# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ABZ-BSAH
_database_code_depnum_ccdc_archive 'CCDC 1834924'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Albendazole benzene sulfonic acid hydrate'
_chemical_name_common            'ABZ BSAH'
_chemical_melting_point          432
_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

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.9020(6)
_cell_length_b                   9.2715(8)
_cell_length_c                   14.2635(12)
_cell_angle_alpha                84.984(7)
_cell_angle_beta                 89.142(6)
_cell_angle_gamma                63.976(7)
_cell_volume                     1053.47(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1375
_cell_measurement_theta_min      2.7237
_cell_measurement_theta_max      26.3143

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.292
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6424
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.729
_diffrn_reflns_theta_max         24.710
_diffrn_reflns_theta_full        24.710
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3587
_reflns_number_gt                2175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+0.2474P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3587
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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 . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.050

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ABZ-PTSAH
_database_code_depnum_ccdc_archive 'CCDC 1834926'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Albendazole paratoulene sulfonic acid hydrate'
_chemical_name_common            ABZ-PTSAH
_chemical_melting_point          356
_chemical_formula_moiety         C12H16N3O2S,C7H7O3S,H2O
_chemical_formula_sum            'C19 H25 N3 O6 S2'
_chemical_formula_weight         455.54

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.900(5)
_cell_length_b                   9.573(5)
_cell_length_c                   14.453(8)
_cell_angle_alpha                83.026(9)
_cell_angle_beta                 72.434(8)
_cell_angle_gamma                63.151(8)
_cell_volume                     1047.3(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6214
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      28.31

_exptl_crystal_description       plate
_exptl_crystal_colour            colorles
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.296
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10722
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.385
_diffrn_reflns_theta_max         26.552
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4246
_reflns_number_gt                3834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1400P)²+0.5969P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4246
_refine_ls_number_parameters     294
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.1945
_refine_ls_wR_factor_gt          0.1889
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.66920(8) 0.21417(7) 0.34413(4) 0.0213(2) Uani 1 1 d . . . . .
S1 S 0.13882(8) 0.66193(7) 0.20252(5) 0.0230(2) Uani 1 1 d . . . . .
O2 O -0.2205(2) 0.0317(2) 0.72028(13) 0.0230(4) Uani 1 1 d . . . . .
N2 N -0.2382(3) 0.3980(2) 0.52536(15) 0.0182(4) Uani 1 1 d . . . . .
O1 O -0.3985(2) 0.2735(2) 0.67927(14) 0.0253(4) Uani 1 1 d . . . . .
O6 O 0.3636(2) 0.0140(2) 0.42740(15) 0.0286(5) Uani 1 1 d D . . . .
N3 N -0.1077(3) 0.1460(3) 0.59612(15) 0.0189(5) Uani 1 1 d . . . . .
N1 N 0.0417(3) 0.2489(3) 0.46365(15) 0.0188(4) Uani 1 1 d . . . . .
O4 O 0.7746(2) 0.1111(2) 0.40676(13) 0.0279(5) Uani 1 1 d . . . . .
C4 C 0.1066(3) 0.4314(3) 0.33455(18) 0.0198(5) Uani 1 1 d . . . . .
H4 H 0.228378 0.365950 0.309903 0.024 Uiso 1 1 calc R U . . .
C8 C -0.2584(3) 0.1609(3) 0.66756(18) 0.0199(5) Uani 1 1 d . . . . .
O5 O 0.5691(3) 0.3728(2) 0.38159(15) 0.0363(5) Uani 1 1 d . . . . .
C1 C -0.1048(3) 0.2615(3) 0.53202(18) 0.0184(5) Uani 1 1 d . . . . .
C2 C -0.1773(3) 0.4803(3) 0.44930(17) 0.0185(5) Uani 1 1 d . . . . .
C6 C -0.1558(3) 0.6724(3) 0.33379(19) 0.0217(5) Uani 1 1 d . . . . .
H6 H -0.208364 0.771530 0.305877 0.026 Uiso 1 1 calc R U . . .
C18 C 0.8390(3) 0.3533(3) 0.20189(19) 0.0214(5) Uani 1 1 d . . . . .
H18 H 0.771551 0.446430 0.240561 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8185(3) 0.2185(3) 0.23229(17) 0.0184(5) Uani 1 1 d . . . . .
O3 O 0.5634(3) 0.1506(3) 0.32209(16) 0.0458(6) Uani 1 1 d . . . . .
C3 C 0.0006(3) 0.3858(3) 0.41054(18) 0.0182(5) Uani 1 1 d . . . . .
C5 C 0.0257(3) 0.5779(3) 0.29615(18) 0.0190(5) Uani 1 1 d . . . . .
C17 C 0.9603(4) 0.3501(3) 0.11361(19) 0.0249(6) Uani 1 1 d . . . . .
H17 H 0.975354 0.442034 0.092539 0.030 Uiso 1 1 calc R U . . .
C10 C 0.3586(3) 0.5066(3) 0.16250(18) 0.0212(5) Uani 1 1 d . . . . .
H10A H 0.439382 0.552922 0.127998 0.025 Uiso 1 1 calc R U . . .
H10B H 0.396313 0.452176 0.219987 0.025 Uiso 1 1 calc R U . . .
C15 C 1.0361(3) 0.0820(3) 0.08860(19) 0.0241(6) Uani 1 1 d . . . . .
H15 H 1.103340 -0.011412 0.050228 0.029 Uiso 1 1 calc R U . . .
C14 C 0.9165(3) 0.0834(3) 0.17604(19) 0.0224(5) Uani 1 1 d . . . . .
H14 H 0.901856 -0.008680 0.197402 0.027 Uiso 1 1 calc R U . . .
C7 C -0.2595(3) 0.6251(3) 0.41007(18) 0.0200(5) Uani 1 1 d . . . . .
H7 H -0.381754 0.689128 0.434517 0.024 Uiso 1 1 calc R U . . .
C16 C 1.0594(3) 0.2159(3) 0.05596(18) 0.0232(6) Uani 1 1 d . . . . .
C9 C -0.3681(4) 0.0289(4) 0.7954(2) 0.0280(6) Uani 1 1 d . . . . .
H9A H -0.426955 0.124806 0.835228 0.042 Uiso 1 1 calc R U . . .
H9B H -0.327310 -0.062271 0.836309 0.042 Uiso 1 1 calc R U . . .
H9C H -0.450419 0.022210 0.765953 0.042 Uiso 1 1 calc R U . . .
C12 C 0.5562(4) 0.2551(3) 0.0655(2) 0.0291(6) Uani 1 1 d . . . . .
H12A H 0.640320 0.298263 0.035257 0.044 Uiso 1 1 calc R U . . .
H12B H 0.561190 0.185631 0.019008 0.044 Uiso 1 1 calc R U . . .
H12C H 0.585724 0.195675 0.122844 0.044 Uiso 1 1 calc R U . . .
C19 C 1.1906(4) 0.2122(4) -0.0394(2) 0.0336(7) Uani 1 1 d . . . . .
H18A H 1.130322 0.254057 -0.090194 0.050 Uiso 1 1 calc R U . . .
H18B H 1.279004 0.104045 -0.056122 0.050 Uiso 1 1 calc R U . . .
H18C H 1.247860 0.276255 -0.033812 0.050 Uiso 1 1 calc R U . . .
C11 C 0.3721(3) 0.3882(3) 0.09583(19) 0.0235(6) Uani 1 1 d . . . . .
H11A H 0.338690 0.441704 0.037123 0.028 Uiso 1 1 calc R U . . .
H11B H 0.288451 0.344360 0.129409 0.028 Uiso 1 1 calc R U . . .
H3A H -0.016(4) 0.073(4) 0.599(2) 0.019(7) Uiso 1 1 d . . . . .
H1A H 0.150(5) 0.176(4) 0.453(2) 0.037(9) Uiso 1 1 d . . . . .
H2A H -0.359(5) 0.436(4) 0.570(3) 0.043(10) Uiso 1 1 d . . . . .
H6A H 0.431(5) 0.059(5) 0.421(3) 0.063(14) Uiso 1 1 d D . . . .
H6B H 0.359(8) -0.025(6) 0.484(2) 0.087(17) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 O5 1.442(2) . ?
S2 O3 1.451(2) . ?
S2 O4 1.460(2) . ?
S2 C13 1.765(3) . ?
S1 C5 1.771(3) . ?
S1 C10 1.808(3) . ?
O2 C8 1.332(3) . ?
O2 C9 1.438(3) . ?
N2 C1 1.328(3) . ?
N2 C2 1.392(3) . ?
O1 C8 1.203(3) . ?
N3 C1 1.358(4) . ?
N3 C8 1.383(3) . ?
N1 C1 1.342(3) . ?
N1 C3 1.390(3) . ?
C4 C3 1.385(4) . ?
C4 C5 1.390(4) . ?
C2 C7 1.387(4) . ?
C2 C3 1.390(3) . ?
C6 C7 1.383(4) . ?
C6 C5 1.412(4) . ?
C18 C13 1.385(4) . ?
C18 C17 1.394(4) . ?
C13 C14 1.380(4) . ?
C17 C16 1.384(4) . ?
C10 C11 1.517(4) . ?
C15 C14 1.382(4) . ?
C15 C16 1.394(4) . ?
C16 C19 1.505(4) . ?
C12 C11 1.522(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S2 O3 113.24(16) . . ?
O5 S2 O4 112.07(13) . . ?
O3 S2 O4 111.78(15) . . ?
O5 S2 C13 107.02(12) . . ?
O3 S2 C13 105.74(13) . . ?
O4 S2 C13 106.41(12) . . ?
C5 S1 C10 104.53(13) . . ?
C8 O2 C9 114.4(2) . . ?
C1 N2 C2 108.4(2) . . ?
C1 N3 C8 122.0(2) . . ?
C1 N1 C3 108.0(2) . . ?
C3 C4 C5 116.6(2) . . ?
O1 C8 O2 126.8(2) . . ?
O1 C8 N3 124.8(2) . . ?
O2 C8 N3 108.5(2) . . ?
N2 C1 N1 110.2(2) . . ?
N2 C1 N3 127.5(2) . . ?
N1 C1 N3 122.4(2) . . ?
C7 C2 C3 120.7(2) . . ?
C7 C2 N2 132.7(2) . . ?
C3 C2 N2 106.6(2) . . ?
C7 C6 C5 122.1(2) . . ?
C13 C18 C17 118.9(2) . . ?
C14 C13 C18 120.5(2) . . ?
C14 C13 S2 118.4(2) . . ?
C18 C13 S2 121.11(19) . . ?
C4 C3 N1 130.3(2) . . ?
C4 C3 C2 122.9(2) . . ?
N1 C3 C2 106.8(2) . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 S1 123.84(19) . . ?
C6 C5 S1 115.6(2) . . ?
C16 C17 C18 121.5(2) . . ?
C11 C10 S1 112.73(18) . . ?
C14 C15 C16 120.9(2) . . ?
C13 C14 C15 119.9(2) . . ?
C6 C7 C2 117.1(2) . . ?
C17 C16 C15 118.3(2) . . ?
C17 C16 C19 121.5(3) . . ?
C15 C16 C19 120.2(3) . . ?
C10 C11 C12 112.2(2) . . ?

