# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_CA1
_database_code_depnum_ccdc_archive 'CCDC 1450966'
_audit_update_record             
;
2016-01-31 deposited with the CCDC.
2016-02-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_NTZ-PABA            
;
RESPONSE: This is due to occupacy oxygen and hydrogen atoms at same postion.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 Acetic acid 2-(5-nitro-thiazol-2-carbamoyl)-phenyl ester-4-amino benzoic acid-4-amino salicylic acid
;
_chemical_name_common            
'Nitazoxanide-p-aminobenzoic acid-p-amino salicylic acid cocrystal alloy'
_chemical_melting_point          426
_chemical_formula_moiety         'C12 H9N3O5S, C7 H7NO2.33'
_chemical_formula_sum            'C19 H16 N4 O7.33 S'
_chemical_formula_weight         449.62

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                   7.3750(8)
_cell_length_b                   11.4414(12)
_cell_length_c                   13.8757(12)
_cell_angle_alpha                108.729(8)
_cell_angle_beta                 97.485(8)
_cell_angle_gamma                107.618(10)
_cell_volume                     1022.72(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1888
_cell_measurement_theta_min      3.3310
_cell_measurement_theta_max      25.999

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             465
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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            7161
_diffrn_reflns_av_unetI/netI     0.1142
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.934
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_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             4006
_reflns_number_gt                1888
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0279P)²] 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         4006
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_restrained_S_all      0.870
_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
O8 O 0.2543(8) 0.2005(6) 0.3036(5) 0.066(3) Uiso 0.329(7) 1 d . . P . .
H8A H 0.2799 0.2455 0.3665 0.099 Uiso 0.329(7) 1 calc R U P . .
S1 S 0.25374(11) 0.65334(9) 0.85074(6) 0.0493(3) Uani 1 1 d . . . . .
O3 O 0.2188(3) 0.4064(2) 0.82615(17) 0.0585(7) Uani 1 1 d . . . . .
O7 O 0.2549(4) 0.5687(2) 0.45517(17) 0.0688(7) Uani 1 1 d . . . . .
H7A H 0.2540 0.5875 0.5173 0.103 Uiso 1 1 calc R U . . .
O1 O -0.0225(3) 0.1283(2) 0.75671(17) 0.0582(7) Uani 1 1 d . . . . .
N2 N 0.2601(3) 0.6455(3) 0.66312(19) 0.0480(7) Uani 1 1 d . . . . .
C2 C 0.2146(4) 0.2306(3) 0.6741(2) 0.0418(8) Uani 1 1 d . . . . .
N1 N 0.2350(4) 0.4474(3) 0.6796(2) 0.0462(7) Uani 1 1 d . . . . .
O2 O -0.1923(3) 0.2139(3) 0.67099(18) 0.0667(7) Uani 1 1 d . . . . .
O6 O 0.2251(3) 0.3730(2) 0.46296(18) 0.0695(7) Uani 1 1 d . . . . .
O4 O 0.2812(4) 1.0017(3) 0.86902(19) 0.0822(8) Uani 1 1 d . . . . .
O5 O 0.2727(4) 0.9143(2) 0.98587(19) 0.0802(8) Uani 1 1 d . . . . .
C3 C 0.3309(4) 0.2123(4) 0.6037(2) 0.0509(9) Uani 1 1 d . . . . .
H12 H 0.4108 0.2850 0.5931 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2501(4) 0.5745(3) 0.7219(2) 0.0427(8) Uani 1 1 d . . . . .
C1 C 0.0977(4) 0.1210(3) 0.6879(2) 0.0461(8) Uani 1 1 d . . . . .
N3 N 0.2757(4) 0.9091(3) 0.8967(2) 0.0606(8) Uani 1 1 d . . . . .
C7 C 0.2218(4) 0.3665(3) 0.7337(3) 0.0453(9) Uani 1 1 d . . . . .
N4 N 0.2597(4) 0.2709(3) -0.0119(2) 0.0743(9) Uani 1 1 d . . . . .
H5A H 0.1879 0.1879 -0.0430 0.089 Uiso 1 1 d R U . . .
H4B H 0.2167 0.3153 -0.0426 0.089 Uiso 1 1 d R U . . .
C5 C 0.2115(5) -0.0201(4) 0.5640(3) 0.0598(10) Uani 1 1 d . . . . .
H5 H 0.2103 -0.1041 0.5271 0.072 Uiso 1 1 calc R U . . .
C17 C 0.2580(4) 0.4420(3) 0.1438(2) 0.0504(9) Uani 1 1 d . . . . .
H17 H 0.2661 0.4993 0.1084 0.061 Uiso 1 1 calc R U . . .
C13 C 0.2461(4) 0.4018(3) 0.3028(2) 0.0412(8) Uani 1 1 d . . . . .
C14 C 0.2387(4) 0.2732(4) 0.2492(3) 0.0505(9) Uani 1 1 d . . . . .
C18 C 0.2549(4) 0.4844(3) 0.2472(2) 0.0471(9) Uani 1 1 d . . . . .
H18 H 0.2588 0.5700 0.2810 0.057 Uiso 1 1 calc R U . . .
C15 C 0.2390(4) 0.2303(3) 0.1457(3) 0.0514(9) Uani 1 1 d . . . . .
H15 H 0.2325 0.1441 0.1115 0.062 Uiso 1 1 calc R U . . .
C16 C 0.2488(4) 0.3124(4) 0.0905(3) 0.0514(9) Uani 1 1 d . . . . .
C12 C 0.2705(4) 0.7899(3) 0.8220(3) 0.0454(8) Uani 1 1 d . . . . .
C11 C 0.2725(4) 0.7680(3) 0.7203(3) 0.0505(9) Uani 1 1 d . . . . .
H26 H 0.2818 0.8328 0.6924 0.061 Uiso 1 1 calc R U . . .
C4 C 0.3295(5) 0.0881(4) 0.5496(3) 0.0585(10) Uani 1 1 d . . . . .
H4 H 0.4088 0.0773 0.5031 0.070 Uiso 1 1 calc R U . . .
C8 C -0.1658(5) 0.1767(4) 0.7408(3) 0.0578(10) Uani 1 1 d . . . . .
C6 C 0.0957(5) -0.0038(4) 0.6328(3) 0.0566(9) Uani 1 1 d . . . . .
H6 H 0.0153 -0.0771 0.6425 0.068 Uiso 1 1 calc R U . . .
C30 C 0.2429(4) 0.4444(4) 0.4131(3) 0.0506(9) Uani 1 1 d . . . . .
C9 C -0.2805(5) 0.1789(4) 0.8209(3) 0.1000(15) Uani 1 1 d . . . . .
