#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/07/2210787.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_2210787
loop_
_publ_author_name
'Hartung, Jens'
'Schneiders, Nina'
'Bergsträsser, Uwe'
_publ_section_title
;
 3-(1-Methyl-1-phenylethoxy)-1,3-thiazole-2(3H)-thione: a
 tertiary thiohydroxamic acid O-ester
;
_journal_coeditor_code           SJ2119
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4713
_journal_page_last               o4714
_journal_paper_doi               10.1107/S1600536806038360
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H15 N O S2'
_chemical_formula_moiety         'C13 H15 N O S2'
_chemical_formula_sum            'C13 H15 N O S2'
_chemical_formula_weight         265.38
_chemical_name_systematic
;
3-(1-Methyl-1-phenylethoxy)-1,3-thiazole-2(3H)-thione
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.16(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7504(16)
_cell_length_b                   18.363(4)
_cell_length_c                   9.788(2)
_cell_measurement_reflns_used    5396
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      2.2
_cell_volume                     1361.8(5)
_computing_cell_refinement       EXPOSE
_computing_data_collection       'EXPOSE in IPDS Software (Stoe & Cie, 1998)'
_computing_data_reduction        EXPOSE
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1994)'
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       φ
_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  0.0904
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10870
_diffrn_reflns_theta_full        24.20
_diffrn_reflns_theta_max         24.20
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0346
_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)+(0.0355P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                1278
_reflns_number_total             2099
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2119.cif
_cod_data_source_block           I
_cod_original_cell_volume        1361.9(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210787
_cod_database_fobs_code          2210787
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
S S1 0.05856(9) 0.42736(4) 0.40161(8) 0.0582(2) Uani d . 1
O O1 0.06957(19) 0.41044(8) 0.01508(17) 0.0436(4) Uani d . 1
S S2 0.37305(9) 0.40749(5) 0.27429(9) 0.0695(3) Uani d . 1
C C2 0.1576(3) 0.41465(12) 0.2618(3) 0.0444(6) Uani d . 1
N N3 0.0275(2) 0.41269(10) 0.1441(2) 0.0415(5) Uani d . 1
C C4 -0.1455(3) 0.42650(12) 0.1604(3) 0.0448(6) Uani d . 1
C C5 -0.1477(3) 0.43484(14) 0.2936(3) 0.0567(7) Uani d . 1
H H5 -0.2501 0.4438 0.3262 0.085 Uiso calc R 1
C C6 -0.2938(3) 0.43151(15) 0.0367(3) 0.0604(7) Uani d . 1
H H6A -0.2505 0.4227 -0.0468 0.091 Uiso calc PR 0.50
H H6B -0.3451 0.4793 0.0325 0.091 Uiso calc PR 0.50
H H6C -0.3817 0.3958 0.0444 0.091 Uiso calc PR 0.50
H H6D -0.4011 0.4425 0.0669 0.091 Uiso calc PR 0.50
H H6E -0.3065 0.3859 -0.0124 0.091 Uiso calc PR 0.50
H H6F -0.2698 0.4694 -0.0243 0.091 Uiso calc PR 0.50
C C7 0.0743(3) 0.33593(13) -0.0495(3) 0.0471(6) Uani d . 1
C C8 0.0960(4) 0.27702(14) 0.0602(3) 0.0685(9) Uani d . 1
H H8A 0.2037 0.2848 0.1277 0.103 Uiso calc R 1
H H8B 0.0998 0.2304 0.0167 0.103 Uiso calc R 1
H H8C -0.0019 0.2784 0.1061 0.103 Uiso calc R 1
C C9 0.2375(3) 0.34231(18) -0.1127(3) 0.0757(9) Uani d . 1
H H9A 0.2191 0.3798 -0.1826 0.114 Uiso calc R 1
H H9B 0.2581 0.2968 -0.1546 0.114 Uiso calc R 1
H H9C 0.3379 0.3544 -0.0406 0.114 Uiso calc R 1
C C10 -0.0927(3) 0.32904(12) -0.1629(3) 0.0427(6) Uani d . 1
C C11 -0.1394(3) 0.38403(14) -0.2596(3) 0.0537(7) Uani d . 1
H H11 -0.0659 0.4243 -0.2560 0.064 Uiso calc R 1
C C12 -0.2918(4) 0.38095(17) -0.3610(3) 0.0671(8) Uani d . 1
H H12 -0.3224 0.4194 -0.4233 0.081 Uiso calc R 1
C C13 -0.3986(4) 0.32065(18) -0.3697(3) 0.0737(9) Uani d . 1
H H13 -0.5013 0.3179 -0.4386 0.088 Uiso calc R 1
C C14 -0.3539(4) 0.26538(17) -0.2778(4) 0.0730(9) Uani d . 1
H H14 -0.4254 0.2243 -0.2847 0.088 Uiso calc R 1
C C15 -0.2026(4) 0.26941(14) -0.1732(3) 0.0585(7) Uani d . 1
H H15 -0.1749 0.2315 -0.1094 0.070 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'
S S 0.1246 0.1234 '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'
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
C2 S1 C5 91.99(13) y
N3 O1 C7 116.41(16) y
N3 C2 S2 128.04(19) y
N3 C2 S1 107.55(16) y
S2 C2 S1 124.40(15) y
C2 N3 O1 120.20(18) y
C2 N3 C4 116.9(2) y
O1 N3 C4 121.86(19) y
C5 C4 N3 110.2(2) y
C5 C4 C6 129.0(2) y
N3 C4 C6 120.7(2) y
C4 C5 S1 113.1(2) y
C4 C5 H5 123.4 ?
