##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
trans-(+-)-Diethyl N,N'-(1,2-cyclohexane-1,2-diyl)bis(2-thiooxamate)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H22 N2 O4 S2'
_chemical_formula_sum     'C14 H22 N2 O4 S2'
_chemical_formula_iupac     'C14 H22 N2 O4 S2'
_chemical_formula_weight     346.46
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.6438(10)
_cell_length_b     9.6656(11)
_cell_length_c     10.3316(11)
_cell_angle_alpha     85.068(9)
_cell_angle_beta     63.887(10)
_cell_angle_gamma     77.155(9)
_cell_volume     843.02(18)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1822
_cell_measurement_theta_min     2
_cell_measurement_theta_max     25
_cell_measurement_temperature     120(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     prism
_exptl_crystal_size_max     0.4
_exptl_crystal_size_mid     0.4
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.365
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     368
_exptl_absorpt_coefficient_mu     0.334
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(Blessing, 1995)'
_exptl_absorpt_correction_T_min     0.840
_exptl_absorpt_correction_T_max     0.935
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_DIFFRN_MEASUREMENT_DEVICE_TYPE     'Kuma KM-4 CCD κ geometry'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6232
_diffrn_reflns_av_R_equivalents     0.0158
_diffrn_reflns_av_sigmaI/netI     0.0212
_diffrn_reflns_theta_min     4.19
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2957
_reflns_number_gt     2587
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0319
_refine_ls_R_factor_gt     0.0272
_refine_ls_wR_factor_gt     0.0696
_refine_ls_wR_factor_ref     0.0717
_refine_ls_goodness_of_fit_ref     1.074
_refine_ls_restrained_S_all     1.074
_refine_ls_number_reflns     2957
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0368P)²+0.2571P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.288
_refine_diff_density_min     -0.254
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_cell_refinement
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
Stereochemical Workstation (Siemens, 1989) and
Mercury (Version 1.4; Macrae et al.,  2006)
;
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
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
    S S1 0.35976(4) 0.69933(4) 0.46565(4) 0.02187(12) Uani d . 1 . .
    S S2 1.19840(4) 0.53228(4) 0.29613(4) 0.02021(11) Uani d . 1 . .
    N N1 0.62809(13) 0.69442(12) 0.48528(13) 0.0139(3) Uani d . 1 . .
    H H1N 0.6804 0.6847 0.5381 0.017 Uiso calc R 1 . .
    N N2 0.92356(13) 0.50755(12) 0.30340(13) 0.0135(3) Uani d . 1 . .
    H H2N 0.8554 0.4542 0.3170 0.016 Uiso calc R 1 . .
    O O1 0.47309(11) 0.72452(11) 0.77377(11) 0.0170(2) Uani d . 1 . .
    O O2 0.30209(12) 0.59896(12) 0.77384(12) 0.0245(3) Uani d . 1 . .
    O O3 1.02185(11) 0.22440(10) 0.27997(11) 0.0156(2) Uani d . 1 . .
    O O4 1.12998(13) 0.23753(11) 0.43211(12) 0.0230(3) Uani d . 1 . .
    C C1 0.71027(16) 0.71874(15) 0.33006(15) 0.0140(3) Uani d . 1 . .
    H H1 0.6649 0.6720 0.2794 0.017 Uiso calc R 1 . .
    C C2 0.88775(16) 0.65738(15) 0.26827(15) 0.0133(3) Uani d . 1 . .
    H H2 0.9352 0.7123 0.3101 0.016 Uiso calc R 1 . .
    C C3 0.96125(17) 0.67708(15) 0.10400(16) 0.0164(3) Uani d . 1 . .
    H H3A 1.0753 0.6338 0.0622 0.020 Uiso calc R 1 . .
    H H3B 0.9109 0.6286 0.0610 0.020 Uiso calc R 1 . .
    C C4 0.93827(18) 0.83488(16) 0.06865(16) 0.0184(3) Uani d . 1 . .
    H H4A 0.9823 0.8462 -0.0372 0.022 Uiso calc R 1 . .
    H H4B 0.9964 0.8814 0.1047 0.022 Uiso calc R 1 . .
