# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_KB473_0m
_database_code_depnum_ccdc_archive 'CCDC 2352670'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Niclosamide dimethyl formamide solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H8 Cl2 N2 O4, C3 H7 N O'
_chemical_formula_sum            'C16 H15 Cl2 N3 O5'
_chemical_formula_weight         400.21

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'
Cl Cl 0.1484 0.1585 '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                   3.9865(6)
_cell_length_b                   37.612(5)
_cell_length_c                   11.9718(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.365(10)
_cell_angle_gamma                90
_cell_volume                     1787.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2822
_cell_measurement_theta_min      2.357
_cell_measurement_theta_max      23.945

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.396
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5251
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12098
_diffrn_reflns_av_unetI/netI     0.0976
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.759
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             3156
_reflns_number_gt                1870
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0361P)²+1.6492P] 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         3156
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.1648
_refine_ls_wR_factor_gt          0.1421
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Cl1 Cl 0.9053(4) 0.25028(4) 0.91714(12) 0.0958(6) Uani 1 1 d . . . . .
Cl2 Cl 0.1147(3) 0.43855(3) 0.52922(8) 0.0664(4) Uani 1 1 d . . . . .
O1 O 0.3444(8) 0.37454(8) 0.9120(2) 0.0698(10) Uani 1 1 d . . . . .
O2 O 0.5516(9) 0.36056(9) 0.5813(3) 0.0681(10) Uani 1 1 d . . . . .
H2O H 0.625(13) 0.3560(14) 0.522(4) 0.09(2) Uiso 1 1 d . . . . .
O3 O -0.4693(10) 0.53523(9) 0.8841(3) 0.0897(12) Uani 1 1 d . . . . .
O4 O -0.4721(11) 0.54444(10) 0.7078(3) 0.0967(13) Uani 1 1 d . . . . .
N1 N 0.2639(9) 0.39672(9) 0.7349(3) 0.0480(10) Uani 1 1 d . . . . .
H1N H 0.292(10) 0.3913(11) 0.669(4) 0.061(15) Uiso 1 1 d . . . . .
N2 N -0.4006(10) 0.52628(11) 0.7912(4) 0.0659(11) Uani 1 1 d . . . . .
C1 C 0.3790(10) 0.37150(11) 0.8123(3) 0.0488(11) Uani 1 1 d . . . . .
C2 C 0.5535(10) 0.33985(11) 0.7677(3) 0.0463(11) Uani 1 1 d . . . . .
C3 C 0.6371(11) 0.33492(12) 0.6583(3) 0.0501(11) Uani 1 1 d . . . . .
C4 C 0.7996(11) 0.30387(12) 0.6293(4) 0.0585(12) Uani 1 1 d . . . . .
H4 H 0.853195 0.300606 0.555999 0.070 Uiso 1 1 calc R U . . .
C5 C 0.8804(12) 0.27813(13) 0.7085(4) 0.0654(13) Uani 1 1 d . . . . .
H5 H 0.991820 0.257645 0.688982 0.079 Uiso 1 1 calc R U . . .
C6 C 0.7971(11) 0.28254(12) 0.8169(4) 0.0602(13) Uani 1 1 d . . . . .
C7 C 0.6379(11) 0.31310(12) 0.8467(4) 0.0565(12) Uani 1 1 d . . . . .
H7 H 0.585721 0.316026 0.920271 0.068 Uiso 1 1 calc R U . . .
C8 C 0.0963(10) 0.42827(11) 0.7528(3) 0.0456(10) Uani 1 1 d . . . . .
C9 C 0.0094(11) 0.43937(12) 0.8582(3) 0.0511(11) Uani 1 1 d . . . . .
H9 H 0.064140 0.425120 0.920711 0.061 Uiso 1 1 calc R U . . .
C10 C -0.1559(11) 0.47106(12) 0.8702(3) 0.0537(12) Uani 1 1 d . . . . .
H10 H -0.216960 0.477884 0.940200 0.064 Uiso 1 1 calc R U . . .
C11 C -0.2303(11) 0.49259(11) 0.7785(3) 0.0502(11) Uani 1 1 d . . . . .
C12 C -0.1507(11) 0.48244(11) 0.6728(3) 0.0522(11) Uani 1 1 d . . . . .
H12 H -0.206125 0.496886 0.610793 0.063 Uiso 1 1 calc R U . . .
C13 C 0.0106(11) 0.45085(11) 0.6617(3) 0.0455(11) Uani 1 1 d . . . . .
O5 O 0.7433(11) 0.34414(11) 0.3889(3) 0.0958(13) Uani 1 1 d . . . . .
N3 N 0.9172(10) 0.35682(11) 0.2212(3) 0.0633(11) Uani 1 1 d . . . . .
C14 C 0.8042(13) 0.36520(15) 0.3176(4) 0.0720(15) Uani 1 1 d . . . . .
H14 H 0.768696 0.389150 0.331798 0.086 Uiso 1 1 calc R U . . .
C15 C 0.9883(16) 0.32045(16) 0.1961(5) 0.104(2) Uani 1 1 d . . . . .
H15A H 0.848836 0.313149 0.130398 0.156 Uiso 1 1 calc R U . . .
H15B H 0.942687 0.305694 0.258342 0.156 Uiso 1 1 calc R U . . .
H15C H 1.221131 0.318158 0.182797 0.156 Uiso 1 1 calc R U . . .
C16 C 0.9742(14) 0.38421(16) 0.1397(4) 0.0952(19) Uani 1 1 d . . . . .
H16A H 1.200183 0.382331 0.118718 0.143 Uiso 1 1 calc R U . . .
H16B H 0.942626 0.407183 0.172015 0.143 Uiso 1 1 calc R U . . .
H16C H 0.817619 0.381227 0.074423 0.143 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
Cl1 C6 1.733(4) . ?
Cl2 C13 1.739(4) . ?
O1 C1 1.219(4) . ?
O2 C3 1.356(5) . ?
O2 H2O 0.81(5) . ?
O3 N2 1.217(4) . ?
O4 N2 1.222(5) . ?
N1 C1 1.375(5) . ?
N1 C8 1.388(5) . ?
N1 H1N 0.83(4) . ?
N2 C11 1.452(5) . ?
C1 C2 1.501(6) . ?
C2 C3 1.394(5) . ?
C2 C7 1.400(5) . ?
C3 C4 1.395(6) . ?
C4 C5 1.372(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(6) . ?
C7 H7 0.9300 . ?
C8 C13 1.399(5) . ?
C8 C9 1.403(5) . ?
C9 C10 1.376(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(5) . ?
C12 C13 1.363(5) . ?
C12 H12 0.9300 . ?
O5 C14 1.206(5) . ?
N3 C14 1.316(6) . ?
N3 C15 1.434(6) . ?
N3 C16 1.451(6) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C3 O2 H2O 111(4) . . ?
C1 N1 C8 128.4(4) . . ?
C1 N1 H1N 114(3) . . ?
C8 N1 H1N 118(3) . . ?
O3 N2 O4 122.5(4) . . ?
O3 N2 C11 119.0(4) . . ?
O4 N2 C11 118.6(4) . . ?
O1 C1 N1 122.3(4) . . ?
O1 C1 C2 121.4(4) . . ?
N1 C1 C2 116.4(4) . . ?
C3 C2 C7 118.4(4) . . ?
C3 C2 C1 126.8(4) . . ?
C7 C2 C1 114.8(4) . . ?
O2 C3 C2 118.5(4) . . ?
O2 C3 C4 121.3(4) . . ?
C2 C3 C4 120.2(4) . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.3(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 Cl1 119.8(4) . . ?
C5 C6 Cl1 120.1(4) . . ?
C6 C7 C2 120.8(4) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
N1 C8 C13 119.0(4) . . ?
N1 C8 C9 123.8(4) . . ?
C13 C8 C9 117.2(4) . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.8(4) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 121.1(4) . . ?
C10 C11 N2 119.9(4) . . ?
C12 C11 N2 119.0(4) . . ?
C13 C12 C11 118.6(4) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C8 122.4(4) . . ?
C12 C13 Cl2 118.4(3) . . ?
C8 C13 Cl2 119.2(3) . . ?
C14 N3 C15 120.2(5) . . ?
C14 N3 C16 120.5(5) . . ?
C15 N3 C16 119.3(4) . . ?
O5 C14 N3 124.9(5) . . ?
O5 C14 H14 117.6 . . ?
N3 C14 H14 117.6 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C8 N1 C1 O1 -0.3(7) . . . . ?
C8 N1 C1 C2 -179.9(4) . . . . ?
O1 C1 C2 C3 -173.4(4) . . . . ?
N1 C1 C2 C3 6.2(6) . . . . ?
O1 C1 C2 C7 6.4(6) . . . . ?
N1 C1 C2 C7 -174.0(4) . . . . ?
C7 C2 C3 O2 179.1(4) . . . . ?
C1 C2 C3 O2 -1.1(6) . . . . ?
C7 C2 C3 C4 0.3(6) . . . . ?
C1 C2 C3 C4 -179.9(4) . . . . ?
O2 C3 C4 C5 -179.3(4) . . . . ?
C2 C3 C4 C5 -0.5(7) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C4 C5 C6 C7 -1.2(7) . . . . ?
C4 C5 C6 Cl1 -179.0(3) . . . . ?
C5 C6 C7 C2 1.0(7) . . . . ?
Cl1 C6 C7 C2 178.8(3) . . . . ?
C3 C2 C7 C6 -0.5(6) . . . . ?
C1 C2 C7 C6 179.6(4) . . . . ?
C1 N1 C8 C13 177.9(4) . . . . ?
C1 N1 C8 C9 -1.3(7) . . . . ?
N1 C8 C9 C10 179.8(4) . . . . ?
C13 C8 C9 C10 0.5(6) . . . . ?
C8 C9 C10 C11 -1.5(6) . . . . ?
C9 C10 C11 C12 2.0(6) . . . . ?
C9 C10 C11 N2 -179.2(4) . . . . ?
O3 N2 C11 C10 1.4(6) . . . . ?
O4 N2 C11 C10 -178.0(4) . . . . ?
O3 N2 C11 C12 -179.7(4) . . . . ?
O4 N2 C11 C12 0.9(6) . . . . ?
C10 C11 C12 C13 -1.4(6) . . . . ?
N2 C11 C12 C13 179.7(4) . . . . ?
C11 C12 C13 C8 0.4(6) . . . . ?
C11 C12 C13 Cl2 -179.2(3) . . . . ?
N1 C8 C13 C12 -179.3(4) . . . . ?
C9 C8 C13 C12 0.0(6) . . . . ?
N1 C8 C13 Cl2 0.3(5) . . . . ?
C9 C8 C13 Cl2 179.6(3) . . . . ?
C15 N3 C14 O5 -2.2(8) . . . . ?
C16 N3 C14 O5 178.4(5) . . . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_KB480_0m
_database_code_depnum_ccdc_archive 'CCDC 2352672'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Niclosamide n,n-dimethyl acetamide solvate 1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H8 Cl2 N2 O4, C4 H9 N O'
_chemical_formula_sum            'C17 H17 Cl2 N3 O5'
_chemical_formula_weight         414.23

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'
Cl Cl 0.1484 0.1585 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.3963(4)
_cell_length_b                   20.4099(7)
_cell_length_c                   9.9364(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.1041(18)
_cell_angle_gamma                90
_cell_volume                     1876.84(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8073
_cell_measurement_theta_min      2.416
_cell_measurement_theta_max      27.156

