# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- crystallographicdata.cif' #============================================================================== _publ_contact_author_name 'Paul D. Beer' _publ_contact_author_address ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; _publ_contact_author_email paul.beer@chem.ox.ac.uk _publ_section_title ; Chloride Anion Triggered Motion in a Bis-Imidazolium Rotaxane ; loop_ _publ_author_name _publ_author_address 'Christopher J. Serpell' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA. UK. ; 'Ricky Chall' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; 'Amber L. Thompson' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; 'Paul D. Beer' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; _publ_section_abstract ; We report the first bis-imidazolium-containing rotaxane, synthesised via anion templated self-assembly. Its co- conformation is controlled by a chloride anion recognition mechanism, thus demonstrating the viability of this protocol as a stimulus for shuttling molecular motion. ; ############################################################# # ***oxford university chemical crystallography group*** # # this structure was solved by amber thompson on 30/05/2008 ############################################################# data_2 _database_code_depnum_ccdc_archive 'CCDC 811551' #TrackingRef '- crystallographicdata.cif' _audit_creation_date 08-05-30 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 5782 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 8.1846(2) _cell_length_b 15.6823(4) _cell_length_c 18.6804(6) _cell_angle_alpha 106.1594(12) _cell_angle_beta 101.0415(11) _cell_angle_gamma 91.8678(13) _cell_volume 2250.93(11) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C38 H10 F10 N13 O9 P4 # Dc = 1.63 Fooo = 1160.00 Mu = 2.79 M = 1106.45 # Found Formula = C34 H30 F24 N10 P4 # Dc = 1.71 FOOO = 1160.00 Mu = 3.09 M = 1158.53 _chemical_formula_sum 'C17 H15 F12 N5 P2' _chemical_formula_moiety 'C17 H15 N5, 2(F6 P)' _chemical_compound_source . _chemical_formula_weight 579.27 _cell_measurement_reflns_used 9168 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.01 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.21 _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.309 # Sheldrick geometric approximatio 0.95 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 1.00 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 34026 _reflns_number_total 10185 _diffrn_reflns_av_R_equivalents 0.068 # Number of reflections with Friedels Law is 10185 # Number of reflections without Friedels Law is 17942 # Theoretical number of reflections is about 6576 _diffrn_reflns_theta_min 5.097 _diffrn_reflns_theta_max 27.455 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.357 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min -20 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _oxford_diffrn_Wilson_B_factor 2.79 _oxford_diffrn_Wilson_scale 13.53 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.50 _refine_diff_density_max 0.54 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 6493 _refine_ls_number_restraints 300 _refine_ls_number_parameters 759 _oxford_refine_ls_R_factor_ref 0.0797 _refine_ls_wR_factor_ref 0.1288 _refine_ls_goodness_of_fit_ref 1.0000 _refine_ls_shift/su_max 0.000356 # The values computed from all data _oxford_reflns_number_all 6493 _refine_ls_R_factor_all 0.0797 _refine_ls_wR_factor_all 0.1288 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4562 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_gt 0.1145 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 2.84P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens P1 P 0.62799(11) 0.64812(7) 0.45419(5) 0.0312 1.0000 Uani D U . . . . . P8 P 0.14680(12) 0.14391(6) -0.05186(5) 0.0308 1.0000 Uani . . . . . . . F9 F 0.0475(3) 0.07017(15) -0.02841(14) 0.0564 1.0000 Uani . . . . . . . F10 F 0.3099(3) 0.13581(17) 0.00730(13) 0.0546 1.0000 Uani . . . . . . . F11 F 0.2004(3) 0.06774(16) -0.11813(13) 0.0534 1.0000 Uani . . . . . . . F12 F 0.0919(3) 0.21930(15) 0.01365(13) 0.0478 1.0000 Uani . . . . . . . F13 F -0.0161(3) 0.15087(17) -0.11131(13) 0.0521 1.0000 Uani . . . . . . . F14 F 0.2487(3) 0.21707(16) -0.07438(13) 0.0503 1.0000 Uani . . . . . . . P15 P 0.34484(12) 0.93396(7) 0.63049(6) 0.0343 1.0000 Uani D U . . . . . P22 P 0.84988(12) 0.43441(7) 0.13523(6) 0.0330 1.0000 Uani . . . . . . . F23 F 0.7921(3) 0.45796(15) 0.21528(12) 0.0492 1.0000 Uani . . . . . . . F24 F 0.9035(3) 0.40913(17) 0.05516(12) 0.0517 1.0000 Uani . . . . . . . F25 F 0.9548(3) 0.35763(16) 0.15651(13) 0.0562 1.0000 Uani . . . . . . . F26 F 1.0098(3) 0.50377(17) 0.17335(14) 0.0594 1.0000 Uani . . . . . . . F27 F 0.6896(3) 0.36398(17) 0.09905(14) 0.0627 1.0000 Uani . . . . . . . F28 F 0.7452(3) 0.51098(17) 0.11424(14) 0.0587 1.0000 Uani . . . . . . . N29 N 0.7078(3) 0.13530(19) 1.00363(16) 0.0294 1.0000 Uani . . . . . . . C30 C 0.6316(4) 0.0572(2) 0.9509(2) 0.0329 1.0000 Uani . . . . . . . C31 C 0.5786(4) 0.0757(2) 0.8854(2) 0.0322 1.0000 Uani . . . . . . . N32 N 0.6248(4) 0.16515(19) 0.89771(16) 0.0297 1.0000 Uani . . . . . . . C33 C 0.7026(5) 0.1996(2) 0.9700(2) 0.0312 1.0000 Uani . . . . . . . C34 C 0.6116(5) 0.2125(2) 0.8417(2) 0.0323 1.0000 Uani . . . . . . . N35 N 0.6246(4) 0.30094(19) 0.86979(16) 0.0303 1.0000 Uani . . . . . . . C36 C 0.6197(5) 0.3453(2) 0.8184(2) 0.0350 1.0000 Uani . . . . . . . N37 N 0.6336(4) 0.44029(19) 0.84928(17) 0.0325 1.0000 Uani . . . . . . . C38 C 0.6085(5) 0.4979(2) 0.8080(2) 0.0348 1.0000 Uani . . . . . . . N39 N 0.6435(4) 0.5792(2) 0.85475(17) 0.0324 1.0000 Uani . . . . . . . C40 C 0.6901(5) 0.5747(3) 0.9281(2) 0.0382 1.0000 Uani . . . . . . . C41 C 0.6842(5) 0.4884(3) 0.9250(2) 0.0371 1.0000 Uani . . . . . . . C42 C 0.6330(6) 0.6621(3) 0.8315(2) 0.0448 1.0000 Uani . . . . . . . C43 C 0.6401(5) 0.6445(3) 0.7508(3) 0.0424 1.0000 Uani . . . . . . . C44 C 0.6462(5) 0.6293(3) 0.6862(3) 0.0545 1.0000 Uani . . . . . . . C45 C 0.6009(6) 0.3061(3) 0.7407(2) 0.0492 1.0000 Uani . . . . . . . C46 C 0.5849(6) 0.2146(3) 0.7146(2) 0.0503 1.0000 Uani . . . . . . . C47 C 0.5913(5) 0.1656(3) 0.7659(2) 0.0440 1.0000 Uani . . . . . . . C48 C 0.7942(5) 0.1437(3) 1.0822(2) 0.0401 1.0000 Uani . . . . . . . C49 