    C C5 0.76336(18) 0.90689(16) 0.13711(17) 0.0214(3) Uani d . 1 . .
    H H5A 0.7087 0.8712 0.0892 0.026 Uiso calc R 1 . .
    H H5B 0.7531 1.0105 0.1215 0.026 Uiso calc R 1 . .
    C C6 0.68366(17) 0.87894(15) 0.29946(17) 0.0185(3) Uani d . 1 . .
    H H6A 0.5690 0.9190 0.3377 0.022 Uiso calc R 1 . .
    H H6B 0.7271 0.9271 0.3496 0.022 Uiso calc R 1 . .
    C C7 0.47662(16) 0.68664(15) 0.54806(16) 0.0154(3) Uani d . 1 . .
    C C8 0.40673(16) 0.66322(15) 0.71070(16) 0.0164(3) Uani d . 1 . .
    C C9 0.42059(18) 0.69739(17) 0.92856(16) 0.0201(3) Uani d . 1 . .
    H H9A 0.4350 0.5940 0.9461 0.024 Uiso calc R 1 . .
    H H9B 0.3074 0.7410 0.9824 0.024 Uiso calc R 1 . .
    C C10 0.51870(19) 0.7615(2) 0.97764(18) 0.0280(4) Uani d . 1 . .
    H H10A 0.4864 0.7447 1.0808 0.042 Uiso calc R 1 . .
    H H10B 0.5030 0.8639 0.9604 0.042 Uiso calc R 1 . .
    H H10C 0.6304 0.7176 0.9236 0.042 Uiso calc R 1 . .
    C C11 1.05620(16) 0.44974(15) 0.31527(15) 0.0150(3) Uani d . 1 . .
    C C12 1.07415(16) 0.29256(15) 0.35109(15) 0.0151(3) Uani d . 1 . .
    C C13 1.01111(18) 0.07662(15) 0.32092(17) 0.0191(3) Uani d . 1 . .
    H H13A 0.9368 0.0484 0.2910 0.023 Uiso calc R 1 . .
    H H13B 0.9681 0.0694 0.4271 0.023 Uiso calc R 1 . .
    C C14 1.16926(19) -0.02452(16) 0.25308(18) 0.0234(4) Uani d . 1 . .
    H H14A 1.1562 -0.1215 0.2833 0.035 Uiso calc R 1 . .
    H H14B 1.2426 0.0016 0.2841 0.035 Uiso calc R 1 . .
    H H14C 1.2114 -0.0192 0.1479 0.035 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    S1 C7 . 1.6659(15) ?
    S2 C11 . 1.6664(14) ?
    N1 C7 . 1.3291(18) ?
    N1 C1 . 1.4678(18) ?
    N1 H1N . 0.8800 ?
    N2 C11 . 1.3312(18) ?
    N2 C2 . 1.4648(18) ?
    N2 H2N . 0.8800 ?
    O1 C8 . 1.3368(18) ?
    O1 C9 . 1.4686(18) ?
    O2 C8 . 1.2080(18) ?
    O3 C12 . 1.3362(17) ?
    O3 C13 . 1.4674(17) ?
    O4 C12 . 1.2110(17) ?
    C1 C2 . 1.5300(19) ?
    C1 C6 . 1.541(2) ?
    C1 H1 . 1.0000 ?
    C2 C3 . 1.538(2) ?
    C2 H2 . 1.0000 ?
    C3 C4 . 1.528(2) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.531(2) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 C6 . 1.535(2) ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C8 . 1.528(2) ?
    C9 C10 . 1.508(2) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 C12 . 1.522(2) ?
    C13 C14 . 1.512(2) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
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
    C7 N1 C1 . . 121.67(12) ?
    C7 N1 H1N . . 119.2 ?
    C1 N1 H1N . . 119.2 ?
    C11 N2 C2 . . 121.92(12) ?
    C11 N2 H2N . . 119.0 ?
    C2 N2 H2N . . 119.0 ?
    C8 O1 C9 . . 115.03(11) ?
    C12 O3 C13 . . 116.13(11) ?
    N1 C1 C2 . . 112.62(11) ?
    N1 C1 C6 . . 110.12(12) ?
    C2 C1 C6 . . 109.01(11) ?
