#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/15/7231513.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_7231513
loop_
_publ_author_name
'Bolla, Geetha'
'Nangia, Ashwini'
_publ_section_title
;
 Novel pharmaceutical salts of albendazole
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              6394
_journal_paper_doi               10.1039/C8CE01311J
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C12 H16 N3 O2 S, C6 H5 O3 S, H2 O'
_chemical_formula_sum            'C18 H23 N3 O6 S2'
_chemical_formula_weight         441.51
_chemical_melting_point          432
_chemical_name_common            'ABZ BSAH'
_chemical_name_systematic        'Albendazole benzene sulfonic acid hydrate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-04-05 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                84.984(7)
_cell_angle_beta                 89.142(6)
_cell_angle_gamma                63.976(7)
_cell_formula_units_Z            2
_cell_length_a                   8.9020(6)
_cell_length_b                   9.2715(8)
_cell_length_c                   14.2635(12)
_cell_measurement_reflns_used    1375
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.3143
_cell_measurement_theta_min      2.7237
_cell_volume                     1053.47(16)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6424
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.710
_diffrn_reflns_theta_max         24.710
_diffrn_reflns_theta_min         2.729
_exptl_absorpt_coefficient_mu    0.292
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0680P)²+0.2474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2175
_reflns_number_total             3587
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01311j2.cif
_cod_data_source_block           ABZ-BSAH
_cod_depositor_comments
'Adding full bibliography for 7231513--7231518.cif.'
_cod_database_code               7231513
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S2 S 0.39237(12) 0.32980(12) 0.34358(7) 0.0588(4) Uani 1 1 d . .
S1 S 0.01059(15) 1.09085(15) 0.80739(9) 0.0846(5) Uani 1 1 d . .
N2 N -0.2246(3) 0.9124(3) 0.4746(2) 0.0529(8) Uani 1 1 d . .
H2A H -0.313601 0.955600 0.439382 0.063 Uiso 1 1 calc R U
N1 N 0.0217(3) 0.7441(3) 0.5300(2) 0.0572(9) Uani 1 1 d . .
H1A H 0.117316 0.661172 0.536484 0.069 Uiso 1 1 calc R U
O1 O -0.3275(3) 0.8158(3) 0.3233(2) 0.0750(9) Uani 1 1 d . .
N3 N -0.0710(3) 0.6735(4) 0.3957(2) 0.0576(9) Uani 1 1 d . .
H3A H 0.022705 0.588940 0.394320 0.069 Uiso 1 1 calc R U
O6 O 0.3301(3) 0.5057(4) 0.5672(2) 0.0743(9) Uani 1 1 d G .
H6A H 0.405364 0.521148 0.594456 0.112 Uiso 1 1 d G U
H6B H 0.363035 0.473040 0.513414 0.112 Uiso 1 1 d G U
C2 C -0.1950(4) 0.9754(4) 0.5521(3) 0.0501(9) Uani 1 1 d . .
C7 C -0.0382(4) 0.8693(4) 0.5879(3) 0.0524(10) Uani 1 1 d . .
C13 C 0.3185(4) 0.3000(5) 0.2369(2) 0.0503(10) Uani 1 1 d . .
O2 O -0.1368(3) 0.5830(3) 0.2724(2) 0.0742(9) Uani 1 1 d . .
C1 C -0.0923(4) 0.7730(4) 0.4633(3) 0.0508(10) Uani 1 1 d . .
O5 O 0.4961(4) 0.1761(3) 0.3891(2) 0.0943(12) Uani 1 1 d . .
O3 O 0.2475(3) 0.4142(3) 0.39820(18) 0.0855(11) Uani 1 1 d . .
C6 C 0.0328(4) 0.8960(5) 0.6647(3) 0.0606(11) Uani 1 1 d . .
H6 H 0.138867 0.822727 0.687360 0.073 Uiso 1 1 calc R U
C5 C -0.0591(5) 1.0371(5) 0.7082(3) 0.0600(11) Uani 1 1 d . .
C4 C -0.2188(5) 1.1438(4) 0.6713(3) 0.0638(12) Uani 1 1 d . .
H4 H -0.280089 1.237151 0.700662 0.077 Uiso 1 1 calc R U
C8 C -0.1918(5) 0.7009(5) 0.3292(3) 0.0607(11) Uani 1 1 d . .
C3 C -0.2880(5) 1.1161(4) 0.5941(3) 0.0602(11) Uani 1 1 d . .
H3 H -0.393539 1.188943 0.570557 0.072 Uiso 1 1 calc R U
C14 C 0.2355(5) 0.4303(5) 0.1719(3) 0.0713(13) Uani 1 1 d . .
H14 H 0.219347 0.532743 0.184574 0.086 Uiso 1 1 calc R U
C18 C 0.3434(5) 0.1505(5) 0.2175(3) 0.0680(12) Uani 1 1 d . .
H18 H 0.401448 0.061934 0.260400 0.082 Uiso 1 1 calc R U
C17 C 0.2824(7) 0.1308(6) 0.1340(3) 0.0898(15) Uani 1 1 d . .
H17 H 0.297073 0.028808 0.121276 0.108 Uiso 1 1 calc R U
O4 O 0.4780(5) 0.4272(5) 0.3173(2) 0.1164(13) Uani 1 1 d . .
C15 C 0.1770(6) 0.4083(7) 0.0888(3) 0.0896(16) Uani 1 1 d . .
H15 H 0.120825 0.496199 0.045117 0.108 Uiso 1 1 calc R U
C16 C 0.2005(6) 0.2593(7) 0.0696(3) 0.0904(16) Uani 1 1 d . .
