# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_vpd_napf6 _audit_creation_date 2013-01-23 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:17:34, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '0.25(C72 H120 N12 Na4 O12), F6 P' _chemical_formula_sum 'C18 H30 F6 N3 Na O3 P' _chemical_formula_weight 504.41 _chemical_absolute_configuration unk _chemical_melting_point ? _chemical_oxdiff_formula 'C12 H20 N2 O2 Na P F6' 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' Na Na 0.0362 0.0249 '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' _space_group_crystal_system trigonal _space_group_IT_number 159 _space_group_name_H-M_alt 'P 3 1 c' _space_group_name_Hall 'P 3 -2c' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-y, x-y, z' 3 '-x+y, -x, z' 4 'y, x, z+1/2' 5 'x-y, -y, z+1/2' 6 '-x, -x+y, z+1/2' _cell_length_a 23.9245(6) _cell_length_b 23.9245(6) _cell_length_c 13.3123(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6598.9(3) _cell_formula_units_Z 12 _cell_measurement_reflns_used 4546 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 29.1580 _cell_measurement_theta_min 2.4862 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 3156 _exptl_crystal_size_max 0.2116 _exptl_crystal_size_mid 0.1894 _exptl_crystal_size_min 0.09 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.2215 _diffrn_reflns_av_unetI/netI 0.1204 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 104425 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.49 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -84.00 8.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -19.0000 -120.0000 92 #__ type_ start__ end____ width___ exp.time_ 2 omega 14.00 57.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -92.0000 -48.0000 43 #__ type_ start__ end____ width___ exp.time_ 3 omega -89.00 5.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -48.0000 167.0000 94 #__ type_ start__ end____ width___ exp.time_ 4 omega -91.00 26.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -19.0000 0.0000 117 #__ type_ start__ end____ width___ exp.time_ 5 omega -39.00 51.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 57.0000 0.0000 90 #__ type_ start__ end____ width___ exp.time_ 6 omega -39.00 51.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 57.0000 -150.0000 90 #__ type_ start__ end____ width___ exp.time_ 7 omega -20.00 33.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 92.0000 -116.0000 53 #__ type_ start__ end____ width___ exp.time_ 8 omega 26.00 84.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -137.0000 176.0000 58 #__ type_ start__ end____ width___ exp.time_ 9 omega -94.00 -34.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -179.0000 -60.0000 60 #__ type_ start__ end____ width___ exp.time_ 10 omega 26.00 51.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -137.0000 -3.0000 25 #__ type_ start__ end____ width___ exp.time_ 11 omega -3.00 87.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 57.0000 150.0000 90 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0244423000 _diffrn_orient_matrix_UB_12 0.0312347000 _diffrn_orient_matrix_UB_13 -0.0149925000 _diffrn_orient_matrix_UB_21 -0.0231437000 _diffrn_orient_matrix_UB_22 0.0040850000 _diffrn_orient_matrix_UB_23 -0.0273755000 _diffrn_orient_matrix_UB_31 -0.0061797000 _diffrn_orient_matrix_UB_32 0.0134315000 _diffrn_orient_matrix_UB_33 0.0431790000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5779 _reflns_number_total 10093 _reflns_odcompleteness_completeness 99.77 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.586 _refine_diff_density_min -0.561 _refine_diff_density_rms 0.122 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(3) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 574 _refine_ls_number_reflns 10093 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1770 _refine_ls_R_factor_gt 0.1126 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1197P)^2^+26.0447P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2853 _refine_ls_wR_factor_ref 0.3214 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H23A,H23B} of C23, {H26A,H26B} of C26, {H35A,H35B} of C35, {H24A,H24B} of C24, {H19A,H19B} of C19, {H15A,H15B} of C15, {H20A,H20B} of C20, {H22A,H22B} of C22, {H14A,H14B} of C14, H17 of C17, {H16A,H16B} of C16, {H11A,H11B} of C11, {H2A,H2B} of C2, {H10A,H10B} of C10, {H8A,H8B} of C8, {H7A,H7B} of C7, {H3A,H3B} of C3, {H12A,H12B} of C12, {H4A,H4B} of C4, H5 of C5, {H28A,H28B} of C28, {H36A,H36B} of C36, {H31A,H31B} of C31, {H27A,H27B} of C27, {H32A, H32B} of C32, {H34A,H34B} of C34, H29 of C29 At 1.5 times of: {H18A,H18B,H18C} of C18, {H6A,H6B,H6C} of C6, {H30A,H30B,H30C} of C30 2. Uiso/Uaniso restraints and constraints Uanis(C1) ~ Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1 Uanis(C21) = Uanis(O4) 3.a Ternary CH refined with riding coordinates: C29(H29), C5(H5), C17(H17) 3.b Secondary CH2 refined with riding coordinates: C35(H35A,H35B), C26(H26A,H26B), C34(H34A,H34B), C32(H32A,H32B), C27(H27A, H27B), C31(H31A,H31B), C36(H36A,H36B), C28(H28A,H28B), C4(H4A,H4B), C12(H12A, H12B), C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C2(H2A,H2B), C11(H11A,H11B), C16(H16A,H16B), C14(H14A,H14B), C22(H22A,H22B), C20(H20A,H20B), C15(H15A,H15B), C19(H19A,H19B), C24(H24A,H24B), C23(H23A,H23B) 3.c Idealised Me refined as rotating group: C30(H30A,H30B,H30C), C6(H6A,H6B,H6C), C18(H18A,H18B,H18C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N6 N 0.9258(4) 0.8060(4) 0.7447(6) 0.0244(17) Uani 1 1 d . . . O5 O 0.9300(3) 0.9201(3) 0.5095(4) 0.0245(15) Uani 1 1 d . . . O6 O 0.9530(3) 0.9140(3) 0.7552(5) 0.0217(14) Uani 1 1 d . . . C35 C 1.0277(5) 0.8139(5) 0.7598(10) 0.037(3) Uani 1 1 d . . . H35A H 1.0469 0.8142 0.6938 0.044 Uiso 1 1 calc R . . H35B H 1.0497 0.8028 0.8126 0.044 Uiso 1 1 calc R . . C26 C 0.8265(4) 0.9203(5) 0.5128(7) 0.026(2) Uani 1 1 d . . . H26A H 0.8236 0.9340 0.4437 0.031 Uiso 1 1 calc R . . H26B H 0.8428 0.9580 0.5583 0.031 Uiso 1 1 calc R . . N5 N 0.8314(4) 0.8250(4) 0.5303(7) 0.034(2) Uani 1 1 d . . . C29 C 0.8559(5) 0.7782(5) 0.5308(8) 0.037(3) Uani 1 1 d . . . H29 H 0.9042 0.8035 0.5304 0.044 Uiso 1 1 calc R . . C33 C 0.9674(5) 0.8695(4) 0.7547(7) 0.030(2) Uani 1 1 d . . . C34 C 1.0331(5) 0.8807(5) 0.7816(7) 0.030(2) Uani 1 1 d . . . H34A H 1.0431 0.8927 0.8532 0.036 Uiso 1 1 calc R . . H34B H 1.0669 0.9151 0.7394 0.036 Uiso 1 1 calc R . . C25 C 0.8701(5) 0.8886(5) 0.5168(7) 0.026(2) Uani 1 1 d . . . C32 C 0.8577(5) 0.7774(5) 0.7316(8) 0.033(2) Uani 1 1 d . . . H32A H 0.8459 0.8116 0.7331 0.040 Uiso 1 1 calc R . . H32B H 0.8353 0.7475 0.7881 0.040 Uiso 1 1 calc R . . C27 C 0.7588(6) 0.8631(6) 0.5498(9) 0.045(3) Uani 1 1 d . . . H27A H 0.7536 0.8657 0.6232 0.054 Uiso 1 1 calc R . . H27B H 0.7228 0.8639 0.5147 0.054 Uiso 1 1 calc R . . C31 C 0.8339(5) 0.7393(5) 0.6301(8) 0.033(2) Uani 1 1 d . . . H31A H 0.8481 0.7069 0.6285 0.040 Uiso 1 1 calc R . . H31B H 0.7861 0.7153 0.6309 0.040 Uiso 1 1 calc R . . C30 C 0.8352(6) 0.7379(6) 0.4438(9) 0.048(3) Uani 1 1 d . . . H30A H 0.7885 0.7083 0.4475 0.072 Uiso 1 1 calc R . . H30B H 0.8576 0.7130 0.4408 0.072 Uiso 1 1 calc R . . H30C H 0.8454 0.7647 0.3835 0.072 Uiso 1 1 calc R . . C36 C 0.9552(5) 0.7666(4) 0.7599(9) 0.029(2) Uani 1 1 d . . . H36A H 0.9433 0.7346 0.7051 0.035 Uiso 1 1 calc R . . H36B H 0.9414 0.7433 0.8248 0.035 Uiso 1 1 calc R . . C28 C 0.7617(4) 0.8012(5) 0.5222(7) 0.027(2) Uani 1 1 d . . . H28A H 0.7366 0.7657 0.5703 0.033 Uiso 1 1 calc R . . H28B H 0.7457 0.7863 0.4533 0.033 Uiso 1 1 calc R . . P1 P 0.31514(12) 0.31055(12) 0.5050(2) 0.0236(5) Uani 1 1 d . . . Na4 Na 0.6667 0.3333 0.6453(5) 0.0207(13) Uani 1 3 d S . . F2 F 0.3064(3) 0.3144(3) 0.6243(4) 0.0374(15) Uani 1 1 d . . . F1 F 0.3249(3) 0.3086(3) 0.3852(4) 0.0394(15) Uani 1 1 d . . . F4 F 0.3699(4) 0.3828(3) 0.5088(5) 0.066(2) Uani 1 1 d . . . O2 O 0.7553(3) 0.3822(3) 0.5250(5) 0.0302(16) Uani 1 1 d . . . N1 N 0.8399(4) 0.5056(4) 0.7520(6) 0.0239(17) Uani 1 1 d . . . O1 O 0.7473(3) 0.4054(3) 0.7649(5) 0.0287(16) Uani 1 1 d . . . F3 F 0.3685(3) 0.2911(4) 0.5259(5) 0.0550(19) Uani 1 1 d . . . C5 C 0.8865(4) 0.4833(4) 0.7476(7) 0.023(2) Uani 1 1 d . . . H5 H 0.8626 0.4351 0.7495 0.028 Uiso 1 1 calc R . . C4 C 0.8594(6) 0.5740(5) 0.7573(10) 0.042(3) Uani 1 1 d . . . H4A H 0.8928 0.5994 0.7065 0.051 Uiso 1 1 calc R . . H4B H 0.8760 0.5919 0.8248 0.051 Uiso 1 1 calc R . . C1 C 0.7743(4) 0.4652(4) 0.7573(7) 0.023(2) Uani 1 1 d U . . F5 F 0.2616(3) 0.3304(4) 0.4824(5) 0.0521(18) Uani 1 1 d . . . F6 F 0.2614(3) 0.2355(3) 0.5006(5) 0.0500(18) Uani 1 1 d . . . N2 N 0.8630(4) 0.4143(4) 0.5370(6) 0.032(2) Uani 1 1 d . . . C9 C 0.7989(5) 0.3691(5) 0.5188(6) 0.026(2) Uani 1 1 d . . . C12 C 0.9048(5) 0.3865(5) 0.5125(7) 0.029(2) Uani 1 1 d . . . H12A H 0.9394 0.3994 0.5632 0.034 Uiso 1 1 calc R . . H12B H 0.9247 0.4010 0.4454 0.034 Uiso 1 1 calc R . . C3 C 0.7957(5) 0.5732(5) 0.7346(8) 0.038(3) Uani 1 1 d . . . H3A H 0.7924 0.6062 0.7748 0.045 Uiso 1 1 calc R . . H3B H 0.7927 0.5814 0.6624 0.045 Uiso 1 1 calc R . . C7 C 0.9272(5) 0.5059(4) 0.6499(7) 0.030(2) Uani 1 1 d . . . H7A H 0.9595 0.4916 0.6519 0.036 Uiso 1 1 calc R . . H7B H 0.9510 0.5537 0.6482 0.036 Uiso 1 1 calc R . . C8 C 0.8870(5) 0.4803(5) 0.5508(7) 0.030(2) Uani 1 1 d . . . H8A H 0.8506 0.4887 0.5528 0.036 Uiso 1 1 calc R . . H8B H 0.9147 0.5041 0.4929 0.036 Uiso 1 1 calc R . . C10 C 0.7941(6) 0.3047(5) 0.4952(10) 0.047(3) Uani 1 1 d . . . H10A H 0.7621 0.2703 0.5393 0.056 Uiso 1 1 calc R . . H10B H 0.7814 0.2924 0.4243 0.056 Uiso 1 1 calc R . . C2 C 0.7450(4) 0.5081(5) 0.7628(7) 0.026(2) Uani 1 1 d . . . H2A H 0.7080 0.4925 0.7161 0.032 Uiso 1 1 calc R . . H2B H 0.7296 0.5081 0.8318 0.032 Uiso 1 1 calc R . . C6 C 0.9289(5) 0.5082(5) 0.8389(7) 0.037(3) Uani 1 1 d . . . H6A H 0.9535 0.5555 0.8370 0.056 Uiso 1 1 calc R . . H6B H 0.9587 0.4914 0.8398 0.056 Uiso 1 1 calc R . . H6C H 0.9020 0.4940 0.8995 0.056 Uiso 1 1 calc R . . C11 C 0.8600(5) 0.3152(5) 0.5141(8) 0.037(3) Uani 1 1 d . . . H11A H 0.8721 0.2940 0.4614 0.044 Uiso 1 1 calc R . . H11B H 0.8617 0.2971 0.5802 0.044 Uiso 1 1 calc R . . Na2 Na 0.6667 0.3333 0.1437(5) 0.0248(13) Uani 1 3 d S . . Na1 Na 0.6667 0.3333 -0.1102(5) 0.0236(12) Uani 1 3 d S . . O4 O 0.5797(3) 0.2836(3) 0.0203(5) 0.0286(13) Uani 1 1 d . . . O3 O 0.5831(3) 0.3125(3) 0.2667(5) 0.0287(16) Uani 1 1 d . . . N3 N 0.4880(4) 0.3139(4) 0.2471(6) 0.0278(18) Uani 1 1 d . . . C16 C 0.4656(5) 0.3607(5) 0.2429(10) 0.039(3) Uani 1 1 d . . . H16A H 0.4412 0.3583 0.3045 0.047 Uiso 1 1 calc R . . H16B H 0.4374 0.3526 0.1838 0.047 Uiso 1 1 calc R . . N4 N 0.4749(4) 0.2028(4) 0.0315(7) 0.036(2) Uani 1 1 d . . . C17 C 0.4476(4) 0.2468(5) 0.2388(7) 0.026(2) Uani 1 1 d . . . H17 H 0.4759 0.2271 0.2378 0.031 Uiso 1 1 calc R . . C14 C 0.5791(5) 0.4143(5) 0.2617(7) 0.034(3) Uani 1 1 d . . . H14A H 0.6151 0.4367 0.2134 0.041 Uiso 1 1 calc R . . H14B H 0.5952 0.4311 0.3299 0.041 Uiso 1 1 calc R . . C21 C 0.5398(5) 0.2259(5) 0.0132(7) 0.0286(13) Uani 1 1 d . . . C13 C 0.5535(5) 0.3445(5) 0.2580(6) 0.024(2) Uani 1 1 d . . . C22 C 0.5487(5) 0.1710(5) -0.0063(10) 0.041(3) Uani 1 1 d . . . H22A H 0.5812 0.1717 0.0406 0.049 Uiso 1 1 calc R . . H22B H 0.5645 0.1732 -0.0757 0.049 Uiso 1 1 calc R . . C20 C 0.4466(5) 0.2415(5) 0.0479(7) 0.030(2) Uani 1 1 d . . . H20A H 0.4189 0.2370 -0.0103 0.036 Uiso 1 1 calc R . . H20B H 0.4812 0.2872 0.0516 0.036 Uiso 1 1 calc R . . C15 C 0.5254(4) 0.4248(5) 0.2349(10) 0.044(3) Uani 1 1 d . . . H15A H 0.5308 0.4418 0.1656 0.053 Uiso 1 1 calc R . . H15B H 0.5236 0.4561 0.2815 0.053 Uiso 1 1 calc R . . C19 C 0.4057(5) 0.2241(5) 0.1446(7) 0.035(2) Uani 1 1 d . . . H19A H 0.3783 0.2442 0.1423 0.042 Uiso 1 1 calc R . . H19B H 0.3770 0.1767 0.1478 0.042 Uiso 1 1 calc R . . C24 C 0.4361(5) 0.1326(4) 0.0091(7) 0.026(2) Uani 1 1 d . . . H24A H 0.4145 0.1254 -0.0569 0.031 Uiso 1 1 calc R . . H24B H 0.4029 0.1100 0.0614 0.031 Uiso 1 1 calc R . . C18 C 0.4017(5) 0.2186(5) 0.3329(7) 0.035(2) Uani 1 1 d . . . H18A H 0.4265 0.2379 0.3943 0.053 Uiso 1 1 calc R . . H18B H 0.3832 0.1717 0.3351 0.053 Uiso 1 1 calc R . . H18C H 0.3669 0.2288 0.3275 0.053 Uiso 1 1 calc R . . C23 C 0.4841(5) 0.1087(5) 0.0080(7) 0.030(2) Uani 1 1 d . . . H23A H 0.4753 0.0783 -0.0481 0.036 Uiso 1 1 calc R . . H23B H 0.4832 0.0873 0.0721 0.036 Uiso 1 1 calc R . . P2 P 0.65127(13) 0.64680(13) 0.2641(2) 0.0274(6) Uani 1 1 d . . . F9 F 0.7269(3) 0.6966(4) 0.2619(5) 0.055(2) Uani 1 1 d . . . F7 F 0.6496(3) 0.6492(3) 0.1445(6) 0.0484(18) Uani 1 1 d . . . F8 F 0.6534(4) 0.6459(4) 0.3828(5) 0.0497(19) Uani 1 1 d . . . F10 F 0.6357(4) 0.7044(3) 0.2702(5) 0.053(2) Uani 1 1 d . . . F12 F 0.6672(4) 0.5887(3) 0.2584(5) 0.060(2) Uani 1 1 d . . . F11 F 0.5755(3) 0.5961(4) 0.2668(6) 0.066(2) Uani 1 1 d . . . Na3 Na 0.6667 0.3333 0.3941(5) 0.0193(11) Uani 1 3 d S . . Na6 Na 1.0000 1.0000 0.6339(4) 0.0171(12) Uani 1 3 d S . . Na5 Na 1.0000 1.0000 0.3856(4) 0.0203(13) Uani 1 3 d S . . 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 N6 0.037(5) 0.017(4) 0.022(4) -0.010(3) -0.007(3) 0.016(4) O5 0.030(4) 0.029(4) 0.017(3) -0.004(3) 0.005(3) 0.016(3) O6 0.033(4) 0.026(3) 0.021(3) -0.008(3) -0.009(3) 0.026(3) C35 0.030(6) 0.026(5) 0.069(8) 0.002(5) -0.007(5) 0.024(5) C26 0.024(5) 0.032(6) 0.027(5) 0.000(4) 0.003(4) 0.018(4) N5 0.029(5) 0.029(5) 0.041(5) 0.006(4) 0.007(4) 0.011(4) C29 0.022(5) 0.035(6) 0.049(7) 0.005(5) 0.013(5) 0.010(5) C33 0.036(6) 0.015(5) 0.023(5) 0.000(4) -0.011(4) 0.001(4) C34 0.023(5) 0.034(6) 0.027(5) -0.022(4) -0.012(4) 0.009(5) C25 0.028(5) 0.019(5) 0.029(5) -0.018(4) -0.016(4) 0.010(4) C32 0.028(5) 0.030(6) 0.040(6) -0.007(5) 0.002(5) 0.013(5) C27 0.051(7) 0.057(8) 0.035(6) -0.005(5) -0.009(5) 0.034(6) C31 0.024(5) 0.024(5) 0.045(6) 0.011(5) -0.006(4) 0.008(4) C30 0.044(7) 0.045(7) 0.063(8) 0.017(6) 0.020(6) 0.028(6) C36 0.029(5) 0.019(5) 0.051(6) 0.009(5) 0.011(5) 0.020(4) C28 0.026(5) 0.033(6) 0.012(4) 0.015(4) 0.011(4) 0.007(5) P1 0.0240(13) 0.0262(13) 0.0200(11) -0.0009(10) 0.0012(10) 0.0120(11) Na4 0.0179(18) 0.0179(18) 0.026(3) 0.000 0.000 0.0089(9) F2 0.059(4) 0.042(4) 0.010(3) 0.004(2) 0.012(3) 0.025(3) F1 0.047(4) 0.041(4) 0.024(3) -0.012(3) -0.012(3) 0.018(3) F4 0.062(5) 0.027(3) 0.046(4) 0.006(3) 0.008(4) -0.025(3) O2 0.018(3) 0.036(4) 0.037(4) 0.003(3) 0.013(3) 0.015(3) N1 0.025(4) 0.024(4) 0.023(4) -0.003(3) -0.005(3) 0.013(4) O1 0.015(3) 0.016(3) 0.038(4) -0.009(3) 0.003(3) -0.006(3) F3 0.056(4) 0.087(6) 0.050(4) -0.006(4) -0.006(3) 0.056(4) C5 0.023(5) 0.020(5) 0.019(5) -0.003(4) -0.003(4) 0.004(4) C4 0.049(7) 0.012(5) 0.058(7) -0.003(5) 0.010(6) 0.009(5) C1 0.026(5) 0.022(5) 0.018(4) 0.010(4) 0.019(4) 0.009(4) F5 0.053(4) 0.080(5) 0.047(4) -0.002(4) -0.009(3) 0.052(4) F6 0.058(5) 0.024(3) 0.053(4) -0.004(3) 0.008(3) 0.009(3) N2 0.038(5) 0.033(5) 0.021(4) 0.001(3) 0.009(4) 0.016(4) C9 0.042(6) 0.031(5) 0.007(4) 0.006(4) 0.008(4) 0.020(5) C12 0.036(6) 0.034(6) 0.023(5) -0.005(4) 0.000(4) 0.022(5) C3 0.044(7) 0.032(6) 0.043(6) 0.009(5) 0.016(5) 0.024(5) C7 0.023(5) 0.019(5) 0.037(6) 0.009(4) 0.006(4) 0.003(4) C8 0.026(5) 0.035(6) 0.027(5) -0.020(4) -0.001(4) 0.015(5) C10 0.054(8) 0.030(6) 0.060(8) 0.006(6) 0.016(6) 0.023(6) C2 0.017(5) 0.033(5) 0.028(5) -0.005(4) 0.000(4) 0.011(4) C6 0.038(6) 0.037(6) 0.027(5) -0.008(4) -0.010(4) 0.012(5) C11 0.054(7) 0.049(7) 0.019(5) -0.007(5) -0.012(5) 0.035(6) Na2 0.0216(19) 0.0216(19) 0.031(4) 0.000 0.000 0.0108(10) Na1 0.0228(18) 0.0228(18) 0.025(3) 0.000 0.000 0.0114(9) O4 0.025(3) 0.027(3) 0.030(3) 0.003(2) -0.013(2) 0.010(2) O3 0.009(3) 0.041(4) 0.038(4) -0.005(3) -0.002(3) 0.014(3) N3 0.013(4) 0.031(4) 0.041(5) 0.011(4) 0.000(3) 0.012(3) C16 0.021(5) 0.025(5) 0.071(8) -0.002(5) 0.013(5) 0.012(5) N4 0.041(5) 0.037(5) 0.044(6) 0.002(4) -0.014(4) 0.031(5) C17 0.015(4) 0.034(5) 0.028(5) -0.010(4) 0.000(4) 0.012(4) C14 0.046(7) 0.026(5) 0.021(5) 0.004(4) -0.015(4) 0.011(5) C21 0.025(3) 0.027(3) 0.030(3) 0.003(2) -0.013(2) 0.010(2) C13 0.035(5) 0.030(5) 0.009(4) -0.006(4) -0.013(4) 0.019(5) C22 0.019(5) 0.027(6) 0.067(8) -0.003(5) -0.006(5) 0.004(5) C20 0.023(5) 0.034(6) 0.030(5) -0.011(4) -0.011(4) 0.013(4) C15 0.013(5) 0.024(5) 0.086(9) 0.007(6) 0.017(5) 0.003(4) C19 0.027(5) 0.038(6) 0.038(6) -0.006(5) -0.004(4) 0.015(5) C24 0.034(5) 0.015(4) 0.023(5) -0.004(4) -0.006(4) 0.008(4) C18 0.031(6) 0.054(7) 0.032(5) 0.015(5) 0.016(4) 0.030(5) C23 0.026(5) 0.027(5) 0.022(5) 0.008(4) -0.004(4) 0.002(4) P2 0.0289(13) 0.0255(13) 0.0272(13) -0.0014(10) -0.0007(10) 0.0133(11) F9 0.040(4) 0.086(6) 0.024(3) 0.004(3) -0.003(3) 0.021(4) F7 0.047(4) 0.059(5) 0.043(4) -0.001(3) -0.006(3) 0.030(4) F8 0.078(5) 0.060(4) 0.021(3) 0.007(3) 0.012(3) 0.042(4) F10 0.095(6) 0.058(4) 0.037(4) 0.014(3) 0.030(4) 0.062(4) F12 0.119(7) 0.053(4) 0.038(4) -0.004(3) -0.007(4) 0.066(5) F11 0.031(4) 0.062(5) 0.076(5) -0.006(4) 0.011(4) 0.002(4) Na3 0.0190(17) 0.0190(17) 0.020(3) 0.000 0.000 0.0095(8) Na6 0.0223(19) 0.0223(19) 0.007(3) 0.000 0.000 0.0112(9) Na5 0.027(2) 0.027(2) 0.006(3) 0.000 0.000 0.0137(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N6 C33 1.342(12) . ? N6 C32 1.428(12) . ? N6 C36 1.448(11) . ? O5 C25 1.246(12) . ? O5 Na6 2.449(7) . ? O5 Na5 2.445(7) . ? O6 C33 1.273(12) . ? O6 Na6 2.407(7) . ? O6 Na5 2.490(7) 4 ? C35 C34 1.564(13) . ? C35 C36 1.526(14) . ? C26 C25 1.568(13) . ? C26 C27 1.587(15) . ? N5 C29 1.502(14) . ? N5 C25 1.340(13) . ? N5 C28 1.472(12) . ? C29 C31 1.550(14) . ? C29 C30 1.428(16) . ? C33 C34 1.500(14) . ? C32 C31 1.569(14) . ? C27 C28 1.560(15) . ? P1 F2 1.610(6) . ? P1 F1 1.616(7) . ? P1 F4 1.562(6) . ? P1 F3 1.587(7) . ? P1 F5 1.603(7) . ? P1 F6 1.604(6) . ? Na4 O2 2.439(7) 2_655 ? Na4 O2 2.439(7) 3_665 ? Na4 O2 2.439(7) . ? Na4 O1 2.430(7) 2_655 ? Na4 O1 2.430(7) . ? Na4 O1 2.430(7) 3_665 ? Na4 Na1 3.255(9) 1_556 ? Na4 Na3 3.344(8) . ? O2 C9 1.233(11) . ? O2 Na3 2.535(8) . ? N1 C5 1.457(12) . ? N1 C4 1.462(12) . ? N1 C1 1.373(11) . ? O1 C1 1.246(11) . ? O1 Na1 2.476(8) 1_556 ? C5 C7 1.551(12) . ? C5 C6 1.501(12) . ? C4 C3 1.544(16) . ? C1 C2 1.505(13) . ? N2 C9 1.385(13) . ? N2 C12 1.487(12) . ? N2 C8 1.396(12) . ? C9 C10 1.520(14) . ? C12 C11 1.494(15) . ? C3 C2 1.466(14) . ? C7 C8 1.565(13) . ? C10 C11 1.488(17) . ? Na2 Na1 3.380(9) . ? Na2 O4 2.443(7) 3_665 ? Na2 O4 2.443(7) . ? Na2 O4 2.443(7) 2_655 ? Na2 O3 2.434(8) . ? Na2 O3 2.434(8) 3_665 ? Na2 O3 2.434(8) 2_655 ? Na2 Na3 3.333(9) . ? Na1 Na4 3.255(9) 1_554 ? Na1 O1 2.476(8) 1_554 ? Na1 O1 2.476(8) 3_664 ? Na1 O1 2.475(8) 2_654 ? Na1 O4 2.508(8) . ? Na1 O4 2.508(8) 2_655 ? Na1 O4 2.508(8) 3_665 ? O4 C21 1.227(11) . ? O3 C13 1.281(11) . ? O3 Na3 2.474(8) . ? N3 C16 1.465(12) . ? N3 C17 1.404(12) . ? N3 C13 1.367(12) . ? C16 C15 1.489(13) . ? N4 C21 1.384(13) . ? N4 C20 1.411(12) . ? N4 C24 1.486(12) . ? C17 C19 1.526(13) . ? C17 C18 1.577(12) . ? C14 C13 1.465(13) . ? C14 C15 1.471(14) . ? C21 C22 1.456(15) . ? C22 C23 1.530(14) . ? C20 C19 1.543(14) . ? C24 C23 1.517(14) . ? P2 F9 1.593(7) . ? P2 F7 1.594(8) . ? P2 F8 1.582(7) . ? P2 F10 1.601(6) . ? P2 F12 1.616(7) . ? P2 F11 1.599(7) . ? Na3 O2 2.535(8) 2_655 ? Na3 O2 2.535(8) 3_665 ? Na3 O3 2.474(8) 3_665 ? Na3 O3 2.474(8) 2_655 ? Na6 O5 2.449(7) 2_765 ? Na6 O5 2.449(7) 3_675 ? Na6 O6 2.407(7) 2_765 ? Na6 O6 2.406(7) 3_675 ? Na6 Na5 3.306(7) . ? Na6 Na5 3.351(7) 4 ? Na5 O5 2.445(7) 3_675 ? Na5 O5 2.445(7) 2_765 ? Na5 O6 2.490(7) 5_674 ? Na5 O6 2.490(7) 4_554 ? Na5 O6 2.490(7) 6_764 ? Na5 Na6 3.351(7) 4_554 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C33 N6 C32 125.4(8) . . ? C33 N6 C36 113.3(8) . . ? C32 N6 C36 121.0(8) . . ? C25 O5 Na6 123.4(6) . . ? C25 O5 Na5 131.0(7) . . ? Na5 O5 Na6 85.0(2) . . ? C33 O6 Na6 120.4(6) . . ? C33 O6 Na5 119.8(6) . 4 ? Na6 O6 Na5 86.3(2) . 4 ? C36 C35 C34 104.0(7) . . ? C25 C26 C27 102.2(8) . . ? C25 N5 C29 122.7(8) . . ? C25 N5 C28 115.8(8) . . ? C28 N5 C29 120.1(8) . . ? N5 C29 C31 108.0(8) . . ? C30 C29 N5 111.6(9) . . ? C30 C29 C31 112.8(10) . . ? N6 C33 C34 110.2(9) . . ? O6 C33 N6 126.0(9) . . ? O6 C33 C34 123.1(8) . . ? C33 C34 C35 103.2(8) . . ? O5 C25 C26 123.2(8) . . ? O5 C25 N5 129.1(9) . . ? N5 C25 C26 107.7(8) . . ? N6 C32 C31 112.3(8) . . ? C28 C27 C26 103.6(8) . . ? C29 C31 C32 118.1(9) . . ? N6 C36 C35 105.0(7) . . ? N5 C28 C27 101.2(8) . . ? F2 P1 F1 178.6(4) . . ? F4 P1 F2 88.1(4) . . ? F4 P1 F1 90.6(4) . . ? F4 P1 F3 88.1(5) . . ? F4 P1 F5 91.7(5) . . ? F4 P1 F6 177.4(5) . . ? F3 P1 F2 89.5(4) . . ? F3 P1 F1 90.8(4) . . ? F3 P1 F5 179.2(4) . . ? F3 P1 F6 89.4(4) . . ? F5 P1 F2 91.3(4) . . ? F5 P1 F1 88.4(4) . . ? F5 P1 F6 90.8(4) . . ? F6 P1 F2 92.7(4) . . ? F6 P1 F1 88.7(4) . . ? O2 Na4 O2 81.6(3) 3_665 2_655 ? O2 Na4 O2 81.6(3) . 2_655 ? O2 Na4 O2 81.6(3) . 3_665 ? O2 Na4 Na1 131.0(2) 2_655 1_556 ? O2 Na4 Na1 131.0(2) 3_665 1_556 ? O2 Na4 Na1 131.0(2) . 1_556 ? O2 Na4 Na3 49.0(2) . . ? O2 Na4 Na3 49.0(2) 3_665 . ? O2 Na4 Na3 49.0(2) 2_655 . ? O1 Na4 O2 121.3(2) 3_665 . ? O1 Na4 O2 84.2(2) . . ? O1 Na4 O2 150.9(2) 3_665 2_655 ? O1 Na4 O2 121.3(2) 2_655 3_665 ? O1 Na4 O2 150.9(2) 2_655 . ? O1 Na4 O2 121.3(2) . 2_655 ? O1 Na4 O2 84.2(2) 2_655 2_655 ? O1 Na4 O2 84.2(2) 3_665 3_665 ? O1 Na4 O2 150.9(2) . 3_665 ? O1 Na4 O1 81.7(3) 3_665 . ? O1 Na4 O1 81.7(3) 3_665 2_655 ? O1 Na4 O1 81.7(3) . 2_655 ? O1 Na4 Na1 49.03(19) 3_665 1_556 ? O1 Na4 Na1 49.03(19) . 1_556 ? O1 Na4 Na1 49.03(19) 2_655 1_556 ? O1 Na4 Na3 130.97(19) 2_655 . ? O1 Na4 Na3 130.97(19) . . ? O1 Na4 Na3 130.97(19) 3_665 . ? Na1 Na4 Na3 180.0 1_556 . ? Na4 O2 Na3 84.5(2) . . ? C9 O2 Na4 124.5(6) . . ? C9 O2 Na3 117.1(6) . . ? C5 N1 C4 122.5(8) . . ? C1 N1 C5 124.1(7) . . ? C1 N1 C4 113.3(8) . . ? Na4 O1 Na1 83.1(2) . 1_556 ? C1 O1 Na4 122.2(6) . . ? C1 O1 Na1 129.1(6) . 1_556 ? N1 C5 C7 111.6(7) . . ? N1 C5 C6 108.1(8) . . ? C6 C5 C7 111.1(8) . . ? N1 C4 C3 102.5(9) . . ? N1 C1 C2 106.4(7) . . ? O1 C1 N1 124.5(8) . . ? O1 C1 C2 128.9(8) . . ? C9 N2 C12 110.0(8) . . ? C9 N2 C8 125.1(9) . . ? C8 N2 C12 123.0(8) . . ? O2 C9 N2 122.4(9) . . ? O2 C9 C10 128.8(10) . . ? N2 C9 C10 108.7(9) . . ? N2 C12 C11 104.4(8) . . ? C2 C3 C4 104.4(8) . . ? C5 C7 C8 114.5(8) . . ? N2 C8 C7 112.3(8) . . ? C11 C10 C9 104.9(9) . . ? C3 C2 C1 107.0(8) . . ? C10 C11 C12 106.5(9) . . ? O4 Na2 Na1 47.8(2) 3_665 . ? O4 Na2 Na1 47.8(2) . . ? O4 Na2 Na1 47.8(2) 2_655 . ? O4 Na2 O4 79.8(3) . 3_665 ? O4 Na2 O4 79.8(3) 2_655 3_665 ? O4 Na2 O4 79.8(3) 2_655 . ? O4 Na2 Na3 132.2(2) 3_665 . ? O4 Na2 Na3 132.2(2) . . ? O4 Na2 Na3 132.2(2) 2_655 . ? O3 Na2 Na1 132.27(19) . . ? O3 Na2 Na1 132.27(19) 3_665 . ? O3 Na2 Na1 132.27(19) 2_655 . ? O3 Na2 O4 151.3(2) . 2_655 ? O3 Na2 O4 151.3(2) 2_655 3_665 ? O3 Na2 O4 122.6(2) 3_665 2_655 ? O3 Na2 O4 86.6(2) 2_655 2_655 ? O3 Na2 O4 86.6(2) 3_665 3_665 ? O3 Na2 O4 86.6(2) . . ? O3 Na2 O4 151.3(2) 3_665 . ? O3 Na2 O4 122.6(2) . 3_665 ? O3 Na2 O4 122.6(2) 2_655 . ? O3 Na2 O3 79.7(3) 2_655 3_665 ? O3 Na2 O3 79.7(3) 2_655 . ? O3 Na2 O3 79.7(3) 3_665 . ? O3 Na2 Na3 47.73(19) 2_655 . ? O3 Na2 Na3 47.73(19) 3_665 . ? O3 Na2 Na3 47.73(19) . . ? Na3 Na2 Na1 180.000(1) . . ? Na4 Na1 Na2 180.0 1_554 . ? O1 Na1 Na4 47.82(19) 2_654 1_554 ? O1 Na1 Na4 47.83(19) 1_554 1_554 ? O1 Na1 Na4 47.82(19) 3_664 1_554 ? O1 Na1 O1 79.9(3) 3_664 1_554 ? O1 Na1 O1 79.9(3) 3_664 2_654 ? O1 Na1 O1 79.9(3) 1_554 2_654 ? O1 Na1 Na2 132.17(19) 3_664 . ? O1 Na1 Na2 132.18(19) 2_654 . ? O1 Na1 Na2 132.17(19) 1_554 . ? O1 Na1 O4 165.5(2) 3_664 3_665 ? O1 Na1 O4 165.5(2) 1_554 . ? O1 Na1 O4 93.30(18) 3_664 2_655 ? O1 Na1 O4 93.30(18) 2_654 . ? O1 Na1 O4 111.7(2) 1_554 2_655 ? O1 Na1 O4 111.7(2) 2_654 3_665 ? O1 Na1 O4 93.30(18) 1_554 3_665 ? O1 Na1 O4 165.5(2) 2_654 2_655 ? O1 Na1 O4 111.7(2) 3_664 . ? O4 Na1 Na4 133.85(18) 2_655 1_554 ? O4 Na1 Na4 133.85(18) . 1_554 ? O4 Na1 Na4 133.85(18) 3_665 1_554 ? O4 Na1 Na2 46.15(18) 3_665 . ? O4 Na1 Na2 46.15(18) . . ? O4 Na1 Na2 46.15(18) 2_655 . ? O4 Na1 O4 77.3(3) . 3_665 ? O4 Na1 O4 77.3(3) 2_655 3_665 ? O4 Na1 O4 77.3(3) 2_655 . ? Na2 O4 Na1 86.1(3) . . ? C21 O4 Na2 126.4(6) . . ? C21 O4 Na1 118.3(7) . . ? Na2 O3 Na3 85.5(2) . . ? C13 O3 Na2 117.3(6) . . ? C13 O3 Na3 125.0(6) . . ? C17 N3 C16 124.5(8) . . ? C13 N3 C16 110.8(8) . . ? C13 N3 C17 124.7(8) . . ? N3 C16 C15 105.0(8) . . ? C21 N4 C20 125.0(9) . . ? C21 N4 C24 111.1(8) . . ? C20 N4 C24 122.6(8) . . ? N3 C17 C19 115.2(8) . . ? N3 C17 C18 111.1(8) . . ? C19 C17 C18 107.9(8) . . ? C13 C14 C15 106.5(9) . . ? O4 C21 N4 121.5(9) . . ? O4 C21 C22 130.2(10) . . ? N4 C21 C22 108.1(8) . . ? O3 C13 N3 121.3(9) . . ? O3 C13 C14 129.6(9) . . ? N3 C13 C14 109.1(8) . . ? C21 C22 C23 108.9(9) . . ? N4 C20 C19 113.6(9) . . ? C14 C15 C16 106.2(9) . . ? C17 C19 C20 112.0(8) . . ? N4 C24 C23 105.3(7) . . ? C24 C23 C22 102.8(8) . . ? F9 P2 F7 89.7(4) . . ? F9 P2 F10 91.4(4) . . ? F9 P2 F12 88.5(5) . . ? F9 P2 F11 179.2(5) . . ? F7 P2 F10 90.0(4) . . ? F7 P2 F12 90.3(4) . . ? F7 P2 F11 90.6(4) . . ? F8 P2 F9 89.7(4) . . ? F8 P2 F7 178.9(4) . . ? F8 P2 F10 89.1(4) . . ? F8 P2 F12 90.6(4) . . ? F8 P2 F11 90.0(4) . . ? F10 P2 F12 179.7(5) . . ? F11 P2 F10 89.4(4) . . ? F11 P2 F12 90.7(5) . . ? O2 Na3 Na4 46.56(17) 2_655 . ? O2 Na3 Na4 46.56(17) 3_665 . ? O2 Na3 Na4 46.56(17) . . ? O2 Na3 O2 77.9(3) . 3_665 ? O2 Na3 O2 77.9(3) . 2_655 ? O2 Na3 O2 77.9(3) 3_665 2_655 ? O2 Na3 Na2 133.44(17) . . ? O2 Na3 Na2 133.44(17) 3_665 . ? O2 Na3 Na2 133.44(17) 2_655 . ? Na2 Na3 Na4 180.000(1) . . ? O3 Na3 Na4 133.27(18) . . ? O3 Na3 Na4 133.27(18) 3_665 . ? O3 Na3 Na4 133.27(18) 2_655 . ? O3 Na3 O2 94.0(2) 2_655 3_665 ? O3 Na3 O2 112.0(2) 3_665 2_655 ? O3 Na3 O2 165.8(2) 3_665 3_665 ? O3 Na3 O2 165.9(2) . . ? O3 Na3 O2 165.8(2) 2_655 2_655 ? O3 Na3 O2 94.0(2) . 2_655 ? O3 Na3 O2 112.0(2) 2_655 . ? O3 Na3 O2 112.0(2) . 3_665 ? O3 Na3 O2 94.0(2) 3_665 . ? O3 Na3 Na2 46.73(18) 3_665 . ? O3 Na3 Na2 46.73(18) . . ? O3 Na3 Na2 46.73(18) 2_655 . ? O3 Na3 O3 78.2(3) 2_655 . ? O3 Na3 O3 78.2(3) 3_665 . ? O3 Na3 O3 78.2(3) 2_655 3_665 ? O5 Na6 O5 79.3(3) . 3_675 ? O5 Na6 O5 79.3(3) . 2_765 ? O5 Na6 O5 79.3(3) 3_675 2_765 ? O5 Na6 Na5 132.54(17) 3_675 4 ? O5 Na6 Na5 132.54(17) . 4 ? O5 Na6 Na5 47.46(17) 2_765 . ? O5 Na6 Na5 47.46(17) . . ? O5 Na6 Na5 47.46(17) 3_675 . ? O5 Na6 Na5 132.54(17) 2_765 4 ? O6 Na6 O5 151.0(2) 3_675 2_765 ? O6 Na6 O5 151.0(2) . 3_675 ? O6 Na6 O5 86.6(2) 2_765 2_765 ? O6 Na6 O5 123.0(2) . 2_765 ? O6 Na6 O5 123.0(2) 2_765 3_675 ? O6 Na6 O5 86.6(2) 3_675 3_675 ? O6 Na6 O5 123.0(2) 3_675 . ? O6 Na6 O5 86.6(2) . . ? O6 Na6 O5 151.0(2) 2_765 . ? O6 Na6 O6 79.9(3) 2_765 . ? O6 Na6 O6 79.9(3) 3_675 . ? O6 Na6 O6 79.9(3) 3_675 2_765 ? O6 Na6 Na5 132.12(17) 2_765 . ? O6 Na6 Na5 47.87(17) 3_675 4 ? O6 Na6 Na5 132.12(17) . . ? O6 Na6 Na5 47.88(17) . 4 ? O6 Na6 Na5 47.88(17) 2_765 4 ? O6 Na6 Na5 132.13(17) 3_675 . ? Na5 Na6 Na5 180.0 . 4 ? O5 Na5 O5 79.5(3) 3_675 . ? O5 Na5 O5 79.5(3) 3_675 2_765 ? O5 Na5 O5 79.5(3) . 2_765 ? O5 Na5 O6 160.7(2) . 5_674 ? O5 Na5 O6 91.7(2) 3_675 5_674 ? O5 Na5 O6 116.0(2) 2_765 5_674 ? O5 Na5 O6 116.0(2) 3_675 4_554 ? O5 Na5 O6 91.7(2) . 4_554 ? O5 Na5 O6 160.7(2) 3_675 6_764 ? O5 Na5 O6 160.7(2) 2_765 4_554 ? O5 Na5 O6 91.7(2) 2_765 6_764 ? O5 Na5 O6 116.0(2) . 6_764 ? O5 Na5 Na6 132.43(17) 2_765 4_554 ? O5 Na5 Na6 47.57(17) . . ? O5 Na5 Na6 47.57(17) 3_675 . ? O5 Na5 Na6 47.57(17) 2_765 . ? O5 Na5 Na6 132.43(17) 3_675 4_554 ? O5 Na5 Na6 132.43(17) . 4_554 ? O6 Na5 O6 76.7(3) 5_674 4_554 ? O6 Na5 O6 76.7(3) 5_674 6_764 ? O6 Na5 O6 76.7(3) 4_554 6_764 ? O6 Na5 Na6 134.21(17) 6_764 . ? O6 Na5 Na6 134.21(17) 4_554 . ? O6 Na5 Na6 134.21(17) 5_674 . ? O6 Na5 Na6 45.79(17) 5_674 4_554 ? O6 Na5 Na6 45.79(17) 4_554 4_554 ? O6 Na5 Na6 45.79(17) 6_764 4_554 ? Na6 Na5 Na6 180.0 . 4_554 ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -1 1 0 0.0597 -1.0000 1.0000 -0.0000 0.0068 0.0272 0.0196 29 -29 -1 0.0597 28.9999 -29.0000 -1.0000 -0.1820 -0.7623 -0.6119 0 -1 2 0.0987 -0.0000 -1.0000 2.0000 -0.0612 -0.0588 0.0729 2 8 -18 0.0987 2.0000 8.0000 -18.0000 0.5686 0.4792 -0.6821 2 0 0 0.0384 2.0000 0.0000 0.0000 0.0489 -0.0463 -0.0124 -32 6 2 0.0384 -32.0000 6.0000 2.0000 -0.6247 0.7104 0.3647 2 0 0 0.0411 2.0000 0.0000 0.0000 0.0489 -0.0463 -0.0124 -27 -2 -5 0.0411 -27.0000 -2.0000 -5.0000 -0.6474 0.7536 -0.0759 0 1 1 0.1012 0.0000 1.0000 1.0000 0.0162 -0.0233 0.0566 1 -18 -15 0.1012 1.0000 -18.0000 -15.0000 -0.3129 0.3140 -0.8956 _database_code_depnum_ccdc_archive 'CCDC 965875' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ap60_17 _audit_creation_date 2012-12-31 _audit_creation_method ; Olex2 1.2 (compiled Nov 5 2012 18:25:38, GUI svn.r4372) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'F6 P, C12 H21 N2 O3' _chemical_formula_sum 'C12 H21 F6 N2 O3 P' _chemical_formula_weight 386.28 _chemical_melting_point ? _chemical_oxdiff_formula 'C12 H20 N2 O3 Li P F6' 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' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' _cell_length_a 11.6287(6) _cell_length_b 13.8824(7) _cell_length_c 20.0682(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3239.7(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 3561 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 32.5485 _cell_measurement_theta_min 2.6757 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.65202 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1600 _exptl_crystal_size_max 0.6976 _exptl_crystal_size_mid 0.1279 _exptl_crystal_size_min 0.1267 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.1202 _diffrn_reflns_av_unetI/netI 0.0619 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 30797 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.68 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -86.00 -34.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -179.0000 90.0000 52 #__ type_ start__ end____ width___ exp.time_ 2 omega -50.00 42.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 38.0000 30.0000 92 #__ type_ start__ end____ width___ exp.time_ 3 omega -92.00 31.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 0.0000 -180.0000 123 #__ type_ start__ end____ width___ exp.time_ 4 omega 60.00 86.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 179.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega 67.00 96.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 179.0000 -180.0000 29 #__ type_ start__ end____ width___ exp.time_ 6 omega 42.00 86.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -127.0000 -142.0000 44 #__ type_ start__ end____ width___ exp.time_ 7 omega -30.00 45.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -57.0000 -120.0000 75 #__ type_ start__ end____ width___ exp.time_ 8 omega 46.00 86.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -127.0000 37.0000 40 #__ type_ start__ end____ width___ exp.time_ 9 omega -96.00 -47.