#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/75/4507572.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4507572
loop_
_publ_author_name
'Cherukuvada, Suryanarayan'
'Bolla, Geetha'
'Sikligar, Kanishka'
'Nangia, Ashwini'
_publ_section_title
;
 4-Aminosalicylic Acid Adducts
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1551
_journal_paper_doi               10.1021/cg301798s
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C14 H16 N2 O10 S'
_chemical_formula_weight         404.35
_space_group_IT_number           32
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 -2ab'
_symmetry_space_group_name_H-M   'P b a 2'
_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                   15.7940(16)
_cell_length_b                   19.897(2)
_cell_length_c                   5.5179(6)
_cell_measurement_reflns_used    6679
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.42
_cell_volume                     1734.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3402
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.9624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0443
_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)+(0.0641P)²+0.5819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                3244
_reflns_number_total             3402
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301798s_si_007.cif
_cod_data_source_block           Bis-4-Ammonium-salicylic-acid-sulfate
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pba2
_cod_database_code               4507572
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.34639(19) 0.72651(15) 0.5945(6) 0.0343(6) Uani 1 1 d .
C2 C 0.33061(19) 0.79790(14) 0.5373(6) 0.0324(6) Uani 1 1 d .
C3 C 0.28351(17) 0.81446(14) 0.3314(5) 0.0318(6) Uani 1 1 d .
C4 C 0.26342(19) 0.88038(16) 0.2799(6) 0.0356(7) Uani 1 1 d .
H4 H 0.2322 0.8913 0.1425 0.043 Uiso 1 1 calc R
C5 C 0.29088(16) 0.92998(13) 0.4380(6) 0.0298(6) Uani 1 1 d .
C6 C 0.3380(2) 0.91563(16) 0.6391(7) 0.0428(8) Uani 1 1 d .
H6 H 0.3560 0.9498 0.7417 0.051 Uiso 1 1 calc R
C7 C 0.3586(2) 0.84918(16) 0.6877(6) 0.0404(7) Uani 1 1 d .
H7 H 0.3916 0.8389 0.8224 0.048 Uiso 1 1 calc R
C8 C 0.6386(2) 0.84636(15) 0.6584(7) 0.0382(7) Uani 1 1 d .
C9 C 0.60179(18) 0.78070(14) 0.5902(6) 0.0312(6) Uani 1 1 d .
C10 C 0.55281(17) 0.77531(13) 0.3798(6) 0.0341(6) Uani 1 1 d .
C11 C 0.52152(17) 0.71270(15) 0.3092(6) 0.0319(6) Uani 1 1 d .
H11 H 0.4901 0.7083 0.1676 0.038 Uiso 1 1 calc R
C12 C 0.53792(16) 0.65784(12) 0.4519(5) 0.0276(6) Uani 1 1 d .
C13 C 0.58558(18) 0.66155(14) 0.6625(6) 0.0326(6) Uani 1 1 d .
H13 H 0.5953 0.6236 0.7570 0.039 Uiso 1 1 calc R
C14 C 0.61805(18) 0.72327(14) 0.7271(6) 0.0334(7) Uani 1 1 d .
H14 H 0.6516 0.7267 0.8651 0.040 Uiso 1 1 calc R
H1 H 0.391(3) 0.665(2) 0.819(9) 0.074(13) Uiso 1 1 d .
H3 H 0.278(3) 0.716(2) 0.220(8) 0.068(13) Uiso 1 1 d .
H1A H 0.214(2) 1.0061(17) 0.470(7) 0.034(8) Uiso 1 1 d .
H2A H 0.535(3) 0.564(2) 0.345(9) 0.067(14) Uiso 1 1 d .
H4A H 0.716(3) 0.886(2) 0.853(8) 0.063(12) Uiso 1 1 d .
H6A H 0.562(3) 0.861(2) 0.279(9) 0.065(13) Uiso 1 1 d .
H1B H 0.301(2) 1.0270(18) 0.469(7) 0.040(10) Uiso 1 1 d .
H2B H 0.467(3) 0.591(2) 0.239(9) 0.072(14) Uiso 1 1 d .
