#------------------------------------------------------------------------------
#$Date: 2019-11-26 06:59:06 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242889 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/30/4133042.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_4133042
loop_
_publ_author_name
'Wu, Yilei'
'Zhou, Jiawang'
'Nelson, Jordan N.'
'Young, Ryan M.'
'Krzyaniak, Matthew D.'
'Wasielewski, Michael R.'
_publ_section_title
;
 Covalent Radical Pairs as Spin Qubits: Influence of Rapid Electron Motion
 between Two Equivalent Sites on Spin Coherence.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13011
_journal_page_last               13021
_journal_paper_doi               10.1021/jacs.8b08105
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C50 H44 N4 O2, 4(F6 P), 0.25(O)'
_chemical_formula_sum            'C50 H44 F24 N4 O2.25 P4'
_chemical_formula_weight         1316.77
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                103.786(3)
_cell_angle_beta                 103.714(3)
_cell_angle_gamma                91.567(3)
_cell_formula_units_Z            1
_cell_length_a                   8.4372(4)
_cell_length_b                   9.7417(5)
_cell_length_c                   17.5976(8)
_cell_measurement_reflns_used    7047
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.779
_cell_measurement_theta_min      2.671
_cell_volume                     1359.28(12)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13555
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        63.843
_diffrn_reflns_theta_max         63.843
_diffrn_reflns_theta_min         2.671
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    2.455
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.6627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1031 before and 0.0461 after correction. The Ratio of minimum to maximum transmission is 0.8808. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_description       plate
_exptl_crystal_F_000             666
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         4428
_refine_ls_number_restraints     561
_refine_ls_restrained_S_all      1.275
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1127P)²+2.6038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1869
_refine_ls_wR_factor_ref         0.1989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3588
_reflns_number_total             4428
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b08105_si_002.cif
_cod_data_source_block           cx1065
_cod_database_code               4133042
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.599
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2A-C12A = O2-C12 = O2-C14 = O2A-C14A = O1-C9 = O1A-C9A = O1A-C13A = O1-C13
 1.4 with sigma of 0.02
 C16-C15 \\sim C16-H16 \\sim C16-C17
 with sigma of 0.01
3. Rigid bond restraints
 O1, O1A, O2, O2A, C13, C13A, C14, C14A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O1 \\sim O1A \\sim O2 \\sim O2A \\sim C13 \\sim C13A \\sim C14 \\sim C14A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C13A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=1-
 FVAR(1)
 Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=FVAR(1)
 Sof(C10A)=Sof(C9A)=Sof(C8A)=Sof(H8A)=Sof(C7A)=Sof(C12A)=Sof(C11A)=Sof(H11A)=1-
 FVAR(2)
 Sof(O1A)=Sof(O2A)=Sof(H9)=Sof(H12)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=
 Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=0.5*(1-FVAR(3))
 Sof(O1)=Sof(O2)=Sof(H9A)=Sof(H12A)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=0.5*FVAR(3)
 Sof(C7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(C10)=Sof(C12)=Sof(C11)=Sof(H11)=FVAR(2)
 Fixed Sof: O1S(0.125)
 Fixed Y: O1S(0)
 Fixed Z: O1S(0.5)
7.a Everything fixed:
 H9, H9A, H8A, H12A, H12, O1S
7.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C20(H20A,H20B)
7.c Me refined with riding coordinates:
 C14A(H14D,H14E,H14F)
7.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C2A(H2A), C3(H3), C3A(H3A), C5(H5), C5A(H5A), C6(H6), C6A(H6A),
 C8(H8), C11(H11), C16(H16), C17(H17), C18(H18), C19(H19), C22(H22), C24(H24),
 C25(H25), C26(H26)
7.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C13A(H13D,H13E,H13F), C14(H14A,H14B,H14C)
;
_olex2_date_sample_data_collection 2017-09-14
_olex2_date_sample_submission    2017-09-12
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a glass fibre in Paratone oil'
_olex2_submission_original_sample_id cx1065
_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
O1 O 0.7402(16) 0.4044(17) 0.4186(5) 0.123(6) Uani 0.395(3) 1 d D U P A 1
O1A O 0.640(2) 0.194(4) 0.3792(16) 0.059(6) Uani 0.105(3) 1 d D U P A -2
O2 O 1.2695(9) 0.0887(10) 0.4657(4) 0.0485(19) Uani 0.395(3) 1 d D U P A 1
O2A O 1.315(3) 0.211(4) 0.4850(18) 0.062(4) Uani 0.105(3) 1 d D U P A -2
N1 N 1.2138(4) 0.1557(3) 0.75549(17) 0.0283(6) Uani 1 1 d . U . . .
