Expanding the structural landscape of niclosamide: a high <i>Z</i>' polymorph, two new solvates and monohydrate H~<i>A~</i>
Sovago, Ioana; Bond, Andrew D.; Acta Crystallographica Section C 71 (2015) 394–401; doi:10.1107/S2053229615005847

data_2019938
_publ_section_title
;
 Expanding the structural landscape of niclosamide: a high <i>Z</i>'
 polymorph, two new solvates and monohydrate H~<i>A~</i>
;
_journal_coeditor_code           FA3363
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              394
_journal_page_last               401
_journal_paper_doi               10.1107/S2053229615005847
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C13 H8 Cl2 N2 O4'
_chemical_formula_moiety         'C13 H8 Cl2 N2 O4'
_chemical_formula_sum            'C13 H8 Cl2 N2 O4'
_chemical_formula_weight         327.11
_chemical_name_common            niclosamide
_chemical_name_systematic
;
5-chloro-<i>N</i>-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 92.282(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   15.3040(5)
_cell_length_b                   12.9458(4)
_cell_length_c                   26.6596(9)
_cell_measurement_reflns_used    8327
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.55
_cell_measurement_theta_min      2.66
_cell_volume                     5277.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Nonius X8 APEXII CCD area-detector'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27935
_diffrn_reflns_theta_full        21.965
_diffrn_reflns_theta_max         21.965
_diffrn_reflns_theta_min         3.514
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
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_refine_diff_density_min         -0.442
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
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_refine_ls_number_reflns         6416
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0311
_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/[\s^2^(Fo^2^)+(0.0444P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0763
_reflns_number_gt                4482
_reflns_number_total             6416
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fa3363sup1.cif
_cod_data_source_block           niclosamide_FormII
_cod_database_code               2019938
_cod_database_fobs_code          2019938
_shelx_estimated_absorpt_t_min   0.785
_shelx_estimated_absorpt_t_max   0.951
_shelx_hkl_checksum              36295
_shelx_res_checksum              39772
_shelxl_version_number           .2013