C 0.6834(5) 0.1496(3) 1.1342(2) 0.0410 1.0000 Uani . . . . . . . C50 C 0.6009(6) 0.1543(3) 1.1805(3) 0.0529 1.0000 Uani . . . . . . . N51 N 0.1785(4) 0.6340(2) 0.49942(16) 0.0307 1.0000 Uani . . . . . . . C52 C 0.1209(4) 0.5539(2) 0.4452(2) 0.0333 1.0000 Uani . . . . . . . C53 C 0.0485(5) 0.5725(2) 0.3813(2) 0.0327 1.0000 Uani . . . . . . . N54 N 0.0620(4) 0.66438(19) 0.39709(16) 0.0299 1.0000 Uani . . . . . . . C55 C 0.1419(4) 0.6992(2) 0.4694(2) 0.0326 1.0000 Uani . . . . . . . C56 C -0.0007(4) 0.7151(2) 0.3462(2) 0.0309 1.0000 Uani . . . . . . . N57 N 0.0621(4) 0.79953(19) 0.36906(17) 0.0312 1.0000 Uani . . . . . . . C58 C 0.0053(5) 0.8483(3) 0.3229(2) 0.0352 1.0000 Uani . . . . . . . C59 C -0.1097(5) 0.8167(3) 0.2545(2) 0.0403 1.0000 Uani . . . . . . . C60 C -0.1690(5) 0.7280(3) 0.2326(2) 0.0430 1.0000 Uani . . . . . . . C61 C -0.1158(5) 0.6751(3) 0.2793(2) 0.0374 1.0000 Uani . . . . . . . N63 N 0.0776(4) 0.9388(2) 0.34854(17) 0.0332 1.0000 Uani . . . . . . . C64 C 0.0710(5) 0.9947(2) 0.3051(2) 0.0329 1.0000 Uani . . . . . . . N65 N 0.1451(4) 1.0731(2) 0.34910(17) 0.0328 1.0000 Uani . . . . . . . C66 C 0.1587(5) 1.1540(3) 0.3241(2) 0.0433 1.0000 Uani . . . . . . . C67 C 0.1629(5) 1.1322(3) 0.2433(3) 0.0396 1.0000 Uani . . . . . . . C68 C 0.1674(5) 1.1138(3) 0.1783(3) 0.0514 1.0000 Uani . . . . . . . C69 C 0.2001(5) 1.0681(3) 0.4216(2) 0.0410 1.0000 Uani . . . . . . . C70 C 0.1602(5) 0.9845(3) 0.4215(2) 0.0378 1.0000 Uani . . . . . . . C71 C 0.2693(5) 0.6442(3) 0.5778(2) 0.0386 1.0000 Uani . . . . . . . C72 C 0.1602(5) 0.6517(3) 0.6316(2) 0.0397 1.0000 Uani . . . . . . . C73 C 0.0808(6) 0.6589(3) 0.6793(3) 0.0487 1.0000 Uani . . . . . . . H301 H 0.6201 0.0027 0.9600 0.0400 1.0000 Uiso R . . . . . . H311 H 0.5213 0.0360 0.8400 0.0372 1.0000 Uiso R . . . . . . H331 H 0.7480 0.2584 0.9933 0.0360 1.0000 Uiso R . . . . . . H381 H 0.5731 0.4831 0.7555 0.0419 1.0000 Uiso R . . . . . . H401 H 0.7206 0.6225 0.9717 0.0431 1.0000 Uiso R . . . . . . H411 H 0.7090 0.4648 0.9657 0.0362 1.0000 Uiso R . . . . . . H421 H 0.5278 0.6855 0.8393 0.0549 1.0000 Uiso R . . . . . . H422 H 0.7249 0.7055 0.8629 0.0551 1.0000 Uiso R . . . . . . H441 H 0.6444 0.6131 0.6338 0.0660 1.0000 Uiso R . . . . . . H451 H 0.6001 0.3401 0.7071 0.0561 1.0000 Uiso R . . . . . . H461 H 0.5678 0.1861 0.6628 0.0531 1.0000 Uiso R . . . . . . H471 H 0.5833 0.1040 0.7496 0.0480 1.0000 Uiso R . . . . . . H482 H 0.8708 0.1974 1.1000 0.0481 1.0000 Uiso R . . . . . . H481 H 0.8563 0.0922 1.0820 0.0480 1.0000 Uiso R . . . . . . H501 H 0.5291 0.1515 1.2137 0.0631 1.0000 Uiso R . . . . . . H521 H 0.1318 0.4978 0.4520 0.0379 1.0000 Uiso R . . . . . . H531 H -0.0033 0.5323 0.3354 0.0371 1.0000 Uiso R . . . . . . H551 H 0.1670 0.7596 0.4944 0.0369 1.0000 Uiso R . . . . . . H591 H -0.1458 0.8542 0.2249 0.0488 1.0000 Uiso R . . . . . . H601 H -0.2453 0.7036 0.1863 0.0451 1.0000 Uiso R . . . . . . H611 H -0.1555 0.6153 0.2660 0.0400 1.0000 Uiso R . . . . . . H641 H 0.0221 0.9806 0.2535 0.0371 1.0000 Uiso R . . . . . . H661 H 0.0649 1.1875 0.3342 0.0511 1.0000 Uiso R . . . . . . H662 H 0.2614 1.1889 0.3533 0.0509 1.0000 Uiso R . . . . . . H681 H 0.1757 1.1007 0.1272 0.0593 1.0000 Uiso R . . . . . . H691 H 0.2560 1.1140 0.4631 0.0469 1.0000 Uiso R . . . . . . H701 H 0.1816 0.9605 0.4621 0.0500 1.0000 Uiso R . . . . . . H712 H 0.3459 0.6980 0.5942 0.0460 1.0000 Uiso R . . . . . . H711 H 0.3324 0.5930 0.5776 0.0461 1.0000 Uiso R . . . . . . H731 H 0.0146 0.6638 0.7156 0.0609 1.0000 Uiso R . . . . . . F20 F 0.8072(4) 0.6360(4) 0.4973(2) 0.0871 0.842(5) Uani D U P . 