#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/52/2225270.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_2225270
loop_
_publ_author_name
'Broker, Grant A.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 2,2'-Iminodiethanaminium 2,2'-(disulfanyldiyl)dibenzoate dihydrate
;
_journal_coeditor_code           HB5342
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o718
_journal_paper_doi               10.1107/S1600536810007117
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C4 H15 N3 +, C14 H8 O4 S2 -, 2H2 O'
_chemical_formula_moiety         'C4 H15 N3 +, C14 H8 O4 S2 -, 2(H2 O)'
_chemical_formula_sum            'C18 H27 N3 O6 S2'
_chemical_formula_weight         445.55
_chemical_name_systematic
;
2,2'-Iminodiethanaminium 2,2'-(disulfanyldiyl)dibenzoate dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.162(9)
_cell_angle_beta                 104.806(4)
_cell_angle_gamma                102.776(7)
_cell_formula_units_Z            2
_cell_length_a                   7.804(3)
_cell_length_b                   11.472(5)
_cell_length_c                   12.701(4)
_cell_measurement_reflns_used    1579
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      2.8
_cell_volume                     1028.2(7)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Rigaku AFC12Κ/SATURN724'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.022
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9871
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.8
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.74
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.28
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3529
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.27
_refine_ls_R_factor_all          0.068
_refine_ls_R_factor_gt           0.067
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0108P)²+6.0488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.174
_refine_ls_wR_factor_ref         0.175
_reflns_number_gt                3380
_reflns_number_total             3529
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5342.cif
_cod_data_source_block           I
_cod_original_cell_volume        1028.1(6)
_cod_database_code               2225270
_cod_database_fobs_code          2225270
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.36783(17) 0.36668(12) 0.05188(10) 0.0220(3) Uani d . 1 . .
S S2 0.27851(18) 0.29462(11) -0.12164(10) 0.0227(3) Uani d . 1 . .
O O1 0.4707(5) 0.4706(4) 0.2733(3) 0.0289(8) Uani d . 1 . .
O O2 0.7336(5) 0.4825(3) 0.4019(3) 0.0259(8) Uani d . 1 . .
O O3 0.2557(5) 0.0464(3) -0.4359(3) 0.0269(8) Uani d . 1 . .
O O4 0.1636(5) 0.2013(3) -0.3519(3) 0.0261(8) Uani d . 1 . .
O O1W 1.0465(5) 0.6687(3) 0.5318(3) 0.0261(8) Uani d D 1 . .
H H1W 0.9510 0.6167 0.4832 0.039 Uiso d D 1 . .
H H2W 1.1163 0.6333 0.5664 0.039 Uiso d D 1 . .
O O2W 0.3984(5) 0.6179(3) 0.4457(3) 0.0276(8) Uani d D 1 . .
H H3W 0.4214 0.5702 0.3947 0.041 Uiso d D 1 . .
H H4W 0.3596 0.5795 0.4885 0.041 Uiso d D 1 . .
N N1 0.2010(6) -0.1911(4) 0.3919(4) 0.0261(10) Uani d . 1 . .
H H1N 0.1997 -0.2594 0.4178 0.039 Uiso calc R 1 . .
H H2N 0.0846 -0.1829 0.3721 0.039 Uiso calc R 1 . .
H H3N 0.2786 -0.1219 0.4476 0.039 Uiso calc R 1 . .
N N2 0.3889(6) 0.0195(4) 0.3355(4) 0.0237(9) Uani d D 1 . .
H H4N 0.4998 0.0098 0.3591 0.036 Uiso d D 1 . .
N N3 0.2433(6) 0.2148(4) 0.4298(4) 0.0247(9) Uani d . 1 . .
H H5N 0.1469 0.2457 0.4346 0.037 Uiso calc R 1 . .
H H6N 0.3517 0.2726 0.4752 0.037 Uiso calc R 1 . .
H H7N 0.2308 0.1443 0.4528 0.037 Uiso calc R 1 . .
C C1 0.6340(7) 0.4671(4) 0.3007(4) 0.0196(10) Uani d . 1 . .
