#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/06/2220684.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2220684
loop_
_publ_author_name
'Karami, Kazem'
'Büyükgüngör, Orhan'
_publ_section_title
;
 (4-Methoxybenzoylmethyl)triphenylphosphonium trifluoromethanesulfonate
;
_journal_coeditor_code           AT2703
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o296
_journal_paper_doi               10.1107/S1600536809000919
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C27 H24 O2 P +, C F3 O3 S -'
_chemical_formula_moiety         'C27 H24 O2 P +, C F3 O3 S -'
_chemical_formula_sum            'C28 H24 F3 O5 P S'
_chemical_formula_weight         560.50
_chemical_melting_point          296
_chemical_name_systematic
;
(4-Methoxybenzoylmethyl)triphenylphosphonium trifluoromethanesulfonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 96.539(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.6641(5)
_cell_length_b                   20.2760(12)
_cell_length_c                   25.0960(11)
_cell_measurement_reflns_used    685
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      1
_cell_volume                     5391.1(5)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDSII'
_diffrn_measurement_method       rotation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focfine-focus us sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            75273
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.29
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32: Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.333
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.287
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     685
_refine_ls_number_reflns         11185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1553
_refine_ls_R_factor_gt           0.0789
_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)+(0.0814P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1880
_reflns_number_gt                6282
_reflns_number_total             11185
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2703.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220684
_cod_database_fobs_code          2220684
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2371(3) 0.4197(2) 0.62037(15) 0.0498(9) Uani d . 1 . .
C C2 0.3253(4) 0.4694(2) 0.62123(18) 0.0650(11) Uani d . 1 . .
H H2 0.3261 0.5035 0.6461 0.078 Uiso calc R 1 . .
C C3 0.4130(4) 0.4678(3) 0.5844(2) 0.0803(14) Uani d . 1 . .
H H3 0.4732 0.5010 0.5845 0.096 Uiso calc R 1 . .
C C4 0.4111(4) 0.4177(3) 0.54798(19) 0.0798(15) Uani d . 1 . .
H H4 0.4699 0.4175 0.5233 0.096 Uiso calc R 1 . .
C C5 0.3252(4) 0.3682(3) 0.54703(17) 0.0723(13) Uani d . 1 . .
H H5 0.3262 0.3339 0.5225 0.087 Uiso calc R 1 . .
C C6 0.2369(4) 0.3695(2) 0.58279(16) 0.0602(11) Uani d . 1 . .
H H6 0.1763 0.3364 0.5818 0.072 Uiso calc R 1 . .
C C7 -0.0308(4) 0.4156(2) 0.61744(15) 0.0528(9) Uani d . 1 . .
C C8 -0.0458(4) 0.4641(2) 0.57783(16) 0.0622(11) Uani d . 1 . .
H H8 0.0151 0.4968 0.5769 0.075 Uiso calc R 1 . .
C C9 -0.1508(4) 0.4638(3) 0.53982(18) 0.0742(13) Uani d . 1 . .
H H9 -0.1609 0.4963 0.5135 0.089 Uiso calc R 1 . .
C C10 -0.2396(5) 0.4153(3) 0.5414(2) 0.0873(16) Uani d . 1 . .
H H10 -0.3085 0.4140 0.5151 0.105 Uiso calc R 1 . .
C C11 -0.2280(5) 0.3693(3) 0.5808(2) 0.1002(19) Uani d . 1 . .
H H11 -0.2912 0.3380 0.5823 0.120 Uiso calc R 1 . .
C C12 -0.1216(4) 0.3684(3) 0.6196(2) 0.0782(14) Uani d . 1 . .
H H12 -0.1133 0.3362 0.6462 0.094 Uiso calc R 1 . .
C C13 0.1237(4) 0.3494(2) 0.70769(15) 0.0543(10) Uani d . 1 . .
C C14 0.0411(5) 0.3450(3) 0.74678(19) 0.0782(14) Uani d . 1 . .
H H14 -0.0195 0.3774 0.7495 0.094 Uiso calc R 1 . .
C C15 0.0505(5) 0.2920(3) 0.7812(2) 0.0906(16) Uani d . 1 . .
H H15 -0.0046 0.2887 0.8073 0.109 Uiso calc R 1 . .
C C16 0.1381(5) 0.2446(3) 0.7779(2) 0.0836(15) Uani d . 1 . .
H H16 0.1435 0.2094 0.8018 0.100 Uiso calc R 1 . .
C C17 0.2186(5) 0.2481(2) 0.7395(2) 0.0775(13) Uani d . 1 . .
H H17 0.2774 0.2147 0.7368 0.093 Uiso calc R 1 . .
C C18 0.2133(4) 0.3009(2) 0.70465(17) 0.0642(11) Uani d . 1 . .
