#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/61/7206198.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_7206198
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, C4 H8 O2'
_chemical_formula_sum            'C18 H26 N4 O6 S2'
_chemical_formula_weight         458.55
_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                65.555(2)
_cell_angle_beta                 68.864(2)
_cell_angle_gamma                76.329(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2924(2)
_cell_length_b                   11.7070(3)
_cell_length_c                   12.1305(3)
_cell_measurement_temperature    173(2)
_cell_volume                     1114.60(5)
_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 0.958
_diffrn_measured_fraction_theta_max 0.958
_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  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5447
_diffrn_reflns_theta_full        67.11
_diffrn_reflns_theta_max         67.11
_diffrn_reflns_theta_min         4.17
_exptl_absorpt_coefficient_mu    2.528
_exptl_absorpt_correction_T_max  0.7861
_exptl_absorpt_correction_T_min  0.5176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo (Otwinowski, Borek, Majewski & Minor,2003)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0444
_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)+(0.0548P)²+0.6176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                3123
_reflns_number_total             3818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05077j.txt
_cod_data_source_block           TE-dioxaneII
_cod_original_cell_volume        1114.61(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7206198
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 0.75610(9) 0.13148(7) 0.76374(6) 0.0510(2) Uani 1 1 d . . .
S2 S 1.12418(7) 0.41109(5) 0.14367(6) 0.03919(19) Uani 1 1 d . . .
O1 O 0.6579(2) 0.33131(19) 0.38168(16) 0.0507(5) Uani 1 1 d . . .
O2 O 0.4182(2) 0.36128(18) 0.50731(16) 0.0460(5) Uani 1 1 d . . .
O3 O 0.7759(2) 0.15314(16) 0.20795(16) 0.0448(5) Uani 1 1 d . . .
O4 O 0.71683(19) 0.32386(15) 0.04851(15) 0.0383(4) Uani 1 1 d . . .
N1 N 0.6003(2) 0.2534(2) 0.59890(19) 0.0386(5) Uani 1 1 d D . .
H1N H 0.523(3) 0.254(3) 0.667(2) 0.046 Uiso 1 1 d D . .
N2 N 0.8574(2) 0.20037(19) 0.50941(18) 0.0352(5) Uani 1 1 d D . .
H2N H 0.824(3) 0.240(2) 0.442(2) 0.042 Uiso 1 1 d D . .
N3 N 1.0024(2) 0.19220(18) 0.27579(17) 0.0310(4) Uani 1 1 d D . .
H3N H 0.931(3) 0.145(2) 0.290(2) 0.037 Uiso 1 1 d D . .
N4 N 0.9052(2) 0.33107(18) 0.11234(17) 0.0308(4) Uani 1 1 d D . .
H4N H 0.904(3) 0.4050(18) 0.051(2) 0.037 Uiso 1 1 d D . .
C1 C 0.1992(3) 0.4728(3) 0.4373(3) 0.0571(8) Uani 1 1 d . . .
H1A H 0.1408 0.3992 0.4898 0.086 Uiso 1 1 calc R . .
H1B H 0.1622 0.5224 0.3632 0.086 Uiso 1 1 calc R . .
H1C H 0.1843 0.5249 0.4870 0.086 Uiso 1 1 calc R . .
C2 C 0.3674(3) 0.4298(3) 0.3944(3) 0.0528(7) Uani 1 1 d . . .
H2A H 0.3836 0.3742 0.3469 0.063 Uiso 1 1 calc R . .
H2B H 0.4272 0.5033 0.3382 0.063 Uiso 1 1 calc R . .
C3 C 0.5670(3) 0.3164(2) 0.4858(2) 0.0398(6) Uani 1 1 d . . .
C4 C 0.7444(3) 0.1960(2) 0.6167(2) 0.0358(6) Uani 1 1 d . . .
C5 C 1.0159(3) 0.1560(2) 0.4842(2) 0.0321(5) Uani 1 1 d . . .
C6 C 1.1013(3) 0.1183(2) 0.5700(2) 0.0392(6) Uani 1 1 d . . .
H6 H 1.0516 0.1159 0.6543 0.047 Uiso 1 1 calc R . .
C7 C 1.2588(3) 0.0846(3) 0.5306(3) 0.0474(7) Uani 1 1 d . . .
H7 H 1.3172 0.0598 0.5885 0.057 Uiso 1 1 calc R . .
C8 C 1.3333(3) 0.0862(3) 0.4090(3) 0.0507(7) Uani 1 1 d . . .
H8 H 1.4420 0.0637 0.3832 0.061 Uiso 1 1 calc R . .
C9 C 1.2485(3) 0.1209(2) 0.3246(3) 0.0413(6) Uani 1 1 d . . .
H9 H 1.2985 0.1208 0.2411 0.050 Uiso 1 1 calc R . .
C10 C 1.0914(3) 0.1556(2) 0.3621(2) 0.0318(5) Uani 1 1 d . . .