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -77.0000 30.0000 49 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0117337000 _diffrn_orient_matrix_UB_12 0.0483570000 _diffrn_orient_matrix_UB_13 0.0091664000 _diffrn_orient_matrix_UB_21 0.0009073000 _diffrn_orient_matrix_UB_22 -0.0136827000 _diffrn_orient_matrix_UB_23 0.0340827000 _diffrn_orient_matrix_UB_31 0.0597972000 _diffrn_orient_matrix_UB_32 -0.0092404000 _diffrn_orient_matrix_UB_33 -0.0023404000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2595 _reflns_number_total 3708 _reflns_odcompleteness_completeness 99.84 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.44 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 0.623 _refine_diff_density_min -0.592 _refine_diff_density_rms 0.091 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 3708 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0618 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1604 _refine_ls_wR_factor_ref 0.1873 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H3A,H3B} of C3, {H4A,H4B} of C4, {H10A,H10B} of C10, {H11A,H11B} of C11, {H2A,H2B} of C2, {H5A,H5B} of C5, {H12A,H12B} of C12, {H8A,H8B} of C8, {H6A, H6B} of C6, {H7A,H7B} of C7 2.a Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C6(H6A,H6B), C8(H8A,H8B), C12(H12A,H12B), C5(H5A,H5B), C2(H2A, H2B), C11(H11A,H11B), C10(H10A,H10B), C4(H4A,H4B), C3(H3A,H3B) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.30520(6) 0.57696(5) 0.59724(4) 0.0277(2) Uani 1 1 d . . . O2 O 0.59630(15) 0.63741(13) 0.16791(8) 0.0219(4) Uani 1 1 d . . . O1 O 0.84613(15) 0.78943(14) 0.16536(9) 0.0258(4) Uani 1 1 d . . . O3 O 0.41631(16) 0.64749(14) -0.05926(9) 0.0268(4) Uani 1 1 d . . . F1 F 0.43273(15) 0.53768(14) 0.58517(9) 0.0427(5) Uani 1 1 d . . . F3 F 0.17758(15) 0.61695(14) 0.60936(9) 0.0412(5) Uani 1 1 d . . . N1 N 0.68429(18) 0.80687(16) 0.22828(10) 0.0208(5) Uani 1 1 d . . . F2 F 0.27794(18) 0.56193(16) 0.52052(9) 0.0502(6) Uani 1 1 d . . . F5 F 0.26217(16) 0.47038(13) 0.61274(10) 0.0469(5) Uani 1 1 d . . . N2 N 0.53574(18) 0.68216(16) 0.02662(10) 0.0205(5) Uani 1 1 d . . . F4 F 0.33273(17) 0.59086(18) 0.67448(9) 0.0575(7) Uani 1 1 d . . . C7 C 0.4923(2) 0.6070(2) 0.13665(12) 0.0227(6) Uani 1 1 d . . . H7A H 0.4318 0.6564 0.1429 0.027 Uiso 1 1 calc R . . H7B H 0.4653 0.5460 0.1569 0.027 Uiso 1 1 calc R . . C6 C 0.5860(2) 0.65042(19) 0.23816(12) 0.0241(6) Uani 1 1 d . . . H6A H 0.5877 0.5874 0.2612 0.029 Uiso 1 1 calc R . . H6B H 0.5127 0.6831 0.2490 0.029 Uiso 1 1 calc R . . C8 C 0.5154(2) 0.59235(18) 0.06297(12) 0.0235(6) Uani 1 1 d . . . H8A H 0.5835 0.5502 0.0578 0.028 Uiso 1 1 calc R . . H8B H 0.4489 0.5588 0.0428 0.028 Uiso 1 1 calc R . . C1 C 0.7601(2) 0.83792(19) 0.18499(12) 0.0207(5) Uani 1 1 d . . . C12 C 0.6160(2) 0.7571(2) 0.04985(13) 0.0263(6) Uani 1 1 d . . . H12A H 0.6913 0.7289 0.0620 0.032 Uiso 1 1 calc R . . H12B H 0.5844 0.7917 0.0889 0.032 Uiso 1 1 calc R . . C5 C 0.6874(2) 0.71194(19) 0.25977(12) 0.0229(6) Uani 1 1 d . . . H5A H 0.6859 0.7197 0.3088 0.027 Uiso 1 1 calc R . . H5B H 0.7599 0.6790 0.2476 0.027 Uiso 1 1 calc R . . C9 C 0.4878(2) 0.70384(19) -0.02978(12) 0.0221(5) Uani 1 1 d . . . F6 F 0.3481(2) 0.68391(15) 0.58285(13) 0.0680(7) Uani 1 1 d . . . C2 C 0.7299(2) 0.93768(19) 0.16143(14) 0.0263(6) Uani 1 1 d . . . H2A H 0.7014 0.9366 0.1150 0.032 Uiso 1 1 calc R . . H2B H 0.7972 0.9812 0.1642 0.032 Uiso 1 1 calc R . . C11 C 0.6273(3) 0.8244(2) -0.01004(14) 0.0348(7) Uani 1 1 d . . . H11A H 0.6996 0.8116 -0.0345 0.042 Uiso 1 1 calc R . . H11B H 0.6264 0.8926 0.0043 0.042 Uiso 1 1 calc R . . C10 C 0.5227(2) 0.8017(2) -0.05354(13) 0.0263(6) Uani 1 1 d . . . H10A H 0.4605 0.8492 -0.0465 0.032 Uiso 1 1 calc R . . H10B H 0.5436 0.8006 -0.1014 0.032 Uiso 1 1 calc R . . C4 C 0.5883(2) 0.8742(2) 0.23907(14) 0.0268(6) Uani 1 1 d . . . H4A H 0.5707 0.8812 0.2871 0.032 Uiso 1 1 calc R . . H4B H 0.5183 0.8528 0.2153 0.032 Uiso 1 1 calc R . . C3 C 0.6353(2) 0.9689(2) 0.20968(14) 0.0325(7) Uani 1 1 d . . . H3A H 0.5740 1.0045 0.1859 0.039 Uiso 1 1 calc R . . H3B H 0.6669 1.0106 0.2452 0.039 Uiso 1 1 calc R . . H3 H 0.391(3) 0.673(3) -0.1021(19) 0.065(12) Uiso 1 1 d . . . 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 0.0252(4) 0.0250(4) 0.0330(4) -0.0072(3) 0.0033(3) -0.0021(3) O2 0.0268(10) 0.0214(10) 0.0176(9) -0.0015(7) 0.0001(7) -0.0024(7) O1 0.0252(9) 0.0277(11) 0.0246(10) -0.0004(8) 0.0058(7) 0.0035(8) O3 0.0277(10) 0.0261(11) 0.0267(10) -0.0002(8) -0.0090(8) -0.0030(8) F1 0.0280(9) 0.0488(13) 0.0512(11) -0.0102(9) 0.0047(7) 0.0055(8) F3 0.0302(10) 0.0436(12) 0.0499(11) -0.0036(9) 0.0027(7) 0.0068(8) N1 0.0226(11) 0.0186(11) 0.0213(11) -0.0012(8) 0.0020(8) -0.0027(8) F2 0.0565(12) 0.0608(15) 0.0333(11) -0.0025(9) -0.0015(8) 0.0142(10) F5 0.0490(12) 0.0309(11) 0.0608(13) 0.0020(9) 0.0092(9) -0.0040(9) N2 0.0233(11) 0.0167(11) 0.0216(11) 0.0002(8) -0.0010(8) -0.0032(9) F4 0.0394(11) 0.0907(18) 0.0426(12) -0.0316(11) -0.0045(8) 0.0072(10) C7 0.0238(13) 0.0220(14) 0.0225(13) 0.0015(10) -0.0042(10) -0.0066(10) C6 0.0300(14) 0.0221(14) 0.0202(13) -0.0007(10) 0.0005(10) -0.0048(11) C8 0.0332(15) 0.0140(13) 0.0231(13) 0.0009(10) -0.0058(10) -0.0033(10) C1 0.0204(13) 0.0213(14) 0.0204(12) -0.0052(10) -0.0009(9) -0.0017(10) C12 0.0324(15) 0.0223(14) 0.0243(13) 0.0025(10) -0.0070(11) -0.0090(11) C5 0.0281(13) 0.0213(14) 0.0193(13) 0.0022(10) -0.0018(10) -0.0032(10) C9 0.0241(13) 0.0198(13) 0.0224(13) -0.0003(10) -0.0008(10) 0.0015(10) F6 0.0612(14) 0.0225(11) 0.120(2) -0.0046(11) 0.0311(13) -0.0098(10) C2 0.0337(15) 0.0178(14) 0.0274(14) -0.0013(11) 0.0022(11) -0.0044(11) C11 0.0474(18) 0.0282(16) 0.0289(15) 0.0044(12) -0.0051(13) -0.0146(14) C10 0.0334(15) 0.0224(14) 0.0232(13) 0.0035(10) -0.0005(11) -0.0021(11) C4 0.0239(14) 0.0251(15) 0.0313(14) -0.0056(11) 0.0048(11) 0.0033(11) C3 0.0385(17) 0.0220(15) 0.0370(16) -0.0053(12) 0.0031(12) 0.0041(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 F1 1.5986(19) . ? P1 F3 1.6031(18) . ? P1 F2 1.5856(19) . ? P1 F5 1.593(2) . ? P1 F4 1.5946(19) . ? P1 F6 1.593(2) . ? O2 C7 1.426(3) . ? O2 C6 1.426(3) . ? O1 C1 1.269(3) . ? O3 C9 1.286(3) . ? N1 C1 1.310(3) . ? N1 C5 1.462(3) . ? N1 C4 1.472(3) . ? N2 C8 1.464(3) . ? N2 C12 1.474(3) . ? N2 C9 1.297(3) . ? C7 C8 1.517(3) . ? C6 C5 1.519(4) . ? C1 C2 1.505(4) . ? C12 C11 1.527(4) . ? C9 C10 1.495(4) . ? C2 C3 1.528(4) . ? C11 C10 1.530(4) . ? C4 C3 1.541(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 P1 F3 179.68(12) . . ? F2 P1 F1 89.63(10) . . ? F2 P1 F3 90.45(10) . . ? F2 P1 F5 90.26(12) . . ? F2 P1 F4 179.38(13) . . ? F2 P1 F6 90.54(13) . . ? F5 P1 F1 90.23(11) . . ? F5 P1 F3 90.07(11) . . ? F5 P1 F4 89.17(12) . . ? F4 P1 F1 90.13(10) . . ? F4 P1 F3 89.80(10) . . ? F6 P1 F1 90.01(12) . . ? F6 P1 F3 89.68(12) . . ? F6 P1 F5 179.17(12) . . ? F6 P1 F4 90.03(14) . . ? C7 O2 C6 113.64(19) . . ? C1 N1 C5 124.5(2) . . ? C1 N1 C4 113.5(2) . . ? C5 N1 C4 121.8(2) . . ? C8 N2 C12 123.1(2) . . ? C9 N2 C8 124.3(2) . . ? C9 N2 C12 112.6(2) . . ? O2 C7 C8 108.5(2) . . ? O2 C6 C5 106.7(2) . . ? N2 C8 C7 113.6(2) . . ? O1 C1 N1 124.2(2) . . ? O1 C1 C2 125.1(2) . . ? N1 C1 C2 110.8(2) . . ? N2 C12 C11 103.7(2) . . ? N1 C5 C6 111.4(2) . . ? O3 C9 N2 122.6(2) . . ? O3 C9 C10 125.5(2) . . ? N2 C9 C10 111.9(2) . . ? C1 C2 C3 103.3(2) . . ? C12 C11 C10 104.8(2) . . ? C9 C10 C11 102.7(2) . . ? N1 C4 C3 102.5(2) . . ? C2 C3 C4 104.8(2) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 -1 28 0.0639 -0.0412 -1.0293 27.9681 0.2061 0.9673 -0.0584 0 1 -28 0.0639 0.0412 1.0293 -27.9681 -0.2061 -0.9673 0.0584 16 -4 -1 0.3278 15.9990 -3.9896 -0.9296 -0.0137 0.0374 0.9957 -16 4 1 0.3278 -15.9990 3.9896 0.9296 0.0137 -0.0374 -0.9957 0 19 4 0.0633 -0.0004 19.0030 4.0741 0.9563 -0.1212 -0.1852 0 -19 -4 0.0633 0.0004 -19.0030 -4.0741 -0.9563 0.1212 0.1852 _database_code_depnum_ccdc_archive 'CCDC 965876' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_napf6 _audit_creation_date 2013-02-04 _audit_creation_method ; Olex2 1.2 (compiled Nov 5 2012 18:25:38, GUI svn.r4372) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'F6 P, C24 H40 N4 Na O6' _chemical_formula_sum 'C24 H40 F6 N4 Na O6 P' _chemical_formula_weight 648.56 _chemical_melting_point ? _chemical_oxdiff_formula 'C14 h10 n2 o2 na p f6' 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' Na Na 0.0362 0.0249 '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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 7.0768(4) _cell_length_b 8.5945(5) _cell_length_c 12.9170(7) _cell_angle_alpha 77.011(5) _cell_angle_beta 77.346(4) _cell_angle_gamma 74.071(5) _cell_volume 725.67(7) _cell_formula_units_Z 1 _cell_measurement_reflns_used 4837 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 32.4934 _cell_measurement_theta_min 2.7367 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_correction_T_min 0.941 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 340 _exptl_crystal_size_max 0.497 _exptl_crystal_size_mid 0.2891 _exptl_crystal_size_min 0.1196 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_unetI/netI 0.0290 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 12472 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.74 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -103.00 -46.00 1.0000 25.0800 omega____ theta____ kappa____ phi______ frames - -26.3429 -179.0000 -60.0000 57 #__ type_ start__ end____ width___ exp.time_ 2 omega -93.00 -17.00 1.0000 25.0800 omega____ theta____ kappa____ phi______ frames - -26.3429 -57.0000 90.0000 76 #__ type_ start__ end____ width___ exp.time_ 3 omega -70.00 47.00 1.0000 25.0800 omega____ theta____ kappa____ phi______ frames - -26.3429 19.0000 -90.0000 117 #__ type_ start__ end____ width___ exp.time_ 4 omega -38.00 32.00 1.0000 25.0800 omega____ theta____ kappa____ phi______ frames - -26.3429 57.0000 -30.0000 70 #__ type_ start__ end____ width___ exp.time_ 5 omega 61.00 99.00 1.0000 25.0800 omega____ theta____ kappa____ phi______ frames - 26.9679 179.0000 30.0000 38 #__ type_ start__ end____ width___ exp.time_ 6 omega 37.00 84.00 1.0000 25.0800 omega____ theta____ kappa____ phi______ frames - 26.9679 -126.0000 -124.0000 47 #__ type_ start__ end____ width___ exp.time_ 7 omega 56.00 98.00 1.0000 25.0800 omega____ theta____ kappa____ phi______ frames - 26.9679 -148.0000 69.0000 42 #__ type_ start__ end____ width___ exp.time_ 8 omega -95.00 -5.00 1.0000 25.0800 omega____ theta____ kappa____ phi______ frames - -26.3429 -57.0000 -60.0000 90 #__ type_ start__ end____ width___ exp.time_ 9 omega -96.00 4.00 1.0000 25.0800 omega____ theta____ kappa____ phi______ frames - -26.3429 -77.0000 -150.0000 100 #__ type_ start__ end____ width___ exp.time_ 10 omega -56.00 44.00 1.0000 25.0800 omega____ theta____ kappa____ phi______ frames - -26.3429 77.0000 -30.0000 100 #__ type_ start__ end____ width___ exp.time_ 11 omega -95.00 -26.00 1.0000 25.0800 omega____ theta____ kappa____ phi______ frames - -26.3429 -57.0000 30.0000 69 #__ type_ start__ end____ width___ exp.time_ 12 omega -43.00 32.00 1.0000 25.0800 omega____ theta____ kappa____ phi______ frames - 26.9679 -77.0000 90.0000 75 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0325788000 _diffrn_orient_matrix_UB_12 -0.0725059000 _diffrn_orient_matrix_UB_13 0.0040569000 _diffrn_orient_matrix_UB_21 0.0078778000 _diffrn_orient_matrix_UB_22 0.0137500000 _diffrn_orient_matrix_UB_23 -0.0568569000 _diffrn_orient_matrix_UB_31 0.1002798000 _diffrn_orient_matrix_UB_32 -0.0464097000 _diffrn_orient_matrix_UB_33 -0.0043389000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2945 _reflns_number_total 3330 _reflns_odcompleteness_completeness 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.44 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.344 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 3330 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0377 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.2493P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0956 _refine_ls_wR_factor_ref 0.0995 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H8A,H8B} of C8, {H4A,H4B} of C4, {H5A,H5B} of C5, {H10A,H10B} of C10, {H9A, H9B} of C9, {H3A,H3B} of C3, {H11A,H11B} of C11, {H2A,H2B} of C2, {H7A,H7B} of C7, {H6A,H6B} of C6 2. Others 1-Sof(F1)=1-Sof(F1)=Sof(F4)=Sof(F5) 3.a Secondary CH2 refined with riding coordinates: C5(H5A,H5B), C8(H8A,H8B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C2(H2A,H2B), C11(H11A,H11B), C3(H3A,H3B), C9(H9A,H9B), C10(H10A,H10B) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.0000 0.0000 0.0000 0.01934(14) Uani 1 2 d S . . F2 F -0.04176(18) -0.15191(14) 0.09043(9) 0.0508(3) Uani 1 1 d . A . F3 F -0.2319(5) 0.0745(8) 0.0219(4) 0.0529(13) Uani 0.662(17) 1 d P A 2 F1 F 0.0273(9) 0.0803(7) 0.0911(4) 0.0755(15) Uani 0.662(17) 1 d P A 2 Na1 Na 0.5000 0.5000 0.5000 0.01665(18) Uani 1 2 d S . . O2 O 0.80282(14) 0.57866(11) 0.37547(8) 0.0178(2) Uani 1 1 d . . . O3 O 0.31909(15) 0.77563(12) 0.47148(8) 0.0230(2) Uani 1 1 d . . . O1 O 0.41382(15) 0.47737(13) 0.33769(7) 0.0212(2) Uani 1 1 d . . . N1 N 0.69442(17) 0.46612(14) 0.20870(9) 0.0168(2) Uani 1 1 d . . . N6 N 0.55548(18) 0.91225(14) 0.37384(9) 0.0185(3) Uani 1 1 d . . . C5 C 0.8372(2) 0.36621(16) 0.27673(11) 0.0176(3) Uani 1 1 d . . . H5A H 0.9354 0.2844 0.2369 0.021 Uiso 1 1 calc R . . H5B H 0.7668 0.3058 0.3414 0.021 Uiso 1 1 calc R . . C12 C 0.3744(2) 0.87949(16) 0.39693(11) 0.0175(3) Uani 1 1 d . . . C1 C 0.4983(2) 0.51409(16) 0.24441(10) 0.0164(3) Uani 1 1 d . . . C8 C 0.7118(2) 0.83379(18) 0.43839(11) 0.0210(3) Uani 1 1 d . . . H8A H 0.6531 0.7768 0.5085 0.025 Uiso 1 1 calc R . . H8B H 0.7668 0.9195 0.4529 0.025 Uiso 1 1 calc R . . C4 C 0.7545(2) 0.52402(19) 0.09378(11) 0.0234(3) Uani 1 1 d . . . H4A H 0.7826 0.4344 0.0519 0.028 Uiso 1 1 calc R . . H4B H 0.8740 0.5689 0.0808 0.028 Uiso 1 1 calc R . . C6 C 0.9454(2) 0.47007(17) 0.31142(12) 0.0200(3) Uani 1 1 d . . . H6A H 1.0478 0.3987 0.3538 0.024 Uiso 1 1 calc R . . H6B H 1.0126 0.5341 0.2473 0.024 Uiso 1 1 calc R . . C7 C 0.8799(2) 0.71110(17) 0.38443(12) 0.0207(3) Uani 1 1 d . . . H7A H 0.9345 0.7644 0.3120 0.025 Uiso 1 1 calc R . . H7B H 0.9885 0.6695 0.4278 0.025 Uiso 1 1 calc R . . C2 C 0.3988(2) 0.61647(19) 0.15056(11) 0.0238(3) Uani 1 1 d . . . H2A H 0.3037 0.7173 0.1712 0.029 Uiso 1 1 calc R . . H2B H 0.3269 0.5529 0.1246 0.029 Uiso 1 1 calc R . . C11 C 0.2465(2) 0.99594(18) 0.31868(12) 0.0251(3) Uani 1 1 d . . . H11A H 0.1397 1.0760 0.3559 0.030 Uiso 1 1 calc R . . H11B H 0.1848 0.9347 0.2843 0.030 Uiso 1 1 calc R . . C3 C 0.5723(2) 0.6589(2) 0.06439(12) 0.0275(3) Uani 1 1 d . . . H3A H 0.5896 0.7686 0.0663 0.033 Uiso 1 1 calc R . . H3B H 0.5497 0.6579 -0.0084 0.033 Uiso 1 1 calc R . . C9 C 0.5748(3) 1.0487(2) 0.28459(13) 0.0331(4) Uani 1 1 d . . . H9A H 0.6963 1.0178 0.2313 0.040 Uiso 1 1 calc R . . H9B H 0.5812 1.1465 0.3110 0.040 Uiso 1 1 calc R . . C10 C 0.3895(3) 1.0824(2) 0.23552(13) 0.0328(4) Uani 1 1 d . . . H10A H 0.4212 1.0386 0.1675 0.039 Uiso 1 1 calc R . . H10B H 0.3304 1.2020 0.2201 0.039 Uiso 1 1 calc R . . F4 F 0.110(3) 0.0466(17) 0.0778(11) 0.097(5) Uani 0.338(17) 1 d P A 1 F5 F -0.194(3) 0.1279(15) 0.0388(9) 0.082(4) Uani 0.338(17) 1 d P A 1 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 0.0184(3) 0.0203(3) 0.0163(2) 0.00080(18) -0.00423(19) -0.00186(19) F2 0.0465(7) 0.0417(6) 0.0496(7) 0.0232(5) -0.0064(5) -0.0129(5) F3 0.0180(12) 0.061(3) 0.0504(16) 0.0241(17) -0.0008(9) 0.0083(13) F1 0.092(3) 0.109(3) 0.0504(17) -0.047(2) -0.001(2) -0.048(2) Na1 0.0173(4) 0.0159(4) 0.0151(4) 0.0004(3) -0.0025(3) -0.0040(3) O2 0.0145(5) 0.0188(5) 0.0208(5) -0.0069(4) 0.0008(4) -0.0054(4) O3 0.0222(5) 0.0177(5) 0.0240(5) 0.0044(4) -0.0005(4) -0.0054(4) O1 0.0163(5) 0.0318(5) 0.0151(5) -0.0020(4) -0.0011(4) -0.0080(4) N1 0.0143(6) 0.0204(5) 0.0140(5) -0.0024(4) -0.0009(4) -0.0031(4) N6 0.0210(6) 0.0155(5) 0.0175(6) -0.0019(4) -0.0001(4) -0.0054(4) C5 0.0154(6) 0.0171(6) 0.0194(6) -0.0037(5) -0.0037(5) -0.0011(5) C12 0.0212(7) 0.0128(6) 0.0174(6) -0.0045(5) -0.0010(5) -0.0027(5) C1 0.0155(6) 0.0194(6) 0.0155(6) -0.0035(5) -0.0029(5) -0.0054(5) C8 0.0222(7) 0.0228(7) 0.0216(7) -0.0079(5) -0.0032(6) -0.0083(6) C4 0.0209(7) 0.0292(7) 0.0158(6) -0.0022(5) 0.0016(5) -0.0040(6) C6 0.0121(6) 0.0231(7) 0.0245(7) -0.0091(5) -0.0009(5) -0.0012(5) C7 0.0174(7) 0.0229(7) 0.0246(7) -0.0058(5) -0.0033(5) -0.0083(5) C2 0.0186(7) 0.0312(8) 0.0173(7) -0.0001(6) -0.0040(5) -0.0013(6) C11 0.0286(8) 0.0231(7) 0.0226(7) 0.0027(6) -0.0077(6) -0.0072(6) C3 0.0262(8) 0.0307(8) 0.0189(7) 0.0041(6) -0.0021(6) -0.0038(6) C9 0.0348(9) 0.0320(8) 0.0284(8) 0.0088(7) -0.0018(7) -0.0156(7) C10 0.0360(9) 0.0289(8) 0.0266(8) 0.0089(6) -0.0041(7) -0.0083(7) F4 0.160(11) 0.101(6) 0.075(6) 0.042(5) -0.099(7) -0.089(7) F5 0.086(7) 0.045(4) 0.048(4) 0.021(3) 0.038(4) 0.032(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 F2 1.5910(10) . ? P1 F2 1.5910(10) 2 ? P1 F3 1.576(4) 2 ? P1 F3 1.576(4) . ? P1 F1 1.561(5) 2 ? P1 F1 1.561(5) . ? P1 F4 1.571(8) 2 ? P1 F4 1.571(8) . ? P1 F5 1.571(8) . ? P1 F5 1.571(8) 2 ? Na1 O2 2.5364(10) 2_666 ? Na1 O2 2.5364(10) . ? Na1 O3 2.3529(10) . ? Na1 O3 2.3529(10) 2_666 ? Na1 O1 2.3694(10) . ? Na1 O1 2.3694(10) 2_666 ? O2 C6 1.4276(15) . ? O2 C7 1.4262(17) . ? O3 C12 1.2320(16) . ? O1 C1 1.2352(16) . ? N1 C5 1.4505(17) . ? N1 C1 1.3417(17) . ? N1 C4 1.4627(17) . ? N6 C12 1.3426(19) . ? N6 C8 1.4546(18) . ? N6 C9 1.4612(18) . ? C5 C6 1.513(2) . ? C12 C11 1.5138(19) . ? C1 C2 1.5144(18) . ? C8 C7 1.5137(19) . ? C4 C3 1.532(2) . ? C2 C3 1.531(2) . ? C11 C10 1.519(2) . ? C9 C10 1.510(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 P1 F2 179.999(1) . 2 ? F3 P1 F2 93.72(18) . 2 ? F3 P1 F2 86.29(18) 2 2 ? F3 P1 F2 86.29(18) . . ? F3 P1 F2 93.71(18) 2 . ? F3 P1 F3 180.0 . 2 ? F1 P1 F2 92.3(2) 2 . ? F1 P1 F2 87.7(2) . . ? F1 P1 F2 87.7(2) 2 2 ? F1 P1 F2 92.3(2) . 2 ? F1 P1 F3 90.4(2) 2 2 ? F1 P1 F3 89.6(2) . 2 ? F1 P1 F3 90.4(2) . . ? F1 P1 F3 89.6(2) 2 . ? F1 P1 F1 180.0 2 . ? F1 P1 F4 21.5(8) . . ? F1 P1 F4 158.5(8) . 2 ? F1 P1 F4 158.5(8) 2 . ? F1 P1 F4 21.5(8) 2 2 ? F1 P1 F5 111.9(7) . 2 ? F1 P1 F5 68.1(7) 2 2 ? F1 P1 F5 68.1(7) . . ? F1 P1 F5 111.9(7) 2 . ? F4 P1 F2 91.2(3) 2 . ? F4 P1 F2 88.8(3) . . ? F4 P1 F2 91.2(3) . 2 ? F4 P1 F2 88.8(3) 2 2 ? F4 P1 F3 68.2(7) . 2 ? F4 P1 F3 111.8(7) 2 2 ? F4 P1 F3 68.2(7) 2 . ? F4 P1 F3 111.8(7) . . ? F4 P1 F4 179.999(1) . 2 ? F4 P1 F5 89.2(5) . . ? F4 P1 F5 90.8(5) 2 . ? F4 P1 F5 90.8(5) . 2 ? F4 P1 F5 89.2(5) 2 2 ? F5 P1 F2 96.5(4) . . ? F5 P1 F2 83.5(4) 2 . ? F5 P1 F2 83.5(4) . 2 ? F5 P1 F2 96.5(4) 2 2 ? F5 P1 F3 155.0(7) . 2 ? F5 P1 F3 155.0(7) 2 . ? F5 P1 F3 25.0(7) 2 2 ? F5 P1 F3 25.0(7) . . ? F5 P1 F5 179.998(1) . 2 ? O2 Na1 O2 180.0 . 2_666 ? O3 Na1 O2 90.27(3) 2_666 2_666 ? O3 Na1 O2 89.73(3) . 2_666 ? O3 Na1 O2 89.73(3) 2_666 . ? O3 Na1 O2 90.27(3) . . ? O3 Na1 O3 180.00(5) 2_666 . ? O3 Na1 O1 86.90(4) . . ? O3 Na1 O1 93.10(4) 2_666 . ? O3 Na1 O1 86.90(4) 2_666 2_666 ? O3 Na1 O1 93.10(4) . 2_666 ? O1 Na1 O2 96.58(3) 2_666 . ? O1 Na1 O2 83.42(3) . . ? O1 Na1 O2 83.42(3) 2_666 2_666 ? O1 Na1 O2 96.58(3) . 2_666 ? O1 Na1 O1 180.0 2_666 . ? C6 O2 Na1 122.93(8) . . ? C7 O2 Na1 123.39(8) . . ? C7 O2 C6 111.35(10) . . ? C12 O3 Na1 122.57(9) . . ? C1 O1 Na1 128.10(9) . . ? C5 N1 C4 122.07(11) . . ? C1 N1 C5 123.79(11) . . ? C1 N1 C4 114.13(11) . . ? C12 N6 C8 123.83(12) . . ? C12 N6 C9 113.70(12) . . ? C8 N6 C9 122.11(12) . . ? N1 C5 C6 111.51(11) . . ? O3 C12 N6 125.81(13) . . ? O3 C12 C11 125.49(13) . . ? N6 C12 C11 108.66(12) . . ? O1 C1 N1 125.40(12) . . ? O1 C1 C2 126.16(12) . . ? N1 C1 C2 108.42(11) . . ? N6 C8 C7 113.04(11) . . ? N1 C4 C3 103.06(11) . . ? O2 C6 C5 108.34(11) . . ? O2 C7 C8 108.29(11) . . ? C1 C2 C3 103.94(12) . . ? C12 C11 C10 104.75(13) . . ? C2 C3 C4 104.45(11) . . ? N6 C9 C10 104.42(13) . . ? C9 C10 C11 105.84(12) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 10 1 3 0.2256 10.0000 1.0000 3.0000 -0.3861 -0.0780 0.9434 -10 -1 -3 0.2256 -10.0000 -1.0000 -3.0000 0.3861 0.0780 -0.9434 -1 -12 -6 0.1445 -1.0000 -12.0000 -6.0000 0.8783 0.1683 0.4827 1 12 6 0.1445 1.0000 12.0000 6.0000 -0.8783 -0.1683 -0.4827 -1 2 -17 0.0598 -1.0000 2.0000 -17.0000 -0.1814 0.9862 -0.1193 1 -2 17 0.0598 1.0000 -2.0000 17.0000 0.1814 -0.9862 0.1193 _database_code_depnum_ccdc_archive 'CCDC 965877' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_bishep_dm001_01 _audit_creation_date 2012-06-26 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H22 F9 N2 Na1.5 O4 P1.5' _chemical_formula_sum 'C12 H22 F9 N2 Na1.50 O4 P1.50' _chemical_formula_weight 510.26 _chemical_melting_point ? _chemical_oxdiff_formula 'C12 H22 N2 O4 Na1.5 P1.5 F9.5' 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' Na Na 0.0362 0.0249 '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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.848(2) _cell_length_b 17.969(3) _cell_length_c 16.913(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.686(18) _cell_angle_gamma 90.00 _cell_volume 4009.8(11) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2314 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.2233 _cell_measurement_theta_min 2.5229 _exptl_absorpt_coefficient_mu 0.314 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_correction_T_min 0.945 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 2080 _exptl_crystal_size_max 0.2738 _exptl_crystal_size_mid 0.1334 _exptl_crystal_size_min 0.0759 _exptl_special_details ; The poor residuals arise from twinning of the overlap of numerous plate-shaped crystals. While the precision is poor the gross structural details are unequivocal ; _diffrn_reflns_av_R_equivalents 0.1991 _diffrn_reflns_av_unetI/netI 0.1674 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 32122 _diffrn_reflns_theta_full 29.29 _diffrn_reflns_theta_max 29.29 _diffrn_reflns_theta_min 2.53 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.910 _diffrn_measured_fraction_theta_max 0.910 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -1.00 48.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 57.0000 150.0000 49 #__ type_ start__ end____ width___ exp.time_ 2 omega -90.00 -44.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -179.0000 -180.0000 46 #__ type_ start__ end____ width___ exp.time_ 3 omega -30.00 43.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 57.0000 120.0000 73 #__ type_ start__ end____ width___ exp.time_ 4 omega -32.00 41.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 38.0000 -90.0000 73 #__ type_ start__ end____ width___ exp.time_ 5 omega -94.00 -34.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -179.0000 -120.0000 60 #__ type_ start__ end____ width___ exp.time_ 6 omega -88.00 12.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -77.0000 0.0000 100 #__ type_ start__ end____ width___ exp.time_ 7 omega -87.00 3.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -57.0000 -150.0000 90 #__ type_ start__ end____ width___ exp.time_ 8 omega -87.00 3.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -57.0000 120.0000 90 #__ type_ start__ end____ width___ exp.time_ 9 omega -3.00 61.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -100.0000 -120.0000 64 #__ type_ start__ end____ width___ exp.time_ 10 omega -3.00 61.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -100.0000 30.0000 64 #__ type_ start__ end____ width___ exp.time_ 11 omega -3.00 22.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -100.0000 90.0000 25 #__ type_ start__ end____ width___ exp.time_ 12 omega -3.00 87.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 57.0000 120.0000 90 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0394306000 _diffrn_orient_matrix_UB_12 0.0191295000 _diffrn_orient_matrix_UB_13 -0.0302432000 _diffrn_orient_matrix_UB_21 -0.0365456000 _diffrn_orient_matrix_UB_22 -0.0214588000 _diffrn_orient_matrix_UB_23 0.0113862000 _diffrn_orient_matrix_UB_31 -0.0017399000 _diffrn_orient_matrix_UB_32 0.0270113000 _diffrn_orient_matrix_UB_33 0.0299401000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2014 _reflns_number_total 5004 _reflns_odcompleteness_completeness 99.88 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 1.038 _refine_diff_density_min -0.705 _refine_diff_density_rms 0.129 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.310 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 274 _refine_ls_number_reflns 5004 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3039 _refine_ls_R_factor_gt 0.1745 _refine_ls_restrained_S_all 1.310 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.4286 _refine_ls_wR_factor_ref 0.4949 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.0000 0.8930(2) 0.2500 0.0551(10) Uani 1 2 d S . . Na2 Na 0.0000 0.5464(2) 0.2500 0.0487(13) Uani 1 2 d S . . P3 P 0.0167(2) 0.74217(18) -0.03107(19) 0.0698(10) Uani 1 1 d . . . Na4 Na -0.0605(3) 0.6988(3) 0.1423(3) 0.0779(14) Uani 1 1 d . . . O5 O 0.1242(5) 0.4622(3) 0.2256(5) 0.0619(19) Uani 1 1 d . . . O6 O 0.0895(4) 0.6482(3) 0.2177(4) 0.0488(15) Uani 1 1 d . . . O7 O 0.1125(5) 0.5650(4) 0.3829(5) 0.073(2) Uani 1 1 d . . . N8 N 0.1975(5) 0.5926(4) 0.1576(5) 0.0489(19) Uani 1 1 d . . . N9 N 0.2244(6) 0.4766(6) 0.4037(5) 0.070(3) Uani 1 1 d . . . C10 C 0.1471(8) 0.4592(5) 0.1502(8) 0.072(3) Uani 1 1 d . . . H10A H 0.1052 0.4205 0.1139 0.086 Uiso 1 1 calc R . . H10B H 0.2193 0.4460 0.1608 0.086 Uiso 1 1 calc R . . F11 F -0.0001(10) 0.8255(4) -0.0607(7) 0.199(6) Uani 1 1 d . . . C12 C 0.2954(7) 0.6056(5) 0.1434(6) 0.059(3) Uani 1 1 d . . . H12A H 0.2867 0.6274 0.0879 0.071 Uiso 1 1 calc R . . H12B H 0.3354 0.5592 0.1492 0.071 Uiso 1 1 calc R . . C13 C 0.1968(8) 0.5453(6) 0.4084(7) 0.068(3) Uani 1 1 d . . . F14 F 0.0365(9) 0.6587(5) -0.0073(6) 0.162(5) Uani 1 1 d . . . C15 C 0.1255(7) 0.5355(6) 0.1072(7) 0.062(3) Uani 1 1 d . . . H15A H 0.1333 0.5322 0.0511 0.075 Uiso 1 1 calc R . . H15B H 0.0548 0.5506 0.1013 0.075 Uiso 1 1 calc R . . C16 C 0.1699(6) 0.6448(4) 0.2009(6) 0.046(2) Uani 1 1 d . . . O17 O -0.1990(6) 0.7741(6) 0.0992(6) 0.110(3) Uani 1 1 d . . . H17A H -0.2676 0.7595 0.0929 0.164 Uiso 1 1 d R . . H17B H -0.1996 0.8261 0.0849 0.164 Uiso 1 1 d R . . C18 C 0.3444(7) 0.6609(6) 0.2126(6) 0.065(3) Uani 1 1 d . . . H18A H 0.3848 0.6348 0.2634 0.078 Uiso 1 1 calc R . . H18B H 0.3889 0.6961 0.1950 0.078 Uiso 1 1 calc R . . F19 F 0.0019(9) 0.7175(4) -0.1213(5) 0.136(4) Uani 1 1 d . . . C20 C 0.1558(9) 0.3954(6) 0.2769(9) 0.091(4) Uani 1 1 d . . . H20A H 0.2238 0.3794 0.2759 0.110 Uiso 1 1 calc R . . H20B H 0.1075 0.3543 0.2548 0.110 Uiso 1 1 calc R . . C21 C 0.3407(9) 0.4614(8) 0.4360(10) 0.096(4) Uani 1 1 d . . . H21A H 0.3580 0.4229 0.4799 0.116 Uiso 1 1 calc R . . H21B H 0.3681 0.4468 0.3906 0.116 Uiso 1 1 calc R . . F22 F 0.0000 0.8086(7) 0.2500 0.213(10) Uani 1 2 d S . . F23 F 0.1272(7) 0.7570(6) -0.0171(9) 0.168(5) Uani 1 1 d . . . F24 F -0.0969(7) 0.7292(10) -0.0512(10) 0.252(10) Uani 1 1 d . . . F25 F 0.0276(9) 0.7643(7) 0.0599(6) 0.184(6) Uani 1 1 d . . . C26 C 0.2565(6) 0.7004(5) 0.2270(7) 0.056(2) Uani 1 1 d . . . H26A H 0.2401 0.7462 0.1930 0.067 Uiso 1 1 calc R . . H26B H 0.2711 0.7139 0.2862 0.067 Uiso 1 1 calc R . . C27 C 0.2905(8) 0.5909(7) 0.4494(11) 0.103(5) Uani 1 1 d . . . H27A H 0.3007 0.6300 0.4115 0.124 Uiso 1 1 calc R . . H27B H 0.2856 0.6146 0.5009 0.124 Uiso 1 1 calc R . . F28 F -0.0711(10) 0.9009(7) 0.1611(6) 0.190(6) Uani 1 1 d . . . C29 C 0.1582(9) 0.4138(6) 0.3664(9) 0.089(4) Uani 1 1 d . . . H29A H 0.0884 0.4254 0.3666 0.107 Uiso 1 1 calc R . . H29B H 0.1810 0.3692 0.4013 0.107 Uiso 1 1 calc R . . F30 F 0.0000 0.9771(8) 0.2500 0.313(18) Uani 1 2 d S . . C32 C 0.3752(12) 0.5346(9) 0.4684(11) 0.120(5) Uani 1 1 d . . . H32A H 0.4280 0.5518 0.4441 0.144 Uiso 1 1 calc R . . H32B H 0.4063 0.5312 0.5292 0.144 Uiso 1 1 calc R . . F34 F -0.0844(12) 0.8847(13) 0.2805(12) 0.307(10) Uani 1 1 d . . . 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 0.054(2) 0.069(2) 0.047(2) 0.000 0.0220(17) 0.000 Na2 0.049(3) 0.038(2) 0.061(3) 0.000 0.020(2) 0.000 P3 0.073(2) 0.083(2) 0.0613(18) -0.0052(15) 0.0332(16) 0.0130(15) Na4 0.058(2) 0.106(3) 0.073(3) 0.015(2) 0.025(2) 0.020(2) O5 0.057(4) 0.032(3) 0.113(6) -0.005(3) 0.050(4) 0.001(3) O6 0.039(3) 0.044(3) 0.071(4) -0.007(3) 0.028(3) -0.009(2) O7 0.052(4) 0.089(5) 0.075(5) 0.002(4) 0.016(4) -0.006(4) N8 0.040(4) 0.051(4) 0.063(5) 0.009(4) 0.026(4) 0.003(3) N9 0.036(4) 0.113(8) 0.066(6) 0.034(5) 0.023(4) -0.010(5) C10 0.070(7) 0.034(5) 0.126(10) -0.023(6) 0.052(7) -0.003(4) F11 0.292(14) 0.054(5) 0.180(11) -0.031(5) -0.035(10) 0.061(6) C12 0.054(5) 0.065(6) 0.071(7) 0.015(5) 0.037(5) 0.004(4) C13 0.067(7) 0.063(7) 0.093(8) 0.035(6) 0.054(7) 0.024(6) F14 0.263(12) 0.088(6) 0.100(6) 0.027(5) 0.004(7) -0.044(7) C15 0.051(5) 0.076(7) 0.074(7) -0.011(5) 0.041(5) -0.010(5) C16 0.051(5) 0.038(5) 0.054(5) 0.001(4) 0.021(4) -0.006(4) O17 0.084(6) 0.136(8) 0.114(8) 0.024(7) 0.037(6) 0.020(5) C18 0.043(5) 0.096(8) 0.062(6) 0.007(6) 0.025(5) -0.020(5) F19 0.276(11) 0.065(4) 0.086(5) -0.014(4) 0.085(7) -0.003(5) C20 0.083(8) 0.039(6) 0.167(14) 0.029(7) 0.061(9) 0.033(5) C21 0.079(9) 0.095(10) 0.127(12) -0.003(8) 0.050(8) 0.004(7) F22 0.197(16) 0.066(8) 0.29(2) 0.000 -0.049(16) 0.000 F23 0.121(7) 0.149(8) 0.269(14) -0.012(9) 0.109(9) -0.038(6) F24 0.083(6) 0.38(2) 0.300(18) -0.239(17) 0.067(9) -0.026(9) F25 0.230(11) 0.254(12) 0.107(7) -0.105(8) 0.111(8) -0.145(10) C26 0.045(5) 0.057(6) 0.072(7) -0.003(5) 0.028(5) -0.009(4) C27 0.058(7) 0.104(10) 0.136(13) 0.021(9) 0.012(8) 0.007(7) F28 0.217(12) 0.210(13) 0.078(6) 0.002(7) -0.050(7) 0.006(9) C29 0.092(8) 0.070(7) 0.132(11) 0.059(8) 0.075(9) 0.035(7) F30 0.25(2) 0.072(9) 0.45(4) 0.000 -0.16(2) 0.000 C32 0.106(11) 0.103(11) 0.132(14) -0.012(10) 0.007(10) 0.042(9) F34 0.214(14) 0.49(3) 0.31(2) -0.04(2) 0.227(17) -0.052(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 F22 1.517(13) . ? P1 F28 1.533(8) . ? P1 F28 1.533(8) 2 ? P1 F30 1.510(15) . ? P1 F34 1.422(9) 2 ? P1 F34 1.422(9) . ? Na2 Na4 3.255(6) . ? Na2 Na4 3.255(6) 2 ? Na2 O5 2.417(6) 2 ? Na2 O5 2.417(6) . ? Na2 O6 2.365(6) 2 ? Na2 O6 2.365(6) . ? Na2 O7 2.337(7) 2 ? Na2 O7 2.337(7) . ? P3 F11 1.573(9) . ? P3 F14 1.556(9) . ? P3 F19 1.541(8) . ? P3 F23 1.500(9) . ? P3 F24 1.523(9) . ? P3 F25 1.551(8) . ? Na4 Na4 3.517(9) 2 ? Na4 O6 2.678(7) 2 ? Na4 O6 2.271(7) . ? Na4 O7 2.508(9) 2 ? Na4 O17 2.279(9) . ? Na4 F22 2.644(11) . ? Na4 F25 2.419(10) . ? O5 C10 1.406(13) . ? O5 C20 1.468(12) . ? O6 Na4 2.678(7) 2 ? O6 C16 1.232(9) . ? O7 Na4 2.508(9) 2 ? O7 C13 1.170(11) . ? N8 C12 1.465(10) . ? N8 C15 1.502(12) . ? N8 C16 1.316(11) . ? N9 C13 1.303(13) . ? N9 C21 1.559(14) . ? N9 C29 1.470(16) . ? C10 C15 1.539(14) . ? C12 C18 1.528(14) . ? C13 C27 1.513(16) . ? C16 C26 1.520(12) . ? C18 C26 1.492(13) . ? C20 C29 1.540(18) . ? C21 C32 1.448(19) . ? F22 Na4 2.644(11) 2 ? C27 C32 1.508(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F22 P1 F28 95.3(5) . . ? F22 P1 F28 95.3(5) . 2 ? F28 P1 F28 169.4(10) . 2 ? F30 P1 F22 180.000(4) . . ? F30 P1 F28 84.7(5) . . ? F30 P1 F28 84.7(5) . 2 ? F34 P1 F22 83.9(9) 2 . ? F34 P1 F22 83.9(9) . . ? F34 P1 F28 90.6(9) 2 2 ? F34 P1 F28 90.5(9) . 2 ? F34 P1 F28 90.5(9) 2 . ? F34 P1 F28 90.6(9) . . ? F34 P1 F30 96.1(9) 2 . ? F34 P1 F30 96.1(9) . . ? F34 P1 F34 167.8(19) 2 . ? Na4 Na2 Na4 65.40(19) . 2 ? O5 Na2 Na4 120.40(18) . . ? O5 Na2 Na4 123.11(18) 2 . ? O5 Na2 Na4 123.11(18) . 2 ? O5 Na2 Na4 120.40(18) 2 2 ? O5 Na2 O5 102.6(3) 2 . ? O6 Na2 Na4 44.24(17) . . ? O6 Na2 Na4 44.24(17) 2 2 ? O6 Na2 Na4 54.15(18) . 2 ? O6 Na2 Na4 54.16(18) 2 . ? O6 Na2 O5 166.7(2) 2 . ? O6 Na2 O5 89.68(18) . . ? O6 Na2 O5 89.67(18) 2 2 ? O6 Na2 O5 166.7(2) . 2 ? O6 Na2 O6 78.6(3) 2 . ? O7 Na2 Na4 50.1(2) . 2 ? O7 Na2 Na4 113.6(2) 2 2 ? O7 Na2 Na4 50.1(2) 2 . ? O7 Na2 Na4 113.6(2) . . ? O7 Na2 O5 103.1(3) . 2 ? O7 Na2 O5 87.3(3) 2 2 ? O7 Na2 O5 87.3(3) . . ? O7 Na2 O5 103.1(3) 2 . ? O7 Na2 O6 84.8(3) . 2 ? O7 Na2 O6 82.4(2) 2 2 ? O7 Na2 O6 82.4(2) . . ? O7 Na2 O6 84.8(3) 2 . ? O7 Na2 O7 163.5(4) 2 . ? F14 P3 F11 175.7(7) . . ? F19 P3 F11 89.8(5) . . ? F19 P3 F14 86.5(5) . . ? F19 P3 F25 177.3(5) . . ? F23 P3 F11 85.7(7) . . ? F23 P3 F14 92.3(7) . . ? F23 P3 F19 91.7(7) . . ? F23 P3 F24 176.1(9) . . ? F23 P3 F25 90.6(7) . . ? F24 P3 F11 91.8(9) . . ? F24 P3 F14 90.0(9) . . ? F24 P3 F19 85.2(7) . . ? F24 P3 F25 92.6(6) . . ? F25 P3 F11 91.8(7) . . ? F25 P3 F14 92.0(6) . . ? Na2 Na4 Na4 57.30(9) . 2 ? O6 Na4 Na2 46.58(15) . . ? O6 Na4 Na2 45.70(13) 2 . ? O6 Na4 Na4 40.22(15) 2 2 ? O6 Na4 Na4 49.59(19) . 2 ? O6 Na4 O6 74.0(2) . 2 ? O6 Na4 O7 83.0(2) . 2 ? O6 Na4 O17 162.7(4) . . ? O6 Na4 F22 82.4(2) . . ? O6 Na4 F25 89.1(4) . . ? O7 Na4 Na2 45.60(19) 2 . ? O7 Na4 Na4 101.4(2) 2 2 ? O7 Na4 O6 73.3(3) 2 2 ? O7 Na4 F22 147.9(3) 2 . ? O17 Na4 Na2 136.6(3) . . ? O17 Na4 Na4 114.9(3) . 2 ? O17 Na4 O6 98.4(3) . 2 ? O17 Na4 O7 110.2(3) . 2 ? O17 Na4 F22 80.6(3) . . ? O17 Na4 F25 92.8(5) . . ? F22 Na4 Na2 105.6(2) . . ? F22 Na4 Na4 48.3(2) . 2 ? F22 Na4 O6 75.3(2) . 2 ? F25 Na4 Na2 130.0(4) . . ? F25 Na4 Na4 115.6(3) . 2 ? F25 Na4 O6 155.8(3) . 2 ? F25 Na4 O7 122.5(3) . 2 ? F25 Na4 F22 85.6(3) . . ? C10 O5 Na2 123.2(6) . . ? C10 O5 C20 113.2(8) . . ? C20 O5 Na2 120.7(6) . . ? Na2 O6 Na4 80.1(2) . 2 ? Na4 O6 Na2 89.2(2) . . ? Na4 O6 Na4 90.2(2) . 