#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/84/2208430.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2208430
loop_
_publ_author_name
'Fonari, Marina S.'
'Ganin, Eduard V.'
'Simonov, Yurii A.'
'Wen-Jwu Wang'
_publ_section_title
;cis-anti-cis-Dicyclohexyl-18-crown-6--thiacetazone--methanol
 (1/2/2)
;
_journal_coeditor_code           SU6265
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o911
_journal_page_last               o913
_journal_paper_doi               10.1107/S1600536806003709
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C20 H36 O6, 2C10 H12 N4 O S, 2C H4 O'
_chemical_formula_moiety         'C20 H36 O6, 2C10 H12 N4 O S, 2C H4 O'
_chemical_formula_sum            'C42 H68 N8 O10 S2'
_chemical_formula_weight         909.16
_chemical_melting_point_gt       240
_chemical_name_common
;
Cis-anti-cis dicyclohexyl-18-crown-6 bis(thiacetazone)
bis methanol clathrate
;
_chemical_name_systematic
;
2,5,8,15,18,21-tricyclo[20.4.0.0^9,14^]hexacosane--bis(4-
acetylaminobenzaldehyde thiosemicarbazone)--methanol (1/1/2)
;
_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                93.17(3)
_cell_angle_beta                 91.38(2)
_cell_angle_gamma                118.649(7)
_cell_formula_units_Z            1
_cell_length_a                   9.6712(18)
_cell_length_b                   9.9236(18)
_cell_length_c                   14.849(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      12.50
_cell_measurement_theta_min      4.38
_cell_volume                     1246.6(5)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       2θ/ω
_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  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4658
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XSCANS; Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4371
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0429
_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)+(0.058P)²+0.2974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                3488
_reflns_number_total             4371
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6265.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_gt' since the value was specified 'more
than' ('>') a certain temperature. The value '>240' was changed to
'240' - it should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_gt' since the value was specified 'more
than' ('>') a certain temperature. The value '>240' was changed to
'240' - it should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1246.7(5)
_cod_database_code               2208430
_cod_database_fobs_code          2208430
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
S1 1.03225(7) 1.40142(6) 0.16405(4) 0.06694(19) Uani d . 1 S
O1 1.33801(15) 1.16556(15) 0.07337(9) 0.0555(3) Uani d . 1 O