H9A H -0.3283 0.0924 0.8237 0.150 Uiso 1 1 calc R U . . .
H9B H -0.3896 0.2035 0.8027 0.150 Uiso 1 1 calc R U . . .
H9C H -0.1978 0.2422 0.8884 0.150 Uiso 1 1 calc R U . . .
H21 H 0.2543(8) 0.2005(6) 0.3036(5) 0.066(3) Uiso 0.671(7) 1 d . . P . .
H1A H 0.235(4) 0.420(3) 0.611(2) 0.048(9) 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
O8 C14 1.310(6) . ?
O8 H8A 0.8200 . ?
O8 H21 0.00(2) . ?
S1 C12 1.706(3) . ?
S1 C10 1.717(3) . ?
O3 C7 1.222(3) . ?
O7 C30 1.322(4) . ?
O7 H7A 0.8200 . ?
O1 C8 1.358(4) . ?
O1 C1 1.385(3) . ?
N2 C10 1.316(3) . ?
N2 C11 1.339(4) . ?
C2 C1 1.377(4) . ?
C2 C3 1.388(4) . ?
C2 C7 1.489(4) . ?
N1 C10 1.345(4) . ?
N1 C7 1.357(4) . ?
N1 H1A 0.90(3) . ?
O2 C8 1.193(3) . ?
O6 C30 1.219(4) . ?
O4 N3 1.229(3) . ?
O5 N3 1.224(3) . ?
C3 C4 1.374(4) . ?
C3 H12 0.9300 . ?
C1 C6 1.381(4) . ?
N3 C12 1.409(4) . ?
N4 C16 1.368(4) . ?
N4 H5A 0.8606 . ?
N4 H4B 0.8612 . ?
C5 C6 1.367(4) . ?
C5 C4 1.371(4) . ?
C5 H5 0.9300 . ?
C17 C18 1.364(4) . ?
C17 C16 1.404(4) . ?
C17 H17 0.9300 . ?
C13 C18 1.392(4) . ?
C13 C14 1.399(4) . ?
C13 C30 1.455(4) . ?
C14 C15 1.361(4) . ?
C14 H21 1.310(6) . ?
C18 H18 0.9300 . ?
C15 C16 1.382(4) . ?
C15 H15 0.9300 . ?
C12 C11 1.355(4) . ?
C11 H26 0.9300 . ?
C4 H4 0.9300 . ?
C8 C9 1.481(4) . ?
C6 H6 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C14 O8 H8A 109.5 . . ?
C14 O8 H21 0.0(4) . . ?
H8A O8 H21 0.0 . . ?
C12 S1 C10 86.93(16) . . ?
C30 O7 H7A 109.5 . . ?
C8 O1 C1 118.2(2) . . ?
C10 N2 C11 110.1(3) . . ?
C1 C2 C3 118.3(3) . . ?
C1 C2 C7 121.8(3) . . ?
C3 C2 C7 119.9(3) . . ?
C10 N1 C7 124.1(3) . . ?
C10 N1 H1A 114.0(19) . . ?
C7 N1 H1A 121.9(19) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H12 119.6 . . ?
C2 C3 H12 119.6 . . ?
N2 C10 N1 120.0(3) . . ?
N2 C10 S1 116.1(3) . . ?
N1 C10 S1 123.9(3) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 O1 123.0(3) . . ?
C6 C1 O1 116.3(3) . . ?
O5 N3 O4 123.4(3) . . ?
O5 N3 C12 117.9(3) . . ?
O4 N3 C12 118.7(3) . . ?
O3 C7 N1 120.4(3) . . ?
O3 C7 C2 123.5(3) . . ?
N1 C7 C2 116.0(3) . . ?
C16 N4 H5A 108.6 . . ?
C16 N4 H4B 109.5 . . ?
H5A N4 H4B 109.5 . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C18 C13 C14 117.9(3) . . ?
C18 C13 C30 122.4(3) . . ?
C14 C13 C30 119.7(3) . . ?
O8 C14 C15 120.4(5) . . ?
O8 C14 C13 118.2(4) . . ?
C15 C14 C13 120.9(3) . . ?
O8 C14 H21 0.0 . . ?
C15 C14 H21 120.4(5) . . ?
C13 C14 H21 118.2(4) . . ?
C17 C18 C13 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C14 C15 C16 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
N4 C16 C15 120.8(4) . . ?
N4 C16 C17 120.8(3) . . ?
C15 C16 C17 118.3(3) . . ?
C11 C12 N3 125.2(3) . . ?
C11 C12 S1 112.2(3) . . ?
N3 C12 S1 122.5(3) . . ?
N2 C11 C12 114.6(3) . . ?
N2 C11 H26 122.7 . . ?
C12 C11 H26 122.7 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
O2 C8 O1 123.3(3) . . ?
O2 C8 C9 125.0(4) . . ?
O1 C8 C9 111.7(3) . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O6 C30 O7 121.9(3) . . ?
O6 C30 C13 124.2(4) . . ?
O7 C30 C13 113.8(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.1(4) . . . . ?
C7 C2 C3 C4 178.6(3) . . . . ?
C11 N2 C10 N1 179.4(3) . . . . ?
C11 N2 C10 S1 0.4(3) . . . . ?
C7 N1 C10 N2 -179.3(3) . . . . ?
C7 N1 C10 S1 -0.3(4) . . . . ?
C12 S1 C10 N2 -0.2(2) . . . . ?
C12 S1 C10 N1 -179.2(3) . . . . ?
C3 C2 C1 C6 -0.3(4) . . . . ?
C7 C2 C1 C6 -179.1(3) . . . . ?
C3 C2 C1 O1 179.4(3) . . . . ?
C7 C2 C1 O1 0.7(5) . . . . ?
C8 O1 C1 C2 60.3(4) . . . . ?
C8 O1 C1 C6 -119.9(3) . . . . ?
C10 N1 C7 O3 1.6(5) . . . . ?
C10 N1 C7 C2 -177.5(3) . . . . ?
C1 C2 C7 O3 38.9(4) . . . . ?
C3 C2 C7 O3 -139.8(3) . . . . ?
C1 C2 C7 N1 -142.0(3) . . . . ?
C3 C2 C7 N1 39.3(4) . . . . ?
C18 C13 C14 O8 171.9(4) . . . . ?
C30 C13 C14 O8 -8.6(5) . . . . ?
C18 C13 C14 C15 -0.3(4) . . . . ?
C30 C13 C14 C15 179.2(3) . . . . ?
C16 C17 C18 C13 1.1(4) . . . . ?
