#------------------------------------------------------------------------------
#$Date: 2016-01-01 09:53:26 +0200 (Fri, 01 Jan 2016) $
#$Revision: 171854 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/82/7118206.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_7118206
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(C12 H12 N O), 2(F6 P), 2(H2 O)'
_chemical_formula_sum            'C92 H104 F12 N2 O20 P2'
_chemical_formula_weight         1847.71
_chemical_name_systematic
;
 ?
;
_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             2015-08-14
_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                108.815(19)
_cell_angle_beta                 93.025(12)
_cell_angle_gamma                100.752(11)
_cell_formula_units_Z            1
_cell_length_a                   12.778(12)
_cell_length_b                   12.983(14)
_cell_length_c                   14.022(14)
_cell_measurement_reflns_used    7692
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4441
_cell_measurement_theta_min      1.5457
_cell_volume                     2147(4)
_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  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 45.3505
              2theta: -19.9355
scan:
    Number of images: 336
               Slice: -110.0000 - 58.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 45.3505
              2theta: -19.9355
scan:
    Number of images: 332
               Slice: -110.0000 - 56.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 45.3505
              2theta: -19.9355
scan:
    Number of images: 200
               Slice: -42.5000 - 57.5000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 45.3505
              2theta: -19.9355
;
_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      0.0030
_diffrn_orient_matrix_UB_12      -0.0234
_diffrn_orient_matrix_UB_13      -0.0767
_diffrn_orient_matrix_UB_21      0.0237
_diffrn_orient_matrix_UB_22      0.0697
_diffrn_orient_matrix_UB_23      -0.0391
_diffrn_orient_matrix_UB_31      0.0756
_diffrn_orient_matrix_UB_32      0.0011
_diffrn_orient_matrix_UB_33      -0.0070
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_laue_measured_fraction_full 0.997
_diffrn_reflns_laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29359
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.385
_diffrn_reflns_theta_min         1.546
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.525
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         9623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.525
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0950
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2632
_refine_ls_wR_factor_ref         0.2738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8297
_reflns_number_total             9623
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc08166a2.cif
_cod_data_source_block           mx4011a
_cod_database_code               7118206
_shelxl_version_number           2013-4
_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             9626
_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:
 O10(H10A,H10B)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,
 H27B), C28(H28A,H28B), 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:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C16(H16), C21(H21), C24(H24),
 N1(H1), C35(H35), C36(H36), C38(H38), C39(H39), C41(H41), C42(H42), C44(H44),
 C45(H45)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C46(H46A,H46B,H46C)
;
_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 0.64274(16) 0.80488(18) 0.11530(16) 0.0365(5) Uani 1 1 d .
O2 O 0.57480(16) 1.00075(17) 0.14280(16) 0.0350(5) Uani 1 1 d .
O3 O 0.12854(18) 0.57503(17) 0.43503(16) 0.0369(5) Uani 1 1 d .
O4 O 0.21420(18) 0.53640(18) 0.61385(17) 0.0396(5) Uani 1 1 d .
O5 O 0.31200(17) 0.75906(17) 0.76318(15) 0.0372(5) Uani 1 1 d .
O6 O 0.06767(19) 0.75867(17) 0.47000(17) 0.0393(5) Uani 1 1 d .
O7 O 0.07545(18) 0.9049(2) 0.67723(17) 0.0439(6) Uani 1 1 d .
O8 O 0.13244(17) 1.09285(18) 0.86219(17) 0.0385(5) Uani 1 1 d .
C1 C 0.1407(2) 0.7011(2) 0.0465(2) 0.0321(6) Uani 1 1 d .
C2 C 0.0584(2) 0.7068(3) -0.0194(2) 0.0338(7) Uani 1 1 d .
H2 H 0.0341 0.7725 -0.0075 0.041 Uiso 1 1 calc R
C3 C 0.0125(2) 0.6127(3) -0.1040(2) 0.0382(7) Uani 1 1 d .
H3 H -0.0433 0.6159 -0.1475 0.046 Uiso 1 1 calc R
C4 C 0.0485(2) 0.5168(3) -0.1229(2) 0.0383(7) Uani 1 1 d .
H4 H 0.0179 0.4554 -0.1798 0.046 Uiso 1 1 calc R
C5 C 0.1316(2) 0.5096(3) -0.0574(2) 0.0348(7) Uani 1 1 d .
