#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/14/7151402.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_7151402
loop_
_publ_author_name
'Simonov, Yurii A.'
'Fonari, Marina S.'
'Zaworotko, Michael J.'
'Abourahma, Heba'
'Lipkowski, Janusz'
'Ganin, Edward V.'
'Yavolovskii, Arkadii A.'
_publ_section_title
;
 From 1D strands to extended molecular assemblies in the binary
 compounds of dithiooxamide and dithiobiurea with crown ethers
;
_journal_issue                   16
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              2922
_journal_paper_doi               10.1039/b301379k
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C10 H20 O5 , C2 H4 N2 S2'
_chemical_formula_sum            'C12 H24 N2 O5 S2'
_chemical_formula_weight         340.45
_chemical_name_common
;1,4,7,10,13-pentaoxacyclopentadecane ethanedithioamide
clathrate
;
_chemical_name_systematic
;
1,4,7,10,13-pentaoxacyclopentadecane ethanedithioamide clathrate
;
_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                80.053(3)
_cell_angle_beta                 81.737(3)
_cell_angle_gamma                75.392(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2660(5)
_cell_length_b                   8.6440(6)
_cell_length_c                   12.5320(10)
_cell_measurement_temperature    293(2)
_cell_volume                     848.73(10)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 2001)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3925
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2943
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0938
_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)+(0.0867P)²+2.3203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2308
_refine_ls_wR_factor_ref         0.2389
_reflns_number_gt                2471
_reflns_number_total             2943
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b301379k.txt
_cod_data_source_block           compound_1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151402
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 0.1650(8) 0.5041(9) 0.7998(8) 0.077(3) Uani 0.592(17) 1 d PD A 1
S2A S 0.3074(8) 0.0365(9) 0.6959(8) 0.081(3) Uani 0.592(17) 1 d PD A 1
N1A N 0.021(2) 0.308(4) 0.7175(18) 0.044(5) Uani 0.592(17) 1 d PDU A 1
H1NA H 0.0305 0.2169 0.6950 0.053 Uiso 0.592(17) 1 calc PR A 1
H1NB H -0.0735 0.3777 0.7180 0.053 Uiso 0.592(17) 1 calc PR A 1
N2A N 0.444(2) 0.233(4) 0.779(3) 0.047(6) Uani 0.592(17) 1 d PDU A 1
H2NA H 0.4358 0.3236 0.8022 0.056 Uiso 0.592(17) 1 calc PR A 1
H2NB H 0.5376 0.1623 0.7785 0.056 Uiso 0.592(17) 1 calc PR A 1
C1A C 0.1551(10) 0.3399(9) 0.7521(6) 0.033(3) Uani 0.592(17) 1 d PD A 1
C2A C 0.3093(10) 0.2035(9) 0.7452(6) 0.035(3) Uani 0.592(17) 1 d PD A 1
S1B S 0.1650(10) 0.5105(6) 0.7965(6) 0.038(3) Uani 0.408(17) 1 d PD A 2
S2B S 0.3031(10) 0.0308(6) 0.7017(7) 0.041(2) Uani 0.408(17) 1 d PD A 2
N1B N 0.434(3) 0.252(6) 0.789(4) 0.060(13) Uani 0.408(17) 1 d PDU A 2
H1NC H 0.4763 0.1555 0.7743 0.072 Uiso 0.408(17) 1 calc PR A 2
H1ND H 0.4943 0.3020 0.8146 0.072 Uiso 0.408(17) 1 calc PR A 2
N2B N 0.033(2) 0.287(6) 0.717(3) 0.060(13) Uani 0.408(17) 1 d PDU A 2
H2NC H -0.0088 0.3814 0.7348 0.072 Uiso 0.408(17) 1 calc PR A 2
H2ND H -0.0298 0.2379 0.6922 0.072 Uiso 0.408(17) 1 calc PR A 2
C1B C 0.2735(15) 0.3246(13) 0.7723(9) 0.037(4) Uani 0.408(17) 1 d PD A 2
C2B C 0.1956(16) 0.2139(12) 0.7279(9) 0.036(4) Uani 0.408(17) 1 d PD A 2
O1 O -0.3115(5) 0.3756(5) 0.5712(3) 0.0615(11) Uani 1 1 d . . .
C2 C -0.2971(8) 0.5373(7) 0.5425(5) 0.0597(15) Uani 1 1 d . . .
H2A H -0.3486 0.5859 0.4761 0.072 Uiso 1 1 calc R . .
