#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/06/2220662.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220662
loop_
_publ_author_name
'Raftery, James'
'Lallbeeharry, Hiteyeshi'
'Bhowon, Minu G.'
'Laulloo, Sabina J.'
'Joule, John A.'
_publ_section_title
N,N'-(2,2'-Dithiodi-o-phenylene)bis(furan-2-carboxamide)
_journal_coeditor_code           WW2132
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o16
_journal_paper_doi               10.1107/S1600536808038828
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H16 N2 O4 S2'
_chemical_formula_moiety         'C22 H16 N2 O4 S2'
_chemical_formula_sum            'C22 H16 N2 O4 S2'
_chemical_formula_weight         436.49
_chemical_melting_point          434
_chemical_name_systematic
;
N,N'-(2,2'-Dithiodi-o-phenylene)bis(furan-2-carboxamide)
;
_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                109.770(2)
_cell_angle_beta                 103.748(2)
_cell_angle_gamma                104.643(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6173(11)
_cell_length_b                   9.9210(11)
_cell_length_c                   11.9906(14)
_cell_measurement_reflns_used    1625
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.156
_cell_measurement_theta_min      2.34
_cell_volume                     973.84(19)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω'
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6177
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.834
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0402
_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)+(0.0233P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0761
_reflns_number_gt                2911
_reflns_number_total             4327
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww2132.cif
_cod_data_source_block           I
_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:

'_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2220662
_cod_database_fobs_code          2220662
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.0310(2) 0.5459(2) 0.2881(2) 0.0182(5) Uani d . 1 . .
C C2 -0.0923(2) 0.4603(2) 0.3075(2) 0.0222(5) Uani d . 1 . .
H H2 -0.1147 0.5039 0.3816 0.027 Uiso calc R 1 . .
C C3 -0.1820(2) 0.3115(3) 0.2187(2) 0.0260(5) Uani d . 1 . .
H H3 -0.2684 0.2539 0.2301 0.031 Uiso calc R 1 . .
C C4 -0.1452(2) 0.2476(3) 0.1137(2) 0.0254(5) Uani d . 1 . .
H H4 -0.2047 0.1440 0.0547 0.031 Uiso calc R 1 . .
C C5 -0.0240(2) 0.3304(2) 0.0922(2) 0.0210(5) Uani d . 1 . .
H H5 -0.0006 0.2842 0.0191 0.025 Uiso calc R 1 . .
C C6 0.0639(2) 0.4823(2) 0.1783(2) 0.0175(5) Uani d . 1 . .
C C7 0.2528(2) 0.5374(2) 0.0722(2) 0.0191(5) Uani d . 1 . .
C C8 0.3733(2) 0.6694(2) 0.08069(19) 0.0177(5) Uani d . 1 . .
C C9 0.4744(2) 0.6804(2) 0.0208(2) 0.0208(5) Uani d . 1 . .
H H9 0.4866 0.5977 -0.0400 0.025 Uiso calc R 1 . .
C C10 0.5592(2) 0.8391(2) 0.0659(2) 0.0269(5) Uani d . 1 . .
H H10 0.6394 0.8836 0.0412 0.032 Uiso calc R 1 . .
C C11 0.5045(2) 0.9148(2) 0.1501(2) 0.0276(5) Uani d . 1 . .
H H11 0.5404 1.0235 0.1946 0.033 Uiso calc R 1 . .
C C12 0.4601(2) 0.7032(2) 0.45289(19) 0.0175(5) Uani d . 1 . .
C C13 0.4594(2) 0.5616(2) 0.37237(19) 0.0175(5) Uani d . 1 . .
C C14 0.5733(2) 0.5626(2) 0.3192(2) 0.0205(5) Uani d . 1 . .
H H14 0.5755 0.4683 0.2652 0.025 Uiso calc R 1 . .
C C15 0.6830(2) 0.7001(2) 0.3446(2) 0.0247(5) Uani d . 1 . .
H H15 0.7581 0.6993 0.3055 0.030 Uiso calc R 1 . .
C C16 0.6855(2) 0.8386(2) 0.4259(2) 0.0249(5) Uani d . 1 . .
H H16 0.7629 0.9323 0.4441 0.030 Uiso calc R 1 . .
C C17 0.5740(2) 0.8393(2) 0.4805(2) 0.0221(5) Uani d . 1 . .
H H17 0.5758 0.9341 0.5374 0.027 Uiso calc R 1 . .
C C18 0.3246(2) 0.2766(2) 0.27812(19) 0.0193(5) Uani d . 1 . .
C C19 0.1878(2) 0.1613(2) 0.2705(2) 0.0193(5) Uani d . 1 . .
C C20 0.1276(2) 0.0073(2) 0.2061(2) 0.0259(5) Uani d . 1 . .
H H20 0.1682 -0.0548 0.1537 0.031 Uiso calc R 1 . .
C C21 -0.0076(2) -0.0446(2) 0.2314(2) 0.0267(5) Uani d . 1 . .
