#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/44/2224468.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_2224468
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
_publ_section_title
;
 4-(2-Hydroxyethyl)anilinium 3-carboxy-4-hydroxybenzenesulfonate
 monohydrate
;
_journal_coeditor_code           TK2580
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3209
_journal_paper_doi               10.1107/S1600536809049745
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H12 N O +, C7 H5 O6 S -, H2 O'
_chemical_formula_moiety         'C8 H12 N O +, C7 H5 O6 S -, H2 O'
_chemical_formula_sum            'C15 H19 N O8 S'
_chemical_formula_weight         373.37
_chemical_melting_point          498
_chemical_name_systematic
;
4-(2-Hydroxyethyl)anilinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate
;
_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                102.169(6)
_cell_angle_beta                 98.538(6)
_cell_angle_gamma                101.366(6)
_cell_formula_units_Z            2
_cell_length_a                   7.7412(6)
_cell_length_b                   8.7977(6)
_cell_length_c                   12.8330(8)
_cell_measurement_reflns_used    4875
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.8
_cell_measurement_theta_min      3.2
_cell_volume                     820.97(11)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction (2009)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction (2009)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction (2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)'
_computing_structure_solution
'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-S CCD-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.024
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10214
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.085
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0575P)²+0.1198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                2756
_reflns_number_total             3215
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2580.cif
_cod_data_source_block           I
_cod_database_code               2224468
_cod_database_fobs_code          2224468
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O11A 0.80608(18) 0.87360(14) 0.00089(10) 0.0341(4) Uani . . 1.000
N N4A 0.78541(19) 0.07130(16) 0.19112(12) 0.0234(4) Uani . . 1.000
C C1A 0.8163(2) 0.53103(17) 0.13072(12) 0.0212(4) Uani . . 1.000
C C2A 0.9359(2) 0.51052(18) 0.21625(12) 0.0244(4) Uani . . 1.000
C C3A 0.9278(2) 0.35998(18) 0.23691(13) 0.0241(5) Uani . . 1.000
C C4A 0.7995(2) 0.23068(17) 0.17042(12) 0.0206(4) Uani . . 1.000
C C5A 0.6827(2) 0.24656(19) 0.08278(14) 0.0299(5) Uani . . 1.000
C C6A 0.6921(2) 0.39667(19) 0.06356(14) 0.0304(5) Uani . . 1.000
C C11A 0.8410(2) 0.72115(19) 0.00469(14) 0.0302(5) Uani . . 1.000
C C21A 0.8142(2) 0.69635(18) 0.11528(13) 0.0247(4) Uani . . 1.000
S S5 0.31926(5) 0.00829(4) 0.26512(3) 0.02030(10) Uani . . 1.000
O O2 0.83804(16) 0.60833(15) 0.51275(10) 0.0334(4) Uani . . 1.000
O O11 0.43638(16) 0.62380(14) 0.25827(10) 0.0310(4) Uani . . 1.000
O O12 0.67893(15) 0.76007(13) 0.38590(10) 0.0323(4) Uani . . 1.000
O O51 0.17800(14) 0.04515(12) 0.19312(9) 0.0253(3) Uani . . 1.000
O O52 0.25277(15) -0.07135(13) 0.34506(9) 0.0289(4) Uani . . 1.000
