) .
S4 O15 1.424(3) .
S4 O16 1.431(3) .
S4 N4 1.553(4) .
S4 C14 1.821(5) .
F1 C11 1.331(5) .
F2 C11 1.329(5) .
F3 C11 1.304(5) .
F4 C12 1.328(5) .
F5 C12 1.327(6) .
F6 C12 1.317(5) .
F7 C13 1.324(5) .
F8 C13 1.324(6) .
F9 C13 1.316(5) .
F10 C14 1.315(6) .
F11 C14 1.332(6) .
F12 C14 1.312(6) .
N1 C3 1.496(6) .
N1 C2 1.497(5) .
N1 C5 1.498(5) .
N1 C4 1.508(5) .
N2 C8 1.495(6) .
N2 C10 1.502(6) .
N2 C9 1.505(6) .
N2 C7 1.503(5) .
O1 C1 1.272(5) .
O1 Nd1 2.408(3) 3
O2 C1 1.236(5) .
O3 C6 1.258(5) .
O3 Nd1 2.454(3) 3
O4 C6 1.249(5) .
C1 C2 1.512(6) .
C6 C7 1.520(6) .
