#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:05:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178420 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/41/4024105.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_4024105
loop_
_publ_author_name
'Bing-Jun Zhao'
'Henry J. Shine'
'John N. Marx'
'Cristina Hofmann'
'Kenton H. Whitmire'
_publ_section_title
;
 Addition of the Phenoxathiin Cation Radical to Alkenes and Nonconjugated
 Dienes. Formation of (E)- and (Z)-(10-Phenoxathiiniumyl)alkenes
 and (E)- and (Z)-(10-Phenoxathiiniumyl)dienes on Basic Alumina
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6154
_journal_page_last               6161
_journal_paper_doi               10.1021/jo070898b
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C16 H15 F6 O P S'
_chemical_formula_weight         400.31
_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                104.630(3)
_cell_angle_beta                 90.817(3)
_cell_angle_gamma                106.220(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5232(17)
_cell_length_b                   9.801(2)
_cell_length_c                   11.406(2)
_cell_measurement_reflns_used    3852
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      50.716
_cell_measurement_theta_min      4.491
_cell_volume                     881.5(3)
_computing_cell_refinement       'SHELXTL 6.10 (Bruker AXS, 2001)'
_computing_data_collection       'SHELXTL 6.10 (Bruker AXS, 2001)'
_computing_data_reduction        'SHELXTL 6.10 (Bruker AXS, 2001)'
_computing_molecular_graphics    'SHELXTL 6.10 (Bruker AXS, 2001)'
_computing_publication_material  'SHELXTL 6.10 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_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  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11006
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Scheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4222
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.0845
_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)+(0.1139P)²+0.2734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1978
_refine_ls_wR_factor_ref         0.2310
_reflns_number_gt                2288
_reflns_number_total             4222
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070898bsi20070429_054543.cif
_cod_data_source_block           Compound_9a
_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.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (20
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (12
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (28
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (66 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4024105
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42930(12) 0.73504(11) 0.19969(9) 0.0495(3) Uani 1 1 d . . .
O1 O 0.4119(4) 0.4168(3) 0.2134(3) 0.0687(9) Uani 1 1 d . . .
C1 C 0.5223(5) 0.5329(5) 0.2923(4) 0.0521(10) Uani 1 1 d . . .
C2 C 0.6192(6) 0.4964(6) 0.3712(4) 0.0660(12) Uani 1 1 d . . .
H2A H 0.6061 0.3981 0.3681 0.079 Uiso 1 1 calc R . .
C3 C 0.7338(6) 0.6060(7) 0.4534(4) 0.0738(14) Uani 1 1 d . . .
H3A H 0.7979 0.5817 0.5069 0.089 Uiso 1 1 calc R . .
C4 C 0.7556(6) 0.7508(7) 0.4582(4) 0.0764(14) Uani 1 1 d . . .
H4A H 0.8346 0.8239 0.5144 0.092 Uiso 1 1 calc R . .
C5 C 0.6623(5) 0.7890(5) 0.3811(4) 0.0650(12) Uani 1 1 d . . .
H5A H 0.6773 0.8877 0.3845 0.078 Uiso 1 1 calc R . .
C6 C 0.5450(4) 0.6792(4) 0.2978(3) 0.0482(9) Uani 1 1 d . . .
C7 C 0.3349(4) 0.5653(4) 0.0939(3) 0.0471(9) Uani 1 1 d . . .
C8 C 0.2554(5) 0.5686(5) -0.0114(4) 0.0632(11) Uani 1 1 d . . .
H8A H 0.2567 0.6584 -0.0251 0.076 Uiso 1 1 calc R . .
C9 C 0.1749(6) 0.4394(7) -0.0953(4) 0.0782(14) Uani 1 1 d . . .
H9A H 0.1194 0.4409 -0.1656 0.094 Uiso 1 1 calc R . .
C10 C 0.1765(6) 0.3072(6) -0.0750(5) 0.0784(14) Uani 1 1 d . . .
H10A H 0.1228 0.2198 -0.1328 0.094 Uiso 1 1 calc R . .
C11 C 0.2545(6) 0.3015(5) 0.0270(4) 0.0690(12) Uani 1 1 d . . .
H11A H 0.2538 0.2110 0.0391 0.083 Uiso 1 1 calc R . .
C12 C 0.3356(5) 0.4313(5) 0.1135(4) 0.0520(10) Uani 1 1 d . . .
