#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:29:14 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/86/7128660.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_7128660
loop_
_publ_author_name
'Mironov, Vladimir F.'
'Dimukhametov, Mudaris N.'
'Ivkova, Gulnara A.'
'Khayarov, Khasan R.'
'Islamov, Daut R.'
'Litvinov, Igor A.'
_publ_section_title
;
 The formation of cage phosphoranes and their rearrangements in the
 reactions of substituted
 2-(3-oxo-3-phenyl)ethoxybenzo[d]-1,3,2-dioxaphospholes with
 perfluorodiacetyl.
;
_journal_issue                   68
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8516
_journal_page_last               8519
_journal_paper_doi               10.1039/d1cc02941j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C20 H15 F6 O6 P'
_chemical_formula_sum            'C20 H15 F6 O6 P'
_chemical_formula_weight         496.29
_chemical_melting_point          418
_chemical_name_common
4',4'-dimethyl-5'-phenyl-4,5-bis(trifluoromethyl)-4',5'-dihydro-2?5-spiro[[1,3,2]dioxaphosphole-2,2'-[2,5]epoxybenzo[d][1,3,6,2]trioxaphosphocine]
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-21 deposited with the CCDC.	2021-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                104.000(7)
_cell_angle_beta                 97.928(6)
_cell_angle_gamma                90.021(7)
_cell_formula_units_Z            4
_cell_length_a                   10.223(2)
_cell_length_b                   13.603(3)
_cell_length_c                   15.047(3)
_cell_measurement_reflns_used    5232
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.33
_cell_volume                     2009.7(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            16714
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.841
_diffrn_reflns_theta_min         1.544
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.745756
_exptl_absorpt_correction_T_min  0.614984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 48041 reflections, Rint = 0.1219
 (14399 with I > 3sig(I), Rint = 0.0810)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: penthane'
_exptl_crystal_size_max          0.484
_exptl_crystal_size_mid          0.368
_exptl_crystal_size_min          0.208
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.0110(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         16714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0788P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1653
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10152
_reflns_number_total             16714
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02941j2.cif
_cod_data_source_block           miro19t5
_cod_depositor_comments
'Adding full bibliography for 7128660--7128661.cif.'
_cod_original_cell_volume        2009.7(8)
_cod_database_code               7128660
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4562(10)
 0.5438(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Me refined with riding coordinates:
 C22A(H22A,H22B,H22C), C22B(H22D,H22E,H22F), C23A(H23A,H23B,H23C), C23B(H23D,
 H23E,H23F)
3.b Aromatic/amide H refined with riding coordinates:
 C12A(H12A), C12B(H12B), C13A(H13A), C13B(H13B), C14A(H14A), C14B(H14B),
 C15A(H15A), C15B(H15B), C17A(H17A), C17B(H17B), C18A(H18A), C18B(H18B),
 C19A(H19A), C19B(H19B), C20A(H20A), C20B(H20B), C21A(H21A), C21B(H21B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C3A C 0.5258(3) 0.1546(3) 0.0967(2) 0.0181(8) Uani 1 1 d . . . . .
C3B C 0.9685(3) 0.5861(3) 0.8893(2) 0.0187(8) Uani 1 1 d . . . . .
C4A C 0.3967(3) 0.1872(3) 0.0932(2) 0.0177(8) Uani 1 1 d . . . . .
C4B C 1.0958(3) 0.6208(3) 0.8873(2) 0.0187(8) Uani 1 1 d . . . . .
C6A C 0.3164(3) 0.1505(3) 0.2234(2) 0.0179(8) Uani 1 1 d . . . . .
C6B C 1.1716(3) 0.5080(3) 0.7598(2) 0.0171(8) Uani 1 1 d . . . . .
C7A C 0.3478(3) 0.2027(3) 0.3268(2) 0.0191(8) Uani 1 1 d . . . . .
C7B C 1.1369(3) 0.4963(3) 0.6546(3) 0.0220(8) Uani 1 1 d . . . . .
C8A C 0.7781(3) 0.0962(3) 0.3557(2) 0.0202(8) Uani 1 1 d . . . . .
C8B C 0.7085(3) 0.3752(3) 0.6432(2) 0.0185(8) Uani 1 1 d . . . . .
C9A C 0.7152(3) 0.0071(3) 0.3300(2) 0.0202(8) Uani 1 1 d . . . . .
C9B C 0.7726(3) 0.3030(3) 0.6747(2) 0.0183(8) Uani 1 1 d . . . . .