H5 H 0.1561 0.4438 -0.0708 0.042 Uiso 1 1 calc R
C6 C 0.1774(2) 0.6018(2) 0.0283(2) 0.0293(6) Uani 1 1 d .
C7 C 0.2654(2) 0.6071(2) 0.1101(2) 0.0299(6) Uani 1 1 d .
C8 C 0.2152(2) 0.6436(2) 0.2101(2) 0.0288(6) Uani 1 1 d .
C9 C 0.1785(2) 0.7420(2) 0.2279(2) 0.0307(6) Uani 1 1 d .
C10 C 0.1969(2) 0.7956(2) 0.1450(2) 0.0293(6) Uani 1 1 d .
C11 C 0.3183(2) 0.8074(2) 0.1350(2) 0.0292(6) Uani 1 1 d .
C12 C 0.3542(2) 0.7089(2) 0.1170(2) 0.0286(6) Uani 1 1 d .
C13 C 0.4619(2) 0.7085(2) 0.1071(2) 0.0314(6) Uani 1 1 d .
H13 H 0.4855 0.6422 0.0934 0.038 Uiso 1 1 calc R
C14 C 0.5351(2) 0.8079(2) 0.1176(2) 0.0323(6) Uani 1 1 d .
C15 C 0.4985(2) 0.9069(2) 0.1345(2) 0.0314(6) Uani 1 1 d .
C16 C 0.3894(2) 0.9065(2) 0.1438(2) 0.0309(6) Uani 1 1 d .
H16 H 0.3647 0.9721 0.1558 0.037 Uiso 1 1 calc R
C17 C 0.6901(2) 0.8263(3) 0.0315(2) 0.0399(7) Uani 1 1 d .
H17A H 0.6806 0.8978 0.0289 0.048 Uiso 1 1 calc R
H17B H 0.6561 0.7690 -0.0317 0.048 Uiso 1 1 calc R
C18 C 0.5354(2) 1.0969(2) 0.1430(2) 0.0360(7) Uani 1 1 d .
H18A H 0.5023 1.1246 0.2042 0.043 Uiso 1 1 calc R
H18B H 0.4818 1.0777 0.0849 0.043 Uiso 1 1 calc R
C19 C 0.3047(2) 0.4994(2) 0.0906(2) 0.0351(7) Uani 1 1 d .
H19A H 0.2452 0.4397 0.0854 0.053 Uiso 1 1 calc GR
H19B H 0.3571 0.5077 0.1456 0.053 Uiso 1 1 calc GR
H19C H 0.3365 0.4829 0.0284 0.053 Uiso 1 1 calc GR
C20 C 0.1560(2) 0.9024(2) 0.1641(2) 0.0340(6) Uani 1 1 d .
H20A H 0.1706 0.9311 0.1099 0.051 Uiso 1 1 calc GR
H20B H 0.1915 0.9566 0.2273 0.051 Uiso 1 1 calc GR
H20C H 0.0800 0.8871 0.1672 0.051 Uiso 1 1 calc GR
C21 C 0.2012(2) 0.5855(2) 0.2788(2) 0.0308(6) Uani 1 1 d .
H21 H 0.2263 0.5202 0.2675 0.037 Uiso 1 1 calc R
C22 C 0.1499(2) 0.6256(2) 0.3641(2) 0.0313(6) Uani 1 1 d .
C23 C 0.1143(2) 0.7261(2) 0.3825(2) 0.0329(6) Uani 1 1 d .
C24 C 0.1287(2) 0.7835(2) 0.3132(2) 0.0314(6) Uani 1 1 d .
H24 H 0.1047 0.8493 0.3245 0.038 Uiso 1 1 calc R
C25 C 0.1720(3) 0.4797(3) 0.4294(2) 0.0366(7) Uani 1 1 d .
H25A H 0.2481 0.4955 0.4232 0.044 Uiso 1 1 calc R
H25B H 0.1368 0.4171 0.3702 0.044 Uiso 1 1 calc R
C26 C 0.1547(3) 0.4512(2) 0.5241(2) 0.0376(7) Uani 1 1 d .
H26A H 0.0789 0.4406 0.5318 0.045 Uiso 1 1 calc R
H26B H 0.1762 0.3816 0.5170 0.045 Uiso 1 1 calc R
C27 C 0.1577(3) 0.6203(3) 0.6638(2) 0.0381(7) Uani 1 1 d .