N2 N 0.7096(3) 0.3028(3) 0.12946(17) 0.0251(6) Uani 1 1 d . U . . .
C1 C 1.2657(5) 0.1384(4) 0.8395(2) 0.0312(8) Uani 1 1 d . U . . .
H1A H 1.380155 0.112808 0.850083 0.037 Uiso 1 1 calc R . . . .
H1B H 1.195638 0.059823 0.844798 0.037 Uiso 1 1 calc R . . . .
C2 C 1.069(3) 0.200(4) 0.7342(17) 0.028(4) Uani 0.40(6) 1 d . U P A 1
H2 H 1.002479 0.217670 0.771293 0.034 Uiso 0.40(6) 1 calc R . P A 1
C2A C 1.052(2) 0.168(3) 0.7221(13) 0.042(5) Uani 0.60(6) 1 d . U P A 2
H2A H 0.973498 0.165974 0.752749 0.050 Uiso 0.60(6) 1 calc R . P A 2
C3 C 1.013(3) 0.222(4) 0.6572(15) 0.030(4) Uani 0.40(6) 1 d . U P A 1
H3 H 0.908223 0.255122 0.641927 0.036 Uiso 0.40(6) 1 calc R . P A 1
C3A C 1.004(3) 0.184(4) 0.6458(12) 0.042(5) Uani 0.60(6) 1 d . U P A 2
H3A H 0.890732 0.189028 0.622893 0.051 Uiso 0.60(6) 1 calc R . P A 2
C4 C 1.1140(5) 0.1923(4) 0.6011(2) 0.0323(7) Uani 1 1 d . U . . .
C5 C 1.270(3) 0.143(4) 0.6314(15) 0.030(5) Uani 0.40(6) 1 d . U P A 1
H5 H 1.342510 0.122259 0.597229 0.036 Uiso 0.40(6) 1 calc R . P A 1
C5A C 1.276(2) 0.180(3) 0.6329(10) 0.030(3) Uani 0.60(6) 1 d . U P A 2
H5A H 1.354743 0.185381 0.602791 0.036 Uiso 0.60(6) 1 calc R . P A 2
C6 C 1.316(3) 0.124(5) 0.7084(15) 0.032(5) Uani 0.40(6) 1 d . U P A 1
H6 H 1.418601 0.090334 0.727307 0.038 Uiso 0.40(6) 1 calc R . P A 1
C6A C 1.322(2) 0.160(3) 0.7100(9) 0.027(3) Uani 0.60(6) 1 d . U P A 2
H6A H 1.433710 0.149529 0.731961 0.032 Uiso 0.60(6) 1 calc R . P A 2
C7 C 1.0514(19) 0.215(2) 0.5196(9) 0.033(2) Uani 0.789(6) 1 d . U P A 1
C8 C 0.9325(8) 0.3038(9) 0.5058(3) 0.063(2) Uani 0.789(6) 1 d . U P A 1
H8 H 0.892076 0.352633 0.549825 0.076 Uiso 0.789(6) 1 calc R . P A 1
C9 C 0.8681(8) 0.3260(8) 0.4304(3) 0.059(2) Uani 0.789(6) 1 d D U P A 1
H9 H 0.789840 0.393470 0.422950 0.071 Uiso 0.1054 1 d . . P A 1
C10 C 0.926(2) 0.256(3) 0.3638(10) 0.034(4) Uani 0.789(6) 1 d . U P A 1
C10A C 0.907(8) 0.253(12) 0.367(4) 0.028(7) Uani 0.211(6) 1 d . U P A -2
C9A C 0.8128(18) 0.198(2) 0.4069(11) 0.033(4) Uani 0.211(6) 1 d D U P A -2
H9A H 0.694720 0.185680 0.396370 0.040 Uiso 0.3946 1 d . . P A -2