C10A C 0.9101(4) 0.1283(3) 0.4121(3) 0.0270(9) Uani 1 1 d . . . . .
C10B C 0.5774(3) 0.3743(3) 0.5864(3) 0.0239(9) Uani 1 1 d . . . . .
C11A C 0.7479(4) -0.0950(3) 0.3449(3) 0.0279(10) Uani 1 1 d . . . . .
C11B C 0.7394(4) 0.1958(3) 0.6699(3) 0.0241(9) Uani 1 1 d . . . . .
C12A C 0.5806(4) 0.1221(3) 0.0166(2) 0.0207(8) Uani 1 1 d . . . . .
H12A H 0.667880 0.098053 0.018880 0.025 Uiso 1 1 calc R . . . .
C12B C 0.9166(3) 0.6033(3) 0.9705(3) 0.0210(8) Uani 1 1 d . . . . .
H12B H 0.829304 0.579859 0.971238 0.025 Uiso 1 1 calc R . . . .
C13A C 0.5074(4) 0.1248(3) -0.0677(3) 0.0230(9) Uani 1 1 d . . . . .
H13A H 0.545450 0.103975 -0.123127 0.028 Uiso 1 1 calc R . . . .
C13B C 0.9927(4) 0.6550(3) 1.0516(3) 0.0252(9) Uani 1 1 d . . . . .
H13B H 0.957461 0.667667 1.108306 0.030 Uiso 1 1 calc R . . . .
C14A C 0.3791(4) 0.1579(3) -0.0709(3) 0.0222(8) Uani 1 1 d . . . . .
H14A H 0.329111 0.159401 -0.128660 0.027 Uiso 1 1 calc R . . . .
C14B C 1.1209(4) 0.6885(3) 1.0502(3) 0.0253(9) Uani 1 1 d . . . . .
H14B H 1.173092 0.723755 1.106039 0.030 Uiso 1 1 calc R . . . .
C15A C 0.3235(4) 0.1888(3) 0.0098(2) 0.0217(8) Uani 1 1 d . . . . .
H15A H 0.235254 0.211030 0.007498 0.026 Uiso 1 1 calc R . . . .
C15B C 1.1723(3) 0.6706(3) 0.9677(3) 0.0214(8) Uani 1 1 d . . . . .
H15B H 1.260240 0.692569 0.966807 0.026 Uiso 1 1 calc R . . . .
C16A C 0.1795(3) 0.1047(3) 0.1869(2) 0.0167(8) Uani 1 1 d . . . . .
C16B C 1.3101(3) 0.4862(3) 0.7954(2) 0.0174(8) Uani 1 1 d . . . . .
C17A C 0.0761(3) 0.1684(3) 0.1754(2) 0.0213(8) Uani 1 1 d . . . . .
H17A H 0.093438 0.239274 0.186676 0.026 Uiso 1 1 calc R . . . .
C17B C 1.3408(3) 0.3949(3) 0.8159(3) 0.0264(9) Uani 1 1 d . . . . .
H17B H 1.273248 0.344405 0.808575 0.032 Uiso 1 1 calc R . . . .
C18A C -0.0517(3) 0.1298(3) 0.1479(3) 0.0270(9) Uani 1 1 d . . . . .
H18A H -0.121978 0.174293 0.141137 0.032 Uiso 1 1 calc R . . . .
C18B C 1.4708(4) 0.3766(3) 0.8473(3) 0.0326(10) Uani 1 1 d . . . . .
H18B H 1.491972 0.313495 0.861320 0.039 Uiso 1 1 calc R . . . .
C19A C -0.0779(4) 0.0275(3) 0.1302(3) 0.0269(9) Uani 1 1 d . . . . .
H19A H -0.166102 0.001040 0.111273 0.032 Uiso 1 1 calc R . . . .
C19B C 1.5691(4) 0.4498(3) 0.8580(3) 0.0276(9) Uani 1 1 d . . . . .
H19B H 1.657776 0.436912 0.879375 0.033 Uiso 1 1 calc R . . . .
C20A C 0.0242(4) -0.0368(3) 0.1399(3) 0.0314(10) Uani 1 1 d . . . . .
H20A H 0.006669 -0.107858 0.126663 0.038 Uiso 1 1 calc R . . . .
C20B C 1.5391(4) 0.5413(3) 0.8380(3) 0.0247(9) Uani 1 1 d . . . . .
H20B H 1.606934 0.591550 0.845377 0.030 Uiso 1 1 calc R . . . .
