#------------------------------------------------------------------------------
#$Date: 2015-05-13 22:38:55 +0300 (Wed, 13 May 2015) $
#$Revision: 136362 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/99/2019941.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2019941
loop_
_publ_author_name
'Sovago, Ioana'
'Bond, Andrew D.'
_publ_section_title
;
 Expanding the structural landscape of niclosamide: a high Z'
 polymorph, two new solvates and monohydrate HA
;
_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 , H2 O'
_chemical_formula_moiety         'C13 H8 Cl2 N2 O4, H2 O'
_chemical_formula_sum            'C13 H10 Cl2 N2 O5'
_chemical_formula_weight         345.13
_chemical_name_common            'niclosamide monohydrate A'
_chemical_name_systematic
;
5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide monohydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           'TOPAS + manual editing'
_cell_angle_alpha                90
_cell_angle_beta                 92.874(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.81342(19)
_cell_length_b                   16.1428(7)
_cell_length_c                   23.0650(11)
_cell_measurement_temperature    298(2)
_cell_volume                     1418.08(12)
_computing_cell_refinement       'TOPAS Academic (Coelho, 2007)'
_computing_data_collection       'Data Collector (PANalytical, 2010)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_structure_refinement  'TOPAS Academic (Coelho, 2007)'
_computing_structure_solution    'DASH (David et al., 2006)'
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device_type  'PANalytical X'Pert Pro'
_diffrn_radiation_monochromator  none
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_exptl_absorpt_coefficient_mu    4.378
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             704
_pd_calc_method                  'Rietveld refinement'
_pd_char_colour                  white
_pd_char_particle_morphology     powder
_pd_meas_2theta_range_inc        0.026
_pd_meas_2theta_range_max        37.47513
_pd_meas_2theta_range_min        5.00113
_pd_meas_number_of_points        1249
_pd_meas_scan_method             cont
_pd_prep_temperature             298(2)
_pd_proc_2theta_range_inc        0.026
_pd_proc_2theta_range_max        37.47513
_pd_proc_2theta_range_min        5.00113
_pd_proc_info_excluded_regions   none
_pd_proc_ls_background_function  'Chebyshev function with 20 terms'
_pd_proc_ls_pref_orient_corr
;
 March (1932)
 Direction:    [1 0 0]   (corresponds to needle axis)
 Scale factor: 0.942 (3)
;
_pd_proc_ls_prof_R_factor        0.0232
_pd_proc_ls_prof_wR_expected     0.0226
_pd_proc_ls_prof_wR_factor       0.0321
_pd_proc_wavelength              1.5418
_pd_spec_mounting                'borosilicate capillary'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_spec_size_axial              3.0
