#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/69/1506954.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_1506954
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 O2 P2'
_chemical_formula_sum            'C48 H28 F12 O2 P2'
_chemical_formula_weight         926.64
_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                 109.824(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.7227(13)
_cell_length_b                   8.4943(4)
_cell_length_c                   17.9976(10)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.00
_cell_volume                     4130.8(4)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0873
_diffrn_reflns_av_sigmaI/netI    0.1100
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9788
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       0.0031(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0656
_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)+(0.1015P)²+5.6391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.2044
_reflns_number_gt                2305
_reflns_number_total             3577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048227csi20040902_075149.cif
_cod_data_source_block           sp0207
_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_sg_symbol_H-M      C2/c
_cod_database_code               1506954
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 0.42514(4) 0.33075(12) 0.22301(6) 0.0362(4) Uani 1 1 d .
O1 O 0.45926(9) 0.2569(3) 0.29547(15) 0.0444(7) Uani 1 1 d .
C1 C 0.48902(14) 0.5657(4) 0.2057(2) 0.0372(9) Uani 1 1 d .
C2 C 0.45135(14) 0.4610(4) 0.1671(2) 0.0372(9) Uani 1 1 d .
C3 C 0.43287(15) 0.4578(5) 0.0834(2) 0.0432(10) Uani 1 1 d .
H3 H 0.4068 0.3878 0.0566 0.052 Uiso 1 1 calc R
C4 C 0.45244(16) 0.5550(5) 0.0410(2) 0.0488(11) Uani 1 1 d .
H4 H 0.4404 0.5483 -0.0150 0.059 Uiso 1 1 calc R
C5 C 0.51008(19) 0.7678(5) 0.0350(3) 0.0578(13) Uani 1 1 d .
H5 H 0.4987 0.7633 -0.0210 0.069 Uiso 1 1 calc R
C6 C 0.5459(2) 0.8743(6) 0.0734(3) 0.0655(14) Uani 1 1 d .
H6 H 0.5591 0.9427 0.0438 0.079 Uiso 1 1 calc R
C7 C 0.56296(19) 0.8834(5) 0.1550(3) 0.0610(14) Uani 1 1 d .
H7 H 0.5873 0.9595 0.1809 0.073 Uiso 1 1 calc R
C8 C 0.54517(18) 0.7839(5) 0.1985(3) 0.0529(12) Uani 1 1 d .
H8 H 0.5576 0.7907 0.2545 0.063 Uiso 1 1 calc R
C9 C 0.50856(15) 0.6711(4) 0.1617(2) 0.0394(10) Uani 1 1 d .
C10 C 0.48970(17) 0.6640(5) 0.0776(3) 0.0450(11) Uani 1 1 d .
C11 C 0.39173(14) 0.1843(5) 0.1515(2) 0.0384(9) Uani 1 1 d .
C12 C 0.41947(15) 0.0694(5) 0.1312(2) 0.0454(10) Uani 1 1 d .
H12 H 0.4545 0.0692 0.1551 0.054 Uiso 1 1 calc R
C13 C 0.39664(16) -0.0443(5) 0.0765(2) 0.0471(10) Uani 1 1 d .
H13 H 0.4159 -0.1230 0.0630 0.056 Uiso 1 1 calc R
C14 C 0.34564(16) -0.0441(5) 0.0413(2) 0.0437(10) Uani 1 1 d .
C15 C 0.31737(16) 0.0681(5) 0.0618(3) 0.0535(12) Uani 1 1 d .
H15 H 0.2824 0.0676 0.0380 0.064 Uiso 1 1 calc R
C16 C 0.34055(15) 0.1814(5) 0.1174(3) 0.0510(11) Uani 1 1 d .
H16 H 0.3212 0.2578 0.1323 0.061 Uiso 1 1 calc R
C17 C 0.32158(19) -0.1642(5) -0.0204(3) 0.0543(12) Uani 1 1 d .
F17C F 0.34380(14) -0.1749(4) -0.07451(18) 0.0928(11) Uani 1 1 d .
F17B F 0.32343(15) -0.3089(3) 0.00886(17) 0.0928(11) Uani 1 1 d .
F17A F 0.27464(12) -0.1340(4) -0.06053(17) 0.0866(10) Uani 1 1 d .
C18 C 0.37982(14) 0.4528(4) 0.2449(2) 0.0374(9) Uani 1 1 d .
C19 C 0.35244(16) 0.5688(5) 0.1941(2) 0.0526(12) Uani 1 1 d .
H19 H 0.3554 0.5816 0.1434 0.063 Uiso 1 1 calc R
C20 C 0.32112(17) 0.6654(6) 0.2169(3) 0.0569(12) Uani 1 1 d .
H20 H 0.3026 0.7446 0.1820 0.068 Uiso 1 1 calc R
C21 C 0.31681(15) 0.6466(5) 0.2908(3) 0.0482(11) Uani 1 1 d .
