#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:54:37 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179603 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/67/4506751.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_4506751
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, C7 H8 N4 O2, C2 H3 N'
_chemical_formula_sum            'C20 H16 Cl2 N6 O6'
_chemical_formula_weight         507.29
_chemical_name_common            Niclosamide-theophylline
_chemical_name_systematic
;2,5-dichloro-4-nitrosalicylanilide, 1,3-dimethyl-7H-purine-2,6-dione  
 ? 
;
_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                 99.924(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1371(7)
_cell_length_b                   10.8809(9)
_cell_length_c                   22.4497(17)
_cell_measurement_reflns_used    2340
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.3152
_cell_measurement_theta_min      2.6210
_cell_volume                     2198.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0946
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10097
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.9401
_exptl_absorpt_correction_T_min  0.9090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0352P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                2389
_reflns_number_total             4499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300784v_si_005.cif
_cod_data_source_block           NCL-THPH
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_sg_symbol_H-M      P21/c
_cod_database_code               4506751
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 0.99053(10) 0.22920(8) 0.39604(4) 0.0579(3) Uani 1 1 d .
Cl2 Cl 1.03831(14) 0.03258(12) 0.78358(5) 0.0899(4) Uani 1 1 d .
O5 O 0.8968(3) 0.4299(2) 0.56298(11) 0.0519(6) Uani 1 1 d .
O4 O 1.1473(3) 0.1996(2) 0.54682(12) 0.0529(7) Uani 1 1 d .
C1 C 0.7763(4) 0.1129(3) 0.44486(15) 0.0360(8) Uani 1 1 d .
N4 N 0.6620(3) 0.3493(2) 0.55581(12) 0.0418(7) Uani 1 1 d .
N1 N 0.8779(3) 0.1208(3) 0.49860(13) 0.0410(7) Uani 1 1 d .
N6 N 0.5789(3) 0.4356(2) 0.37779(14) 0.0498(8) Uani 1 1 d .
O3 O 0.7456(3) 0.0317(2) 0.56420(11) 0.0633(7) Uani 1 1 d .
O6 O 0.4303(3) 0.2673(2) 0.55059(12) 0.0586(7) Uani 1 1 d .
N3 N 0.4897(3) 0.3436(2) 0.46408(14) 0.0440(7) Uani 1 1 d .
N5 N 0.8057(4) 0.4876(3) 0.42699(14) 0.0472(8) Uani 1 1 d .
C15 C 0.5957(4) 0.4019(3) 0.43709(16) 0.0408(8) Uani 1 1 d .
C18 C 0.7769(4) 0.4066(3) 0.53115(16) 0.0399(8) Uani 1 1 d .
C17 C 0.7323(4) 0.4316(3) 0.46866(16) 0.0385(8) Uani 1 1 d .
C8 C 0.9848(4) 0.1064(3) 0.60637(15) 0.0401(8) Uani 1 1 d .
C6 C 0.6370(4) 0.0581(3) 0.44007(15) 0.0443(9) Uani 1 1 d .
H6 H 0.6088 0.0225 0.4740 0.053 Uiso 1 1 calc R
C13 C 1.1205(4) 0.1631(3) 0.60201(16) 0.0423(9) Uani 1 1 d .
C5 C 0.5405(4) 0.0558(3) 0.38573(16) 0.0489(9) Uani 1 1 d .
H5 H 0.4481 0.0182 0.3827 0.059 Uiso 1 1 calc R
C7 C 0.8597(4) 0.0819(3) 0.55526(16) 0.0418(9) Uani 1 1 d .
C14 C 0.5221(4) 0.3175(3) 0.52441(18) 0.0451(9) Uani 1 1 d .
C2 C 0.8162(4) 0.1641(3) 0.39233(16) 0.0413(8) Uani 1 1 d .
C4 C 0.5831(4) 0.1102(3) 0.33569(16) 0.0478(9) Uani 1 1 d .
C20 C 0.3454(4) 0.3084(3) 0.42931(18) 0.0591(11) Uani 1 1 d .
H20A H 0.3307 0.2217 0.4335 0.089 Uiso 1 1 calc R
H20B H 0.3427 0.3278 0.3874 0.089 Uiso 1 1 calc R
H20C H 0.2681 0.3525 0.4441 0.089 Uiso 1 1 calc R
C10 C 1.0687(4) 0.0850(3) 0.71337(16) 0.0539(10) Uani 1 1 d .
C3 C 0.7210(4) 0.1640(3) 0.33843(16) 0.0456(9) Uani 1 1 d .
H3 H 0.7483 0.1993 0.3043 0.055 Uiso 1 1 calc R
C9 C 0.9622(4) 0.0677(3) 0.66333(15) 0.0451(9) Uani 1 1 d .
H9 H 0.8733 0.0296 0.6673 0.054 Uiso 1 1 calc R
C19 C 0.6892(4) 0.3231(3) 0.62116(15) 0.0555(10) Uani 1 1 d .
H19A H 0.6331 0.3794 0.6413 0.083 Uiso 1 1 calc R
H19B H 0.7931 0.3325 0.6369 0.083 Uiso 1 1 calc R
H19C H 0.6591 0.2405 0.6279 0.083 Uiso 1 1 calc R
C16 C 0.7104(4) 0.4870(3) 0.37511(18) 0.0517(10) Uani 1 1 d .
H16 H 0.7336 0.5198 0.3396 0.062 Uiso 1 1 calc R
O2 O 0.5149(3) 0.1654(3) 0.23541(13) 0.0950(11) Uani 1 1 d .