_refine_diff_density_max         1.154
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.131

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1834925'

_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;
_publcif_datablock.id            {2ed12076-2690-4ab7-b6f4-ff62c28ab8e3}

# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 N3 O5 S2'
_chemical_formula_weight         437.52

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.2992(17)
_cell_length_b                   9.7420(9)
_cell_length_c                   15.8825(14)
_cell_angle_alpha                90
_cell_angle_beta                 115.573(12)
_cell_angle_gamma                90
_cell_volume                     2135.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.284
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8071
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.844
_diffrn_reflns_theta_max         24.712
_diffrn_reflns_theta_full        24.712
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3638
_reflns_number_gt                2203
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0778P)²+1.4566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3638
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.2105
_refine_ls_wR_factor_gt          0.1883
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.72036(9) 0.55055(15) 0.10838(8) 0.0599(4) Uani 1 1 d . . . . .
S1 S 0.87203(12) 0.41077(19) 0.67021(9) 0.0836(6) Uani 1 1 d . . . . .
O3 O 0.7517(3) 0.6933(4) 0.1151(2) 0.0722(11) Uani 1 1 d . . . . .
O4 O 0.7507(3) 0.4901(4) 0.1998(2) 0.0687(10) Uani 1 1 d . . . . .
N1 N 0.8634(3) 0.6308(4) 0.3617(2) 0.0507(10) Uani 1 1 d . . . . .
H1A H 0.820023 0.585987 0.316210 0.061 Uiso 1 1 calc R U . . .
C1 C 0.9137(3) 0.7373(5) 0.3535(3) 0.0502(12) Uani 1 1 d . . . . .
N2 N 0.9765(3) 0.7798(4) 0.4370(2) 0.0530(10) Uani 1 1 d . . . . .
H2A H 1.018035 0.844929 0.448191 0.064 Uiso 1 1 calc R U . . .
N3 N 0.8987(3) 0.7916(4) 0.2712(2) 0.0557(11) Uani 1 1 d . . . . .
H3A H 0.859993 0.749749 0.221292 0.067 Uiso 1 1 calc R U . . .
C2 C 0.9634(3) 0.7002(5) 0.5037(3) 0.0513(12) Uani 1 1 d . . . . .
O2 O 0.8988(3) 0.9517(4) 0.1737(2) 0.0943(14) Uani 1 1 d . . . . .
O1 O 1.0079(3) 0.9672(4) 0.3238(3) 0.0859(13) Uani 1 1 d . . . . .
C13 C 0.7836(3) 0.4612(5) 0.0551(3) 0.0541(13) Uani 1 1 d . . . . .
C6 C 0.8606(3) 0.5101(5) 0.5013(3) 0.0551(13) Uani 1 1 d . . . . .
H6 H 0.812968 0.445848 0.468727 0.066 Uiso 1 1 calc R U . . .
O5 O 0.6198(2) 0.5323(4) 0.0487(2) 0.0710(10) Uani 1 1 d . . . . .
C5 C 0.9036(4) 0.5167(5) 0.5986(3) 0.0567(13) Uani 1 1 d . . . . .
C14 C 0.8831(4) 0.4735(6) 0.0892(3) 0.0654(15) Uani 1 1 d . . . . .
H14 H 0.916645 0.529771 0.140373 0.078 Uiso 1 1 calc R U . . .
C4 C 0.9758(4) 0.6137(6) 0.6456(3) 0.0627(15) Uani 1 1 d . . . . .
H4 H 1.003384 0.615420 0.710471 0.075 Uiso 1 1 calc R U . . .
C7 C 0.8929(3) 0.6042(5) 0.4562(3) 0.0486(12) Uani 1 1 d . . . . .
C8 C 0.9421(4) 0.9113(6) 0.2619(4) 0.0688(15) Uani 1 1 d . . . . .
C3 C 1.0073(4) 0.7057(5) 0.6003(3) 0.0594(14) Uani 1 1 d . . . . .
H3 H 1.055835 0.768987 0.632618 0.071 Uiso 1 1 calc R U . . .
C16 C 0.8849(5) 0.3192(7) -0.0252(4) 0.0784(17) Uani 1 1 d . . . . .
C18 C 0.7353(4) 0.3760(6) -0.0198(3) 0.0678(16) Uani 1 1 d . . . . .
H18 H 0.668402 0.365974 -0.043573 0.081 Uiso 1 1 calc R U . . .
C17 C 0.7853(5) 0.3067(7) -0.0587(4) 0.0795(18) Uani 1 1 d . . . . .
H17 H 0.751994 0.249293 -0.109314 0.095 Uiso 1 1 calc R U . . .
C15 C 0.9323(4) 0.4054(7) 0.0496(4) 0.0748(17) Uani 1 1 d . . . . .
H15 H 0.999054 0.416576 0.072955 0.090 Uiso 1 1 calc R U . . .
C9 C 0.9316(7) 1.0809(8) 0.1557(5) 0.143(4) Uani 1 1 d . . . . .
H9A H 0.920343 1.085196 0.091435 0.214 Uiso 1 1 calc R U . . .
H9B H 0.999719 1.090626 0.194971 0.214 Uiso 1 1 calc R U . . .
H9C H 0.896956 1.153764 0.168662 0.214 Uiso 1 1 calc R U . . .
C19 C 0.9388(5) 0.2408(8) -0.0704(5) 0.114(3) Uani 1 1 d . . . . .
H19A H 0.921128 0.145617 -0.075184 0.171 Uiso 1 1 calc R U . . .
H19B H 1.007283 0.249996 -0.033079 0.171 Uiso 1 1 calc R U . . .
H19C H 0.922083 0.277172 -0.131625 0.171 Uiso 1 1 calc R U . . .
C10 C 0.7769(7) 0.3047(10) 0.5920(5) 0.159(4) Uani 1 1 d . . . . .
H10A H 0.722471 0.361693 0.552991 0.191 Uiso 1 1 calc R U . . .
H10B H 0.799183 0.255711 0.551771 0.191 Uiso 1 1 calc R U . . .
C11 C 0.7421(8) 0.1956(13) 0.6480(7) 0.180(5) Uani 1 1 d . . . . .
H11A H 0.703594 0.122295 0.607795 0.215 Uiso 1 1 calc R U . . .
H11B H 0.796462 0.156852 0.701189 0.215 Uiso 1 1 calc R U . . .
C12 C 0.6865(7) 0.2824(14) 0.6755(8) 0.181(5) Uani 1 1 d . . . . .
H12A H 0.727535 0.350733 0.717587 0.271 Uiso 1 1 calc R U . . .
H12B H 0.655770 0.229706 0.706273 0.271 Uiso 1 1 calc R U . . .
H12C H 0.637889 0.326513 0.621538 0.271 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 O5 1.428(3) . ?
S2 O4 1.446(3) . ?
S2 O3 1.459(4) . ?
S2 C13 1.765(5) . ?
S1 C5 1.751(5) . ?
S1 C10 1.779(8) . ?
N1 C1 1.331(6) . ?
N1 C7 1.393(5) . ?
N1 H1A 0.8600 . ?
C1 N2 1.325(5) . ?
C1 N3 1.334(5) . ?
N2 C2 1.394(6) . ?
N2 H2A 0.8600 . ?
N3 C8 1.381(7) . ?
N3 H3A 0.8600 . ?
C2 C7 1.381(6) . ?
C2 C3 1.386(6) . ?
O2 C8 1.324(6) . ?
O2 C9 1.430(7) . ?
O1 C8 1.193(6) . ?
C13 C18 1.375(7) . ?
C13 C14 1.384(7) . ?
C6 C7 1.379(6) . ?
C6 C5 1.395(6) . ?
C6 H6 0.9300 . ?
C5 C4 1.400(7) . ?
C14 C15 1.346(7) . ?
C14 H14 0.9300 . ?
C4 C3 1.361(7) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C16 C15 1.377(8) . ?
C16 C17 1.385(8) . ?
C16 C19 1.512(9) . ?
C18 C17 1.354(8) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C15 H15 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C10 C11 1.616(12) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.397(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S2 O4 113.7(2) . . ?
O5 S2 O3 113.2(2) . . ?
O4 S2 O3 111.2(2) . . ?
O5 S2 C13 106.1(2) . . ?
O4 S2 C13 106.0(2) . . ?
O3 S2 C13 105.9(2) . . ?
C5 S1 C10 105.1(3) . . ?
C1 N1 C7 108.6(4) . . ?
C1 N1 H1A 125.7 . . ?
C7 N1 H1A 125.7 . . ?
N2 C1 N1 110.2(4) . . ?
N2 C1 N3 126.9(5) . . ?
N1 C1 N3 122.8(4) . . ?
C1 N2 C2 107.9(4) . . ?
C1 N2 H2A 126.1 . . ?
C2 N2 H2A 126.1 . . ?
C1 N3 C8 123.5(4) . . ?
C1 N3 H3A 118.3 . . ?
C8 N3 H3A 118.3 . . ?
C7 C2 C3 121.4(5) . . ?
C7 C2 N2 107.3(4) . . ?
C3 C2 N2 131.3(5) . . ?
C8 O2 C9 114.5(5) . . ?
C18 C13 C14 118.7(5) . . ?
C18 C13 S2 120.7(4) . . ?
C14 C13 S2 120.6(4) . . ?
C7 C6 C5 116.2(5) . . ?
C7 C6 H6 121.9 . . ?
C5 C6 H6 121.9 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 S1 124.2(4) . . ?
C4 C5 S1 115.3(4) . . ?
C15 C14 C13 121.2(5) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C3 C4 C5 122.8(4) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C6 C7 C2 122.5(4) . . ?
C6 C7 N1 131.4(4) . . ?
C2 C7 N1 105.9(4) . . ?
O1 C8 O2 126.5(6) . . ?
O1 C8 N3 124.8(5) . . ?
O2 C8 N3 108.6(5) . . ?
C4 C3 C2 116.5(5) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
C15 C16 C17 117.9(6) . . ?
C15 C16 C19 121.7(6) . . ?
C17 C16 C19 120.5(6) . . ?
C17 C18 C13 119.8(5) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C18 C17 C16 121.7(6) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C14 C15 C16 120.7(6) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
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 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C10 S1 111.2(5) . . ?
C11 C10 H10A 109.4 . . ?
S1 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
S1 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 99.4(11) . . ?
C12 C11 H11A 111.9 . . ?
C10 C11 H11A 111.9 . . ?
C12 C11 H11B 111.9 . . ?
C10 C11 H11B 111.9 . . ?
H11A C11 H11B 109.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.058


