#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:05:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178420 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/41/4024104.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_4024104
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            'C32 H31 F12 N O2 P2 S2'
_chemical_formula_weight         815.64
_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                 113.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.415(3)
_cell_length_b                   12.538(2)
_cell_length_c                   17.415(3)
_cell_measurement_reflns_used    20001
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      56.055
_cell_measurement_theta_min      4.291
_cell_volume                     3500.2(11)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42811
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Scheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.606
_refine_diff_density_min         -1.070
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         8561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0582
_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)+(0.0829P)²+2.6481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.1795
_reflns_number_gt                5861
_reflns_number_total             8561
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070898bsi20070429_054455.cif
_cod_data_source_block           Compound_6c
_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.

'_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 (39
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 (14
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 (54
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 (34 times).

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               4024104
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.21342(4) 0.80724(6) 0.10937(4) 0.03919(17) Uani 1 1 d . . .
S1 S 0.28952(4) 0.96413(6) -0.03477(4) 0.04270(18) Uani 1 1 d . . .
C14 C 0.16318(15) 0.8579(2) -0.00022(15) 0.0370(5) Uani 1 1 d . . .
H14A H 0.1157 0.8110 -0.0297 0.044 Uiso 1 1 calc R . .
O2 O 0.06550(12) 0.65735(17) 0.06359(13) 0.0509(5) Uani 1 1 d . . .
C26 C 0.13194(17) 0.8137(2) 0.14455(16) 0.0409(6) Uani 1 1 d . . .
C1 C 0.34204(17) 0.9890(2) 0.07300(17) 0.0436(6) Uani 1 1 d . . .
C6 C 0.40254(18) 0.9186(2) 0.12094(19) 0.0484(7) Uani 1 1 d . . .
O1 O 0.42766(14) 0.83298(18) 0.08676(15) 0.0596(6) Uani 1 1 d . . .
C15 C 0.21329(18) 0.6695(2) 0.09120(17) 0.0429(6) Uani 1 1 d . . .
C21 C 0.06684(17) 0.7420(2) 0.11413(17) 0.0436(6) Uani 1 1 d . . .
C25 C 0.1327(2) 0.8939(3) 0.20002(19) 0.0527(7) Uani 1 1 d . . .
H25A H 0.1778 0.9404 0.2216 0.063 Uiso 1 1 calc R . .
C28 C 0.18770(17) 0.8085(3) -0.13331(17) 0.0470(7) Uani 1 1 d . . .
H28A H 0.2323 0.8106 -0.1543 0.056 Uiso 1 1 calc R . .
C16 C 0.28634(19) 0.6194(3) 0.09489(19) 0.0502(7) Uani 1 1 d . . .
H16A H 0.3366 0.6564 0.1131 0.060 Uiso 1 1 calc R . .
C20 C 0.13901(18) 0.6134(2) 0.06695(18) 0.0457(6) Uani 1 1 d . . .
C23 C -0.0005(2) 0.8342(3) 0.1899(2) 0.0611(9) Uani 1 1 d . . .
H23A H -0.0460 0.8423 0.2047 0.073 Uiso 1 1 calc R . .
C12 C 0.37405(19) 0.9075(3) -0.0527(2) 0.0514(7) Uani 1 1 d . . .
C27 C 0.12816(18) 0.9688(2) 0.00012(19) 0.0469(6) Uani 1 1 d . . .
H27A H 0.1025 0.9947 -0.0561 0.070 Uiso 1 1 calc R . .
H27B H 0.1725 1.0160 0.0322 0.070 Uiso 1 1 calc R . .
H27C H 0.0874 0.9658 0.0245 0.070 Uiso 1 1 calc R . .
C22 C -0.00111(19) 0.7534(3) 0.1361(2) 0.0544(8) Uani 1 1 d . . .
H22A H -0.0464 0.7073 0.1148 0.065 Uiso 1 1 calc R . .
C19 C 0.1369(2) 0.5080(3) 0.0441(2) 0.0588(8) Uani 1 1 d . . .
H19A H 0.0874 0.4695 0.0279 0.071 Uiso 1 1 calc R . .
