#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220494.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_2220494
loop_
_publ_author_name
'Vennila, Jasmine P.'
'Kavitha, Helen P.'
'Thiruvadigal, D. John'
'Venkatraman, B. R.'
'Manivannan, V.'
_publ_section_title
;
 3-Aminophenyl naphthalene-1-sulfonate
;
_journal_coeditor_code           GK2179
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o72
_journal_paper_doi               10.1107/S1600536808041032
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H13 N O3 S'
_chemical_formula_moiety         'C16 H13 N O3 S'
_chemical_formula_sum            'C16 H13 N O3 S'
_chemical_formula_weight         299.33
_chemical_name_systematic
;
3-Aminophenyl naphthalene-1-sulfonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.321(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4558(2)
_cell_length_b                   8.6712(3)
_cell_length_c                   19.5915(6)
_cell_measurement_reflns_used    4818
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.21
_cell_volume                     1413.24(7)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEX2'
_diffrn_measurement_method       'ω and φ'
_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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19808
_diffrn_reflns_theta_full        32.23
_diffrn_reflns_theta_max         32.23
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.9539
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.438
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0550
_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)+(0.0763P)²+0.3485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1739
_reflns_number_gt                3126
_reflns_number_total             4981
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2179.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_hbond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_hbond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220494
_cod_database_fobs_code          2220494
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 C1 0.34222(19) 0.8581(2) 0.10826(8) 0.0475(4) Uani d . 1 . .
C C2 0.2573(3) 0.9698(3) 0.13547(12) 0.0688(6) Uani d . 1 . .
H H2 0.2543 0.9701 0.1827 0.083 Uiso calc R 1 . .
C C3 0.1749(3) 1.0837(3) 0.09239(19) 0.0876(8) Uani d . 1 . .
H H3 0.1173 1.1596 0.1109 0.105 Uiso calc R 1 . .
C C4 0.1793(3) 1.0828(3) 0.02504(18) 0.0858(8) Uani d . 1 . .
H H4 0.1241 1.1593 -0.0029 0.103 Uiso calc R 1 . .
C C5 0.2639(2) 0.9713(2) -0.00569(11) 0.0634(5) Uani d . 1 . .
C C6 0.2687(4) 0.9715(4) -0.07762(13) 0.0910(9) Uani d . 1 . .
H H6 0.2122 1.0468 -0.1058 0.109 Uiso calc R 1 . .
C C7 0.3515(4) 0.8673(4) -0.10559(13) 0.1015(12) Uani d . 1 . .
H H7 0.3537 0.8711 -0.1529 0.122 Uiso calc R 1 . .
C C8 0.4342(4) 0.7536(3) -0.06564(14) 0.0872(9) Uani d . 1 . .
H H8 0.4913 0.6808 -0.0863 0.105 Uiso calc R 1 . .
C C9 0.4342(2) 0.7451(2) 0.00414(11) 0.0619(5) Uani d . 1 . .
H H9 0.4904 0.6666 0.0303 0.074 Uiso calc R 1 . .
C C10 0.34948(19) 0.85482(19) 0.03643(8) 0.0458(4) Uani d . 1 . .
C C11 0.21070(19) 0.52112(19) 0.14424(9) 0.0466(4) Uani d . 1 . .
C C12 0.0822(2) 0.5617(2) 0.09445(10) 0.0595(5) Uani d . 1 . .
H H12 0.0949 0.6176 0.0553 0.071 Uiso calc R 1 . .
C C13 -0.0674(2) 0.5150(3) 0.10555(12) 0.0696(6) Uani d . 1 . .
H H13 -0.1582 0.5414 0.0734 0.084 Uiso calc R 1 . .
C C14 -0.0850(2) 0.4309(2) 0.16279(11) 0.0637(5) Uani d . 1 . .
H H14 -0.1874 0.4025 0.1692 0.076 Uiso calc R 1 . .
C C15 0.0471(2) 0.3876(2) 0.21112(10) 0.0561(4) Uani d . 1 . .
C C16 0.1979(2) 0.4357(2) 0.20153(9) 0.0511(4) Uani d . 1 . .
H H16 0.2890 0.4101 0.2336 0.061 Uiso calc R 1 . .
O O1 0.36734(15) 0.56180(15) 0.13433(7) 0.0580(3) Uani d . 1 . .
O O2 0.3993(2) 0.7447(2) 0.23185(7) 0.0915(6) Uani d . 1 . .
O O3 0.60456(18) 0.7106(2) 0.15880(10) 0.0903(6) Uani d . 1 . .
N N1 0.0316(3) 0.3014(3) 0.26868(11) 0.0868(6) Uani d . 1 . .
H H1A -0.0621 0.2733 0.2752 0.104 Uiso calc R 1 . .
H H1B 0.1156 0.2758 0.2981 0.104 Uiso calc R 1 . .
S S1 0.44040(6) 0.72128(7) 0.16539(2) 0.06166(18) Uani 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'
O O 0.0106 0.0060 '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'
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
C2 C1 C10 . . 121.24(18) ?
C2 C1 S1 . . 117.12(15) ?
C10 C1 S1 . . 121.63(13) ?
C1 C2 C3 . . 120.2(2) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C4 C3 C2 . . 119.7(2) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 122.6(2) ?
C3 C4 H4 . . 118.7 ?
C5 C4 H4 . . 118.7 ?
C4 C5 C6 . . 122.3(3) ?
C4 C5 C10 . . 119.2(2) ?
C6 C5 C10 . . 118.5(2) ?
C7 C6 C5 . . 121.6(3) ?
C7 C6 H6 . . 119.2 ?
C5 C6 H6 . . 119.2 ?
