#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:43:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180352 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/21/7202172.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_7202172
loop_
_publ_author_name
'Piotrkowska, Barbara'
'Wasilewska, Aleksandra'
'Gdaniec, Maria'
'Połoński, Tadeusz'
_publ_section_title
;
 Strong N--H⋯N hydrogen bonds and weak N--H⋯S  C
 interactions in controlling the structure of the co-crystals of
 dithiooxamide with nitrogen heterocycles
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1421
_journal_paper_doi               10.1039/b806061d
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C2 H4 N2 S2, 2(C12 H8 N2)'
_chemical_formula_sum            'C26 H20 N6 S2'
_chemical_formula_weight         480.60
_chemical_name_common            'dithiooxamide-1,10-phenanthroline (1/1)'
_chemical_name_systematic
;
dithiooxamide-1,10-phenanthroline (1/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.110(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7438(9)
_cell_length_b                   10.0220(9)
_cell_length_c                   10.9457(10)
_cell_measurement_reflns_used    2354
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      3.2
_cell_volume                     1171.88(18)
_computing_cell_refinement
;
CrysAlis CCD
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_molecular_graphics
; Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Macrae et al., 2006)
;
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω 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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6999
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.24
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.9049
_exptl_absorpt_correction_T_min  0.8832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing (1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2064
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0487
_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)+(0.0850P)²+0.1893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1467
_reflns_number_gt                1647
_reflns_number_total             2064
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b806061d.txt
_cod_data_source_block           dtox-6
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7202172
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'
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
N1A N 0.30395(18) 0.5463(2) 0.35982(17) 0.0629(5) Uani 1 1 d . . .
C2A C 0.2204(3) 0.4526(3) 0.3740(3) 0.0817(8) Uani 1 1 d . . .
H2A H 0.1830 0.4107 0.3037 0.098 Uiso 1 1 calc R . .
C3A C 0.1843(3) 0.4119(3) 0.4870(3) 0.0880(9) Uani 1 1 d . . .
H3C H 0.1236 0.3463 0.4910 0.106 Uiso 1 1 calc R . .
C4A C 0.2390(3) 0.4696(3) 0.5902(3) 0.0779(8) Uani 1 1 d . . .
H4A H 0.2175 0.4432 0.6666 0.093 Uiso 1 1 calc R . .
C5A C 0.3885(2) 0.6375(3) 0.6873(2) 0.0745(8) Uani 1 1 d . . .
H5A H 0.3661 0.6161 0.7648 0.089 Uiso 1 1 calc R . .
C6A C 0.4753(2) 0.7300(3) 0.6772(2) 0.0766(8) Uani 1 1 d . . .
H6A H 0.5149 0.7726 0.7497 0.092 Uiso 1 1 d R . .
C7A C 0.6032(2) 0.8632(3) 0.5461(2) 0.0735(8) Uani 1 1 d . . .
H7A H 0.6449 0.9057 0.6177 0.088 Uiso 1 1 d R . .
C8A C 0.6322(2) 0.8959(3) 0.4318(2) 0.0711(7) Uani 1 1 d . . .
H8A H 0.6950 0.9616 0.4204 0.085 Uiso 1 1 d R . .
C9A C 0.5705(2) 0.8310(2) 0.3317(2) 0.0611(6) Uani 1 1 d . . .
H9A H 0.5901 0.8544 0.2509 0.073 Uiso 1 1 d R . .
N10A N 0.48331(16) 0.73881(18) 0.33978(15) 0.0526(5) Uani 1 1 d . . .
C11A C 0.45242(17) 0.7061(2) 0.45259(17) 0.0459(5) Uani 1 1 d . . .
C12A C 0.51114(19) 0.7669(2) 0.55982(19) 0.0576(6) Uani 1 1 d . . .
C13A C 0.35903(18) 0.6047(2) 0.46357(18) 0.0487(5) Uani 1 1 d . . .
C14A C 0.3284(2) 0.5695(2) 0.5814(2) 0.0587(6) Uani 1 1 d . . .
S1 S 0.61439(7) 0.67735(8) 0.02422(10) 0.0640(4) Uani 0.937(4) 1 d P . .
N3 N 0.4321(2) 0.5616(3) 0.1286(2) 0.0547(8) Uani 0.937(4) 1 d P . .
H3A H 0.384(2) 0.493(3) 0.132(2) 0.061(7) Uiso 0.937(4) 1 d P . .
H3B H 0.437(2) 0.620(3) 0.187(2) 0.064(7) Uiso 0.937(4) 1 d P . .
C2 C 0.50800(18) 0.5602(2) 0.04317(17) 0.0461(6) Uani 0.937(4) 1 d P . .