C11 C 1.0057(3) 0.3043(2) 0.1812(2) 0.0299(5) Uani 1 1 d . . .
C12 C 0.7960(3) 0.2581(2) 0.1306(2) 0.0335(5) Uani 1 1 d . . .
C13 C 0.5998(4) 0.2636(3) 0.0458(3) 0.0579(8) Uani 1 1 d . . .
H13A H 0.5152 0.2456 0.1270 0.069 Uiso 1 1 calc R . .
H13B H 0.6455 0.1832 0.0326 0.069 Uiso 1 1 calc R . .
C14 C 0.5394(3) 0.3519(3) -0.0602(3) 0.0512(7) Uani 1 1 d . . .
H14A H 0.4982 0.4322 -0.0475 0.077 Uiso 1 1 calc R . .
H14B H 0.4566 0.3157 -0.0632 0.077 Uiso 1 1 calc R . .
H14C H 0.6235 0.3664 -0.1402 0.077 Uiso 1 1 calc R . .
O100 O 0.0330(2) 0.17652(17) 0.92248(17) 0.0464(5) Uani 1 1 d . . .
O200 O 0.3385(2) 0.24582(16) 0.81262(16) 0.0415(4) Uani 1 1 d . . .
C100 C 0.1638(3) 0.0841(3) 0.9271(3) 0.0493(7) Uani 1 1 d . . .
H10A H 0.1935 0.0572 0.8538 0.059 Uiso 1 1 calc R . .
H10B H 0.1365 0.0092 1.0056 0.059 Uiso 1 1 calc R . .
C200 C 0.2988(3) 0.1365(3) 0.9243(3) 0.0453(6) Uani 1 1 d . . .
H20A H 0.2713 0.1588 1.0002 0.054 Uiso 1 1 calc R . .
H20B H 0.3892 0.0717 0.9261 0.054 Uiso 1 1 calc R . .
C300 C 0.2071(3) 0.3382(2) 0.8078(2) 0.0395(6) Uani 1 1 d . . .
H30A H 0.2343 0.4129 0.7290 0.047 Uiso 1 1 calc R . .
H30B H 0.1775 0.3656 0.8808 0.047 Uiso 1 1 calc R . .
C400 C 0.0731(3) 0.2854(2) 0.8112(2) 0.0417(6) Uani 1 1 d . . .
H40A H -0.0173 0.3502 0.8092 0.050 Uiso 1 1 calc R . .
H40B H 0.1006 0.2629 0.7353 0.050 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 115.21(19) . . ?
C12 O4 C13 117.88(19) . . ?
C3 N1 C4 127.3(2) . . ?
C3 N1 H1N 115.7(19) . . ?
C4 N1 H1N 116.9(19) . . ?
C4 N2 C5 132.7(2) . . ?
C4 N2 H2N 111.9(18) . . ?
C5 N2 H2N 115.4(18) . . ?
C11 N3 C10 123.04(19) . . ?
C11 N3 H3N 116.3(17) . . ?
C10 N3 H3N 120.0(17) . . ?
C11 N4 C12 128.04(19) . . ?
C11 N4 H4N 118.7(17) . . ?
C12 N4 H4N 113.2(17) . . ?
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 107.3(2) . . ?
O2 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
O2 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
O1 C3 O2 124.3(2) . . ?
O1 C3 N1 126.0(2) . . ?
O2 C3 N1 109.7(2) . . ?
N2 C4 N1 114.0(2) . . ?
N2 C4 S1 127.99(19) . . ?
N1 C4 S1 118.00(18) . . ?
C10 C5 C6 119.1(2) . . ?
C10 C5 N2 115.9(2) . . ?
C6 C5 N2 125.0(2) . . ?
C7 C6 C5 119.2(2) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 121.4(2) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C5 120.9(2) . . ?
C9 C10 N3 120.4(2) . . ?
C5 C10 N3 118.7(2) . . ?
N3 C11 N4 116.9(2) . . ?
N3 C11 S2 123.82(18) . . ?
N4 C11 S2 119.24(17) . . ?
O3 C12 O4 126.1(2) . . ?
O3 C12 N4 126.0(2) . . ?
O4 C12 N4 107.92(19) . . ?
O4 C13 C14 107.0(2) . . ?
O4 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
O4 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.6 . . ?
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 . . ?
C400 O100 C100 109.7(2) . . ?
C200 O200 C300 109.77(19) . . ?
O100 C100 C200 110.6(2) . . ?
O100 C100 H10A 109.5 . . ?
C200 C100 H10A 109.5 . . ?
O100 C100 H10B 109.5 . . ?
C200 C100 H10B 109.5 . . ?
H10A C100 H10B 108.1 . . ?
O200 C200 C100 110.4(2) . . ?
O200 C200 H20A 109.6 . . ?
C100 C200 H20A 109.6 . . ?
O200 C200 H20B 109.6 . . ?
