#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/61/7206194.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_7206194
loop_
_publ_author_name
'Nauha, Elisa'
'Ojala, Antti'
'Nissinen, Maija'
'Saxell, Heidi'
_publ_section_title
;
 Comparison of the polymorphs and solvates of two analogous
 fungicides---a case study of the applicability of a supramolecular
 synthon approach in crystal engineering
;
_journal_issue                   15
_journal_name_full               CrystEngComm
_journal_page_first              4956
_journal_paper_doi               10.1039/c1ce05077j
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C14 H18 N4 O4 S2'
_chemical_formula_sum            'C14 H18 N4 O4 S2'
_chemical_formula_weight         370.44
_chemical_name_common            thiphanate-ethyl
_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                 93.750(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.72710(10)
_cell_length_b                   16.0239(3)
_cell_length_c                   22.6450(4)
_cell_measurement_temperature    173(2)
_cell_volume                     1711.61(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4691
_diffrn_reflns_theta_full        66.65
_diffrn_reflns_theta_max         66.65
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    3.066
_exptl_absorpt_correction_T_max  0.7491
_exptl_absorpt_correction_T_min  0.7491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo (Otwinowski, Borek, Majewski & Minor,2003)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0550
_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)+(0.0427P)²+1.4457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                2074
_reflns_number_total             2931
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05077j.txt
_cod_data_source_block           TE-formII
_cod_original_sg_symbol_H-M      p2(1)/c
_cod_database_code               7206194
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
S1 S -0.3843(2) 0.55043(6) 0.08720(4) 0.0409(3) Uani 1 1 d . . .
S2 S -0.0263(2) 0.92559(5) 0.07849(4) 0.0342(3) Uani 1 1 d . . .
O1 O 0.1153(6) 0.68567(15) -0.05070(11) 0.0400(6) Uani 1 1 d . . .
O2 O -0.1722(6) 0.60723(15) -0.11197(11) 0.0416(7) Uani 1 1 d . . .
O3 O 0.6272(6) 0.80769(15) -0.03744(11) 0.0383(6) Uani 1 1 d . . .
O4 O 0.4674(6) 0.91080(15) -0.09934(11) 0.0401(6) Uani 1 1 d . . .
N1 N -0.2290(7) 0.60008(18) -0.01593(13) 0.0361(7) Uani 1 1 d D . .
H1N H -0.363(6) 0.5634(19) -0.0294(17) 0.043 Uiso 1 1 d D . .
N2 N -0.0324(7) 0.67655(18) 0.06149(13) 0.0348(7) Uani 1 1 d D . .
H2N H 0.047(8) 0.697(2) 0.0294(12) 0.042 Uiso 1 1 d D . .
N3 N 0.3430(6) 0.80401(17) 0.06172(13) 0.0312(7) Uani 1 1 d D . .
H3N H 0.478(6) 0.788(2) 0.0383(14) 0.037 Uiso 1 1 d D . .
N4 N 0.2914(6) 0.90364(17) -0.01212(13) 0.0311(7) Uani 1 1 d D . .
H4N H 0.182(7) 0.9477(17) -0.0231(16) 0.037 Uiso 1 1 d D . .
C1 C -0.1154(10) 0.5776(3) -0.21286(17) 0.0508(11) Uani 1 1 d . . .
H1A H -0.0685 0.5191 -0.2042 0.076 Uiso 1 1 calc R . .
H1B H -0.0238 0.5952 -0.2484 0.076 Uiso 1 1 calc R . .
H1C H -0.3214 0.5835 -0.2195 0.076 Uiso 1 1 calc R . .
C2 C -0.0120(9) 0.6312(2) -0.16141(16) 0.0428(10) Uani 1 1 d . . .
H2A H 0.1931 0.6221 -0.1519 0.051 Uiso 1 1 calc R . .
H2B H -0.0429 0.6909 -0.1709 0.051 Uiso 1 1 calc R . .