H H18 0.2699 0.3038 0.6792 0.077 Uiso calc R 1 . .
C C19 0.1036(4) 0.4932(2) 0.70104(15) 0.0539(10) Uani d . 1 . .
H H19A 0.1028 0.5307 0.6770 0.065 Uiso calc R 1 . .
H H19B 0.0247 0.4935 0.7169 0.065 Uiso calc R 1 . .
C C20 0.2119(4) 0.5012(2) 0.74527(15) 0.0503(9) Uani d . 1 . .
C C21 0.1997(3) 0.55009(19) 0.78769(15) 0.0495(9) Uani d . 1 . .
C C22 0.1026(4) 0.5967(2) 0.78495(17) 0.0592(10) Uani d . 1 . .
H H22 0.0417 0.5973 0.7553 0.071 Uiso calc R 1 . .
C C23 0.0962(4) 0.6414(2) 0.82528(17) 0.0652(11) Uani d . 1 . .
H H23 0.0316 0.6725 0.8228 0.078 Uiso calc R 1 . .
C C24 0.1854(4) 0.6404(2) 0.86965(17) 0.0637(11) Uani d . 1 . .
C C25 0.2826(4) 0.5952(2) 0.87317(16) 0.0637(12) Uani d . 1 . .
H H25 0.3433 0.5948 0.9029 0.076 Uiso calc R 1 . .
C C26 0.2887(4) 0.5508(2) 0.83254(16) 0.0574(10) Uani d . 1 . .
H H26 0.3542 0.5202 0.8350 0.069 Uiso calc R 1 . .
C C27 0.2565(6) 0.6850(4) 0.9558(2) 0.119(2) Uani d . 1 . .
H H27A 0.2362 0.7201 0.9790 0.179 Uiso calc R 1 . .
H H27B 0.3415 0.6903 0.9473 0.179 Uiso calc R 1 . .
H H27C 0.2489 0.6434 0.9735 0.179 Uiso calc R 1 . .
C C28 0.6457(3) 0.3595(2) 0.76582(15) 0.0513(9) Uani d . 1 . .
C C29 0.5704(4) 0.3669(2) 0.71752(17) 0.0659(12) Uani d . 1 . .
H H29 0.5308 0.4070 0.7090 0.079 Uiso calc R 1 . .
C C30 0.5537(5) 0.3152(3) 0.68215(19) 0.0781(14) Uani d . 1 . .
H H30 0.5015 0.3201 0.6501 0.094 Uiso calc R 1 . .
C C31 0.6134(5) 0.2572(3) 0.6939(2) 0.0835(15) Uani d . 1 . .
H H31 0.6030 0.2224 0.6696 0.100 Uiso calc R 1 . .
C C32 0.6883(5) 0.2494(3) 0.7409(2) 0.0913(16) Uani d . 1 . .
H H32 0.7285 0.2092 0.7486 0.110 Uiso calc R 1 . .
C C33 0.7055(4) 0.3002(2) 0.77731(18) 0.0702(12) Uani d . 1 . .
H H33 0.7571 0.2946 0.8094 0.084 Uiso calc R 1 . .
C C34 0.5360(4) 0.40709(19) 0.85901(15) 0.0517(9) Uani d . 1 . .
C C35 0.4350(4) 0.3661(2) 0.84246(18) 0.0716(13) Uani d . 1 . .
H H35 0.4278 0.3472 0.8085 0.086 Uiso calc R 1 . .
C C36 0.3453(5) 0.3534(3) 0.8767(2) 0.1001(19) Uani d . 1 . .
H H36 0.2769 0.3262 0.8658 0.120 Uiso calc R 1 . .
C C37 0.3577(6) 0.3812(4) 0.9268(3) 0.104(2) Uani d . 1 . .
H H37 0.2983 0.3717 0.9501 0.125 Uiso calc R 1 . .
C C38 0.4554(6) 0.4223(3) 0.9431(2) 0.0998(18) Uani d . 1 . .
H H38 0.4620 0.4412 0.9770 0.120 Uiso calc R 1 . .
C C39 0.5447(5) 0.4357(2) 0.90883(18) 0.0732(13) Uani d . 1 . .
H H39 0.6110 0.4643 0.9196 0.088 Uiso calc R 1 . .
C C40 0.8025(4) 0.4269(2) 0.85787(16) 0.0548(10) Uani d . 1 . .
C C41 0.8310(4) 0.3769(2) 0.89511(18) 0.0698(12) Uani d . 1 . .
H H41 0.7763 0.3413 0.8965 0.084 Uiso calc R 1 . .
C C42 0.9406(5) 0.3798(3) 0.9301(2) 0.0839(15) Uani d . 1 . .