C22 C 0.34321(17) 0.5308(5) 0.3412(3) 0.0538(12) Uani 1 1 d .
H22 H 0.3399 0.5176 0.3916 0.065 Uiso 1 1 calc R
C23 C 0.37459(15) 0.4340(5) 0.3183(2) 0.0428(10) Uani 1 1 d .
H23 H 0.3927 0.3540 0.3530 0.051 Uiso 1 1 calc R
C24 C 0.2832(2) 0.7551(8) 0.3140(4) 0.0787(17) Uani 1 1 d .
F24C F 0.28205(19) 0.7331(7) 0.3840(3) 0.155(2) Uani 1 1 d .
F24B F 0.2942(3) 0.8996(6) 0.3119(5) 0.222(4) Uani 1 1 d .
F24A F 0.23818(16) 0.7498(8) 0.2701(3) 0.169(3) 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'
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
O1 P1 C18 111.21(17) .
O1 P1 C11 111.56(17) .
C18 P1 C11 107.51(17) .
O1 P1 C2 118.05(16) .
C18 P1 C2 103.58(17) .
C11 P1 C2 104.10(18) .
C2 C1 C9 120.6(3) .
C2 C1 C1 120.3(3) 2_655
C9 C1 C1 119.0(3) 2_655
C1 C2 C3 119.4(4) .
C1 C2 P1 120.7(3) .
C3 C2 P1 119.9(3) .
C4 C3 C2 120.3(4) .
C4 C3 H3 119.8 .
C2 C3 H3 119.8 .
C3 C4 C10 122.0(4) .
C3 C4 H4 119.0 .
C10 C4 H4 119.0 .
C6 C5 C10 121.0(5) .
C6 C5 H5 119.5 .
C10 C5 H5 119.5 .
C5 C6 C7 120.6(4) .
C5 C6 H6 119.7 .
C7 C6 H6 119.7 .
C8 C7 C6 120.5(5) .
C8 C7 H7 119.8 .
C6 C7 H7 119.8 .
C7 C8 C9 121.1(4) .
C7 C8 H8 119.5 .
C9 C8 H8 119.5 .
C8 C9 C10 118.8(4) .
C8 C9 C1 122.3(4) .
C10 C9 C1 118.8(4) .
C4 C10 C5 123.1(4) .
C4 C10 C9 118.9(4) .
C5 C10 C9 118.0(4) .
C12 C11 C16 119.2(4) .
C12 C11 P1 117.2(3) .
C16 C11 P1 123.6(3) .
C13 C12 C11 120.4(4) .
C13 C12 H12 119.8 .
C11 C12 H12 119.8 .
C12 C13 C14 120.0(4) .
C12 C13 H13 120.0 .
C14 C13 H13 120.0 .
C15 C14 C13 120.4(4) .
C15 C14 C17 120.3(4) .
C13 C14 C17 119.3(4) .
C14 C15 C16 119.4(4) .
C14 C15 H15 120.3 .
C16 C15 H15 120.3 .
C15 C16 C11 120.6(4) .
C15 C16 H16 119.7 .
C11 C16 H16 119.7 .
F17A C17 F17B 107.0(4) .
F17A C17 F17C 105.4(4) .
F17B C17 F17C 105.1(4) .
F17A C17 C14 113.8(4) .
F17B C17 C14 113.0(4) .
F17C C17 C14 111.9(4) .
C23 C18 C19 119.1(4) .
C23 C18 P1 117.3(3) .
C19 C18 P1 123.4(3) .
C20 C19 C18 120.5(4) .
C20 C19 H19 119.8 .
C18 C19 H19 119.8 .
C19 C20 C21 119.7(4) .
C19 C20 H20 120.1 .
C21 C20 H20 120.1 .
C22 C21 C20 120.4(4) .
C22 C21 C24 121.3(4) .
C20 C21 C24 118.3(4) .
C21 C22 C23 119.8(4) .
C21 C22 H22 120.1 .
C23 C22 H22 120.1 .
C22 C23 C18 120.5(4) .
C22 C23 H23 119.7 .
C18 C23 H23 119.7 .
F24A C24 F24B 103.1(7) .
F24A C24 F24C 104.3(6) .
F24B C24 F24C 105.0(6) .
F24A C24 C21 115.0(5) .
F24B C24 C21 113.4(5) .
F24C C24 C21 114.8(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O1 1.479(3) .
P1 C18 1.809(4) .
P1 C11 1.812(4) .
P1 C2 1.821(4) .
C1 C2 1.391(5) .
C1 C9 1.431(5) .
C1 C1 1.503(7) 2_655
C2 C3 1.418(5) .
C3 C4 1.368(6) .
C3 H3 0.9500 .
C4 C10 1.400(6) .
C4 H4 0.9500 .
C5 C6 1.368(7) .
C5 C10 1.418(6) .
C5 H5 0.9500 .
C6 C7 1.383(7) .
C6 H6 0.9500 .
