#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:46:09 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179423 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/20/4332060.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4332060
loop_
_publ_author_name
'Timosheva, Natalya V.'
'Chandrasekaran, A.'
'Holmes, Robert R.'
_publ_section_title
;
 Biologically Relevant Phosphoranes:  Structural Characterization
 of Glucofuranose- and Xylofuranose-Based Phosphoranes1
;
_journal_issue                   7
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3113
_journal_page_last               3123
_journal_paper_doi               10.1021/ic052105e
_journal_volume                  45
_journal_year                    2006
_chemical_formula_sum            'C39 H58 F O8 P'
_chemical_formula_weight         704.82
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 106.8839(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.0550(2)
_cell_length_b                   5.85400(10)
_cell_length_c                   23.4593(3)
_cell_measurement_reflns_used    3775
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      4.08
_cell_volume                     1978.39(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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    0.0299
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6325
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         4.10
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9702
_exptl_absorpt_correction_T_min  0.8878
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6325
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0534
_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)+(0.0874P)²+1.1115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1505
_reflns_number_gt                5902
_reflns_number_total             6325
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic052105esup1.cif
_cod_data_source_block           ntp25(Compound=1)
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4332060
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
P P 0.17052(5) 0.38224(14) 0.18492(3) 0.0342(2) Uani 1 1 d .
F F 0.15959(11) 0.6220(3) 0.21542(8) 0.0409(4) Uani 1 1 d .
O1 O 0.33094(15) 0.2334(4) 0.04866(10) 0.0452(5) Uani 1 1 d .
O2 O 0.48459(16) 0.1295(5) 0.06136(12) 0.0579(7) Uani 1 1 d .
O3 O 0.51507(15) 0.4251(4) 0.12747(11) 0.0530(6) Uani 1 1 d .
O4 O 0.30858(17) 0.7293(5) 0.04301(12) 0.0582(7) Uani 1 1 d .
O5 O 0.19616(14) 0.5264(4) 0.13353(9) 0.0394(5) Uani 1 1 d .
O6 O 0.18623(14) 0.1375(4) 0.15412(9) 0.0406(5) Uani 1 1 d .
O7 O 0.06294(13) 0.3227(4) 0.17421(8) 0.0360(5) Uani 1 1 d .
O8 O 0.24812(13) 0.2996(4) 0.24344(9) 0.0400(5) Uani 1 1 d .
C1 C 0.4159(2) 0.2956(6) 0.03886(15) 0.0447(8) Uani 1 1 d .
H1 H 0.4077 0.3230 -0.0036 0.054 Uiso 1 1 calc R
C2 C 0.4490(2) 0.5100(6) 0.07493(16) 0.0460(8) Uani 1 1 d .
H2 H 0.4756 0.6225 0.0536 0.055 Uiso 1 1 calc R
C3 C 0.3641(2) 0.5984(6) 0.09014(16) 0.0437(8) Uani 1 1 d .
H3 H 0.3810 0.6837 0.1277 0.052 Uiso 1 1 calc R
C4 C 0.31515(19) 0.3752(6) 0.09543(13) 0.0386(7) Uani 1 1 d .
H4 H 0.3446 0.3052 0.1343 0.046 Uiso 1 1 calc R
C5 C 0.2111(2) 0.3888(7) 0.08530(13) 0.0415(7) Uani 1 1 d .
H5 H 0.1802 0.4570 0.0465 0.050 Uiso 1 1 calc R
C6 C 0.1681(2) 0.1587(6) 0.09222(14) 0.0452(8) Uani 1 1 d .
H6A H 0.1019 0.1583 0.0724 0.054 Uiso 1 1 calc R
H6B H 0.1970 0.0361 0.0762 0.054 Uiso 1 1 calc R
C7 C 0.5510(2) 0.2129(7) 0.11406(18) 0.0546(9) Uani 1 1 d .
C8 C 0.5566(4) 0.0541(10) 0.1644(2) 0.0925(17) Uani 1 1 d .
H8A H 0.6018 0.1094 0.1995 0.139 Uiso 1 1 calc R
H8B H 0.5745 -0.0949 0.1546 0.139 Uiso 1 1 calc R
H8C H 0.4971 0.0451 0.1715 0.139 Uiso 1 1 calc R
C9 C 0.6421(3) 0.2499(10) 0.1014(2) 0.0835(15) Uani 1 1 d .
H9A H 0.6871 0.3039 0.1367 0.125 Uiso 1 1 calc R
H9B H 0.6343 0.3610 0.0702 0.125 Uiso 1 1 calc R
H9C H 0.6629 0.1083 0.0890 0.125 Uiso 1 1 calc R
C10 C 0.00519(18) 0.3933(6) 0.20845(12) 0.0353(6) Uani 1 1 d .
