#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:24:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180392 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/61/7206196.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_7206196
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, C H Cl3'
_chemical_formula_sum            'C15 H19 Cl3 N4 O4 S2'
_chemical_formula_weight         489.81
_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                 112.739(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5158(3)
_cell_length_b                   18.0503(4)
_cell_length_c                   8.5922(2)
_cell_measurement_temperature    173(2)
_cell_volume                     2219.34(10)
_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       '95mm CCD camera on κ-goniostat'
_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  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2817
_diffrn_reflns_theta_full        66.57
_diffrn_reflns_theta_max         66.57
_diffrn_reflns_theta_min         3.94
_exptl_absorpt_coefficient_mu    5.755
_exptl_absorpt_correction_T_max  0.4240
_exptl_absorpt_correction_T_min  0.3272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo (Otwinowski, Borek, Majewski & Minor,2003)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.067
_refine_diff_density_min         -0.925
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0755
_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)+(0.0996P)²+12.3692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1918
_refine_ls_wR_factor_ref         0.2058
_reflns_number_gt                1554
_reflns_number_total             1907
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05077j.txt
_cod_data_source_block           TE-chloroform
_cod_original_cell_volume        2219.34(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7206196
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 0.18743(8) 0.14490(6) 1.00705(14) 0.0466(4) Uani 1 1 d . . .
O1 O 0.0826(3) 0.22327(17) 0.4588(4) 0.0509(9) Uani 1 1 d . . .
O2 O 0.1809(2) 0.31790(16) 0.5739(4) 0.0375(7) Uani 1 1 d . . .
N1 N 0.1683(2) 0.22993(18) 0.7442(4) 0.0308(8) Uani 1 1 d . . .
H1N H 0.2105 0.2575 0.8206 0.037 Uiso 1 1 calc R . .
N2 N 0.0729(2) 0.12729(17) 0.6877(4) 0.0302(8) Uani 1 1 d . . .
H2N H 0.0493 0.1439 0.5833 0.036 Uiso 1 1 calc R . .
C1 C 0.2149(4) 0.4170(3) 0.4236(7) 0.0558(14) Uani 1 1 d . . .
H1A H 0.1990 0.4546 0.4904 0.084 Uiso 1 1 calc R . .
H1B H 0.2037 0.4369 0.3113 0.084 Uiso 1 1 calc R . .
H1C H 0.2810 0.4035 0.4802 0.084 Uiso 1 1 calc R . .
C2 C 0.1555(3) 0.3497(3) 0.4065(6) 0.0424(11) Uani 1 1 d . . .
H2A H 0.0886 0.3635 0.3592 0.051 Uiso 1 1 calc R . .
H2B H 0.1665 0.3134 0.3299 0.051 Uiso 1 1 calc R . .
C3 C 0.1381(3) 0.2542(2) 0.5799(5) 0.0331(9) Uani 1 1 d . . .
C4 C 0.1394(3) 0.1668(2) 0.8025(5) 0.0279(9) Uani 1 1 d . . .
C5 C 0.0374(3) 0.0589(2) 0.7246(5) 0.0261(8) Uani 1 1 d . . .
C6 C 0.0746(3) -0.0077(2) 0.6990(5) 0.0285(9) Uani 1 1 d . . .
H6 H 0.1263 -0.0081 0.6656 0.034 Uiso 1 1 calc R . .
C7 C 0.03552(15) -0.07387(12) 0.7227(3) 0.0272(8) Uani 1 1 d . . .
H7 H 0.0589 -0.1196 0.7004 0.033 Uiso 1 1 calc R . .
Cl1 Cl -0.05511(15) 0.32831(12) 0.5454(3) 0.0768(10) Uani 0.50 1 d PR A -1
Cl2 Cl -0.00692(15) 0.47407(12) 0.6024(3) 0.159(3) Uani 0.50 1 d PR A -1
Cl3 Cl 0.02866(15) 0.36611(12) 0.8749(3) 0.124(2) Uani 0.50 1 d PR A -1
C10 C -0.05103(15) 0.39411(12) 0.6606(3) 0.131(11) Uani 0.50 1 d PR A -1
H10 H -0.1147 0.4042 0.6591 0.157 Uiso 0.50 1 calc PR B -1
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'
Cl Cl 0.3639 0.7018 '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 115.4(3) . . ?
C3 N1 C4 127.1(3) . . ?
C3 N1 H1N 116.5 . . ?
C4 N1 H1N 116.5 . . ?
C4 N2 C5 123.6(3) . . ?
C4 N2 H2N 118.2 . . ?
C5 N2 H2N 118.2 . . ?
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 107.6(4) . . ?
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 124.5(4) . . ?
O1 C3 N1 125.9(4) . . ?
O2 C3 N1 109.7(3) . . ?
N2 C4 N1 116.1(3) . . ?
N2 C4 S1 123.9(3) . . ?
N1 C4 S1 120.0(3) . . ?
C5 C5 C6 120.0(2) 2_556 . ?
C5 C5 N2 120.5(2) 2_556 . ?
C6 C5 N2 119.4(4) . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C7 C7 C6 120.69(19) 2_556 . ?
C7 C7 H7 119.7 2_556 . ?
C6 C7 H7 119.7 . . ?
Cl1 C10 Cl2 112.2 . . ?
Cl1 C10 Cl3 106.1 . . ?
Cl2 C10 Cl3 109.0 . . ?
Cl1 C10 H10 109.8 . . ?
Cl2 C10 H10 109.8 . . ?
Cl3 C10 H10 109.8 . . ?
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 1.670(4) . ?
O1 C3 1.201(5) . ?
O2 C3 1.338(5) . ?
O2 C2 1.455(5) . ?
N1 C3 1.376(5) . ?
N1 C4 1.387(5) . ?
N1 H1N 0.8800 . ?
N2 C4 1.326(5) . ?
N2 C5 1.437(5) . ?
N2 H2N 0.8800 . ?
C1 C2 1.497(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 C5 1.387(8) 2_556 ?
C5 C6 1.387(5) . ?
C6 C7 1.390(4) . ?
C6 H6 0.9500 . ?
C7 C7 1.355(5) 2_556 ?
C7 H7 0.9500 . ?
Cl1 C10 1.5317 . ?
Cl2 C10 1.7511 . ?
Cl3 C10 1.8482 . ?
C10 H10 1.0000 . ?
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 0.88 2.45 3.315(3) 168.1 7_557
N2 H2N O1 0.88 1.97 2.669(4) 134.9 .
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 -176.0(4) . . . . ?
C2 O2 C3 O1 0.5(6) . . . . ?
C2 O2 C3 N1 179.7(4) . . . . ?
C4 N1 C3 O1 -1.7(7) . . . . ?
C4 N1 C3 O2 179.0(4) . . . . ?
C5 N2 C4 N1 177.5(3) . . . . ?
C5 N2 C4 S1 -3.1(6) . . . . ?
C3 N1 C4 N2 -2.8(6) . . . . ?
C3 N1 C4 S1 177.7(3) . . . . ?
C4 N2 C5 C5 89.2(6) . . . 2_556 ?
C4 N2 C5 C6 -94.8(5) . . . . ?
C5 C5 C6 C7 0.8(6) 2_556 . . . ?
N2 C5 C6 C7 -175.2(3) . . . . ?
C5 C6 C7 C7 -2.9(5) . . . 2_556 ?