C8A C 0.879(2) 0.177(2) 0.4815(11) 0.034(4) Uani 0.211(6) 1 d . U P A -2
H8A H 0.809540 0.139320 0.509930 0.041 Uiso 0.2108 1 d . . P A -2
C7A C 1.069(9) 0.213(11) 0.517(4) 0.047(9) Uani 0.211(6) 1 d . U P A -2
C12A C 1.150(2) 0.260(4) 0.4796(15) 0.061(6) Uani 0.211(6) 1 d D U P A -2
C12 C 1.1213(7) 0.1548(7) 0.4542(3) 0.0425(13) Uani 0.789(6) 1 d D U P A 1
H12A H 1.257150 0.233640 0.492740 0.051 Uiso 0.3946 1 d . . P A -2
C11A C 1.073(3) 0.284(4) 0.4016(17) 0.069(9) Uani 0.211(6) 1 d . U P A -2
H11A H 1.15(4) 0.32(3) 0.389(17) 0.083 Uiso 0.211(6) 1 d R . P A -2
C11 C 1.0536(7) 0.1758(7) 0.3780(3) 0.0393(13) Uani 0.789(6) 1 d . U P A 1
H11 H 1.098301 0.132442 0.334395 0.047 Uiso 0.789(6) 1 calc R . P A 1
H12 H 1.217050 0.103330 0.460640 0.047 Uiso 0.1054 1 d . . P A 1
C13 C 0.678(3) 0.468(3) 0.4856(8) 0.134(7) Uani 0.395(3) 1 d D U P A 1
H13A H 0.767238 0.491887 0.534908 0.201 Uiso 0.395(3) 1 calc GR . P A 1
H13B H 0.594624 0.401674 0.491284 0.201 Uiso 0.395(3) 1 calc GR . P A 1
H13C H 0.628404 0.554742 0.476841 0.201 Uiso 0.395(3) 1 calc GR . P A 1
C13A C 0.516(3) 0.161(4) 0.4171(17) 0.023(5) Uani 0.105(3) 1 d D U P A -2
H13D H 0.566456 0.130813 0.465801 0.035 Uiso 0.105(3) 1 calc GR . P A -2
H13E H 0.437461 0.084676 0.379404 0.035 Uiso 0.105(3) 1 calc GR . P A -2
H13F H 0.458185 0.245711 0.431808 0.035 Uiso 0.105(3) 1 calc GR . P A -2
C14 C 1.3695(17) 0.0648(18) 0.4098(8) 0.066(3) Uani 0.395(3) 1 d D U P A 1
H14A H 1.468920 0.023710 0.432639 0.099 Uiso 0.395(3) 1 calc GR . P A 1
H14B H 1.399528 0.155088 0.399296 0.099 Uiso 0.395(3) 1 calc GR . P A 1
H14C H 1.308790 -0.000842 0.359162 0.099 Uiso 0.395(3) 1 calc GR . P A 1
C14A C 1.442(6) 0.186(7) 0.441(3) 0.070(6) Uani 0.105(3) 1 d D U P A -2
H14D H 1.535250 0.151073 0.473753 0.105 Uiso 0.105(3) 1 calc R . P A -2
H14E H 1.398272 0.115285 0.389843 0.105 Uiso 0.105(3) 1 calc R . P A -2
H14F H 1.477001 0.274921 0.430750 0.105 Uiso 0.105(3) 1 calc R . P A -2
C15 C 0.8444(4) 0.2722(4) 0.2819(2) 0.0284(7) Uani 1 1 d D U . . .
C16 C 0.6856(4) 0.2906(5) 0.2565(2) 0.0380(9) Uani 1 1 d D U . . .