C11 C -0.0713(2) 0.5336(6) 0.18300(14) 0.0383(7) Uani 1 1 d .
C12 C -0.1276(2) 0.5838(6) 0.21898(15) 0.0453(8) Uani 1 1 d .
H12 H -0.1786 0.6783 0.2036 0.054 Uiso 1 1 calc R
C13 C -0.1123(2) 0.5013(7) 0.27649(15) 0.0456(8) Uani 1 1 d .
C14 C -0.0366(2) 0.3598(7) 0.29889(14) 0.0464(8) Uani 1 1 d .
H14 H -0.0249 0.3027 0.3374 0.056 Uiso 1 1 calc R
C15 C 0.0228(2) 0.3004(6) 0.26537(14) 0.0394(7) Uani 1 1 d .
C16 C 0.1070(2) 0.1467(6) 0.29110(14) 0.0406(7) Uani 1 1 d .
H16 H 0.1249 0.0848 0.2572 0.049 Uiso 1 1 calc R
C17 C 0.0864(3) -0.0577(7) 0.32584(17) 0.0566(10) Uani 1 1 d .
H17A H 0.1416 -0.1475 0.3407 0.085 Uiso 1 1 calc R
H17B H 0.0386 -0.1497 0.3000 0.085 Uiso 1 1 calc R
H17C H 0.0660 -0.0041 0.3586 0.085 Uiso 1 1 calc R
C18 C 0.1887(2) 0.2917(6) 0.32733(14) 0.0426(7) Uani 1 1 d .
C19 C 0.1952(2) 0.3555(7) 0.38520(14) 0.0500(8) Uani 1 1 d .
H19 H 0.1498 0.3079 0.4023 0.060 Uiso 1 1 calc R
C20 C 0.2688(3) 0.4903(7) 0.41834(16) 0.0566(9) Uani 1 1 d .
C21 C 0.3358(3) 0.5515(7) 0.39198(16) 0.0558(9) Uani 1 1 d .
H21 H 0.3862 0.6360 0.4145 0.067 Uiso 1 1 calc R
C22 C 0.3334(2) 0.4958(7) 0.33412(15) 0.0477(8) Uani 1 1 d .
C23 C 0.2561(2) 0.3685(6) 0.30231(13) 0.0415(7) Uani 1 1 d .
C24 C -0.0956(2) 0.6262(7) 0.11861(14) 0.0444(8) Uani 1 1 d .
C25 C -0.1761(3) 0.5703(8) 0.31465(19) 0.0624(11) Uani 1 1 d .
C26 C 0.2744(4) 0.5676(8) 0.48262(17) 0.0743(14) Uani 1 1 d .
C27 C 0.4118(2) 0.5749(8) 0.30848(18) 0.0593(10) Uani 1 1 d .
C28 C -0.0186(2) 0.7767(8) 0.10863(18) 0.0601(10) Uani 1 1 d .
H28A H 0.0382 0.6914 0.1177 0.090 Uiso 1 1 calc R
H28B H -0.0104 0.9081 0.1341 0.090 Uiso 1 1 calc R
H28C H -0.0353 0.8254 0.0678 0.090 Uiso 1 1 calc R
C29 C -0.1139(3) 0.4259(8) 0.07457(16) 0.0633(11) Uani 1 1 d .
H29A H -0.0601 0.3294 0.0831 0.095 Uiso 1 1 calc R
H29B H -0.1270 0.4837 0.0347 0.095 Uiso 1 1 calc R
H29C H -0.1661 0.3395 0.0783 0.095 Uiso 1 1 calc R
C30 C -0.1831(2) 0.7753(8) 0.10330(18) 0.0639(11) Uani 1 1 d .