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.380
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4848
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23012
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.416
_diffrn_reflns_theta_max         27.498
_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             4308
_reflns_number_gt                3010
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0504P)²+0.7797P] 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         4308
_refine_ls_number_parameters     255
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.053
_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
O1 O 0.43928(19) 0.59845(8) 0.44347(18) 0.0661(5) Uani 1 1 d . . . . .
N1 N 0.45196(19) 0.70945(8) 0.4616(2) 0.0427(4) Uani 1 1 d D . . . .
H1N H 0.495(2) 0.7402(10) 0.525(2) 0.051(7) Uiso 1 1 d D . . . .
Cl1 Cl 0.76629(10) 0.48843(3) 0.95632(8) 0.0927(3) Uani 1 1 d . . . . .
C1 C 0.4903(2) 0.64754(10) 0.5185(2) 0.0421(5) Uani 1 1 d . . . . .
Cl2 Cl 0.41627(7) 0.85285(3) 0.42004(6) 0.05488(19) Uani 1 1 d . . . . .
C2 C 0.5995(2) 0.64250(10) 0.6819(2) 0.0401(5) Uani 1 1 d . . . . .
O2 O 0.63480(19) 0.75689(8) 0.72661(19) 0.0582(5) Uani 1 1 d . . . . .
H2O H 0.679(3) 0.7838(14) 0.792(3) 0.075(9) Uiso 1 1 d . . . . .
N2 N 0.0530(2) 0.79387(10) -0.1192(2) 0.0511(5) Uani 1 1 d . . . . .
C3 C 0.6674(2) 0.69478(10) 0.7793(2) 0.0429(5) Uani 1 1 d . . . . .
O3 O -0.0153(2) 0.75348(9) -0.21599(19) 0.0706(5) Uani 1 1 d . . . . .
N3 N 0.8470(2) 0.93624(9) 1.0497(3) 0.0616(6) Uani 1 1 d . . . . .
C4 C 0.7667(2) 0.68289(12) 0.9292(2) 0.0524(6) Uani 1 1 d . . . . .
H4 H 0.812412 0.717903 0.993133 0.063 Uiso 1 1 calc R U . . .
O4 O 0.0423(2) 0.85257(8) -0.1419(2) 0.0751(6) Uani 1 1 d . . . . .
C5 C 0.7977(3) 0.62009(12) 0.9831(3) 0.0553(6) Uani 1 1 d . . . . .
H5 H 0.864033 0.612329 1.083247 0.066 Uiso 1 1 calc R U . . .
O5 O 0.7782(2) 0.83984(8) 0.9367(2) 0.0763(6) Uani 1 1 d . . . . .
C6 C 0.7292(3) 0.56830(11) 0.8870(3) 0.0536(6) Uani 1 1 d . . . . .
C7 C 0.6325(2) 0.57879(10) 0.7389(2) 0.0461(5) Uani 1 1 d . . . . .
H7 H 0.588421 0.543308 0.675861 0.055 Uiso 1 1 calc R U . . .
C8 C 0.3509(2) 0.72760(9) 0.3168(2) 0.0385(4) Uani 1 1 d . . . . .
C9 C 0.2706(2) 0.68297(10) 0.2022(2) 0.0467(5) Uani 1 1 d . . . . .
H9 H 0.283956 0.638275 0.221948 0.056 Uiso 1 1 calc R U . . .
C10 C 0.1719(2) 0.70407(10) 0.0603(2) 0.0473(5) Uani 1 1 d . . . . .
H10 H 0.118309 0.673937 -0.014592 0.057 Uiso 1 1 calc R U . . .
C11 C 0.1539(2) 0.77029(10) 0.0312(2) 0.0416(5) Uani 1 1 d . . . . .
C12 C 0.2309(2) 0.81593(10) 0.1410(2) 0.0423(5) Uani 1 1 d . . . . .
H12 H 0.218226 0.860507 0.119553 0.051 Uiso 1 1 calc R U . . .
C13 C 0.3264(2) 0.79447(10) 0.2821(2) 0.0401(5) Uani 1 1 d . . . . .
C14 C 0.7673(3) 0.90071(13) 0.9291(3) 0.0595(6) Uani 1 1 d . . . . .
C15 C 0.6640(4) 0.93330(17) 0.7849(4) 0.0926(10) Uani 1 1 d . . . . .
H15A H 0.710899 0.969771 0.764683 0.139 Uiso 1 1 calc R U . . .
H15B H 0.581230 0.948548 0.794551 0.139 Uiso 1 1 calc R U . . .
H15C H 0.633742 0.902454 0.703243 0.139 Uiso 1 1 calc R U . . .
C16 C 0.9482(3) 0.90395(14) 1.1875(3) 0.0705(7) Uani 1 1 d . . . . .
H16A H 0.953647 0.858258 1.167670 0.106 Uiso 1 1 calc R U . . .
H16B H 0.915890 0.908686 1.263362 0.106 Uiso 1 1 calc R U . . .
H16C H 1.041939 0.923512 1.222545 0.106 Uiso 1 1 calc R U . . .
C17 C 0.8388(5) 1.00712(13) 1.0555(5) 0.1028(12) Uani 1 1 d . . . . .
H17A H 0.914725 1.026385 1.039094 0.154 Uiso 1 1 calc R U . . .
H17B H 0.849211 1.020098 1.152782 0.154 Uiso 1 1 calc R U . . .
H17C H 0.746905 1.021736 0.978312 0.154 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
O1 C1 1.217(2) . ?
N1 C1 1.367(3) . ?
N1 C8 1.391(3) . ?
N1 H1N 0.858(16) . ?
Cl1 C6 1.743(2) . ?
C1 C2 1.502(3) . ?
Cl2 C13 1.733(2) . ?
C2 C3 1.397(3) . ?
C2 C7 1.397(3) . ?
O2 C3 1.354(3) . ?
O2 H2O 0.82(3) . ?
N2 O4 1.215(2) . ?
N2 O3 1.219(2) . ?
N2 C11 1.461(3) . ?
C3 C4 1.394(3) . ?
N3 C14 1.320(3) . ?
N3 C16 1.450(3) . ?
N3 C17 1.452(3) . ?
C4 C5 1.370(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
O5 C14 1.247(3) . ?
C6 C7 1.369(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(3) . ?
C8 C13 1.402(3) . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C14 C15 1.499(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C1 N1 C8 127.90(18) . . ?
C1 N1 H1N 114.6(16) . . ?
C8 N1 H1N 117.5(16) . . ?
O1 C1 N1 122.96(19) . . ?
O1 C1 C2 120.65(19) . . ?
N1 C1 C2 116.38(18) . . ?
C3 C2 C7 118.48(19) . . ?
C3 C2 C1 126.25(18) . . ?
C7 C2 C1 115.26(18) . . ?
C3 O2 H2O 112(2) . . ?
O4 N2 O3 123.3(2) . . ?
O4 N2 C11 118.51(19) . . ?
O3 N2 C11 118.22(18) . . ?
O2 C3 C4 120.61(19) . . ?
O2 C3 C2 119.26(18) . . ?
C4 C3 C2 120.13(19) . . ?
C14 N3 C16 119.5(2) . . ?
C14 N3 C17 124.0(3) . . ?
C16 N3 C17 116.5(3) . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 Cl1 119.54(18) . . ?
C5 C6 Cl1 119.30(18) . . ?
C6 C7 C2 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N1 C8 C9 123.91(18) . . ?
N1 C8 C13 118.72(18) . . ?
C9 C8 C13 117.37(18) . . ?
C10 C9 C8 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 121.47(19) . . ?
C10 C11 N2 120.24(19) . . ?
C12 C11 N2 118.29(18) . . ?
C13 C12 C11 118.86(19) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C8 121.93(18) . . ?
C12 C13 Cl2 117.90(16) . . ?
C8 C13 Cl2 120.17(16) . . ?
O5 C14 N3 119.4(2) . . ?
O5 C14 C15 120.4(3) . . ?
N3 C14 C15 120.2(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C8 N1 C1 O1 1.5(4) . . . . ?
C8 N1 C1 C2 -177.84(19) . . . . ?
O1 C1 C2 C3 179.1(2) . . . . ?
N1 C1 C2 C3 -1.5(3) . . . . ?
O1 C1 C2 C7 -1.9(3) . . . . ?
N1 C1 C2 C7 177.48(19) . . . . ?
C7 C2 C3 O2 -178.9(2) . . . . ?
C1 C2 C3 O2 0.1(3) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C4 179.8(2) . . . . ?
O2 C3 C4 C5 178.8(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C4 C5 C6 Cl1 -179.0(2) . . . . ?
C5 C6 C7 C2 -0.7(4) . . . . ?
Cl1 C6 C7 C2 178.95(18) . . . . ?
C3 C2 C7 C6 0.0(3) . . . . ?
C1 C2 C7 C6 -179.1(2) . . . . ?
C1 N1 C8 C9 -0.5(3) . . . . ?
C1 N1 C8 C13 179.1(2) . . . . ?
N1 C8 C9 C10 -179.9(2) . . . . ?
C13 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C9 C10 C11 N2 178.4(2) . . . . ?
O4 N2 C11 C10 -178.3(2) . . . . ?
O3 N2 C11 C10 1.0(3) . . . . ?
O4 N2 C11 C12 0.9(3) . . . . ?
O3 N2 C11 C12 -179.8(2) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
N2 C11 C12 C13 -179.66(19) . . . . ?
C11 C12 C13 C8 1.8(3) . . . . ?
C11 C12 C13 Cl2 -177.44(16) . . . . ?
N1 C8 C13 C12 178.52(19) . . . . ?
C9 C8 C13 C12 -1.8(3) . . . . ?
N1 C8 C13 Cl2 -2.3(3) . . . . ?
C9 C8 C13 Cl2 177.44(16) . . . . ?
C16 N3 C14 O5 1.5(4) . . . . ?
C17 N3 C14 O5 -177.3(3) . . . . ?
C16 N3 C14 C15 -179.0(3) . . . . ?
C17 N3 C14 C15 2.2(4) . . . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_KB490_0m
_database_code_depnum_ccdc_archive 'CCDC 2352671'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Niclosamide dimethyl sulfoxide solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H8 Cl2 N2 O4, C2 H6 O S'
_chemical_formula_sum            'C15 H14 Cl2 N2 O5 S'
_chemical_formula_weight         405.24

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'
Cl Cl 0.1484 0.1585 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   16.821(16)
_cell_length_b                   11.538(10)
_cell_length_c                   9.082(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.92(2)
_cell_angle_gamma                90
_cell_volume                     1753(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4942
_cell_measurement_theta_min      2.440
_cell_measurement_theta_max      24.974

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.518
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6456
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19293
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.435
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_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             4002
_reflns_number_gt                2255
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0497P)²+0.1095P] 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         4002
_refine_ls_number_parameters     275
_refine_ls_number_restraints     110
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.047
_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
Cl1 Cl 0.99271(4) 0.07040(6) 1.18310(7) 0.0716(2) Uani 1 1 d . . . . .
Cl2 Cl 0.64597(4) 0.47732(5) 0.59224(7) 0.0675(2) Uani 1 1 d . . . . .
O1 O 0.75781(10) 0.07556(13) 0.76367(18) 0.0660(5) Uani 1 1 d . . . . .
O2 O 0.80003(10) 0.42568(14) 0.85163(18) 0.0605(5) Uani 1 1 d . . . . .
H2O H 0.8080(16) 0.499(2) 0.890(3) 0.081(9) Uiso 1 1 d . . . . .
O3 O 0.44132(12) 0.11460(19) 0.2189(2) 0.0929(7) Uani 1 1 d . . . . .
O4 O 0.43745(12) 0.30020(19) 0.1948(2) 0.0845(6) Uani 1 1 d . . . . .
N1 N 0.71811(11) 0.26012(17) 0.70690(19) 0.0437(5) Uani 1 1 d . . . . .
H1N H 0.7254(13) 0.329(2) 0.733(2) 0.049(7) Uiso 1 1 d . . . . .
N2 N 0.46562(13) 0.2114(2) 0.2529(2) 0.0650(6) Uani 1 1 d . . . . .
C1 C 0.76553(13) 0.17973(19) 0.7841(2) 0.0445(5) Uani 1 1 d . . . . .
C2 C 0.82874(13) 0.22678(18) 0.8972(2) 0.0414(5) Uani 1 1 d . . . . .
C3 C 0.84496(14) 0.34369(18) 0.9273(2) 0.0459(6) Uani 1 1 d . . . . .
C4 C 0.90738(14) 0.3745(2) 1.0335(2) 0.0567(6) Uani 1 1 d . . . . .
H4 H 0.918520 0.452409 1.051882 0.068 Uiso 1 1 calc R U . . .
C5 C 0.95219(15) 0.2919(2) 1.1105(3) 0.0583(7) Uani 1 1 d . . . . .
H5 H 0.993421 0.313338 1.181376 0.070 Uiso 1 1 calc R U . . .
C6 C 0.93606(14) 0.1761(2) 1.0827(2) 0.0509(6) Uani 1 1 d . . . . .
C7 C 0.87570(13) 0.14383(19) 0.9770(2) 0.0477(6) Uani 1 1 d . . . . .
H7 H 0.865999 0.065564 0.958467 0.057 Uiso 1 1 calc R U . . .
C8 C 0.65608(13) 0.24280(18) 0.5955(2) 0.0427(5) Uani 1 1 d . . . . .
C9 C 0.62959(14) 0.1340(2) 0.5442(2) 0.0518(6) Uani 1 1 d . . . . .
H9 H 0.653924 0.067542 0.585604 0.062 Uiso 1 1 calc R U . . .
C10 C 0.56764(14) 0.1240(2) 0.4327(2) 0.0546(6) Uani 1 1 d . . . . .
H10 H 0.550348 0.051120 0.399355 0.066 Uiso 1 1 calc R U . . .
C11 C 0.53176(13) 0.2216(2) 0.3713(2) 0.0502(6) Uani 1 1 d . . . . .
C12 C 0.55558(14) 0.3313(2) 0.4177(2) 0.0495(6) Uani 1 1 d . . . . .
H12 H 0.530915 0.397110 0.375075 0.059 Uiso 1 1 calc R U . . .
C13 C 0.61729(14) 0.33987(18) 0.5297(2) 0.0461(6) Uani 1 1 d . . . . .
O5 O 0.8160(2) 0.6382(3) 0.9242(4) 0.0825(9) Uani 0.9240(17) 1 d . U P A 1
S1 S 0.81833(5) 0.69021(6) 1.08110(8) 0.0631(3) Uani 0.9240(17) 1 d . U P A 1
C14 C 0.7190(2) 0.7046(3) 1.1184(4) 0.0877(11) Uani 0.9240(17) 1 d . U P A 1
H14A H 0.688330 0.739552 1.035055 0.132 Uiso 0.9240(17) 1 calc R U P A 1
H14B H 0.716588 0.752594 1.204207 0.132 Uiso 0.9240(17) 1 calc R U P A 1
H14C H 0.697436 0.629481 1.136602 0.132 Uiso 0.9240(17) 1 calc R U P A 1
C15 C 0.8411(3) 0.8372(3) 1.0535(4) 0.0906(11) Uani 0.9240(17) 1 d . U P A 1
H15A H 0.893864 0.843353 1.022986 0.136 Uiso 0.9240(17) 1 calc R U P A 1
H15B H 0.838651 0.879051 1.144319 0.136 Uiso 0.9240(17) 1 calc R U P A 1
H15C H 0.803080 0.869210 0.978308 0.136 Uiso 0.9240(17) 1 calc R U P A 1
O5D O 0.836(3) 0.639(3) 0.962(6) 0.075(3) Uani 0.0760(17) 1 d D U P A 2
S1D S 0.7903(7) 0.7508(9) 0.9820(13) 0.085(2) Uani 0.0760(17) 1 d D U P A 2
C14D C 0.716(4) 0.743(4) 1.056(5) 0.080(3) Uani 0.0760(17) 1 d . U P A 2
H14D H 0.694268 0.666183 1.044801 0.121 Uiso 0.0760(17) 1 calc R U P A 2
H14E H 0.677257 0.797597 1.010860 0.121 Uiso 0.0760(17) 1 calc R U P A 2
H14F H 0.727098 0.760969 1.158961 0.121 Uiso 0.0760(17) 1 calc R U P A 2
C15D C 0.8752(19) 0.775(4) 1.098(4) 0.078(3) Uani 0.0760(17) 1 d D U P A 2
H15D H 0.866864 0.838634 1.161826 0.117 Uiso 0.0760(17) 1 calc R U P A 2
H15E H 0.918459 0.792173 1.040242 0.117 Uiso 0.0760(17) 1 calc R U P A 2
H15F H 0.887914 0.706464 1.155952 0.117 Uiso 0.0760(17) 1 calc R U P A 2