C14 C13 C18 C17 -0.6(4) . . . . ?
C30 C13 C18 C17 179.9(3) . . . . ?
O8 C14 C15 C16 -171.4(4) . . . . ?
C13 C14 C15 C16 0.7(5) . . . . ?
C14 C15 C16 N4 176.5(3) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C18 C17 C16 N4 -177.4(2) . . . . ?
C18 C17 C16 C15 -0.7(4) . . . . ?
O5 N3 C12 C11 179.9(3) . . . . ?
O4 N3 C12 C11 0.5(5) . . . . ?
O5 N3 C12 S1 1.8(4) . . . . ?
O4 N3 C12 S1 -177.6(2) . . . . ?
C10 S1 C12 C11 -0.1(2) . . . . ?
C10 S1 C12 N3 178.2(3) . . . . ?
C10 N2 C11 C12 -0.4(4) . . . . ?
N3 C12 C11 N2 -177.9(3) . . . . ?
S1 C12 C11 N2 0.3(3) . . . . ?
C6 C5 C4 C3 -0.3(5) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C1 O1 C8 O2 -0.5(5) . . . . ?
C1 O1 C8 C9 -179.7(3) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
O1 C1 C6 C5 -179.3(3) . . . . ?
C18 C13 C30 O6 176.1(3) . . . . ?
C14 C13 C30 O6 -3.4(5) . . . . ?
C18 C13 C30 O7 -1.8(4) . . . . ?
C14 C13 C30 O7 178.7(3) . . . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_CA2
_database_code_depnum_ccdc_archive 'CCDC 1450967'
_audit_update_record             
;
2016-01-31 deposited with the CCDC.
2016-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1
_chemical_name_systematic        
; 
 Acetic acid 2-(5-nitro-thiazol-2-carbamoyl)-phenyl ester-4-amino benzoic acid-4-amino salicylic acid
;
_chemical_name_common            
'Nitazoxanide-p-aminobenzoic acid-p-amino salicylic acid cocrystal alloy'
_chemical_melting_point          426
_chemical_formula_moiety         'C12 H9N3O5S, C7 H7NO2.25'
_chemical_formula_sum            'C19 H15.25 N4 O7.25 S'
_chemical_formula_weight         447.66

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                   7.377(2)
_cell_length_b                   11.371(5)
_cell_length_c                   13.888(5)
_cell_angle_alpha                108.933(13)
_cell_angle_beta                 97.742(13)
_cell_angle_gamma                108.643(19)
_cell_volume                     1006.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3011
_cell_measurement_theta_min      3.3310
_cell_measurement_theta_max      26.000

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             462
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CMOS detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9829
_diffrn_reflns_av_unetI/netI     0.2602
_diffrn_reflns_av_R_equivalents  0.2029
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.923
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.763
_diffrn_measured_fraction_theta_full 0.746
_diffrn_reflns_Laue_measured_fraction_max 0.763
_diffrn_reflns_Laue_measured_fraction_full 0.746
_diffrn_reflns_point_group_measured_fraction_max 0.763
_diffrn_reflns_point_group_measured_fraction_full 0.746
_reflns_number_total             3011
_reflns_number_gt                1202
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_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)+(0.0807P)²] 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         3011
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2263
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.1857
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   0.842
_refine_ls_restrained_S_all      0.842
_refine_ls_shift/su_max          0.017
_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
S1 S 0.2386(2) 0.84540(13) 0.14755(10) 0.0301(4) Uani 1 1 d . . . . .
O4 O 0.2210(7) 0.5831(4) 0.0116(3) 0.0418(11) Uani 1 1 d . . . . .
O2 O 0.6893(6) 1.2862(4) 0.3299(3) 0.0403(10) Uani 1 1 d . . . . .
O004 O 0.2734(6) 1.0945(3) 0.1729(3) 0.0365(10) Uani 1 1 d . . . . .
O1 O 0.5248(6) 1.3789(4) 0.2467(3) 0.0365(10) Uani 1 1 d . . . . .
N2 N 0.2368(7) 0.8525(4) 0.3357(3) 0.0296(11) Uani 1 1 d . . . . .
N3 N 0.2211(7) 0.5873(4) 0.1006(3) 0.0334(12) Uani 1 1 d . . . . .
C9 C 0.2726(8) 1.1358(5) 0.2659(4) 0.0279(13) Uani 1 1 d . . . . .
C7 C 0.6637(9) 1.3261(5) 0.2613(4) 0.0346(14) Uani 1 1 d . . . . .
N1 N 0.2616(7) 1.0542(4) 0.3212(3) 0.0291(11) Uani 1 1 d . . . . .
H1A H 0.2654 1.0876 0.3885 0.035 Uiso 1 1 calc R U . . .
C12 C 0.2222(8) 0.7071(5) 0.1758(4) 0.0267(13) Uani 1 1 d . . . . .
C13 C 0.7419(8) 0.9028(5) 0.3042(4) 0.0306(13) Uani 1 1 d . . . . .
C5 C 0.2881(9) 1.5246(6) 0.4382(4) 0.0356(15) Uani 1 1 d . . . . .
H5 H 0.2894 1.6109 0.4769 0.043 Uiso 1 1 calc R U . . .
C11 C 0.2210(8) 0.7268(5) 0.2780(4) 0.0308(14) Uani 1 1 d . . . . .
H11 H 0.2102 0.6593 0.3056 0.037 Uiso 1 1 calc R U . . .
C15 C 0.7336(9) 0.7292(5) 0.1454(4) 0.0304(13) Uani 1 1 d . . . . .
H15 H 0.7295 0.6411 0.1102 0.037 Uiso 1 1 calc R U . . .
C18 C 0.7471(8) 0.9853(5) 0.2462(4) 0.0311(14) Uani 1 1 d . . . . .
H18 H 0.7480 1.0728 0.2803 0.037 Uiso 1 1 calc R U . . .
O7 O 0.7544(7) 1.0712(4) 0.4559(3) 0.0443(11) Uani 1 1 d . . . . .
H017 H 0.7499 1.0899 0.5190 0.066 Uiso 1 1 calc R U . . .
O6 O 0.7233(7) 0.8722(4) 0.4637(3) 0.0445(11) Uani 1 1 d . . . . .
C2 C 0.2811(9) 1.2720(5) 0.3272(4) 0.0282(13) Uani 1 1 d . . . . .
O3 O 0.2183(7) 0.4944(4) 0.1305(3) 0.0491(12) Uani 1 1 d . . . . .
C10 C 0.2449(8) 0.9241(5) 0.2768(4) 0.0285(13) Uani 1 1 d . . . . .