H2B H -0.1798 0.5422 0.5310 0.072 Uiso 1 1 calc R . .
C3 C -0.3865(7) 0.6243(7) 0.6360(5) 0.0571(15) Uani 1 1 d . . .
H3A H -0.3958 0.7395 0.6162 0.068 Uiso 1 1 calc R . .
H3B H -0.4989 0.6060 0.6537 0.068 Uiso 1 1 calc R . .
O4 O -0.2942(4) 0.5656(5) 0.7267(3) 0.0561(10) Uani 1 1 d . . .
C5 C -0.3843(7) 0.6039(7) 0.8275(5) 0.0531(14) Uani 1 1 d . . .
H5A H -0.4998 0.5962 0.8297 0.064 Uiso 1 1 calc R . .
H5B H -0.3848 0.7136 0.8357 0.064 Uiso 1 1 calc R . .
C6 C -0.3018(7) 0.4884(7) 0.9174(5) 0.0520(14) Uani 1 1 d . . .
H6A H -0.1813 0.4789 0.9062 0.062 Uiso 1 1 calc R . .
H6B H -0.3441 0.5273 0.9866 0.062 Uiso 1 1 calc R . .
O7 O -0.3368(5) 0.3365(5) 0.9188(3) 0.0543(10) Uani 1 1 d . . .
C8 C -0.2275(7) 0.2078(7) 0.9785(5) 0.0548(14) Uani 1 1 d . . .
H8A H -0.2281 0.2319 1.0513 0.066 Uiso 1 1 calc R . .
H8B H -0.1136 0.1951 0.9429 0.066 Uiso 1 1 calc R . .
C9 C -0.2837(8) 0.0547(8) 0.9849(5) 0.0601(15) Uani 1 1 d . . .
H9A H -0.2094 -0.0318 1.0272 0.072 Uiso 1 1 calc R . .
H9B H -0.3959 0.0675 1.0231 0.072 Uiso 1 1 calc R . .
O10 O -0.2851(5) 0.0096(5) 0.8803(3) 0.0548(10) Uani 1 1 d . . .
C11 C -0.1281(7) -0.0784(6) 0.8360(5) 0.0527(14) Uani 1 1 d . . .
H11A H -0.1015 -0.1871 0.8752 0.063 Uiso 1 1 calc R . .
H11B H -0.0395 -0.0259 0.8416 0.063 Uiso 1 1 calc R . .
C12 C -0.1428(8) -0.0832(7) 0.7179(5) 0.0595(15) Uani 1 1 d . . .
H12A H -0.0466 -0.1594 0.6882 0.071 Uiso 1 1 calc R . .
H12B H -0.2438 -0.1174 0.7118 0.071 Uiso 1 1 calc R . .
O13 O -0.1498(5) 0.0728(5) 0.6598(3) 0.0595(11) Uani 1 1 d . . .
C14 C -0.2147(7) 0.0980(7) 0.5592(4) 0.0533(14) Uani 1 1 d . . .
H14A H -0.3290 0.0840 0.5701 0.064 Uiso 1 1 calc R . .
H14B H -0.1472 0.0206 0.5134 0.064 Uiso 1 1 calc R . .
C15 C -0.2119(8) 0.2661(7) 0.5060(5) 0.0596(15) Uani 1 1 d . . .
H15A H -0.0974 0.2796 0.4953 0.071 Uiso 1 1 calc R . .
H15B H -0.2537 0.2856 0.4352 0.071 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'
N N 0.0061 0.0033 '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
C1A N1A H1NA 120.0 . . ?
C1A N1A H1NB 120.0 . . ?
H1NA N1A H1NB 120.0 . . ?
C2A N2A H2NA 120.0 . . ?
C2A N2A H2NB 120.0 . . ?
H2NA N2A H2NB 120.0 . . ?
N1A C1A C2A 112.5(16) . . ?
N1A C1A S1A 128.2(15) . . ?
C2A C1A S1A 119.3(7) . . ?
N2A C2A C1A 113.3(17) . . ?
N2A C2A S2A 125.2(16) . . ?
C1A C2A S2A 121.4(7) . . ?
C1B N1B H1NC 120.0 . . ?
C1B N1B H1ND 120.0 . . ?
H1NC N1B H1ND 120.0 . . ?
C2B N2B H2NC 120.0 . . ?
C2B N2B H2ND 120.0 . . ?
H2NC N2B H2ND 120.0 . . ?
N1B C1B C2B 110(2) . . ?
N1B C1B S1B 128(2) . . ?
C2B C1B S1B 121.9(10) . . ?
