#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/19/2201944.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2201944
loop_
_publ_author_name
'Akashi, Haruo'
'Yamauchi, Tsutomu'
_publ_section_title
;
 Tetrasodium tetrahydroxytetrathiacalix[4]arenetetrasulfonate
 tetradecahydrate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m336
_journal_page_last               m338
_journal_paper_doi               10.1107/S1600536803009784
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '4Na 1+, C24 H12 O16 S8 4-, 14H2 O1'
_chemical_formula_moiety         'C24 H40 Na4 O30 S8'
_chemical_formula_sum            'C24 H40 Na4 O30 S8'
_chemical_formula_weight         1157.00
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                95.743(4)
_cell_angle_beta                 102.490(2)
_cell_angle_gamma                97.897(4)
_cell_formula_units_Z            1
_cell_length_a                   8.2974(7)
_cell_length_b                   8.8446(6)
_cell_length_c                   15.7890(10)
_cell_measurement_reflns_used    4591
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     1110.42(14)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC 2001)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC 2001)'
_computing_structure_refinement  'CrystalStructure (Rigaku/MSC 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9223
_diffrn_measured_fraction_theta_max 0.9171
_diffrn_measurement_device_type  'Rigaku R-AXIS-IV'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8541
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   'multi-scan (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             596.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.54
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.844
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4233
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.001Fo² + σ²(Fo) + 0.5]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0910
_reflns_number_gt                3541
_reflns_number_total             4678
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            cv6187.cif
_cod_data_source_block           I
_cod_original_cell_volume        1110.40(10)
_cod_database_code               2201944
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.43010(7) 0.27994(7) 0.45382(4) 0.00550(10) Uani d . 1.00 . . S
S2 0.16572(7) -0.33281(7) 0.45344(4) 0.00510(10) Uani d . 1.00 . . S
S3 0.21040(7) -0.09787(7) 0.14849(4) 0.00530(10) Uani d . 1.00 . . S