O2 1.14770(14) 1.23492(13) -0.04789(8) 0.0523(3) Uani d . 1 O
O3 0.86478(15) 1.10527(14) -0.15644(8) 0.0532(3) Uani d . 1 O
O4 0.8448(2) 0.31868(17) 0.41805(10) 0.0711(4) Uani d . 1 O
O5 0.6666(3) 0.4218(3) 0.69884(13) 0.1139(7) Uani d D 1 O
H1O 0.754(4) 0.467(5) 0.735(3) 0.179(19) Uiso d D 1 H
N1 0.7502(2) 0.43447(17) 0.51568(12) 0.0565(4) Uani d . 1 N
H1A 0.713(2) 0.428(2) 0.5675(14) 0.057(6) Uiso d . 1 H
N2 0.9140(2) 1.02901(17) 0.29149(11) 0.0571(4) Uani d . 1 N
N3 0.9416(2) 1.1732(2) 0.26938(13) 0.0645(5) Uani d . 1 N
H3A 0.925(3) 1.229(3) 0.3081(15) 0.065(6) Uiso d . 1 H
N4 1.0106(2) 1.1255(2) 0.13103(12) 0.0583(4) Uani d . 1 N
H4A 0.996(3) 1.038(3) 0.1462(15) 0.074(7) Uiso d . 1 H
H4B 1.053(2) 1.153(2) 0.0807(15) 0.058(6) Uiso d . 1 H
C1 1.3002(2) 0.9825(2) 0.18067(13) 0.0545(5) Uani d . 1 C
H1 1.3377 0.9101 0.2001 0.065 Uiso calc R 1 H
C2 1.3201(2) 1.0922(3) 0.26181(13) 0.0620(5) Uani d . 1 C
H2A 1.2571 1.0326 0.3111 0.074 Uiso calc R 1 H
H2B 1.2803 1.1630 0.2448 0.074 Uiso calc R 1 H
C3 1.4931(3) 1.1856(3) 0.29518(16) 0.0786(7) Uani d . 1 C
H3C 1.5042 1.2605 0.3455 0.094 Uiso calc R 1 H
H3D 1.5297 1.1157 0.3184 0.094 Uiso calc R 1 H
C4 1.5951(3) 1.2713(3) 0.21926(17) 0.0773(7) Uani d . 1 C
H4C 1.7075 1.3248 0.2413 0.093 Uiso calc R 1 H
H4D 1.5670 1.3500 0.2012 0.093 Uiso calc R 1 H
C5 1.5726(2) 1.1613(3) 0.13748(16) 0.0703(6) Uani d . 1 C
H5A 1.6116 1.0896 0.1540 0.084 Uiso calc R 1 H
H5B 1.6358 1.2210 0.0883 0.084 Uiso calc R 1 H
C6 1.3992(2) 1.0687(2) 0.10368(13) 0.0539(5) Uani d . 1 C
H6A 1.3880 0.9929 0.0530 0.065 Uiso calc R 1 H
C7 1.3796(3) 1.2152(3) -0.01399(15) 0.0699(6) Uani d . 1 C
H7A 1.3361 1.1252 -0.0589 0.084 Uiso calc R 1 H
H7B 1.4959 1.2702 -0.0166 0.084 Uiso calc R 1 H
C8 1.3144(2) 1.3205(3) -0.03535(16) 0.0687(6) Uani d . 1 C
H8A 1.3443 1.4011 0.0148 0.082 Uiso calc R 1 H
H8B 1.3595 1.3717 -0.0909 0.082 Uiso calc R 1 H
C9 1.0813(2) 1.3255(2) -0.08135(14) 0.0566(5) Uani d . 1 C
H9A 1.1212 1.3600 -0.1412 0.068 Uiso calc R 1 H
H9B 1.1118 1.4177 -0.0395 0.068 Uiso calc R 1 H
C10 0.9061(2) 1.2287(2) -0.08905(14) 0.0567(5) Uani d . 1 C
H10A 0.8672 1.1871 -0.0303 0.068 Uiso calc R 1 H
H10B 0.8568 1.2918 -0.1060 0.068 Uiso calc R 1 H
C11 0.7245(3) 0.1894(3) 0.54867(18) 0.0811(7) Uani d . 1 C
H11A 0.8087 0.1634 0.5602 0.122 Uiso calc R 1 H
H11B 0.6317 0.0991 0.5197 0.122 Uiso calc R 1 H
H11C 0.6963 0.2211 0.6060 0.122 Uiso calc R 1 H
C12 0.7808(2) 0.3196(2) 0.48727(13) 0.0539(5) Uani d . 1 C
C13 0.7843(2) 0.5709(2) 0.47471(12) 0.0533(5) Uani d . 1 C
C14 0.7463(4) 0.6717(3) 0.52225(16) 0.0914(9) Uani d . 1 C
H14A 0.6995 0.6463 0.5787 0.110 Uiso calc R 1 H
C15 0.7762(4) 0.8089(3) 0.48781(17) 0.1067(11) Uani d . 1 C
H15A 0.7519 0.8780 0.5218 0.128 Uiso calc R 1 H
C16 0.8408(3) 0.8479(2) 0.40466(14) 0.0655(6) Uani d . 1 C
C17 0.8777(2) 0.7454(2) 0.35790(12) 0.0536(5) Uani d . 1 C
