#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/81/4518166.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_4518166
loop_
_publ_author_name
'Yahia, Hamdi Ben'
'Sabri, Souhir'
'Essehli, Rachid'
'Kasak, Peter'
'Drogosz-Stachowicz, Joanna'
'Janecka, Anna'
'El Bali, Brahim'
_publ_section_title
;
 Crystal Growth, Single Crystal Structure, and Biological Activity of
 Thiazolo-Pyridine Dicarboxylic Acid Derivatives
;
_journal_issue                   43
_journal_name_full               'ACS Omega'
_journal_page_first              27756
_journal_page_last               27765
_journal_paper_doi               10.1021/acsomega.0c01769
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C9 H5 N O5 S, H2 O, 2(H4 N)'
_chemical_formula_sum            'C9 H15 N3 O6 S'
_chemical_formula_weight         293.3
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                67.751(2)
_cell_angle_beta                 80.440(2)
_cell_angle_gamma                83.967(2)
_cell_formula_units_Z            2
_cell_length_a                   5.6564(3)
_cell_length_b                   10.7717(6)
_cell_length_c                   11.2333(6)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.26
_cell_volume                     624.01(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2016)'
_computing_data_collection       'Apex 3'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    Diamond
_computing_structure_refinement  Jana2006
_computing_structure_solution    'Direct method'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'four circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       multi-scan
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9883
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.19
_refine_ls_extinction_coef       5300(1000)
_refine_ls_extinction_method
'B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)'
_refine_ls_goodness_of_fit_gt    1.20
_refine_ls_goodness_of_fit_ref   1.12
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    48
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.0053
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(σ²(I)+0.0035999999I²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                2144
_reflns_number_total             3089
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            ao0c01769_si_005.cif
_cod_data_source_block           (4)
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4518166--4518169.cif.
;
_cod_original_formula_sum        'C9 H15 N3 O6 S1'
_cod_database_code               4518166
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.49810(9) 0.18604(5) 1.04691(4) Uani 0.03142(18) 2 1 d . . .
N1 N 0.3687(2) 0.34983(13) 0.82931(12) Uani 0.0185(5) 2 1 d . . .
O1 O 0.2313(2) 0.45441(12) 0.63444(12) Uani 0.0301(5) 2 1 d . . .
C1 C 0.2147(3) 0.15737(18) 1.00826(17) Uani 0.0297(7) 2 1 d . . .
O5 O 0.5478(3) 0.14917(15) 0.74543(15) Uani 0.0456(6) 2 1 d . . .
C5 C 0.6795(3) 0.54760(16) 0.77539(16) Uani 0.0206(6) 2 1 d . . .
O2 O 0.9981(2) 0.64499(13) 0.81862(13) Uani 0.0335(5) 2 1 d . . .
N2 N 0.9159(3) 0.30990(15) 0.56994(15) Uani 0.0303(6) 2 1 d . . .
C2 C 0.2221(3) 0.23365(15) 0.86175(15) Uani 0.0194(6) 2 1 d . . .
O4 O 0.1833(2) 0.07612(13) 0.76854(14) Uani 0.0391(6) 2 1 d . . .
O3 O 0.8151(2) 0.76459(12) 0.64639(12) Uani 0.0317(5) 2 1 d . . .
N3 N 0.7037(3) 0.13049(15) 0.32850(15) Uani 0.0275(6) 2 1 d . . .
C3 C 0.3694(3) 0.45441(16) 0.71194(15) Uani 0.0205(6) 2 1 d . . .
C4 C 0.5323(3) 0.55578(16) 0.68749(16) Uani 0.0225(6) 2 1 d . . .
C9 C 0.3270(3) 0.14634(16) 0.78282(15) Uani 0.0222(6) 2 1 d . . .
C8 C 0.8464(3) 0.66080(17) 0.74578(17) Uani 0.0227(6) 2 1 d . . .
C6 C 0.6770(3) 0.43624(16) 0.89294(16) Uani 0.0220(6) 2 1 d . . .