H30A H -0.2340 0.6888 0.1091 0.096 Uiso 1 1 calc R
H30B H -0.1978 0.8232 0.0625 0.096 Uiso 1 1 calc R
H30C H -0.1724 0.9071 0.1287 0.096 Uiso 1 1 calc R
C31 C -0.2738(6) 0.4565(17) 0.2848(4) 0.085(2) Uiso 0.60 1 d P
C32 C -0.1444(6) 0.4692(18) 0.3772(4) 0.090(3) Uiso 0.60 1 d P
C33 C -0.1873(6) 0.8258(18) 0.3146(4) 0.090(3) Uiso 0.60 1 d P
C31' C -0.2603(10) 0.743(3) 0.2773(7) 0.101(4) Uiso 0.40 1 d P
C32' C -0.2252(10) 0.371(3) 0.3305(6) 0.097(4) Uiso 0.40 1 d P
C33' C -0.1202(12) 0.690(3) 0.3707(8) 0.114(5) Uiso 0.40 1 d P
C34 C 0.3648(8) 0.456(2) 0.5247(5) 0.109(3) Uiso 0.60 1 d P
C35 C 0.1885(8) 0.490(2) 0.5019(5) 0.118(4) Uiso 0.60 1 d P
C36 C 0.2813(7) 0.823(2) 0.4866(5) 0.100(3) Uiso 0.60 1 d P
C34' C 0.1927(13) 0.731(4) 0.4812(8) 0.128(6) Uiso 0.40 1 d P
C35' C 0.2880(10) 0.365(3) 0.5261(7) 0.102(4) Uiso 0.40 1 d P
C36' C 0.3661(15) 0.715(4) 0.5116(9) 0.136(6) Uiso 0.40 1 d P
C37 C 0.3747(3) 0.7443(9) 0.2579(2) 0.0742(13) Uani 1 1 d .
H37A H 0.4242 0.7915 0.2424 0.111 Uiso 1 1 calc R
H37B H 0.3498 0.8751 0.2726 0.111 Uiso 1 1 calc R
H37C H 0.3268 0.6730 0.2269 0.111 Uiso 1 1 calc R
C38 C 0.4542(3) 0.3705(11) 0.2848(3) 0.0913(16) Uani 1 1 d .
H38A H 0.5032 0.4227 0.2695 0.137 Uiso 1 1 calc R
H38B H 0.4071 0.2973 0.2535 0.137 Uiso 1 1 calc R
H38C H 0.4786 0.2636 0.3165 0.137 Uiso 1 1 calc R
C39 C 0.4922(3) 0.6903(11) 0.3543(2) 0.0931(17) Uani 1 1 d .
H39A H 0.5389 0.7332 0.3358 0.140 Uiso 1 1 calc R
H39B H 0.5183 0.5863 0.3864 0.140 Uiso 1 1 calc R
H39C H 0.4700 0.8242 0.3695 0.140 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'
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
F P O5 87.32(11) y
F P O6 177.73(11) y
F P O7 91.73(10) y
F P O8 91.49(11) y
O5 P O6 91.80(12) y
O5 P O7 116.62(11) y
O5 P O8 121.90(11) y
O6 P O7 90.53(11) y
O6 P O8 87.21(12) y
O7 P O8 121.47(11) y
C5 O5 P 114.6(2) y
C6 O6 P 111.5(2) y
C10 O7 P 127.63(18) y
C23 O8 P 126.04(19) y
C1 O1 C4 109.3(2) ?
C1 O2 C7 110.0(3) ?
C7 O3 C2 109.1(3) ?
O2 C1 O1 111.3(3) ?
O2 C1 C2 106.0(3) ?
O1 C1 C2 106.9(3) ?
O3 C2 C3 109.8(3) ?
O3 C2 C1 103.1(3) ?
C3 C2 C1 104.5(3) ?
O4 C3 C2 110.5(3) ?
O4 C3 C4 109.9(3) ?
C2 C3 C4 100.8(3) ?
O1 C4 C5 107.5(2) ?
O1 C4 C3 103.9(2) ?
C5 C4 C3 116.4(3) ?
O5 C5 C4 107.0(2) ?
O5 C5 C6 103.9(2) ?
C4 C5 C6 112.9(3) ?
O6 C6 C5 103.2(3) ?
O3 C7 O2 105.8(3) ?
O3 C7 C8 107.9(4) ?
O2 C7 C8 109.7(4) ?
O3 C7 C9 110.2(4) ?
O2 C7 C9 109.1(3) ?
C8 C7 C9 113.8(4) ?
C15 C10 C11 122.8(3) ?
C15 C10 O7 117.1(3) ?
C11 C10 O7 119.8(2) ?
C12 C11 C10 115.9(3) ?
C12 C11 C24 120.5(3) ?
C10 C11 C24 123.7(3) ?
C13 C12 C11 124.0(3) ?
C14 C13 C12 117.6(3) ?
C14 C13 C25 121.3(3) ?
C12 C13 C25 121.1(3) ?
C13 C14 C15 121.8(3) ?
C10 C15 C14 117.9(3) ?
C10 C15 C16 120.9(3) ?
C14 C15 C16 121.2(3) ?
C15 C16 C17 113.4(3) ?
C15 C16 C18 109.4(3) ?