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ABZ-BSA
_database_code_depnum_ccdc_archive 'CCDC 1834929'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Albendazole benzenesulfonic acid'
_chemical_name_common            ABZ-BSA
_chemical_melting_point          432
_chemical_formula_moiety         'C12 H16 N3 O2 S, C6 H5 O3 S'
_chemical_formula_sum            'C18 H21 N3 O5 S2'
_chemical_formula_weight         423.50

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.5042(7)
_cell_length_b                   9.4678(7)
_cell_length_c                   26.084(2)
_cell_angle_alpha                96.005(6)
_cell_angle_beta                 93.966(7)
_cell_angle_gamma                102.377(7)
_cell_volume                     2031.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2033
_cell_measurement_theta_min      2.6507
_cell_measurement_theta_max      26.3144

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    ?
_shelx_estimated_absorpt_T_min   0.296
_shelx_estimated_absorpt_T_max   1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76516
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13242
_diffrn_reflns_av_unetI/netI     0.1463
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.656
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_full        24.713
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6906
_reflns_number_gt                2993
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1140P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6906
_refine_ls_number_parameters     509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1844
_refine_ls_R_factor_gt           0.0844
_refine_ls_wR_factor_ref         0.2723
_refine_ls_wR_factor_gt          0.2121
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S3 S 0.1605(2) 0.92383(15) 0.43018(8) 0.0465(5) Uani 1 1 d . . . . .
S2 S 0.5869(2) 0.60126(18) 0.65078(8) 0.0629(6) Uani 1 1 d . . . . .
O6 O 0.2118(5) 1.0142(4) 0.48039(17) 0.0487(12) Uani 1 1 d . . . . .
O5 O 0.0512(5) 0.9820(4) 0.3974(2) 0.0553(14) Uani 1 1 d . . . . .
O2 O -0.0988(5) 0.2232(4) 0.33174(19) 0.0534(13) Uani 1 1 d . . . . .
C7 C 0.2921(7) 0.4231(6) 0.5228(3) 0.0360(16) Uani 1 1 d . . . . .
N2 N 0.1502(6) 0.5016(5) 0.4606(2) 0.0424(14) Uani 1 1 d . . . . .
H2 H 0.108581 0.557599 0.442531 0.051 Uiso 1 1 calc R U . . .
O1 O -0.0385(6) 0.4546(4) 0.3706(2) 0.0630(15) Uani 1 1 d . . . . .
N1 N 0.2112(6) 0.3072(5) 0.4854(2) 0.0426(14) Uani 1 1 d . . . . .
H1 H 0.215556 0.217436 0.485912 0.051 Uiso 1 1 calc R U . . .
O7 O 0.1000(5) 0.7725(4) 0.4354(2) 0.0580(14) Uani 1 1 d . . . . .
C5 C 0.4563(7) 0.5677(6) 0.5946(3) 0.0407(17) Uani 1 1 d . . . . .
C1 C 0.1281(7) 0.3565(6) 0.4495(3) 0.0364(16) Uani 1 1 d . . . . .
C8 C -0.0354(7) 0.3283(6) 0.3699(3) 0.0437(17) Uani 1 1 d . . . . .
N3 N 0.0399(6) 0.2724(5) 0.4083(2) 0.0450(15) Uani 1 1 d . . . . .
H3 H 0.030720 0.179681 0.405974 0.054 Uiso 1 1 calc R U . . .
C3 C 0.3118(8) 0.6831(6) 0.5337(3) 0.0494(19) Uani 1 1 d . . . . .
H3A H 0.285016 0.766110 0.522870 0.059 Uiso 1 1 calc R U . . .
C25 C 0.3393(8) 0.9356(6) 0.3987(3) 0.0435(18) Uani 1 1 d . . . . .
C2 C 0.2518(7) 0.5465(6) 0.5064(3) 0.0373(16) Uani 1 1 d . . . . .
C6 C 0.3947(8) 0.4279(6) 0.5657(3) 0.0429(17) Uani 1 1 d . . . . .
H6 H 0.422967 0.344533 0.575706 0.052 Uiso 1 1 calc R U . . .
C27 C 0.6220(9) 0.9377(6) 0.4022(3) 0.055(2) Uani 1 1 d . . . . .
H27 H 0.718099 0.934483 0.420882 0.066 Uiso 1 1 calc R U . . .
C9 C -0.1908(9) 0.2665(8) 0.2893(3) 0.067(2) Uani 1 1 d . . . . .
H9A H -0.238623 0.182387 0.265023 0.100 Uiso 1 1 calc R U . . .
H9B H -0.120051 0.336108 0.272313 0.100 Uiso 1 1 calc R U . . .
H9C H -0.274381 0.309531 0.302688 0.100 Uiso 1 1 calc R U . . .
C4 C 0.4125(8) 0.6895(6) 0.5774(3) 0.0453(18) Uani 1 1 d . . . . .
H4 H 0.454028 0.779912 0.596629 0.054 Uiso 1 1 calc R U . . .
C26 C 0.4800(8) 0.9253(6) 0.4263(3) 0.0489(19) Uani 1 1 d . . . . .
H26 H 0.479714 0.910190 0.460983 0.059 Uiso 1 1 calc R U . . .
C28 C 0.6196(10) 0.9549(7) 0.3503(4) 0.057(2) Uani 1 1 d . . . . .
H28 H 0.714052 0.961775 0.333850 0.069 Uiso 1 1 calc R U . . .
C30 C 0.3414(11) 0.9543(7) 0.3472(4) 0.068(2) Uani 1 1 d . . . . .
H30 H 0.247688 0.962065 0.328158 0.082 Uiso 1 1 calc R U . . .
C10 C 0.6253(9) 0.4307(7) 0.6642(4) 0.077(3) Uani 1 1 d . . . . .
H10A H 0.524486 0.360296 0.664998 0.093 Uiso 1 1 calc R U . . .
H10B H 0.685871 0.393350 0.637769 0.093 Uiso 1 1 calc R U . . .
C29 C 0.4830(13) 0.9617(7) 0.3237(3) 0.071(2) Uani 1 1 d . . . . .
H29 H 0.482842 0.971517 0.288619 0.085 Uiso 1 1 calc R U . . .
S4 S 0.5210(2) 0.03881(16) 0.15546(8) 0.0537(6) Uani 1 1 d . . . . .
S1 S 0.1273(3) 0.3940(3) -0.06450(11) 0.1026(10) Uani 1 1 d . . . . .
O4 O 0.7689(6) 0.7323(5) 0.2643(2) 0.0587(14) Uani 1 1 d . . . . .
O9 O 0.4928(6) -0.0474(5) 0.1050(2) 0.0639(14) Uani 1 1 d . . . . .
O10 O 0.6110(5) -0.0270(4) 0.1920(2) 0.0603(15) Uani 1 1 d . . . . .
N4 N 0.4802(7) 0.6597(5) 0.1074(2) 0.0538(16) Uani 1 1 d . . . . .
H4A H 0.478488 0.750131 0.107221 0.065 Uiso 1 1 calc R U . . .
O8 O 0.5918(6) 0.1904(4) 0.1538(2) 0.0706(17) Uani 1 1 d . . . . .
N6 N 0.6391(7) 0.6876(5) 0.1862(2) 0.0537(16) Uani 1 1 d . . . . .
H6A H 0.648007 0.780341 0.188806 0.064 Uiso 1 1 calc R U . . .
O3 O 0.7127(7) 0.5032(5) 0.2238(2) 0.0791(18) Uani 1 1 d . . . . .
C13 C 0.5555(8) 0.6058(6) 0.1433(3) 0.0485(19) Uani 1 1 d . . . . .
N5 N 0.5287(7) 0.4616(5) 0.1320(2) 0.0522(16) Uani 1 1 d . . . . .
H5 H 0.563807 0.403154 0.150726 0.063 Uiso 1 1 calc R U . . .
C17 C 0.2496(9) 0.4181(9) -0.0056(3) 0.068(2) Uani 1 1 d . . . . .
C20 C 0.7107(8) 0.6315(7) 0.2259(3) 0.054(2) Uani 1 1 d . . . . .
C18 C 0.3140(9) 0.5504(7) 0.0240(3) 0.058(2) Uani 1 1 d . . . . .
H18 H 0.297316 0.637414 0.013563 0.070 Uiso 1 1 calc R U . . .
C32 C 0.3162(9) 0.1220(7) 0.2209(3) 0.058(2) Uani 1 1 d . . . . .
H32 H 0.405301 0.193393 0.235682 0.070 Uiso 1 1 calc R U . . .
C15 C 0.3756(9) 0.2890(7) 0.0559(3) 0.063(2) Uani 1 1 d . . . . .
H15 H 0.394693 0.203138 0.066787 0.076 Uiso 1 1 calc R U . . .
C19 C 0.4034(8) 0.5477(7) 0.0695(3) 0.0498(19) Uani 1 1 d . . . . .
C31 C 0.3305(8) 0.0298(6) 0.1784(3) 0.051(2) Uani 1 1 d . . . . .
C16 C 0.2870(10) 0.2893(8) 0.0099(4) 0.072(3) Uani 1 1 d . . . . .
H16 H 0.250359 0.202139 -0.011701 0.087 Uiso 1 1 calc R U . . .
C14 C 0.4349(8) 0.4221(7) 0.0852(3) 0.054(2) Uani 1 1 d . . . . .
C21 C 0.8454(9) 0.6858(8) 0.3083(3) 0.070(2) Uani 1 1 d . . . . .
H21A H 0.932193 0.642677 0.297670 0.104 Uiso 1 1 calc R U . . .
H21B H 0.767650 0.615328 0.322696 0.104 Uiso 1 1 calc R U . . .
H21C H 0.887519 0.768220 0.333881 0.104 Uiso 1 1 calc R U . . .
C33 C 0.1707(11) 0.1097(8) 0.2418(4) 0.075(3) Uani 1 1 d . . . . .
H33 H 0.163310 0.170682 0.271510 0.090 Uiso 1 1 calc R U . . .
C23 C 0.0051(12) 0.5647(14) -0.1260(4) 0.118(4) Uani 1 1 d . . . . .
H23A H -0.099525 0.500081 -0.124785 0.142 Uiso 1 1 calc R U . . .
H23B H 0.058460 0.523824 -0.153703 0.142 Uiso 1 1 calc R U . . .