2 ? C16 O6 Na2 126.1(5) . . ? C16 O6 Na4 128.7(6) . . ? C16 O6 Na4 127.6(6) . 2 ? Na2 O7 Na4 84.3(3) . 2 ? C13 O7 Na2 127.6(8) . . ? C13 O7 Na4 123.7(7) . 2 ? C12 N8 C15 120.3(7) . . ? C16 N8 C12 114.7(7) . . ? C16 N8 C15 123.1(7) . . ? C13 N9 C21 115.8(10) . . ? C13 N9 C29 126.6(9) . . ? C29 N9 C21 117.4(10) . . ? O5 C10 C15 109.1(7) . . ? N8 C12 C18 101.3(7) . . ? O7 C13 N9 122.9(11) . . ? O7 C13 C27 128.8(10) . . ? N9 C13 C27 108.3(9) . . ? N8 C15 C10 109.9(9) . . ? O6 C16 N8 126.8(7) . . ? O6 C16 C26 126.1(8) . . ? N8 C16 C26 107.0(7) . . ? C26 C18 C12 103.8(7) . . ? O5 C20 C29 108.5(8) . . ? C32 C21 N9 99.2(10) . . ? P1 F22 Na4 138.3(2) . 2 ? P1 F22 Na4 138.3(2) . . ? Na4 F22 Na4 83.4(4) . 2 ? P3 F25 Na4 122.1(5) . . ? C18 C26 C16 104.5(8) . . ? C32 C27 C13 103.7(11) . . ? N9 C29 C20 114.3(9) . . ? C21 C32 C27 112.5(13) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 -2 2 0.0672 -0.0147 -2.0130 2.0031 -0.0985 0.0665 0.0056 1 18 -16 0.0672 1.1231 18.0979 -16.0170 0.7863 -0.6118 0.0073 0 -3 1 0.0645 -0.0139 -3.0095 0.9994 -0.0872 0.0765 -0.0513 -1 24 -6 0.0645 -0.8955 24.0751 -5.9951 0.6772 -0.5522 0.4724 -2 0 0 0.0345 -1.9979 0.0180 -0.0113 0.0795 0.0725 0.0036 19 3 -3 0.0345 19.0017 2.8482 -2.8973 -0.6071 -0.7885 -0.0429 -1 3 3 0.1197 -1.0012 2.9986 3.0056 0.0059 0.0065 0.1727 5 -17 -18 0.1197 5.0117 -16.9808 -18.0383 0.0231 -0.0242 -1.0075 -3 -2 0 0.0353 -3.0034 -1.9760 -0.0192 0.0812 0.1519 -0.0487 16 10 4 0.0353 15.9995 9.8508 4.1121 -0.5668 -0.7493 0.3614 2 -3 0 0.0421 1.9880 -3.0225 0.0080 -0.1364 -0.0077 -0.0849 -11 16 -7 0.0421 -10.9071 16.1582 -7.0631 0.9528 -0.0286 0.2440 _database_code_depnum_ccdc_archive 'CCDC 965878' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12srv067 _audit_creation_date 2012-12-30 _audit_creation_method ; Olex2 1.2 (compiled Nov 5 2012 18:25:38, GUI svn.r4372) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '3(F6 P), C48 H80 N8 Na3 O12, 0.28(H2O)' _chemical_formula_sum 'C48 H80.56 F18 N8 Na3 O12.28 P3' _chemical_formula_weight 1470.16 _chemical_melting_point ? _chemical_oxdiff_formula 'C12 H20 N2 O3 Na P F6' 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' Na Na 0.0362 0.0249 '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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 13.2010(4) _cell_length_b 13.6768(4) _cell_length_c 18.1009(5) _cell_angle_alpha 85.700(2) _cell_angle_beta 84.890(2) _cell_angle_gamma 88.882(2) _cell_volume 3245.65(16) _cell_formula_units_Z 2 _cell_measurement_reflns_used 12895 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 29.2198 _cell_measurement_theta_min 2.6150 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.983 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1525 _exptl_crystal_size_max 0.7422 _exptl_crystal_size_mid 0.4462 _exptl_crystal_size_min 0.1434 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0868 _diffrn_reflns_av_unetI/netI 0.0638 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 76405 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.62 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -79.00 11.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -77.0000 -60.0000 90 #__ type_ start__ end____ width___ exp.time_ 2 omega -88.00 11.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -77.0000 90.0000 99 #__ type_ start__ end____ width___ exp.time_ 3 omega -73.00 -46.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -179.0000 -30.0000 27 #__ type_ start__ end____ width___ exp.time_ 4 omega 38.00 87.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 57.0000 120.0000 49 #__ type_ start__ end____ width___ exp.time_ 5 omega 36.00 67.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -125.0000 42.0000 31 #__ type_ start__ end____ width___ exp.time_ 6 omega 18.00 70.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -125.0000 -120.0000 52 #__ type_ start__ end____ width___ exp.time_ 7 omega -49.00 39.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -57.0000 -150.0000 88 #__ type_ start__ end____ width___ exp.time_ 8 omega -50.00 38.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -57.0000 -30.0000 88 #__ type_ start__ end____ width___ exp.time_ 9 omega -87.00 3.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -57.0000 120.0000 90 #__ type_ start__ end____ width___ exp.time_ 10 omega -94.00 -34.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -179.0000 -180.0000 60 #__ type_ start__ end____ width___ exp.time_ 11 omega -94.00 -34.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -179.0000 30.0000 60 #__ type_ start__ end____ width___ exp.time_ 12 omega -90.00 8.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -38.0000 -180.0000 98 #__ type_ start__ end____ width___ exp.time_ 13 omega -3.00 61.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -100.0000 60.0000 64 #__ type_ start__ end____ width___ exp.time_ 14 omega -7.00 91.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 38.0000 60.0000 98 #__ type_ start__ end____ width___ exp.time_ 15 omega -39.00 51.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 57.0000 150.0000 90 #__ type_ start__ end____ width___ exp.time_ 16 omega -39.00 -14.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 57.0000 -90.0000 25 #__ type_ start__ end____ width___ exp.time_ 17 omega 18.00 76.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -125.0000 -137.0000 58 #__ type_ start__ end____ width___ exp.time_ 18 omega -3.00 61.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -100.0000 -30.0000 64 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0199504000 _diffrn_orient_matrix_UB_12 -0.0482653000 _diffrn_orient_matrix_UB_13 0.0055205000 _diffrn_orient_matrix_UB_21 0.0114799000 _diffrn_orient_matrix_UB_22 -0.0014418000 _diffrn_orient_matrix_UB_23 -0.0389400000 _diffrn_orient_matrix_UB_31 0.0487932000 _diffrn_orient_matrix_UB_32 0.0193303000 _diffrn_orient_matrix_UB_33 0.0030718000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 10349 _reflns_number_total 14788 _reflns_odcompleteness_completeness 99.89 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.526 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.066 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 894 _refine_ls_number_reflns 14788 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0563 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+2.0947P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1197 _refine_ls_wR_factor_ref 0.1370 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H6A,H6B} of C6, {H41,H3} of C41, {H22A,H22B} of C22, {H16A,H16B} of C16, {H23A,H23B} of C23, {H20A,H20B} of C20, {H29A,H29B} of C29, {H30A,H30B} of C30, {H15A,H15B} of C15, {H18A,H18B} of C18, {H44A,H44B} of C44, {H7A,H7B} of C7, {H27A,H27B} of C27, {H40A,H40B} of C40, {H47A,H47B} of C47, {H14A,H14B} of C14, {H2A,H2B} of C2, {H48A,H48B} of C48, {H4A,H4B} of C4, {H39A,H39B} of C39, {H43A,H43B} of C43, {H35A,H35B} of C35, {H38A,H38B} of C38, {H42A,H42B} of C42, {H46A,H46B} of C46, {H8A,H8B} of C8, {H34A,H34B} of C34, {H17A,H17B} of C17, {H28A,H28B} of C28, {H24A,H24B} of C24, {H31A,H31B} of C31, {H19A, H19B} of C19, {H36A,H36B} of C36, {H32,H2} of C32, {H5A,H5B} of C5, {H26A, H26B} of C26, {H11A,H11B} of C11, {H3A,H3B} of C3, {H12A,H12B} of C12, {H10A, H10B} of C10 2. Others Sof(F7A)=Sof(F9A)=Sof(F8A)=Sof(F10)=Sof(F11A)=Sof(F12A)=1-Sof(F9A)=1-Sof(F9A)= 1-Sof(F9A)=1-Sof(F9A)=1-Sof(F9A)=1-Sof(F9A) 3.a Secondary CH2 refined with riding coordinates: C6(H6A,H6B), C41(H41,H3), C22(H22A,H22B), C16(H16A,H16B), C23(H23A,H23B), C20(H20A,H20B), C29(H29A,H29B), C30(H30A,H30B), C15(H15A,H15B), C26(H26A,H26B), C5(H5A,H5B), C32(H32,H2), C36(H36A,H36B), C19(H19A,H19B), C31(H31A,H31B), C24(H24A,H24B), C28(H28A,H28B), C17(H17A,H17B), C34(H34A,H34B), C8(H8A,H8B), C46(H46A,H46B), C42(H42A,H42B), C38(H38A,H38B), C35(H35A,H35B), C18(H18A,H18B), C44(H44A,H44B), C7(H7A,H7B), C27(H27A,H27B), C40(H40A,H40B), C47(H47A,H47B), C14(H14A,H14B), C2(H2A,H2B), C48(H48A,H48B), C4(H4A,H4B), C39(H39A,H39B), C43(H43A,H43B), C10(H10A,H10B), C12(H12A,H12B), C3(H3A,H3B), C11(H11A,H11B) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.75194(5) 0.36956(5) 0.22373(4) 0.02468(15) Uani 1 1 d . . . F2 F 0.79886(12) 0.47264(10) 0.23769(9) 0.0338(4) Uani 1 1 d . . . F3 F 0.70438(13) 0.26703(11) 0.20913(11) 0.0478(5) Uani 1 1 d . . . F5 F 0.68514(13) 0.42251(12) 0.16236(9) 0.0403(4) Uani 1 1 d . . . F4 F 0.66123(12) 0.38711(12) 0.28617(9) 0.0417(4) Uani 1 1 d . . . F6 F 0.81712(14) 0.31686(12) 0.28621(10) 0.0462(4) Uani 1 1 d . . . F1 F 0.84259(13) 0.35229(14) 0.16201(10) 0.0517(5) Uani 1 1 d . . . P2 P 0.80275(6) 0.75427(6) -0.00383(4) 0.03609(18) Uani 1 1 d . . . Na1 Na 0.71961(7) 0.13326(6) -0.24393(5) 0.0212(2) Uani 1 1 d . . . Na2 Na 0.71300(7) 0.35430(6) -0.18440(5) 0.0203(2) Uani 1 1 d . . . Na3 Na 0.74035(7) 0.32584(7) -0.35942(5) 0.0229(2) Uani 1 1 d . . . O5 O 0.83770(12) 0.40159(12) -0.10223(9) 0.0235(4) Uani 1 1 d . . . O6 O 0.83834(12) 0.28914(12) -0.26022(9) 0.0218(4) Uani 1 1 d . . . O9 O 0.69808(13) 0.48100(12) -0.28436(9) 0.0270(4) Uani 1 1 d . . . O4 O 0.71725(13) 0.19807(12) -0.11992(9) 0.0242(4) Uani 1 1 d . . . O7 O 0.61173(12) 0.27786(11) -0.26432(9) 0.0207(3) Uani 1 1 d . . . O8 O 0.56619(12) 0.42781(12) -0.12740(9) 0.0230(4) Uani 1 1 d . . . O1 O 0.84049(13) 0.01368(12) -0.23244(10) 0.0282(4) Uani 1 1 d . . . O2 O 1.19466(12) -0.03298(12) -0.20345(9) 0.0245(4) Uani 1 1 d . . . N3 N 0.78276(14) 0.22664(14) -0.01073(10) 0.0200(4) Uani 1 1 d . . . N1 N 0.94147(15) -0.12363(14) -0.23051(11) 0.0220(4) Uani 1 1 d . . . N6 N 0.62352(15) 0.60808(14) -0.22227(11) 0.0222(4) Uani 1 1 d . . . O11 O 0.66992(13) 0.35311(12) -0.48339(9) 0.0261(4) Uani 1 1 d . . . O12 O 0.74942(15) 0.15441(13) -0.37327(10) 0.0323(4) Uani 1 1 d . . . N5 N 0.45077(14) 0.30234(14) -0.20919(11) 0.0199(4) Uani 1 1 d . . . N4 N 0.98845(14) 0.34623(14) -0.22746(11) 0.0209(4) Uani 1 1 d . . . N7 N 0.86151(16) 0.45765(15) -0.52734(11) 0.0252(5) Uani 1 1 d . . . C21 C 0.93137(17) 0.28101(16) -0.25594(12) 0.0190(5) Uani 1 1 d . . . O10 O 0.89151(13) 0.35165(13) -0.42819(10) 0.0311(4) Uani 1 1 d . . . C25 C 0.51974(17) 0.29750(16) -0.26740(13) 0.0186(5) Uani 1 1 d . . . C33 C 0.64448(18) 0.55650(17) -0.28214(14) 0.0230(5) Uani 1 1 d . . . C6 C 1.11890(18) -0.07097(17) -0.24413(13) 0.0225(5) Uani 1 1 d . . . H6A H 1.1422 -0.1344 -0.2631 0.027 Uiso 1 1 calc R . . H6B H 1.1060 -0.0248 -0.2871 0.027 Uiso 1 1 calc R . . N2 N 0.42046(15) -0.01052(15) -0.16239(12) 0.0272(5) Uani 1 1 d . . . C41 C 0.76727(19) 0.50024(18) -0.49574(15) 0.0279(6) Uani 1 1 d . . . H41 H 0.7643 0.5707 -0.5126 0.034 Uiso 1 1 calc R . . H3 H 0.7665 0.4951 -0.4408 0.034 Uiso 1 1 calc R . . N8 N 0.72287(17) 0.14907(15) -0.49541(11) 0.0276(5) Uani 1 1 d . . . C22 C 0.99898(17) 0.19911(17) -0.28308(14) 0.0244(5) Uani 1 1 d . . . H22A H 1.0136 0.2067 -0.3378 0.029 Uiso 1 1 calc R . . H22B H 0.9672 0.1346 -0.2691 0.029 Uiso 1 1 calc R . . C16 C 0.85996(19) 0.18793(18) 0.03748(14) 0.0250(5) Uani 1 1 d . . . H16A H 0.8325 0.1828 0.0903 0.030 Uiso 1 1 calc R . . H16B H 0.9206 0.2301 0.0319 0.030 Uiso 1 1 calc R . . C37 C 0.91364(18) 0.38617(17) -0.49205(14) 0.0233(5) Uani 1 1 d . . . C23 C 1.09593(18) 0.20899(18) -0.24399(16) 0.0279(6) Uani 1 1 d . . . H23A H 1.0935 0.1670 -0.1969 0.033 Uiso 1 1 calc R . . H23B H 1.1569 0.1911 -0.2763 0.033 Uiso 1 1 calc R . . C13 C 0.77376(18) 0.17559(17) -0.06993(13) 0.0212(5) Uani 1 1 d . . . C20 C 0.95381(19) 0.44388(17) -0.20818(14) 0.0249(5) Uani 1 1 d . . . H20A H 0.8922 0.4616 -0.2339 0.030 Uiso 1 1 calc R . . H20B H 1.0071 0.4917 -0.2269 0.030 Uiso 1 1 calc R . . C29 C 0.47259(18) 0.28105(17) -0.13226(13) 0.0217(5) Uani 1 1 d . . . H29A H 0.5375 0.2437 -0.1309 0.026 Uiso 1 1 calc R . . H29B H 0.4181 0.2397 -0.1059 0.026 Uiso 1 1 calc R . . C30 C 0.48024(18) 0.37382(18) -0.09260(13) 0.0242(5) Uani 1 1 d . . . H30A H 0.4173 0.4138 -0.0961 0.029 Uiso 1 1 calc R . . H30B H 0.4892 0.3573 -0.0394 0.029 Uiso 1 1 calc R . . C15 C 0.8859(2) 0.08679(19) 0.01021(14) 0.0288(6) Uani 1 1 d . . . H15A H 0.8530 0.0348 0.0446 0.035 Uiso 1 1 calc R . . H15B H 0.9603 0.0751 0.0062 0.035 Uiso 1 1 calc R . . C26 C 0.46697(19) 0.31845(19) -0.33740(14) 0.0269(5) Uani 1 1 d . . . H26A H 0.4566 0.2572 -0.3615 0.032 Uiso 1 1 calc R . . H26B H 0.5069 0.3643 -0.3731 0.032 Uiso 1 1 calc R . . C5 C 1.02230(18) -0.08508(19) -0.19277(13) 0.0240(5) Uani 1 1 d . . . H5A H 1.0363 -0.1308 -0.1497 0.029 Uiso 1 1 calc R . . H5B H 1.0002 -0.0214 -0.1737 0.029 Uiso 1 1 calc R . . C32 C 0.65481(19) 0.57995(18) -0.14851(14) 0.0262(5) Uani 1 1 d . . . H32 H 0.6701 0.6398 -0.1242 0.031 Uiso 1 1 calc R . . H2 H 0.7180 0.5399 -0.1534 0.031 Uiso 1 1 calc R . . O3 O 0.57155(15) 0.04877(16) -0.21648(13) 0.0488(6) Uani 1 1 d . . . C1 C 0.85718(18) -0.07251(18) -0.24503(13) 0.0225(5) Uani 1 1 d . . . C36 C 0.55662(19) 0.69286(18) -0.23477(15) 0.0272(6) Uani 1 1 d . . . H36A H 0.5823 0.7515 -0.2138 0.033 Uiso 1 1 calc R . . H36B H 0.4866 0.6796 -0.2124 0.033 Uiso 1 1 calc R . . C19 C 0.92967(19) 0.45281(18) -0.12602(14) 0.0272(6) Uani 1 1 d . . . H19A H 0.9861 0.4244 -0.0984 0.033 Uiso 1 1 calc R . . H19B H 0.9214 0.5228 -0.1158 0.033 Uiso 1 1 calc R . . C31 C 0.57430(19) 0.52218(18) -0.09978(14) 0.0260(5) Uani 1 1 d . . . H31A H 0.5931 0.5149 -0.0479 0.031 Uiso 1 1 calc R . . H31B H 0.5081 0.5574 -0.1002 0.031 Uiso 1 1 calc R . . C24 C 1.09637(17) 0.31756(18) -0.22924(15) 0.0252(5) Uani 1 1 d . . . H24A H 1.1239 0.3270 -0.1812 0.030 Uiso 1 1 calc R . . H24B H 1.1372 0.3559 -0.2695 0.030 Uiso 1 1 calc R . . C28 C 0.34825(17) 0.32812(18) -0.22933(14) 0.0240(5) Uani 1 1 d . . . H28A H 0.3175 0.3802 -0.1991 0.029 Uiso 1 1 calc R . . H28B H 0.3036 0.2702 -0.2227 0.029 Uiso 1 1 calc R . . C17 C 0.73611(19) 0.32226(17) -0.00082(13) 0.0241(5) Uani 1 1 d . . . H17A H 0.7113 0.3263 0.0521 0.029 Uiso 1 1 calc R . . H17B H 0.6768 0.3303 -0.0306 0.029 Uiso 1 1 calc R . . C34 C 0.5909(2) 0.60595(18) -0.34543(14) 0.0276(6) Uani 1 1 d . . . H34A H 0.5304 0.5685 -0.3546 0.033 Uiso 1 1 calc R . . H34B H 0.6371 0.6122 -0.3917 0.033 Uiso 1 1 calc R . . C45 C 0.7779(2) 0.13300(18) -0.43708(14) 0.0280(6) Uani 1 1 d . . . C9 C 0.5218(2) -0.0010(2) -0.16751(16) 0.0323(6) Uani 1 1 d . . . C8 C 0.3559(2) 0.04772(18) -0.20973(15) 0.0303(6) Uani 1 1 d . . . H8A H 0.3996 0.0882 -0.2469 0.036 Uiso 1 1 calc R . . H8B H 0.3143 0.0930 -0.1789 0.036 Uiso 1 1 calc R . . C46 C 0.8776(2) 0.0862(2) -0.46236(16) 0.0386(7) Uani 1 1 d . . . H46A H 0.8807 0.0168 -0.4425 0.046 Uiso 1 1 calc R . . H46B H 0.9351 0.1216 -0.4456 0.046 Uiso 1 1 calc R . . C42 C 0.6742(2) 0.45008(19) -0.51791(15) 0.0311(6) Uani 1 1 d . . . H42A H 0.6119 0.4873 -0.5020 0.037 Uiso 1 1 calc R . . H42B H 0.6782 0.4479 -0.5726 0.037 Uiso 1 1 calc R . . C38 C 1.0038(2) 0.3577(2) -0.54291(16) 0.0337(6) Uani 1 1 d . . . H38A H 1.0007 0.2876 -0.5526 0.040 Uiso 1 1 calc R . . H38B H 1.0679 0.3689 -0.5205 0.040 Uiso 1 1 calc R . . C35 C 0.5600(2) 0.70668(18) -0.31933(15) 0.0294(6) Uani 1 1 d . . . H35A H 0.6105 0.7566 -0.3393 0.035 Uiso 1 1 calc R . . H35B H 0.4925 0.7271 -0.3353 0.035 Uiso 1 1 calc R . . C18 C 0.8099(2) 0.40442(18) -0.02418(13) 0.0271(6) Uani 1 1 d . . . H18A H 0.7777 0.4684 -0.0136 0.032 Uiso 1 1 calc R . . H18B H 0.8711 0.3957 0.0037 0.032 Uiso 1 1 calc R . . C44 C 0.6194(2) 0.1862(2) -0.48847(15) 0.0325(6) Uani 1 1 d . . . H44A H 0.5943 0.1841 -0.4352 0.039 Uiso 1 1 calc R . . H44B H 0.5756 0.1434 -0.5134 0.039 Uiso 1 1 calc R . . C7 C 1.28546(19) -0.01097(19) -0.25035(14) 0.0275(6) Uani 1 1 d . . . H7A H 1.2682 0.0271 -0.2963 0.033 Uiso 1 1 calc R . . H7B H 1.3199 -0.0726 -0.2645 0.033 Uiso 1 1 calc R . . F7A F 0.8424(4) 0.6780(5) -0.0612(4) 0.0626(15) Uani 0.686(8) 1 d P A 1 C27 C 0.3657(2) 0.3645(2) -0.31100(15) 0.0331(6) Uani 1 1 d . . . H27A H 0.3106 0.3430 -0.3395 0.040 Uiso 1 1 calc R . . H27B H 0.3691 0.4370 -0.3166 0.040 Uiso 1 1 calc R . . C40 C 0.9045(2) 0.4871(2) -0.60283(15) 0.0340(6) Uani 1 1 d . . . H40A H 0.9232 0.5572 -0.6074 0.041 Uiso 1 1 calc R . . H40B H 0.8555 0.4762 -0.6396 0.041 Uiso 1 1 calc R . . F9A F 0.7603(4) 0.8211(5) 0.0594(3) 0.079(2) Uani 0.686(8) 1 d P A 1 C47 C 0.8811(2) 0.0933(2) -0.54680(16) 0.0420(7) Uani 1 1 d . . . H47A H 0.9056 0.0308 -0.5667 0.050 Uiso 1 1 calc R . . H47B H 0.9267 0.1466 -0.5685 0.050 Uiso 1 1 calc R . . C14 C 0.8447(2) 0.0883(2) -0.06617(15) 0.0330(6) Uani 1 1 d . . . H14A H 0.9008 0.0952 -0.1062 0.040 Uiso 1 1 calc R . . H14B H 0.8079 0.0271 -0.0712 0.040 Uiso 1 1 calc R . . C2 C 0.7866(2) -0.1385(2) -0.27906(17) 0.0361(7) Uani 1 1 d . . . H2A H 0.7197 -0.1423 -0.2497 0.043 Uiso 1 1 calc R . . H2B H 0.7764 -0.1140 -0.3308 0.043 Uiso 1 1 calc R . . C48 C 0.7715(2) 0.1154(2) -0.56455(15) 0.0396(7) Uani 1 1 d . . . H48A H 0.7690 0.1669 -0.6058 0.047 Uiso 1 1 calc R . . H48B H 0.7384 0.0557 -0.5782 0.047 Uiso 1 1 calc R . . C4 C 0.9389(2) -0.22592(19) -0.24694(18) 0.0382(7) Uani 1 1 d . . . H4A H 0.9438 -0.2698 -0.2013 0.046 Uiso 1 1 calc R . . H4B H 0.9956 -0.2417 -0.2840 0.046 Uiso 1 1 calc R . . C39 C 0.9978(2) 0.4222(2) -0.61433(16) 0.0412(7) Uani 1 1 d . . . H39A H 1.0596 0.4626 -0.6248 0.049 Uiso 1 1 calc R . . H39B H 0.9919 0.3816 -0.6567 0.049 Uiso 1 1 calc R . . C43 C 0.6109(2) 0.2905(2) -0.52237(15) 0.0314(6) Uani 1 1 d . . . H43A H 0.6362 0.2936 -0.5756 0.038 Uiso 1 1 calc R . . H43B H 0.5388 0.3124 -0.5186 0.038 Uiso 1 1 calc R . . C10 C 0.5630(2) -0.0592(2) -0.10287(17) 0.0428(7) Uani 1 1 d . . . H10A H 0.5840 -0.0153 -0.0660 0.051 Uiso 1 1 calc R . . H10B H 0.6222 -0.0999 -0.1197 0.051 Uiso 1 1 calc R . . F8A F 0.7656(3) 0.6637(3) 0.0563(3) 0.0752(16) Uani 0.686(8) 1 d P A 1 F10 F 0.8418(7) 0.8407(5) -0.0552(4) 0.098(3) Uani 0.686(8) 1 d P A 1 P3 P 0.74127(6) 0.80534(5) 0.47775(4) 0.03824(19) Uani 1 1 d . . . F13 F 0.80281(13) 0.72696(12) 0.42857(9) 0.0423(4) Uani 1 1 d . . . F18 F 0.77204(14) 0.74477(15) 0.55154(10) 0.0533(5) Uani 1 1 d . . . F14 F 0.64331(14) 0.73831(16) 0.48210(11) 0.0607(6) Uani 1 1 d . . . F16 F 0.8419(2) 0.86621(18) 0.47416(19) 0.1166(12) Uani 1 1 d . . . F15 F 0.6828(2) 0.88292(17) 0.52657(14) 0.0913(8) Uani 1 1 d . . . F17 F 0.7062(2) 0.85992(18) 0.40406(13) 0.1009(10) Uani 1 1 d . . . C12 C 0.3801(2) -0.0694(2) -0.09588(16) 0.0376(7) Uani 1 1 d . . . H12A H 0.3287 -0.1160 -0.1080 0.045 Uiso 1 1 calc R . . H12B H 0.3490 -0.0272 -0.0576 0.045 Uiso 1 1 calc R . . C3 C 0.8388(3) -0.2363(2) -0.2775(2) 0.0535(9) Uani 1 1 d . . . H3A H 0.7969 -0.2851 -0.2457 0.064 Uiso 1 1 calc R . . H3B H 0.8489 -0.2590 -0.3283 0.064 Uiso 1 1 calc R . . F11A F 0.6938(3) 0.7528(3) -0.0318(2) 0.0643(14) Uani 0.686(8) 1 d P A 1 C11 C 0.4743(2) -0.1235(2) -0.06961(17) 0.0446(8) Uani 1 1 d . . . H11A H 0.4805 -0.1898 -0.0882 0.054 Uiso 1 1 calc R . . H11B H 0.4717 -0.1296 -0.0146 0.054 Uiso 1 1 calc R . . F12A F 0.9088(3) 0.7458(5) 0.0324(3) 0.096(2) Uani 0.686(8) 1 d P A 1 O1W O 0.5226(8) 0.9651(10) 0.6348(8) 0.115(7) Uani 0.284(10) 1 d P . . F9B F 0.7250(9) 0.8436(7) 0.0227(7) 0.072(4) Uani 0.314(8) 1 d P A 2 F8B F 0.7273(8) 0.6707(7) 0.0090(6) 0.077(4) Uani 0.314(8) 1 d P A 2 F11B F 0.7537(10) 0.7813(6) -0.0874(6) 0.096(5) Uani 0.314(8) 1 d P A 2 F10A F 0.8763(12) 0.8420(14) -0.0336(12) 0.097(7) Uani 0.314(8) 1 d P A 2 F7B F 0.8801(9) 0.6850(9) -0.0454(10) 0.063(4) Uani 0.314(8) 1 d P A 2 F12B F 0.846(2) 0.7400(9) 0.0632(9) 0.192(11) Uani 0.314(8) 1 d P A 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 0.0262(3) 0.0197(3) 0.0293(4) -0.0068(3) -0.0048(3) 0.0006(3) F2 0.0370(9) 0.0232(8) 0.0426(9) -0.0025(7) -0.0089(7) -0.0083(6) F3 0.0498(11) 0.0252(8) 0.0727(13) -0.0179(8) -0.0166(9) -0.0032(7) F5 0.0456(10) 0.0394(9) 0.0384(9) -0.0054(7) -0.0171(8) 0.0034(8) F4 0.0395(9) 0.0445(10) 0.0400(10) -0.0090(8) 0.0090(7) -0.0070(8) F6 0.0562(11) 0.0304(9) 0.0546(11) 0.0024(8) -0.0255(9) 0.0046(8) F1 0.0368(10) 0.0670(12) 0.0528(11) -0.0277(10) 0.0064(8) 0.0046(9) P2 0.0345(4) 0.0345(4) 0.0394(4) -0.0088(3) 0.0029(3) -0.0084(3) Na1 0.0209(5) 0.0201(5) 0.0225(5) -0.0007(4) -0.0025(4) -0.0018(4) Na2 0.0199(5) 0.0215(5) 0.0195(5) -0.0018(4) -0.0026(4) -0.0001(4) Na3 0.0225(5) 0.0254(5) 0.0202(5) 0.0021(4) -0.0018(4) -0.0024(4) O5 0.0253(9) 0.0243(9) 0.0219(9) -0.0035(7) -0.0051(7) -0.0033(7) O6 0.0167(8) 0.0275(9) 0.0215(9) -0.0026(7) -0.0025(7) -0.0001(7) O9 0.0326(10) 0.0226(9) 0.0254(9) -0.0010(7) -0.0012(8) 0.0024(8) O4 0.0288(9) 0.0248(9) 0.0196(9) -0.0010(7) -0.0064(7) 0.0005(7) O7 0.0167(8) 0.0227(8) 0.0229(9) -0.0023(7) -0.0019(7) -0.0002(7) O8 0.0228(9) 0.0225(9) 0.0238(9) -0.0056(7) 0.0016(7) -0.0005(7) O1 0.0266(9) 0.0200(9) 0.0391(11) -0.0045(8) -0.0073(8) 0.0022(7) O2 0.0225(9) 0.0271(9) 0.0244(9) -0.0015(7) -0.0040(7) -0.0055(7) N3 0.0215(10) 0.0212(10) 0.0172(10) 0.0001(8) -0.0035(8) 0.0020(8) N1 0.0233(11) 0.0181(10) 0.0256(11) -0.0045(8) -0.0053(8) 0.0008(8) N6 0.0222(10) 0.0198(10) 0.0249(11) -0.0025(8) -0.0038(8) -0.0021(8) O11 0.0289(9) 0.0266(9) 0.0231(9) 0.0012(7) -0.0053(7) -0.0029(7) O12 0.0465(12) 0.0277(10) 0.0227(10) -0.0041(8) -0.0012(8) -0.0016(8) N5 0.0158(10) 0.0200(10) 0.0242(11) -0.0019(8) -0.0032(8) -0.0007(8) N4 0.0155(10) 0.0187(10) 0.0288(11) -0.0023(8) -0.0026(8) -0.0008(8) N7 0.0305(12) 0.0226(11) 0.0215(11) 0.0011(8) 0.0014(9) -0.0017(9) C21 0.0197(12) 0.0201(11) 0.0162(11) 0.0043(9) -0.0010(9) -0.0022(9) O10 0.0247(9) 0.0343(10) 0.0320(10) 0.0095(8) 0.0005(8) -0.0024(8) C25 0.0194(12) 0.0132(11) 0.0236(12) -0.0027(9) -0.0022(9) -0.0025(9) C33 0.0231(12) 0.0188(12) 0.0268(13) 0.0004(10) -0.0004(10) -0.0067(10) C6 0.0239(12) 0.0215(12) 0.0230(13) -0.0039(10) -0.0052(10) -0.0008(10) N2 0.0238(11) 0.0287(11) 0.0293(12) 0.0010(9) -0.0038(9) -0.0068(9) C41 0.0334(14) 0.0211(12) 0.0286(14) 0.0010(10) -0.0018(11) 0.0015(11) N8 0.0392(13) 0.0226(11) 0.0212(11) -0.0054(9) 0.0006(9) -0.0039(9) C22 0.0196(12) 0.0208(12) 0.0326(14) -0.0032(10) -0.0004(10) 0.0000(10) C16 0.0265(13) 0.0264(13) 0.0229(13) 0.0000(10) -0.0082(10) 0.0037(10) C37 0.0254(13) 0.0173(11) 0.0273(14) -0.0011(10) -0.0031(10) -0.0047(10) C23 0.0201(12) 0.0213(12) 0.0421(16) 0.0002(11) -0.0041(11) 0.0018(10) C13 0.0236(12) 0.0219(12) 0.0172(12) 0.0009(9) 0.0008(10) -0.0020(10) C20 0.0219(12) 0.0168(11) 0.0352(15) -0.0007(10) -0.0002(10) -0.0007(9) C29 0.0182(12) 0.0240(12) 0.0217(12) 0.0028(10) 0.0010(9) -0.0001(9) C30 0.0200(12) 0.0321(14) 0.0198(12) -0.0017(10) 0.0019(10) 0.0006(10) C15 0.0322(14) 0.0259(13) 0.0288(14) -0.0010(11) -0.0082(11) 0.0080(11) C26 0.0248(13) 0.0324(14) 0.0243(13) -0.0033(11) -0.0067(10) 0.0029(11) C5 0.0217(12) 0.0298(13) 0.0219(13) -0.0069(10) -0.0056(10) -0.0002(10) C32 0.0270(13) 0.0252(13) 0.0281(14) -0.0062(10) -0.0077(11) -0.0009(10) O3 0.0282(11) 0.0563(14) 0.0605(15) 0.0084(11) -0.0020(10) -0.0214(10) C1 0.0204(12) 0.0259(13) 0.0214(12) -0.0026(10) -0.0009(10) -0.0020(10) C36 0.0244(13) 0.0206(12) 0.0366(15) -0.0035(11) -0.0022(11) 0.0002(10) C19 0.0245(13) 0.0233(13) 0.0353(15) -0.0063(11) -0.0063(11) -0.0027(10) C31 0.0305(14) 0.0253(13) 0.0229(13) -0.0072(10) -0.0025(10) 0.0024(10) C24 0.0143(12) 0.0258(13) 0.0353(15) -0.0003(11) -0.0029(10) -0.0019(10) C28 0.0160(12) 0.0213(12) 0.0350(14) -0.0040(10) -0.0039(10) 0.0014(9) C17 0.0286(13) 0.0252(13) 0.0189(12) -0.0039(10) -0.0042(10) 0.0071(10) C34 0.0298(14) 0.0266(13) 0.0262(14) 0.0004(11) -0.0030(11) -0.0009(11) C45 0.0391(15) 0.0204(12) 0.0248(14) -0.0046(10) -0.0007(11) -0.0078(11) C9 0.0276(14) 0.0334(15) 0.0376(16) -0.0074(12) -0.0074(12) -0.0051(12) C8 0.0294(14) 0.0221(13) 0.0393(16) 0.0060(11) -0.0083(12) -0.0062(11) C46 0.0425(17) 0.0340(15) 0.0397(17) -0.0089(13) -0.0020(13) 0.0060(13) C42 0.0323(15) 0.0307(14) 0.0299(14) 0.0025(11) -0.0051(11) 0.0050(11) C38 0.0329(15) 0.0265(14) 0.0400(16) -0.0049(12) 0.0093(12) -0.0016(11) C35 0.0302(14) 0.0237(13) 0.0340(15) 0.0031(11) -0.0060(11) 0.0000(11) C18 0.0395(15) 0.0219(12) 0.0213(13) -0.0056(10) -0.0080(11) 0.0006(11) C44 0.0331(15) 0.0354(15) 0.0303(15) -0.0048(12) -0.0051(12) -0.0101(12) C7 0.0255(13) 0.0280(13) 0.0283(14) 0.0034(11) -0.0032(11) -0.0043(11) F7A 0.056(4) 0.057(2) 0.078(3) -0.0335(19) -0.001(3) 0.008(3) C27 0.0294(14) 0.0426(16) 0.0288(14) -0.0060(12) -0.0100(11) 0.0097(12) C40 0.0475(17) 0.0308(14) 0.0233(14) -0.0009(11) -0.0004(12) -0.0051(13) F9A 0.070(3) 0.096(5) 0.074(3) -0.058(3) 0.028(2) -0.030(3) C47 0.0513(19) 0.0351(16) 0.0385(17) -0.0129(13) 0.0120(14) -0.0095(14) C14 0.0421(16) 0.0295(14) 0.0283(15) -0.0048(11) -0.0083(12) 0.0131(12) C2 0.0249(14) 0.0362(15) 0.0506(18) -0.0165(13) -0.0104(12) -0.0028(12) C48 0.060(2) 0.0346(16) 0.0243(15) -0.0070(12) -0.0003(13) 0.0032(14) C4 0.0334(15) 0.0220(13) 0.061(2) -0.0121(13) -0.0062(14) 0.0008(11) C39 0.0435(18) 0.0504(19) 0.0289(16) -0.0060(13) 0.0038(13) 0.0000(14) C43 0.0303(14) 0.0373(15) 0.0285(14) -0.0040(12) -0.0106(11) -0.0035(12) C10 0.0367(17) 0.0509(19) 0.0431(18) -0.0062(15) -0.0149(14) 0.0047(14) F8A 0.051(2) 0.087(3) 0.078(3) 0.041(3) 0.0120(19) -0.0068(18) F10 0.146(7) 0.033(3) 0.094(4) 0.028(3) 0.071(5) 0.014(4) P3 0.0480(5) 0.0252(4) 0.0406(4) -0.0018(3) 0.0009(4) -0.0023(3) F13 0.0545(11) 0.0362(9) 0.0346(9) -0.0021(7) 0.0061(8) -0.0014(8) F18 0.0532(11) 0.0719(13) 0.0369(10) -0.0105(9) -0.0130(8) 0.0136(10) F14 0.0369(10) 0.0911(15) 0.0545(12) 0.0032(11) -0.0098(9) -0.0145(10) F16 0.106(2) 0.0718(16) 0.172(3) -0.0525(18) 0.0427(19) -0.0641(16) F15 0.126(2) 0.0623(15) 0.0822(17) -0.0207(13) 0.0121(15) 0.0416(14) F17 0.154(3) 0.0740(16) 0.0610(15) 0.0404(13) 0.0168(15) 0.0502(16) C12 0.0353(16) 0.0457(17) 0.0302(15) 0.0056(13) -0.0015(12) -0.0024(13) C3 0.051(2) 0.0304(16) 0.085(3) -0.0193(17) -0.0320(19) -0.0011(14) F11A 0.057(2) 0.083(3) 0.059(3) -0.025(2) -0.0282(18) 0.0228(18) C11 0.0496(19) 0.0499(19) 0.0339(17) 0.0047(14) -0.0089(14) 0.0055(15) F12A 0.032(2) 0.185(6) 0.071(3) -0.006(3) -0.0020(17) -0.028(2) O1W 0.070(8) 0.142(13) 0.143(13) -0.079(10) -0.019(7) 0.006(7) F9B 0.066(7) 0.049(4) 0.092(9) -0.002(5) 0.042(6) 0.010(4) F8B 0.084(7) 0.068(6) 0.077(7) -0.032(6) 0.037(6) -0.053(6) F11B 0.152(11) 0.070(6) 0.078(8) -0.027(5) -0.070(8) 0.028(6) F10A 0.056(6) 0.057(8) 0.178(17) -0.033(9) 0.025(7) -0.024(5) F7B 0.045(7) 0.027(4) 0.113(11) -0.009(5) 0.013(6) 0.013(4) F12B 0.43(3) 0.082(8) 0.087(10) 0.028(8) -0.164(16) -0.015(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 F2 1.5969(15) . ? P1 F3 1.5968(16) . ? P1 F5 1.6015(17) . ? P1 F4 1.5991(17) . ? P1 F6 1.6018(17) . ? P1 F1 1.5894(17) . ? P2 F7A 1.577(7) . ? P2 F9A 1.575(4) . ? P2 F8A 1.639(3) . ? P2 F10 1.517(5) . ? P2 F11A 1.568(3) . ? P2 F12A 1.597(4) . ? P2 F9B 1.652(10) . ? P2 F8B 1.522(6) . ? P2 F11B 1.710(8) . ? P2 F10A 1.590(15) . ? P2 F7B 1.562(14) . ? P2 F12B 1.384(10) . ? Na1 Na2 3.2818(13) . ? Na1 Na3 3.2376(13) . ? Na1 O6 2.6537(18) . ? Na1 O4 2.4719(18) . ? Na1 O7 2.4392(18) . ? Na1 O1 2.2739(19) . ? Na1 O12 2.336(2) . ? Na1 O3 2.287(2) . ? Na2 Na3 3.2084(13) . ? Na2 O5 2.4417(18) . ? Na2 O6 2.2665(18) . ? Na2 O9 2.4281(19) . ? Na2 O4 2.3588(18) . ? Na2 O7 2.3662(18) . ? Na2 O8 2.3568(18) . ? Na3 O6 2.3244(18) . ? Na3 O9 2.6290(19) . ? Na3 O7 2.3728(17) . ? Na3 O11 2.5044(19) . ? Na3 O12 2.376(2) . ? Na3 O10 2.2749(19) . ? Na3 C45 3.092(3) . ? O5 C19 1.430(3) . ? O5 C18 1.431(3) . ? O6 C21 1.240(3) . ? O9 C33 1.241(3) . ? O4 C13 1.241(3) . ? O7 C25 1.244(3) . ? O8 C30 1.437(3) . ? O8 C31 1.428(3) . ? O1 C1 1.229(3) . ? O2 C6 1.422(3) . ? O2 C7 1.429(3) . ? N3 C16 1.466(3) . ? N3 C13 1.337(3) . ? N3 C17 1.451(3) . ? N1 C5 1.445(3) . ? N1 C1 1.338(3) . ? N1 C4 1.454(3) . ? N6 C33 1.342(3) . ? N6 C32 1.455(3) . ? N6 C36 1.460(3) . ? O11 C42 1.423(3) . ? O11 C43 1.433(3) . ? O12 C45 1.237(3) . ? N5 C25 1.334(3) . ? N5 C29 1.454(3) . ? N5 C28 1.462(3) . ? N4 C21 1.339(3) . ? N4 C20 1.460(3) . ? N4 C24 1.469(3) . ? N7 C41 1.452(3) . ? N7 C37 1.340(3) . ? N7 C40 1.463(3) . ? C21 C22 1.503(3) . ? O10 C37 1.228(3) . ? C25 C26 1.506(3) . ? C33 C34 1.510(3) . ? C6 C5 1.516(3) . ? N2 C9 1.341(3) . ? N2 C8 1.448(3) . ? N2 C12 1.462(3) . ? C41 C42 1.518(4) . ? N8 C45 1.336(3) . ? N8 C44 1.447(3) . ? N8 C48 1.457(3) . ? C22 C23 1.529(3) . ? C16 C15 1.526(3) . ? C37 C38 1.502(3) . ? C23 C24 1.528(3) . ? C13 C14 1.505(3) . ? C20 C19 1.506(4) . ? C29 C30 1.513(3) . ? C15 C14 1.528(4) . ? C26 C27 1.520(4) . ? C32 C31 1.514(3) . ? O3 C9 1.226(3) . ? C1 C2 1.510(3) . ? C36 C35 1.525(4) . ? C28 C27 1.523(4) . ? C17 C18 1.513(3) . ? C34 C35 1.526(4) . ? C45 C46 1.503(4) . ? C9 C10 1.501(4) . ? C8 C7 1.513(3) 1_455 ? C46 C47 1.521(4) . ? C38 C39 1.517(4) . ? C44 C43 1.516(4) . ? C7 C8 1.513(3) 1_655 ? C40 C39 1.513(4) . ? C47 C48 1.529(4) . ? C2 C3 1.492(4) . ? C4 C3 1.491(4) . ? C10 C11 1.530(4) . ? P3 F13 1.6068(18) . ? P3 F18 1.5977(19) . ? P3 F14 1.593(2) . ? P3 F16 1.575(2) . ? P3 F15 1.578(2) . ? P3 F17 1.580(2) . ? C12 C11 1.529(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 P1 F5 90.14(8) . . ? F2 P1 F4 89.74(9) . . ? F2 P1 F6 89.88(9) . . ? F3 P1 F2 179.42(10) . . ? F3 P1 F5 89.28(9) . . ? F3 P1 F4 90.28(9) . . ? F3 P1 F6 90.70(9) . . ? F5 P1 F6 178.99(11) . . ? F4 P1 F5 89.46(10) . . ? F4 P1 F6 89.53(10) . . ? F1 P1 F2 90.03(9) . . ? F1 P1 F3 89.96(10) . . ? F1 P1 F5 90.81(10) . . ? F1 P1 F4 179.65(10) . . ? F1 P1 F6 90.20(10) . . ? F7A P2 F8A 89.8(4) . . ? F7A P2 F12A 89.9(3) . . ? F7A P2 F9B 151.7(5) . . ? F7A P2 F11B 69.5(4) . . ? F7A P2 F10A 98.2(9) . . ? F9A P2 F7A 174.1(4) . . ? F9A P2 F8A 84.3(4) . . ? F9A P2 F12A 89.3(3) . . ? F9A P2 F9B 31.5(4) . . ? F9A P2 F11B 114.3(4) . . ? F9A P2 F10A 87.0(8) . . ? F8A P2 F9B 101.5(4) . . ? F8A P2 F11B 124.8(4) . . ? F10 P2 F7A 92.5(4) . . ? F10 P2 F9A 93.3(4) . . ? F10 P2 F8A 175.8(4) . . ? F10 P2 F11A 96.7(4) . . ? F10 P2 F12A 90.4(4) . . ? F10 P2 F9B 78.0(5) . . ? F10 P2 F8B 146.3(6) . . ? F10 P2 F11B 59.3(5) . . ? F10 P2 F10A 23.1(8) . . ? F10 P2 F7B 90.0(6) . . ? F11A P2 F7A 90.6(2) . . ? F11A P2 F9A 89.4(2) . . ? F11A P2 F8A 86.8(2) . . ? F11A P2 F12A 172.9(3) . . ? F11A P2 F9B 64.6(5) . . ? F11A P2 F11B 45.2(4) . . ? F11A P2 F10A 118.8(7) . . ? F12A P2 F8A 86.1(2) . . ? F12A P2 F9B 116.4(6) . . ? F12A P2 F11B 141.1(5) . . ? F9B P2 F11B 82.9(5) . . ? F8B P2 F7A 75.2(4) . . ? F8B P2 F9A 100.2(3) . . ? F8B P2 F8A 37.8(4) . . ? F8B P2 F11A 53.2(5) . . ? F8B P2 F12A 120.3(6) . . ? F8B P2 F9B 98.0(6) . . ? F8B P2 F11B 87.0(6) . . ? F8B P2 F10A 168.8(8) . . ? F8B P2 F7B 89.4(6) . . ? F10A P2 F8A 152.8(7) . . ? F10A P2 F12A 68.0(7) . . ? F10A P2 F9B 83.6(9) . . ? F10A P2 F11B 82.1(7) . . ? F7B P2 F7A 22.3(5) . . ? F7B P2 F9A 156.8(5) . . ? F7B P2 F8A 90.8(6) . . ? F7B P2 F11A 112.9(5) . . ? F7B P2 F12A 67.8(6) . . ? F7B P2 F9B 167.1(7) . . ? F7B P2 F11B 87.0(6) . . ? F7B P2 F10A 87.2(9) . . ? F12B P2 F7A 112.9(9) . . ? F12B P2 F9A 63.6(9) . . ? F12B P2 F8A 59.6(8) . . ? F12B P2 F10 116.2(8) . . ? F12B P2 F11A 137.3(13) . . ? F12B P2 F12A 36.8(12) . . ? F12B P2 F9B 95.0(9) . . ? F12B P2 F8B 97.4(9) . . ? F12B P2 F11B 175.4(7) . . ? F12B P2 F10A 93.5(11) . . ? F12B P2 F7B 94.5(11) . . ? Na3 Na1 Na2 58.96(3) . . ? O6 Na1 Na2 43.30(4) . . ? O6 Na1 Na3 45.14(4) . . ? O4 Na1 Na2 45.77(4) . . ? O4 Na1 Na3 104.46(5) . . ? O4 Na1 O6 73.54(6) . . ? O7 Na1 Na2 46.00(4) . . ? O7 Na1 Na3 46.85(4) . . ? O7 Na1 O6 72.21(5) . . ? O7 Na1 O4 80.76(6) . . ? O1 Na1 Na2 129.00(6) . . ? O1 Na1 Na3 125.04(6) . . ? O1 Na1 O6 99.29(6) . . ? O1 Na1 O4 99.70(7) . . ? O1 Na1 O7 171.08(7) . . ? O1 Na1 O12 93.99(7) . . ? O1 Na1 O3 102.70(8) . . ? O12 Na1 Na2 105.99(5) . . ? O12 Na1 Na3 47.12(5) . . ? O12 Na1 O6 78.55(6) . . ? O12 Na1 O4 150.50(7) . . ? O12 Na1 O7 81.81(7) . . ? O3 Na1 Na2 114.17(7) . . ? O3 Na1 Na3 123.33(7) . . ? O3 Na1 O6 156.46(8) . . ? O3 Na1 O4 94.41(8) . . ? O3 Na1 O7 86.11(7) . . ? O3 Na1 O12 107.97(8) . . ? Na3 Na2 Na1 59.83(3) . . ? O5 Na2 Na1 120.33(5) . . ? O5 Na2 Na3 129.57(5) . . ? O6 Na2 Na1 53.42(5) . . ? O6 Na2 Na3 46.41(5) . . ? O6 Na2 O5 90.51(6) . . ? O6 Na2 O9 86.12(6) . . ? O6 Na2 O4 83.20(7) . . ? O6 Na2 O7 80.89(6) . . ? O6 Na2 O8 168.58(7) . . ? O9 Na2 Na1 112.24(5) . . ? O9 Na2 Na3 53.45(5) . . ? O9 Na2 O5 110.00(6) . . ? O4 Na2 Na1 48.67(5) . . ? O4 Na2 Na3 108.21(5) . . ? O4 Na2 O5 86.27(6) . . ? O4 Na2 O9 160.63(7) . . ? O4 Na2 O7 84.66(6) . . ? O7 Na2 Na1 47.87(4) . . ? O7 Na2 Na3 47.47(4) . . ? O7 Na2 O5 168.17(7) . . ? O7 Na2 O9 77.71(6) . . ? O8 Na2 Na1 124.00(5) . . ? O8 Na2 Na3 122.17(5) . . ? O8 Na2 O5 99.41(6) . . ? O8 Na2 O9 85.19(6) . . ? O8 Na2 O4 102.94(7) . . ? O8 Na2 O7 90.02(6) . . ? Na2 Na3 Na1 61.21(3) . . ? O6 Na3 Na1 54.02(5) . . ? O6 Na3 Na2 44.93(5) . . ? O6 Na3 O9 80.46(6) . . ? O6 Na3 O7 79.58(6) . . ? O6 Na3 O11 167.07(7) . . ? O6 Na3 O12 84.75(7) . . ? O6 Na3 C45 98.13(7) . . ? O9 Na3 Na1 108.15(5) . . ? O9 Na3 Na2 47.90(4) . . ? O9 Na3 C45 174.95(7) . . ? O7 Na3 Na1 48.59(4) . . ? O7 Na3 Na2 47.30(4) . . ? O7 Na3 O9 73.74(6) . . ? O7 Na3 O11 111.46(6) . . ? O7 Na3 O12 82.40(6) . . ? O7 Na3 C45 101.26(7) . . ? O11 Na3 Na1 127.98(5) . . ? O11 Na3 Na2 147.88(6) . . ? O11 Na3 O9 108.61(6) . . ? O11 Na3 C45 73.62(7) . . ? O12 Na3 Na1 46.09(5) . . ? O12 Na3 Na2 107.21(5) . . ? O12 Na3 O9 153.78(7) . . ? O12 Na3 O11 89.95(7) . . ? O12 Na3 C45 21.45(6) . . ? O10 Na3 Na1 118.19(6) . . ? O10 Na3 Na2 121.96(6) . . ? O10 Na3 O6 85.36(7) . . ? O10 Na3 O9 107.87(7) . . ? O10 Na3 O7 164.40(7) . . ? O10 Na3 O11 83.06(7) . . ? O10 Na3 O12 92.25(7) . . ? O10 Na3 C45 76.75(7) . . ? C45 Na3 Na1 67.37(5) . . ? C45 Na3 Na2 128.09(6) . . ? C19 O5 Na2 125.02(14) . . ? C19 O5 C18 112.73(18) . . ? C18 O5 Na2 120.08(14) . . ? Na2 O6 Na1 83.27(6) . . ? Na2 O6 Na3 88.66(6) . . ? Na3 O6 Na1 80.85(5) . . ? C21 O6 Na1 121.24(14) . . ? C21 O6 Na2 131.66(15) . . ? C21 O6 Na3 132.75(15) . . ? Na2 O9 Na3 78.65(6) . . ? C33 O9 Na2 126.82(16) . . ? C33 O9 Na3 143.52(16) . . ? Na2 O4 Na1 85.55(6) . . ? C13 O4 Na1 128.36(15) . . ? C13 O4 Na2 123.93(15) . . ? Na2 O7 Na1 86.13(6) . . ? Na2 O7 Na3 85.22(6) . . ? Na3 O7 Na1 84.56(6) . . ? C25 O7 Na1 138.10(14) . . ? C25 O7 Na2 122.46(14) . . ? C25 O7 Na3 124.13(15) . . ? C30 O8 Na2 123.91(14) . . ? C31 O8 Na2 118.78(14) . . ? C31 O8 C30 112.98(18) . . ? C1 O1 Na1 140.90(16) . . ? C6 O2 C7 111.19(18) . . ? C13 N3 C16 114.4(2) . . ? C13 N3 C17 124.0(2) . . ? C17 N3 C16 120.64(19) . . ? C5 N1 C4 122.2(2) . . ? C1 N1 C5 123.3(2) . . ? C1 N1 C4 114.0(2) . . ? C33 N6 C32 124.8(2) . . ? C33 N6 C36 114.1(2) . . ? C32 N6 C36 120.8(2) . . ? C42 O11 Na3 117.06(14) . . ? C42 O11 C43 111.57(19) . . ? C43 O11 Na3 130.64(14) . . ? Na1 O12 Na3 86.79(7) . . ? C45 O12 Na1 157.75(18) . . ? C45 O12 Na3 113.91(16) . . ? C25 N5 C29 124.14(19) . . ? C25 N5 C28 113.95(19) . . ? C29 N5 C28 121.88(19) . . ? C21 N4 C20 124.8(2) . . ? C21 N4 C24 113.1(2) . . ? C20 N4 C24 121.29(18) . . ? C41 N7 C40 121.8(2) . . ? C37 N7 C41 123.7(2) . . ? C37 N7 C40 114.5(2) . . ? O6 C21 N4 124.8(2) . . ? O6 C21 C22 126.3(2) . . ? N4 C21 C22 108.81(19) . . ? C37 O10 Na3 132.76(17) . . ? O7 C25 N5 125.8(2) . . ? O7 C25 C26 125.9(2) . . ? N5 C25 C26 108.4(2) . . ? O9 C33 N6 125.6(2) . . ? O9 C33 C34 126.4(2) . . ? N6 C33 C34 108.0(2) . . ? O2 C6 C5 108.47(19) . . ? C9 N2 C8 122.7(2) . . ? C9 N2 C12 113.6(2) . . ? C8 N2 C12 122.6(2) . . ? N7 C41 C42 112.3(2) . . ? C45 N8 C44 122.5(2) . . ? C45 N8 C48 114.3(2) . . ? C44 N8 C48 122.8(2) . . ? C21 C22 C23 103.93(19) . . ? N3 C16 C15 103.71(19) . . ? N7 C37 C38 108.7(2) . . ? O10 C37 N7 125.1(2) . . ? O10 C37 C38 126.3(2) . . ? C24 C23 C22 103.52(19) . . ? O4 C13 N3 125.2(2) . . ? O4 C13 C14 126.2(2) . . ? N3 C13 C14 108.6(2) . . ? N4 C20 C19 114.2(2) . . ? N5 C29 C30 111.70(19) . . ? O8 C30 C29 108.10(18) . . ? C16 C15 C14 105.1(2) . . ? C25 C26 C27 104.2(2) . . ? N1 C5 C6 111.60(19) . . ? N6 C32 C31 112.6(2) . . ? C9 O3 Na1 143.9(2) . . ? O1 C1 N1 125.4(2) . . ? O1 C1 C2 126.1(2) . . ? N1 C1 C2 108.5(2) . . ? N6 C36 C35 103.2(2) . . ? O5 C19 C20 108.85(19) . . ? O8 C31 C32 109.0(2) . . ? N4 C24 C23 103.36(18) . . ? N5 C28 C27 103.19(19) . . ? N3 C17 C18 111.8(2) . . ? C33 C34 C35 104.4(2) . . ? O12 C45 Na3 44.64(12) . . ? O12 C45 N8 124.3(3) . . ? O12 C45 C46 126.8(3) . . ? N8 C45 Na3 101.37(16) . . ? N8 C45 C46 108.9(2) . . ? C46 C45 Na3 128.37(17) . . ? N2 C9 C10 108.8(2) . . ? O3 C9 N2 125.0(3) . . ? O3 C9 C10 126.1(3) . . ? N2 C8 C7 114.7(2) . 