#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/39/2003945.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_2003945
loop_
_publ_author_name
'Ehlinger, N.'
'Perrin, M.'
_publ_section_title
;
 4-(4-Hydroxy-3,5-dimethylphenylazo)benzenesulfonic Acid
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1846
_journal_page_last               1849
_journal_paper_doi               10.1107/S0108270195002496
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source        'slow evaporation of water solution'
_chemical_formula_moiety         'C14 H14 N2 O4 S , H2 O'
_chemical_formula_sum            'C14 H16 N2 O5 S'
_chemical_formula_weight         324.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source           IntTabC
_cell_angle_alpha                90
_cell_angle_beta                 101.83(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.586(2)
_cell_length_b                   8.583(1)
_cell_length_c                   12.186(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      51
_cell_measurement_theta_min      15
_cell_volume                     1493.2(4)
_diffrn_measurement_device       'Nonius CAD-4'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54056
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6239
_diffrn_reflns_theta_max         73
_diffrn_standards_decay_%        -6.5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.120
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.7228
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.57
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   0.994
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2972
_refine_ls_R_factor_obs          0.0393
_refine_ls_shift/esd_max         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/{σ(Fₒ²)+[0.0225(Fₒ²+2Fc²)]²}'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1077
_reflns_number_observed          2106
_reflns_number_total             2972
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            pa1174.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '
1/{\s(F~o~^2^)+[0.0225(F~o~^2^+2F~c~^2^)]^2^}' was changed to 'calc'.
New tag '_refine_ls_weighting_details' was created. The value of the
new tag was set to 'w =
1/{\s(F~o~^2^)+[0.0225(F~o~^2^+2F~c~^2^)]^2^}'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1493.0(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2003945
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,1/2+z
-x,-y,-z
1/2-x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
O(1) -0.1332(1) 0.9763(2) 1.1363(1) 3.58(4)
C(1) -0.0975(1) 0.8795(2) 1.0729(2) 2.66(4)
C(2) -0.0007(1) 0.8393(2) 1.0933(2) 2.54(4)
C(3) 0.0295(1) 0.7420(2) 1.0194(2) 2.63(4)
C(4) -0.0337(1) 0.6800(2) 0.9260(2) 2.71(4)
C(5) -0.1297(1) 0.7168(3) 0.9105(2) 3.24(5)
C(6) -0.1630(1) 0.8164(2) 0.9805(2) 3.10(4)
C(7) -0.2643(2) 0.8627(3) 0.9627(2) 4.65(6)
C(8) 0.0664(2) 0.9028(3) 1.1931(2) 3.58(5)