O6 O 0.7939(3) 0.03548(13) 0.58466(12) Uani 0.0352(5) 2 1 d . . .
C7 C 0.5220(3) 0.33834(16) 0.91607(15) Uani 0.0197(6) 2 1 d . . .
H1c1 H 0.203253 0.063184 1.027934 Uiso 0.0356 2 1 d . . .
H2c1 H 0.085107 0.194175 1.053619 Uiso 0.0356 2 1 d . . .
H1c2 H 0.062702 0.260583 0.840036 Uiso 0.0233 2 1 d . . .
H1c4 H 0.539174 0.631907 0.607254 Uiso 0.027 2 1 d . . .
H1c6 H 0.781006 0.429426 0.954765 Uiso 0.0264 2 1 d . . .
H1n3 H 0.7166(15) 0.0660(7) 0.2988(10) Uiso 0.0329 2 1 d . . .
H2n3 H 0.741087 0.099131 0.406961 Uiso 0.0329 2 1 d . . .
H3n3 H 0.800455 0.193093 0.27875 Uiso 0.0329 2 1 d . . .
H4n3 H 0.556798 0.163785 0.32951 Uiso 0.0329 2 1 d . . .
H1n2 H 0.9881(13) 0.2557(8) 0.5330(9) Uiso 0.0364 2 1 d . . .
H2n2 H 0.84876 0.377805 0.512952 Uiso 0.0364 2 1 d . . .
H3n2 H 0.806709 0.26745 0.632546 Uiso 0.0364 2 1 d . . .
H4n2 H 1.020134 0.338631 0.601269 Uiso 0.0364 2 1 d . . .
H1o6 H 0.816(3) -0.0598(5) 0.6158(15) Uiso 0.0423 2 1 d . . .
H2o6 H 0.688(3) 0.0532(16) 0.6524(12) Uiso 0.0423 2 1 d . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
S 0.1246 0.1234 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?
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
C1 S1 C7 . . . 91.49(8) ?
C2 N1 C3 . . . 120.74(15) ?
C2 N1 C7 . . . 115.64(12) ?
C3 N1 C7 . . . 123.18(14) ?
S1 C1 C2 . . . 105.56(12) ?
S1 C1 H1c1 . . . 109.47 ?
S1 C1 H2c1 . . . 109.47 ?
C2 C1 H1c1 . . . 109.47 ?
C2 C1 H2c1 . . . 109.47 ?
H1c1 C1 H2c1 . . . 113.11 ?
C9 O5 H2o6 . . . 121.1(6) ?
C4 C5 C8 . . . 119.47(13) ?
C4 C5 C6 . . . 120.67(16) ?
C8 C5 C6 . . . 119.85(17) ?
H1n2 N2 H2n2 . . . 109.47 ?
H1n2 N2 H3n2 . . . 109.47 ?
H1n2 N2 H4n2 . . . 109.47 ?
H2n2 N2 H3n2 . . . 109.47 ?
H2n2 N2 H4n2 . . . 109.47 ?
H3n2 N2 H4n2 . . . 109.47 ?
N1 C2 C1 . . . 105.94(16) ?
N1 C2 C9 . . . 111.14(12) ?
N1 C2 H1c2 . . . 111.81 ?
C1 C2 C9 . . . 112.49(13) ?
C1 C2 H1c2 . . . 110.43 ?
C9 C2 H1c2 . . . 105.16 ?
C8 O3 H1o6 . . 1_565 132.3(6) ?
H1n3 N3 H2n3 . . . 109.47 ?
H1n3 N3 H3n3 . . . 109.47 ?
H1n3 N3 H4n3 . . . 109.47 ?
H2n3 N3 H3n3 . . . 109.47 ?
H2n3 N3 H4n3 . . . 109.47 ?
H3n3 N3 H4n3 . . . 109.47 ?
N1 C3 O1 . . . 119.45(15) ?
N1 C3 C4 . . . 115.58(16) ?
O1 C3 C4 . . . 124.97(13) ?
C5 C4 C3 . . . 121.60(13) ?
C5 C4 H1c4 . . . 119.2 ?