C21A C 0.1528(4) 0.0020(3) 0.1690(3) 0.0253(9) Uani 1 1 d . . . . .
H21A H 0.222739 -0.042506 0.176612 0.030 Uiso 1 1 calc R . . . .
C21B C 1.4103(3) 0.5599(3) 0.8072(2) 0.0216(8) Uani 1 1 d . . . . .
H21B H 1.389624 0.623334 0.793904 0.026 Uiso 1 1 calc R . . . .
C22A C 0.3041(4) 0.1377(3) 0.3864(3) 0.0264(9) Uani 1 1 d . . . . .
H22A H 0.207315 0.133796 0.379150 0.040 Uiso 1 1 calc R . . . .
H22B H 0.337511 0.069377 0.367469 0.040 Uiso 1 1 calc R . . . .
H22C H 0.339041 0.167686 0.451403 0.040 Uiso 1 1 calc R . . . .
C22B C 1.1786(4) 0.3967(3) 0.5986(3) 0.0299(10) Uani 1 1 d . . . . .
H22D H 1.275208 0.396692 0.603714 0.045 Uiso 1 1 calc R . . . .
H22E H 1.147215 0.341143 0.622165 0.045 Uiso 1 1 calc R . . . .
H22F H 1.140467 0.387579 0.533616 0.045 Uiso 1 1 calc R . . . .
C23A C 0.3038(4) 0.3105(3) 0.3532(3) 0.0233(9) Uani 1 1 d . . . . .
H23A H 0.207054 0.310886 0.345009 0.035 Uiso 1 1 calc R . . . .
H23B H 0.338709 0.341161 0.418033 0.035 Uiso 1 1 calc R . . . .
H23C H 0.337161 0.349518 0.313624 0.035 Uiso 1 1 calc R . . . .
C23B C 1.1760(4) 0.5864(3) 0.6204(3) 0.0296(10) Uani 1 1 d . . . . .
H23D H 1.272590 0.592307 0.626530 0.044 Uiso 1 1 calc R . . . .
H23E H 1.138342 0.576947 0.555320 0.044 Uiso 1 1 calc R . . . .
H23F H 1.142556 0.648230 0.657361 0.044 Uiso 1 1 calc R . . . .
O1A O 0.7091(2) 0.16990(19) 0.32763(17) 0.0221(6) Uani 1 1 d . . . . .
O1B O 0.7782(2) 0.46291(18) 0.66295(17) 0.0205(6) Uani 1 1 d . . . . .
O2A O 0.6056(2) 0.15700(19) 0.18074(16) 0.0202(6) Uani 1 1 d . . . . .
O2B O 0.8860(2) 0.53959(18) 0.80711(16) 0.0187(6) Uani 1 1 d . . . . .
O3A O 0.5928(2) 0.01232(18) 0.27899(16) 0.0194(6) Uani 1 1 d . . . . .
O3B O 0.8968(2) 0.33876(18) 0.72181(17) 0.0198(6) Uani 1 1 d . . . . .
O5A O 0.3467(2) 0.22580(18) 0.17529(16) 0.0179(5) Uani 1 1 d . . . . .
O5B O 1.1405(2) 0.61050(18) 0.80284(16) 0.0193(6) Uani 1 1 d . . . . .
O8A O 0.4934(2) 0.20610(18) 0.34018(16) 0.0195(6) Uani 1 1 d . . . . .
O8B O 0.9906(2) 0.49101(18) 0.64382(16) 0.0202(6) Uani 1 1 d . . . . .
O9A O 0.4122(2) 0.07571(17) 0.21099(16) 0.0164(5) Uani 1 1 d . . . . .
O9B O 1.0788(2) 0.44104(17) 0.77786(16) 0.0169(5) Uani 1 1 d . . . . .
F1A F 0.9750(2) 0.19043(18) 0.37658(17) 0.0367(6) Uani 1 1 d . . . . .
F1B F 0.5892(2) 0.3665(2) 0.49840(15) 0.0467(7) Uani 1 1 d . . . . .
F2A F 0.9843(2) 0.0497(2) 0.41528(19) 0.0493(8) Uani 1 1 d . . . . .
F2B F 0.4985(2) 0.29848(18) 0.58949(17) 0.0404(7) Uani 1 1 d . . . . .
F3A F 0.9002(2) 0.1777(3) 0.49752(17) 0.0699(10) Uani 1 1 d . . . . .