_pd_spec_size_equat              0.1
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.11
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.42
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           fullcycle
_refine_ls_number_constraints    0
_refine_ls_number_parameters     148
_refine_ls_number_restraints     80
_refine_ls_R_factor_all          0.014
_refine_ls_shift/su_max          0.001
_refine_ls_weighting_scheme      sigma
_cod_data_source_file            fa3363sup1.cif
_cod_data_source_block           niclosamide_HA
_cod_original_cell_volume        1418.08(11)
_cod_database_code               2019941
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl CL1 -0.0615(10) 0.7759(2) 0.29885(15) 0.048(3) 1 4
Cl CL2 0.7616(11) 0.3943(2) 0.06746(15) 0.048(3) 1 4
O O1 -0.343(3) 0.5946(4) 0.5304(2) 0.048(3) 1 4
O O2 -0.482(2) 0.7234(3) 0.5052(3) 0.048(3) 1 4
O O3 0.283(2) 0.4644(3) 0.2704(3) 0.048(3) 1 4
O O4 0.3496(16) 0.6957(3) 0.18573(18) 0.048(3) 1 4
N N1 -0.3828(17) 0.6516(2) 0.49257(15) 0.048(3) 1 4
N N2 0.1497(15) 0.6027(2) 0.27318(14) 0.048(3) 1 4
C C1 0.0208(12) 0.6116(2) 0.32708(13) 0.048(3) 1 4
C C2 -0.0914(15) 0.6917(2) 0.34455(16) 0.048(3) 1 4
C C3 -0.2278(15) 0.7038(2) 0.39850(15) 0.048(3) 1 4
C C4 -0.2520(16) 0.6370(2) 0.43623(15) 0.048(3) 1 4
C C5 -0.1460(15) 0.5574(2) 0.42043(15) 0.048(3) 1 4
C C6 -0.0103(13) 0.5456(2) 0.36647(15) 0.048(3) 1 4
C C7 0.2824(15) 0.5339(2) 0.24699(16) 0.048(3) 1 4
C C8 0.4149(15) 0.5484(2) 0.18837(15) 0.048(3) 1 4
C C9 0.5197(14) 0.4775(2) 0.15847(15) 0.048(3) 1 4
C C10 0.6454(15) 0.4832(2) 0.10376(16) 0.048(3) 1 4
C C11 0.6670(14) 0.5597(2) 0.07633(15) 0.048(3) 1 4
C C12 0.5632(14) 0.6295(2) 0.10464(15) 0.048(3) 1 4
C C13 0.4392(14) 0.6260(2) 0.15971(15) 0.048(3) 1 4
H H2 0.17088 0.65695 0.24914 0.058 1 4
H H3 -0.31272 0.76515 0.41136 0.058 1 4
H H4 0.41554 0.75044 0.16678 0.058 1 4
H H5 -0.17290 0.50556 0.44992 0.058 1 4
H H6 0.06269 0.48397 0.35309 0.058 1 4
H H9 0.49949 0.41774 0.17991 0.058 1 4
H H11 0.76197 0.56404 0.03266 0.058 1 4
H H12 0.57692 0.68960 0.08338 0.058 1 4
O O1W 0.4905(11) 0.8479(5) 0.14960(17) 0.048(3) 1 4
H H1W 0.56546 0.86438 0.11104 0.058 1 4
H H2W 0.58308 0.88856 0.17851 0.058 1 4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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_publ_flag
C13 O4 H4 117.7 no
O2 N1 O1 122.4(5) no
O2 N1 C4 118.9(4) no
O1 N1 C4 117.8(5) no
C1 N2 C7 130.0(3) no
C1 N2 H2 115.9 no
C7 N2 H2 113.9 no
N2 C1 C2 118.6(3) no
N2 C1 C6 123.5(3) no
C2 C1 C6 117.8(3) no
C1 C2 CL1 120.7(3) no
C1 C2 C3 120.9(3) no
CL1 C2 C3 118.3(3) no
C2 C3 C4 119.4(3) no
C2 C3 H3 120.2 no
C4 C3 H3 120.3 no
C3 C4 N1 118.4(3) no
C3 C4 C5 121.3(4) no
N1 C4 C5 120.3(3) no
C4 C5 C6 119.0(3) no
C4 C5 H5 120.4 no
C6 C5 H5 120.5 no
C5 C6 C1 121.5(3) no
C5 C6 H6 119.7 no
C1 C6 H6 118.7 no
N2 C7 O3 122.1(5) no