C36 C 0.1974(11) -0.0738(9) 0.1574(4) 0.088(3) Uani 1 1 d . . . . .
H36 H 0.207244 -0.140945 0.129814 0.106 Uiso 1 1 calc R U . . .
C34 C 0.0356(11) 0.0084(10) 0.2195(4) 0.088(3) Uani 1 1 d . . . . .
H34 H -0.063300 0.000364 0.233377 0.105 Uiso 1 1 calc R U . . .
C35 C 0.0520(12) -0.0806(10) 0.1759(5) 0.113(4) Uani 1 1 d . . . . .
H35 H -0.038415 -0.146424 0.158929 0.136 Uiso 1 1 calc R U . . .
C24 C -0.0171(15) 0.7126(16) -0.1362(6) 0.180(7) Uani 1 1 d . . . . .
H24A H -0.079457 0.704715 -0.168910 0.270 Uiso 1 1 calc R U . . .
H24B H 0.086723 0.776424 -0.137032 0.270 Uiso 1 1 calc R U . . .
H24C H -0.072781 0.751430 -0.109199 0.270 Uiso 1 1 calc R U . . .
C22 C 0.1039(11) 0.5774(10) -0.0760(4) 0.096(3) Uani 1 1 d . . . . .
H22A H 0.051087 0.618522 -0.048204 0.115 Uiso 1 1 calc R U . . .
H22B H 0.209129 0.641019 -0.077204 0.115 Uiso 1 1 calc R U . . .
C11 C 0.7260(15) 0.4594(11) 0.7184(7) 0.168(8) Uani 1 1 d . . . . .
H11A H 0.838001 0.491047 0.711581 0.201 Uiso 1 1 calc R U . . .
H11B H 0.697040 0.543332 0.736699 0.201 Uiso 1 1 calc R U . . .
C12 C 0.7254(18) 0.370(2) 0.7502(5) 0.231(11) Uani 1 1 d . . . . .
H12A H 0.618705 0.309887 0.749127 0.347 Uiso 1 1 calc R U . . .
H12B H 0.756787 0.421653 0.784355 0.347 Uiso 1 1 calc R U . . .
H12C H 0.800231 0.310540 0.741739 0.347 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S3 O7 1.439(4) . ?
S3 O5 1.451(4) . ?
S3 O6 1.471(4) . ?
S3 C25 1.766(7) . ?
S2 C5 1.735(7) . ?
S2 C10 1.779(7) . ?
O2 C8 1.326(7) . ?
O2 C9 1.455(8) . ?
C7 C6 1.362(9) . ?
C7 C2 1.385(8) . ?
C7 N1 1.410(7) . ?
N2 C1 1.344(7) . ?
N2 C2 1.394(8) . ?
N2 H2 0.8600 . ?
O1 C8 1.200(7) . ?
N1 C1 1.317(8) . ?
N1 H1 0.8600 . ?
C5 C4 1.393(9) . ?
C5 C6 1.425(8) . ?
C1 N3 1.344(7) . ?
C8 N3 1.364(8) . ?
N3 H3 0.8600 . ?
C3 C4 1.365(9) . ?
C3 C2 1.384(8) . ?
C3 H3A 0.9300 . ?
C25 C30 1.375(10) . ?
C25 C26 1.381(9) . ?
C6 H6 0.9300 . ?
C27 C28 1.379(10) . ?
C27 C26 1.389(9) . ?
C27 H27 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C4 H4 0.9300 . ?
C26 H26 0.9300 . ?
C28 C29 1.328(10) . ?
C28 H28 0.9300 . ?
C30 C29 1.380(11) . ?
C30 H30 0.9300 . ?
C10 C11 1.568(14) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C29 H29 0.9300 . ?
S4 O8 1.439(4) . ?
S4 O9 1.450(5) . ?
S4 O10 1.452(5) . ?
S4 C31 1.754(7) . ?
S1 C17 1.759(8) . ?
S1 C22 1.843(10) . ?
O4 C20 1.299(7) . ?
O4 C21 1.435(9) . ?
N4 C13 1.306(8) . ?
N4 C19 1.386(8) . ?
N4 H4A 0.8600 . ?
N6 C13 1.353(8) . ?
N6 C20 1.376(9) . ?
N6 H6A 0.8600 . ?
O3 C20 1.213(7) . ?
C13 N5 1.333(7) . ?
N5 C14 1.382(8) . ?
N5 H5 0.8600 . ?
C17 C18 1.383(9) . ?
C17 C16 1.416(11) . ?
C18 C19 1.369(10) . ?
C18 H18 0.9300 . ?
C32 C31 1.366(9) . ?
C32 C33 1.374(10) . ?
C32 H32 0.9300 . ?
C15 C16 1.373(11) . ?
C15 C14 1.378(9) . ?
C15 H15 0.9300 . ?
C19 C14 1.371(9) . ?
C31 C36 1.368(10) . ?
C16 H16 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C33 C34 1.378(11) . ?
C33 H33 0.9300 . ?
C23 C22 1.481(12) . ?
C23 C24 1.501(15) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C36 C35 1.349(11) . ?
C36 H36 0.9300 . ?
C34 C35 1.376(12) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C11 C12 1.244(16) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 S3 O5 112.8(3) . . ?
O7 S3 O6 112.7(3) . . ?
O5 S3 O6 112.7(2) . . ?
O7 S3 C25 107.0(3) . . ?
O5 S3 C25 106.1(3) . . ?
O6 S3 C25 104.7(3) . . ?
C5 S2 C10 107.0(3) . . ?
C8 O2 C9 115.4(5) . . ?
C6 C7 C2 122.8(5) . . ?
C6 C7 N1 132.0(5) . . ?
C2 C7 N1 105.2(6) . . ?
C1 N2 C2 108.8(5) . . ?
C1 N2 H2 125.6 . . ?
C2 N2 H2 125.6 . . ?
C1 N1 C7 110.1(5) . . ?
C1 N1 H1 125.0 . . ?
C7 N1 H1 125.0 . . ?
C4 C5 C6 119.5(6) . . ?
C4 C5 S2 115.6(5) . . ?
C6 C5 S2 124.9(5) . . ?
N1 C1 N2 108.9(5) . . ?
N1 C1 N3 124.1(5) . . ?
N2 C1 N3 127.0(6) . . ?
O1 C8 O2 126.1(7) . . ?
O1 C8 N3 124.2(6) . . ?
O2 C8 N3 109.7(5) . . ?
C1 N3 C8 122.6(5) . . ?
C1 N3 H3 118.7 . . ?
C8 N3 H3 118.7 . . ?
C4 C3 C2 116.5(6) . . ?
C4 C3 H3A 121.7 . . ?
C2 C3 H3A 121.7 . . ?
C30 C25 C26 119.2(7) . . ?
C30 C25 S3 121.5(6) . . ?
C26 C25 S3 119.4(6) . . ?
C3 C2 C7 121.4(6) . . ?
C3 C2 N2 131.4(6) . . ?
C7 C2 N2 107.1(5) . . ?
C7 C6 C5 116.4(6) . . ?
C7 C6 H6 121.8 . . ?
C5 C6 H6 121.8 . . ?
C28 C27 C26 119.5(7) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 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 . . ?
C3 C4 C5 123.3(6) . . ?
C3 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C25 C26 C27 119.8(8) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C29 C28 C27 120.3(8) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C25 C30 C29 119.9(8) . . ?
C25 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C11 C10 S2 106.4(6) . . ?
C11 C10 H10A 110.4 . . ?
S2 C10 H10A 110.4 . . ?
C11 C10 H10B 110.4 . . ?
S2 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
C28 C29 C30 121.3(9) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
O8 S4 O9 113.5(3) . . ?
O8 S4 O10 112.9(3) . . ?
O9 S4 O10 110.8(3) . . ?
O8 S4 C31 106.9(3) . . ?
O9 S4 C31 106.3(3) . . ?
O10 S4 C31 105.8(3) . . ?
C17 S1 C22 105.7(4) . . ?
C20 O4 C21 115.8(5) . . ?
C13 N4 C19 109.1(5) . . ?
C13 N4 H4A 125.4 . . ?
C19 N4 H4A 125.4 . . ?
C13 N6 C20 124.0(5) . . ?
C13 N6 H6A 118.0 . . ?
C20 N6 H6A 118.0 . . ?
N4 C13 N5 109.6(6) . . ?
N4 C13 N6 123.3(6) . . ?
N5 C13 N6 127.0(7) . . ?
C13 N5 C14 108.3(6) . . ?
C13 N5 H5 125.9 . . ?
C14 N5 H5 125.9 . . ?
C18 C17 C16 119.6(7) . . ?
C18 C17 S1 125.2(7) . . ?
C16 C17 S1 115.1(6) . . ?
O3 C20 O4 126.9(7) . . ?
O3 C20 N6 122.2(7) . . ?
O4 C20 N6 110.9(6) . . ?
C19 C18 C17 117.1(7) . . ?
C19 C18 H18 121.5 . . ?
C17 C18 H18 121.5 . . ?
C31 C32 C33 120.3(6) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C16 C15 C14 116.7(7) . . ?
C16 C15 H15 121.7 . . ?
C14 C15 H15 121.7 . . ?
C18 C19 C14 123.0(6) . . ?
C18 C19 N4 130.7(6) . . ?
C14 C19 N4 106.3(6) . . ?
C32 C31 C36 118.6(7) . . ?
C32 C31 S4 119.3(5) . . ?
C36 C31 S4 122.0(6) . . ?
C15 C16 C17 122.1(7) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C19 C14 C15 121.3(7) . . ?
C19 C14 N5 106.6(6) . . ?
C15 C14 N5 132.0(7) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C32 C33 C34 120.9(8) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
C22 C23 C24 109.5(10) . . ?
C22 C23 H23A 109.8 . . ?
C24 C23 H23A 109.8 . . ?
C22 C23 H23B 109.8 . . ?
C24 C23 H23B 109.8 . . ?
H23A C23 H23B 108.2 . . ?
C35 C36 C31 121.4(8) . . ?
C35 C36 H36 119.3 . . ?
C31 C36 H36 119.3 . . ?
C35 C34 C33 117.7(8) . . ?
C35 C34 H34 121.1 . . ?
C33 C34 H34 121.1 . . ?
C36 C35 C34 120.9(8) . . ?
C36 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C22 S1 108.3(8) . . ?
C23 C22 H22A 110.0 . . ?
S1 C22 H22A 110.0 . . ?
C23 C22 H22B 110.0 . . ?
S1 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
C12 C11 C10 126.1(10) . . ?
C12 C11 H11A 105.8 . . ?
C10 C11 H11A 105.8 . . ?
C12 C11 H11B 105.8 . . ?
C10 C11 H11B 105.8 . . ?
H11A C11 H11B 106.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.961
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.081

