#------------------------------------------------------------------------------
#$Date: 2019-11-25 02:24:38 +0200 (Mon, 25 Nov 2019) $
#$Revision: 239961 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/35/06/4350608.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_4350608
loop_
_publ_author_name
'Timosheva, Natalya V.'
'Chandrasekaran, A.'
'Holmes, Robert R.'
_publ_section_title
;
 Biologically relevant phosphoranes: synthesis and structural
 characterization of glucofuranose-derived phosphoranes with penta- and
 hexacoordination at phosphorus.
;
_journal_issue                   26
_journal_name_full               'Inorganic chemistry'
_journal_page_first              10836
_journal_page_last               10848
_journal_paper_doi               10.1021/ic061596f
_journal_volume                  45
_journal_year                    2006
_chemical_formula_moiety         'C33 H44 F3 O9 P S'
_chemical_formula_sum            'C33 H44 F3 O9 P S'
_chemical_formula_weight         704.71
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9547(2)
_cell_length_b                   17.7766(5)
_cell_length_c                   21.0860(6)
_cell_measurement_reflns_used    3492
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      4.08
_cell_volume                     3731.39(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius KappaCCD area detector'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6406
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.8691
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0352P)²+1.5941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1039
_reflns_number_gt                5541
_reflns_number_total             6406
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic061596fsi20060918_073923.cif
_cod_data_source_block           ntp40_(compound_=_6)
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4350608
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
P P 0.71686(7) 0.02157(4) 0.01779(4) 0.04366(18) Uani 1 1 d .
S S 0.64954(8) -0.00603(4) -0.09615(4) 0.0515(2) Uani 1 1 d .
O1 O 0.9306(2) 0.25306(12) 0.03244(11) 0.0650(6) Uani 1 1 d .
O2 O 1.0438(3) 0.2993(2) 0.12039(14) 0.1181(13) Uani 1 1 d .
O3 O 0.8689(3) 0.25886(15) 0.17733(12) 0.0786(7) Uani 1 1 d .
O4 O 0.6436(3) 0.28178(17) 0.04728(19) 0.1161(12) Uani 1 1 d .
H4 H 0.5950 0.2542 0.0261 0.174 Uiso 1 1 calc R
O5 O 0.67532(17) 0.11033(10) 0.00417(10) 0.0490(5) Uani 1 1 d .
O6 O 0.86752(17) 0.03403(10) -0.01222(10) 0.0498(5) Uani 1 1 d .
O7 O 0.55388(18) 0.00515(11) 0.03359(9) 0.0514(5) Uani 1 1 d .
O8 O 0.7469(2) -0.07225(10) 0.02088(9) 0.0494(5) Uani 1 1 d .
O9 O 0.75482(18) 0.03307(11) 0.09190(9) 0.0501(5) Uani 1 1 d .
F1 F 0.8489(3) 0.0479(2) 0.21498(13) 0.1488(14) Uani 1 1 d .
F2 F 0.6477(4) 0.0783(2) 0.20534(14) 0.1511(14) Uani 1 1 d .
F3 F 0.6983(3) -0.02338(18) 0.24967(11) 0.1258(10) Uani 1 1 d .
C1 C 0.9333(4) 0.3082(2) 0.08084(19) 0.0761(11) Uani 1 1 d .
H1 H 0.9302 0.3590 0.0629 0.091 Uiso 1 1 calc R
C2 C 0.8129(4) 0.2935(2) 0.12346(19) 0.0705(10) Uani 1 1 d .
H2 H 0.7635 0.3396 0.1338 0.085 Uiso 1 1 calc R
C3 C 0.7280(3) 0.23728(19) 0.08648(19) 0.0664(9) Uani 1 1 d .
H3 H 0.6768 0.2038 0.1144 0.080 Uiso 1 1 calc R
C4 C 0.8343(3) 0.19571(15) 0.04904(15) 0.0490(7) Uani 1 1 d .
H4A H 0.8774 0.1582 0.0764 0.059 Uiso 1 1 calc R
C5 C 0.7872(3) 0.15824(16) -0.01138(15) 0.0509(7) Uani 1 1 d .
H5 H 0.7590 0.1965 -0.0421 0.061 Uiso 1 1 calc R
C6 C 0.8866(3) 0.10506(17) -0.04199(16) 0.0559(8) Uani 1 1 d .