N2 C7 C8 115.0(3) no
O3 C7 C8 122.9(4) no
C7 C8 C9 115.9(3) no
C7 C8 C13 126.5(3) no
C9 C8 C13 117.6(3) no
C8 C9 C10 121.1(3) no
C8 C9 H9 118.1 no
C10 C9 H9 120.8 no
C9 C10 CL2 119.8(3) no
C9 C10 C11 120.6(4) no
CL2 C10 C11 119.5(3) no
C10 C11 C12 119.2(4) no
C10 C11 H11 120.5 no
C12 C11 H11 120.3 no
C11 C12 C13 121.7(3) no
C11 C12 H12 119.7 no
C13 C12 H12 118.5 no
C12 C13 C8 119.9(3) no
C12 C13 O4 119.3(3) no
C8 C13 O4 120.8(4) no
H1W O1W H2W 108.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
CL1 C2 1.728(5) no
CL2 C10 1.730(5) no
O1 N1 1.272(7) no
O2 N1 1.258(7) no
O3 C7 1.245(6) no
O4 C13 1.328(6) no
O4 H4 1.02 no
N1 C4 1.435(6) no
N2 C1 1.367(5) no
N2 C7 1.373(5) no
N2 H2 1.04 no
C1 C2 1.425(5) no
C1 C6 1.410(5) no
C2 C3 1.387(6) no
C3 C4 1.392(5) no
C3 H3 1.09 no
C4 C5 1.401(5) no
C5 C6 1.385(6) no
C5 H5 1.09 no
C6 H6 1.08 no
C7 C8 1.486(6) no
C8 C9 1.404(5) no
C8 C13 1.421(5) no
C9 C10 1.375(6) no
C9 H9 1.09 no
C10 C11 1.391(5) no
C11 C12 1.371(5) no
C11 H11 1.09 no
C12 C13 1.379(5) no
C12 H12 1.09 no
O1W H1W 0.98 no
O1W H2W 0.99 no
loop_
_pd_meas_2theta_scan
_pd_proc_ls_weight
_pd_proc_intensity_total
_pd_calc_intensity_total
5.00113 0.00067 1489.96020 1552.39266
5.02713 0.00063 1584.03990 1545.87097
5.05313 0.00063 1584.03990 1539.78121
5.07913 0.00065 1528.81020 1534.06688
5.10513 0.00066 1505.43990 1528.67659
5.13113 0.00066 1505.43990 1523.56377
5.15713 0.00067 1489.96020 1518.68633
5.18313 0.00065 1528.81020 1514.00633
5.20913 0.00064 1560.25000 1509.48971
5.23513 0.00066 1521.00000 1505.10600
5.26113 0.00067 1497.69010 1500.82806
5.28713 0.00067 1482.25000 1496.63183
5.31313 0.00066 1513.21010 1492.49613
5.33913 0.00065 1528.81020 1488.40236
5.36513 0.00067 1482.25000 1484.33439
5.39113 0.00067 1482.25000 1480.27829
5.41713 0.00066 1521.00000 1476.22219
5.44313 0.00066 1505.43990 1472.15607
5.46913 0.00068 1466.88990 1468.07163
5.49513 0.00069 1459.24010 1463.96215
5.52113 0.00070 1436.41020 1459.82228
5.54713 0.00071 1413.76010 1455.64799
5.57313 0.00071 1406.25000 1451.43637
5.59913 0.00072 1391.28990 1447.18558
5.62513 0.00069 1459.24010 1442.89470
5.65113 0.00070 1436.41020 1438.56362
5.67713 0.00071 1406.25000 1434.19299
5.70313 0.00069 1459.24010 1429.78408
5.72913 0.00069 1459.24010 1425.33874
5.75513 0.00071 1413.76010 1420.85930
5.78113 0.00073 1369.00000 1416.34852
5.80713 0.00072 1391.28990 1411.80950
5.83313 0.00069 1444.00000 1407.24564
5.85913 0.00069 1451.61020 1402.66057
5.88513 0.00075 1339.56020 1398.05813
5.91113 0.00074 1354.24000 1393.44227
5.93713 0.00071 1413.76010 1388.81711
5.96313 0.00071 1406.25000 1384.18684
5.98913 0.00074 1346.89000 1379.55571
6.01513 0.00074 1354.24000 1374.92802
6.04113 0.00076 1310.44010 1370.30808
6.06713 0.00073 1369.00000 1365.70027
6.09313 0.00076 1317.68990 1361.10901
6.11913 0.00071 1406.25000 1356.53880
6.14513 0.00072 1383.84010 1351.99431
