#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/67/4506748.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_4506748
loop_
_publ_author_name
'Sanphui, Palash'
'Kumar, S. Sudalai'
'Nangia, Ashwini'
_publ_section_title
;
 Pharmaceutical Cocrystals of Niclosamide
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4588
_journal_paper_doi               10.1021/cg300784v
_journal_volume                  12
_journal_year                    2012
_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
;2,5-dichloro-4-nitrosalicylanilide  
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.345(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.485(2)
_cell_length_b                   7.0669(11)
_cell_length_c                   13.510(2)
_cell_measurement_reflns_used    5661
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.97
_cell_measurement_theta_min      3.05
_cell_volume                     1273.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12392
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.527
_exptl_absorpt_correction_T_max  0.8928
_exptl_absorpt_correction_T_min  0.8089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0537P)²+0.5288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                2326
_reflns_number_total             2490
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300784v_si_002.cif
_cod_data_source_block           NCL
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1273.9(3)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4506748
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.24560(3) 0.18881(6) 0.39301(3) 0.01831(14) Uani 1 1 d .
Cl2 Cl -0.36871(3) 0.38053(6) 0.51279(3) 0.02024(14) Uani 1 1 d .
O3 O -0.00371(9) 0.18244(18) 0.64865(9) 0.0196(3) Uani 1 1 d .
N1 N 0.09394(10) 0.1911(2) 0.52503(11) 0.0139(3) Uani 1 1 d .
N2 N 0.48100(11) -0.0099(2) 0.70644(11) 0.0199(3) Uani 1 1 d .
O2 O 0.54815(10) -0.0024(2) 0.65504(10) 0.0328(4) Uani 1 1 d .
O4 O 0.00934(9) 0.31567(18) 0.34946(9) 0.0184(3) Uani 1 1 d .
C13 C -0.07769(12) 0.3351(2) 0.38837(13) 0.0144(3) Uani 1 1 d .
C1 C 0.18738(12) 0.1356(2) 0.57481(12) 0.0135(3) Uani 1 1 d .
C4 C 0.37931(12) 0.0399(2) 0.66081(13) 0.0164(4) Uani 1 1 d .
O1 O 0.49434(10) -0.0571(2) 0.79426(10) 0.0342(4) Uani 1 1 d .
C7 C 0.00627(12) 0.2168(2) 0.56213(12) 0.0137(3) Uani 1 1 d .
C12 C -0.16352(13) 0.4012(2) 0.32893(13) 0.0168(4) Uani 1 1 d .
H12 H -0.1605 0.4356 0.2615 0.020 Uiso 1 1 calc R
C9 C -0.17067(13) 0.3082(2) 0.52643(13) 0.0155(4) Uani 1 1 d .
H9 H -0.1739 0.2789 0.5945 0.019 Uiso 1 1 calc R
C11 C -0.25294(13) 0.4175(2) 0.36629(13) 0.0167(4) Uani 1 1 d .
H11 H -0.3115 0.4612 0.3250 0.020 Uiso 1 1 calc R
C8 C -0.07986(12) 0.2895(2) 0.48918(12) 0.0138(3) Uani 1 1 d .
C10 C -0.25588(12) 0.3688(2) 0.46527(13) 0.0159(4) Uani 1 1 d .
C2 C 0.26766(13) 0.1350(2) 0.51927(12) 0.0145(3) Uani 1 1 d .
C3 C 0.36377(13) 0.0910(2) 0.56082(13) 0.0162(4) Uani 1 1 d .
H3 H 0.4175 0.0955 0.5226 0.019 Uiso 1 1 calc R
C5 C 0.30271(13) 0.0320(2) 0.71756(13) 0.0165(4) Uani 1 1 d .
H5 H 0.3156 -0.0067 0.7855 0.020 Uiso 1 1 calc R
C6 C 0.20660(13) 0.0810(2) 0.67491(13) 0.0155(4) Uani 1 1 d .
H6 H 0.1535 0.0773 0.7140 0.019 Uiso 1 1 calc R
H1 H 0.0908(15) 0.217(3) 0.4631(16) 0.015(5) Uiso 1 1 d .
H2 H 0.0009(17) 0.318(3) 0.2913(18) 0.025(6) Uiso 1 1 d .
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
C7 N1 C1 129.17(15)
C7 N1 H1 114.3(14)
C1 N1 H1 116.5(14)
O2 N2 O1 123.27(15)
O2 N2 C4 118.53(15)
O1 N2 C4 118.19(15)
C13 O4 H2 112.3(17)
O4 C13 C12 120.21(15)
O4 C13 C8 119.48(15)
C12 C13 C8 120.31(15)
C6 C1 N1 124.96(15)
C6 C1 C2 117.93(15)
N1 C1 C2 117.11(15)
C5 C4 C3 122.37(16)
C5 C4 N2 119.33(15)
C3 C4 N2 118.29(15)
O3 C7 N1 123.25(15)
O3 C7 C8 120.99(15)
N1 C7 C8 115.76(14)
C11 C12 C13 121.05(16)
C11 C12 H12 119.5
C13 C12 H12 119.5
C10 C9 C8 120.69(15)
C10 C9 H9 119.7
C8 C9 H9 119.7
C12 C11 C10 118.79(16)
C12 C11 H11 120.6
C10 C11 H11 120.6
C9 C8 C13 118.09(15)
C9 C8 C7 115.55(14)
C13 C8 C7 126.34(15)
C9 C10 C11 121.03(16)
C9 C10 Cl2 119.38(13)
C11 C10 Cl2 119.59(13)
C3 C2 C1 122.56(15)
C3 C2 Cl1 118.06(13)
C1 C2 Cl1 119.38(13)
C2 C3 C4 117.31(16)
C2 C3 H3 121.3
C4 C3 H3 121.3
C4 C5 C6 119.48(16)
C4 C5 H5 120.3
C6 C5 H5 120.3
C5 C6 C1 120.28(16)
C5 C6 H6 119.9
C1 C6 H6 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.7308(17)
Cl2 C10 1.7372(17)
O3 C7 1.220(2)
N1 C7 1.362(2)
N1 C1 1.396(2)
N1 H1 0.85(2)
N2 O2 1.220(2)
N2 O1 1.220(2)
N2 C4 1.463(2)
O4 C13 1.361(2)
O4 H2 0.78(2)
C13 C12 1.390(2)
C13 C8 1.404(2)
C1 C6 1.394(2)
C1 C2 1.404(2)
C4 C5 1.374(2)
C4 C3 1.385(2)
C7 C8 1.501(2)
C12 C11 1.378(2)
C12 H12 0.9500
C9 C10 1.383(2)
C9 C8 1.396(2)
C9 H9 0.9500
C11 C10 1.387(3)
C11 H11 0.9500
C2 C3 1.371(2)
C3 H3 0.9500
C5 C6 1.384(2)
C5 H5 0.9500
C6 H6 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4322
