#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/97/2209709.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_2209709
loop_
_publ_author_name
'Ke-Jian Li'
'Shu-Rong Ban'
'Xiao-Feng Cheng'
'Hong-Jun Liu'
'Wen-Bin Chen'
_publ_section_title
;
 1-Butyl-3-(4-chloro-1,3-benzothiazol-2-yl)urea monohydrate
;
_journal_coeditor_code           XU2050
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2755
_journal_page_last               o2756
_journal_paper_doi               10.1107/S1600536806021118
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H14 Cl N3 O S, H2 O'
_chemical_formula_moiety         'C12 H14 Cl N3 O S, H2 O'
_chemical_formula_sum            'C12 H16 Cl N3 O2 S'
_chemical_formula_weight         301.8
_chemical_name_systematic
;
1-Butyl-3-(4-chlorobenzo[d]thiazol-2-yl)urea hydrate
;
_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                96.568(4)
_cell_angle_beta                 91.451(4)
_cell_angle_gamma                114.775(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0075(16)
_cell_length_b                   7.6324(18)
_cell_length_c                   14.826(3)
_cell_measurement_reflns_used    1660
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.8
_cell_volume                     712.9(3)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.027
_diffrn_reflns_av_sigmaI/netI    0.042
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3635
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.8
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2507
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.035
_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)+(0.0458P)²+0.1733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.086
_refine_ls_wR_factor_ref         0.096
_reflns_number_gt                1939
_reflns_number_total             2507
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2050.cif
_cod_data_source_block           I
_cod_database_code               2209709
_cod_database_fobs_code          2209709
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 1.64422(9) 1.31310(10) 0.30212(4) 0.0601(2) Uani d . 1
S S1 0.85576(8) 0.87168(8) 0.17938(4) 0.04047(18) Uani d . 1
O O1 0.7215(2) 0.6745(2) 0.01314(10) 0.0467(4) Uani d . 1
N N1 1.2642(3) 1.0310(2) 0.16851(11) 0.0337(4) Uani d . 1
N N2 1.0790(3) 0.8288(2) 0.03696(11) 0.0368(4) Uani d . 1
H H2 1.1964 0.8539 0.0129 0.044 Uiso calc R 1
N N3 0.9211(3) 0.6183(3) -0.09393(12) 0.0420(4) Uani d . 1
H H3 1.0471 0.6459 -0.1091 0.050 Uiso calc R 1
C C1 1.3802(3) 1.2164(3) 0.32347(14) 0.0392(5) Uani d . 1
C C2 1.3225(4) 1.2626(3) 0.40802(15) 0.0470(6) Uani d . 1
H H2A 1.4255 1.3445 0.4534 0.056 Uiso calc R 1
C C3 1.1119(4) 1.1874(3) 0.42564(16) 0.0506(6) Uani d . 1
H H3A 1.0751 1.2195 0.4830 0.061 Uiso calc R 1
C C4 0.9565(4) 1.0664(3) 0.36005(15) 0.0469(6) Uani d . 1
H H4 0.8153 1.0169 0.3720 0.056 Uiso calc R 1
C C5 1.0162(3) 1.0197(3) 0.27484(14) 0.0371(5) Uani d . 1
C C6 1.2279(3) 1.0927(3) 0.25531(13) 0.0332(5) Uani d . 1
C C7 1.0856(3) 0.9153(3) 0.12350(13) 0.0323(5) Uani d . 1
C C8 0.8935(3) 0.7023(3) -0.01451(14) 0.0348(5) Uani d . 1
C C9 0.7433(3) 0.4812(3) -0.15551(14) 0.0408(5) Uani d . 1
H H9A 0.6423 0.5357 -0.1635 0.049 Uiso calc R 1
H H9B 0.6737 0.3615 -0.1294 0.049 Uiso calc R 1
C C10 0.8155(3) 0.4373(3) -0.24681(13) 0.0378(5) Uani d . 1