C C2 0.7199(7) 0.4399(4) 0.2082(4) 0.0200(10) Uani d . 1 . .
C C3 0.6121(7) 0.3884(4) 0.0920(4) 0.0210(10) Uani d . 1 . .
C C4 0.7005(7) 0.3573(5) 0.0129(4) 0.0247(11) Uani d . 1 . .
H H4 0.6293 0.3201 -0.0648 0.030 Uiso calc R 1 . .
C C5 0.8917(7) 0.3796(5) 0.0455(5) 0.0265(11) Uani d . 1 . .
H H5 0.9492 0.3573 -0.0101 0.032 Uiso calc R 1 . .
C C6 0.9987(7) 0.4334(5) 0.1573(4) 0.0249(11) Uani d . 1 . .
H H6 1.1296 0.4508 0.1789 0.030 Uiso calc R 1 . .
C C7 0.9117(7) 0.4620(5) 0.2382(4) 0.0224(10) Uani d . 1 . .
H H7 0.9846 0.4974 0.3158 0.027 Uiso calc R 1 . .
C C8 0.2166(6) 0.1048(4) -0.3544(4) 0.0210(10) Uani d . 1 . .
C C9 0.2344(6) 0.0572(4) -0.2513(4) 0.0200(10) Uani d . 1 . .
C C10 0.2594(7) 0.1319(4) -0.1426(4) 0.0226(11) Uani d . 1 . .
C C11 0.2712(8) 0.0787(5) -0.0541(5) 0.0320(13) Uani d . 1 . .
H H11 0.2877 0.1289 0.0195 0.038 Uiso calc R 1 . .
C C12 0.2593(9) -0.0472(5) -0.0706(5) 0.0358(14) Uani d . 1 . .
H H12 0.2676 -0.0819 -0.0085 0.043 Uiso calc R 1 . .
C C13 0.2359(7) -0.1201(5) -0.1749(5) 0.0292(12) Uani d . 1 . .
H H13 0.2278 -0.2059 -0.1863 0.035 Uiso calc R 1 . .
C C14 0.2238(6) -0.0689(4) -0.2650(4) 0.0222(10) Uani d . 1 . .
H H14 0.2079 -0.1205 -0.3380 0.027 Uiso calc R 1 . .
C C15 0.2665(7) -0.2058(5) 0.2913(4) 0.0271(11) Uani d . 1 . .
H H15A 0.1831 -0.2816 0.2311 0.033 Uiso calc R 1 . .
H H15B 0.3924 -0.2159 0.3125 0.033 Uiso calc R 1 . .
C C16 0.2700(8) -0.0929(5) 0.2468(4) 0.0272(11) Uani d . 1 . .
H H16A 0.3167 -0.1029 0.1810 0.033 Uiso calc R 1 . .
H H16B 0.1428 -0.0858 0.2212 0.033 Uiso calc R 1 . .
C C17 0.4030(7) 0.1345(5) 0.3004(5) 0.0261(11) Uani d . 1 . .
H H17A 0.4037 0.1170 0.2208 0.031 Uiso calc R 1 . .
H H17B 0.5212 0.1977 0.3487 0.031 Uiso calc R 1 . .
C C18 0.2445(7) 0.1852(5) 0.3100(4) 0.0275(11) Uani d . 1 . .
H H18A 0.2561 0.2615 0.2845 0.033 Uiso calc R 1 . .
H H18B 0.1263 0.1230 0.2603 0.033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 S1 S2 . . 104.23(17) ?
C10 S2 S1 . . 103.71(18) ?
H1W O1W H2W . . 111.4 ?
H3W O2W H4W . . 111.4 ?
C15 N1 H1N . . 109.5 ?
C15 N1 H2N . . 109.5 ?
H1N N1 H2N . . 109.5 ?
C15 N1 H3N . . 109.5 ?
H1N N1 H3N . . 109.5 ?
H2N N1 H3N . . 109.5 ?
C16 N2 C17 . . 114.3(4) ?
C16 N2 H4N . . 108.1 ?
C17 N2 H4N . . 109.8 ?
