#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/14/7151405.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_7151405
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         'C12 H24 O6 , C2 H6 N4 S2'
_chemical_formula_sum            'C14 H30 N4 O6 S2'
_chemical_formula_weight         414.54
_chemical_name_common
;1,4,7,10,13,16-hexaoxacyclooctadecane N,N'-
(thiocarbamoyl)hydrazine clathrate
;
_chemical_name_systematic
;
1,4,7,10,13,16-hexaoxacyclooctadecane
N,N'-(thiocarbamoyl)hydrazine clathrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.18(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.196(3)
_cell_length_b                   7.187(2)
_cell_length_c                   19.552(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1993.4(8)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       phi-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4532
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0334
_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)+(0.0312P)²+0.8022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0782
_reflns_number_gt                3860
_reflns_number_total             4532
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b301379k.txt
_cod_data_source_block           compound_4
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7151405
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.77624(7) 1.02704(13) -0.24061(5) 0.0183(2) Uani 1 1 d . . .
C2 C 0.86221(10) 1.0074(2) -0.27563(7) 0.0210(3) Uani 1 1 d . . .
H2A H 0.8775 1.1234 -0.2981 0.025 Uiso 1 1 calc R . .
H2B H 0.8555 0.9111 -0.3102 0.025 Uiso 1 1 calc R . .
C3 C 0.93888(10) 0.95679(19) -0.22449(7) 0.0218(3) Uani 1 1 d . . .
H3A H 0.9248 0.8386 -0.2032 0.026 Uiso 1 1 calc R . .
H3B H 0.9984 0.9453 -0.2469 0.026 Uiso 1 1 calc R . .
O4 O 0.94465(7) 1.10036(13) -0.17416(5) 0.0205(2) Uani 1 1 d . . .
C5 C 1.01158(10) 1.0593(2) -0.12033(7) 0.0228(3) Uani 1 1 d . . .
H5A H 1.0746 1.0571 -0.1378 0.027 Uiso 1 1 calc R . .
H5B H 0.9985 0.9382 -0.1010 0.027 Uiso 1 1 calc R . .
C6 C 1.00481(10) 1.2065(2) -0.06668(8) 0.0237(3) Uani 1 1 d . . .
H6A H 1.0572 1.1955 -0.0336 0.028 Uiso 1 1 calc R . .
H6B H 1.0072 1.3288 -0.0875 0.028 Uiso 1 1 calc R . .
O7 O 0.91779(7) 1.18341(13) -0.03344(5) 0.0203(2) Uani 1 1 d . . .
C8 C 0.89723(10) 1.33613(18) 0.00946(7) 0.0199(3) Uani 1 1 d . . .
H8A H 0.8925 1.4494 -0.0174 0.024 Uiso 1 1 calc R . .
H8B H 0.9474 1.3519 0.0440 0.024 Uiso 1 1 calc R . .
C9 C 0.80596(10) 1.29995(19) 0.04299(7) 0.0200(3) Uani 1 1 d . . .
H9A H 0.8108 1.1876 0.0704 0.024 Uiso 1 1 calc R . .
H9B H 0.7912 1.4029 0.0728 0.024 Uiso 1 1 calc R . .
O10 O 0.73362(7) 1.27935(13) -0.00898(5) 0.0180(2) Uani 1 1 d . . .
C11 C 0.64288(10) 1.26601(19) 0.01956(7) 0.0212(3) Uani 1 1 d . . .
H11A H 0.6216 1.3885 0.0330 0.025 Uiso 1 1 calc R . .
H11B H 0.6463 1.1875 0.0599 0.025 Uiso 1 1 calc R . .
C12 C 0.57498(10) 1.18500(18) -0.03261(7) 0.0211(3) Uani 1 1 d . . .
H12A H 0.5945 1.0600 -0.0443 0.025 Uiso 1 1 calc R . .
H12B H 0.5127 1.1779 -0.0140 0.025 Uiso 1 1 calc R . .
O13 O 0.57206(7) 1.29893(12) -0.09242(5) 0.0199(2) Uani 1 1 d . . .
C14 C 0.49799(10) 1.24699(19) -0.13997(8) 0.0224(3) Uani 1 1 d . . .