H17A 0.9232 0.7700 0.3011 0.064 Uiso calc R 1 H
C18 0.8499(2) 0.6090(2) 0.39194(12) 0.0529(5) Uani d . 1 C
H18A 0.8758 0.5407 0.3584 0.063 Uiso calc R 1 H
C19 0.8712(3) 0.9946(3) 0.37037(15) 0.0788(7) Uani d . 1 C
H19A 0.8582 1.0668 0.4091 0.095 Uiso calc R 1 H
C20 0.9936(2) 1.2213(2) 0.18835(13) 0.0498(4) Uani d . 1 C
C21 0.5427(5) 0.3862(6) 0.7461(3) 0.1617(18) Uani d . 1 C
H21A 0.5703 0.4636 0.7970 0.242 Uiso calc R 1 H
H21B 0.5074 0.2848 0.7691 0.242 Uiso calc R 1 H
H21C 0.4576 0.3838 0.7077 0.242 Uiso calc R 1 H
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'
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 O1 C6 . . 114.52(15) no
C8 O2 C9 . . 112.03(14) no
C10 O3 C1 . 2_775 114.52(14) no
C21 O5 H1O . . 110(3) no
C12 N1 C13 . . 128.89(17) yes
C12 N1 H1A . . 116.1(14) no
C13 N1 H1A . . 114.7(14) no
C19 N2 N3 . . 115.99(17) yes
C20 N3 N2 . . 119.86(17) yes
C20 N3 H3A . . 121.8(15) no
N2 N3 H3A . . 118.3(15) no
C20 N4 H4A . . 121.4(15) no
C20 N4 H4B . . 121.7(14) no
H4A N4 H4B . . 116(2) no
O3 C1 C2 2_775 . 107.37(15) no
O3 C1 C6 2_775 . 113.84(15) no
C2 C1 C6 . . 111.49(17) no
O3 C1 H1 2_775 . 108.0 no
C2 C1 H1 . . 108.0 no
C6 C1 H1 . . 108.0 no
C1 C2 C3 . . 110.85(17) no
C1 C2 H2A . . 109.5 no
C3 C2 H2A . . 109.5 no
C1 C2 H2B . . 109.5 no
C3 C2 H2B . . 109.5 no
H2A C2 H2B . . 108.1 no
C4 C3 C2 . . 110.85(19) no
C4 C3 H3C . . 109.5 no
C2 C3 H3C . . 109.5 no
C4 C3 H3D . . 109.5 no
C2 C3 H3D . . 109.5 no
H3C C3 H3D . . 108.1 no
C3 C4 C5 . . 111.3(2) no
C3 C4 H4C . . 109.4 no
C5 C4 H4C . . 109.4 no
C3 C4 H4D . . 109.4 no
C5 C4 H4D . . 109.4 no
H4C C4 H4D . . 108.0 no
C4 C5 C6 . . 111.64(17) no
C4 C5 H5A . . 109.3 no
C6 C5 H5A . . 109.3 no
C4 C5 H5B . . 109.3 no
C6 C5 H5B . . 109.3 no
H5A C5 H5B . . 108.0 no
O1 C6 C1 . . 107.20(14) no
O1 C6 C5 . . 112.10(16) no
C1 C6 C5 . . 109.44(17) no
O1 C6 H6A . . 109.3 no
C1 C6 H6A . . 109.3 no
C5 C6 H6A . . 109.3 no
O1 C7 C8 . . 108.93(17) no
O1 C7 H7A . . 109.9 no
C8 C7 H7A . . 109.9 no
O1 C7 H7B . . 109.9 no
C8 C7 H7B . . 109.9 no
H7A C7 H7B . . 108.3 no
O2 C8 C7 . . 109.79(17) no
O2 C8 H8A . . 109.7 no
C7 C8 H8A . . 109.7 no
O2 C8 H8B . . 109.7 no
C7 C8 H8B . . 109.7 no
H8A C8 H8B . . 108.2 no
O2 C9 C10 . . 108.39(14) no
O2 C9 H9A . . 110.0 no
C10 C9 H9A . . 110.0 no
O2 C9 H9B . . 110.0 no
C10 C9 H9B . . 110.0 no
H9A C9 H9B . . 108.4 no
O3 C10 C9 . . 108.77(16) no
O3 C10 H10A . . 109.9 no
C9 C10 H10A . . 109.9 no
O3 C10 H10B . . 109.9 no
C9 C10 H10B . . 109.9 no
H10A C10 H10B . . 108.3 no
C12 C11 H11A . . 109.5 no
C12 C11 H11B . . 109.5 no
H11A C11 H11B . . 109.5 no
C12 C11 H11C . . 109.5 no
H11A C11 H11C . . 109.5 no
H11B C11 H11C . . 109.5 no
O4 C12 N1 . . 123.72(18) yes
O4 C12 C11 . . 122.43(18) yes
N1 C12 C11 . . 113.83(19) yes
C18 C13 C14 . . 118.96(17) yes
C18 C13 N1 . . 125.11(17) yes
C14 C13 N1 . . 115.93(17) yes
C15 C14 C13 . . 120.16(19) yes