1_455 ? C45 C46 C47 104.9(2) . . ? O11 C42 C41 109.0(2) . . ? C37 C38 C39 105.8(2) . . ? C36 C35 C34 104.3(2) . . ? O5 C18 C17 107.86(19) . . ? N8 C44 C43 112.1(2) . . ? O2 C7 C8 109.7(2) . 1_655 ? C26 C27 C28 104.5(2) . . ? N7 C40 C39 104.4(2) . . ? C46 C47 C48 105.2(2) . . ? C13 C14 C15 105.3(2) . . ? C3 C2 C1 104.9(2) . . ? N8 C48 C47 103.6(2) . . ? N1 C4 C3 104.5(2) . . ? C40 C39 C38 106.6(2) . . ? O11 C43 C44 109.0(2) . . ? C9 C10 C11 104.4(2) . . ? F18 P3 F13 89.56(10) . . ? F14 P3 F13 89.15(10) . . ? F14 P3 F18 87.63(11) . . ? F16 P3 F13 88.42(12) . . ? F16 P3 F18 90.20(16) . . ? F16 P3 F14 176.76(15) . . ? F16 P3 F15 90.57(15) . . ? F16 P3 F17 93.15(18) . . ? F15 P3 F13 178.90(14) . . ? F15 P3 F18 89.99(12) . . ? F15 P3 F14 91.84(14) . . ? F15 P3 F17 91.20(14) . . ? F17 P3 F13 89.31(11) . . ? F17 P3 F18 176.44(15) . . ? F17 P3 F14 88.97(14) . . ? N2 C12 C11 103.1(2) . . ? C4 C3 C2 107.9(2) . . ? C12 C11 C10 104.2(2) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 1 1 -25 0.0852 1.0000 1.0000 -25.0000 -0.1663 0.9835 -0.0087 0 -1 25 0.0361 0.0000 -1.0000 25.0000 0.1863 -0.9721 0.0575 -17 -8 -5 0.3295 -17.0000 -8.0000 -5.0001 0.0194 0.0111 -0.9995 2 -19 -3 0.2963 2.0000 -19.0000 -3.0001 0.9404 0.1672 -0.2789 13 -14 0 0.2588 13.0000 -14.0000 -0.0000 0.9351 0.1694 0.3637 14 12 5 0.2338 14.0000 12.0000 5.0001 -0.2723 -0.0513 0.9304 -1 19 3 0.1364 -1.0000 19.0000 3.0001 -0.9204 -0.1557 0.3277 _database_code_depnum_ccdc_archive 'CCDC 965879' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_bishep_napf6_dmp _audit_creation_date 2013-01-29 _audit_creation_method ; Olex2 1.2 (compiled Nov 5 2012 18:25:38, GUI svn.r4372) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H48 F12 N4 Na2 O8 P2' _chemical_formula_sum 'C26 H48 F12 N4 Na2 O8 P2' _chemical_formula_weight 880.60 _chemical_melting_point ? _chemical_oxdiff_formula 'C12 H20 N2 O3 Na P F6' 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' Na Na 0.0362 0.0249 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 11.1886(5) _cell_length_b 13.3508(5) _cell_length_c 13.6275(6) _cell_angle_alpha 90.00 _cell_angle_beta 111.547(5) _cell_angle_gamma 90.00 _cell_volume 1893.37(14) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2442 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 28.9219 _cell_measurement_theta_min 2.5306 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.2888 _exptl_crystal_size_mid 0.1892 _exptl_crystal_size_min 0.0992 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_unetI/netI 0.0690 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 13061 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.54 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.978 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -84.00 -11.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -57.0000 -60.0000 73 #__ type_ start__ end____ width___ exp.time_ 2 omega -46.00 -4.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -57.0000 -150.0000 42 #__ type_ start__ end____ width___ exp.time_ 3 omega -81.00 -14.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -57.0000 -180.0000 67 #__ type_ start__ end____ width___ exp.time_ 4 omega 11.00 58.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 18.5616 -100.0000 -180.0000 47 #__ type_ start__ end____ width___ exp.time_ 5 omega -87.00 -50.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 -57.0000 30.0000 37 #__ type_ start__ end____ width___ exp.time_ 6 omega -39.00 51.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.9366 57.0000 -30.0000 90 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0531317000 _diffrn_orient_matrix_UB_12 0.0052672000 _diffrn_orient_matrix_UB_13 0.0161661000 _diffrn_orient_matrix_UB_21 -0.0424719000 _diffrn_orient_matrix_UB_22 -0.0119804000 _diffrn_orient_matrix_UB_23 -0.0518120000 _diffrn_orient_matrix_UB_31 0.0044562000 _diffrn_orient_matrix_UB_32 -0.0514760000 _diffrn_orient_matrix_UB_33 0.0136913000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2880 _reflns_number_total 4262 _reflns_odcompleteness_completeness 99.85 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.555 _refine_diff_density_min -0.527 _refine_diff_density_rms 0.074 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 248 _refine_ls_number_reflns 4262 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0985 _refine_ls_R_factor_gt 0.0618 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+2.6586P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1266 _refine_ls_wR_factor_ref 0.1480 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H3A,H3B} of C3, {H5A,H5B} of C5, {H6A,H6B} of C6, {H4A,H4B} of C4, {H7A, H7B} of C7, {H8A,H8B} of C8, {H11A,H11B} of C11, {H10A,H10B} of C10, {H12A, H12B} of C12, {H2A,H2B} of C2 At 1.5 times of: H4 of O4, {H13A,H13B,H13C} of C13 2. Restrained distances O4-H4 0.87 with sigma of 0.01 C13-H4 1.896724 with sigma of 0.02 3.a Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C4(H4A,H4B), C6(H6A,H6B), C5(H5A,H5B), C3(H3A,H3B), C2(H2A,H2B), C8(H8A,H8B), C11(H11A,H11B), C10(H10A,H10B), C12(H12A,H12B) 3.b Idealised Me refined as rotating group: C13(H13A,H13B,H13C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.79651(8) 0.67832(7) 0.58307(7) 0.0270(2) Uani 1 1 d . . . F3 F 0.8024(2) 0.6611(2) 0.47001(18) 0.0645(8) Uani 1 1 d . . . F1 F 0.6852(2) 0.75954(15) 0.53291(18) 0.0442(6) Uani 1 1 d . . . F6 F 0.9031(2) 0.76285(17) 0.60794(19) 0.0478(6) Uani 1 1 d . . . F2 F 0.7856(2) 0.69506(19) 0.69479(17) 0.0540(7) Uani 1 1 d . . . F4 F 0.6882(2) 0.59333(15) 0.55700(18) 0.0439(6) Uani 1 1 d . . . F5 F 0.9037(2) 0.59608(17) 0.6328(2) 0.0621(8) Uani 1 1 d . . . N1 N 0.2752(3) 0.69336(19) 0.4767(2) 0.0246(6) Uani 1 1 d . . . O1 O 0.3465(2) 0.83024(15) 0.41343(17) 0.0228(5) Uani 1 1 d . . . O2 O 0.4714(2) 0.77213(14) 0.66093(15) 0.0192(5) Uani 1 1 d . . . C7 C 0.5019(3) 0.7987(2) 0.7692(2) 0.0225(7) Uani 1 1 d . . . H7A H 0.5903 0.7769 0.8121 0.027 Uiso 1 1 calc R . . H7B H 0.4416 0.7654 0.7969 0.027 Uiso 1 1 calc R . . C4 C 0.1545(4) 0.6530(3) 0.4802(3) 0.0429(10) Uani 1 1 d . . . H4A H 0.1565 0.6519 0.5534 0.051 Uiso 1 1 calc R . . H4B H 0.1387 0.5843 0.4510 0.051 Uiso 1 1 calc R . . C6 C 0.4560(3) 0.6665(2) 0.6455(2) 0.0260(7) Uani 1 1 d . . . H6A H 0.3977 0.6404 0.6793 0.031 Uiso 1 1 calc R . . H6B H 0.5401 0.6325 0.6775 0.031 Uiso 1 1 calc R . . C5 C 0.3999(3) 0.6466(2) 0.5278(2) 0.0280(8) Uani 1 1 d . . . H5A H 0.4598 0.6721 0.4954 0.034 Uiso 1 1 calc R . . H5B H 0.3912 0.5734 0.5157 0.034 Uiso 1 1 calc R . . C3 C 0.0549(4) 0.7232(5) 0.4138(5) 0.086(2) Uani 1 1 d . . . H3A H -0.0054 0.6876 0.3517 0.103 Uiso 1 1 calc R . . H3B H 0.0055 0.7508 0.4548 0.103 Uiso 1 1 calc R . . C2 C 0.1180(3) 0.8042(3) 0.3796(3) 0.0393(9) Uani 1 1 d . . . H2A H 0.1013 0.8693 0.4068 0.047 Uiso 1 1 calc R . . H2B H 0.0865 0.8074 0.3017 0.047 Uiso 1 1 calc R . . C1 C 0.2589(3) 0.7798(2) 0.4244(2) 0.0212(7) Uani 1 1 d . . . C8 C 0.4908(3) 0.9111(2) 0.7754(2) 0.0232(7) Uani 1 1 d . . . H8A H 0.5084 0.9304 0.8496 0.028 Uiso 1 1 calc R . . H8B H 0.5567 0.9431 0.7533 0.028 Uiso 1 1 calc R . . N2 N 0.3644(2) 0.94847(18) 0.70933(19) 0.0192(6) Uani 1 1 d . . . C11 C 0.1423(3) 0.9821(3) 0.6438(3) 0.0329(8) Uani 1 1 d . . . H11A H 0.0816 0.9311 0.6003 0.039 Uiso 1 1 calc R . . H11B H 0.0943 1.0299 0.6711 0.039 Uiso 1 1 calc R . . C9 C 0.3438(3) 1.0014(2) 0.6213(2) 0.0204(7) Uani 1 1 d . . . C10 C 0.2070(3) 1.0363(3) 0.5793(3) 0.0378(9) Uani 1 1 d . . . H10A H 0.1652 1.0193 0.5036 0.045 Uiso 1 1 calc R . . H10B H 0.2025 1.1097 0.5876 0.045 Uiso 1 1 calc R . . C12 C 0.2500(3) 0.9325(3) 0.7346(3) 0.0314(8) Uani 1 1 d . . . H12A H 0.2596 0.9642 0.8028 0.038 Uiso 1 1 calc R . . H12B H 0.2330 0.8601 0.7385 0.038 Uiso 1 1 calc R . . Na1 Na 0.54854(11) 0.88169(9) 0.54793(9) 0.0203(3) Uani 1 1 d . . . O3 O 0.4263(2) 1.01906(16) 0.58304(16) 0.0232(5) Uani 1 1 d . . . O4 O 0.7123(2) 0.97666(18) 0.6674(2) 0.0401(7) Uani 1 1 d D . . H4 H 0.700(3) 1.0384(11) 0.647(3) 0.060 Uiso 1 1 d D . . C13 C 0.8263(4) 0.9638(3) 0.7546(3) 0.0435(10) Uani 1 1 d D . . H13A H 0.8991 0.9615 0.7309 0.065 Uiso 1 1 calc R . . H13B H 0.8223 0.9009 0.7903 0.065 Uiso 1 1 calc R . . H13C H 0.8376 1.0198 0.8036 0.065 Uiso 1 1 calc R . . 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 0.0289(5) 0.0247(5) 0.0237(4) -0.0004(4) 0.0054(4) 0.0068(4) F3 0.0437(14) 0.120(2) 0.0336(13) -0.0160(14) 0.0185(11) 0.0079(15) F1 0.0370(12) 0.0325(12) 0.0654(16) 0.0153(11) 0.0216(11) 0.0154(10) F6 0.0377(13) 0.0464(14) 0.0582(15) 0.0031(12) 0.0163(11) -0.0063(11) F2 0.0711(17) 0.0649(16) 0.0275(12) -0.0105(11) 0.0200(12) -0.0195(13) F4 0.0403(13) 0.0287(11) 0.0517(14) -0.0080(10) 0.0039(11) -0.0019(10) F5 0.0438(14) 0.0427(14) 0.0746(18) 0.0005(13) -0.0081(13) 0.0162(12) N1 0.0328(16) 0.0186(14) 0.0228(14) -0.0046(11) 0.0106(12) -0.0091(12) O1 0.0214(11) 0.0216(11) 0.0246(12) 0.0037(9) 0.0075(9) 0.0001(9) O2 0.0290(12) 0.0137(10) 0.0157(10) 0.0004(8) 0.0093(9) -0.0019(9) C7 0.0308(18) 0.0205(16) 0.0126(14) 0.0039(12) 0.0036(13) 0.0003(14) C4 0.053(3) 0.035(2) 0.054(3) -0.0109(19) 0.034(2) -0.0231(19) C6 0.040(2) 0.0145(15) 0.0234(17) 0.0031(13) 0.0114(15) -0.0010(14) C5 0.045(2) 0.0154(16) 0.0225(16) -0.0019(13) 0.0111(16) 0.0013(15) C3 0.025(2) 0.120(5) 0.099(4) 0.046(4) 0.008(3) -0.023(3) C2 0.0219(18) 0.040(2) 0.057(3) -0.0061(19) 0.0156(18) 0.0020(16) C1 0.0234(16) 0.0213(16) 0.0196(15) -0.0061(13) 0.0087(13) -0.0026(14) C8 0.0310(18) 0.0226(16) 0.0129(14) -0.0024(13) 0.0046(13) -0.0042(14) N2 0.0249(14) 0.0182(13) 0.0177(13) -0.0020(10) 0.0117(11) -0.0014(11) C11 0.0262(18) 0.040(2) 0.036(2) -0.0019(17) 0.0150(16) -0.0020(16) C9 0.0301(17) 0.0139(15) 0.0187(15) -0.0016(12) 0.0107(13) -0.0026(13) C10 0.032(2) 0.044(2) 0.042(2) 0.0161(18) 0.0180(18) 0.0105(17) C12 0.039(2) 0.0301(19) 0.0340(19) 0.0067(15) 0.0243(17) 0.0043(16) Na1 0.0215(6) 0.0191(6) 0.0200(6) 0.0049(5) 0.0075(5) 0.0001(5) O3 0.0271(12) 0.0223(11) 0.0239(11) 0.0071(9) 0.0136(10) -0.0008(10) O4 0.0302(13) 0.0265(13) 0.0444(15) 0.0126(12) -0.0091(12) -0.0045(11) C13 0.035(2) 0.045(2) 0.038(2) 0.0097(19) -0.0018(18) 0.0021(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 F3 1.583(2) . ? P1 F1 1.603(2) . ? P1 F6 1.586(2) . ? P1 F2 1.587(2) . ? P1 F4 1.602(2) . ? P1 F5 1.583(2) . ? F1 Na1 2.295(2) . ? N1 C4 1.470(4) . ? N1 C5 1.452(4) . ? N1 C1 1.334(4) . ? O1 C1 1.242(4) . ? O1 Na1 2.428(2) . ? O2 C7 1.432(3) . ? O2 C6 1.427(3) . ? O2 Na1 2.496(2) . ? C7 C8 1.510(4) . ? C4 C3 1.483(6) . ? C6 C5 1.515(4) . ? C3 C2 1.457(6) . ? C2 C1 1.503(5) . ? C8 N2 1.458(4) . ? N2 C9 1.337(4) . ? N2 C12 1.458(4) . ? C11 C10 1.513(5) . ? C11 C12 1.525(5) . ? C9 C10 1.497(5) . ? C9 O3 1.238(3) . ? Na1 Na1 3.439(2) 3_676 ? Na1 O3 2.322(2) 3_676 ? Na1 O3 2.438(2) . ? Na1 O4 2.329(3) . ? O3 Na1 2.322(2) 3_676 ? O4 C13 1.398(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F3 P1 F1 89.25(14) . . ? F3 P1 F6 90.82(14) . . ? F3 P1 F2 178.12(14) . . ? F3 P1 F4 88.86(14) . . ? F3 P1 F5 91.15(15) . . ? F6 P1 F1 90.89(12) . . ? F6 P1 F2 90.66(13) . . ? F6 P1 F4 179.52(14) . . ? F2 P1 F1 89.56(14) . . ? F2 P1 F4 89.66(13) . . ? F4 P1 F1 88.76(12) . . ? F5 P1 F1 178.49(14) . . ? F5 P1 F6 90.56(13) . . ? F5 P1 F2 90.00(15) . . ? F5 P1 F4 89.80(13) . . ? P1 F1 Na1 151.81(15) . . ? C5 N1 C4 124.0(3) . . ? C1 N1 C4 112.8(3) . . ? C1 N1 C5 123.2(3) . . ? C1 O1 Na1 128.2(2) . . ? C7 O2 Na1 119.03(17) . . ? C6 O2 C7 111.5(2) . . ? C6 O2 Na1 122.60(17) . . ? O2 C7 C8 108.1(2) . . ? N1 C4 C3 104.0(3) . . ? O2 C6 C5 108.1(2) . . ? N1 C5 C6 112.6(3) . . ? C2 C3 C4 108.7(3) . . ? C3 C2 C1 105.6(3) . . ? N1 C1 C2 108.7(3) . . ? O1 C1 N1 125.1(3) . . ? O1 C1 C2 126.2(3) . . ? N2 C8 C7 112.8(3) . . ? C8 N2 C12 122.7(3) . . ? C9 N2 C8 123.0(3) . . ? C9 N2 C12 114.3(3) . . ? C10 C11 C12 105.9(3) . . ? N2 C9 C10 108.8(3) . . ? O3 C9 N2 124.7(3) . . ? O3 C9 C10 126.5(3) . . ? C9 C10 C11 105.6(3) . . ? N2 C12 C11 104.2(3) . . ? F1 Na1 O1 101.39(9) . . ? F1 Na1 O2 91.78(8) . . ? F1 Na1 Na1 138.31(8) . 3_676 ? F1 Na1 O3 93.68(9) . 3_676 ? F1 Na1 O3 172.76(10) . . ? F1 Na1 O4 94.04(10) . . ? O1 Na1 O2 82.13(8) . . ? O1 Na1 Na1 84.06(7) . 3_676 ? O1 Na1 O3 85.82(8) . . ? O2 Na1 Na1 129.80(7) . 3_676 ? O3 Na1 O1 85.61(8) 3_676 . ? O3 Na1 O2 88.49(8) . . ? O3 Na1 O2 167.35(9) 3_676 . ? O3 Na1 Na1 42.42(5) . 3_676 ? O3 Na1 Na1 45.11(6) 3_676 3_676 ? O3 Na1 O3 87.52(8) 3_676 . ? O3 Na1 O4 86.58(9) 3_676 . ? O4 Na1 O1 163.10(9) . . ? O4 Na1 O2 104.42(9) . . ? O4 Na1 Na1 79.81(7) . 3_676 ? O4 Na1 O3 78.89(9) . . ? C9 O3 Na1 138.8(2) . 3_676 ? C9 O3 Na1 119.88(19) . . ? Na1 O3 Na1 92.47(8) 3_676 . ? C13 O4 Na1 139.9(2) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 5 -12 -14 0.0946 5.0000 -12.0000 -14.0000 -0.5552 0.6568 0.4483 -5 12 14 0.0946 -5.0000 12.0000 14.0000 0.5552 -0.6568 -0.4483 4 12 -15 0.1193 4.0000 12.0000 -15.0000 -0.3918 0.4635 -0.8053 -4 -12 15 0.1193 -4.0000 -12.0000 15.0000 0.3918 -0.4635 0.8053 -14 1 -1 0.0496 -14.0000 1.0000 -1.0000 0.7329 0.6344 -0.1276 14 -1 1 0.0496 14.0000 -1.0000 1.0000 -0.7329 -0.6344 0.1276 _database_code_depnum_ccdc_archive 'CCDC 965880' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ap76_3b _audit_creation_date 2013-05-13 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H48 N4 Na2 O10, 2(C24 H20 B)' _chemical_formula_sum 'C72 H88 B2 N4 Na2 O10' _chemical_formula_weight 1237.06 _chemical_melting_point ? _chemical_oxdiff_formula C36H40N2O3BNa 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' B B 0.0013 0.0007 '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' Na Na 0.0362 0.0249 '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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 11.9380(5) _cell_length_b 12.1701(5) _cell_length_c 13.1018(7) _cell_angle_alpha 67.444(4) _cell_angle_beta 75.171(4) _cell_angle_gamma 78.989(3) _cell_volume 1690.16(13) _cell_formula_units_Z 1 _cell_measurement_reflns_used 5119 _cell_measurement_temperature 120 _cell_measurement_theta_max 32.5554 _cell_measurement_theta_min 2.6670 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_correction_T_min 0.985 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 660 _exptl_crystal_size_max 0.5581 _exptl_crystal_size_mid 0.241 _exptl_crystal_size_min 0.1241 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_unetI/netI 0.0602 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 28252 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.67 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -30.00 43.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -26.1867 38.0000 120.0000 73 #__ type_ start__ end____ width___ exp.time_ 2 omega -91.00 35.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -26.1867 0.0000 90.0000 126 #__ type_ start__ end____ width___ exp.time_ 3 omega 61.00 92.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 179.0000 -60.0000 31 #__ type_ start__ end____ width___ exp.time_ 4 omega 60.00 103.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 179.0000 90.0000 43 #__ type_ start__ end____ width___ exp.time_ 5 omega 42.00 74.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -109.0000 -83.0000 32 #__ type_ start__ end____ width___ exp.time_ 6 omega 60.00 103.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 179.0000 -120.0000 43 #__ type_ start__ end____ width___ exp.time_ 7 omega 10.00 99.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 38.0000 -60.0000 89 #__ type_ start__ end____ width___ exp.time_ 8 omega 12.00 74.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -109.0000 96.0000 62 #__ type_ start__ end____ width___ exp.time_ 9 omega -95.00 -5.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -26.1867 -57.0000 -60.0000 90 #__ type_ start__ end____ width___ exp.time_ 10 omega -102.00 -34.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -26.1867 -179.0000 150.0000 68 #__ type_ start__ end____ width___ exp.time_ 11 omega -96.00 4.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -26.1867 -77.0000 150.0000 100 #__ type_ start__ end____ width___ exp.time_ 12 omega -102.00 -77.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -26.1867 -179.0000 60.0000 25 #__ type_ start__ end____ width___ exp.time_ 13 omega -95.00 -5.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -26.1867 -57.0000 30.0000 90 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0011168000 _diffrn_orient_matrix_UB_12 -0.0147097000 _diffrn_orient_matrix_UB_13 -0.0476809000 _diffrn_orient_matrix_UB_21 0.0044776000 _diffrn_orient_matrix_UB_22 -0.0616968000 _diffrn_orient_matrix_UB_23 0.0334936000 _diffrn_orient_matrix_UB_31 -0.0616246000 _diffrn_orient_matrix_UB_32 0.0018659000 _diffrn_orient_matrix_UB_33 0.0136643000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_special_details ? _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5539 _reflns_number_total 7743 _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.44 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.377 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.043 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 422 _refine_ls_number_reflns 7743 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0791 _refine_ls_R_factor_gt 0.0502 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.2426P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1006 _refine_ls_wR_factor_ref 0.1132 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C5(H5C,H5D), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C4(H4C,H4D), C2(H2A,H2B), C3(H3A,H3B), C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B) 2.b Aromatic/amide H refined with riding coordinates: C18(H18), C14(H14), C26(H26), C16(H16), C36(H36), C17(H17), C15(H15), C27(H27), C24(H24), C32(H32), C20(H20), C33(H33), C28(H28), C30(H30), C35(H35), C34(H34), C21(H21), C23(H23), C29(H29), C22(H22) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Na1 Na 0.12547(5) 0.45265(6) 0.42276(5) 0.02484(16) Uani 1 1 d . . . O1 O 0.20974(9) 0.54296(11) 0.22027(9) 0.0244(3) Uani 1 1 d . . . O2 O -0.04547(10) 0.59690(11) 0.38532(10) 0.0273(3) Uani 1 1 d . . . O3 O 0.19335(10) 0.61485(11) 0.44157(10) 0.0296(3) Uani 1 1 d . . . O4 O 0.00969(12) 0.31020(13) 0.43073(13) 0.0359(3) Uani 1 1 d . . . N1 N 0.33386(11) 0.67847(12) 0.28234(11) 0.0216(3) Uani 1 1 d . . . N2 N -0.00831(11) 0.68308(13) 0.19330(11) 0.0246(3) Uani 1 1 d . . . O5 O 0.27459(15) 0.28842(14) 0.43158(14) 0.0451(4) Uani 1 1 d . . . C13 C 0.68824(13) 0.42724(14) 0.19970(13) 0.0212(4) Uani 1 1 d . . . C25 C 0.65442(14) 0.21034(15) 0.20662(13) 0.0237(4) Uani 1 1 d . . . C31 C 0.62168(14) 0.24922(15) 0.39723(14) 0.0242(4) Uani 1 1 d . . . C9 C -0.04338(13) 0.68594(16) 0.29826(14) 0.0237(4) Uani 1 1 d . . . C1 C 0.24848(13) 0.69509(15) 0.36516(14) 0.0231(4) Uani 1 1 d . . . C5 C 0.37925(14) 0.56210(15) 0.27414(14) 0.0233(4) Uani 1 1 d . . . H5C H 0.3567 0.4991 0.3484 0.028 Uiso 1 1 calc R . . H5D H 0.4654 0.5567 0.2541 0.028 Uiso 1 1 calc R . . C19 C 0.84154(14) 0.23749(15) 0.26676(15) 0.0254(4) Uani 1 1 d . . . C18 C 0.63833(14) 0.48142(15) 0.10371(13) 0.0240(4) Uani 1 1 d . . . H18 H 0.6096 0.4320 0.0771 0.029 Uiso 1 1 calc R . . C14 C 0.72870(14) 0.50620(15) 0.23393(15) 0.0256(4) Uani 1 1 d . . . H14 H 0.7644 0.4740 0.2978 0.031 Uiso 1 1 calc R . . C26 C 0.53450(15) 0.21272(15) 0.21333(14) 0.0275(4) Uani 1 1 d . . . H26 H 0.4811 0.2589 0.2525 0.033 Uiso 1 1 calc R . . C6 C 0.33373(14) 0.54073(16) 0.18645(15) 0.0261(4) Uani 1 1 d . . . H6A H 0.3551 0.6037 0.1119 0.031 Uiso 1 1 calc R . . H6B H 0.3683 0.4622 0.1804 0.031 Uiso 1 1 calc R . . C16 C 0.66912(15) 0.67884(16) 0.08294(15) 0.0312(4) Uani 1 1 d . . . H16 H 0.6629 0.7629 0.0440 0.037 Uiso 1 1 calc R . . C36 C 0.56474(14) 0.33311(16) 0.44777(14) 0.0255(4) Uani 1 1 d . . . H36 H 0.5782 0.4147 0.4085 0.031 Uiso 1 1 calc R . . C7 C 0.15630(14) 0.55213(17) 0.13128(14) 0.0276(4) Uani 1 1 d . . . H7A H 0.1765 0.4774 0.1142 0.033 Uiso 1 1 calc R . . H7B H 0.1843 0.6193 0.0622 0.033 Uiso 1 1 calc R . . C8 C 0.02606(14) 0.57342(16) 0.16878(15) 0.0267(4) Uani 1 1 d . . . H8A H -0.0125 0.5775 0.1087 0.032 Uiso 1 1 calc R . . H8B H -0.0008 0.5051 0.2371 0.032 Uiso 1 1 calc R . . C17 C 0.62912(15) 0.60446(16) 0.04576(14) 0.0289(4) Uani 1 1 d . . . H17 H 0.5953 0.6372 -0.0193 0.035 Uiso 1 1 calc R . . C15 C 0.71873(14) 0.62906(16) 0.17832(16) 0.0304(4) Uani 1 1 d . . . H15 H 0.7458 0.6793 0.2053 0.036 Uiso 1 1 calc R . . C27 C 0.49072(17) 0.15060(16) 0.16524(15) 0.0324(4) Uani 1 1 d . . . H27 H 0.4090 0.1554 0.1717 0.039 Uiso 1 1 calc R . . C24 C 0.92689(15) 0.29463(17) 0.17483(16) 0.0308(4) Uani 1 1 d . . . H24 H 0.9029 0.3651 0.1176 0.037 Uiso 1 1 calc R . . C32 C 0.59808(17) 0.13063(17) 0.46230(15) 0.0326(4) Uani 1 1 d . . . H32 H 0.6344 0.0696 0.4327 0.039 Uiso 1 1 calc R . . C4 C 0.38430(15) 0.78702(15) 0.20314(14) 0.0276(4) Uani 1 1 d . . . H4C H 0.3878 0.7951 0.1243 0.033 Uiso 1 1 calc R . . H4D H 0.4638 0.7875 0.2128 0.033 Uiso 1 1 calc R . . C2 C 0.23174(15) 0.82485(16) 0.35200(16) 0.0301(4) Uani 1 1 d . . . H2A H 0.2624 0.8370 0.4099 0.036 Uiso 1 1 calc R . . H2B H 0.1482 0.8557 0.3585 0.036 Uiso 1 1 calc R . . B22 B 0.70164(16) 0.28224(17) 0.26853(16) 0.0225(4) Uani 1 1 d . . . C20 C 0.88463(16) 0.13498(16) 0.34803(16) 0.0330(4) Uani 1 1 d . . . H20 H 0.8312 0.0928 0.4126 0.040 Uiso 1 1 calc R . . C3 C 0.30083(16) 0.88713(16) 0.23363(16) 0.0341(4) Uani 1 1 d . . . H3A H 0.3445 0.9485 0.2337 0.041 Uiso 1 1 calc R . . H3B H 0.2482 0.9259 0.1794 0.041 Uiso 1 1 calc R . . C33 C 0.52436(18) 0.09838(18) 0.56754(16) 0.0392(5) Uani 1 1 d . . . H33 H 0.5122 0.0167 0.6085 0.047 Uiso 1 1 calc R . . C28 C 0.56504(18) 0.08181(17) 0.10807(15) 0.0367(5) Uani 1 1 d . . . H28 H 0.5353 0.0383 0.0759 0.044 Uiso 1 1 calc R . . C30 C 0.72661(16) 0.14075(17) 0.14676(15) 0.0312(4) Uani 1 1 d . . . H30 H 0.8086 0.1364 0.1386 0.037 Uiso 1 1 calc R . . C35 C 0.48927(16) 0.30257(18) 0.55298(15) 0.0336(4) Uani 1 1 d . . . H35 H 0.4521 0.3628 0.5834 0.040 Uiso 1 1 calc R . . C10 C -0.07964(16) 0.81436(16) 0.28946(16) 0.0328(4) Uani 1 1 d . . . H10A H -0.0495 0.8330 0.3440 0.039 Uiso 1 1 calc R . . H10B H -0.1655 0.8314 0.3035 0.039 Uiso 1 1 calc R . . C34 C 0.46872(17) 0.1847(2) 0.61280(16) 0.0396(5) Uani 1 1 d . . . H34 H 0.4170 0.1632 0.6842 0.047 Uiso 1 1 calc R . . C21 C 1.00192(19) 0.09254(19) 0.33812(19) 0.0453(6) Uani 1 1 d . . . H21 H 1.0269 0.0227 0.3954 0.054 Uiso 1 1 calc R . . C12 C -0.01302(17) 0.80117(17) 0.10482(16) 0.0356(5) Uani 1 1 d . . . H12A H -0.0808 0.8152 0.0692 0.043 Uiso 1 1 calc R . . H12B H 0.0591 0.8103 0.0459 0.043 Uiso 1 1 calc R . . C23 C 1.04492(16) 0.25332(19) 0.16333(19) 0.0392(5) Uani 1 1 d . . . H23 H 1.0993 0.2950 0.0994 0.047 Uiso 1 1 calc R . . C29 C 0.68369(18) 0.07760(18) 0.09864(16) 0.0389(5) Uani 1 1 d . . . H29 H 0.7363 0.0313 0.0591 0.047 Uiso 1 1 calc R . . C22 C 1.08246(18) 0.1510(2) 0.2458(2) 0.0460(6) Uani 1 1 d . . . H22 H 1.1627 0.1216 0.2388 0.055 Uiso 1 1 calc R . . C11 C -0.02520(19) 0.88590(18) 0.16847(17) 0.0433(5) Uani 1 1 d . . . H11A H -0.0763 0.9596 0.1373 0.052 Uiso 1 1 calc R . . H11B H 0.0518 0.9081 0.1644 0.052 Uiso 1 1 calc R . . H4A H -0.061(2) 0.336(2) 0.466(2) 0.081(9) Uiso 1 1 d . . . H4B H -0.004(2) 0.282(2) 0.390(2) 0.061(8) Uiso 1 1 d . . . H5A H 0.236(3) 0.229(3) 0.443(3) 0.110(13) Uiso 1 1 d . . . H5B H 0.334(3) 0.264(3) 0.458(3) 0.102(12) Uiso 1 1 d . . . 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 Na1 0.0234(3) 0.0272(4) 0.0246(4) -0.0113(3) -0.0010(3) -0.0048(3) O1 0.0184(6) 0.0345(7) 0.0227(6) -0.0133(5) -0.0027(5) -0.0032(5) O2 0.0279(6) 0.0294(7) 0.0231(6) -0.0096(5) -0.0025(5) -0.0029(5) O3 0.0271(6) 0.0322(7) 0.0317(7) -0.0163(6) 0.0040(5) -0.0110(5) O4 0.0322(8) 0.0420(9) 0.0427(9) -0.0288(7) 0.0040(6) -0.0114(6) N1 0.0197(7) 0.0222(7) 0.0233(7) -0.0086(6) -0.0033(5) -0.0032(5) N2 0.0222(7) 0.0292(8) 0.0224(7) -0.0093(6) -0.0049(6) -0.0017(6) O5 0.0348(9) 0.0403(9) 0.0567(10) -0.0167(8) -0.0082(7) 0.0017(7) C13 0.0161(8) 0.0215(9) 0.0224(9) -0.0074(7) 0.0012(6) -0.0014(6) C25 0.0310(9) 0.0191(9) 0.0189(8) -0.0007(7) -0.0093(7) -0.0044(7) C31 0.0275(9) 0.0232(9) 0.0235(9) -0.0045(7) -0.0116(7) -0.0057(7) C9 0.0171(8) 0.0295(10) 0.0268(9) -0.0118(8) -0.0052(7) -0.0025(7) C1 0.0184(8) 0.0286(9) 0.0276(9) -0.0147(8) -0.0059(7) -0.0027(7) C5 0.0179(8) 0.0261(9) 0.0256(9) -0.0107(7) -0.0022(7) -0.0013(7) C19 0.0287(9) 0.0232(9) 0.0326(10) -0.0172(8) -0.0118(7) 0.0017(7) C18 0.0236(8) 0.0246(9) 0.0201(8) -0.0080(7) 0.0004(7) -0.0002(7) C14 0.0206(8) 0.0246(9) 0.0309(10) -0.0096(7) -0.0042(7) -0.0026(7) C26 0.0329(10) 0.0212(9) 0.0260(9) -0.0014(7) -0.0103(7) -0.0057(7) C6 0.0197(8) 0.0319(10) 0.0293(9) -0.0167(8) -0.0002(7) -0.0021(7) C16 0.0261(9) 0.0212(9) 0.0336(10) -0.0029(8) 0.0052(7) -0.0023(7) C36 0.0280(9) 0.0251(9) 0.0232(9) -0.0054(7) -0.0081(7) -0.0053(7) C7 0.0245(9) 0.0376(11) 0.0258(9) -0.0169(8) -0.0041(7) -0.0043(7) C8 0.0253(9) 0.0344(10) 0.0249(9) -0.0150(8) -0.0040(7) -0.0050(7) C17 0.0282(9) 0.0274(10) 0.0206(9) -0.0033(7) 0.0012(7) 0.0020(7) C15 0.0202(9) 0.0238(9) 0.0455(11) -0.0137(8) 0.0007(8) -0.0055(7) C27 0.0397(11) 0.0265(10) 0.0282(10) 0.0039(8) -0.0161(8) -0.0131(8) C24 0.0283(9) 0.0318(10) 0.0395(11) -0.0203(9) -0.0086(8) -0.0006(8) C32 0.0476(11) 0.0259(10) 0.0274(10) -0.0045(8) -0.0149(8) -0.0116(8) C4 0.0298(9) 0.0276(10) 0.0236(9) -0.0055(7) -0.0043(7) -0.0077(7) C2 0.0263(9) 0.0283(10) 0.0393(11) -0.0172(8) -0.0051(8) -0.0017(7) B22 0.0246(10) 0.0209(10) 0.0230(10) -0.0079(8) -0.0069(8) -0.0016(7) C20 0.0406(11) 0.0276(10) 0.0373(11) -0.0183(8) -0.0170(9) 0.0086(8) C3 0.0348(10) 0.0246(10) 0.0435(11) -0.0090(8) -0.0129(9) -0.0037(8) C33 0.0573(13) 0.0371(12) 0.0253(10) 0.0017(9) -0.0156(9) -0.0272(10) C28 0.0571(13) 0.0329(11) 0.0261(10) -0.0051(8) -0.0158(9) -0.0195(9) C30 0.0340(10) 0.0337(11) 0.0297(10) -0.0135(8) -0.0076(8) -0.0057(8) C35 0.0322(10) 0.0451(12) 0.0258(10) -0.0134(9) -0.0058(8) -0.0078(8) C10 0.0302(10) 0.0307(10) 0.0397(11) -0.0156(9) -0.0090(8) 0.0017(8) C34 0.0417(11) 0.0566(14) 0.0199(9) -0.0052(9) -0.0035(8) -0.0254(10) C21 0.0517(13) 0.0405(12) 0.0549(14) -0.0288(11) -0.0301(11) 0.0213(10) C12 0.0347(10) 0.0354(11) 0.0284(10) -0.0020(8) -0.0073(8) -0.0031(8) C23 0.0280(10) 0.0460(13) 0.0571(14) -0.0360(11) -0.0051(9) -0.0019(9) C29 0.0515(13) 0.0398(12) 0.0327(11) -0.0193(9) -0.0075(9) -0.0091(9) C22 0.0334(11) 0.0524(14) 0.0698(16) -0.0428(13) -0.0231(11) 0.0176(10) C11 0.0499(13) 0.0283(11) 0.0465(13) -0.0062(9) -0.0133(10) -0.0024(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Na1 Na1 3.4303(12) 2_566 ? Na1 O1 2.4652(12) . ? Na1 O2 2.3293(13) 2_566 ? Na1 O2 2.4434(13) . ? Na1 O3 2.3876(13) . ? Na1 O4 2.3726(15) . ? Na1 O5 2.3971(17) . ? O1 C6 1.4304(19) . ? O1 C7 1.4257(19) . ? O2 Na1 2.3293(13) 2_566 ? O2 C9 1.234(2) . ? O3 C1 1.2439(19) . ? N1 C1 1.334(2) . ? N1 C5 1.451(2) . ? N1 C4 1.455(2) . ? N2 C9 1.343(2) . ? N2 C8 1.451(2) . ? N2 C12 1.462(2) . ? C13 C18 1.403(2) . ? C13 C14 1.406(2) . ? C13 B22 1.643(2) . ? C25 C26 1.407(2) . ? C25 B22 1.646(3) . ? C25 C30 1.400(2) . ? C31 C36 1.402(2) . ? C31 C32 1.406(2) . ? C31 B22 1.649(3) . ? C9 C10 1.507(2) . ? C1 C2 1.501(2) . ? C5 C6 1.512(2) . ? C19 C24 1.404(2) . ? C19 B22 1.652(2) . ? C19 C20 1.404(2) . ? C18 C17 1.392(2) . ? C14 C15 1.386(2) . ? C26 C27 1.388(3) . ? C16 C17 1.381(3) . ? C16 C15 1.393(3) . ? C36 C35 1.396(2) . ? C7 C8 1.510(2) . ? C27 C28 1.381(3) . ? C24 C23 1.393(3) . ? C32 C33 1.388(3) . ? C4 C3 1.531(2) . ? C2 C3 1.530(3) . ? C20 C21 1.388(3) . ? C33 C34 1.380(3) . ? C28 C29 1.383(3) . ? C30 C29 1.392(3) . ? C35 C34 1.381(3) . ? C10 C11 1.524(3) . ? C21 C22 1.378(3) . ? C12 C11 1.523(3) . ? C23 C22 1.386(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Na1 Na1 128.71(4) . 2_566 ? O2 Na1 Na1 45.39(3) 2_566 2_566 ? O2 Na1 Na1 42.74(3) . 