_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
Cl1 C6 1.745(2) . ?
Cl2 C13 1.736(2) . ?
O1 C1 1.221(3) . ?
O2 C3 1.353(3) . ?
O2 H2O 0.92(3) . ?
O3 N2 1.218(3) . ?
O4 N2 1.225(3) . ?
N1 C1 1.368(3) . ?
N1 C8 1.391(3) . ?
N1 H1N 0.84(2) . ?
N2 C11 1.470(3) . ?
C1 C2 1.502(3) . ?
C2 C7 1.395(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.396(3) . ?
C4 C5 1.363(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(3) . ?
C8 C13 1.399(3) . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
O5 S1 1.543(3) . ?
S1 C14 1.747(4) . ?
S1 C15 1.762(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O5D S1D 1.52(2) . ?
S1D C14D 1.49(6) . ?
S1D C15D 1.704(19) . ?
C14D H14D 0.9600 . ?
C14D H14E 0.9600 . ?
C14D H14F 0.9600 . ?
C15D H15D 0.9600 . ?
C15D H15E 0.9600 . ?
C15D H15F 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
C3 O2 H2O 113.7(16) . . ?
C1 N1 C8 128.99(19) . . ?
C1 N1 H1N 116.1(15) . . ?
C8 N1 H1N 114.8(15) . . ?
O3 N2 O4 123.6(2) . . ?
O3 N2 C11 117.9(2) . . ?
O4 N2 C11 118.5(2) . . ?
O1 C1 N1 122.8(2) . . ?
O1 C1 C2 121.09(19) . . ?
N1 C1 C2 116.08(19) . . ?
C7 C2 C3 118.15(19) . . ?
C7 C2 C1 115.49(19) . . ?
C3 C2 C1 126.35(19) . . ?
O2 C3 C4 120.9(2) . . ?
O2 C3 C2 119.21(19) . . ?
C4 C3 C2 119.9(2) . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 Cl1 120.00(19) . . ?
C5 C6 Cl1 119.59(18) . . ?
C6 C7 C2 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
N1 C8 C9 124.2(2) . . ?
N1 C8 C13 118.52(18) . . ?
C9 C8 C13 117.3(2) . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 121.9(2) . . ?
C10 C11 N2 120.0(2) . . ?
C12 C11 N2 118.1(2) . . ?
C13 C12 C11 117.6(2) . . ?
C13 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C12 C13 C8 122.7(2) . . ?
C12 C13 Cl2 117.96(18) . . ?
C8 C13 Cl2 119.35(16) . . ?
O5 S1 C14 106.4(2) . . ?
O5 S1 C15 103.2(2) . . ?
C14 S1 C15 99.34(18) . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14D S1D O5D 118(3) . . ?
C14D S1D C15D 115(3) . . ?
O5D S1D C15D 79(2) . . ?
S1D C14D H14D 109.5 . . ?
S1D C14D H14E 109.5 . . ?
H14D C14D H14E 109.5 . . ?
S1D C14D H14F 109.5 . . ?
H14D C14D H14F 109.5 . . ?
H14E C14D H14F 109.5 . . ?
S1D C15D H15D 109.5 . . ?
S1D C15D H15E 109.5 . . ?
H15D C15D H15E 109.5 . . ?
S1D C15D H15F 109.5 . . ?
H15D C15D H15F 109.5 . . ?
H15E C15D H15F 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
C8 N1 C1 O1 -0.8(4) . . . . ?
C8 N1 C1 C2 179.2(2) . . . . ?
O1 C1 C2 C7 -1.2(3) . . . . ?
N1 C1 C2 C7 178.85(19) . . . . ?
O1 C1 C2 C3 177.9(2) . . . . ?
N1 C1 C2 C3 -2.1(3) . . . . ?
C7 C2 C3 O2 -179.8(2) . . . . ?
C1 C2 C3 O2 1.2(3) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C4 -178.3(2) . . . . ?
O2 C3 C4 C5 179.5(2) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C4 C5 C6 Cl1 -179.20(19) . . . . ?
C5 C6 C7 C2 -0.9(4) . . . . ?
Cl1 C6 C7 C2 178.90(17) . . . . ?
C3 C2 C7 C6 0.2(3) . . . . ?
C1 C2 C7 C6 179.4(2) . . . . ?
C1 N1 C8 C9 1.7(4) . . . . ?
C1 N1 C8 C13 -178.3(2) . . . . ?
N1 C8 C9 C10 -179.8(2) . . . . ?
C13 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C9 C10 C11 N2 -179.8(2) . . . . ?
O3 N2 C11 C10 4.4(4) . . . . ?
O4 N2 C11 C10 -176.3(2) . . . . ?
O3 N2 C11 C12 -175.3(2) . . . . ?
O4 N2 C11 C12 4.0(3) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
N2 C11 C12 C13 179.5(2) . . . . ?
C11 C12 C13 C8 0.5(3) . . . . ?
C11 C12 C13 Cl2 -178.35(17) . . . . ?
N1 C8 C13 C12 179.5(2) . . . . ?
C9 C8 C13 C12 -0.5(3) . . . . ?
N1 C8 C13 Cl2 -1.7(3) . . . . ?
C9 C8 C13 Cl2 178.36(17) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_KB744_0m
_database_code_depnum_ccdc_archive 'CCDC 2352674'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Niclosamide dioxane solvate 1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H8 Cl2 N2 O4, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C15 H12 Cl2 N2 O5'
_chemical_formula_weight         371.17

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'
Cl Cl 0.1484 0.1585 '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                   7.5264(10)
_cell_length_b                   9.7054(12)
_cell_length_c                   11.9792(14)
_cell_angle_alpha                69.028(4)
_cell_angle_beta                 85.313(4)
_cell_angle_gamma                77.701(4)
_cell_volume                     798.31(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5252
_cell_measurement_theta_min      2.377
_cell_measurement_theta_max      24.628

_exptl_crystal_description       PLATE
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.435
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5845
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14740
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.292
_diffrn_reflns_theta_max         27.496
_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             3664
_reflns_number_gt                1987
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0462P)²+0.2373P] 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         3664
_refine_ls_number_parameters     244
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.010
_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
Cl1 Cl 0.81168(14) 0.66922(10) 0.84985(7) 0.1052(3) Uani 1 1 d . . . . .
Cl2 Cl 0.65394(10) 0.49849(7) 0.18568(6) 0.0733(2) Uani 1 1 d . . . . .
O1 O 0.5341(3) 0.8602(2) 0.42588(18) 0.0937(7) Uani 1 1 d . . . . .
O2 O 0.7775(3) 0.4161(2) 0.47810(15) 0.0668(5) Uani 1 1 d . . . . .
H2O H 0.833(4) 0.326(3) 0.499(2) 0.081(9) Uiso 1 1 d . . . . .
O3 O 0.1305(3) 1.0745(2) -0.11737(19) 0.0985(7) Uani 1 1 d . . . . .
O4 O 0.2113(4) 0.8649(3) -0.1462(2) 0.1461(12) Uani 1 1 d . . . . .
N1 N 0.6040(3) 0.6810(2) 0.34069(17) 0.0552(5) Uani 1 1 d . . . . .
H1N H 0.663(3) 0.583(3) 0.356(2) 0.075(8) Uiso 1 1 d . . . . .
N2 N 0.2123(3) 0.9444(3) -0.0888(2) 0.0825(7) Uani 1 1 d . . . . .
C1 C 0.6060(3) 0.7330(3) 0.4331(2) 0.0589(6) Uani 1 1 d . . . . .
C2 C 0.7048(3) 0.6256(2) 0.54306(19) 0.0519(6) Uani 1 1 d . . . . .
C3 C 0.7893(3) 0.4754(3) 0.5636(2) 0.0523(6) Uani 1 1 d . . . . .
C4 C 0.8821(3) 0.3894(3) 0.6691(2) 0.0602(6) Uani 1 1 d . . . . .
H4 H 0.939456 0.290396 0.680969 0.072 Uiso 1 1 calc R U . . .
C5 C 0.8901(4) 0.4493(3) 0.7563(2) 0.0639(7) Uani 1 1 d . . . . .
H5 H 0.952730 0.391716 0.826960 0.077 Uiso 1 1 calc R U . . .
C6 C 0.8040(4) 0.5954(3) 0.7375(2) 0.0644(7) Uani 1 1 d . . . . .
C7 C 0.7132(3) 0.6833(3) 0.6337(2) 0.0635(7) Uani 1 1 d . . . . .
H7 H 0.656749 0.782077 0.623352 0.076 Uiso 1 1 calc R U . . .
C8 C 0.5105(3) 0.7532(2) 0.2335(2) 0.0518(6) Uani 1 1 d . . . . .
C9 C 0.4039(3) 0.8980(3) 0.2010(2) 0.0633(7) Uani 1 1 d . . . . .
H9 H 0.398303 0.953550 0.250874 0.076 Uiso 1 1 calc R U . . .
C10 C 0.3069(3) 0.9597(3) 0.0961(2) 0.0674(7) Uani 1 1 d . . . . .
H10 H 0.235640 1.055944 0.075599 0.081 Uiso 1 1 calc R U . . .
C11 C 0.3158(3) 0.8791(3) 0.0224(2) 0.0619(7) Uani 1 1 d . . . . .
C12 C 0.4229(3) 0.7380(3) 0.0486(2) 0.0599(6) Uani 1 1 d . . . . .
H12 H 0.429685 0.685180 -0.003322 0.072 Uiso 1 1 calc R U . . .
C13 C 0.5198(3) 0.6766(3) 0.1532(2) 0.0530(6) Uani 1 1 d . . . . .
O5 O 0.9382(3) 0.14186(18) 0.50696(15) 0.0764(5) Uani 1 1 d . . . . .
C14 C 0.8648(11) 0.0965(8) 0.4230(6) 0.0872(19) Uani 0.862(11) 1 d . U P A 1
H14A H 0.824040 0.183448 0.352543 0.105 Uiso 0.862(11) 1 calc R U P A 1
H14B H 0.761170 0.050871 0.457932 0.105 Uiso 0.862(11) 1 calc R U P A 1
C15 C 1.0079(11) -0.0141(4) 0.3890(4) 0.0853(17) Uani 0.862(11) 1 d . U P A 1
H15A H 0.960595 -0.044105 0.330168 0.102 Uiso 0.862(11) 1 calc R U P A 1
H15B H 1.111769 0.031321 0.354265 0.102 Uiso 0.862(11) 1 calc R U P A 1
C14D C 0.911(7) 0.116(6) 0.393(4) 0.084(4) Uani 0.138(11) 1 d . U P A 2
H14C H 0.801755 0.181623 0.352722 0.100 Uiso 0.138(11) 1 calc R U P A 2
H14D H 1.014287 0.133518 0.339908 0.100 Uiso 0.138(11) 1 calc R U P A 2
C15D C 0.895(6) -0.034(3) 0.432(3) 0.087(4) Uani 0.138(11) 1 d . U P A 2
H15C H 0.869781 -0.057454 0.363342 0.104 Uiso 0.138(11) 1 calc R U P A 2
H15D H 0.792774 -0.047940 0.486427 0.104 Uiso 0.138(11) 1 calc R U P A 2


_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
Cl1 C6 1.746(2) . ?
Cl2 C13 1.731(2) . ?
O1 C1 1.213(3) . ?
O2 C3 1.359(3) . ?
O2 H2O 0.84(3) . ?
O3 N2 1.218(3) . ?
O4 N2 1.205(3) . ?
N1 C1 1.373(3) . ?
N1 C8 1.389(3) . ?
N1 H1N 0.92(3) . ?
N2 C11 1.463(3) . ?
C1 C2 1.491(3) . ?
C2 C7 1.400(3) . ?
C2 C3 1.401(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(3) . ?
C8 C13 1.401(3) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(3) . ?
C12 C13 1.374(3) . ?
C12 H12 0.9300 . ?
O5 C15 1.420(4) 2_756 ?
O5 C14 1.422(8) . ?
O5 C15D 1.50(3) 2_756 ?
O5 C14D 1.50(5) . ?
C14 C15 1.492(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14D C15D 1.39(7) . ?
C14D H14C 0.9700 . ?
C14D H14D 0.9700 . ?
C15D H15C 0.9700 . ?
C15D H15D 0.9700 . ?