F3B F 0.5159(2) 0.45922(17) 0.61440(16) 0.0350(6) Uani 1 1 d . . . . .
F4A F 0.8306(3) -0.1430(2) 0.28876(19) 0.0509(7) Uani 1 1 d . . . . .
F4B F 0.6673(2) 0.14936(16) 0.59076(16) 0.0359(6) Uani 1 1 d . . . . .
F5A F 0.6411(2) -0.15481(19) 0.32842(19) 0.0511(8) Uani 1 1 d . . . . .
F5B F 0.6709(2) 0.18623(18) 0.73771(16) 0.0383(6) Uani 1 1 d . . . . .
F6A F 0.8048(3) -0.0901(2) 0.42987(17) 0.0481(7) Uani 1 1 d . . . . .
F6B F 0.8480(2) 0.14356(16) 0.68014(17) 0.0359(6) Uani 1 1 d . . . . .
P1A P 0.55836(9) 0.12544(7) 0.26688(7) 0.0179(2) Uani 1 1 d . . . . .
P1B P 0.93063(9) 0.45623(7) 0.72337(7) 0.0178(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'
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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4A C3A O2A 121.9(3) . . ?
C12A C3A C4A 120.3(3) . . ?
C12A C3A O2A 117.8(3) . . ?
C4B C3B O2B 120.9(3) . . ?
C12B C3B C4B 120.9(3) . . ?
C12B C3B O2B 118.0(3) . . ?
C15A C4A C3A 120.3(3) . . ?
C15A C4A O5A 120.4(3) . . ?
O5A C4A C3A 119.1(3) . . ?
C15B C4B C3B 120.0(4) . . ?
C15B C4B O5B 120.6(3) . . ?
O5B C4B C3B 119.2(3) . . ?
C16A C6A C7A 118.2(3) . . ?
O5A C6A C7A 105.6(3) . . ?
O5A C6A C16A 110.5(3) . . ?
O9A C6A C7A 103.0(3) . . ?
O9A C6A C16A 110.9(3) . . ?
O9A C6A O5A 108.0(3) . . ?
C16B C6B C7B 117.3(3) . . ?
O5B C6B C7B 106.0(3) . . ?
O5B C6B C16B 110.3(3) . . ?
O9B C6B C7B 102.8(3) . . ?
O9B C6B C16B 111.4(3) . . ?
O9B C6B O5B 108.4(3) . . ?
C22A C7A C6A 111.8(3) . . ?
C23A C7A C6A 114.9(3) . . ?
C23A C7A C22A 113.1(3) . . ?
O8A C7A C6A 101.3(3) . . ?
O8A C7A C22A 107.3(3) . . ?
O8A C7A C23A 107.4(3) . . ?
C22B C7B C6B 112.7(3) . . ?
C22B C7B C23B 113.2(3) . . ?
C23B C7B C6B 115.1(3) . . ?
O8B C7B C6B 100.8(3) . . ?
O8B C7B C22B 106.6(3) . . ?
O8B C7B C23B 107.1(3) . . ?
C9A C8A C10A 130.9(4) . . ?
C9A C8A O1A 113.4(3) . . ?
O1A C8A C10A 115.7(3) . . ?
C9B C8B C10B 131.7(3) . . ?
C9B C8B O1B 113.4(3) . . ?
O1B C8B C10B 114.8(3) . . ?
C8A C9A C11A 133.6(3) . . ?
C8A C9A O3A 111.3(3) . . ?
O3A C9A C11A 115.1(3) . . ?
C8B C9B C11B 133.6(3) . . ?
C8B C9B O3B 110.9(3) . . ?
O3B C9B C11B 115.5(3) . . ?
F1A C10A C8A 111.1(3) . . ?
F2A C10A C8A 111.3(3) . . ?
F2A C10A F1A 107.4(3) . . ?
F3A C10A C8A 112.3(3) . . ?
F3A C10A F1A 106.2(3) . . ?
F3A C10A F2A 108.3(3) . . ?
F1B C10B C8B 111.3(3) . . ?
F2B C10B C8B 112.5(3) . . ?
F2B C10B F1B 107.5(3) . . ?
F3B C10B C8B 111.4(3) . . ?
F3B C10B F1B 106.5(3) . . ?
F3B C10B F2B 107.3(3) . . ?
F4A C11A C9A 112.6(3) . . ?
F5A C11A C9A 111.3(3) . . ?
F5A C11A F4A 106.0(3) . . ?
F6A C11A C9A 112.1(3) . . ?