H H42 0.9601 0.3459 0.9546 0.101 Uiso calc R 1 . .
C C43 1.0204(5) 0.4323(3) 0.9288(2) 0.0912(17) Uani d . 1 . .
H H43 1.0938 0.4343 0.9526 0.109 Uiso calc R 1 . .
C C44 0.9928(5) 0.4816(3) 0.8928(2) 0.0897(16) Uani d . 1 . .
H H44 1.0476 0.5172 0.8920 0.108 Uiso calc R 1 . .
C C45 0.8839(4) 0.4793(2) 0.8573(2) 0.0727(13) Uani d . 1 . .
H H45 0.8656 0.5134 0.8329 0.087 Uiso calc R 1 . .
C C46 0.6179(4) 0.50060(19) 0.78234(16) 0.0514(9) Uani d . 1 . .
H H46A 0.5295 0.5006 0.7679 0.062 Uiso calc R 1 . .
H H46B 0.6304 0.5360 0.8084 0.062 Uiso calc R 1 . .
C C47 0.6978(4) 0.5137(2) 0.73732(16) 0.0534(10) Uani d . 1 . .
C C48 0.6536(3) 0.56138(19) 0.69497(15) 0.0495(9) Uani d . 1 . .
C C49 0.5466(4) 0.6000(2) 0.69589(17) 0.0607(11) Uani d . 1 . .
H H49 0.5008 0.5974 0.7252 0.073 Uiso calc R 1 . .
C C50 0.5068(4) 0.6422(2) 0.65444(19) 0.0709(12) Uani d . 1 . .
H H50 0.4345 0.6676 0.6556 0.085 Uiso calc R 1 . .
C C51 0.5753(4) 0.6464(2) 0.61101(17) 0.0660(12) Uani d . 1 . .
C C52 0.6829(5) 0.6085(3) 0.6100(2) 0.0819(15) Uani d . 1 . .
H H52 0.7296 0.6115 0.5810 0.098 Uiso calc R 1 . .
C C53 0.7206(4) 0.5672(2) 0.65113(18) 0.0676(12) Uani d . 1 . .
H H53 0.7932 0.5421 0.6499 0.081 Uiso calc R 1 . .
C C54 0.4351(6) 0.7247(3) 0.5649(2) 0.110(2) Uani d . 1 . .
H H54A 0.4263 0.7492 0.5320 0.165 Uiso calc R 1 . .
H H54B 0.4419 0.7546 0.5947 0.165 Uiso calc R 1 . .
H H54C 0.3625 0.6970 0.5663 0.165 Uiso calc R 1 . .
C C55 -0.0022(5) 0.6781(3) 0.5545(2) 0.0789(14) Uani d . 1 . .
C C56 0.8050(6) 0.8346(3) 0.4279(3) 0.0893(16) Uani d . 1 . .
F F1 -0.0619(3) 0.6251(2) 0.53358(14) 0.1184(12) Uani d . 1 . .
F F2 -0.0878(3) 0.72038(18) 0.56646(15) 0.1195(12) Uani d . 1 . .
F F3 0.0579(4) 0.7046(2) 0.51722(14) 0.1332(14) Uani d . 1 . .
F F4 0.8159(4) 0.8128(3) 0.47665(15) 0.1514(17) Uani d . 1 . .
F F5 0.8797(5) 0.8827(3) 0.4279(3) 0.211(3) Uani d . 1 . .
F F6 0.8564(4) 0.7876(2) 0.40148(19) 0.1530(16) Uani d . 1 . .
O O1 0.3065(3) 0.46701(15) 0.74453(11) 0.0653(8) Uani d . 1 . .
O O2 0.1719(3) 0.68647(18) 0.90766(14) 0.0893(11) Uani d . 1 . .
O O3 0.7972(3) 0.48392(16) 0.73638(12) 0.0718(9) Uani d . 1 . .
O O4 0.5451(4) 0.68504(19) 0.56762(13) 0.0946(11) Uani d . 1 . .
O O5 0.0177(4) 0.6331(2) 0.64958(14) 0.1079(13) Uani d . 1 . .
O O6 0.1662(4) 0.71576(19) 0.6272(2) 0.1266(16) Uani d . 1 . .
O O7 0.1802(3) 0.60495(18) 0.59502(17) 0.0979(12) Uani d . 1 . .
O O8 0.5820(5) 0.7954(3) 0.4125(3) 0.183(3) Uani d . 1 . .
O O9 0.6181(6) 0.9064(3) 0.4313(2) 0.157(2) Uani d . 1 . .
O O10 0.6530(6) 0.8681(3) 0.34844(17) 0.154(2) Uani d . 1 . .
P P1 0.11235(9) 0.41867(5) 0.66285(4) 0.0478(3) Uani d . 1 . .
