#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/47/7204713.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_7204713
loop_
_publ_author_name
'Tahir Khan'
'Joseph J. W. McDouall'
'Eric J. L. McInnes'
'Peter J. Skabara'
'Pierre Frère'
'Simon J. Coles'
'Michael B. Hursthouse'
_publ_section_title
;
 A combined substituent and supramolecular approach for improving the
 electron donor properties of 1,3-dithiole-2-thione derivatives
;
_journal_issue                   10
_journal_name_full               'J. Mater. Chem.'
_journal_page_first              2490
_journal_page_last               2498
_journal_paper_doi               10.1039/b307025e
_journal_volume                  13
_journal_year                    2003
_chemical_formula_sum            'C21 H18 O6 S2'
_chemical_formula_weight         430.47
_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                94.82(3)
_cell_angle_beta                 111.22(3)
_cell_angle_gamma                107.38(3)
_cell_formula_units_Z            2
_cell_length_a                   9.913(2)
_cell_length_b                   10.263(2)
_cell_length_c                   10.766(2)
_cell_measurement_reflns_used    10790
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.96
_cell_volume                     951.4(5)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'CAMERON (Watkin, Pearce 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald Sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10790
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.879
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_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          0.1183
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                2988
_reflns_number_total             4254
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b307025e.txt
_cod_data_source_block           compound_8d
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'multi-scans' was replaced
with 'multi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        951.4(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204713
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 0.10254(6) 0.42267(6) 0.29678(5) 0.03087(17) Uani 1 1 d . . .
S2 S -0.02634(7) 0.11137(6) 0.19843(5) 0.03283(18) Uani 1 1 d . . .
O1 O -0.27617(18) 0.86947(16) 0.47675(15) 0.0361(4) Uani 1 1 d . . .
O2 O 0.02563(18) 0.64061(16) 0.36138(16) 0.0378(4) Uani 1 1 d . . .
O3 O -0.81475(19) -0.35234(16) 0.06170(15) 0.0365(4) Uani 1 1 d . . .
O4 O -0.28444(19) -0.11295(16) 0.13034(16) 0.0367(4) Uani 1 1 d . . .
O5 O -0.32971(17) 0.25851(14) 0.25642(13) 0.0270(3) Uani 1 1 d . . .
O6 O 0.25514(19) 0.27294(18) 0.24181(15) 0.0403(4) Uani 1 1 d . . .
C2 C 0.1335(3) 0.2700(2) 0.2457(2) 0.0325(5) Uani 1 1 d . . .
C3 C -0.0875(3) 0.3376(2) 0.27497(19) 0.0278(5) Uani 1 1 d . . .
C4 C -0.1490(3) 0.1889(2) 0.22855(19) 0.0269(5) Uani 1 1 d . . .
C5 C -0.2008(2) 0.3776(2) 0.29177(19) 0.0252(4) Uani 1 1 d . . .
C6 C -0.2235(2) 0.5053(2) 0.33555(19) 0.0257(4) Uani 1 1 d . . .
C7 C -0.3627(3) 0.4991(2) 0.3415(2) 0.0299(5) Uani 1 1 d . . .
H7 H -0.4423 0.4128 0.3142 0.036 Uiso 1 1 calc R . .
C8 C -0.3876(3) 0.6172(2) 0.3868(2) 0.0307(5) Uani 1 1 d . . .
H8 H -0.4819 0.6100 0.3902 0.037 Uiso 1 1 calc R . .
C9 C -0.2685(3) 0.7461(2) 0.4269(2) 0.0295(5) Uani 1 1 d . . .
C10 C -0.1293(3) 0.7566(2) 0.4194(2) 0.0297(5) Uani 1 1 d . . .
H10 H -0.0509 0.8435 0.4451 0.036 Uiso 1 1 calc R . .
C11 C -0.1063(3) 0.6383(2) 0.3736(2) 0.0285(5) Uani 1 1 d . . .
C12 C -0.4154(3) 0.8637(2) 0.4883(2) 0.0390(6) Uani 1 1 d . . .
H12A H -0.4978 0.8375 0.3989 0.059 Uiso 1 1 calc R . .
H12B H -0.4033 0.9538 0.5333 0.059 Uiso 1 1 calc R . .
H12C H -0.4396 0.7958 0.5405 0.059 Uiso 1 1 calc R . .
C13 C 0.1476(3) 0.7716(2) 0.3976(3) 0.0430(6) Uani 1 1 d . . .
H13A H 0.1112 0.8332 0.3430 0.065 Uiso 1 1 calc R . .
H13B H 0.2324 0.7580 0.3820 0.065 Uiso 1 1 calc R . .
H13C H 0.1817 0.8119 0.4924 0.065 Uiso 1 1 calc R . .
C14 C -0.2984(3) 0.1427(2) 0.21695(19) 0.0260(5) Uani 1 1 d . . .
C15 C -0.4298(3) 0.0126(2) 0.17643(19) 0.0255(5) Uani 1 1 d . . .
C16 C -0.5703(3) 0.0120(2) 0.17718(19) 0.0278(5) Uani 1 1 d . . .