2_566 ? O2 Na1 O1 169.22(5) 2_566 . ? O2 Na1 O1 86.64(4) . . ? O2 Na1 O2 88.13(5) 2_566 . ? O2 Na1 O3 84.74(5) 2_566 . ? O2 Na1 O4 84.89(5) 2_566 . ? O2 Na1 O5 99.09(5) 2_566 . ? O3 Na1 Na1 81.10(4) . 2_566 ? O3 Na1 O1 85.24(4) . . ? O3 Na1 O2 82.54(5) . . ? O3 Na1 O5 111.29(6) . . ? O4 Na1 Na1 83.33(4) . 2_566 ? O4 Na1 O1 104.08(5) . . ? O4 Na1 O2 85.51(5) . . ? O4 Na1 O3 164.40(5) . . ? O4 Na1 O5 81.87(6) . . ? O5 Na1 Na1 142.62(5) . 2_566 ? O5 Na1 O1 88.24(5) . . ? O5 Na1 O2 164.81(6) . . ? C6 O1 Na1 118.12(9) . . ? C7 O1 Na1 124.47(9) . . ? C7 O1 C6 112.25(12) . . ? Na1 O2 Na1 91.86(5) 2_566 . ? C9 O2 Na1 122.43(10) . . ? C9 O2 Na1 138.17(11) . 2_566 ? C1 O3 Na1 126.87(11) . . ? C1 N1 C5 123.84(14) . . ? C1 N1 C4 114.30(14) . . ? C5 N1 C4 121.74(13) . . ? C9 N2 C8 123.66(14) . . ? C9 N2 C12 113.69(15) . . ? C8 N2 C12 122.59(14) . . ? C18 C13 C14 115.22(15) . . ? C18 C13 B22 123.79(15) . . ? C14 C13 B22 120.98(15) . . ? C26 C25 B22 120.99(15) . . ? C30 C25 C26 114.66(16) . . ? C30 C25 B22 124.33(15) . . ? C36 C31 C32 114.37(16) . . ? C36 C31 B22 124.95(15) . . ? C32 C31 B22 120.49(16) . . ? O2 C9 N2 124.56(16) . . ? O2 C9 C10 127.24(16) . . ? N2 C9 C10 108.19(15) . . ? O3 C1 N1 124.97(16) . . ? O3 C1 C2 125.95(15) . . ? N1 C1 C2 109.07(14) . . ? N1 C5 C6 111.61(13) . . ? C24 C19 B22 120.90(15) . . ? C20 C19 C24 114.61(16) . . ? C20 C19 B22 124.18(16) . . ? C17 C18 C13 122.87(17) . . ? C15 C14 C13 122.73(17) . . ? C27 C26 C25 122.91(18) . . ? O1 C6 C5 108.23(13) . . ? C17 C16 C15 119.17(17) . . ? C35 C36 C31 123.17(17) . . ? O1 C7 C8 108.20(13) . . ? N2 C8 C7 112.24(14) . . ? C16 C17 C18 119.96(17) . . ? C14 C15 C16 120.03(18) . . ? C28 C27 C26 120.52(18) . . ? C23 C24 C19 123.35(18) . . ? C33 C32 C31 123.27(19) . . ? N1 C4 C3 103.70(13) . . ? C1 C2 C3 104.44(14) . . ? C13 B22 C25 111.00(13) . . ? C13 B22 C31 110.64(14) . . ? C13 B22 C19 108.03(13) . . ? C25 B22 C31 106.29(13) . . ? C25 B22 C19 107.84(14) . . ? C31 B22 C19 113.03(14) . . ? C21 C20 C19 122.87(19) . . ? C2 C3 C4 104.82(14) . . ? C34 C33 C32 120.13(18) . . ? C27 C28 C29 118.53(18) . . ? C29 C30 C25 122.94(18) . . ? C34 C35 C36 119.92(19) . . ? C9 C10 C11 103.89(15) . . ? C33 C34 C35 119.12(18) . . ? C22 C21 C20 120.47(19) . . ? N2 C12 C11 103.10(15) . . ? C22 C23 C24 119.6(2) . . ? C28 C29 C30 120.44(19) . . ? C21 C22 C23 119.14(18) . . ? C12 C11 C10 104.10(15) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 -16 0 0.0967 0.0000 -16.0000 0.0000 0.2354 0.9871 -0.0299 0 16 0 0.0967 -0.0000 16.0000 -0.0000 -0.2354 -0.9871 0.0299 -14 7 0 0.2232 -14.0000 7.0000 0.0000 -0.1186 -0.4946 0.8758 -15 -8 0 0.2111 -15.0000 -8.0000 0.0000 0.1009 0.4264 0.9094 16 1 0 0.2524 16.0000 1.0000 -0.0000 0.0032 0.0099 -0.9841 0 -1 -17 0.0620 0.0000 -1.0000 -17.0000 0.8253 -0.5077 -0.2342 0 1 17 0.0620 -0.0000 1.0000 17.0000 -0.8253 0.5077 0.2342 _database_code_depnum_ccdc_archive 'CCDC 965881' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ap74_16a _audit_creation_date 2013-07-08 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C48 H80 N8 Na2 O12, 2(C24 H20 B)' _chemical_formula_sum 'C96 H120 B2 N8 Na2 O12' _chemical_formula_weight 1645.60 _chemical_melting_point ? _chemical_oxdiff_formula NaBC48H60N4O6 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 11.5127(6) _cell_length_b 13.7549(9) _cell_length_c 15.9209(7) _cell_angle_alpha 71.514(5) _cell_angle_beta 79.756(4) _cell_angle_gamma 66.772(5) _cell_volume 2193.2(2) _cell_formula_units_Z 1 _cell_measurement_reflns_used 6602 _cell_measurement_temperature 120 _cell_measurement_theta_max 32.6616 _cell_measurement_theta_min 2.6974 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.4125 _exptl_crystal_size_mid 0.2418 _exptl_crystal_size_min 0.1581 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_unetI/netI 0.0646 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 31465 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 2.70 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -92.00 -17.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -57.0000 90.0000 75 #__ type_ start__ end____ width___ exp.time_ 2 omega -95.00 -64.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -57.0000 60.0000 31 #__ type_ start__ end____ width___ exp.time_ 3 omega -48.00 42.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 57.0000 -150.0000 90 #__ type_ start__ end____ width___ exp.time_ 4 omega -78.00 -32.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 179.0000 -180.0000 46 #__ type_ start__ end____ width___ exp.time_ 5 omega 30.00 63.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -100.0000 30.0000 33 #__ type_ start__ end____ width___ exp.time_ 6 omega 43.00 69.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -100.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 7 omega 6.00 32.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -100.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 33.00 69.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -100.0000 -90.0000 36 #__ type_ start__ end____ width___ exp.time_ 9 omega 42.00 69.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -100.0000 -150.0000 27 #__ type_ start__ end____ width___ exp.time_ 10 omega -36.00 48.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 26.9679 -38.0000 -60.0000 84 #__ type_ start__ end____ width___ exp.time_ 11 omega -95.00 -5.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -57.0000 -30.0000 90 #__ type_ start__ end____ width___ exp.time_ 12 omega -95.00 -5.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -57.0000 150.0000 90 #__ type_ start__ end____ width___ exp.time_ 13 omega -103.00 -78.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -179.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 14 omega -95.00 -5.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -26.3429 -57.0000 -120.0000 90 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0652741000 _diffrn_orient_matrix_UB_12 0.0257549000 _diffrn_orient_matrix_UB_13 0.0109331000 _diffrn_orient_matrix_UB_21 0.0134038000 _diffrn_orient_matrix_UB_22 0.0404582000 _diffrn_orient_matrix_UB_23 0.0109818000 _diffrn_orient_matrix_UB_31 -0.0084384000 _diffrn_orient_matrix_UB_32 0.0332046000 _diffrn_orient_matrix_UB_33 -0.0444374000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_special_details ? _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 6919 _reflns_number_total 9579 _reflns_odcompleteness_completeness 99.93 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.44 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.543 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 541 _refine_ls_number_reflns 9579 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0513 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+0.4208P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1090 _refine_ls_wR_factor_ref 0.1235 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C4(H4A,H4B), C5(H5A,H5B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C24(H24A,H24B), C3(H3A,H3B), C12(H12A,H12B), C11(H11A,H11B), C20(H20A,H20B), C10(H10A,H10B), C17(H17A,H17B), C16(H16A,H16B), C18(H18A,H18B), C14(H14A,H14B), C19(H19A,H19B), C23(H23A,H23B), C15(H15A,H15B), C22(H22A,H22B) 2.b Aromatic/amide H refined with riding coordinates: C36(H36), C44(H44), C30(H30), C48(H48), C32(H32), C34(H34), C45(H45), C35(H35), C42(H42), C38(H38), C33(H33), C46(H46), C29(H29), C26(H26), C47(H47), C28(H28), C39(H39), C41(H41), C40(H40), C27(H27) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Na1 Na 0.97756(7) 0.40749(6) 0.10086(4) 0.02268(17) Uani 1 1 d . . . O1 O 1.04198(12) 0.55592(11) 0.05220(8) 0.0236(3) Uani 1 1 d . . . O2 O 1.02369(12) 0.38676(11) 0.25438(8) 0.0244(3) Uani 1 1 d . . . O5 O 1.43582(13) 0.20305(12) -0.02926(8) 0.0308(3) Uani 1 1 d . . . O3 O 0.77918(12) 0.42618(12) 0.16433(8) 0.0312(3) Uani 1 1 d . . . N1 N 1.07681(14) 0.59293(12) 0.17437(9) 0.0204(3) Uani 1 1 d . . . O4 O 1.11019(14) 0.23364(12) 0.11504(9) 0.0375(4) Uani 1 1 d . . . N2 N 0.80619(14) 0.32208(13) 0.30891(9) 0.0224(3) Uani 1 1 d . . . O6 O 1.42616(16) 0.38382(13) 0.19542(11) 0.0500(4) Uani 1 1 d . . . N4 N 1.47407(15) 0.23735(14) 0.13958(10) 0.0257(4) Uani 1 1 d . . . N3 N 1.23119(14) 0.11901(14) 0.03036(11) 0.0267(4) Uani 1 1 d . . . C43 C 0.00434(16) 0.23112(15) 0.61406(11) 0.0165(4) Uani 1 1 d . . . C31 C 0.19365(16) 0.07073(14) 0.55354(11) 0.0155(4) Uani 1 1 d . . . C37 C 0.14822(15) 0.05274(15) 0.72786(11) 0.0171(4) Uani 1 1 d . . . C25 C 0.25122(15) 0.19948(14) 0.61747(11) 0.0174(4) Uani 1 1 d . . . C36 C 0.11213(16) 0.06657(15) 0.50037(11) 0.0179(4) Uani 1 1 d . . . H36 H 0.0242 0.1079 0.5059 0.022 Uiso 1 1 calc R . . C44 C -0.10221(16) 0.20092(15) 0.64614(11) 0.0187(4) Uani 1 1 d . . . H44 H -0.0887 0.1260 0.6763 0.022 Uiso 1 1 calc R . . C1 C 1.10599(17) 0.57955(14) 0.09264(11) 0.0198(4) Uani 1 1 d . . . C30 C 0.28178(16) 0.25875(14) 0.53224(12) 0.0196(4) Uani 1 1 d . . . H30 H 0.2403 0.2641 0.4836 0.024 Uiso 1 1 calc R . . C48 C -0.02425(16) 0.34305(15) 0.56903(11) 0.0200(4) Uani 1 1 d . . . H48 H 0.0437 0.3684 0.5456 0.024 Uiso 1 1 calc R . . C32 C 0.32245(16) 0.00736(15) 0.54088(12) 0.0204(4) Uani 1 1 d . . . H32 H 0.3818 0.0079 0.5751 0.025 Uiso 1 1 calc R . . C34 C 0.28262(17) -0.05756(15) 0.42991(12) 0.0213(4) Uani 1 1 d . . . H34 H 0.3120 -0.1006 0.3888 0.026 Uiso 1 1 calc R . . C45 C -0.22621(16) 0.27519(16) 0.63585(11) 0.0205(4) Uani 1 1 d . . . H45 H -0.2949 0.2509 0.6596 0.025 Uiso 1 1 calc R . . C35 C 0.15515(17) 0.00400(15) 0.43956(11) 0.0207(4) Uani 1 1 d . . . H35 H 0.0966 0.0036 0.4045 0.025 Uiso 1 1 calc R . . C42 C 0.19299(16) -0.06197(15) 0.74462(12) 0.0204(4) Uani 1 1 d . . . H42 H 0.2291 -0.0930 0.6962 0.024 Uiso 1 1 calc R . . C38 C 0.09649(16) 0.09172(15) 0.80320(11) 0.0207(4) Uani 1 1 d . . . H38 H 0.0648 0.1688 0.7959 0.025 Uiso 1 1 calc R . . C33 C 0.36681(17) -0.05552(15) 0.48119(12) 0.0224(4) Uani 1 1 d . . . H33 H 0.4546 -0.0972 0.4753 0.027 Uiso 1 1 calc R . . C46 C -0.24940(17) 0.38495(16) 0.59079(12) 0.0226(4) Uani 1 1 d . . . H46 H -0.3337 0.4362 0.5832 0.027 Uiso 1 1 calc R . . C29 C 0.36945(17) 0.30976(15) 0.51576(12) 0.0231(4) Uani 1 1 d . . . H29 H 0.3859 0.3496 0.4571 0.028 Uiso 1 1 calc R . . C26 C 0.31736(17) 0.19457(16) 0.68542(12) 0.0220(4) Uani 1 1 d . . . H26 H 0.3008 0.1558 0.7444 0.026 Uiso 1 1 calc R . . C8 C 0.93303(17) 0.24548(15) 0.29727(12) 0.0223(4) Uani 1 1 d . . . H8A H 0.9471 0.2387 0.2359 0.027 Uiso 1 1 calc R . . H8B H 0.9413 0.1722 0.3382 0.027 Uiso 1 1 calc R . . C47 C -0.14768(17) 0.41842(15) 0.55717(12) 0.0225(4) Uani 1 1 d . . . H47 H -0.1621 0.4932 0.5259 0.027 Uiso 1 1 calc R . . B1 B 0.14898(18) 0.13898(16) 0.62867(12) 0.0157(4) Uani 1 1 d . . . C28 C 0.43268(17) 0.30251(16) 0.58488(13) 0.0256(4) Uani 1 1 d . . . H28 H 0.4931 0.3369 0.5743 0.031 Uiso 1 1 calc R . . C39 C 0.08974(17) 0.02262(16) 0.88764(12) 0.0245(4) Uani 1 1 d . . . H39 H 0.0539 0.0528 0.9365 0.029 Uiso 1 1 calc R . . C41 C 0.18696(17) -0.13267(16) 0.82887(12) 0.0243(4) Uani 1 1 d . . . H41 H 0.2184 -0.2099 0.8369 0.029 Uiso 1 1 calc R . . C4 C 1.17681(18) 0.60784(16) 0.20878(12) 0.0250(4) Uani 1 1 d . . . H4A H 1.2298 0.5380 0.2482 0.030 Uiso 1 1 calc R . . H4B H 1.1407 0.6644 0.2417 0.030 Uiso 1 1 calc R . . C40 C 0.13507(18) -0.09028(16) 0.90091(12) 0.0258(4) Uani 1 1 d . . . H40 H 0.1306 -0.1379 0.9586 0.031 Uiso 1 1 calc R . . C5 C 0.96610(18) 0.57963(16) 0.23011(12) 0.0247(4) Uani 1 1 d . . . H5A H 0.9014 0.5891 0.1917 0.030 Uiso 1 1 calc R . . H5B H 0.9298 0.6384 0.2609 0.030 Uiso 1 1 calc R . . C9 C 0.74073(17) 0.40475(16) 0.24328(12) 0.0247(4) Uani 1 1 d . . . C2 C 1.22975(18) 0.59581(17) 0.05803(12) 0.0259(4) Uani 1 1 d . . . H2A H 1.2229 0.6467 -0.0025 0.031 Uiso 1 1 calc R . . H2B H 1.2989 0.5249 0.0568 0.031 Uiso 1 1 calc R . . C6 C 0.9940(2) 0.46943(16) 0.29860(12) 0.0268(4) Uani 1 1 d . . . H6A H 1.0662 0.4542 0.3326 0.032 Uiso 1 1 calc R . . H6B H 0.9193 0.4699 0.3406 0.032 Uiso 1 1 calc R . . C13 C 1.17050(18) 0.14071(16) 0.10605(13) 0.0255(4) Uani 1 1 d . . . C27 C 0.40673(18) 0.24456(17) 0.66968(13) 0.0266(4) Uani 1 1 d . . . H27 H 0.4500 0.2387 0.7177 0.032 Uiso 1 1 calc R . . C7 C 1.03410(18) 0.28076(16) 0.31456(12) 0.0251(4) Uani 1 1 d . . . H7A H 1.0231 0.2849 0.3766 0.030 Uiso 1 1 calc R . . H7B H 1.1191 0.2260 0.3059 0.030 Uiso 1 1 calc R . . C24 C 1.49970(19) 0.11932(17) 0.17118(12) 0.0273(4) Uani 1 1 d . . . H24A H 1.5919 0.0766 0.1701 0.033 Uiso 1 1 calc R . . H24B H 1.4594 0.0964 0.1347 0.033 Uiso 1 1 calc R . . C3 C 1.2530(2) 0.64534(18) 0.12437(13) 0.0307(5) Uani 1 1 d . . . H3A H 1.3441 0.6171 0.1349 0.037 Uiso 1 1 calc R . . H3B H 1.2223 0.7266 0.1028 0.037 Uiso 1 1 calc R . . C12 C 0.73660(19) 0.31481(17) 0.39587(12) 0.0285(5) Uani 1 1 d . . . H12A H 0.7904 0.3050 0.4422 0.034 Uiso 1 1 calc R . . H12B H 0.7057 0.2530 0.4130 0.034 Uiso 1 1 calc R . . C11 C 0.6273(2) 0.4242(2) 0.38199(15) 0.0466(6) Uani 1 1 d . . . H11A H 0.6462 0.4764 0.4033 0.056 Uiso 1 1 calc R . . H11B H 0.5488 0.4148 0.4140 0.056 Uiso 1 1 calc R . . C20 C 1.5013(2) 0.29212(18) 0.04861(13) 0.0321(5) Uani 1 1 d . . . H20A H 1.5875 0.2488 0.0289 0.039 Uiso 1 1 calc R . . H20B H 1.5005 0.3652 0.0461 0.039 Uiso 1 1 calc R . . C10 C 0.61361(18) 0.46515(18) 0.28251(13) 0.0315(5) Uani 1 1 d . . . H10A H 0.5461 0.4479 0.2665 0.038 Uiso 1 1 calc R . . H10B H 0.5931 0.5456 0.2613 0.038 Uiso 1 1 calc R . . C17 C 1.22961(18) 0.20463(18) -0.05179(13) 0.0313(5) Uani 1 1 d . . . H17A H 1.1796 0.2771 -0.0406 0.038 Uiso 1 1 calc R . . H17B H 1.1864 0.1960 -0.0960 0.038 Uiso 1 1 calc R . . C16 C 1.3029(2) 0.00288(18) 0.03911(15) 0.0394(6) Uani 1 1 d . . . H16A H 1.3951 -0.0123 0.0324 0.047 Uiso 1 1 calc R . . H16B H 1.2805 -0.0215 -0.0059 0.047 Uiso 1 1 calc R . . C18 C 1.35987(19) 0.2033(2) -0.09043(13) 0.0343(5) Uani 1 1 d . . . H18A H 1.4040 0.1371 -0.1123 0.041 Uiso 1 1 calc R . . H18B H 1.3506 0.2686 -0.1420 0.041 Uiso 1 1 calc R . . C14 C 1.1866(2) 0.03388(17) 0.17661(14) 0.0343(5) Uani 1 1 d . . . H14A H 1.2305 0.0286 0.2269 0.041 Uiso 1 1 calc R . . H14B H 1.1035 0.0272 0.1991 0.041 Uiso 1 1 calc R . . C21 C 1.44364(19) 0.28693(19) 0.20561(14) 0.0335(5) Uani 1 1 d . . . C19 C 1.4084(2) 0.30698(18) -0.01482(13) 0.0344(5) Uani 1 1 d . . . H19A H 1.3206 0.3345 0.0108 0.041 Uiso 1 1 calc R . . H19B H 1.4168 0.3610 -0.0717 0.041 Uiso 1 1 calc R . . C23 C 1.4412(2) 0.1043(2) 0.26572(13) 0.0391(6) Uani 1 1 d . . . H23A H 1.3545 0.1046 0.2681 0.047 Uiso 1 1 calc R . . H23B H 1.4933 0.0343 0.3054 0.047 Uiso 1 1 calc R . . C15 C 1.2653(3) -0.0537(2) 0.1310(2) 0.0788(11) Uani 1 1 d . . . H15A H 1.3415 -0.1041 0.1640 0.095 Uiso 1 1 calc R . . H15B H 1.2157 -0.0971 0.1282 0.095 Uiso 1 1 calc R . . C22 C 1.4384(2) 0.2020(2) 0.29232(14) 0.0395(6) Uani 1 1 d . . . H22A H 1.3598 0.2303 0.3284 0.047 Uiso 1 1 calc R . . H22B H 1.5121 0.1814 0.3269 0.047 Uiso 1 1 calc R . . 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 Na1 0.0309(4) 0.0216(4) 0.0175(3) -0.0063(3) 0.0002(3) -0.0115(3) O1 0.0338(7) 0.0242(7) 0.0179(6) -0.0062(5) -0.0028(5) -0.0149(6) O2 0.0364(7) 0.0201(7) 0.0185(6) -0.0039(5) -0.0030(6) -0.0126(6) O5 0.0320(8) 0.0339(9) 0.0241(7) -0.0083(6) -0.0055(6) -0.0076(7) O3 0.0306(7) 0.0359(9) 0.0202(7) -0.0020(6) -0.0039(6) -0.0083(7) N1 0.0292(8) 0.0172(8) 0.0164(7) -0.0053(6) -0.0024(6) -0.0092(7) O4 0.0496(9) 0.0242(8) 0.0306(8) -0.0099(6) 0.0104(7) -0.0086(7) N2 0.0247(8) 0.0223(9) 0.0181(8) -0.0037(6) 0.0020(6) -0.0092(7) O6 0.0636(11) 0.0308(10) 0.0524(10) -0.0185(8) -0.0219(9) -0.0007(8) N4 0.0274(8) 0.0263(9) 0.0233(8) -0.0071(7) -0.0039(7) -0.0085(7) N3 0.0236(8) 0.0249(9) 0.0299(9) -0.0132(7) -0.0010(7) -0.0030(7) C43 0.0196(9) 0.0176(9) 0.0142(8) -0.0078(7) -0.0009(7) -0.0062(7) C31 0.0178(8) 0.0127(9) 0.0148(8) -0.0014(7) -0.0010(7) -0.0062(7) C37 0.0140(8) 0.0186(9) 0.0211(9) -0.0051(7) -0.0033(7) -0.0076(7) C25 0.0143(8) 0.0138(9) 0.0231(9) -0.0080(7) -0.0004(7) -0.0019(7) C36 0.0158(8) 0.0177(9) 0.0188(9) -0.0038(7) 0.0001(7) -0.0060(7) C44 0.0209(9) 0.0173(9) 0.0198(9) -0.0071(7) -0.0035(7) -0.0063(8) C1 0.0290(10) 0.0120(9) 0.0160(8) -0.0004(7) -0.0046(7) -0.0063(8) C30 0.0173(9) 0.0153(9) 0.0241(9) -0.0049(7) -0.0035(7) -0.0030(7) C48 0.0193(9) 0.0200(10) 0.0199(9) -0.0048(7) 0.0012(7) -0.0078(8) C32 0.0175(9) 0.0186(10) 0.0271(10) -0.0083(8) -0.0023(7) -0.0065(8) C34 0.0273(10) 0.0172(10) 0.0204(9) -0.0085(7) 0.0040(7) -0.0089(8) C45 0.0178(9) 0.0259(10) 0.0221(9) -0.0110(8) 0.0001(7) -0.0094(8) C35 0.0245(9) 0.0199(10) 0.0188(9) -0.0040(7) -0.0023(7) -0.0098(8) C42 0.0204(9) 0.0196(10) 0.0217(9) -0.0058(7) -0.0043(7) -0.0064(8) C38 0.0214(9) 0.0183(10) 0.0210(9) -0.0044(7) -0.0019(7) -0.0063(8) C33 0.0185(9) 0.0199(10) 0.0269(10) -0.0081(8) 0.0032(8) -0.0056(8) C46 0.0170(9) 0.0252(11) 0.0248(10) -0.0115(8) -0.0050(7) -0.0015(8) C29 0.0210(9) 0.0153(10) 0.0275(10) -0.0021(8) 0.0011(8) -0.0049(8) C26 0.0219(9) 0.0240(10) 0.0221(9) -0.0090(8) 0.0009(7) -0.0090(8) C8 0.0269(10) 0.0168(10) 0.0216(9) -0.0035(7) -0.0027(8) -0.0071(8) C47 0.0240(9) 0.0166(10) 0.0225(9) -0.0027(7) -0.0025(8) -0.0042(8) B1 0.0158(9) 0.0134(10) 0.0173(9) -0.0043(8) -0.0015(8) -0.0045(8) C28 0.0196(9) 0.0221(10) 0.0392(11) -0.0128(9) 0.0033(8) -0.0104(8) C39 0.0261(10) 0.0278(11) 0.0194(9) -0.0067(8) 0.0004(8) -0.0102(9) C41 0.0277(10) 0.0171(10) 0.0280(10) -0.0020(8) -0.0078(8) -0.0088(8) C4 0.0327(11) 0.0222(10) 0.0240(10) -0.0093(8) -0.0073(8) -0.0093(9) C40 0.0299(10) 0.0266(11) 0.0195(9) 0.0008(8) -0.0048(8) -0.0129(9) C5 0.0305(10) 0.0227(11) 0.0200(9) -0.0074(8) 0.0029(8) -0.0093(9) C9 0.0249(10) 0.0253(11) 0.0234(10) -0.0034(8) -0.0030(8) -0.0104(9) C2 0.0309(10) 0.0269(11) 0.0217(9) -0.0056(8) -0.0029(8) -0.0126(9) C6 0.0384(11) 0.0264(11) 0.0182(9) -0.0079(8) 0.0027(8) -0.0149(9) C13 0.0245(10) 0.0230(11) 0.0302(10) -0.0084(8) -0.0017(8) -0.0086(9) C27 0.0240(10) 0.0315(12) 0.0313(11) -0.0157(9) -0.0020(8) -0.0116(9) C7 0.0308(10) 0.0196(10) 0.0228(9) -0.0004(8) -0.0055(8) -0.0096(9) C24 0.0307(10) 0.0274(11) 0.0267(10) -0.0042(8) -0.0053(8) -0.0145(9) C3 0.0375(11) 0.0304(12) 0.0310(11) -0.0061(9) -0.0068(9) -0.0190(10) C12 0.0340(11) 0.0303(12) 0.0207(10) -0.0055(8) 0.0045(8) -0.0148(9) C11 0.0362(13) 0.0483(16) 0.0348(12) -0.0060(11) 0.0105(10) -0.0037(11) C20 0.0396(12) 0.0288(12) 0.0281(11) -0.0023(9) -0.0029(9) -0.0164(10) C10 0.0247(10) 0.0306(12) 0.0360(12) -0.0095(9) -0.0015(9) -0.0064(9) C17 0.0272(10) 0.0374(13) 0.0237(10) -0.0100(9) -0.0056(8) -0.0029(9) C16 0.0347(12) 0.0308(13) 0.0519(14) -0.0225(11) -0.0169(10) 0.0038(10) C18 0.0324(11) 0.0434(14) 0.0229(10) -0.0122(9) -0.0045(9) -0.0058(10) C14 0.0424(12) 0.0253(12) 0.0353(12) -0.0001(9) -0.0104(10) -0.0154(10) C21 0.0290(11) 0.0332(13) 0.0361(12) -0.0139(10) -0.0117(9) -0.0013(10) C19 0.0378(12) 0.0295(12) 0.0261(11) -0.0040(9) -0.0057(9) -0.0032(10) C23 0.0425(13) 0.0520(15) 0.0256(11) -0.0051(10) -0.0029(9) -0.0239(12) C15 0.0654(19) 0.0231(14) 0.114(3) -0.0088(15) 0.0438(18) -0.0092(13) C22 0.0361(12) 0.0499(15) 0.0279(11) -0.0153(10) -0.0032(9) -0.0066(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Na1 Na1 3.5102(14) 2_765 ? Na1 O1 2.3600(13) 2_765 ? Na1 O1 2.3033(15) . ? Na1 O2 2.4976(14) . ? Na1 O3 2.2769(15) . ? Na1 O4 2.2363(16) . ? O1 Na1 2.3600(13) 2_765 ? O1 C1 1.246(2) . ? O2 C6 1.421(2) . ? O2 C7 1.441(2) . ? O5 C18 1.419(2) . ? O5 C19 1.422(3) . ? O3 C9 1.238(2) . ? N1 C1 1.337(2) . ? N1 C4 1.466(2) . ? N1 C5 1.458(2) . ? O4 C13 1.232(2) . ? N2 C8 1.446(2) . ? N2 C9 1.343(2) . ? N2 C12 1.466(2) . ? O6 C21 1.227(3) . ? N4 C24 1.460(3) . ? N4 C20 1.448(2) . ? N4 C21 1.352(3) . ? N3 C13 1.339(2) . ? N3 C17 1.453(3) . ? N3 C16 1.453(3) . ? C43 C44 1.408(2) . ? C43 C48 1.406(2) . ? C43 B1 1.649(3) . ? C31 C36 1.399(2) . ? C31 C32 1.409(2) . ? C31 B1 1.640(3) . ? C37 C42 1.402(3) . ? C37 C38 1.408(2) . ? C37 B1 1.648(2) . ? C25 C30 1.409(2) . ? C25 C26 1.400(2) . ? C25 B1 1.647(3) . ? C36 C35 1.395(2) . ? C44 C45 1.391(2) . ? C1 C2 1.509(3) . ? C30 C29 1.388(2) . ? C48 C47 1.392(2) . ? C32 C33 1.383(3) . ? C34 C35 1.384(2) . ? C34 C33 1.387(3) . ? C45 C46 1.389(3) . ? C42 C41 1.394(2) . ? C38 C39 1.388(2) . ? C46 C47 1.384(3) . ? C29 C28 1.382(3) . ? C26 C27 1.397(3) . ? C8 C7 1.520(3) . ? C28 C27 1.382(3) . ? C39 C40 1.386(3) . ? C41 C40 1.385(3) . ? C4 C3 1.529(3) . ? C5 C6 1.511(3) . ? C9 C10 1.506(3) . ? C2 C3 1.533(3) . ? C13 C14 1.506(3) . ? C24 C23 1.521(3) . ? C12 C11 1.513(3) . ? C11 C10 1.518(3) . ? C20 C19 1.512(3) . ? C17 C18 1.512(3) . ? C16 C15 1.500(4) . ? C14 C15 1.503(3) . ? C21 C22 1.509(3) . ? C23 C22 1.519(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Na1 Na1 40.57(3) 2_765 2_765 ? O1 Na1 Na1 41.79(3) . 2_765 ? O1 Na1 O1 82.35(5) . 2_765 ? O1 Na1 O2 170.06(5) 2_765 . ? O1 Na1 O2 88.37(5) . . ? O2 Na1 Na1 130.06(5) . 2_765 ? O3 Na1 Na1 120.53(5) . 2_765 ? O3 Na1 O1 120.69(6) . . ? O3 Na1 O1 104.92(5) . 2_765 ? O3 Na1 O2 82.88(5) . . ? O4 Na1 Na1 114.14(5) . 2_765 ? O4 Na1 O1 94.01(5) . 2_765 ? O4 Na1 O1 123.48(6) . . ? O4 Na1 O2 88.12(5) . . ? O4 Na1 O3 114.73(6) . . ? Na1 O1 Na1 97.65(5) . 2_765 ? C1 O1 Na1 131.44(11) . 2_765 ? C1 O1 Na1 126.81(11) . . ? C6 O2 Na1 128.84(10) . . ? C6 O2 C7 112.92(13) . . ? C7 O2 Na1 113.38(10) . . ? C18 O5 C19 115.21(15) . . ? C9 O3 Na1 130.86(12) . . ? C1 N1 C4 113.15(15) . . ? C1 N1 C5 124.69(15) . . ? C5 N1 C4 121.66(14) . . ? C13 O4 Na1 165.44(15) . . ? C8 N2 C12 121.78(15) . . ? C9 N2 C8 124.54(15) . . ? C9 N2 C12 113.67(16) . . ? C20 N4 C24 123.09(16) . . ? C21 N4 C24 113.47(16) . . ? C21 N4 C20 122.49(18) . . ? C13 N3 C17 122.77(17) . . ? C13 N3 C16 113.82(17) . . ? C16 N3 C17 123.36(17) . . ? C44 C43 B1 120.90(15) . . ? C48 C43 C44 114.55(15) . . ? C48 C43 B1 124.54(15) . . ? C36 C31 C32 115.04(16) . . ? C36 C31 B1 125.00(15) . . ? C32 C31 B1 119.93(15) . . ? C42 C37 C38 114.74(16) . . ? C42 C37 B1 124.43(15) . . ? C38 C37 B1 120.80(16) . . ? C30 C25 B1 119.10(15) . . ? C26 C25 C30 114.79(16) . . ? C26 C25 B1 126.05(16) . . ? C35 C36 C31 122.47(16) . . ? C45 C44 C43 123.32(17) . . ? O1 C1 N1 125.36(17) . . ? O1 C1 C2 125.61(16) . . ? N1 C1 C2 109.03(15) . . ? C29 C30 C25 123.34(16) . . ? C47 C48 C43 122.99(17) . . ? C33 C32 C31 123.32(16) . . ? C35 C34 C33 119.04(17) . . ? C46 C45 C44 119.88(17) . . ? C34 C35 C36 120.38(16) . . ? C41 C42 C37 123.13(17) . . ? C39 C38 C37 122.98(18) . . ? C32 C33 C34 119.76(16) . . ? C47 C46 C45 118.95(16) . . ? C28 C29 C30 119.84(17) . . ? C27 C26 C25 122.47(17) . . ? N2 C8 C7 112.63(16) . . ? C46 C47 C48 120.30(17) . . ? C31 B1 C43 111.08(13) . . ? C31 B1 C37 109.25(14) . . ? C31 B1 C25 106.32(13) . . ? C37 B1 C43 107.70(13) . . ? C25 B1 C43 110.50(14) . . ? C25 B1 C37 112.02(13) . . ? C29 C28 C27 119.02(17) . . ? C40 C39 C38 120.18(17) . . ? C40 C41 C42 119.96(18) . . ? N1 C4 C3 102.79(14) . . ? C41 C40 C39 119.01(17) . . ? N1 C5 C6 113.81(16) . . ? O3 C9 N2 125.32(18) . . ? O3 C9 C10 126.52(17) . . ? N2 C9 C10 108.15(16) . . ? C1 C2 C3 103.87(15) . . ? O2 C6 C5 108.70(14) . . ? O4 C13 N3 124.76(18) . . ? O4 C13 C14 126.21(18) . . ? N3 C13 C14 109.02(18) . . ? C28 C27 C26 120.52(17) . . ? O2 C7 C8 109.38(14) . . ? N4 C24 C23 103.30(17) . . ? C4 C3 C2 103.83(15) . . ? N2 C12 C11 103.42(16) . . ? C12 C11 C10 104.85(17) . . ? N4 C20 C19 113.52(17) . . ? C9 C10 C11 104.64(16) . . ? N3 C17 C18 113.70(16) . . ? N3 C16 C15 104.26(18) . . ? O5 C18 C17 113.72(16) . . ? C15 C14 C13 104.71(19) . . ? O6 C21 N4 125.0(2) . . ? O6 C21 C22 126.9(2) . . ? N4 C21 C22 108.07(19) . . ? O5 C19 C20 107.89(16) . . ? C22 C23 C24 104.59(18) . . ? C16 C15 C14 107.5(2) . . ? C21 C22 C23 104.68(17) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -1 -16 -16 0.1138 -1.0000 -16.0000 -16.0000 -0.5217 -0.8364 0.1882 1 16 15 0.1057 1.0000 16.0000 15.0000 0.5108 0.8255 -0.1437 1 2 22 0.1732 1.0000 2.0000 22.0000 0.2268 0.3359 -0.9197 0 -15 5 0.1685 -0.0000 -15.0000 5.0000 -0.3317 -0.5520 -0.7203 0 14 -9 0.1824 0.0000 14.0000 -9.0000 0.2622 0.4676 0.8648 16 6 -1 0.0592 16.0000 6.0000 -1.0000 -0.9008 0.4462 0.1087 -15 -3 -7 0.0950 -15.0000 -3.0000 -7.0000 0.8253 -0.3993 0.3380 -15 -6 4 0.0919 -15.0000 -6.0000 4.0000 0.8683 -0.3999 -0.2504 0 -3 -22 0.1583 0.0000 -3.0000 -22.0000 -0.3178 -0.3630 0.8780 _database_code_depnum_ccdc_archive 'CCDC 965882' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12srv081 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H40 F6 K N4 O6 P' _chemical_formula_weight 664.67 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' K K 0.2009 0.2494 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0028(2) _cell_length_b 8.6199(3) _cell_length_c 13.2814(4) _cell_angle_alpha 79.410(3) _cell_angle_beta 79.591(3) _cell_angle_gamma 74.036(3) _cell_volume 750.45(4) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_max 30.6025 _cell_measurement_theta_min 2.7398 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5484 _exptl_crystal_size_mid 0.4243 _exptl_crystal_size_min 0.1448 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.996 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0584960000 _diffrn_orient_matrix_UB_12 -0.0232769000 _diffrn_orient_matrix_UB_13 0.0468978000 _diffrn_orient_matrix_UB_21 -0.0291922000 _diffrn_orient_matrix_UB_22 0.0818771000 _diffrn_orient_matrix_UB_23 0.0100469000 _diffrn_orient_matrix_UB_31 -0.0839004000 _diffrn_orient_matrix_UB_32 0.0151577000 _diffrn_orient_matrix_UB_33 -0.0266186000 _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19534 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3441 _reflns_number_gt 2977 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.2981P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3441 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0917 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group K1 K 0.5000 0.0000 0.5000 0.01987(11) Uani 1 2 d S . . O1 O 0.33288(17) 0.31798(13) 0.48794(9) 0.0278(3) Uani 1 1 d . . . O3 O 0.40872(15) 0.00042(15) 0.31556(8) 0.0294(3) Uani 1 1 d . . . N2 N 0.69830(17) -0.02946(15) 0.20057(9) 0.0200(3) Uani 1 1 d . . . N1 N 0.58799(19) 0.40136(15) 0.37588(10) 0.0224(3) Uani 1 1 d . . . C8 C 0.8332(2) -0.13660(18) 0.26895(11) 0.0200(3) Uani 1 1 d . . . H8A H 0.9242 -0.2244 0.2319 0.024 Uiso 1 1 calc R . . H8B H 0.7545 -0.1879 0.3289 0.024 Uiso 1 1 calc R . . C1 C 0.3967(2) 0.39231(17) 0.40595(11) 0.0210(3) Uani 1 1 d . . . C2 C 0.2738(3) 0.4875(2) 0.32203(13) 0.0283(3) Uani 1 1 d . . . H2A H 0.1498 0.5618 0.3515 0.034 Uiso 1 1 calc R . . H2B H 0.2368 0.4133 0.2845 0.034 Uiso 1 1 calc R . . C9 C 0.5006(2) 0.02917(19) 0.22880(11) 0.0216(3) Uani 1 1 d . . . C12 C 0.7663(2) 0.0190(2) 0.09132(11) 0.0266(3) Uani 1 1 d . . . H12A H 0.7901 -0.0721 0.0511 0.032 Uiso 1 1 calc R . . H12B H 0.8910 0.0559 0.0828 0.032 Uiso 1 1 calc R . . C11 C 0.5913(3) 0.1596(2) 0.05765(13) 0.0323(4) Uani 1 1 d . . . H11A H 0.6166 0.2662 0.0603 0.039 Uiso 1 1 calc R . . H11B H 0.5701 0.1560 -0.0135 0.039 Uiso 1 1 calc R . . C5 C 0.7515(2) 0.3215(2) 0.43573(13) 0.0278(3) Uani 1 1 d . . . H5A H 0.6967 0.2689 0.5033 0.033 Uiso 1 1 calc R . . H5B H 0.8132 0.4048 0.4492 0.033 Uiso 1 1 calc R . . C10 C 0.4106(2) 0.1322(2) 0.13553(12) 0.0306(4) Uani 1 1 d . . . H10A H 0.3217 0.2372 0.1537 0.037 Uiso 1 1 calc R . . H10B H 0.3324 0.0743 0.1075 0.037 Uiso 1 1 calc R . . C4 C 0.6211(3) 0.4872(2) 0.27095(13) 0.0335(4) Uani 1 1 d . . . H4A H 0.6817 0.4094 0.2207 0.040 Uiso 1 1 calc R . . H4B H 0.7094 0.5608 0.2672 0.040 Uiso 1 1 calc R . . C3 C 0.4106(3) 0.5837(2) 0.25040(14) 0.0376(4) Uani 1 1 d . . . H3A H 0.3815 0.6958 0.2672 0.045 Uiso 1 1 calc R . . H3B H 0.3945 0.5895 0.1772 0.045 Uiso 1 1 calc R . . P1 P 0.0000 0.5000 0.0000 0.02147(13) Uani 1 2 d S . . F3 F 0.22643(15) 0.41334(14) -0.03857(9) 0.0491(3) Uani 1 1 d . . . F2 F 0.02749(15) 0.66656(13) -0.07022(9) 0.0421(3) Uani 1 1 d . . . F1 F 0.0704(2) 0.54835(17) 0.09472(10) 0.0578(4) Uani 1 1 d . . . O2 O 0.82353(14) 0.07046(12) 0.36840(8) 0.0213(2) Uani 1 1 d . . . C7 C 0.9567(2) -0.04554(19) 0.30714(12) 0.0232(3) Uani 1 1 d . . . H7A H 1.0551 -0.1229 0.3491 0.028 Uiso 1 1 calc R . . H7B H 1.0308 0.0109 0.2477 0.028 Uiso 1 1 calc R . . C6 C 0.9120(2) 0.1942(2) 0.38216(14) 0.0288(4) Uani 1 1 d . . . H6A H 0.9683 0.2447 0.3142 0.035 Uiso 1 1 calc R . . H6B H 1.0222 0.1463 0.4246 0.035 Uiso 1 1 calc R . . 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 K1 0.0208(2) 0.0187(2) 0.0172(2) -0.00036(15) 0.00074(16) -0.00383(16) O1 0.0275(6) 0.0203(5) 0.0284(6) 0.0015(4) 0.0053(5) -0.0030(4) O3 0.0159(5) 0.0504(7) 0.0220(5) -0.0063(5) -0.0002(4) -0.0093(5) N2 0.0168(6) 0.0250(6) 0.0177(6) -0.0038(5) -0.0004(5) -0.0054(5) N1 0.0230(6) 0.0196(6) 0.0238(6) -0.0049(5) 0.0018(5) -0.0060(5) C8 0.0168(6) 0.0203(7) 0.0224(7) -0.0050(5) -0.0011(5) -0.0036(5) C1 0.0233(7) 0.0139(6) 0.0244(7) -0.0053(5) 0.0012(6) -0.0032(5) C2 0.0301(8) 0.0250(8) 0.0289(8) -0.0009(6) -0.0061(6) -0.0059(6) C9 0.0173(7) 0.0294(8) 0.0203(7) -0.0068(6) -0.0039(5) -0.0063(6) C12 0.0263(8) 0.0323(8) 0.0192(7) -0.0028(6) 0.0022(6) -0.0080(7) C11 0.0368(9) 0.0331(9) 0.0248(8) 0.0007(7) -0.0059(7) -0.0069(7) C5 0.0230(8) 0.0283(8) 0.0360(9) -0.0146(7) -0.0051(6) -0.0056(6) C10 0.0251(8) 0.0415(9) 0.0234(8) -0.0061(7) -0.0079(6) -0.0013(7) C4 0.0365(9) 0.0320(9) 0.0298(9) 0.0007(7) 0.0057(7) -0.0147(7) C3 0.0433(10) 0.0314(9) 0.0316(9) 0.0068(7) -0.0007(8) -0.0088(8) P1 0.0175(3) 0.0234(3) 0.0212(3) 0.0012(2) -0.0023(2) -0.0045(2) F3 0.0262(5) 0.0516(7) 0.0453(6) 0.0151(5) 0.0080(5) 0.0074(5) F2 0.0335(6) 0.0319(6) 0.0522(7) 0.0142(5) -0.0021(5) -0.0095(4) F1 0.0746(9) 0.0645(8) 0.0460(7) -0.0121(6) -0.0275(6) -0.0215(7) O2 0.0152(5) 0.0222(5) 0.0277(5) -0.0106(4) 0.0014(4) -0.0051(4) C7 0.0147(7) 0.0261(8) 0.0286(8) -0.0110(6) -0.0012(6) -0.0009(6) C6 0.0181(7) 0.0303(8) 0.0426(9) -0.0160(7) -0.0023(6) -0.0078(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag K1 O3 2.6401(11) . ? K1 O3 2.6401(11) 2_656 ? K1 O1 2.6552(11) . ? K1 O1 2.6552(11) 2_656 ? K1 O2 2.7373(10) 2_656 ? K1 O2 2.7373(10) . ? K1 C1 3.3087(14) . ? K1 C1 3.3087(14) 2_656 ? O1 C1 1.2335(18) . ? O3 C9 1.2321(18) . ? N2 C9 1.3453(18) . ? N2 C8 1.4463(18) . ? N2 C12 1.4641(18) . ? N1 C1 1.3463(19) . ? N1 C5 1.453(2) . ? N1 C4 1.464(2) . ? C8 C7 1.516(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C1 C2 1.509(2) . ? C2 C3 1.525(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C9 C10 1.514(2) . ? C12 C11 1.534(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C11 C10 1.526(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C5 C6 1.515(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C4 C3 1.526(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? P1 F1 1.5902(11) 2_565 ? P1 F1 1.5902(11) . ? P1 F3 1.5907(10) 2_565 ? P1 F3 1.5907(10) . ? P1 F2 1.6010(10) 2_565 ? P1 F2 1.6010(10) . ? O2 C6 1.4249(18) . ? O2 C7 1.4294(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 K1 O3 180.0 . 2_656 ? O3 K1 O1 90.25(4) . . ? O3 K1 O1 89.75(4) 2_656 . ? O3 K1 O1 89.75(4) . 2_656 ? O3 K1 O1 90.25(4) 2_656 2_656 ? O1 K1 O1 180.0 . 2_656 ? O3 K1 O2 103.24(3) . 2_656 ? O3 K1 O2 76.76(3) 2_656 2_656 ? O1 K1 O2 91.67(3) . 2_656 ? O1 K1 O2 88.33(3) 2_656 2_656 ? O3 K1 O2 76.76(3) . . ? O3 K1 O2 103.24(3) 2_656 . ? O1 K1 O2 88.33(3) . . ? O1 K1 O2 91.67(3) 2_656 . ? O2 K1 O2 180.00(4) 2_656 . ? O3 K1 C1 77.57(4) . . ? O3 K1 C1 102.43(4) 2_656 . ? O1 K1 C1 20.33(3) . . ? O1 K1 C1 159.67(3) 2_656 . ? O2 K1 C1 109.86(3) 2_656 . ? O2 K1 C1 70.14(3) . . ? O3 K1 C1 102.43(4) . 2_656 ? O3 K1 C1 77.57(4) 2_656 2_656 ? O1 K1 C1 159.67(3) . 2_656 ? O1 K1 C1 20.33(3) 2_656 2_656 ? O2 K1 C1 70.14(3) 2_656 2_656 ? O2 K1 C1 109.86(3) . 2_656 ? C1 K1 C1 180.0 . 