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_2019940
_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 , C2 H3 N'
_chemical_formula_moiety         'C13 H8 Cl2 N2 O4, C2 H3 N'
_chemical_formula_sum            'C15 H11 Cl2 N3 O4'
_chemical_formula_weight         368.17
_chemical_name_common            'niclosamide acetonitrile solvate'
_chemical_name_systematic
;
5-chloro-<i>N</i>-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide--acetonitrile
(1/1)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                87.976(2)
_cell_angle_beta                 87.124(2)
_cell_angle_gamma                84.077(3)
_cell_formula_units_Z            2
_cell_length_a                   3.8301(2)
_cell_length_b                   11.7321(5)
_cell_length_c                   16.9034(7)
_cell_measurement_reflns_used    2967
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      47.25
_cell_measurement_theta_min      3.74
_cell_volume                     754.20(6)
_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      120(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1517
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5506
_diffrn_reflns_theta_full        65.000
_diffrn_reflns_theta_max         66.498
_diffrn_reflns_theta_min         7.877
_exptl_absorpt_coefficient_mu    4.129
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.181
_refine_diff_density_min         -0.707
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0818
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1444P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2011
_refine_ls_wR_factor_ref         0.2281
_reflns_number_gt                1690
_reflns_number_total             2571
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fa3363sup1.cif
_cod_data_source_block           niclosamide_acetonitrile
_cod_database_code               2019940
_cod_database_fobs_code          2019940
_shelx_estimated_absorpt_t_min   0.683
_shelx_estimated_absorpt_t_max   0.922
_shelx_hkl_checksum              84375
_shelx_res_checksum              50137
_shelxl_version_number           .2013