#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:24:55 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180392 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/61/7206195.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_7206195
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, C3 H6 O'
_chemical_formula_sum            'C17 H24 N4 O5 S2'
_chemical_formula_weight         428.52
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 111.432(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0607(2)
_cell_length_b                   17.4629(2)
_cell_length_c                   8.45600(10)
_cell_measurement_temperature    173(2)
_cell_volume                     2207.63(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 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2547
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         3.89
_exptl_absorpt_coefficient_mu    2.482
_exptl_absorpt_correction_T_max  0.6367
_exptl_absorpt_correction_T_min  0.5758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo (Otwinowski, Borek, Majewski & Minor,2003)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1878
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0359
_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)+(0.0464P)²+1.9628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                1719
_reflns_number_total             1878
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05077j.txt
_cod_data_source_block           TE-acetone
_cod_original_cell_volume        2207.63(5)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7206195
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.18336(3) 0.35391(3) 0.50617(6) 0.0478(2) Uani 1 1 d . . .
O1 O 0.18311(9) 0.17643(7) 0.06860(16) 0.0420(3) Uani 1 1 d . . .
O2 O 0.07716(10) 0.26643(7) -0.04231(16) 0.0493(4) Uani 1 1 d . . .
N1 N 0.16550(10) 0.26461(8) 0.24240(18) 0.0348(3) Uani 1 1 d D . .
H1N H 0.2088(12) 0.2376(11) 0.321(2) 0.042 Uiso 1 1 d D . .
N2 N 0.07077(9) 0.36904(8) 0.18696(18) 0.0315(3) Uani 1 1 d D . .
H2N H 0.0506(13) 0.3533(10) 0.081(2) 0.038 Uiso 1 1 d D . .
C1 C 0.22095(16) 0.07601(13) -0.0822(3) 0.0597(6) Uani 1 1 d . . .
H1A H 0.2831 0.0938 -0.0342 0.090 Uiso 1 1 calc R . .
H1B H 0.2095 0.0530 -0.1940 0.090 Uiso 1 1 calc R . .
H1C H 0.2107 0.0377 -0.0065 0.090 Uiso 1 1 calc R . .
C2 C 0.15911(14) 0.14247(11) -0.1006(2) 0.0470(5) Uani 1 1 d . . .
H2A H 0.1664 0.1804 -0.1815 0.056 Uiso 1 1 calc R . .
H2B H 0.0961 0.1249 -0.1430 0.056 Uiso 1 1 calc R . .
C3 C 0.13598(12) 0.23815(9) 0.0768(2) 0.0350(4) Uani 1 1 d . . .
C4 C 0.13613(11) 0.32933(9) 0.3010(2) 0.0311(4) Uani 1 1 d . . .
C5 C 0.03634(11) 0.43970(9) 0.22428(19) 0.0278(3) Uani 1 1 d . . .
C6 C 0.07336(11) 0.50857(9) 0.2000(2) 0.0302(4) Uani 1 1 d . . .
H6 H 0.1235 0.5086 0.1657 0.036 Uiso 1 1 calc R . .
C7 C 0.03687(11) 0.57736(9) 0.2259(2) 0.0306(4) Uani 1 1 d . . .
H7 H 0.0625 0.6245 0.2106 0.037 Uiso 1 1 calc R . .
O100 O 0.0000 -0.00252(17) 0.2500 0.1048(11) Uani 1 2 d S . .
C100 C 0.0000 0.0667(2) 0.2500 0.0631(9) Uani 1 2 d S . .
C101 C 0.0474(2) 0.11049(19) 0.4098(4) 0.0871(9) Uani 1 1 d . . .
H10A H 0.0458 0.0812 0.5075 0.131 Uiso 1 1 calc R . .
H10B H 0.0177 0.1599 0.4050 0.131 Uiso 1 1 calc R . .
H10C H 0.1097 0.1190 0.4217 0.131 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 O1 C2 115.25(13) . . ?
C3 N1 C4 126.85(14) . . ?
C3 N1 H1N 117.3(13) . . ?
C4 N1 H1N 115.9(13) . . ?
C4 N2 C5 123.65(14) . . ?
C4 N2 H2N 118.4(13) . . ?
C5 N2 H2N 117.8(13) . . ?
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 . . ?
O1 C2 C1 106.54(16) . . ?
O1 C2 H2A 110.4 . . ?
C1 C2 H2A 110.4 . . ?
O1 C2 H2B 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
O2 C3 O1 125.00(16) . . ?
O2 C3 N1 125.63(15) . . ?
O1 C3 N1 109.37(14) . . ?
N2 C4 N1 116.56(15) . . ?
N2 C4 S1 123.74(13) . . ?
N1 C4 S1 119.70(12) . . ?
C5 C5 C6 120.07(9) 2 . ?
C5 C5 N2 120.37(9) 2 . ?
C6 C5 N2 119.47(14) . . ?
C7 C6 C5 119.81(15) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C7 C7 C6 120.11(10) 2 . ?
C7 C7 H7 119.9 2 . ?
C6 C7 H7 119.9 . . ?
O100 C100 C101 120.70(18) . 2 ?
O100 C100 C101 120.70(18) . . ?
C101 C100 C101 118.6(4) 2 . ?
C100 C101 H10A 109.5 . . ?
C100 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
C100 C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 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 1.6753(17) . ?
O1 C3 1.333(2) . ?
O1 C2 1.464(2) . ?
O2 C3 1.207(2) . ?
N1 C3 1.383(2) . ?
N1 C4 1.384(2) . ?
N1 H1N 0.899(15) . ?
N2 C4 1.332(2) . ?
N2 C5 1.434(2) . ?
N2 H2N 0.875(15) . ?
C1 C2 1.498(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 C5 1.387(3) 2 ?
C5 C6 1.390(2) . ?
C6 C7 1.389(2) . ?
C6 H6 0.9500 . ?
C7 C7 1.386(3) 2 ?
C7 H7 0.9500 . ?
O100 C100 1.210(4) . ?
C100 C101 1.496(3) 2 ?
C100 C101 1.496(3) . ?
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 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 0.899(15) 2.418(16) 3.3054(14) 169.4(18) 7_556
N2 H2N O2 0.875(15) 1.976(17) 2.6693(18) 135.2(17) .
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 O1 C2 C1 178.56(17) . . . . ?
C2 O1 C3 O2 0.0(3) . . . . ?
C2 O1 C3 N1 -179.67(16) . . . . ?
C4 N1 C3 O2 -2.7(3) . . . . ?
C4 N1 C3 O1 176.90(16) . . . . ?
C5 N2 C4 N1 -176.22(15) . . . . ?
C5 N2 C4 S1 3.4(2) . . . . ?
C3 N1 C4 N2 2.1(3) . . . . ?
C3 N1 C4 S1 -177.53(14) . . . . ?
C4 N2 C5 C5 -91.9(2) . . . 2 ?
C4 N2 C5 C6 91.5(2) . . . . ?
C5 C5 C6 C7 -0.6(3) 2 . . . ?
N2 C5 C6 C7 176.09(14) . . . . ?
C5 C6 C7 C7 -0.7(3) . . . 2 ?