H16 H 0.160992 0.244760 0.012901 0.108 Uiso 1 1 calc R U
C9 C -0.2532(6) 0.5946(6) 0.2010(3) 0.0971(17) Uani 1 1 d . .
H9A H -0.198579 0.512203 0.159133 0.146 Uiso 1 1 calc R U
H9B H -0.294363 0.698562 0.166189 0.146 Uiso 1 1 calc R U
H9C H -0.344884 0.580861 0.229624 0.146 Uiso 1 1 calc R U
C10 C 0.1931(7) 0.9154(9) 0.8482(4) 0.161(4) Uani 1 1 d . .
H10A H 0.192108 0.828371 0.815421 0.193 Uiso 1 1 calc R U
H10B H 0.287007 0.932720 0.824267 0.193 Uiso 1 1 calc R U
C11 C 0.2284(10) 0.8632(12) 0.9275(6) 0.301(9) Uani 1 1 d . .
H11B H 0.128031 0.857053 0.950344 0.361 Uiso 1 1 calc R U
H11A H 0.232293 0.951793 0.957144 0.361 Uiso 1 1 calc R U
C12 C 0.3576(9) 0.7267(9) 0.9743(5) 0.189(4) Uani 1 1 d . .
H12A H 0.416113 0.650239 0.929783 0.283 Uiso 1 1 calc R U
H12C H 0.311205 0.678698 1.021417 0.283 Uiso 1 1 calc R U
H12B H 0.433908 0.757812 1.003659 0.283 Uiso 1 1 calc R U
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
O5 S2 O4 114.3(2)
O5 S2 O3 110.97(19)
O4 S2 O3 111.7(2)
O5 S2 C13 107.69(18)
O4 S2 C13 105.09(19)
O3 S2 C13 106.61(16)
C5 S1 C10 104.8(3)
C1 N2 C2 108.7(3)
C1 N2 H2A 125.7
C2 N2 H2A 125.7
C1 N1 C7 108.9(3)
C1 N1 H1A 125.5
C7 N1 H1A 125.5
C1 N3 C8 122.9(3)
C1 N3 H3A 118.5
C8 N3 H3A 118.5
H6A O6 H6B 109.5
N2 C2 C7 107.1(3)
N2 C2 C3 132.7(3)
C7 C2 C3 120.3(4)
C6 C7 C2 122.8(4)
C6 C7 N1 131.2(3)
C2 C7 N1 106.1(3)
C18 C13 C14 119.8(4)
C18 C13 S2 120.8(3)
C14 C13 S2 119.4(3)
C8 O2 C9 115.4(3)
N1 C1 N2 109.3(3)
N1 C1 N3 123.2(3)
N2 C1 N3 127.5(3)
C7 C6 C5 117.8(3)
C7 C6 H6 121.1
C5 C6 H6 121.1
C6 C5 C4 118.8(4)
C6 C5 S1 124.3(3)
C4 C5 S1 116.9(3)
C3 C4 C5 122.8(4)
C3 C4 H4 118.6
C5 C4 H4 118.6
O1 C8 O2 125.6(4)
O1 C8 N3 124.6(4)
O2 C8 N3 109.8(3)
C4 C3 C2 117.5(3)
C4 C3 H3 121.2
C2 C3 H3 121.2
C15 C14 C13 119.8(4)
C15 C14 H14 120.1
C13 C14 H14 120.1
C13 C18 C17 119.6(4)
C13 C18 H18 120.2
C17 C18 H18 120.2
C16 C17 C18 120.7(5)
C16 C17 H17 119.6
C18 C17 H17 119.6
C16 C15 C14 120.5(4)
C16 C15 H15 119.8
C14 C15 H15 119.8
C15 C16 C17 119.6(5)
C15 C16 H16 120.2
C17 C16 H16 120.2
O2 C9 H9A 109.5
O2 C9 H9B 109.5
H9A C9 H9B 109.5
O2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 S1 125.9(6)
C11 C10 H10A 105.9
S1 C10 H10A 105.9
C11 C10 H10B 105.9
S1 C10 H10B 105.9
H10A C10 H10B 106.2
C10 C11 C12 135.4(9)
C10 C11 H11B 103.3
C12 C11 H11B 103.3
C10 C11 H11A 103.3
C12 C11 H11A 103.3
H11B C11 H11A 105.2
C11 C12 H12A 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
H12C C12 H12B 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 O5 1.417(3)
S2 O4 1.440(4)
S2 O3 1.440(3)
S2 C13 1.757(4)
S1 C5 1.748(4)
S1 C10 1.780(6)
N2 C1 1.333(4)
N2 C2 1.374(5)
N2 H2A 0.8600
N1 C1 1.325(4)
N1 C7 1.387(5)
N1 H1A 0.8600
O1 C8 1.208(4)
N3 C1 1.346(5)
N3 C8 1.367(5)
N3 H3A 0.8600
O6 H6A 0.8500
O6 H6B 0.8497
C2 C7 1.381(4)
C2 C3 1.385(5)
C7 C6 1.367(5)
C13 C18 1.358(5)
C13 C14 1.381(5)
O2 C8 1.328(5)
O2 C9 1.427(5)
C6 C5 1.397(5)
C6 H6 0.9300
C5 C4 1.405(5)
C4 C3 1.366(5)
C4 H4 0.9300
C3 H3 0.9300
C14 C15 1.368(6)
C14 H14 0.9300
C18 C17 1.376(6)
C18 H18 0.9300
C17 C16 1.364(6)
C17 H17 0.9300
C15 C16 1.356(7)
C15 H15 0.9300
C16 H16 0.9300
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.181(7)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.403(8)
C11 H11B 0.9700
C11 H11A 0.9700
C12 H12A 0.9600
C12 H12C 0.9600
C12 H12B 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139205060
