#------------------------------------------------------------------------------
#$Date: 2016-01-01 09:53:26 +0200 (Fri, 01 Jan 2016) $
#$Revision: 171854 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/82/7118203.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_7118203
loop_
_publ_author_name
'Han, Ying'
'Meng, Zheng'
'Chen, Chuan-Feng'
_publ_section_title
;
 Acid/base controllable complexation of a triptycene-derived
 macrotricyclic host and protonated 4,4'-bipyridinium/pyridinium salts.
;
_journal_issue                   3
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              590
_journal_page_last               593
_journal_paper_doi               10.1039/c5cc08166a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety
'C68 H76 O16, 2(C10 H9 N2), 2(F6 P), 4(C2 H3 N), 2(H2 O)'
_chemical_formula_sum            'C96 H110 F12 N8 O18 P2'
_chemical_formula_weight         1953.85
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-09-28 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                106.161(3)
_cell_angle_beta                 102.667(3)
_cell_angle_gamma                98.0070(10)
_cell_formula_units_Z            1
_cell_length_a                   12.010(2)
_cell_length_b                   13.437(3)
_cell_length_c                   16.320(3)
_cell_measurement_reflns_used    8322
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4848
_cell_measurement_theta_min      1.6152
_cell_volume                     2411.0(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
????
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 40.0300
              2theta: -20.7292
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 40.0300
              2theta: -20.7292
scan:
    Number of images: 344
               Slice: -110.0000 - 62.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 40.0300
              2theta: -20.7292
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0075
_diffrn_orient_matrix_UB_12      0.0030
_diffrn_orient_matrix_UB_13      0.0870
_diffrn_orient_matrix_UB_21      -0.0178
_diffrn_orient_matrix_UB_22      -0.0743
_diffrn_orient_matrix_UB_23      0.0211
_diffrn_orient_matrix_UB_31      0.0562
_diffrn_orient_matrix_UB_32      -0.0320
_diffrn_orient_matrix_UB_33      0.0143
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_laue_measured_fraction_full 0.997
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31774
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.615
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     620
_refine_ls_number_reflns         11027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0815
_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)+(0.0547P)²+3.5486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.1939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10416
_reflns_number_total             11027
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc08166a2.cif
_cod_data_source_block           mx3910
_cod_original_cell_volume        2411.1(8)
_cod_database_code               7118203
_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.
;
_diffrn_number_total             11027
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O9(H9A,H9B)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B),
 C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C14(H14), C22(H22), C25(H25),
 N1(H1), C35(H35), C36(H36), C38(H38), C39(H39), C41(H41), C42(H42), C43(H43),
 C44(H44)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C28(H28A,H28B,H28C), C45(H45A,H45B,H45C), C47(H47A,H47B,H47C)
;
_shelx_shelxl_version_number     2014/7
_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
O1 O 0.54147(18) 0.47287(15) 0.11723(14) 0.0359(4) Uani 1 1 d .
O2 O 0.6695(2) 0.68477(15) 0.16759(13) 0.0397(5) Uani 1 1 d .
O3 O 0.60097(18) 0.80615(14) 0.31875(12) 0.0324(4) Uani 1 1 d .
O4 O 0.50442(16) 0.85729(15) 0.46630(11) 0.0301(4) Uani 1 1 d .
O5 O 0.28652(16) 0.81521(16) 0.46105(11) 0.0315(4) Uani 1 1 d .
O6 O 0.10019(19) 0.74545(17) 0.29577(13) 0.0407(5) Uani 1 1 d .
O7 O 0.1923(2) 0.59455(17) 0.18136(14) 0.0418(5) Uani 1 1 d .
O8 O 0.32808(17) 0.43761(15) 0.12237(13) 0.0348(4) Uani 1 1 d .
C1 C 0.5407(2) 0.04777(19) 0.15040(15) 0.0263(5) Uani 1 1 d .
C2 C 0.4219(2) 0.02332(19) 0.14741(16) 0.0262(5) Uani 1 1 d .
C3 C 0.3523(3) -0.0733(2) 0.09116(17) 0.0315(5) Uani 1 1 d .
H3 H 0.2737 -0.0897 0.0890 0.038 Uiso 1 1 calc R
C4 C 0.4005(3) -0.1456(2) 0.03788(17) 0.0368(6) Uani 1 1 d .
H4 H 0.3540 -0.2107 0.0006 0.044 Uiso 1 1 calc R
C5 C 0.5172(3) -0.1211(2) 0.04025(17) 0.0355(6) Uani 1 1 d .
