#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/23/2202381.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_2202381
loop_
_publ_author_name
'P. G. Aravindan'
'D. Velmurugan'
'M. Dhanasekaran'
'P. Rajakumar'
_publ_section_title
9,17-Dioxa-1,3-dithiatetracyclo[18.2.2.2^23,24^.1²⁵]heptacosa-5,7,11,13,15-(25),18,20,23,26-nonene
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1677
_journal_page_last               o1679
_journal_paper_doi               10.1107/S1600536803020129
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C23 H22 O2 S2'
_chemical_formula_sum            'C23 H22 O2 S2'
_chemical_formula_weight         394.53
_chemical_name_systematic
;
9, 17-Dioxa-1,3-dithiatetracyclo[18. 2. 2. 2^23, 24^. 1²⁵] heptacosan-5, 7,
11,13, 15 (25), 18, 20, 23, 26 nonene
;
_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                101.84(5)
_cell_angle_beta                 91.14(5)
_cell_angle_gamma                109.01(5)
_cell_formula_units_Z            2
_cell_length_a                   9.995(5)
_cell_length_b                   10.372(7)
_cell_length_c                   10.508(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.6
_cell_measurement_theta_min      1.8
_cell_volume                     1003.6(10)
_computing_cell_refinement       'CAD4 Express'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;
ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990)
;
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Enraf Nonius FR590
;
_diffrn_measurement_method       'non-profiled w/2θ 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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6133
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.255
_refine_ls_extinction_coef       0.070(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         5832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0415
_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)+(0.0631P)²] where P = (Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                3032
_reflns_number_total             5832
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6351.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1003.5(10)
_cod_original_sg_symbol_H-M      ' P -1'
_cod_database_code               2202381
_cod_database_fobs_code          2202381
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 -0.37039(5) -0.18755(6) 0.59690(6) 0.06067(18) Uani d . 1 . . S
S2 -0.21438(6) -0.38690(6) 0.52576(5) 0.05563(17) Uani d . 1 . . S
O1 0.08204(13) 0.39596(13) 0.97943(12) 0.0515(3) Uani d . 1 . . O
O2 0.42171(14) 0.02889(15) 0.82650(17) 0.0660(4) Uani d . 1 . . O
C1 0.33671(18) 0.33670(19) 0.93297(18) 0.0441(4) Uani d . 1 . . C
H1 0.2881 0.3051 1.0013 0.053 Uiso calc R 1 . . H
C2 0.43220(18) 0.27419(19) 0.87843(18) 0.0437(4) Uani d . 1 . . C
C3 0.50688(19) 0.3252(2) 0.77861(19) 0.0510(5) Uani d . 1 . . C
H3 0.5712 0.2850 0.7402 0.061 Uiso calc R 1 . . H
C4 0.4858(2) 0.4351(2) 0.7366(2) 0.0547(5) Uani d . 1 . . C
H4 0.5376 0.4701 0.6713 0.066 Uiso calc R 1 . . H
C5 0.3879(2) 0.4939(2) 0.79078(19) 0.0509(5) Uani d . 1 . . C
H5 0.3736 0.5672 0.7608 0.061 Uiso calc R 1 . . H
C6 0.31161(18) 0.44420(18) 0.88901(18) 0.0429(4) Uani d . 1 . . C
C7 0.2003(2) 0.5014(2) 0.9476(2) 0.0535(5) Uani d . 1 . . C
