#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/71/2217141.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_2217141
loop_
_publ_author_name
'Chao Shen-Tu'
'Lin-Lin Ma'
'Wei Xu'
'Ying Chen'
'Zhi-Min Jin'
_publ_section_title
;
 Redetermination of ethylenediammonium
 bis(p-methylbenzenesulfonate) monohydrate
;
_journal_coeditor_code           IS2252
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o346
_journal_page_last               o346
_journal_paper_doi               10.1107/S1600536807066573
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C2 H10 N2 2+, 2C7 H7 O3 S -, H2 O'
_chemical_formula_moiety         'C2 H10 N2 2+, 2(C7 H7 O3 S -), H2 O'
_chemical_formula_sum            'C16 H26 N2 O7 S2'
_chemical_formula_weight         422.53
_chemical_name_systematic
;
ethylenediammonium bis(p-methylbenzenesulfonate) monohydrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 111.770(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.302(2)
_cell_length_b                   7.7240(10)
_cell_length_c                   12.648(2)
_cell_measurement_reflns_used    31
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.28
_cell_measurement_theta_min      3.28
_cell_volume                     1025.4(3)
_computing_cell_refinement       'XSCANS (Siemens, 1994)'
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'SHELXTL (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  'SHELXTL (Bruker, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_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  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2942
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        4.97
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.452
_refine_ls_abs_structure_details 'Flack (1983), 631 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.13(14)
_refine_ls_extinction_coef       0.041(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         2693
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0525
_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)+(0.0975P)²+0.2733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1512
_reflns_number_gt                2293
_reflns_number_total             2693
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2252.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2217141
_cod_database_fobs_code          2217141
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_disorder_assembly
_atom_site_disorder_group
S S1 0.39487(9) 1.37382(17) 0.69865(8) 0.0449(3) Uani d . 1 . .
S S2 0.23545(10) 0.3854(2) 0.30145(8) 0.0486(3) Uani d D 1 . .
N N1 0.1694(3) 1.0595(6) 0.4993(3) 0.0493(9) Uani d . 1 . .
H H1A 0.0876 1.0493 0.4898 0.074 Uiso calc R 1 . .
H H1B 0.1759 1.1189 0.4415 0.074 Uiso calc R 1 . .
H H1C 0.2108 1.1151 0.5642 0.074 Uiso calc R 1 . .
N N2 0.4215(4) 0.7319(6) 0.5269(4) 0.0572(10) Uani d . 1 . .
H H2A 0.5031 0.7456 0.5365 0.086 Uiso calc R 1 . .
H H2B 0.3816 0.6734 0.4629 0.086 Uiso calc R 1 . .
H H2C 0.4163 0.6734 0.5856 0.086 Uiso calc R 1 . .
O O3 0.4599(3) 1.3428(6) 0.6225(3) 0.0651(11) Uani d . 1 . .
O O1 0.3297(4) 1.5388(6) 0.6770(4) 0.0644(11) Uani d . 1 . .
O O2 0.3079(4) 1.2347(7) 0.6970(4) 0.0806(14) Uani d . 1 . .
O O4 0.3036(16) 0.5455(15) 0.3399(9) 0.074(4) Uani d PD 0.412(14) A 1
O O5 0.1256(9) 0.3402(16) 0.3317(8) 0.073(4) Uani d PD 0.412(14) A 1
O O6 0.3193(14) 0.2405(15) 0.3414(10) 0.074(4) Uani d PD 0.412(14) A 1
O O4' 0.3607(7) 0.4619(15) 0.3379(6) 0.072(3) Uani d PD 0.588(14) A 2
O O5' 0.1431(8) 0.4885(14) 0.3320(7) 0.090(4) Uani d PD 0.588(14) A 2
O O6' 0.2406(12) 0.2116(11) 0.3368(8) 0.091(3) Uani d PD 0.588(14) A 2
O O7 0.0703(3) 0.4716(7) 0.5140(3) 0.0804(14) Uani d D 1 . .