F6A C11A F4A 106.4(3) . . ?
F6A C11A F5A 108.0(3) . . ?
F4B C11B C9B 112.9(3) . . ?
F4B C11B F5B 106.6(3) . . ?
F4B C11B F6B 107.7(3) . . ?
F5B C11B C9B 112.2(3) . . ?
F6B C11B C9B 111.1(3) . . ?
F6B C11B F5B 105.9(3) . . ?
C3A C12A H12A 120.2 . . ?
C3A C12A C13A 119.6(4) . . ?
C13A C12A H12A 120.2 . . ?
C3B C12B H12B 120.4 . . ?
C3B C12B C13B 119.2(4) . . ?
C13B C12B H12B 120.4 . . ?
C12A C13A H13A 120.0 . . ?
C14A C13A C12A 120.0(4) . . ?
C14A C13A H13A 120.0 . . ?
C12B C13B H13B 119.9 . . ?
C12B C13B C14B 120.1(4) . . ?
C14B C13B H13B 119.9 . . ?
C13A C14A H14A 119.9 . . ?
C15A C14A C13A 120.2(3) . . ?
C15A C14A H14A 119.9 . . ?
C13B C14B H14B 119.9 . . ?
C15B C14B C13B 120.1(3) . . ?
C15B C14B H14B 119.9 . . ?
C4A C15A C14A 119.6(3) . . ?
C4A C15A H15A 120.2 . . ?
C14A C15A H15A 120.2 . . ?
C4B C15B C14B 119.6(3) . . ?
C4B C15B H15B 120.2 . . ?
C14B C15B H15B 120.2 . . ?
C17A C16A C6A 118.9(3) . . ?
C21A C16A C6A 122.0(3) . . ?
C21A C16A C17A 118.9(3) . . ?
C17B C16B C6B 121.4(3) . . ?
C17B C16B C21B 119.3(3) . . ?
C21B C16B C6B 119.3(3) . . ?
C16A C17A H17A 119.7 . . ?
C18A C17A C16A 120.6(3) . . ?
C18A C17A H17A 119.7 . . ?
C16B C17B H17B 120.0 . . ?
C16B C17B C18B 119.9(4) . . ?
C18B C17B H17B 120.0 . . ?
C17A C18A H18A 119.8 . . ?
C19A C18A C17A 120.3(4) . . ?
C19A C18A H18A 119.8 . . ?
C17B C18B H18B 119.9 . . ?
C19B C18B C17B 120.1(4) . . ?
C19B C18B H18B 119.9 . . ?
C18A C19A H19A 120.2 . . ?
C18A C19A C20A 119.7(3) . . ?
C20A C19A H19A 120.2 . . ?
C18B C19B H19B 119.9 . . ?
C20B C19B C18B 120.2(4) . . ?
C20B C19B H19B 119.9 . . ?
C19A C20A H20A 119.9 . . ?
C19A C20A C21A 120.1(4) . . ?
C21A C20A H20A 119.9 . . ?
C19B C20B H20B 120.1 . . ?
C19B C20B C21B 119.8(3) . . ?
C21B C20B H20B 120.1 . . ?
C16A C21A C20A 120.4(4) . . ?
C16A C21A H21A 119.8 . . ?
C20A C21A H21A 119.8 . . ?
C16B C21B H21B 119.7 . . ?
C20B C21B C16B 120.6(3) . . ?
C20B C21B H21B 119.7 . . ?
C7A C22A H22A 109.5 . . ?
C7A C22A H22B 109.5 . . ?
C7A C22A H22C 109.5 . . ?
H22A C22A H22B 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C7B C22B H22D 109.5 . . ?
C7B C22B H22E 109.5 . . ?
C7B C22B H22F 109.5 . . ?
H22D C22B H22E 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C7A C23A H23A 109.5 . . ?
C7A C23A H23B 109.5 . . ?
C7A C23A H23C 109.5 . . ?
H23A C23A H23B 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C7B C23B H23D 109.5 . . ?
C7B C23B H23E 109.5 . . ?
C7B C23B H23F 109.5 . . ?
H23D C23B H23E 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C8A O1A P1A 111.7(2) . . ?
C8B O1B P1B 112.2(2) . . ?
C3A O2A P1A 125.3(2) . . ?
C3B O2B P1B 125.1(2) . . ?
C9A O3A P1A 113.8(2) . . ?
C9B O3B P1B 113.9(2) . . ?
C4A O5A C6A 114.5(3) . . ?