H16 H -0.5788 0.0964 0.2049 0.033 Uiso 1 1 calc R . .
C17 C -0.6974(3) -0.1097(2) 0.1382(2) 0.0299(5) Uani 1 1 d . . .
H17 H -0.7897 -0.1067 0.1395 0.036 Uiso 1 1 calc R . .
C18 C -0.6857(3) -0.2360(2) 0.09724(19) 0.0294(5) Uani 1 1 d . . .
C19 C -0.5484(3) -0.2400(2) 0.0939(2) 0.0309(5) Uani 1 1 d . . .
H19 H -0.5410 -0.3249 0.0658 0.037 Uiso 1 1 calc R . .
C20 C -0.4225(3) -0.1174(2) 0.1324(2) 0.0285(5) Uani 1 1 d . . .
C21 C -0.8053(3) -0.4838(2) 0.0197(2) 0.0379(6) Uani 1 1 d . . .
H21A H -0.7814 -0.4826 -0.0591 0.057 Uiso 1 1 calc R . .
H21B H -0.9026 -0.5569 -0.0025 0.057 Uiso 1 1 calc R . .
H21C H -0.7255 -0.5002 0.0925 0.057 Uiso 1 1 calc R . .
C22 C -0.2756(3) -0.2368(2) 0.0674(2) 0.0411(6) Uani 1 1 d . . .
H22A H -0.2968 -0.3093 0.1159 0.062 Uiso 1 1 calc R . .
H22B H -0.1737 -0.2174 0.0697 0.062 Uiso 1 1 calc R . .
H22C H -0.3503 -0.2668 -0.0256 0.062 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 0.0033 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'
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 S1 C2 95.68(11) . . ?
C4 S2 C2 95.42(11) . . ?
C9 O1 C12 116.98(19) . . ?
C11 O2 C13 118.39(17) . . ?
C18 O3 C21 117.37(18) . . ?
C20 O4 C22 118.53(19) . . ?
C5 O5 C14 109.61(17) . . ?
O6 C2 S1 122.40(19) . . ?
O6 C2 S2 122.10(18) . . ?
S1 C2 S2 115.50(13) . . ?
C5 C3 C4 107.6(2) . . ?
C5 C3 S1 135.65(17) . . ?
C4 C3 S1 116.73(16) . . ?
C14 C4 C3 107.74(19) . . ?
C14 C4 S2 135.58(17) . . ?
C3 C4 S2 116.67(17) . . ?
C3 C5 O5 107.59(18) . . ?
C3 C5 C6 139.1(2) . . ?
O5 C5 C6 113.29(18) . . ?
C7 C6 C11 117.57(19) . . ?
C7 C6 C5 120.48(19) . . ?
C11 C6 C5 121.95(19) . . ?
C6 C7 C8 122.5(2) . . ?
C7 C8 C9 118.6(2) . . ?
O1 C9 C10 114.9(2) . . ?
O1 C9 C8 124.6(2) . . ?
C10 C9 C8 120.48(19) . . ?
C11 C10 C9 120.3(2) . . ?
O2 C11 C10 123.6(2) . . ?
O2 C11 C6 115.80(18) . . ?
C10 C11 C6 120.6(2) . . ?
C4 C14 O5 107.43(18) . . ?
C4 C14 C15 139.65(19) . . ?
O5 C14 C15 112.92(18) . . ?
C16 C15 C20 116.9(2) . . ?
C16 C15 C14 121.03(18) . . ?
C20 C15 C14 122.0(2) . . ?
C17 C16 C15 122.3(2) . . ?
C16 C17 C18 119.3(2) . . ?
O3 C18 C17 116.3(2) . . ?
O3 C18 C19 123.40(19) . . ?
C17 C18 C19 120.3(2) . . ?
C20 C19 C18 119.76(19) . . ?
O4 C20 C19 123.07(19) . . ?
O4 C20 C15 115.51(19) . . ?
C19 C20 C15 121.4(2) . . ?
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 C3 1.741(2) . ?
S1 C2 1.766(2) . ?
S2 C4 1.743(2) . ?
S2 C2 1.776(3) . ?
O1 C9 1.367(3) . ?
O1 C12 1.414(3) . ?
O2 C11 1.355(3) . ?
O2 C13 1.422(3) . ?
O3 C18 1.366(3) . ?
O3 C21 1.427(3) . ?
O4 C20 1.364(3) . ?
O4 C22 1.431(2) . ?
O5 C5 1.381(3) . ?
O5 C14 1.386(2) . ?
O6 C2 1.213(3) . ?
C3 C5 1.368(3) . ?
C3 C4 1.430(3) . ?
C4 C14 1.368(3) . ?
C5 C6 1.463(3) . ?
C6 C7 1.387(3) . ?
C6 C11 1.412(3) . ?
C7 C8 1.391(3) . ?
C8 C9 1.390(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.384(3) . ?
C14 C15 1.457(3) . ?
C15 C16 1.393(3) . ?
C15 C20 1.410(3) . ?
C16 C17 1.383(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.387(3) . ?
C19 C20 1.383(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4421059
