#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/31/2223199.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_2223199
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
'Young, David J.'
_publ_section_title
;
 8-Ammonionaphthalene-2-sulfonate monohydrate: the zwitterionic hydrate
 of 1,7-Cleve's acid
;
_journal_coeditor_code           TK2500
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2110
_journal_paper_doi               10.1107/S1600536809030396
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H9 N O3 S, H2 O'
_chemical_formula_moiety         'C10 H9 N O3 S, H2 O'
_chemical_formula_sum            'C10 H11 N O4 S'
_chemical_formula_weight         241.27
_chemical_name_common
;
1-naphthylamine-7-sulfonic acid monohydrate; 1,7-Cleve's acid
monoydrate
;
_chemical_name_systematic
;
8-Ammonionaphthalene-2-sulfonate monohydrate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1616(3)
_cell_length_b                   16.4608(7)
_cell_length_c                   8.9059(3)
_cell_measurement_reflns_used    2826
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      32.3
_cell_measurement_theta_min      3.1
_cell_volume                     1049.88(7)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection
'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-S CCD-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.041
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5904
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.1
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flat prism'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details 'Flack (1983), 974 Friedel pairs'
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.91
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2252
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.91
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0476P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.072
_refine_ls_wR_factor_ref         0.076
_reflns_number_gt                1830
_reflns_number_total             2252
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2500.cif
_cod_data_source_block           I
_cod_database_code               2223199
_cod_database_fobs_code          2223199
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, 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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S2 0.91078(7) 0.91246(3) 0.30596(6) 0.0279(2) Uani . . 1.000
O O21 0.9227(3) 0.98981(10) 0.38255(19) 0.0426(6) Uani . . 1.000
O O22 1.0718(2) 0.89287(11) 0.21446(19) 0.0432(6) Uani . . 1.000
O O23 0.7375(3) 0.90447(11) 0.21899(17) 0.0386(6) Uani . . 1.000
N N8 0.7911(4) 0.89568(12) 0.9061(2) 0.0316(7) Uani . . 1.000
C C1 0.8622(3) 0.85751(14) 0.5919(3) 0.0244(6) Uani . . 1.000
C C2 0.8963(3) 0.83679(13) 0.4461(2) 0.0247(6) Uani . . 1.000
C C3 0.9158(4) 0.75485(14) 0.4020(3) 0.0313(7) Uani . . 1.000
C C4 0.8930(4) 0.69545(14) 0.5046(3) 0.0328(7) Uani . . 1.000
C C5 0.8196(4) 0.65100(14) 0.7627(3) 0.0350(7) Uani . . 1.000
C C6 0.7800(4) 0.66940(15) 0.9072(3) 0.0377(8) Uani . . 1.000
C C7 0.7701(4) 0.75056(16) 0.9537(2) 0.0344(8) Uani . . 1.000
C C8 0.8000(3) 0.81129(15) 0.8546(2) 0.0266(7) Uani . . 1.000
C C9 0.8386(3) 0.79617(14) 0.7015(2) 0.0244(6) Uani . . 1.000
C C10 0.8515(3) 0.71317(14) 0.6564(3) 0.0270(7) Uani . . 1.000
O O1W 0.6039(4) 1.01561(13) 0.7583(3) 0.0636(9) Uani . . 1.000
H H1 0.85450 0.91190 0.61930 0.0290 Uiso calc R 1.000
H H3 0.94410 0.74190 0.30290 0.0380 Uiso calc R 1.000
H H4 0.90490 0.64150 0.47490 0.0390 Uiso calc R 1.000
H H5 0.82590 0.59690 0.73300 0.0420 Uiso calc R 1.000
H H6 0.75920 0.62790 0.97610 0.0450 Uiso calc R 1.000