P P2 0.65496(9) 0.42347(5) 0.81549(4) 0.0482(3) Uani d . 1 . .
S S1 0.10381(12) 0.65597(6) 0.61330(5) 0.0681(3) Uani d . 1 . .
S S2 0.64543(14) 0.85241(7) 0.40166(5) 0.0844(4) Uani d . 1 . .
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.7(4) ?
C2 C1 P1 . . 123.3(3) ?
C6 C1 P1 . . 116.8(3) ?
C1 C2 C3 . . 118.9(5) ?
C1 C2 H2 . . 120.6 ?
C3 C2 H2 . . 120.6 ?
C4 C3 C2 . . 120.2(5) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C5 C4 C3 . . 121.4(4) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
C4 C5 C6 . . 119.1(5) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
C5 C6 C1 . . 120.7(4) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.6 ?
C12 C7 C8 . . 119.9(4) ?
C12 C7 P1 . . 123.5(3) ?
C8 C7 P1 . . 116.6(3) ?
C9 C8 C7 . . 120.4(4) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C10 C9 C8 . . 119.4(5) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C11 C10 C9 . . 120.6(5) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C10 C11 C12 . . 120.9(5) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
C7 C12 C11 . . 118.7(5) ?
C7 C12 H12 . . 120.6 ?
C11 C12 H12 . . 120.6 ?
C18 C13 C14 . . 119.4(4) ?
C18 C13 P1 . . 121.4(3) ?
C14 C13 P1 . . 119.2(3) ?
C15 C14 C13 . . 119.0(5) ?
C15 C14 H14 . . 120.5 ?
C13 C14 H14 . . 120.5 ?
C16 C15 C14 . . 121.2(5) ?
C16 C15 H15 . . 119.4 ?
C14 C15 H15 . . 119.4 ?
C15 C16 C17 . . 120.2(5) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C16 C17 C18 . . 120.3(5) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C17 C18 C13 . . 119.9(4) ?
C17 C18 H18 . . 120.1 ?
C13 C18 H18 . . 120.1 ?
C20 C19 P1 . . 113.4(3) ?
C20 C19 H19A . . 108.9 ?
P1 C19 H19A . . 108.9 ?
C20 C19 H19B . . 108.9 ?
P1 C19 H19B . . 108.9 ?
H19A C19 H19B . . 107.7 ?
O1 C20 C21 . . 122.2(3) ?
O1 C20 C19 . . 119.2(3) ?
C21 C20 C19 . . 118.6(3) ?
C26 C21 C22 . . 117.9(4) ?
C26 C21 C20 . . 119.0(4) ?
C22 C21 C20 . . 123.1(3) ?
C23 C22 C21 . . 120.8(4) ?
C23 C22 H22 . . 119.6 ?
C21 C22 H22 . . 119.6 ?
C22 C23 C24 . . 120.0(4) ?
C22 C23 H23 . . 120.0 ?
C24 C23 H23 . . 120.0 ?
O2 C24 C25 . . 123.6(4) ?
O2 C24 C23 . . 116.0(4) ?
C25 C24 C23 . . 120.4(4) ?
C26 C25 C24 . . 119.3(4) ?
C26 C25 H25 . . 120.3 ?
C24 C25 H25 . . 120.3 ?
C25 C26 C21 . . 121.7(4) ?
C25 C26 H26 . . 119.2 ?
C21 C26 H26 . . 119.2 ?
O2 C27 H27A . . 109.5 ?
O2 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
O2 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C33 C28 C29 . . 119.1(4) ?
C33 C28 P2 . . 119.9(3) ?
C29 C28 P2 . . 120.8(3) ?
C30 C29 C28 . . 120.3(4) ?
C30 C29 H29 . . 119.8 ?
C28 C29 H29 . . 119.8 ?
C31 C30 C29 . . 120.0(4) ?
C31 C30 H30 . . 120.0 ?
C29 C30 H30 . . 120.0 ?
C30 C31 C32 . . 120.4(5) ?
C30 C31 H31 . . 119.8 ?
C32 C31 H31 . . 119.8 ?
C31 C32 C33 . . 120.7(5) ?
C31 C32 H32 . . 119.6 ?
C33 C32 H32 . . 119.6 ?
C28 C33 C32 . . 119.5(4) ?
C28 C33 H33 . . 120.3 ?
C32 C33 H33 . . 120.3 ?
C39 C34 C35 . . 119.7(4) ?
C39 C34 P2 . . 119.8(3) ?
C35 C34 P2 . . 120.5(3) ?
C36 C35 C34 . . 119.7(5) ?
C36 C35 H35 . . 120.2 ?
C34 C35 H35 . . 120.2 ?
C37 C36 C35 . . 119.5(5) ?
C37 C36 H36 . . 120.2 ?