C13 C 0.1848(6) 0.6677(6) 0.3559(4) 0.0778(14) Uani 1 1 d . . .
H13A H 0.0987 0.6993 0.3975 0.117 Uiso 1 1 calc R . .
H13B H 0.2652 0.6647 0.4142 0.117 Uiso 1 1 calc R . .
H13C H 0.1396 0.5712 0.3014 0.117 Uiso 1 1 calc R . .
C14 C 0.2639(5) 0.7734(5) 0.2851(4) 0.0593(11) Uani 1 1 d . . .
C15 C 0.2254(6) 0.8902(5) 0.2749(5) 0.0821(15) Uani 1 1 d . . .
H15A H 0.1400 0.9102 0.3194 0.098 Uiso 1 1 calc R . .
C16 C 0.2978(8) 0.9972(6) 0.2025(7) 0.115(2) Uani 1 1 d . . .
H16A H 0.2419 1.0715 0.2144 0.173 Uiso 1 1 calc R . .
H16B H 0.2856 0.9457 0.1177 0.173 Uiso 1 1 calc R . .
H16C H 0.4121 1.0429 0.2290 0.173 Uiso 1 1 calc R . .
P1 P -0.14742(18) 0.16228(14) 0.24972(13) 0.0778(5) Uani 1 1 d D . .
F11 F -0.2652(14) 0.2335(10) 0.1985(10) 0.157(5) Uani 0.50 1 d PD A 1
F12 F -0.2394(16) 0.1721(14) 0.3603(7) 0.211(8) Uani 0.50 1 d PD A 1
F13 F -0.0391(13) 0.0874(13) 0.2937(12) 0.226(10) Uani 0.50 1 d PD A 1
F14 F -0.0717(13) 0.1472(16) 0.1263(8) 0.280(13) Uani 0.50 1 d PD A 1
F15 F -0.0275(16) 0.3088(9) 0.2982(12) 0.297(14) Uani 0.50 1 d PD A 1
F16 F -0.2739(10) 0.0098(7) 0.1895(8) 0.110(3) Uani 0.50 1 d PD A 1
F21 F 0.0249(13) 0.2040(15) 0.2120(13) 0.265(12) Uani 0.50 1 d PD A 2
F22 F -0.3089(7) 0.1278(12) 0.3090(10) 0.153(5) Uani 0.50 1 d PD A 2
F23 F -0.0928(11) 0.3077(8) 0.3583(8) 0.117(3) Uani 0.50 1 d PD A 2
F26 F -0.2055(18) 0.2429(15) 0.1752(10) 0.310(15) Uani 0.50 1 d PD A 2
F24 F -0.1971(19) 0.0215(11) 0.1567(10) 0.281(12) Uani 0.50 1 d PD A 2
F25 F -0.0816(10) 0.0876(10) 0.3393(10) 0.136(5) Uani 0.50 1 d PD A 2
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
C7 S1 C6 100.52(19) . . y
C7 S1 C14 103.32(18) . . y
C6 S1 C14 104.41(19) . . y
C1 O1 C12 122.2(3) . . y
O1 C1 C6 125.4(4) . . y
O1 C1 C2 115.4(4) . . y
C6 C1 C2 119.2(4) . . y
C3 C2 C1 119.5(4) . . y
C4 C3 C2 120.9(4) . . y
C5 C4 C3 120.5(5) . . y
C4 C5 C6 119.2(4) . . y
C1 C6 C5 120.7(4) . . y
C1 C6 S1 122.1(3) . . y
C5 C6 S1 117.2(3) . . y
C8 C7 C12 120.1(4) . . y
C8 C7 S1 117.3(3) . . y
C12 C7 S1 122.7(3) . . y
C9 C8 C7 119.9(5) . . y
C8 C9 C10 119.5(5) . . y
C11 C10 C9 121.5(5) . . y
C10 C11 C12 119.6(5) . . y
O1 C12 C11 116.3(4) . . y
O1 C12 C7 124.4(4) . . y
C11 C12 C7 119.3(4) . . y
C15 C14 C13 127.9(4) . . y
C15 C14 S1 115.1(4) . . y
C13 C14 S1 116.9(3) . . y
C14 C15 C16 129.9(5) . . y
F24 P1 F26 94.7(5) . . n