H27A H 0.0848 0.5857 0.6682 0.046 Uiso 1 1 calc R
H27B H 0.1546 0.6700 0.6253 0.046 Uiso 1 1 calc R
C28 C 0.2155(2) 0.6854(3) 0.7691(2) 0.0370(7) Uani 1 1 d .
H28A H 0.1691 0.7283 0.8097 0.044 Uiso 1 1 calc R
H28B H 0.2333 0.6343 0.8017 0.044 Uiso 1 1 calc R
C29 C 0.3709(3) 0.8141(3) 0.8616(2) 0.0372(7) Uani 1 1 d .
H29A H 0.3974 0.7604 0.8855 0.045 Uiso 1 1 calc R
H29B H 0.3242 0.8481 0.9089 0.045 Uiso 1 1 calc R
C30 C 0.0361(2) 0.8626(2) 0.4978(2) 0.0354(7) Uani 1 1 d .
H30A H -0.0179 0.8623 0.4464 0.043 Uiso 1 1 calc R
H30B H 0.0973 0.9225 0.5050 0.043 Uiso 1 1 calc R
C31 C -0.0088(3) 0.8782(3) 0.5976(2) 0.0381(7) Uani 1 1 d .
H31A H -0.0479 0.9377 0.6111 0.046 Uiso 1 1 calc R
H31B H -0.0584 0.8103 0.5940 0.046 Uiso 1 1 calc R
C32 C 0.0397(3) 0.9064(3) 0.7720(2) 0.0407(7) Uani 1 1 d .
H32A H 0.0241 0.8313 0.7745 0.049 Uiso 1 1 calc R
H32B H -0.0255 0.9348 0.7798 0.049 Uiso 1 1 calc R
C33 C 0.1262(3) 0.9798(3) 0.8569(2) 0.0406(7) Uani 1 1 d .
H33A H 0.1088 0.9711 0.9208 0.049 Uiso 1 1 calc R
H33B H 0.1946 0.9593 0.8436 0.049 Uiso 1 1 calc R
C34 C 0.1905(2) 1.1734(3) 0.9538(2) 0.0402(7) Uani 1 1 d .
H34A H 0.1579 1.1599 1.0108 0.048 Uiso 1 1 calc R
H34B H 0.1831 1.2468 0.9550 0.048 Uiso 1 1 calc R
O9 O 0.7713(2) -0.2334(2) 0.39069(19) 0.0511(6) Uani 1 1 d .
N1 N 0.5167(2) 0.3436(2) 0.5839(2) 0.0454(7) Uani 1 1 d .
H1 H 0.4866 0.3997 0.6026 0.054 Uiso 1 1 calc R
C35 C 0.5142(3) 0.2758(3) 0.6389(3) 0.0435(8) Uani 1 1 d .
H35 H 0.4806 0.2912 0.6976 0.052 Uiso 1 1 calc R
C36 C 0.5593(3) 0.1852(3) 0.6115(2) 0.0398(7) Uani 1 1 d .
H36 H 0.5575 0.1405 0.6517 0.048 Uiso 1 1 calc R
C37 C 0.6088(2) 0.1594(3) 0.5221(2) 0.0376(7) Uani 1 1 d .
C38 C 0.6131(3) 0.2344(3) 0.4684(3) 0.0450(8) Uani 1 1 d .
H38 H 0.6484 0.2228 0.4107 0.054 Uiso 1 1 calc R
C39 C 0.5662(3) 0.3239(3) 0.4997(3) 0.0491(9) Uani 1 1 d .
H39 H 0.5685 0.3718 0.4624 0.059 Uiso 1 1 calc R
C40 C 0.6533(2) 0.0579(3) 0.4869(2) 0.0371(7) Uani 1 1 d .
C41 C 0.6692(3) -0.0051(3) 0.5494(2) 0.0390(7) Uani 1 1 d .
H41 H 0.6517 0.0182 0.6154 0.047 Uiso 1 1 calc R
C42 C 0.7091(3) -0.0990(3) 0.5166(2) 0.0406(7) Uani 1 1 d .
H42 H 0.7196 -0.1381 0.5602 0.049 Uiso 1 1 calc R
C43 C 0.7342(3) -0.1365(3) 0.4169(3) 0.0412(8) Uani 1 1 d .