C17 C16 C18 113.1(3) ?
C19 C18 C23 118.4(3) ?
C19 C18 C16 120.7(3) ?
C23 C18 C16 120.9(3) ?
C18 C19 C20 121.1(3) ?
C21 C20 C19 117.6(3) ?
C21 C20 C26 121.4(4) ?
C19 C20 C26 121.0(4) ?
C20 C21 C22 124.4(4) ?
C21 C22 C23 115.4(3) ?
C21 C22 C27 120.4(3) ?
C23 C22 C27 124.3(3) ?
C18 C23 C22 123.0(3) ?
C18 C23 O8 117.2(3) ?
C22 C23 O8 119.7(3) ?
C28 C24 C29 109.5(3) ?
C28 C24 C30 105.9(3) ?
C29 C24 C30 107.6(3) ?
C28 C24 C11 112.2(3) ?
C29 C24 C11 109.6(3) ?
C30 C24 C11 111.8(3) ?
C32' C25 C33' 109.7(9) ?
C33 C25 C32 112.9(6) ?
C32' C25 C13 112.2(7) ?
C33 C25 C13 110.4(5) ?
C33' C25 C13 110.1(7) ?
C32 C25 C13 112.5(5) ?
C33 C25 C31 109.2(6) ?
C32 C25 C31 104.7(6) ?
C13 C25 C31 106.7(4) ?
C32' C25 C31' 104.6(9) ?
C33' C25 C31' 108.9(10) ?
C13 C25 C31' 111.2(6) ?
C35' C26 C34' 116.2(10) ?
C36 C26 C20 109.6(5) ?
C35' C26 C20 112.3(7) ?
C34' C26 C20 109.9(8) ?
C36 C26 C35 108.7(8) ?
C20 C26 C35 112.4(6) ?
C36 C26 C34 110.1(7) ?
C20 C26 C34 106.4(6) ?
C35 C26 C34 109.6(7) ?
C35' C26 C36' 101.6(10) ?
C34' C26 C36' 104.9(12) ?
C20 C26 C36' 111.5(8) ?
C37 C27 C39 107.3(4) ?
C37 C27 C38 108.8(4) ?
C39 C27 C38 105.8(4) ?
C37 C27 C22 110.5(3) ?
C39 C27 C22 113.5(4) ?
C38 C27 C22 110.6(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P F 1.605(2) y
P O5 1.608(2) y
P O6 1.652(2) y
P O7 1.604(2) y
P O8 1.598(2) y
O1 C1 1.411(4) ?
O1 C4 1.449(4) ?
O2 C1 1.406(4) ?
O2 C7 1.432(5) ?
O3 C7 1.426(5) ?
O3 C2 1.430(4) ?
O4 C3 1.404(4) ?
O5 C5 1.459(4) ?
O6 C6 1.403(4) ?
O7 C10 1.406(3) ?
O8 C23 1.410(4) ?
C1 C2 1.515(5) ?
C2 C3 1.515(4) ?
C3 C4 1.523(5) ?
C4 C5 1.517(4) ?
C5 C6 1.523(5) ?
C7 C8 1.486(6) ?
C7 C9 1.500(5) ?
C10 C15 1.394(4) ?
C10 C11 1.400(4) ?
C11 C12 1.389(4) ?
C11 C24 1.545(4) ?
C12 C13 1.388(5) ?
C13 C14 1.383(5) ?
C13 C25 1.545(5) ?
C14 C15 1.396(4) ?
C15 C16 1.528(4) ?
C16 C17 1.529(5) ?
C16 C18 1.532(5) ?
C18 C19 1.384(5) ?
C18 C23 1.388(5) ?
C19 C20 1.399(6) ?
C20 C21 1.375(6) ?
C20 C26 1.553(5) ?
C21 C22 1.386(5) ?
C22 C23 1.401(5) ?
C22 C27 1.543(5) ?
C24 C28 1.527(5) ?
C24 C29 1.534(6) ?
C24 C30 1.534(5) ?
C25 C32' 1.487(18) ?
C25 C33 1.505(12) ?
C25 C33' 1.511(18) ?
C25 C32 1.525(10) ?
C25 C31 1.581(10) ?
C25 C31' 1.660(17) ?
C26 C36 1.499(13) ?
C26 C35' 1.537(18) ?
C26 C34' 1.55(2) ?
C26 C35 1.558(13) ?
C26 C34 1.573(12) ?
C26 C36' 1.60(2) ?
C27 C37 1.522(6) ?
C27 C39 1.524(5) ?
C27 C38 1.535(7) ?