C15 C14 H14A . . 119.9 no
C13 C14 H14A . . 119.9 no
C14 C15 C16 . . 121.4(2) yes
C14 C15 H15A . . 119.3 no
C16 C15 H15A . . 119.3 no
C15 C16 C17 . . 117.58(18) yes
C15 C16 C19 . . 119.91(18) no
C17 C16 C19 . . 122.49(18) no
C18 C17 C16 . . 121.50(17) yes
C18 C17 H17A . . 119.3 no
C16 C17 H17A . . 119.3 no
C17 C18 C13 . . 120.34(16) yes
C17 C18 H18A . . 119.8 no
C13 C18 H18A . . 119.8 no
N2 C19 C16 . . 122.59(19) yes
N2 C19 H19A . . 118.7 no
C16 C19 H19A . . 118.7 no
N4 C20 N3 . . 117.77(17) yes
N4 C20 S1 . . 123.29(15) no
N3 C20 S1 . . 118.94(15) no
O5 C21 H21A . . 109.5 no
O5 C21 H21B . . 109.5 no
H21A C21 H21B . . 109.5 no
O5 C21 H21C . . 109.5 no
H21A C21 H21C . . 109.5 no
H21B C21 H21C . . 109.5 no
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 C20 . 1.7034(18) yes
O1 C7 . 1.412(2) no
O1 C6 . 1.434(2) no
O2 C8 . 1.418(2) no
O2 C9 . 1.433(2) no
O3 C10 . 1.427(2) no
O3 C1 2_775 1.428(2) no
O4 C12 . 1.214(2) yes
O5 C21 . 1.310(4) yes
O5 H1O . 0.889(19) no
N1 C12 . 1.358(2) yes
N1 C13 . 1.409(2) yes
N1 H1A . 0.85(2) no
N2 C19 . 1.262(3) yes
N2 N3 . 1.384(2) yes
N3 C20 . 1.339(2) yes
N3 H3A . 0.84(2) no
N4 C20 . 1.313(3) yes
N4 H4A . 0.86(3) no
N4 H4B . 0.86(2) no
C1 O3 2_775 1.428(2) no
C1 C2 . 1.522(3) no
C1 C6 . 1.527(3) no
C1 H1 . 1.0000 no
C2 C3 . 1.525(3) no
C2 H2A . 0.9900 no
C2 H2B . 0.9900 no
C3 C4 . 1.524(4) no
C3 H3C . 0.9900 no
C3 H3D . 0.9900 no
C4 C5 . 1.525(3) no
C4 H4C . 0.9900 no
C4 H4D . 0.9900 no
C5 C6 . 1.530(3) no
C5 H5A . 0.9900 no
C5 H5B . 0.9900 no
C6 H6A . 1.0000 no
C7 C8 . 1.500(3) no
C7 H7A . 0.9900 no
C7 H7B . 0.9900 no
C8 H8A . 0.9900 no
C8 H8B . 0.9900 no
C9 C10 . 1.492(3) no
C9 H9A . 0.9900 no
C9 H9B . 0.9900 no
C10 H10A . 0.9900 no
C10 H10B . 0.9900 no
C11 C12 . 1.509(3) yes
C11 H11A . 0.9800 no
C11 H11B . 0.9800 no
C11 H11C . 0.9800 no
C13 C18 . 1.384(3) yes
C13 C14 . 1.386(3) yes
C14 C15 . 1.380(3) yes
C14 H14A . 0.9500 no
C15 C16 . 1.387(3) yes
C15 H15A . 0.9500 no
C16 C17 . 1.388(3) yes
C16 C19 . 1.464(3) yes
C17 C18 . 1.376(3) yes
C17 H17A . 0.9500 no
C18 H18A . 0.9500 no
C19 H19A . 0.9500 no
C21 H21A . 0.9800 no
C21 H21B . 0.9800 no
C21 H21C . 0.9800 no
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
_geom_hbond_publ_flag
O5 H1O S1 2_776 0.89(2) 2.30(2) 3.182(3) 174(4) yes
N1 H1A O5 . 0.85(2) 2.01(2) 2.848(3) 169(2) yes
N3 H3A O4 1_565 0.84(2) 2.15(2) 2.980(2) 167(2) yes
N4 H4A O3 2_775 0.86(3) 2.38(2) 3.092(2) 140(2) yes
N4 H4B O2 . 0.86(2) 2.16(2) 3.017(2) 175(2) yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C6 O1 C7 . . . -160.6(2) yes
C6 O1 C7 C8 . . . -177.5(2) yes
O1 C7 C8 O2 . . . -70.1(2) yes
C7 C8 O2 C9 . . . -171.5(2) yes
C8 O2 C9 C10 . . . -177.8(2) yes
O2 C9 C10 O3 . . . -65.4(2) yes
C9 C10 O3 C1 . . 2_776 112.0(2) yes
C10 O3 C1 C6 . 2_776 2_776 140.9(2) yes
O3 C1 C6 O1 2_776 2_776 2_776 96.9(2) yes