H H7D 0.0782 0.4933 0.4533 0.097 Uiso d D 1 . .
H H7E 0.1349 0.4841 0.5713 0.097 Uiso d D 1 . .
C C1 0.5101(3) 1.3818(7) 0.8381(3) 0.0373(7) Uani d . 1 . .
C C2 0.4835(4) 1.4629(7) 0.9233(4) 0.0482(10) Uani d . 1 . .
H H2 0.4066 1.5206 0.9070 0.058 Uiso calc R 1 . .
C C3 0.5726(4) 1.4581(7) 1.0342(4) 0.0531(11) Uani d . 1 . .
H H3 0.5544 1.5137 1.0916 0.064 Uiso calc R 1 . .
C C4 0.6870(4) 1.3731(8) 1.0608(3) 0.0462(9) Uani d . 1 . .
C C5 0.7114(4) 1.2905(7) 0.9742(4) 0.0496(11) Uani d . 1 . .
H H5 0.7879 1.2313 0.9911 0.060 Uiso calc R 1 . .
C C6 0.6248(4) 1.2935(7) 0.8628(4) 0.0463(10) Uani d . 1 . .
H H6 0.6429 1.2375 0.8055 0.056 Uiso calc R 1 . .
C C7 0.7803(5) 1.3664(10) 1.1808(4) 0.0645(13) Uani d . 1 . .
H H7A 0.7475 1.4305 1.2290 0.097 Uiso calc R 1 . .
H H7B 0.8597 1.4161 1.1848 0.097 Uiso calc R 1 . .
H H7C 0.7937 1.2481 1.2058 0.097 Uiso calc R 1 . .
C C8 0.1792(3) 0.3870(7) 0.1514(3) 0.0392(8) Uani d . 1 A .
C C9 0.0644(4) 0.4651(7) 0.0900(4) 0.0467(10) Uani d . 1 . .
H H9 0.0167 0.5167 0.1275 0.056 Uiso calc R 1 A .
C C10 0.0205(4) 0.4663(8) -0.0284(4) 0.0529(12) Uani d . 1 A .
H H10 -0.0564 0.5204 -0.0696 0.063 Uiso calc R 1 . .
C C11 0.0887(4) 0.3890(8) -0.0854(3) 0.0514(10) Uani d . 1 . .
C C12 0.2040(4) 0.3120(7) -0.0222(4) 0.0515(11) Uani d . 1 A .
H H12 0.2520 0.2607 -0.0595 0.062 Uiso calc R 1 . .
C C13 0.2487(4) 0.3101(7) 0.0948(4) 0.0484(10) Uani d . 1 . .
H H13 0.3259 0.2568 0.1358 0.058 Uiso calc R 1 A .
C C14 0.0403(7) 0.3881(13) -0.2143(4) 0.0838(18) Uani d . 1 A .
H H14A -0.0405 0.4460 -0.2442 0.126 Uiso calc R 1 . .
H H14B 0.0307 0.2707 -0.2411 0.126 Uiso calc R 1 . .
H H14C 0.1002 0.4470 -0.2391 0.126 Uiso calc R 1 . .
C C15 0.2250(4) 0.8868(9) 0.5035(4) 0.0552(11) Uani d . 1 . .
H H15A 0.1797 0.8254 0.4332 0.066 Uiso calc R 1 . .
H H15B 0.2170 0.8209 0.5659 0.066 Uiso calc R 1 . .
C C16 0.3611(5) 0.9038(9) 0.5199(6) 0.0727(16) Uani d . 1 . .
H H16A 0.4054 0.9679 0.5893 0.087 Uiso calc R 1 . .
H H16B 0.3684 0.9683 0.4568 0.087 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
_geom_angle_publ_flag
O3 S1 O1 111.9(2) ?
O3 S1 O2 112.4(3) ?
O1 S1 O2 110.8(3) ?
O3 S1 C1 107.82(18) ?