H2C H 0.468(3) 0.570(2) 0.497(9) 0.074(14) Uiso 1 1 d .
H3C H 0.263(2) 1.0030(17) 0.228(7) 0.039(10) Uiso 1 1 d .
N1 N 0.26443(16) 0.99936(13) 0.3923(6) 0.0342(5) Uani 1 1 d .
N2 N 0.50308(17) 0.59267(12) 0.3803(6) 0.0341(5) Uani 1 1 d .
O1 O 0.38512(16) 0.71679(11) 0.8008(5) 0.0454(6) Uani 1 1 d .
O2 O 0.32531(15) 0.68034(11) 0.4608(4) 0.0461(6) Uani 1 1 d .
O3 O 0.25499(19) 0.76762(14) 0.1721(6) 0.0603(7) Uani 1 1 d .
O4 O 0.68852(14) 0.84546(11) 0.8450(4) 0.0440(6) Uani 1 1 d .
O5 O 0.62350(16) 0.89764(11) 0.5429(6) 0.0557(7) Uani 1 1 d .
O6 O 0.53326(18) 0.82767(12) 0.2369(5) 0.0541(7) Uani 1 1 d .
O7 O 0.41092(14) 0.59524(10) 0.9448(4) 0.0433(6) Uani 1 1 d .
O8 O 0.39061(14) 0.48161(10) 1.0699(4) 0.0384(5) Uani 1 1 d .
O9 O 0.38561(14) 0.51124(11) 0.6461(4) 0.0374(5) Uani 1 1 d .
O10 O 0.27311(12) 0.54301(10) 0.9145(4) 0.0362(5) Uani 1 1 d .
S1 S 0.36592(4) 0.53216(3) 0.89607(14) 0.02668(17) Uani 1 1 d .
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
O2 C1 O1 122.8(3)
O2 C1 C2 123.2(3)
O1 C1 C2 114.1(3)
C7 C2 C3 118.9(3)
C7 C2 C1 121.7(3)
C3 C2 C1 119.4(3)
O3 C3 C4 116.3(3)
O3 C3 C2 122.7(3)
C4 C3 C2 120.9(3)
C3 C4 C5 118.4(3)
C6 C5 C4 122.2(3)
C6 C5 N1 119.5(3)
C4 C5 N1 118.3(3)
C5 C6 C7 118.9(3)
C2 C7 C6 120.7(3)
O5 C8 O4 122.8(3)
O5 C8 C9 121.8(3)
O4 C8 C9 115.4(3)
C14 C9 C10 119.3(3)
C14 C9 C8 120.9(3)
C10 C9 C8 119.7(3)
O6 C10 C11 116.6(3)
O6 C10 C9 123.7(3)
C11 C10 C9 119.7(3)
C12 C11 C10 118.9(3)
C11 C12 C13 122.8(2)
C11 C12 N2 118.7(3)
C13 C12 N2 118.5(3)
C14 C13 C12 117.8(3)
C13 C14 C9 121.5(3)
O8 S1 O7 110.08(14)
O8 S1 O9 111.60(14)
O7 S1 O9 108.12(14)
O8 S1 O10 108.81(13)
O7 S1 O10 109.94(13)
O9 S1 O10 108.27(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.224(4)
C1 O1 1.307(4)
C1 C2 1.476(4)
C2 C7 1.388(4)
C2 C3 1.398(4)
C3 O3 1.358(4)
C3 C4 1.379(4)
C4 C5 1.387(4)
C5 C6 1.366(5)
C5 N1 1.464(4)
C6 C7 1.388(5)
C8 O5 1.226(4)
C8 O4 1.297(4)
C8 C9 1.479(4)
C9 C14 1.393(4)
C9 C10 1.400(4)
C10 O6 1.343(4)
C10 C11 1.396(4)
C11 C12 1.371(4)
C12 C13 1.387(4)
C12 N2 1.463(3)
C13 C14 1.378(4)
O7 S1 1.467(2)
O8 S1 1.443(2)
O9 S1 1.474(2)
O10 S1 1.485(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652526
2 PubChem 139146446
