#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/84/2218452.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_2218452
loop_
_publ_author_name
'Vennila, Jasmine P.'
'Thilagavathi, R.'
'Kavipriya, R.'
'Kavitha, Helen P.'
'Manivannan, V.'
_publ_section_title
;
 4-Aminophenyl naphthalene-1-sulfonate
;
_journal_coeditor_code           IS2293
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1124
_journal_paper_doi               10.1107/S1600536808014438
_journal_volume                  64
_journal_year                    2008
_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
;
4-Aminophenyl naphthalene-1-sulfonate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0456(3)
_cell_length_b                   12.4789(6)
_cell_length_c                   15.8064(8)
_cell_measurement_reflns_used    4586
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      2.8
_cell_volume                     1389.72(11)
_computing_cell_refinement       'APEX2 (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'APEX2 (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 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19808
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.85
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.9623
_exptl_absorpt_correction_T_min  0.9179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.371
_refine_ls_abs_structure_details 'Flack (1983), 1972 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4629
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0513
_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)+(0.0956P)²+0.1498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1637
_reflns_number_gt                3267
_reflns_number_total             4629
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2293.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_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 (6 times).

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

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_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 (6
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2218452
_cod_database_fobs_code          2218452
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
C C1 0.2028(3) -0.04132(18) 0.71108(14) 0.0415(4) Uani d U 1
C C2 0.0284(3) -0.0930(2) 0.71475(17) 0.0508(6) Uani d . 1
H H2 -0.0763 -0.0641 0.6871 0.061 Uiso calc R 1
C C3 0.0110(3) -0.1874(2) 0.7597(2) 0.0545(6) Uani d . 1
H H3 -0.1064 -0.2211 0.7637 0.065 Uiso calc R 1
C C4 0.1674(3) -0.23186(18) 0.79873(15) 0.0443(5) Uani d . 1
C C5 0.3412(3) -0.18155(19) 0.79520(16) 0.0488(5) Uani d . 1
H H5 0.4463 -0.2117 0.8217 0.059 Uiso calc R 1
C C6 0.3577(3) -0.08513(19) 0.75158(17) 0.0503(5) Uani d . 1
H H6 0.4740 -0.0500 0.7497 0.060 Uiso calc R 1
C C7 0.2918(4) -0.0253(2) 0.51224(15) 0.0462(5) Uani d . 1
C C8 0.4146(4) -0.1082(2) 0.5015(2) 0.0569(6) Uani d . 1
H H8 0.5286 -0.1097 0.5311 0.068 Uiso calc R 1
C C9 0.3689(6) -0.1918(2) 0.4455(2) 0.0699(8) Uani d . 1
H H9 0.4551 -0.2472 0.4370 0.084 Uiso calc R 1
C C10 0.2039(6) -0.1927(2) 0.40449(19) 0.0634(7) Uani d . 1
H H10 0.1759 -0.2496 0.3685 0.076 Uiso calc R 1
C C11 0.0689(4) -0.1083(2) 0.41450(18) 0.0539(6) Uani d . 1
C C12 -0.1042(5) -0.1111(3) 0.3724(2) 0.0664(8) Uani d . 1
H H12 -0.1329 -0.1691 0.3377 0.080 Uiso calc R 1
C C13 -0.2326(5) -0.0302(3) 0.38116(19) 0.0685(8) Uani d . 1
H H13 -0.3481 -0.0328 0.3527 0.082 Uiso calc R 1
C C14 -0.1884(4) 0.0572(3) 0.43368(18) 0.0621(7) Uani d . 1
H H14 -0.2748 0.1131 0.4393 0.074 Uiso calc R 1
C C15 -0.0212(4) 0.0612(2) 0.47630(17) 0.0515(6) Uani d . 1