1 . . F30 F 0.5554(5) 0.5665(2) 0.4765(2) 0.0772 0.842(5) Uani D U P . 1 . . F40 F 0.4465(4) 0.6587(4) 0.4137(2) 0.0898 0.842(5) Uani D U P . 1 . . F50 F 0.7032(5) 0.7293(2) 0.4348(2) 0.0772 0.842(5) Uani D U P . 1 . . F60 F 0.6609(5) 0.5853(3) 0.3776(2) 0.0771 0.842(5) Uani D U P . 1 . . F70 F 0.5928(5) 0.7111(2) 0.5316(2) 0.0655 0.842(5) Uani D U P . 1 . . F21 F 0.708(2) 0.5641(8) 0.4659(8) 0.0757 0.158(5) Uani D U P . 2 . . F31 F 0.4554(13) 0.5941(11) 0.4131(9) 0.0678 0.158(5) Uani D U P . 2 . . F41 F 0.549(2) 0.7344(8) 0.4399(7) 0.0638 0.158(5) Uani D U P . 2 . . F51 F 0.7995(12) 0.7048(10) 0.4922(7) 0.0462 0.158(5) Uani D U P . 2 . . F61 F 0.6764(19) 0.6286(11) 0.3734(5) 0.0476 0.158(5) Uani D U P . 2 . . F71 F 0.576(2) 0.6701(11) 0.5329(6) 0.0602 0.158(5) Uani D U P . 2 . . F160 F 0.3201(7) 0.9786(4) 0.7131(2) 0.0563 0.636(6) Uani D U P . 1 . . F170 F 0.3721(6) 0.8883(3) 0.5458(2) 0.0463 0.636(6) Uani D U P . 1 . . F180 F 0.4467(6) 0.8598(3) 0.6562(2) 0.0747 0.636(6) Uani D U P . 1 . . F190 F 0.5157(6) 0.9945(4) 0.6459(4) 0.0896 0.636(6) Uani D U P . 1 . . F200 F 0.2472(7) 1.0069(3) 0.6017(2) 0.0714 0.636(6) Uani D U P . 1 . . F210 F 0.1792(5) 0.8714(3) 0.6118(3) 0.0708 0.636(6) Uani D U P . 1 . . F161 F 0.2777(12) 1.0010(7) 0.7006(5) 0.0577 0.364(6) Uani D U P . 2 . . F171 F 0.4083(13) 0.8676(7) 0.5661(5) 0.0801 0.364(6) Uani D U P . 2 . . F181 F 0.5139(7) 0.9409(5) 0.6897(4) 0.0561 0.364(6) Uani D U P . 2 . . F191 F 0.4085(13) 1.0161(4) 0.6104(4) 0.0696 0.364(6) Uani D U P . 2 . . F201 F 0.1662(7) 0.9274(7) 0.5775(4) 0.0638 0.364(6) Uani D U P . 2 . . F211 F 0.2743(13) 0.8538(5) 0.6562(5) 0.0889 0.364(6) Uani D U P . 2 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0312(5) 0.0367(6) 0.0292(5) 0.0145(4) 0.0072(4) 0.0051(4) P8 0.0327(5) 0.0303(6) 0.0307(6) 0.0112(4) 0.0061(4) 0.0038(4) F9 0.0733(17) 0.0396(14) 0.0655(17) 0.0192(12) 0.0320(14) -0.0039(12) F10 0.0493(14) 0.0721(18) 0.0447(14) 0.0252(13) 0.0009(11) 0.0203(13) F11 0.0512(14) 0.0518(15) 0.0513(15) -0.0007(12) 0.0195(12) 0.0080(12) F12 0.0498(14) 0.0407(14) 0.0477(14) -0.0008(11) 0.0169(11) 0.0084(11) F13 0.0358(13) 0.0721(17) 0.0458(14) 0.0169(13) 0.0018(11) 0.0103(12) F14 0.0508(14) 0.0516(15) 0.0538(15) 0.0253(12) 0.0106(12) -0.0073(12) P15 0.0324(5) 0.0323(6) 0.0321(5) 0.0024(4) 0.0019(4) 0.0033(4) P22 0.0341(6) 0.0331(6) 0.0278(5) 0.0046(4) 0.0030(4) 0.0035(4) F23 0.0633(15) 0.0474(15) 0.0347(13) 0.0034(11) 0.0177(11) 0.0054(12) F24 0.0573(15) 0.0665(17) 0.0343(13) 0.0138(12) 0.0166(11) 0.0139(13) F25 0.0757(17) 0.0513(15) 0.0471(15) 0.0199(12) 0.0139(13) 0.0293(13) F26 0.0416(14) 0.0574(17) 0.0647(17) -0.0015(13) 0.0071(12) -0.0084(12) F27 0.0446(14) 0.0577(17) 0.0632(17) -0.0186(13) 