    N1 C1 H1 . . 108.3 ?
    C2 C1 H1 . . 108.3 ?
    C6 C1 H1 . . 108.3 ?
    N2 C2 C1 . . 112.54(11) ?
    N2 C2 C3 . . 110.48(11) ?
    C1 C2 C3 . . 108.87(11) ?
    N2 C2 H2 . . 108.3 ?
    C1 C2 H2 . . 108.3 ?
    C3 C2 H2 . . 108.3 ?
    C4 C3 C2 . . 110.10(12) ?
    C4 C3 H3A . . 109.6 ?
    C2 C3 H3A . . 109.6 ?
    C4 C3 H3B . . 109.6 ?
    C2 C3 H3B . . 109.6 ?
    H3A C3 H3B . . 108.2 ?
    C3 C4 C5 . . 111.16(12) ?
    C3 C4 H4A . . 109.4 ?
    C5 C4 H4A . . 109.4 ?
    C3 C4 H4B . . 109.4 ?
    C5 C4 H4B . . 109.4 ?
    H4A C4 H4B . . 108.0 ?
    C4 C5 C6 . . 111.90(12) ?
    C4 C5 H5A . . 109.2 ?
    C6 C5 H5A . . 109.2 ?
    C4 C5 H5B . . 109.2 ?
    C6 C5 H5B . . 109.2 ?
    H5A C5 H5B . . 107.9 ?
    C5 C6 C1 . . 111.12(12) ?
    C5 C6 H6A . . 109.4 ?
    C1 C6 H6A . . 109.4 ?
    C5 C6 H6B . . 109.4 ?
    C1 C6 H6B . . 109.4 ?
    H6A C6 H6B . . 108.0 ?
    N1 C7 C8 . . 115.68(12) ?
    N1 C7 S1 . . 126.01(12) ?
    C8 C7 S1 . . 118.31(10) ?
    O2 C8 O1 . . 124.61(14) ?
    O2 C8 C7 . . 123.49(13) ?
    O1 C8 C7 . . 111.89(12) ?
    O1 C9 C10 . . 107.65(12) ?
    O1 C9 H9A . . 110.2 ?
    C10 C9 H9A . . 110.2 ?
    O1 C9 H9B . . 110.2 ?
    C10 C9 H9B . . 110.2 ?
    H9A C9 H9B . . 108.5 ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    N2 C11 C12 . . 114.68(12) ?
    N2 C11 S2 . . 126.56(11) ?
    C12 C11 S2 . . 118.76(10) ?
    O4 C12 O3 . . 125.05(13) ?
    O4 C12 C11 . . 124.11(13) ?
    O3 C12 C11 . . 110.83(12) ?
    O3 C13 C14 . . 112.42(12) ?
    O3 C13 H13A . . 109.1 ?
    C14 C13 H13A . . 109.1 ?
    O3 C13 H13B . . 109.1 ?
    C14 C13 H13B . . 109.1 ?
    H13A C13 H13B . . 107.9 ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
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
    C7 N1 C1 C2 . . . . -153.12(13) y
    C7 N1 C1 C6 . . . . 84.98(16) y
    C11 N2 C2 C1 . . . . -151.70(13) y
    C11 N2 C2 C3 . . . . 86.37(15) y
    N1 C1 C2 N2 . . . . 52.61(15) y
    C6 C1 C2 N2 . . . . 175.14(11) ?
    N1 C1 C2 C3 . . . . 175.44(11) ?
    C6 C1 C2 C3 . . . . -62.03(14) ?
    N2 C2 C3 C4 . . . . -174.06(11) ?
    C1 C2 C3 C4 . . . . 61.88(14) ?
    C2 C3 C4 C5 . . . . -56.87(16) ?
    C3 C4 C5 C6 . . . . 52.72(17) ?
    C4 C5 C6 C1 . . . . -53.51(16) ?
    N1 C1 C6 C5 . . . . -177.87(11) ?
    C2 C1 C6 C5 . . . . 58.11(15) ?
    C1 N1 C7 C8 . . . . -179.09(12) ?
    C1 N1 C7 S1 . . . . 1.2(2) ?