2_656 ? C1 O1 K1 111.27(9) . . ? C9 O3 K1 130.33(9) . . ? C9 N2 C8 124.19(12) . . ? C9 N2 C12 113.83(12) . . ? C8 N2 C12 121.92(12) . . ? C1 N1 C5 124.40(13) . . ? C1 N1 C4 113.14(13) . . ? C5 N1 C4 122.20(13) . . ? N2 C8 C7 111.68(12) . . ? N2 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? N2 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? O1 C1 N1 125.77(14) . . ? O1 C1 C2 125.77(14) . . ? N1 C1 C2 108.46(13) . . ? O1 C1 K1 48.40(7) . . ? N1 C1 K1 96.55(9) . . ? C2 C1 K1 131.14(10) . . ? C1 C2 C3 104.55(14) . . ? C1 C2 H2A 110.8 . . ? C3 C2 H2A 110.8 . . ? C1 C2 H2B 110.8 . . ? C3 C2 H2B 110.8 . . ? H2A C2 H2B 108.9 . . ? O3 C9 N2 125.42(14) . . ? O3 C9 C10 126.10(14) . . ? N2 C9 C10 108.46(13) . . ? N2 C12 C11 103.26(12) . . ? N2 C12 H12A 111.1 . . ? C11 C12 H12A 111.1 . . ? N2 C12 H12B 111.1 . . ? C11 C12 H12B 111.1 . . ? H12A C12 H12B 109.1 . . ? C10 C11 C12 104.41(13) . . ? C10 C11 H11A 110.9 . . ? C12 C11 H11A 110.9 . . ? C10 C11 H11B 110.9 . . ? C12 C11 H11B 110.9 . . ? H11A C11 H11B 108.9 . . ? N1 C5 C6 113.09(13) . . ? N1 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? N1 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C9 C10 C11 104.38(13) . . ? C9 C10 H10A 110.9 . . ? C11 C10 H10A 110.9 . . ? C9 C10 H10B 110.9 . . ? C11 C10 H10B 110.9 . . ? H10A C10 H10B 108.9 . . ? N1 C4 C3 103.37(13) . . ? N1 C4 H4A 111.1 . . ? C3 C4 H4A 111.1 . . ? N1 C4 H4B 111.1 . . ? C3 C4 H4B 111.1 . . ? H4A C4 H4B 109.1 . . ? C2 C3 C4 103.95(13) . . ? C2 C3 H3A 111.0 . . ? C4 C3 H3A 111.0 . . ? C2 C3 H3B 111.0 . . ? C4 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? F1 P1 F1 180.00(4) 2_565 . ? F1 P1 F3 89.80(7) 2_565 2_565 ? F1 P1 F3 90.20(7) . 2_565 ? F1 P1 F3 90.20(7) 2_565 . ? F1 P1 F3 89.80(7) . . ? F3 P1 F3 180.00(9) 2_565 . ? F1 P1 F2 90.95(7) 2_565 2_565 ? F1 P1 F2 89.05(7) . 2_565 ? F3 P1 F2 89.89(6) 2_565 2_565 ? F3 P1 F2 90.11(6) . 2_565 ? F1 P1 F2 89.05(7) 2_565 . ? F1 P1 F2 90.95(7) . . ? F3 P1 F2 90.11(6) 2_565 . ? F3 P1 F2 89.89(6) . . ? F2 P1 F2 180.00(9) 2_565 . ? C6 O2 C7 112.75(11) . . ? C6 O2 K1 121.83(9) . . ? C7 O2 K1 121.81(8) . . ? O2 C7 C8 108.29(11) . . ? O2 C7 H7A 110.0 . . ? C8 C7 H7A 110.0 . . ? O2 C7 H7B 110.0 . . ? C8 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? O2 C6 C5 108.36(12) . . ? O2 C6 H6A 110.0 . . ? C5 C6 H6A 110.0 . . ? O2 C6 H6B 110.0 . . ? C5 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.355 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 965883' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ap61_1 _audit_creation_date 2013-01-25 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:17:34, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C48 H84 F24 K4 N8 O14 P4' _chemical_formula_sum 'C48 H84 F24 K4 N8 O14 P4' _chemical_formula_weight 1733.51 _chemical_melting_point ? _chemical_oxdiff_formula 'C12 H20 N2 O3 K P F6' 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' 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' F F 0.0171 0.0103 '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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.4413(11) _cell_length_b 12.8337(3) _cell_length_c 23.8944(8) _cell_angle_alpha 90.00 _cell_angle_beta 120.757(5) _cell_angle_gamma 90.00 _cell_volume 7494.9(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 14684 _cell_measurement_temperature 120 _cell_measurement_theta_max 32.2487 _cell_measurement_theta_min 2.6810 _exptl_absorpt_coefficient_mu 0.443 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.72909 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.536 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 3568 _exptl_crystal_size_max 0.941 _exptl_crystal_size_mid 0.6432 _exptl_crystal_size_min 0.3017 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_unetI/netI 0.0223 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 57703 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.69 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -52.00 38.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -31.8604 57.0000 120.0000 90 #__ type_ start__ end____ width___ exp.time_ 2 omega -100.00 -3.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -31.8604 -57.0000 -30.0000 97 #__ type_ start__ end____ width___ exp.time_ 3 omega -114.00 -35.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -31.8604 179.0000 -180.0000 79 #__ type_ start__ end____ width___ exp.time_ 4 omega -35.00 45.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 32.3292 -57.0000 -180.0000 80 #__ type_ start__ end____ width___ exp.time_ 5 omega 68.00 93.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 32.3292 179.0000 -90.0000 25 #__ type_ start__ end____ width___ exp.time_ 6 omega 47.00 96.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 32.3292 -127.0000 147.0000 49 #__ type_ start__ end____ width___ exp.time_ 7 omega -18.00 71.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 32.3292 0.0000 -30.0000 89 #__ type_ start__ end____ width___ exp.time_ 8 omega -105.00 -2.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -31.8604 -57.0000 60.0000 103 #__ type_ start__ end____ width___ exp.time_ 9 omega -105.00 -2.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -31.8604 -57.0000 -150.0000 103 #__ type_ start__ end____ width___ exp.time_ 10 omega -119.00 -32.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -31.8604 179.0000 -90.0000 87 #__ type_ start__ end____ width___ exp.time_ 11 omega -107.00 5.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -31.8604 -77.0000 150.0000 112 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0128049000 _diffrn_orient_matrix_UB_12 -0.0044629000 _diffrn_orient_matrix_UB_13 0.0187484000 _diffrn_orient_matrix_UB_21 0.0256829000 _diffrn_orient_matrix_UB_22 0.0071095000 _diffrn_orient_matrix_UB_23 0.0289124000 _diffrn_orient_matrix_UB_31 -0.0043836000 _diffrn_orient_matrix_UB_32 0.0546146000 _diffrn_orient_matrix_UB_33 -0.0022143000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 7330 _reflns_number_total 8606 _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.44 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.150 _refine_diff_density_min -1.179 _refine_diff_density_rms 0.074 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 561 _refine_ls_number_reflns 8606 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0677 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+32.6055P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1611 _refine_ls_wR_factor_ref 0.1688 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H19A,H19B} of C19, {H20A,H20B} of C20, {H24A,H24B} of C24, {H22A,H22B} of C22, {H23A,H23B} of C23, {H2AA,H2AB} of C2A, {H3AA,H3AB} of C3A, {H4AA,H4AB} of C4A, {H10C,H10D} of C10A, {H11C,H11D} of C11A, {H12C,H12D} of C12A, {H14A, H14B} of C14, {H7A,H7B} of C7, {H1,H5} of C5, {H17A,H17B} of C17, {H15A,H15B} of C15, {H18A,H18B} of C18, {H10A,H10B} of C10B, {H16A,H16B} of C16, {H4BA, H4BB} of C4B, {H2BA,H2BB} of C2B, {H3BA,H3BB} of C3B, {H11A,H11B} of C11B, {H8A,H8B} of C8, {H12A,H12B} of C12B, {H6A,H6B} of C6 2. Others 1-Sof(O1B)=1-Sof(O1B)=1-Sof(O1B)=1-Sof(O1B)=1-Sof(O1B)=1-Sof(O1B)=1-Sof(O1B)= 1-Sof(O1B)=1-Sof(O1B)=1-Sof(O1B)=1-Sof(O1B)=Sof(O1A)=Sof(C1A)=Sof(C2A)= Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB) 1-Sof(C10B)=1-Sof(C10B)=1-Sof(C10B)=1-Sof(C10B)=1-Sof(C10B)=1-Sof(C10B)=1- Sof(C10B)=1-Sof(C10B)=1-Sof(C10B)=1-Sof(C10B)=1-Sof(C10B)=Sof(O3A)=Sof(C9A)= Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)= Sof(H12C)=Sof(H12D) Fixed Sof: O1S(0.5) O2S(0.5) 3.a Secondary CH2 refined with riding coordinates: C18(H18A,H18B), C15(H15A,H15B), C17(H17A,H17B), C5(H1,H5), C7(H7A,H7B), C14(H14A,H14B), C10B(H10A,H10B), C16(H16A,H16B), C4B(H4BA,H4BB), C2B(H2BA, H2BB), C3B(H3BA,H3BB), C11B(H11A,H11B), C8(H8A,H8B), C12B(H12A,H12B), C6(H6A, H6B), C19(H19A,H19B), C20(H20A,H20B), C24(H24A,H24B), C22(H22A,H22B), C23(H23A, H23B), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C10A(H10C,H10D), C11A(H11C,H11D), C12A(H12C,H12D) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group K1 K 0.08137(3) 0.41054(5) 0.30795(4) 0.03617(17) Uani 1 1 d . . . P2 P 0.11724(3) 0.87079(7) 0.48114(4) 0.03173(19) Uani 1 1 d . . . K2 K 0.06747(3) 0.73229(6) 0.33339(3) 0.03864(19) Uani 1 1 d . . . P1 P 0.19229(5) 0.26517(8) 0.30614(6) 0.0508(3) Uani 1 1 d . . . O2 O 0.12243(9) 0.27565(19) 0.42211(11) 0.0393(5) Uani 1 1 d . A . O4 O -0.03467(10) 0.8187(2) 0.28831(12) 0.0513(7) Uani 1 1 d . . . N3 N -0.10379(12) 0.9215(2) 0.27884(15) 0.0434(7) Uani 1 1 d . A . N1 N 0.01331(14) 0.2003(3) 0.37394(17) 0.0523(8) Uani 1 1 d . . . F3 F 0.17959(12) 0.1812(3) 0.25312(16) 0.0917(11) Uani 1 1 d . A . C13 C -0.06373(12) 0.8508(3) 0.30910(16) 0.0402(8) Uani 1 1 d . . . F2 F 0.13232(14) 0.2380(2) 0.2947(2) 0.1016(13) Uani 1 1 d . A . F4 F 0.24902(12) 0.2921(3) 0.31467(19) 0.0943(11) Uani 1 1 d . A . C18 C -0.17242(16) 0.9340(3) 0.16118(19) 0.0498(9) Uani 1 1 d . A . H18A H -0.2019 0.9512 0.1701 0.060 Uiso 1 1 calc R . . H18B H -0.1806 0.9690 0.1203 0.060 Uiso 1 1 calc R . . C15 C -0.10767(18) 0.8749(4) 0.3711(2) 0.0590(11) Uani 1 1 d . . . H15A H -0.1347 0.8238 0.3687 0.071 Uiso 1 1 calc R A . H15B H -0.0943 0.9167 0.4113 0.071 Uiso 1 1 calc R . . C17 C -0.11826(17) 0.9706(3) 0.2164(2) 0.0511(9) Uani 1 1 d . . . H17A H -0.0894 0.9549 0.2061 0.061 Uiso 1 1 calc R A . H17B H -0.1195 1.0471 0.2207 0.061 Uiso 1 1 calc R . . C5 C 0.05151(18) 0.1562(3) 0.3575(2) 0.0549(10) Uani 1 1 d . A . H1 H 0.0467 0.1910 0.3179 0.066 Uiso 1 1 calc R . . H5 H 0.0432 0.0813 0.3474 0.066 Uiso 1 1 calc R . . C9B C 0.0986(6) 0.5114(10) 0.4567(6) 0.036(2) Uani 0.54(2) 1 d P A 2 C7 C 0.17667(16) 0.2891(4) 0.4745(2) 0.0657(13) Uani 1 1 d . . . H7A H 0.2027 0.2568 0.4638 0.079 Uiso 1 1 calc R A . H7B H 0.1811 0.2551 0.5141 0.079 Uiso 1 1 calc R . . C1B C -0.0144(7) 0.2735(12) 0.3443(8) 0.032(3) Uani 0.48(2) 1 d P A 2 N2 N 0.15103(19) 0.4560(3) 0.50246(16) 0.0702(11) Uani 1 1 d . . . O1B O -0.0132(3) 0.3207(10) 0.2986(6) 0.044(3) Uani 0.48(2) 1 d P . 2 C14 C -0.06063(15) 0.8194(4) 0.37174(19) 0.0590(11) Uani 1 1 d . A . H14A H -0.0253 0.8411 0.4098 0.071 Uiso 1 1 calc R . . H14B H -0.0644 0.7429 0.3734 0.071 Uiso 1 1 calc R . . C10B C 0.0646(7) 0.5350(14) 0.4851(9) 0.060(3) Uani 0.54(2) 1 d P A 2 H10A H 0.0574 0.6107 0.4835 0.072 Uiso 0.54(2) 1 calc PR A 2 H10B H 0.0293 0.4974 0.4617 0.072 Uiso 0.54(2) 1 calc PR A 2 C16 C -0.1331(2) 0.9436(5) 0.3130(3) 0.0785(16) Uani 1 1 d . A . H16A H -0.1725 0.9278 0.2849 0.094 Uiso 1 1 calc R . . H16B H -0.1290 1.0178 0.3260 0.094 Uiso 1 1 calc R . . C4B C -0.0035(9) 0.1346(19) 0.4090(11) 0.069(5) Uani 0.48(2) 1 d P A 2 H4BA H 0.0267 0.1232 0.4543 0.083 Uiso 0.48(2) 1 calc PR A 2 H4BB H -0.0169 0.0665 0.3871 0.083 Uiso 0.48(2) 1 calc PR A 2 F6 F 0.21647(19) 0.1817(3) 0.35877(18) 0.1355(18) Uani 1 1 d . A . C2B C -0.0486(9) 0.311(2) 0.3711(9) 0.063(4) Uani 0.48(2) 1 d P A 2 H2BA H -0.0854 0.3334 0.3364 0.075 Uiso 0.48(2) 1 calc PR A 2 H2BB H -0.0306 0.3679 0.4030 0.075 Uiso 0.48(2) 1 calc PR A 2 F5 F 0.16445(19) 0.3510(4) 0.2534(3) 0.184(3) Uani 1 1 d . A . F1 F 0.1989(2) 0.3531(3) 0.3534(3) 0.159(2) Uani 1 1 d . A . C3B C -0.0510(8) 0.201(3) 0.4067(13) 0.124(12) Uani 0.48(2) 1 d P A 2 H3BA H -0.0442 0.2144 0.4510 0.149 Uiso 0.48(2) 1 calc PR A 2 H3BB H -0.0868 0.1657 0.3806 0.149 Uiso 0.48(2) 1 calc PR A 2 C11B C 0.0975(9) 0.499(3) 0.5526(10) 0.100(8) Uani 0.54(2) 1 d P A 2 H11A H 0.0735 0.4647 0.5659 0.120 Uiso 0.54(2) 1 calc PR A 2 H11B H 0.1156 0.5588 0.5818 0.120 Uiso 0.54(2) 1 calc PR A 2 C8 C 0.1881(2) 0.4033(5) 0.4864(3) 0.0851(18) Uani 1 1 d . A . H8A H 0.2262 0.4132 0.5226 0.102 Uiso 1 1 calc R . . H8B H 0.1848 0.4358 0.4470 0.102 Uiso 1 1 calc R . . C12B C 0.1408(9) 0.4210(15) 0.5585(8) 0.074(5) Uani 0.54(2) 1 d P A 2 H12A H 0.1269 0.3486 0.5517 0.089 Uiso 0.54(2) 1 calc PR A 2 H12B H 0.1747 0.4261 0.6016 0.089 Uiso 0.54(2) 1 calc PR A 2 C6 C 0.10934(16) 0.1676(3) 0.4107(2) 0.0490(9) Uani 1 1 d . . . H6A H 0.1146 0.1342 0.4509 0.059 Uiso 1 1 calc R A . H6B H 0.1338 0.1328 0.3984 0.059 Uiso 1 1 calc R . . F7 F 0.09279(9) 0.91639(17) 0.40878(9) 0.0496(5) Uani 1 1 d . A . F8 F 0.07010(8) 0.78482(19) 0.45174(10) 0.0516(6) Uani 1 1 d . A . F9 F 0.14177(9) 0.8231(2) 0.55178(9) 0.0548(6) Uani 1 1 d . . . F10 F 0.15482(9) 0.79400(19) 0.46853(11) 0.0516(5) Uani 1 1 d . A . O5 O -0.16959(9) 0.82592(19) 0.15504(11) 0.0385(5) Uani 1 1 d . . . F11 F 0.16388(11) 0.9564(2) 0.50858(13) 0.0758(9) Uani 1 1 d . . . F12 F 0.07864(12) 0.9471(3) 0.49172(12) 0.0817(10) Uani 1 1 d . . . C19 C -0.22082(12) 0.7826(3) 0.10545(15) 0.0432(9) Uani 1 1 d . A . H19A H -0.2293 0.8074 0.0620 0.052 Uiso 1 1 calc R . . H19B H -0.2507 0.8052 0.1126 0.052 Uiso 1 1 calc R . . C20 C -0.21629(12) 0.6669(3) 0.10862(14) 0.0397(8) Uani 1 1 d . . . H20A H -0.2507 0.6362 0.0733 0.048 Uiso 1 1 calc R A . H20B H -0.1862 0.6452 0.1018 0.048 Uiso 1 1 calc R . . N4 N -0.20591(10) 0.6275(2) 0.17083(12) 0.0327(6) Uani 1 1 d . A . C21 C -0.15648(12) 0.6027(2) 0.21948(15) 0.0310(6) Uani 1 1 d . . . C24 C -0.24833(15) 0.6252(4) 0.18876(19) 0.0521(10) Uani 1 1 d . . . H24A H -0.2817 0.5892 0.1551 0.063 Uiso 1 1 calc R A . H24B H -0.2581 0.6965 0.1950 0.063 Uiso 1 1 calc R . . O3B O 0.0840(6) 0.5338(6) 0.3994(3) 0.047(2) Uani 0.54(2) 1 d P A 2 O6 O -0.11403(8) 0.60024(18) 0.21706(11) 0.0370(5) Uani 1 1 d . . . C22 C -0.16054(15) 0.5791(3) 0.27860(17) 0.0452(8) Uani 1 1 d . A . H22A H -0.1459 0.6375 0.3101 0.054 Uiso 1 1 calc R . . H22B H -0.1401 0.5148 0.3004 0.054 Uiso 1 1 calc R . . C23 C -0.22109(16) 0.5650(3) 0.25211(19) 0.0520(10) Uani 1 1 d . A . H23A H -0.2316 0.5934 0.2827 0.062 Uiso 1 1 calc R . . H23B H -0.2313 0.4904 0.2444 0.062 Uiso 1 1 calc R . . O1S O -0.00675(16) 0.5716(3) 0.2821(2) 0.0317(9) Uani 0.50 1 d P . . O2S O -0.0152(2) 0.5895(5) 0.3445(3) 0.0573(14) Uani 0.50 1 d P A . O1A O -0.0012(3) 0.3665(8) 0.3267(5) 0.035(2) Uani 0.52(2) 1 d P . 1 C1A C -0.0082(6) 0.3047(13) 0.3591(8) 0.038(3) Uani 0.52(2) 1 d P A 1 C2A C -0.0416(8) 0.312(2) 0.3919(10) 0.093(7) Uani 0.52(2) 1 d P A 1 H2AA H -0.0386 0.3833 0.4093 0.111 Uiso 0.52(2) 1 calc PR A 1 H2AB H -0.0805 0.2987 0.3595 0.111 Uiso 0.52(2) 1 calc PR A 1 C3A C -0.0255(9) 0.2484(17) 0.4367(11) 0.098(6) Uani 0.52(2) 1 d P A 1 H3AA H -0.0574 0.2156 0.4357 0.118 Uiso 0.52(2) 1 calc PR A 1 H3AB H -0.0039 0.2849 0.4789 0.118 Uiso 0.52(2) 1 calc PR A 1 C4A C 0.0073(10) 0.1702(15) 0.4314(9) 0.066(4) Uani 0.52(2) 1 d P A 1 H4AA H -0.0105 0.1013 0.4240 0.079 Uiso 0.52(2) 1 calc PR A 1 H4AB H 0.0436 0.1669 0.4718 0.079 Uiso 0.52(2) 1 calc PR A 1 O3A O 0.1144(6) 0.5437(4) 0.4140(4) 0.031(2) Uani 0.46(2) 1 d P A 1 C9A C 0.1222(8) 0.5178(11) 0.4668(8) 0.042(3) Uani 0.46(2) 1 d P A 1 C10A C 0.0906(9) 0.5538(15) 0.4993(8) 0.062(5) Uani 0.46(2) 1 d P A 1 H10C H 0.0857 0.6304 0.4962 0.074 Uiso 0.46(2) 1 calc PR A 1 H10D H 0.0542 0.5202 0.4789 0.074 Uiso 0.46(2) 1 calc PR A 1 C11A C 0.1250(10) 0.521(3) 0.5672(10) 0.093(8) Uani 0.46(2) 1 d P A 1 H11C H 0.1432 0.5815 0.5959 0.111 Uiso 0.46(2) 1 calc PR A 1 H11D H 0.1031 0.4841 0.5826 0.111 Uiso 0.46(2) 1 calc PR A 1 C12A C 0.1650(8) 0.4511(16) 0.5661(8) 0.066(4) Uani 0.46(2) 1 d P A 1 H12C H 0.2028 0.4761 0.5954 0.079 Uiso 0.46(2) 1 calc PR A 1 H12D H 0.1614 0.3794 0.5787 0.079 Uiso 0.46(2) 1 calc PR A 1 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 K1 0.0511(4) 0.0274(3) 0.0470(4) 0.0001(3) 0.0374(3) 0.0040(3) P2 0.0249(4) 0.0400(4) 0.0227(3) -0.0013(3) 0.0067(3) 0.0027(3) K2 0.0290(3) 0.0442(4) 0.0314(3) -0.0115(3) 0.0073(3) 0.0099(3) P1 0.0678(7) 0.0344(5) 0.0763(7) -0.0072(5) 0.0558(6) 0.0001(4) O2 0.0326(11) 0.0466(13) 0.0361(11) 0.0045(10) 0.0157(10) 0.0193(10) O4 0.0289(12) 0.0713(18) 0.0422(13) -0.0178(13) 0.0098(10) 0.0092(12) N3 0.0423(16) 0.0396(15) 0.0534(17) -0.0004(13) 0.0281(14) 0.0058(13) N1 0.0512(18) 0.058(2) 0.063(2) 0.0299(17) 0.0407(17) 0.0125(16) F3 0.0720(18) 0.136(3) 0.098(2) -0.067(2) 0.0657(17) -0.0410(18) C13 0.0215(14) 0.0485(19) 0.0403(17) -0.0119(15) 0.0083(13) -0.0042(13) F2 0.112(2) 0.0470(14) 0.218(4) -0.030(2) 0.136(3) -0.0099(15) F4 0.0650(18) 0.087(2) 0.152(3) -0.048(2) 0.071(2) -0.0282(16) C18 0.051(2) 0.049(2) 0.052(2) 0.0203(17) 0.0284(18) 0.0194(17) C15 0.059(2) 0.076(3) 0.046(2) -0.004(2) 0.030(2) 0.009(2) C17 0.065(2) 0.0328(18) 0.071(3) 0.0097(17) 0.046(2) 0.0090(17) C5 0.060(2) 0.041(2) 0.077(3) 0.0017(19) 0.045(2) -0.0004(18) C9B 0.048(6) 0.033(4) 0.027(4) -0.004(3) 0.020(5) 0.002(5) C7 0.040(2) 0.096(4) 0.042(2) -0.013(2) 0.0069(17) 0.028(2) C1B 0.029(5) 0.030(6) 0.044(7) 0.002(4) 0.024(5) -0.002(4) N2 0.102(3) 0.071(3) 0.0327(17) -0.0122(17) 0.0310(19) 0.009(2) O1B 0.036(3) 0.053(6) 0.048(5) 0.023(5) 0.025(3) 0.009(3) C14 0.0314(18) 0.091(3) 0.044(2) 0.009(2) 0.0115(16) 0.010(2) C10B 0.073(8) 0.060(7) 0.065(8) 0.018(5) 0.047(8) 0.031(7) C16 0.061(3) 0.113(4) 0.081(3) 0.029(3) 0.051(3) 0.040(3) C4B 0.061(9) 0.093(14) 0.072(12) 0.046(9) 0.047(10) 0.022(9) F6 0.145(4) 0.099(3) 0.086(2) 0.036(2) 0.004(2) -0.042(3) C2B 0.047(6) 0.102(10) 0.047(9) 0.026(8) 0.030(6) 0.016(6) F5 0.112(3) 0.128(4) 0.238(6) 0.112(4) 0.036(4) -0.028(3) F1 0.222(5) 0.099(3) 0.258(6) -0.116(4) 0.196(5) -0.074(3) C3B 0.078(12) 0.22(3) 0.127(18) 0.113(19) 0.086(13) 0.065(14) C11B 0.123(15) 0.144(17) 0.064(11) 0.045(12) 0.070(12) 0.077(16) C8 0.059(3) 0.126(5) 0.059(3) -0.047(3) 0.022(2) -0.021(3) C12B 0.101(12) 0.094(11) 0.042(6) 0.023(6) 0.048(8) 0.038(8) C6 0.056(2) 0.0385(18) 0.065(2) 0.0189(17) 0.040(2) 0.0243(17) F7 0.0594(13) 0.0457(12) 0.0296(9) 0.0069(8) 0.0126(9) 0.0037(10) F8 0.0304(10) 0.0704(15) 0.0427(11) 0.0051(10) 0.0105(9) -0.0142(10) F9 0.0521(13) 0.0771(16) 0.0241(9) 0.0067(10) 0.0114(9) 0.0064(11) F10 0.0433(11) 0.0634(14) 0.0553(13) 0.0064(11) 0.0305(10) 0.0158(10) O5 0.0312(11) 0.0481(14) 0.0356(11) 0.0157(10) 0.0165(10) 0.0139(10) F11 0.0572(15) 0.0516(14) 0.0649(16) 0.0037(12) -0.0076(12) -0.0187(12) F12 0.0742(17) 0.105(2) 0.0512(14) -0.0138(14) 0.0217(13) 0.0479(16) C19 0.0213(14) 0.076(3) 0.0292(15) 0.0183(16) 0.0106(12) 0.0122(15) C20 0.0195(13) 0.074(2) 0.0211(13) 0.0026(14) 0.0073(11) -0.0026(14) N4 0.0219(11) 0.0519(16) 0.0255(12) 0.0019(11) 0.0130(10) 0.0012(11) C21 0.0269(14) 0.0283(14) 0.0342(15) -0.0018(12) 0.0131(12) -0.0019(11) C24 0.0355(18) 0.083(3) 0.051(2) 0.021(2) 0.0318(17) 0.0158(18) O3B 0.049(7) 0.055(3) 0.026(3) -0.003(2) 0.012(3) 0.018(3) O6 0.0239(10) 0.0401(12) 0.0440(12) 0.0080(10) 0.0153(9) 0.0025(9) C22 0.049(2) 0.049(2) 0.0351(17) 0.0108(15) 0.0197(16) 0.0067(16) C23 0.056(2) 0.064(2) 0.055(2) 0.0208(19) 0.042(2) 0.0250(19) O1S 0.0239(19) 0.034(2) 0.037(2) 0.0002(18) 0.0148(17) 0.0043(16) O2S 0.052(3) 0.058(3) 0.048(3) 0.003(3) 0.015(3) 0.009(3) O1A 0.031(3) 0.043(4) 0.036(4) 0.014(3) 0.020(3) 0.015(3) C1A 0.025(5) 0.045(8) 0.045(7) 0.019(5) 0.018(5) 0.013(5) C2A 0.065(9) 0.171(15) 0.083(13) 0.077(12) 0.067(10) 0.074(9) C3A 0.106(14) 0.129(14) 0.113(14) 0.055(11) 0.094(12) 0.041(11) C4A 0.081(10) 0.075(10) 0.061(9) 0.039(7) 0.051(9) 0.016(8) O3A 0.041(6) 0.027(3) 0.024(3) 0.0022(19) 0.016(4) 0.008(3) C9A 0.067(9) 0.025(4) 0.046(7) -0.007(4) 0.037(8) 0.001(6) C10A 0.094(12) 0.051(8) 0.047(7) 0.017(5) 0.040(9) 0.046(9) C11A 0.118(17) 0.133(16) 0.035(7) 0.021(8) 0.045(11) 0.065(17) C12A 0.081(11) 0.084(10) 0.035(5) 0.001(5) 0.032(7) 0.009(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag K1 O2 2.923(2) . ? K1 F2 2.751(3) . ? K1 O1B 2.553(7) 2 ? K1 O1B 2.829(7) . ? K1 F1 3.029(6) . ? K1 O3B 2.667(5) . ? K1 O6 2.777(2) 2 ? K1 O1S 3.057(4) . ? K1 O1S 2.955(4) 2 ? K1 O1A 2.667(5) . ? K1 O1A 2.893(8) 2 ? K1 O3A 2.790(7) . ? P2 F7 1.608(2) . ? P2 F8 1.595(2) . ? P2 F9 1.583(2) . ? P2 F10 1.592(2) . ? P2 F11 1.584(2) . ? P2 F12 1.585(2) . ? K2 O4 2.789(3) 2 ? K2 O4 2.762(2) . ? K2 F7 2.832(2) . ? K2 F8 2.871(2) . ? K2 F10 3.003(2) . ? K2 O5 3.023(2) 2 ? K2 O3B 2.906(7) . ? K2 O6 2.777(2) 2 ? K2 O1S 3.158(4) 2 ? K2 O1S 2.751(4) . ? K2 O2S 3.099(6) . ? K2 O3A 2.953(7) . ? P1 F3 1.558(3) . ? P1 F2 1.622(3) . ? P1 F4 1.558(3) . ? P1 F6 1.522(4) . ? P1 F5 1.551(4) . ? P1 F1 1.539(3) . ? O2 C7 1.415(4) . ? O2 C6 1.426(5) . ? O4 K2 2.789(3) 2 ? O4 C13 1.233(4) . ? N3 C13 1.343(4) . ? N3 C17 1.471(5) . ? N3 C16 1.461(5) . ? N1 C5 1.446(5) . ? N1 C1B 1.198(18) . ? N1 C4B 1.43(2) . ? N1 C1A 1.440(16) . ? N1 C4A 1.518(17) . ? C13 C14 1.509(5) . ? C18 C17 1.502(6) . ? C18 O5 1.402(5) . ? C15 C14 1.509(6) . ? C15 C16 1.485(6) . ? C5 C6 1.485(6) . ? C9B N2 1.502(13) . ? C9B C10B 1.468(17) . ? C9B O3B 1.244(13) . ? C7 C8 1.496(8) . ? C1B O1B 1.263(19) . ? C1B C2B 1.49(3) . ? N2 C8 1.459(7) . ? N2 C12B 1.574(14) . ? N2 C9A 1.146(17) . ? N2 C12A 1.363(16) . ? O1B K1 2.553(7) 2 ? C10B C11B 1.47(2) . ? C4B C3B 1.58(3) . ? C2B C3B 1.67(4) . ? C11B C12B 1.53(3) . ? O5 K2 3.023(2) 2 ? O5 C19 1.439(4) . ? C19 C20 1.490(6) . ? C20 N4 1.450(4) . ? N4 C21 1.326(4) . ? N4 C24 1.473(4) . ? C21 O6 1.238(4) . ? C21 C22 1.506(5) . ? C24 C23 1.513(5) . ? O6 K1 2.778(2) 2 ? O6 K2 2.777(2) 2 ? C22 C23 1.511(5) . ? O1S K1 2.955(4) 2 ? O1S K2 3.158(4) 2 ? O1S O1S 1.760(9) 2 ? O1S O2S 1.644(7) . ? O1A K1 2.892(8) 2 ? O1A C1A 1.194(17) . ? C1A C2A 1.51(2) . ? C2A C3A 1.23(3) . ? C3A C4A 1.42(3) . ? O3A C9A 1.211(16) . ? C9A C10A 1.531(19) . ? C10A C11A 1.46(3) . ? C11A C12A 1.46(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 K1 F1 71.35(12) . . ? O2 K1 O1S 118.95(9) . . ? O2 K1 O1S 152.74(9) . 2 ? F2 K1 O2 69.38(10) . . ? F2 K1 O1B 101.4(3) . . ? F2 K1 F1 45.27(9) . . ? F2 K1 O6 115.28(8) . 2 ? F2 K1 O1S 134.72(13) . 2 ? F2 K1 O1S 161.08(12) . . ? F2 K1 O1A 82.9(2) . 2 ? F2 K1 O3A 130.1(3) . . ? O1B K1 O2 75.07(14) . . ? O1B K1 O2 113.6(4) 2 . ? O1B K1 F2 72.4(3) 2 . ? O1B K1 O1B 62.0(5) 2 . ? O1B K1 F1 139.39(19) . . ? O1B K1 F1 112.53(17) 2 . ? O1B K1 O3B 140.7(4) 2 . ? O1B K1 O6 110.4(4) 2 2 ? O1B K1 O1S 88.7(3) 2 . ? O1B K1 O1S 72.2(4) 2 2 ? O1B K1 O1S 67.1(2) . . ? O1B K1 O1S 85.84(14) . 2 ? O1B K1 O1A 77.7(4) 2 . ? O1B K1 O1A 69.9(4) . 2 ? O1B K1 O1A 15.9(2) 2 2 ? O1B K1 O3A 156.0(3) 2 . ? F1 K1 O1S 151.26(11) . . ? O3B K1 O2 75.88(13) . . ? O3B K1 F2 140.8(2) . . ? O3B K1 O1B 86.2(5) . . ? O3B K1 F1 106.7(3) . . ? O3B K1 O6 77.5(2) . 2 ? O3B K1 O1S 83.72(18) . 2 ? O3B K1 O1S 56.1(3) . . ? O3B K1 O1A 134.7(3) . 2 ? O3B K1 O1A 69.3(4) . . ? O3B K1 O3A 15.78(14) . . ? O6 K1 O2 134.58(7) 2 . ? O6 K1 O1B 138.54(18) 2 . ? O6 K1 F1 82.04(10) 2 . ? O6 K1 O1S 72.17(9) 2 . ? O6 K1 O1S 54.91(9) 2 2 ? O6 K1 O1A 95.3(2) 2 2 ? O6 K1 O3A 70.38(14) 2 . ? O1S K1 F1 132.93(13) 2 . ? O1S K1 O1S 33.98(16) 2 . ? O1A K1 O2 71.55(12) . . ? O1A K1 O2 129.3(2) 2 . ? O1A K1 F2 114.2(2) . . ? O1A K1 O1B 16.90(15) . . ? O1A K1 F1 116.66(14) 2 . ? O1A K1 F1 142.45(15) . . ? O1A K1 O6 129.95(19) . 2 ? O1A K1 O1S 58.41(17) . . ? O1A K1 O1S 78.98(19) 2 . ? O1A K1 O1S 84.50(13) . 2 ? O1A K1 O1S 57.5(2) 2 2 ? O1A K1 O1A 83.4(3) . 2 ? O1A K1 O3A 83.9(4) . . ? O3A K1 O2 74.16(13) . . ? O3A K1 O1B 100.7(4) . . ? O3A K1 F1 91.5(3) . . ? O3A K1 O1S 90.9(2) . 2 ? O3A K1 O1S 68.3(3) . . ? O3A K1 O1A 146.9(3) . 2 ? F7 P2 K2 51.50(8) . . ? F8 P2 K2 52.83(9) . . ? F8 P2 F7 88.53(12) . . ? F9 P2 K2 127.09(10) . . ? F9 P2 F7 178.45(14) . . ? F9 P2 F8 90.86(13) . . ? F9 P2 F10 89.43(13) . . ? F9 P2 F11 90.44(14) . . ? F9 P2 F12 91.85(14) . . ? F10 P2 K2 57.64(9) . . ? F10 P2 F7 89.13(12) . . ? F10 P2 F8 89.01(13) . . ? F11 P2 K2 125.79(13) . . ? F11 P2 F7 90.16(13) . . ? F11 P2 F8 178.56(15) . . ? F11 P2 F10 90.38(15) . . ? F11 P2 F12 90.41(18) . . ? F12 P2 K2 120.88(10) . . ? F12 P2 F7 89.58(14) . . ? F12 P2 F8 90.16(16) . . ? F12 P2 F10 178.49(14) . . ? O4 K2 O4 73.12(11) . 2 ? O4 K2 F7 77.75(7) . . ? O4 K2 F7 99.92(8) 2 . ? O4 K2 F8 77.42(7) . . ? O4 K2 F8 139.46(9) 2 . ? O4 K2 F10 131.90(8) 2 . ? O4 K2 F10 116.11(7) . . ? O4 K2 O5 74.38(7) 2 2 ? O4 K2 O5 130.24(9) . 2 ? O4 K2 O3B 142.14(14) 2 . ? O4 K2 O3B 114.2(3) . . ? O4 K2 O6 135.70(7) . 2 ? O4 K2 O1S 85.71(9) . 2 ? O4 K2 O1S 66.86(10) 2 2 ? O4 K2 O2S 65.02(12) . . ? O4 K2 O2S 117.41(11) 2 . ? O4 K2 O3A 128.2(3) . . ? O4 K2 O3A 143.53(12) 2 . ? F7 K2 F8 46.16(6) . . ? F7 K2 F10 45.14(6) . . ? F7 K2 O5 71.96(7) . 2 ? F7 K2 O3B 117.92(13) . . ? F7 K2 O1S 161.47(9) . 2 ? F7 K2 O2S 113.36(12) . . ? F7 K2 O3A 112.72(16) . . ? F8 K2 F10 44.64(6) . . ? F8 K2 O5 106.07(6) . 2 ? F8 K2 O3B 75.86(12) . . ? F8 K2 O1S 137.81(9) . 2 ? F8 K2 O2S 72.14(12) . . ? F8 K2 O3A 76.99(11) . . ? F10 K2 O5 64.47(6) . 2 ? F10 K2 O1S 153.31(9) . 2 ? F10 K2 O2S 108.11(11) . . ? O5 K2 O1S 114.22(9) 2 2 ? O5 K2 O2S 164.46(12) 2 . ? O3B K2 F10 80.3(2) . . ? O3B K2 O5 114.7(3) . 2 ? O3B K2 O1S 76.46(19) . 2 ? O3B K2 O2S 49.8(3) . . ? O3B K2 O3A 14.85(13) . . ? O6 K2 O4 76.68(8) 2 2 ? O6 K2 F7 139.71(7) 2 . ? O6 K2 F8 142.46(7) 2 . ? O6 K2 F10 108.17(6) 2 . ? O6 K2 O5 68.47(6) 2 2 ? O6 K2 O3B 73.72(18) 2 . ? O6 K2 O1S 52.51(9) 2 2 ? O6 K2 O2S 103.14(12) 2 . ? O6 K2 O3A 68.02(14) 2 . ? O1S K2 O4 93.55(11) . 2 ? O1S K2 O4 73.31(10) . . ? O1S K2 F7 142.82(10) . . ? O1S K2 F8 104.05(10) . . ? O1S K2 F10 134.53(10) . . ? O1S K2 O5 145.22(10) . 2 ? O1S K2 O3B 57.2(3) . . ? O1S K2 O6 77.08(10) . 2 ? O1S K2 O1S 33.76(16) . 2 ? O1S K2 O2S 31.94(14) . . ? O1S K2 O3A 70.4(3) . . ? O2S K2 O1S 65.68(13) . 2 ? O3A K2 F10 70.5(2) . . ? O3A K2 O5 100.0(3) . 2 ? O3A K2 O1S 84.1(2) . 2 ? O3A K2 O2S 64.5(3) . . ? F3 P1 K1 121.05(13) . . ? F3 P1 F2 85.89(16) . . ? F3 P1 F4 93.07(16) . . ? F2 P1 K1 43.74(9) . . ? F4 P1 K1 136.20(13) . . ? F4 P1 F2 178.1(2) . . ? F6 P1 K1 112.0(2) . . ? F6 P1 F3 90.2(2) . . ? F6 P1 F2 88.8(2) . . ? F6 P1 F4 92.7(2) . . ? F6 P1 F5 176.1(3) . . ? F6 P1 F1 94.3(3) . . ? F5 P1 K1 64.2(3) . . ? F5 P1 F3 91.2(3) . . ? F5 P1 F2 87.7(2) . . ? F5 P1 F4 90.8(2) . . ? F1 P1 K1 53.4(2) . . ? F1 P1 F3 173.9(3) . . ? F1 P1 F2 90.2(2) . . ? F1 P1 F4 90.7(2) . . ? F1 P1 F5 84.0(4) . . ? C7 O2 K1 119.2(3) . . ? C7 O2 C6 110.4(3) . . ? C6 O2 K1 117.2(2) . . ? K2 O4 K2 88.36(7) . 2 ? C13 O4 K2 128.1(2) . 2 ? C13 O4 K2 139.9(2) . . ? C13 N3 C17 123.8(3) . . ? C13 N3 C16 113.6(3) . . ? C16 N3 C17 122.6(3) . . ? C5 N1 C4A 126.5(9) . . ? C1B N1 C5 120.3(9) . . ? C1B N1 C4B 119.5(13) . . ? C1B N1 C1A 19.4(9) . . ? C1B N1 C4A 113.0(12) . . ? C4B N1 C5 116.8(10) . . ? C4B N1 C1A 117.7(12) . . ? C4B N1 C4A 25.2(10) . . ? C1A N1 C5 125.5(7) . . ? C1A N1 C4A 103.2(11) . . ? O4 C13 N3 124.6(4) . . ? O4 C13 C14 126.8(3) . . ? N3 C13 C14 108.6(3) . . ? P1 F2 K1 112.22(13) . . ? O5 C18 C17 108.3(3) . . ? C16 C15 C14 107.2(3) . . ? N3 C17 C18 112.7(3) . . ? N1 C5 C6 112.7(4) . . ? C10B C9B N2 113.8(10) . . ? O3B C9B N2 124.0(9) . . ? O3B C9B C10B 122.2(11) . . ? O2 C7 C8 108.7(4) . . ? N1 C1B O1B 125.9(14) . . ? N1 C1B C2B 111.9(16) . . ? O1B C1B C2B 122.0(15) . . ? C9B N2 C12B 102.0(9) . . ? C8 N2 C9B 127.5(6) . . ? C8 N2 C12B 124.4(7) . . ? C9A N2 C9B 20.8(9) . . ? C9A N2 C8 117.6(9) . . ? C9A N2 C12B 117.2(11) . . ? C9A N2 C12A 123.4(11) . . ? C12A N2 C9B 116.6(10) . . ? C12A N2 C8 115.8(9) . . ? C12A N2 C12B 27.5(8) . . ? K1 O1B K1 95.79(17) 2 . ? C1B O1B K1 124.8(9) . . ? C1B O1B K1 137.4(9) . 2 ? C13 C14 C15 105.2(3) . . ? C11B C10B C9B 104.1(11) . . ? N3 C16 C15 105.2(3) . . ? N1 C4B C3B 101.5(15) . . ? C1B C2B C3B 98.9(19) . . ? P1 F5 K1 90.9(3) . . ? P1 F1 K1 102.6(3) . . ? C4B C3B C2B 102.4(14) . . ? C10B C11B C12B 109.7(15) . . ? N2 C8 C7 112.8(5) . . ? C11B C12B N2 103.0(12) . . ? O2 C6 C5 109.0(3) . . ? P2 F7 K2 102.11(10) . . ? P2 F8 K2 100.89(10) . . ? P2 F10 K2 95.77(10) . . ? C18 O5 K2 119.2(2) . 2 ? C18 O5 C19 112.4(3) . . ? C19 O5 K2 116.29(19) . 2 ? O5 C19 C20 108.6(2) . . ? N4 C20 C19 111.5(3) . . ? C20 N4 C24 122.5(3) . . ? C21 N4 C20 123.5(3) . . ? C21 N4 C24 113.5(3) . . ? N4 C21 K1 118.4(2) . 2 ? N4 C21 C22 108.4(3) . . ? O6 C21 K1 43.78(16) . 2 ? O6 C21 N4 125.9(3) . . ? O6 C21 C22 125.7(3) . . ? C22 C21 K1 112.2(2) . 2 ? N4 C24 C23 103.0(3) . . ? K1 O3B K2 98.40(19) . . ? C9B O3B K1 128.2(7) . . ? C9B O3B K2 132.1(7) . . ? K2 O6 K1 98.94(7) 2 2 ? C21 O6 K1 118.3(2) . 2 ? C21 O6 K2 134.2(2) . 2 ? C21 C22 C23 104.4(3) . . ? C22 C23 C24 104.4(3) . . ? K1 O1S K1 83.34(11) 2 . ? K1 O1S K2 130.07(14) . 2 ? K1 O1S K2 87.29(11) 2 2 ? K2 O1S K1 161.93(17) . 2 ? K2 O1S K1 93.09(12) . . ? K2 O1S K2 81.48(11) . 2 ? O1S O1S K1 69.81(18) 2 . ? O1S O1S K1 76.21(19) 2 2 ? O1S O1S K2 60.32(17) 2 2 ? O1S O1S K2 85.92(19) 2 . ? O2S O1S K1 112.0(3) . 2 ? O2S O1S K1 113.4(3) . . ? O2S O1S K2 115.6(3) . 2 ? O2S O1S K2 85.8(3) . . ? O2S O1S O1S 171.2(3) . 2 ? O1S O2S K2 62.3(2) . . ? K1 O1A K1 91.87(18) . 2 ? C1A O1A K1 123.7(8) . 