#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/69/1506956.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_1506956
loop_
_publ_author_name
'Wu, Hai-Chen'
'Yu, Jin-Quan'
'Spencer, Jonathan B.'
_publ_section_title
;
 Stereospecific deoxygenation of phosphine oxides with retention of
 configuration using triphenylphosphine or triethyl phosphite as an oxygen
 acceptor.
;
_journal_issue                   25
_journal_name_full               'Organic letters'
_journal_page_first              4675
_journal_page_last               4678
_journal_paper_doi               10.1021/ol048227c
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety         'C48 H28 F12 P2'
_chemical_formula_sum            'C48 H28 F12 P2'
_chemical_formula_weight         894.64
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 110.0500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.4224(6)
_cell_length_b                   8.0575(2)
_cell_length_c                   18.7865(6)
_cell_measurement_reflns_used    8712
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.00
_cell_volume                     4041.61(19)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12761
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.65
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0608
_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)+(0.0905P)²+9.6517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1610
_refine_ls_wR_factor_ref         0.1713
_reflns_number_gt                2856
_reflns_number_total             3554
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048227csi20040902_075219.cif
_cod_data_source_block           sp0301
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        4041.61(18)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1506956
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
P1 P 0.43134(3) 0.17936(9) 0.22173(4) 0.0304(2) Uani 1 1 d .
C1 C 0.49120(10) -0.0806(3) 0.20735(14) 0.0278(6) Uani 1 1 d .
C2 C 0.45455(10) 0.0314(3) 0.16683(15) 0.0292(6) Uani 1 1 d .
C3 C 0.43976(11) 0.0335(4) 0.08670(15) 0.0327(6) Uani 1 1 d .
H3 H 0.4144 0.1086 0.0587 0.039 Uiso 1 1 calc R
C4 C 0.46113(11) -0.0702(4) 0.04889(16) 0.0344(7) Uani 1 1 d .
H4 H 0.4508 -0.0645 -0.0048 0.041 Uiso 1 1 calc R
C5 C 0.52147(12) -0.2942(4) 0.05112(17) 0.0399(7) Uani 1 1 d .
H5 H 0.5119 -0.2903 -0.0025 0.048 Uiso 1 1 calc R
C6 C 0.55724(12) -0.4043(4) 0.09114(18) 0.0417(8) Uani 1 1 d .
H6 H 0.5725 -0.4756 0.0651 0.050 Uiso 1 1 calc R
C7 C 0.57170(12) -0.4131(4) 0.17049(18) 0.0403(7) Uani 1 1 d .
H7 H 0.5967 -0.4902 0.1978 0.048 Uiso 1 1 calc R
C8 C 0.54995(11) -0.3109(3) 0.20858(16) 0.0332(6) Uani 1 1 d .
H8 H 0.5597 -0.3190 0.2621 0.040 Uiso 1 1 calc R
C9 C 0.51318(10) -0.1935(3) 0.16934(15) 0.0277(6) Uani 1 1 d .
C10 C 0.49846(11) -0.1860(3) 0.08845(16) 0.0315(6) Uani 1 1 d .
C11 C 0.39349(11) 0.3201(3) 0.14718(16) 0.0311(6) Uani 1 1 d .
C12 C 0.34157(12) 0.3254(4) 0.11926(19) 0.0448(8) Uani 1 1 d .
H12 H 0.3229 0.2501 0.1381 0.054 Uiso 1 1 calc R
C13 C 0.31661(12) 0.4403(4) 0.0639(2) 0.0493(9) Uani 1 1 d .
H13 H 0.2810 0.4423 0.0448 0.059 Uiso 1 1 calc R
C14 C 0.34326(11) 0.5508(4) 0.03677(16) 0.0372(7) Uani 1 1 d .
C15 C 0.39517(12) 0.5489(4) 0.06557(17) 0.0388(7) Uani 1 1 d .
H15 H 0.4137 0.6261 0.0474 0.047 Uiso 1 1 calc R
C16 C 0.41999(11) 0.4352(4) 0.12050(17) 0.0369(7) Uani 1 1 d .
H16 H 0.4556 0.4355 0.1404 0.044 Uiso 1 1 calc R
C17 C 0.31798(14) 0.6741(4) -0.02321(19) 0.0470(8) Uani 1 1 d .
F171 F 0.26987(9) 0.6402(3) -0.05943(13) 0.0733(7) Uani 1 1 d .
F172 F 0.33898(10) 0.6841(3) -0.07650(12) 0.0723(7) Uani 1 1 d .
F173 F 0.31980(10) 0.8289(3) 0.00382(13) 0.0725(7) Uani 1 1 d .
C18 C 0.38466(10) 0.0527(3) 0.24406(16) 0.0316(6) Uani 1 1 d .
C19 C 0.38224(12) 0.0688(4) 0.31634(17) 0.0406(7) Uani 1 1 d .
