#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/34/2223456.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_2223456
loop_
_publ_author_name
'Fu, Xue-qun'
_publ_section_title
;
 Bis(4-ethoxyanilinium) sulfate trihydrate
;
_journal_coeditor_code           JH2104
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2520
_journal_paper_doi               10.1107/S1600536809036290
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '2C8 H12 N O +, S O4 2-, 3H2 O'
_chemical_formula_moiety         '2(C8 H12 N O +), S O4 2-, 3(H2 O)'
_chemical_formula_sum            'C16 H30 N2 O9 S'
_chemical_formula_weight         426.48
_chemical_name_systematic
;
Bis(4-ethoxyanilinium) sulfate trihydrate
;
_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           SHELXL97
_cell_angle_alpha                101.40(3)
_cell_angle_beta                 94.53(3)
_cell_angle_gamma                90.18(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0455(14)
_cell_length_b                   10.969(2)
_cell_length_c                   13.787(3)
_cell_measurement_reflns_used    5008
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      3.025
_cell_volume                     1041.0(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku SCXmini'
_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  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10835
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.616
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0626P)²+0.4014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                3947
_reflns_number_total             4748
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2104.cif
_cod_data_source_block           I
_cod_database_code               2223456
_cod_database_fobs_code          2223456
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
C C10 0.0896(3) 0.6806(2) 0.58350(17) 0.0449(5) Uani d . 1 . .
H H10A -0.0396 0.6635 0.5538 0.054 Uiso calc R 1 . .
H H10B 0.1251 0.7648 0.5791 0.054 Uiso calc R 1 . .
C C13 0.1606(3) 0.6525(2) 0.27781(16) 0.0376(5) Uani d . 1 . .
H H13A 0.0981 0.7046 0.2406 0.045 Uiso calc R 1 . .
C C14 0.2775(3) 0.56205(18) 0.23343(15) 0.0298(4) Uani d . 1 . .
C C11 0.2290(3) 0.5885(2) 0.43338(15) 0.0338(4) Uani d . 1 . .
C C16 0.3460(3) 0.4968(2) 0.38719(16) 0.0405(5) Uani d . 1 . .
H H16A 0.4083 0.4440 0.4238 0.049 Uiso calc R 1 . .
C C12 0.1355(3) 0.6664(2) 0.37864(17) 0.0394(5) Uani d . 1 . .
H H12A 0.0564 0.7276 0.4089 0.047 Uiso calc R 1 . .
C C15 0.3701(3) 0.4838(2) 0.28761(16) 0.0383(5) Uani d . 1 . .
H H15A 0.4487 0.4224 0.2570 0.046 Uiso calc R 1 . .
N N2 0.2998(2) 0.54499(16) 0.12718(12) 0.0323(4) Uani d . 1 . .
H H2C 0.2325 0.6016 0.1020 0.049 Uiso calc R 1 . .
H H2D 0.2583 0.4692 0.0971 0.049 Uiso calc R 1 . .
H H2E 0.4222 0.5538 0.1177 0.049 Uiso calc R 1 . .
O O6 0.2170(2) 0.59385(16) 0.53274(11) 0.0454(4) Uani d . 1 . .
C C7 0.4295(3) 0.1249(2) 0.29676(16) 0.0383(5) Uani d . 1 . .
H H7A 0.5285 0.1591 0.2695 0.046 Uiso calc R 1 . .
C C8 0.4180(3) 0.1505(2) 0.39883(16) 0.0402(5) Uani d . 1 . .
H H8A 0.5088 0.2020 0.4400 0.048 Uiso calc R 1 . .
C C6 0.2953(3) 0.04922(18) 0.23606(14) 0.0284(4) Uani d . 1 . .
C C3 0.2702(3) 0.09881(19) 0.43898(15) 0.0329(4) Uani d . 1 . .
C C5 0.1461(3) -0.0017(2) 0.27536(15) 0.0348(5) Uani d . 1 . .
H H5A 0.0550 -0.0525 0.2338 0.042 Uiso calc R 1 . .