0.0134(12) -0.0113(12) F28 0.0667(17) 0.0587(16) 0.0528(16) 0.0209(13) 0.0069(13) 0.0275(13) N29 0.0315(17) 0.0283(17) 0.0286(17) 0.0090(14) 0.0057(13) 0.0043(14) C30 0.037(2) 0.025(2) 0.039(2) 0.0108(18) 0.0104(18) 0.0033(17) C31 0.034(2) 0.026(2) 0.036(2) 0.0061(17) 0.0090(17) -0.0009(17) N32 0.0342(17) 0.0260(17) 0.0279(18) 0.0074(14) 0.0043(14) 0.0033(14) C33 0.040(2) 0.025(2) 0.028(2) 0.0081(17) 0.0060(17) 0.0065(17) C34 0.037(2) 0.027(2) 0.030(2) 0.0071(17) 0.0036(17) 0.0006(17) N35 0.0353(17) 0.0280(18) 0.0283(17) 0.0111(14) 0.0039(14) 0.0041(14) C36 0.035(2) 0.035(2) 0.033(2) 0.0101(19) 0.0007(17) 0.0034(18) N37 0.0385(18) 0.0273(18) 0.0315(18) 0.0120(15) 0.0017(14) 0.0015(14) C38 0.040(2) 0.032(2) 0.034(2) 0.0148(19) 0.0036(18) 0.0012(18) N39 0.0348(17) 0.0296(19) 0.0355(19) 0.0151(15) 0.0050(14) 0.0043(14) C40 0.043(2) 0.032(2) 0.037(2) 0.0091(18) 0.0046(18) 0.0013(18) C41 0.048(2) 0.034(2) 0.027(2) 0.0102(18) 0.0008(18) 0.0033(19) C42 0.062(3) 0.031(2) 0.045(3) 0.019(2) 0.009(2) 0.005(2) C43 0.039(2) 0.040(2) 0.051(3) 0.022(2) 0.002(2) 0.0044(19) C44 0.048(3) 0.069(3) 0.051(3) 0.031(3) 0.001(2) 0.005(2) C45 0.068(3) 0.046(3) 0.033(2) 0.015(2) 0.006(2) 0.004(2) C46 0.073(3) 0.040(3) 0.031(2) 0.006(2) 0.001(2) 0.001(2) C47 0.059(3) 0.032(2) 0.038(2) 0.008(2) 0.005(2) 0.003(2) C48 0.053(2) 0.037(2) 0.032(2) 0.0152(19) 0.0036(19) 0.006(2) C49 0.056(3) 0.031(2) 0.037(2) 0.0128(19) 0.008(2) 0.003(2) C50 0.068(3) 0.054(3) 0.044(3) 0.022(2) 0.015(2) 0.006(2) N51 0.0303(17) 0.0335(18) 0.0281(17) 0.0092(15) 0.0057(13) 0.0018(14) C52 0.035(2) 0.029(2) 0.036(2) 0.0113(18) 0.0050(18) 0.0020(17) C53 0.038(2) 0.025(2) 0.030(2) 0.0026(17) 0.0054(17) -0.0003(17) N54 0.0359(17) 0.0268(17) 0.0256(17) 0.0051(14) 0.0074(14) 0.0006(14) C55 0.039(2) 0.028(2) 0.031(2) 0.0079(18) 0.0077(18) 0.0046(17) C56 0.037(2) 0.029(2) 0.028(2) 0.0093(17) 0.0084(17) 0.0033(17) N57 0.0400(18) 0.0249(17) 0.0310(17) 0.0100(14) 0.0102(14) 0.0029(14) C58 0.041(2) 0.034(2) 0.032(2) 0.0100(18) 0.0110(18) 0.0036(18) C59 0.049(2) 0.039(2) 0.034(2) 0.0154(19) 0.0053(19) 0.000(2) C60 0.047(2) 0.048(3) 0.030(2) 0.010(2) 0.0014(19) -0.003(2) C61 0.044(2) 0.031(2) 0.034(2) 0.0059(18) 0.0056(19) -0.0022(18) N63 0.0385(18) 0.0288(18) 0.0317(18) 0.0091(15) 0.0057(15) -0.0010(14) C64 0.037(2) 0.030(2) 0.034(2) 0.0128(19) 0.0059(17) 0.0072(18) N65 0.0356(18) 0.0263(18) 0.0371(19) 0.0109(15) 0.0067(15) 0.0024(14) C66 0.055(3) 0.027(2) 0.051(3) 0.014(2) 0.014(2) 0.0061(19) C67 0.033(2) 0.036(2) 0.053(3) 0.020(2) 0.006(2) 0.0025(18) C68 0.053(3) 0.051(3) 0.051(3) 0.020(2) 0.006(2) 0.004(2) C69 0.039(2) 0.039(2) 0.042(3) 0.010(2) 0.0035(19) 0.0018(19) C70 0.045(2) 0.032(2) 0.036(2) 0.0121(18) 0.0034(19) -0.0003(18) C71 0.042(2) 0.039(2) 0.034(2) 0.0121(19) 0.0014(18) 0.0057(19) C72 0.048(2) 0.036(2) 0.034(2) 0.0146(19) 0.000(2) 0.0051(19) C73 0.064(3) 0.042(3) 0.044(3) 0.015(2) 0.016(2) 0.007(2) F20 0.0387(13) 0.168(4) 0.077(2) 0.068(3) 0.0124(13) 0.0341(18) F30 0.103(3) 0.0474(15) 0.103(3) 0.0348(16) 0.057(2) 0.0033(16) F40 0.0389(12) 0.194(5) 0.059(2) 0.070(3) 0.0100(12) 0.0313(18) F50 0.108(3) 0.0527(16) 0.094(3) 