    C9 O1 C8 O2 . . . . 5.7(2) ?
    C9 O1 C8 C7 . . . . -175.52(11) ?
    N1 C7 C8 O2 . . . . -148.80(14) ?
    S1 C7 C8 O2 . . . . 30.94(19) y
    N1 C7 C8 O1 . . . . 32.43(17) ?
    S1 C7 C8 O1 . . . . -147.83(10) ?
    C8 O1 C9 C10 . . . . 174.37(12) ?
    C2 N2 C11 C12 . . . . -179.51(12) ?
    C2 N2 C11 S2 . . . . 1.0(2) ?
    C13 O3 C12 O4 . . . . 9.3(2) ?
    C13 O3 C12 C11 . . . . -171.39(11) ?
    N2 C11 C12 O4 . . . . -141.38(14) ?
    S2 C11 C12 O4 . . . . 38.18(19) y
    N2 C11 C12 O3 . . . . 39.32(17) ?
    S2 C11 C12 O3 . . . . -141.12(11) ?
    C12 O3 C13 C14 . . . . -79.71(16) ?
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
    N1 H1N O4 2_766 0.88 2.27 3.0226(16) 144
    N1 H1N S2 2_766 0.88 2.96 3.6806(13) 141
    N2 H2N O2 2_666 0.88 2.27 3.0163(16) 143
    N2 H2N S1 2_666 0.88 2.87 3.6093(13) 143
    C1 H1 O2 2_666 1.00 2.64 3.3820(18) 131
    C2 H2 O4 2_766 1.00 2.52 3.2620(18) 131
data_II
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(+-)-N,N'-diethyl (1,2-diphenylethane-1,2-diyl)bis(2-thiooxamate)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H24 N2 O4 S2'
_chemical_formula_sum     'C22 H24 N2 O4 S2'
_chemical_formula_iupac     'C22 H24 N2 O4 S2'
_chemical_formula_weight     444.55
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     9.2414(4)
_cell_length_b     21.7781(10)
_cell_length_c     11.4322(6)
_cell_angle_alpha     90.00
_cell_angle_beta     100.273(4)
_cell_angle_gamma     90.00
_cell_volume     2263.96(19)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4659
_cell_measurement_theta_min     4
_cell_measurement_theta_max     25
_cell_measurement_temperature     110.0(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.304
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     936
_exptl_absorpt_coefficient_mu     0.265
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(Blessing, 1995)'
_exptl_absorpt_correction_T_min     0.906
_exptl_absorpt_correction_T_max     0.979
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     110.0(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_DIFFRN_MEASUREMENT_DEVICE_TYPE     'Kuma KM-4 CCD κ geometry'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16375
_diffrn_reflns_av_R_equivalents     0.0262
_diffrn_reflns_av_sigmaI/netI     0.0268
_diffrn_reflns_theta_min     4.08
_diffrn_reflns_theta_max     26.37
_diffrn_reflns_theta_full     26.37
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -25
_diffrn_reflns_limit_k_max     27
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4613
_reflns_number_gt     3649
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0439
_refine_ls_R_factor_gt     0.0319
_refine_ls_wR_factor_gt     0.0799
_refine_ls_wR_factor_ref     0.0835
_refine_ls_goodness_of_fit_ref     1.084
_refine_ls_restrained_S_all     1.084
_refine_ls_number_reflns     4613
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;calc w=1/[\\s\^2\^(Fo\^2\^)+(0.0469P)\^2\^+0.1761P]
where
 P=(Fo\^2\^+2Fc\^2\^)/3'
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.003
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.258
_refine_diff_density_min     -0.244
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_cell_refinement
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
Stereochemical Workstation (Siemens, 1989) and
Mercury (Version 1.4; Macrae et al.,  2006)
;
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
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
    S S1 1.10727(4) 0.577807(18) 0.44121(3) 0.02186(11) Uani d . 1 . .
    S S2 0.40946(4) 0.559452(17) 0.65132(3) 0.02230(11) Uani d . 1 . .
    O O1 0.96788(11) 0.47620(5) 0.25722(10) 0.0263(3) Uani d . 1 . .
    O O2 0.49931(11) 0.42075(5) 0.67245(10) 0.0254(3) Uani d . 1 . .