C18 N3 H5N . . 109.5 ?
C18 N3 H6N . . 109.5 ?
H5N N3 H6N . . 109.5 ?
C18 N3 H7N . . 109.5 ?
H5N N3 H7N . . 109.5 ?
H6N N3 H7N . . 109.5 ?
O1 C1 O2 . . 124.6(4) ?
O1 C1 C2 . . 118.2(4) ?
O2 C1 C2 . . 117.2(4) ?
C7 C2 C3 . . 118.9(4) ?
C7 C2 C1 . . 118.8(4) ?
C3 C2 C1 . . 122.3(4) ?
C4 C3 C2 . . 118.7(5) ?
C4 C3 S1 . . 122.1(4) ?
C2 C3 S1 . . 119.3(4) ?
C3 C4 C5 . . 121.1(5) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C6 C5 C4 . . 120.9(5) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C7 . . 118.8(5) ?
C5 C6 H6 . . 120.6 ?
C7 C6 H6 . . 120.6 ?
C6 C7 C2 . . 121.6(5) ?
C6 C7 H7 . . 119.2 ?
C2 C7 H7 . . 119.2 ?
O3 C8 O4 . . 124.8(5) ?
O3 C8 C9 . . 118.1(4) ?
O4 C8 C9 . . 117.1(4) ?
C14 C9 C10 . . 118.2(5) ?
C14 C9 C8 . . 118.1(4) ?
C10 C9 C8 . . 123.7(4) ?
C11 C10 C9 . . 119.1(5) ?
C11 C10 S2 . . 121.7(4) ?
C9 C10 S2 . . 119.3(4) ?
C10 C11 C12 . . 121.4(5) ?
C10 C11 H11 . . 119.3 ?
C12 C11 H11 . . 119.3 ?
C13 C12 C11 . . 120.1(5) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C14 . . 119.6(5) ?
C12 C13 H13 . . 120.2 ?
C14 C13 H13 . . 120.2 ?
C13 C14 C9 . . 121.6(5) ?
C13 C14 H14 . . 119.2 ?
C9 C14 H14 . . 119.2 ?
N1 C15 C16 . . 110.4(4) ?
N1 C15 H15A . . 109.6 ?
C16 C15 H15A . . 109.6 ?
N1 C15 H15B . . 109.6 ?
C16 C15 H15B . . 109.6 ?
H15A C15 H15B . . 108.1 ?
N2 C16 C15 . . 110.1(4) ?
N2 C16 H16A . . 109.6 ?
C15 C16 H16A . . 109.6 ?
N2 C16 H16B . . 109.6 ?
C15 C16 H16B . . 109.6 ?
H16A C16 H16B . . 108.2 ?
N2 C17 C18 . . 111.2(4) ?
N2 C17 H17A . . 109.4 ?
C18 C17 H17A . . 109.4 ?
N2 C17 H17B . . 109.4 ?
C18 C17 H17B . . 109.4 ?
H17A C17 H17B . . 108.0 ?
N3 C18 C17 . . 110.3(4) ?
N3 C18 H18A . . 109.6 ?
C17 C18 H18A . . 109.6 ?
N3 C18 H18B . . 109.6 ?
C17 C18 H18B . . 109.6 ?
H18A C18 H18B . . 108.1 ?
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 C3 . 1.787(5) ?
S1 S2 . 2.0540(18) ?
S2 C10 . 1.796(5) ?
O1 C1 . 1.244(6) ?
O2 C1 . 1.273(6) ?
O3 C8 . 1.253(6) ?
O4 C8 . 1.262(6) ?
O1W H1W . 0.8400 ?
O1W H2W . 0.8400 ?
O2W H3W . 0.8400 ?
O2W H4W . 0.8400 ?
N1 C15 . 1.484(6) ?
N1 H1N . 0.9100 ?
N1 H2N . 0.9100 ?
N1 H3N . 0.9100 ?
N2 C16 . 1.455(7) ?
N2 C17 . 1.470(7) ?
N2 H4N . 0.8800 ?
N3 C18 . 1.491(7) ?
N3 H5N . 0.9100 ?