C C4 0.1337(3) 0.0235(2) 0.37657(16) 0.0365(5) Uani d . 1 . .
H H4A 0.0333 -0.0101 0.4033 0.044 Uiso calc R 1 . .
N N1 0.3073(2) 0.02291(16) 0.12851(12) 0.0316(4) Uani d . 1 . .
H H1D 0.4093 0.0617 0.1140 0.047 Uiso calc R 1 . .
H H1E 0.2031 0.0497 0.0991 0.047 Uiso calc R 1 . .
H H1F 0.3168 -0.0587 0.1070 0.047 Uiso calc R 1 . .
O O4 0.8618(2) 0.76777(14) 1.06802(12) 0.0419(4) Uani d . 1 . .
O O3 0.9964(2) 0.84402(14) 0.93687(12) 0.0411(4) Uani d . 1 . .
O O1 1.2016(2) 0.76811(14) 1.05715(11) 0.0376(3) Uani d . 1 . .
C C9 0.1020(4) 0.6671(3) 0.69069(18) 0.0547(7) Uani d . 1 . .
H H9A 0.0183 0.7250 0.7268 0.082 Uiso calc R 1 . .
H H9B 0.2304 0.6839 0.7192 0.082 Uiso calc R 1 . .
H H9C 0.0651 0.5839 0.6942 0.082 Uiso calc R 1 . .
C C2 0.3919(3) 0.1835(2) 0.60656(16) 0.0435(5) Uani d . 1 . .
H H2A 0.4021 0.2688 0.5976 0.052 Uiso calc R 1 . .
H H2B 0.5136 0.1442 0.5956 0.052 Uiso calc R 1 . .
S S1 1.01303(6) 0.75062(4) 0.99930(3) 0.02523(14) Uani d . 1 . .
O O2 1.0005(2) 0.62454(13) 0.93962(12) 0.0415(4) Uani d . 1 . .
O O5 0.2452(2) 0.11746(16) 0.53811(11) 0.0425(4) Uani d . 1 . .
C C1 0.3390(4) 0.1809(3) 0.70955(17) 0.0509(6) Uani d . 1 . .
H H1A 0.4344 0.2252 0.7572 0.076 Uiso calc R 1 . .
H H1B 0.3307 0.0962 0.7178 0.076 Uiso calc R 1 . .
H H1C 0.2181 0.2195 0.7195 0.076 Uiso calc R 1 . .
O O7W 1.3057(3) 0.4580(2) 0.89486(15) 0.0507(5) Uani d . 1 . .
O O8W 1.2987(2) 0.98944(19) 0.89593(15) 0.0476(4) Uani d . 1 . .
O O9W 0.5193(3) 0.7333(2) 0.92324(17) 0.0644(5) Uani d . 1 . .
H H7D 1.249(5) 0.393(3) 0.893(2) 0.072(10) Uiso d . 1 . .
H H8D 1.255(4) 1.052(3) 0.899(2) 0.050(9) Uiso d . 1 . .
H H7C 1.227(5) 0.514(3) 0.900(2) 0.067(10) Uiso d . 1 . .
H H9E 0.427(6) 0.747(4) 0.968(3) 0.104(14) Uiso d . 1 . .
H H8C 1.209(5) 0.932(3) 0.899(2) 0.077(10) Uiso d . 1 . .
H H9D 0.614(7) 0.757(4) 0.985(3) 0.132(17) Uiso d . 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
O6 C10 C9 . . 107.7(2) ?
O6 C10 H10A . . 110.2 ?
C9 C10 H10A . . 110.2 ?
O6 C10 H10B . . 110.2 ?
C9 C10 H10B . . 110.2 ?
H10A C10 H10B . . 108.5 ?
C14 C13 C12 . . 120.0(2) ?
C14 C13 H13A . . 120.0 ?
C12 C13 H13A . . 120.0 ?
C13 C14 C15 . . 120.56(19) ?
C13 C14 N2 . . 120.11(18) ?
C15 C14 N2 . . 119.29(18) ?