H H7 0.74290 0.76270 1.05330 0.0410 Uiso calc R 1.000
H H81 0.762(4) 0.8959(14) 1.002(3) 0.038(6) Uiso . . 1.000
H H82 0.904(5) 0.9182(18) 0.897(4) 0.051(9) Uiso . . 1.000
H H83 0.690(7) 0.927(3) 0.860(4) 0.056(10) Uiso . . 1.000
H H11W 0.502(6) 1.0367(18) 0.746(4) 0.076(10) Uiso . . 1.000
H H12W 0.699(4) 1.0497(17) 0.738(3) 0.082(8) 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
O21 S2 O22 . . . 114.47(11) no
O21 S2 O23 . . . 112.16(11) no
O21 S2 C2 . . . 106.91(10) no
O22 S2 O23 . . . 110.86(10) no
O22 S2 C2 . . . 106.70(10) no
O23 S2 C2 . . . 105.06(10) no
H11W O1W H12W . . . 113(3) no
H81 N8 H83 . . . 103(3) no
H82 N8 H83 . . . 114(2) no
C8 N8 H81 . . . 108.6(15) no
C8 N8 H82 . . . 109(2) no
H81 N8 H82 . . . 108(3) no
C8 N8 H83 . . . 111(3) no
C2 C1 C9 . . . 120.0(2) no
S2 C2 C3 . . . 118.12(16) no
S2 C2 C1 . . . 120.44(17) no
C1 C2 C3 . . . 121.4(2) no
C2 C3 C4 . . . 119.5(2) no
C3 C4 C10 . . . 121.6(2) no
C6 C5 C10 . . . 120.6(2) no
C5 C6 C7 . . . 120.4(2) no
C6 C7 C8 . . . 120.3(2) no
N8 C8 C9 . . . 118.54(19) no
C7 C8 C9 . . . 122.1(2) no
N8 C8 C7 . . . 119.38(18) no
C1 C9 C10 . . . 118.78(19) no
C8 C9 C10 . . . 116.9(2) no
C1 C9 C8 . . . 124.3(2) no
C5 C10 C9 . . . 119.6(2) no
C4 C10 C9 . . . 118.7(2) no
C4 C10 C5 . . . 121.7(2) no
C2 C1 H1 . . . 120.00 no
C9 C1 H1 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 119.00 no
C10 C4 H4 . . . 119.00 no
C10 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C7 C6 H6 . . . 120.00 no
C6 C7 H7 . . . 120.00 no
C8 C7 H7 . . . 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
S2 O21 . . 1.4470(17) no
S2 O22 . . 1.4484(16) no
S2 O23 . . 1.469(2) no
S2 C2 . . 1.766(2) no
O1W H12W . . 0.90(3) no
O1W H11W . . 0.82(4) no
N8 C8 . . 1.464(3) no
N8 H81 . . 0.88(3) no
N8 H82 . . 0.89(4) no
N8 H83 . . 0.98(4) no
C1 C2 . . 1.365(3) no
C1 C9 . . 1.415(3) no
C2 C3 . . 1.412(3) no
C3 C4 . . 1.348(4) no
C4 C10 . . 1.415(4) no
C5 C10 . . 1.413(4) no
C5 C6 . . 1.352(4) no
C6 C7 . . 1.401(4) no
C7 C8 . . 1.351(3) no
C8 C9 . . 1.413(3) no
C9 C10 . . 1.427(3) no
C1 H1 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C7 H7 . . 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
O1W H11W O23 2_675 0.82(4) 1.98(4) 2.798(3) 176(3) yes
O1W H12W O22 2_775 0.90(3) 1.91(3) 2.796(3) 169(3) yes
N8 H81 O23 1_556 0.88(3) 1.95(3) 2.817(2) 171(2) yes
N8 H82 O21 2_775 0.89(4) 1.96(3) 2.793(3) 154(3) yes
N8 H83 O1W . 0.98(4) 1.82(4) 2.725(3) 152(4) yes
C1 H1 O21 . 0.9300 2.5200 2.899(3) 105.00 no
C1 H1 N8 . 0.9300 2.6100 2.913(3) 100.00 no
C6 H6 O22 4_466 0.9300 2.5300 3.281(3) 137.00 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
O21 S2 C2 C1 . . . . 12.5(2) no
O21 S2 C2 C3 . . . . -169.2(2) no
O22 S2 C2 C1 . . . . 135.40(18) no
O22 S2 C2 C3 . . . . -46.3(2) no
O23 S2 C2 C1 . . . . -106.85(19) no
O23 S2 C2 C3 . . . . 71.4(2) no
C9 C1 C2 S2 . . . . 175.82(16) no
C9 C1 C2 C3 . . . . -2.4(3) no
C2 C1 C9 C8 . . . . -179.0(2) no
C2 C1 C9 C10 . . . . 0.1(3) no
S2 C2 C3 C4 . . . . -175.6(2) no
C1 C2 C3 C4 . . . . 2.7(4) no
C2 C3 C4 C10 . . . . -0.6(4) no
C3 C4 C10 C5 . . . . 177.2(3) no
C3 C4 C10 C9 . . . . -1.7(4) no
C10 C5 C6 C7 . . . . 0.0(4) no
C6 C5 C10 C4 . . . . -180.0(3) no
C6 C5 C10 C9 . . . . -1.1(4) no
C5 C6 C7 C8 . . . . 0.0(4) no
C6 C7 C8 N8 . . . . -179.3(2) no
C6 C7 C8 C9 . . . . 1.2(4) no
N8 C8 C9 C1 . . . . -2.7(3) no
N8 C8 C9 C10 . . . . 178.2(2) no
C7 C8 C9 C1 . . . . 176.9(2) no
C7 C8 C9 C10 . . . . -2.2(3) no
C1 C9 C10 C4 . . . . 1.9(3) no
C1 C9 C10 C5 . . . . -177.0(2) no
C8 C9 C10 C4 . . . . -179.0(2) no
C8 C9 C10 C5 . . . . 2.1(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655863
