#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:43:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180352 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/21/7202170.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_7202170
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         'C6 H12 N2, C2 H4 N2 S2'
_chemical_formula_sum            'C8 H16 N4 S2'
_chemical_formula_weight         232.37
_chemical_name_common
'1,4-diazabicyclo(2.2.2)octane - dithiooxamide (1/1)'
_chemical_name_systematic
;
1,4-diazabicyclo[2.2.2]octane - dithiooxamide (1/1)
;
_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                77.833(4)
_cell_angle_beta                 88.565(8)
_cell_angle_gamma                69.780(8)
_cell_formula_units_Z            2
_cell_length_a                   6.0414(8)
_cell_length_b                   8.3514(4)
_cell_length_c                   12.3639(6)
_cell_measurement_reflns_used    3188
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      4
_cell_volume                     571.44(9)
_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      140(2)
_diffrn_measured_fraction_theta_full 0.889
_diffrn_measured_fraction_theta_max 0.889
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8961
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing (1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0439
_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)+(0.0873P)²+0.2318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1443
_reflns_number_gt                1827
_reflns_number_total             2090
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b806061d.txt
_cod_data_source_block           dtox-4(lt)
_cod_database_code               7202170
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
S1A S 0.17265(13) 0.19389(9) 0.53106(6) 0.0290(2) Uani 1 1 d . . .
C2A C 0.4582(5) 0.0756(3) 0.53114(17) 0.0171(5) Uani 1 1 d . . .
N3A N 0.6282(4) 0.1016(3) 0.58107(17) 0.0201(5) Uani 1 1 d . . .
H3AA H 0.596(7) 0.184(5) 0.618(3) 0.038(9) Uiso 1 1 d . . .
H3AB H 0.766(8) 0.037(5) 0.577(3) 0.032(9) Uiso 1 1 d . . .
S1B S -0.16015(12) 0.83397(9) 0.94415(6) 0.0280(2) Uani 1 1 d . . .
C2B C 0.0320(4) 0.9289(3) 0.96560(17) 0.0146(5) Uani 1 1 d . . .
N3B N 0.2430(4) 0.8907(3) 0.92733(17) 0.0204(5) Uani 1 1 d . . .
H3BA H 0.293(7) 0.807(5) 0.892(3) 0.034(9) Uiso 1 1 d . . .
H3BB H 0.326(8) 0.943(5) 0.945(3) 0.036(9) Uiso 1 1 d . . .
N1 N 0.5257(4) 0.3795(3) 0.69483(16) 0.0192(5) Uani 1 1 d . . .
N2 N 0.4159(4) 0.6150(3) 0.81181(16) 0.0192(5) Uani 1 1 d . . .
C1 C 0.3600(6) 0.5453(3) 0.6308(2) 0.0296(7) Uani 1 1 d . . .
H1A H 0.2259 0.5275 0.6023 0.036 Uiso 1 1 d R . .
H1B H 0.4405 0.5871 0.5690 0.036 Uiso 1 1 d R . .
C2 C 0.2793(6) 0.6826(3) 0.7042(2) 0.0269(6) Uani 1 1 d . . .
H2A H 0.3024 0.7888 0.6672 0.032 Uiso 1 1 d R . .
H2B H 0.1139 0.7084 0.7159 0.032 Uiso 1 1 d R . .
C3 C 0.7393(6) 0.4082(4) 0.7284(3) 0.0341(7) Uani 1 1 d . . .
H3A H 0.8209 0.4384 0.6636 0.041 Uiso 1 1 d R . .
H3B H 0.8433 0.3027 0.7746 0.041 Uiso 1 1 d R . .
C4 C 0.6687(6) 0.5596(4) 0.7919(3) 0.0348(7) Uani 1 1 d . . .
H4A H 0.7569 0.5198 0.8618 0.042 Uiso 1 1 d R . .
H4B H 0.7071 0.6568 0.7501 0.042 Uiso 1 1 d R . .
C5 C 0.4119(5) 0.3244(3) 0.7959(2) 0.0226(6) Uani 1 1 d . . .
H5A H 0.5121 0.2120 0.8363 0.027 Uiso 1 1 d R . .
H5B H 0.2656 0.3143 0.7759 0.027 Uiso 1 1 d R . .
C6 C 0.3606(5) 0.4608(3) 0.86994(19) 0.0236(6) Uani 1 1 d . . .
H6A H 0.1978 0.4956 0.8887 0.028 Uiso 1 1 d R . .
H6B H 0.4563 0.4083 0.9376 0.028 Uiso 1 1 d 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'
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
N3A C2A C2A 114.8(3) . 2_656 ?
N3A C2A S1A 124.35(18) . . ?