S1B S 0.6400(10) 0.6510(12) -0.0248(15) 0.064(4) Uiso 0.063(4) 1 d PD A 2
C2B C 0.5464(18) 0.5182(18) -0.0460(13) 0.064(4) Uiso 0.063(4) 1 d PD . 2
N3B N 0.541(5) 0.439(5) -0.140(4) 0.064(4) Uiso 0.063(4) 1 d PD . 2
H3BA H 0.5913 0.4547 -0.1992 0.064(4) Uiso 0.063(4) 1 d PR A 2
H3BB H 0.4884 0.3695 -0.1458 0.064(4) Uiso 0.063(4) 1 d PR A 2
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'
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
C2A N1A C13A 116.8(2) . . ?
N1A C2A C3A 124.6(3) . . ?
N1A C2A H2A 117.7 . . ?
C3A C2A H2A 117.7 . . ?
C4A C3A C2A 118.7(3) . . ?
C4A C3A H3C 120.7 . . ?
C2A C3A H3C 120.7 . . ?
C3A C4A C14A 119.5(2) . . ?
C3A C4A H4A 120.3 . . ?
C14A C4A H4A 120.3 . . ?
C6A C5A C14A 121.5(2) . . ?
C6A C5A H5A 119.3 . . ?
C14A C5A H5A 119.3 . . ?
C5A C6A C12A 121.0(2) . . ?
C5A C6A H6A 119.6 . . ?
C12A C6A H6A 119.3 . . ?
C8A C7A C12A 119.9(2) . . ?
C8A C7A H7A 120.7 . . ?
C12A C7A H7A 119.5 . . ?
C7A C8A C9A 118.5(2) . . ?
C7A C8A H8A 121.1 . . ?
C9A C8A H8A 120.3 . . ?
N10A C9A C8A 123.9(2) . . ?
N10A C9A H9A 117.3 . . ?
C8A C9A H9A 118.8 . . ?
C9A N10A C11A 118.31(18) . . ?
N10A C11A C12A 121.54(19) . . ?
N10A C11A C13A 119.18(18) . . ?
C12A C11A C13A 119.27(18) . . ?
C7A C12A C11A 117.8(2) . . ?
C7A C12A C6A 122.4(2) . . ?
C11A C12A C6A 119.8(2) . . ?
N1A C13A C14A 122.3(2) . . ?
N1A C13A C11A 118.66(17) . . ?
C14A C13A C11A 119.03(19) . . ?
C4A C14A C13A 118.2(2) . . ?
C4A C14A C5A 122.5(2) . . ?
C13A C14A C5A 119.4(2) . . ?
C2 N3 H3A 116.4(17) . . ?
C2 N3 H3B 123.2(17) . . ?
H3A N3 H3B 120(2) . . ?
N3 C2 C2 114.4(2) . 3_665 ?
N3 C2 S1 124.79(19) . . ?
C2 C2 S1 120.8(2) 3_665 . ?
N3B C2B C2B 113.6(7) . 3_665 ?
N3B C2B S1B 124.9(7) . . ?
C2B C2B S1B 121.4(6) 3_665 . ?
C2B N3B H3BA 119.5 . . ?
C2B N3B H3BB 120.5 . . ?
H3BA N3B H3BB 120.0 . . ?
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
N1A C2A 1.320(3) . ?
N1A C13A 1.356(3) . ?
C2A C3A 1.397(4) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.347(4) . ?
C3A H3C 0.9300 . ?
C4A C14A 1.397(4) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.328(4) . ?
C5A C14A 1.438(4) . ?
C5A H5A 0.9300 . ?
C6A C12A 1.428(3) . ?
C6A H6A 0.9600 . ?
C7A C8A 1.361(4) . ?
C7A C12A 1.401(4) . ?
C7A H7A 0.9600 . ?
C8A C9A 1.382(3) . ?
C8A H8A 0.9600 . ?
C9A N10A 1.325(3) . ?
C9A H9A 0.9599 . ?
N10A C11A 1.353(3) . ?
C11A C12A 1.411(3) . ?
C11A C13A 1.442(3) . ?
C13A C14A 1.409(3) . ?
S1 C2 1.667(2) . ?
N3 C2 1.305(3) . ?
N3 H3A 0.86(3) . ?
N3 H3B 0.87(3) . ?
C2 C2 1.531(4) 3_665 ?
S1B C2B 1.669(5) . ?
C2B N3B 1.291(5) . ?
C2B C2B 1.5349(11) 3_665 ?
N3B H3BA 0.9000 . ?
N3B H3BB 0.8999 . ?
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
N3 H3A S1 0.86(3) 2.42(3) 2.934(3) 119(2) 3_665
N3 H3B N10A 0.87(3) 2.07(3) 2.920(3) 168(2) .
N3 H3B N1A 0.87(3) 2.59(3) 3.011(3) 111(2) .
N3B H3BB S1B 0.90 2.45 2.933(16) 114.3 3_665
N3B H3BA N1A 0.90 2.19 3.073(13) 168.1 3_665