C35 C36 H36 . . 120.2 ?
C38 C37 C36 . . 121.2(5) ?
C38 C37 H37 . . 119.4 ?
C36 C37 H37 . . 119.4 ?
C37 C38 C39 . . 119.5(5) ?
C37 C38 H38 . . 120.2 ?
C39 C38 H38 . . 120.2 ?
C34 C39 C38 . . 120.3(5) ?
C34 C39 H39 . . 119.9 ?
C38 C39 H39 . . 119.9 ?
C45 C40 C41 . . 118.8(4) ?
C45 C40 P2 . . 122.4(3) ?
C41 C40 P2 . . 118.7(3) ?
C42 C41 C40 . . 120.1(4) ?
C42 C41 H41 . . 120.0 ?
C40 C41 H41 . . 120.0 ?
C43 C42 C41 . . 120.2(5) ?
C43 C42 H42 . . 119.9 ?
C41 C42 H42 . . 119.9 ?
C44 C43 C42 . . 120.1(4) ?
C44 C43 H43 . . 119.9 ?
C42 C43 H43 . . 119.9 ?
C43 C44 C45 . . 120.5(5) ?
C43 C44 H44 . . 119.7 ?
C45 C44 H44 . . 119.7 ?
C40 C45 C44 . . 120.3(4) ?
C40 C45 H45 . . 119.8 ?
C44 C45 H45 . . 119.8 ?
C47 C46 P2 . . 112.7(3) ?
C47 C46 H46A . . 109.0 ?
P2 C46 H46A . . 109.0 ?
C47 C46 H46B . . 109.0 ?
P2 C46 H46B . . 109.0 ?
H46A C46 H46B . . 107.8 ?
O3 C47 C48 . . 121.1(4) ?
O3 C47 C46 . . 119.3(3) ?
C48 C47 C46 . . 119.5(3) ?
C53 C48 C49 . . 117.8(4) ?
C53 C48 C47 . . 118.5(4) ?
C49 C48 C47 . . 123.7(4) ?
C50 C49 C48 . . 121.5(4) ?
C50 C49 H49 . . 119.2 ?
C48 C49 H49 . . 119.2 ?
C49 C50 C51 . . 119.3(4) ?
C49 C50 H50 . . 120.4 ?
C51 C50 H50 . . 120.4 ?
O4 C51 C50 . . 124.9(4) ?
O4 C51 C52 . . 115.5(4) ?
C50 C51 C52 . . 119.6(4) ?
C53 C52 C51 . . 120.3(4) ?
C53 C52 H52 . . 119.8 ?
C51 C52 H52 . . 119.8 ?
C52 C53 C48 . . 121.5(4) ?
C52 C53 H53 . . 119.2 ?
C48 C53 H53 . . 119.2 ?
O4 C54 H54A . . 109.5 ?
O4 C54 H54B . . 109.5 ?
H54A C54 H54B . . 109.5 ?
O4 C54 H54C . . 109.5 ?
H54A C54 H54C . . 109.5 ?
H54B C54 H54C . . 109.5 ?
F3 C55 F2 . . 107.8(5) ?
F3 C55 F1 . . 107.7(5) ?
F2 C55 F1 . . 107.8(5) ?
F3 C55 S1 . . 111.9(4) ?
F2 C55 S1 . . 111.1(4) ?
F1 C55 S1 . . 110.4(4) ?
F5 C56 F4 . . 106.1(6) ?
F5 C56 F6 . . 105.2(6) ?
F4 C56 F6 . . 103.4(5) ?
F5 C56 S2 . . 114.7(5) ?
F4 C56 S2 . . 113.3(5) ?
F6 C56 S2 . . 113.2(4) ?
C24 O2 C27 . . 118.3(4) ?
C51 O4 C54 . . 119.2(4) ?
C13 P1 C1 . . 112.27(19) ?
C13 P1 C19 . . 109.13(19) ?
C1 P1 C19 . . 113.18(19) ?
C13 P1 C7 . . 111.24(19) ?
C1 P1 C7 . . 104.86(17) ?
C19 P1 C7 . . 105.94(18) ?
C28 P2 C46 . . 108.42(18) ?
C28 P2 C34 . . 107.57(19) ?
C46 P2 C34 . . 108.02(17) ?
C28 P2 C40 . . 114.50(18) ?
C46 P2 C40 . . 111.87(19) ?
C34 P2 C40 . . 106.16(18) ?
O6 S1 O7 . . 115.7(3) ?
O6 S1 O5 . . 115.9(3) ?
O7 S1 O5 . . 113.5(3) ?
O6 S1 C55 . . 102.9(3) ?
O7 S1 C55 . . 104.1(3) ?
O5 S1 C55 . . 102.2(2) ?