S1 C5 H5 123.4 ?
C4 C6 H6A 109.5 ?
C4 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C4 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
C4 C6 H6D 109.5 ?
H6A C6 H6D 141.1 ?
H6B C6 H6D 56.3 ?
H6C C6 H6D 56.3 ?
C4 C6 H6E 109.5 ?
H6A C6 H6E 56.3 ?
H6B C6 H6E 141.1 ?
H6C C6 H6E 56.3 ?
H6D C6 H6E 109.5 ?
C4 C6 H6F 109.5 ?
H6A C6 H6F 56.3 ?
H6B C6 H6F 56.3 ?
H6C C6 H6F 141.1 ?
H6D C6 H6F 109.5 ?
H6E C6 H6F 109.5 ?
C8 C7 O1 111.1(2) ?
C8 C7 C10 114.1(2) ?
O1 C7 C10 106.76(18) ?
C8 C7 C9 111.5(2) ?
O1 C7 C9 101.28(19) ?
C10 C7 C9 111.2(2) ?
C7 C8 H8A 109.5 ?
C7 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C7 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C7 C9 H9A 109.5 ?
C7 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C7 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C15 C10 C11 117.6(2) ?
C15 C10 C7 122.5(2) ?
C11 C10 C7 119.9(2) ?
C12 C11 C10 121.8(2) ?
C12 C11 H11 119.1 ?
C10 C11 H11 119.1 ?
C13 C12 C11 119.5(3) ?
C13 C12 H12 120.3 ?
C11 C12 H12 120.3 ?
C14 C13 C12 119.8(3) ?
C14 C13 H13 120.1 ?
C12 C13 H13 120.1 ?
C13 C14 C15 120.6(3) ?
C13 C14 H14 119.7 ?
C15 C14 H14 119.7 ?
C10 C15 C14 120.7(3) ?
C10 C15 H15 119.7 ?
C14 C15 H15 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 1.720(3) y
S1 C5 1.727(3) y
O1 N3 1.370(2) y
O1 C7 1.511(3) y
S2 C2 1.654(2) y
C2 N3 1.362(3) y
N3 C4 1.406(3) y
C4 C5 1.317(4) y
C4 C6 1.487(4) y
C5 H5 0.9300 ?
C6 H6A 0.9600 ?
C6 H6B 0.9600 ?
C6 H6C 0.9600 ?
C6 H6D 0.9600 ?
C6 H6E 0.9600 ?
C6 H6F 0.9600 ?
C7 C8 1.509(4) ?
C7 C10 1.523(3) ?
C7 C9 1.524(4) ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 C15 1.378(3) ?
C10 C11 1.379(3) ?
C11 C12 1.375(4) ?
C11 H11 0.9300 ?
C12 C13 1.374(4) ?
C12 H12 0.9300 ?
C13 C14 1.352(4) ?
C13 H13 0.9300 ?
C14 C15 1.387(4) ?
C14 H14 0.9300 ?
C15 H15 0.9300 ?
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
C5 H5 S2 1_455 0.93 2.93 3.713(3) 142.2
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
_geom_torsion_publ_flag
C5 S1 C2 N3 -3.45(18) ?
C5 S1 C2 S2 175.86(17) ?
S2 C2 N3 O1 -5.9(3) y
S1 C2 N3 O1 173.41(14) ?
S2 C2 N3 C4 -174.52(17) ?
S1 C2 N3 C4 4.8(2) ?
C7 O1 N3 C2 95.6(2) y
C7 O1 N3 C4 -96.3(2) ?
C2 N3 C4 C5 -3.7(3) ?
O1 N3 C4 C5 -172.2(2) ?
C2 N3 C4 C6 175.0(2) ?
O1 N3 C4 C6 6.5(3) ?
N3 C4 C5 S1 0.8(3) ?
C6 C4 C5 S1 -177.8(2) ?
C2 S1 C5 C4 1.6(2) ?
N3 O1 C7 C8 -20.5(3) ?
N3 O1 C7 C10 104.5(2) ?
N3 O1 C7 C9 -139.0(2) ?
C8 C7 C10 C15 -7.5(3) ?
O1 C7 C10 C15 -130.7(2) ?
C9 C7 C10 C15 119.7(3) ?
C8 C7 C10 C11 172.0(2) ?
O1 C7 C10 C11 48.9(3) ?
C9 C7 C10 C11 -60.8(3) ?
C15 C10 C11 C12 1.5(4) ?
C7 C10 C11 C12 -178.1(3) ?
C10 C11 C12 C13 -2.0(4) ?
C11 C12 C13 C14 0.7(5) ?
C12 C13 C14 C15 1.0(5) ?
C11 C10 C15 C14 0.2(4) ?
C7 C10 C15 C14 179.8(3) ?
C13 C14 C15 C10 -1.5(5) ?
