#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/23/4022390.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_4022390
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            'C18 H18 Cl N O4 S2'
_chemical_formula_weight         411.90
_chemical_name_systematic
;
  ?
;
_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                69.264(2)
_cell_angle_beta                 85.923(2)
_cell_angle_gamma                80.198(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6869(11)
_cell_length_b                   11.4845(16)
_cell_length_c                   12.1644(17)
_cell_measurement_reflns_used    2598
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      46.565
_cell_measurement_theta_min      5.378
_cell_volume                     989.6(2)
_computing_cell_refinement       'SHELXTL 6.10 (Burker, 2001)'
_computing_data_collection       'SHELXTL 6.10 (Burker, 2001)'
_computing_data_reduction        'SHELXTL 6.10 (Burker, 2001)'
_computing_molecular_graphics    'SHELXTL 6.10 (Burker, 2001)'
_computing_publication_material  'SHELXTL 6.10 (Burker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Burker SMART 1k; CCD'
_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  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4527
_diffrn_reflns_theta_full        23.32
_diffrn_reflns_theta_max         23.32
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.919743
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            clorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1045P)²+0.7048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.1907
_reflns_number_gt                2285
_reflns_number_total             2844
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo030173h_12.cif
_cod_data_source_block
"'(z)-2-(5-thianthreniumyl)-2-butene(ClO4)_zth15a'"
_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.

'_exptl_absorpt_correction_type' value 'Multiscan' changed to
'multi-scan' 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_database_code               4022390
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
S1 S 0.86822(13) -0.27300(9) 0.69751(9) 0.0536(4) Uani 1 1 d .
S2 S 0.8206(2) -0.57058(11) 0.88222(12) 0.0835(5) Uani 1 1 d .
C1 C 0.9909(5) -0.4138(4) 0.6882(3) 0.0523(10) Uani 1 1 d .
C2 C 1.1138(6) -0.3972(5) 0.5969(4) 0.0677(12) Uani 1 1 d .
H2A H 1.1317 -0.3164 0.5498 0.081 Uiso 1 1 calc R
C3 C 1.2089(6) -0.4997(6) 0.5760(5) 0.0827(16) Uani 1 1 d .
H3A H 1.2908 -0.4887 0.5144 0.099 Uiso 1 1 calc R
C4 C 1.1824(7) -0.6189(6) 0.6466(5) 0.0820(15) Uani 1 1 d .
H4A H 1.2468 -0.6886 0.6325 0.098 Uiso 1 1 calc R
C5 C 1.0623(7) -0.6364(5) 0.7375(5) 0.0771(13) Uani 1 1 d .
H5A H 1.0456 -0.7177 0.7839 0.092 Uiso 1 1 calc R
C6 C 0.9649(5) -0.5341(4) 0.7615(4) 0.0574(10) Uani 1 1 d .
C7 C 0.7674(6) -0.4328(4) 0.9163(4) 0.0592(10) Uani 1 1 d .
C8 C 0.6924(7) -0.4477(5) 1.0282(4) 0.0754(13) Uani 1 1 d .
H8A H 0.6787 -0.5278 1.0796 0.090 Uiso 1 1 calc R
C9 C 0.6395(7) -0.3460(6) 1.0623(5) 0.0836(15) Uani 1 1 d .
H9A H 0.5883 -0.3574 1.1362 0.100 Uiso 1 1 calc R
C10 C 0.6609(7) -0.2270(6) 0.9888(5) 0.0811(15) Uani 1 1 d .
H10A H 0.6241 -0.1582 1.0128 0.097 Uiso 1 1 calc R
C11 C 0.7365(6) -0.2098(4) 0.8799(4) 0.0684(12) Uani 1 1 d .
H11A H 0.7546 -0.1297 0.8308 0.082 Uiso 1 1 calc R
C12 C 0.7858(5) -0.3112(4) 0.8432(3) 0.0536(10) Uani 1 1 d .
C13 C 0.5587(6) -0.3428(6) 0.6451(5) 0.0892(16) Uani 1 1 d .
H17A H 0.4653 -0.3174 0.5891 0.134 Uiso 1 1 calc R
H17B H 0.5095 -0.3489 0.7213 0.134 Uiso 1 1 calc R
H17C H 0.6224 -0.4234 0.6480 0.134 Uiso 1 1 calc R
C14 C 0.6804(5) -0.2484(5) 0.6093(4) 0.0641(12) Uani 1 1 d .