C7 C 0.43113(19) 0.8467(3) 0.0097(2) 0.0558(8) Uani 1 1 d . . .
C30 C 0.1578(2) 0.6932(3) -0.1399(2) 0.0663(9) Uani 1 1 d . . .
H30A H 0.1339 0.6723 -0.1975 0.100 Uiso 1 1 calc R . .
H30B H 0.1166 0.6871 -0.1163 0.100 Uiso 1 1 calc R . .
H30C H 0.2042 0.6476 -0.1101 0.100 Uiso 1 1 calc R . .
C17 C 0.2825(2) 0.5146(3) 0.0711(2) 0.0624(9) Uani 1 1 d . . .
H17A H 0.3303 0.4803 0.0724 0.075 Uiso 1 1 calc R . .
C24 C 0.0657(2) 0.9032(3) 0.2223(2) 0.0628(9) Uani 1 1 d . . .
H24A H 0.0651 0.9562 0.2594 0.075 Uiso 1 1 calc R . .
C2 C 0.3210(2) 1.0766(3) 0.1092(2) 0.0546(7) Uani 1 1 d . . .
H2A H 0.2822 1.1260 0.0764 0.065 Uiso 1 1 calc R . .
C29 C 0.1189(2) 0.8821(3) -0.1882(2) 0.0671(10) Uani 1 1 d . . .
H29A H 0.0973 0.8560 -0.2445 0.101 Uiso 1 1 calc R . .
H29B H 0.1410 0.9526 -0.1868 0.101 Uiso 1 1 calc R . .
H29C H 0.0749 0.8844 -0.1680 0.101 Uiso 1 1 calc R . .
C3 C 0.3584(2) 1.0893(3) 0.1941(2) 0.0705(10) Uani 1 1 d . . .
H3A H 0.3449 1.1477 0.2193 0.085 Uiso 1 1 calc R . .
C9 C 0.5002(3) 0.8080(4) -0.0798(4) 0.0902(15) Uani 1 1 d . . .
H9A H 0.5427 0.7734 -0.0897 0.108 Uiso 1 1 calc R . .
C11 C 0.3797(2) 0.9209(3) -0.1296(2) 0.0659(9) Uani 1 1 d . . .
H11A H 0.3415 0.9627 -0.1712 0.079 Uiso 1 1 calc R . .
C18 C 0.2081(3) 0.4600(3) 0.0453(2) 0.0661(9) Uani 1 1 d . . .
H18A H 0.2061 0.3894 0.0284 0.079 Uiso 1 1 calc R . .
C5 C 0.4388(2) 0.9310(3) 0.2062(2) 0.0617(9) Uani 1 1 d . . .
H5A H 0.4784 0.8824 0.2391 0.074 Uiso 1 1 calc R . .
C10 C 0.4446(3) 0.8695(4) -0.1418(3) 0.0839(14) Uani 1 1 d . . .
H10A H 0.4504 0.8767 -0.1924 0.101 Uiso 1 1 calc R . .
C8 C 0.4953(2) 0.7960(3) -0.0041(3) 0.0767(12) Uani 1 1 d . . .
H8A H 0.5341 0.7547 0.0374 0.092 Uiso 1 1 calc R . .
C4 C 0.4159(2) 1.0157(4) 0.2419(2) 0.0710(10) Uani 1 1 d . . .
H4A H 0.4394 1.0238 0.2996 0.085 Uiso 1 1 calc R . .
P1 P 0.11033(5) 0.22255(7) 0.14896(5) 0.0504(2) Uiso 1 1 d . . .
F6 F 0.04154(16) 0.3124(2) 0.11695(15) 0.0925(8) Uani 1 1 d . . .
F5 F 0.04297(16) 0.1357(2) 0.10056(19) 0.1013(9) Uani 1 1 d . . .
F4 F 0.08825(17) 0.2071(2) 0.22851(15) 0.0880(7) Uani 1 1 d . . .
F3 F 0.13178(18) 0.2371(2) 0.06947(16) 0.0916(8) Uani 1 1 d . . .