H5 H 0.5486 -0.1694 0.0041 0.043 Uiso 1 1 calc R
C6 C 0.5879(3) -0.0241(2) 0.09675(16) 0.0301(5) Uani 1 1 d .
H6 H 0.6663 -0.0078 0.0983 0.036 Uiso 1 1 calc R
C7 C 0.6064(2) 0.15680(19) 0.21548(16) 0.0246(5) Uani 1 1 d .
C8 C 0.7349(2) 0.1825(2) 0.21891(18) 0.0304(5) Uani 1 1 d .
H8A H 0.7726 0.1300 0.2358 0.046 Uiso 1 1 calc GR
H8B H 0.7710 0.2511 0.2616 0.046 Uiso 1 1 calc GR
H8C H 0.7423 0.1827 0.1616 0.046 Uiso 1 1 calc GR
C9 C 0.5364(2) 0.23454(19) 0.18794(15) 0.0246(5) Uani 1 1 d .
C10 C 0.4191(2) 0.21151(19) 0.18463(15) 0.0250(5) Uani 1 1 d .
C11 C 0.3453(2) 0.2761(2) 0.16148(16) 0.0270(5) Uani 1 1 d .
H11 H 0.2665 0.2599 0.1588 0.032 Uiso 1 1 calc R
C12 C 0.3907(2) 0.3651(2) 0.14230(16) 0.0285(5) Uani 1 1 d .
C13 C 0.5079(2) 0.38600(19) 0.14146(16) 0.0279(5) Uani 1 1 d .
C14 C 0.5815(2) 0.32188(19) 0.16574(16) 0.0259(5) Uani 1 1 d .
H14 H 0.6600 0.3370 0.1672 0.031 Uiso 1 1 calc R
C15 C 0.6569(3) 0.4943(2) 0.10791(19) 0.0353(6) Uani 1 1 d .
H15A H 0.6656 0.4399 0.0578 0.042 Uiso 1 1 calc R
H15B H 0.7138 0.4961 0.1609 0.042 Uiso 1 1 calc R
C16 C 0.6745(3) 0.6012(2) 0.09337(19) 0.0404(7) Uani 1 1 d .
H16A H 0.7498 0.6160 0.0817 0.048 Uiso 1 1 calc R
H16B H 0.6147 0.5986 0.0416 0.048 Uiso 1 1 calc R
C17 C 0.5545(3) 0.7004(2) 0.1671(2) 0.0443(7) Uani 1 1 d .
H17A H 0.5131 0.6460 0.1847 0.053 Uiso 1 1 calc R
H17B H 0.5116 0.6959 0.1080 0.053 Uiso 1 1 calc R
C18 C 0.5637(3) 0.8080(2) 0.23093(19) 0.0447(8) Uani 1 1 d .
H18A H 0.6191 0.8604 0.2212 0.054 Uiso 1 1 calc R
H18B H 0.4883 0.8276 0.2213 0.054 Uiso 1 1 calc R
C19 C 0.6214(3) 0.9093(2) 0.38049(17) 0.0327(6) Uani 1 1 d .
H19A H 0.5606 0.9452 0.3617 0.039 Uiso 1 1 calc R
H19B H 0.6959 0.9505 0.3830 0.039 Uiso 1 1 calc R
C20 C 0.6221(2) 0.9010(2) 0.47055(17) 0.0295(5) Uani 1 1 d .
H20A H 0.6734 0.8554 0.4857 0.035 Uiso 1 1 calc R
H20B H 0.6493 0.9705 0.5152 0.035 Uiso 1 1 calc R
C21 C 0.4820(2) 0.85229(19) 0.54407(16) 0.0252(5) Uani 1 1 d .
C22 C 0.5675(2) 0.87127(19) 0.62268(16) 0.0249(5) Uani 1 1 d .
H22 H 0.6462 0.8863 0.6246 0.030 Uiso 1 1 calc R
C23 C 0.5340(2) 0.86760(18) 0.69865(15) 0.0237(5) Uani 1 1 d .
C24 C 0.4162(2) 0.84404(18) 0.69550(15) 0.0233(5) Uani 1 1 d .
C25 C 0.3306(2) 0.82377(18) 0.61665(16) 0.0249(5) Uani 1 1 d .
H25 H 0.2521 0.8072 0.6146 0.030 Uiso 1 1 calc R
C26 C 0.3633(2) 0.82839(19) 0.54076(16) 0.0255(5) Uani 1 1 d .