H6A H 0.8699 0.1013 -0.0872 0.067 Uiso 1 1 calc R
H6B H 0.9778 0.1227 -0.0355 0.067 Uiso 1 1 calc R
C7 C 1.0022(4) 0.2838(3) 0.1830(2) 0.0821(12) Uani 1 1 d .
C8 C 1.0823(7) 0.2194(4) 0.2110(3) 0.155(3) Uani 1 1 d .
H8A H 1.1745 0.2343 0.2155 0.233 Uiso 1 1 calc R
H8B H 1.0768 0.1766 0.1834 0.233 Uiso 1 1 calc R
H8C H 1.0463 0.2066 0.2518 0.233 Uiso 1 1 calc R
C9 C 1.0121(6) 0.3537(3) 0.2222(2) 0.1144(18) Uani 1 1 d .
H9A H 1.1047 0.3678 0.2267 0.172 Uiso 1 1 calc R
H9B H 0.9741 0.3446 0.2633 0.172 Uiso 1 1 calc R
H9C H 0.9637 0.3937 0.2018 0.172 Uiso 1 1 calc R
C10 C 0.4515(3) -0.00090(15) -0.00951(15) 0.0491(7) Uani 1 1 d .
C11 C 0.3179(3) 0.00638(17) 0.01197(17) 0.0576(8) Uani 1 1 d .
C12 C 0.2189(3) -0.0060(2) -0.03352(19) 0.0715(10) Uani 1 1 d .
H12 H 0.1297 -0.0025 -0.0208 0.086 Uiso 1 1 calc R
C13 C 0.2442(3) -0.0232(2) -0.0963(2) 0.0777(11) Uani 1 1 d .
C14 C 0.3758(3) -0.02467(18) -0.11670(16) 0.0632(8) Uani 1 1 d .
H14 H 0.3953 -0.0327 -0.1593 0.076 Uiso 1 1 calc R
C15 C 0.4801(3) -0.01402(17) -0.07295(15) 0.0508(7) Uani 1 1 d .
C16 C 0.7222(3) -0.09637(15) -0.08970(14) 0.0462(7) Uani 1 1 d .
C17 C 0.7430(3) -0.14095(17) -0.14283(15) 0.0540(8) Uani 1 1 d .
H17 H 0.7123 -0.1252 -0.1823 0.065 Uiso 1 1 calc R
C18 C 0.8096(4) -0.20895(19) -0.13681(16) 0.0603(8) Uani 1 1 d .
C19 C 0.8480(3) -0.23091(16) -0.07621(15) 0.0547(8) Uani 1 1 d .
H19 H 0.8901 -0.2773 -0.0719 0.066 Uiso 1 1 calc R
C20 C 0.8281(3) -0.18860(15) -0.02135(15) 0.0456(7) Uani 1 1 d .
C21 C 0.7658(3) -0.11822(15) -0.02993(14) 0.0424(6) Uani 1 1 d .
C22 C 0.2851(3) 0.0263(2) 0.08097(17) 0.0648(9) Uani 1 1 d .
C23 C 0.8723(3) -0.21711(16) 0.04397(15) 0.0511(8) Uani 1 1 d .
C24 C 0.7219(4) -0.0177(2) 0.14076(15) 0.0728(10) Uani 1 1 d .
H24A H 0.7825 -0.0604 0.1396 0.087 Uiso 1 1 calc R
H24B H 0.6310 -0.0361 0.1348 0.087 Uiso 1 1 calc R
C25 C 0.7326(5) 0.0202(3) 0.20170(18) 0.0860(12) Uani 1 1 d .
C26 C 0.1338(3) 0.0412(3) 0.0900(2) 0.0968(14) Uani 1 1 d .
H26A H 0.1064 0.0818 0.0630 0.145 Uiso 1 1 calc R
H26B H 0.1168 0.0543 0.1335 0.145 Uiso 1 1 calc R
H26C H 0.0841 -0.0033 0.0793 0.145 Uiso 1 1 calc R
C27 C 0.3235(4) -0.0395(2) 0.1238(2) 0.0885(12) Uani 1 1 d .