F2 F 0.17657(17) 0.3094(2) 0.19760(17) 0.0960(8) Uani 1 1 d . . .
F1 F 0.17807(17) 0.1312(2) 0.1815(2) 0.1032(9) Uani 1 1 d . . .
P2 P 0.25108(6) 1.25927(8) -0.13493(6) 0.0626(3) Uiso 1 1 d . . .
C13 C 0.22662(16) 0.8419(2) -0.04068(16) 0.0374(5) Uani 1 1 d . . .
H13A H 0.2651 0.7853 -0.0098 0.045 Uiso 1 1 calc R . .
F26 F 0.2093(2) 1.2007(3) -0.0814(2) 0.1302(13) Uani 1 1 d . . .
F25 F 0.31538(18) 1.1660(2) -0.1202(3) 0.1252(12) Uani 1 1 d . . .
F24 F 0.1861(2) 1.3513(3) -0.1466(2) 0.1184(10) Uani 1 1 d . . .
F23 F 0.3122(2) 1.3193(3) -0.0555(2) 0.1314(12) Uani 1 1 d . . .
F22 F 0.2892(3) 1.3197(3) -0.1884(3) 0.1568(16) Uani 1 1 d . . .
F21 F 0.1891(2) 1.2029(4) -0.2129(3) 0.1678(18) Uani 1 1 d . . .
C101 C 0.0526(3) 1.0223(5) -0.3905(3) 0.0926(15) Uani 1 1 d . . .
C102 C 0.1308(3) 1.0618(4) -0.3882(3) 0.0976(15) Uani 1 1 d . . .
H201 H 0.1223 1.0960 -0.4402 0.146 Uiso 1 1 calc R . .
H202 H 0.1690 1.0034 -0.3794 0.146 Uiso 1 1 calc R . .
H203 H 0.1534 1.1122 -0.3435 0.146 Uiso 1 1 calc R . .
N101 N -0.0081(3) 0.9914(6) -0.3917(3) 0.139(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'
P P 0.1023 0.0942 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 S2 C15 99.47(14) . . y
C26 S2 C14 102.76(12) . . y
C15 S2 C14 100.51(12) . . y
C1 S1 C12 97.89(14) . . y
C1 S1 C13 104.68(12) . . y
C12 S1 C13 99.88(13) . . y
C27 C14 C13 118.8(2) . . y
C27 C14 S2 109.55(18) . . y
C13 C14 S2 106.84(17) . . y
C21 O2 C20 120.0(2) . . y
C21 C26 C25 121.4(3) . . y
C21 C26 S2 119.4(2) . . y
C25 C26 S2 119.1(2) . . y
C6 C1 C2 120.5(3) . . y
C6 C1 S1 119.1(2) . . y
C2 C1 S1 120.3(2) . . y
C5 C6 C1 120.1(3) . . y
C5 C6 O1 117.6(3) . . y
C1 C6 O1 122.3(3) . . y
C7 O1 C6 117.7(3) . . y
C20 C15 C16 120.7(3) . . y
C20 C15 S2 119.3(2) . . y
C16 C15 S2 119.8(2) . . y
O2 C21 C26 123.7(3) . . y
O2 C21 C22 117.0(3) . . y
C26 C21 C22 119.2(3) . . y
C24 C25 C26 118.6(3) . . y
C29 C28 C30 111.5(3) . . y
C29 C28 C13 114.2(3) . . y
C30 C28 C13 109.5(3) . . y
C17 C16 C15 118.7(3) . . y
O2 C20 C19 117.0(3) . . y
O2 C20 C15 123.5(3) . . y
C19 C20 C15 119.5(3) . . y
C24 C23 C22 121.6(3) . . y
C7 C12 C11 121.6(3) . . y
C7 C12 S1 118.4(2) . . y
C11 C12 S1 119.9(3) . . y
C23 C22 C21 118.9(3) . . y
C18 C19 C20 119.6(3) . . y
O1 C7 C12 122.9(3) . . y
O1 C7 C8 117.1(4) . . y
C12 C7 C8 119.9(4) . . y