C44 C 0.7209(3) -0.0766(3) 0.3523(2) 0.0427(8) Uani 1 1 d .
H44 H 0.7388 -0.1005 0.2865 0.051 Uiso 1 1 calc R
C45 C 0.6806(3) 0.0192(3) 0.3876(2) 0.0396(7) Uani 1 1 d .
H45 H 0.6714 0.0589 0.3443 0.048 Uiso 1 1 calc R
C46 C 0.7963(4) -0.2770(4) 0.2886(3) 0.0577(10) Uani 1 1 d .
H46A H 0.7328 -0.2940 0.2418 0.087 Uiso 1 1 calc GR
H46B H 0.8228 -0.3435 0.2803 0.087 Uiso 1 1 calc GR
H46C H 0.8502 -0.2225 0.2756 0.087 Uiso 1 1 calc GR
P1 P 0.67628(7) 0.73461(8) 0.73015(7) 0.0424(3) Uani 1 1 d .
F1 F 0.71869(18) 0.84761(17) 0.82303(17) 0.0558(6) Uani 1 1 d .
F2 F 0.57447(17) 0.70275(17) 0.78678(17) 0.0539(6) Uani 1 1 d .
F3 F 0.6085(2) 0.7987(2) 0.67764(18) 0.0670(7) Uani 1 1 d .
F4 F 0.6308(2) 0.6215(2) 0.63636(19) 0.0712(7) Uani 1 1 d .
F5 F 0.77604(18) 0.7641(2) 0.67326(18) 0.0607(6) Uani 1 1 d .
F6 F 0.74422(18) 0.67206(18) 0.78324(17) 0.0564(6) Uani 1 1 d .
O10 O 0.4124(2) 0.5067(2) 0.6756(3) 0.0682(9) Uani 1 1 d .
H10A H 0.4584 0.5666 0.7063 0.102 Uiso 1 1 d G
H10B H 0.3530 0.5222 0.6616 0.102 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
C14 O1 C17 115.9(2) . .
C15 O2 C18 116.3(2) . .
C22 O3 C25 118.6(2) . .
C27 O4 C26 114.6(2) . .
C29 O5 C28 110.1(2) . .
C23 O6 C30 118.3(2) . .
C31 O7 C32 114.0(2) . .
C34 O8 C33 113.9(2) . .
C2 C1 C6 120.1(3) . .
C2 C1 C10 125.9(3) . .
C6 C1 C10 113.9(2) . .
C1 C2 H2 120.3 . .
C1 C2 C3 119.5(3) . .
C3 C2 H2 120.3 . .
C2 C3 H3 119.6 . .
C4 C3 C2 120.8(3) . .
C4 C3 H3 119.6 . .
C3 C4 H4 119.7 . .
C3 C4 C5 120.6(3) . .
C5 C4 H4 119.7 . .
C4 C5 H5 120.2 . .
C6 C5 C4 119.6(3) . .
C6 C5 H5 120.2 . .
C1 C6 C7 114.0(2) . .
C5 C6 C1 119.4(3) . .
C5 C6 C7 126.6(3) . .
C6 C7 C8 104.0(2) . .
C6 C7 C12 105.1(2) . .
C8 C7 C12 104.7(2) . .
C19 C7 C6 113.9(2) . .
C19 C7 C8 113.9(2) . .
C19 C7 C12 114.1(2) . .
C9 C8 C7 114.0(2) . .
C9 C8 C21 119.9(3) . .
C21 C8 C7 126.1(3) . .
C8 C9 C10 114.3(3) . .
C24 C9 C8 120.7(3) . .
C24 C9 C10 125.0(3) . .
C9 C10 C1 103.4(2) . .
C9 C10 C11 104.8(2) . .
C11 C10 C1 104.8(2) . .
C20 C10 C1 113.4(2) . .
C20 C10 C9 114.2(2) . .
C20 C10 C11 115.1(2) . .
C12 C11 C10 114.4(2) . .
C12 C11 C16 120.6(3) . .
C16 C11 C10 125.0(3) . .
C11 C12 C7 114.0(3) . .
C13 C12 C7 126.0(3) . .
C13 C12 C11 120.0(3) . .
C12 C13 H13 119.9 . .
C12 C13 C14 120.2(3) . .
C14 C13 H13 119.9 . .
O1 C14 C13 118.0(3) . .