H7A 0.2430 0.5730 1.0260 0.064 Uiso calc R 1 . . H
H7B 0.1672 0.5450 0.8861 0.064 Uiso calc R 1 . . H
C8 -0.01096(18) 0.30194(19) 0.87890(17) 0.0423(4) Uani d . 1 . . C
C9 -0.0037(2) 0.3030(2) 0.74767(18) 0.0496(5) Uani d . 1 . . C
H9 0.0700 0.3705 0.7209 0.060 Uiso calc R 1 . . H
C10 -0.1075(2) 0.2025(2) 0.65635(18) 0.0514(5) Uani d . 1 . . C
H10 -0.1023 0.2042 0.5684 0.062 Uiso calc R 1 . . H
C11 -0.21866(18) 0.0995(2) 0.69210(17) 0.0438(4) Uani d . 1 . . C
C12 -0.22253(19) 0.1004(2) 0.82433(18) 0.0471(4) Uani d . 1 . . C
H12 -0.2955 0.0324 0.8513 0.057 Uiso calc R 1 . . H
C13 -0.12109(19) 0.1994(2) 0.91630(17) 0.0453(4) Uani d . 1 . . C
H13 -0.1264 0.1976 1.0042 0.054 Uiso calc R 1 . . H
C14 -0.3349(2) -0.0058(2) 0.5931(2) 0.0569(5) Uani d . 1 . . C
H14A -0.3098 0.0063 0.5065 0.068 Uiso calc R 1 . . H
H14B -0.4220 0.0153 0.6066 0.068 Uiso calc R 1 . . H
C15 -0.22261(19) -0.2196(2) 0.51659(19) 0.0513(5) Uani d . 1 . . C
H15A -0.2325 -0.2152 0.4257 0.062 Uiso calc R 1 . . H
H15B -0.1348 -0.1473 0.5574 0.062 Uiso calc R 1 . . H
C16 -0.1411(2) -0.3537(2) 0.69394(19) 0.0580(5) Uani d . 1 . . C
H16A -0.2039 -0.3215 0.7516 0.070 Uiso calc R 1 . . H
H16B -0.1392 -0.4411 0.7121 0.070 Uiso calc R 1 . . H
C17 0.0065(2) -0.2474(2) 0.72490(18) 0.0478(5) Uani d . 1 . . C
C18 0.1248(2) -0.2841(2) 0.6884(2) 0.0525(5) Uani d . 1 . . C
H18 0.1121 -0.3740 0.6407 0.063 Uiso calc R 1 . . H
C19 0.2608(2) -0.1888(2) 0.7222(2) 0.0528(5) Uani d . 1 . . C
H19 0.3386 -0.2152 0.6971 0.063 Uiso calc R 1 . . H
C20 0.28187(19) -0.0548(2) 0.7930(2) 0.0496(5) Uani d . 1 . . C
C21 0.1649(2) -0.0150(2) 0.8249(2) 0.0563(5) Uani d . 1 . . C
H21 0.1771 0.0760 0.8691 0.068 Uiso calc R 1 . . H
C22 0.0292(2) -0.1125(2) 0.7901(2) 0.0532(5) Uani d . 1 . . C
H22 -0.0488 -0.0852 0.8119 0.064 Uiso calc R 1 . . H
C23 0.4525(2) 0.1549(2) 0.9260(2) 0.0580(5) Uani d . 1 . . C
H23A 0.5501 0.1827 0.9628 0.070 Uiso calc R 1 . . H
H23B 0.3916 0.1356 0.9954 0.070 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'
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
_geom_angle_publ_flag
C15 S1 C14 100.70(10) y
C15 S2 C16 101.70(10) y
C8 O1 C7 118.0(2) y
C20 O2 C23 118.4(2) y
C6 C1 C2 122.1(2) ?
C6 C1 H1 118.9 ?
C2 C1 H1 118.9 ?
C1 C2 C3 118.2(2) ?
C1 C2 C23 120.4(2) ?
C3 C2 C23 121.4(2) ?
C4 C3 C2 120.2(2) ?
C4 C3 H3 119.9 ?
C2 C3 H3 119.9 ?
C3 C4 C5 120.6(2) ?
C3 C4 H4 119.7 ?
C5 C4 H4 119.7 ?
C6 C5 C4 120.4(2) ?
C6 C5 H5 119.8 ?
C4 C5 H5 119.8 ?
C5 C6 C1 118.6(2) ?
C5 C6 C7 122.2(2) ?
C1 C6 C7 119.2(2) ?
O1 C7 C6 112.5(2) ?
O1 C7 H7A 109.1 ?
C6 C7 H7A 109.1 ?
O1 C7 H7B 109.1 ?
C6 C7 H7B 109.1 ?
H7A C7 H7B 107.8 ?
O1 C8 C9 125.7(2) ?
O1 C8 C13 115.1(2) ?
C9 C8 C13 119.2(2) ?
C8 C9 C10 119.4(2) ?
C8 C9 H9 120.3 ?
C10 C9 H9 120.3 ?
C11 C10 C9 122.1(2) ?
C11 C10 H10 118.9 ?
C9 C10 H10 118.9 ?
C10 C11 C12 117.2(2) ?
C10 C11 C14 121.9(2) ?
C12 C11 C14 120.9(2) ?
C13 C12 C11 121.6(2) ?
C13 C12 H12 119.2 ?
C11 C12 H12 119.2 ?
C12 C13 C8 120.5(2) ?
C12 C13 H13 119.8 ?
C8 C13 H13 119.8 ?
C11 C14 S1 115.70(10) ?
C11 C14 H14A 108.3 ?
S1 C14 H14A 108.3 ?
C11 C14 H14B 108.3 ?
S1 C14 H14B 108.3 ?
H14A C14 H14B 107.4 ?
S2 C15 S1 111.20(10) y
S2 C15 H15A 109.4 ?
S1 C15 H15A 109.4 ?
S2 C15 H15B 109.4 ?
S1 C15 H15B 109.4 ?
H15A C15 H15B 108.0 ?
C17 C16 S2 114.20(10) ?