C3 C -0.0769(8) 0.6362(2) -0.05906(16) 0.0354(9) Uani 1 1 d . . .
C4 C -0.2022(8) 0.6125(2) 0.04492(16) 0.0327(8) Uani 1 1 d . . .
C5 C 0.0822(8) 0.7024(2) 0.11788(15) 0.0303(8) Uani 1 1 d . . .
C6 C 0.0156(9) 0.6699(2) 0.17185(16) 0.0371(9) Uani 1 1 d . . .
H6 H -0.1238 0.6273 0.1734 0.045 Uiso 1 1 calc R . .
C7 C 0.1526(8) 0.6994(2) 0.22384(16) 0.0387(9) Uani 1 1 d . . .
H7 H 0.1048 0.6769 0.2607 0.046 Uiso 1 1 calc R . .
C8 C 0.3569(9) 0.7609(2) 0.22302(17) 0.0410(9) Uani 1 1 d . . .
H8 H 0.4517 0.7794 0.2589 0.049 Uiso 1 1 calc R . .
C9 C 0.4228(9) 0.7953(2) 0.16928(16) 0.0385(9) Uani 1 1 d . . .
H9 H 0.5623 0.8379 0.1682 0.046 Uiso 1 1 calc R . .
C10 C 0.2829(7) 0.7671(2) 0.11709(15) 0.0308(8) Uani 1 1 d . . .
C11 C 0.2174(7) 0.8745(2) 0.04227(15) 0.0293(8) Uani 1 1 d . . .
C12 C 0.4804(8) 0.8677(2) -0.04834(15) 0.0320(8) Uani 1 1 d . . .
C13 C 0.6589(9) 0.8838(2) -0.14318(16) 0.0439(10) Uani 1 1 d . . .
H13A H 0.6123 0.8264 -0.1567 0.053 Uiso 1 1 calc R . .
H13B H 0.8577 0.8849 -0.1264 0.053 Uiso 1 1 calc R . .
C14 C 0.6182(10) 0.9443(2) -0.19353(17) 0.0492(11) Uani 1 1 d . . .
H14A H 0.4191 0.9439 -0.2086 0.074 Uiso 1 1 calc R . .
H14B H 0.7386 0.9281 -0.2252 0.074 Uiso 1 1 calc R . .
H14C H 0.6704 1.0005 -0.1797 0.074 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 O2 C2 116.1(3) . . ?
C12 O4 C13 116.1(3) . . ?
C3 N1 C4 128.7(3) . . ?
C3 N1 H1N 115(3) . . ?
C4 N1 H1N 116(3) . . ?
C4 N2 C5 131.5(3) . . ?
C4 N2 H2N 109(2) . . ?
C5 N2 H2N 118(3) . . ?
C11 N3 C10 121.9(3) . . ?
C11 N3 H3N 112(2) . . ?
C10 N3 H3N 126(2) . . ?
C12 N4 C11 126.9(3) . . ?
C12 N4 H4N 123(2) . . ?
C11 N4 H4N 110(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C1 106.8(3) . . ?
O2 C2 H2A 110.4 . . ?
C1 C2 H2A 110.4 . . ?
O2 C2 H2B 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
O1 C3 O2 125.0(3) . . ?
O1 C3 N1 125.8(4) . . ?
O2 C3 N1 109.2(3) . . ?
N2 C4 N1 113.6(3) . . ?
N2 C4 S1 128.4(3) . . ?
N1 C4 S1 118.0(3) . . ?
C6 C5 C10 118.8(3) . . ?
C6 C5 N2 126.2(3) . . ?
C10 C5 N2 115.0(3) . . ?
C5 C6 C7 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 119.5(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C10 119.5(4) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C5 120.8(3) . . ?
C9 C10 N3 119.9(3) . . ?
C5 C10 N3 119.3(3) . . ?
N3 C11 N4 116.4(3) . . ?