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
C3 O2 H2O 110.9(19) . . ?
C1 N1 C8 127.9(2) . . ?
C1 N1 H1N 114.6(16) . . ?
C8 N1 H1N 117.2(16) . . ?
O4 N2 O3 123.8(3) . . ?
O4 N2 C11 117.6(3) . . ?
O3 N2 C11 118.6(3) . . ?
O1 C1 N1 122.3(2) . . ?
O1 C1 C2 121.2(2) . . ?
N1 C1 C2 116.5(2) . . ?
C7 C2 C3 117.7(2) . . ?
C7 C2 C1 115.6(2) . . ?
C3 C2 C1 126.7(2) . . ?
O2 C3 C4 120.9(2) . . ?
O2 C3 C2 118.5(2) . . ?
C4 C3 C2 120.6(2) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 Cl1 119.7(2) . . ?
C5 C6 Cl1 118.6(2) . . ?
C6 C7 C2 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N1 C8 C9 123.9(2) . . ?
N1 C8 C13 118.7(2) . . ?
C9 C8 C13 117.4(2) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 121.6(2) . . ?
C10 C11 N2 119.8(2) . . ?
C12 C11 N2 118.6(2) . . ?
C13 C12 C11 118.6(2) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C8 121.8(2) . . ?
C12 C13 Cl2 118.24(19) . . ?
C8 C13 Cl2 119.97(17) . . ?
C15 O5 C14 109.2(4) 2_756 . ?
C15 O5 C15D 38.8(17) 2_756 2_756 ?
C14 O5 C15D 113.1(9) . 2_756 ?
C15D O5 C14D 109(2) 2_756 . ?
O5 C14 C15 109.1(6) . . ?
O5 C14 H14A 109.9 . . ?
C15 C14 H14A 109.9 . . ?
O5 C14 H14B 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
O5 C15 C14 108.8(6) 2_756 . ?
O5 C15 H15A 109.9 2_756 . ?
C14 C15 H15A 109.9 . . ?
O5 C15 H15B 109.9 2_756 . ?
C14 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C15D C14D O5 104(3) . . ?
C15D C14D H14C 110.9 . . ?
O5 C14D H14C 110.9 . . ?
C15D C14D H14D 110.9 . . ?
O5 C14D H14D 110.9 . . ?
H14C C14D H14D 109.0 . . ?
C14D C15D H15C 108.8 . . ?
O5 C15D H15C 108.8 2_756 . ?
C14D C15D H15D 108.8 . . ?
O5 C15D H15D 108.8 2_756 . ?
H15C C15D H15D 107.7 . . ?

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 N1 C1 O1 -6.7(4) . . . . ?
C8 N1 C1 C2 174.4(2) . . . . ?
O1 C1 C2 C7 -2.1(4) . . . . ?
N1 C1 C2 C7 176.8(2) . . . . ?
O1 C1 C2 C3 178.3(2) . . . . ?
N1 C1 C2 C3 -2.8(4) . . . . ?
C7 C2 C3 O2 177.9(2) . . . . ?
C1 C2 C3 O2 -2.5(4) . . . . ?
C7 C2 C3 C4 -1.8(3) . . . . ?
C1 C2 C3 C4 177.8(2) . . . . ?
O2 C3 C4 C5 -178.6(2) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C4 C5 C6 Cl1 178.91(18) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
Cl1 C6 C7 C2 -179.59(18) . . . . ?
C3 C2 C7 C6 1.1(4) . . . . ?
C1 C2 C7 C6 -178.6(2) . . . . ?
C1 N1 C8 C9 2.0(4) . . . . ?
C1 N1 C8 C13 -176.8(2) . . . . ?
N1 C8 C9 C10 -176.5(2) . . . . ?
C13 C8 C9 C10 2.4(4) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 -1.5(4) . . . . ?
C9 C10 C11 N2 179.8(2) . . . . ?
O4 N2 C11 C10 -173.7(3) . . . . ?
O3 N2 C11 C10 5.3(4) . . . . ?
O4 N2 C11 C12 7.5(4) . . . . ?
O3 N2 C11 C12 -173.5(2) . . . . ?
C10 C11 C12 C13 1.4(4) . . . . ?
N2 C11 C12 C13 -179.9(2) . . . . ?
C11 C12 C13 C8 0.7(4) . . . . ?
C11 C12 C13 Cl2 179.82(18) . . . . ?
N1 C8 C13 C12 176.4(2) . . . . ?
C9 C8 C13 C12 -2.5(3) . . . . ?
N1 C8 C13 Cl2 -2.7(3) . . . . ?
C9 C8 C13 Cl2 178.36(18) . . . . ?
C15 O5 C14 C15 -61.3(10) 2_756 . . . ?
O5 C14 C15 O5 61.0(8) . . . 2_756 ?
C15D O5 C14D C15D 59(5) 2_756 . . . ?
O5 C14D C15D O5 -62(5) . . . 2_756 ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_KB750_0m
_database_code_depnum_ccdc_archive 'CCDC 2352675'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Niclosamide dioxane solvate 2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H8 Cl2 N2 O4), 1.5(C4 H8 O2)'
_chemical_formula_sum            'C32 H28 Cl4 N4 O11'
_chemical_formula_weight         786.38

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'
Cl Cl 0.1484 0.1585 '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                   11.4503(5)
_cell_length_b                   12.5985(5)
_cell_length_c                   14.5875(7)
_cell_angle_alpha                66.0849(14)
_cell_angle_beta                 87.5929(15)
_cell_angle_gamma                64.4525(12)
_cell_volume                     1712.94(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.321
_cell_measurement_theta_max      27.589