S4 0.43052(7) 0.52342(7) 0.78607(4) 0.00550(10) Uani d . 1.00 . . S
Na1 0.59680(10) 0.08050(10) 0.11192(6) 0.0091(2) Uani d . 1.00 . . Na
Na2 0.17600(10) -0.50270(10) 0.08505(6) 0.0102(2) Uani d . 1.00 . . Na
O1 0.3103(2) 0.0041(2) 0.53190(10) 0.0080(4) Uani d . 1.00 . . O
O2 0.3151(2) 0.0318(2) 0.12640(10) 0.0086(4) Uani d . 1.00 . . O
O3 0.2526(2) -0.2459(2) 0.12050(10) 0.0096(4) Uani d . 1.00 . . O
O4 0.0314(2) -0.0916(2) 0.11680(10) 0.0105(4) Uani d . 1.00 . . O
O5 0.0644(2) 0.2550(2) 0.42690(10) 0.0079(4) Uani d . 1.00 . . O
O6 0.3848(2) 0.6765(2) 0.79650(10) 0.0105(4) Uani d . 1.00 . . O
O7 0.3704(2) 0.4248(2) 0.84570(10) 0.0108(5) Uani d . 1.00 . . O
O8 0.6086(2) 0.5273(2) 0.79070(10) 0.0096(4) Uani d . 1.00 . . O
O9 0.8835(2) 0.1779(2) 0.12510(10) 0.0127(5) Uani d . 1.00 . . O
O10 0.7461(2) -0.0932(2) 0.20880(10) 0.0134(5) Uani d . 1.00 . . O
O11 0.4993(2) 0.1736(2) -0.02060(10) 0.0108(5) Uani d . 1.00 . . O
O12 0.2069(2) -0.7417(2) 0.02650(10) 0.0107(4) Uani d . 1.00 . . O
O13 0.1253(2) -0.4631(2) -0.06510(10) 0.0114(5) Uani d . 1.00 . . O
O14 0.1040(2) 0.3651(2) 0.26380(10) 0.0136(5) Uani d . 1.00 . . O
O15 0.7472(2) 0.1531(2) 0.33720(10) 0.0101(4) Uani d . 1.00 . . O
C1 0.2861(3) -0.0281(3) 0.44450(10) 0.0057(6) Uani d . 1.00 . . C
C2 0.2199(3) -0.1744(3) 0.3970(2) 0.0062(6) Uani d . 1.00 . . C
C3 0.2034(3) -0.1983(3) 0.3067(2) 0.0072(6) Uani d . 1.00 . . C
C4 0.2483(3) -0.0743(3) 0.2637(2) 0.0060(6) Uani d . 1.00 . . C
C5 0.3118(3) 0.0708(3) 0.3097(2) 0.0063(6) Uani d . 1.00 . . C
C6 0.3312(3) 0.0948(3) 0.3997(2) 0.0054(6) Uani d . 1.00 . . C
C7 0.1421(3) 0.3105(3) 0.5108(2) 0.0060(6) Uani d . 1.00 . . C
C8 0.0573(3) 0.3548(3) 0.5748(2) 0.0056(6) Uani d . 1.00 . . C
C9 0.1484(3) 0.4215(3) 0.6580(2) 0.0069(6) Uani d . 1.00 . . C
C10 0.3220(3) 0.4378(3) 0.6790(2) 0.0065(6) Uani d . 1.00 . . C
C11 0.4065(3) 0.3875(3) 0.6173(2) 0.0060(6) Uani d . 1.00 . . C
C12 0.3166(3) 0.3260(3) 0.5330(2) 0.0054(6) Uani d . 1.00 . . C
H1 0.285 -0.083 0.554 0.0100 Uiso c . 1.00 . . H
H2 0.157 -0.301 0.279 0.0086 Uiso c . 1.00 . . H
H3 0.345 0.161 0.280 0.0073 Uiso c . 1.00 . . H
H4 -0.038 0.244 0.419 0.0095 Uiso c . 1.00 . . H
H5 0.096 0.455 0.701 0.0083 Uiso c . 1.00 . . H
H6 0.528 0.402 0.636 0.0075 Uiso c . 1.00 . . H
H7 0.938 0.101 0.111 0.0162 Uiso c . 1.00 . . H
H8 0.955 0.235 0.172 0.0162 Uiso c . 1.00 . . H
H9 0.842 -0.092 0.191 0.0168 Uiso c . 1.00 . . H
H10 0.700 -0.193 0.200 0.0169 Uiso c . 1.00 . . H
H11 0.554 0.218 -0.058 0.0143 Uiso c . 1.00 . . H
