#------------------------------------------------------------------------------
#$Date: 2024-09-06 03:12:54 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/91/7249108.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249108
loop_
_publ_author_name
'Kuri, Prasitaditya'
'Nanubolu, Jagadeesh Babu'
_publ_section_title
;
 Why does the niclosamide drug form solvates or hydrates?
;
_journal_issue                   32
_journal_name_full               CrystEngComm
_journal_page_first              4313
_journal_page_last               4328
_journal_paper_doi               10.1039/D4CE00463A
_journal_volume                  26
_journal_year                    2024
_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
_chemical_name_systematic        'Niclosamide n,n-dimethyl acetamide solvate 2'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-02 deposited with the CCDC.	2024-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                100.902(3)
_cell_angle_beta                 100.288(4)
_cell_angle_gamma                91.378(4)
_cell_formula_units_Z            4
_cell_length_a                   7.4340(8)
_cell_length_b                   14.1832(16)
_cell_length_c                   18.431(2)
_cell_measurement_reflns_used    6550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.025
_cell_measurement_theta_min      2.929
_cell_volume                     1874.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            50878
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.465
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.381
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5282
_exptl_absorpt_correction_type   multi-scan
_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_crystal_density_diffrn    1.468
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         8604
_refine_ls_number_restraints     186
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0613P)²+0.1468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1614
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3526
_reflns_number_total             8604
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00463a2.cif
_cod_data_source_block           KB497_0m
_cod_depositor_comments
'Adding full bibliography for 7249103--7249108.cif.'
_cod_database_code               7249108
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.875
_shelx_estimated_absorpt_t_max   0.956
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_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
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'
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_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_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) . . . . ?