O O53 0.43041(14) -0.08330(13) 0.20599(9) 0.0292(3) Uani . . 1.000
C C1 0.5791(2) 0.47935(17) 0.36674(12) 0.0205(4) Uani . . 1.000
C C2 0.7134(2) 0.47689(18) 0.45347(12) 0.0226(4) Uani . . 1.000
C C3 0.7206(2) 0.33328(19) 0.48234(13) 0.0257(5) Uani . . 1.000
C C4 0.5988(2) 0.19310(18) 0.42610(12) 0.0227(5) Uani . . 1.000
C C5 0.46674(19) 0.19342(17) 0.33820(12) 0.0192(4) Uani . . 1.000
C C6 0.45641(19) 0.33538(17) 0.30967(12) 0.0201(4) Uani . . 1.000
C C11 0.5704(2) 0.63262(18) 0.33854(13) 0.0233(5) Uani . . 1.000
O O1W 0.9577(2) 0.04283(16) 0.39011(11) 0.0352(4) Uani . . 1.000
H H2A 1.02240 0.59840 0.26020 0.0290 Uiso calc R 1.000
H H3A 1.00740 0.34710 0.29440 0.0290 Uiso calc R 1.000
H H5A 0.59910 0.15770 0.03750 0.0360 Uiso calc R 1.000
H H6A 0.61400 0.40810 0.00480 0.0370 Uiso calc R 1.000
H H11A 0.824(3) 0.894(3) -0.0554(19) 0.047(6) Uiso . . 1.000
H H12A 0.75870 0.63730 -0.05290 0.0360 Uiso calc R 1.000
H H13A 0.96310 0.71970 -0.00400 0.0360 Uiso calc R 1.000
H H21A 0.90780 0.77360 0.17060 0.0300 Uiso calc R 1.000
H H22A 0.70000 0.71900 0.12720 0.0300 Uiso calc R 1.000
H H41A 0.858(3) 0.075(2) 0.2578(17) 0.040(5) Uiso . . 1.000
H H42A 0.818(3) 0.009(3) 0.1367(19) 0.049(6) Uiso . . 1.000
H H43A 0.668(3) 0.026(2) 0.1963(15) 0.035(5) Uiso . . 1.000
H H2 0.823(3) 0.685(3) 0.491(2) 0.062(8) Uiso . . 1.000
H H3 0.80840 0.33250 0.54000 0.0310 Uiso calc R 1.000
H H4 0.60390 0.09830 0.44620 0.0270 Uiso calc R 1.000
H H6 0.36750 0.33520 0.25230 0.0240 Uiso calc R 1.000
H H11 0.434(3) 0.715(3) 0.2491(17) 0.047(6) Uiso . . 1.000
H H11W 0.883(4) -0.035(3) 0.403(2) 0.069(8) Uiso . . 1.000
H H12W 1.047(3) 0.002(3) 0.3819(17) 0.046(6) Uiso . . 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O51 S5 O53 . . . 113.02(7) no
O51 S5 C5 . . . 106.82(7) no
O52 S5 O53 . . . 110.32(7) no
O52 S5 C5 . . . 107.10(7) no
O53 S5 C5 . . . 105.72(7) no
O51 S5 O52 . . . 113.33(7) no
C11A O11A H11A . . . 109.8(18) no
C2 O2 H2 . . . 109.8(18) no
C11 O11 H11 . . . 110.7(16) no
H11W O1W H12W . . . 102(3) no
H41A N4A H43A . . . 105.5(18) no
H41A N4A H42A . . . 110(2) no
C4A N4A H41A . . . 112.1(11) no
C4A N4A H43A . . . 111.1(12) no
H42A N4A H43A . . . 110(2) no
C4A N4A H42A . . . 108.5(17) no
C2A C1A C6A . . . 118.47(14) no
C2A C1A C21A . . . 120.69(14) no
C6A C1A C21A . . . 120.74(14) no
C1A C2A C3A . . . 120.99(14) no
C2A C3A C4A . . . 118.74(14) no
N4A C4A C5A . . . 118.38(14) no
C3A C4A C5A . . . 121.53(15) no
N4A C4A C3A . . . 120.08(14) no
C4A C5A C6A . . . 119.01(15) no
C1A C6A C5A . . . 121.20(15) no
O11A C11A C21A . . . 106.35(13) no
C1A C21A C11A . . . 115.37(13) no
C1A C2A H2A . . . 120.00 no
C3A C2A H2A . . . 119.00 no
C4A C3A H3A . . . 121.00 no
C2A C3A H3A . . . 121.00 no
C4A C5A H5A . . . 121.00 no
C6A C5A H5A . . . 120.00 no
C5A C6A H6A . . . 119.00 no
C1A C6A H6A . . . 119.00 no
C21A C11A H12A . . . 110.00 no
C21A C11A H13A . . . 110.00 no
H12A C11A H13A . . . 109.00 no
O11A C11A H12A . . . 110.00 no
O11A C11A H13A . . . 110.00 no
C1A C21A H22A . . . 108.00 no
C1A C21A H21A . . . 108.00 no
H21A C21A H22A . . . 107.00 no
C11A C21A H21A . . . 108.00 no
C11A C21A H22A . . . 108.00 no
C2 C1 C11 . . . 119.52(14) no
C6 C1 C11 . . . 121.67(14) no
C2 C1 C6 . . . 118.82(14) no
O2 C2 C3 . . . 116.62(14) no
C1 C2 C3 . . . 120.02(14) no
O2 C2 C1 . . . 123.35(14) no
C2 C3 C4 . . . 120.56(15) no