C16 C17 C18 120.3(3) . . y
C25 C24 C23 120.1(3) . . y
C3 C2 C1 118.9(3) . . y
C2 C3 C4 120.1(4) . . y
C8 C9 C10 122.1(4) . . y
C10 C11 C12 117.3(4) . . y
C19 C18 C17 121.2(3) . . y
C4 C5 C6 119.0(3) . . y
C9 C10 C11 120.5(4) . . y
C9 C8 C7 118.5(5) . . y
C5 C4 C3 121.2(3) . . y
F2 P1 F3 91.00(15) . . n
F2 P1 F6 89.53(16) . . n
F3 P1 F6 90.86(15) . . n
F2 P1 F5 179.30(16) . . n
F3 P1 F5 89.57(15) . . n
F6 P1 F5 90.05(16) . . n
F2 P1 F1 91.19(16) . . n
F3 P1 F1 89.90(16) . . n
F6 P1 F1 178.94(16) . . n
F5 P1 F1 89.22(17) . . n
F2 P1 F4 89.50(15) . . n
F3 P1 F4 179.50(16) . . n
F6 P1 F4 89.19(14) . . n
F5 P1 F4 89.93(15) . . n
F1 P1 F4 90.04(15) . . n
F22 P2 F21 90.7(3) . . n
F22 P2 F26 177.8(2) . . n
F21 P2 F26 88.9(3) . . n
F22 P2 F23 89.6(2) . . n
F21 P2 F23 178.3(2) . . n
F26 P2 F23 90.8(2) . . n
F22 P2 F25 91.0(2) . . n
F21 P2 F25 90.7(2) . . n
F26 P2 F25 91.18(18) . . n
F23 P2 F25 91.05(19) . . n
F22 P2 F24 91.1(2) . . n
F21 P2 F24 90.1(2) . . n
F26 P2 F24 86.74(18) . . n
F23 P2 F24 88.18(19) . . n
F25 P2 F24 177.8(2) . . n
C14 C13 C28 114.4(2) . . n
C14 C13 S1 112.30(18) . . n
C28 C13 S1 106.83(18) . . n
N101 C101 C102 179.6(6) . . 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
S2 C26 1.753(3) . y
S2 C15 1.755(3) . y
S2 C14 1.872(3) . y
S1 C1 1.765(3) . y
S1 C12 1.769(3) . y
S1 C13 1.863(3) . y
C14 C27 1.520(4) . y
C14 C13 1.538(3) . y
O2 C21 1.373(4) . y
O2 C20 1.374(3) . y
C26 C21 1.381(4) . y
C26 C25 1.391(4) . y
C1 C6 1.378(4) . y
C1 C2 1.384(4) . y
C6 C5 1.377(4) . y
C6 O1 1.379(4) . y
O1 C7 1.378(4) . y
C15 C20 1.386(4) . y
C15 C16 1.398(4) . y
C21 C22 1.386(4) . y
C25 C24 1.370(5) . y
C28 C29 1.519(5) . y
C28 C30 1.526(5) . y
C28 C13 1.543(4) . y
C16 C17 1.371(5) . y
C20 C19 1.377(4) . y
C23 C24 1.373(5) . y
C23 C22 1.378(5) . y
C12 C7 1.380(5) . y
C12 C11 1.391(5) . y
C19 C18 1.370(5) . y
C7 C8 1.386(5) . y
C17 C18 1.376(5) . y
C2 C3 1.372(5) . y
C3 C4 1.377(6) . y
C9 C8 1.363(7) . y
C9 C10 1.372(7) . y
C11 C10 1.388(6) . y
C5 C4 1.367(6) . y
P1 F2 1.571(2) . n
P1 F3 1.579(2) . n
P1 F6 1.579(2) . n
P1 F5 1.581(2) . n
P1 F1 1.581(2) . n
P1 F4 1.588(2) . n
P2 F22 1.537(3) . n
P2 F21 1.538(3) . n
P2 F26 1.571(3) . n
P2 F23 1.569(3) . n
P2 F25 1.569(3) . n
P2 F24 1.573(3) . n
C101 N101 1.118(7) . n
C101 C102 1.435(7) . n