C17 C16 H16A 108.7 ?
S2 C16 H16A 108.7 ?
C17 C16 H16B 108.7 ?
S2 C16 H16B 108.7 ?
H16A C16 H16B 107.6 ?
C22 C17 C18 117.8(2) ?
C22 C17 C16 121.5(2) ?
C18 C17 C16 120.8(2) ?
C19 C18 C17 120.9(2) ?
C19 C18 H18 119.5 ?
C17 C18 H18 119.5 ?
C18 C19 C20 120.4(2) ?
C18 C19 H19 119.8 ?
C20 C19 H19 119.8 ?
O2 C20 C19 115.4(2) ?
O2 C20 C21 125.4(2) ?
C19 C20 C21 119.2(2) ?
C20 C21 C22 119.3(2) ?
C20 C21 H21 120.3 ?
C22 C21 H21 120.3 ?
C17 C22 C21 122.2(2) ?
C17 C22 H22 118.9 ?
C21 C22 H22 118.9 ?
O2 C23 C2 113.9(2) ?
O2 C23 H23A 108.8 ?
C2 C23 H23A 108.8 ?
O2 C23 H23B 108.8 ?
C2 C23 H23B 108.8 ?
H23A C23 H23B 107.7 ?
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 C15 . 1.805(2) y
S1 C14 . 1.810(3) y
S2 C15 . 1.786(2) y
S2 C16 . 1.820(2) y
O1 C8 . 1.370(2) y
O1 C7 . 1.425(2) y
O2 C20 . 1.377(2) y
O2 C23 . 1.435(3) y
C1 C6 . 1.382(3) ?
C1 C2 . 1.390(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.393(3) ?
C2 C23 . 1.495(3) ?
C3 C4 . 1.377(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.509(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.384(3) ?
C8 C13 . 1.387(3) ?
C9 C10 . 1.389(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.387(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.389(3) ?
C11 C14 . 1.511(3) ?
C12 C13 . 1.375(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.508(3) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C22 . 1.368(3) ?
C17 C18 . 1.394(3) ?
C18 C19 . 1.382(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.381(3) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.387(3) ?
C21 C22 . 1.389(3) ?
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
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_publ_flag
C6 C1 C2 C3 1.7(3) ?
C6 C1 C2 C23 -177.9(2) ?
C1 C2 C3 C4 0.2(3) ?
C23 C2 C3 C4 179.9(2) ?
C2 C3 C4 C5 -1.5(3) ?
C3 C4 C5 C6 0.9(3) ?
C4 C5 C6 C1 1.0(3) ?
C4 C5 C6 C7 -177.8(2) ?
C2 C1 C6 C5 -2.3(3) ?
C2 C1 C6 C7 176.5(2) ?
C6 C7 O1 C8 -72.7(2) y
C5 C6 C7 O1 143.5(2) ?
C1 C6 C7 O1 -35.3(2) ?
C7 O1 C8 C9 -2.7(3) ?
C7 O1 C8 C13 178.0(2) ?
O1 C8 C9 C10 -178.6(2) ?
C13 C8 C9 C10 0.6(3) ?
C8 C9 C10 C11 -0.4(3) ?
C9 C10 C11 C12 0.0(3) ?
C9 C10 C11 C14 177.2(2) ?
C10 C11 C12 C13 0.3(3) ?
C14 C11 C12 C13 -177.0(2) ?
C11 C12 C13 C8 -0.1(3) ?
O1 C8 C13 C12 179.0(2) ?
C9 C8 C13 C12 -0.4(3) ?
C10 C11 C14 S1 128.6(2) ?
C12 C11 C14 S1 -54.2(2) ?
C11 C14 S1 C15 -77.0(2) y
S1 C15 S2 C16 -76.30(10) y
S2 C15 S1 C14 171.80(10) y
C17 C16 S2 C15 -63.1(2) y
S2 C16 C17 C22 101.7(2) ?
S2 C16 C17 C18 -78.8(2) ?
C22 C17 C18 C19 2.8(3) ?
C16 C17 C18 C19 -176.8(2) ?
C17 C18 C19 C20 -0.1(3) ?
C23 O2 C20 C19 -164.6(2) ?
C23 O2 C20 C21 15.2(3) ?
C18 C19 C20 O2 177.0(2) ?
C18 C19 C20 C21 -2.8(3) ?
O2 C20 C21 C22 -176.9(2) ?
C19 C20 C21 C22 2.9(3) ?
C18 C17 C22 C21 -2.7(3) ?
C16 C17 C22 C21 176.9(2) ?
C20 C21 C22 C17 -0.1(3) ?
C2 C23 O2 C20 -80.5(2) y
C1 C2 C23 O2 120.9(2) ?
C3 C2 C23 O2 -58.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9375327