C19 C 0.7380(9) 0.9446(5) 0.4128(4) 0.0331(14) Uani 1 1 d . . . . .
C1 C 0.4051(9) 1.3849(5) 0.3139(4) 0.0318(14) Uani 1 1 d . . . . .
C6 C 0.4065(9) 1.5120(6) 0.3695(4) 0.0377(15) Uani 1 1 d . . . . .
H6 H 0.4880 1.5890 0.3602 0.045 Uiso 1 1 calc R U . . .
C14 C 0.7326(9) 0.7713(5) 0.2484(4) 0.0329(14) Uani 1 1 d . . . . .
C16 C 0.7406(9) 0.8130(5) 0.0899(4) 0.0323(14) Uani 1 1 d . . . . .
N4 N 0.7470(8) 0.7724(5) -0.0120(3) 0.0432(14) Uani 1 1 d . . . . .
H4A H 0.6968 0.6837 -0.0414 0.052 Uiso 1 1 d R U . . .
H4B H 0.6766 0.8036 -0.0457 0.052 Uiso 1 1 d R U . . .
C17 C 0.7508(9) 0.9441(5) 0.1445(4) 0.0355(14) Uani 1 1 d . . . . .
H17 H 0.7605 1.0038 0.1092 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1688(9) 1.4134(5) 0.4507(4) 0.0328(14) Uani 1 1 d . . . . .
H4 H 0.0866 1.4229 0.4974 0.039 Uiso 1 1 calc R U . . .
C3 C 0.1676(8) 1.2882(5) 0.3960(4) 0.0298(14) Uani 1 1 d . . . . .
H3 H 0.0864 1.2121 0.4065 0.036 Uiso 1 1 calc R U . . .
C8 C 0.7788(11) 1.3306(8) 0.1832(5) 0.0576(19) Uani 1 1 d . . . . .
H8A H 0.8842 1.2985 0.1971 0.086 Uiso 1 1 calc R U . . .
H8B H 0.8380 1.4235 0.1883 0.086 Uiso 1 1 calc R U . . .
H8C H 0.6911 1.2726 0.1121 0.086 Uiso 1 1 calc R U . . .
O8 O 0.7590 0.7016 0.3054 0.031(4) Uani 0.2505 1 d . . P . .
H8 H 0.7833 0.7493 0.3697 0.046 Uiso 0.25 1 calc R U P . .


_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
S1 C12 1.712(5) . ?
S1 C10 1.713(5) . ?
O4 N3 1.222(6) . ?
O2 C7 1.199(7) . ?
O004 C9 1.224(6) . ?
O1 C7 1.366(7) . ?
O1 C1 1.370(7) . ?
N2 C10 1.322(7) . ?
N2 C11 1.350(6) . ?
N3 O3 1.250(6) . ?
N3 C12 1.418(7) . ?
C9 N1 1.374(7) . ?
C9 C2 1.482(7) . ?
C7 C8 1.468(9) . ?
N1 C10 1.362(6) . ?
C12 C11 1.365(7) . ?
C13 C14 1.416(7) . ?
C13 C18 1.418(8) . ?
C13 C19 1.435(8) . ?
C5 C4 1.369(8) . ?
C5 C6 1.381(8) . ?
C15 C14 1.355(8) . ?
C15 C16 1.401(8) . ?
C18 C17 1.343(8) . ?
O7 C19 1.325(6) . ?
O6 C19 1.237(7) . ?
C2 C3 1.360(8) . ?
C2 C1 1.402(8) . ?
C1 C6 1.396(8) . ?
C14 O8 1.326(6) . ?
C16 N4 1.351(7) . ?
C16 C17 1.407(7) . ?
C4 C3 1.376(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
C12 S1 C10 86.5(3) . . ?
C7 O1 C1 117.9(4) . . ?
C10 N2 C11 110.7(4) . . ?
O4 N3 O3 125.4(4) . . ?
O4 N3 C12 117.2(4) . . ?
O3 N3 C12 117.5(5) . . ?
O004 C9 N1 120.5(5) . . ?
O004 C9 C2 124.6(5) . . ?
N1 C9 C2 114.9(5) . . ?
O2 C7 O1 124.3(6) . . ?
O2 C7 C8 125.9(6) . . ?
O1 C7 C8 109.8(5) . . ?
C10 N1 C9 123.1(4) . . ?
C11 C12 N3 124.1(5) . . ?
C11 C12 S1 113.4(4) . . ?
N3 C12 S1 122.4(4) . . ?
C14 C13 C18 116.7(5) . . ?
C14 C13 C19 120.1(5) . . ?
C18 C13 C19 123.2(5) . . ?
C4 C5 C6 120.4(5) . . ?
N2 C11 C12 112.8(4) . . ?
C14 C15 C16 121.3(5) . . ?
C17 C18 C13 122.2(5) . . ?
C3 C2 C1 119.6(5) . . ?
C3 C2 C9 120.2(5) . . ?
C1 C2 C9 120.2(5) . . ?
N2 C10 N1 119.5(4) . . ?
N2 C10 S1 116.5(4) . . ?
N1 C10 S1 124.0(4) . . ?
O6 C19 O7 122.0(5) . . ?
O6 C19 C13 124.5(5) . . ?
O7 C19 C13 113.5(5) . . ?
O1 C1 C6 116.5(5) . . ?
O1 C1 C2 123.9(5) . . ?
C6 C1 C2 119.5(5) . . ?
C5 C6 C1 119.3(5) . . ?
O8 C14 C15 121.0(5) . . ?
O8 C14 C13 116.8(5) . . ?
C15 C14 C13 121.0(6) . . ?
N4 C16 C15 121.3(5) . . ?
N4 C16 C17 120.4(5) . . ?
C15 C16 C17 118.2(5) . . ?
C18 C17 C16 120.5(5) . . ?
C5 C4 C3 120.3(6) . . ?
C2 C3 C4 120.8(5) . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.084



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_NTZ-PABA
_database_code_depnum_ccdc_archive 'CCDC 1450968'
_audit_update_record             
;
2016-01-31 deposited with the CCDC.