N2B C2B C1B 109(2) . . ?
N2B C2B S2B 129(2) . . ?
C1B C2B S2B 122.3(10) . . ?
C15 O1 C2 116.1(5) . . ?
O1 C2 C3 106.3(5) . . ?
O1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
O1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
O4 C3 C2 108.7(4) . . ?
O4 C3 H3A 110.0 . . ?
C2 C3 H3A 110.0 . . ?
O4 C3 H3B 110.0 . . ?
C2 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
C3 O4 C5 114.5(4) . . ?
O4 C5 C6 108.8(4) . . ?
O4 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
O4 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
O7 C6 C5 108.8(4) . . ?
O7 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
O7 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C6 O7 C8 113.4(4) . . ?
O7 C8 C9 109.7(4) . . ?
O7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
O7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O10 C9 C8 113.3(5) . . ?
O10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
O10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 O10 C9 114.7(4) . . ?
O10 C11 C12 107.3(4) . . ?
O10 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
O10 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
O13 C12 C11 108.5(5) . . ?
O13 C12 H12A 110.0 . . ?
C11 C12 H12A 110.0 . . ?
O13 C12 H12B 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C14 O13 C12 114.0(4) . . ?
O13 C14 C15 108.2(4) . . ?
O13 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O13 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
O1 C15 C14 109.5(5) . . ?
O1 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
O1 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
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
S1A C1A 1.657(9) . ?
S2A C2A 1.670(9) . ?
N1A C1A 1.352(16) . ?
N1A H1NA 0.8600 . ?
N1A H1NB 0.8600 . ?
N2A C2A 1.343(17) . ?
N2A H2NA 0.8600 . ?
N2A H2NB 0.8600 . ?
C1A C2A 1.506(11) . ?
S1B C1B 1.686(11) . ?
S2B C2B 1.670(10) . ?
N1B C1B 1.347(19) . ?
N1B H1NC 0.8600 . ?
N1B H1ND 0.8600 . ?
N2B C2B 1.351(18) . ?
N2B H2NC 0.8600 . ?
N2B H2ND 0.8600 . ?
C1B C2B 1.496(14) . ?
O1 C15 1.387(7) . ?
O1 C2 1.413(7) . ?
C2 C3 1.503(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O4 1.410(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C5 1.418(7) . ?
C5 C6 1.491(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O7 1.411(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C8 1.419(6) . ?
C8 C9 1.495(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O10 1.433(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O10 C11 1.419(6) . ?
C11 C12 1.510(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O13 1.409(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O13 C14 1.401(6) . ?
C14 C15 1.495(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
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
N1A H1NA O13 0.86 2.30 2.98(3) 136.4 .
N1A H1NB O4 0.86 2.12 2.97(3) 174.0 .
N1A H1NA S2A 0.86 2.42 2.90(3) 115.4 .
N2A H2NA O7 0.86 2.58 3.07(2) 117.3 1_655
N2A H2NB O10 0.86 2.12 2.85(2) 143.0 1_655
N2A H2NA S1A 0.86 2.38 2.86(3) 115.1 .
N1B H1NC O10 0.86 2.48 2.93(3) 112.9 1_655
N1B H1ND O7 0.86 2.15 2.96(4) 157.2 1_655
N2B H2NC S1B 0.86 2.31 2.83(4) 118.9 .
N2B H2NC O4 0.86 2.50 3.14(3) 132.2 .
N2B H2ND O13 0.86 2.05 2.89(4) 165.4 .
N1B H1NC S2B 0.86 2.35 2.85(5) 117.4 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 O4 68.4(6) . . . . ?
C2 C3 O4 C5 -163.9(5) . . . . ?
C3 O4 C5 C6 158.9(5) . . . . ?
O4 C5 C6 O7 -73.1(5) . . . . ?
C5 C6 O7 C8 162.7(5) . . . . ?
C6 O7 C8 C9 174.5(5) . . . . ?
O7 C8 C9 O10 59.9(7) . . . . ?
C8 C9 O10 C11 84.5(6) . . . . ?
C9 O10 C11 C12 -167.7(5) . . . . ?
O10 C11 C12 O13 70.8(6) . . . . ?
C11 C12 O13 C14 -161.2(5) . . . . ?
C12 O13 C14 C15 -179.0(5) . . . . ?
O13 C14 C15 O1 -60.9(6) . . . . ?
C14 C15 O1 C2 168.5(5) . . . . ?
C15 O1 C2 C3 -168.5(5) . . . . ?