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.413
_shelx_estimated_absorpt_T_min   0.866
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6463
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31623
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.081
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             7828
_reflns_number_gt                4583
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0713P)²+0.5855P] 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         7828
_refine_ls_number_parameters     541
_refine_ls_number_restraints     210
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1671
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.031
_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
C1A C 0.4081(2) 0.1489(2) -0.14884(17) 0.0462(5) Uani 1 1 d . . . . .
Cl1A Cl -0.0898(4) 0.3585(10) -0.1483(5) 0.0909(13) Uani 0.73(2) 1 d . U P A 1
Cl1D Cl -0.0779(12) 0.304(2) -0.1281(11) 0.080(2) Uani 0.27(2) 1 d . U P A 2
N1A N 0.53290(19) 0.11988(19) -0.11507(16) 0.0467(5) Uani 1 1 d . . . . .
H1AN H 0.544(2) 0.134(2) -0.0661(18) 0.046(7) Uiso 1 1 d . . . . .
O1A O 0.38183(17) 0.1294(2) -0.21838(14) 0.0668(5) Uani 1 1 d . . . . .
C2A C 0.3023(2) 0.2095(2) -0.09515(16) 0.0419(5) Uani 1 1 d . . . . .
Cl2A Cl 0.76608(6) 0.08633(7) -0.00630(6) 0.0704(2) Uani 1 1 d . . . . .
N2A N 1.0090(3) -0.1048(2) -0.2469(2) 0.0739(7) Uani 1 1 d . . . . .
O2A O 0.44191(17) 0.1935(2) 0.03024(16) 0.0658(6) Uani 1 1 d . . . . .
H2AO H 0.445(3) 0.196(3) 0.083(2) 0.074(10) Uiso 1 1 d . . . . .
C3A C 0.3187(2) 0.2324(2) -0.01204(18) 0.0455(5) Uani 1 1 d . . . . .
O3A O 1.0079(2) -0.1214(2) -0.32316(18) 0.0894(7) Uani 1 1 d . . . . .
C4A C 0.2102(2) 0.2919(2) 0.02779(18) 0.0523(6) Uani 1 1 d . . . . .
H4A H 0.222090 0.307764 0.082772 0.063 Uiso 1 1 calc R U . . .
O4A O 1.1089(2) -0.1348(3) -0.1958(2) 0.1211(10) Uani 1 1 d . . . . .
C5A C 0.0861(2) 0.3274(2) -0.01264(19) 0.0553(6) Uani 1 1 d . . . . .
H5A H 0.014023 0.367628 0.014217 0.066 Uiso 1 1 calc R U . . .
C6A C 0.0697(2) 0.3028(3) -0.0932(2) 0.0581(7) Uani 1 1 d . . . . .
C7A C 0.1755(2) 0.2456(2) -0.13438(18) 0.0535(6) Uani 1 1 d . . . . .
H7A H 0.161962 0.230751 -0.189568 0.064 Uiso 1 1 calc R U . . .
C8A C 0.6482(2) 0.0648(2) -0.15093(17) 0.0438(5) Uani 1 1 d . . . . .
C9A C 0.6534(2) 0.0280(2) -0.23003(18) 0.0519(6) Uani 1 1 d . . . . .
H9A H 0.576723 0.040717 -0.261885 0.062 Uiso 1 1 calc R U . . .
C10A C 0.7713(3) -0.0272(2) -0.26136(19) 0.0572(6) Uani 1 1 d . . . . .
H10A H 0.773885 -0.050728 -0.314416 0.069 Uiso 1 1 calc R U . . .
C11A C 0.8840(2) -0.0468(2) -0.2139(2) 0.0546(6) Uani 1 1 d . . . . .
C12A C 0.8835(2) -0.0120(2) -0.1358(2) 0.0565(6) Uani 1 1 d . . . . .
H12A H 0.960962 -0.025780 -0.104318 0.068 Uiso 1 1 calc R U . . .
C13A C 0.7658(2) 0.0435(2) -0.10513(18) 0.0491(6) Uani 1 1 d . . . . .
C14A C 0.6118(6) 0.1330(5) 0.2496(5) 0.0795(16) Uani 0.825(5) 1 d . U P B 1
H14A H 0.633721 0.204175 0.233456 0.095 Uiso 0.825(5) 1 calc R U P B 1
H14B H 0.665427 0.079138 0.216940 0.095 Uiso 0.825(5) 1 calc R U P B 1
C15A C 0.6368(4) 0.0527(5) 0.3638(4) 0.0909(14) Uani 0.825(5) 1 d . U P B 1
H15A H 0.615888 -0.018928 0.378908 0.109 Uiso 0.825(5) 1 calc R U P B 1
H15B H 0.728994 0.016194 0.389581 0.109 Uiso 0.825(5) 1 calc R U P B 1
C16A C 0.4242(3) 0.1882(6) 0.3727(3) 0.0886(13) Uani 0.825(5) 1 d . U P B 1
H16A H 0.372219 0.241633 0.406166 0.106 Uiso 0.825(5) 1 calc R U P B 1
H16B H 0.397368 0.120816 0.385855 0.106 Uiso 0.825(5) 1 calc R U P B 1
C17A C 0.4004(4) 0.2714(5) 0.2596(4) 0.0864(14) Uani 0.825(5) 1 d . U P B 1
H17A H 0.307814 0.313947 0.232413 0.104 Uiso 0.825(5) 1 calc R U P B 1
H17B H 0.429284 0.337693 0.245221 0.104 Uiso 0.825(5) 1 calc R U P B 1
O5A O 0.4766(5) 0.1824(4) 0.2147(4) 0.0741(12) Uani 0.825(5) 1 d . U P B 1
O6A O 0.5601(3) 0.1297(4) 0.4128(3) 0.0909(11) Uani 0.825(5) 1 d . U P B 1
C14D C 0.610(4) 0.091(3) 0.267(3) 0.086(3) Uani 0.175(5) 1 d . U P B 2
H14E H 0.591150 0.023002 0.316282 0.104 Uiso 0.175(5) 1 calc R U P B 2
H14F H 0.674191 0.055663 0.228020 0.104 Uiso 0.175(5) 1 calc R U P B 2
C15D C 0.6463(17) 0.155(3) 0.3106(18) 0.090(3) Uani 0.175(5) 1 d . U P B 2
H15E H 0.727733 0.092987 0.357434 0.108 Uiso 0.175(5) 1 calc R U P B 2
H15F H 0.663645 0.221161 0.256982 0.108 Uiso 0.175(5) 1 calc R U P B 2
C16D C 0.4236(18) 0.283(3) 0.321(2) 0.086(3) Uani 0.175(5) 1 d . U P B 2
H16E H 0.404051 0.367552 0.265586 0.104 Uiso 0.175(5) 1 calc R U P B 2
H16F H 0.371704 0.296711 0.372772 0.104 Uiso 0.175(5) 1 calc R U P B 2
C17D C 0.395(2) 0.204(3) 0.2832(19) 0.086(3) Uani 0.175(5) 1 d . U P B 2
H17E H 0.301719 0.239158 0.260372 0.104 Uiso 0.175(5) 1 calc R U P B 2
H17F H 0.429655 0.113364 0.332072 0.104 Uiso 0.175(5) 1 calc R U P B 2
O6D O 0.5582(13) 0.2136(19) 0.3608(13) 0.084(3) Uani 0.175(5) 1 d . U P B 2
O5D O 0.474(3) 0.225(2) 0.193(2) 0.084(3) Uani 0.175(5) 1 d . U P B 2
C1B C 0.5884(2) 0.3656(2) 0.65437(18) 0.0508(6) Uani 1 1 d . . . . .
N1B N 0.46771(18) 0.38477(19) 0.62235(16) 0.0481(5) Uani 1 1 d . . . . .
H1BN H 0.465(3) 0.358(3) 0.576(2) 0.070(8) Uiso 1 1 d . . . . .
O1B O 0.60772(18) 0.3977(2) 0.71834(16) 0.0792(6) Uani 1 1 d . . . . .
Cl1B Cl 1.08145(7) 0.20419(10) 0.64584(8) 0.0935(3) Uani 1 1 d . . . . .
C2B C 0.6999(2) 0.3005(2) 0.60750(17) 0.0446(5) Uani 1 1 d . . . . .
N2B N -0.0253(2) 0.6289(2) 0.7227(2) 0.0697(7) Uani 1 1 d . . . . .
O2B O 0.57480(18) 0.2730(2) 0.50116(17) 0.0781(7) Uani 1 1 d . . . . .
H2BO H 0.580(3) 0.229(3) 0.473(3) 0.086(11) Uiso 1 1 d . . . . .
Cl2B Cl 0.24778(6) 0.39735(7) 0.51497(5) 0.0651(2) Uani 1 1 d . . . . .
C3B C 0.6924(2) 0.2567(2) 0.53513(18) 0.0500(6) Uani 1 1 d . . . . .
O3B O -0.0336(2) 0.6439(2) 0.80059(16) 0.0787(6) Uani 1 1 d . . . . .
C4B C 0.8043(2) 0.1979(2) 0.49778(19) 0.0549(6) Uani 1 1 d . . . . .
H4B H 0.798140 0.169795 0.449099 0.066 Uiso 1 1 calc R U . . .
O4B O -0.1203(2) 0.6699(3) 0.6609(2) 0.1242(11) Uani 1 1 d . . . . .
C5B C 0.9230(2) 0.1812(2) 0.53180(19) 0.0551(6) Uani 1 1 d . . . . .
H5B H 0.997504 0.142083 0.506502 0.066 Uiso 1 1 calc R U . . .
O5B O 0.4373(3) 0.5460(3) 0.90246(19) 0.1092(8) Uani 1 1 d . . . . .
C6B C 0.9311(2) 0.2229(2) 0.6040(2) 0.0541(6) Uani 1 1 d . . . . .
C7B C 0.8217(2) 0.2821(2) 0.64143(18) 0.0517(6) Uani 1 1 d . . . . .
H7B H 0.829340 0.310118 0.689869 0.062 Uiso 1 1 calc R U . . .
C8B C 0.3484(2) 0.4433(2) 0.65207(17) 0.0442(5) Uani 1 1 d . . . . .
C9B C 0.3344(2) 0.4908(2) 0.72529(18) 0.0511(6) Uani 1 1 d . . . . .
H9B H 0.407745 0.482746 0.757981 0.061 Uiso 1 1 calc R U . . .
C10B C 0.2124(2) 0.5496(2) 0.74962(18) 0.0531(6) Uani 1 1 d . . . . .
H10B H 0.203533 0.580248 0.799051 0.064 Uiso 1 1 calc R U . . .
C11B C 0.1045(2) 0.5625(2) 0.70031(18) 0.0513(6) Uani 1 1 d . . . . .
C12B C 0.1140(2) 0.5164(2) 0.62787(19) 0.0519(6) Uani 1 1 d . . . . .
H12B H 0.039787 0.525811 0.595173 0.062 Uiso 1 1 calc R U . . .
C13B C 0.2358(2) 0.4563(2) 0.60530(17) 0.0469(5) Uani 1 1 d . . . . .
C14B C 0.5620(3) 0.4345(4) 0.9423(3) 0.0977(11) Uani 1 1 d . . . . .
H14C H 0.612191 0.430298 0.887516 0.117 Uiso 1 1 calc R U . . .
H14D H 0.549916 0.356430 0.972069 0.117 Uiso 1 1 calc R U . . .
C15B C 0.3658(3) 0.5608(4) 0.9812(3) 0.1023(12) Uani 1 1 d . . . . .
H15C H 0.344598 0.488569 1.013040 0.123 Uiso 1 1 calc R U . . .
H15D H 0.284015 0.640460 0.952487 0.123 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
C1A O1A 1.213(3) . ?
C1A N1A 1.371(3) . ?
C1A C2A 1.507(3) . ?
Cl1A C6A 1.743(4) . ?
Cl1D C6A 1.782(10) . ?
N1A C8A 1.394(3) . ?
N1A H1AN 0.83(2) . ?
C2A C7A 1.391(3) . ?
C2A C3A 1.392(3) . ?
Cl2A C13A 1.733(2) . ?
N2A O3A 1.213(3) . ?
N2A O4A 1.215(3) . ?
N2A C11A 1.463(3) . ?
O2A C3A 1.357(3) . ?
O2A H2AO 0.78(3) . ?
C3A C4A 1.390(3) . ?
C4A C5A 1.369(3) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.369(3) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.373(3) . ?
C7A H7A 0.9300 . ?
C8A C13A 1.396(3) . ?
C8A C9A 1.398(3) . ?
C9A C10A 1.382(3) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.366(4) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.377(4) . ?
C12A C13A 1.377(3) . ?
C12A H12A 0.9300 . ?
C14A O5A 1.422(9) . ?
C14A C15A 1.519(9) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C15A O6A 1.413(4) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C16A O6A 1.430(4) . ?
C16A C17A 1.512(8) . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
C17A O5A 1.467(7) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C14D C15D 1.41(4) . ?
C14D O5D 1.69(5) . ?
C14D H14E 0.9700 . ?
C14D H14F 0.9700 . ?
C15D O6D 1.35(2) . ?
C15D H15E 0.9700 . ?
C15D H15F 0.9700 . ?
C16D O6D 1.41(2) . ?
C16D C17D 1.47(3) . ?
C16D H16E 0.9700 . ?
C16D H16F 0.9700 . ?
C17D O5D 1.57(4) . ?
C17D H17E 0.9700 . ?
C17D H17F 0.9700 . ?
C1B O1B 1.218(3) . ?
C1B N1B 1.364(3) . ?
C1B C2B 1.500(3) . ?
N1B C8B 1.392(3) . ?
N1B H1BN 0.88(3) . ?
Cl1B C6B 1.736(3) . ?
C2B C7B 1.390(3) . ?
C2B C3B 1.396(3) . ?
N2B O4B 1.217(3) . ?
N2B O3B 1.219(3) . ?
N2B C11B 1.457(3) . ?
O2B C3B 1.355(3) . ?
O2B H2BO 0.79(3) . ?
Cl2B C13B 1.731(2) . ?
C3B C4B 1.392(3) . ?
C4B C5B 1.365(3) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.376(3) . ?
C5B H5B 0.9300 . ?
O5B C15B 1.410(4) . ?
O5B C14B 1.424(4) . ?
C6B C7B 1.375(3) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.395(3) . ?
C8B C13B 1.399(3) . ?
C9B C10B 1.380(3) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.370(3) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.378(3) . ?
C12B C13B 1.371(3) . ?
C12B H12B 0.9300 . ?
C14B C15B 1.452(5) 2_667 ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?