C100 C200 H20B 109.6 . . ?
H20A C200 H20B 108.1 . . ?
O200 C300 C400 110.6(2) . . ?
O200 C300 H30A 109.5 . . ?
C400 C300 H30A 109.5 . . ?
O200 C300 H30B 109.5 . . ?
C400 C300 H30B 109.5 . . ?
H30A C300 H30B 108.1 . . ?
O100 C400 C300 110.9(2) . . ?
O100 C400 H40A 109.5 . . ?
C300 C400 H40A 109.5 . . ?
O100 C400 H40B 109.5 . . ?
C300 C400 H40B 109.5 . . ?
H40A C400 H40B 108.1 . . ?
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 1.658(2) . ?
S2 C11 1.674(2) . ?
O1 C3 1.207(3) . ?
O2 C3 1.329(3) . ?
O2 C2 1.456(3) . ?
O3 C12 1.206(3) . ?
O4 C12 1.323(3) . ?
O4 C13 1.445(3) . ?
N1 C3 1.372(3) . ?
N1 C4 1.397(3) . ?
N1 H1N 0.882(17) . ?
N2 C4 1.335(3) . ?
N2 C5 1.406(3) . ?
N2 H2N 0.881(17) . ?
N3 C11 1.337(3) . ?
N3 C10 1.432(3) . ?
N3 H3N 0.881(16) . ?
N4 C11 1.369(3) . ?
N4 C12 1.378(3) . ?
N4 H4N 0.880(16) . ?
C1 C2 1.491(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 C10 1.393(3) . ?
C5 C6 1.399(3) . ?
C6 C7 1.379(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C13 C14 1.478(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O100 C400 1.422(3) . ?
O100 C100 1.425(3) . ?
O200 C200 1.427(3) . ?
O200 C300 1.428(3) . ?
C100 C200 1.505(4) . ?
C100 H10A 0.9900 . ?
C100 H10B 0.9900 . ?
C200 H20A 0.9900 . ?
C200 H20B 0.9900 . ?
C300 C400 1.497(4) . ?
C300 H30A 0.9900 . ?
C300 H30B 0.9900 . ?
C400 H40A 0.9900 . ?
C400 H40B 0.9900 . ?
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 O200 0.882(17) 1.953(18) 2.831(3) 173(3) .
N2 H2N O1 0.881(17) 1.86(2) 2.636(3) 146(3) .
N3 H3N O3 0.881(16) 2.00(2) 2.708(3) 137(2) .
N4 H4N S2 0.880(16) 2.497(18) 3.3607(19) 167(2) 2_765
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 -179.8(2) . . . . ?
C2 O2 C3 O1 1.4(4) . . . . ?
C2 O2 C3 N1 -179.6(2) . . . . ?
C4 N1 C3 O1 1.0(5) . . . . ?
C4 N1 C3 O2 -178.0(2) . . . . ?
C5 N2 C4 N1 179.7(2) . . . . ?
C5 N2 C4 S1 -0.6(4) . . . . ?
C3 N1 C4 N2 -3.2(4) . . . . ?
C3 N1 C4 S1 177.0(2) . . . . ?
C4 N2 C5 C10 167.6(2) . . . . ?
C4 N2 C5 C6 -15.2(4) . . . . ?
C10 C5 C6 C7 1.5(3) . . . . ?
N2 C5 C6 C7 -175.6(2) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C7 C8 C9 C10 1.2(4) . . . . ?
C8 C9 C10 C5 -0.2(4) . . . . ?
C8 C9 C10 N3 179.8(2) . . . . ?
C6 C5 C10 C9 -1.1(3) . . . . ?
N2 C5 C10 C9 176.3(2) . . . . ?
C6 C5 C10 N3 178.9(2) . . . . ?
N2 C5 C10 N3 -3.7(3) . . . . ?
C11 N3 C10 C9 -75.7(3) . . . . ?
C11 N3 C10 C5 104.2(3) . . . . ?
C10 N3 C11 N4 -174.7(2) . . . . ?
C10 N3 C11 S2 5.3(3) . . . . ?
C12 N4 C11 N3 2.3(3) . . . . ?
C12 N4 C11 S2 -177.74(19) . . . . ?
C13 O4 C12 O3 -3.2(4) . . . . ?
C13 O4 C12 N4 177.1(2) . . . . ?
C11 N4 C12 O3 -4.3(4) . . . . ?
C11 N4 C12 O4 175.5(2) . . . . ?
C12 O4 C13 C14 -175.1(2) . . . . ?
C400 O100 C100 C200 57.9(3) . . . . ?
C300 O200 C200 C100 57.6(3) . . . . ?
O100 C100 C200 O200 -58.3(3) . . . . ?
C200 O200 C300 C400 -57.6(3) . . . . ?
C100 O100 C400 C300 -57.9(3) . . . . ?
O200 C300 C400 O100 58.2(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653783
