#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/13/2221398.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_2221398
loop_
_publ_author_name
'Arfan, Mohammad'
'Tahir, M. Nawaz'
'Shah, Muhammad Ishaq Ali'
'Khan, Rassol'
'Iqbal, Mohammad S.'
_publ_section_title
;
 2-[6-Thioxo-5-(2,4,6-trimethylphenyl)-1,3,5-thiadiazinan-3-yl]acetic
 acid
;
_journal_coeditor_code           HK2650
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o902
_journal_paper_doi               10.1107/S1600536809011027
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H18 N2 O2 S2'
_chemical_formula_moiety         'C14 H18 N2 O2 S2'
_chemical_formula_sum            'C14 H18 N2 O2 S2'
_chemical_formula_weight         310.42
_chemical_name_systematic
;
2-[6-Thioxo-5-(2,4,6-trimethylphenyl)-1,3,5-thiadiazinan-3-yl]acetic acid
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.9134(4)
_cell_length_b                   17.6934(11)
_cell_length_c                   24.9073(15)
_cell_measurement_reflns_used    3957
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.83
_cell_measurement_theta_min      2.44
_cell_volume                     3046.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.40
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18229
_diffrn_reflns_theta_full        28.83
_diffrn_reflns_theta_max         28.83
_diffrn_reflns_theta_min         2.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0462
_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)+(0.0418P)²+2.0698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                2120
_reflns_number_total             3957
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2650.cif
_cod_data_source_block           I
_cod_database_code               2221398
_cod_database_fobs_code          2221398
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.05204(10) 0.04895(4) 0.06455(3) 0.0462(3) Uani . . 1.000
S S2 -0.05342(10) 0.17988(4) 0.12532(3) 0.0502(3) Uani . . 1.000
O O1 0.4812(3) -0.14565(11) 0.15003(8) 0.0521(7) Uani . . 1.000
O O2 0.5343(4) -0.12709(11) 0.06276(9) 0.0639(9) Uani . . 1.000
N N1 0.3157(3) 0.14751(11) 0.10199(8) 0.0342(7) Uani . . 1.000
N N2 0.4407(3) 0.02387(12) 0.07081(9) 0.0409(8) Uani . . 1.000
C C1 0.3789(4) 0.21613(14) 0.12872(11) 0.0355(8) Uani . . 1.000
C C2 0.4250(4) 0.27902(14) 0.09806(11) 0.0382(9) Uani . . 1.000
C C3 0.4943(4) 0.34268(15) 0.12500(13) 0.0465(10) Uani . . 1.000
C C4 0.5158(4) 0.34412(16) 0.18049(13) 0.0494(10) Uani . . 1.000
C C5 0.4705(4) 0.27966(16) 0.20908(13) 0.0508(11) Uani . . 1.000
C C6 0.4040(4) 0.21442(15) 0.18430(12) 0.0423(9) Uani . . 1.000