H12 0.427 0.236 -0.012 0.0144 Uiso c . 1.00 . . H
H13 0.234 -0.812 0.062 0.0126 Uiso c . 1.00 . . H
H14 0.121 -0.793 -0.016 0.0127 Uiso c . 1.00 . . H
H15 0.193 -0.502 -0.096 0.0150 Uiso c . 1.00 . . H
H16 0.139 -0.363 -0.071 0.0149 Uiso c . 1.00 . . H
H17 0.112 0.343 0.3188 0.0168 Uiso c . 1.00 . . H
H18 0.211 0.389 0.260 0.0169 Uiso c . 1.00 . . H
H19 0.698 0.215 0.302 0.0126 Uiso c . 1.00 . . H
H20 0.742 0.066 0.302 0.0125 Uiso c . 1.00 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Na Na 0.036 0.025
;
International Tables for Crystallography
(1992, 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 S1 C12 . . 105.61(11) yes
C2 S2 C8 . 2_556 100.93(11) yes
O2 S3 O3 . . 112.97(11) yes
O2 S3 O4 . . 111.40(11) yes
O3 S3 O4 . . 112.24(11) yes
O2 S3 C4 . . 106.15(11) yes
O3 S3 C4 . . 107.77(11) yes
O4 S3 C4 . . 105.79(11) yes
O6 S4 O7 . . 112.21(11) yes
O6 S4 O8 . . 113.01(11) yes
O7 S4 O8 . . 112.27(11) yes
O6 S4 C10 . . 105.68(11) yes
O7 S4 C10 . . 106.04(11) yes
O8 S4 C10 . . 107.00(11) yes
C1 O1 H1 . . 108.8 no
S3 O2 Na1 . . 134.69(11) yes
S3 O3 Na2 . . 148.88(12) yes
C7 O5 H4 . . 112.6 no
S4 O6 Na1 . 2_666 149.38(11) yes
S4 O8 Na2 . 2_656 127.90(10) yes
H7 O9 H8 . . 104.5 no
H9 O10 H10 . . 104.5 no
Na1 O11 Na1 . 2_655 96.80(7) yes
H11 O11 H12 . . 104.5 no
H13 O12 H14 . . 104.5 no
Na2 O13 Na2 . 2_545 94.18(7) yes
H15 O13 H16 . . 104.5 no
H17 O14 H18 . . 104.5 no
H19 O15 H20 . . 104.5 no
O1 C1 C2 . . 124.1(2) yes
O1 C1 C6 . . 116.6(2) yes
C2 C1 C6 . . 119.3(2) yes
S2 C2 C1 . . 119.80(18) yes
S2 C2 C3 . . 119.92(19) yes
C1 C2 C3 . . 120.2(2) yes
C2 C3 C4 . . 119.4(2) yes
C2 C3 H2 . . 114.9 no
C4 C3 H2 . . 125.7 no
S3 C4 C3 . . 120.07(19) yes
S3 C4 C5 . . 118.89(19) yes
C3 C4 C5 . . 120.9(2) yes
C4 C5 C6 . . 120.1(2) yes
C4 C5 H3 . . 121.7 no
C6 C5 H3 . . 118.2 no
S1 C6 C1 . . 122.96(18) yes
S1 C6 C5 . . 116.68(19) yes
C1 C6 C5 . . 120.1(2) yes
O5 C7 C8 . . 123.5(2) yes
O5 C7 C12 . . 117.0(2) yes
C8 C7 C12 . . 119.4(2) yes
S2 C8 C9 2_556 . 120.93(18) yes
S2 C8 C7 2_556 . 119.39(18) yes
C7 C8 C9 . . 119.6(2) yes
C8 C9 C10 . . 120.2(2) yes
C8 C9 H5 . . 121.4 no
C10 C9 H5 . . 118.3 no
S4 C10 C9 . . 118.03(18) yes
S4 C10 C11 . . 121.50(18) yes
C9 C10 C11 . . 120.5(2) yes
C10 C11 C12 . . 119.5(2) yes
C10 C11 H6 . . 116.6 no
C12 C11 H6 . . 123.8 no
S1 C12 C7 . . 121.24(18) yes
S1 C12 C11 . . 118.07(18) yes
C7 C12 C11 . . 120.6(2) yes
O2 Na1 O6 . 2_666 85.21(7) yes
O2 Na1 O9 . . 166.16(8) yes
O2 Na1 O10 . . 104.32(7) yes
O2 Na1 O11 . . 88.49(7) yes
O2 Na1 O11 . 2_655 79.91(7) yes
