#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/81/4518167.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_4518167
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 H9 N1 Na1 O7 P1 S1'
_chemical_formula_sum            'C9 H9 N Na O7 P S'
_chemical_formula_weight         329.2
_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                97.642(2)
_cell_angle_beta                 93.975(2)
_cell_angle_gamma                103.694(2)
_cell_formula_units_Z            2
_cell_length_a                   6.2307(3)
_cell_length_b                   9.0432(4)
_cell_length_c                   11.7429(5)
_cell_measurement_reflns_used    8781
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.35
_cell_volume                     633.64(5)
_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      150
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_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  0.02
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8781
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_T_max  0.7491
_exptl_absorpt_correction_T_min  0.7042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.7254
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.23
_refine_ls_extinction_coef       400(800)
_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   1.19
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    22
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3842
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.0039
_refine_ls_shift/su_mean         0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(σ²(I)+0.0038439999I²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                3689
_reflns_number_total             3842
_reflns_threshold_expression     I>0σ(I)
_cod_data_source_file            ao0c01769_si_004.cif
_cod_data_source_block           (3)
_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 H9 N1 Na1 O7 P1 S1'
_cod_database_code               4518167
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 -0.09202(6) 0.20599(5) 0.22679(4) Uani 0.02380(13) 2 1 d . . .
C1 C -0.0289(3) 0.38563(19) 0.16746(15) Uani 0.0234(5) 2 1 d . . .
C2 C 0.2237(2) 0.43121(16) 0.17236(12) Uani 0.0155(4) 2 1 d . . .
N1 N 0.3055(2) 0.38227(13) 0.27739(10) Uani 0.0143(3) 2 1 d . . .
C3 C 0.5198(2) 0.44742(16) 0.32909(12) Uani 0.0151(4) 2 1 d . . .
O1 O 0.63674(17) 0.55970(12) 0.29359(9) Uani 0.0196(3) 2 1 d . . .
C4 C 0.5861(2) 0.37511(17) 0.42171(12) Uani 0.0168(4) 2 1 d . . .
C5 C 0.4425(2) 0.25635(16) 0.45863(12) Uani 0.0166(4) 2 1 d . . .
C6 C 0.2222(2) 0.19870(17) 0.40639(12) Uani 0.0178(4) 2 1 d . . .
C7 C 0.1614(2) 0.26259(17) 0.31429(12) Uani 0.0160(4) 2 1 d . . .
C8 C 0.5173(3) 0.18989(17) 0.56073(12) Uani 0.0178(4) 2 1 d . . .
O2 O 0.38883(19) 0.10447(12) 0.61113(9) Uani 0.0216(3) 2 1 d . . .
O3 O 0.7326(2) 0.23600(15) 0.58892(11) Uani 0.0292(4) 2 1 d . . .
H1o3 H 0.775(3) 0.186(2) 0.6511(12) Uiso 0.035 2 1 d . . .
C9 C 0.3029(2) 0.35693(16) 0.06394(12) Uani 0.0145(4) 2 1 d . . .
O4 O 0.22575(19) 0.36912(14) -0.03083(9) Uani 0.0251(4) 2 1 d . . .
O5 O 0.45531(18) 0.28272(13) 0.08320(9) Uani 0.0194(3) 2 1 d . . .
H1o5 H 0.496(3) 0.2381(19) 0.0116(8) Uiso 0.0232 2 1 d . . .
Na1 Na 0.74862(9) 0.77456(7) 0.21683(5) Uani 0.01767(19) 2 1 d . . .
P1 P 1.28913(6) 0.91595(4) 0.15022(3) Uani 0.01623(12) 2 1 d . . .
O6 O 1.44820(19) 0.82207(14) 0.11022(10) Uani 0.0248(4) 2 1 d . . .
O7 O 1.12522(17) 0.84898(13) 0.22887(9) Uani 0.0206(3) 2 1 d . . .
H1p1 H 1.185(3) 0.934(2) 0.0595(16) Uiso 0.022(5) 2 1 d . . .
H2p1 H 1.411(3) 1.047(2) 0.1996(17) Uiso 0.029(5) 2 1 d . . .
H1c1 H -0.092271 0.367451 0.088456 Uiso 0.028 2 1 d . . .
H2c1 H -0.077945 0.462786 0.215759 Uiso 0.028 2 1 d . . .
H1c2 H 0.280022 0.540117 0.174733 Uiso 0.0186 2 1 d . . .
H1c4 H 0.735092 0.410785 0.458948 Uiso 0.0202 2 1 d . . .
H1c6 H 0.119639 0.118025 0.434442 Uiso 0.0213 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'
Na 0.0362 0.0249 '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'
P 0.1023 0.0942 '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 . . . 90.80(7) ?
