#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/97/2209794.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_2209794
loop_
_publ_author_name
'Bing Liu'
'Ke-Jian Li'
'Hai-Bin Song'
'Qiang Liu'
_publ_section_title
;
 1-(4-Chloro-1,3-benzothiazol-2-yl)-3-propylurea monohydrate
;
_journal_coeditor_code           CI2092
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3322
_journal_page_last               o3323
_journal_paper_doi               10.1107/S1600536806026596
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H12 Cl N3 O S, H2 O'
_chemical_formula_moiety         'C11 H12 Cl N3 O S, H2 O'
_chemical_formula_sum            'C11 H14 Cl N3 O2 S'
_chemical_formula_weight         287.76
_chemical_name_systematic
;
1-(4-Chloro-1,3-benzothiazol-2-yl)-3-propylurea monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                97.509(5)
_cell_angle_beta                 94.600(8)
_cell_angle_gamma                111.419(8)
_cell_formula_units_Z            2
_cell_length_a                   6.8742(15)
_cell_length_b                   7.2537(16)
_cell_length_c                   14.729(2)
_cell_measurement_reflns_used    2025
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.4
_cell_volume                     671.3(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure (Rigaku/MSC, 2005)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6546
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         2.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_T_max  0.9575
_exptl_absorpt_correction_T_min  0.8928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0371
_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)+(0.0605P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                2212
_reflns_number_total             3134
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2092.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2209794
_cod_database_fobs_code          2209794
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 0.65745(8) 0.20674(9) -0.34818(3) 0.0739(2) Uani d . 1
S S1 0.18237(6) 0.09879(6) -0.08242(3) 0.04468(14) Uani d . 1
O O1 0.31248(16) 0.21940(18) 0.09797(8) 0.0486(3) Uani d . 1
O O2 0.05218(19) 0.4550(2) 0.11095(11) 0.0631(4) Uani d D 1
H H2A 0.109(3) 0.372(3) 0.1144(18) 0.112(10) Uiso d D 1
H H2B 0.150(3) 0.5680(18) 0.1315(14) 0.075(7) Uiso d D 1
N N1 0.53997(19) 0.22033(19) -0.15000(9) 0.0416(3) Uani d . 1
N N2 0.58161(19) 0.2885(2) 0.01096(9) 0.0449(3) Uani d D 1
H H2 0.7187(15) 0.342(3) 0.0103(13) 0.064(6) Uiso d D 1
N N3 0.6492(2) 0.3636(2) 0.16931(9) 0.0459(3) Uani d D 1
H H3 0.7851(17) 0.397(3) 0.1604(14) 0.077(6) Uiso d D 1
C C1 0.4575(2) 0.2114(2) -0.07324(11) 0.0390(3) Uani d . 1
C C2 0.3809(2) 0.1313(2) -0.22443(11) 0.0410(4) Uani d . 1
C C3 0.4061(3) 0.1115(3) -0.31747(12) 0.0482(4) Uani d . 1
C C4 0.2329(3) 0.0166(3) -0.38434(13) 0.0565(5) Uani d . 1
H H4 0.2508 0.0019 -0.4464 0.068 Uiso calc R 1
C C5 0.0320(3) -0.0571(3) -0.35931(13) 0.0606(5) Uani d . 1
H H5 -0.0836 -0.1198 -0.4052 0.073 Uiso calc R 1
C C6 0.0004(3) -0.0393(3) -0.26848(12) 0.0532(4) Uani d . 1
H H6 -0.1347 -0.0892 -0.2521 0.064 Uiso calc R 1