O1 C14 C15 122.2(2) . .
C15 C14 C13 119.8(3) . .
O2 C15 C14 116.4(3) . .
O2 C15 C16 123.9(3) . .
C14 C15 C16 119.7(2) . .
C11 C16 C15 119.7(3) . .
C11 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
O1 C17 H17A 110.1 . .
O1 C17 H17B 110.1 . .
O1 C17 C34 107.9(3) . 2_676
H17A C17 H17B 108.4 . .
C34 C17 H17A 110.1 2_676 .
C34 C17 H17B 110.1 2_676 .
O2 C18 H18A 110.0 . .
O2 C18 H18B 110.0 . .
O2 C18 C29 108.6(3) . 2_676
H18A C18 H18B 108.4 . .
C29 C18 H18A 110.0 2_676 .
C29 C18 H18B 110.0 2_676 .
C7 C19 H19A 109.5 . .
C7 C19 H19B 109.5 . .
C7 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C10 C20 H20A 109.5 . .
C10 C20 H20B 109.5 . .
C10 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C8 C21 H21 120.0 . .
C22 C21 C8 120.0(3) . .
C22 C21 H21 120.0 . .
O3 C22 C21 125.6(3) . .
O3 C22 C23 114.5(3) . .
C21 C22 C23 119.9(3) . .
O6 C23 C22 114.6(2) . .
O6 C23 C24 125.8(3) . .
C24 C23 C22 119.6(3) . .
C9 C24 C23 120.0(3) . .
C9 C24 H24 120.0 . .
C23 C24 H24 120.0 . .
O3 C25 H25A 109.9 . .
O3 C25 H25B 109.9 . .
O3 C25 C26 108.9(3) . .
H25A C25 H25B 108.3 . .
C26 C25 H25A 109.9 . .
C26 C25 H25B 109.9 . .
O4 C26 C25 112.6(3) . .
O4 C26 H26A 109.1 . .
O4 C26 H26B 109.1 . .
C25 C26 H26A 109.1 . .
C25 C26 H26B 109.1 . .
H26A C26 H26B 107.8 . .
O4 C27 H27A 109.9 . .
O4 C27 H27B 109.9 . .
O4 C27 C28 108.9(3) . .
H27A C27 H27B 108.3 . .
C28 C27 H27A 109.9 . .
C28 C27 H27B 109.9 . .
O5 C28 C27 110.0(2) . .
O5 C28 H28A 109.7 . .
O5 C28 H28B 109.7 . .
C27 C28 H28A 109.7 . .
C27 C28 H28B 109.7 . .
H28A C28 H28B 108.2 . .
O5 C29 C18 109.7(2) . 2_676
O5 C29 H29A 109.7 . .
O5 C29 H29B 109.7 . .
C18 C29 H29A 109.7 2_676 .
C18 C29 H29B 109.7 2_676 .
H29A C29 H29B 108.2 . .
O6 C30 H30A 110.4 . .
O6 C30 H30B 110.4 . .
O6 C30 C31 106.8(2) . .
H30A C30 H30B 108.6 . .
C31 C30 H30A 110.4 . .
C31 C30 H30B 110.4 . .
O7 C31 C30 110.1(3) . .
O7 C31 H31A 109.6 . .
O7 C31 H31B 109.6 . .
C30 C31 H31A 109.6 . .
C30 C31 H31B 109.6 . .
H31A C31 H31B 108.1 . .
O7 C32 H32A 109.8 . .
O7 C32 H32B 109.8 . .
O7 C32 C33 109.2(3) . .
H32A C32 H32B 108.3 . .
C33 C32 H32A 109.8 . .
C33 C32 H32B 109.8 . .
O8 C33 C32 107.8(3) . .
O8 C33 H33A 110.1 . .
O8 C33 H33B 110.1 . .
C32 C33 H33A 110.1 . .
C32 C33 H33B 110.1 . .
H33A C33 H33B 108.5 . .
O8 C34 C17 115.0(3) . 2_676
O8 C34 H34A 108.5 . .
O8 C34 H34B 108.5 . .
C17 C34 H34A 108.5 2_676 .
C17 C34 H34B 108.5 2_676 .
H34A C34 H34B 107.5 . .
C43 O9 C46 117.4(3) . .
C35 N1 H1 120.0 . .
C35 N1 C39 120.1(3) . .