O9 S2 O8 . . 114.9(4) ?
O9 S2 O10 . . 112.2(4) ?
O8 S2 O10 . . 117.8(4) ?
O9 S2 C56 . . 102.3(3) ?
O8 S2 C56 . . 103.0(3) ?
O10 S2 C56 . . 104.2(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.378(6) ?
C1 C6 . 1.387(6) ?
C1 P1 . 1.797(4) ?
C2 C3 . 1.389(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.365(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.357(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.373(6) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.368(6) ?
C7 C8 . 1.394(6) ?
C7 P1 . 1.799(4) ?
C8 C9 . 1.386(6) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.369(7) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.355(8) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.409(7) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C18 . 1.379(6) ?
C13 C14 . 1.394(6) ?
C13 P1 . 1.795(4) ?
C14 C15 . 1.376(7) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.349(7) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.364(7) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.379(6) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 C20 . 1.517(5) ?
C19 P1 . 1.798(4) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 O1 . 1.226(4) ?
C20 C21 . 1.471(5) ?
C21 C26 . 1.387(5) ?
C21 C22 . 1.398(6) ?
C22 C23 . 1.366(6) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.380(6) ?
C23 H23 . 0.9300 ?
C24 O2 . 1.355(5) ?
C24 C25 . 1.379(6) ?
C25 C26 . 1.367(6) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
C27 O2 . 1.423(6) ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
C28 C33 . 1.376(6) ?
C28 C29 . 1.384(5) ?
C28 P2 . 1.794(4) ?
C29 C30 . 1.371(6) ?
C29 H29 . 0.9300 ?
C30 C31 . 1.355(7) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.357(7) ?
C31 H31 . 0.9300 ?
C32 C33 . 1.376(7) ?
C32 H32 . 0.9300 ?
C33 H33 . 0.9300 ?
C34 C39 . 1.372(6) ?
C34 C35 . 1.387(6) ?
C34 P2 . 1.796(4) ?
C35 C36 . 1.381(7) ?
C35 H35 . 0.9300 ?
C36 C37 . 1.370(8) ?
C36 H36 . 0.9300 ?
C37 C38 . 1.360(9) ?
C37 H37 . 0.9300 ?
C38 C39 . 1.380(7) ?
C38 H38 . 0.9300 ?
C39 H39 . 0.9300 ?
C40 C45 . 1.373(6) ?
C40 C41 . 1.390(6) ?
C40 P2 . 1.797(4) ?
C41 C42 . 1.380(6) ?
C41 H41 . 0.9300 ?
C42 C43 . 1.366(7) ?
C42 H42 . 0.9300 ?
C43 C44 . 1.356(7) ?
C43 H43 . 0.9300 ?
C44 C45 . 1.382(6) ?
C44 H44 . 0.9300 ?
C45 H45 . 0.9300 ?
C46 C47 . 1.514(5) ?
C46 P2 . 1.794(4) ?
C46 H46A . 0.9700 ?
C46 H46B . 0.9700 ?
C47 O3 . 1.223(5) ?
C47 C48 . 1.473(5) ?
C48 C53 . 1.384(6) ?
C48 C49 . 1.386(5) ?
C49 C50 . 1.376(6) ?
C49 H49 . 0.9300 ?
C50 C51 . 1.382(6) ?
C50 H50 . 0.9300 ?
C51 O4 . 1.350(5) ?
C51 C52 . 1.384(7) ?
C52 C53 . 1.354(6) ?
C52 H52 . 0.9300 ?
C53 H53 . 0.9300 ?
C54 O4 . 1.417(6) ?
C54 H54A . 0.9600 ?
C54 H54B . 0.9600 ?
C54 H54C . 0.9600 ?
C55 F3 . 1.308(6) ?
C55 F2 . 1.312(6) ?
C55 F1 . 1.326(6) ?
C55 S1 . 1.811(5) ?
C56 F5 . 1.260(7) ?
C56 F4 . 1.293(7) ?
C56 F6 . 1.317(6) ?
C56 S2 . 1.791(7) ?
O5 S1 . 1.441(4) ?
O6 S1 . 1.408(4) ?
O7 S1 . 1.424(4) ?
O8 S2 . 1.381(5) ?
O9 S2 . 1.374(5) ?
O10 S2 . 1.384(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C19 H19A O5 . 0.97 2.34 3.207(6) 149 yes
C19 H19B O3 1_455 0.97 2.54 3.487(5) 166 yes
C33 H33 O6 2_646 0.93 2.34 3.130(6) 143 yes
C45 H45 O3 . 0.93 2.52 3.071(6) 118 yes
C46 H46A O1 . 0.97 2.48 3.417(5) 162 yes
C46 H46B O10 4_576 0.97 2.19 3.137(7) 165 yes
C44 H44 Cg4 1_655 0.93 2.83 3.640(6) 147 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.4(6) ?