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ABZ-OAH
_database_code_depnum_ccdc_archive 'CCDC 1834927'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Albendazole oxalic acid hydrate'
_chemical_name_common            ABZ-OAH
_chemical_melting_point          411
_chemical_formula_moiety         'C12 H12 N3 O2 S, C2 H O4, H2 O'
_chemical_formula_sum            'C14 H15 N3 O7 S'
_chemical_formula_weight         369.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.2659(7)
_cell_length_b                   28.337(4)
_cell_length_c                   11.2029(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.925(2)
_cell_angle_gamma                90
_cell_volume                     1667.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6197
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.02

_exptl_crystal_description       Plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15227
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.437
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_full        24.713
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2841
_reflns_number_gt                2755
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+3.5220P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2841
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1589
_refine_ls_goodness_of_fit_ref   1.326
_refine_ls_restrained_S_all      1.326
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C13A C 0.9594(15) 0.0125(3) 0.7090(7) 0.038(2) Uani 0.560(10) 1 d . . P A 1
H13A H 0.999608 -0.016957 0.752049 0.057 Uiso 0.560(10) 1 calc R U P A 1
H13B H 1.078969 0.037153 0.737642 0.057 Uiso 0.560(10) 1 calc R U P A 1
H13C H 0.973609 0.007547 0.623090 0.057 Uiso 0.560(10) 1 calc R U P A 1
C13B C 0.572(2) 0.0065(3) 0.6234(9) 0.045(3) Uani 0.440(10) 1 d . . P A 2
H13D H 0.662526 0.013341 0.551863 0.068 Uiso 0.440(10) 1 calc R U P A 2
H13E H 0.401942 0.020790 0.615021 0.068 Uiso 0.440(10) 1 calc R U P A 2
H13F H 0.555717 -0.027694 0.632826 0.068 Uiso 0.440(10) 1 calc R U P A 2
S1 S 0.83333(18) 0.05769(3) 0.96301(9) 0.0274(3) Uani 1 1 d . . . . .
O2 O -0.0917(4) 0.33964(8) 0.6943(2) 0.0225(6) Uani 1 1 d . . . . .
O1 O 0.2846(4) 0.33784(8) 0.8044(2) 0.0220(6) Uani 1 1 d . . . . .
O4 O 0.3604(4) 0.34666(8) 0.1377(2) 0.0205(5) Uani 1 1 d . . . . .
O5 O -0.1852(4) 0.31298(9) -0.0334(2) 0.0227(6) Uani 1 1 d . . . . .
O6 O -0.0735(5) 0.38295(9) 0.0459(2) 0.0255(6) Uani 1 1 d . . . . .
N2 N 0.4629(5) 0.25016(11) 0.8585(3) 0.0169(6) Uani 1 1 d . . . . .
O7 O 0.4822(5) 0.41150(10) 0.9585(3) 0.0277(6) Uani 1 1 d . . . . .
O3 O 0.2005(4) 0.27350(8) 0.1105(2) 0.0207(5) Uani 1 1 d . . . . .
N1 N 0.2345(6) 0.19336(10) 0.7755(2) 0.0166(6) Uani 1 1 d . . . . .
N3 N 0.0889(5) 0.27063(10) 0.7325(3) 0.0184(6) Uani 1 1 d . . . . .
C6 C 0.4940(6) 0.12477(12) 0.8614(3) 0.0191(7) Uani 1 1 d . . . . .
H2 H 0.389892 0.100193 0.827293 0.023 Uiso 1 1 calc R U . . .
C14 C 0.1958(6) 0.31708(12) 0.0995(3) 0.0173(7) Uani 1 1 d . . . . .
C4 C 0.8647(6) 0.15229(13) 0.9836(3) 0.0199(7) Uani 1 1 d . . . . .
H3 H 1.015837 0.144633 1.030806 0.024 Uiso 1 1 calc R U . . .
C15 C -0.0441(6) 0.33772(12) 0.0297(3) 0.0179(7) Uani 1 1 d . . . . .
C1 C 0.2592(6) 0.23965(11) 0.7868(3) 0.0151(7) Uani 1 1 d . . . . .
C3 C 0.7992(6) 0.19905(12) 0.9690(3) 0.0181(7) Uani 1 1 d . . . . .
H4 H 0.898618 0.223625 1.006215 0.022 Uiso 1 1 calc R U . . .
C8 C 0.1079(6) 0.31791(12) 0.7483(3) 0.0179(7) Uani 1 1 d . . . . .
C7 C 0.4326(6) 0.17177(12) 0.8440(3) 0.0156(7) Uani 1 1 d . . . . .
C2 C 0.5797(6) 0.20833(12) 0.8969(3) 0.0167(7) Uani 1 1 d . . . . .
C5 C 0.7169(7) 0.11537(12) 0.9315(3) 0.0201(7) Uani 1 1 d . . . . .
C9 C -0.0972(7) 0.39026(12) 0.7101(3) 0.0269(8) Uani 1 1 d . . . . .
H9A H -0.075128 0.397783 0.795522 0.040 Uiso 1 1 calc R U . . .
H9B H -0.260985 0.402641 0.677030 0.040 Uiso 1 1 calc R U . . .
H9C H 0.040894 0.404666 0.668324 0.040 Uiso 1 1 calc R U . . .
C11 C 0.7140(10) 0.02622(17) 0.7288(4) 0.0493(13) Uani 1 1 d . . . . .
C10 C 0.6517(8) 0.02033(13) 0.8578(4) 0.0342(10) Uani 1 1 d . . . . .
H2A H 0.503(6) 0.2751(13) 0.870(3) -0.001(8) Uiso 1 1 d . . . . .
H7A H 0.396(11) 0.3999(19) 1.017(5) 0.058(16) Uiso 1 1 d . . . . .
H1A H 0.117(9) 0.1818(17) 0.741(4) 0.040(14) Uiso 1 1 d . . . . .
H6A H -0.211(10) 0.3917(18) 0.014(5) 0.050(15) Uiso 1 1 d . . . . .
H7B H 0.452(12) 0.395(2) 0.898(6) 0.07(2) Uiso 1 1 d . . . . .
H3A H -0.048(10) 0.2576(18) 0.688(5) 0.050(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C13A C11 1.382(9) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C13B C11 1.465(11) . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
S1 C5 1.773(3) . ?
S1 C10 1.808(4) . ?
O2 C8 1.328(4) . ?
O2 C9 1.446(4) . ?
O1 C8 1.224(4) . ?
O4 C14 1.260(4) . ?
O5 C15 1.213(4) . ?
O6 C15 1.305(4) . ?
O6 H6A 0.82(6) . ?
N2 C1 1.329(4) . ?
N2 C2 1.390(4) . ?
N2 H2A 0.75(3) . ?
O7 H7A 0.89(6) . ?
O7 H7B 0.82(7) . ?
O3 C14 1.241(4) . ?
N1 C1 1.323(4) . ?
N1 C7 1.393(4) . ?
N1 H1A 0.78(5) . ?
N3 C8 1.354(5) . ?
N3 C1 1.368(4) . ?
N3 H3A 0.93(5) . ?
C6 C7 1.381(5) . ?
C6 C5 1.393(5) . ?
C6 H2 0.9500 . ?
C14 C15 1.553(4) . ?
C4 C3 1.376(5) . ?
C4 C5 1.407(5) . ?
C4 H3 0.9500 . ?
C3 C2 1.390(5) . ?
C3 H4 0.9500 . ?
C7 C2 1.401(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C10 1.513(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C13A H13A 109.5 . . ?
C11 C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C11 C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11 C13B H13D 109.5 . . ?
C11 C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C11 C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C5 S1 C10 104.47(17) . . ?
C8 O2 C9 115.2(3) . . ?
C15 O6 H6A 110(4) . . ?
C1 N2 C2 108.5(3) . . ?
C1 N2 H2A 122(3) . . ?
C2 N2 H2A 130(3) . . ?
H7A O7 H7B 108(5) . . ?
C1 N1 C7 108.5(3) . . ?
C1 N1 H1A 122(4) . . ?
C7 N1 H1A 129(4) . . ?
C8 N3 C1 122.4(3) . . ?
C8 N3 H3A 121(3) . . ?
C1 N3 H3A 117(3) . . ?
C7 C6 C5 116.4(3) . . ?
C7 C6 H2 121.8 . . ?
C5 C6 H2 121.8 . . ?
O3 C14 O4 128.3(3) . . ?
O3 C14 C15 115.8(3) . . ?
O4 C14 C15 115.9(3) . . ?
C3 C4 C5 122.7(3) . . ?
C3 C4 H3 118.7 . . ?
C5 C4 H3 118.7 . . ?
O5 C15 O6 125.1(3) . . ?
O5 C15 C14 121.3(3) . . ?
O6 C15 C14 113.6(3) . . ?
N1 C1 N2 110.5(3) . . ?
N1 C1 N3 122.4(3) . . ?
N2 C1 N3 127.1(3) . . ?
C4 C3 C2 116.3(3) . . ?
C4 C3 H4 121.9 . . ?
C2 C3 H4 121.9 . . ?
O1 C8 O2 124.8(3) . . ?
O1 C8 N3 124.8(3) . . ?
O2 C8 N3 110.5(3) . . ?
C6 C7 N1 131.3(3) . . ?
C6 C7 C2 122.4(3) . . ?
N1 C7 C2 106.2(3) . . ?
C3 C2 N2 132.4(3) . . ?
C3 C2 C7 121.3(3) . . ?
N2 C2 C7 106.2(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 S1 123.7(3) . . ?
C4 C5 S1 115.4(3) . . ?
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 . . ?
C13A C11 C10 112.9(5) . . ?
C13B C11 C10 126.6(6) . . ?
C11 C10 S1 114.7(3) . . ?

_refine_diff_density_max         0.728
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.083

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ABZ-26DHBA
_database_code_depnum_ccdc_archive 'CCDC 1834928'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Albendazole-26dihydroxy benzoic acid'
_chemical_name_common            ABZ-26DHBA
_chemical_melting_point          451
_chemical_formula_moiety         'C12 H8 N3 O2 S, C12 H8 N3 O2 S, 2(C7 H5 O4)'
_chemical_formula_sum            'C38 H26 N6 O12 S2'
_chemical_formula_weight         822.77

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.176(5)
_cell_length_b                   9.293(3)
_cell_length_c                   25.789(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.950(5)
_cell_angle_gamma                90
_cell_volume                     3958(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6900
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.85