C39 N1 H1 120.0 . .
N1 C35 H35 119.0 . .
N1 C35 C36 122.0(3) . .
C36 C35 H35 119.0 . .
C35 C36 H36 120.1 . .
C35 C36 C37 119.8(3) . .
C37 C36 H36 120.1 . .
C36 C37 C40 121.2(3) . .
C38 C37 C36 116.5(3) . .
C38 C37 C40 122.3(3) . .
C37 C38 H38 119.5 . .
C39 C38 C37 120.9(3) . .
C39 C38 H38 119.5 . .
N1 C39 C38 120.6(3) . .
N1 C39 H39 119.7 . .
C38 C39 H39 119.7 . .
C41 C40 C37 122.4(3) . .
C45 C40 C37 120.8(3) . .
C45 C40 C41 116.8(3) . .
C40 C41 H41 118.8 . .
C42 C41 C40 122.4(3) . .
C42 C41 H41 118.8 . .
C41 C42 H42 120.2 . .
C41 C42 C43 119.6(3) . .
C43 C42 H42 120.2 . .
O9 C43 C42 115.0(3) . .
O9 C43 C44 124.8(3) . .
C44 C43 C42 120.3(3) . .
C43 C44 H44 120.4 . .
C45 C44 C43 119.1(3) . .
C45 C44 H44 120.4 . .
C40 C45 H45 119.1 . .
C44 C45 C40 121.9(3) . .
C44 C45 H45 119.1 . .
O9 C46 H46A 109.5 . .
O9 C46 H46B 109.5 . .
O9 C46 H46C 109.5 . .
H46A C46 H46B 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
F1 P1 F2 90.33(13) . .
F1 P1 F3 89.46(15) . .
F1 P1 F4 178.63(13) . .
F1 P1 F6 89.98(14) . .
F3 P1 F2 89.81(14) . .
F4 P1 F2 88.83(14) . .
F4 P1 F3 89.46(17) . .
F5 P1 F1 90.50(14) . .
F5 P1 F2 179.14(14) . .
F5 P1 F3 90.39(14) . .
F5 P1 F4 90.34(15) . .
F5 P1 F6 89.57(14) . .
F6 P1 F2 90.23(14) . .
F6 P1 F3 179.43(16) . .
F6 P1 F4 91.11(15) . .
H10A O10 H10B 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C14 1.385(4) .
O1 C17 1.431(4) .
O2 C15 1.379(3) .
O2 C18 1.430(4) .
O3 C22 1.370(3) .
O3 C25 1.430(4) .
O4 C26 1.440(4) .
O4 C27 1.433(4) .
O5 C28 1.436(3) .
O5 C29 1.427(4) .
O6 C23 1.369(4) .
O6 C30 1.420(4) .
O7 C31 1.418(4) .
O7 C32 1.424(4) .
O8 C33 1.432(4) .
O8 C34 1.427(4) .
C1 C2 1.391(4) .
C1 C6 1.405(4) .
C1 C10 1.550(4) .
C2 H2 0.9300 .
C2 C3 1.403(4) .
C3 H3 0.9300 .
C3 C4 1.358(5) .
C4 H4 0.9300 .
C4 C5 1.404(4) .
C5 H5 0.9300 .
C5 C6 1.399(4) .
C6 C7 1.540(4) .
C7 C8 1.543(4) .
C7 C12 1.546(4) .
C7 C19 1.520(4) .
C8 C9 1.394(4) .
C8 C21 1.402(4) .
C9 C10 1.543(4) .
C9 C24 1.385(4) .
C10 C11 1.548(4) .
C10 C20 1.521(4) .
C11 C12 1.391(4) .
C11 C16 1.395(4) .
C12 C13 1.390(4) .
C13 H13 0.9300 .
C13 C14 1.405(4) .
C14 C15 1.402(4) .
C15 C16 1.407(4) .
C16 H16 0.9300 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 C34 1.528(5) 2_676
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C18 C29 1.521(4) 2_676
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21 0.9300 .
C21 C22 1.393(4) .
C22 C23 1.412(4) .
C23 C24 1.403(4) .
C24 H24 0.9300 .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C25 C26 1.505(4) .
C26 H26A 0.9700 .
C26 H26B 0.9700 .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C27 C28 1.513(4) .
C28 H28A 0.9700 .
C28 H28B 0.9700 .