H16 H 0.617862 0.292999 0.292869 0.046 Uiso 1 1 calc DR . . . .
C17 C 0.6182(4) 0.3055(4) 0.1831(2) 0.0348(8) Uani 1 1 d D U . . .
H17 H 0.504802 0.318150 0.168143 0.042 Uiso 1 1 calc R . . . .
C18 C 0.8687(4) 0.2814(5) 0.1504(2) 0.0349(9) Uani 1 1 d . U . . .
H18 H 0.932616 0.276383 0.112251 0.042 Uiso 1 1 calc R . . . .
C19 C 0.9401(4) 0.2667(4) 0.2260(2) 0.0343(8) Uani 1 1 d . U . . .
H19 H 1.053218 0.252872 0.240617 0.041 Uiso 1 1 calc R . . . .
C20 C 0.6385(4) 0.3287(4) 0.0488(2) 0.0300(7) Uani 1 1 d . U . . .
H20A H 0.517619 0.322152 0.038130 0.036 Uiso 1 1 calc R . . . .
H20B H 0.668399 0.254629 0.006562 0.036 Uiso 1 1 calc R . . . .
C21 C 0.7001(4) 0.4734(4) 0.0447(2) 0.0267(7) Uani 1 1 d . U . . .
C22 C 0.6918(4) 0.5950(4) 0.1035(2) 0.0277(7) Uani 1 1 d . U . . .
H22 H 0.648416 0.587290 0.147552 0.033 Uiso 1 1 calc R . . . .
C23 C 0.7463(4) 0.7276(4) 0.0984(2) 0.0281(7) Uani 1 1 d . U . . .
C24 C 0.8075(4) 0.7386(4) 0.0332(2) 0.0320(7) Uani 1 1 d . U . . .
H24 H 0.847013 0.828617 0.029807 0.038 Uiso 1 1 calc R . . . .
C25 C 0.8108(5) 0.6179(4) -0.0267(2) 0.0344(8) Uani 1 1 d . U . . .
H25 H 0.848242 0.626564 -0.072372 0.041 Uiso 1 1 calc R . . . .
C26 C 0.7602(4) 0.4843(4) -0.0211(2) 0.0313(7) Uani 1 1 d . U . . .
H26 H 0.766397 0.401755 -0.061523 0.038 Uiso 1 1 calc R . . . .
P1 P 0.26009(12) 0.99576(11) 0.13198(6) 0.0336(3) Uani 1 1 d . U . . .
F1 F 0.4076(3) 1.0221(3) 0.09237(15) 0.0478(6) Uani 1 1 d . U . . .
F2 F 0.1131(3) 0.9678(3) 0.17114(16) 0.0524(6) Uani 1 1 d . U . . .
F3 F 0.1505(3) 0.9177(3) 0.04424(15) 0.0554(7) Uani 1 1 d . U . . .
F4 F 0.1965(3) 1.1437(3) 0.12204(14) 0.0476(6) Uani 1 1 d . U . . .
F5 F 0.3728(3) 1.0704(3) 0.21951(14) 0.0505(6) Uani 1 1 d . U . . .
F6 F 0.3272(3) 0.8470(3) 0.14222(16) 0.0530(7) Uani 1 1 d . U . . .
P2 P 0.67210(16) 0.43755(14) 0.71597(8) 0.0547(4) Uani 1 1 d . U . . .
F7 F 0.5656(4) 0.4203(3) 0.7771(2) 0.0693(8) Uani 1 1 d . U . . .
F8 F 0.7831(6) 0.4556(4) 0.6571(3) 0.1009(12) Uani 1 1 d . U . . .
F9 F 0.8354(4) 0.4333(4) 0.7817(2) 0.0836(9) Uani 1 1 d . U . . .
F10 F 0.6621(4) 0.2682(3) 0.6842(2) 0.0803(10) Uani 1 1 d . U . . .
F11 F 0.5085(5) 0.4423(4) 0.6503(2) 0.0995(11) Uani 1 1 d . U . . .