    O O3 0.79147(10) 0.54746(4) 0.19994(8) 0.0195(2) Uani d . 1 . .
    O O4 0.70910(10) 0.45238(4) 0.78833(9) 0.0189(2) Uani d . 1 . .
    N N1 0.81645(12) 0.57864(5) 0.43173(10) 0.0162(3) Uani d . 1 . .
    H H1N 0.7291 0.5644 0.4002 0.019 Uiso calc R 1 . .
    N N2 0.69531(12) 0.55176(5) 0.64079(10) 0.0159(3) Uani d . 1 . .
    H H2N 0.7769 0.5300 0.6522 0.019 Uiso calc R 1 . .
    C C1 0.82927(15) 0.62231(6) 0.53043(12) 0.0164(3) Uani d . 1 . .
    H H1 0.9221 0.6131 0.5874 0.020 Uiso calc R 1 . .
    C C2 0.69867(15) 0.61482(6) 0.59676(12) 0.0163(3) Uani d . 1 . .
    H H2 0.6056 0.6225 0.5392 0.020 Uiso calc R 1 . .
    C C3 0.93355(15) 0.56004(6) 0.38864(12) 0.0169(3) Uani d . 1 . .
    C C4 0.57279(15) 0.52636(6) 0.66405(12) 0.0165(3) Uani d . 1 . .
    C C5 0.90036(15) 0.52134(7) 0.27626(13) 0.0189(3) Uani d . 1 . .
    C C6 0.58841(15) 0.46044(7) 0.70675(12) 0.0171(3) Uani d . 1 . .
    C C7 0.75031(17) 0.51735(7) 0.08505(13) 0.0247(3) Uani d . 1 . .
    H H7A 0.7053 0.4768 0.0946 0.030 Uiso calc R 1 . .
    H H7B 0.8379 0.5112 0.0476 0.030 Uiso calc R 1 . .
    C C8 0.73393(16) 0.38900(7) 0.82938(15) 0.0253(3) Uani d . 1 . .
    H H8A 0.7317 0.3612 0.7605 0.030 Uiso calc R 1 . .
    H H8B 0.6557 0.3762 0.8731 0.030 Uiso calc R 1 . .
    C C9 0.64184(19) 0.55885(8) 0.01005(14) 0.0316(4) Uani d . 1 . .
    H H9A 0.6114 0.5405 -0.0688 0.047 Uiso calc R 1 . .
    H H9B 0.6877 0.5988 0.0020 0.047 Uiso calc R 1 . .
    H H9C 0.5556 0.5643 0.0480 0.047 Uiso calc R 1 . .
    C C10 0.88098(17) 0.38546(8) 0.90941(15) 0.0300(4) Uani d . 1 . .
    H H10A 0.8988 0.3433 0.9383 0.045 Uiso calc R 1 . .
    H H10B 0.8824 0.4132 0.9771 0.045 Uiso calc R 1 . .
    H H10C 0.9579 0.3976 0.8651 0.045 Uiso calc R 1 . .
    C C11 0.83808(15) 0.68767(6) 0.48626(12) 0.0174(3) Uani d . 1 . .
    C C12 0.73369(17) 0.71090(7) 0.39422(13) 0.0246(3) Uani d . 1 . .
    H H12A 0.6558 0.6854 0.3563 0.030 Uiso calc R 1 . .
    C C13 0.74327(19) 0.77137(8) 0.35763(15) 0.0315(4) Uani d . 1 . .
    H H13A 0.6718 0.7871 0.2946 0.038 Uiso calc R 1 . .
    C C14 0.85608(19) 0.80885(7) 0.41222(15) 0.0310(4) Uani d . 1 . .
    H H14A 0.8623 0.8501 0.3865 0.037 Uiso calc R 1 . .
    C C15 0.95956(18) 0.78618(7) 0.50409(15) 0.0288(4) Uani d . 1 . .
    H H15A 1.0367 0.8119 0.5424 0.035 Uiso calc R 1 . .
    C C16 0.95072(16) 0.72572(7) 0.54045(13) 0.0227(3) Uani d . 1 . .
    H H16A 1.0227 0.7102 0.6033 0.027 Uiso calc R 1 . .