H H15 0.0046 0.1198 0.5108 0.062 Uiso calc R 1
C C16 0.1133(3) -0.02101(18) 0.46937(15) 0.0451(5) Uani d . 1
N N1 0.1446(3) -0.32773(15) 0.83938(13) 0.0487(5) Uani d . 1
H H1A 0.2400 -0.3580 0.8635 0.058 Uiso calc R 1
H H1B 0.0348 -0.3578 0.8408 0.058 Uiso calc R 1
O O1 0.2166(3) 0.05975(15) 0.66776(12) 0.0592(5) Uani d U 1
O O2 0.3197(4) 0.17748(15) 0.55522(14) 0.0706(6) Uani d . 1
O O3 0.5453(3) 0.04850(19) 0.61441(14) 0.0659(6) Uani d . 1
S S1 0.35628(9) 0.07323(5) 0.58673(4) 0.04995(18) Uani d U 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
C6 C1 C2 119.8(2)
C6 C1 O1 121.0(2)
C2 C1 O1 119.1(2)
C3 C2 C1 119.7(2)
C3 C2 H2 120.1
C1 C2 H2 120.1
C4 C3 C2 120.1(2)
C4 C3 H3 119.9
C2 C3 H3 119.9
N1 C4 C5 121.5(2)
N1 C4 C3 117.9(2)
C5 C4 C3 120.6(2)
C4 C5 C6 119.2(2)
C4 C5 H5 120.4
C6 C5 H5 120.4
C1 C6 C5 120.5(2)
C1 C6 H6 119.8
C5 C6 H6 119.8
C8 C7 C16 121.9(2)
C8 C7 S1 116.8(2)
C16 C7 S1 121.19(19)
C7 C8 C9 119.9(3)
C7 C8 H8 120.1
C9 C8 H8 120.1
C10 C9 C8 120.9(3)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C10 C11 121.4(3)
C9 C10 H10 119.3
C11 C10 H10 119.3
C12 C11 C16 120.2(3)
C12 C11 C10 120.8(3)
C16 C11 C10 119.0(3)
C13 C12 C11 121.0(3)
C13 C12 H12 119.5
C11 C12 H12 119.5
C12 C13 C14 119.2(3)
C12 C13 H13 120.4
C14 C13 H13 120.4
C15 C14 C13 120.9(3)
C15 C14 H14 119.5
C13 C14 H14 119.5
C14 C15 C16 121.4(3)
C14 C15 H15 119.3
C16 C15 H15 119.3
C15 C16 C11 117.3(2)
C15 C16 C7 125.8(2)
C11 C16 C7 116.9(2)
C4 N1 H1A 120.0
C4 N1 H1B 120.0
H1A N1 H1B 120.0
C1 O1 S1 120.50(15)
O2 S1 O3 118.25(13)
O2 S1 O1 105.20(13)
O3 S1 O1 107.43(12)
O2 S1 C7 111.02(13)
O3 S1 C7 107.04(13)
O1 S1 C7 107.38(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.378(3)
C1 C2 1.389(3)
C1 O1 1.438(3)
C2 C3 1.381(4)
C2 H2 0.9300
C3 C4 1.380(3)
C3 H3 0.9300
C4 N1 1.368(3)
C4 C5 1.377(3)
C5 C6 1.392(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.360(4)
C7 C16 1.430(3)
C7 S1 1.762(3)
C8 C9 1.404(4)
C8 H8 0.9300
C9 C10 1.332(5)
C9 H9 0.9300
C10 C11 1.428(5)
C10 H10 0.9300
C11 C12 1.390(4)
C11 C16 1.427(3)
C12 C13 1.362(5)
C12 H12 0.9300
C13 C14 1.406(5)
C13 H13 0.9300
C14 C15 1.358(4)
C14 H14 0.9300
C15 C16 1.401(4)
C15 H15 0.9300
N1 H1A 0.8600
N1 H1B 0.8600
O2 S1 1.417(2)
O3 S1 1.436(2)
O1 S1 1.624(2)
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
C6 H6 O3 . 0.93 2.52 3.038(3) 116 y
C8 H8 O3 . 0.93 2.38 2.804(4) 108 y
C15 H15 O2 . 0.93 2.44 3.071(4) 125 y
N1 H1B O1 4_546 0.86 2.05 2.909(3) 173 y
N1 H1A O3 4_646 0.86 1.94 2.773(3) 162 y
C6 H6 Cg 2_555 0.93 2.84 3.380(3) 107 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
C6 C1 C2 C3 0.7(4)
O1 C1 C2 C3 -176.8(2)
C1 C2 C3 C4 -1.9(4)
C2 C3 C4 N1 -177.2(2)
C2 C3 C4 C5 1.6(4)
N1 C4 C5 C6 178.7(2)
C3 C4 C5 C6 -0.1(4)
C2 C1 C6 C5 0.9(4)
O1 C1 C6 C5 178.3(2)
C4 C5 C6 C1 -1.1(4)
C16 C7 C8 C9 1.4(4)
S1 C7 C8 C9 177.6(2)
C7 C8 C9 C10 -2.0(5)
C8 C9 C10 C11 1.2(5)
C9 C10 C11 C12 -178.9(3)
C9 C10 C11 C16 0.4(4)
C16 C11 C12 C13 1.4(4)
C10 C11 C12 C13 -179.4(3)
C11 C12 C13 C14 0.0(4)
C12 C13 C14 C15 -0.8(4)
C13 C14 C15 C16 0.3(4)
C14 C15 C16 C11 1.1(4)
C14 C15 C16 C7 -179.1(2)
C12 C11 C16 C15 -1.9(4)
C10 C11 C16 C15 178.9(2)
C12 C11 C16 C7 178.3(2)
C10 C11 C16 C7 -1.0(3)
C8 C7 C16 C15 -179.7(3)
S1 C7 C16 C15 4.3(3)
C8 C7 C16 C11 0.1(3)
S1 C7 C16 C11 -175.90(18)
C6 C1 O1 S1 63.1(3)
C2 C1 O1 S1 -119.4(2)
C1 O1 S1 O2 174.10(17)
C1 O1 S1 O3 -59.1(2)
C1 O1 S1 C7 55.8(2)
C8 C7 S1 O2 137.0(2)
C16 C7 S1 O2 -46.8(2)
C8 C7 S1 O3 6.6(2)
C16 C7 S1 O3 -177.21(18)
C8 C7 S1 O1 -108.5(2)
C16 C7 S1 O1 67.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24740099