F12 F 0.6805(4) 0.6052(3) 0.7481(2) 0.0839(10) Uani 1 1 d . U . . .
O1S O 0.503000 0.000000 0.500000 0.088 Uani 0.125 1 d . U P B -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
C9 O1 H9 20.3 . .
C9 O1 C13 118.9(8) . .
C13 O1 H9 119.0 . .
C9A O1A H9A 22.2 . .
C9A O1A C13A 129(2) . .
C13A O1A H9A 107.4 . .
C12 O2 H12 8.8 . .
C12 O2 C14 124.4(7) . .
C14 O2 H12 125.4 . .
C12A O2A H12A 16.5 . .
C14A O2A C12A 143(3) . .
C14A O2A H12A 157.2 . .
C2 N1 C1 116.7(12) . .
C2 N1 C6 125.2(17) . .
C2A N1 C1 119.9(9) . .
C6 N1 C1 118.1(11) . .
C6A N1 C1 122.1(7) . .
C6A N1 C2A 118.0(11) . .
C17 N2 C20 121.1(3) . .
C18 N2 C17 119.3(3) . .
C18 N2 C20 119.5(3) . .
N1 C1 H1A 109.2 . .
N1 C1 H1B 109.2 . .
N1 C1 C23 111.9(3) . 2_766
H1A C1 H1B 107.9 . .
C23 C1 H1A 109.2 2_766 .
C23 C1 H1B 109.2 2_766 .
N1 C2 H2 119.8 . .
N1 C2 C3 120(2) . .
C3 C2 H2 119.8 . .
N1 C2A H2A 119.8 . .
C3A C2A N1 120.3(17) . .
C3A C2A H2A 119.8 . .
C2 C3 H3 120.3 . .
C2 C3 C4 119(3) . .
C4 C3 H3 120.3 . .
C2A C3A H3A 119.3 . .
C2A C3A C4 121.3(18) . .
C4 C3A H3A 119.3 . .
C3 C4 C5 115.1(16) . .
C3 C4 C7 118.5(13) . .
C3A C4 C5A 119.5(12) . .
C3A C4 C7A 124(3) . .
C5 C4 C7 126.3(11) . .
C5A C4 C7A 116(3) . .
C4 C5 H5 119.1 . .
C6 C5 C4 122(2) . .
C6 C5 H5 119.1 . .
C4 C5A H5A 120.9 . .
C4 C5A C6A 118.2(15) . .
C6A C5A H5A 120.9 . .
N1 C6 C5 118(2) . .
N1 C6 H6 120.9 . .
C5 C6 H6 120.9 . .
N1 C6A C5A 122.6(14) . .
N1 C6A H6A 118.7 . .
C5A C6A H6A 118.7 . .
C8 C7 C4 120.7(10) . .
C8 C7 C12 117.1(11) . .
C12 C7 C4 122.0(10) . .
C7 C8 H8 118.6 . .
C7 C8 C9 122.8(8) . .
C9 C8 H8 118.6 . .
O1 C9 C8 120.1(6) . .
O1 C9 H9 9.0 . .
O1 C9 C10 119.4(8) . .
C8 C9 H9 121.0 . .
C8 C9 C10 120.2(8) . .
C10 C9 H9 118.6 . .
C9 C10 C15 119.1(12) . .
C11 C10 C9 117.6(10) . .
C11 C10 C15 123.3(12) . .
C9A C10A C11A 119(4) . .
C9A C10A C15 124(6) . .
C11A C10A C15 117(5) . .
O1A C9A H9A 11.4 . .
C10A C9A O1A 118(3) . .
C10A C9A H9A 129.9 . .
C10A C9A C8A 121(3) . .
C8A C9A O1A 119.2(17) . .
C8A C9A H9A 108.2 . .
C9A C8A H8A 120.0 . .
C9A C8A C7A 117(3) . .
C7A C8A H8A 122.9 . .
C4 C7A C8A 108(4) . .
C12A C7A C4 131(6) . .
C12A C7A C8A 120(5) . .
