#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:39:56 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178401 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/23/4022381.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_4022381
loop_
_publ_author_name
'Henry J. Shine'
'Bingjun Zhao'
'Ding-Quan Qian'
'John N. Marx'
'Ilse Y. Guzmán-Jiménez'
'John H. Thurston'
'T. Ould-Ely'
'Kenton H. Whitmire'
_publ_contact_author
;
Henry J. Shine
Department of Chemistry and Biochemistry
Texas Tech University
Lubbock, Texas 79409
;
_publ_contact_author_email       henry.shine@ttu.edu
_publ_contact_author_fax         '806 742 1289'
_publ_contact_author_phone       '806 742 3067'
_publ_section_title
;
 Adducts of Phenoxathiin and Thianthrene Cation Radicals
 with Alkenes and Cycloalkenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8910
_journal_page_last               8917
_journal_paper_doi               10.1021/jo030173h
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C31 H28 Cl2 O10 S2'
_chemical_formula_weight         695.55
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 108.00(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.198(3)
_cell_length_b                   13.998(3)
_cell_length_c                   15.977(3)
_cell_measurement_reflns_used    5643
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.500
_cell_measurement_theta_min      4.202
_cell_volume                     3019.9(10)
_computing_cell_refinement       'SHELXTL 5.10 (Bruker AXS,1997)'
_computing_data_collection       'SHELXTL 5.10 (Bruker AXS,1997)'
_computing_data_reduction        'SHELXTL 5.10 (Bruker AXS,1997)'
_computing_molecular_graphics    'SHELXTL 5.10 (Bruker AXS,1997)'
_computing_publication_material  'SHELXTL 5.10 (Bruker AXS,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker AXS'
_diffrn_measurement_method       2thetaω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            7357
_diffrn_reflns_theta_full        23.30
_diffrn_reflns_theta_max         23.30
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.413
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.611334
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.31
_refine_diff_density_max         1.100
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         4022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0766
_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)+(0.1475P)²+4.9295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2275
_refine_ls_wR_factor_ref         0.2449
_reflns_number_gt                3053
_reflns_number_total             4022
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo030173h_03.cif
_cod_data_source_block
"'1,2-bis(5-phenoxathiiniumyl)cyclopentane(ClO4)2_qpo2'"
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022381
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S1 S 0.15289(10) 0.83612(9) 0.03610(9) 0.0364(4) Uani 1 1 d .
O1 O 0.0795(3) 0.6587(3) 0.1052(3) 0.0521(11) Uani 1 1 d .
C1 C 0.0652(4) 0.8321(4) 0.0930(4) 0.0379(13) Uani 1 1 d .
C2 C 0.0215(4) 0.9158(4) 0.1080(4) 0.0484(15) Uani 1 1 d .
H2A H 0.0379 0.9739 0.0878 0.058 Uiso 1 1 calc R
C3 C -0.0465(5) 0.9119(5) 0.1531(5) 0.0591(18) Uani 1 1 d .
H3A H -0.0755 0.9678 0.1650 0.071 Uiso 1 1 calc R
C4 C -0.0718(5) 0.8246(6) 0.1810(5) 0.0623(19) Uani 1 1 d .
H4A H -0.1180 0.8228 0.2115 0.075 Uiso 1 1 calc R
C5 C -0.0309(5) 0.7417(5) 0.1651(5) 0.0549(17) Uani 1 1 d .
H5A H -0.0493 0.6837 0.1839 0.066 Uiso 1 1 calc R
C6 C 0.0395(4) 0.7444(4) 0.1199(4) 0.0439(14) Uani 1 1 d .
C7 C 0.1066(4) 0.6481(4) 0.0308(4) 0.0409(13) Uani 1 1 d .
C8 C 0.1057(4) 0.5555(4) -0.0009(5) 0.0537(17) Uani 1 1 d .
H8A H 0.0919 0.5039 0.0300 0.064 Uiso 1 1 calc R
C9 C 0.1258(5) 0.5415(5) -0.0792(5) 0.0618(19) Uani 1 1 d .
H9A H 0.1241 0.4800 -0.1017 0.074 Uiso 1 1 calc R
C10 C 0.1481(4) 0.6167(5) -0.1244(4) 0.0575(18) Uani 1 1 d .
H10A H 0.1604 0.6056 -0.1775 0.069 Uiso 1 1 calc R
C11 C 0.1528(4) 0.7090(5) -0.0925(4) 0.0480(15) Uani 1 1 d .
H11A H 0.1677 0.7601 -0.1234 0.058 Uiso 1 1 calc R
C12 C 0.1346(4) 0.7231(4) -0.0130(4) 0.0374(13) Uani 1 1 d .
S2 S 0.45990(10) 0.74858(9) 0.13199(9) 0.0382(4) Uani 1 1 d .
O2 O 0.4119(3) 0.6734(3) -0.0523(3) 0.0506(11) Uani 1 1 d .