O6 C11 C12 . . 124.93(19) ?
O6 C11 C16 . . 115.39(19) ?
C12 C11 C16 . . 119.7(2) ?
C15 C16 C11 . . 120.4(2) ?
C15 C16 H16A . . 119.8 ?
C11 C16 H16A . . 119.8 ?
C11 C12 C13 . . 119.60(19) ?
C11 C12 H12A . . 120.2 ?
C13 C12 H12A . . 120.2 ?
C16 C15 C14 . . 119.79(19) ?
C16 C15 H15A . . 120.1 ?
C14 C15 H15A . . 120.1 ?
C14 N2 H2C . . 109.5 ?
C14 N2 H2D . . 109.5 ?
H2C N2 H2D . . 109.5 ?
C14 N2 H2E . . 109.5 ?
H2C N2 H2E . . 109.5 ?
H2D N2 H2E . . 109.5 ?
C11 O6 C10 . . 118.27(18) ?
C6 C7 C8 . . 120.18(19) ?
C6 C7 H7A . . 119.9 ?
C8 C7 H7A . . 119.9 ?
C3 C8 C7 . . 119.60(19) ?
C3 C8 H8A . . 120.2 ?
C7 C8 H8A . . 120.2 ?
C7 C6 C5 . . 120.63(19) ?
C7 C6 N1 . . 120.03(17) ?
C5 C6 N1 . . 119.33(18) ?
O5 C3 C8 . . 124.56(19) ?
O5 C3 C4 . . 115.74(18) ?
C8 C3 C4 . . 119.69(19) ?
C4 C5 C6 . . 119.50(19) ?
C4 C5 H5A . . 120.2 ?
C6 C5 H5A . . 120.2 ?
C5 C4 C3 . . 120.39(19) ?
C5 C4 H4A . . 119.8 ?
C3 C4 H4A . . 119.8 ?
C6 N1 H1D . . 109.5 ?
C6 N1 H1E . . 109.5 ?
H1D N1 H1E . . 109.5 ?
C6 N1 H1F . . 109.5 ?
H1D N1 H1F . . 109.5 ?
H1E N1 H1F . . 109.5 ?
C10 C9 H9A . . 109.5 ?
C10 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C10 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O5 C2 C1 . . 107.52(19) ?
O5 C2 H2A . . 110.2 ?
C1 C2 H2A . . 110.2 ?
O5 C2 H2B . . 110.2 ?
C1 C2 H2B . . 110.2 ?
H2A C2 H2B . . 108.5 ?
O2 S1 O3 . . 111.43(10) ?
O2 S1 O4 . . 109.70(10) ?
O3 S1 O4 . . 109.51(9) ?
O2 S1 O1 . . 108.58(9) ?
O3 S1 O1 . . 108.27(9) ?
O4 S1 O1 . . 109.31(10) ?
C3 O5 C2 . . 118.10(16) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
H7D O7W H7C . . 108(3) ?
H8D O8W H8C . . 111(3) ?
H9E O9W H9D . . 85(3) ?
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
C10 O6 . 1.430(3) ?
C10 C9 . 1.510(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C13 C14 . 1.372(3) ?
C13 C12 . 1.394(3) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.378(3) ?
C14 N2 . 1.461(3) ?
C11 O6 . 1.369(3) ?
C11 C12 . 1.383(3) ?
C11 C16 . 1.389(3) ?
C16 C15 . 1.376(3) ?
C16 H16A . 0.9300 ?
C12 H12A . 0.9300 ?
C15 H15A . 0.9300 ?
N2 H2C . 0.8900 ?
N2 H2D . 0.8900 ?
N2 H2E . 0.8900 ?
C7 C6 . 1.371(3) ?
C7 C8 . 1.389(3) ?
C7 H7A . 0.9300 ?
C8 C3 . 1.386(3) ?
C8 H8A . 0.9300 ?
C6 C5 . 1.384(3) ?
C6 N1 . 1.463(2) ?
C3 O5 . 1.367(2) ?