O2A C12A H12A 10.0 . .
C7A C12A O2A 116(4) . .
C7A C12A H12A 109.9 . .
C7A C12A C11A 120(4) . .
C11A C12A O2A 114(2) . .
C11A C12A H12A 123.4 . .
O2 C12 C7 122.2(7) . .
O2 C12 H12 4.2 . .
C7 C12 H12 122.8 . .
C11 C12 O2 118.0(5) . .
C11 C12 C7 119.4(7) . .
C11 C12 H12 117.8 . .
C10A C11A C12A 122(3) . .
C10A C11A H11A 135(10) . .
C12A C11A H11A 103(10) . .
C10 C11 C12 122.5(7) . .
C10 C11 H11 118.8 . .
C12 C11 H11 118.8 . .
O1 C13 H13A 109.5 . .
O1 C13 H13B 109.5 . .
O1 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O1A C13A H13D 109.5 . .
O1A C13A H13E 109.5 . .
O1A C13A H13F 109.5 . .
H13D C13A H13E 109.5 . .
H13D C13A H13F 109.5 . .
H13E C13A H13F 109.5 . .
O2 C14 H14A 109.5 . .
O2 C14 H14B 109.5 . .
O2 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O2A C14A H14D 109.5 . .
O2A C14A H14E 109.5 . .
O2A C14A H14F 109.5 . .
H14D C14A H14E 109.5 . .
H14D C14A H14F 109.5 . .
H14E C14A H14F 109.5 . .
C16 C15 C10 125.2(6) . .
C16 C15 C10A 118(2) . .
C16 C15 C19 116.8(3) . .
C19 C15 C10 118.1(6) . .
C19 C15 C10A 125(2) . .
C15 C16 H16 118.4 . .
C17 C16 C15 123.2(4) . .
C17 C16 H16 118.4 . .
N2 C17 H17 119.8 . .
C16 C17 N2 120.5(3) . .
C16 C17 H17 119.8 . .
N2 C18 H18 119.6 . .
N2 C18 C19 120.9(3) . .
C19 C18 H18 119.6 . .
C15 C19 H19 120.3 . .
C18 C19 C15 119.3(3) . .
C18 C19 H19 120.3 . .
N2 C20 H20A 109.4 . .
N2 C20 H20B 109.4 . .
N2 C20 C21 111.2(3) . .
H20A C20 H20B 108.0 . .
C21 C20 H20A 109.4 . .
C21 C20 H20B 109.4 . .
C22 C21 C20 121.1(3) . .
C22 C21 C26 119.9(3) . .
C26 C21 C20 118.9(3) . .
C21 C22 H22 119.7 . .
C23 C22 C21 120.7(3) . .
C23 C22 H22 119.7 . .
C22 C23 C1 121.6(3) . 2_766
C22 C23 C24 119.5(3) . .
C24 C23 C1 118.9(3) . 2_766
C23 C24 H24 120.1 . .
C25 C24 C23 119.8(4) . .
C25 C24 H24 120.1 . .
C24 C25 H25 119.5 . .
C24 C25 C26 121.0(3) . .
C26 C25 H25 119.5 . .
C21 C26 H26 120.5 . .
C25 C26 C21 119.0(4) . .
C25 C26 H26 120.5 . .
F2 P1 F1 179.42(15) . .
F2 P1 F6 90.42(14) . .
F3 P1 F1 89.24(14) . .
F3 P1 F2 90.48(15) . .
F3 P1 F6 89.51(15) . .
F4 P1 F1 90.16(13) . .
F4 P1 F2 90.35(14) . .
F4 P1 F3 90.93(14) . .
F4 P1 F5 90.47(14) . .
F4 P1 F6 179.11(15) . .
F5 P1 F1 90.13(14) . .
F5 P1 F2 90.14(14) . .
F5 P1 F3 178.46(15) . .
F5 P1 F6 89.07(14) . .
F6 P1 F1 89.07(14) . .
F7 P2 F10 89.71(18) . .
F8 P2 F7 178.3(2) . .
