#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/41/4504151.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_4504151
loop_
_publ_author_name
'Barreiro, Elena'
'Casas, José S.'
'Couce, María D.'
'Sánchez, Agustín'
'Sordo, José'
'Varela, José M.'
'Vázquez-López, Ezequiel M.'
_publ_section_title
;
 The Influence of 5-Substituents on the Supramolecular Structures of
 Rhodanine Derivatives
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1964
_journal_paper_doi               10.1021/cg060859d
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C11 H7 D3 N O2.5 S2.5'
_chemical_formula_weight         279.37
_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                 106.507(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.264(3)
_cell_length_b                   6.3290(8)
_cell_length_c                   18.977(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2448.7(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7013
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.511
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.480229
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          .16
_exptl_crystal_size_mid          .22
_exptl_crystal_size_min          .63
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.096
_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     160
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0627
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.1771
_reflns_number_gt                1843
_reflns_number_total             2840
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060859dsi20070710_043617.cif
_cod_data_source_block           2.0.5DMSO
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C11 H7 D3 N O2.50 S2.50'
_cod_database_code               4504151
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
S1 S 0.33372(4) 0.11020(14) -0.00045(5) 0.0546(3) Uani 1 1 d .
S2 S 0.34612(5) 0.47619(19) 0.10111(6) 0.0738(4) Uani 1 1 d .
N1 N 0.42648(12) 0.3787(4) 0.02040(15) 0.0532(7) Uani 1 1 d .
H1 H 0.4507 0.4869 0.0367 0.064 Uiso 1 1 calc R
O1 O 0.48829(11) 0.2665(4) -0.05317(14) 0.0665(7) Uani 1 1 d .
O2 O 0.43712(12) -0.3542(4) -0.18391(17) 0.0736(8) Uani 1 1 d .
H2 H 0.4527 -0.4631 -0.1953 0.110 Uiso 1 1 calc R
C1 C 0.44142(15) 0.2426(5) -0.02872(18) 0.0506(8) Uani 1 1 d .
C2 C 0.37228(15) 0.3378(5) 0.04270(17) 0.0505(8) Uani 1 1 d .
C3 C 0.39233(15) 0.0719(5) -0.04772(17) 0.0468(7) Uani 1 1 d .
C4 C 0.39806(15) -0.0792(5) -0.09504(18) 0.0503(8) Uani 1 1 d .
H4A H 0.4351 -0.0665 -0.1115 0.060 Uiso 1 1 calc R
C5 C 0.35707(14) -0.2582(5) -0.12510(16) 0.0458(7) Uani 1 1 d .
C6 C 0.37845(16) -0.3978(5) -0.17165(18) 0.0509(8) Uani 1 1 d .
C7 C 0.34045(17) -0.5698(5) -0.20318(19) 0.0563(8) Uani 1 1 d .
H7 H 0.3547 -0.6593 -0.2344 0.068 Uiso 1 1 calc R
C8 C 0.28162(17) -0.6089(6) -0.18859(19) 0.0603(9) Uani 1 1 d .
H8 H 0.2568 -0.7260 -0.2093 0.072 Uiso 1 1 calc R
C9 C 0.25921(18) -0.4739(6) -0.14303(19) 0.0604(9) Uani 1 1 d .
H9 H 0.2193 -0.4991 -0.1335 0.073 Uiso 1 1 calc R
C10 C 0.29695(16) -0.3027(6) -0.11229(18) 0.0551(8) Uani 1 1 d .
H10 H 0.2818 -0.2132 -0.0818 0.066 Uiso 1 1 calc R
S1D S 0.47816(7) -0.8496(3) -0.23175(9) 0.0473(4) Uani 0.50 1 d P
O1D O 0.5000 -0.6232(5) -0.2500 0.0652(9) Uani 1 2 d S
C1D C 0.55095(19) -0.9761(7) -0.1870(3) 0.0822(13) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C2 S1 C3 92.69(15) . .
C2 N1 C1 118.2(3) . .
O1 C1 N1 123.5(3) . .
O1 C1 C3 126.5(3) . .
N1 C1 C3 110.0(3) . .
N1 C2 S2 126.3(2) . .
N1 C2 S1 109.8(2) . .
S2 C2 S1 123.9(2) . .
C4 C3 C1 119.6(3) . .
C4 C3 S1 131.0(3) . .
C1 C3 S1 109.4(2) . .
C3 C4 C5 131.7(3) . .
C10 C5 C6 117.1(3) . .
C10 C5 C4 124.7(3) . .
C6 C5 C4 118.2(3) . .
O2 C6 C7 122.4(3) . .
O2 C6 C5 117.0(3) . .
C7 C6 C5 120.6(3) . .
C8 C7 C6 120.3(3) . .
C7 C8 C9 120.3(3) . .
C10 C9 C8 119.0(3) . .
C9 C10 C5 122.5(3) . .
S1D S1D O1D 65.48(7) 2_654 .
S1D S1D C1D 69.38(19) 2_654 2_654
O1D S1D C1D 106.55(19) . 2_654
S1D S1D C1D 65.8(2) 2_654 .
O1D S1D C1D 104.47(17) . .
C1D S1D C1D 105.8(3) 2_654 .
S1D O1D S1D 49.03(15) 2_654 .
S1D C1D S1D 44.81(14) 2_654 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.743(3) .
S1 C3 1.747(3) .
S2 C2 1.630(3) .
N1 C2 1.361(4) .
N1 C1 1.371(4) .
O1 C1 1.222(4) .
O2 C6 1.361(4) .
C1 C3 1.474(4) .
C3 C4 1.341(4) .
C4 C5 1.444(4) .
C5 C10 1.396(4) .
C5 C6 1.413(4) .
C6 C7 1.386(4) .
C7 C8 1.378(5) .
C8 C9 1.392(5) .
C9 C10 1.375(5) .
S1D S1D 1.307(3) 2_654
S1D O1D 1.575(3) .
S1D C1D 1.692(4) 2_654
S1D C1D 1.736(4) .
O1D S1D 1.575(3) 2_654
C1D S1D 1.692(4) 2_654
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
O2 H2 O1D 0.82 1.93 2.686(3) 153.7 .
O2 H2 S1D 0.82 2.64 3.445(3) 167.5 .
N1 H1 O1 0.86 2.00 2.841(4) 167.2 5_665
C10 H10 S1 0.93 2.61 3.317(3) 133.1 .
C7 H7 S1D 0.93 2.88 3.592(4) 134.9 .