H14A H 0.4979 1.3331 -0.1782 0.027 Uiso 1 1 calc R . .
H14B H 0.4384 1.2617 -0.1178 0.027 Uiso 1 1 calc R . .
C15 C 0.50279(10) 1.04979(19) -0.16810(8) 0.0223(3) Uani 1 1 d . . .
H15A H 0.4920 0.9637 -0.1310 0.027 Uiso 1 1 calc R . .
H15B H 0.4516 1.0338 -0.2019 0.027 Uiso 1 1 calc R . .
O16 O 0.58883(7) 0.99911(12) -0.19880(5) 0.0197(2) Uani 1 1 d . . .
C17 C 0.61557(10) 1.12552(18) -0.25063(7) 0.0189(3) Uani 1 1 d . . .
H17A H 0.6325 1.2444 -0.2301 0.023 Uiso 1 1 calc R . .
H17B H 0.5629 1.1454 -0.2828 0.023 Uiso 1 1 calc R . .
C18 C 0.69767(10) 1.04959(19) -0.28759(7) 0.0197(3) Uani 1 1 d . . .
H18A H 0.6810 0.9306 -0.3081 0.024 Uiso 1 1 calc R . .
H18B H 0.7141 1.1342 -0.3239 0.024 Uiso 1 1 calc R . .
S1G S 0.72315(3) 0.77592(5) 0.028017(17) 0.02041(9) Uani 1 1 d . . .
S2G S 0.76431(3) 0.53786(5) -0.278494(17) 0.02138(9) Uani 1 1 d . . .
N1G N 0.78149(9) 0.89905(16) -0.09144(7) 0.0207(3) Uani 1 1 d . . .
H1N1 H 0.8136(13) 0.984(3) -0.0682(9) 0.037(5) Uiso 1 1 d . . .
H2N1 H 0.7755(12) 0.912(2) -0.1345(10) 0.032(5) Uiso 1 1 d . . .
N2G N 0.67356(9) 0.66179(16) -0.09644(6) 0.0179(2) Uani 1 1 d . . .
H1N2 H 0.6449(11) 0.579(2) -0.0790(8) 0.021(4) Uiso 1 1 d . . .
N3G N 0.68304(9) 0.64495(16) -0.16660(6) 0.0180(2) Uani 1 1 d . . .
H1N3 H 0.6619(11) 0.727(2) -0.1891(8) 0.019(4) Uiso 1 1 d . . .
N4G N 0.78820(9) 0.40527(17) -0.15151(7) 0.0215(3) Uani 1 1 d . . .
H1N4 H 0.8224(13) 0.325(2) -0.1677(9) 0.028(5) Uiso 1 1 d . . .
H2N4 H 0.7683(13) 0.389(2) -0.1101(10) 0.034(5) Uiso 1 1 d . . .
C1G C 0.72800(9) 0.78126(17) -0.05800(7) 0.0159(3) Uani 1 1 d . . .
C2G C 0.74635(9) 0.52654(17) -0.19407(7) 0.0162(3) Uani 1 1 d . . .
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'
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
C18 O1 C2 111.32(10) . . ?
O1 C2 C3 108.48(11) . . ?
O1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
O1 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
O4 C3 C2 107.86(11) . . ?
O4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
O4 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C5 O4 C3 112.32(10) . . ?
O4 C5 C6 108.26(11) . . ?
O4 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
O4 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
O7 C6 C5 108.48(11) . . ?
O7 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
O7 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
C8 O7 C6 112.36(10) . . ?
O7 C8 C9 109.00(11) . . ?
O7 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
O7 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
O10 C9 C8 108.54(11) . . ?
O10 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
O10 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C9 O10 C11 111.41(10) . . ?
O10 C11 C12 109.13(11) . . ?
O10 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
O10 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
O13 C12 C11 109.49(11) . . ?
O13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
O13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C14 O13 C12 112.44(10) . . ?
O13 C14 C15 115.90(11) . . ?
O13 C14 H14A 108.3 . . ?
C15 C14 H14A 108.3 . . ?
O13 C14 H14B 108.3 . . ?
C15 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
O16 C15 C14 116.09(11) . . ?
O16 C15 H15A 108.3 . . ?
C14 C15 H15A 108.3 . . ?