P1 C1 C2 C3 . . . . -175.8(3) ?
C1 C2 C3 C4 . . . . 0.1(7) ?
C2 C3 C4 C5 . . . . -0.6(8) ?
C3 C4 C5 C6 . . . . 1.4(7) ?
C4 C5 C6 C1 . . . . -1.7(7) ?
C2 C1 C6 C5 . . . . 1.2(6) ?
P1 C1 C6 C5 . . . . 176.9(3) ?
C12 C7 C8 C9 . . . . -1.5(7) ?
P1 C7 C8 C9 . . . . 177.4(3) ?
C7 C8 C9 C10 . . . . -0.3(7) ?
C8 C9 C10 C11 . . . . 2.5(8) ?
C9 C10 C11 C12 . . . . -3.0(9) ?
C8 C7 C12 C11 . . . . 1.1(7) ?
P1 C7 C12 C11 . . . . -177.8(4) ?
C10 C11 C12 C7 . . . . 1.2(9) ?
C18 C13 C14 C15 . . . . -0.4(7) ?
P1 C13 C14 C15 . . . . -179.7(4) ?
C13 C14 C15 C16 . . . . 0.2(8) ?
C14 C15 C16 C17 . . . . -0.8(9) ?
C15 C16 C17 C18 . . . . 1.6(8) ?
C16 C17 C18 C13 . . . . -1.8(7) ?
C14 C13 C18 C17 . . . . 1.2(7) ?
P1 C13 C18 C17 . . . . -179.5(3) ?
P1 C19 C20 O1 . . . . 15.7(5) ?
P1 C19 C20 C21 . . . . -164.4(3) ?
O1 C20 C21 C26 . . . . -10.1(6) ?
C19 C20 C21 C26 . . . . 170.1(4) ?
O1 C20 C21 C22 . . . . 169.4(4) ?
C19 C20 C21 C22 . . . . -10.5(6) ?
C26 C21 C22 C23 . . . . 0.0(6) ?
C20 C21 C22 C23 . . . . -179.5(4) ?
C21 C22 C23 C24 . . . . -0.7(7) ?
C22 C23 C24 O2 . . . . 180.0(4) ?
C22 C23 C24 C25 . . . . 1.1(7) ?
O2 C24 C25 C26 . . . . -179.6(4) ?
C23 C24 C25 C26 . . . . -0.8(7) ?
C24 C25 C26 C21 . . . . 0.1(7) ?
C22 C21 C26 C25 . . . . 0.3(6) ?
C20 C21 C26 C25 . . . . 179.8(4) ?
C33 C28 C29 C30 . . . . 1.3(7) ?
P2 C28 C29 C30 . . . . -173.3(4) ?
C28 C29 C30 C31 . . . . -1.5(8) ?
C29 C30 C31 C32 . . . . 1.0(8) ?
C30 C31 C32 C33 . . . . -0.3(9) ?
C29 C28 C33 C32 . . . . -0.6(7) ?
P2 C28 C33 C32 . . . . 174.0(4) ?
C31 C32 C33 C28 . . . . 0.2(8) ?
C39 C34 C35 C36 . . . . -1.2(7) ?
P2 C34 C35 C36 . . . . 179.2(4) ?
C34 C35 C36 C37 . . . . -0.5(9) ?
C35 C36 C37 C38 . . . . 1.6(10) ?
C36 C37 C38 C39 . . . . -0.8(10) ?
C35 C34 C39 C38 . . . . 1.9(7) ?
P2 C34 C39 C38 . . . . -178.5(4) ?
C37 C38 C39 C34 . . . . -0.9(9) ?
C45 C40 C41 C42 . . . . -1.0(7) ?
P2 C40 C41 C42 . . . . -176.7(4) ?
C40 C41 C42 C43 . . . . 0.9(8) ?
C41 C42 C43 C44 . . . . -0.5(9) ?
C42 C43 C44 C45 . . . . 0.2(9) ?
C41 C40 C45 C44 . . . . 0.7(7) ?
P2 C40 C45 C44 . . . . 176.2(4) ?
C43 C44 C45 C40 . . . . -0.3(9) ?
P2 C46 C47 O3 . . . . -19.7(5) ?
P2 C46 C47 C48 . . . . 159.4(3) ?
O3 C47 C48 C53 . . . . 6.2(6) ?
C46 C47 C48 C53 . . . . -172.8(4) ?
O3 C47 C48 C49 . . . . -175.2(4) ?
C46 C47 C48 C49 . . . . 5.8(6) ?
C53 C48 C49 C50 . . . . 0.9(7) ?