O6 Na1 O9 2_666 . 81.28(7) yes
O9 Na1 O10 . . 76.97(7) yes
O9 Na1 O11 . . 95.64(7) yes
O9 Na1 O11 . 2_655 113.65(7) yes
O10 Na1 O11 . . 155.35(8) yes
O11 Na1 O11 . 2_655 83.20(7) yes
S3 Na2 O12 . . 165.22(6) yes
O3 Na2 O12 . . 153.71(8) yes
O3 Na2 O13 . . 87.89(7) yes
O3 Na2 O8 . 2_656 87.03(7) yes
O3 Na2 O12 . . 153.71(8) yes
O3 Na2 O13 . 2_545 102.85(7) yes
O8 Na2 O12 2_656 . 87.12(7) yes
O8 Na2 O13 2_656 . 143.44(7) yes
O8 Na2 O13 2_656 2_545 130.56(7) yes
O12 Na2 O13 . . 81.71(7) yes
O12 Na2 O13 . 2_545 100.41(7) yes
O13 Na2 O13 . 2_545 85.82(7) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C6 . . 1.770(2) yes
S1 C12 . . 1.769(2) yes
S2 C2 . . 1.792(2) yes
S2 C8 . 2_556 1.785(2) yes
S3 O2 . . 1.4590(18) yes
S3 O3 . . 1.4524(18) yes
S3 O4 . . 1.4715(18) yes
S3 C4 . . 1.763(2) yes
S4 O6 . . 1.4590(18) yes
S4 O7 . . 1.4635(18) yes
S4 O8 . . 1.4593(18) yes
S4 C10 . . 1.772(2) yes
O1 C1 . . 1.347(3) yes
O1 H1 . . 0.89 no
O5 C7 . . 1.350(3) yes
O5 H4 . . 0.82 no
O9 H7 . . 0.90 no
O9 H8 . . 0.90 no
O10 H9 . . 0.90 no
O10 H10 . . 0.90 no
O11 H11 . . 0.90 no
O11 H12 . . 0.90 no
O12 H13 . . 0.90 no
O12 H14 . . 0.90 no
O13 H15 . . 0.90 no
O13 H16 . . 0.898 no
O14 H17 . . 0.90 no
O14 H18 . . 0.90 no
O15 H19 . . 0.90 no
O15 H20 . . 0.90 no
C1 C2 . . 1.404(4) yes
C1 C6 . . 1.406(3) yes
C2 C3 . . 1.395(3) yes
C3 C4 . . 1.396(3) yes
C3 H2 . . 0.96 no
C4 C5 . . 1.383(4) yes
C5 C6 . . 1.386(3) yes
C5 H3 . . 1.00 no
C7 C8 . . 1.405(3) yes
C7 C12 . . 1.398(3) yes
C8 C9 . . 1.393(3) yes
C9 C10 . . 1.390(3) yes
C9 H5 . . 0.92 no
C10 C11 . . 1.390(3) yes
C11 C12 . . 1.392(3) yes
C11 H6 . . 0.98 no
Na1 O2 . . 2.382(2) yes
Na1 O6 . 2_666 2.434(2) yes
Na1 O9 . . 2.373(2) yes
Na1 O10 . . 2.531(2) yes
Na1 O11 . . 2.347(2) yes
Na1 O11 . 2_655 2.475(2) yes
Na2 O3 . . 2.252(2) yes
Na2 O8 . 2_656 2.402(2) yes
Na2 O12 . . 2.292(2) yes
Na2 O13 . . 2.387(2) yes
Na2 O13 . 2_545 2.423(2) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O15 2_656 0.90 1.95 2.693(2) 140
O5 H4 O15 1_455 0.82 1.97 2.688(2) 146
O9 H7 O4 1_655 0.90 1.97 2.831(3) 159
O9 H8 O14 1_655 0.90 1.86 2.756(3) 176
O10 H9 O4 1_655 0.90 2.16 3.033(3) 166
O10 H9 O9 . 0.90 2.71 3.055(3) 104
O10 H10 O7 2_656 0.90 2.06 2.939(3) 165
O11 H11 O3 2_655 0.90 2.06 2.894(2) 153
O11 H12 O12 1_565 0.90 2.07 2.858(3) 146
O12 H13 O2 1_545 0.90 1.91 2.796(3) 171
O12 H14 O4 2_545 0.90 1.90 2.793(3) 170
O13 H15 O7 1_544 0.90 2.04 2.935(3) 173
O13 H16 O9 2_655 0.90 1.93 2.787(3) 159
O14 H17 O5 . 0.90 2.04 2.910(3) 163