C15 C 0.6684(8) -0.1446(6) 0.5137(5) 0.0864(16) Uani 1 1 d .
H15A H 0.5704 -0.1301 0.4673 0.104 Uiso 1 1 calc R
C16 C 0.7886(11) -0.0486(6) 0.4704(6) 0.118(2) Uani 1 1 d .
H18A H 0.7417 0.0165 0.4000 0.177 Uiso 1 1 calc R
H18B H 0.9031 -0.0878 0.4538 0.177 Uiso 1 1 calc R
H18C H 0.7987 -0.0126 0.5294 0.177 Uiso 1 1 calc R
N100 N 0.7778(7) 0.2254(5) 0.1945(5) 0.1059(15) Uani 1 1 d .
C100 C 0.7860(7) 0.1488(5) 0.1579(5) 0.0790(14) Uiso 1 1 d .
C101 C 0.7993(9) 0.0510(6) 0.1101(6) 0.115(2) Uiso 1 1 d .
H10A H 0.6833 0.0348 0.1021 0.173 Uiso 1 1 calc R
H10B H 0.8674 -0.0241 0.1616 0.173 Uiso 1 1 calc R
H10C H 0.8563 0.0765 0.0344 0.173 Uiso 1 1 calc R
Cl1 Cl 1.31770(14) -0.16538(10) 0.27274(10) 0.0644(4) Uiso 1 1 d .
O1 O 1.2196(14) -0.1182(8) 0.3431(8) 0.263(5) Uani 1 1 d .
O2 O 1.2265(13) -0.1355(8) 0.1756(6) 0.231(4) Uani 1 1 d .
O3 O 1.4654(8) -0.1106(6) 0.2398(8) 0.200(3) Uani 1 1 d .
O4 O 1.3627(7) -0.2961(4) 0.3222(6) 0.164(2) 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'
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'
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
C1 S1 C12 105.98(19)
C1 S1 C14 103.02(19)
C12 S1 C14 105.2(2)
C6 S2 C7 105.4(2)
C2 C1 C6 120.9(4)
C2 C1 S1 114.8(3)
C6 C1 S1 124.3(3)
C3 C2 C1 120.1(5)
C2 C3 C4 119.5(5)
C5 C4 C3 120.8(5)
C4 C5 C6 120.9(5)
C5 C6 C1 117.6(4)
C5 C6 S2 116.0(4)
C1 C6 S2 126.4(3)
C12 C7 C8 117.2(4)
C12 C7 S2 127.0(3)
C8 C7 S2 115.8(3)
C9 C8 C7 120.7(5)
C8 C9 C10 120.8(5)
C11 C10 C9 119.8(5)
C10 C11 C12 119.9(5)
C11 C12 C7 121.4(4)
C11 C12 S1 114.7(3)
C7 C12 S1 123.8(3)
C15 C14 C13 126.7(5)
C15 C14 S1 114.3(4)
C13 C14 S1 119.0(4)
C14 C15 C16 129.5(5)
N100 C100 C101 179.1(7)
O1 Cl1 O2 107.2(7)
O1 Cl1 O3 110.9(6)
O2 Cl1 O3 106.2(5)
O1 Cl1 O4 112.2(5)
O2 Cl1 O4 109.8(5)
O3 Cl1 O4 110.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.764(4)
S1 C12 1.766(4)
S1 C14 1.784(4)
S2 C6 1.747(4)
S2 C7 1.749(4)
C1 C2 1.387(6)
C1 C6 1.393(6)
C2 C3 1.370(7)
C3 C4 1.376(8)
C4 C5 1.369(7)
C5 C6 1.393(6)
C7 C12 1.390(6)
C7 C8 1.405(6)
C8 C9 1.363(7)
C9 C10 1.373(8)
C10 C11 1.369(7)
C11 C12 1.376(6)
C13 C14 1.481(7)
C14 C15 1.333(7)
C15 C16 1.488(9)
N100 C100 1.110(7)
C100 C101 1.422(8)
Cl1 O1 1.301(6)
Cl1 O2 1.325(6)
Cl1 O3 1.359(5)
Cl1 O4 1.396(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658559