S1 C1 C2 . . . 104.71(12) ?
S1 C1 H1c1 . . . 109.47 ?
S1 C1 H2c1 . . . 109.47 ?
C2 C1 H1c1 . . . 109.47 ?
C2 C1 H2c1 . . . 109.47 ?
H1c1 C1 H2c1 . . . 113.84 ?
C1 C2 N1 . . . 105.73(12) ?
C1 C2 C9 . . . 111.16(11) ?
C1 C2 H1c2 . . . 111.88 ?
N1 C2 C9 . . . 112.37(13) ?
N1 C2 H1c2 . . . 110.66 ?
C9 C2 H1c2 . . . 105.17 ?
C2 N1 C3 . . . 120.89(12) ?
C2 N1 C7 . . . 115.25(11) ?
C3 N1 C7 . . . 123.71(13) ?
N1 C3 O1 . . . 119.79(14) ?
N1 C3 C4 . . . 114.67(12) ?
O1 C3 C4 . . . 125.54(13) ?
C3 C4 C5 . . . 121.53(13) ?
C3 C4 H1c4 . . . 119.23 ?
C5 C4 H1c4 . . . 119.23 ?
C4 C5 C6 . . . 121.55(14) ?
C4 C5 C8 . . . 119.31(12) ?
C6 C5 C8 . . . 119.09(13) ?
C5 C6 C7 . . . 117.10(13) ?
C5 C6 H1c6 . . . 121.45 ?
C7 C6 H1c6 . . . 121.45 ?
S1 C7 N1 . . . 111.44(11) ?
S1 C7 C6 . . . 127.22(11) ?
N1 C7 C6 . . . 121.31(12) ?
C5 C8 O2 . . . 122.70(14) ?
C5 C8 O3 . . . 112.49(13) ?
C5 C8 H1o3 . . . 141.2(5) ?
O2 C8 O3 . . . 124.80(15) ?
O2 C8 H1o3 . . . 96.0(5) ?
C8 O3 H1o3 . . . 109.9(11) ?
C2 C9 O4 . . . 120.24(14) ?
C2 C9 O5 . . . 114.94(12) ?
C2 C9 H1o5 . . . 143.6(4) ?
O4 C9 O5 . . . 124.81(14) ?
O4 C9 H1o5 . . . 96.2(4) ?
C9 O5 H1o5 . . . 110.6(11) ?
O6 P1 O7 . . . 116.91(7) ?
O6 P1 H1p1 . . . 105.4(9) ?
O6 P1 H2p1 . . . 105.7(10) ?
O7 P1 H1p1 . . . 109.1(8) ?
O7 P1 H2p1 . . . 110.4(9) ?
H1p1 P1 H2p1 . . . 109.0(12) ?
H1o5 O6 P1 2_765 . . 132.6(7) ?
H1o3 O7 P1 2_766 . . 116.8(7) ?
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 . . 1.8208(18) ?
S1 C7 . . 1.7501(14) ?
C1 C2 . . 1.524(2) ?
C1 H1c1 . . 0.96 ?
C1 H2c1 . . 0.96 ?
C2 N1 . . 1.463(2) ?
C2 C9 . . 1.527(2) ?
C2 H1c2 . . 0.96 ?
N1 C3 . . 1.3855(17) ?
N1 C7 . . 1.3724(18) ?
C3 O1 . . 1.2408(18) ?
C3 C4 . . 1.427(2) ?
C4 C5 . . 1.366(2) ?
C4 H1c4 . . 0.96 ?
C5 C6 . . 1.411(2) ?
C5 C8 . . 1.504(2) ?
C6 C7 . . 1.364(2) ?
C6 H1c6 . . 0.96 ?
C8 O2 . . 1.2175(19) ?
C8 O3 . . 1.3115(19) ?
O3 H1o3 . . 0.960(18) ?
C9 O4 . . 1.2104(18) ?
C9 O5 . . 1.310(2) ?
O5 H1o5 . . 0.960(13) ?
P1 O6 . . 1.5102(14) ?
P1 O7 . . 1.4998(11) ?
P1 H1p1 . . 1.256(19) ?
P1 H2p1 . . 1.287(17) ?
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
O3 H1o3 O7 . . 2_766 0.960(18) 1.602(17) 2.5396(18) 164.3(16) ?
O5 H1o5 O6 . . 2_765 0.960(13) 1.554(12) 2.5109(16) 174.1(18) ?
C1 H2c1 O1 . . 1_455 0.96 2.35 3.221(2) 150.84 ?
C4 H1c4 O3 . . . 0.96 2.34 2.688(2) 100.80 ?
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
O3 . H1o3 . 0.96 0.001
O5 . H1o5 . 0.96 0.001
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 168346843