6.17113 0.00073 1376.41020 1347.48055
6.19713 0.00073 1361.61010 1343.00314
6.22313 0.00074 1354.24000 1338.56907
6.24913 0.00072 1383.84010 1334.18882
6.27513 0.00075 1324.96010 1329.88692
6.30113 0.00076 1317.68990 1325.74904
6.32713 0.00074 1346.89000 1321.84073
6.35313 0.00077 1296.00000 1318.12828
6.37913 0.00076 1310.44010 1314.71781
6.40513 0.00074 1354.24000 1311.70875
6.43113 0.00075 1339.56020 1309.19066
6.45713 0.00078 1288.81010 1307.21243
6.48313 0.00080 1246.09000 1305.99433
6.50913 0.00076 1310.44010 1305.81097
6.53513 0.00077 1303.21020 1307.09013
6.56113 0.00075 1324.96010 1310.54117
6.58713 0.00073 1369.00000 1317.56068
6.61313 0.00075 1339.56020 1331.17524
6.63913 0.00075 1324.96010 1358.30052
6.66513 0.00076 1317.68990 1411.03183
6.69113 0.00065 1536.64000 1442.02499
6.71713 0.00074 1346.89000 1348.77963
6.74313 0.00079 1267.36010 1281.53400
6.76913 0.00077 1303.21020 1263.44313
6.79513 0.00078 1288.81010 1256.89793
6.82113 0.00081 1239.04000 1252.39447
6.84713 0.00080 1246.09000 1248.55717
6.87313 0.00082 1225.00000 1245.05304
6.89913 0.00082 1225.00000 1241.75047
6.92513 0.00079 1267.36010 1238.58669
6.95113 0.00081 1239.04000 1235.52658
6.97713 0.00081 1239.04000 1232.54003
7.00313 0.00079 1260.25000 1229.62775
7.02913 0.00078 1274.49010 1226.85682
7.05513 0.00079 1267.36010 1224.16070
7.08113 0.00080 1253.16020 1221.55160
7.10713 0.00083 1211.03990 1219.13925
7.13313 0.00084 1197.16020 1216.87862
7.15913 0.00082 1225.00000 1214.82907
7.18513 0.00081 1239.04000 1213.08623
7.21113 0.00085 1183.36010 1211.86142
7.23713 0.00081 1239.04000 1211.76015
7.26313 0.00079 1260.25000 1212.81088
7.28913 0.00081 1232.01010 1212.92739
7.31513 0.00084 1197.16020 1214.03557
7.34113 0.00082 1225.00000 1218.81928
7.36713 0.00079 1260.25000 1230.70103
7.39313 0.00080 1246.09000 1252.37665
7.41913 0.00078 1288.81010 1284.35632
7.44513 0.00075 1339.56020 1331.35190
7.47113 0.00074 1354.24000 1398.83922
7.49713 0.00071 1406.25000 1494.51034
7.52313 0.00066 1513.21010 1630.61604
7.54913 0.00056 1780.84010 1827.78661
7.57513 0.00047 2125.21020 2124.99758
7.60113 0.00038 2621.44020 2609.32537
7.62713 0.00028 3540.25000 3493.62723
7.65313 0.00020 5097.96040 5070.05946
7.67913 0.00017 5867.55960 6062.22201
7.70513 0.00024 4147.36040 3904.59758
7.73113 0.00048 2079.36010 1959.82511
7.75713 0.00076 1317.68990 1412.88894
7.78313 0.00084 1190.25000 1287.94171
7.80913 0.00085 1183.36010 1240.64763
7.83513 0.00086 1162.81020 1214.94653
7.86113 0.00087 1156.00000 1198.71481
7.88713 0.00084 1197.16020 1187.41637
7.91313 0.00083 1204.09010 1178.92864
7.93913 0.00085 1169.64000 1172.10682
7.96513 0.00088 1142.43990 1166.21088
7.99113 0.00087 1156.00000 1160.46221
8.01713 0.00088 1142.43990 1154.85544
8.04313 0.00091 1095.61010 1151.27782
8.06913 0.00089 1122.25000 1148.02880
8.09513 0.00089 1128.96020 1144.28629