C4B O5B C6B 113.9(3) . . ?
C7A O8A P1A 115.3(2) . . ?
C7B O8B P1B 115.0(2) . . ?
C6A O9A P1A 109.4(2) . . ?
C6B O9B P1B 109.5(2) . . ?
O2A P1A O1A 87.30(12) . . ?
O2A P1A O3A 117.03(14) . . ?
O2A P1A O9A 95.57(12) . . ?
O3A P1A O1A 89.81(12) . . ?
O3A P1A O9A 86.68(12) . . ?
O8A P1A O1A 88.03(12) . . ?
O8A P1A O2A 119.68(14) . . ?
O8A P1A O3A 123.05(14) . . ?
O8A P1A O9A 92.68(12) . . ?
O9A P1A O1A 176.21(13) . . ?
O2B P1B O1B 87.78(12) . . ?
O2B P1B O3B 115.79(14) . . ?
O2B P1B O9B 95.79(12) . . ?
O3B P1B O1B 89.69(12) . . ?
O3B P1B O9B 86.88(12) . . ?
O8B P1B O1B 87.34(12) . . ?
O8B P1B O2B 119.61(14) . . ?
O8B P1B O3B 124.33(14) . . ?
O8B P1B O9B 92.69(12) . . ?
O9B P1B O1B 175.86(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3A C4A 1.390(5) . ?
C3A C12A 1.375(5) . ?
C3A O2A 1.401(4) . ?
C3B C4B 1.390(5) . ?
C3B C12B 1.368(5) . ?
C3B O2B 1.405(4) . ?
C4A C15A 1.375(5) . ?
C4A O5A 1.386(4) . ?
C4B C15B 1.370(5) . ?
C4B O5B 1.385(4) . ?
C6A C7A 1.535(5) . ?
C6A C16A 1.507(5) . ?
C6A O5A 1.446(4) . ?
C6A O9A 1.409(4) . ?
C6B C7B 1.542(5) . ?
C6B C16B 1.500(5) . ?
C6B O5B 1.444(4) . ?
C6B O9B 1.411(4) . ?
C7A C22A 1.511(5) . ?
C7A C23A 1.510(5) . ?
C7A O8A 1.474(4) . ?
C7B C22B 1.507(5) . ?
C7B C23B 1.513(5) . ?
C7B O8B 1.482(4) . ?
C8A C9A 1.318(5) . ?
C8A C10A 1.495(5) . ?
C8A O1A 1.344(4) . ?
C8B C9B 1.325(5) . ?
C8B C10B 1.485(5) . ?
C8B O1B 1.338(4) . ?
C9A C11A 1.491(5) . ?
C9A O3A 1.386(4) . ?
C9B C11B 1.480(5) . ?
C9B O3B 1.391(4) . ?
C10A F1A 1.326(4) . ?
C10A F2A 1.318(5) . ?
C10A F3A 1.316(4) . ?
C10B F1B 1.325(4) . ?
C10B F2B 1.323(4) . ?
C10B F3B 1.321(4) . ?
C11A F4A 1.336(5) . ?
C11A F5A 1.320(4) . ?
C11A F6A 1.316(4) . ?
C11B F4B 1.324(4) . ?
C11B F5B 1.346(4) . ?
C11B F6B 1.330(4) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.389(5) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.382(5) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.386(5) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.392(5) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.385(5) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.382(5) . ?
C15A H15A 0.9500 . ?
C15B H15B 0.9500 . ?
C16A C17A 1.386(5) . ?
C16A C21A 1.376(5) . ?
C16B C17B 1.377(5) . ?
C16B C21B 1.395(5) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.378(5) . ?
C17B H17B 0.9500 . ?
C17B C18B 1.391(5) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.372(5) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.380(5) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.377(5) . ?
C19B H19B 0.9500 . ?
C19B C20B 1.375(5) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.388(5) . ?
C20B H20B 0.9500 . ?
C20B C21B 1.379(5) . ?
C21A H21A 0.9500 . ?
C21B H21B 0.9500 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
O1A P1A 1.709(2) . ?
O1B P1B 1.707(2) . ?
O2A P1A 1.593(3) . ?
O2B P1B 1.597(3) . ?
O3A P1A 1.626(3) . ?
O3B P1B 1.629(3) . ?
O8A P1A 1.574(2) . ?
O8B P1B 1.584(3) . ?
O9A P1A 1.666(2) . ?
O9B P1B 1.658(2) . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.4562(10)
2 0.5438(10)