C29 C18 1.521(4) 2_676
C29 H29A 0.9700 .
C29 H29B 0.9700 .
C30 H30A 0.9700 .
C30 H30B 0.9700 .
C30 C31 1.508(4) .
C31 H31A 0.9700 .
C31 H31B 0.9700 .
C32 H32A 0.9700 .
C32 H32B 0.9700 .
C32 C33 1.512(4) .
C33 H33A 0.9700 .
C33 H33B 0.9700 .
C34 C17 1.528(5) 2_676
C34 H34A 0.9700 .
C34 H34B 0.9700 .
O9 C43 1.373(4) .
O9 C46 1.437(5) .
N1 H1 0.8600 .
N1 C35 1.342(4) .
N1 C39 1.343(5) .
C35 H35 0.9300 .
C35 C36 1.359(5) .
C36 H36 0.9300 .
C36 C37 1.405(5) .
C37 C38 1.405(4) .
C37 C40 1.482(5) .
C38 H38 0.9300 .
C38 C39 1.364(5) .
C39 H39 0.9300 .
C40 C41 1.409(4) .
C40 C45 1.407(5) .
C41 H41 0.9300 .
C41 C42 1.361(5) .
C42 H42 0.9300 .
C42 C43 1.402(5) .
C43 C44 1.392(5) .
C44 H44 0.9300 .
C44 C45 1.387(5) .
C45 H45 0.9300 .
C46 H46A 0.9600 .
C46 H46B 0.9600 .
C46 H46C 0.9600 .
P1 F1 1.593(3) .
P1 F2 1.617(2) .
P1 F3 1.607(2) .
P1 F4 1.606(3) .
P1 F5 1.591(3) .
P1 F6 1.597(2) .
O10 H10A 0.8501 .
O10 H10B 0.8502 .
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
N1 H1 O10 0.86 1.88 2.719(5) 162.9
O10 H10A F2 0.85 2.04 2.887(4) 174.9
O10 H10A F4 0.85 2.53 3.074(5) 122.5
O10 H10B O4 0.85 1.92 2.768(4) 171.5
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_4
O1 C14 C15 O2 3.8(4) .
O1 C14 C15 C16 -175.2(3) .
O2 C15 C16 C11 -179.5(3) .
O3 C22 C23 O6 2.2(4) .
O3 C22 C23 C24 -177.9(2) .
O3 C25 C26 O4 -65.6(3) .
O4 C27 C28 O5 74.4(3) .
O6 C23 C24 C9 179.2(3) .
O6 C30 C31 O7 73.8(3) .
O7 C32 C33 O8 70.1(3) .
C1 C2 C3 C4 -1.0(4) .
C1 C6 C7 C8 55.1(3) .
C1 C6 C7 C12 -54.7(3) .
C1 C6 C7 C19 179.7(2) .
C1 C10 C11 C12 -54.5(3) .
C1 C10 C11 C16 126.2(3) .
C2 C1 C6 C5 1.0(4) .
C2 C1 C6 C7 -177.7(3) .
C2 C1 C10 C9 122.3(3) .
C2 C1 C10 C11 -128.2(3) .
C2 C1 C10 C20 -1.9(4) .
C2 C3 C4 C5 0.9(4) .
C3 C4 C5 C6 0.2(4) .
C4 C5 C6 C1 -1.1(4) .
C4 C5 C6 C7 177.4(3) .
C5 C6 C7 C8 -123.5(3) .
C5 C6 C7 C12 126.8(3) .
C5 C6 C7 C19 1.2(4) .
C6 C1 C2 C3 0.0(4) .
C6 C1 C10 C9 -55.4(3) .
C6 C1 C10 C11 54.1(3) .
C6 C1 C10 C20 -179.7(2) .
C6 C7 C8 C9 -55.0(3) .
C6 C7 C8 C21 122.8(3) .
C6 C7 C12 C11 54.6(3) .
C6 C7 C12 C13 -125.6(3) .
C7 C8 C9 C10 -0.8(3) .
C7 C8 C9 C24 178.1(2) .
C7 C8 C21 C22 -177.0(2) .
C7 C12 C13 C14 -178.3(3) .
C8 C7 C12 C11 -54.7(3) .
C8 C7 C12 C13 125.1(3) .
C8 C9 C10 C1 55.8(3) .
C8 C9 C10 C11 -53.7(3) .