C C7 0.1766(2) 0.0556(2) -0.20139(11) 0.0426(4) Uani d . 1
C C8 0.5028(2) 0.2867(2) 0.09500(11) 0.0394(4) Uani d . 1
C C9 0.5905(2) 0.3697(2) 0.26137(11) 0.0441(4) Uani d . 1
H H9A 0.5199 0.2335 0.2723 0.053 Uiso calc R 1
H H9B 0.4924 0.4373 0.2664 0.053 Uiso calc R 1
C C10 0.7810(3) 0.4783(3) 0.33358(12) 0.0516(4) Uani d . 1
H H10A 0.8797 0.4114 0.3281 0.062 Uiso calc R 1
H H10B 0.8508 0.6147 0.3229 0.062 Uiso calc R 1
C C11 0.7214(4) 0.4835(4) 0.42981(14) 0.0755(6) Uani d . 1
H H11A 0.8461 0.5524 0.4740 0.113 Uiso calc R 1
H H11B 0.6534 0.3486 0.4408 0.113 Uiso calc R 1
H H11C 0.6267 0.5528 0.4360 0.113 Uiso calc R 1
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'
S S 0.1246 0.1234 '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 S1 C1 87.74(7)
H2A O2 H2B 104.6(17)
C1 N1 C2 109.47(12)
C1 N2 C8 123.83(12)
C1 N2 H2 116.6(12)
C8 N2 H2 119.5(12)
C8 N3 C9 120.92(13)
C8 N3 H3 117.6(13)
C9 N3 H3 121.0(13)
N1 C1 N2 121.18(13)
N1 C1 S1 117.21(12)
N2 C1 S1 121.61(11)
N1 C2 C3 126.57(14)
N1 C2 C7 115.18(13)
C3 C2 C7 118.25(14)
C4 C3 C2 120.25(16)
C4 C3 Cl1 120.48(14)
C2 C3 Cl1 119.27(13)
C3 C4 C5 120.16(17)
C3 C4 H4 119.9
C5 C4 H4 119.9
C6 C5 C4 121.39(17)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C7 117.99(16)
C5 C6 H6 121.0
C7 C6 H6 121.0
C6 C7 C2 121.95(15)
C6 C7 S1 127.65(13)
C2 C7 S1 110.40(11)
O1 C8 N3 124.19(14)
O1 C8 N2 121.02(14)
N3 C8 N2 114.78(12)
N3 C9 C10 111.27(13)
N3 C9 H9A 109.4
C10 C9 H9A 109.4
N3 C9 H9B 109.4
C10 C9 H9B 109.4
H9A C9 H9B 108.0
C11 C10 C9 111.60(15)
C11 C10 H10A 109.3
C9 C10 H10A 109.3
C11 C10 H10B 109.3
C9 C10 H10B 109.3
H10A C10 H10B 108.0
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.7328(18)
S1 C7 1.7341(17)
S1 C1 1.7505(15)
O1 C8 1.2247(17)
O2 H2A 0.830(9)
O2 H2B 0.847(9)
N1 C1 1.304(2)
N1 C2 1.3861(19)
N2 C1 1.371(2)
N2 C8 1.390(2)
N2 H2 0.880(9)
N3 C8 1.333(2)
N3 C9 1.445(2)
N3 H3 0.901(9)
C2 C3 1.390(2)
C2 C7 1.397(2)
C3 C4 1.377(3)
C4 C5 1.387(2)
C4 H4 0.93
C5 C6 1.370(3)
C5 H5 0.93
C6 C7 1.393(2)
C6 H6 0.93
C9 C10 1.507(2)
C9 H9A 0.97
C9 H9B 0.97
C10 C11 1.506(3)
C10 H10A 0.97
C10 H10B 0.97
C11 H11A 0.96
C11 H11B 0.96
C11 H11C 0.96
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2A O1 . 0.830(9) 2.090(12) 2.891(2) 162(2) yes
O2 H2B N1 2_665 0.847(9) 2.092(13) 2.8816(19) 155(2) yes
N2 H2 O2 1_655 0.880(9) 2.426(14) 3.164(2) 142(2) yes
N3 H3 O2 1_655 0.901(9) 1.952(10) 2.8358(19) 167(2) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 N1 C1 N2 179.72(13)
C2 N1 C1 S1 -0.72(17)
C8 N2 C1 N1 178.80(14)
C8 N2 C1 S1 -0.7(2)
C7 S1 C1 N1 0.89(13)
C7 S1 C1 N2 -179.55(14)
C1 N1 C2 C3 -179.95(15)
C1 N1 C2 C7 0.09(19)
N1 C2 C3 C4 179.11(16)
C7 C2 C3 C4 -0.9(2)
N1 C2 C3 Cl1 -0.7(2)
C7 C2 C3 Cl1 179.22(12)
C2 C3 C4 C5 1.0(3)
Cl1 C3 C4 C5 -179.20(14)
C3 C4 C5 C6 -0.5(3)
C4 C5 C6 C7 0.1(3)
C5 C6 C7 C2 -0.1(3)
C5 C6 C7 S1 179.82(13)
N1 C2 C7 C6 -179.53(15)
C3 C2 C7 C6 0.5(2)
N1 C2 C7 S1 0.55(17)
C3 C2 C7 S1 -179.41(12)
C1 S1 C7 C6 179.33(17)
C1 S1 C7 C2 -0.75(11)
C9 N3 C8 O1 1.0(3)
C9 N3 C8 N2 -179.32(14)
C1 N2 C8 O1 -2.2(2)
C1 N2 C8 N3 178.14(14)
C8 N3 C9 C10 -175.28(14)
N3 C9 C10 C11 -179.44(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127796