C27 C 0.6179(2) 0.88838(19) 0.79058(15) 0.0243(5) Uani 1 1 d .
C28 C 0.7464(2) 0.9140(2) 0.79479(17) 0.0310(5) Uani 1 1 d .
H28A H 0.7631 0.9770 0.7789 0.047 Uiso 1 1 calc GR
H28B H 0.7649 0.8559 0.7542 0.047 Uiso 1 1 calc GR
H28C H 0.7926 0.9253 0.8539 0.047 Uiso 1 1 calc GR
C29 C 0.1654(2) 0.8053(2) 0.45789(18) 0.0340(6) Uani 1 1 d .
H29A H 0.1562 0.8564 0.5099 0.041 Uiso 1 1 calc R
H29B H 0.1328 0.7347 0.4571 0.041 Uiso 1 1 calc R
C30 C 0.1030(3) 0.8252(3) 0.37557(19) 0.0387(6) Uani 1 1 d .
H30A H 0.0235 0.8290 0.3774 0.046 Uiso 1 1 calc R
H30B H 0.1412 0.8933 0.3748 0.046 Uiso 1 1 calc R
C31 C 0.1895(3) 0.7731(3) 0.2567(2) 0.0457(7) Uani 1 1 d .
H31A H 0.2653 0.7765 0.2947 0.055 Uiso 1 1 calc R
H31B H 0.1883 0.8422 0.2494 0.055 Uiso 1 1 calc R
C32 C 0.1690(4) 0.6909(3) 0.1685(2) 0.0482(8) Uani 1 1 d .
H32A H 0.0887 0.6793 0.1342 0.058 Uiso 1 1 calc R
H32B H 0.2198 0.7150 0.1360 0.058 Uiso 1 1 calc R
C33 C 0.1593(3) 0.5096(2) 0.1003(2) 0.0404(7) Uani 1 1 d .
H33A H 0.1900 0.5315 0.0563 0.049 Uiso 1 1 calc R
H33B H 0.0748 0.4898 0.0783 0.049 Uiso 1 1 calc R
C34 C 0.2067(3) 0.4162(2) 0.1154(2) 0.0368(6) Uani 1 1 d .
H34A H 0.1939 0.4060 0.1694 0.044 Uiso 1 1 calc R
H34B H 0.1674 0.3523 0.0663 0.044 Uiso 1 1 calc R
N1 N 0.3397(2) 0.5019(2) 0.37810(18) 0.0415(6) Uani 1 1 d .
H1 H 0.2667 0.4976 0.3750 0.050 Uiso 1 1 calc R
N2 N 0.9216(2) 0.5214(2) 0.3671(2) 0.0479(7) Uani 1 1 d .
C35 C 0.8610(3) 0.5866(3) 0.3383(2) 0.0461(7) Uani 1 1 d .
H35 H 0.8957 0.6324 0.3131 0.055 Uiso 1 1 calc R
C36 C 0.7488(2) 0.5884(2) 0.3445(2) 0.0367(6) Uani 1 1 d .
H36 H 0.7085 0.6347 0.3238 0.044 Uiso 1 1 calc R
C37 C 0.6962(2) 0.5201(2) 0.38217(17) 0.0295(5) Uani 1 1 d .
C38 C 0.7617(3) 0.4551(2) 0.4143(2) 0.0390(6) Uani 1 1 d .
H38 H 0.7305 0.4102 0.4418 0.047 Uiso 1 1 calc R
C39 C 0.8738(3) 0.4573(3) 0.4053(2) 0.0483(8) Uani 1 1 d .
H39 H 0.9169 0.4129 0.4265 0.058 Uiso 1 1 calc R
C40 C 0.5729(2) 0.5148(2) 0.38426(16) 0.0276(5) Uani 1 1 d .
C41 C 0.5209(3) 0.6005(2) 0.3813(2) 0.0357(6) Uani 1 1 d .
H41 H 0.5644 0.6635 0.3814 0.043 Uiso 1 1 calc R
C42 C 0.4046(3) 0.5911(2) 0.3781(2) 0.0434(7) Uani 1 1 d .
H42 H 0.3700 0.6484 0.3759 0.052 Uiso 1 1 calc R
C43 C 0.3884(3) 0.4190(2) 0.38300(19) 0.0362(6) Uani 1 1 d .
