#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/11/7201154.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7201154
loop_
_publ_author_name
'Nauha, Elisa'
'Saxell, Heidi'
'Nissinen, Maija'
'Kolehmainen, Erkki'
'Schäfer, Ansgar'
'Schlecker, Rainer'
_publ_section_title
;
 Polymorphism and versatile solvate formation of thiophanate-methyl
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              2536
_journal_paper_doi               10.1039/b905511h
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C12 H14 N4 O4 S2'
_chemical_formula_sum            'C12 H14 N4 O4 S2'
_chemical_formula_weight         342.39
_chemical_name_common            thiophanate-methyl
_chemical_name_systematic
;
?
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.48(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9524(18)
_cell_length_b                   20.073(4)
_cell_length_c                   8.9959(18)
_cell_measurement_temperature    173(2)
_cell_volume                     1541.9(6)
_computing_cell_refinement       Denzo
_computing_data_collection       'Collect (Bruker AXS, 2004)'
_computing_data_reduction        Denzo
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Nonius Kappa CCD Apex II detector'
_diffrn_measurement_method       'psi and omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2657
_diffrn_reflns_theta_full        66.82
_diffrn_reflns_theta_max         66.82
_diffrn_reflns_theta_min         4.41
_exptl_absorpt_coefficient_mu    3.356
_exptl_absorpt_correction_T_max  0.6889
_exptl_absorpt_correction_T_min  0.5834
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
Denzo (Otwinowski, Borek, Majewski & Minor,2003)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0415
_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)+(0.0614P)²+1.0354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                2371
_reflns_number_total             2657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905511h.txt
_cod_data_source_block           TM_formII
_cod_original_cell_volume        1541.9(5)
_cod_original_sg_symbol_H-M      p2(1)/c
_cod_database_code               7201154
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.22538(7) 0.63460(3) 0.25773(7) 0.0372(2) Uani 1 1 d . . .
S1 S -0.57951(7) 0.67693(3) -0.12234(7) 0.0372(2) Uani 1 1 d . . .
N1 N -0.4737(2) 0.78949(9) 0.0216(2) 0.0328(4) Uani 1 1 d D . .
H1 H -0.557(2) 0.8075(13) -0.046(3) 0.039 Uiso 1 1 d D . .
N2 N -0.3321(2) 0.69565(9) 0.1256(2) 0.0312(4) Uani 1 1 d D . .
H2 H -0.269(3) 0.7245(12) 0.190(3) 0.037 Uiso 1 1 d D . .
N3 N -0.0562(2) 0.66903(9) 0.0672(2) 0.0291(4) Uani 1 1 d D . .
H3 H -0.115(3) 0.7005(11) 0.006(3) 0.035 Uiso 1 1 d D . .
N4 N 0.1351(2) 0.74940(10) 0.1186(2) 0.0336(4) Uani 1 1 d D . .
H4 H 0.228(2) 0.7604(14) 0.181(3) 0.040 Uiso 1 1 d D . .
O1 O -0.2590(2) 0.82140(8) 0.2232(2) 0.0418(4) Uani 1 1 d . . .
O2 O -0.4331(2) 0.89618(8) 0.0825(2) 0.0387(4) Uani 1 1 d . . .
O3 O -0.0908(2) 0.79289(8) -0.0485(2) 0.0406(4) Uani 1 1 d . . .
O4 O 0.1064(2) 0.85820(8) 0.0906(2) 0.0417(4) Uani 1 1 d . . .
C1 C -0.3494(3) 0.94835(13) 0.1849(3) 0.0455(6) Uani 1 1 d . . .
H1A H -0.3595 0.9417 0.2894 0.068 Uiso 1 1 calc R . .
H1B H -0.3935 0.9917 0.1445 0.068 Uiso 1 1 calc R . .
H1C H -0.2385 0.9469 0.1903 0.068 Uiso 1 1 calc R . .
C2 C -0.3771(3) 0.83477(12) 0.1205(3) 0.0335(5) Uani 1 1 d . . .
C3 C -0.4537(3) 0.72156(11) 0.0166(3) 0.0289(5) Uani 1 1 d . . .
C4 C -0.2846(3) 0.62758(11) 0.1256(3) 0.0288(5) Uani 1 1 d . . .
C5 C -0.3754(3) 0.57580(12) 0.1540(3) 0.0365(5) Uani 1 1 d . . .
H5 H -0.4716 0.5851 0.1741 0.044 Uiso 1 1 calc R . .
C6 C -0.3251(3) 0.51066(12) 0.1528(3) 0.0375(6) Uani 1 1 d . . .
H6 H -0.3876 0.4751 0.1708 0.045 Uiso 1 1 calc R . .
C7 C -0.1844(3) 0.49723(11) 0.1256(3) 0.0340(5) Uani 1 1 d . . .
H7 H -0.1508 0.4524 0.1242 0.041 Uiso 1 1 calc R . .
C8 C -0.0916(3) 0.54873(10) 0.1001(3) 0.0303(5) Uani 1 1 d . . .
H8 H 0.0060 0.5392 0.0831 0.036 Uiso 1 1 calc R . .
C9 C -0.1419(2) 0.61423(10) 0.0996(2) 0.0264(5) Uani 1 1 d . . .