H H21 -0.0758 -0.1480 0.1991 0.032 Uiso calc R 1 . .
C C22 -0.0201(2) 0.0812(2) 0.3100(2) 0.0270(5) Uani d . 1 . .
H H22 -0.1007 0.0805 0.3429 0.032 Uiso calc R 1 . .
N N1 0.18360(17) 0.57613(18) 0.15935(16) 0.0187(4) Uani d . 1 . .
H H1 0.2194 0.6744 0.2112 0.022 Uiso calc R 1 . .
N N2 0.34384(17) 0.42539(18) 0.34788(15) 0.0180(4) Uani d . 1 . .
H H2A 0.2740 0.4374 0.3823 0.022 Uiso calc R 1 . .
O O1 0.21966(16) 0.40672(16) -0.00702(15) 0.0279(4) Uani d . 1 . .
O O2 0.39021(15) 0.81377(15) 0.16313(14) 0.0227(3) Uani d . 1 . .
O O3 0.41169(15) 0.23672(16) 0.22600(14) 0.0271(4) Uani d . 1 . .
O O4 0.09859(15) 0.21068(15) 0.33633(14) 0.0229(4) Uani d . 1 . .
S S1 0.14557(6) 0.73663(6) 0.40340(5) 0.02100(14) Uani d . 1 . .
S S2 0.31812(6) 0.70909(6) 0.52536(5) 0.02075(14) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.24(19) ?
C2 C1 S1 . . 119.34(17) ?
C6 C1 S1 . . 120.42(15) ?
C3 C2 C1 . . 119.9(2) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
C4 C3 C2 . . 119.50(19) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 121.6(2) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C4 C5 C6 . . 119.6(2) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C5 C6 N1 . . 122.76(19) ?
C5 C6 C1 . . 119.09(18) ?
N1 C6 C1 . . 118.14(18) ?
O1 C7 N1 . . 124.76(19) ?
O1 C7 C8 . . 121.70(19) ?
N1 C7 C8 . . 113.54(18) ?
C9 C8 O2 . . 110.26(18) ?
C9 C8 C7 . . 132.45(19) ?
O2 C8 C7 . . 117.28(17) ?
C8 C9 C10 . . 106.59(18) ?
C8 C9 H9 . . 126.7 ?
C10 C9 H9 . . 126.7 ?
C11 C10 C9 . . 106.89(18) ?
C11 C10 H10 . . 126.6 ?
C9 C10 H10 . . 126.6 ?
C10 C11 O2 . . 110.59(18) ?
C10 C11 H11 . . 124.7 ?
O2 C11 H11 . . 124.7 ?
C17 C12 C13 . . 120.33(18) ?
C17 C12 S2 . . 119.14(15) ?
C13 C12 S2 . . 120.49(15) ?
C14 C13 N2 . . 122.53(18) ?
C14 C13 C12 . . 118.45(19) ?
N2 C13 C12 . . 119.02(17) ?
C15 C14 C13 . . 120.27(19) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C16 . . 121.12(19) ?
C14 C15 H15 . . 119.4 ?
C16 C15 H15 . . 119.4 ?
C15 C16 C17 . . 119.2(2) ?
C15 C16 H16 . . 120.4 ?
C17 C16 H16 . . 120.4 ?
C12 C17 C16 . . 120.5(2) ?
C12 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?
O3 C18 N2 . . 125.09(19) ?
O3 C18 C19 . . 120.47(18) ?
N2 C18 C19 . . 114.43(18) ?
C20 C19 O4 . . 110.13(18) ?
C20 C19 C18 . . 131.36(19) ?
O4 C19 C18 . . 118.50(17) ?
C19 C20 C21 . . 106.93(19) ?
C19 C20 H20 . . 126.5 ?
C21 C20 H20 . . 126.5 ?
C22 C21 C20 . . 106.23(19) ?
C22 C21 H21 . . 126.9 ?
C20 C21 H21 . . 126.9 ?
C21 C22 O4 . . 110.92(18) ?
C21 C22 H22 . . 124.5 ?
O4 C22 H22 . . 124.5 ?
C7 N1 C6 . . 129.57(17) ?
C7 N1 H1 . . 115.2 ?
C6 N1 H1 . . 115.2 ?
C18 N2 C13 . . 129.03(17) ?
C18 N2 H2A . . 115.5 ?
C13 N2 H2A . . 115.5 ?
C11 O2 C8 . . 105.66(16) ?
C22 O4 C19 . . 105.80(15) ?
C1 S1 S2 . . 103.80(7) ?
C12 S2 S1 . . 104.78(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.392(3) ?
C1 C6 . 1.403(3) ?
C1 S1 . 1.777(2) ?
C2 C3 . 1.383(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.378(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.380(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.393(3) ?
C5 H5 . 0.9500 ?
C6 N1 . 1.403(2) ?
C7 O1 . 1.224(2) ?
C7 N1 . 1.368(2) ?
C7 C8 . 1.468(3) ?
C8 C9 . 1.343(3) ?