8.12113 0.00091 1102.24000 1140.24447
8.14713 0.00088 1135.69010 1138.19880
8.17313 0.00088 1135.69010 1136.24560
8.19913 0.00090 1108.88990 1134.45053
8.22513 0.00090 1108.88990 1132.65503
8.25113 0.00088 1142.43990 1130.85884
8.27713 0.00086 1162.81020 1129.06176
8.30313 0.00089 1128.96020 1127.26362
8.32913 0.00089 1122.25000 1125.46430
8.35513 0.00087 1156.00000 1123.66370
8.38113 0.00089 1128.96020 1121.86177
8.40713 0.00088 1135.69010 1120.05849
8.43313 0.00089 1128.96020 1118.25387
8.45913 0.00088 1135.69010 1116.44795
8.48513 0.00088 1135.69010 1114.64082
8.51113 0.00092 1082.41020 1112.83258
8.53713 0.00089 1122.25000 1111.02336
8.56313 0.00088 1142.43990 1109.21332
8.58913 0.00088 1142.43990 1107.40263
8.61513 0.00091 1102.24000 1105.59152
8.64113 0.00088 1135.69010 1103.78020
8.66713 0.00088 1135.69010 1101.96892
8.69313 0.00089 1122.25000 1100.15794
8.71913 0.00092 1089.00000 1098.34756
8.74513 0.00088 1142.43990 1096.53807
8.77113 0.00086 1162.81020 1094.72979
8.79713 0.00092 1082.41020 1092.92303
8.82313 0.00088 1135.69010 1091.11906
8.84913 0.00094 1062.76010 1089.32496
8.87513 0.00096 1043.28990 1087.55839
8.90113 0.00089 1122.25000 1085.84697
8.92713 0.00089 1122.25000 1084.23372
8.95313 0.00088 1142.43990 1082.79001
8.97913 0.00094 1062.76010 1081.63525
9.00513 0.00092 1089.00000 1080.96656
9.03113 0.00090 1108.88990 1081.13210
9.05713 0.00090 1115.56010 1082.84024
9.08313 0.00088 1135.69010 1087.96051
9.10913 0.00089 1128.96020 1099.05736
9.13513 0.00083 1211.03990 1115.69303
9.16113 0.00087 1156.00000 1145.38583
9.18713 0.00076 1317.68990 1213.91797
9.21313 0.00073 1361.61010 1344.08525
9.23913 0.00064 1560.25000 1556.37735
9.26513 0.00056 1797.76010 1882.01447
9.29113 0.00043 2323.24000 2382.15175
9.31713 0.00033 3036.01030 3160.31446
9.34313 0.00023 4303.35990 4436.13610
9.36913 0.00015 6855.84030 6792.68802
9.39513 0.00008 11363.55960 11410.52134
9.42113 0.00003 17529.76170 17247.13056
9.44713 0.00004 16744.36330 16763.56893
9.47313 0.00013 7867.69090 8204.03209
9.49913 0.00037 2683.24000 2647.23129
9.52513 0.00070 1421.29000 1495.09850
9.55113 0.00079 1267.36010 1283.94208
9.57713 0.00081 1232.01010 1199.28515
9.60313 0.00087 1149.21010 1151.41580
9.62913 0.00091 1102.24000 1120.64322
9.65513 0.00092 1089.00000 1098.61701
9.68113 0.00092 1082.41020 1080.48042
9.70713 0.00094 1069.29000 1063.22823
9.73313 0.00091 1102.24000 1048.41486
9.75913 0.00095 1049.76010 1037.32745
9.78513 0.00098 1024.00000 1029.59942
9.81113 0.00098 1024.00000 1027.42831
9.83713 0.00094 1069.29000 1025.95803
9.86313 0.00103 973.44010 1024.50077
9.88913 0.00102 979.69010 1023.05656
9.91513 0.00099 1011.24010 1021.62544
9.94113 0.00097 1030.41020 1020.20742
9.96713 0.00096 1036.84010 1018.80252
9.99313 0.00098 1017.61000 1017.41072
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_cod_database_fobs_code 2019941