C3 C4 H1c4 . . . 119.2 ?
O5 C9 C2 . . . 117.17(18) ?
O5 C9 O4 . . . 127.13(19) ?
C2 C9 O4 . . . 115.61(15) ?
C5 C8 O2 . . . 118.65(13) ?
C5 C8 O3 . . . 115.59(17) ?
O2 C8 O3 . . . 125.77(17) ?
C5 C6 C7 . . . 117.76(17) ?
C5 C6 H1c6 . . . 121.12 ?
C7 C6 H1c6 . . . 121.12 ?
H1o6 O6 H2o6 . . . 104.5(13) ?
S1 C7 N1 . . . 111.79(12) ?
S1 C7 C6 . . . 127.03(14) ?
N1 C7 C6 . . . 121.11(13) ?
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
S1 C1 . . 1.814(2) ?
S1 C7 . . 1.7391(14) ?
N1 C2 . . 1.469(2) ?
N1 C3 . . 1.3717(18) ?
N1 C7 . . 1.372(2) ?
O1 C3 . . 1.263(2) ?
C1 C2 . . 1.531(2) ?
C1 H1c1 . . 0.96 ?
C1 H2c1 . . 0.96 ?
O5 C9 . . 1.250(2) ?
C5 C4 . . 1.367(3) ?
C5 C8 . . 1.523(3) ?
C5 C6 . . 1.407(2) ?
O2 C8 . . 1.238(2) ?
N2 H1n2 . . 0.870(10) ?
N2 H2n2 . . 0.87 ?
N2 H3n2 . . 0.87 ?
N2 H4n2 . . 0.87 ?
C2 C9 . . 1.537(3) ?
C2 H1c2 . . 0.96 ?
O4 C9 . . 1.234(3) ?
O3 C8 . . 1.2676(18) ?
N3 H1n3 . . 0.870(11) ?
N3 H2n3 . . 0.87 ?
N3 H3n3 . . 0.87 ?
N3 H4n3 . . 0.87 ?
C3 C4 . . 1.420(3) ?
C4 H1c4 . . 0.96 ?
C6 C7 . . 1.364(3) ?
C6 H1c6 . . 0.96 ?
O6 H1o6 . . 0.953(6) ?
O6 H2o6 . . 0.953(15) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
N3 H1n3 O4 . . 2_656 0.870(11) 1.946(10) 2.803(3) 168.1(8) ?
N3 H2n3 O6 . . . 0.87 1.91 2.781(2) 174.69 ?
N3 H3n3 O2 . . 2_766 0.87 2.02 2.8860(19) 170.84 ?
N3 H4n3 O3 . . 2_666 0.87 2.17 3.039(2) 174.06 ?
N2 H1n2 O3 . . 2_766 0.870(10) 2.210(10) 2.976(2) 146.7(7) ?
N2 H2n2 O1 . . 2_666 0.87 2.01 2.8612(18) 167.36 ?
N2 H3n2 O5 . . . 0.87 1.98 2.833(2) 165.90 ?
N2 H4n2 O1 . . 1_655 0.87 1.98 2.828(2) 163.39 ?
O6 H1o6 O3 . . 1_545 0.953(6) 1.790(7) 2.7261(19) 166.7(18) ?
O6 H2o6 O5 . . . 0.953(15) 1.778(17) 2.680(2) 156.8(14) ?
loop_
_restr_angle_atom_site_label_1
_restr_angle_site_symmetry_1
_restr_angle_atom_site_label_2
_restr_angle_site_symmetry_2
_restr_angle_atom_site_label_3
_restr_angle_site_symmetry_3
_restr_angle_target
_restr_angle_target_weight_param
H1o6 . O6 . H2o6 . 104.45 0.05
loop_
_restr_distance_atom_site_label_1
_restr_distance_site_symmetry_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
N3 . H1n3 . 0.87 0.0015
N2 . H1n2 . 0.87 0.001
O6 . H1o6 . 0.96 0.005
O6 . H2o6 . 0.96 0.005
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
? ? ? ? ? ? ? ? ? ? ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346842