C3 C4 C5 . . . 119.94(15) no
C4 C5 C6 . . . 120.10(14) no
S5 C5 C4 . . . 118.07(12) no
S5 C5 C6 . . . 121.82(12) no
C1 C6 C5 . . . 120.53(14) no
O11 C11 O12 . . . 121.98(15) no
O11 C11 C1 . . . 115.13(14) no
O12 C11 C1 . . . 122.89(14) no
C4 C3 H3 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C1 C6 H6 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S5 O51 . . 1.4563(12) no
S5 O52 . . 1.4581(12) no
S5 O53 . . 1.4747(12) no
S5 C5 . . 1.7723(16) no
O11A C11A . . 1.429(2) no
O11A H11A . . 0.81(2) no
O2 C2 . . 1.348(2) no
O11 C11 . . 1.327(2) no
O12 C11 . . 1.234(2) no
O2 H2 . . 0.80(3) no
O11 H11 . . 0.84(3) no
O1W H11W . . 0.87(3) no
O1W H12W . . 0.85(2) no
N4A C4A . . 1.468(2) no
N4A H41A . . 0.94(2) no
N4A H42A . . 0.89(2) no
N4A H43A . . 0.94(2) no
C1A C6A . . 1.393(2) no
C1A C2A . . 1.394(2) no
C1A C21A . . 1.512(2) no
C2A C3A . . 1.396(2) no
C3A C4A . . 1.379(2) no
C4A C5A . . 1.384(2) no
C5A C6A . . 1.384(2) no
C11A C21A . . 1.518(2) no
C2A H2A . . 0.9300 no
C3A H3A . . 0.9300 no
C5A H5A . . 0.9300 no
C6A H6A . . 0.9300 no
C11A H12A . . 0.9700 no
C11A H13A . . 0.9700 no
C21A H21A . . 0.9700 no
C21A H22A . . 0.9700 no
C1 C2 . . 1.413(2) no
C1 C11 . . 1.479(2) no
C1 C6 . . 1.404(2) no
C2 C3 . . 1.398(2) no
C3 C4 . . 1.377(2) no
C4 C5 . . 1.406(2) no
C5 C6 . . 1.387(2) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C6 H6 . . 0.9300 no
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
O2 H2 O12 . 0.80(3) 1.93(3) 2.6302(18) 145(2) yes
O11 H11 O53 1_565 0.84(3) 1.97(3) 2.8034(17) 172(2) yes
O11A H11A O51 2_665 0.81(2) 1.95(2) 2.7444(17) 169(2) yes
N4A H41A O1W . 0.94(2) 1.86(2) 2.784(2) 166.5(19) yes
N4A H42A O11A 1_545 0.89(2) 1.87(2) 2.7287(19) 161(2) yes
N4A H43A O53 . 0.94(2) 1.94(2) 2.8689(19) 175.6(18) yes
O1W H11W O12 1_545 0.87(3) 2.10(3) 2.9396(19) 164(2) yes
O1W H12W O52 1_655 0.85(2) 1.92(2) 2.759(2) 171(2) yes
C3A H3A O2 2_766 0.93 2.50 3.373(2) 157 no
C6 H6 O51 . 0.93 2.57 2.9437(19) 104 no
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
O52 S5 C5 C4 . . . . 48.08(14) no
O52 S5 C5 C6 . . . . -133.01(13) no
O53 S5 C5 C4 . . . . -69.56(13) no
O53 S5 C5 C6 . . . . 109.35(13) no
O51 S5 C5 C6 . . . . -11.28(15) no
O51 S5 C5 C4 . . . . 169.81(12) no
C6A C1A C21A C11A . . . . -59.7(2) no
C2A C1A C21A C11A . . . . 123.94(16) no
C6A C1A C2A C3A . . . . -2.3(2) no
C21A C1A C2A C3A . . . . 174.16(15) no
C2A C1A C6A C5A . . . . 2.1(2) no
C21A C1A C6A C5A . . . . -174.34(15) no
C1A C2A C3A C4A . . . . 0.5(2) no
C2A C3A C4A C5A . . . . 1.6(2) no
C2A C3A C4A N4A . . . . -178.94(14) no
N4A C4A C5A C6A . . . . 178.74(15) no
C3A C4A C5A C6A . . . . -1.8(2) no
C4A C5A C6A C1A . . . . -0.1(2) no
O11A C11A C21A C1A . . . . 170.97(13) no
C6 C1 C2 O2 . . . . 179.56(14) no
C6 C1 C2 C3 . . . . -1.1(2) no
C11 C1 C2 O2 . . . . -0.7(2) no
C11 C1 C2 C3 . . . . 178.66(14) no
C2 C1 C6 C5 . . . . 0.2(2) no
C11 C1 C6 C5 . . . . -179.57(14) no
C2 C1 C11 O11 . . . . -177.96(14) no
C2 C1 C11 O12 . . . . 1.9(2) no
C6 C1 C11 O11 . . . . 1.8(2) no
C6 C1 C11 O12 . . . . -178.40(15) no
O2 C2 C3 C4 . . . . -179.87(14) no
C1 C2 C3 C4 . . . . 0.7(2) no
C2 C3 C4 C5 . . . . 0.6(2) no
C3 C4 C5 S5 . . . . 177.44(12) no
C3 C4 C5 C6 . . . . -1.5(2) no
S5 C5 C6 C1 . . . . -177.77(12) no
C4 C5 C6 C1 . . . . 1.1(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26000971