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
O1A C1A N1A 123.1(2) . . ?
O1A C1A C2A 120.9(2) . . ?
N1A C1A C2A 115.97(19) . . ?
C1A N1A C8A 128.2(2) . . ?
C1A N1A H1AN 118.0(17) . . ?
C8A N1A H1AN 113.8(17) . . ?
C7A C2A C3A 117.7(2) . . ?
C7A C2A C1A 115.19(19) . . ?
C3A C2A C1A 127.1(2) . . ?
O3A N2A O4A 123.5(3) . . ?
O3A N2A C11A 118.5(3) . . ?
O4A N2A C11A 118.0(3) . . ?
C3A O2A H2AO 113(2) . . ?
O2A C3A C4A 120.9(2) . . ?
O2A C3A C2A 118.98(19) . . ?
C4A C3A C2A 120.1(2) . . ?
C5A C4A C3A 121.0(2) . . ?
C5A C4A H4A 119.5 . . ?
C3A C4A H4A 119.5 . . ?
C6A C5A C4A 119.0(2) . . ?
C6A C5A H5A 120.5 . . ?
C4A C5A H5A 120.5 . . ?
C5A C6A C7A 120.8(2) . . ?
C5A C6A Cl1A 118.1(2) . . ?
C7A C6A Cl1A 120.9(2) . . ?
C5A C6A Cl1D 121.8(4) . . ?
C7A C6A Cl1D 115.5(5) . . ?
C6A C7A C2A 121.2(2) . . ?
C6A C7A H7A 119.4 . . ?
C2A C7A H7A 119.4 . . ?
N1A C8A C13A 118.7(2) . . ?
N1A C8A C9A 123.6(2) . . ?
C13A C8A C9A 117.7(2) . . ?
C10A C9A C8A 120.7(2) . . ?
C10A C9A H9A 119.7 . . ?
C8A C9A H9A 119.7 . . ?
C11A C10A C9A 119.6(2) . . ?
C11A C10A H10A 120.2 . . ?
C9A C10A H10A 120.2 . . ?
C10A C11A C12A 121.7(2) . . ?
C10A C11A N2A 119.9(2) . . ?
C12A C11A N2A 118.4(3) . . ?
C11A C12A C13A 118.6(2) . . ?
C11A C12A H12A 120.7 . . ?
C13A C12A H12A 120.7 . . ?
C12A C13A C8A 121.8(2) . . ?
C12A C13A Cl2A 118.3(2) . . ?
C8A C13A Cl2A 119.93(17) . . ?
O5A C14A C15A 107.6(5) . . ?
O5A C14A H14A 110.2 . . ?
C15A C14A H14A 110.2 . . ?
O5A C14A H14B 110.2 . . ?
C15A C14A H14B 110.2 . . ?
H14A C14A H14B 108.5 . . ?
O6A C15A C14A 111.0(4) . . ?
O6A C15A H15A 109.4 . . ?
C14A C15A H15A 109.4 . . ?
O6A C15A H15B 109.4 . . ?
C14A C15A H15B 109.4 . . ?
H15A C15A H15B 108.0 . . ?
O6A C16A C17A 110.1(4) . . ?
O6A C16A H16A 109.6 . . ?
C17A C16A H16A 109.6 . . ?
O6A C16A H16B 109.6 . . ?
C17A C16A H16B 109.6 . . ?
H16A C16A H16B 108.1 . . ?
O5A C17A C16A 106.0(5) . . ?
O5A C17A H17A 110.5 . . ?
C16A C17A H17A 110.5 . . ?
O5A C17A H17B 110.5 . . ?
C16A C17A H17B 110.5 . . ?
H17A C17A H17B 108.7 . . ?
C14A O5A C17A 108.0(5) . . ?
C15A O6A C16A 110.1(3) . . ?
C15D C14D O5D 94(2) . . ?
C15D C14D H14E 112.9 . . ?
O5D C14D H14E 112.9 . . ?
C15D C14D H14F 112.9 . . ?
O5D C14D H14F 112.9 . . ?
H14E C14D H14F 110.4 . . ?
O6D C15D C14D 116(2) . . ?
O6D C15D H15E 108.2 . . ?
C14D C15D H15E 108.2 . . ?
O6D C15D H15F 108.2 . . ?
C14D C15D H15F 108.2 . . ?
H15E C15D H15F 107.4 . . ?
O6D C16D C17D 106.4(17) . . ?
O6D C16D H16E 110.5 . . ?
C17D C16D H16E 110.5 . . ?
O6D C16D H16F 110.5 . . ?
C17D C16D H16F 110.5 . . ?
H16E C16D H16F 108.7 . . ?
C16D C17D O5D 94(2) . . ?
C16D C17D H17E 112.8 . . ?
O5D C17D H17E 112.8 . . ?
C16D C17D H17F 112.8 . . ?
O5D C17D H17F 112.8 . . ?
H17E C17D H17F 110.3 . . ?
C15D O6D C16D 120.4(15) . . ?
C17D O5D C14D 91(2) . . ?
O1B C1B N1B 123.0(2) . . ?
O1B C1B C2B 120.3(2) . . ?
N1B C1B C2B 116.7(2) . . ?
C1B N1B C8B 128.6(2) . . ?
C1B N1B H1BN 115.6(18) . . ?
C8B N1B H1BN 115.8(18) . . ?
C7B C2B C3B 118.1(2) . . ?
C7B C2B C1B 115.5(2) . . ?
C3B C2B C1B 126.4(2) . . ?
O4B N2B O3B 123.2(2) . . ?
O4B N2B C11B 118.1(2) . . ?
O3B N2B C11B 118.7(2) . . ?
C3B O2B H2BO 114(2) . . ?
O2B C3B C4B 120.5(2) . . ?
O2B C3B C2B 119.2(2) . . ?
C4B C3B C2B 120.3(2) . . ?
C5B C4B C3B 120.7(2) . . ?
C5B C4B H4B 119.6 . . ?
C3B C4B H4B 119.6 . . ?
C4B C5B C6B 119.2(2) . . ?
C4B C5B H5B 120.4 . . ?
C6B C5B H5B 120.4 . . ?
C15B O5B C14B 110.9(3) . . ?
C7B C6B C5B 121.2(2) . . ?
C7B C6B Cl1B 119.6(2) . . ?
C5B C6B Cl1B 119.27(18) . . ?
C6B C7B C2B 120.6(2) . . ?
C6B C7B H7B 119.7 . . ?
C2B C7B H7B 119.7 . . ?
N1B C8B C9B 123.8(2) . . ?
N1B C8B C13B 118.19(19) . . ?
C9B C8B C13B 118.0(2) . . ?
C10B C9B C8B 120.5(2) . . ?
C10B C9B H9B 119.7 . . ?
C8B C9B H9B 119.7 . . ?
C11B C10B C9B 119.4(2) . . ?
C11B C10B H10B 120.3 . . ?
C9B C10B H10B 120.3 . . ?
C10B C11B C12B 121.9(2) . . ?
C10B C11B N2B 119.9(2) . . ?
C12B C11B N2B 118.2(2) . . ?
C13B C12B C11B 118.2(2) . . ?
C13B C12B H12B 120.9 . . ?
C11B C12B H12B 120.9 . . ?
C12B C13B C8B 121.9(2) . . ?
C12B C13B Cl2B 118.16(19) . . ?
C8B C13B Cl2B 119.96(17) . . ?
O5B C14B C15B 111.2(3) . 2_667 ?
O5B C14B H14C 109.4 . . ?
C15B C14B H14C 109.4 2_667 . ?
O5B C14B H14D 109.4 . . ?
C15B C14B H14D 109.4 2_667 . ?
H14C C14B H14D 108.0 . . ?
O5B C15B C14B 112.2(3) . 2_667 ?
O5B C15B H15C 109.2 . . ?
C14B C15B H15C 109.2 2_667 . ?
O5B C15B H15D 109.2 . . ?
C14B C15B H15D 109.2 2_667 . ?
H15C C15B H15D 107.9 . . ?

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
O1A C1A N1A C8A -0.3(4) . . . . ?
C2A C1A N1A C8A -179.5(2) . . . . ?
O1A C1A C2A C7A -2.9(3) . . . . ?
N1A C1A C2A C7A 176.2(2) . . . . ?
O1A C1A C2A C3A 177.1(2) . . . . ?
N1A C1A C2A C3A -3.7(3) . . . . ?
C7A C2A C3A O2A 177.5(2) . . . . ?
C1A C2A C3A O2A -2.6(4) . . . . ?
C7A C2A C3A C4A -1.3(3) . . . . ?
C1A C2A C3A C4A 178.7(2) . . . . ?
O2A C3A C4A C5A -177.9(2) . . . . ?
C2A C3A C4A C5A 0.8(4) . . . . ?
C3A C4A C5A C6A 0.4(4) . . . . ?
C4A C5A C6A C7A -1.2(4) . . . . ?
C4A C5A C6A Cl1A -175.9(5) . . . . ?
C4A C5A C6A Cl1D 162.5(9) . . . . ?
C5A C6A C7A C2A 0.7(4) . . . . ?
Cl1A C6A C7A C2A 175.3(5) . . . . ?
Cl1D C6A C7A C2A -163.9(8) . . . . ?
C3A C2A C7A C6A 0.5(4) . . . . ?
C1A C2A C7A C6A -179.5(2) . . . . ?
C1A N1A C8A C13A 179.9(2) . . . . ?
C1A N1A C8A C9A -0.9(4) . . . . ?
N1A C8A C9A C10A -179.4(2) . . . . ?
C13A C8A C9A C10A -0.2(4) . . . . ?
C8A C9A C10A C11A 0.6(4) . . . . ?
C9A C10A C11A C12A -0.6(4) . . . . ?
C9A C10A C11A N2A -179.8(2) . . . . ?
O3A N2A C11A C10A 7.8(4) . . . . ?
O4A N2A C11A C10A -171.6(3) . . . . ?
O3A N2A C11A C12A -171.5(2) . . . . ?
O4A N2A C11A C12A 9.2(4) . . . . ?
C10A C11A C12A C13A 0.2(4) . . . . ?
N2A C11A C12A C13A 179.5(2) . . . . ?
C11A C12A C13A C8A 0.2(4) . . . . ?
C11A C12A C13A Cl2A 179.71(19) . . . . ?
N1A C8A C13A C12A 179.1(2) . . . . ?
C9A C8A C13A C12A -0.2(3) . . . . ?
N1A C8A C13A Cl2A -0.4(3) . . . . ?
C9A C8A C13A Cl2A -179.70(18) . . . . ?
O5A C14A C15A O6A -60.2(6) . . . . ?
O6A C16A C17A O5A 62.3(6) . . . . ?
C15A C14A O5A C17A 64.5(6) . . . . ?
C16A C17A O5A C14A -65.8(6) . . . . ?
C14A C15A O6A C16A 56.9(6) . . . . ?
C17A C16A O6A C15A -58.7(6) . . . . ?
O5D C14D C15D O6D 59(3) . . . . ?
O6D C16D C17D O5D -69(2) . . . . ?
C14D C15D O6D C16D -42(4) . . . . ?
C17D C16D O6D C15D 43(3) . . . . ?
C16D C17D O5D C14D 91(2) . . . . ?
C15D C14D O5D C17D -84(3) . . . . ?
O1B C1B N1B C8B 1.4(4) . . . . ?
C2B C1B N1B C8B -179.3(2) . . . . ?
O1B C1B C2B C7B -0.6(4) . . . . ?
N1B C1B C2B C7B -180.0(2) . . . . ?
O1B C1B C2B C3B 178.7(3) . . . . ?
N1B C1B C2B C3B -0.6(4) . . . . ?
C7B C2B C3B O2B 179.7(2) . . . . ?
C1B C2B C3B O2B 0.4(4) . . . . ?
C7B C2B C3B C4B -0.8(4) . . . . ?
C1B C2B C3B C4B 179.8(2) . . . . ?
O2B C3B C4B C5B -180.0(2) . . . . ?
C2B C3B C4B C5B 0.6(4) . . . . ?
C3B C4B C5B C6B 0.1(4) . . . . ?
C4B C5B C6B C7B -0.7(4) . . . . ?
C4B C5B C6B Cl1B -178.9(2) . . . . ?
C5B C6B C7B C2B 0.4(4) . . . . ?
Cl1B C6B C7B C2B 178.70(19) . . . . ?
C3B C2B C7B C6B 0.3(4) . . . . ?
C1B C2B C7B C6B 179.7(2) . . . . ?
C1B N1B C8B C9B -1.9(4) . . . . ?
C1B N1B C8B C13B 177.6(2) . . . . ?
N1B C8B C9B C10B 178.9(2) . . . . ?
C13B C8B C9B C10B -0.5(4) . . . . ?
C8B C9B C10B C11B -0.8(4) . . . . ?
C9B C10B C11B C12B 1.1(4) . . . . ?
C9B C10B C11B N2B -177.7(2) . . . . ?
O4B N2B C11B C10B 160.5(3) . . . . ?
O3B N2B C11B C10B -17.4(4) . . . . ?
O4B N2B C11B C12B -18.4(4) . . . . ?
O3B N2B C11B C12B 163.7(2) . . . . ?
C10B C11B C12B C13B -0.1(4) . . . . ?
N2B C11B C12B C13B 178.7(2) . . . . ?
C11B C12B C13B C8B -1.3(4) . . . . ?
C11B C12B C13B Cl2B 179.53(19) . . . . ?
N1B C8B C13B C12B -177.9(2) . . . . ?
C9B C8B C13B C12B 1.6(4) . . . . ?
N1B C8B C13B Cl2B 1.3(3) . . . . ?
C9B C8B C13B Cl2B -179.23(18) . . . . ?
C15B O5B C14B C15B -54.4(5) . . . 2_667 ?
C14B O5B C15B C14B 55.0(5) . . . 2_667 ?

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_KB497_0m
_database_code_depnum_ccdc_archive 'CCDC 2352673'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Niclosamide n,n-dimethyl acetamide solvate 2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H8 Cl2 N2 O4, C4 H9 N O'
_chemical_formula_sum            'C17 H17 Cl2 N3 O5'
_chemical_formula_weight         414.23

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'
Cl Cl 0.1484 0.1585 '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                   7.4340(8)
_cell_length_b                   14.1832(16)
_cell_length_c                   18.431(2)
_cell_angle_alpha                100.902(3)
_cell_angle_beta                 100.288(4)
_cell_angle_gamma                91.378(4)
_cell_volume                     1874.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6550
_cell_measurement_theta_min      2.929
_cell_measurement_theta_max      21.025