H43 H 0.3429 0.3577 0.3843 0.043 Uiso 1 1 calc R
C44 C 0.5043(2) 0.4229(2) 0.38619(17) 0.0309(5) Uani 1 1 d .
H44 H 0.5368 0.3648 0.3896 0.037 Uiso 1 1 calc R
P1 P 0.92186(9) 0.80837(9) 0.59409(6) 0.0551(3) Uani 1 1 d .
F1 F 0.87260(19) 0.91017(19) 0.63217(16) 0.0663(6) Uani 1 1 d .
F2 F 0.7905(2) 0.74078(19) 0.5579(2) 0.0856(9) Uani 1 1 d .
F3 F 0.9088(2) 0.8302(2) 0.50360(15) 0.0670(6) Uani 1 1 d .
F4 F 0.9329(4) 0.7845(5) 0.6839(2) 0.170(2) Uani 1 1 d .
F5 F 1.0517(2) 0.8777(4) 0.62859(19) 0.1317(17) Uani 1 1 d .
F6 F 0.9693(3) 0.7065(3) 0.5533(3) 0.1209(14) Uani 1 1 d .
N3 N 1.1203(5) 0.6561(6) 0.9189(5) 0.136(3) Uani 1 1 d .
C45 C 1.0335(5) 0.8126(7) 0.8920(5) 0.131(3) Uani 1 1 d .
H45A H 0.9916 0.7954 0.8308 0.197 Uiso 1 1 calc GR
H45B H 1.0962 0.8730 0.9078 0.197 Uiso 1 1 calc GR
H45C H 0.9814 0.8286 0.9284 0.197 Uiso 1 1 calc GR
C46 C 1.0808(4) 0.7228(7) 0.9054(4) 0.106(2) Uani 1 1 d .
N4 N 1.0959(14) 1.1313(12) 0.9420(8) 0.380(12) Uani 1 1 d .
C47 C 1.1086(5) 1.1094(5) 0.7915(5) 0.112(2) Uani 1 1 d .
H47A H 1.0483 1.1360 0.7603 0.168 Uiso 1 1 calc GR
H47B H 1.1000 1.0353 0.7612 0.168 Uiso 1 1 calc GR
H47C H 1.1836 1.1474 0.7936 0.168 Uiso 1 1 calc GR
C48 C 1.0997(8) 1.1232(7) 0.8759(6) 0.145(3) Uani 1 1 d .
O9 O 0.1208(2) 0.5192(3) 0.3209(2) 0.0673(8) Uani 1 1 d .
H9A H 0.1195 0.5659 0.2949 0.101 Uiso 1 1 d G
H9B H 0.0659 0.5188 0.3460 0.101 Uiso 1 1 d G
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'
N N 0.0061 0.0033 '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
C13 O1 C15 118.4(2) . .
C16 O2 C17 114.0(2) . .
C18 O3 C19 110.8(2) . .
C21 O4 C20 117.05(19) . .
C26 O5 C29 117.5(2) . .
C31 O6 C30 113.4(2) . .
C33 O7 C32 111.8(2) . .
C12 O8 C34 117.6(2) . .
C2 C1 C7 114.0(2) . .
C6 C1 C2 120.0(2) . .
C6 C1 C7 126.0(2) . .
C1 C2 C27 114.0(2) . 2_666
C3 C2 C1 119.8(2) . .
C3 C2 C27 126.2(2) . 2_666
C2 C3 H3 120.1 . .
C2 C3 C4 119.9(3) . .
C4 C3 H3 120.1 . .
C3 C4 H4 119.9 . .
C5 C4 C3 120.3(3) . .
C5 C4 H4 119.9 . .
C4 C5 H5 119.9 . .
C4 C5 C6 120.2(2) . .
C6 C5 H5 119.9 . .
C1 C6 C5 119.8(3) . .
C1 C6 H6 120.1 . .
C5 C6 H6 120.1 . .
C1 C7 C24 104.55(19) . 2_666
C8 C7 C1 113.8(2) . .
C8 C7 C9 114.3(2) . .
C8 C7 C24 114.1(2) . 2_666
C9 C7 C1 104.7(2) . .
C9 C7 C24 104.29(18) . 2_666
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 C7 114.6(2) . .
C10 C9 C14 120.2(2) . .
C14 C9 C7 125.2(2) . .
C9 C10 C11 120.8(2) . .
C9 C10 C27 114.1(2) . 2_666
C11 C10 C27 125.2(2) . 2_666
C10 C11 H11 120.4 . .
