#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/03/2230314.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_2230314
loop_
_publ_author_name
'Kuyinu, Ore'
'Purdy, Andrew P.'
'Butcher, Ray J.'
_publ_section_title
;
 Sulfonated 1,3-bis(4-pyridyl)propane
;
_journal_coeditor_code           FL2337
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1534
_journal_paper_doi               10.1107/S1600536811018563
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H14 N2 O6 S2'
_chemical_formula_moiety         'C13 H14 N2 O6 S2'
_chemical_formula_sum            'C13 H14 N2 O6 S2'
_chemical_formula_weight         358.38
_chemical_name_systematic
;
4-[3-(3-sulfonatopyridin-1-ium-4-yl)propyl]pyridin-1-ium-3-sulfonate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7132(2)
_cell_length_b                   11.2624(2)
_cell_length_c                   13.5369(2)
_cell_measurement_reflns_used    3437
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      77.3813
_cell_measurement_theta_min      4.5485
_cell_volume                     1480.85(5)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Ruby Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3960
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         77.58
_diffrn_reflns_theta_min         5.11
_exptl_absorpt_coefficient_mu    3.589
_exptl_absorpt_correction_T_max  0.626
_exptl_absorpt_correction_T_min  0.290
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis PRO (Oxford Diffraction, 2007), based on expressions derived
by
Clark & Reid (1995)]
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.7731
_exptl_crystal_size_mid          0.2511
_exptl_crystal_size_min          0.1900
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.518
_refine_ls_abs_structure_details 'Flack (1983), 899 Friedel pairs'
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2714
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0380
_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)+(0.0719P)²+0.3816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1056
_reflns_number_gt                2593
_reflns_number_total             2714
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2337.cif
_cod_data_source_block           I
_cod_database_code               2230314
_cod_database_fobs_code          2230314
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.28273(7) 0.82506(6) 0.18353(4) 0.03490(17) Uani d . 1 1 . .
S S2 0.25484(7) 0.69702(6) 0.73312(6) 0.0450(2) Uani d . 1 1 . .
O O1A 0.1398(2) 0.8521(2) 0.16464(17) 0.0501(6) Uani d . 1 1 . .
O O2A 0.3744(3) 0.8523(3) 0.10328(15) 0.0587(7) Uani d . 1 1 . .
O O3A 0.3027(2) 0.70553(17) 0.22295(16) 0.0444(5) Uani d . 1 1 . .
O O1B 0.2815(3) 0.6781(2) 0.8361(2) 0.0741(8) Uani d U 1 1 . .
O O2B 0.3281(3) 0.80026(19) 0.69595(18) 0.0521(5) Uani d . 1 1 . .
O O3B 0.1119(3) 0.6967(3) 0.7050(3) 0.0883(11) Uani d U 1 1 . .
N N1A 0.4665(3) 1.0862(2) 0.3287(2) 0.0478(6) Uani d . 1 1 . .
H H1AA 0.5265 1.1394 0.3135 0.057 Uiso calc R 1 1 . .
N N1B 0.4929(2) 0.4168(2) 0.68491(18) 0.0356(5) Uani d . 1 1 . .
H H1BA 0.5502 0.3772 0.7204 0.043 Uiso calc R 1 1 . .
C C1 0.1965(3) 0.8097(3) 0.41421(19) 0.0386(6) Uani d . 1 1 . .
H H1A 0.1477 0.7738 0.3593 0.046 Uiso calc R 1 1 . .
H H1B 0.1293 0.8374 0.4620 0.046 Uiso calc R 1 1 . .
C C2 0.2932(3) 0.7187(3) 0.4620(2) 0.0424(6) Uani d . 1 1 . .
H H2A 0.3445 0.7570 0.5147 0.051 Uiso calc R 1 1 . .
H H2B 0.3588 0.6912 0.4131 0.051 Uiso calc R 1 1 . .
C C3 0.2151(3) 0.6114(3) 0.5045(2) 0.0479(7) Uani d . 1 1 . .
H H3A 0.1350 0.6384 0.5409 0.057 Uiso calc R 1 1 . .
H H3B 0.1841 0.5605 0.4512 0.057 Uiso calc R 1 1 . .
C C1A 0.2832(3) 0.9119(2) 0.37844(17) 0.0326(5) Uani d . 1 1 . .
C C2A 0.3323(3) 0.9228(2) 0.28185(18) 0.0301(5) Uani d . 1 1 . .
C C3A 0.4240(3) 1.0107(2) 0.2592(2) 0.0391(6) Uani d . 1 1 . .
