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#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/11/7201168.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_7201168
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, C6 H6'
_chemical_formula_sum            'C18 H20 N4 O4 S2'
_chemical_formula_weight         420.50
_chemical_name_common            'thiophanate-methyl, benzene'
_chemical_name_systematic
;
?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.946(4)
_cell_angle_beta                 101.732(5)
_cell_angle_gamma                96.683(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4106(8)
_cell_length_b                   9.9524(9)
_cell_length_c                   12.9517(12)
_cell_measurement_temperature    103(2)
_cell_volume                     991.01(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8528
_diffrn_reflns_theta_full        58.06
_diffrn_reflns_theta_max         58.06
_diffrn_reflns_theta_min         3.71
_exptl_absorpt_coefficient_mu    2.720
_exptl_absorpt_correction_T_max  0.8760
_exptl_absorpt_correction_T_min  0.7726
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0165(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0373
_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)+(0.0497P)²+0.3689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                2237
_reflns_number_total             2494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905511h.txt
_cod_data_source_block           TM_benzene
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               7201168
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.17080(8) 0.22742(7) 0.90664(5) 0.0355(2) Uani 1 1 d . . .
S2 S 0.24494(7) 0.39462(6) 0.46318(5) 0.0257(2) Uani 1 1 d . . .
O1 O 0.44715(19) -0.07763(17) 0.70336(13) 0.0278(4) Uani 1 1 d . . .
O2 O 0.56670(18) -0.08619(16) 0.87282(12) 0.0229(4) Uani 1 1 d . . .
O3 O 0.54952(18) 0.31170(17) 0.76600(13) 0.0252(4) Uani 1 1 d . . .
O4 O 0.74727(18) 0.46480(16) 0.74166(12) 0.0226(4) Uani 1 1 d . . .
N1 N 0.3800(2) 0.05286(19) 0.86313(16) 0.0198(5) Uani 1 1 d D . .
H1 H 0.409(3) 0.077(2) 0.9367(14) 0.024 Uiso 1 1 d D . .
N2 N 0.1966(2) 0.0638(2) 0.70819(15) 0.0193(5) Uani 1 1 d D . .
H2 H 0.245(3) 0.005(2) 0.6666(18) 0.023 Uiso 1 1 d D . .
N3 N 0.2554(2) 0.2834(2) 0.63004(16) 0.0199(5) Uani 1 1 d D . .
H3 H 0.325(2) 0.269(2) 0.6855(16) 0.024 Uiso 1 1 d D . .
N4 N 0.4985(2) 0.4108(2) 0.62611(16) 0.0209(5) Uani 1 1 d D . .
H4 H 0.552(3) 0.459(2) 0.5932(19) 0.025 Uiso 1 1 d D . .
C1 C 0.6653(3) -0.1829(3) 0.8180(2) 0.0334(7) Uani 1 1 d . . .
H1A H 0.5924 -0.2616 0.7539 0.050 Uiso 1 1 calc R . .
H1B H 0.7253 -0.2225 0.8715 0.050 Uiso 1 1 calc R . .
H1C H 0.7447 -0.1296 0.7919 0.050 Uiso 1 1 calc R . .
C2 C 0.4631(3) -0.0409(2) 0.8041(2) 0.0209(6) Uani 1 1 d . . .
C3 C 0.2502(3) 0.1103(2) 0.82012(19) 0.0205(6) Uani 1 1 d . . .
C4 C 0.0587(3) 0.1081(2) 0.65082(18) 0.0180(5) Uani 1 1 d . . .
C5 C -0.1011(3) 0.0393(2) 0.63621(19) 0.0237(6) Uani 1 1 d . . .
H5 H -0.1198 -0.0374 0.6641 0.028 Uiso 1 1 calc R . .
C6 C -0.2335(3) 0.0821(3) 0.5811(2) 0.0256(6) Uani 1 1 d . . .
H6 H -0.3433 0.0350 0.5710 0.031 Uiso 1 1 calc R . .
C7 C -0.2061(3) 0.1935(2) 0.54052(18) 0.0236(6) Uani 1 1 d . . .
H7 H -0.2976 0.2233 0.5033 0.028 Uiso 1 1 calc R . .
C8 C -0.0470(3) 0.2623(2) 0.55352(18) 0.0215(5) Uani 1 1 d . . .
H8 H -0.0296 0.3388 0.5253 0.026 Uiso 1 1 calc R . .
C9 C 0.0876(3) 0.2192(2) 0.60802(18) 0.0189(5) Uani 1 1 d . . .
C10 C 0.3310(3) 0.3585(2) 0.57728(19) 0.0209(6) Uani 1 1 d . . .
C11 C 0.5962(3) 0.3885(2) 0.71651(19) 0.0207(6) Uani 1 1 d . . .
C12 C 0.8676(3) 0.4427(3) 0.8293(2) 0.0291(6) Uani 1 1 d . . .
H12A H 0.8333 0.4721 0.8996 0.044 Uiso 1 1 calc R . .
H12B H 0.9760 0.5004 0.8395 0.044 Uiso 1 1 calc R . .
H12C H 0.8749 0.3406 0.8080 0.044 Uiso 1 1 calc R . .
C13 C 0.3103(3) 0.6693(3) 0.9576(2) 0.0298(6) Uani 1 1 d . . .
H13 H 0.3792 0.6410 1.0118 0.036 Uiso 1 1 calc R . .
C14 C 0.3076(3) 0.6116(3) 0.8457(2) 0.0314(6) Uani 1 1 d . . .
H14 H 0.3754 0.5438 0.8230 0.038 Uiso 1 1 calc R . .
C15 C 0.2074(3) 0.6516(3) 0.7668(2) 0.0329(7) Uani 1 1 d . . .