C3 C4 . 1.390(3) ?
C5 C4 . 1.378(3) ?
C5 H5A . 0.9300 ?
C4 H4A . 0.9300 ?
N1 H1D . 0.8900 ?
N1 H1E . 0.8900 ?
N1 H1F . 0.8900 ?
O4 S1 . 1.4693(15) ?
O3 S1 . 1.4621(15) ?
O1 S1 . 1.4861(15) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C2 O5 . 1.434(3) ?
C2 C1 . 1.502(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
S1 O2 . 1.4613(15) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
O7W H7D . 0.81(4) ?
O7W H7C . 0.83(4) ?
O8W H8D . 0.75(3) ?
O8W H8C . 0.90(4) ?
O9W H9E . 0.92(4) ?
O9W H9D . 1.03(5) ?
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
N2 H2C O1 1_454 0.89 2.05 2.870(2) 153.2
N2 H2C S1 1_454 0.89 2.77 3.649(2) 171.6
N2 H2D O2 2_666 0.89 2.07 2.788(2) 137.4
N2 H2E O7W 2_766 0.89 1.94 2.819(3) 168.8
N1 H1D O8W 2_766 0.89 2.14 2.823(2) 132.8
N1 H1D O9W 2_666 0.89 2.46 3.166(3) 136.3
N1 H1E O3 2_666 0.89 1.93 2.785(2) 161.8
N1 H1F O1 1_444 0.89 2.03 2.849(2) 152.2
O7W H7D O4 2_767 0.81(4) 2.11(4) 2.893(3) 163(3)
O8W H8D O4 2_777 0.75(3) 2.12(3) 2.864(3) 172(3)
O9W H9E O1 1_455 0.92(4) 2.07(4) 2.991(3) 175(4)
O9W H9E S1 1_455 0.92(4) 2.98(4) 3.791(2) 147(3)
O7W H7C O2 . 0.83(4) 2.05(4) 2.851(3) 164(3)
O8W H8C O3 . 0.90(4) 1.94(4) 2.815(3) 164(3)
O8W H8C S1 . 0.90(4) 3.02(4) 3.852(2) 154(3)
O9W H9D O4 . 1.03(5) 2.00(5) 2.981(3) 158(4)
O9W H9D S1 . 1.03(5) 2.81(5) 3.547(2) 129(3)
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
C12 C13 C14 C15 . . . . 0.4(3) ?
C12 C13 C14 N2 . . . . 178.24(19) ?
O6 C11 C16 C15 . . . . -179.3(2) ?
C12 C11 C16 C15 . . . . 0.4(3) ?
O6 C11 C12 C13 . . . . 179.3(2) ?
C16 C11 C12 C13 . . . . -0.4(3) ?
C14 C13 C12 C11 . . . . 0.0(3) ?
C11 C16 C15 C14 . . . . -0.1(3) ?
C13 C14 C15 C16 . . . . -0.3(3) ?
N2 C14 C15 C16 . . . . -178.2(2) ?
C12 C11 O6 C10 . . . . 4.3(3) ?
C16 C11 O6 C10 . . . . -176.0(2) ?
C9 C10 O6 C11 . . . . 179.48(19) ?
C6 C7 C8 C3 . . . . 0.2(4) ?
C8 C7 C6 C5 . . . . 0.5(3) ?
C8 C7 C6 N1 . . . . 179.7(2) ?
C7 C8 C3 O5 . . . . 179.9(2) ?
C7 C8 C3 C4 . . . . -1.0(4) ?
C7 C6 C5 C4 . . . . -0.4(3) ?
N1 C6 C5 C4 . . . . -179.62(19) ?
C6 C5 C4 C3 . . . . -0.4(3) ?
O5 C3 C4 C5 . . . . -179.7(2) ?
C8 C3 C4 C5 . . . . 1.1(3) ?
C8 C3 O5 C2 . . . . -7.2(3) ?
C4 C3 O5 C2 . . . . 173.6(2) ?
C1 C2 O5 C3 . . . . -174.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655893
