#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/24/4102425.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_4102425
loop_
_publ_author_name
'Radu Custelcean'
'Aurelien Bock'
'Bruce A. Moyer'
_publ_contact_author_email       custelceanr@ornl.gov
_publ_contact_author_name        'Radu Custelcean'
_publ_section_title
;
 Selectivity Principles in Anion Separation by Crystallization of
 Hydrogen-Bonding Capsules
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7177
_journal_page_last               7185
_journal_paper_doi               10.1021/ja101354r
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C24 H34 N10 O16.5 S2'
_chemical_formula_weight         790.73
_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                 105.8500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.4727(13)
_cell_length_b                   14.7923(10)
_cell_length_c                   13.2274(9)
_cell_measurement_temperature    173(2)
_cell_volume                     3477.0(4)
_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_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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35527
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.15
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.9671
_exptl_absorpt_correction_T_min  0.9445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.779
_refine_diff_density_min         -0.806
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         8662
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0873
_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)+(0.1626P)²+5.5734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2547
_refine_ls_wR_factor_ref         0.2724
_reflns_number_gt                6968
_reflns_number_total             8662
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja101354r_si_002.cif
_cod_data_source_block           c:\frames\235\work\p21c
_cod_original_formula_sum        'C24 H34 N10 O16.50 S2'
_cod_database_code               4102425
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
S1 S 0.09443(4) 0.36932(5) 0.17064(6) 0.0204(2) Uani 1 1 d .
O1 O -0.34192(16) -0.07783(19) -0.4672(2) 0.0386(6) Uani 1 1 d .
O1W O -0.2132(5) -0.1754(6) -0.4974(7) 0.154(3) Uani 1 1 d .
N1 N -0.16323(15) -0.08445(18) -0.1506(2) 0.0224(5) Uani 1 1 d .
H9 H -0.1822 -0.0263 -0.1662 0.027 Uiso 1 1 calc R
C1 C -0.2007(2) -0.1446(2) -0.2420(3) 0.0296(7) Uani 1 1 d .
H31A H -0.1802 -0.2066 -0.2270 0.035 Uiso 1 1 calc R
H31B H -0.1872 -0.1228 -0.3053 0.035 Uiso 1 1 calc R
S2 S 0.39848(5) 0.61460(7) 0.62922(8) 0.0361(3) Uani 1 1 d .
O2 O -0.18369(13) 0.08220(16) -0.24076(19) 0.0275(5) Uani 1 1 d U
O2W O 0.3098(4) 0.3627(5) 0.3520(9) 0.104(4) Uani 0.50 1 d P
N2 N -0.32356(17) -0.0620(2) -0.2910(3) 0.0330(7) Uani 1 1 d .
H20 H -0.3280 -0.0263 -0.2398 0.040 Uiso 1 1 calc R
C2 C -0.2862(2) -0.1490(3) -0.2664(3) 0.0354(8) Uani 1 1 d .
H29A H -0.3055 -0.1903 -0.3267 0.043 Uiso 1 1 calc R
H29B H -0.2996 -0.1753 -0.2051 0.043 Uiso 1 1 calc R
O3 O -0.08810(14) 0.12748(18) 0.0629(2) 0.0349(6) Uani 1 1 d U
O3W O 0.3579(9) 0.3796(8) 0.5056(16) 0.176(9) Uani 0.50 1 d P
N3 N -0.39193(18) 0.0435(2) -0.4029(3) 0.0375(7) Uani 1 1 d .
H27 H -0.3935 0.0710 -0.3446 0.045 Uiso 1 1 calc R
C3 C -0.35150(18) -0.0357(2) -0.3921(3) 0.0312(7) Uani 1 1 d .
O4 O 0.07116(16) 0.33139(19) 0.2590(2) 0.0385(6) Uani 1 1 d .
O4W O 0.02518(15) 0.30410(18) 0.8677(2) 0.0335(6) Uani 1 1 d .
N4 N -0.4669(2) 0.1038(3) -0.6826(3) 0.0501(9) Uani 1 1 d .
H43 H -0.4635 0.0860 -0.7446 0.060 Uiso 1 1 calc R
C4 C -0.4309(2) 0.0847(3) -0.4976(3) 0.0361(8) Uani 1 1 d .
O5 O 0.08170(18) 0.3032(2) 0.0858(2) 0.0437(7) Uani 1 1 d U
O5W O 0.5352(5) 0.4397(6) 0.6195(5) 0.152(3) Uani 1 1 d .
N5 N -0.05632(16) 0.07528(18) -0.1979(2) 0.0246(6) Uani 1 1 d .
H13 H -0.0136 0.1042 -0.1724 0.030 Uiso 1 1 calc R
C5 C -0.4276(2) 0.0568(3) -0.5962(3) 0.0447(10) Uani 1 1 d .