H27A H 0.3018 -0.0274 0.1669 0.133 Uiso 1 1 calc R
H27B H 0.4182 -0.0488 0.1202 0.133 Uiso 1 1 calc R
H27C H 0.2748 -0.0835 0.1110 0.133 Uiso 1 1 calc R
C28 C 0.3573(4) 0.09903(19) 0.1010(2) 0.0779(11) Uani 1 1 d .
H28A H 0.3318 0.1392 0.0730 0.117 Uiso 1 1 calc R
H28B H 0.4527 0.0916 0.0987 0.117 Uiso 1 1 calc R
H28C H 0.3325 0.1117 0.1436 0.117 Uiso 1 1 calc R
C29 C 0.1300(4) -0.0373(3) -0.1428(2) 0.1187(18) Uani 1 1 d .
H29A H 0.0900 0.0098 -0.1547 0.178 Uiso 1 1 calc R
H29B H 0.0636 -0.0688 -0.1232 0.178 Uiso 1 1 calc R
H29C H 0.1646 -0.0619 -0.1800 0.178 Uiso 1 1 calc R
C30 C 0.8407(6) -0.2571(2) -0.19393(19) 0.0982(15) Uani 1 1 d .
H30A H 0.7674 -0.2911 -0.2015 0.147 Uiso 1 1 calc R
H30B H 0.9212 -0.2854 -0.1862 0.147 Uiso 1 1 calc R
H30C H 0.8533 -0.2255 -0.2304 0.147 Uiso 1 1 calc R
C31 C 0.9332(4) -0.2961(2) 0.04106(19) 0.0738(11) Uani 1 1 d .
H31A H 1.0100 -0.2958 0.0136 0.111 Uiso 1 1 calc R
H31B H 0.8675 -0.3308 0.0250 0.111 Uiso 1 1 calc R
H31C H 0.9601 -0.3114 0.0828 0.111 Uiso 1 1 calc R
C32 C 0.9818(3) -0.1643(2) 0.07066(19) 0.0715(10) Uani 1 1 d .
H32A H 1.0558 -0.1621 0.0415 0.107 Uiso 1 1 calc R
H32B H 1.0125 -0.1832 0.1108 0.107 Uiso 1 1 calc R
H32C H 0.9452 -0.1148 0.0763 0.107 Uiso 1 1 calc R
C33 C 0.7516(3) -0.2216(2) 0.08867(17) 0.0673(9) Uani 1 1 d .
H33A H 0.7805 -0.2395 0.1294 0.101 Uiso 1 1 calc R
H33B H 0.6861 -0.2556 0.0715 0.101 Uiso 1 1 calc R
H33C H 0.7124 -0.1725 0.0932 0.101 Uiso 1 1 calc R
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_publ_flag
O5 P O6 91.87(10) y
O5 P O7 87.64(10) y
O5 P O8 171.00(11) y
O5 P O9 96.04(11) y
O6 P O7 168.64(11) y
O6 P O8 89.24(10) y
O6 P O9 98.13(10) y
O7 P O8 89.52(10) y
O7 P O9 93.20(10) y
O8 P O9 92.64(10) y
O5 P S 87.37(8) y
O6 P S 84.41(8) y
O7 P S 84.23(7) y
O8 P S 83.85(7) y
O9 P S 175.65(8) y
C15 S C16 107.31(14) y
C15 S P 90.31(10) y
C16 S P 89.69(10) y
C1 O1 C4 109.1(2) ?
C1 O2 C7 110.6(3) ?
C7 O3 C2 107.7(3) ?
C5 O5 P 114.20(16) y
C6 O6 P 114.29(17) y
C10 O7 P 126.88(19) y
C21 O8 P 125.80(17) y
C24 O9 P 124.78(18) y
O2 C1 O1 111.7(3) ?
O2 C1 C2 104.5(3) ?
O1 C1 C2 107.0(3) ?
O3 C2 C1 103.9(3) ?
O3 C2 C3 110.2(3) ?
C1 C2 C3 104.3(3) ?
O4 C3 C4 112.5(3) ?
O4 C3 C2 105.1(3) ?
C4 C3 C2 101.6(3) ?
O1 C4 C5 108.2(2) ?
O1 C4 C3 104.3(2) ?
C5 C4 C3 116.0(3) ?
O5 C5 C4 108.0(2) ?
O5 C5 C6 103.5(2) ?
C4 C5 C6 115.6(3) ?
O6 C6 C5 106.2(2) ?
O3 C7 O2 105.1(3) ?