O1 S1 C1 107.1(2) ?
O2 S1 C1 106.6(2) ?
O6 S2 O4 110.5(8) ?
O6 S2 O5 103.5(8) n
O4 S2 O5 120.8(8) n
O6' S2 O4' 111.6(6) ?
O6' S2 O5' 112.4(6) ?
O4' S2 O5' 113.7(6) ?
O6' S2 C8 107.7(4) ?
O6 S2 C8 108.2(5) ?
O4 S2 C8 107.0(5) ?
O4' S2 C8 105.1(3) ?
O5 S2 C8 106.2(4) ?
O5' S2 C8 105.7(3) ?
C15 N1 H1A 109.5 ?
C15 N1 H1B 109.5 ?
H1A N1 H1B 109.5 ?
C15 N1 H1C 109.5 ?
H1A N1 H1C 109.5 ?
H1B N1 H1C 109.5 ?
C16 N2 H2A 109.5 ?
C16 N2 H2B 109.5 ?
H2A N2 H2B 109.5 ?
C16 N2 H2C 109.5 ?
H2A N2 H2C 109.5 ?
H2B N2 H2C 109.5 ?
H7D O7 H7E 115.5 ?
C2 C1 C6 120.2(4) ?
C2 C1 S1 120.4(3) ?
C6 C1 S1 119.2(3) ?
C1 C2 C3 119.5(4) ?
C1 C2 H2 120.2 ?
C3 C2 H2 120.2 ?
C4 C3 C2 121.5(4) ?
C4 C3 H3 119.2 ?
C2 C3 H3 119.2 ?
C3 C4 C5 118.2(4) ?
C3 C4 C7 120.7(4) ?
C5 C4 C7 121.1(4) ?
C4 C5 C6 121.7(4) ?
C4 C5 H5 119.2 ?
C6 C5 H5 119.2 ?
C5 C6 C1 118.9(4) ?
C5 C6 H6 120.5 ?
C1 C6 H6 120.5 ?
C4 C7 H7A 109.5 ?
C4 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C4 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C13 C8 C9 119.6(4) ?
C13 C8 S2 120.6(3) ?
C9 C8 S2 119.8(3) ?
C8 C9 C10 119.6(4) ?
C8 C9 H9 120.2 ?
C10 C9 H9 120.2 ?
C11 C10 C9 121.1(4) ?
C11 C10 H10 119.4 ?
C9 C10 H10 119.4 ?
C10 C11 C12 118.4(4) ?
C10 C11 C14 121.2(5) ?
C12 C11 C14 120.4(5) ?
C13 C12 C11 121.2(4) ?
C13 C12 H12 119.4 ?
C11 C12 H12 119.4 ?
C12 C13 C8 120.1(4) ?
C12 C13 H13 119.9 ?
C8 C13 H13 119.9 ?
C11 C14 H14A 109.5 ?
C11 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C11 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
N1 C15 C16 109.5(5) ?
N1 C15 H15A 109.8 ?
C16 C15 H15A 109.8 ?
N1 C15 H15B 109.8 ?
C16 C15 H15B 109.8 ?
H15A C15 H15B 108.2 ?
C15 C16 N2 111.2(5) ?
C15 C16 H16A 109.4 ?
N2 C16 H16A 109.4 ?
C15 C16 H16B 109.4 ?
N2 C16 H16B 109.4 ?
H16A C16 H16B 108.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O3 1.432(3) n
S1 O1 1.446(4) n
S1 O2 1.451(4) n
S1 C1 1.762(4) ?
S2 O6' 1.410(8) ?
S2 O6 1.432(9) n
S2 O4 1.442(8) n
S2 O4' 1.442(7) ?
S2 O5 1.471(8) n
S2 O5' 1.473(7) ?
S2 C8 1.764(4) ?
N1 C15 1.468(8) n
N1 H1A 0.8900 ?
N1 H1B 0.8900 ?