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35767
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.280
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_full        24.713
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6738
_reflns_number_gt                5057
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1032P)²+4.4613P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6738
_refine_ls_number_parameters     621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.2099
_refine_ls_wR_factor_gt          0.1946
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2A S 0.19614(8) 0.69391(17) 0.21240(6) 0.0626(5) Uani 0.873(4) 1 d . . P A 1
S1B S 0.57294(9) 0.49914(19) 0.90868(7) 0.0515(6) Uani 0.676(3) 1 d . . P B 2
O3 O -0.20170(15) 1.2151(3) 0.03152(10) 0.0437(7) Uani 1 1 d . . . . .
N2 N -0.07796(19) 1.0461(4) 0.09435(12) 0.0372(7) Uani 1 1 d . . . . .
N1 N 0.03114(18) 1.0515(4) 0.06636(12) 0.0379(7) Uani 1 1 d . . . . .
O4 O -0.16078(16) 1.3568(3) -0.02776(11) 0.0510(7) Uani 1 1 d . . . . .
C11 C -0.0232(2) 0.9527(4) 0.12741(14) 0.0369(9) Uani 1 1 d . . . . .
N3 N -0.07480(19) 1.1994(4) 0.01971(13) 0.0409(8) Uani 1 1 d . . . . .
C16 C 0.0464(2) 0.9573(4) 0.10946(15) 0.0386(9) Uani 1 1 d . . . . .
C15 C 0.1142(2) 0.8756(4) 0.13359(16) 0.0453(10) Uani 1 1 d . . . . .
H26 H 0.160912 0.875700 0.120616 0.054 Uiso 1 1 calc R U . . .
C10 C -0.0440(2) 1.1034(4) 0.05887(15) 0.0356(8) Uani 1 1 d . . . . .
C17 C -0.1512(2) 1.2555(4) 0.00982(15) 0.0417(9) Uani 1 1 d . . . . .
C13 C 0.0398(3) 0.7887(5) 0.19608(17) 0.0523(11) Uani 1 1 d . . . . .
C12 C -0.0279(2) 0.8685(5) 0.17063(16) 0.0464(10) Uani 1 1 d . . . . .
H23 H -0.075681 0.865580 0.182392 0.056 Uiso 1 1 calc R U . . .
C14 C 0.1102(3) 0.7937(5) 0.17763(17) 0.0523(11) Uani 1 1 d . . . . .
C18 C -0.2389(2) 1.4236(5) -0.0439(2) 0.0593(12) Uani 1 1 d . . . . .
H30A H -0.278836 1.354386 -0.064157 0.089 Uiso 1 1 calc R U . . .
H30B H -0.236918 1.506993 -0.066797 0.089 Uiso 1 1 calc R U . . .
H30C H -0.254329 1.455176 -0.011864 0.089 Uiso 1 1 calc R U . . .
O5 O 0.87180(14) 0.8410(3) -0.00916(10) 0.0396(6) Uani 1 1 d . . . . .
O1 O 0.28040(15) 0.9626(3) 1.06992(11) 0.0469(7) Uani 1 1 d . . . . .
O6 O 0.96271(16) 0.6661(3) 0.01437(12) 0.0503(7) Uani 1 1 d . . . . .
N5 N 0.50084(19) 0.8653(4) 1.04332(14) 0.0407(8) Uani 1 1 d . . . . .
O7 O 0.75090(15) 0.8512(3) 0.03213(11) 0.0444(7) Uani 1 1 d . . . . .
N4 N 0.3706(2) 0.8333(4) 1.01019(13) 0.0418(8) Uani 1 1 d . . . . .
C28 C 0.7861(2) 0.7381(4) 0.06329(15) 0.0376(9) Uani 1 1 d . . . . .
O2 O 0.34958(16) 1.1294(3) 1.12804(12) 0.0540(8) Uani 1 1 d . . . . .
O8 O 0.95558(18) 0.4832(3) 0.08578(14) 0.0556(8) Uani 1 1 d . . . . .
C31 C 0.8994(2) 0.7298(4) 0.01825(15) 0.0372(9) Uani 1 1 d . . . . .
C29 C 0.8570(2) 0.6720(4) 0.05683(14) 0.0343(8) Uani 1 1 d . . . . .
C1 C 0.4281(2) 0.9022(4) 1.04742(15) 0.0391(9) Uani 1 1 d . . . . .
N6 N 0.41706(19) 0.9968(4) 1.08450(14) 0.0428(8) Uani 1 1 d . . . . .
C8 C 0.3422(2) 1.0245(5) 1.09251(16) 0.0425(9) Uani 1 1 d . . . . .
C24 C 0.8891(2) 0.5540(4) 0.08998(16) 0.0428(9) Uani 1 1 d . . . . .
C6 C 0.3753(3) 0.6556(5) 0.93765(17) 0.0545(11) Uani 1 1 d . . . . .
H33 H 0.318465 0.642871 0.924002 0.065 Uiso 1 1 calc R U . . .
C7 C 0.4073(2) 0.7474(4) 0.98017(16) 0.0436(9) Uani 1 1 d . . . . .
C27 C 0.7501(2) 0.6882(5) 0.10181(16) 0.0458(10) Uani 1 1 d . . . . .
H10 H 0.702240 0.732205 0.105859 0.055 Uiso 1 1 calc R U . . .
C26 C 0.7848(3) 0.5735(5) 0.13439(17) 0.0491(10) Uani 1 1 d . . . . .
H11 H 0.760727 0.541150 0.161369 0.059 Uiso 1 1 calc R U . . .
C2 C 0.4909(2) 0.7683(4) 1.00131(16) 0.0430(9) Uani 1 1 d . . . . .
C32 C 0.5453(3) 0.6975(5) 0.97961(18) 0.0537(11) Uani 1 1 d . . . . .
H17 H 0.602098 0.711178 0.993089 0.064 Uiso 1 1 calc R U . . .
C25 C 0.8528(3) 0.5053(5) 0.12872(17) 0.0495(10) Uani 1 1 d . . . . .
H12 H 0.874952 0.425699 0.151030 0.059 Uiso 1 1 calc R U . . .
C4 C 0.5118(4) 0.6039(5) 0.93639(19) 0.0647(14) Uani 1 1 d . . . . .
C9 C 0.2737(3) 1.1743(6) 1.1383(2) 0.0662(14) Uani 1 1 d . . . . .
H31A H 0.250910 1.093828 1.153878 0.099 Uiso 1 1 calc R U . . .