C10 C 0.0927(3) 0.68493(11) 0.1411(3) 0.0280(5) Uani 1 1 d . . .
C11 C 0.0375(3) 0.80002(11) 0.0442(3) 0.0321(5) Uani 1 1 d . . .
C12 C 0.0190(4) 0.91646(12) 0.0198(3) 0.0455(7) Uani 1 1 d . . .
H12A H -0.0006 0.9147 -0.0933 0.068 Uiso 1 1 calc R . .
H12B H 0.0793 0.9566 0.0616 0.068 Uiso 1 1 calc R . .
H12C H -0.0811 0.9176 0.0432 0.068 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C2 127.6(2) . . ?
C3 N1 H1 118.2(19) . . ?
C2 N1 H1 114.2(18) . . ?
C3 N2 C4 123.34(19) . . ?
C3 N2 H2 116.4(18) . . ?
C4 N2 H2 119.2(18) . . ?
C10 N3 C9 126.99(19) . . ?
C10 N3 H3 116.7(17) . . ?
C9 N3 H3 114.7(17) . . ?
C11 N4 C10 127.0(2) . . ?
C11 N4 H4 117.8(19) . . ?
C10 N4 H4 113.0(19) . . ?
C2 O2 C1 114.99(19) . . ?
C11 O4 C12 115.76(19) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 125.2(2) . . ?
O1 C2 N1 125.6(2) . . ?
O2 C2 N1 109.16(19) . . ?
N2 C3 N1 116.6(2) . . ?
N2 C3 S1 124.03(17) . . ?
N1 C3 S1 119.37(17) . . ?
C5 C4 C9 120.3(2) . . ?
C5 C4 N2 121.6(2) . . ?
C9 C4 N2 118.2(2) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 119.7(2) . . ?
C8 C9 N3 122.6(2) . . ?
C4 C9 N3 117.70(19) . . ?
N3 C10 N4 115.30(19) . . ?
N3 C10 S2 125.68(17) . . ?
N4 C10 S2 119.01(17) . . ?
O3 C11 O4 125.2(2) . . ?
O3 C11 N4 125.6(2) . . ?
O4 C11 N4 109.3(2) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C10 1.668(2) . ?
S1 C3 1.670(2) . ?
N1 C3 1.378(3) . ?
N1 C2 1.380(3) . ?
N1 H1 0.883(17) . ?
N2 C3 1.333(3) . ?
N2 C4 1.431(3) . ?
N2 H2 0.892(17) . ?
N3 C10 1.338(3) . ?
N3 C9 1.421(3) . ?
N3 H3 0.896(17) . ?
N4 C11 1.376(3) . ?
N4 C10 1.380(3) . ?
N4 H4 0.882(17) . ?
O1 C2 1.207(3) . ?
O2 C2 1.336(3) . ?
O2 C1 1.446(3) . ?
O3 C11 1.209(3) . ?
O4 C11 1.328(3) . ?
O4 C12 1.444(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.390(3) . ?
C4 C9 1.392(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S2 0.883(17) 2.492(18) 3.372(2) 175(2) 4_475
N2 H2 O1 0.892(17) 1.97(2) 2.688(3) 137(2) .
N2 H2 O3 0.892(17) 2.44(2) 3.084(3) 130(2) 4_576
N3 H3 O3 0.896(17) 1.95(2) 2.677(2) 137(2) .
N3 H3 O1 0.896(17) 2.52(2) 3.088(3) 122(2) 4_575
N4 H4 S1 0.882(17) 2.419(19) 3.251(2) 157(2) 4_676
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 -5.9(4) . . . . ?
C1 O2 C2 N1 175.5(2) . . . . ?
C3 N1 C2 O1 -1.9(4) . . . . ?
C3 N1 C2 O2 176.7(2) . . . . ?
C4 N2 C3 N1 -172.4(2) . . . . ?
C4 N2 C3 S1 7.5(3) . . . . ?
C2 N1 C3 N2 4.3(4) . . . . ?
C2 N1 C3 S1 -175.52(19) . . . . ?
C3 N2 C4 C5 -69.1(3) . . . . ?
C3 N2 C4 C9 112.3(2) . . . . ?
C9 C4 C5 C6 -1.5(3) . . . . ?
N2 C4 C5 C6 180.0(2) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C4 0.4(3) . . . . ?
C7 C8 C9 N3 -177.0(2) . . . . ?
C5 C4 C9 C8 0.8(3) . . . . ?
N2 C4 C9 C8 179.45(19) . . . . ?
C5 C4 C9 N3 178.4(2) . . . . ?
N2 C4 C9 N3 -3.0(3) . . . . ?
C10 N3 C9 C8 -56.2(3) . . . . ?
C10 N3 C9 C4 126.3(2) . . . . ?
C9 N3 C10 N4 -162.3(2) . . . . ?
C9 N3 C10 S2 16.3(3) . . . . ?
C11 N4 C10 N3 7.9(3) . . . . ?
C11 N4 C10 S2 -170.85(19) . . . . ?
C12 O4 C11 O3 -1.4(4) . . . . ?
C12 O4 C11 N4 178.8(2) . . . . ?
C10 N4 C11 O3 -21.2(4) . . . . ?
C10 N4 C11 O4 158.6(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2297683