H15 H 0.2050 0.6104 0.6898 0.039 Uiso 1 1 calc R . .
C16 C 0.1101(3) 0.7516(3) 0.7996(2) 0.0326(6) Uani 1 1 d . . .
H16 H 0.0415 0.7801 0.7454 0.039 Uiso 1 1 calc R . .
C17 C 0.1134(3) 0.8100(3) 0.9121(2) 0.0316(6) Uani 1 1 d . . .
H17 H 0.0472 0.8790 0.9353 0.038 Uiso 1 1 calc R . .
C18 C 0.2128(3) 0.7680(3) 0.9903(2) 0.0290(6) Uani 1 1 d . . .
H18 H 0.2139 0.8074 1.0672 0.035 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
C2 O2 C1 114.55(17) . . ?
C11 O4 C12 115.58(17) . . ?
C2 N1 C3 127.3(2) . . ?
C3 N2 C4 122.71(19) . . ?
C10 N3 C9 130.6(2) . . ?
C11 N4 C10 128.3(2) . . ?
O1 C2 O2 124.1(2) . . ?
O1 C2 N1 125.4(2) . . ?
O2 C2 N1 110.5(2) . . ?
N2 C3 N1 115.9(2) . . ?
N2 C3 S1 124.35(17) . . ?
N1 C3 S1 119.75(17) . . ?
C5 C4 C9 120.5(2) . . ?
C5 C4 N2 120.11(19) . . ?
C9 C4 N2 119.43(19) . . ?
C6 C5 C4 120.0(2) . . ?
C5 C6 C7 119.9(2) . . ?
C6 C7 C8 120.7(2) . . ?
C7 C8 C9 119.9(2) . . ?
C8 C9 C4 119.0(2) . . ?
C8 C9 N3 125.5(2) . . ?
C4 C9 N3 115.4(2) . . ?
N3 C10 N4 114.3(2) . . ?
N3 C10 S2 127.29(18) . . ?
N4 C10 S2 118.37(17) . . ?
O3 C11 O4 125.5(2) . . ?
O3 C11 N4 125.0(2) . . ?
O4 C11 N4 109.47(19) . . ?
C18 C13 C14 119.6(2) . . ?
C15 C14 C13 120.4(2) . . ?
C14 C15 C16 120.0(2) . . ?
C15 C16 C17 119.5(2) . . ?
C18 C17 C16 120.0(2) . . ?
C13 C18 C17 120.4(2) . . ?
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
S1 C3 1.656(2) . ?
S2 C10 1.670(2) . ?
O1 C2 1.215(3) . ?
O2 C2 1.334(3) . ?
O2 C1 1.457(3) . ?
O3 C11 1.218(3) . ?
O4 C11 1.323(3) . ?
O4 C12 1.449(3) . ?
N1 C2 1.369(3) . ?
N1 C3 1.386(3) . ?
N2 C3 1.338(3) . ?
N2 C4 1.436(3) . ?
N3 C10 1.346(3) . ?
N3 C9 1.413(3) . ?
N4 C11 1.381(3) . ?
N4 C10 1.385(3) . ?
C4 C5 1.383(3) . ?
C4 C9 1.400(3) . ?
C5 C6 1.381(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.382(3) . ?
C8 C9 1.392(3) . ?
C13 C18 1.374(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.375(4) . ?
C15 C16 1.382(4) . ?
C16 C17 1.385(4) . ?
C17 C18 1.377(4) . ?
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
N2 H2 O1 0.863(16) 2.01(2) 2.668(2) 132(2) .
N3 H3 O3 0.888(16) 1.894(19) 2.657(2) 143(2) .
N1 H1 O2 0.881(16) 2.407(18) 3.263(2) 164(2) 2_657
N4 H4 S2 0.881(16) 2.476(17) 3.3420(19) 167(2) 2_666
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 1.4(3) . . . . ?
C1 O2 C2 N1 -177.97(18) . . . . ?
C3 N1 C2 O1 8.1(4) . . . . ?
C3 N1 C2 O2 -172.50(19) . . . . ?
C4 N2 C3 N1 177.19(18) . . . . ?
C4 N2 C3 S1 -2.2(3) . . . . ?
C2 N1 C3 N2 2.9(3) . . . . ?
C2 N1 C3 S1 -177.71(17) . . . . ?
C3 N2 C4 C5 -83.2(3) . . . . ?
C3 N2 C4 C9 98.1(2) . . . . ?
C9 C4 C5 C6 -1.3(3) . . . . ?
N2 C4 C5 C6 180.0(2) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C4 -1.3(3) . . . . ?
C7 C8 C9 N3 -177.7(2) . . . . ?
C5 C4 C9 C8 1.9(3) . . . . ?
N2 C4 C9 C8 -179.35(19) . . . . ?
C5 C4 C9 N3 178.76(19) . . . . ?
N2 C4 C9 N3 -2.5(3) . . . . ?
C10 N3 C9 C8 -25.4(4) . . . . ?
C10 N3 C9 C4 158.0(2) . . . . ?
C9 N3 C10 N4 177.4(2) . . . . ?
C9 N3 C10 S2 -2.1(3) . . . . ?
C11 N4 C10 N3 3.9(3) . . . . ?
C11 N4 C10 S2 -176.55(17) . . . . ?
C12 O4 C11 O3 5.8(3) . . . . ?
C12 O4 C11 N4 -175.03(18) . . . . ?
C10 N4 C11 O3 3.3(4) . . . . ?
C10 N4 C11 O4 -175.9(2) . . . . ?
C18 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C14 C13 C18 C17 -0.4(4) . . . . ?
C16 C17 C18 C13 0.7(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653610