H31B H 0.235256 1.203631 1.104270 0.099 Uiso 1 1 calc R U . . .
H31C H 0.283920 1.255439 1.163489 0.099 Uiso 1 1 calc R U . . .
C5 C 0.4279(3) 0.5835(5) 0.91581(19) 0.0618(12) Uani 1 1 d . . . . .
O9 O 0.28446(16) 0.4536(3) 0.63393(11) 0.0453(7) Uani 1 1 d . . . . .
O11 O 0.13350(14) 0.5081(3) 0.60770(11) 0.0436(7) Uani 1 1 d . . . . .
O10 O 0.11388(18) 0.2518(4) 0.73530(13) 0.0568(8) Uani 1 1 d . . . . .
O12 O 0.05433(14) 0.4101(3) 0.65359(11) 0.0481(7) Uani 1 1 d . . . . .
C30 C 0.1232(2) 0.4291(4) 0.64548(15) 0.0373(9) Uani 1 1 d . . . . .
C21 C 0.1943(2) 0.3566(4) 0.68175(14) 0.0349(8) Uani 1 1 d . . . . .
C20 C 0.1868(2) 0.2728(4) 0.72539(15) 0.0406(9) Uani 1 1 d . . . . .
C22 C 0.2724(2) 0.3730(4) 0.67492(14) 0.0365(9) Uani 1 1 d . . . . .
C23 C 0.3393(2) 0.3093(4) 0.70971(15) 0.0431(9) Uani 1 1 d . . . . .
H5 H 0.391623 0.322605 0.704765 0.052 Uiso 1 1 calc R U . . .
C33 C 0.2531(2) 0.2067(5) 0.75955(16) 0.0472(10) Uani 1 1 d . . . . .
H3 H 0.246729 0.148072 0.788287 0.057 Uiso 1 1 calc R U . . .
C19 C 0.3292(3) 0.2259(5) 0.75183(17) 0.0491(10) Uani 1 1 d . . . . .
H4 H 0.374881 0.181379 0.775744 0.059 Uiso 1 1 calc R U . . .
C39 C 0.5892(7) 0.4377(14) 0.8098(4) 0.081(3) Uani 0.676(3) 1 d . . P B 2
C38 C 0.5360(6) 0.5253(11) 0.8356(3) 0.072(3) Uani 0.676(3) 1 d . . P B 2
C40 C 0.5862(6) 0.2789(11) 0.8180(4) 0.082(3) Uani 0.676(3) 1 d . . P B 2
C43 C 0.0889(4) 0.2893(6) 0.1774(2) 0.0845(18) Uani 1 1 d . . . . .
C42 C 0.1025(4) 0.4362(8) 0.2017(4) 0.116(3) Uani 1 1 d . . . . .
C41 C 0.1629(5) 0.5063(10) 0.1838(5) 0.140(4) Uani 0.873(4) 1 d . . P . .
S1C S 0.4173(2) 0.4630(5) 0.86434(15) 0.0619(13) Uani 0.324(3) 1 d . . P B 3
S2B S 0.0724(6) 0.6879(13) 0.2519(4) 0.071(4) Uani 0.127(4) 1 d . . P A 2
C1A C 0.045(2) 0.509(4) 0.218(2) 0.085(16) Uani 0.127(4) 1 d . . P . .
C1C C 0.4921(11) 0.480(3) 0.8289(8) 0.074(7) Uani 0.324(3) 1 d . . P B 3
C1B C 0.533(3) 0.379(3) 0.8422(10) 0.18(2) Uani 0.324(3) 1 d . . P B 3
C1D C 0.623(2) 0.431(5) 0.8034(17) 0.158(17) Uani 0.324(3) 1 d . . P B 3
H3A H -0.042(2) 1.243(4) 0.0046(15) 0.036(10) Uiso 1 1 d . . . . .
H2A H -0.124(3) 1.070(4) 0.0963(15) 0.039(11) Uiso 1 1 d . . . . .
H1A H 0.069(3) 1.089(5) 0.0441(19) 0.074(15) Uiso 1 1 d . . . . .
H6A H 0.462(3) 1.038(5) 1.1115(19) 0.065(14) Uiso 1 1 d . . . . .
H5A H 0.542(2) 0.906(4) 1.0648(15) 0.034(10) Uiso 1 1 d . . . . .
H4A H 0.318(3) 0.835(6) 1.004(2) 0.076(16) Uiso 1 1 d . . . . .
H10A H 0.082(3) 0.306(5) 0.707(2) 0.066(15) Uiso 1 1 d . . . . .
H7A H 0.786(3) 0.878(5) 0.0131(19) 0.067(14) Uiso 1 1 d . . . . .
H9A H 0.237(3) 0.488(6) 0.614(2) 0.074(16) Uiso 1 1 d . . . . .
H8A H 0.967(3) 0.521(6) 0.058(2) 0.09(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2A C14 1.766(4) . ?
S2A C41 1.918(11) . ?
S1B C4 1.725(5) . ?
S1B C38 1.833(9) . ?
O3 C17 1.214(5) . ?
N2 C10 1.325(5) . ?
N2 C11 1.386(5) . ?
N2 H2A 0.83(4) . ?
N1 C10 1.341(5) . ?
N1 C16 1.382(5) . ?
N1 H1A 1.03(5) . ?
O4 C17 1.329(5) . ?
O4 C18 1.432(5) . ?
C11 C12 1.382(5) . ?
C11 C16 1.397(5) . ?
N3 C10 1.342(5) . ?
N3 C17 1.370(5) . ?
N3 H3A 0.86(4) . ?
C16 C15 1.387(5) . ?
C15 C14 1.384(6) . ?
C15 H26 0.9500 . ?
C13 C12 1.383(6) . ?
C13 C14 1.416(6) . ?
C13 S2B 1.679(11) . ?
C12 H23 0.9500 . ?
C18 H30A 0.9800 . ?
C18 H30B 0.9800 . ?
C18 H30C 0.9800 . ?
O5 C31 1.268(4) . ?
O1 C8 1.207(5) . ?
O6 C31 1.267(4) . ?
N5 C1 1.328(5) . ?
N5 C2 1.383(5) . ?
N5 H5A 0.86(4) . ?
O7 C28 1.359(5) . ?
O7 H7A 0.91(5) . ?
N4 C1 1.336(5) . ?
N4 C7 1.379(5) . ?
N4 H4A 0.88(5) . ?
C28 C27 1.385(5) . ?
C28 C29 1.415(5) . ?
O2 C8 1.320(5) . ?
O2 C9 1.460(5) . ?
O8 C24 1.348(5) . ?
O8 H8A 0.85(6) . ?
C31 C29 1.485(5) . ?
C29 C24 1.406(5) . ?
C1 N6 1.350(5) . ?
N6 C8 1.381(5) . ?
N6 H6A 0.97(5) . ?
C24 C25 1.390(6) . ?
C6 C5 1.364(7) . ?
C6 C7 1.379(6) . ?
C6 H33 0.9500 . ?
C7 C2 1.402(6) . ?
C27 C26 1.386(6) . ?
C27 H10 0.9500 . ?
C26 C25 1.372(6) . ?
C26 H11 0.9500 . ?
C2 C32 1.380(6) . ?
C32 C4 1.406(7) . ?
C32 H17 0.9500 . ?
C25 H12 0.9500 . ?
C4 C5 1.404(7) . ?
C9 H31A 0.9800 . ?
C9 H31B 0.9800 . ?
C9 H31C 0.9800 . ?
C5 S1C 1.708(6) . ?
O9 C22 1.357(4) . ?
O9 H9A 0.90(6) . ?