H H3AA 0.4569 1.0178 0.1950 0.047 Uiso calc R 1 1 . .
C C4A 0.4185(4) 1.0818(3) 0.4211(3) 0.0553(9) Uani d . 1 1 . .
H H4AA 0.4473 1.1374 0.4675 0.066 Uiso calc R 1 1 . .
C C5A 0.3276(4) 0.9959(3) 0.4470(2) 0.0486(7) Uani d . 1 1 . .
H H5AA 0.2945 0.9929 0.5114 0.058 Uiso calc R 1 1 . .
C C1B 0.3094(3) 0.5428(2) 0.57229(19) 0.0356(5) Uani d . 1 1 . .
C C2B 0.3329(3) 0.5730(2) 0.67150(19) 0.0310(5) Uani d . 1 1 . .
C C3B 0.4251(3) 0.5075(2) 0.72588(19) 0.0338(5) Uani d . 1 1 . .
H H3BA 0.4405 0.5264 0.7918 0.041 Uiso calc R 1 1 . .
C C4B 0.4747(3) 0.3857(2) 0.5911(2) 0.0401(6) Uani d . 1 1 . .
H H4BA 0.5246 0.3229 0.5645 0.048 Uiso calc R 1 1 . .
C C5B 0.3826(3) 0.4462(3) 0.53385(19) 0.0414(6) Uani d . 1 1 . .
H H5BA 0.3684 0.4230 0.4687 0.050 Uiso calc R 1 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2A S1 O1A . . 114.62(15) ?
O2A S1 O3A . . 112.98(15) ?
O1A S1 O3A . . 112.74(14) ?
O2A S1 C2A . . 105.27(13) ?
O1A S1 C2A . . 105.09(12) ?
O3A S1 C2A . . 105.00(11) ?
O1B S2 O3B . . 115.5(2) ?
O1B S2 O2B . . 111.54(16) ?
O3B S2 O2B . . 112.5(2) ?
O1B S2 C2B . . 105.08(15) ?
O3B S2 C2B . . 106.43(15) ?
O2B S2 C2B . . 104.76(13) ?
C3A N1A C4A . . 121.9(3) ?
C3A N1A H1AA . . 119.1 ?
C4A N1A H1AA . . 119.1 ?
C4B N1B C3B . . 122.2(2) ?
C4B N1B H1BA . . 118.9 ?
C3B N1B H1BA . . 118.9 ?
C1A C1 C2 . . 107.7(2) ?
C1A C1 H1A . . 110.2 ?
C2 C1 H1A . . 110.2 ?
C1A C1 H1B . . 110.2 ?
C2 C1 H1B . . 110.2 ?
H1A C1 H1B . . 108.5 ?
C1 C2 C3 . . 112.4(2) ?
C1 C2 H2A . . 109.1 ?
C3 C2 H2A . . 109.1 ?
C1 C2 H2B . . 109.1 ?
C3 C2 H2B . . 109.1 ?
H2A C2 H2B . . 107.9 ?
C1B C3 C2 . . 109.3(2) ?
C1B C3 H3A . . 109.8 ?
C2 C3 H3A . . 109.8 ?
C1B C3 H3B . . 109.8 ?
C2 C3 H3B . . 109.8 ?
H3A C3 H3B . . 108.3 ?
C5A C1A C2A . . 117.2(3) ?
C5A C1A C1 . . 118.5(2) ?
C2A C1A C1 . . 124.0(2) ?
C3A C2A C1A . . 119.8(2) ?
C3A C2A S1 . . 116.9(2) ?
C1A C2A S1 . . 123.30(19) ?
N1A C3A C2A . . 120.4(3) ?
N1A C3A H3AA . . 119.8 ?
C2A C3A H3AA . . 119.8 ?
N1A C4A C5A . . 119.7(3) ?
N1A C4A H4AA . . 120.1 ?
C5A C4A H4AA . . 120.1 ?
C4A C5A C1A . . 120.9(3) ?
C4A C5A H5AA . . 119.5 ?
C1A C5A H5AA . . 119.5 ?
C5B C1B C2B . . 117.5(2) ?
C5B C1B C3 . . 118.7(3) ?
C2B C1B C3 . . 123.8(3) ?
C3B C2B C1B . . 119.2(2) ?
C3B C2B S2 . . 116.38(19) ?
C1B C2B S2 . . 124.4(2) ?
N1B C3B C2B . . 120.6(2) ?
N1B C3B H3BA . . 119.7 ?
C2B C3B H3BA . . 119.7 ?
N1B C4B C5B . . 119.9(3) ?