2016-02-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_NTZ-PABA            
;
RESPONSE: The crystal quality was not good.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 Acetic acid 2-(5-nitro-thiazol-2-carbamoyl)-phenyl ester-4-amino benzoic acid
;
_chemical_name_common            'Nitazoxanide-p-aminobenzoic acid cocrystal'
_chemical_melting_point          431
_chemical_formula_moiety         'C12H9N3O5S, C7H7NO2'
_chemical_formula_sum            'C19 H16 N4 O7 S'
_chemical_formula_weight         444.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   7.4607(6)
_cell_length_b                   11.3799(12)
_cell_length_c                   13.9457(15)
_cell_angle_alpha                66.488(10)
_cell_angle_beta                 83.048(8)
_cell_angle_gamma                71.106(9)
_cell_volume                     1027.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1389
_cell_measurement_theta_min      4.4470
_cell_measurement_theta_max      71.2270

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    1.851
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89932
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3343
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.456
_diffrn_reflns_theta_max         63.691
_diffrn_reflns_theta_full        63.691
_diffrn_measured_fraction_theta_max 0.753
_diffrn_measured_fraction_theta_full 0.753
_diffrn_reflns_Laue_measured_fraction_max 0.753
_diffrn_reflns_Laue_measured_fraction_full 0.753
_diffrn_reflns_point_group_measured_fraction_max 0.753
_diffrn_reflns_point_group_measured_fraction_full 0.753
_reflns_number_total             2551
_reflns_number_gt                1938
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0649P)²] 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         2551
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
S1 S 0.39185(11) -0.15148(8) 0.84944(6) 0.0463(2) Uani 1 1 d . . . . .
O3 O 0.1791(3) 0.0967(2) 0.82476(18) 0.0564(6) Uani 1 1 d . . . . .
O1 O 0.1511(3) 0.3810(2) 0.75192(19) 0.0568(6) Uani 1 1 d . . . . .
O2 O 0.4012(3) 0.2852(3) 0.67130(19) 0.0629(7) Uani 1 1 d . . . . .
O4 O 0.7187(4) -0.5014(3) 0.8678(2) 0.0777(8) Uani 1 1 d . . . . .
O5 O 0.6371(4) -0.4127(3) 0.9844(2) 0.0751(8) Uani 1 1 d . . . . .
N3 N 0.6300(4) -0.4089(3) 0.8959(2) 0.0584(8) Uani 1 1 d . . . . .
N2 N 0.3807(4) -0.1446(3) 0.6625(2) 0.0472(7) Uani 1 1 d . . . . .
N1 N 0.2050(3) 0.0557(3) 0.6781(2) 0.0449(6) Uani 1 1 d . . . . .
H1A H 0.1734 0.0873 0.6133 0.054 Uiso 1 1 d R U . . .
C1 C 0.0220(4) 0.3875(3) 0.6833(2) 0.0459(8) Uani 1 1 d . . . . .
C2 C -0.0988(5) 0.5130(3) 0.6287(3) 0.0548(9) Uani 1 1 d . . . . .
H2 H -0.0897 0.5880 0.6371 0.066 Uiso 1 1 calc R U . . .
C3 C -0.2326(5) 0.5276(4) 0.5619(3) 0.0559(9) Uani 1 1 d . . . . .
H3 H -0.3149 0.6122 0.5254 0.067 Uiso 1 1 calc R U . . .
C4 C -0.2442(4) 0.4166(4) 0.5491(3) 0.0555(9) Uani 1 1 d . . . . .
H4 H -0.3344 0.4264 0.5036 0.067 Uiso 1 1 calc R U . . .
C5 C -0.1231(4) 0.2911(3) 0.6032(3) 0.0495(8) Uani 1 1 d . . . . .
H5 H -0.1316 0.2169 0.5933 0.059 Uiso 1 1 calc R U . . .
C6 C 0.0119(4) 0.2732(3) 0.6727(2) 0.0445(7) Uani 1 1 d . . . . .
C7 C 0.1377(4) 0.1372(3) 0.7335(3) 0.0461(8) Uani 1 1 d . . . . .
C8 C 0.3410(5) 0.3264(4) 0.7384(3) 0.0569(9) Uani 1 1 d . . . . .
C9 C 0.4551(6) 0.3261(6) 0.8183(4) 0.1055(18) Uani 1 1 d . . . . .
H9A H 0.4146 0.4135 0.8218 0.158 Uiso 1 1 calc R U . . .
H9B H 0.5865 0.3044 0.7998 0.158 Uiso 1 1 calc R U . . .
H9C H 0.4382 0.2604 0.8852 0.158 Uiso 1 1 calc R U . . .
C12 C 0.5145(4) -0.2909(3) 0.8209(3) 0.0460(8) Uani 1 1 d . . . . .
C11 C 0.4920(4) -0.2684(3) 0.7193(3) 0.0499(8) Uani 1 1 d . . . . .
H11 H 0.5488 -0.3332 0.6912 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3184(4) -0.0727(3) 0.7207(2) 0.0414(7) Uani 1 1 d . . . . .
O7 O 0.3099(4) -0.0658(2) 0.45370(19) 0.0672(7) Uani 1 1 d . . . . .
H7A H 0.3298 -0.0837 0.5152 0.101 Uiso 1 1 d R U . . .
O6 O 0.1507(3) 0.1338(2) 0.45990(19) 0.0638(7) Uani 1 1 d . . . . .
N4 N 0.0188(5) 0.2318(4) -0.0134(2) 0.0773(10) Uani 1 1 d . . . . .
H4A H 0.0626 0.1782 -0.0458 0.093 Uiso 1 1 d R U . . .
H4B H -0.0551 0.3115 -0.0454 0.093 Uiso 1 1 d R U . . .
C13 C 0.0662(5) 0.1906(4) 0.0880(3) 0.0524(8) Uani 1 1 d . . . . .
C14 C 0.1850(5) 0.0614(4) 0.1419(3) 0.0515(8) Uani 1 1 d . . . . .
H14 H 0.2335 0.0028 0.1074 0.062 Uiso 1 1 calc R U . . .
C15 C 0.2316(4) 0.0191(3) 0.2455(2) 0.0469(8) Uani 1 1 d . . . . .
H15 H 0.3136 -0.0667 0.2794 0.056 Uiso 1 1 calc R U . . .
C16 C 0.1573(4) 0.1034(3) 0.3004(2) 0.0445(7) Uani 1 1 d . . . . .
C17 C 0.0375(4) 0.2319(3) 0.2465(3) 0.0500(8) Uani 1 1 d . . . . .
H17A H -0.0135 0.2894 0.2818 0.060 Uiso 1 1 calc R U . . .
C18 C -0.0070(4) 0.2759(3) 0.1434(3) 0.0528(8) Uani 1 1 d . . . . .
H18 H -0.0862 0.3626 0.1095 0.063 Uiso 1 1 calc R U . . .
C19 C 0.2033(4) 0.0606(3) 0.4104(3) 0.0478(8) Uani 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
S1 C10 1.721(3) . ?
S1 C12 1.729(3) . ?
O3 C7 1.210(4) . ?
O1 C8 1.374(4) . ?