C C7 0.3984(5) 0.28082(17) 0.03821(12) 0.0554(11) Uani . . 1.000
C C8 0.5854(5) 0.41477(18) 0.20860(15) 0.0693(14) Uani . . 1.000
C C9 0.3599(5) 0.14439(18) 0.21674(12) 0.0617(11) Uani . . 1.000
C C10 0.1280(4) 0.13078(13) 0.09810(10) 0.0356(8) Uani . . 1.000
C C11 0.2787(4) 0.01152(15) 0.03629(12) 0.0455(10) Uani . . 1.000
C C12 0.4777(4) 0.10269(14) 0.07749(13) 0.0451(10) Uani . . 1.000
C C13 0.4446(4) -0.02219(15) 0.11916(11) 0.0465(10) Uani . . 1.000
C C14 0.4921(4) -0.10347(15) 0.10630(13) 0.0444(10) Uani . . 1.000
H H1 0.49414 -0.19027 0.14189 0.0625 Uiso . . 1.000
H H3 0.52712 0.38540 0.10524 0.0556 Uiso . . 1.000
H H5 0.48496 0.27999 0.24620 0.0610 Uiso . . 1.000
H H7A 0.43567 0.32952 0.02473 0.0833 Uiso . . 1.000
H H7B 0.47751 0.24253 0.02198 0.0833 Uiso . . 1.000
H H7C 0.26508 0.27157 0.02968 0.0833 Uiso . . 1.000
H H8A 0.62761 0.45096 0.18238 0.1037 Uiso . . 1.000
H H8B 0.48151 0.43591 0.22931 0.1037 Uiso . . 1.000
H H8C 0.69113 0.40233 0.23195 0.1037 Uiso . . 1.000
H H9A 0.35779 0.15697 0.25423 0.0926 Uiso . . 1.000
H H9B 0.23599 0.12472 0.20634 0.0926 Uiso . . 1.000
H H9C 0.45771 0.10699 0.21028 0.0926 Uiso . . 1.000
H H11A 0.30305 0.03556 0.00195 0.0545 Uiso . . 1.000
H H11B 0.26428 -0.04230 0.03002 0.0545 Uiso . . 1.000
H H12A 0.59162 0.10850 0.09985 0.0542 Uiso . . 1.000
H H12B 0.50755 0.12413 0.04261 0.0542 Uiso . . 1.000
H H13A 0.54067 -0.00223 0.14376 0.0558 Uiso . . 1.000
H H13B 0.31956 -0.01976 0.13673 0.0558 Uiso . . 1.000
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'
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 S1 C11 . . . 102.97(13) no
C14 O1 H1 . . . 109.00 no
C1 N1 C12 . . . 113.8(2) no
C10 N1 C12 . . . 125.4(2) no
C1 N1 C10 . . . 120.8(2) no
C11 N2 C12 . . . 111.1(2) no
C12 N2 C13 . . . 116.6(2) no
C11 N2 C13 . . . 115.3(2) no
N1 C1 C2 . . . 119.2(2) no
C2 C1 C6 . . . 122.4(2) no
N1 C1 C6 . . . 118.3(2) no
C1 C2 C3 . . . 117.5(3) no
C1 C2 C7 . . . 122.4(2) no
C3 C2 C7 . . . 120.1(2) no
C2 C3 C4 . . . 122.0(3) no
C3 C4 C5 . . . 118.3(3) no
C5 C4 C8 . . . 121.1(3) no
C3 C4 C8 . . . 120.6(3) no
C4 C5 C6 . . . 122.2(3) no
C1 C6 C5 . . . 117.7(3) no
C1 C6 C9 . . . 121.6(2) no
C5 C6 C9 . . . 120.8(3) no
S1 C10 S2 . . . 113.48(16) no
S1 C10 N1 . . . 120.62(19) no
S2 C10 N1 . . . 125.84(19) no
S1 C11 N2 . . . 112.5(2) no
N1 C12 N2 . . . 115.4(2) no
N2 C13 C14 . . . 111.2(2) no
O1 C14 C13 . . . 110.5(2) no
O2 C14 C13 . . . 125.3(3) no
O1 C14 O2 . . . 124.2(2) no
C2 C3 H3 . . . 119.00 no
C4 C3 H3 . . . 119.00 no
C4 C5 H5 . . . 119.00 no
C6 C5 H5 . . . 119.00 no
C2 C7 H7A . . . 109.00 no
C2 C7 H7B . . . 109.00 no
C2 C7 H7C . . . 109.00 no
H7A C7 H7B . . . 109.00 no