C13 C 0.4128(4) 0.6339(4) 0.0954(4) 0.0417(14) Uani 1 1 d .
C14 C 0.3960(5) 0.5685(5) 0.1544(5) 0.0572(17) Uani 1 1 d .
H14A H 0.4083 0.5846 0.2133 0.069 Uiso 1 1 calc R
C15 C 0.3610(5) 0.4799(5) 0.1242(6) 0.070(2) Uani 1 1 d .
H15A H 0.3494 0.4351 0.1629 0.083 Uiso 1 1 calc R
C16 C 0.3428(5) 0.4566(5) 0.0363(6) 0.070(2) Uani 1 1 d .
H16A H 0.3173 0.3967 0.0163 0.084 Uiso 1 1 calc R
C17 C 0.3617(5) 0.5199(4) -0.0214(5) 0.0578(17) Uani 1 1 d .
H17A H 0.3517 0.5029 -0.0798 0.069 Uiso 1 1 calc R
C18 C 0.3960(4) 0.6099(4) 0.0085(4) 0.0427(14) Uani 1 1 d .
C19 C 0.4957(4) 0.7314(4) -0.0240(4) 0.0448(15) Uani 1 1 d .
C20 C 0.5441(5) 0.7530(5) -0.0847(5) 0.0566(17) Uani 1 1 d .
H20A H 0.5182 0.7329 -0.1428 0.068 Uiso 1 1 calc R
C21 C 0.6293(5) 0.8036(5) -0.0590(6) 0.066(2) Uani 1 1 d .
H21A H 0.6614 0.8188 -0.0999 0.080 Uiso 1 1 calc R
C22 C 0.6690(5) 0.8329(5) 0.0265(6) 0.067(2) Uani 1 1 d .
H22A H 0.7293 0.8649 0.0435 0.080 Uiso 1 1 calc R
C23 C 0.6206(4) 0.8153(4) 0.0880(5) 0.0527(16) Uani 1 1 d .
H23A H 0.6465 0.8364 0.1458 0.063 Uiso 1 1 calc R
C24 C 0.5318(4) 0.7650(4) 0.0606(4) 0.0414(14) Uani 1 1 d .
C25 C 0.2739(4) 0.8197(4) 0.1251(4) 0.0346(12) Uani 1 1 d .
H25A H 0.2766 0.7548 0.1486 0.041 Uiso 1 1 calc R
C26 C 0.3525(4) 0.8294(3) 0.0778(4) 0.0352(12) Uani 1 1 d .
H26A H 0.3224 0.8053 0.0179 0.042 Uiso 1 1 calc R
C27 C 0.3883(4) 0.9300(4) 0.0692(4) 0.0446(14) Uani 1 1 d .
H27A H 0.3310 0.9716 0.0508 0.054 Uiso 1 1 calc R
H27B H 0.4186 0.9300 0.0224 0.054 Uiso 1 1 calc R
C28 C 0.4624(5) 0.9734(4) 0.1516(5) 0.0555(17) Uani 1 1 d .
H28A H 0.5159 0.9280 0.1741 0.067 Uiso 1 1 calc R
H28B H 0.4907 1.0301 0.1339 0.067 Uiso 1 1 calc R
C29 C 0.4234(5) 1.0005(4) 0.2260(5) 0.0598(18) Uani 1 1 d .
H29A H 0.3752 1.0514 0.2061 0.072 Uiso 1 1 calc R
H29B H 0.4776 1.0255 0.2741 0.072 Uiso 1 1 calc R
C30 C 0.3752(5) 0.9186(5) 0.2604(4) 0.0576(17) Uani 1 1 d .
H30A H 0.4186 0.8635 0.2704 0.069 Uiso 1 1 calc R
H30B H 0.3676 0.9370 0.3166 0.069 Uiso 1 1 calc R
C31 C 0.2746(4) 0.8908(4) 0.1980(4) 0.0485(15) Uani 1 1 d .
H31A H 0.2413 0.9485 0.1706 0.058 Uiso 1 1 calc R
H31B H 0.2358 0.8639 0.2326 0.058 Uiso 1 1 calc R
Cl1 Cl 0.14070(12) 0.17782(12) 0.12246(11) 0.0567(5) Uani 1 1 d .
O11 O 0.0461(4) 0.1590(4) 0.1337(4) 0.0844(16) Uiso 1 1 d .
O12 O 0.1354(5) 0.2633(4) 0.0742(4) 0.0907(17) Uiso 1 1 d .
O13 O 0.2153(5) 0.1833(4) 0.2062(4) 0.0947(18) Uiso 1 1 d .
O14 O 0.1642(4) 0.0999(3) 0.0748(4) 0.0702(13) Uiso 1 1 d .
Cl2 Cl 0.25018(12) 0.91089(12) -0.22443(11) 0.0563(5) Uani 1 1 d .
O21 O 0.1553(6) 0.8747(5) -0.2601(5) 0.116(2) Uiso 1 1 d .