N1B C4B H4BA . . 120.1 ?
C5B C4B H4BA . . 120.1 ?
C4B C5B C1B . . 120.6(2) ?
C4B C5B H5BA . . 119.7 ?
C1B C5B H5BA . . 119.7 ?
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 O2A . 1.438(2) ?
S1 O1A . 1.444(2) ?
S1 O3A . 1.461(2) ?
S1 C2A . 1.793(3) ?
S2 O1B . 1.433(3) ?
S2 O3B . 1.439(3) ?
S2 O2B . 1.453(2) ?
S2 C2B . 1.795(2) ?
N1A C3A . 1.334(4) ?
N1A C4A . 1.337(5) ?
N1A H1AA . 0.8600 ?
N1B C4B . 1.329(4) ?
N1B C3B . 1.336(3) ?
N1B H1BA . 0.8600 ?
C1 C1A . 1.506(4) ?
C1 C2 . 1.534(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.539(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C1B . 1.509(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C1A C5A . 1.394(4) ?
C1A C2A . 1.397(3) ?
C2A C3A . 1.366(4) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.356(5) ?
C4A H4AA . 0.9300 ?
C5A H5AA . 0.9300 ?
C1B C5B . 1.400(4) ?
C1B C2B . 1.404(4) ?
C2B C3B . 1.375(4) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.366(4) ?
C4B H4BA . 0.9300 ?
C5B H5BA . 0.9300 ?
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
N1A H1AA O3A 3_655 0.86 1.88 2.706(3) 159
N1A H1AA S1 3_655 0.86 2.79 3.633(3) 165
N1B H1BA O2B 3_646 0.86 1.85 2.710(3) 176
N1B H1BA S2 3_646 0.86 2.85 3.655(2) 158
C3B H3BA O1A 4_566 0.93 2.44 3.008(3) 119
C4B H4BA O2A 3_645 0.93 2.50 3.035(3) 117
C5B H5BA O1B 2_564 0.93 2.58 3.416(4) 150
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1A C1 C2 C3 . . . . 178.2(2) ?
C1 C2 C3 C1B . . . . -165.5(3) ?
C2 C1 C1A C5A . . . . -78.8(3) ?
C2 C1 C1A C2A . . . . 95.4(3) ?
C5A C1A C2A C3A . . . . 2.3(4) ?
C1 C1A C2A C3A . . . . -172.0(2) ?
C5A C1A C2A S1 . . . . -178.4(2) ?
C1 C1A C2A S1 . . . . 7.3(4) ?
O2A S1 C2A C3A . . . . 9.9(2) ?
O1A S1 C2A C3A . . . . -111.5(2) ?
O3A S1 C2A C3A . . . . 129.4(2) ?
O2A S1 C2A C1A . . . . -169.4(2) ?
O1A S1 C2A C1A . . . . 69.2(2) ?
O3A S1 C2A C1A . . . . -50.0(2) ?
C4A N1A C3A C2A . . . . -2.3(5) ?
C1A C2A C3A N1A . . . . -0.2(4) ?
S1 C2A C3A N1A . . . . -179.5(2) ?
C3A N1A C4A C5A . . . . 2.4(5) ?
N1A C4A C5A C1A . . . . -0.1(5) ?
C2A C1A C5A C4A . . . . -2.2(5) ?
C1 C1A C5A C4A . . . . 172.4(3) ?
C2 C3 C1B C5B . . . . -94.3(3) ?
C2 C3 C1B C2B . . . . 82.9(3) ?
C5B C1B C2B C3B . . . . -0.1(4) ?
C3 C1B C2B C3B . . . . -177.4(3) ?
C5B C1B C2B S2 . . . . 177.4(2) ?
C3 C1B C2B S2 . . . . 0.2(4) ?
O1B S2 C2B C3B . . . . -15.5(3) ?
O3B S2 C2B C3B . . . . -138.4(3) ?
O2B S2 C2B C3B . . . . 102.2(2) ?
O1B S2 C2B C1B . . . . 166.9(2) ?
O3B S2 C2B C1B . . . . 44.0(3) ?
O2B S2 C2B C1B . . . . -75.4(2) ?
C4B N1B C3B C2B . . . . -0.1(4) ?
C1B C2B C3B N1B . . . . 0.7(4) ?
S2 C2B C3B N1B . . . . -177.00(19) ?
C3B N1B C4B C5B . . . . -1.0(4) ?
N1B C4B C5B C1B . . . . 1.6(4) ?
C2B C1B C5B C4B . . . . -1.0(4) ?
C3 C1B C5B C4B . . . . 176.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656700