2 ? C1A O1A K1 134.6(8) . . ? N1 C1A C2A 103.4(14) . . ? O1A C1A N1 125.9(12) . . ? O1A C1A C2A 130.6(15) . . ? C3A C2A C1A 110.9(17) . . ? C2A C3A C4A 111.1(17) . . ? C3A C4A N1 106.5(14) . . ? K1 O3A K2 94.6(2) . . ? C9A O3A K1 125.2(7) . . ? C9A O3A K2 133.3(7) . . ? N2 C9A O3A 130.2(13) . . ? N2 C9A C10A 102.3(12) . . ? O3A C9A C10A 127.2(13) . . ? C11A C10A C9A 104.0(12) . . ? C12A C11A C10A 104.0(15) . . ? N2 C12A C11A 102.0(14) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 13 2 22 0.2721 12.9865 1.9981 21.9868 0.2370 0.9834 0.0035 -13 -2 -22 0.2721 -12.9865 -1.9981 -21.9868 -0.2370 -0.9834 -0.0035 -5 18 0 0.4853 -5.0038 17.9876 0.0036 -0.0161 -0.0005 1.0043 8 -17 6 0.3643 8.0005 -16.9884 5.9928 0.0857 0.2580 -0.9762 -29 -1 32 0.1509 -28.9677 -0.9991 31.9723 0.9748 0.1733 0.0016 29 1 -32 0.1509 28.9677 0.9991 -31.9723 -0.9748 -0.1733 -0.0016 -10 12 -16 0.4271 -9.9964 11.9920 -15.9872 -0.2253 -0.6337 0.7342 38 2 -26 0.1689 37.9581 1.9982 -25.9749 -0.9820 0.2381 0.0003 9 14 14 0.3774 8.9843 13.9899 13.9949 0.0849 0.7348 0.6937 -36 -2 28 0.1590 -35.9601 -1.9982 27.9738 0.9938 -0.1290 -0.0134 _database_code_depnum_ccdc_archive 'CCDC 965884' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_bishep_kpf6_meoh _audit_creation_date 2013-02-04 _audit_creation_method ; Olex2 1.2 (compiled Nov 5 2012 18:25:38, GUI svn.r4372) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C48 H84 F24 K4 N8 O14 P4' _chemical_formula_sum 'C48 H84 F24 K4 N8 O14 P4' _chemical_formula_weight 1733.49 _chemical_melting_point ? _chemical_oxdiff_formula 'C12 H20 N2 O3 K P F6' 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' 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' K K 0.2009 0.2494 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 41.2572(13) _cell_length_b 12.8318(4) _cell_length_c 45.5789(17) _cell_angle_alpha 90.00 _cell_angle_beta 111.458(4) _cell_angle_gamma 90.00 _cell_volume 22457.2(13) _cell_formula_units_Z 12 _cell_measurement_reflns_used 5277 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 28.4084 _cell_measurement_theta_min 2.5519 _exptl_absorpt_coefficient_mu 0.443 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_correction_T_min 0.853 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 10704 _exptl_crystal_size_max 0.6726 _exptl_crystal_size_mid 0.1765 _exptl_crystal_size_min 0.0362 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.2077 _diffrn_reflns_av_unetI/netI 0.1902 _diffrn_reflns_limit_h_max 52 _diffrn_reflns_limit_h_min -53 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 55 _diffrn_reflns_limit_l_min -59 _diffrn_reflns_number 118863 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.63 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.9985 _diffrn_measured_fraction_theta_max 0.9985 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 2.00 34.25 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - -25.4065 38.0000 -30.0000 43 #__ type_ start__ end____ width___ exp.time_ 2 omega -33.00 47.25 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - -25.4065 38.0000 120.0000 107 #__ type_ start__ end____ width___ exp.time_ 3 omega -67.00 29.00 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - -25.4065 95.0000 -3.0000 128 #__ type_ start__ end____ width___ exp.time_ 4 omega 60.00 113.25 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - 25.7190 179.0000 -150.0000 71 #__ type_ start__ end____ width___ exp.time_ 5 omega -100.00 5.75 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - -25.4065 -57.0000 0.0000 141 #__ type_ start__ end____ width___ exp.time_ 6 omega -115.00 -34.00 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - -25.4065 -179.0000 120.0000 108 #__ type_ start__ end____ width___ exp.time_ 7 omega -100.00 5.75 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - -25.4065 -57.0000 -180.0000 141 #__ type_ start__ end____ width___ exp.time_ 8 omega -7.00 86.00 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - 25.7190 57.0000 -30.0000 124 #__ type_ start__ end____ width___ exp.time_ 9 omega -23.00 28.00 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - 25.7190 95.0000 176.0000 68 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0165522000 _diffrn_orient_matrix_UB_12 -0.0224892000 _diffrn_orient_matrix_UB_13 0.0082463000 _diffrn_orient_matrix_UB_21 0.0048257000 _diffrn_orient_matrix_UB_22 0.0088358000 _diffrn_orient_matrix_UB_23 -0.0132251000 _diffrn_orient_matrix_UB_31 0.0066268000 _diffrn_orient_matrix_UB_32 0.0496900000 _diffrn_orient_matrix_UB_33 0.0060746000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 10209 _reflns_number_total 25414 _reflns_odcompleteness_completeness 99.85 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.890 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.100 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 1387 _refine_ls_number_reflns 25414 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2262 _refine_ls_R_factor_gt 0.0973 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2059 _refine_ls_wR_factor_ref 0.2819 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H6A,H6B} of C6, {H8A,H8B} of C8, {H21A,H21B} of C21, {H5A,H5B} of C5, {H2C, H2D} of C2, {H50A,H50B} of C50, {H56A,H56B} of C56, {H66A,H66B} of C66, {H64A, H64B} of C64, {H52A,H52B} of C52, {H16A,H16B} of C16, {H26A,H26B} of C26, {H38A,H38B} of C38, {H20,H2B} of C20, {H34A,H34B} of C34, {H29A,H29B} of C29, {H47A,H47B} of C47, {H57A,H57B} of C57, {H65A,H65B} of C65, {H6,H68} of C68, {H31A,H31B} of C31, {H53A,H53B} of C53, {H9A,H9B} of C9, {H51A,H51B} of C51, {H40A,H40B} of C40, {H45A,H45B} of C45, {H54A,H54B} of C54, {H55A,H55B} of C55, {H27A,H27B} of C27, {H23A,H23B} of C23, {H4,H41} of C41, {H22A,H22B} of C22, {H43A,H43B} of C43, {H15A,H15B} of C15, {H4A,H4B} of C4, {H18A,H18B} of C18, {H14A,H14B} of C14, {H19A,H19B} of C19, {H62A,H62B} of C62, {H7A,H7B} of C7, {H32A,H32B} of C32, {H33A,H33B} of C33, {H44A,H44B} of C44, {H42A,H42B} of C42, {H35A,H35B} of C35, {H11A,H11B} of C11, {H2A,H17} of C17, {H63A,H63B} of C63, {H46A,H46B} of C46, {H59A,H59B} of C59, {H10A,H10B} of C10, {H30A, H30B} of C30, {H67A,H67B} of C67, {H3A,H3B} of C3, {H71A,H71B} of C71, {H28A, H28B} of C28, {H39A,H39B} of C39, {H70A,H70B} of C70, {H69A,H69B} of C69, {H58A,H58B} of C58 2. Others Fixed Sof: O3S(0.5) O4S(0.5) 3.a Secondary CH2 refined with riding coordinates: C6(H6A,H6B), C8(H8A,H8B), C21(H21A,H21B), C5(H5A,H5B), C2(H2C,H2D), C23(H23A, H23B), C41(H4,H41), C22(H22A,H22B), C43(H43A,H43B), C15(H15A,H15B), C4(H4A, H4B), C18(H18A,H18B), C14(H14A,H14B), C19(H19A,H19B), C62(H62A,H62B), C7(H7A, H7B), C32(H32A,H32B), C33(H33A,H33B), C44(H44A,H44B), C42(H42A,H42B), C35(H35A, H35B), C11(H11A,H11B), C17(H2A,H17), C63(H63A,H63B), C46(H46A,H46B), C59(H59A, H59B), C10(H10A,H10B), C30(H30A,H30B), C67(H67A,H67B), C3(H3A,H3B), C50(H50A, H50B), C56(H56A,H56B), C66(H66A,H66B), C64(H64A,H64B), C52(H52A,H52B), C16(H16A,H16B), C26(H26A,H26B), C38(H38A,H38B), C20(H20,H2B), C34(H34A,H34B), C29(H29A,H29B), C47(H47A,H47B), C57(H57A,H57B), C65(H65A,H65B), C68(H6,H68), C31(H31A,H31B), C53(H53A,H53B), C9(H9A,H9B), C51(H51A,H51B), C40(H40A,H40B), C45(H45A,H45B), C54(H54A,H54B), C55(H55A,H55B), C27(H27A,H27B), C58(H58A,H58B), C69(H69A,H69B), C70(H70A,H70B), C39(H39A,H39B), C28(H28A,H28B), C71(H71A,H71B) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group K5 K 0.94938(3) 0.98931(11) 0.23057(3) 0.0341(4) Uani 1 1 d . . . K2 K 0.88231(3) 0.51662(11) -0.06570(3) 0.0356(4) Uani 1 1 d . . . K4 K 0.78120(4) 0.84578(11) -0.12046(3) 0.0330(3) Uani 1 1 d . . . K1 K 0.78203(4) 0.53297(11) -0.09824(3) 0.0364(4) Uani 1 1 d . . . K3 K 0.87684(3) 0.84796(11) -0.05354(3) 0.0333(3) Uani 1 1 d . . . P2 P 0.94966(4) 0.39778(14) -0.08608(4) 0.0335(4) Uani 1 1 d . . . K6 K 0.95812(4) 1.31599(12) 0.21264(3) 0.0413(4) Uani 1 1 d . . . P5 P 0.88440(5) 0.86831(14) 0.25086(4) 0.0365(4) Uani 1 1 d . . . P1 P 0.71598(4) 0.37796(14) -0.08669(4) 0.0359(4) Uani 1 1 d . . . P4 P 0.74321(5) 0.98971(15) -0.19516(5) 0.0426(5) Uani 1 1 d . . . P3 P 0.91610(5) 0.98915(15) 0.01964(5) 0.0438(5) Uani 1 1 d . . . F29 F 0.90682(9) 0.9679(3) 0.26817(9) 0.0408(9) Uani 1 1 d . . . F28 F 0.85024(9) 0.9205(3) 0.25276(9) 0.0456(10) Uani 1 1 d . . . F5 F 0.74846(9) 0.3318(3) -0.09438(10) 0.0471(10) Uani 1 1 d . . . F26 F 0.91961(10) 0.8178(3) 0.24898(10) 0.0479(11) Uani 1 1 d . . . O10 O 0.80853(11) 0.8883(3) -0.05723(10) 0.0385(11) Uani 1 1 d . . . F30 F 0.89275(10) 0.8141(3) 0.28448(9) 0.0480(10) Uani 1 1 d . . . F3 F 0.68434(10) 0.4259(3) -0.07906(9) 0.0519(11) Uani 1 1 d . . . O11 O 0.73385(11) 0.9833(3) -0.10615(10) 0.0364(11) Uani 1 1 d . . . F1 F 0.71128(10) 0.4667(3) -0.11296(9) 0.0474(10) Uani 1 1 d . . . O8 O 0.93190(11) 0.9880(3) -0.06427(11) 0.0427(12) Uani 1 1 d . . . F25 F 0.87737(10) 0.9248(3) 0.21759(9) 0.0512(11) Uani 1 1 d . . . F4 F 0.74248(10) 0.4538(3) -0.06113(9) 0.0521(11) Uani 1 1 d . . . F22 F 0.77240(11) 1.0526(4) -0.20207(10) 0.0619(12) Uani 1 1 d . . . O3 O 0.83266(11) 0.4344(4) -0.11839(11) 0.0460(13) Uani 1 1 d . . . O4 O 0.83184(12) 0.4384(4) -0.04655(12) 0.0508(13) Uani 1 1 d . . . O5 O 0.92204(11) 0.4318(3) -0.00379(10) 0.0395(12) Uani 1 1 d . . . F27 F 0.86286(11) 0.7700(3) 0.23346(11) 0.0646(13) Uani 1 1 d . . . O12 O 0.73931(11) 0.7115(3) -0.10491(11) 0.0393(11) Uani 1 1 d . . . N1 N 0.73923(13) 0.6352(4) -0.19541(11) 0.0326(13) Uani 1 1 d . . . O6 O 0.88361(11) 0.6615(3) -0.02106(10) 0.0381(11) Uani 1 1 d . . . F13 F 0.89083(12) 1.0199(3) -0.01565(9) 0.0648(14) Uani 1 1 d . . . O16 O 0.92784(10) 1.1834(3) 0.24515(10) 0.0372(11) Uani 1 1 d . . . N4 N 0.93005(13) 0.6310(4) 0.02466(11) 0.0327(13) Uani 1 1 d . . . F6 F 0.72154(11) 0.2914(3) -0.06048(10) 0.0609(13) Uani 1 1 d . . . F2 F 0.69048(11) 0.3034(3) -0.11271(11) 0.0681(13) Uani 1 1 d . . . O2 O 0.74304(10) 0.4390(3) -0.16496(10) 0.0375(11) Uani 1 1 d . . . O1 O 0.78549(10) 0.6574(3) -0.14923(10) 0.0369(11) Uani 1 1 d . . . O9 O 0.84225(12) 0.9438(4) -0.10917(11) 0.0445(12) Uani 1 1 d . . . F19 F 0.76169(14) 1.0218(3) -0.15889(10) 0.0770(15) Uani 1 1 d . . . N7 N 0.78980(15) 1.0499(4) -0.04918(13) 0.0443(15) Uani 1 1 d . . . F23 F 0.72041(12) 1.0918(4) -0.20115(12) 0.0787(15) Uani 1 1 d . . . F24 F 0.72623(13) 0.9574(4) -0.23087(10) 0.0792(15) Uani 1 1 d . . . N2 N 0.80502(12) 0.3329(4) -0.16123(13) 0.0335(13) Uani 1 1 d . . . N6 N 0.87708(14) 1.0681(4) -0.11813(13) 0.0385(14) Uani 1 1 d . . . O13 O 1.00299(12) 0.9283(5) 0.21167(14) 0.080(2) Uani 1 1 d . . . C1 C 0.77235(16) 0.6575(5) -0.17847(16) 0.0327(15) Uani 1 1 d . . . N3 N 0.85918(14) 0.3353(4) -0.00393(13) 0.0393(14) Uani 1 1 d . . . F18 F 0.94073(14) 0.9581(4) 0.05401(10) 0.0900(18) Uani 1 1 d . . . C24 C 0.89718(17) 0.6568(5) 0.00822(16) 0.0358(16) Uani 1 1 d . . . O14 O 0.91846(12) 0.8671(4) 0.17037(11) 0.0462(13) Uani 1 1 d . . . C12 C 0.82961(15) 0.4011(5) -0.14463(16) 0.0327(16) Uani 1 1 d . . . N5 N 0.96792(14) 0.8003(5) -0.07293(15) 0.0476(16) Uani 1 1 d . . . F21 F 0.76692(14) 0.8882(3) -0.18724(11) 0.0781(16) Uani 1 1 d . . . N11 N 0.87095(13) 1.2326(4) 0.23163(14) 0.0425(15) Uani 1 1 d . . . C6 C 0.71017(15) 0.4848(5) -0.18294(15) 0.0372(17) Uani 1 1 d . . . H6A H 0.6925 0.4636 -0.1742 0.045 Uiso 1 1 calc R . . H6B H 0.7024 0.4609 -0.2051 0.045 Uiso 1 1 calc R . . O15 O 0.93885(17) 1.1232(4) 0.18307(12) 0.0686(18) Uani 1 1 d . . . C8 C 0.77913(16) 0.2881(5) -0.15057(15) 0.0379(17) Uani 1 1 d . . . H8A H 0.7856 0.3035 -0.1279 0.046 Uiso 1 1 calc R . . H8B H 0.7792 0.2115 -0.1530 0.046 Uiso 1 1 calc R . . N8 N 0.69398(14) 0.8079(4) -0.10154(15) 0.0423(15) Uani 1 1 d . . . O18 O 0.97890(12) 1.4064(5) 0.27205(12) 0.0690(18) Uani 1 1 d . . . O1S O 0.80858(13) 0.6683(4) -0.04345(12) 0.0583(15) Uani 1 1 d . . . C21 C 0.93822(18) 0.6302(6) 0.05888(16) 0.0462(19) Uani 1 1 d . . . H21A H 0.9610 0.6637 0.0703 0.055 Uiso 1 1 calc R . . H21B H 0.9387 0.5581 0.0668 0.055 Uiso 1 1 calc R . . C5 C 0.71402(16) 0.6007(5) -0.18160(15) 0.0346(16) Uani 1 1 d . . . H5A H 0.6911 0.6333 -0.1932 0.041 Uiso 1 1 calc R . . H5B H 0.7218 0.6240 -0.1594 0.041 Uiso 1 1 calc R . . C2 C 0.79094(18) 0.6768(5) -0.20030(16) 0.0435(18) Uani 1 1 d . . . H2C H 0.8056 0.6161 -0.2008 0.052 Uiso 1 1 calc R . . H2D H 0.8060 0.7392 -0.1937 0.052 Uiso 1 1 calc R . . C23 C 0.87862(17) 0.6787(6) 0.03039(15) 0.0418(18) Uani 1 1 d . . . H23A H 0.8633 0.6199 0.0309 0.050 Uiso 1 1 calc R . . H23B H 0.8645 0.7431 0.0243 0.050 Uiso 1 1 calc R . . N12 N 0.93789(17) 1.5281(4) 0.27042(13) 0.0454(16) Uani 1 1 d . . . O17 O 0.89601(12) 1.4138(4) 0.21416(11) 0.0475(13) Uani 1 1 d . . . C36 C 0.85719(17) 0.9835(5) -0.12568(15) 0.0348(16) Uani 1 1 d . . . C48 C 0.72057(17) 0.7396(5) -0.09053(17) 0.0385(17) Uani 1 1 d . . . C41 C 0.78260(17) 1.0924(5) -0.08004(15) 0.0397(17) Uani 1 1 d . . . H4 H 0.7960 1.0528 -0.0905 0.048 Uiso 1 1 calc R . . H41 H 0.7908 1.1655 -0.0779 0.048 Uiso 1 1 calc R . . O7 O 0.91342(12) 0.7357(4) -0.08219(12) 0.0561(15) Uani 1 1 d . . . O2S O 0.84543(11) 0.6872(3) -0.10041(10) 0.0410(12) Uani 1 1 d . . . C49 C 1.00352(17) 0.8857(7) 0.18778(18) 0.052(2) Uani 1 1 d . . . C22 C 0.90881(18) 0.6922(6) 0.06256(16) 0.0475(19) Uani 1 1 d . . . H22A H 0.9153 0.7665 0.0668 0.057 Uiso 1 1 calc R . . H22B H 0.9024 0.6641 0.0799 0.057 Uiso 1 1 calc R . . C43 C 0.69755(16) 0.9764(6) -0.12470(17) 0.0441(18) Uani 1 1 d . . . H43A H 0.6927 1.0124 -0.1451 0.053 Uiso 1 1 calc R . . H43B H 0.6840 1.0114 -0.1136 0.053 Uiso 1 1 calc R . . C25 C 0.93838(18) 0.7525(6) -0.09041(19) 0.048(2) Uani 1 1 d . . . F17 F 0.89654(18) 1.0741(5) 0.03146(12) 0.137(3) Uani 1 1 d . . . C13 C 0.83495(17) 0.4048(5) -0.02081(17) 0.0399(17) Uani 1 1 d . . . C15 C 0.8308(2) 0.3824(7) 0.03064(18) 0.059(2) Uani 1 1 d . . . H15A H 0.8418 0.4353 0.0471 0.071 Uiso 1 1 calc R . . H15B H 0.8135 0.3428 0.0365 0.071 Uiso 1 1 calc R . . C4 C 0.73082(19) 0.6388(6) -0.22957(15) 0.049(2) Uani 1 1 d . . . H4A H 0.7092 0.6788 -0.2403 0.058 Uiso 1 1 calc R . . H4B H 0.7281 0.5677 -0.2386 0.058 Uiso 1 1 calc R . . C18 C 0.92064(18) 0.3220(5) 0.00120(18) 0.049(2) Uani 1 1 d . . . H18A H 0.9278 0.3068 0.0240 0.059 Uiso 1 1 calc R . . H18B H 0.9365 0.2846 -0.0070 0.059 Uiso 1 1 calc R . . C14 C 0.81346(18) 0.4343(6) -0.00120(16) 0.050(2) Uani 1 1 d . . . H14A H 0.8131 0.5109 0.0012 0.060 Uiso 1 1 calc R . . H14B H 0.7892 0.4093 -0.0114 0.060 Uiso 1 1 calc R . . C37 C 0.80082(16) 0.9520(6) -0.04076(16) 0.0377(17) Uani 1 1 d . . . C19 C 0.95594(17) 0.4727(6) 0.01297(17) 0.0462(19) Uani 1 1 d . . . H19A H 0.9727 0.4461 0.0037 0.055 Uiso 1 1 calc R . . H19B H 0.9640 0.4512 0.0354 0.055 Uiso 1 1 calc R . . F15 F 0.93159(17) 0.8990(4) 0.00621(11) 0.110(2) Uani 1 1 d . . . C62 C 0.90202(18) 1.2047(5) 0.28527(16) 0.0432(18) Uani 1 1 d . . . H62A H 0.9149 1.2655 0.2974 0.052 Uiso 1 1 calc R . . H62B H 0.9125 1.1400 0.2967 0.052 Uiso 1 1 calc R . . C61 C 0.90214(17) 1.2044(5) 0.25232(17) 0.0373(17) Uani 1 1 d . . . C7 C 0.74309(17) 0.3280(5) -0.16807(18) 0.0443(19) Uani 1 1 d . . . H7A H 0.7356 0.3087 -0.1906 0.053 Uiso 1 1 calc R . . H7B H 0.7266 0.2965 -0.1594 0.053 Uiso 1 1 calc R . . C32 C 0.88844(19) 1.1168(5) -0.08722(17) 0.0479(19) Uani 1 1 d . . . H32A H 0.8741 1.0899 -0.0756 0.058 Uiso 1 1 calc R . . H32B H 0.8845 1.1929 -0.0899 0.058 Uiso 1 1 calc R . . N9 N 0.98635(16) 0.7996(5) 0.17546(14) 0.0469(16) Uani 1 1 d . . . C33 C 0.8922(2) 1.0942(6) -0.14142(17) 0.059(2) Uani 1 1 d . . . H33A H 0.9173 1.0759 -0.1337 0.071 Uiso 1 1 calc R . . H33B H 0.8897 1.1695 -0.1465 0.071 Uiso 1 1 calc R . . N10 N 0.90155(16) 1.0582(6) 0.13627(14) 0.0566(19) Uani 1 1 d . . . C44 C 0.68649(18) 0.8648(6) -0.13061(17) 0.0474(19) Uani 1 1 d . . . H44A H 0.6612 0.8617 -0.1430 0.057 Uiso 1 1 calc R . . H44B H 0.6987 0.8316 -0.1432 0.057 Uiso 1 1 calc R . . C42 C 0.74459(18) 1.0899(5) -0.10076(16) 0.0411(17) Uani 1 1 d . . . H42A H 0.7307 1.1269 -0.0903 0.049 Uiso 1 1 calc R . . H42B H 0.7410 1.1250 -0.1211 0.049 Uiso 1 1 calc R . . C35 C 0.85480(19) 0.9444(6) -0.15775(15) 0.0448(19) Uani 1 1 d . . . H35A H 0.8674 0.8776 -0.1559 0.054 Uiso 1 1 calc R . . H35B H 0.8302 0.9342 -0.1718 0.054 Uiso 1 1 calc R . . C11 C 0.85118(18) 0.4294(6) -0.16353(18) 0.055(2) Uani 1 1 d . . . H11A H 0.8758 0.4098 -0.1522 0.066 Uiso 1 1 calc R . . H11B H 0.8499 0.5052 -0.1678 0.066 Uiso 1 1 calc R . . C17 C 0.88385(19) 0.2874(5) -0.01589(18) 0.051(2) Uani 1 1 d . . . H2A H 0.8770 0.3047 -0.0385 0.061 Uiso 1 1 calc R . . H17 H 0.8826 0.2108 -0.0141 0.061 Uiso 1 1 calc R . . C63 C 0.86325(19) 1.2114(7) 0.27986(18) 0.059(2) Uani 1 1 d . . . H63A H 0.8594 1.2544 0.2963 0.071 Uiso 1 1 calc R . . H63B H 0.8533 1.1412 0.2799 0.071 Uiso 1 1 calc R . . C46 C 0.6913(2) 0.7474(7) -0.0537(2) 0.082(3) Uani 1 1 d . . . H46A H 0.6970 0.7749 -0.0321 0.099 Uiso 1 1 calc R . . H46B H 0.6735 0.6921 -0.0576 0.099 Uiso 1 1 calc R . . C59 C 0.9492(2) 1.1453(6) 0.13399(16) 0.053(2) Uani 1 1 d . . . H59A H 0.9696 1.1000 0.1369 0.064 Uiso 1 1 calc R . . H59B H 0.9573 1.2182 0.1387 0.064 Uiso 1 1 calc R . . C10 C 0.8359(2) 0.3688(7) -0.19389(17) 0.058(2) Uani 1 1 d . . . H10A H 0.8288 0.4168 -0.2122 0.069 Uiso 1 1 calc R . . H10B H 0.8533 0.3193 -0.1961 0.069 Uiso 1 1 calc R . . C30 C 0.96769(17) 0.9680(6) -0.04594(19) 0.053(2) Uani 1 1 d . . . H30A H 0.9739 0.9989 -0.0247 0.063 Uiso 1 1 calc R . . H30B H 0.9827 0.9998 -0.0562 0.063 Uiso 1 1 calc R . . F14 F 0.94210(14) 1.0702(4) 0.01799(16) 0.130(3) Uani 1 1 d . . . C67 C 0.8948(2) 1.5242(6) 0.21574(19) 0.066(3) Uani 1 1 d . . . H67A H 0.8761 1.5457 0.2233 0.080 Uiso 1 1 calc R . . H67B H 0.8897 1.5547 0.1946 0.080 Uiso 1 1 calc R . . C3 C 0.76237(19) 0.6939(6) -0.23259(17) 0.051(2) Uani 1 1 d . . . H3A H 0.7688 0.6624 -0.2495 0.061 Uiso 1 1 calc R . . H3B H 0.7577 0.7691 -0.2370 0.061 Uiso 1 1 calc R . . C50 C 1.02423(17) 0.9202(6) 0.16799(19) 0.059(2) Uani 1 1 d . . . H50A H 1.0493 0.9052 0.1789 0.070 Uiso 1 1 calc R . . H50B H 1.0212 0.9958 0.1634 0.070 Uiso 1 1 calc R . . C56 C 0.8780(2) 1.0040(8) 0.14894(19) 0.072(3) Uani 1 1 d . . . H56A H 0.8536 1.0191 0.1354 0.087 Uiso 1 1 calc R . . H56B H 0.8820 1.0305 0.1704 0.087 Uiso 1 1 calc R . . C66 C 0.86341(18) 1.3700(6) 0.19341(18) 0.055(2) Uani 1 1 d . . . H66A H 0.8600 1.3849 0.1712 0.066 Uiso 1 1 calc R . . H66B H 0.8438 1.4008 0.1980 0.066 Uiso 1 1 calc R . . C64 C 0.84708(19) 1.2630(7) 0.24723(18) 0.056(2) Uani 1 1 d . . . H64A H 0.8233 1.2364 0.2356 0.067 Uiso 1 1 calc R . . H64B H 0.8462 1.3397 0.2491 0.067 Uiso 1 1 calc R . . C52 C 0.9909(2) 0.7651(6) 0.14649(18) 0.061(2) Uani 1 1 d . . . H52A H 0.9681 0.7507 0.1296 0.073 Uiso 1 1 calc R . . H52B H 1.0054 0.7014 0.1503 0.073 Uiso 1 1 calc R . . F16 F 0.88822(15) 0.9095(6) 0.0207(2) 0.166(4) Uani 1 1 d . . . C16 C 0.8579(2) 0.3104(6) 0.02717(17) 0.059(2) Uani 1 1 d . . . H16A H 0.8808 0.3228 0.0441 0.071 Uiso 1 1 calc R . . H16B H 0.8512 0.2367 0.0280 0.071 Uiso 1 1 calc R . . C26 C 0.9410(2) 0.7216(6) -0.12140(19) 0.061(2) Uani 1 1 d . . . H26A H 0.9351 0.6470 -0.1259 0.073 Uiso 1 1 calc R . . H26B H 0.9251 0.7640 -0.1389 0.073 Uiso 1 1 calc R . . C38 C 0.8019(2) 0.9336(6) -0.00779(17) 0.054(2) Uani 1 1 d . . . H38A H 0.7848 0.8797 -0.0077 0.065 Uiso 1 1 calc R . . H38B H 0.8254 0.9106 0.0062 0.065 Uiso 1 1 calc R . . C20 C 0.95365(16) 0.5886(5) 0.01044(15) 0.0396(17) Uani 1 1 d . . . H20 H 0.9771 0.6189 0.0211 0.047 Uiso 1 1 calc R . . H2B H 0.9454 0.6089 -0.0121 0.047 Uiso 1 1 calc R . . C34 C 0.8717(2) 1.0293(7) -0.1702(2) 0.075(3) Uani 1 1 d . . . H34A H 0.8538 1.0723 -0.1860 0.090 Uiso 1 1 calc R . . H34B H 0.8873 0.9990 -0.1800 0.090 Uiso 1 1 calc R . . C29 C 0.97323(18) 0.8518(6) -0.04331(17) 0.052(2) Uani 1 1 d . . . H29A H 0.9973 0.8376 -0.0286 0.062 Uiso 1 1 calc R . . H29B H 0.9571 0.8211 -0.0341 0.062 Uiso 1 1 calc R . . C47 C 0.7236(2) 0.7066(6) -0.05828(19) 0.053(2) Uani 1 1 d . . . H47A H 0.7449 0.7363 -0.0422 0.064 Uiso 1 1 calc R . . H47B H 0.7247 0.6297 -0.0565 0.064 Uiso 1 1 calc R . . C60 C 0.9303(2) 1.1108(6) 0.15460(18) 0.053(2) Uani 1 1 d . . . C57 C 0.8993(2) 1.0491(9) 0.10355(18) 0.086(3) Uani 1 1 d . . . H57A H 0.8751 1.0592 0.0886 0.103 Uiso 1 1 calc R . . H57B H 0.9078 0.9804 0.0996 0.103 Uiso 1 1 calc R . . F20 F 0.71454(16) 0.9254(4) -0.18759(14) 0.105(2) Uani 1 1 d . . . C65 C 0.86489(18) 1.2553(7) 0.19894(17) 0.054(2) Uani 1 1 d . . . H65A H 0.8427 1.2231 0.1853 0.065 Uiso 1 1 calc R . . H65B H 0.8839 1.2248 0.1933 0.065 Uiso 1 1 calc R . . C68 C 0.9297(2) 1.5617(6) 0.23824(19) 0.066(3) Uani 1 1 d . . . H6 H 0.9480 1.5361 0.2309 0.080 Uiso 1 1 calc R . . H68 H 0.9301 1.6388 0.2377 0.080 Uiso 1 1 calc R . . C31 C 0.92621(19) 1.0975(6) -0.06788(17) 0.051(2) Uani 1 1 d . . . H31A H 0.9410 1.1280 -0.0785 0.061 Uiso 1 1 calc R . . H31B H 0.9324 1.1308 -0.0469 0.061 Uiso 1 1 calc R . . C53 C 0.9647(3) 0.7434(6) 0.1885(2) 0.067(3) Uani 1 1 d . . . H53A H 0.9703 0.7659 0.2105 0.080 Uiso 1 1 calc R . . H53B H 0.9700 0.6681 0.1887 0.080 Uiso 1 1 calc R . . C9 C 0.8049(2) 0.3108(7) -0.19256(19) 0.069(3) Uani 1 1 d . . . H9A H 0.7831 0.3361 -0.2090 0.083 Uiso 1 1 calc R . . H9B H 0.8071 0.2350 -0.1955 0.083 Uiso 1 1 calc R . . C51 C 1.0089(2) 0.8559(7) 0.1377(2) 0.067(3) Uani 1 1 d . . . H51A H 0.9921 0.8978 0.1207 0.080 Uiso 1 1 calc R . . H51B H 1.0275 0.8310 0.1306 0.080 Uiso 1 1 calc R . . C40 C 0.7812(2) 1.1059(6) -0.02505(18) 0.068(3) Uani 1 1 d . . . H40A H 0.7558 1.1188 -0.0320 0.081 Uiso 1 1 calc R . . H40B H 0.7937 1.1734 -0.0200 0.081 Uiso 1 1 calc R . . C45 C 0.6787(2) 0.8348(7) -0.0783(2) 0.070(3) Uani 1 1 d . . . H45A H 0.6530 0.8360 -0.0880 0.084 Uiso 1 1 calc R . . H45B H 0.6871 0.9036 -0.0687 0.084 Uiso 1 1 calc R . . C54 C 0.9263(2) 0.7594(6) 0.1703(2) 0.066(3) Uani 1 1 d . . . H54A H 0.9201 0.7345 0.1484 0.079 Uiso 1 1 calc R . . H54B H 0.9126 0.7191 0.1803 0.079 Uiso 1 1 calc R . . C55 C 0.88381(19) 0.8890(8) 0.15035(18) 0.071(3) Uani 1 1 d . . . H55A H 0.8674 0.8545 0.1585 0.086 Uiso 1 1 calc R . . H55B H 0.8795 0.8618 0.1289 0.086 Uiso 1 1 calc R . . C27 C 0.9778(3) 0.7412(8) -0.1175(3) 0.104(4) Uani 1 1 d . . . H27A H 0.9791 0.7744 -0.1367 0.124 Uiso 1 1 calc R . . H27B H 0.9911 0.6752 -0.1136 0.124 Uiso 1 1 calc R . . C58 C 0.9227(2) 1.1361(7) 0.10085(18) 0.071(3) Uani 1 1 d . . . H58A H 0.9340 1.1179 0.0858 0.085 Uiso 1 1 calc R . . H58B H 0.9095 1.2018 0.0940 0.085 Uiso 1 1 calc R . . C69 C 0.9233(2) 1.5786(6) 0.29134(18) 0.067(3) Uani 1 1 d . . . H69A H 0.8977 1.5861 0.2811 0.081 Uiso 1 1 calc R . . H69B H 0.9338 1.6483 0.2978 0.081 Uiso 1 1 calc R . . C70 C 0.9327(2) 1.5047(7) 0.31958(19) 0.065(2) Uani 1 1 d . . . H70A H 0.9137 1.4545 0.3172 0.078 Uiso 1 1 calc R . . H70B H 0.9381 1.5437 0.3396 0.078 Uiso 1 1 calc R . . C39 C 0.7932(4) 1.0340(10) 0.0027(2) 0.141(6) Uani 1 1 d . . . H39A H 0.8138 1.0634 0.0195 0.170 Uiso 1 1 calc R . . H39B H 0.7745 1.0247 0.0112 0.170 Uiso 1 1 calc R . . C28 C 0.9921(2) 0.8129(7) -0.0897(2) 0.081(3) Uani 1 1 d . . . H28A H 1.0160 0.7924 -0.0761 0.097 Uiso 1 1 calc R . . H28B H 0.9924 0.8859 -0.0965 0.097 Uiso 1 1 calc R . . P6 P 0.92197(5) 0.45913(15) 0.13447(5) 0.0479(5) Uani 1 1 d . . . F31 F 0.93932(12) 0.5613(3) 0.12748(9) 0.0588(12) Uani 1 1 d . . . F34 F 0.89136(11) 0.5246(4) 0.13739(12) 0.0781(15) Uani 1 1 d . . . F35 F 0.94308(14) 0.4840(4) 0.17162(11) 0.0885(17) Uani 1 1 d . . . F36 F 0.90720(14) 0.3575(3) 0.14424(14) 0.0911(18) Uani 1 1 d . . . F33 F 0.90257(19) 0.4382(5) 0.09945(13) 0.140(3) Uani 1 1 d . . . F32 F 0.95412(15) 0.3958(4) 0.13394(19) 0.128(3) Uani 1 1 d . . . O3S O 0.9962(2) 1.1525(6) 0.2655(2) 0.036(2) Uani 0.50 1 d P . . O4S O 1.0113(2) 1.1854(8) 0.1974(2) 0.054(3) Uani 0.50 1 d P . . F7 F 0.92231(9) 0.4865(3) -0.10427(9) 0.0458(10) Uani 1 1 d . . . F9 F 0.92121(10) 0.3508(3) -0.07349(10) 0.0523(11) Uani 1 1 d . . . F11 F 0.97744(10) 0.4463(3) -0.09873(10) 0.0578(12) Uani 1 1 d . . . F12 F 0.97637(9) 0.3100(3) -0.06770(10) 0.0528(11) Uani 1 1 d . . . F8 F 0.93532(10) 0.3245(3) -0.11615(9) 0.0535(11) Uani 1 1 d . . . F10 F 0.96317(11) 0.4723(3) -0.05593(9) 0.0567(12) Uani 1 1 d . . . C72 C 0.96202(19) 1.4559(6) 0.28473(17) 0.0437(18) Uani 1 1 d . . . C71 C 0.9651(2) 1.4498(6) 0.31824(18) 0.056(2) Uani 1 1 d . . . H71A H 0.9866 1.4851 0.3321 0.068 Uiso 1 1 calc R . . H71B H 0.9658 1.3762 0.3250 0.068 Uiso 1 1 calc R . . 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 K5 0.0272(8) 0.0428(8) 0.0331(8) 0.0048(7) 0.0120(6) 0.0024(6) K2 0.0255(7) 0.0458(9) 0.0316(8) -0.0060(7) 0.0057(6) 0.0033(7) K4 0.0321(8) 0.0362(8) 0.0304(8) -0.0003(7) 0.0111(6) -0.0046(6) K1 0.0276(8) 0.0412(8) 0.0375(9) 0.0055(7) 0.0087(7) 0.0026(7) K3 0.0293(8) 0.0383(8) 0.0299(8) -0.0028(7) 0.0078(6) 0.0001(6) P2 0.0231(9) 0.0406(10) 0.0348(10) -0.0036(8) 0.0082(8) 0.0003(8) K6 0.0334(8) 0.0544(10) 0.0321(9) 0.0073(7) 0.0073(7) -0.0076(7) P5 0.0309(10) 0.0373(10) 0.0418(11) -0.0018(9) 0.0141(8) -0.0028(8) P1 0.0294(10) 0.0447(11) 0.0354(10) 0.0021(9) 0.0141(8) 0.0012(8) P4 0.0529(12) 0.0418(11) 0.0355(11) 0.0062(9) 0.0190(10) 0.0026(9) P3 0.0492(12) 0.0436(11) 0.0342(11) -0.0018(9) 0.0101(9) 0.0034(10) F29 0.033(2) 0.040(2) 0.046(2) -0.0025(19) 0.0106(18) -0.0035(17) F28 0.026(2) 0.064(3) 0.047(3) 0.000(2) 0.0138(18) 0.0044(19) F5 0.036(2) 0.047(2) 0.065(3) -0.003(2) 0.027(2) 0.0044(19) F26 0.038(2) 0.046(2) 0.067(3) 0.001(2) 0.029(2) 0.0043(19) O10 0.037(3) 0.042(3) 0.037(3) 0.002(2) 0.015(2) 0.008(2) F30 0.051(3) 0.049(2) 0.049(3) 0.020(2) 0.024(2) 0.005(2) F3 0.040(2) 0.070(3) 0.051(3) 0.011(2) 0.023(2) 0.019(2) O11 0.035(3) 0.039(3) 0.034(3) 0.000(2) 0.012(2) 0.003(2) F1 0.040(2) 0.059(3) 0.043(2) 0.018(2) 0.0147(19) 0.009(2) O8 0.036(3) 0.044(3) 0.041(3) -0.008(2) 0.006(2) -0.008(2) F25 0.053(3) 0.072(3) 0.028(2) 0.004(2) 0.0140(19) -0.003(2) F4 0.043(2) 0.064(3) 0.040(2) -0.011(2) 0.0033(19) -0.002(2) F22 0.047(3) 0.090(3) 0.050(3) 0.006(2) 0.019(2) -0.010(2) O3 0.027(3) 0.067(3) 0.040(3) -0.021(3) 0.007(2) -0.006(2) O4 0.036(3) 0.071(4) 0.039(3) 0.019(3) 0.007(2) 0.007(3) O5 0.030(3) 0.039(3) 0.041(3) 0.000(2) 0.004(2) 0.007(2) F27 0.057(3) 0.066(3) 0.074(3) -0.022(3) 0.026(3) -0.022(2) O12 0.040(3) 0.039(3) 0.046(3) 0.005(2) 0.025(2) 0.006(2) N1 0.029(3) 0.050(3) 0.019(3) -0.003(3) 0.008(2) -0.007(3) O6 0.032(3) 0.047(3) 0.030(3) 0.002(2) 0.005(2) 0.008(2) F13 0.091(3) 0.046(2) 0.034(2) -0.010(2) -0.004(2) 0.016(2) O16 0.021(2) 0.051(3) 0.043(3) 0.000(2) 0.016(2) 0.002(2) N4 0.030(3) 0.048(3) 0.019(3) -0.001(3) 0.006(2) -0.002(3) F6 0.060(3) 0.064(3) 0.068(3) 0.033(2) 0.034(2) 0.015(2) F2 0.048(3) 0.078(3) 0.070(3) -0.025(3) 0.012(2) -0.025(2) O2 0.027(2) 0.049(3) 0.032(3) 0.003(2) 0.005(2) 0.000(2) O1 0.024(2) 0.048(3) 0.034(3) -0.001(2) 0.006(2) -0.004(2) O9 0.041(3) 0.058(3) 0.035(3) 0.005(2) 0.014(2) -0.014(2) F19 0.131(5) 0.055(3) 0.035(3) 0.003(2) 0.019(3) -0.002(3) N7 0.046(4) 0.050(4) 0.033(3) -0.004(3) 0.009(3) 0.016(3) F23 0.065(3) 0.073(3) 0.097(4) 0.001(3) 0.028(3) 0.022(3) F24 0.090(4) 0.088(4) 0.037(3) -0.005(3) -0.004(3) -0.018(3) N2 0.020(3) 0.043(3) 0.038(3) -0.011(3) 0.012(2) -0.006(2) N6 0.045(4) 0.042(3) 0.032(3) -0.004(3) 0.018(3) -0.006(3) O13 0.025(3) 0.138(5) 0.073(4) -0.066(4) 0.013(3) -0.004(3) C1 0.030(4) 0.033(4) 0.034(4) -0.003(3) 0.011(3) 0.001(3) N3 0.042(3) 0.037(3) 0.036(3) 0.005(3) 0.010(3) -0.006(3) F18 0.116(4) 0.091(4) 0.035(3) 0.002(3) -0.005(3) 0.052(3) C24 0.031(4) 0.036(4) 0.035(4) 0.008(3) 0.005(3) 0.001(3) O14 0.036(3) 0.056(3) 0.049(3) -0.012(3) 0.019(2) -0.013(2) C12 0.015(3) 0.044(4) 0.034(4) -0.009(3) 0.002(3) 0.000(3) N5 0.025(3) 0.054(4) 0.067(4) -0.015(3) 0.021(3) -0.007(3) F21 0.106(4) 0.049(3) 0.061(3) -0.004(2) 0.009(3) 0.022(3) N11 0.024(3) 0.059(4) 0.047(4) 0.013(3) 0.015(3) 0.003(3) C6 0.021(3) 0.050(4) 0.033(4) 0.005(3) 0.001(3) -0.003(3) O15 0.130(5) 0.044(3) 0.028(3) 0.005(3) 0.024(3) -0.004(3) C8 0.034(4) 0.039(4) 0.035(4) -0.006(3) 0.005(3) -0.005(3) N8 0.030(3) 0.042(3) 0.063(4) 0.010(3) 0.026(3) 0.004(3) O18 0.032(3) 0.107(5) 0.060(4) -0.047(3) 0.007(3) 0.017(3) O1S 0.044(3) 0.066(4) 0.058(4) 0.003(3) 0.011(3) 0.003(3) C21 0.043(4) 0.067(5) 0.032(4) 0.004(4) 0.018(3) 0.012(4) C5 0.024(3) 0.052(4) 0.028(4) 0.000(3) 0.009(3) 0.000(3) C2 0.044(4) 0.045(4) 0.046(5) -0.001(4) 0.021(4) -0.002(3) C23 0.032(4) 0.053(5) 0.041(4) 0.001(4) 0.014(3) 0.010(3) N12 0.074(5) 0.037(3) 0.034(4) 0.006(3) 0.031(3) 0.010(3) O17 0.041(3) 0.053(3) 0.045(3) 0.017(3) 0.012(2) 0.009(2) C36 0.032(4) 0.041(4) 0.029(4) 0.004(3) 0.008(3) -0.005(3) C48 0.037(4) 0.033(4) 0.051(5) -0.003(3) 0.023(4) 0.002(3) C41 0.047(4) 0.040(4) 0.033(4) 0.006(3) 0.015(3) 0.003(3) O7 0.030(3) 0.079(4) 0.062(4) -0.029(3) 0.020(3) -0.010(3) O2S 0.039(3) 0.044(3) 0.036(3) -0.002(2) 0.008(2) -0.004(2) C49 0.021(4) 0.075(6) 0.046(5) -0.025(4) -0.004(3) 0.009(4) C22 0.048(5) 0.063(5) 0.034(4) 0.005(4) 0.017(4) 0.016(4) C43 0.022(4) 0.063(5) 0.043(4) 0.010(4) 0.007(3) 0.008(3) C25 0.033(4) 0.046(4) 0.064(6) -0.018(4) 0.017(4) 0.003(4) F17 0.180(7) 0.185(6) 0.043(3) 0.020(4) 0.036(4) 0.130(5) C13 0.026(4) 0.047(4) 0.040(4) 0.006(4) 0.003(3) -0.002(3) C15 0.060(5) 0.074(6) 0.041(5) 0.014(4) 0.016(4) 0.000(5) C4 0.047(5) 0.073(5) 0.025(4) -0.008(4) 0.014(3) -0.014(4) C18 0.045(5) 0.049(5) 0.052(5) 0.007(4) 0.015(4) 0.018(4) C14 0.036(4) 0.072(5) 0.039(4) 0.003(4) 0.011(4) -0.011(4) C37 0.026(4) 0.050(5) 0.033(4) 0.007(4) 0.007(3) 0.003(3) C19 0.027(4) 0.065(5) 0.042(4) -0.005(4) 0.007(3) 0.007(4) F15 0.155(6) 0.095(4) 0.054(3) -0.017(3) 0.007(3) 0.074(4) C62 0.045(4) 0.044(4) 0.046(5) 0.008(4) 0.023(4) 0.012(3) C61 0.031(4) 0.036(4) 0.044(4) 0.004(3) 0.013(3) -0.004(3) C7 0.034(4) 0.037(4) 0.063(5) -0.004(4) 0.019(4) -0.005(3) C32 0.053(5) 0.043(4) 0.045(5) -0.007(4) 0.014(4) -0.009(4) N9 0.049(4) 0.057(4) 0.038(4) 0.000(3) 0.019(3) 0.008(3) C33 0.063(5) 0.079(6) 0.035(4) -0.006(4) 0.016(4) -0.035(5) N10 0.035(4) 0.106(6) 0.030(4) 0.010(4) 0.012(3) 0.029(4) C44 0.029(4) 0.059(5) 0.054(5) 0.007(4) 0.015(4) -0.001(4) C42 0.048(4) 0.040(4) 0.033(4) 0.001(3) 0.013(3) 0.000(3) C35 0.044(4) 0.057(5) 0.030(4) -0.008(4) 0.010(3) -0.010(4) C11 0.026(4) 0.079(6) 0.058(5) 0.006(5) 0.014(4) -0.010(4) C17 0.060(5) 0.036(4) 0.054(5) -0.003(4) 0.019(4) 0.006(4) C63 0.047(5) 0.086(6) 0.053(5) 0.033(5) 0.029(4) 0.018(4) C46 0.083(7) 0.085(7) 0.107(8) 0.043(6) 0.070(6) 0.038(6) C59 0.081(6) 0.042(4) 0.034(4) -0.001(4) 0.020(4) 0.016(4) C10 0.058(5) 0.082(6) 0.034(5) -0.007(4) 0.017(4) 0.003(5) C30 0.029(4) 0.059(5) 0.062(5) -0.024(4) 0.007(4) -0.010(4) F14 0.069(4) 0.098(4) 0.171(6) 0.059(4) -0.020(4) -0.044(3) C67 0.099(7) 0.057(5) 0.042(5) 0.019(4) 0.024(5) 0.020(5) C3 0.061(5) 0.064(5) 0.038(4) -0.008(4) 0.031(4) -0.023(4) C50 0.019(4) 0.076(6) 0.073(6) -0.031(5) 0.007(4) 0.000(4) C56 0.037(5) 0.147(9) 0.037(5) 0.021(6) 0.018(4) 0.036(6) C66 0.034(4) 0.083(6) 0.044(5) 0.013(5) 0.008(4) 0.015(4) C64 0.043(5) 0.082(6) 0.058(5) 0.017(5) 0.036(4) 0.016(4) C52 0.079(6) 0.061(5) 0.049(5) -0.016(4) 0.031(5) -0.013(5) F16 0.063(4) 0.170(6) 0.246(9) 0.144(6) 0.034(5) 0.005(4) C16 0.063(6) 0.068(5) 0.036(5) 0.012(4) 0.007(4) 0.003(5) C26 0.074(6) 0.055(5) 0.061(6) -0.023(4) 0.034(5) -0.019(4) C38 0.057(5) 0.072(5) 0.035(4) 0.004(4) 0.019(4) 0.014(4) C20 0.022(3) 0.064(5) 0.028(4) -0.002(4) 0.004(3) -0.005(3) C34 0.093(7) 0.093(7) 0.052(6) -0.019(5) 0.042(5) -0.033(6) C29 0.032(4) 0.067(5) 0.044(5) -0.021(4) 0.001(3) 0.002(4) C47 0.069(6) 0.044(4) 0.067(6) 0.021(4) 0.049(5) 0.020(4) C60 0.065(6) 0.054(5) 0.034(5) 0.005(4) 0.013(4) 0.026(4) C57 0.039(5) 0.183(11) 0.032(5) -0.010(6) 0.010(4) -0.016(6) F20 0.122(5) 0.103(4) 0.122(5) 0.011(4) 0.081(4) -0.030(4) C65 0.027(4) 0.095(6) 0.037(4) 0.005(4) 0.008(3) -0.009(4) C68 0.101(8) 0.048(5) 0.053(6) 0.007(4) 0.032(5) 0.000(5) C31 0.058(5) 0.052(5) 0.039(5) -0.019(4) 0.013(4) -0.017(4) C53 0.112(8) 0.047(5) 0.056(6) 0.000(4) 0.047(6) 0.019(5) C9 0.046(5) 0.110(7) 0.058(6) -0.038(5) 0.027(4) -0.031(5) C51 0.049(5) 0.093(7) 0.066(6) -0.024(5) 0.030(5) -0.012(5) C40 0.086(7) 0.070(6) 0.043(5) -0.020(4) 0.018(5) 0.030(5) C45 0.067(6) 0.080(6) 0.088(7) 0.021(5) 0.060(5) 0.029(5) C54 0.086(7) 0.051(5) 0.074(7) -0.019(5) 0.046(6) -0.021(5) C55 0.027(4) 0.157(10) 0.032(5) -0.022(6) 0.013(3) -0.029(5) C27 0.110(9) 0.124(9) 0.116(9) -0.080(8) 0.088(8) -0.058(7) C58 0.070(6) 0.106(7) 0.036(5) 0.008(5) 0.018(4) 0.017(6) C69 0.091(7) 0.069(6) 0.044(5) -0.001(4) 0.027(5) 0.042(5) C70 0.072(6) 0.083(6) 0.050(5) -0.003(5) 0.034(5) 0.011(5) C39 0.216(15) 0.173(12) 0.047(7) 0.034(8) 0.062(8) 0.107(11) C28 0.067(6) 0.096(7) 0.105(8) -0.035(6) 0.061(6) -0.021(5) P6 0.0498(13) 0.0432(11) 0.0562(14) 0.0027(10) 0.0258(11) -0.0013(10) F31 0.089(3) 0.049(2) 0.036(2) -0.006(2) 0.019(2) -0.027(2) F34 0.043(3) 0.074(3) 0.110(4) -0.005(3) 0.019(3) 0.020(2) F35 0.093(4) 0.119(4) 0.042(3) 0.026(3) 0.011(3) -0.017(3) F36 0.107(4) 0.052(3) 0.149(5) 0.006(3) 0.088(4) -0.008(3) F33 0.184(7) 0.169(6) 0.056(4) -0.044(4) 0.033(4) -0.110(5) F32 0.096(5) 0.059(3) 0.274(9) -0.022(4) 0.119(6) 0.004(3) O3S 0.026(5) 0.028(4) 0.050(6) 0.009(4) 0.009(4) 0.004(4) O4S 0.040(6) 0.075(7) 0.047(7) -0.004(6) 0.013(5) -0.005(5) F7 0.033(2) 0.049(2) 0.050(3) 0.011(2) 0.0098(19) 0.0093(18) F9 0.050(3) 0.045(2) 0.075(3) 0.001(2) 0.039(2) 0.000(2) F11 0.039(2) 0.062(3) 0.082(3) 0.004(2) 0.034(2) -0.001(2) F12 0.031(2) 0.056(3) 0.062(3) 0.004(2) 0.005(2) 0.0076(19) F8 0.050(3) 0.060(3) 0.045(3) -0.022(2) 0.010(2) 0.002(2) F10 0.067(3) 0.055(3) 0.034(2) -0.015(2) 0.002(2) -0.004(2) C72 0.044(4) 0.045(4) 0.042(5) -0.003(4) 0.016(4) 0.001(4) C71 0.063(5) 0.058(5) 0.046(5) -0.007(4) 0.018(4) 0.006(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag K5 P5 3.503(2) . ? K5 F29 2.880(4) . ? K5 F26 2.795(4) . ? K5 F25 2.929(4) . ? K5 O16 2.805(5) . ? K5 O13 2.761(5) 2_755 ? K5 O13 2.764(5) . ? K5 O14 3.009(5) . ? K5 O15 2.672(5) . ? K5 O3S 2.899(8) . ? K5 O3S 3.027(8) 2_755 ? K2 O3 2.734(5) . ? K2 O4 2.727(5) . ? K2 O5 2.907(5) . ? K2 O6 2.742(5) . ? K2 O7 3.290(6) . ? K2 O2S 2.802(5) . ? K2 F7 2.844(4) . ? K2 F9 2.765(4) . ? K2 F10 3.250(5) . ? K4 O10 2.738(5) . ? K4 O11 2.879(4) . ? K4 O12 2.712(4) . ? K4 O1 2.786(5) . ? K4 O9 2.691(5) . ? K4 F19 2.790(4) . ? K4 C1 3.501(7) . ? K4 F21 2.932(5) . ? K4 O2S 3.198(5) . ? K1 F5 2.965(4) . ? K1 F1 2.874(4) . ? K1 F4 2.928(4) . ? K1 O3 2.865(5) . ? K1 O4 2.776(5) . ? K1 O12 2.838(4) . ? K1 O2 3.116(4) . ? K1 O1 2.866(5) . ? K1 O1S 2.907(5) . ? K1 O2S 3.311(5) . ? K3 O10 2.810(4) . ? K3 O8 3.073(5) . ? K3 O6 2.774(5) . ? K3 F13 2.730(4) . ? K3 O9 2.707(5) . ? K3 O7 2.738(5) . ? K3 O2S 2.910(4) . ? K3 F15 2.906(5) . ? K3 F16 3.338(9) . ? P2 F7 1.604(4) . ? P2 F9 1.601(4) . ? P2 F11 1.587(4) . ? P2 F12 1.584(4) . ? P2 F8 1.588(4) . ? P2 F10 1.598(4) . ? K6 O16 2.830(5) . ? K6 O15 2.790(5) . ? K6 O18 2.694(5) 2_755 ? K6 O18 2.777(5) . ? K6 O17 2.877(5) . ? K6 F35 2.772(5) 1_565 ? K6 F36 3.102(6) 1_565 ? K6 O3S 2.752(8) 2_755 ? K6 O3S 3.148(8) . ? K6 O4S 3.037(10) . ? P5 F29 1.605(4) . ? P5 F28 1.591(4) . ? P5 F26 1.621(4) . ? P5 F30 1.601(4) . ? P5 F25 1.608(4) . ? P5 F27 1.580(4) . ? P1 F5 1.616(4) . ? P1 F3 1.593(4) . ? P1 F1 1.611(4) . ? P1 F4 1.602(4) . ? P1 F6 1.585(4) . ? P1 F2 1.587(4) . ? P4 F22 1.574(4) . ? P4 F19 1.600(5) . ? P4 F23 1.577(5) . ? P4 F24 1.574(5) . ? P4 F21 1.590(5) . ? P4 F20 1.580(5) . ? P3 F13 1.613(4) . ? P3 F18 1.575(5) . ? P3 F17 1.564(5) . ? P3 F15 1.552(5) . ? P3 F14 1.516(5) . ? P3 F16 1.553(6) . ? O10 C37 1.227(8) . ? O11 C43 1.428(7) . ? O11 C42 1.432(7) . ? O8 C30 1.429(8) . ? O8 C31 1.424(8) . ? O3 C12 1.232(7) . ? O4 C13 1.212(8) . ? O5 C18 1.432(8) . ? O5 C19 1.426(7) . ? O12 C48 1.236(7) . ? N1 C1 1.332(8) . ? N1 C5 1.467(7) . ? N1 C4 1.467(8) . ? O6 C24 1.246(7) . ? O16 C61 1.247(7) . ? N4 C24 1.329(8) . ? N4 C21 1.470(8) . ? N4 C20 1.458(8) . ? O2 C6 1.429(7) . ? O2 C7 1.432(7) . ? O1 C1 1.242(7) . ? O9 C36 1.243(7) . ? N7 C41 1.435(8) . ? N7 C37 1.343(8) . ? N7 C40 1.462(8) . ? N2 C12 1.344(7) . ? N2 C8 1.444(8) . ? N2 C9 1.454(9) . ? N6 C36 1.327(8) . ? N6 C32 1.453(8) . ? N6 C33 1.455(8) . ? O13 K5 2.761(5) 2_755 ? O13 C49 1.226(8) . ? C1 C2 1.482(9) . ? N3 C13 1.351(8) . ? N3 C17 1.455(8) . ? N3 C16 1.473(8) . ? C24 C23 1.501(9) . ? O14 C54 1.419(9) . ? O14 C55 1.415(9) . ? C12 C11 1.492(9) . ? N5 C25 1.336(8) . ? N5 C29 1.446(8) . ? N5 C28 1.469(9) . ? N11 C61 1.337(8) . ? N11 C64 1.463(8) . ? N11 C65 1.447(8) . ? C6 C5 1.494(9) . ? O15 C60 1.225(8) . ? C8 C7 1.497(8) . ? N8 C48 1.349(8) . ? N8 C44 1.444(8) . ? N8 C45 1.458(9) . ? O18 K6 2.694(5) 2_755 ? O18 C72 1.231(8) . ? C21 C22 1.511(9) . ? C2 C3 1.528(9) . ? C23 C22 1.547(9) . ? N12 C68 1.445(9) . ? N12 C69 1.453(8) . ? N12 C72 1.341(9) . ? O17 C67 1.420(8) . ? O17 C66 1.445(8) . ? C36 C35 1.515(9) . ? C48 C47 1.490(9) . ? C41 C42 1.506(9) . ? O7 C25 1.237(8) . ? C49 N9 1.322(9) . ? C49 C50 1.518(11) . ? C43 C44 1.496(9) . ? C25 C26 1.509(10) . ? C13 C14 1.519(10) . ? C15 C14 1.517(9) . ? C15 C16 1.503(10) . ? C4 C3 1.531(9) . ? C18 C17 1.497(10) . ? C37 C38 1.506(9) . ? C19 C20 1.492(9) . ? C62 C61 1.504(9) . ? C62 C63 1.529(9) . ? C32 C31 1.504(9) . ? N9 C52 1.468(9) . ? N9 C53 1.434(9) . ? C33 C34 1.523(10) . ? N10 C56 1.473(10) . ? N10 C60 1.355(10) . ? N10 C57 1.464(9) . ? C35 C34 1.510(10) . ? C11 C10 1.509(10) . ? C63 C64 1.539(10) . ? C46 C47 1.516(10) . ? C46 C45 1.537(11) . ? C59 C60 1.490(10) . ? C59 C58 1.511(10) . ? C10 C9 1.501(10) . ? C30 C29 1.507(10) . ? C67 C68 1.510(11) . ? C50 C51 1.532(10) . ? C56 C55 1.492(12) . ? C66 C65 1.491(10) . ? C52 C51 1.513(10) . ? C26 C27 1.483(11) . ? C38 C39 1.464(12) . ? C57 C58 1.511(12) . ? C53 C54 1.508(11) . ? C40 C39 1.496(12) . ? C27 C28 1.503(11) . ? C69 C70 1.530(10) . ? C70 C71 1.532(10) . ? P6 F31 1.580(4) . ? P6 F34 1.562(5) . ? P6 F35 1.627(5) . ? P6 F36 1.571(5) . ? P6 F33 1.525(5) . ? P6 F32 1.563(5) . ? F35 K6 2.772(5) 1_545 ? F36 K6 3.102(6) 1_545 ? O3S K5 3.027(8) 2_755 ? O3S K6 2.752(8) 2_755 ? O3S O3S 1.556(17) 2_755 ? C72 C71 1.488(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P5 K5 K5 132.61(6) . 