C8 C9 C10 C20 179.5(2) .
C8 C9 C24 C23 -0.2(4) .
C8 C21 C22 O3 177.9(3) .
C8 C21 C22 C23 -1.5(4) .
C9 C8 C21 C22 0.7(4) .
C9 C10 C11 C12 54.0(3) .
C9 C10 C11 C16 -125.3(3) .
C10 C1 C2 C3 -177.6(3) .
C10 C1 C6 C5 178.9(2) .
C10 C1 C6 C7 0.2(3) .
C10 C9 C24 C23 178.6(2) .
C10 C11 C12 C7 0.2(3) .
C10 C11 C12 C13 -179.6(2) .
C10 C11 C16 C15 179.2(3) .
C11 C12 C13 C14 1.5(4) .
C12 C7 C8 C9 55.1(3) .
C12 C7 C8 C21 -127.1(3) .
C12 C11 C16 C15 -0.1(4) .
C12 C13 C14 O1 174.9(3) .
C12 C13 C14 C15 -2.3(4) .
C13 C14 C15 O2 -179.2(3) .
C13 C14 C15 C16 1.9(4) .
C14 O1 C17 C34 176.4(3) 2_676
C14 C15 C16 C11 -0.7(4) .
C15 O2 C18 C29 -172.5(2) 2_676
C16 C11 C12 C7 179.6(2) .
C16 C11 C12 C13 -0.3(4) .
C17 O1 C14 C13 114.9(3) .
C17 O1 C14 C15 -68.0(4) .
C18 O2 C15 C14 169.9(3) .
C18 O2 C15 C16 -11.2(4) .
C19 C7 C8 C9 -179.6(2) .
C19 C7 C8 C21 -1.9(4) .
C19 C7 C12 C11 -179.9(2) .
C19 C7 C12 C13 -0.1(4) .
C20 C10 C11 C12 -179.6(2) .
C20 C10 C11 C16 1.0(4) .
C21 C8 C9 C10 -178.7(2) .
C21 C8 C9 C24 0.2(4) .
C21 C22 C23 O6 -178.3(2) .
C21 C22 C23 C24 1.6(4) .
C22 O3 C25 C26 170.1(2) .
C22 C23 C24 C9 -0.7(4) .
C23 O6 C30 C31 -178.2(2) .
C24 C9 C10 C1 -123.0(3) .
C24 C9 C10 C11 127.5(3) .
C24 C9 C10 C20 0.7(4) .
C25 O3 C22 C21 7.5(4) .
C25 O3 C22 C23 -173.0(2) .
C26 O4 C27 C28 165.2(2) .
C27 O4 C26 C25 90.4(3) .
C28 O5 C29 C18 -172.4(3) 2_676
C29 O5 C28 C27 -175.5(3) .
C30 O6 C23 C22 175.9(2) .
C30 O6 C23 C24 -4.0(4) .
C31 O7 C32 C33 -156.2(3) .
C32 O7 C31 C30 -172.0(3) .
C33 O8 C34 C17 65.4(4) 2_676
C34 O8 C33 C32 165.0(3) .
O9 C43 C44 C45 178.7(3) .
N1 C35 C36 C37 -1.1(5) .
C35 N1 C39 C38 0.9(5) .
C35 C36 C37 C38 3.2(4) .
C35 C36 C37 C40 -176.5(3) .
C36 C37 C38 C39 -3.3(5) .
C36 C37 C40 C41 -13.5(4) .
C36 C37 C40 C45 165.6(3) .
C37 C38 C39 N1 1.4(5) .
C37 C40 C41 C42 179.3(3) .
C37 C40 C45 C44 -179.0(3) .
C38 C37 C40 C41 166.8(3) .
C38 C37 C40 C45 -14.1(4) .
C39 N1 C35 C36 -1.0(5) .
C40 C37 C38 C39 176.4(3) .
C40 C41 C42 C43 -1.0(5) .
C41 C40 C45 C44 0.2(4) .
C41 C42 C43 O9 -178.4(3) .
C41 C42 C43 C44 1.5(5) .
C42 C43 C44 C45 -1.2(5) .
C43 C44 C45 C40 0.3(5) .
C45 C40 C41 C42 0.2(4) .
C46 O9 C43 C42 178.8(3) .
C46 O9 C43 C44 -1.1(5) .