H19 H 0.4029 0.1481 0.3502 0.049 Uiso 1 1 calc R
C20 C 0.35029(14) -0.0286(4) 0.3398(2) 0.0506(9) Uani 1 1 d .
H20 H 0.3492 -0.0169 0.3896 0.061 Uiso 1 1 calc R
C21 C 0.31987(12) -0.1435(4) 0.2904(2) 0.0463(8) Uani 1 1 d .
C22 C 0.32131(12) -0.1607(4) 0.2183(2) 0.0468(8) Uani 1 1 d .
H22 H 0.3002 -0.2390 0.1844 0.056 Uiso 1 1 calc R
C23 C 0.35369(11) -0.0635(4) 0.19511(17) 0.0411(7) Uani 1 1 d .
H23 H 0.3548 -0.0763 0.1454 0.049 Uiso 1 1 calc R
C24 C 0.28568(18) -0.2521(6) 0.3148(3) 0.0754(13) Uani 1 1 d .
F241 F 0.2955(2) -0.4081(5) 0.3130(4) 0.202(3) Uani 1 1 d .
F242 F 0.2853(2) -0.2265(8) 0.3801(2) 0.199(3) Uani 1 1 d .
F243 F 0.24008(14) -0.2503(7) 0.2713(3) 0.166(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'
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'
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_3
C18 P1 C11 103.74(13) .
C18 P1 C2 101.19(13) .
C11 P1 C2 101.62(12) .
C2 C1 C9 120.9(2) .
C2 C1 C1 119.7(2) 2_655
C9 C1 C1 119.3(2) 2_655
C1 C2 C3 118.9(2) .
C1 C2 P1 117.3(2) .
C3 C2 P1 123.7(2) .
C4 C3 C2 121.5(3) .
C4 C3 H3 119.3 .
C2 C3 H3 119.3 .
C3 C4 C10 121.1(3) .
C3 C4 H4 119.5 .
C10 C4 H4 119.5 .
C6 C5 C10 120.8(3) .
C6 C5 H5 119.6 .
C10 C5 H5 119.6 .
C5 C6 C7 120.6(3) .
C5 C6 H6 119.7 .
C7 C6 H6 119.7 .
C8 C7 C6 120.2(3) .
C8 C7 H7 119.9 .
C6 C7 H7 119.9 .
C7 C8 C9 121.0(3) .
C7 C8 H8 119.5 .
C9 C8 H8 119.5 .
C8 C9 C1 122.5(2) .
C8 C9 C10 118.4(2) .
C1 C9 C10 119.1(2) .
C5 C10 C4 122.5(3) .
C5 C10 C9 119.0(3) .
C4 C10 C9 118.5(2) .
C12 C11 C16 118.7(3) .
C12 C11 P1 125.2(2) .
C16 C11 P1 116.0(2) .
C11 C12 C13 120.5(3) .
C11 C12 H12 119.8 .
C13 C12 H12 119.8 .
C14 C13 C12 120.2(3) .
C14 C13 H13 119.9 .
C12 C13 H13 119.9 .
C13 C14 C15 119.7(3) .
C13 C14 C17 121.9(3) .
C15 C14 C17 118.4(3) .
C16 C15 C14 120.1(3) .
C16 C15 H15 119.9 .
C14 C15 H15 119.9 .
C15 C16 C11 120.7(3) .
C15 C16 H16 119.6 .
C11 C16 H16 119.6 .
F171 C17 F172 106.0(3) .
F171 C17 F173 106.5(3) .
F172 C17 F173 105.0(3) .
F171 C17 C14 113.2(3) .
F172 C17 C14 112.6(3) .
F173 C17 C14 112.8(3) .
C19 C18 C23 118.4(3) .
C19 C18 P1 117.0(2) .
C23 C18 P1 124.5(2) .
C20 C19 C18 121.2(3) .
C20 C19 H19 119.4 .
C18 C19 H19 119.4 .
C19 C20 C21 119.5(3) .
C19 C20 H20 120.2 .
C21 C20 H20 120.2 .
C22 C21 C20 120.4(3) .
C22 C21 C24 119.1(4) .
C20 C21 C24 120.5(4) .
C21 C22 C23 119.9(3) .
C21 C22 H22 120.0 .
C23 C22 H22 120.0 .
C22 C23 C18 120.6(3) .
C22 C23 H23 119.7 .
C18 C23 H23 119.7 .
F242 C24 F243 106.2(5) .
F242 C24 F241 105.2(5) .
F243 C24 F241 100.2(6) .
F242 C24 C21 115.6(5) .
F243 C24 C21 115.0(4) .
F241 C24 C21 113.1(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C18 1.833(3) .
P1 C11 1.836(3) .
P1 C2 1.840(3) .
C1 C2 1.391(4) .
C1 C9 1.426(4) .
C1 C1 1.506(5) 2_655
C2 C3 1.418(4) .
C3 C4 1.366(4) .