N2 N 0.4793(4) 0.1114(3) 0.27833(16) 0.0700(10) Uani 1 1 d .
C12 C 1.2275(4) 0.1802(3) 0.65342(17) 0.0539(10) Uani 1 1 d .
H12 H 1.3169 0.2182 0.6501 0.065 Uiso 1 1 calc R
C11 C 1.2026(4) 0.1417(3) 0.70902(18) 0.0602(11) Uani 1 1 d .
H11 H 1.2744 0.1534 0.7433 0.072 Uiso 1 1 calc R
O1 O 0.3593(4) 0.0625(4) 0.27574(14) 0.1194(14) Uani 1 1 d .
H2 H 1.240(4) 0.222(3) 0.5478(18) 0.078(14) Uiso 1 1 d .
H1 H 0.963(4) 0.156(3) 0.4947(17) 0.080(14) Uiso 1 1 d .
H5A H 0.905(4) 0.517(3) 0.4362(15) 0.062(11) 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
C13 O4 H2 112(3)
N1 C1 C6 123.9(3)
N1 C1 C2 118.1(3)
C6 C1 C2 118.0(3)
C14 N4 C18 126.2(3)
C14 N4 C19 116.0(3)
C18 N4 C19 117.8(3)
C7 N1 C1 127.8(3)
C7 N1 H1 118(3)
C1 N1 H1 114(3)
C16 N6 C15 101.9(3)
C14 N3 C15 118.8(3)
C14 N3 C20 119.7(3)
C15 N3 C20 121.4(3)
C16 N5 C17 105.6(3)
C16 N5 H5A 130(2)
C17 N5 H5A 124(2)
C17 C15 N6 112.5(3)
C17 C15 N3 121.9(3)
N6 C15 N3 125.6(3)
O5 C18 N4 120.8(3)
O5 C18 C17 127.7(3)
N4 C18 C17 111.5(3)
C15 C17 N5 105.1(3)
C15 C17 C18 123.3(3)
N5 C17 C18 131.6(3)
C9 C8 C13 117.9(3)
C9 C8 C7 115.8(3)
C13 C8 C7 126.3(3)
C5 C6 C1 120.9(3)
C5 C6 H6 119.6
C1 C6 H6 119.6
O4 C13 C12 120.3(3)
O4 C13 C8 119.4(3)
C12 C13 C8 120.3(3)
C6 C5 C4 119.0(3)
C6 C5 H5 120.5
C4 C5 H5 120.5
O3 C7 N1 122.0(3)
O3 C7 C8 120.9(3)
N1 C7 C8 117.1(3)
O6 C14 N3 121.1(3)
O6 C14 N4 120.6(3)
N3 C14 N4 118.3(3)
C3 C2 C1 121.7(3)
C3 C2 Cl1 119.0(3)
C1 C2 Cl1 119.4(3)
C3 C4 C5 121.8(3)
C3 C4 N2 118.9(3)
C5 C4 N2 119.3(3)
N3 C20 H20A 109.5
N3 C20 H20B 109.5
H20A C20 H20B 109.5
N3 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C9 C10 C11 121.0(3)
C9 C10 Cl2 119.8(3)
C11 C10 Cl2 119.2(3)
C2 C3 C4 118.6(3)
C2 C3 H3 120.7
C4 C3 H3 120.7
C10 C9 C8 121.0(3)
C10 C9 H9 119.5
C8 C9 H9 119.5
N4 C19 H19A 109.5
N4 C19 H19B 109.5
H19A C19 H19B 109.5
N4 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
N5 C16 N6 114.9(3)
N5 C16 H16 122.5
N6 C16 H16 122.5
O1 N2 O2 122.5(4)
O1 N2 C4 118.9(4)
O2 N2 C4 118.6(3)
C11 C12 C13 120.7(3)
C11 C12 H12 119.6
C13 C12 H12 119.6
C12 C11 C10 119.1(4)
C12 C11 H11 120.5
C10 C11 H11 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.732(3)
Cl2 C10 1.743(4)
O5 C18 1.227(4)
O4 C13 1.363(4)
O4 H2 0.88(4)
C1 N1 1.393(4)
C1 C6 1.393(4)
C1 C2 1.408(4)
N4 C14 1.392(4)
N4 C18 1.413(4)
N4 C19 1.473(4)
N1 C7 1.378(4)
N1 H1 0.88(4)
N6 C16 1.336(4)
N6 C15 1.364(4)
O3 C7 1.224(4)
O6 C14 1.233(3)
N3 C14 1.365(4)
N3 C15 1.381(4)
N3 C20 1.463(4)
N5 C16 1.329(5)
N5 C17 1.383(4)
N5 H5A 0.95(3)
C15 C17 1.364(4)
C18 C17 1.418(5)
C8 C9 1.395(4)
C8 C13 1.404(4)
C8 C7 1.497(5)
C6 C5 1.376(5)
C6 H6 0.9300
C13 C12 1.391(5)
C5 C4 1.383(4)
C5 H5 0.9300
C2 C3 1.363(5)
C4 C3 1.381(5)
C4 N2 1.462(5)
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C10 C9 1.366(5)
C10 C11 1.389(5)
C3 H3 0.9300
C9 H9 0.9300
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C16 H16 0.9300
O2 N2 1.220(4)
N2 O1 1.211(4)
C12 C11 1.372(5)
C12 H12 0.9300
C11 H11 0.9300