N3 H6N . 0.9100 ?
N3 H7N . 0.9100 ?
C1 C2 . 1.506(7) ?
C2 C7 . 1.396(7) ?
C2 C3 . 1.419(7) ?
C3 C4 . 1.388(7) ?
C4 C5 . 1.391(7) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.375(7) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.393(7) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C9 . 1.509(7) ?
C9 C14 . 1.401(7) ?
C9 C10 . 1.403(7) ?
C10 C11 . 1.380(7) ?
C11 C12 . 1.393(8) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.353(8) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.384(8) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 C16 . 1.515(7) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.500(7) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
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
N1 H1N O1W 1_445 0.91 2.27 2.939(6) 130
N1 H1N O2W 1_545 0.91 2.33 3.038(6) 135
N1 H2N O4 2_555 0.91 1.85 2.731(7) 164
N1 H3N O3 1_556 0.91 2.24 2.981(6) 138
N2 H4N O3 2_655 0.88 2.21 3.069(6) 166
N3 H5N O1W 2_666 0.91 2.06 2.961(6) 172
N3 H6N O2W 2_666 0.91 1.94 2.844(6) 170
N3 H7N O3 1_556 0.91 1.98 2.835(6) 156
O1w H1W O2 1_555 0.84 1.90 2.720(5) 167
O1w H2W O2 2_766 0.84 1.99 2.803(5) 162
O2w H3W O1 1_555 0.84 1.89 2.732(6) 176
O2w H4W O2 2_666 0.84 1.92 2.751(5) 171
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
C3 S1 S2 C10 . . . . 81.3(2) ?
O1 C1 C2 C7 . . . . 166.2(4) ?
O2 C1 C2 C7 . . . . -15.1(7) ?
O1 C1 C2 C3 . . . . -16.1(7) ?
O2 C1 C2 C3 . . . . 162.6(4) ?
C7 C2 C3 C4 . . . . 2.6(7) ?
C1 C2 C3 C4 . . . . -175.1(4) ?
C7 C2 C3 S1 . . . . -177.0(4) ?
C1 C2 C3 S1 . . . . 5.3(6) ?
S2 S1 C3 C4 . . . . -0.7(4) ?
S2 S1 C3 C2 . . . . 178.9(3) ?
C2 C3 C4 C5 . . . . -2.1(7) ?
S1 C3 C4 C5 . . . . 177.5(4) ?
C3 C4 C5 C6 . . . . -0.1(8) ?
C4 C5 C6 C7 . . . . 1.9(8) ?
C5 C6 C7 C2 . . . . -1.5(8) ?
C3 C2 C7 C6 . . . . -0.8(7) ?
C1 C2 C7 C6 . . . . 177.0(4) ?
O3 C8 C9 C14 . . . . -23.8(7) ?
O4 C8 C9 C14 . . . . 156.5(4) ?
O3 C8 C9 C10 . . . . 156.8(5) ?
O4 C8 C9 C10 . . . . -22.9(7) ?
C14 C9 C10 C11 . . . . -0.5(7) ?
C8 C9 C10 C11 . . . . 179.0(5) ?
C14 C9 C10 S2 . . . . 178.7(4) ?
C8 C9 C10 S2 . . . . -1.9(7) ?
S1 S2 C10 C11 . . . . 10.9(5) ?
S1 S2 C10 C9 . . . . -168.2(4) ?
C9 C10 C11 C12 . . . . 0.2(8) ?
S2 C10 C11 C12 . . . . -178.9(5) ?
C10 C11 C12 C13 . . . . 0.1(9) ?
C11 C12 C13 C14 . . . . 0.0(9) ?
C12 C13 C14 C9 . . . . -0.3(8) ?
C10 C9 C14 C13 . . . . 0.5(7) ?
C8 C9 C14 C13 . . . . -178.9(5) ?
C17 N2 C16 C15 . . . . 179.5(4) ?
N1 C15 C16 N2 . . . . 57.9(6) ?
C16 N2 C17 C18 . . . . 83.9(5) ?
N2 C17 C18 N3 . . . . 60.3(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656021