O16 C15 H15B 108.3 . . ?
C14 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
C17 O16 C15 113.08(10) . . ?
O16 C17 C18 110.16(11) . . ?
O16 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
O16 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
O1 C18 C17 109.53(11) . . ?
O1 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
O1 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C1G N1G H1N1 118.9(12) . . ?
C1G N1G H2N1 121.6(12) . . ?
H1N1 N1G H2N1 117.8(16) . . ?
C1G N2G N3G 121.71(11) . . ?
C1G N2G H1N2 121.1(11) . . ?
N3G N2G H1N2 115.2(11) . . ?
C2G N3G N2G 122.27(12) . . ?
C2G N3G H1N3 119.4(12) . . ?
N2G N3G H1N3 115.8(11) . . ?
C2G N4G H1N4 118.2(12) . . ?
C2G N4G H2N4 121.1(11) . . ?
H1N4 N4G H2N4 118.3(16) . . ?
N1G C1G N2G 117.00(12) . . ?
N1G C1G S1G 123.52(11) . . ?
N2G C1G S1G 119.48(10) . . ?
N4G C2G N3G 116.63(12) . . ?
N4G C2G S2G 124.43(11) . . ?
N3G C2G S2G 118.92(10) . . ?
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
O1 C18 1.4270(17) . ?
O1 C2 1.4289(16) . ?
C2 C3 1.495(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O4 1.4261(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C5 1.4218(17) . ?
C5 C6 1.496(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O7 1.4271(17) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C8 1.4185(16) . ?
C8 C9 1.4969(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O10 1.4248(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O10 C11 1.4265(16) . ?
C11 C12 1.495(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O13 1.4268(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O13 C14 1.4267(17) . ?
C14 C15 1.523(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O16 1.4285(17) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O16 C17 1.4232(16) . ?
C17 C18 1.4974(19) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
S1G C1G 1.6863(14) . ?
S2G C2G 1.6817(14) . ?
N1G C1G 1.3260(17) . ?
N1G H1N1 0.876(19) . ?
N1G H2N1 0.847(18) . ?
N2G C1G 1.3620(17) . ?
N2G N3G 1.3888(16) . ?
N2G H1N2 0.802(16) . ?
N3G C2G 1.3628(17) . ?
N3G H1N3 0.790(16) . ?
N4G C2G 1.3295(18) . ?
N4G H1N4 0.824(18) . ?
N4G H2N4 0.876(18) . ?
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
N1G H2N1 O1 0.847(18) 2.233(19) 3.0563(16) 163.8(16) .
N1G H1N1 O7 0.876(19) 2.15(2) 3.0067(16) 164.6(16) .
N2G H1N2 O13 0.802(16) 2.276(16) 2.9819(16) 147.1(15) 1_545
N3G H1N3 O16 0.790(16) 2.216(17) 2.9326(16) 151.0(15) .
N4G H1N4 O4 0.824(18) 2.378(19) 3.1632(17) 159.5(16) 1_545
N4G H2N4 O10 0.876(18) 2.201(19) 3.0576(16) 166.1(15) 1_545
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 -58.51(14) . . . . ?
C2 C3 O4 C5 176.03(11) . . . . ?
C3 O4 C5 C6 -173.80(11) . . . . ?
O4 C5 C6 O7 70.29(14) . . . . ?
C5 C6 O7 C8 -169.25(11) . . . . ?
C6 O7 C8 C9 -179.21(11) . . . . ?
O7 C8 C9 O10 -60.10(14) . . . . ?
C8 C9 O10 C11 -173.23(10) . . . . ?
C9 O10 C11 C12 -161.96(11) . . . . ?
O10 C11 C12 O13 -58.15(14) . . . . ?
C11 C12 O13 C14 -170.60(11) . . . . ?
C12 O13 C14 C15 -60.83(15) . . . . ?
O13 C14 C15 O16 -54.22(17) . . . . ?
C14 C15 O16 C17 -53.39(16) . . . . ?
C15 O16 C17 C18 -171.54(11) . . . . ?
O16 C17 C18 O1 -61.45(14) . . . . ?
C17 C18 O1 C2 -163.14(10) . . . . ?
C18 O1 C2 C3 -171.81(11) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21141481