H41 H -0.3985 0.0055 -0.6036 0.054 Uiso 1 1 calc R
O6 O 0.17501(14) 0.39377(19) 0.2074(2) 0.0381(6) Uani 1 1 d U
O6W O 0.6021(4) 0.6161(9) 0.7586(12) 0.167(8) Uani 0.50 1 d P
N6 N -0.11534(15) 0.21369(18) -0.2145(2) 0.0237(5) Uani 1 1 d .
H7 H -0.0695 0.2360 -0.1937 0.028 Uiso 1 1 calc R
C6 C -0.5092(3) 0.1739(4) -0.6786(4) 0.0536(12) Uani 1 1 d .
H46 H -0.5351 0.2044 -0.7413 0.064 Uiso 1 1 calc R
O7 O 0.05084(13) 0.45279(16) 0.13306(19) 0.0279(5) Uani 1 1 d .
O7W O 0.6244(6) 0.7380(8) 0.9090(9) 0.197(4) Uiso 1 1 d .
N7 N -0.20863(18) 0.43015(19) -0.2530(2) 0.0287(6) Uani 1 1 d .
H10 H -0.1951 0.4873 -0.2449 0.034 Uiso 1 1 calc R
C7 C -0.5157(3) 0.2028(3) -0.5840(4) 0.0517(12) Uani 1 1 d .
H45 H -0.5473 0.2527 -0.5804 0.062 Uiso 1 1 calc R
O8 O 0.4302(3) 0.6338(3) 0.7408(3) 0.0879(17) Uani 1 1 d .
N8 N -0.19436(16) 0.0430(2) 0.0019(2) 0.0282(6) Uani 1 1 d .
H8 H -0.2424 0.0440 -0.0324 0.034 Uiso 1 1 calc R
C8 C -0.4761(2) 0.1589(3) -0.4919(4) 0.0453(10) Uani 1 1 d .
H40 H -0.4800 0.1796 -0.4256 0.054 Uiso 1 1 calc R
O9 O 0.35642(16) 0.6920(2) 0.5766(3) 0.0551(9) Uani 1 1 d .
N9 N -0.20208(15) 0.1964(2) -0.0073(2) 0.0253(6) Uani 1 1 d .
H4 H -0.2502 0.1859 -0.0359 0.030 Uiso 1 1 calc R
C9 C -0.07901(17) -0.0808(2) -0.1371(3) 0.0267(7) Uani 1 1 d .
H11A H -0.0540 -0.0577 -0.0658 0.032 Uiso 1 1 calc R
H11B H -0.0605 -0.1430 -0.1420 0.032 Uiso 1 1 calc R
O10 O 0.4599(2) 0.5961(3) 0.5818(4) 0.0695(11) Uani 1 1 d .
N10 N -0.09023(16) 0.4043(2) 0.0396(2) 0.0262(6) Uani 1 1 d .
H5 H -0.0428 0.4215 0.0596 0.031 Uiso 1 1 calc R
C10 C -0.05622(18) -0.0219(2) -0.2172(3) 0.0250(6) Uani 1 1 d .
H18A H -0.0051 -0.0399 -0.2194 0.030 Uiso 1 1 calc R
H18B H -0.0909 -0.0344 -0.2874 0.030 Uiso 1 1 calc R
O11 O 0.34837(18) 0.5344(2) 0.6173(3) 0.0492(8) Uani 1 1 d .
C11 C -0.12221(18) 0.1206(2) -0.2194(2) 0.0221(6) Uani 1 1 d .
C12 C -0.17442(18) 0.2752(2) -0.2397(2) 0.0216(6) Uani 1 1 d .
C13 C -0.15481(19) 0.3664(2) -0.2293(2) 0.0234(6) Uani 1 1 d .
H19 H -0.1034 0.3835 -0.2054 0.028 Uiso 1 1 calc R
C14 C -0.2820(2) 0.4104(3) -0.2885(3) 0.0335(8) Uani 1 1 d .
H33 H -0.3183 0.4573 -0.3059 0.040 Uiso 1 1 calc R
C15 C -0.3040(2) 0.3213(3) -0.2994(3) 0.0326(7) Uani 1 1 d .
H34 H -0.3560 0.3066 -0.3241 0.039 Uiso 1 1 calc R
C16 C -0.25094(19) 0.2528(2) -0.2746(3) 0.0282(7) Uani 1 1 d .
H38 H -0.2663 0.1913 -0.2811 0.034 Uiso 1 1 calc R
C17 C -0.1800(2) -0.1137(2) -0.0506(3) 0.0289(7) Uani 1 1 d .
H23A H -0.1525 -0.1704 -0.0257 0.035 Uiso 1 1 calc R
H23B H -0.2345 -0.1264 -0.0652 0.035 Uiso 1 1 calc R
C18 C -0.1579(2) -0.0429(3) 0.0357(3) 0.0315(7) Uani 1 1 d .
H37A H -0.1722 -0.0643 0.0985 0.038 Uiso 1 1 calc R
H37B H -0.1026 -0.0345 0.0556 0.038 Uiso 1 1 calc R
C19 C -0.15577(18) 0.1218(2) 0.0224(2) 0.0243(6) Uani 1 1 d .