_exptl_crystal_description       PLATE
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.381
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5282
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50878
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.465
_diffrn_reflns_theta_max         27.497
_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             8604
_reflns_number_gt                3526
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0613P)²+0.1468P] 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         8604
_refine_ls_number_parameters     567
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1614
_refine_ls_wR_factor_gt          0.1146
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.003
_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
Cl1A Cl 0.46732(14) -0.20661(6) 0.10486(6) 0.0967(3) Uani 1 1 d . . . . .
Cl2A Cl 0.77432(11) 0.36357(5) 0.40972(5) 0.0714(3) Uani 1 1 d . . . . .
N1A N 0.7264(3) 0.15214(18) 0.37372(15) 0.0553(7) Uani 1 1 d . . . . .
H1AN H 0.689(4) 0.192(2) 0.3440(18) 0.077(11) Uiso 1 1 d . . . . .
O1A O 0.7394(3) -0.00826(15) 0.36985(13) 0.0888(7) Uani 1 1 d . . . . .
N2A N 1.1143(4) 0.3104(2) 0.66404(16) 0.0692(7) Uani 1 1 d . . . . .
N3A N 0.4127(4) 0.44750(19) 0.12031(17) 0.0792(8) Uani 1 1 d . . . . .
O2A O 0.5493(3) 0.20095(15) 0.24923(13) 0.0764(7) Uani 1 1 d D . . . .
H2AO H 0.513(5) 0.235(2) 0.2182(17) 0.101(14) Uiso 1 1 d D . . . .
O3A O 1.1785(4) 0.25739(19) 0.70536(14) 0.1025(9) Uani 1 1 d . . . . .
O4A O 1.1367(4) 0.39759(19) 0.68088(14) 0.1013(8) Uani 1 1 d . . . . .
O5A O 0.4352(3) 0.30425(15) 0.15125(12) 0.0761(6) Uani 1 1 d . . . . .
C1A C 0.6924(4) 0.0579(2) 0.33820(17) 0.0583(8) Uani 1 1 d . . . . .
C2A C 0.5966(4) 0.0382(2) 0.25787(17) 0.0547(7) Uani 1 1 d . . . . .
C3A C 0.5315(4) 0.1065(2) 0.21580(18) 0.0596(8) Uani 1 1 d . . . . .
C4A C 0.4477(5) 0.0778(2) 0.14141(19) 0.0752(10) Uani 1 1 d . . . . .
H4A H 0.402636 0.123787 0.114127 0.090 Uiso 1 1 calc R U . . .
C5A C 0.4298(5) -0.0177(2) 0.1070(2) 0.0782(10) Uani 1 1 d . . . . .
H5A H 0.376001 -0.036328 0.056487 0.094 Uiso 1 1 calc R U . . .
C6A C 0.4927(4) -0.0851(2) 0.14838(19) 0.0650(9) Uani 1 1 d . . . . .
C7A C 0.5739(4) -0.0582(2) 0.22190(18) 0.0601(8) Uani 1 1 d . . . . .
H7A H 0.615212 -0.105111 0.248833 0.072 Uiso 1 1 calc R U . . .
C8A C 0.8192(4) 0.1881(2) 0.44616(17) 0.0508(7) Uani 1 1 d . . . . .
C9A C 0.8854(4) 0.1304(2) 0.49814(17) 0.0613(8) Uani 1 1 d . . . . .
H9A H 0.864773 0.063962 0.484451 0.074 Uiso 1 1 calc R U . . .
C10A C 0.9799(4) 0.1704(2) 0.56867(18) 0.0621(8) Uani 1 1 d . . . . .
H10A H 1.024234 0.131271 0.602233 0.074 Uiso 1 1 calc R U . . .
C11A C 1.0085(4) 0.2683(2) 0.58935(17) 0.0553(8) Uani 1 1 d . . . . .
C12A C 0.9436(4) 0.3284(2) 0.54176(17) 0.0573(8) Uani 1 1 d . . . . .
H12A H 0.961720 0.394824 0.557112 0.069 Uiso 1 1 calc R U . . .
C13A C 0.8508(4) 0.2879(2) 0.47071(17) 0.0536(7) Uani 1 1 d . . . . .
C14A C 0.4590(4) 0.3944(3) 0.1699(2) 0.0674(9) Uani 1 1 d . . . . .
C15A C 0.5419(5) 0.4413(2) 0.24909(18) 0.0827(10) Uani 1 1 d . . . . .
H15A H 0.656406 0.474575 0.249724 0.124 Uiso 1 1 calc R U . . .
H15B H 0.562444 0.393140 0.279393 0.124 Uiso 1 1 calc R U . . .
H15C H 0.460044 0.486363 0.268908 0.124 Uiso 1 1 calc R U . . .
C16A C 0.3316(6) 0.4007(3) 0.0430(2) 0.1036(13) Uani 1 1 d . . . . .
H16A H 0.256987 0.444750 0.019279 0.155 Uiso 1 1 calc R U . . .
H16B H 0.257363 0.344720 0.043732 0.155 Uiso 1 1 calc R U . . .
H16C H 0.427256 0.382163 0.015415 0.155 Uiso 1 1 calc R U . . .
C17A C 0.4345(6) 0.5540(2) 0.1381(2) 0.1022(13) Uani 1 1 d . . . . .
H17A H 0.422250 0.578003 0.092194 0.153 Uiso 1 1 calc R U . . .
H17B H 0.553334 0.573959 0.168129 0.153 Uiso 1 1 calc R U . . .
H17C H 0.341874 0.579106 0.165388 0.153 Uiso 1 1 calc R U . . .
Cl1B Cl 1.08058(15) 0.48631(7) 0.88042(6) 0.1041(4) Uani 1 1 d . . . . .
Cl2B Cl 0.73329(12) 0.91534(5) 0.59473(5) 0.0738(3) Uani 1 1 d . . . . .
N1B N 0.7775(3) 0.72081(18) 0.62622(15) 0.0544(6) Uani 1 1 d . . . . .
H1BN H 0.814(4) 0.777(2) 0.6565(16) 0.066(10) Uiso 1 1 d . . . . .
O1B O 0.7694(3) 0.56031(15) 0.62540(12) 0.0835(7) Uani 1 1 d . . . . .
N2B N 0.3850(4) 0.7366(3) 0.33876(17) 0.0747(8) Uani 1 1 d . . . . .
O2B O 0.9584(3) 0.83131(16) 0.75272(13) 0.0756(7) Uani 1 1 d D . . . .
H2BO H 0.981(5) 0.8813(18) 0.7852(16) 0.096(13) Uiso 1 1 d D . . . .
O3B O 0.3089(4) 0.6631(2) 0.29832(14) 0.1029(9) Uani 1 1 d . . . . .
O4B O 0.3742(4) 0.8154(2) 0.32172(15) 0.1099(9) Uani 1 1 d . . . . .
C1B C 0.8169(4) 0.6425(2) 0.65877(17) 0.0576(8) Uani 1 1 d . . . . .
C2B C 0.9218(4) 0.6617(2) 0.73799(16) 0.0523(7) Uani 1 1 d . . . . .
C3B C 0.9887(4) 0.7515(2) 0.78202(18) 0.0590(8) Uani 1 1 d . . . . .
C4B C 1.0858(4) 0.7572(2) 0.85392(18) 0.0703(9) Uani 1 1 d . . . . .
H4B H 1.132301 0.816866 0.882403 0.084 Uiso 1 1 calc R U . . .
C5B C 1.1151(4) 0.6769(3) 0.88412(19) 0.0729(9) Uani 1 1 d . . . . .
H5B H 1.180152 0.681879 0.932844 0.088 Uiso 1 1 calc R U . . .
C6B C 1.0472(4) 0.5886(2) 0.84169(19) 0.0670(9) Uani 1 1 d . . . . .
C7B C 0.9528(4) 0.5802(2) 0.76974(18) 0.0598(8) Uani 1 1 d . . . . .
H7B H 0.908995 0.519827 0.741739 0.072 Uiso 1 1 calc R U . . .
C8B C 0.6827(4) 0.7213(2) 0.55440(16) 0.0509(7) Uani 1 1 d . . . . .
C9B C 0.6119(4) 0.6375(2) 0.50175(17) 0.0613(8) Uani 1 1 d . . . . .
H9B H 0.630490 0.577536 0.514313 0.074 Uiso 1 1 calc R U . . .
C10B C 0.5160(4) 0.6434(2) 0.43238(18) 0.0634(8) Uani 1 1 d . . . . .
H10B H 0.467504 0.587694 0.398462 0.076 Uiso 1 1 calc R U . . .
C11B C 0.4914(4) 0.7310(2) 0.41275(17) 0.0566(8) Uani 1 1 d . . . . .
C12B C 0.5602(4) 0.8148(2) 0.46173(17) 0.0586(8) Uani 1 1 d . . . . .
H12B H 0.544480 0.873969 0.447413 0.070 Uiso 1 1 calc R U . . .
C13B C 0.6527(4) 0.8095(2) 0.53223(17) 0.0536(7) Uani 1 1 d . . . . .
N3B N 1.0452(5) 1.1383(3) 0.8946(2) 0.0723(11) Uani 0.797(5) 1 d . U P A 1
O5B O 1.0418(15) 0.9798(4) 0.8567(3) 0.0769(16) Uani 0.797(5) 1 d D U P A 1
C14B C 1.0124(6) 1.0601(3) 0.8416(3) 0.0654(12) Uani 0.797(5) 1 d D U P A 1
C15B C 0.9402(15) 1.0668(6) 0.7637(4) 0.0762(19) Uani 0.797(5) 1 d . U P A 1
H15D H 0.944594 1.005498 0.731535 0.114 Uiso 0.797(5) 1 calc R U P A 1
H15E H 1.012777 1.114295 0.749130 0.114 Uiso 0.797(5) 1 calc R U P A 1
H15F H 0.815654 1.084824 0.759403 0.114 Uiso 0.797(5) 1 calc R U P A 1
C16B C 1.1043(8) 1.1286(6) 0.9724(4) 0.0881(18) Uani 0.797(5) 1 d . U P A 1
H16D H 1.003455 1.138391 0.998475 0.132 Uiso 0.797(5) 1 calc R U P A 1
H16E H 1.202376 1.175570 0.996335 0.132 Uiso 0.797(5) 1 calc R U P A 1
H16F H 1.146045 1.065237 0.973557 0.132 Uiso 0.797(5) 1 calc R U P A 1
C17B C 1.0213(10) 1.2363(4) 0.8816(3) 0.0883(18) Uani 0.797(5) 1 d . U P A 1
H17D H 1.127731 1.259051 0.865753 0.133 Uiso 0.797(5) 1 calc R U P A 1
H17E H 1.005118 1.277697 0.927355 0.133 Uiso 0.797(5) 1 calc R U P A 1
H17F H 0.915399 1.236488 0.843272 0.133 Uiso 0.797(5) 1 calc R U P A 1
C16D C 1.178(3) 1.119(2) 0.9672(14) 0.072(3) Uani 0.203(5) 1 d D U P A 2
H16G H 1.279802 1.151202 0.954628 0.108 Uiso 0.203(5) 1 calc R U P A 2
H16H H 1.223025 1.071989 0.996502 0.108 Uiso 0.203(5) 1 calc R U P A 2
H16I H 1.112167 1.164548 0.995745 0.108 Uiso 0.203(5) 1 calc R U P A 2
N3D N 0.995(2) 1.1187(11) 0.8387(9) 0.072(2) Uani 0.203(5) 1 d D U P A 2
C17D C 0.997(4) 1.2278(14) 0.8485(14) 0.079(3) Uani 0.203(5) 1 d D U P A 2
H17G H 1.103042 1.256097 0.884308 0.119 Uiso 0.203(5) 1 calc R U P A 2
H17H H 0.888377 1.250062 0.866305 0.119 Uiso 0.203(5) 1 calc R U P A 2
H17I H 0.999243 1.245875 0.801074 0.119 Uiso 0.203(5) 1 calc R U P A 2
C14D C 1.049(2) 1.0672(13) 0.8940(9) 0.073(2) Uani 0.203(5) 1 d D U P A 2
C15D C 0.926(6) 1.085(3) 0.7562(14) 0.072(3) Uani 0.203(5) 1 d D U P A 2
H15G H 0.873802 1.137632 0.735246 0.109 Uiso 0.203(5) 1 calc R U P A 2
H15H H 0.835183 1.033531 0.748234 0.109 Uiso 0.203(5) 1 calc R U P A 2
H15I H 1.026513 1.063421 0.732245 0.109 Uiso 0.203(5) 1 calc R U P A 2
O5D O 1.033(6) 0.9779(16) 0.8765(15) 0.071(3) Uani 0.203(5) 1 d D U P A 2