C12 C11 C10 119.2(2) . .
C12 C11 H11 120.4 . .
O8 C12 C11 124.7(2) . .
O8 C12 C13 115.0(2) . .
C11 C12 C13 120.2(2) . .
O1 C13 C12 115.1(2) . .
O1 C13 C14 124.7(2) . .
C14 C13 C12 120.1(2) . .
C9 C14 H14 120.3 . .
C13 C14 C9 119.3(2) . .
C13 C14 H14 120.3 . .
O1 C15 H15A 110.4 . .
O1 C15 H15B 110.4 . .
O1 C15 C16 106.6(2) . .
H15A C15 H15B 108.6 . .
C16 C15 H15A 110.4 . .
C16 C15 H15B 110.4 . .
O2 C16 C15 112.5(2) . .
O2 C16 H16A 109.1 . .
O2 C16 H16B 109.1 . .
C15 C16 H16A 109.1 . .
C15 C16 H16B 109.1 . .
H16A C16 H16B 107.8 . .
O2 C17 H17A 110.0 . .
O2 C17 H17B 110.0 . .
O2 C17 C18 108.4(3) . .
H17A C17 H17B 108.4 . .
C18 C17 H17A 110.0 . .
C18 C17 H17B 110.0 . .
O3 C18 C17 109.5(2) . .
O3 C18 H18A 109.8 . .
O3 C18 H18B 109.8 . .
C17 C18 H18A 109.8 . .
C17 C18 H18B 109.8 . .
H18A C18 H18B 108.2 . .
O3 C19 H19A 109.8 . .
O3 C19 H19B 109.8 . .
O3 C19 C20 109.6(2) . .
H19A C19 H19B 108.2 . .
C20 C19 H19A 109.8 . .
C20 C19 H19B 109.8 . .
O4 C20 C19 106.9(2) . .
O4 C20 H20A 110.3 . .
O4 C20 H20B 110.3 . .
C19 C20 H20A 110.3 . .
C19 C20 H20B 110.3 . .
H20A C20 H20B 108.6 . .
O4 C21 C22 124.4(2) . .
O4 C21 C26 115.2(2) . .
C22 C21 C26 120.4(2) . .
C21 C22 H22 120.3 . .
C21 C22 C23 119.3(2) . .
C23 C22 H22 120.3 . .
C22 C23 C27 125.4(2) . .
C24 C23 C22 120.3(2) . .
C24 C23 C27 114.2(2) . .
C23 C24 C7 114.1(2) . 2_666
C25 C24 C7 125.5(2) . 2_666
C25 C24 C23 120.4(2) . .
C24 C25 H25 120.2 . .
C24 C25 C26 119.6(2) . .
C26 C25 H25 120.2 . .
O5 C26 C21 115.6(2) . .
O5 C26 C25 124.4(2) . .
C25 C26 C21 119.9(2) . .
C2 C27 C10 104.68(19) 2_666 2_666
C2 C27 C23 104.15(19) 2_666 .
C23 C27 C10 104.03(19) . 2_666
C28 C27 C2 114.0(2) . 2_666
C28 C27 C10 114.1(2) . 2_666
C28 C27 C23 114.7(2) . .
C27 C28 H28A 109.5 . .
C27 C28 H28B 109.5 . .
C27 C28 H28C 109.5 . .
H28A C28 H28B 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
O5 C29 H29A 110.0 . .
O5 C29 H29B 110.0 . .
O5 C29 C30 108.5(2) . .
H29A C29 H29B 108.4 . .
C30 C29 H29A 110.0 . .
C30 C29 H29B 110.0 . .
O6 C30 C29 113.4(2) . .
O6 C30 H30A 108.9 . .
O6 C30 H30B 108.9 . .
C29 C30 H30A 108.9 . .
C29 C30 H30B 108.9 . .
H30A C30 H30B 107.7 . .
O6 C31 H31A 110.0 . .
O6 C31 H31B 110.0 . .
O6 C31 C32 108.6(3) . .
H31A C31 H31B 108.3 . .
C32 C31 H31A 110.0 . .
C32 C31 H31B 110.0 . .
O7 C32 C31 109.3(3) . .
O7 C32 H32A 109.8 . .
O7 C32 H32B 109.8 . .
C31 C32 H32A 109.8 . .
C31 C32 H32B 109.8 . .
H32A C32 H32B 108.3 . .
O7 C33 H33A 109.8 . .