F24 P1 F15 148.8(7) . . n
F26 P1 F15 80.7(8) . . n
F24 P1 F13 80.6(8) . . n
F26 P1 F13 158.2(8) . . n
F15 P1 F13 92.3(5) . . n
F24 P1 F12 116.4(7) . . n
F26 P1 F12 107.4(8) . . n
F15 P1 F12 94.2(5) . . n
F13 P1 F12 93.6(5) . . n
F24 P1 F21 93.5(5) . . n
F26 P1 F21 93.0(5) . . n
F15 P1 F21 56.2(7) . . n
F13 P1 F21 66.3(7) . . n
F12 P1 F21 141.2(6) . . n
F24 P1 F22 92.8(5) . . n
F26 P1 F22 93.2(5) . . n
F15 P1 F22 118.2(7) . . n
F13 P1 F22 108.2(7) . . n
F12 P1 F22 29.6(5) . . n
F21 P1 F22 170.7(6) . . n
F24 P1 F14 60.1(7) . . n
F26 P1 F14 68.1(8) . . n
F15 P1 F14 90.0(5) . . n
F13 P1 F14 91.5(5) . . n
F12 P1 F14 173.2(5) . . n
F21 P1 F14 45.3(6) . . n
F22 P1 F14 143.9(5) . . n
F24 P1 F11 96.5(7) . . n
F26 P1 F11 21.6(8) . . n
F15 P1 F11 90.3(5) . . n
F13 P1 F11 177.1(5) . . n
F12 P1 F11 87.5(5) . . n
F21 P1 F11 114.3(7) . . n
F22 P1 F11 71.6(7) . . n
F14 P1 F11 87.2(5) . . n
F24 P1 F16 28.7(7) . . n
F26 P1 F16 95.9(7) . . n
F15 P1 F16 175.9(5) . . n
F13 P1 F16 90.0(4) . . n
F12 P1 F16 89.0(4) . . n
F21 P1 F16 122.0(6) . . n
F22 P1 F16 64.1(5) . . n
F14 P1 F16 86.6(4) . . n
F11 P1 F16 87.3(4) . . n
F24 P1 F25 90.2(5) . . n
F26 P1 F25 175.1(6) . . n
F15 P1 F25 95.4(7) . . n
F13 P1 F25 23.8(7) . . n
F12 P1 F25 69.8(7) . . n
F21 P1 F25 87.2(5) . . n
F22 P1 F25 86.1(4) . . n
F14 P1 F25 115.1(7) . . n
F11 P1 F25 156.9(7) . . n
F16 P1 F25 88.1(5) . . n
F24 P1 F23 175.4(6) . . n
F26 P1 F23 89.7(5) . . n
F15 P1 F23 33.6(6) . . n
F13 P1 F23 95.8(6) . . n
F12 P1 F23 60.7(5) . . n
F21 P1 F23 87.6(5) . . n
F22 P1 F23 85.5(4) . . n
F14 P1 F23 123.2(5) . . n
F11 P1 F23 87.0(5) . . n
F16 P1 F23 149.4(4) . . n
F25 P1 F23 85.4(4) . . n
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
S1 C7 1.756(4) . y
S1 C6 1.762(4) . y
S1 C14 1.796(4) . y
O1 C1 1.361(5) . y
O1 C12 1.362(5) . y
C1 C6 1.377(5) . y
C1 C2 1.388(5) . y
C2 C3 1.367(7) . y
C3 C4 1.365(7) . y
C4 C5 1.363(6) . y
C5 C6 1.384(6) . y
C7 C8 1.382(5) . y
C7 C12 1.387(5) . y
C8 C9 1.369(7) . y
C9 C10 1.376(8) . y
C10 C11 1.354(7) . y
C11 C12 1.387(6) . y
C13 C14 1.492(6) . y
C14 C15 1.307(6) . y
C15 C16 1.501(8) . y
P1 F24 1.459(6) . n
P1 F26 1.462(6) . n
P1 F15 1.475(6) . n
P1 F13 1.481(6) . n
P1 F12 1.491(6) . n
P1 F21 1.510(7) . n
P1 F22 1.532(6) . n
P1 F14 1.548(7) . n
P1 F11 1.555(6) . n
P1 F16 1.558(6) . n
P1 F25 1.577(6) . n
P1 F23 1.582(6) . n