    C C17 0.70980(15) 0.66189(6) 0.69635(12) 0.0164(3) Uani d . 1 . .
    C C18 0.82724(16) 0.66136(7) 0.79099(13) 0.0229(3) Uani d . 1 . .
    H H18A 0.8979 0.6293 0.7975 0.028 Uiso calc R 1 . .
    C C19 0.84170(17) 0.70749(7) 0.87609(14) 0.0276(4) Uani d . 1 . .
    H H19A 0.9230 0.7072 0.9400 0.033 Uiso calc R 1 . .
    C C20 0.73777(17) 0.75398(7) 0.86819(14) 0.0261(3) Uani d . 1 . .
    H H20A 0.7484 0.7857 0.9260 0.031 Uiso calc R 1 . .
    C C21 0.61919(16) 0.75392(7) 0.77623(14) 0.0243(3) Uani d . 1 . .
    H H21A 0.5467 0.7852 0.7716 0.029 Uiso calc R 1 . .
    C C22 0.60529(15) 0.70818(7) 0.69025(13) 0.0204(3) Uani d . 1 . .
    H H22A 0.5236 0.7086 0.6267 0.024 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    S1 C3 . 1.6565(14) ?
    S2 C4 . 1.6554(14) ?
    O1 C5 . 1.2048(17) ?
    O2 C6 . 1.2097(17) ?
    O3 C5 . 1.3358(17) ?
    O3 C7 . 1.4566(17) ?
    O4 C6 . 1.3318(16) ?
    O4 C8 . 1.4626(17) ?
    N1 C3 . 1.3296(17) ?
    N1 C1 . 1.4642(17) ?
    N1 H1N . 0.8800 ?
    N2 C4 . 1.3290(17) ?
    N2 C2 . 1.4648(18) ?
    N2 H2N . 0.8800 ?
    C1 C11 . 1.517(2) ?
    C1 C2 . 1.5443(18) ?
    C1 H1 . 1.0000 ?
    C2 C17 . 1.5219(19) ?
    C2 H2 . 1.0000 ?
    C3 C5 . 1.521(2) ?
    C4 C6 . 1.515(2) ?
    C7 C9 . 1.500(2) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C10 . 1.499(2) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 C16 . 1.387(2) ?
    C11 C12 . 1.390(2) ?
    C12 C13 . 1.389(2) ?
    C12 H12A . 0.9500 ?
    C13 C14 . 1.382(2) ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.379(2) ?
    C14 H14A . 0.9500 ?
    C15 C16 . 1.388(2) ?
    C15 H15A . 0.9500 ?
    C16 H16A . 0.9500 ?
    C17 C22 . 1.3892(19) ?
    C17 C18 . 1.389(2) ?
    C18 C19 . 1.388(2) ?
    C18 H18A . 0.9500 ?
    C19 C20 . 1.387(2) ?
    C19 H19A . 0.9500 ?
    C20 C21 . 1.377(2) ?
    C20 H20A . 0.9500 ?
    C21 C22 . 1.389(2) ?
    C21 H21A . 0.9500 ?
    C22 H22A . 0.9500 ?
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
    C5 O3 C7 . . 116.25(11) ?
    C6 O4 C8 . . 114.39(11) ?
    C3 N1 C1 . . 121.60(12) ?
    C3 N1 H1N . . 119.2 ?
    C1 N1 H1N . . 119.2 ?
    C4 N2 C2 . . 122.01(11) ?
    C4 N2 H2N . . 119.0 ?
    C2 N2 H2N . . 119.0 ?
    N1 C1 C11 . . 110.77(11) ?
    N1 C1 C2 . . 110.30(11) ?
    C11 C1 C2 . . 110.82(11) ?
    N1 C1 H1 . . 108.3 ?
    C11 C1 H1 . . 108.3 ?
    C2 C1 H1 . . 108.3 ?
    N2 C2 C17 . . 112.16(11) ?
    N2 C2 C1 . . 109.51(11) ?
    C17 C2 C1 . . 109.99(11) ?
    N2 C2 H2 . . 108.4 ?
    C17 C2 H2 . . 108.4 ?