O1 C1 1.403(4) . ?
O2 C8 1.187(4) . ?
O4 N3 1.231(3) . ?
O5 N3 1.224(4) . ?
N3 C12 1.410(5) . ?
N2 C10 1.319(3) . ?
N2 C11 1.347(4) . ?
N1 C10 1.353(4) . ?
N1 C7 1.373(3) . ?
N1 H1A 0.8599 . ?
C1 C2 1.377(5) . ?
C1 C6 1.392(4) . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.483(5) . ?
C8 C9 1.481(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 C11 1.357(4) . ?
C11 H11 0.9300 . ?
O7 C19 1.323(4) . ?
O7 H7A 0.8195 . ?
O6 C19 1.227(3) . ?
N4 C13 1.352(4) . ?
N4 H4A 0.8593 . ?
N4 H4B 0.8592 . ?
C13 C14 1.396(5) . ?
C13 C18 1.411(4) . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(5) . ?
C16 C19 1.460(4) . ?
C17 C18 1.364(5) . ?
C17 H17A 0.9300 . ?
C18 H18 0.9300 . ?

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
C10 S1 C12 86.93(15) . . ?
C8 O1 C1 118.3(2) . . ?
O5 N3 O4 124.1(4) . . ?
O5 N3 C12 118.2(3) . . ?
O4 N3 C12 117.6(3) . . ?
C10 N2 C11 110.6(3) . . ?
C10 N1 C7 123.2(3) . . ?
C10 N1 H1A 118.2 . . ?
C7 N1 H1A 118.6 . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 O1 116.5(3) . . ?
C6 C1 O1 122.1(3) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 117.4(3) . . ?
C5 C6 C7 120.8(3) . . ?
C1 C6 C7 121.8(3) . . ?
O3 C7 N1 120.7(3) . . ?
O3 C7 C6 124.7(3) . . ?
N1 C7 C6 114.6(3) . . ?
O2 C8 O1 123.3(3) . . ?
O2 C8 C9 126.0(4) . . ?
O1 C8 C9 110.7(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C12 N3 126.2(3) . . ?
C11 C12 S1 111.9(3) . . ?
N3 C12 S1 121.8(2) . . ?
N2 C11 C12 114.5(3) . . ?
N2 C11 H11 122.8 . . ?
C12 C11 H11 122.8 . . ?
N2 C10 N1 120.0(3) . . ?
N2 C10 S1 116.1(2) . . ?
N1 C10 S1 123.9(2) . . ?
C19 O7 H7A 109.4 . . ?
C13 N4 H4A 119.9 . . ?
C13 N4 H4B 120.1 . . ?
H4A N4 H4B 120.0 . . ?
N4 C13 C14 121.2(3) . . ?
N4 C13 C18 120.9(3) . . ?
C14 C13 C18 117.9(3) . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 117.9(3) . . ?
C17 C16 C19 120.2(3) . . ?
C15 C16 C19 121.9(3) . . ?
C18 C17 C16 121.9(3) . . ?
C18 C17 H17A 119.1 . . ?
C16 C17 H17A 119.1 . . ?
C17 C18 C13 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
O6 C19 O7 121.7(3) . . ?
O6 C19 C16 124.1(3) . . ?
O7 C19 C16 114.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 O1 C1 C2 -123.0(3) . . . . ?
C8 O1 C1 C6 58.8(4) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
O1 C1 C2 C3 -178.4(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C1 -1.4(4) . . . . ?
C4 C5 C6 C7 178.0(3) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
O1 C1 C6 C5 179.3(2) . . . . ?
C2 C1 C6 C7 -178.2(3) . . . . ?
O1 C1 C6 C7 -0.1(4) . . . . ?
C10 N1 C7 O3 0.5(4) . . . . ?
C10 N1 C7 C6 -178.6(3) . . . . ?
C5 C6 C7 O3 -138.1(3) . . . . ?
C1 C6 C7 O3 41.2(4) . . . . ?
C5 C6 C7 N1 40.9(4) . . . . ?
C1 C6 C7 N1 -139.8(3) . . . . ?
C1 O1 C8 O2 0.4(5) . . . . ?
C1 O1 C8 C9 -179.2(4) . . . . ?
O5 N3 C12 C11 179.0(3) . . . . ?
O4 N3 C12 C11 -0.5(5) . . . . ?
O5 N3 C12 S1 2.5(4) . . . . ?
O4 N3 C12 S1 -177.0(2) . . . . ?
C10 S1 C12 C11 0.1(2) . . . . ?
C10 S1 C12 N3 177.0(3) . . . . ?
C10 N2 C11 C12 0.0(4) . . . . ?
N3 C12 C11 N2 -176.8(3) . . . . ?
S1 C12 C11 N2 -0.1(4) . . . . ?
C11 N2 C10 N1 179.4(3) . . . . ?
C11 N2 C10 S1 0.1(3) . . . . ?
C7 N1 C10 N2 -178.8(3) . . . . ?
C7 N1 C10 S1 0.5(4) . . . . ?
C12 S1 C10 N2 -0.1(2) . . . . ?
C12 S1 C10 N1 -179.4(3) . . . . ?
N4 C13 C14 C15 -179.3(3) . . . . ?
C18 C13 C14 C15 -1.0(5) . . . . ?
C13 C14 C15 C16 1.6(5) . . . . ?
C14 C15 C16 C17 -1.0(4) . . . . ?
C14 C15 C16 C19 179.5(3) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C19 C16 C17 C18 179.3(3) . . . . ?
C16 C17 C18 C13 0.8(5) . . . . ?
N4 C13 C18 C17 178.2(3) . . . . ?
C14 C13 C18 C17 -0.2(5) . . . . ?
C17 C16 C19 O6 -4.0(5) . . . . ?
C15 C16 C19 O6 175.4(3) . . . . ?
C17 C16 C19 O7 176.5(3) . . . . ?
C15 C16 C19 O7 -4.0(4) . . . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.055



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_NTZ-PASA
_database_code_depnum_ccdc_archive 'CCDC 1450969'
_audit_update_record             
;
2016-01-31 deposited with the CCDC.