0.0374(16) 0.052(2) 0.0006(17) F60 0.087(2) 0.074(2) 0.0604(17) -0.0136(16) 0.0426(17) -0.012(2) F70 0.076(2) 0.063(2) 0.0516(15) -0.0055(14) 0.0319(15) -0.0039(19) F21 0.114(12) 0.047(5) 0.054(8) 0.022(6) -0.025(8) 0.022(6) F31 0.037(5) 0.083(9) 0.057(8) -0.021(8) 0.010(5) -0.008(5) F41 0.092(10) 0.058(6) 0.033(8) 0.010(6) -0.008(7) 0.042(6) F51 0.035(4) 0.065(8) 0.030(6) 0.000(7) 0.009(4) -0.005(4) F61 0.040(7) 0.079(10) 0.022(4) 0.012(5) 0.003(4) 0.018(7) F71 0.066(9) 0.082(11) 0.032(4) 0.015(6) 0.017(5) -0.026(8) F160 0.061(3) 0.070(3) 0.0306(14) 0.0036(15) 0.0060(18) 0.023(2) F170 0.051(3) 0.053(3) 0.0340(14) 0.0087(14) 0.0114(17) 0.0164(18) F180 0.098(3) 0.090(3) 0.049(2) 0.031(2) 0.022(2) 0.062(3) F190 0.055(2) 0.074(3) 0.108(4) -0.035(3) 0.036(3) -0.0265(19) F200 0.107(4) 0.067(3) 0.058(3) 0.030(2) 0.033(3) 0.053(3) F210 0.0489(19) 0.059(3) 0.087(4) -0.017(2) 0.032(2) -0.0156(16) F161 0.043(4) 0.080(5) 0.041(3) -0.002(3) 0.012(3) 0.018(4) F171 0.050(4) 0.072(5) 0.077(4) -0.041(4) 0.006(3) 0.010(4) F181 0.033(2) 0.067(6) 0.056(4) 0.006(3) -0.005(2) 0.013(3) F191 0.102(7) 0.056(3) 0.054(5) 0.021(3) 0.019(4) -0.013(4) F201 0.039(2) 0.104(7) 0.038(3) 0.012(3) -0.003(2) 0.015(3) F211 0.108(7) 0.060(4) 0.086(6) 0.034(3) -0.021(4) -0.041(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2861(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 . F20 . 1.577(3) yes P1 . F30 . 1.583(3) yes P1 . F40 . 1.569(3) yes P1 . F50 . 1.557(3) yes P1 . F60 . 1.572(3) yes P1 . F70 . 1.591(3) yes P8 . F9 . 1.596(2) yes P8 . F10 . 1.595(2) yes P8 . F11 . 1.603(2) yes P8 . F12 . 1.593(2) yes P8 . F13 . 1.591(2) yes P8 . F14 . 1.590(2) yes P15 . F160 . 1.562(4) yes P15 . F170 . 1.607(4) yes P15 . F180 . 1.581(4) yes P15 . F190 . 1.595(4) yes P15 . F200 . 1.572(4) yes P15 . F210 . 1.569(4) yes P22 . F23 . 1.604(2) yes P22 . F24 . 1.587(2) yes P22 . F25 . 1.596(2) yes P22 . F26 . 1.588(2) yes P22 . F27 . 1.596(2) yes P22 . F28 . 1.591(2) yes N29 . C30 . 1.379(5) yes N29 . C33 . 1.325(4) yes N29 . C48 . 1.470(5) yes C30 . C31 . 1.330(5) yes C30 . H301 . 0.923 no C31 . N32 . 1.384(4) yes C31 . H311 . 0.928 no N32 . C33 . 1.328(4) yes N32 . C34 . 1.432(5) yes C33 . H331 . 0.933 no C34 . N35 . 1.333(4) yes C34 . C47 . 1.377(5) yes N35 . C36 . 1.329(5) yes C36 . N37 . 1.431(5) yes C36 . C45 . 1.386(5) yes N37 . C38 . 1.338(5) yes N37 . C41 . 1.380(5) yes C38 . N39 . 1.315(5) yes C38 . H381 . 0.928 no N39 . C40 . 1.372(5) yes N39 . C42 . 1.481(5) yes C40 . C41 . 1.337(5) yes C40 . H401 . 0.926 no C41 . H411 . 0.927 no C42 . C43 . 1.468(6) yes C42 . H421 . 0.968 no C42 . H422 . 0.973 no C43 . C44 . 1.175(6) yes C44 . H441 . 0.938 no C45 . C46 . 1.374(6) yes C45 . H451 . 0.929 no C46 . C47 . 1.379(6) yes C46 . H461 . 0.926 no C47 . H471 . 0.925 no C48 . C49 . 1.438(6) yes C48 . H482 . 0.971 no C48 . H481 . 0.967 no C49 . C50 . 1.183(6) yes C50 . H501 . 0.941 no N51 . C52 . 1.377(5) yes N51 . C55 . 1.313(5) yes N51 . C71 . 1.472(5) yes C52 . C53 . 1.340(5) yes C52 . H521 . 0.929 no C53 . N54 . 1.383(4) yes C53 . H531 . 0.925 no N54 . C55 . 1.334(4) yes N54 . C56 . 1.435(5) yes C55 . H551 . 0.929 no C56 . N57 . 