H H10A 0.8852 0.5578 -0.2724 0.045 Uiso calc R 1
H H10B 0.9179 0.3848 -0.2381 0.045 Uiso calc R 1
C C11 0.6375(4) 0.2946(3) -0.31352(15) 0.0440(5) Uani d . 1
H H11A 0.5363 0.3482 -0.3232 0.053 Uiso calc R 1
H H11B 0.5661 0.1749 -0.2876 0.053 Uiso calc R 1
C C12 0.7120(5) 0.2484(4) -0.40465(16) 0.0625(7) Uani d . 1
H H12A 0.7831 0.3664 -0.4307 0.094 Uiso calc R 1
H H12B 0.5928 0.1597 -0.4450 0.094 Uiso calc R 1
H H12C 0.8073 0.1898 -0.3959 0.094 Uiso calc R 1
O O2 0.6166(2) 0.2439(2) 0.06225(11) 0.0519(4) Uani d D 1
H H2B 0.5382 0.1697 0.0980 0.062 Uiso d RD 1
H H2C 0.5680 0.3147 0.0388 0.062 Uiso d RD 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'
S S 0.1246 0.1234 '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
C5 S1 C7 87.86(10)
C7 N1 C6 109.48(17)
C7 N2 C8 123.79(17)
C7 N2 H2 118.1
C8 N2 H2 118.1
C8 N3 C9 121.55(18)
C8 N3 H3 119.2
C9 N3 H3 119.2
C2 C1 C6 120.4(2)
C2 C1 Cl1 119.75(18)
C6 C1 Cl1 119.81(16)
C1 C2 C3 120.3(2)
C1 C2 H2A 119.9
C3 C2 H2A 119.9
C4 C3 C2 121.2(2)
C4 C3 H3A 119.4
C2 C3 H3A 119.4
C3 C4 C5 118.2(2)
C3 C4 H4 120.9
C5 C4 H4 120.9
C4 C5 C6 121.8(2)
C4 C5 S1 128.39(18)
C6 C5 S1 109.77(15)
N1 C6 C1 126.35(19)
N1 C6 C5 115.56(18)
C1 C6 C5 118.08(18)
N1 C7 N2 120.95(18)
N1 C7 S1 117.29(15)
N2 C7 S1 121.75(15)
O1 C8 N3 124.48(19)
O1 C8 N2 120.86(19)
N3 C8 N2 114.65(18)
N3 C9 C10 110.71(18)
N3 C9 H9A 109.5
C10 C9 H9A 109.5
N3 C9 H9B 109.5
C10 C9 H9B 109.5
H9A C9 H9B 108.1
C11 C10 C9 113.10(18)
C11 C10 H10A 109.0
C9 C10 H10A 109.0
C11 C10 H10B 109.0
C9 C10 H10B 109.0
H10A C10 H10B 107.8
C10 C11 C12 112.8(2)
C10 C11 H11A 109.0
C12 C11 H11A 109.0
C10 C11 H11B 109.0
C12 C11 H11B 109.0
H11A C11 H11B 107.8
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
H2B O2 H2C 115.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.734(2) ?
S1 C5 1.741(2) y
S1 C7 1.753(2) y
O1 C8 1.223(2) y
N1 C6 1.386(2) y
N1 C7 1.300(3) y
N2 C7 1.365(3) y
N2 C8 1.391(3) y
N2 H2 0.8600 ?
N3 C8 1.333(3) y
N3 C9 1.453(3) y
N3 H3 0.8600 ?
C1 C2 1.379(3) ?
C1 C6 1.390(3) ?
C2 C3 1.386(3) ?
C2 H2A 0.9300 ?
C3 C4 1.372(3) ?
C3 H3A 0.9300 ?
C4 C5 1.395(3) ?
C4 H4 0.9300 ?
C5 C6 1.401(3) ?
C9 C10 1.508(3) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C11 1.507(3) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 C12 1.518(3) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
O2 H2B 0.8525 ?
O2 H2C 0.8486 ?
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
N2 H2 O2 2_765 0.86 2.05 2.826(2) 149
N3 H3 O2 2_765 0.86 2.21 2.962(2) 147
O2 H2B N1 1_445 0.85 2.13 2.939(2) 158
O2 H2C O1 2_665 0.85 2.19 2.918(2) 144
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
C6 C1 C2 C3 -0.6(3)
Cl1 C1 C2 C3 179.49(17)
C1 C2 C3 C4 -0.1(4)
C2 C3 C4 C5 0.4(3)
C3 C4 C5 C6 -0.1(3)
C3 C4 C5 S1 -179.91(17)
C7 S1 C5 C4 -178.6(2)
C7 S1 C5 C6 1.53(15)
C7 N1 C6 C1 179.51(19)
C7 N1 C6 C5 0.2(2)
C2 C1 C6 N1 -178.38(19)
Cl1 C1 C6 N1 1.6(3)
C2 C1 C6 C5 0.9(3)
Cl1 C1 C6 C5 -179.16(15)
C4 C5 C6 N1 178.76(18)
S1 C5 C6 N1 -1.4(2)
C4 C5 C6 C1 -0.6(3)
S1 C5 C6 C1 179.29(15)
C6 N1 C7 N2 -177.55(17)
C6 N1 C7 S1 1.1(2)
C8 N2 C7 N1 179.38(18)
C8 N2 C7 S1 0.8(3)
C5 S1 C7 N1 -1.58(17)
C5 S1 C7 N2 177.04(17)
C9 N3 C8 O1 -0.6(3)
C9 N3 C8 N2 179.55(17)
C7 N2 C8 O1 6.4(3)
C7 N2 C8 N3 -173.81(18)
C8 N3 C9 C10 169.40(19)
N3 C9 C10 C11 179.66(18)
C9 C10 C11 C12 -178.95(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127839