C20 C -0.17957(18) 0.2861(2) 0.0038(2) 0.0230(6) Uani 1 1 d .
C21 C -0.10490(19) 0.3153(2) 0.0350(2) 0.0259(6) Uani 1 1 d .
H16 H -0.0650 0.2727 0.0528 0.031 Uiso 1 1 calc R
C22 C -0.14294(19) 0.4685(2) 0.0158(3) 0.0280(7) Uani 1 1 d .
H30 H -0.1293 0.5305 0.0192 0.034 Uiso 1 1 calc R
C23 C -0.2179(2) 0.4430(3) -0.0141(3) 0.0290(7) Uani 1 1 d .
H32 H -0.2563 0.4876 -0.0306 0.035 Uiso 1 1 calc R
C24 C -0.23649(18) 0.3526(2) -0.0197(2) 0.0261(6) Uani 1 1 d .
H28 H -0.2879 0.3349 -0.0395 0.031 Uiso 1 1 calc R
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'
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
O5 S1 O4 109.69(19)
O5 S1 O6 110.70(18)
O4 S1 O6 108.64(17)
O5 S1 O7 109.97(15)
O4 S1 O7 109.62(15)
O6 S1 O7 108.18(15)
C17 N1 C1 112.1(3)
C17 N1 C9 111.0(2)
C1 N1 C9 110.3(3)
N1 C1 C2 114.6(3)
O9 S2 O8 110.3(3)
O9 S2 O10 108.6(2)
O8 S2 O10 109.0(3)
O9 S2 O11 110.05(19)
O8 S2 O11 109.2(2)
O10 S2 O11 109.8(2)
C3 N2 C2 120.4(3)
N2 C2 C1 114.2(3)
C3 N3 C4 126.5(4)
O1 C3 N2 123.6(4)
O1 C3 N3 122.9(4)
N2 C3 N3 113.4(3)
C6 N4 C5 123.8(5)
C5 C4 C8 117.8(4)
C5 C4 N3 124.6(4)
C8 C4 N3 117.6(4)
C11 N5 C10 119.7(3)
N4 C5 C4 119.1(4)
C11 N6 C12 125.8(3)
N4 C6 C7 119.4(4)
C14 N7 C13 122.8(3)
C6 C7 C8 120.0(5)
C19 N8 C18 121.2(3)
C4 C8 C7 119.8(5)
C19 N9 C20 126.0(3)
C10 C9 N1 114.2(3)
C22 N10 C21 124.2(3)
N5 C10 C9 115.4(3)
O2 C11 N5 122.8(3)
O2 C11 N6 122.5(3)
N5 C11 N6 114.7(3)
N6 C12 C13 116.4(3)
N6 C12 C16 125.4(3)
C13 C12 C16 118.2(3)
N7 C13 C12 120.0(3)
N7 C14 C15 119.3(3)
C14 C15 C16 120.3(3)
C15 C16 C12 119.3(3)
N1 C17 C18 112.7(3)
N8 C18 C17 111.4(3)
O3 C19 N8 124.5(3)
O3 C19 N9 123.3(3)
N8 C19 N9 112.2(3)
N9 C20 C21 124.8(3)
N9 C20 C24 117.4(3)
C21 C20 C24 117.8(3)
N10 C21 C20 119.2(3)
N10 C22 C23 118.8(3)
C24 C23 C22 119.7(3)
C23 C24 C20 120.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O5 1.459(3)
S1 O4 1.463(3)
S1 O6 1.479(3)
S1 O7 1.484(2)
O1 C3 1.225(5)
N1 C17 1.501(4)
N1 C1 1.508(4)
N1 C9 1.518(4)
C1 C2 1.525(5)
S2 O9 1.450(3)
S2 O8 1.460(4)
S2 O10 1.465(4)
S2 O11 1.487(3)
O2 C11 1.232(4)
N2 C3 1.353(5)
N2 C2 1.454(5)
O3 C19 1.221(4)
N3 C3 1.375(5)
N3 C4 1.402(5)
N4 C6 1.308(7)
N4 C5 1.365(6)
C4 C5 1.384(6)
C4 C8 1.393(6)
N5 C11 1.350(4)
N5 C10 1.460(4)
N6 C11 1.383(4)
N6 C12 1.390(4)
C6 C7 1.358(8)
N7 C14 1.339(5)
N7 C13 1.344(4)
C7 C8 1.398(7)
N8 C19 1.355(5)
N8 C18 1.450(4)
N9 C19 1.386(4)
N9 C20 1.386(4)
C9 C10 1.517(4)
N10 C22 1.334(4)
N10 C21 1.343(5)
C12 C13 1.394(4)
C12 C16 1.401(5)
C14 C15 1.375(5)
C15 C16 1.386(5)
C17 C18 1.521(5)
C20 C21 1.396(5)
C20 C24 1.410(5)
C22 C23 1.385(5)
C23 C24 1.378(5)