1.326(4) yes C56 . C61 . 1.385(5) yes N57 . C58 . 1.335(5) yes C58 . C59 . 1.385(5) yes C58 . N63 . 1.432(5) yes C59 . C60 . 1.378(5) yes C59 . H591 . 0.932 no C60 . C61 . 1.385(5) yes C60 . H601 . 0.937 no C61 . H611 . 0.932 no N63 . C64 . 1.346(5) yes N63 . C70 . 1.378(5) yes C64 . N65 . 1.324(5) yes C64 . H641 . 0.932 no N65 . C66 . 1.476(5) yes N65 . C69 . 1.369(5) yes C66 . C67 . 1.461(6) yes C66 . H661 . 0.963 no C66 . H662 . 0.965 no C67 . C68 . 1.174(6) yes C68 . H681 . 0.937 no C69 . C70 . 1.340(5) yes C69 . H691 . 0.928 no C70 . H701 . 0.926 no C71 . C72 . 1.451(6) yes C71 . H712 . 0.974 no C71 . H711 . 0.968 no C72 . C73 . 1.183(6) yes C73 . H731 . 0.935 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag F20 . P1 . F30 . 88.9(2) yes F20 . P1 . F40 . 177.64(19) yes F30 . P1 . F40 . 89.1(2) yes F20 . P1 . F50 . 89.7(2) yes F30 . P1 . F50 . 178.2(2) yes F40 . P1 . F50 . 92.3(2) yes F20 . P1 . F60 . 90.4(2) yes F30 . P1 . F60 . 91.9(2) yes F40 . P1 . F60 . 90.9(2) yes F50 . P1 . F60 . 89.2(2) yes F20 . P1 . F70 . 90.0(2) yes F30 . P1 . F70 . 87.64(19) yes F40 . P1 . F70 . 88.7(2) yes F50 . P1 . F70 . 91.25(19) yes F60 . P1 . F70 . 179.4(2) yes F9 . P8 . F10 . 89.45(14) yes F9 . P8 . F11 . 90.33(13) yes F10 . P8 . F11 . 90.66(13) yes F9 . P8 . F12 . 89.42(13) yes F10 . P8 . F12 . 89.75(13) yes F11 . P8 . F12 . 179.51(13) yes F9 . P8 . F13 . 90.19(14) yes F10 . P8 . F13 . 179.38(15) yes F11 . P8 . F13 . 88.84(13) yes F12 . P8 . F13 . 90.75(13) yes F9 . P8 . F14 . 179.00(14) yes F10 . P8 . F14 . 89.56(13) yes F11 . P8 . F14 . 89.53(13) yes F12 . P8 . F14 . 90.73(13) yes F13 . P8 . F14 . 90.80(13) yes F160 . P15 . F170 . 179.5(3) yes F160 . P15 . F180 . 92.1(2) yes F170 . P15 . F180 . 87.7(2) yes F160 . P15 . F190 . 91.5(3) yes F170 . P15 . F190 . 88.0(3) yes F180 . P15 . F190 . 89.6(3) yes F160 . P15 . F200 . 90.3(2) yes F170 . P15 . F200 . 89.9(2) yes F180 . P15 . F200 . 177.4(2) yes F190 . P15 . F200 . 89.5(3) yes F160 . P15 . F210 . 91.2(3) yes F170 . P15 . F210 . 89.3(3) yes F180 . P15 . F210 . 89.6(3) yes F190 . P15 . F210 . 177.2(2) yes F200 . P15 . F210 . 91.3(3) yes F23 . P22 . F24 . 178.58(14) yes F23 . P22 . F25 . 90.78(13) yes F24 . P22 . F25 . 89.02(13) yes F23 . P22 . F26 . 89.73(13) yes F24 . P22 . F26 . 91.67(14) yes F25 . P22 . F26 . 89.55(15) yes F23 . P22 . F27 . 89.00(13) yes F24 . P22 . F27 . 89.59(13) yes F25 . P22 . F27 . 89.52(15) yes F26 . P22 . F27 . 178.42(16) yes F23 . P22 . F28 . 89.06(13) yes F24 . P22 . F28 . 91.14(14) yes F25 . P22 . F28 . 179.83(14) yes F26 . P22 . F28 . 90.46(15) yes F27 . P22 . F28 . 90.46(15) yes C30 . N29 . C33 . 108.9(3) yes C30 . N29 . C48 . 125.4(3) yes C33 . N29 . C48 . 125.6(3) yes N29 . C30 . C31 . 107.3(3) yes N29 . C30 . H301 . 125.7 no C31 . C30 . H301 . 127.0 no C30 . C31 . N32 . 107.2(3) yes C30 . C31 . H311 . 126.3 no N32 . C31 . H311 . 126.5 no C31 . N32 . C33 . 108.6(3) yes C31 . N32 . C34 . 127.1(3) yes C33 . N32 . C34 . 123.9(3) yes N32 . C33 . N29 . 108.1(3) yes N32 . C33 . H331 . 126.3 no N29 . C33 . H331 . 125.5 no N32 . C34 . N35 . 114.8(3) yes N32 . C34 . C47 . 119.5(3) yes N35 . C34 . C47 . 