O7 C33 H33B 109.8 . .
O7 C33 C34 109.2(2) . .
H33A C33 H33B 108.3 . .
C34 C33 H33A 109.8 . .
C34 C33 H33B 109.8 . .
O8 C34 C33 107.9(2) . .
O8 C34 H34A 110.1 . .
O8 C34 H34B 110.1 . .
C33 C34 H34A 110.1 . .
C33 C34 H34B 110.1 . .
H34A C34 H34B 108.4 . .
C42 N1 H1 120.0 . .
C42 N1 C43 120.0(3) . .
C43 N1 H1 120.0 . .
C35 N2 C39 119.4(3) . .
N2 C35 H35 118.9 . .
N2 C35 C36 122.2(3) . .
C36 C35 H35 118.9 . .
C35 C36 H36 120.4 . .
C35 C36 C37 119.3(3) . .
C37 C36 H36 120.4 . .
C36 C37 C40 120.6(2) . .
C38 C37 C36 117.8(3) . .
C38 C37 C40 121.5(3) . .
C37 C38 H38 120.2 . .
C39 C38 C37 119.5(3) . .
C39 C38 H38 120.2 . .
N2 C39 C38 121.8(3) . .
N2 C39 H39 119.1 . .
C38 C39 H39 119.1 . .
C41 C40 C37 120.6(2) . .
C41 C40 C44 118.0(2) . .
C44 C40 C37 121.3(2) . .
C40 C41 H41 120.3 . .
C42 C41 C40 119.3(3) . .
C42 C41 H41 120.3 . .
N1 C42 C41 121.8(3) . .
N1 C42 H42 119.1 . .
C41 C42 H42 119.1 . .
N1 C43 H43 119.4 . .
N1 C43 C44 121.2(3) . .
C44 C43 H43 119.4 . .
C40 C44 H44 120.2 . .
C43 C44 C40 119.6(2) . .
C43 C44 H44 120.2 . .
F1 P1 F2 88.42(13) . .
F1 P1 F5 90.79(17) . .
F3 P1 F1 90.68(14) . .
F3 P1 F2 89.05(15) . .
F3 P1 F4 178.9(3) . .
F3 P1 F5 89.65(17) . .
F3 P1 F6 87.85(16) . .
F4 P1 F1 89.71(19) . .
F4 P1 F2 89.9(3) . .
F4 P1 F5 91.4(3) . .
F4 P1 F6 91.7(2) . .
F5 P1 F2 178.5(2) . .
F6 P1 F1 178.40(18) . .
F6 P1 F2 90.93(19) . .
F6 P1 F5 89.8(2) . .
H45A C45 H45B 109.5 . .
H45A C45 H45C 109.5 . .
H45B C45 H45C 109.5 . .
C46 C45 H45A 109.5 . .
C46 C45 H45B 109.5 . .
C46 C45 H45C 109.5 . .
N3 C46 C45 177.3(9) . .
H47A C47 H47B 109.5 . .
H47A C47 H47C 109.5 . .
H47B C47 H47C 109.5 . .
C48 C47 H47A 109.5 . .
C48 C47 H47B 109.5 . .
C48 C47 H47C 109.5 . .
N4 C48 C47 177.0(17) . .
H9A O9 H9B 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.370(3) .
O1 C15 1.426(3) .
O2 C16 1.423(3) .
O2 C17 1.425(4) .
O3 C18 1.413(3) .
O3 C19 1.420(3) .
O4 C20 1.432(3) .
O4 C21 1.371(3) .
O5 C26 1.369(3) .
O5 C29 1.430(3) .
O6 C30 1.428(3) .
O6 C31 1.420(4) .
O7 C32 1.423(3) .
O7 C33 1.419(4) .
O8 C12 1.376(3) .
O8 C34 1.419(3) .
C1 C2 1.405(4) .
C1 C6 1.385(3) .
C1 C7 1.530(3) .
C2 C3 1.387(4) .
C2 C27 1.537(3) 2_666
C3 H3 0.9300 .
C3 C4 1.394(4) .
C4 H4 0.9300 .
C4 C5 1.383(4) .
C5 H5 0.9300 .
C5 C6 1.396(4) .
C6 H6 0.9300 .
C7 C8 1.518(3) .
C7 C9 1.530(3) .
C7 C24 1.538(3) 2_666
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 C10 1.386(3) .
C9 C14 1.395(3) .
C10 C11 1.389(3) .