H7A C7 H7C . . . 109.00 no
H7B C7 H7C . . . 109.00 no
C4 C8 H8A . . . 109.00 no
C4 C8 H8B . . . 109.00 no
C4 C8 H8C . . . 109.00 no
H8A C8 H8B . . . 109.00 no
H8A C8 H8C . . . 109.00 no
H8B C8 H8C . . . 109.00 no
C6 C9 H9A . . . 109.00 no
C6 C9 H9B . . . 109.00 no
C6 C9 H9C . . . 109.00 no
H9A C9 H9B . . . 109.00 no
H9A C9 H9C . . . 109.00 no
H9B C9 H9C . . . 109.00 no
S1 C11 H11A . . . 109.00 no
S1 C11 H11B . . . 109.00 no
N2 C11 H11A . . . 109.00 no
N2 C11 H11B . . . 109.00 no
H11A C11 H11B . . . 108.00 no
N1 C12 H12A . . . 108.00 no
N1 C12 H12B . . . 108.00 no
N2 C12 H12A . . . 108.00 no
N2 C12 H12B . . . 108.00 no
H12A C12 H12B . . . 107.00 no
N2 C13 H13A . . . 109.00 no
N2 C13 H13B . . . 109.00 no
C14 C13 H13A . . . 109.00 no
C14 C13 H13B . . . 109.00 no
H13A C13 H13B . . . 108.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C10 . . 1.752(2) no
S1 C11 . . 1.841(3) no
S2 C10 . . 1.670(3) no
O1 C14 . . 1.323(4) no
O2 C14 . . 1.198(4) no
O1 H1 . . 0.8200 no
N1 C1 . . 1.452(3) no
N1 C12 . . 1.502(3) no
N1 C10 . . 1.335(3) no
N2 C12 . . 1.428(3) no
N2 C13 . . 1.454(3) no
N2 C11 . . 1.429(4) no
C1 C6 . . 1.396(4) no
C1 C2 . . 1.387(4) no
C2 C3 . . 1.396(4) no
C2 C7 . . 1.502(4) no
C3 C4 . . 1.390(5) no
C4 C5 . . 1.381(4) no
C4 C8 . . 1.511(4) no
C5 C6 . . 1.387(4) no
C6 C9 . . 1.510(4) no
C13 C14 . . 1.510(4) no
C3 H3 . . 0.9300 no
C5 H5 . . 0.9300 no
C7 H7A . . 0.9600 no
C7 H7B . . 0.9600 no
C7 H7C . . 0.9600 no
C8 H8A . . 0.9600 no
C8 H8B . . 0.9600 no
C8 H8C . . 0.9600 no
C9 H9A . . 0.9600 no
C9 H9B . . 0.9600 no
C9 H9C . . 0.9600 no
C11 H11A . . 0.9700 no
C11 H11B . . 0.9700 no
C12 H12A . . 0.9700 no
C12 H12B . . 0.9700 no
C13 H13A . . 0.9700 no
C13 H13B . . 0.9700 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 C11 3.561(3) . 5_555 no
S1 S1 3.7226(11) . 5_555 no
S2 O1 3.187(2) . 7_555 no
S2 C6 3.540(3) . . no
S1 H7A 3.2000 . 3_455 no
S1 H3 3.1100 . 7_545 no
S1 H13B 2.8500 . . no
S2 H12A 2.8300 . 1_455 no
S2 H9A 3.0900 . 6_455 no
S2 H9B 3.0000 . . no
S2 H1 2.3700 . 7_555 no
O1 C3 3.352(3) . 7_545 no
O1 S2 3.187(2) . 7_545 no
O1 C2 3.367(3) . 7_545 no
O2 N2 2.756(3) . . no
O2 C11 3.094(4) . . no
O1 H5 2.9100 . 4_645 no
O2 H11B 2.5300 . . no
O2 H11A 2.5500 . 5_655 no
O2 H12B 2.6400 . 5_655 no
O2 H7C 2.8600 . 7_545 no
N2 O2 2.756(3) . . no
N2 C11 3.357(4) . 5_655 no
N1 H9B 2.6900 . . no
N1 H7B 2.8400 . . no
N1 H7C 2.8600 . . no
N2 H11A 2.7400 . 5_655 no
C2 O1 3.367(3) . 7_555 no
C2 C14 3.561(4) . 7_555 no
C3 O1 3.352(3) . 7_555 no
C3 C14 3.526(4) . 7_555 no
C6 S2 3.540(3) . . no
C7 C12 3.345(4) . . no
C7 C10 3.573(4) . . no
C9 C10 3.371(4) . . no
C10 C7 3.573(4) . . no