F8 P2 F10 90.61(18) . .
F8 P2 F12 90.08(18) . .
F9 P2 F7 90.66(19) . .
F9 P2 F8 87.7(2) . .
F9 P2 F10 89.5(2) . .
F9 P2 F11 179.8(2) . .
F9 P2 F12 90.6(2) . .
F11 P2 F7 89.3(2) . .
F11 P2 F8 92.4(3) . .
F11 P2 F10 90.7(2) . .
F11 P2 F12 89.2(2) . .
F12 P2 F7 89.60(17) . .
F12 P2 F10 179.31(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C9 1.343(9) .
O1 H9 0.4291 .
O1 C13 1.419(12) .
O1A C9A 1.419(17) .
O1A H9A 0.5076 .
O1A C13A 1.436(19) .
O2 C12 1.416(8) .
O2 H12 0.4639 .
O2 C14 1.423(11) .
O2A C12A 1.466(19) .
O2A H12A 0.5703 .
O2A C14A 1.45(2) .
N1 C1 1.490(4) .
N1 C2 1.30(2) .
N1 C2A 1.374(15) .
N1 C6 1.33(2) .
N1 C6A 1.356(14) .
N2 C17 1.349(5) .
N2 C18 1.341(5) .
N2 C20 1.487(4) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 C23 1.513(5) 2_766
C2 H2 0.9500 .
C2 C3 1.39(2) .
C2A H2A 0.9500 .
C2A C3A 1.354(18) .
C3 H3 0.9500 .
C3 C4 1.44(2) .
C3A H3A 0.9500 .
C3A C4 1.367(16) .
C4 C5 1.44(2) .
C4 C5A 1.368(15) .
C4 C7 1.476(16) .
C4 C7A 1.50(6) .
C5 H5 0.9500 .
C5 C6 1.37(2) .
C5A H5A 0.9500 .
C5A C6A 1.381(15) .
C6 H6 0.9500 .
C6A H6A 0.9500 .
C7 C8 1.360(15) .
C7 C12 1.427(15) .
C8 H8 0.9500 .
C8 C9 1.380(7) .
C9 H9 0.9529 .
C9 C10 1.407(18) .
C10 C11 1.361(18) .
C10 C15 1.488(15) .
C10A C9A 1.35(8) .
C10A C11A 1.38(8) .
C10A C15 1.52(5) .
C9A H9A 0.9679 .
C9A C8A 1.37(2) .
C8A H8A 0.9700 .
C8A C7A 1.57(8) .
C7A C12A 1.20(8) .
C12A H12A 0.9331 .
C12A C11A 1.45(3) .
C12 C11 1.392(7) .
C12 H12 0.9604 .
C11A H11A 0.8(3) .
C11 H11 0.9500 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C13A H13D 0.9800 .
C13A H13E 0.9800 .
C13A H13F 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C14A H14D 0.9800 .
C14A H14E 0.9800 .
C14A H14F 0.9800 .
C15 C16 1.339(4) .
C15 C19 1.406(5) .
C16 H16 0.9500 .
C16 C17 1.327(4) .
C17 H17 0.9500 .
C18 H18 0.9500 .
C18 C19 1.367(5) .
C19 H19 0.9500 .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C20 C21 1.514(5) .
C21 C22 1.390(5) .
C21 C26 1.393(5) .
C22 H22 0.9500 .
C22 C23 1.389(5) .
C23 C24 1.390(5) .
C24 H24 0.9500 .
C24 C25 1.386(6) .
C25 H25 0.9500 .
C25 C26 1.392(6) .
C26 H26 0.9500 .
P1 F1 1.606(3) .
P1 F2 1.601(3) .
P1 F3 1.594(3) .
P1 F4 1.586(2) .
P1 F5 1.594(2) .
P1 F6 1.604(3) .
P2 F7 1.591(3) .
P2 F8 1.587(3) .
P2 F9 1.584(4) .
P2 F10 1.604(3) .
P2 F11 1.586(4) .
P2 F12 1.589(3) .
