#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/03/2230311.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_2230311
loop_
_publ_author_name
'Lu, Xu-Jia'
'Zhao, Hong-Bin'
'Chen, Liang'
'Yang, De-Liang'
'Wang, Bang-Ying'
_publ_section_title
;
 [(1,3-Benzothiazol-2-yl)aminocarbonyl]methyl
 piperidine-1-carbodithioate monohydrate
;
_journal_coeditor_code           FJ2417
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1488
_journal_paper_doi               10.1107/S1600536811018460
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H17 N3 O S3, H2 O'
_chemical_formula_moiety         'C15 H17 N3 O S3, H2 O'
_chemical_formula_sum            'C15 H19 N3 O2 S3'
_chemical_formula_weight         369.39
_chemical_name_systematic
;
{[(1,3-Benzothiazol-2-yl)aminocarbonyl]methyl} piperidine-1-carbodithioate
monohydrate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 113.133(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6326(3)
_cell_length_b                   12.0735(3)
_cell_length_c                   14.7824(4)
_cell_measurement_reflns_used    8358
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.00
_cell_volume                     1745.08(8)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15147
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.9178
_exptl_absorpt_correction_T_min  0.9178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0336
_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)+(0.0424P)²+0.6208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                3497
_reflns_number_total             3992
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2417.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230311
_cod_database_fobs_code          2230311
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_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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S3 -0.11155(5) 0.39341(3) 0.39288(3) 0.04084(12) Uani d . 1 1 . .
S S2 0.14706(5) 0.19374(3) 0.16270(3) 0.04125(12) Uani d . 1 1 . .
S S1 0.34529(6) 0.24704(5) 0.36726(3) 0.05848(15) Uani d . 1 1 . .
O O1 0.00460(15) 0.32824(10) 0.26734(10) 0.0505(3) Uani d . 1 1 . .
N N3 -0.14307(15) 0.20161(10) 0.46198(10) 0.0387(3) Uani d . 1 1 . .
N N1 0.37483(17) 0.30273(14) 0.20291(11) 0.0504(4) Uani d . 1 1 . .
N N2 -0.02961(10) 0.18869(7) 0.35648(7) 0.0398(3) Uani d . 1 1 . .
H H3 -0.0250 0.1209 0.3715 0.060 Uiso d R 1 1 . .
C C15 -0.19188(10) 0.38955(7) 0.47513(7) 0.0390(3) Uani d R 1 1 . .
C C14 -0.24377(10) 0.47707(7) 0.51145(7) 0.0524(4) Uani d R 1 1 . .
H H14 -0.2375 0.5497 0.4927 0.063 Uiso calc R 1 1 . .
C C13 -0.3046(2) 0.45284(17) 0.57595(18) 0.0621(5) Uani d . 1 1 . .
H H13 -0.3404 0.5099 0.6008 0.075 Uiso calc R 1 1 . .
C C12 -0.3132(2) 0.34427(18) 0.60443(17) 0.0607(5) Uani d . 1 1 . .
H H12 -0.3539 0.3300 0.6486 0.073 Uiso calc R 1 1 . .
C C11 -0.2626(2) 0.25758(15) 0.56845(15) 0.0506(4) Uani d . 1 1 . .
H H11 -0.2696 0.1852 0.5874 0.061 Uiso calc R 1 1 . .
C C10 -0.20087(17) 0.28022(13) 0.50311(12) 0.0381(3) Uani d . 1 1 . .
C C9 -0.09440(16) 0.24949(12) 0.40459(11) 0.0344(3) Uani d . 1 1 . .
C C8 0.01508(18) 0.23052(13) 0.28907(12) 0.0389(3) Uani d . 1 1 . .
C C7 0.0712(2) 0.14189(14) 0.24244(13) 0.0450(4) Uani d . 1 1 . .
H H7A -0.0025 0.0920 0.2054 0.054 Uiso calc R 1 1 . .
H H7B 0.1392 0.0992 0.2943 0.054 Uiso calc R 1 1 . .
C C6 0.30123(18) 0.25403(13) 0.24634(12) 0.0401(3) Uani d . 1 1 . .
C C1 0.3334(2) 0.31304(17) 0.09552(13) 0.0524(5) Uani d . 1 1 . .
H H1A 0.2466 0.2758 0.0618 0.063 Uiso calc R 1 1 . .