2016-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 Acetic acid 2-(5-nitro-thiazol-2-carbamoyl)-phenyl ester-4-amino salicylic acid
;
_chemical_name_common            'Nitazoxanide-p-aminobenzoic acid cocrystal'
_chemical_melting_point          432
_chemical_formula_moiety         'C12 H9 N3 O5 S, C7 H7 N O3'
_chemical_formula_sum            'C19 H16 N4 O8 S'
_chemical_formula_weight         460.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   7.2396(4)
_cell_length_b                   11.6008(9)
_cell_length_c                   13.8909(12)
_cell_angle_alpha                109.021(7)
_cell_angle_beta                 97.558(6)
_cell_angle_gamma                104.385(6)
_cell_volume                     1039.19(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1823
_cell_measurement_theta_min      4.2330
_cell_measurement_theta_max      71.0250

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.889
_shelx_estimated_absorpt_T_min   0.550
_shelx_estimated_absorpt_T_max   0.805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94417
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3291
_diffrn_reflns_number            6589
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.460
_diffrn_reflns_theta_max         71.766
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3974
_reflns_number_gt                2950
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;

_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;

_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0714P)²] 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         3974
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.24324(9) 0.65746(6) 0.35275(4) 0.04685(18) Uani 1 1 d . . . . .
O1 O -0.0106(3) 0.14875(17) 0.26684(13) 0.0541(4) Uani 1 1 d . . . . .
O2 O -0.2055(3) 0.2130(2) 0.17078(15) 0.0678(6) Uani 1 1 d . . . . .
O4 O 0.2648(4) 0.9170(2) 0.48671(16) 0.0879(7) Uani 1 1 d . . . . .
O5 O 0.2814(4) 1.0018(2) 0.36993(18) 0.0869(7) Uani 1 1 d . . . . .
O3 O 0.2118(3) 0.41347(17) 0.32950(13) 0.0563(5) Uani 1 1 d . . . . .
N2 N 0.2577(3) 0.6482(2) 0.16521(15) 0.0471(5) Uani 1 1 d . . . . .
N1 N 0.2294(3) 0.45221(19) 0.18203(15) 0.0447(5) Uani 1 1 d . . . . .
H1A H 0.2207 0.4155 0.1156 0.054 Uiso 1 1 d R U . . .
C3 C 0.3296(4) 0.2185(3) 0.10355(19) 0.0486(6) Uani 1 1 d . . . . .
H3 H 0.4046 0.2870 0.0905 0.058 Uiso 1 1 calc R U . . .
C8 C -0.1695(4) 0.1857(3) 0.2449(2) 0.0571(7) Uani 1 1 d . . . . .
C10 C 0.2436(3) 0.5791(2) 0.22402(17) 0.0412(5) Uani 1 1 d . . . . .
C1 C 0.1069(3) 0.1359(2) 0.19455(18) 0.0450(5) Uani 1 1 d . . . . .
C7 C 0.2183(3) 0.3742(2) 0.23776(18) 0.0445(5) Uani 1 1 d . . . . .
C2 C 0.2173(3) 0.2412(2) 0.17751(18) 0.0442(5) Uani 1 1 d . . . . .
N3 N 0.2702(4) 0.9113(2) 0.39782(18) 0.0625(6) Uani 1 1 d . . . . .
C11 C 0.2709(4) 0.7705(2) 0.22179(19) 0.0517(6) Uani 1 1 d . . . . .
H11 H 0.2833 0.8340 0.1937 0.062 Uiso 1 1 calc R U . . .
C12 C 0.2644(4) 0.7922(2) 0.32236(19) 0.0493(6) Uani 1 1 d . . . . .
C5 C 0.2213(4) -0.0066(3) 0.0677(2) 0.0580(7) Uani 1 1 d . . . . .
H5 H 0.2228 -0.0892 0.0312 0.070 Uiso 1 1 calc R U . . .
C6 C 0.1092(4) 0.0139(2) 0.1405(2) 0.0536(6) Uani 1 1 d . . . . .
H6 H 0.0347 -0.0551 0.1533 0.064 Uiso 1 1 calc R U . . .
C4 C 0.3313(4) 0.0959(3) 0.0493(2) 0.0555(6) Uani 1 1 d . . . . .
H4 H 0.4070 0.0825 0.0000 0.067 Uiso 1 1 calc R U . . .
C9 C -0.2841(6) 0.1911(5) 0.3276(3) 0.1007(14) Uani 1 1 d . . . . .
H9A H -0.2014 0.2498 0.3944 0.151 Uiso 1 1 calc R U . . .
H9B H -0.3309 0.1073 0.3299 0.151 Uiso 1 1 calc R U . . .
H9C H -0.3936 0.2198 0.3116 0.151 Uiso 1 1 calc R U . . .
O6 O 0.7564(3) 0.61352(18) 0.03174(13) 0.0606(5) Uani 1 1 d . . . . .
O7 O 0.7440(3) 0.42414(18) 0.04212(14) 0.0630(5) Uani 1 1 d . . . . .
H7A H 0.7569 0.4104 -0.0208 0.095 Uiso 1 1 d R U . . .
O8 O 0.7514(3) 0.80013(18) 0.19549(15) 0.0641(5) Uani 1 1 d . . . . .
H8A H 0.7434 0.7640 0.1351 0.096 Uiso 1 1 d R U . . .
N4 N 0.7403(5) 0.7268(3) 0.51033(19) 0.0717(7) Uani 1 1 d . . . . .
C19 C 0.7483(4) 0.5446(2) 0.08386(19) 0.0481(6) Uani 1 1 d . . . . .
C13 C 0.7443(3) 0.5903(2) 0.19323(17) 0.0436(5) Uani 1 1 d . . . . .
C15 C 0.7505(4) 0.7636(3) 0.35099(19) 0.0514(6) Uani 1 1 d . . . . .
H15 H 0.7568 0.8486 0.3847 0.062 Uiso 1 1 calc R U . . .
C14 C 0.7484(4) 0.7182(2) 0.24592(19) 0.0464(5) Uani 1 1 d . . . . .
C17 C 0.7342(4) 0.5542(3) 0.35492(19) 0.0503(6) Uani 1 1 d . . . . .
H17 H 0.7269 0.4990 0.3910 0.060 Uiso 1 1 calc R U . . .
C18 C 0.7361(3) 0.5109(2) 0.25137(18) 0.0470(5) Uani 1 1 d . . . . .
H18 H 0.7319 0.4262 0.2182 0.056 Uiso 1 1 calc R U . . .
C16 C 0.7433(4) 0.6829(3) 0.40733(19) 0.0507(6) Uani 1 1 d . . . . .
H4A H 0.751(5) 0.678(3) 0.545(3) 0.083(11) Uiso 1 1 d . . . . .
H4B H 0.763(5) 0.814(4) 0.548(3) 0.091(12) 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
S2 C10 1.722(2) . ?
S2 C12 1.725(2) . ?
O1 C8 1.356(3) . ?
O1 C1 1.394(3) . ?
O2 C8 1.187(3) . ?
O4 N3 1.221(3) . ?
O5 N3 1.221(3) . ?