C10 C9 3.371(4) . . no
C10 C13 3.520(4) . . no
C11 S1 3.561(3) . 5_555 no
C11 O2 3.094(4) . . no
C11 N2 3.357(4) . 5_655 no
C11 C11 3.577(4) . 5_655 no
C12 C7 3.345(4) . . no
C13 C10 3.520(4) . . no
C14 C3 3.526(4) . 7_545 no
C14 C2 3.561(4) . 7_545 no
C1 H1 3.0800 . 7_555 no
C7 H12B 2.8800 . . no
C10 H9B 2.8000 . . no
C12 H7B 2.8300 . . no
C14 H11B 2.6900 . . no
H1 S2 2.3700 . 7_545 no
H1 C1 3.0800 . 7_545 no
H3 H7A 2.3200 . . no
H3 H8A 2.3500 . . no
H3 S1 3.1100 . 7_555 no
H5 H9A 2.3600 . . no
H5 O1 2.9100 . 4_655 no
H7A H3 2.3200 . . no
H7A S1 3.2000 . 3_555 no
H7B N1 2.8400 . . no
H7B C12 2.8300 . . no
H7B H12B 2.1700 . . no
H7B H7C 2.3800 . 3_555 no
H7C N1 2.8600 . . no
H7C H7B 2.3800 . 3_455 no
H7C O2 2.8600 . 7_555 no
H8A H3 2.3500 . . no
H8B H8C 2.3100 . 6_455 no
H8C H8B 2.3100 . 6_555 no
H9A H5 2.3600 . . no
H9A S2 3.0900 . 6_555 no
H9B S2 3.0000 . . no
H9B N1 2.6900 . . no
H9B C10 2.8000 . . no
H11A H12B 2.3400 . . no
H11A O2 2.5500 . 5_655 no
H11A N2 2.7400 . 5_655 no
H11B O2 2.5300 . . no
H11B C14 2.6900 . . no
H12A S2 2.8300 . 1_655 no
H12A H13A 2.2700 . . no
H12B C7 2.8800 . . no
H12B H7B 2.1700 . . no
H12B H11A 2.3400 . . no
H12B O2 2.6400 . 5_655 no
H13A H12A 2.2700 . . no
H13B S1 2.8500 . . no
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
O1 H1 S2 7_545 0.82 2.37 3.187(2) 174 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 S1 C10 S2 . . . . 176.80(15) no
C11 S1 C10 N1 . . . . -5.7(2) no
C10 S1 C11 N2 . . . . 35.4(2) no
C10 N1 C1 C2 . . . . -98.6(3) no
C10 N1 C1 C6 . . . . 85.9(3) no
C12 N1 C1 C2 . . . . 77.9(3) no
C12 N1 C1 C6 . . . . -97.7(3) no
C1 N1 C10 S1 . . . . 178.62(18) no
C1 N1 C10 S2 . . . . -4.3(3) no
C12 N1 C10 S1 . . . . 2.6(3) no
C12 N1 C10 S2 . . . . 179.7(2) no
C1 N1 C12 N2 . . . . 155.3(2) no
C10 N1 C12 N2 . . . . -28.4(4) no
C12 N2 C11 S1 . . . . -63.8(3) no
C13 N2 C11 S1 . . . . 71.7(2) no
C11 N2 C12 N1 . . . . 60.6(3) no
C13 N2 C12 N1 . . . . -74.3(3) no
C11 N2 C13 C14 . . . . 72.2(3) no
C12 N2 C13 C14 . . . . -154.8(2) no
N1 C1 C2 C3 . . . . -176.9(2) no
N1 C1 C2 C7 . . . . 4.5(4) no
C6 C1 C2 C3 . . . . -1.6(4) no
C6 C1 C2 C7 . . . . 179.9(3) no
N1 C1 C6 C5 . . . . 177.9(2) no
N1 C1 C6 C9 . . . . -2.3(4) no
C2 C1 C6 C5 . . . . 2.6(4) no
C2 C1 C6 C9 . . . . -177.7(3) no
C1 C2 C3 C4 . . . . -0.5(4) no
C7 C2 C3 C4 . . . . 178.1(3) no
C2 C3 C4 C5 . . . . 1.4(4) no
C2 C3 C4 C8 . . . . -178.1(3) no
C3 C4 C5 C6 . . . . -0.3(4) no
C8 C4 C5 C6 . . . . 179.2(3) no
C4 C5 C6 C1 . . . . -1.6(4) no
C4 C5 C6 C9 . . . . 178.7(3) no
N2 C13 C14 O1 . . . . -175.4(2) no
N2 C13 C14 O2 . . . . 4.7(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742049