H H1B 0.4010 0.2776 0.0763 0.063 Uiso calc R 1 1 . .
C C2 0.3200(2) 0.43266(18) 0.06582(15) 0.0607(5) Uani d . 1 1 . .
H H2A 0.2454 0.4658 0.0785 0.073 Uiso calc R 1 1 . .
H H2B 0.2983 0.4380 -0.0042 0.073 Uiso calc R 1 1 . .
C C3 0.4502(3) 0.4956(2) 0.1215(2) 0.0794(7) Uani d . 1 1 . .
H H3A 0.4357 0.5738 0.1057 0.095 Uiso calc R 1 1 . .
H H3B 0.5218 0.4697 0.1016 0.095 Uiso calc R 1 1 . .
C C4 0.4948(3) 0.4796(2) 0.23209(18) 0.0701(6) Uani d . 1 1 . .
H H4A 0.5832 0.5144 0.2661 0.084 Uiso calc R 1 1 . .
H H4B 0.4295 0.5156 0.2534 0.084 Uiso calc R 1 1 . .
C C5 0.5044(2) 0.3595(2) 0.25880(17) 0.0632(5) Uani d . 1 1 . .
H H5A 0.5774 0.3253 0.2449 0.076 Uiso calc R 1 1 . .
H H5B 0.5261 0.3520 0.3287 0.076 Uiso calc R 1 1 . .
O O2 0.99835(17) 0.03537(10) 0.61071(10) 0.0591(4) Uani d . 1 1 . .
H H2'A 0.9501 0.0735 0.5538 0.089 Uiso d R 1 1 . .
H H2'B 1.0111 0.0822 0.6617 0.089 Uiso d R 1 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 S3 C9 . . 87.99(6) ?
C6 S2 C7 . . 102.54(8) ?
C9 N3 C10 . . 109.94(13) ?
C6 N1 C5 . . 122.35(16) ?
C6 N1 C1 . . 124.96(15) ?
C5 N1 C1 . . 112.56(16) ?
C8 N2 C9 . . 124.72(11) ?
C8 N2 H3 . . 123.5 ?
C9 N2 H3 . . 111.7 ?
C14 C15 C10 . . 121.23(8) ?
C14 C15 S3 . . 128.8 ?
C10 C15 S3 . . 109.98(9) ?
C13 C14 C15 . . 118.06(9) ?
C13 C14 H14 . . 121.0 ?
C15 C14 H14 . . 121.0 ?
C14 C13 C12 . . 120.96(16) ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C11 C12 C13 . . 121.18(18) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
C12 C11 C10 . . 118.79(17) ?
C12 C11 H11 . . 120.6 ?
C10 C11 H11 . . 120.6 ?
C11 C10 N3 . . 125.33(15) ?
C11 C10 C15 . . 119.77(14) ?
N3 C10 C15 . . 114.89(13) ?
N3 C9 N2 . . 120.70(13) ?
N3 C9 S3 . . 117.19(12) ?
N2 C9 S3 . . 122.09(10) ?
O1 C8 N2 . . 122.14(14) ?
O1 C8 C7 . . 125.17(15) ?
N2 C8 C7 . . 112.63(13) ?
C8 C7 S2 . . 114.45(12) ?
C8 C7 H7A . . 108.6 ?
S2 C7 H7A . . 108.6 ?
C8 C7 H7B . . 108.6 ?
S2 C7 H7B . . 108.6 ?
H7A C7 H7B . . 107.6 ?
N1 C6 S1 . . 124.85(14) ?
N1 C6 S2 . . 113.75(12) ?
S1 C6 S2 . . 121.40(10) ?
N1 C1 C2 . . 110.48(16) ?
N1 C1 H1A . . 109.6 ?
C2 C1 H1A . . 109.6 ?
N1 C1 H1B . . 109.6 ?
C2 C1 H1B . . 109.6 ?
H1A C1 H1B . . 108.1 ?
C1 C2 C3 . . 111.35(19) ?
C1 C2 H2A . . 109.4 ?
C3 C2 H2A . . 109.4 ?
C1 C2 H2B . . 109.4 ?
C3 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
C2 C3 C4 . . 110.69(19) ?
C2 C3 H3A . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
C5 C4 C3 . . 111.4(2) ?
C5 C4 H4A . . 109.3 ?
C3 C4 H4A . . 109.3 ?
C5 C4 H4B . . 109.3 ?