O11 C30 1.270(4) . ?
O10 C20 1.359(5) . ?
O10 H10A 0.93(5) . ?
O12 C30 1.269(4) . ?
C30 C21 1.481(5) . ?
C21 C20 1.404(5) . ?
C21 C22 1.408(5) . ?
C20 C33 1.379(6) . ?
C22 C23 1.381(5) . ?
C23 C19 1.384(6) . ?
C23 H5 0.9500 . ?
C33 C19 1.386(6) . ?
C33 H3 0.9500 . ?
C19 H4 0.9500 . ?
C39 C40 1.494(16) . ?
C39 C38 1.507(14) . ?
C43 C42 1.493(9) . ?
C42 C1A 1.36(4) . ?
C42 C41 1.405(11) . ?
S1C C1C 1.777(18) . ?
S2B C1A 1.88(4) . ?
C1C C1B 1.16(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 S2A C41 99.4(3) . . ?
C4 S1B C38 105.9(3) . . ?
C10 N2 C11 108.9(3) . . ?
C10 N2 H2A 123(3) . . ?
C11 N2 H2A 128(3) . . ?
C10 N1 C16 107.8(3) . . ?
C10 N1 H1A 121(3) . . ?
C16 N1 H1A 131(3) . . ?
C17 O4 C18 115.9(3) . . ?
C12 C11 N2 132.1(3) . . ?
C12 C11 C16 122.0(4) . . ?
N2 C11 C16 105.9(3) . . ?
C10 N3 C17 123.5(3) . . ?
C10 N3 H3A 119(3) . . ?
C17 N3 H3A 117(3) . . ?
N1 C16 C15 131.1(3) . . ?
N1 C16 C11 107.2(3) . . ?
C15 C16 C11 121.6(4) . . ?
C14 C15 C16 116.3(4) . . ?
C14 C15 H26 121.8 . . ?
C16 C15 H26 121.8 . . ?
N2 C10 N1 110.1(3) . . ?
N2 C10 N3 129.0(3) . . ?
N1 C10 N3 120.8(3) . . ?
O3 C17 O4 126.5(4) . . ?
O3 C17 N3 124.4(4) . . ?
O4 C17 N3 109.0(3) . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 S2B 138.1(5) . . ?
C14 C13 S2B 101.1(4) . . ?
C11 C12 C13 117.3(4) . . ?
C11 C12 H23 121.3 . . ?
C13 C12 H23 121.3 . . ?
C15 C14 C13 122.3(4) . . ?
C15 C14 S2A 118.8(3) . . ?
C13 C14 S2A 118.9(3) . . ?
O4 C18 H30A 109.5 . . ?
O4 C18 H30B 109.5 . . ?
H30A C18 H30B 109.5 . . ?
O4 C18 H30C 109.5 . . ?
H30A C18 H30C 109.5 . . ?
H30B C18 H30C 109.5 . . ?
C1 N5 C2 108.4(3) . . ?
C1 N5 H5A 117(3) . . ?
C2 N5 H5A 134(3) . . ?
C28 O7 H7A 106(3) . . ?
C1 N4 C7 108.6(3) . . ?
C1 N4 H4A 130(3) . . ?
C7 N4 H4A 122(3) . . ?
O7 C28 C27 118.0(3) . . ?
O7 C28 C29 121.5(3) . . ?
C27 C28 C29 120.5(4) . . ?
C8 O2 C9 114.6(3) . . ?
C24 O8 H8A 104(4) . . ?
O6 C31 O5 122.3(3) . . ?
O6 C31 C29 118.3(3) . . ?
O5 C31 C29 119.5(3) . . ?
C24 C29 C28 118.2(3) . . ?
C24 C29 C31 120.5(3) . . ?
C28 C29 C31 121.2(3) . . ?
N5 C1 N4 110.1(4) . . ?
N5 C1 N6 122.9(3) . . ?
N4 C1 N6 127.0(3) . . ?
C1 N6 C8 123.0(3) . . ?
C1 N6 H6A 122(3) . . ?
C8 N6 H6A 114(3) . . ?
O1 C8 O2 126.2(4) . . ?
O1 C8 N6 124.8(4) . . ?
O2 C8 N6 109.0(3) . . ?
O8 C24 C25 117.1(4) . . ?
O8 C24 C29 122.1(4) . . ?
C25 C24 C29 120.8(4) . . ?
C5 C6 C7 117.9(4) . . ?
C5 C6 H33 121.1 . . ?
C7 C6 H33 121.1 . . ?
N4 C7 C6 131.4(4) . . ?
N4 C7 C2 106.2(3) . . ?
C6 C7 C2 122.4(4) . . ?
C28 C27 C26 119.4(4) . . ?
C28 C27 H10 120.3 . . ?
C26 C27 H10 120.3 . . ?
C25 C26 C27 121.8(4) . . ?
C25 C26 H11 119.1 . . ?
C27 C26 H11 119.1 . . ?
C32 C2 N5 132.6(4) . . ?
C32 C2 C7 120.7(4) . . ?
N5 C2 C7 106.7(3) . . ?
C2 C32 C4 116.2(4) . . ?
C2 C32 H17 121.9 . . ?
C4 C32 H17 121.9 . . ?
C26 C25 C24 119.3(4) . . ?
C26 C25 H12 120.3 . . ?
C24 C25 H12 120.3 . . ?
C5 C4 C32 122.5(4) . . ?
C5 C4 S1B 116.5(4) . . ?
C32 C4 S1B 120.9(4) . . ?
O2 C9 H31A 109.5 . . ?
O2 C9 H31B 109.5 . . ?
H31A C9 H31B 109.5 . . ?
O2 C9 H31C 109.5 . . ?
H31A C9 H31C 109.5 . . ?
H31B C9 H31C 109.5 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 S1C 134.5(4) . . ?
C4 C5 S1C 105.1(4) . . ?
C22 O9 H9A 109(3) . . ?
C20 O10 H10A 99(3) . . ?
O12 C30 O11 122.6(3) . . ?
O12 C30 C21 118.5(3) . . ?
O11 C30 C21 118.9(3) . . ?
C20 C21 C22 117.5(3) . . ?
C20 C21 C30 121.1(3) . . ?
C22 C21 C30 121.4(3) . . ?
O10 C20 C33 117.3(4) . . ?
O10 C20 C21 121.6(3) . . ?
C33 C20 C21 121.2(3) . . ?
O9 C22 C23 117.7(3) . . ?
O9 C22 C21 120.7(3) . . ?
C23 C22 C21 121.6(3) . . ?
C22 C23 C19 119.2(4) . . ?
C22 C23 H5 120.4 . . ?
C19 C23 H5 120.4 . . ?
C20 C33 C19 119.8(4) . . ?
C20 C33 H3 120.1 . . ?
C19 C33 H3 120.1 . . ?
C23 C19 C33 120.8(4) . . ?
C23 C19 H4 119.6 . . ?
C33 C19 H4 119.6 . . ?
C40 C39 C38 115.0(10) . . ?
C39 C38 S1B 107.6(6) . . ?
C1A C42 C41 122.5(18) . . ?
C1A C42 C43 122.6(17) . . ?
C41 C42 C43 109.3(8) . . ?
C42 C41 S2A 117.7(8) . . ?
C5 S1C C1C 113.9(8) . . ?
C13 S2B C1A 96.3(16) . . ?
C42 C1A S2B 118(2) . . ?
C1B C1C S1C 104(3) . . ?

_refine_diff_density_max         1.218
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.079