    C1 C2 H2 . . 108.4 ?
    N1 C3 C5 . . 115.26(12) ?
    N1 C3 S1 . . 126.49(11) ?
    C5 C3 S1 . . 118.17(10) ?
    N2 C4 C6 . . 115.05(12) ?
    N2 C4 S2 . . 126.67(11) ?
    C6 C4 S2 . . 118.28(10) ?
    O1 C5 O3 . . 125.70(13) ?
    O1 C5 C3 . . 124.87(13) ?
    O3 C5 C3 . . 109.30(11) ?
    O2 C6 O4 . . 124.71(14) ?
    O2 C6 C4 . . 123.53(13) ?
    O4 C6 C4 . . 111.74(12) ?
    O3 C7 C9 . . 106.53(12) ?
    O3 C7 H7A . . 110.4 ?
    C9 C7 H7A . . 110.4 ?
    O3 C7 H7B . . 110.4 ?
    C9 C7 H7B . . 110.4 ?
    H7A C7 H7B . . 108.6 ?
    O4 C8 C10 . . 108.53(12) ?
    O4 C8 H8A . . 110.0 ?
    C10 C8 H8A . . 110.0 ?
    O4 C8 H8B . . 110.0 ?
    C10 C8 H8B . . 110.0 ?
    H8A C8 H8B . . 108.4 ?
    C7 C9 H9A . . 109.5 ?
    C7 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C7 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C8 C10 H10A . . 109.5 ?
    C8 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C8 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C16 C11 C12 . . 119.01(14) ?
    C16 C11 C1 . . 119.49(13) ?
    C12 C11 C1 . . 121.48(13) ?
    C13 C12 C11 . . 120.01(15) ?
    C13 C12 H12A . . 120.0 ?
    C11 C12 H12A . . 120.0 ?
    C14 C13 C12 . . 120.48(15) ?
    C14 C13 H13A . . 119.8 ?
    C12 C13 H13A . . 119.8 ?
    C15 C14 C13 . . 119.81(15) ?
    C15 C14 H14A . . 120.1 ?
    C13 C14 H14A . . 120.1 ?
    C14 C15 C16 . . 119.86(15) ?
    C14 C15 H15A . . 120.1 ?
    C16 C15 H15A . . 120.1 ?
    C11 C16 C15 . . 120.84(14) ?
    C11 C16 H16A . . 119.6 ?
    C15 C16 H16A . . 119.6 ?
    C22 C17 C18 . . 119.00(13) ?
    C22 C17 C2 . . 119.84(13) ?
    C18 C17 C2 . . 121.08(12) ?
    C19 C18 C17 . . 120.26(14) ?
    C19 C18 H18A . . 119.9 ?
    C17 C18 H18A . . 119.9 ?
    C20 C19 C18 . . 120.23(15) ?
    C20 C19 H19A . . 119.9 ?
    C18 C19 H19A . . 119.9 ?
    C21 C20 C19 . . 119.78(15) ?
    C21 C20 H20A . . 120.1 ?
    C19 C20 H20A . . 120.1 ?
    C20 C21 C22 . . 120.10(14) ?
    C20 C21 H21A . . 119.9 ?
    C22 C21 H21A . . 119.9 ?
    C21 C22 C17 . . 120.60(14) ?
    C21 C22 H22A . . 119.7 ?
    C17 C22 H22A . . 119.7 ?
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
    C3 N1 C1 C11 . . . . 81.42(15) y
    C3 N1 C1 C2 . . . . -155.52(12) y
    C4 N2 C2 C17 . . . . 81.00(16) y
    C4 N2 C2 C1 . . . . -156.60(12) y
    N1 C1 C2 N2 . . . . 58.36(14) y
    C11 C1 C2 N2 . . . . -178.60(11) ?
    N1 C1 C2 C17 . . . . -177.95(11) ?
    C11 C1 C2 C17 . . . . -54.91(15) ?
    C1 N1 C3 C5 . . . . -172.35(12) ?
    C1 N1 C3 S1 . . . . 4.36(19) ?
    C2 N2 C4 C6 . . . . 178.93(12) ?
    C2 N2 C4 S2 . . . . -1.3(2) ?