C10 C27 1.542(3) 2_666
C11 H11 0.9300 .
C11 C12 1.389(4) .
C12 C13 1.400(4) .
C13 C14 1.388(4) .
C14 H14 0.9300 .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 C16 1.514(4) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 C18 1.502(4) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C19 C20 1.503(3) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 C22 1.390(3) .
C21 C26 1.402(3) .
C22 H22 0.9300 .
C22 C23 1.396(3) .
C23 C24 1.392(3) .
C23 C27 1.540(3) .
C24 C7 1.538(3) 2_666
C24 C25 1.390(3) .
C25 H25 0.9300 .
C25 C26 1.393(3) .
C27 C2 1.537(3) 2_666
C27 C10 1.542(3) 2_666
C27 C28 1.515(3) .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
C29 H29A 0.9700 .
C29 H29B 0.9700 .
C29 C30 1.500(4) .
C30 H30A 0.9700 .
C30 H30B 0.9700 .
C31 H31A 0.9700 .
C31 H31B 0.9700 .
C31 C32 1.496(4) .
C32 H32A 0.9700 .
C32 H32B 0.9700 .
C33 H33A 0.9700 .
C33 H33B 0.9700 .
C33 C34 1.507(4) .
C34 H34A 0.9700 .
C34 H34B 0.9700 .
N1 H1 0.8600 .
N1 C42 1.336(4) .
N1 C43 1.341(4) .
N2 C35 1.333(4) .
N2 C39 1.334(5) .
C35 H35 0.9300 .
C35 C36 1.378(4) .
C36 H36 0.9300 .
C36 C37 1.393(4) .
C37 C38 1.388(4) .
C37 C40 1.481(4) .
C38 H38 0.9300 .
C38 C39 1.382(4) .
C39 H39 0.9300 .
C40 C41 1.392(4) .
C40 C44 1.398(4) .
C41 H41 0.9300 .
C41 C42 1.373(4) .
C42 H42 0.9300 .
C43 H43 0.9300 .
C43 C44 1.374(4) .
C44 H44 0.9300 .
P1 F1 1.588(2) .
P1 F2 1.599(3) .
P1 F3 1.563(2) .
P1 F4 1.568(3) .
P1 F5 1.592(3) .
P1 F6 1.587(3) .
N3 C46 1.122(8) .
C45 H45A 0.9600 .
C45 H45B 0.9600 .
C45 H45C 0.9600 .
C45 C46 1.452(10) .
N4 C48 1.065(12) .
C47 H47A 0.9600 .
C47 H47B 0.9600 .
C47 H47C 0.9600 .
C47 C48 1.369(11) .
O9 H9A 0.8498 .
O9 H9B 0.8498 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O9 0.86 1.88 2.655(4) 149.0 .
O9 H9A O6 0.85 2.45 3.215(4) 149.7 .
O9 H9A O7 0.85 2.32 2.975(3) 134.6 .
O9 H9B N2 0.85 1.84 2.663(4) 162.0 1_455
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C13 C14 C9 -179.1(2) . .
O1 C15 C16 O2 63.6(3) . .
O2 C17 C18 O3 -73.4(3) . .
O3 C19 C20 O4 -70.0(3) . .
O4 C21 C22 C23 177.7(2) . .
O4 C21 C26 O5 -1.1(3) . .
O4 C21 C26 C25 -178.5(2) . .
O5 C29 C30 O6 66.9(3) . .
O6 C31 C32 O7 -70.3(4) . .
O7 C33 C34 O8 -76.0(3) . .
O8 C12 C13 O1 -2.7(3) . .
O8 C12 C13 C14 176.1(2) . .
C1 C2 C3 C4 0.0(4) . .
C1 C7 C9 C10 54.8(3) . .
C1 C7 C9 C14 -124.1(2) . .
C2 C1 C6 C5 -0.5(4) . .
C2 C1 C7 C8 179.6(2) . .
C2 C1 C7 C9 -54.9(2) . .
C2 C1 C7 C24 54.5(3) . 2_666
C2 C3 C4 C5 -0.6(4) . .
C3 C4 C5 C6 0.7(4) . .
C4 C5 C6 C1 -0.1(4) . .
C6 C1 C2 C3 0.5(3) . .
C6 C1 C2 C27 -178.9(2) . 2_666
C6 C1 C7 C8 -0.9(3) . .
C6 C1 C7 C9 124.6(2) . .