C3 H3 0.9500 .
C4 C10 1.417(4) .
C4 H4 0.9500 .
C5 C6 1.364(5) .
C5 C10 1.412(4) .
C5 H5 0.9500 .
C6 C7 1.406(4) .
C6 H6 0.9500 .
C7 C8 1.369(4) .
C7 H7 0.9500 .
C8 C9 1.415(4) .
C8 H8 0.9500 .
C9 C10 1.433(4) .
C11 C12 1.387(4) .
C11 C16 1.392(4) .
C12 C13 1.391(5) .
C12 H12 0.9500 .
C13 C14 1.376(4) .
C13 H13 0.9500 .
C14 C15 1.386(4) .
C14 C17 1.489(4) .
C15 C16 1.380(4) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 F171 1.330(4) .
C17 F172 1.332(4) .
C17 F173 1.341(4) .
C18 C19 1.389(4) .
C18 C23 1.394(4) .
C19 C20 1.382(5) .
C19 H19 0.9500 .
C20 C21 1.385(5) .
C20 H20 0.9500 .
C21 C22 1.376(5) .
C21 C24 1.493(5) .
C22 C23 1.387(4) .
C22 H22 0.9500 .
C23 H23 0.9500 .
C24 F242 1.248(6) .
C24 F243 1.273(6) .
C24 F241 1.290(6) .
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_site_symmetry_1
C9 C1 C2 C3 -0.9(4) .
C1 C1 C2 C3 177.8(2) 2_655
C9 C1 C2 P1 -176.57(19) .
C1 C1 C2 P1 2.1(3) 2_655
C18 P1 C2 C1 -82.7(2) .
C11 P1 C2 C1 170.5(2) .
C18 P1 C2 C3 101.9(2) .
C11 P1 C2 C3 -4.9(3) .
C1 C2 C3 C4 -0.9(4) .
P1 C2 C3 C4 174.5(2) .
C2 C3 C4 C10 1.0(4) .
C10 C5 C6 C7 0.5(5) .
C5 C6 C7 C8 0.0(5) .
C6 C7 C8 C9 -0.9(4) .
C7 C8 C9 C1 -177.4(3) .
C7 C8 C9 C10 1.2(4) .
C2 C1 C9 C8 -179.0(3) .
C1 C1 C9 C8 2.4(4) 2_655
C2 C1 C9 C10 2.5(4) .
C1 C1 C9 C10 -176.2(2) 2_655
C6 C5 C10 C4 -179.9(3) .
C6 C5 C10 C9 -0.1(4) .
C3 C4 C10 C5 -179.7(3) .
C3 C4 C10 C9 0.5(4) .
C8 C9 C10 C5 -0.7(4) .
C1 C9 C10 C5 178.0(3) .
C8 C9 C10 C4 179.1(2) .
C1 C9 C10 C4 -2.2(4) .
C18 P1 C11 C12 2.1(3) .
C2 P1 C11 C12 106.8(3) .
C18 P1 C11 C16 178.4(2) .
C2 P1 C11 C16 -76.9(2) .
C16 C11 C12 C13 2.1(5) .
P1 C11 C12 C13 178.3(3) .
C11 C12 C13 C14 -0.6(5) .
C12 C13 C14 C15 -0.9(5) .
C12 C13 C14 C17 179.1(3) .
C13 C14 C15 C16 0.8(5) .
C17 C14 C15 C16 -179.2(3) .
C14 C15 C16 C11 0.7(4) .
C12 C11 C16 C15 -2.1(4) .
P1 C11 C16 C15 -178.7(2) .
C13 C14 C17 F171 -15.4(5) .
C15 C14 C17 F171 164.6(3) .
C13 C14 C17 F172 -135.6(3) .
C15 C14 C17 F172 44.4(4) .
C13 C14 C17 F173 105.7(4) .
C15 C14 C17 F173 -74.3(4) .
C11 P1 C18 C19 -115.2(2) .
C2 P1 C18 C19 139.8(2) .
C11 P1 C18 C23 68.4(3) .
C2 P1 C18 C23 -36.7(3) .
C23 C18 C19 C20 0.5(5) .
P1 C18 C19 C20 -176.2(3) .
C18 C19 C20 C21 -0.5(5) .
C19 C20 C21 C22 -0.1(5) .
C19 C20 C21 C24 179.0(3) .
C20 C21 C22 C23 0.5(5) .
C24 C21 C22 C23 -178.5(3) .
C21 C22 C23 C18 -0.5(5) .
C19 C18 C23 C22 -0.1(5) .
P1 C18 C23 C22 176.4(2) .
C22 C21 C24 F242 -178.0(5) .
C20 C21 C24 F242 2.9(7) .
C22 C21 C24 F243 -53.7(6) .
C20 C21 C24 F243 127.3(5) .
C22 C21 C24 F241 60.6(6) .
C20 C21 C24 F241 -118.5(6) .