O3 C7 C9 111.7(4) ?
O2 C7 C9 109.6(4) ?
O3 C7 C8 107.0(4) ?
O2 C7 C8 111.1(5) ?
C9 C7 C8 112.2(4) ?
O7 C10 C15 120.0(2) ?
O7 C10 C11 118.8(3) ?
C15 C10 C11 121.3(3) ?
C12 C11 C10 115.5(3) ?
C12 C11 C22 122.7(3) ?
C10 C11 C22 121.8(3) ?
C13 C12 C11 124.5(3) ?
C14 C13 C12 118.4(3) ?
C14 C13 C29 120.4(4) ?
C12 C13 C29 121.2(4) ?
C13 C14 C15 119.8(3) ?
C10 C15 C14 120.3(3) ?
C10 C15 S 116.8(2) ?
C14 C15 S 122.5(3) ?
C17 C16 C21 121.8(3) ?
C17 C16 S 121.2(2) ?
C21 C16 S 116.9(2) ?
C18 C17 C16 119.7(3) ?
C17 C18 C19 117.5(3) ?
C17 C18 C30 121.4(3) ?
C19 C18 C30 121.2(3) ?
C18 C19 C20 124.9(3) ?
C19 C20 C21 115.8(3) ?
C19 C20 C23 121.8(2) ?
C21 C20 C23 122.4(3) ?
O8 C21 C16 120.2(2) ?
O8 C21 C20 119.6(2) ?
C16 C21 C20 120.2(3) ?
C27 C22 C11 109.3(3) ?
C27 C22 C28 111.4(3) ?
C11 C22 C28 110.8(3) ?
C27 C22 C26 107.7(3) ?
C11 C22 C26 111.5(3) ?
C28 C22 C26 106.2(3) ?
C33 C23 C31 106.7(3) ?
C33 C23 C20 110.3(3) ?
C31 C23 C20 112.4(3) ?
C33 C23 C32 111.2(3) ?
C31 C23 C32 107.0(3) ?
C20 C23 C32 109.2(3) ?
O9 C24 C25 109.4(3) ?
F1 C25 F3 106.8(4) ?
F1 C25 F2 105.1(4) ?
F3 C25 F2 104.3(4) ?
F1 C25 C24 115.8(4) ?
F3 C25 C24 112.7(4) ?
F2 C25 C24 111.2(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P O5 1.6563(19) y
P O6 1.6429(19) y
P O7 1.682(2) y
P O8 1.6954(19) y
P O9 1.621(2) y
P S 2.5422(11) y
S C15 1.762(3) ?
S C16 1.767(3) ?
O1 C1 1.415(4) ?
O1 C4 1.443(3) ?
O2 C1 1.390(5) ?
O2 C7 1.410(5) ?
O3 C7 1.404(4) ?
O3 C2 1.408(4) ?
O4 C3 1.420(4) ?
O5 C5 1.440(3) ?
O6 C6 1.423(3) ?
O7 C10 1.370(3) ?
O8 C21 1.361(3) ?
O9 C24 1.408(4) ?
F1 C25 1.289(5) ?
F2 C25 1.336(5) ?
F3 C25 1.319(5) ?
C1 C2 1.521(5) ?
C2 C3 1.524(5) ?
C3 C4 1.513(4) ?
C4 C5 1.512(4) ?
C5 C6 1.513(4) ?
C7 C9 1.497(6) ?
C7 C8 1.514(7) ?
C10 C15 1.387(4) ?
C10 C11 1.410(4) ?
C11 C12 1.393(4) ?
C11 C22 1.533(5) ?
C12 C13 1.382(5) ?
C13 C14 1.379(5) ?
C13 C29 1.522(5) ?
C14 C15 1.402(4) ?
C16 C17 1.388(4) ?
C16 C21 1.388(4) ?
C17 C18 1.384(4) ?
C18 C19 1.390(5) ?
C18 C30 1.510(5) ?
C19 C20 1.394(4) ?
C20 C21 1.408(4) ?
C20 C23 1.532(4) ?
C22 C27 1.526(5) ?
C22 C28 1.538(4) ?
C22 C26 1.541(5) ?
C23 C33 1.529(5) ?
C23 C31 1.531(4) ?
C23 C32 1.545(4) ?
C24 C25 1.455(5) ?