N1 H1C 0.8900 ?
N2 C16 1.480(7) n
N2 H2A 0.8900 ?
N2 H2B 0.8900 ?
N2 H2C 0.8900 ?
O7 H7D 0.8228 ?
O7 H7E 0.8218 ?
C1 C2 1.372(6) n
C1 C6 1.394(6) n
C2 C3 1.391(7) n
C2 H2 0.9300 ?
C3 C4 1.376(7) n
C3 H3 0.9300 ?
C4 C5 1.381(7) n
C4 C7 1.494(6) ?
C5 C6 1.386(7) n
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
C8 C13 1.379(6) n
C8 C9 1.379(6) n
C9 C10 1.392(6) n
C9 H9 0.9300 ?
C10 C11 1.372(7) n
C10 H10 0.9300 ?
C11 C12 1.385(7) n
C11 C14 1.515(6) ?
C12 C13 1.374(7) n
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 C16 1.480(7) n
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
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
_geom_hbond_publ_flag
N1 H1A O7 2_556 0.89 1.87 2.736(7) 165 y
N1 H1B O5 1_565 0.89 2.14 2.942(8) 149 y
N1 H1B O6 1_565 0.89 2.57 3.365(5) 148 y
N1 H1B O6' 1_565 0.89 1.88 2.735(8) 162 y
N1 H1C O2 1_555 0.89 1.87 2.761(6) 176 y
N2 H2A O6 2_656 0.89 2.03 2.780(7) 142 y
N2 H2B O4 1_555 0.89 1.78 2.665(5) 177 y
N2 H2C O1 1_545 0.89 2.05 2.893(6) 157 y
O7 H7D O5 1_555 0.82 2.15 2.793(5) 134 y
O7 H7E O1 1_545 0.82 2.15 2.938(9) 160 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
_geom_torsion_publ_flag
O3 S1 C1 C2 158.9(4) ?
O1 S1 C1 C2 38.3(5) ?
O2 S1 C1 C2 -80.3(5) ?
O3 S1 C1 C6 -26.0(5) ?
O1 S1 C1 C6 -146.6(4) ?
O2 S1 C1 C6 94.8(4) ?
C6 C1 C2 C3 0.8(7) ?
S1 C1 C2 C3 175.9(4) ?
C1 C2 C3 C4 -0.3(8) ?
C2 C3 C4 C5 -0.5(8) ?
C2 C3 C4 C7 -178.8(5) ?
C3 C4 C5 C6 0.7(8) ?
C7 C4 C5 C6 179.0(5) ?
C4 C5 C6 C1 -0.2(8) ?
C2 C1 C6 C5 -0.6(7) ?
S1 C1 C6 C5 -175.7(4) ?
O6' S2 C8 C13 -63.6(7) ?
O6 S2 C8 C13 -24.9(9) ?
O4 S2 C8 C13 94.2(9) ?
O4' S2 C8 C13 55.5(7) ?
O5 S2 C8 C13 -135.5(7) ?
O5' S2 C8 C13 176.0(6) ?
O6' S2 C8 C9 116.2(7) ?
O6 S2 C8 C9 154.9(8) ?
O4 S2 C8 C9 -86.0(9) ?
O4' S2 C8 C9 -124.7(6) ?
O5 S2 C8 C9 44.3(7) ?
O5' S2 C8 C9 -4.2(6) ?
C13 C8 C9 C10 -0.4(7) ?
S2 C8 C9 C10 179.9(4) ?
C8 C9 C10 C11 0.8(8) ?
C9 C10 C11 C12 -1.2(9) ?
C9 C10 C11 C14 179.2(6) ?
C10 C11 C12 C13 1.0(9) ?
C14 C11 C12 C13 -179.4(6) ?
C11 C12 C13 C8 -0.6(8) ?
C9 C8 C13 C12 0.2(7) ?
S2 C8 C13 C12 180.0(4) ?
N1 C15 C16 N2 178.9(4) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139074040