_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
Cl1A C6A 1.748(3) . ?
Cl2A C13A 1.731(3) . ?
N1A C1A 1.369(3) . ?
N1A C8A 1.384(4) . ?
N1A H1AN 0.88(3) . ?
O1A C1A 1.221(3) . ?
N2A O3A 1.215(3) . ?
N2A O4A 1.217(3) . ?
N2A C11A 1.466(4) . ?
N3A C14A 1.296(4) . ?
N3A C16A 1.466(4) . ?
N3A C17A 1.483(4) . ?
O2A C3A 1.357(3) . ?
O2A H2AO 0.829(18) . ?
O5A C14A 1.259(4) . ?
C1A C2A 1.495(4) . ?
C2A C7A 1.393(4) . ?
C2A C3A 1.395(4) . ?
C3A C4A 1.380(4) . ?
C4A C5A 1.375(4) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.373(4) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.359(4) . ?
C7A H7A 0.9300 . ?
C8A C13A 1.403(4) . ?
C8A C9A 1.406(4) . ?
C9A C10A 1.371(4) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.369(4) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.372(4) . ?
C12A C13A 1.376(4) . ?
C12A H12A 0.9300 . ?
C14A C15A 1.499(4) . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
Cl1B C6B 1.738(3) . ?
Cl2B C13B 1.731(3) . ?
N1B C1B 1.373(4) . ?
N1B C8B 1.386(4) . ?
N1B H1BN 0.89(3) . ?
O1B C1B 1.222(3) . ?
N2B O4B 1.218(3) . ?
N2B O3B 1.220(3) . ?
N2B C11B 1.467(4) . ?
O2B C3B 1.350(3) . ?
O2B H2BO 0.829(18) . ?
C1B C2B 1.499(4) . ?
C2B C7B 1.397(4) . ?
C2B C3B 1.401(4) . ?
C3B C4B 1.378(4) . ?
C4B C5B 1.364(4) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.376(4) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.367(4) . ?
C7B H7B 0.9300 . ?
C8B C13B 1.398(4) . ?
C8B C9B 1.408(4) . ?
C9B C10B 1.366(4) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.365(4) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.374(4) . ?
C12B C13B 1.374(4) . ?
C12B H12B 0.9300 . ?
N3B C14B 1.318(6) . ?
N3B C16B 1.456(8) . ?
N3B C17B 1.464(6) . ?
O5B C14B 1.238(6) . ?
C14B C15B 1.460(7) . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
C16D C14D 1.550(18) . ?
C16D H16G 0.9600 . ?
C16D H16H 0.9600 . ?
C16D H16I 0.9600 . ?
N3D C14D 1.373(17) . ?
N3D C15D 1.494(19) . ?
N3D C17D 1.523(17) . ?
C17D H17G 0.9600 . ?
C17D H17H 0.9600 . ?
C17D H17I 0.9600 . ?
C14D O5D 1.244(18) . ?
C15D H15G 0.9600 . ?
C15D H15H 0.9600 . ?
C15D H15I 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
C1A N1A C8A 127.9(3) . . ?
C1A N1A H1AN 113(2) . . ?
C8A N1A H1AN 119(2) . . ?
O3A N2A O4A 123.2(3) . . ?
O3A N2A C11A 119.1(3) . . ?
O4A N2A C11A 117.7(3) . . ?
C14A N3A C16A 118.9(3) . . ?
C14A N3A C17A 123.2(3) . . ?
C16A N3A C17A 117.9(3) . . ?
C3A O2A H2AO 111(3) . . ?
O1A C1A N1A 122.1(3) . . ?
O1A C1A C2A 120.6(3) . . ?
N1A C1A C2A 117.3(3) . . ?
C7A C2A C3A 117.6(3) . . ?
C7A C2A C1A 116.0(3) . . ?
C3A C2A C1A 126.4(3) . . ?
O2A C3A C4A 120.7(3) . . ?
O2A C3A C2A 119.2(3) . . ?
C4A C3A C2A 120.1(3) . . ?
C5A C4A C3A 121.1(3) . . ?
C5A C4A H4A 119.5 . . ?
C3A C4A H4A 119.5 . . ?
C6A C5A C4A 118.9(3) . . ?
C6A C5A H5A 120.5 . . ?
C4A C5A H5A 120.5 . . ?
C7A C6A C5A 120.7(3) . . ?
C7A C6A Cl1A 120.4(3) . . ?
C5A C6A Cl1A 118.9(3) . . ?
C6A C7A C2A 121.6(3) . . ?
C6A C7A H7A 119.2 . . ?
C2A C7A H7A 119.2 . . ?
N1A C8A C13A 119.3(3) . . ?
N1A C8A C9A 124.0(3) . . ?
C13A C8A C9A 116.7(3) . . ?
C10A C9A C8A 121.2(3) . . ?
C10A C9A H9A 119.4 . . ?
C8A C9A H9A 119.4 . . ?
C11A C10A C9A 119.6(3) . . ?
C11A C10A H10A 120.2 . . ?
C9A C10A H10A 120.2 . . ?
C10A C11A C12A 122.0(3) . . ?
C10A C11A N2A 119.3(3) . . ?
C12A C11A N2A 118.8(3) . . ?
C11A C12A C13A 118.3(3) . . ?
C11A C12A H12A 120.9 . . ?
C13A C12A H12A 120.9 . . ?
C12A C13A C8A 122.3(3) . . ?
C12A C13A Cl2A 118.3(2) . . ?
C8A C13A Cl2A 119.4(2) . . ?
O5A C14A N3A 120.1(3) . . ?
O5A C14A C15A 120.5(3) . . ?
N3A C14A C15A 119.4(3) . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
N3A C16A H16A 109.5 . . ?
N3A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
N3A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
N3A C17A H17A 109.5 . . ?
N3A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
N3A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C1B N1B C8B 127.7(3) . . ?
C1B N1B H1BN 114.5(19) . . ?
C8B N1B H1BN 117.8(19) . . ?
O4B N2B O3B 123.5(3) . . ?
O4B N2B C11B 117.7(3) . . ?
O3B N2B C11B 118.8(3) . . ?
C3B O2B H2BO 112(3) . . ?
O1B C1B N1B 122.2(3) . . ?
O1B C1B C2B 120.7(3) . . ?
N1B C1B C2B 117.1(3) . . ?
C7B C2B C3B 118.2(3) . . ?
C7B C2B C1B 115.1(3) . . ?
C3B C2B C1B 126.7(3) . . ?
O2B C3B C4B 121.0(3) . . ?
O2B C3B C2B 119.2(3) . . ?
C4B C3B C2B 119.8(3) . . ?
C5B C4B C3B 121.3(3) . . ?
C5B C4B H4B 119.4 . . ?
C3B C4B H4B 119.4 . . ?
C4B C5B C6B 119.3(3) . . ?
C4B C5B H5B 120.4 . . ?
C6B C5B H5B 120.4 . . ?
C7B C6B C5B 121.0(3) . . ?
C7B C6B Cl1B 119.5(3) . . ?
C5B C6B Cl1B 119.5(3) . . ?
C6B C7B C2B 120.4(3) . . ?
C6B C7B H7B 119.8 . . ?
C2B C7B H7B 119.8 . . ?
N1B C8B C13B 119.0(3) . . ?
N1B C8B C9B 123.7(3) . . ?
C13B C8B C9B 117.3(3) . . ?
C10B C9B C8B 120.6(3) . . ?
C10B C9B H9B 119.7 . . ?
C8B C9B H9B 119.7 . . ?
C11B C10B C9B 120.2(3) . . ?
C11B C10B H10B 119.9 . . ?
C9B C10B H10B 119.9 . . ?
C10B C11B C12B 121.4(3) . . ?
C10B C11B N2B 119.7(3) . . ?
C12B C11B N2B 118.9(3) . . ?
C13B C12B C11B 118.7(3) . . ?
C13B C12B H12B 120.6 . . ?
C11B C12B H12B 120.6 . . ?
C12B C13B C8B 121.8(3) . . ?
C12B C13B Cl2B 118.6(2) . . ?
C8B C13B Cl2B 119.6(2) . . ?
C14B N3B C16B 119.0(5) . . ?
C14B N3B C17B 124.6(5) . . ?
C16B N3B C17B 116.4(4) . . ?
O5B C14B N3B 120.8(6) . . ?
O5B C14B C15B 118.8(5) . . ?
N3B C14B C15B 120.5(6) . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
N3B C16B H16D 109.5 . . ?
N3B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
N3B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
N3B C17B H17D 109.5 . . ?
N3B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
N3B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C14D C16D H16G 109.5 . . ?
C14D C16D H16H 109.5 . . ?
H16G C16D H16H 109.5 . . ?
C14D C16D H16I 109.5 . . ?
H16G C16D H16I 109.5 . . ?
H16H C16D H16I 109.5 . . ?
C14D N3D C15D 130(2) . . ?
C14D N3D C17D 126.5(18) . . ?
C15D N3D C17D 103.0(19) . . ?
N3D C17D H17G 109.5 . . ?
N3D C17D H17H 109.5 . . ?
H17G C17D H17H 109.5 . . ?
N3D C17D H17I 109.5 . . ?
H17G C17D H17I 109.5 . . ?
H17H C17D H17I 109.5 . . ?
O5D C14D N3D 118(2) . . ?
O5D C14D C16D 121(2) . . ?
N3D C14D C16D 118(2) . . ?
N3D C15D H15G 109.5 . . ?
N3D C15D H15H 109.5 . . ?
H15G C15D H15H 109.5 . . ?
N3D C15D H15I 109.5 . . ?
H15G C15D H15I 109.5 . . ?
H15H C15D H15I 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
C8A N1A C1A O1A 2.3(5) . . . . ?
C8A N1A C1A C2A -177.0(3) . . . . ?
O1A C1A C2A C7A -3.0(4) . . . . ?
N1A C1A C2A C7A 176.2(2) . . . . ?
O1A C1A C2A C3A 178.2(3) . . . . ?
N1A C1A C2A C3A -2.6(4) . . . . ?
C7A C2A C3A O2A 179.2(3) . . . . ?
C1A C2A C3A O2A -1.9(5) . . . . ?
C7A C2A C3A C4A 0.2(4) . . . . ?
C1A C2A C3A C4A 179.0(3) . . . . ?
O2A C3A C4A C5A 179.7(3) . . . . ?
C2A C3A C4A C5A -1.3(5) . . . . ?
C3A C4A C5A C6A 1.6(5) . . . . ?
C4A C5A C6A C7A -1.0(5) . . . . ?
C4A C5A C6A Cl1A 179.2(2) . . . . ?
C5A C6A C7A C2A -0.1(5) . . . . ?
Cl1A C6A C7A C2A 179.7(2) . . . . ?
C3A C2A C7A C6A 0.5(4) . . . . ?
C1A C2A C7A C6A -178.4(3) . . . . ?
C1A N1A C8A C13A 175.6(3) . . . . ?
C1A N1A C8A C9A -4.4(5) . . . . ?
N1A C8A C9A C10A 178.6(3) . . . . ?
C13A C8A C9A C10A -1.5(4) . . . . ?
C8A C9A C10A C11A 0.8(4) . . . . ?
C9A C10A C11A C12A 0.7(4) . . . . ?
C9A C10A C11A N2A -178.2(3) . . . . ?
O3A N2A C11A C10A 1.9(4) . . . . ?
O4A N2A C11A C10A -179.7(3) . . . . ?
O3A N2A C11A C12A -177.1(3) . . . . ?
O4A N2A C11A C12A 1.3(4) . . . . ?
C10A C11A C12A C13A -1.5(4) . . . . ?
N2A C11A C12A C13A 177.4(2) . . . . ?
C11A C12A C13A C8A 0.8(4) . . . . ?
C11A C12A C13A Cl2A -178.2(2) . . . . ?
N1A C8A C13A C12A -179.4(2) . . . . ?
C9A C8A C13A C12A 0.6(4) . . . . ?
N1A C8A C13A Cl2A -0.4(4) . . . . ?
C9A C8A C13A Cl2A 179.7(2) . . . . ?
C16A N3A C14A O5A 0.4(5) . . . . ?
C17A N3A C14A O5A 179.3(3) . . . . ?
C16A N3A C14A C15A -179.9(3) . . . . ?
C17A N3A C14A C15A -1.1(5) . . . . ?
C8B N1B C1B O1B 0.1(5) . . . . ?
C8B N1B C1B C2B -179.8(2) . . . . ?
O1B C1B C2B C7B -2.2(4) . . . . ?
N1B C1B C2B C7B 177.7(2) . . . . ?
O1B C1B C2B C3B 178.2(3) . . . . ?
N1B C1B C2B C3B -1.9(4) . . . . ?
C7B C2B C3B O2B -179.2(3) . . . . ?
C1B C2B C3B O2B 0.3(4) . . . . ?
C7B C2B C3B C4B 1.5(4) . . . . ?
C1B C2B C3B C4B -178.9(3) . . . . ?
O2B C3B C4B C5B 179.2(3) . . . . ?
C2B C3B C4B C5B -1.5(5) . . . . ?
C3B C4B C5B C6B 0.4(5) . . . . ?
C4B C5B C6B C7B 0.7(5) . . . . ?
C4B C5B C6B Cl1B -178.9(2) . . . . ?
C5B C6B C7B C2B -0.6(5) . . . . ?
Cl1B C6B C7B C2B 178.9(2) . . . . ?
C3B C2B C7B C6B -0.4(4) . . . . ?
C1B C2B C7B C6B 179.9(3) . . . . ?
C1B N1B C8B C13B 178.5(3) . . . . ?
C1B N1B C8B C9B -0.9(4) . . . . ?
N1B C8B C9B C10B 178.5(3) . . . . ?
C13B C8B C9B C10B -0.8(4) . . . . ?
C8B C9B C10B C11B 1.5(4) . . . . ?
C9B C10B C11B C12B -0.5(4) . . . . ?
C9B C10B C11B N2B -178.7(3) . . . . ?
O4B N2B C11B C10B -176.2(3) . . . . ?
O3B N2B C11B C10B 5.4(4) . . . . ?
O4B N2B C11B C12B 5.6(4) . . . . ?
O3B N2B C11B C12B -172.8(3) . . . . ?
C10B C11B C12B C13B -1.2(4) . . . . ?
N2B C11B C12B C13B 177.1(2) . . . . ?
C11B C12B C13B C8B 1.8(4) . . . . ?
C11B C12B C13B Cl2B -178.1(2) . . . . ?
N1B C8B C13B C12B 179.8(2) . . . . ?
C9B C8B C13B C12B -0.8(4) . . . . ?
N1B C8B C13B Cl2B -0.3(4) . . . . ?
C9B C8B C13B Cl2B 179.1(2) . . . . ?
C16B N3B C14B O5B -4.3(9) . . . . ?
C17B N3B C14B O5B 177.6(7) . . . . ?
C16B N3B C14B C15B 175.5(7) . . . . ?
C17B N3B C14B C15B -2.6(8) . . . . ?
C15D N3D C14D O5D -4(4) . . . . ?
C17D N3D C14D O5D 178(3) . . . . ?
C15D N3D C14D C16D 158(3) . . . . ?
C17D N3D C14D C16D -20(3) . . . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042