O3 C7 1.217(3) . ?
N2 C10 1.314(3) . ?
N2 C11 1.352(3) . ?
N1 C7 1.364(3) . ?
N1 C10 1.367(3) . ?
N1 H1A 0.8676 . ?
C3 C4 1.380(4) . ?
C3 C2 1.391(3) . ?
C3 H3 0.9300 . ?
C8 C9 1.498(4) . ?
C1 C6 1.375(4) . ?
C1 C2 1.393(3) . ?
C7 C2 1.494(3) . ?
N3 C12 1.423(3) . ?
C11 C12 1.346(3) . ?
C11 H11 0.9300 . ?
C5 C6 1.376(4) . ?
C5 C4 1.377(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C4 H4 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O6 C19 1.238(3) . ?
O7 C19 1.317(3) . ?
O7 H7A 0.8573 . ?
O8 C14 1.350(3) . ?
O8 H8A 0.7932 . ?
N4 C16 1.359(3) . ?
N4 H4A 0.87(4) . ?
N4 H4B 0.93(4) . ?
C19 C13 1.444(3) . ?
C13 C18 1.405(3) . ?
C13 C14 1.415(3) . ?
C15 C14 1.377(3) . ?
C15 C16 1.399(4) . ?
C15 H15 0.9300 . ?
C17 C18 1.364(3) . ?
C17 C16 1.411(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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
C10 S2 C12 86.32(11) . . ?
C8 O1 C1 117.11(19) . . ?
C10 N2 C11 110.5(2) . . ?
C7 N1 C10 123.9(2) . . ?
C7 N1 H1A 115.8 . . ?
C10 N1 H1A 120.2 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
O2 C8 O1 123.0(2) . . ?
O2 C8 C9 126.1(3) . . ?
O1 C8 C9 110.9(3) . . ?
N2 C10 N1 120.0(2) . . ?
N2 C10 S2 116.36(18) . . ?
N1 C10 S2 123.62(17) . . ?
C6 C1 C2 121.2(2) . . ?
C6 C1 O1 116.8(2) . . ?
C2 C1 O1 122.0(2) . . ?
O3 C7 N1 121.0(2) . . ?
O3 C7 C2 124.3(2) . . ?
N1 C7 C2 114.7(2) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 C7 121.0(2) . . ?
C1 C2 C7 121.3(2) . . ?
O5 N3 O4 124.0(2) . . ?
O5 N3 C12 118.0(2) . . ?
O4 N3 C12 118.0(2) . . ?
C12 C11 N2 113.9(2) . . ?
C12 C11 H11 123.0 . . ?
N2 C11 H11 123.0 . . ?
C11 C12 N3 125.3(2) . . ?
C11 C12 S2 112.88(19) . . ?
N3 C12 S2 121.78(19) . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C1 C6 C5 120.2(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C19 O7 H7A 107.1 . . ?
C14 O8 H8A 110.0 . . ?
C16 N4 H4A 118(2) . . ?
C16 N4 H4B 121(2) . . ?
H4A N4 H4B 118(3) . . ?
O6 C19 O7 121.4(2) . . ?
O6 C19 C13 122.7(2) . . ?
O7 C19 C13 115.9(2) . . ?
C18 C13 C14 117.4(2) . . ?
C18 C13 C19 121.9(2) . . ?
C14 C13 C19 120.6(2) . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
O8 C14 C15 117.6(2) . . ?
O8 C14 C13 121.4(2) . . ?
C15 C14 C13 121.0(2) . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 122.0(2) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
N4 C16 C15 120.5(3) . . ?
N4 C16 C17 120.5(3) . . ?
C15 C16 C17 119.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C8 O2 -3.7(4) . . . . ?
C1 O1 C8 C9 178.2(3) . . . . ?
C11 N2 C10 N1 -179.8(2) . . . . ?
C11 N2 C10 S2 0.5(3) . . . . ?
C7 N1 C10 N2 178.6(2) . . . . ?
C7 N1 C10 S2 -1.7(3) . . . . ?
C12 S2 C10 N2 -0.2(2) . . . . ?
C12 S2 C10 N1 -179.9(2) . . . . ?
C8 O1 C1 C6 -112.6(3) . . . . ?
C8 O1 C1 C2 67.5(3) . . . . ?
C10 N1 C7 O3 3.3(4) . . . . ?
C10 N1 C7 C2 -176.1(2) . . . . ?
C4 C3 C2 C1 -0.1(4) . . . . ?
C4 C3 C2 C7 178.9(2) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
O1 C1 C2 C3 -179.9(2) . . . . ?
C6 C1 C2 C7 -178.7(2) . . . . ?
O1 C1 C2 C7 1.2(3) . . . . ?
O3 C7 C2 C3 -142.5(3) . . . . ?
N1 C7 C2 C3 36.8(3) . . . . ?
O3 C7 C2 C1 36.4(4) . . . . ?
N1 C7 C2 C1 -144.3(2) . . . . ?
C10 N2 C11 C12 -0.7(3) . . . . ?
N2 C11 C12 N3 -178.3(2) . . . . ?
N2 C11 C12 S2 0.6(3) . . . . ?
O5 N3 C12 C11 0.2(4) . . . . ?
O4 N3 C12 C11 -179.4(3) . . . . ?
O5 N3 C12 S2 -178.6(2) . . . . ?
O4 N3 C12 S2 1.9(4) . . . . ?
C10 S2 C12 C11 -0.2(2) . . . . ?
C10 S2 C12 N3 178.7(2) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
O1 C1 C6 C5 179.9(2) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C6 C5 C4 C3 0.1(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
O6 C19 C13 C18 -179.7(2) . . . . ?
O7 C19 C13 C18 -0.1(4) . . . . ?
O6 C19 C13 C14 0.4(4) . . . . ?
O7 C19 C13 C14 -180.0(2) . . . . ?
C16 C15 C14 O8 178.6(2) . . . . ?
C16 C15 C14 C13 -1.8(4) . . . . ?
C18 C13 C14 O8 -178.4(2) . . . . ?
C19 C13 C14 O8 1.6(4) . . . . ?
C18 C13 C14 C15 2.0(4) . . . . ?
C19 C13 C14 C15 -178.0(2) . . . . ?
C16 C17 C18 C13 -0.9(4) . . . . ?
C14 C13 C18 C17 -0.7(4) . . . . ?
C19 C13 C18 C17 179.4(2) . . . . ?
C14 C15 C16 N4 -178.3(3) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C18 C17 C16 N4 179.6(3) . . . . ?
C18 C17 C16 C15 1.2(4) . . . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.071



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
_chemical_compound_source        synthetic