C8 O2 . 1.380(2) ?
C9 C10 . 1.415(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.341(3) ?
C10 H10 . 0.9500 ?
C11 O2 . 1.367(2) ?
C11 H11 . 0.9500 ?
C12 C17 . 1.382(3) ?
C12 C13 . 1.407(3) ?
C12 S2 . 1.7871(19) ?
C13 C14 . 1.392(3) ?
C13 N2 . 1.402(2) ?
C14 C15 . 1.380(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.380(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.382(3) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C18 O3 . 1.224(2) ?
C18 N2 . 1.366(2) ?
C18 C19 . 1.469(3) ?
C19 C20 . 1.344(3) ?
C19 O4 . 1.369(2) ?
C20 C21 . 1.415(3) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.340(3) ?
C21 H21 . 0.9500 ?
C22 O4 . 1.366(2) ?
C22 H22 . 0.9500 ?
N1 H1 . 0.8800 ?
N2 H2A . 0.8800 ?
S1 S2 . 2.0768(8) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A S2 . 0.88 2.52 3.0104(16) 116.1
N2 H2A O4 . 0.88 2.24 2.688(2) 111.4
N1 H1 S1 . 0.88 2.50 2.9805(18) 115.3
N1 H1 O2 . 0.88 2.19 2.651(2) 112.4
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.5(3) ?
S1 C1 C2 C3 . . . . -179.76(15) ?
C1 C2 C3 C4 . . . . 2.2(3) ?
C2 C3 C4 C5 . . . . -2.5(3) ?
C3 C4 C5 C6 . . . . 0.1(3) ?
C4 C5 C6 N1 . . . . -176.52(18) ?
C4 C5 C6 C1 . . . . 2.6(3) ?
C2 C1 C6 C5 . . . . -2.9(3) ?
S1 C1 C6 C5 . . . . 177.37(15) ?
C2 C1 C6 N1 . . . . 176.30(17) ?
S1 C1 C6 N1 . . . . -3.5(2) ?
O1 C7 C8 C9 . . . . -6.0(4) ?
N1 C7 C8 C9 . . . . 174.5(2) ?
O1 C7 C8 O2 . . . . 172.76(18) ?
N1 C7 C8 O2 . . . . -6.8(3) ?
O2 C8 C9 C10 . . . . -0.6(2) ?
C7 C8 C9 C10 . . . . 178.2(2) ?
C8 C9 C10 C11 . . . . 0.0(2) ?
C9 C10 C11 O2 . . . . 0.6(3) ?
C17 C12 C13 C14 . . . . -1.6(3) ?
S2 C12 C13 C14 . . . . -179.28(15) ?
C17 C12 C13 N2 . . . . 178.93(18) ?
S2 C12 C13 N2 . . . . 1.2(3) ?
N2 C13 C14 C15 . . . . 178.88(19) ?
C12 C13 C14 C15 . . . . -0.6(3) ?
C13 C14 C15 C16 . . . . 2.1(3) ?
C14 C15 C16 C17 . . . . -1.4(3) ?
C13 C12 C17 C16 . . . . 2.3(3) ?
S2 C12 C17 C16 . . . . -179.97(16) ?
C15 C16 C17 C12 . . . . -0.8(3) ?
O3 C18 C19 C20 . . . . -5.0(4) ?
N2 C18 C19 C20 . . . . 175.9(2) ?
O3 C18 C19 O4 . . . . 176.19(18) ?
N2 C18 C19 O4 . . . . -2.9(3) ?
O4 C19 C20 C21 . . . . 0.4(3) ?
C18 C19 C20 C21 . . . . -178.5(2) ?
C19 C20 C21 C22 . . . . -0.4(3) ?
C20 C21 C22 O4 . . . . 0.2(3) ?
O1 C7 N1 C6 . . . . -0.5(3) ?
C8 C7 N1 C6 . . . . 179.00(18) ?
C5 C6 N1 C7 . . . . -11.6(3) ?
C1 C6 N1 C7 . . . . 169.31(19) ?
O3 C18 N2 C13 . . . . 2.0(3) ?
C19 C18 N2 C13 . . . . -178.95(18) ?
C14 C13 N2 C18 . . . . 3.7(3) ?
C12 C13 N2 C18 . . . . -176.88(19) ?
C10 C11 O2 C8 . . . . -1.0(2) ?
C9 C8 O2 C11 . . . . 1.0(2) ?
C7 C8 O2 C11 . . . . -178.06(18) ?
C21 C22 O4 C19 . . . . 0.0(2) ?
C20 C19 O4 C22 . . . . -0.3(2) ?
C18 C19 O4 C22 . . . . 178.75(18) ?
C2 C1 S1 S2 . . . . 90.48(16) ?
C6 C1 S1 S2 . . . . -89.74(16) ?
C17 C12 S2 S1 . . . . 88.52(16) ?
C13 C12 S2 S1 . . . . -93.76(16) ?
C1 S1 S2 C12 . . . . 84.72(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1076522