    C7 O3 C5 O1 . . . . 1.4(2) ?
    C7 O3 C5 C3 . . . . 177.46(11) ?
    N1 C3 C5 O1 . . . . -138.24(15) ?
    S1 C3 C5 O1 . . . . 44.77(19) y
    N1 C3 C5 O3 . . . . 45.63(16) ?
    S1 C3 C5 O3 . . . . -131.37(11) ?
    C8 O4 C6 O2 . . . . 4.37(19) ?
    C8 O4 C6 C4 . . . . -177.43(11) ?
    N2 C4 C6 O2 . . . . -137.14(14) ?
    S2 C4 C6 O2 . . . . 43.06(18) y
    N2 C4 C6 O4 . . . . 44.63(16) ?
    S2 C4 C6 O4 . . . . -135.16(10) ?
    C5 O3 C7 C9 . . . . -172.71(12) ?
    C6 O4 C8 C10 . . . . 173.51(12) ?
    N1 C1 C11 C16 . . . . -128.69(13) ?
    C2 C1 C11 C16 . . . . 108.54(14) ?
    N1 C1 C11 C12 . . . . 52.81(17) ?
    C2 C1 C11 C12 . . . . -69.96(17) ?
    C16 C11 C12 C13 . . . . 0.1(2) ?
    C1 C11 C12 C13 . . . . 178.63(14) ?
    C11 C12 C13 C14 . . . . -0.1(2) ?
    C12 C13 C14 C15 . . . . -0.3(2) ?
    C13 C14 C15 C16 . . . . 0.6(2) ?
    C12 C11 C16 C15 . . . . 0.2(2) ?
    C1 C11 C16 C15 . . . . -178.34(13) ?
    C14 C15 C16 C11 . . . . -0.6(2) ?
    N2 C2 C17 C22 . . . . -124.30(13) ?
    C1 C2 C17 C22 . . . . 113.57(14) ?
    N2 C2 C17 C18 . . . . 58.99(17) ?
    C1 C2 C17 C18 . . . . -63.14(16) ?
    C22 C17 C18 C19 . . . . -1.8(2) ?
    C2 C17 C18 C19 . . . . 174.90(13) ?
    C17 C18 C19 C20 . . . . 0.9(2) ?
    C18 C19 C20 C21 . . . . 0.7(2) ?
    C19 C20 C21 C22 . . . . -1.4(2) ?
    C20 C21 C22 C17 . . . . 0.5(2) ?
    C18 C17 C22 C21 . . . . 1.1(2) ?
    C2 C17 C22 C21 . . . . -175.63(13) ?
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 H2N O1 3_766 0.88 2.40 3.1819(15) 147
    N2 H2N S1 3_766 0.88 2.87 3.5749(12) 139
    N1 H1N O2 3_666 0.88 2.15 2.9487(15) 151
    N1 H1N S2 3_666 0.88 3.00 3.6875(12) 137
    C1 H1 O1 3_766 1.00 2.71 3.5195(17) 139
    C2 H2 O2 3_666 1.00 2.62 3.3781(18) 133
data_global
_journal_date_recd_electronic     2007-10-08
_journal_date_accepted     2007-10-10
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2007
_journal_volume     63
_journal_issue     12
_journal_page_first     o693
_journal_page_last     o696
_journal_paper_category     FO
_journal_coeditor_code     GD3156
_publ_contact_author_name
;
Gdaniec, Maria
;
_publ_contact_author_address
;
Faculty of Chemistry
Adam Mickiewicz University
60-780 Poznań
Poland
;
_publ_contact_author_email     magdan@amu.edu.pl
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Supramolecular structures of bis-thionooxalamic acid esters derived from
(+-)-1,2-diaminocyclohexane and (+-)-1,2-diphenylethylenediamine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Piotrkowska, Barbara' .
;
Department of Chemistry
Gdańsk University of Technology
80-952 Gdańsk
Poland
;
    'Połoński, Tadeusz' .
;
Department of Chemistry
Gdańsk University of Technology
80-952 Gdańsk
Poland
;
    'Gdaniec, Maria' .
;
Faculty of Chemistry
Adam Mickiewicz University
60-780 Poznań
Poland
;