O22 O 0.2845(8) 0.8957(7) -0.1330(8) 0.170(4) Uiso 1 1 d .
O23 O 0.2454(6) 1.0139(6) -0.2322(6) 0.132(3) Uiso 1 1 d .
O24 O 0.3114(7) 0.8919(7) -0.2721(7) 0.159(3) Uiso 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C12 S1 C1 99.9(2)
C12 S1 C25 101.8(2)
C1 S1 C25 103.5(3)
C7 O1 C6 119.0(4)
C2 C1 C6 121.5(5)
C2 C1 S1 119.4(4)
C6 C1 S1 119.1(4)
C3 C2 C1 118.9(6)
C2 C3 C4 119.8(6)
C5 C4 C3 121.7(6)
C4 C5 C6 119.2(6)
O1 C6 C1 123.8(5)
O1 C6 C5 117.4(5)
C1 C6 C5 118.8(5)
O1 C7 C12 124.0(5)
O1 C7 C8 116.5(5)
C12 C7 C8 119.6(6)
C9 C8 C7 118.8(6)
C10 C9 C8 121.0(6)
C9 C10 C11 121.2(6)
C10 C11 C12 118.0(6)
C11 C12 C7 121.2(5)
C11 C12 S1 119.8(5)
C7 C12 S1 119.0(4)
C24 S2 C13 98.1(3)
C24 S2 C26 99.9(2)
C13 S2 C26 103.0(2)
C18 O2 C19 117.0(5)
C18 C13 C14 120.8(6)
C18 C13 S2 119.0(4)
C14 C13 S2 120.1(5)
C15 C14 C13 118.7(7)
C14 C15 C16 120.3(7)
C17 C16 C15 121.2(7)
C16 C17 C18 118.7(7)
C13 C18 C17 120.3(6)
C13 C18 O2 122.4(5)
C17 C18 O2 117.3(6)
C24 C19 C20 120.0(6)
C24 C19 O2 122.6(5)
C20 C19 O2 117.3(6)
C21 C20 C19 119.5(7)
C20 C21 C22 121.0(7)
C21 C22 C23 120.8(6)
C22 C23 C24 117.8(7)
C19 C24 C23 120.7(6)
C19 C24 S2 118.5(4)
C23 C24 S2 120.7(5)
C31 C25 C26 118.9(4)
C31 C25 S1 106.7(4)
C26 C25 S1 104.5(4)
C27 C26 C25 116.3(4)
C27 C26 S2 110.7(4)
C25 C26 S2 109.2(4)
C26 C27 C28 116.7(5)
C29 C28 C27 117.0(5)
C28 C29 C30 114.3(5)
C31 C30 C29 113.1(6)
C30 C31 C25 116.8(5)
O12 Cl1 O14 109.8(3)
O12 Cl1 O13 111.4(4)
O14 Cl1 O13 108.2(3)
O12 Cl1 O11 109.3(3)
O14 Cl1 O11 108.0(3)
O13 Cl1 O11 110.2(4)
O24 Cl2 O21 114.2(5)
O24 Cl2 O22 118.7(6)
O21 Cl2 O22 110.7(5)
O24 Cl2 O23 99.8(5)
O21 Cl2 O23 108.4(5)
O22 Cl2 O23 103.5(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C12 1.749(5)
S1 C1 1.755(5)
S1 C25 1.875(6)
O1 C7 1.367(7)
O1 C6 1.378(7)
C1 C2 1.381(8)
C1 C6 1.386(8)
C2 C3 1.373(9)
C3 C4 1.385(10)
C4 C5 1.357(9)
C5 C6 1.401(8)
C7 C12 1.388(8)
C7 C8 1.391(8)
C8 C9 1.380(10)
C9 C10 1.368(10)
C10 C11 1.382(9)
C11 C12 1.386(8)
S2 C24 1.766(6)
S2 C13 1.768(6)
S2 C26 1.882(5)
O2 C18 1.386(7)
O2 C19 1.396(7)
C13 C18 1.376(8)
C13 C14 1.386(8)
C14 C15 1.367(10)
C15 C16 1.386(12)
C16 C17 1.365(10)
C17 C18 1.381(8)
C19 C24 1.372(9)
C19 C20 1.385(9)
C20 C21 1.350(10)
C21 C22 1.369(11)
C22 C23 1.384(10)
C23 C24 1.391(8)
C25 C31 1.529(8)
C25 C26 1.535(7)
C26 C27 1.518(7)
C27 C28 1.534(9)
C28 C29 1.508(9)
C29 C30 1.523(9)
C30 C31 1.518(9)
Cl1 O12 1.413(6)
Cl1 O14 1.427(5)
Cl1 O13 1.428(7)
Cl1 O11 1.433(6)
Cl2 O24 1.347(10)
Cl2 O21 1.386(8)
Cl2 O22 1.405(12)
Cl2 O23 1.447(8)