C7 C8 1.363(6) .
C7 H7 0.9500 .
C8 C9 1.411(6) .
C8 H8 0.9500 .
C9 C10 1.425(6) .
C11 C12 1.385(5) .
C11 C16 1.388(6) .
C12 C13 1.376(6) .
C12 H12 0.9500 .
C13 C14 1.385(6) .
C13 H13 0.9500 .
C14 C15 1.380(6) .
C14 C17 1.493(6) .
C15 C16 1.385(6) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 F17A 1.321(5) .
C17 F17B 1.331(5) .
C17 F17C 1.337(6) .
C18 C23 1.388(5) .
C18 C19 1.392(5) .
C19 C20 1.378(6) .
C19 H19 0.9500 .
C20 C21 1.387(6) .
C20 H20 0.9500 .
C21 C22 1.378(6) .
C21 C24 1.493(7) .
C22 C23 1.383(6) .
C22 H22 0.9500 .
C23 H23 0.9500 .
C24 F24A 1.268(7) .
C24 F24B 1.271(7) .
C24 F24C 1.284(7) .
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 1.0(5) .
C1 C1 C2 C3 -176.9(3) 2_655
C9 C1 C2 P1 -178.2(3) .
C1 C1 C2 P1 3.9(5) 2_655
O1 P1 C2 C1 -40.2(4) .
C18 P1 C2 C1 83.2(3) .
C11 P1 C2 C1 -164.5(3) .
O1 P1 C2 C3 140.6(3) .
C18 P1 C2 C3 -96.0(3) .
C11 P1 C2 C3 16.4(3) .
C1 C2 C3 C4 1.0(6) .
P1 C2 C3 C4 -179.8(3) .
C2 C3 C4 C10 -2.3(6) .
C10 C5 C6 C7 -0.1(7) .
C5 C6 C7 C8 1.4(7) .
C6 C7 C8 C9 -0.9(7) .
C7 C8 C9 C10 -0.9(6) .
C7 C8 C9 C1 -179.7(4) .
C2 C1 C9 C8 177.0(4) .
C1 C1 C9 C8 -5.0(6) 2_655
C2 C1 C9 C10 -1.7(5) .
C1 C1 C9 C10 176.2(3) 2_655
C3 C4 C10 C5 -179.0(4) .
C3 C4 C10 C9 1.5(6) .
C6 C5 C10 C4 178.8(4) .
C6 C5 C10 C9 -1.6(6) .
C8 C9 C10 C4 -178.3(4) .
C1 C9 C10 C4 0.5(5) .
C8 C9 C10 C5 2.2(5) .
C1 C9 C10 C5 -179.0(3) .
O1 P1 C11 C12 -52.6(3) .
C18 P1 C11 C12 -174.8(3) .
C2 P1 C11 C12 75.8(3) .
O1 P1 C11 C16 126.9(4) .
C18 P1 C11 C16 4.7(4) .
C2 P1 C11 C16 -104.8(4) .
C16 C11 C12 C13 1.4(6) .
P1 C11 C12 C13 -179.1(3) .
C11 C12 C13 C14 0.2(6) .
C12 C13 C14 C15 -1.2(6) .
C12 C13 C14 C17 177.4(4) .
C13 C14 C15 C16 0.6(6) .
C17 C14 C15 C16 -178.0(4) .
C14 C15 C16 C11 1.0(7) .
C12 C11 C16 C15 -2.0(6) .
P1 C11 C16 C15 178.6(3) .
C15 C14 C17 F17A 11.4(6) .
C13 C14 C17 F17A -167.2(4) .
C15 C14 C17 F17B -110.9(5) .
C13 C14 C17 F17B 70.5(5) .
C15 C14 C17 F17C 130.7(4) .
C13 C14 C17 F17C -47.9(5) .
O1 P1 C18 C23 -14.8(4) .
C11 P1 C18 C23 107.6(3) .
C2 P1 C18 C23 -142.6(3) .
O1 P1 C18 C19 161.5(3) .
C11 P1 C18 C19 -76.1(4) .
C2 P1 C18 C19 33.7(4) .
C23 C18 C19 C20 1.0(6) .
P1 C18 C19 C20 -175.2(4) .
C18 C19 C20 C21 -0.1(7) .
C19 C20 C21 C22 -0.8(7) .
C19 C20 C21 C24 179.0(5) .
C20 C21 C22 C23 0.7(7) .
C24 C21 C22 C23 -179.0(4) .
C21 C22 C23 C18 0.2(6) .
C19 C18 C23 C22 -1.0(6) .
P1 C18 C23 C22 175.4(3) .
C22 C21 C24 F24A -119.7(7) .
C20 C21 C24 F24A 60.6(8) .
C22 C21 C24 F24B 122.1(7) .
C20 C21 C24 F24B -57.6(8) .
C22 C21 C24 F24C 1.3(8) .
C20 C21 C24 F24C -178.4(5) .