C2A C2A S1A 120.8(2) 2_656 . ?
C2A N3A H3AA 121(3) . . ?
C2A N3A H3AB 118(3) . . ?
H3AA N3A H3AB 121(4) . . ?
N3B C2B C2B 115.1(3) . 2_577 ?
N3B C2B S1B 124.08(18) . . ?
C2B C2B S1B 120.9(2) 2_577 . ?
C2B N3B H3BA 119(3) . . ?
C2B N3B H3BB 116(3) . . ?
H3BA N3B H3BB 124(4) . . ?
C1 N1 C3 109.0(2) . . ?
C1 N1 C5 108.3(2) . . ?
C3 N1 C5 108.3(2) . . ?
C4 N2 C6 108.6(2) . . ?
C4 N2 C2 109.1(2) . . ?
C6 N2 C2 107.7(2) . . ?
N1 C1 C2 110.22(19) . . ?
N1 C1 H1A 110.5 . . ?
C2 C1 H1A 110.4 . . ?
N1 C1 H1B 108.1 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 108.3 . . ?
N2 C2 C1 110.3(2) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.9 . . ?
N2 C2 H2B 109.9 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 108.4 . . ?
N1 C3 C4 109.8(2) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.3 . . ?
N1 C3 H3B 109.5 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.3 . . ?
N2 C4 C3 110.6(2) . . ?
N2 C4 H4A 108.9 . . ?
C3 C4 H4A 109.1 . . ?
N2 C4 H4B 110.1 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C6 110.4(2) . . ?
N1 C5 H5A 109.8 . . ?
C6 C5 H5A 110.1 . . ?
N1 C5 H5B 109.6 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 108.0 . . ?
N2 C6 C5 110.08(19) . . ?
N2 C6 H6A 110.0 . . ?
C5 C6 H6A 110.2 . . ?
N2 C6 H6B 109.6 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
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
S1A C2A 1.665(3) . ?
C2A N3A 1.313(3) . ?
C2A C2A 1.546(4) 2_656 ?
N3A H3AA 0.87(4) . ?
N3A H3AB 0.83(4) . ?
S1B C2B 1.669(2) . ?
C2B N3B 1.305(3) . ?
C2B C2B 1.541(4) 2_577 ?
N3B H3BA 0.86(4) . ?
N3B H3BB 0.83(4) . ?
N1 C1 1.472(3) . ?
N1 C3 1.475(4) . ?
N1 C5 1.476(3) . ?
N2 C4 1.466(4) . ?
N2 C6 1.477(3) . ?
N2 C2 1.479(3) . ?
C1 C2 1.551(3) . ?
C1 H1A 0.9603 . ?
C1 H1B 0.9640 . ?
C2 H2A 0.9627 . ?
C2 H2B 0.9612 . ?
C3 C4 1.557(3) . ?
C3 H3A 0.9639 . ?
C3 H3B 0.9598 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9632 . ?
C5 C6 1.553(3) . ?
C5 H5A 0.9599 . ?
C5 H5B 0.9605 . ?
C6 H6A 0.9614 . ?
C6 H6B 0.9599 . ?
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
N3A H3AA N1 0.87(4) 1.98(4) 2.844(3) 177(3) .
N3B H3BA N2 0.86(4) 1.98(4) 2.843(3) 179(4) .
N3A H3AB S1A 0.83(4) 2.49(4) 2.960(2) 117(3) 2_656
N3A H3AB S1A 0.83(4) 3.15(4) 3.640(3) 121(3) 1_655
N3B H3BB S1B 0.83(4) 2.46(4) 2.961(2) 119(3) 2_577
N3B H3BB S1B 0.83(4) 2.92(4) 3.477(3) 127(3) 1_655
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 -63.0(3) . . . . ?
C5 N1 C1 C2 54.7(3) . . . . ?
C4 N2 C2 C1 54.0(3) . . . . ?
C6 N2 C2 C1 -63.7(3) . . . . ?
N1 C1 C2 N2 7.5(3) . . . . ?
C1 N1 C3 C4 54.8(3) . . . . ?
C5 N1 C3 C4 -62.9(3) . . . . ?
C6 N2 C4 C3 54.9(3) . . . . ?
C2 N2 C4 C3 -62.2(3) . . . . ?
N1 C3 C4 N2 6.9(4) . . . . ?
C1 N1 C5 C6 -62.7(3) . . . . ?
C3 N1 C5 C6 55.4(3) . . . . ?
C4 N2 C6 C5 -62.4(3) . . . . ?
C2 N2 C6 C5 55.6(3) . . . . ?
N1 C5 C6 N2 6.3(3) . . . . ?
