#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/57/2005712.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_2005712
loop_
_publ_author_name
'Coupar, P. I.'
'Ferguson, G.'
'Glidewell, C.'
_publ_section_title
;
 Piperazine--4,4'-Sulfonyldiphenol (1/2): a Self-Assembled Channel
 Structure
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              3052
_journal_page_last               3055
_journal_paper_doi               10.1107/S010827019601133X
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'C4 H12 N2 2+ , 2C12 H9 O4 S -'
_chemical_formula_moiety         '(C4 H12 N2) 2+ , 2(C12 H9 O4 S) -'
_chemical_formula_sum            'C28 H30 N2 O8 S2'
_chemical_formula_weight         586.66
_chemical_name_common            'Piperazine--4,4'-sulfonyldiphenol (1/2)'
_chemical_name_systematic
;
piperazin-1,4-diium di(4,4'-sulfonyldiphenolate)
.
;
_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                100.619(13)
_cell_angle_beta                 92.757(7)
_cell_angle_gamma                96.479(8)
_cell_formula_units_Z            1
_cell_length_a                   5.6703(5)
_cell_length_b                   11.4012(12)
_cell_length_c                   11.6108(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      20.52
_cell_measurement_theta_min      10.35
_cell_volume                     731.22(13)
_computing_cell_refinement       'SET4 and CELDIM in CAD-4/PC'
_computing_data_collection       'CAD4/PC Software (Enraf-Nonius, 1992)'
_computing_data_reduction
'DATRD2 in NRCVAX94 (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_molecular_graphics
'NRCVAX94, PLATON (Spek, 1995a), PLUTON (Spek 1995b), ORTEPII (Johnson, 1976)'
_computing_publication_material
'NRCVAX94, SHELXL93 and WordPerfect macro PREPCIF'
_computing_structure_refinement  'NRCVAX94 and SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SOLVER in NRCVAX'
_diffrn_ambient_temperature      294.0(10)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3165
_diffrn_reflns_theta_max         26.9
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        4.8
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  1.0
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.981
_refine_ls_goodness_of_fit_obs   1.127
_refine_ls_hydrogen_treatment
'H atoms riding (C-H 0.93 and 0.97, N-H 0.90, O-H 0.82\%A)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_restrained_S_obs      1.127
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_obs          0.0531
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0789P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1416
_refine_ls_wR_factor_obs         0.1276
_reflns_number_observed          2005
_reflns_number_total             3165
_reflns_observed_criterion       >2\s(I)
_cod_data_source_file            ab1418.cif
_cod_data_source_block           9645
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0789P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed
to 'calc'. New tag '_refine_ls_weighting_details' was created. The
value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0789P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2005712
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
S1 1 0.07376(12) 0.21301(6) 0.22491(5) 0.0332(2) Uani d . S
O11 1 0.3226(3) 0.2010(2) 0.2425(2) 0.0417(5) Uani d . O
O12 1 -0.0953(4) 0.1398(2) 0.2791(2) 0.0448(5) Uani d . O
O14 1 -0.1826(4) 0.1347(2) -0.2818(2) 0.0431(5) Uani d . O
O24 1 -0.0528(4) 0.7193(2) 0.3898(2) 0.0563(6) Uani d . O
C11 1 -0.0015(4) 0.1857(2) 0.0740(2) 0.0307(6) Uani d . C
C12 1 0.1632(5) 0.2198(3) -0.0011(2) 0.0472(7) Uani d . C
C13 1 0.1023(5) 0.2032(3) -0.1199(2) 0.0494(8) Uani d . C
C14 1 -0.1241(5) 0.1500(2) -0.1668(2) 0.0337(6) Uani d . C
C15 1 -0.2844(5) 0.1152(3) -0.0898(2) 0.0462(7) Uani d . C
C16 1 -0.2255(5) 0.1332(3) 0.0294(2) 0.0448(7) Uani d . C
C21 1 0.0381(5) 0.3643(2) 0.2767(2) 0.0330(6) Uani d . C
C22 1 -0.1554(5) 0.3951(3) 0.3379(3) 0.0470(7) Uani d . C
C23 1 -0.1809(6) 0.5139(3) 0.3758(3) 0.0515(8) Uani d . C
C24 1 -0.0179(5) 0.6038(2) 0.3523(2) 0.0400(6) Uani d . C
C25 1 0.1763(6) 0.5732(3) 0.2918(3) 0.0551(8) Uani d . C
C26 1 0.2059(6) 0.4539(3) 0.2553(3) 0.0504(8) Uani d . C
N1 1 -0.5003(4) -0.0353(2) -0.3886(2) 0.0295(5) Uani d . N
C2 1 -0.3893(5) -0.1046(2) -0.4873(2) 0.0345(6) Uani d . C
C3 1 -0.6986(4) 0.0225(2) -0.4317(2) 0.0343(6) Uani d . C
H24 1 0.0364 0.7631 0.3579 0.084 Uiso calc R H
H12 1 0.3157 0.2541 0.0286 0.057 Uiso calc R H
H13 1 0.2137 0.2278 -0.1696 0.059 Uiso calc R H
H15 1 -0.4359 0.0787 -0.1190 0.055 Uiso calc R H
H16 1 -0.3371 0.1098 0.0795 0.054 Uiso calc R H
H22 1 -0.2684 0.3353 0.3535 0.056 Uiso calc R H
H23 1 -0.3105 0.5341 0.4182 0.062 Uiso calc R H
H25 1 0.2879 0.6331 0.2755 0.066 Uiso calc R H
H26 1 0.3392 0.4338 0.2162 0.060 Uiso calc R H
H1A 1 -0.3903 0.0215 -0.3464 0.035 Uiso calc R H
H1B 1 -0.5552 -0.0847 -0.3411 0.035 Uiso calc R H
H2A 1 -0.5047 -0.1690 -0.5301 0.041 Uiso calc R H
H2B 1 -0.2573 -0.1401 -0.4573 0.041 Uiso calc R H
H3A 1 -0.7671 0.0685 -0.3656 0.041 Uiso calc R H
H3B 1 -0.8217(4) -0.0387(2) -0.4733(2) 0.041 Uiso calc R H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 1 -5
0 -4 -5
-2 -3 0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O11 S1 O12 . 118.03(11) y
O11 S1 C11 . 108.17(12) y
O11 S1 C21 . 107.59(12) y
O12 S1 C11 . 108.71(12) y
O12 S1 C21 . 107.78(12) y
C11 S1 C21 . 105.93(11) y
S1 C11 C12 . 119.7(2) ?