C47 C48 C49 C50 . . . . -177.7(4) ?
C48 C49 C50 C51 . . . . -0.4(7) ?
C49 C50 C51 O4 . . . . 179.0(4) ?
C49 C50 C51 C52 . . . . -0.3(7) ?
O4 C51 C52 C53 . . . . -178.9(5) ?
C50 C51 C52 C53 . . . . 0.5(8) ?
C51 C52 C53 C48 . . . . 0.1(8) ?
C49 C48 C53 C52 . . . . -0.7(7) ?
C47 C48 C53 C52 . . . . 178.0(4) ?
C25 C24 O2 C27 . . . . -5.1(7) ?
C23 C24 O2 C27 . . . . 176.0(5) ?
C50 C51 O4 C54 . . . . -0.3(8) ?
C52 C51 O4 C54 . . . . 179.0(5) ?
C18 C13 P1 C1 . . . . -5.4(4) ?
C14 C13 P1 C1 . . . . 173.9(3) ?
C18 C13 P1 C19 . . . . -131.8(3) ?
C14 C13 P1 C19 . . . . 47.5(4) ?
C18 C13 P1 C7 . . . . 111.7(4) ?
C14 C13 P1 C7 . . . . -69.0(4) ?
C2 C1 P1 C13 . . . . -117.5(3) ?
C6 C1 P1 C13 . . . . 66.9(3) ?
C2 C1 P1 C19 . . . . 6.6(4) ?
C6 C1 P1 C19 . . . . -169.0(3) ?
C2 C1 P1 C7 . . . . 121.6(3) ?
C6 C1 P1 C7 . . . . -54.0(3) ?
C20 C19 P1 C13 . . . . 55.0(3) ?
C20 C19 P1 C1 . . . . -70.8(3) ?
C20 C19 P1 C7 . . . . 174.8(3) ?
C12 C7 P1 C13 . . . . 3.7(5) ?
C8 C7 P1 C13 . . . . -175.2(3) ?
C12 C7 P1 C1 . . . . 125.3(4) ?
C8 C7 P1 C1 . . . . -53.6(4) ?
C12 C7 P1 C19 . . . . -114.8(4) ?
C8 C7 P1 C19 . . . . 66.4(4) ?
C33 C28 P2 C46 . . . . 160.1(3) ?
C29 C28 P2 C46 . . . . -25.3(4) ?
C33 C28 P2 C34 . . . . -83.3(4) ?
C29 C28 P2 C34 . . . . 91.3(4) ?
C33 C28 P2 C40 . . . . 34.5(4) ?
C29 C28 P2 C40 . . . . -151.0(3) ?
C47 C46 P2 C28 . . . . -53.4(3) ?
C47 C46 P2 C34 . . . . -169.7(3) ?
C47 C46 P2 C40 . . . . 73.8(3) ?
C39 C34 P2 C28 . . . . 160.9(3) ?
C35 C34 P2 C28 . . . . -19.6(4) ?
C39 C34 P2 C46 . . . . -82.2(4) ?
C35 C34 P2 C46 . . . . 97.3(4) ?
C39 C34 P2 C40 . . . . 37.9(4) ?
C35 C34 P2 C40 . . . . -142.6(3) ?
C45 C40 P2 C28 . . . . 114.2(4) ?
C41 C40 P2 C28 . . . . -70.3(4) ?
C45 C40 P2 C46 . . . . -9.7(5) ?
C41 C40 P2 C46 . . . . 165.8(3) ?
C45 C40 P2 C34 . . . . -127.3(4) ?
C41 C40 P2 C34 . . . . 48.2(4) ?
F3 C55 S1 O6 . . . . 55.2(5) ?
F2 C55 S1 O6 . . . . -65.4(4) ?
F1 C55 S1 O6 . . . . 175.1(4) ?
F3 C55 S1 O7 . . . . -65.9(5) ?
F2 C55 S1 O7 . . . . 173.5(4) ?
F1 C55 S1 O7 . . . . 54.0(4) ?
F3 C55 S1 O5 . . . . 175.7(4) ?
F2 C55 S1 O5 . . . . 55.1(4) ?
F1 C55 S1 O5 . . . . -64.4(4) ?
F5 C56 S2 O9 . . . . -53.1(7) ?
F4 C56 S2 O9 . . . . 68.9(5) ?
F6 C56 S2 O9 . . . . -173.7(5) ?
F5 C56 S2 O8 . . . . -172.5(6) ?
F4 C56 S2 O8 . . . . -50.5(6) ?
F6 C56 S2 O8 . . . . 66.8(6) ?
F5 C56 S2 O10 . . . . 64.0(6) ?
F4 C56 S2 O10 . . . . -174.0(5) ?
F6 C56 S2 O10 . . . . -56.7(6) ?