N3 C11 S2 123.9(3) . . ?
N4 C11 S2 119.6(2) . . ?
O3 C12 O4 125.5(3) . . ?
O3 C12 N4 126.9(3) . . ?
O4 C12 N4 107.5(3) . . ?
O4 C13 C14 105.8(3) . . ?
O4 C13 H13A 110.6 . . ?
C14 C13 H13A 110.6 . . ?
O4 C13 H13B 110.6 . . ?
C14 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
S1 C4 1.659(4) . ?
S2 C11 1.671(4) . ?
O1 C3 1.212(4) . ?
O2 C3 1.335(4) . ?
O2 C2 1.444(4) . ?
O3 C12 1.202(4) . ?
O4 C12 1.344(4) . ?
O4 C13 1.452(4) . ?
N1 C3 1.377(5) . ?
N1 C4 1.390(5) . ?
N1 H1N 0.902(19) . ?
N2 C4 1.342(4) . ?
N2 C5 1.416(4) . ?
N2 H2N 0.899(19) . ?
N3 C11 1.337(4) . ?
N3 C10 1.432(4) . ?
N3 H3N 0.892(18) . ?
N4 C12 1.378(5) . ?
N4 C11 1.383(4) . ?
N4 H4N 0.899(18) . ?
C1 C2 1.504(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 C6 1.384(5) . ?
C5 C10 1.406(5) . ?
C6 C7 1.390(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(5) . ?
C9 H9 0.9500 . ?
C13 C14 1.499(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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 H1N S1 0.902(19) 2.50(2) 3.373(3) 162(3) 3_465
N2 H2N O1 0.899(19) 1.87(3) 2.682(4) 149(3) .
N3 H3N O3 0.892(18) 1.92(3) 2.692(4) 143(3) .
N4 H4N S2 0.899(18) 2.47(2) 3.327(3) 159(3) 3_575
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
C3 O2 C2 C1 167.8(3) . . . . ?
C2 O2 C3 O1 6.6(5) . . . . ?
C2 O2 C3 N1 -172.7(3) . . . . ?
C4 N1 C3 O1 1.1(6) . . . . ?
C4 N1 C3 O2 -179.6(3) . . . . ?
C5 N2 C4 N1 -169.7(3) . . . . ?
C5 N2 C4 S1 12.2(6) . . . . ?
C3 N1 C4 N2 10.1(5) . . . . ?
C3 N1 C4 S1 -171.6(3) . . . . ?
C4 N2 C5 C6 -7.6(6) . . . . ?
C4 N2 C5 C10 172.1(4) . . . . ?
C10 C5 C6 C7 -2.0(5) . . . . ?
N2 C5 C6 C7 177.7(3) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
C6 C7 C8 C9 1.5(6) . . . . ?
C7 C8 C9 C10 -0.3(6) . . . . ?
C8 C9 C10 C5 -2.0(5) . . . . ?
C8 C9 C10 N3 178.1(3) . . . . ?
C6 C5 C10 C9 3.1(5) . . . . ?
N2 C5 C10 C9 -176.6(3) . . . . ?
C6 C5 C10 N3 -176.9(3) . . . . ?
N2 C5 C10 N3 3.4(5) . . . . ?
C11 N3 C10 C9 -83.5(4) . . . . ?
C11 N3 C10 C5 96.5(4) . . . . ?
C10 N3 C11 N4 -179.5(3) . . . . ?
C10 N3 C11 S2 -1.7(5) . . . . ?
C12 N4 C11 N3 0.1(5) . . . . ?
C12 N4 C11 S2 -177.8(3) . . . . ?
C13 O4 C12 O3 -3.1(5) . . . . ?
C13 O4 C12 N4 178.3(3) . . . . ?
C11 N4 C12 O3 -5.1(6) . . . . ?
C11 N4 C12 O4 173.6(3) . . . . ?
C12 O4 C13 C14 -176.3(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2297684