C6 C7 C8 . . 120.6(2) ?
C6 C7 H7 . . 119.7 ?
C8 C7 H7 . . 119.7 ?
C9 C8 C7 . . 121.2(3) ?
C9 C8 H8 . . 119.4 ?
C7 C8 H8 . . 119.4 ?
C8 C9 C10 . . 120.2(2) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C9 C10 C5 . . 117.90(18) ?
C9 C10 C1 . . 125.09(18) ?
C5 C10 C1 . . 117.02(17) ?
C16 C11 C12 . . 123.72(16) ?
C16 C11 O1 . . 117.47(15) ?
C12 C11 O1 . . 118.71(16) ?
C11 C12 C13 . . 116.40(18) ?
C11 C12 H12 . . 121.8 ?
C13 C12 H12 . . 121.8 ?
C14 C13 C12 . . 121.48(18) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C13 C14 C15 . . 120.92(18) ?
C13 C14 H14 . . 119.5 ?
C15 C14 H14 . . 119.5 ?
N1 C15 C14 . . 121.64(19) ?
N1 C15 C16 . . 119.91(19) ?
C14 C15 C16 . . 118.43(17) ?
C11 C16 C15 . . 119.01(16) ?
C11 C16 H16 . . 120.5 ?
C15 C16 H16 . . 120.5 ?
C11 O1 S1 . . 118.20(11) ?
C15 N1 H1A . . 120.0 ?
C15 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
O3 S1 O2 . . 119.75(11) ?
O3 S1 O1 . . 103.16(10) ?
O2 S1 O1 . . 109.45(9) ?
O3 S1 C1 . . 110.36(9) ?
O2 S1 C1 . . 108.99(11) ?
O1 S1 C1 . . 103.85(7) ?
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
C1 C2 . 1.370(3) ?
C1 C10 . 1.420(2) ?
C1 S1 . 1.7368(19) ?
C2 C3 . 1.401(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.327(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.401(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.417(3) ?
C5 C10 . 1.418(3) ?
C6 C7 . 1.321(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.370(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.369(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.408(3) ?
C9 H9 . 0.9300 ?
C11 C16 . 1.365(2) ?
C11 C12 . 1.370(2) ?
C11 O1 . 1.4173(19) ?
C12 C13 . 1.382(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.368(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.381(3) ?
C14 H14 . 0.9300 ?
C15 N1 . 1.378(3) ?
C15 C16 . 1.386(2) ?
C16 H16 . 0.9300 ?
O1 S1 . 1.5905(14) ?
O2 S1 . 1.4212(16) ?
O3 S1 . 1.4199(16) ?
N1 H1A . 0.8600 ?
N1 H1B . 0.8600 ?
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
C2 H2 O2 . 0.93 2.41 2.829(3) 107 y
C9 H9 O3 . 0.93 2.56 3.127(3) 120 y
N1 H1B O3 2_645 0.86 2.43 3.246(3) 158 y
C7 H7 O2 4_575 0.93 2.56 3.422(3) 153.7 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C3 . . . . 0.2(3) ?
S1 C1 C2 C3 . . . . -179.87(16) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C2 C3 C4 C5 . . . . 0.1(4) ?
C3 C4 C5 C6 . . . . -179.7(2) ?
C3 C4 C5 C10 . . . . -0.5(3) ?
C4 C5 C6 C7 . . . . 178.7(2) ?
C10 C5 C6 C7 . . . . -0.6(3) ?
C5 C6 C7 C8 . . . . 0.9(4) ?
C6 C7 C8 C9 . . . . -0.4(4) ?
C7 C8 C9 C10 . . . . -0.5(3) ?
C8 C9 C10 C5 . . . . 0.8(3) ?
C8 C9 C10 C1 . . . . -179.44(16) ?
C4 C5 C10 C9 . . . . -179.52(17) ?
C6 C5 C10 C9 . . . . -0.3(2) ?
C4 C5 C10 C1 . . . . 0.7(2) ?
C6 C5 C10 C1 . . . . 179.93(16) ?
C2 C1 C10 C9 . . . . 179.68(17) ?
S1 C1 C10 C9 . . . . -0.3(2) ?
C2 C1 C10 C5 . . . . -0.6(2) ?
S1 C1 C10 C5 . . . . 179.50(12) ?
C16 C11 C12 C13 . . . . 1.8(3) ?
O1 C11 C12 C13 . . . . 178.00(17) ?
C11 C12 C13 C14 . . . . -0.9(3) ?
C12 C13 C14 C15 . . . . -1.0(3) ?
C13 C14 C15 N1 . . . . -179.3(2) ?
C13 C14 C15 C16 . . . . 2.1(3) ?
C12 C11 C16 C15 . . . . -0.7(3) ?
O1 C11 C16 C15 . . . . -176.96(15) ?
N1 C15 C16 C11 . . . . -179.90(18) ?
C14 C15 C16 C11 . . . . -1.3(3) ?
C16 C11 O1 S1 . . . . -91.61(17) ?
C12 C11 O1 S1 . . . . 91.97(18) ?
C11 O1 S1 O3 . . . . 168.69(12) ?
C11 O1 S1 O2 . . . . 40.15(16) ?
C11 O1 S1 C1 . . . . -76.12(13) ?
C2 C1 S1 O3 . . . . -127.86(16) ?
C10 C1 S1 O3 . . . . 52.09(16) ?
C2 C1 S1 O2 . . . . 5.58(17) ?
C10 C1 S1 O2 . . . . -174.48(13) ?
C2 C1 S1 O1 . . . . 122.16(14) ?
C10 C1 S1 O1 . . . . -57.89(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14204911