S1 C11 C16 . 120.6(2) ?
C12 C11 C16 . 119.6(2) ?
C11 C12 C13 . 120.2(3) ?
C12 C13 C14 . 121.0(3) ?
O14 C14 C13 . 120.8(2) ?
O14 C14 C15 . 121.7(2) ?
C13 C14 C15 . 117.6(2) ?
C14 C15 C16 . 121.7(3) ?
C11 C16 C15 . 119.9(3) ?
S1 C21 C22 . 121.0(2) ?
S1 C21 C26 . 119.5(2) ?
C22 C21 C26 . 119.5(3) ?
C21 C22 C23 . 119.9(3) ?
C22 C23 C24 . 121.1(3) ?
O24 C24 C23 . 118.9(3) ?
O24 C24 C25 . 122.1(3) ?
C23 C24 C25 . 119.1(3) ?
C24 C25 C26 . 120.3(3) ?
C21 C26 C25 . 120.2(3) ?
C2 N1 C3 . 111.0(2) y
N1 C2 C3 2_454 109.6(2) y
N1 C3 C2 2_454 110.2(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O11 . 1.442(2) y
S1 O12 . 1.443(2) y
S1 C11 . 1.746(2) y
S1 C21 . 1.757(3) y
O14 C14 . 1.335(3) y
O24 C24 . 1.348(3) y
C11 C12 . 1.380(4) ?
C11 C16 . 1.375(4) ?
C12 C13 . 1.379(4) ?
C13 C14 . 1.395(4) ?
C14 C15 . 1.383(4) ?
C15 C16 . 1.380(4) ?
C21 C22 . 1.380(4) ?
C21 C26 . 1.381(4) ?
C22 C23 . 1.372(4) ?
C23 C24 . 1.376(4) ?
C24 C25 . 1.378(4) ?
C25 C26 . 1.379(4) ?
N1 C2 . 1.477(3) y
N1 C3 . 1.477(3) y
C2 C3 2_454 1.508(3) y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O11 S1 C11 C16 . 147.6(2) y
O12 S1 C11 C16 . 18.3(3) y
C21 S1 C11 C16 . -97.3(2) y
O11 S1 C11 C12 . -34.1(3) y
O12 S1 C11 C12 . -163.4(2) y
C21 S1 C11 C12 . 81.0(2) y
C16 C11 C12 C13 . 1.1(4) ?
S1 C11 C12 C13 . -177.3(2) ?
C11 C12 C13 C14 . -1.1(5) ?
C12 C13 C14 O14 . 179.6(3) ?
C12 C13 C14 C15 . 0.2(4) ?
O14 C14 C15 C16 . -178.7(3) ?
C13 C14 C15 C16 . 0.7(4) ?
C12 C11 C16 C15 . -0.1(4) ?
S1 C11 C16 C15 . 178.2(2) ?
C14 C15 C16 C11 . -0.8(4) ?
O11 S1 C21 C26 . 40.1(2) y
O12 S1 C21 C26 . 168.4(2) y
C11 S1 C21 C26 . -75.4(2) y
O11 S1 C21 C22 . -140.1(2) y
O12 S1 C21 C22 . -11.9(3) y
C11 S1 C21 C22 . 104.3(2) y
C26 C21 C22 C23 . 0.7(4) ?
S1 C21 C22 C23 . -179.0(2) ?
C21 C22 C23 C24 . 1.0(5) ?
C22 C23 C24 O24 . 178.9(3) ?
C22 C23 C24 C25 . -1.4(5) ?
O24 C24 C25 C26 . 179.8(3) ?
C23 C24 C25 C26 . 0.2(5) ?
C24 C25 C26 C21 . 1.5(5) ?
C22 C21 C26 C25 . -2.0(4) ?
S1 C21 C26 C25 . 177.8(2) ?
C3 N1 C2 C3 2_454 58.0(3) y
C2 N1 C3 C2 2_454 -58.4(3) y