N(1) -0.0124(1) 0.5857(2) 0.8451(1) 2.81(4)
N(2) 0.0725(1) 0.5473(2) 0.8468(1) 2.67(4)
C(9) 0.0933(1) 0.4532(2) 0.7596(2) 2.44(4)
C(10) 0.1829(1) 0.3938(2) 0.7729(2) 2.82(4)
C(11) 0.2059(1) 0.3018(2) 0.6891(2) 2.72(4)
C(12) 0.1387(1) 0.2684(2) 0.5938(2) 2.37(4)
C(13) 0.0491(1) 0.3297(3) 0.5819(2) 3.39(5)
C(14) 0.0254(1) 0.4224(3) 0.6645(2) 3.29(5)
S 0.16530(3) 0.14628(6) 0.48728(4) 2.51(1)
O(2) 0.26688(9) 0.1426(2) 0.5038(1) 3.50(3)
O(3) 0.1212(1) 0.2173(2) 0.3820(1) 3.45(3)
O(4) 0.1258(1) -0.0050(2) 0.5044(1) 3.85(4)
O(5) -0.0647(1) 1.1321(2) 1.3127(1) 3.74(4)
H(1) -0.100(2) 1.020(3) 1.193(2) O
H(3) 0.0926(1) 0.7161(2) 1.0308(2) O
H(5) -0.1715(1) 0.6720(3) 0.8509(2) O
H(7D) -0.3006(2) 0.799(2) 0.905(1) O
H(7E) -0.2708(2) 0.9701(7) 0.941(2) O
H(7F) -0.2861(4) 0.848(2) 1.0312(5) O
H(8D) 0.1283(2) 0.865(1) 1.1928(7) O
H(8E) 0.0478(6) 0.869(1) 1.2605(2) O
H(8F) 0.0659(8) 1.0146(3) 1.1900(7) O
H(20) 0.122(2) 0.578(3) 0.906(2) 0.064(8)
H(10) 0.2273(1) 0.4152(2) 0.8375(2) O
H(11) 0.2663(1) 0.2625(2) 0.6967(2) O
H(13) 0.0045(1) 0.3081(3) 0.5174(2) O
H(14) -0.0347(1) 0.4631(3) 0.6566(2) O
H(50) -0.077(2) 1.083(3) 1.370(2) 0.067(9)
H(51) -0.008(2) 1.146(3) 1.328(2) 0.062(8)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O(1) C(1) C(2) 123.3(2) yes
O(1) C(1) C(6) 115.0(2) yes
C(2) C(1) C(6) 121.7(2) yes
C(1) C(2) C(3) 118.4(2) yes
C(1) C(2) C(8) 120.8(2) yes
C(3) C(2) C(8) 120.8(2) yes
C(2) C(3) C(4) 121.1(2) yes
C(3) C(4) C(5) 119.2(2) yes
C(3) C(4) N(1) 126.9(2) yes
C(5) C(4) N(1) 113.9(2) yes
C(4) C(5) C(6) 121.8(2) yes
C(9) C(14) C(13) 118.4(2) yes
C(13) C(12) S 119.30(10) yes
C(12) S O(2) 106.33(8) yes
C(12) S O(4) 105.70(10) yes
O(2) S O(4) 112.56(9) yes
C(1) C(6) C(5) 117.6(2) yes
C(1) C(6) C(7) 119.6(2) yes
C(5) C(6) C(7) 122.8(2) yes
C(4) N(1) N(2) 120.4(2) yes
N(1) N(2) C(9) 119.4(2) yes
N(2) C(9) C(10) 117.8(2) yes
N(2) C(9) C(14) 120.6(2) yes
C(10) C(9) C(14) 121.6(2) yes
C(9) C(10) C(11) 119.3(2) yes
C(10) C(11) C(12) 119.9(2) yes
C(11) C(12) C(13) 119.9(2) yes
C(11) C(12) S 120.80(10) yes
C(12) C(13) C(14) 120.8(2) yes
C(12) S O(3) 106.05(9) yes
O(2) S O(3) 112.76(9) yes
O(3) S O(4) 112.76(9) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.313(3) yes
C(2) C(3) 1.365(3) yes
C(4) C(5) 1.411(3) yes
C(6) C(7) 1.501(3) yes
C(2) C(8) 1.499(3) yes
N(1) N(2) 1.276(2) yes
C(9) C(10) 1.380(3) yes
C(11) C(12) 1.386(2) yes
C(13) C(14) 1.382(3) yes
C(12) S 1.773(2) yes
S O(3) 1.4470(10) yes
C(1) C(2) 1.424(3) yes
C(3) C(4) 1.413(2) yes
C(5) C(6) 1.366(3) yes
C(1) C(6) 1.426(3) yes
C(4) N(1) 1.359(3) yes
N(2) C(9) 1.417(3) yes
C(10) C(11) 1.386(3) yes
C(12) C(13) 1.388(3) yes
C(9) C(14) 1.386(3) yes
S O(2) 1.4540(10) yes
S O(4) 1.453(2) yes
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
_geom_torsion_publ_flag
C(5) C(4) N(1) N(2) 177.7(3) yes
C(4) N(1) N(2) C(9) -177.9(3) yes
N(1) N(2) C(9) C10) -170.0(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139054470