C3 C4 H4B . . 109.3 ?
H4A C4 H4B . . 108.0 ?
N1 C5 C4 . . 110.63(18) ?
N1 C5 H5A . . 109.5 ?
C4 C5 H5A . . 109.5 ?
N1 C5 H5B . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
H2'A O2 H2'B . . 107.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S3 C15 . 1.7395(10) ?
S3 C9 . 1.7486(15) ?
S2 C6 . 1.7757(18) ?
S2 C7 . 1.7828(17) ?
S1 C6 . 1.6624(16) ?
O1 C8 . 1.2163(19) ?
N3 C9 . 1.291(2) ?
N3 C10 . 1.394(2) ?
N1 C6 . 1.329(2) ?
N1 C5 . 1.468(3) ?
N1 C1 . 1.477(2) ?
N2 C8 . 1.3586(18) ?
N2 C9 . 1.3799(17) ?
N2 H3 . 0.8445 ?
C15 C14 . 1.3936 ?
C15 C10 . 1.3978(18) ?
C14 C13 . 1.377(2) ?
C14 H14 . 0.9300 ?
C13 C12 . 1.391(3) ?
C13 H13 . 0.9300 ?
C12 C11 . 1.376(3) ?
C12 H12 . 0.9300 ?
C11 C10 . 1.392(2) ?
C11 H11 . 0.9300 ?
C8 C7 . 1.517(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C1 C2 . 1.500(3) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.508(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.525(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.496(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
O2 H2'A . 0.9186 ?
O2 H2'B . 0.9083 ?
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 H3 O2 3_656 0.844 1.910 2.745(2) 170
O2 H2'A N3 1_655 0.919 2.040 2.920(2) 160
O2 H2'B O1 4_666 0.908 1.923 2.821(2) 169
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 S3 C15 C14 . . . . 179.51(6) ?
C9 S3 C15 C10 . . . . -0.94(11) ?
C10 C15 C14 C13 . . . . -0.05(14) ?
S3 C15 C14 C13 . . . . 179.45(15) ?
C15 C14 C13 C12 . . . . 0.4(3) ?
C14 C13 C12 C11 . . . . -0.7(4) ?
C13 C12 C11 C10 . . . . 0.6(3) ?
C12 C11 C10 N3 . . . . 178.85(19) ?
C12 C11 C10 C15 . . . . -0.3(3) ?
C9 N3 C10 C11 . . . . -179.96(17) ?
C9 N3 C10 C15 . . . . -0.8(2) ?
C14 C15 C10 C11 . . . . 0.00(19) ?
S3 C15 C10 C11 . . . . -179.59(14) ?
C14 C15 C10 N3 . . . . -179.20(9) ?
S3 C15 C10 N3 . . . . 1.21(17) ?
C10 N3 C9 N2 . . . . 178.87(14) ?
C10 N3 C9 S3 . . . . 0.03(19) ?
C8 N2 C9 N3 . . . . 174.61(15) ?
C8 N2 C9 S3 . . . . -6.6(2) ?
C15 S3 C9 N3 . . . . 0.55(13) ?
C15 S3 C9 N2 . . . . -178.26(14) ?
C9 N2 C8 O1 . . . . 2.2(3) ?
C9 N2 C8 C7 . . . . -175.06(14) ?
O1 C8 C7 S2 . . . . 8.9(3) ?
N2 C8 C7 S2 . . . . -173.96(12) ?
C6 S2 C7 C8 . . . . 71.97(15) ?
C5 N1 C6 S1 . . . . -1.7(3) ?
C1 N1 C6 S1 . . . . -177.38(15) ?
C5 N1 C6 S2 . . . . 178.72(16) ?
C1 N1 C6 S2 . . . . 3.1(2) ?
C7 S2 C6 N1 . . . . -177.71(13) ?
C7 S2 C6 S1 . . . . 2.73(12) ?
C6 N1 C1 C2 . . . . 118.0(2) ?
C5 N1 C1 C2 . . . . -58.0(2) ?
N1 C1 C2 C3 . . . . 55.5(2) ?
C1 C2 C3 C4 . . . . -53.5(3) ?
C2 C3 C4 C5 . . . . 53.3(3) ?
C6 N1 C5 C4 . . . . -118.4(2) ?
C1 N1 C5 C4 . . . . 57.7(2) ?
C3 C4 C5 N1 . . . . -54.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656699