125.7(4) yes C34 . N35 . C36 . 115.1(3) yes N35 . C36 . N37 . 114.5(3) yes N35 . C36 . C45 . 124.8(4) yes N37 . C36 . C45 . 120.7(3) yes C36 . N37 . C38 . 125.0(3) yes C36 . N37 . C41 . 126.7(3) yes C38 . N37 . C41 . 108.3(3) yes N37 . C38 . N39 . 108.2(3) yes N37 . C38 . H381 . 126.0 no N39 . C38 . H381 . 125.8 no C38 . N39 . C40 . 109.2(3) yes C38 . N39 . C42 . 125.2(3) yes C40 . N39 . C42 . 125.6(3) yes N39 . C40 . C41 . 107.3(3) yes N39 . C40 . H401 . 126.5 no C41 . C40 . H401 . 126.2 no N37 . C41 . C40 . 107.0(3) yes N37 . C41 . H411 . 125.9 no C40 . C41 . H411 . 127.0 no N39 . C42 . C43 . 111.0(3) yes N39 . C42 . H421 . 108.3 no C43 . C42 . H421 . 109.0 no N39 . C42 . H422 . 109.4 no C43 . C42 . H422 . 109.6 no H421 . C42 . H422 . 109.5 no C42 . C43 . C44 . 179.1(5) yes C43 . C44 . H441 . 175.3 no C36 . C45 . C46 . 117.8(4) yes C36 . C45 . H451 . 121.5 no C46 . C45 . H451 . 120.6 no C45 . C46 . C47 . 119.5(4) yes C45 . C46 . H461 . 120.2 no C47 . C46 . H461 . 120.3 no C46 . C47 . C34 . 117.1(4) yes C46 . C47 . H471 . 120.9 no C34 . C47 . H471 . 121.9 no N29 . C48 . C49 . 113.6(3) yes N29 . C48 . H482 . 108.1 no C49 . C48 . H482 . 108.3 no N29 . C48 . H481 . 108.6 no C49 . C48 . H481 . 108.5 no H482 . C48 . H481 . 109.7 no C48 . C49 . C50 . 175.8(5) yes C49 . C50 . H501 . 173.3 no C52 . N51 . C55 . 109.0(3) yes C52 . N51 . C71 . 125.2(3) yes C55 . N51 . C71 . 125.8(3) yes N51 . C52 . C53 . 107.2(3) yes N51 . C52 . H521 . 125.8 no C53 . C52 . H521 . 127.0 no C52 . C53 . N54 . 107.1(3) yes C52 . C53 . H531 . 127.2 no N54 . C53 . H531 . 125.8 no C53 . N54 . C55 . 108.1(3) yes C53 . N54 . C56 . 127.0(3) yes C55 . N54 . C56 . 125.0(3) yes N54 . C55 . N51 . 108.8(3) yes N54 . C55 . H551 . 125.5 no N51 . C55 . H551 . 125.8 no N54 . C56 . N57 . 114.3(3) yes N54 . C56 . C61 . 120.4(3) yes N57 . C56 . C61 . 125.3(3) yes C56 . N57 . C58 . 115.6(3) yes N57 . C58 . C59 . 124.9(4) yes N57 . C58 . N63 . 114.2(3) yes C59 . C58 . N63 . 120.9(3) yes C58 . C59 . C60 . 117.3(4) yes C58 . C59 . H591 . 121.1 no C60 . C59 . H591 . 121.6 no C59 . C60 . C61 . 119.9(4) yes C59 . C60 . H601 . 120.1 no C61 . C60 . H601 . 120.0 no C60 . C61 . C56 . 117.1(4) yes C60 . C61 . H611 . 121.4 no C56 . C61 . H611 . 121.5 no C58 . N63 . C64 . 125.1(3) yes C58 . N63 . C70 . 126.5(3) yes C64 . N63 . C70 . 108.3(3) yes N63 . C64 . N65 . 107.8(3) yes N63 . C64 . H641 . 125.9 no N65 . C64 . H641 . 126.3 no C64 . N65 . C66 . 125.0(3) yes C64 . N65 . C69 . 109.3(3) yes C66 . N65 . C69 . 125.6(3) yes N65 . C66 . C67 . 111.7(3) yes N65 . C66 . H661 . 108.5 no C67 . C66 . H661 . 110.2 no N65 . C66 . H662 . 108.0 no C67 . C66 . H662 . 108.6 no H661 . C66 . H662 . 109.8 no C66 . C67 . C68 . 179.2(5) yes C67 . C68 . H681 . 177.4 no N65 . C69 . C70 . 107.5(3) yes N65 . C69 . H691 . 126.2 no C70 . C69 . H691 . 126.3 no N63 . C70 . C69 . 107.1(4) yes N63 . C70 . H701 . 125.1 no C69 . C70 . H701 . 127.8 no N51 . C71 . C72 . 113.2(3) yes N51 . C71 . H712 . 108.2 no C72 . C71 . H712 . 108.4 no N51 . C71 . H711 . 108.4 no C72 . C71 . H711 . 109.1 no H712 . C71 . H711 . 109.5 no C71 . C72 . C73 . 175.5(4) yes C72 . C73 . H731 . 177.9 no