2_755 ? F29 K5 K5 121.00(9) . 2_755 ? F29 K5 P5 26.95(8) . . ? F29 K5 F25 45.49(10) . . ? F29 K5 O14 110.21(12) . . ? F29 K5 O3S 99.83(18) . . ? F29 K5 O3S 129.14(18) . 2_755 ? F26 K5 K5 112.30(9) . 2_755 ? F26 K5 P5 26.96(8) . . ? F26 K5 F29 46.82(10) . . ? F26 K5 F25 46.63(11) . . ? F26 K5 O16 114.57(12) . . ? F26 K5 O14 77.12(13) . . ? F26 K5 O3S 157.65(19) . 2_755 ? F26 K5 O3S 132.96(19) . . ? F25 K5 K5 158.71(9) . 2_755 ? F25 K5 P5 27.13(8) . . ? F25 K5 O14 66.93(12) . . ? F25 K5 O3S 152.03(18) . 2_755 ? O16 K5 K5 105.80(9) . 2_755 ? O16 K5 P5 89.51(10) . . ? O16 K5 F29 68.20(11) . . ? O16 K5 F25 84.99(12) . . ? O16 K5 O14 127.85(14) . . ? O16 K5 O3S 70.39(17) . 2_755 ? O16 K5 O3S 55.50(18) . . ? O13 K5 K5 45.21(11) 2_755 2_755 ? O13 K5 K5 45.13(11) . 2_755 ? O13 K5 P5 88.22(11) 2_755 . ? O13 K5 P5 137.19(15) . . ? O13 K5 F29 152.84(17) . . ? O13 K5 F29 77.39(13) 2_755 . ? O13 K5 F26 74.21(14) 2_755 . ? O13 K5 F26 111.10(17) . . ? O13 K5 F25 136.49(14) . . ? O13 K5 F25 115.34(13) 2_755 . ? O13 K5 O16 133.20(17) . . ? O13 K5 O16 101.69(18) 2_755 . ? O13 K5 O13 81.1(2) 2_755 . ? O13 K5 O14 129.65(18) 2_755 . ? O13 K5 O14 71.87(14) . . ? O13 K5 O3S 83.5(2) 2_755 2_755 ? O13 K5 O3S 63.5(2) . 2_755 ? O13 K5 O3S 85.8(2) . . ? O13 K5 O3S 65.3(2) 2_755 . ? O14 K5 K5 116.18(10) . 2_755 ? O14 K5 P5 84.24(10) . . ? O14 K5 O3S 118.18(19) . 2_755 ? O15 K5 K5 101.42(14) . 2_755 ? O15 K5 P5 125.85(15) . . ? O15 K5 F29 126.13(16) . . ? O15 K5 F26 142.25(16) . . ? O15 K5 F25 99.55(16) . . ? O15 K5 O16 69.48(15) . . ? O15 K5 O13 143.44(18) . 2_755 ? O15 K5 O13 80.9(2) . . ? O15 K5 O14 72.98(15) . . ? O15 K5 O3S 81.9(2) . . ? O15 K5 O3S 60.0(2) . 2_755 ? O3S K5 K5 50.34(15) . 2_755 ? O3S K5 K5 47.49(15) 2_755 2_755 ? O3S K5 P5 156.05(16) 2_755 . ? O3S K5 P5 126.57(17) . . ? O3S K5 F25 137.57(18) . . ? O3S K5 O14 148.50(19) . . ? O3S K5 O3S 30.4(3) . 2_755 ? K1 K2 K3 84.06(4) . . ? P2 K2 K1 138.54(5) . . ? P2 K2 K3 122.46(5) . . ? O3 K2 K1 47.91(10) . . ? O3 K2 K3 115.88(11) . . ? O3 K2 P2 90.63(10) . . ? O3 K2 O5 133.11(15) . . ? O3 K2 O6 135.92(14) . . ? O3 K2 O7 111.01(14) . . ? O3 K2 O2S 74.21(14) . . ? O3 K2 F7 79.77(13) . . ? O3 K2 F9 82.76(14) . . ? O3 K2 F10 117.03(12) . . ? O4 K2 K1 46.03(10) . . ? O4 K2 K3 103.91(11) . . ? O4 K2 P2 133.06(12) . . ? O4 K2 O3 74.03(15) . . ? O4 K2 O5 77.11(14) . . ? O4 K2 O6 79.75(15) . . ? O4 K2 O7 142.68(14) . . ? O4 K2 O2S 98.51(14) . . ? O4 K2 F7 146.28(15) . . ? O4 K2 F9 107.74(14) . . ? O4 K2 F10 139.24(13) . . ? O5 K2 K1 122.57(10) . . ? O5 K2 K3 106.40(9) . . ? O5 K2 P2 82.91(10) . . ? O5 K2 O7 114.40(13) . . ? O5 K2 F10 67.38(12) . . ? O6 K2 K1 88.60(10) . . ? O6 K2 K3 38.97(9) . . ? O6 K2 P2 132.48(10) . . ? O6 K2 O5 71.49(13) . . ? O6 K2 O7 71.74(13) . . ? O6 K2 O2S 75.43(13) . . ? O6 K2 F7 133.83(13) . . ? O6 K2 F9 139.65(13) . . ? O6 K2 F10 106.04(12) . . ? O7 K2 K1 108.61(9) . . ? O7 K2 K3 39.50(9) . . ? O7 K2 P2 84.26(9) . . ? O2S K2 K1 57.03(9) . . ? O2S K2 K3 42.06(9) . . ? O2S K2 P2 119.97(11) . . ? O2S K2 O5 146.88(13) . . ? O2S K2 O7 51.67(13) . . ? O2S K2 F7 94.32(13) . . ? O2S K2 F10 122.15(13) . . ? F7 K2 K1 123.60(9) . . ? F7 K2 K3 106.46(9) . . ? F7 K2 P2 25.84(8) . . ? F7 K2 O5 107.49(12) . . ? F7 K2 O7 67.15(12) . . ? F7 K2 F10 42.45(10) . . ? F9 K2 K1 125.73(10) . . ? F9 K2 K3 146.81(9) . . ? F9 K2 P2 25.34(8) . . ? F9 K2 O5 71.86(13) . . ? F9 K2 O7 109.58(12) . . ? F9 K2 O2S 138.57(14) . . ? F9 K2 F7 47.22(11) . . ? F9 K2 F10 42.96(11) . . ? F10 K2 K1 164.85(8) . . ? F10 K2 K3 104.75(8) . . ? F10 K2 P2 26.51(7) . . ? F10 K2 O7 73.39(11) . . ? P4 K4 K3 131.89(5) . . ? O10 K4 K3 44.44(9) . . ? O10 K4 P4 138.18(11) . . ? O10 K4 O11 72.04(13) . . ? O10 K4 O1 126.57(14) . . ? O10 K4 F19 114.37(14) . . ? O10 K4 C1 145.25(15) . . ? O10 K4 F21 154.77(14) . . ? O10 K4 C48 75.38(15) . . ? O10 K4 O2S 81.20(12) . . ? O11 K4 K3 112.59(10) . . ? O11 K4 P4 78.90(10) . . ? O11 K4 C1 134.60(14) . . ? O11 K4 F21 103.08(13) . . ? O11 K4 C48 60.89(14) . . ? O11 K4 O2S 152.29(13) . . ? O12 K4 K3 110.47(10) . . ? O12 K4 P4 117.64(11) . . ? O12 K4 O10 84.73(14) . . ? O12 K4 O11 77.29(13) . . ? O12 K4 O1 74.23(13) . . ? O12 K4 F19 127.83(15) . . ? O12 K4 C1 81.88(15) . . ? O12 K4 F21 118.94(15) . . ? O12 K4 C48 17.20(13) . . ? O12 K4 O2S 93.55(13) . . ? O1 K4 K3 98.61(9) . . ? O1 K4 P4 94.52(10) . . ? O1 K4 O11 143.47(13) . . ? O1 K4 F19 117.38(14) . . ? O1 K4 C1 18.71(13) . . ? O1 K4 F21 72.27(13) . . ? O1 K4 C48 91.33(14) . . ? O1 K4 O2S 52.69(12) . . ? O9 K4 K3 42.21(10) . . ? O9 K4 P4 89.68(11) . . ? O9 K4 O10 73.10(14) . . ? O9 K4 O11 109.61(14) . . ? O9 K4 O12 152.67(15) . . ? O9 K4 O1 106.20(14) . . ? O9 K4 F19 77.10(15) . . ? O9 K4 C1 107.36(15) . . ? O9 K4 F21 86.00(15) . . ? O9 K4 C48 148.44(16) . . ? O9 K4 O2S 67.84(13) . . ? F19 K4 K3 116.72(11) . . ? F19 K4 P4 23.92(9) . . ? F19 K4 O11 65.32(14) . . ? F19 K4 C1 99.07(14) . . ? F19 K4 F21 45.23(12) . . ? F19 K4 C48 118.19(16) . . ? F19 K4 O2S 135.47(15) . . ? C1 K4 K3 112.40(11) . . ? C1 K4 P4 75.89(11) . . ? C1 K4 C48 97.63(16) . . ? F21 K4 K3 123.82(12) . . ? F21 K4 P4 24.63(9) . . ? F21 K4 C1 54.41(14) . . ? F21 K4 C48 124.82(16) . . ? F21 K4 O2S 104.21(13) . . ? C48 K4 K3 110.37(12) . . ? C48 K4 P4 115.38(12) . . ? O2S K4 K3 45.95(8) . . ? O2S K4 P4 127.69(10) . . ? O2S K4 C1 67.87(13) . . ? O2S K4 C48 105.92(14) . . ? P1 K1 K2 133.11(5) . . ? F5 K1 K2 112.86(8) . . ? F5 K1 P1 26.69(7) . . ? F5 K1 O2 68.63(12) . . ? F5 K1 O2S 156.02(11) . . ? F1 K1 K2 158.23(9) . . ? F1 K1 P1 26.29(8) . . ? F1 K1 F5 45.54(10) . . ? F1 K1 F4 45.51(10) . . ? F1 K1 O2 62.61(11) . . ? F1 K1 O1S 114.13(14) . . ? F1 K1 O2S 156.36(11) . . ? F4 K1 K2 120.34(9) . . ? F4 K1 P1 26.31(8) . . ? F4 K1 F5 44.97(11) . . ? F4 K1 O2 103.39(11) . . ? F4 K1 O2S 146.94(12) . . ? O3 K1 K2 45.08(9) . . ? O3 K1 P1 119.17(11) . . ? O3 K1 F5 92.64(12) . . ? O3 K1 F1 126.28(13) . . ? O3 K1 F4 131.12(14) . . ? O3 K1 O2 72.13(12) . . ? O3 K1 O1 74.18(14) . . ? O3 K1 O1S 116.69(14) . . ? O3 K1 O2S 65.01(12) . . ? O4 K1 K2 44.99(10) . . ? O4 K1 P1 89.96(11) . . ? O4 K1 F5 77.63(13) . . ? O4 K1 F1 116.23(13) . . ? O4 K1 F4 75.76(13) . . ? O4 K1 O3 71.27(15) . . ? O4 K1 O12 132.99(15) . . ? O4 K1 O2 128.08(14) . . ? O4 K1 O1 133.70(14) . . ? O4 K1 O1S 66.60(15) . . ? O4 K1 O2S 86.51(13) . . ? O12 K1 K2 128.46(10) . . ? O12 K1 P1 89.32(10) . . ? O12 K1 F5 115.08(12) . . ? O12 K1 F1 71.11(12) . . ? O12 K1 F4 83.50(12) . . ? O12 K1 O3 144.96(14) . . ? O12 K1 O2 97.41(13) . . ? O12 K1 O1 71.13(13) . . ? O12 K1 O1S 68.53(14) . . ? O12 K1 O2S 88.89(12) . . ? O2 K1 K2 116.90(9) . . ? O2 K1 P1 77.21(9) . . ? O2 K1 O2S 109.49(12) . . ? O1 K1 K2 88.70(9) . . ? O1 K1 P1 134.28(10) . . ? O1 K1 F5 134.11(13) . . ? O1 K1 F1 108.86(12) . . ? O1 K1 F4 149.92(12) . . ? O1 K1 O2 65.49(12) . . ? O1 K1 O1S 104.41(14) . . ? O1 K1 O2S 50.83(11) . . ? O1S K1 K2 71.82(10) . . ? O1S K1 P1 105.95(11) . . ? O1S K1 F5 120.44(14) . . ? O1S K1 F4 79.96(13) . . ? O1S K1 O2 165.29(14) . . ? O1S K1 O2S 67.35(13) . . ? O2S K1 K2 45.23(8) . . ? O2S K1 P1 173.24(10) . . ? K4 K3 K2 88.76(4) . . ? P3 K3 K2 125.93(5) . . ? P3 K3 K4 133.58(5) . . ? O10 K3 K2 105.85(10) . . ? O10 K3 K4 43.03(10) . . ? O10 K3 P3 93.66(11) . . ? O10 K3 O8 131.79(13) . . ? O10 K3 O2S 85.36(13) . . ? O10 K3 F15 115.68(15) . . ? O10 K3 F16 77.46(14) . . ? O8 K3 K2 118.72(10) . . ? O8 K3 K4 117.53(9) . . ? O8 K3 P3 75.29(9) . . ? O8 K3 F16 100.68(14) . . ? O6 K3 K2 38.44(9) . . ? O6 K3 K4 106.20(10) . . ? O6 K3 P3 90.94(10) . . ? O6 K3 O10 95.39(13) . . ? O6 K3 O8 130.81(13) . . ? O6 K3 O2S 73.21(13) . . ? O6 K3 F15 78.59(15) . . ? O6 K3 F16 73.35(14) . . ? F13 K3 K2 150.56(10) . . ? F13 K3 K4 114.10(10) . . ? F13 K3 P3 24.78(9) . . ? F13 K3 O10 82.19(14) . . ? F13 K3 O8 68.32(14) . . ? F13 K3 O6 113.77(13) . . ? F13 K3 O7 134.49(15) . . ? F13 K3 O2S 166.22(14) . . ? F13 K3 F15 46.64(12) . . ? F13 K3 F16 41.29(14) . . ? O9 K3 K2 111.25(11) . . ? O9 K3 K4 41.90(10) . . ? O9 K3 P3 122.76(11) . . ? O9 K3 O10 71.73(13) . . ? O9 K3 O8 75.67(13) . . ? O9 K3 O6 143.83(14) . . ? O9 K3 F13 98.19(14) . . ? O9 K3 O7 89.19(16) . . ? O9 K3 O2S 72.17(13) . . ? O9 K3 F15 137.57(16) . . ? O9 K3 F16 132.28(16) . . ? O7 K3 K2 49.84(12) . . ? O7 K3 K4 101.21(11) . . ? O7 K3 P3 124.35(11) . . ? O7 K3 O10 141.65(14) . . ? O7 K3 O8 70.32(14) . . ? O7 K3 O6 80.52(15) . . ? O7 K3 O2S 56.80(13) . . ? O7 K3 F15 100.97(15) . . ? O7 K3 F16 135.27(16) . . ? O2S K3 K2 40.16(9) . . ? O2S K3 K4 52.16(9) . . ? O2S K3 P3 163.92(10) . . ? O2S K3 O8 117.01(13) . . ? O2S K3 F16 140.50(15) . . ? F15 K3 K2 106.48(10) . . ? F15 K3 K4 157.80(12) . . ? F15 K3 P3 24.58(10) . . ? F15 K3 O8 69.58(16) . . ? F15 K3 O2S 146.31(14) . . ? F15 K3 F16 39.07(15) . . ? F16 K3 K2 111.70(12) . . ? F16 K3 K4 120.49(11) . . ? F16 K3 P3 25.41(10) . . ? F7 P2 K2 50.60(15) . . ? F9 P2 K2 47.65(14) . . ? F9 P2 F7 89.0(2) . . ? F11 P2 K2 131.29(17) . . ? F11 P2 F7 89.9(2) . . ? F11 P2 F9 178.9(2) . . ? F11 P2 F8 90.5(2) . . ? F11 P2 F10 90.4(2) . . ? F12 P2 K2 128.47(18) . . ? F12 P2 F7 179.1(3) . . ? F12 P2 F9 90.1(2) . . ? F12 P2 F11 90.9(2) . . ? F12 P2 F8 90.1(2) . . ? F12 P2 F10 90.9(2) . . ? F8 P2 K2 113.40(16) . . ? F8 P2 F7 90.3(2) . . ? F8 P2 F9 89.8(2) . . ? F8 P2 F10 178.6(2) . . ? F10 P2 K2 65.25(17) . . ? F10 P2 F7 88.7(2) . . ? F10 P2 F9 89.3(2) . . ? O16 K6 K6 87.84(10) . 2_755 ? O16 K6 O17 71.46(13) . . ? O16 K6 P6 133.28(10) . 1_565 ? O16 K6 F36 111.30(13) . 1_565 ? O16 K6 O3S 52.46(17) . . ? O16 K6 O4S 106.4(2) . . ? O15 K6 K6 115.51(12) . 2_755 ? O15 K6 O16 67.51(15) . . ? O15 K6 O17 107.44(17) . . ? O15 K6 P6 91.77(11) . 1_565 ? O15 K6 F36 72.44(14) . 1_565 ? O15 K6 O3S 75.70(18) . . ? O15 K6 O4S 60.2(2) . . ? O18 K6 K6 45.96(11) 2_755 2_755 ? O18 K6 K6 44.21(10) . 2_755 ? O18 K6 O16 133.80(14) 2_755 . ? O18 K6 O16 77.22(16) . . ? O18 K6 O15 140.64(17) . . ? O18 K6 O15 125.8(2) 2_755 . ? O18 K6 O18 69.1(2) 2_755 . ? O18 K6 O17 126.08(17) 2_755 . ? O18 K6 O17 75.77(14) . . ? O18 K6 P6 126.02(14) . 1_565 ? O18 K6 P6 92.59(11) 2_755 1_565 ? O18 K6 F35 78.25(16) 2_755 1_565 ? O18 K6 F36 139.63(15) . 1_565 ? O18 K6 F36 114.87(14) 2_755 1_565 ? O18 K6 O3S 69.1(2) . . ? O18 K6 O3S 85.69(18) 2_755 . ? O18 K6 O3S 76.5(2) 2_755 2_755 ? O18 K6 O4S 117.5(2) . . ? O18 K6 O4S 65.6(2) 2_755 . ? O17 K6 K6 119.75(11) . 2_755 ? O17 K6 P6 76.35(10) . 1_565 ? O17 K6 F36 70.59(13) . 1_565 ? O17 K6 O3S 118.16(18) . . ? O17 K6 O4S 166.1(2) . . ? P6 K6 K6 138.16(6) 1_565 2_755 ? F35 K6 K6 120.13(11) 1_565 2_755 ? F35 K6 O16 142.03(15) 1_565 . ? F35 K6 O15 114.21(16) 1_565 . ? F35 K6 O18 104.22(18) 1_565 . ? F35 K6 O17 72.25(15) 1_565 . ? F35 K6 P6 22.50(11) 1_565 1_565 ? F35 K6 F36 44.46(13) 1_565 1_565 ? F35 K6 O3S 163.93(19) 1_565 . ? F35 K6 O4S 106.1(2) 1_565 . ? F36 K6 K6 160.77(10) 1_565 2_755 ? F36 K6 P6 23.71(9) 1_565 1_565 ? F36 K6 O3S 148.07(18) 1_565 . ? O3S K6 K6 44.78(15) . 2_755 ? O3S K6 K6 53.69(17) 2_755 2_755 ? O3S K6 O16 74.17(19) 2_755 . ? O3S K6 O15 62.3(2) 2_755 . ? O3S K6 O18 92.3(2) 2_755 . ? O3S K6 O17 145.3(2) 2_755 . ? O3S K6 P6 133.67(18) 2_755 1_565 ? O3S K6 P6 162.93(16) . 1_565 ? O3S K6 F35 142.4(2) 2_755 1_565 ? O3S K6 F36 128.1(2) 2_755 1_565 ? O3S K6 O3S 29.6(3) 2_755 . ? O3S K6 O4S 37.4(2) 2_755 . ? O4S K6 K6 73.34(18) . 2_755 ? O4S K6 P6 96.95(19) . 1_565 ? O4S K6 F36 98.4(2) . 1_565 ? O4S K6 O3S 66.9(2) . . ? F29 P5 K5 54.39(14) . . ? F29 P5 F26 88.7(2) . . ? F29 P5 F25 88.7(2) . . ? F28 P5 K5 127.33(16) . . ? F28 P5 F29 90.0(2) . . ? F28 P5 F26 178.6(2) . . ? F28 P5 F30 90.9(2) . . ? F28 P5 F25 90.2(2) . . ? F26 P5 K5 51.40(14) . . ? F30 P5 K5 121.85(16) . . ? F30 P5 F29 89.5(2) . . ? F30 P5 F26 89.6(2) . . ? F30 P5 F25 177.9(2) . . ? F25 P5 K5 56.13(15) . . ? F25 P5 F26 89.2(2) . . ? F27 P5 K5 124.47(18) . . ? F27 P5 F29 178.8(3) . . ? F27 P5 F28 91.0(2) . . ? F27 P5 F26 90.3(2) . . ? F27 P5 F30 91.0(2) . . ? F27 P5 F25 90.7(2) . . ? F5 P1 K1 55.48(14) . . ? F3 P1 K1 123.25(17) . . ? F3 P1 F5 178.7(2) . . ? F3 P1 F1 90.2(2) . . ? F3 P1 F4 90.1(2) . . ? F1 P1 K1 52.20(14) . . ? F1 P1 F5 89.0(2) . . ? F4 P1 K1 54.10(16) . . ? F4 P1 F5 88.9(2) . . ? F4 P1 F1 88.6(2) . . ? F6 P1 K1 126.48(18) . . ? F6 P1 F5 90.2(2) . . ? F6 P1 F3 90.6(2) . . ? F6 P1 F1 178.7(3) . . ? F6 P1 F4 90.3(2) . . ? F6 P1 F2 90.8(3) . . ? F2 P1 K1 124.06(19) . . ? F2 P1 F5 89.6(2) . . ? F2 P1 F3 91.4(2) . . ? F2 P1 F1 90.2(2) . . ? F2 P1 F4 178.1(3) . . ? F22 P4 K4 110.13(18) . . ? F22 P4 F19 88.0(3) . . ? F22 P4 F23 89.5(3) . . ? F22 P4 F24 90.7(3) . . ? F22 P4 F21 90.7(3) . . ? F22 P4 F20 178.8(3) . . ? F19 P4 K4 45.00(16) . . ? F23 P4 K4 127.0(2) . . ? F23 P4 F19 89.7(3) . . ? F23 P4 F21 177.1(3) . . ? F23 P4 F20 91.4(3) . . ? F24 P4 K4 134.6(2) . . ? F24 P4 F19 178.1(3) . . ? F24 P4 F23 91.6(3) . . ? F24 P4 F21 91.3(3) . . ? F24 P4 F20 90.1(3) . . ? F21 P4 K4 50.24(18) . . ? F21 P4 F19 87.4(3) . . ? F20 P4 K4 68.6(2) . . ? F20 P4 F19 91.2(3) . . ? F20 P4 F21 88.3(3) . . ? F13 P3 K3 45.18(15) . . ? F18 P3 K3 134.3(2) . . ? F18 P3 F13 179.5(3) . . ? F17 P3 K3 123.6(3) . . ? F17 P3 F13 86.9(3) . . ? F17 P3 F18 93.5(3) . . ? F15 P3 K3 51.2(2) . . ? F15 P3 F13 89.9(3) . . ? F15 P3 F18 89.7(3) . . ? F15 P3 F17 173.8(4) . . ? F15 P3 F16 86.5(4) . . ? F14 P3 K3 112.6(3) . . ? F14 P3 F13 89.6(3) . . ? F14 P3 F18 90.7(3) . . ? F14 P3 F17 90.1(4) . . ? F14 P3 F15 95.2(4) . . ? F14 P3 F16 177.6(3) . . ? F16 P3 K3 67.2(4) . . ? F16 P3 F13 88.7(3) . . ? F16 P3 F18 91.0(4) . . ? F16 P3 F17 88.1(4) . . ? P5 F29 K5 98.67(18) . . ? P1 F5 K1 97.83(17) . . ? P5 F26 K5 101.64(17) . . ? K4 O10 K3 92.53(14) . . ? C37 O10 K4 132.6(4) . . ? C37 O10 K3 124.4(4) . . ? C43 O11 K4 118.6(4) . . ? C43 O11 C42 110.7(5) . . ? C42 O11 K4 115.6(4) . . ? P1 F1 K1 101.51(17) . . ? C30 O8 K3 117.9(4) . . ? C31 O8 K3 119.7(4) . . ? C31 O8 C30 109.7(5) . . ? P5 F25 K5 96.74(18) . . ? P1 F4 K1 99.60(19) . . ? K2 O3 K1 87.02(14) . . ? C12 O3 K2 139.8(4) . . ? C12 O3 K1 129.5(4) . . ? K2 O4 K1 88.98(15) . . ? C13 O4 K2 128.2(4) . . ? C13 O4 K1 139.5(4) . . ? C18 O5 K2 118.8(4) . . ? C19 O5 K2 118.4(4) . . ? C19 O5 C18 111.5(5) . . ? K4 O12 K1 96.36(14) . . ? C48 O12 K4 122.4(4) . . ? C48 O12 K1 131.5(4) . . ? C1 N1 C5 123.7(5) . . ? C1 N1 C4 113.7(5) . . ? C5 N1 C4 122.4(5) . . ? K2 O6 K3 102.59(15) . . ? C24 O6 K2 129.9(4) . . ? C24 O6 K3 122.1(4) . . ? P3 F13 K3 110.0(2) . . ? K5 O16 K6 99.84(14) . . ? C61 O16 K5 128.8(4) . . ? C61 O16 K6 126.0(4) . . ? C24 N4 C21 113.0(5) . . ? C24 N4 C20 123.5(5) . . ? C20 N4 C21 122.5(5) . . ? C6 O2 K1 116.3(4) . . ? C6 O2 C7 112.8(5) . . ? C7 O2 K1 117.6(4) . . ? K4 O1 K1 94.07(14) . . ? C1 O1 K4 115.2(4) . . ? C1 O1 K1 137.7(4) . . ? K4 O9 K3 95.90(15) . . ? C36 O9 K4 135.5(4) . . ? C36 O9 K3 123.0(4) . . ? P4 F19 K4 111.1(2) . . ? C41 N7 C40 122.0(6) . . ? C37 N7 C41 124.3(6) . . ? C37 N7 C40 113.3(6) . . ? C12 N2 C8 124.6(6) . . ? C12 N2 C9 114.3(6) . . ? C8 N2 C9 121.0(5) . . ? C36 N6 C32 123.5(6) . . ? C36 N6 C33 112.9(6) . . ? C32 N6 C33 122.4(6) . . ? K5 O13 K5 89.66(16) 2_755 . ? C49 O13 K5 132.8(4) . . ? C49 O13 K5 137.4(4) . 2_755 ? N1 C1 K4 112.8(4) . . ? N1 C1 C2 108.7(6) . . ? O1 C1 K4 46.1(3) . . ? O1 C1 N1 125.1(6) . . ? O1 C1 C2 126.2(6) . . ? C2 C1 K4 117.1(4) . . ? C13 N3 C17 122.6(6) . . ? C13 N3 C16 114.3(6) . . ? C17 N3 C16 123.1(6) . . ? O6 C24 N4 125.6(6) . . ? O6 C24 C23 124.9(6) . . ? N4 C24 C23 109.5(6) . . ? C54 O14 K5 119.2(5) . . ? C55 O14 K5 118.4(4) . . ? C55 O14 C54 111.7(6) . . ? O3 C12 N2 124.1(6) . . ? O3 C12 C11 127.2(6) . . ? N2 C12 C11 108.7(6) . . ? C25 N5 C29 124.1(6) . . ? C25 N5 C28 112.6(7) . . ? C29 N5 C28 122.3(6) . . ? P4 F21 K4 105.1(2) . . ? C61 N11 C64 112.0(6) . . ? C61 N11 C65 122.7(6) . . ? C65 N11 C64 123.6(6) . . ? O2 C6 C5 108.7(5) . . ? K5 O15 K6 104.22(17) . . ? C60 O15 K5 132.3(5) . . ? C60 O15 K6 123.2(5) . . ? N2 C8 C7 113.4(5) . . ? C48 N8 C44 122.8(6) . . ? C48 N8 C45 113.1(6) . . ? C44 N8 C45 122.8(6) . . ? K6 O18 K6 89.83(15) 2_755 . ? C72 O18 K6 139.3(5) . 2_755 ? C72 O18 K6 130.3(5) . . ? N4 C21 C22 103.4(5) . . ? N1 C5 C6 111.3(5) . . ? C1 C2 C3 105.3(6) . . ? C24 C23 C22 103.1(5) . . ? C68 N12 C69 122.3(6) . . ? C72 N12 C68 123.8(6) . . ? C72 N12 C69 113.6(6) . . ? C67 O17 K6 119.1(5) . . ? C67 O17 C66 112.3(6) . . ? C66 O17 K6 116.0(4) . . ? O9 C36 N6 125.1(6) . . ? O9 C36 C35 125.2(6) . . ? N6 C36 C35 109.7(6) . . ? O12 C48 K4 40.4(3) . . ? O12 C48 N8 125.0(7) . . ? O12 C48 C47 126.6(6) . . ? N8 C48 K4 101.6(4) . . ? N8 C48 C47 108.4(6) . . ? C47 C48 K4 132.5(5) . . ? N7 C41 C42 113.7(6) . . ? K3 O7 K2 90.66(14) . . ? C25 O7 K2 131.0(5) . . ? C25 O7 K3 135.9(5) . . ? K2 O2S K4 151.72(17) . . ? K2 O2S K1 77.74(11) . . ? K2 O2S K3 97.78(14) . . ? K4 O2S K1 78.91(10) . . ? K3 O2S K4 81.89(11) . . ? K3 O2S K1 123.12(15) . . ? O13 C49 N9 124.7(8) . . ? O13 C49 C50 126.5(8) . . ? N9 C49 C50 108.8(7) . . ? C21 C22 C23 103.7(5) . . ? O11 C43 C44 110.5(5) . . ? N5 C25 C26 108.4(6) . . ? O7 C25 N5 125.3(7) . . ? O7 C25 C26 126.3(7) . . ? O4 C13 N3 125.5(7) . . ? O4 C13 C14 127.1(6) . . ? N3 C13 C14 107.4(6) . . ? C16 C15 C14 106.1(6) . . ? N1 C4 C3 103.4(5) . . ? O5 C18 C17 107.5(5) . . ? C15 C14 C13 106.3(6) . . ? O10 C37 N7 125.7(6) . . ? O10 C37 C38 125.9(6) . . ? N7 C37 C38 108.4(6) . . ? O5 C19 C20 107.7(5) . . ? P3 F15 K3 104.3(3) . . ? C61 C62 C63 103.0(6) . . ? O16 C61 N11 124.4(7) . . ? O16 C61 C62 125.1(6) . . ? N11 C61 C62 110.5(6) . . ? O2 C7 C8 108.9(5) . . ? N6 C32 C31 113.3(6) . . ? C49 N9 C52 114.2(7) . . ? C49 N9 C53 124.3(7) . . ? C53 N9 C52 121.6(6) . . ? N6 C33 C34 104.4(6) . . ? C60 N10 C56 123.2(7) . . ? C60 N10 C57 112.5(7) . . ? C57 N10 C56 123.7(7) . . ? N8 C44 C43 111.7(6) . . ? O11 C42 C41 108.3(5) . . ? C34 C35 C36 104.3(6) . . ? C12 C11 C10 105.5(6) . . ? N3 C17 C18 113.3(6) . . ? C62 C63 C64 103.8(6) . . ? C47 C46 C45 103.3(6) . . ? C60 C59 C58 104.7(7) . . ? C9 C10 C11 107.2(6) . . ? O8 C30 C29 108.6(5) . . ? O17 C67 C68 108.0(7) . . ? C2 C3 C4 103.2(5) . . ? C49 C50 C51 103.9(6) . . ? N10 C56 C55 111.5(7) . . ? O17 C66 C65 107.6(6) . . ? N11 C64 C63 102.9(6) . . ? N9 C52 C51 104.0(6) . . ? P3 F16 K3 87.4(3) . . ? N3 C16 C15 104.9(6) . . ? C27 C26 C25 105.4(7) . . ? C39 C38 C37 105.5(7) . . ? N4 C20 C19 111.8(6) . . ? C35 C34 C33 105.0(6) . . ? N5 C29 C30 114.3(6) . . ? C48 C47 C46 106.1(6) . . ? O15 C60 N10 124.4(8) . . ? O15 C60 C59 128.0(8) . . ? N10 C60 C59 107.5(7) . . ? N10 C57 C58 102.7(7) . . ? N11 C65 C66 110.7(7) . . ? N12 C68 C67 113.9(7) . . ? O8 C31 C32 108.8(5) . . ? N9 C53 C54 113.2(7) . . ? N2 C9 C10 104.2(6) . . ? C52 C51 C50 105.0(7) . . ? N7 C40 C39 103.7(7) . . ? N8 C45 C46 103.8(6) . . ? O14 C54 C53 109.0(6) . . ? O14 C55 C56 109.4(7) . . ? C26 C27 C28 105.7(7) . . ? C59 C58 C57 103.1(7) . . ? N12 C69 C70 103.7(6) . . ? C69 C70 C71 102.1(6) . . ? C38 C39 C40 108.1(7) . . ? N5 C28 C27 104.0(7) . . ? F31 P6 K6 122.62(18) . 1_545 ? F31 P6 F35 86.4(2) . . ? F34 P6 K6 103.4(2) . 1_545 ? F34 P6 F31 90.7(3) . . ? F34 P6 F35 87.0(3) . . ? F34 P6 F36 90.7(3) . . ? F34 P6 F32 176.1(4) . . ? F35 P6 K6 40.66(19) . 1_545 ? F36 P6 K6 52.6(2) . 1_545 ? F36 P6 F31 175.2(3) . . ? F36 P6 F35 89.0(3) . . ? F33 P6 K6 140.6(3) . 1_545 ? F33 P6 F31 92.2(3) . . ? F33 P6 F34 93.0(4) . . ? F33 P6 F35 178.6(3) . . ? F33 P6 F36 92.4(3) . . ? F33 P6 F32 90.9(4) . . ? F32 P6 K6 73.7(3) . 1_545 ? F32 P6 F31 88.8(3) . . ? F32 P6 F35 89.1(4) . . ? F32 P6 F36 89.6(3) . . ? P6 F35 K6 116.8(3) . 1_545 ? P6 F36 K6 103.7(3) . 1_545 ? K5 O3S K5 82.2(2) . 2_755 ? K5 O3S K6 90.9(2) . . ? K5 O3S K6 131.1(3) 2_755 . ? K6 O3S K5 96.4(2) 2_755 2_755 ? K6 O3S K5 168.6(3) 2_755 . ? K6 O3S K6 81.5(2) 2_755 . ? O3S O3S K5 70.3(4) 2_755 2_755 ? O3S O3S K5 79.4(4) 2_755 . ? O3S O3S K6 61.0(4) 2_755 . ? O3S O3S K6 89.4(4) 2_755 2_755 ? P2 F7 K2 103.56(18) . . ? P2 F9 K2 107.00(19) . . ? P2 F10 K2 88.24(18) . . ? O18 C72 N12 125.1(7) . . ? O18 C72 C71 127.1(7) . . ? N12 C72 C71 107.8(6) . . ? C72 C71 C70 105.5(6) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 46 -1 18 0.0883 46.0000 -1.0000 18.0002 0.9323 -0.0249 0.3645 52 -7 -7 0.1033 52.0000 -7.0001 -6.9999 0.9604 0.2817 -0.0458 -34 -1 62 0.0181 -33.9997 -0.9999 61.9992 -0.0290 -0.9929 0.1016 2 -18 -11 0.3722 2.0003 -18.0000 -11.0008 0.3472 -0.0039 -0.9480 29 13 19 0.2484 28.9998 13.0000 19.0008 0.3443 0.0035 0.9536 -30 15 -3 0.2103 -30.0003 15.0000 -2.9994 -0.8586 0.0274 0.5283 -44 8 -13 0.1000 -44.0001 8.0000 -12.9999 -1.0154 0.0303 0.0270 -46 1 -18 0.0883 -46.0000 1.0000 -18.0002 -0.9323 0.0249 -0.3645 34 1 -62 0.0181 33.9997 0.9999 -61.9992 0.0290 0.9929 -0.1016 _database_code_depnum_ccdc_archive 'CCDC 965885' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12srv076 _audit_creation_date 2012-12-31 _audit_creation_method ; Olex2 1.2 (compiled Nov 5 2012 18:25:38, GUI svn.r4372) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H20 Cl2 N2 O3 Zn' _chemical_formula_sum 'C12 H20 Cl2 N2 O3 Zn' _chemical_formula_weight 376.57 _chemical_melting_point ? _chemical_oxdiff_formula 'C14 H20 N2 O3 Zn Cl2' 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' Cl Cl 0.1484 0.1585 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.3180(6) _cell_length_b 8.6628(3) _cell_length_c 16.7004(9) _cell_angle_alpha 90.00 _cell_angle_beta 107.888(6) _cell_angle_gamma 90.00 _cell_volume 1558.26(13) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3613 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 29.0233 _cell_measurement_theta_min 2.5568 _exptl_absorpt_coefficient_mu 1.926 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 776 _exptl_crystal_size_max 0.4654 _exptl_crystal_size_mid 0.197 _exptl_crystal_size_min 0.0541 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_unetI/netI 0.0529 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 15272 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.56 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean 16.1511 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -78.00 -8.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.0044 -19.0000 -150.0000 70 #__ type_ start__ end____ width___ exp.time_ 2 omega -81.00 37.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.0044 0.0000 -90.0000 118 #__ type_ start__ end____ width___ exp.time_ 3 omega 29.00 54.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 17.6294 -141.0000 50.0000 25 #__ type_ start__ end____ width___ exp.time_ 4 omega -88.00 5.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.0044 -38.0000 120.0000 93 #__ type_ start__ end____ width___ exp.time_ 5 omega -36.00 51.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.0044 57.0000 -60.0000 87 #__ type_ start__ end____ width___ exp.time_ 6 omega -3.00 59.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 17.6294 -100.0000 120.0000 62 #__ type_ start__ end____ width___ exp.time_ 7 omega -11.00 30.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 17.6294 77.0000 60.0000 41 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0355116000 _diffrn_orient_matrix_UB_12 -0.0616821000 _diffrn_orient_matrix_UB_13 0.0085943000 _diffrn_orient_matrix_UB_21 0.0256455000 _diffrn_orient_matrix_UB_22 0.0141619000 _diffrn_orient_matrix_UB_23 0.0437395000 _diffrn_orient_matrix_UB_31 -0.0491935000 _diffrn_orient_matrix_UB_32 0.0519660000 _diffrn_orient_matrix_UB_33 -0.0017179000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2795 _reflns_number_total 3543 _reflns_odcompleteness_completeness 99.88 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.473 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.094 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 3543 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0370 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0255P)^2^+0.8512P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.0787 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H12A,H12B} of C12, {H2A,H2B} of C2, {H11A,H11B} of C11, {H8A,H8B} of C8, {H5A,H5B} of C5, {H10A,H10B} of C10, {H4A,H4B} of C4, {H3A,H3B} of C3, {H6A, H6B} of C6, {H7A,H7B} of C7 2.a Secondary CH2 refined with riding coordinates: C12(H12A,H12B), C2(H2A,H2B), C11(H11A,H11B), C8(H8A,H8B), C5(H5A,H5B), C10(H10A,H10B), C4(H4A,H4B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.87816(3) 0.35487(3) 0.13168(2) 0.01397(10) Uani 1 1 d . . . Cl1 Cl 1.08466(6) 0.34236(8) 0.18730(5) 0.02018(16) Uani 1 1 d . . . Cl2 Cl 0.79096(6) 0.57752(8) 0.08135(5) 0.02188(17) Uani 1 1 d . . . O1 O 0.81083(16) 0.2867(2) 0.22324(12) 0.0172(4) Uani 1 1 d . . . O3 O 0.82747(17) 0.1841(2) 0.04793(12) 0.0166(4) Uani 1 1 d . . . N2 N 0.84056(19) 0.0592(3) -0.06888(14) 0.0146(5) Uani 1 1 d . . . N1 N 0.92170(19) 0.3112(3) 0.36168(14) 0.0146(5) Uani 1 1 d . . . C1 C 0.8841(2) 0.2331(3) 0.29055(17) 0.0144(6) Uani 1 1 d . . . C12 C 0.8815(3) 0.0845(3) -0.14320(18) 0.0195(6) Uani 1 1 d . . . H12A H 0.8227 0.0377 -0.1940 0.023 Uiso 1 1 calc R . . H12B H 0.9652 0.0407 -0.1348 0.023 Uiso 1 1 calc R . . C2 C 0.9379(3) 0.0733(3) 0.30253(19) 0.0212(6) Uani 1 1 d . . . H2A H 0.9746 0.0470 0.2576 0.025 Uiso 1 1 calc R . . H2B H 0.8738 -0.0043 0.3027 0.025 Uiso 1 1 calc R . . C11 C 0.8828(3) 0.2604(3) -0.15041(18) 0.0212(6) Uani 1 1 d . . . H11A H 0.8052 0.2982 -0.1916 0.025 Uiso 1 1 calc R . . H11B H 0.9543 0.2953 -0.1681 0.025 Uiso 1 1 calc R . . C8 C 0.8090(2) -0.0952(3) -0.04636(18) 0.0158(6) Uani 1 1 d . . . H8A H 0.8071 -0.0941 0.0125 0.019 Uiso 1 1 calc R . . H8B H 0.8744 -0.1687 -0.0497 0.019 Uiso 1 1 calc R . . C9 C 0.8502(2) 0.1833(3) -0.02153(17) 0.0140(6) Uani 1 1 d . . . C5 C 0.8831(2) 0.4687(3) 0.37242(18) 0.0181(6) Uani 1 1 d . . . H5A H 0.8808 0.4822 0.4308 0.022 Uiso 1 1 calc R . . H5B H 0.7982 0.4862 0.3339 0.022 Uiso 1 1 calc R . . C10 C 0.8940(2) 0.3181(3) -0.06166(18) 0.0163(6) Uani 1 1 d . . . H10A H 0.9810 0.3449 -0.0305 0.020 Uiso 1 1 calc R . . H10B H 0.8408 0.4097 -0.0637 0.020 Uiso 1 1 calc R . . C4 C 1.0043(3) 0.2228(3) 0.43160(18) 0.0197(6) Uani 1 1 d . . . H4A H 0.9614 0.1925 0.4726 0.024 Uiso 1 1 calc R . . H4B H 1.0796 0.2829 0.4610 0.024 Uiso 1 1 calc R . . C3 C 1.0370(3) 0.0811(4) 0.3877(2) 0.0322(8) Uani 1 1 d . . . H3A H 1.1204 0.0928 0.3808 0.039 Uiso 1 1 calc R . . H3B H 1.0361 -0.0136 0.4207 0.039 Uiso 1 1 calc R . . C6 C 0.9701(2) 0.5859(3) 0.35459(19) 0.0181(6) Uani 1 1 d . . . H6A H 0.9734 0.5736 0.2964 0.022 Uiso 1 1 calc R . . H6B H 0.9411 0.6917 0.3609 0.022 Uiso 1 1 calc R . . O2 O 1.09037(16) 0.5606(2) 0.41356(12) 0.0169(4) Uani 1 1 d . . . C7 C 1.1849(2) 0.6500(3) 0.39662(18) 0.0170(6) Uani 1 1 d . . . H7A H 1.1731 0.7605 0.4071 0.020 Uiso 1 1 calc R . . H7B H 1.1814 0.6377 0.3370 0.020 Uiso 1 1 calc R . . 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 Zn1 0.01556(17) 0.01546(17) 0.00959(17) -0.00034(13) 0.00193(13) -0.00001(13) Cl1 0.0151(3) 0.0224(4) 0.0207(4) -0.0006(3) 0.0020(3) 0.0017(3) Cl2 0.0221(4) 0.0204(4) 0.0230(4) 0.0057(3) 0.0067(3) 0.0061(3) O1 0.0166(10) 0.0251(11) 0.0086(10) 0.0013(8) 0.0016(8) -0.0009(8) O3 0.0233(10) 0.0170(10) 0.0099(10) -0.0028(8) 0.0055(8) -0.0034(8) N2 0.0154(11) 0.0170(12) 0.0121(13) -0.0012(10) 0.0054(10) -0.0001(9) N1 0.0121(11) 0.0195(12) 0.0095(12) 0.0017(9) -0.0008(9) -0.0008(9) C1 0.0116(13) 0.0204(15) 0.0125(15) 0.0011(11) 0.0056(11) -0.0049(11) C12 0.0213(15) 0.0240(15) 0.0150(16) -0.0018(12) 0.0079(12) -0.0008(12) C2 0.0227(15) 0.0192(15) 0.0214(17) -0.0003(12) 0.0062(13) 0.0003(12) C11 0.0246(16) 0.0242(16) 0.0155(16) 0.0008(12) 0.0069(13) -0.0054(12) C8 0.0164(14) 0.0157(14) 0.0136(15) 0.0013(11) 0.0023(11) 0.0013(11) C9 0.0098(12) 0.0180(14) 0.0117(15) -0.0010(11) -0.0003(11) -0.0004(10) C5 0.0145(14) 0.0226(15) 0.0150(15) -0.0022(12) 0.0012(12) 0.0037(11) C10 0.0151(14) 0.0192(14) 0.0139(15) -0.0005(11) 0.0033(12) -0.0017(11) C4 0.0190(14) 0.0226(15) 0.0133(16) 0.0045(12) -0.0011(12) -0.0012(12) C3 0.0332(18) 0.0284(17) 0.026(2) -0.0003(14) -0.0035(15) 0.0104(15) C6 0.0185(14) 0.0167(14) 0.0164(16) -0.0015(12) 0.0015(12) 0.0034(11) O2 0.0148(10) 0.0203(10) 0.0137(11) 0.0016(8) 0.0018(8) -0.0012(8) C7 0.0209(15) 0.0127(13) 0.0170(15) 0.0028(11) 0.0055(12) 0.0002(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 Cl1 2.2368(7) . ? Zn1 Cl2 2.2116(7) . ? Zn1 O1 1.9958(18) . ? Zn1 O3 1.9952(18) . ? O1 C1 1.263(3) . ? O3 C9 1.263(3) . ? N2 C12 1.468(3) . ? N2 C8 1.463(3) . ? N2 C9 1.319(3) . ? N1 C1 1.319(3) . ? N1 C5 1.460(3) . ? N1 C4 1.468(3) . ? C1 C2 1.501(4) . ? C12 C11 1.529(4) . ? C2 C3 1.519(4) . ? C11 C10 1.532(4) . ? C8 C7 1.511(4) 4_565 ? C9 C10 1.504(4) . ? C5 C6 1.507(4) . ? C4 C3 1.532(4) . ? C6 O2 1.431(3) . ? O2 C7 1.418(3) . ? C7 C8 1.511(4) 4_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Zn1 Cl1 119.17(3) . . ? O1 Zn1 Cl1 105.29(6) . . ? O1 Zn1 Cl2 108.57(6) . . ? O3 Zn1 Cl1 107.10(6) . . ? O3 Zn1 Cl2 112.43(6) . . ? O3 Zn1 O1 102.85(8) . . ? C1 O1 Zn1 119.35(16) . . ? C9 O3 Zn1 123.51(17) . . ? C8 N2 C12 121.2(2) . . ? C9 N2 C12 113.3(2) . . ? C9 N2 C8 125.0(2) . . ? C1 N1 C5 124.3(2) . . ? C1 N1 C4 113.5(2) . . ? C5 N1 C4 122.1(2) . . ? O1 C1 N1 123.7(3) . . ? O1 C1 C2 125.9(3) . . ? N1 C1 C2 110.3(2) . . ? N2 C12 C11 103.2(2) . . ? C1 C2 C3 103.7(2) . . ? C12 C11 C10 104.4(2) . . ? N2 C8 C7 112.2(2) . 4_565 ? O3 C9 N2 123.5(2) . . ? O3 C9 C10 126.4(2) . . ? N2 C9 C10 110.1(2) . . ? N1 C5 C6 111.5(2) . . ? C9 C10 C11 103.7(2) . . ? N1 C4 C3 103.0(2) . . ? C2 C3 C4 105.5(2) . . ? O2 C6 C5 107.6(2) . . ? C7 O2 C6 113.3(2) . . ? O2 C7 C8 108.4(2) . 4_666 ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -13 -7 5 0.0736 -12.9999 -7.0000 5.0000 0.9364 -0.2138 0.2672 11 9 -4 0.0723 10.9999 9.0000 -4.0000 -0.9801 0.2346 -0.0666 -9 10 4 0.2139 -9.0000 10.0000 4.0000 -0.2628 0.0858 0.9555 -14 6 5 0.2100 -13.9999 6.0000 5.0000 0.1700 -0.0554 0.9919 -3 1 -21 0.0270 -3.0000 1.0000 -21.0000 -0.1356 -0.9813 0.2356 3 -1 21 0.0270 3.0000 -1.0000 21.0000 0.1356 0.9813 -0.2356 12 -8 -5 0.2098 11.9999 -8.0000 -5.0000 0.0243 -0.0242 -0.9975 _database_code_depnum_ccdc_archive 'CCDC 965886'