C6 C1 C7 C24 -126.0(2) . 2_666
C7 C1 C2 C3 -179.9(2) . .
C7 C1 C2 C27 0.6(3) . 2_666
C7 C1 C6 C5 -180.0(2) . .
C7 C9 C10 C11 179.4(2) . .
C7 C9 C10 C27 0.0(3) . 2_666
C7 C9 C14 C13 179.7(2) . .
C7 C24 C25 C26 179.2(2) 2_666 .
C8 C7 C9 C10 180.0(2) . .
C8 C7 C9 C14 1.0(3) . .
C9 C10 C11 C12 -0.6(4) . .
C10 C9 C14 C13 0.8(3) . .
C10 C11 C12 O8 -177.0(2) . .
C10 C11 C12 C13 3.6(4) . .
C11 C12 C13 O1 176.8(2) . .
C11 C12 C13 C14 -4.4(4) . .
C12 O8 C34 C33 175.8(2) . .
C12 C13 C14 C9 2.2(4) . .
C13 O1 C15 C16 -172.5(2) . .
C14 C9 C10 C11 -1.6(4) . .
C14 C9 C10 C27 179.0(2) . 2_666
C15 O1 C13 C12 -175.0(2) . .
C15 O1 C13 C14 6.2(4) . .
C16 O2 C17 C18 -162.9(2) . .
C17 O2 C16 C15 -86.6(3) . .
C18 O3 C19 C20 161.6(3) . .
C19 O3 C18 C17 174.3(3) . .
C20 O4 C21 C22 -10.3(3) . .
C20 O4 C21 C26 168.3(2) . .
C21 O4 C20 C19 -173.7(2) . .
C21 C22 C23 C24 0.7(3) . .
C21 C22 C23 C27 -179.0(2) . .
C22 C21 C26 O5 177.5(2) . .
C22 C21 C26 C25 0.1(4) . .
C22 C23 C24 C7 -179.9(2) . 2_666
C22 C23 C24 C25 0.1(3) . .
C22 C23 C27 C2 125.0(2) . 2_666
C22 C23 C27 C10 -125.6(2) . 2_666
C22 C23 C27 C28 -0.3(3) . .
C23 C24 C25 C26 -0.8(3) . .
C24 C7 C9 C10 -54.8(3) 2_666 .
C24 C7 C9 C14 126.3(2) 2_666 .
C24 C23 C27 C2 -54.8(3) . 2_666
C24 C23 C27 C10 54.7(3) . 2_666
C24 C23 C27 C28 179.9(2) . .
C24 C25 C26 O5 -176.5(2) . .
C24 C25 C26 C21 0.7(4) . .
C26 O5 C29 C30 162.9(2) . .
C26 C21 C22 C23 -0.8(4) . .
C27 C2 C3 C4 179.4(2) 2_666 .
C27 C10 C11 C12 178.7(2) 2_666 .
C27 C23 C24 C7 -0.2(3) . 2_666
C27 C23 C24 C25 179.8(2) . .
C29 O5 C26 C21 -171.6(2) . .
C29 O5 C26 C25 5.7(4) . .
C30 O6 C31 C32 -172.9(2) . .
C31 O6 C30 C29 -96.8(3) . .
C32 O7 C33 C34 169.2(3) . .
C33 O7 C32 C31 172.0(3) . .
C34 O8 C12 C11 -4.2(4) . .
C34 O8 C12 C13 175.2(2) . .
N1 C43 C44 C40 0.0(4) . .
N2 C35 C36 C37 0.0(5) . .
C35 N2 C39 C38 1.3(5) . .
C35 C36 C37 C38 1.9(4) . .
C35 C36 C37 C40 -175.7(3) . .
C36 C37 C38 C39 -2.2(4) . .
C36 C37 C40 C41 -24.6(4) . .
C36 C37 C40 C44 153.2(3) . .
C37 C38 C39 N2 0.7(5) . .
C37 C40 C41 C42 176.2(3) . .
C37 C40 C44 C43 -176.3(2) . .
C38 C37 C40 C41 157.8(3) . .
C38 C37 C40 C44 -24.4(4) . .
C39 N2 C35 C36 -1.7(5) . .
C40 C37 C38 C39 175.4(3) . .
C40 C41 C42 N1 0.2(5) . .
C41 C40 C44 C43 1.5(4) . .
C42 N1 C43 C44 -1.4(5) . .
C43 N1 C42 C41 1.3(5) . .
C44 C40 C41 C42 -1.6(4) . .
