# Electronic Supplementary Material (ESI) for CrystEngComm # 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_1 #============================================================================ # start Validation Reply Form # ALERT LEVEL B _vrf_PLAT910_1 ; PROBLEM: Missing # of FCF Reflections Below Th(Min) ..... 15 RESPONSE: Data completeness is 99.2%, which is enough for a good refinement of data. Most of the missing reflections were excluded by the SHEL command in order to avoid problems related to extinction and saturation common to low theta reflections. ; # ALERTS LEVEL C _vrf_PLAT213_1 ; PROBLEM: Atom O2W has ADP max/min Ratio ..... 3.2 prola RESPONSE: This atom is affected by thermal vibrational disorder giving a prolate ellipsoid. ; _vrf_PLAT342_1 ; PROBLEM: Low Bond Precision on C-C Bonds ............... 0.0133 Ang. RESPONSE: The low bond precision on the C-C bonds may derived from the low quality of data. As an example, the R1 value between the resolution range 0.83-0.86 A is of 0.159, which significantly affect data quality. ; _vrf_PLAT480_1 ; PROBLEM: Long H...A H-Bond Reported H1X .. O15 .. 2.62 Ang. RESPONSE: All the structural features in the asymmetric unit appear in similar pairs. For this reason the Long H1X...O15 bond was included for preservation of this non-crystallographic symmetry also in the hydrogen bond network. The "pair" of this hydrogen bond is the bond H2X...O7 with a distance of 2.52 A. ; _vrf_PLAT906_1 ; PROBLEM: Large K value in the Analysis of Variance ...... 3.762 RESPONSE: The K value is large only for weak reflections with Fc/Fcmax lower than 0.021. ; _vrf_PLAT911_1 ; PROBLEM: Missing # FCF Refl Between THmin & STh/L= 0.600 27 RESPONSE: Please see our response to _vrf_PLAT910. ; _vrf_PLAT971_1 ; PROBLEM: Large Calcd. Non-Metal Positive Residual Density 2.46 eA-3 RESPONSE: This alert arises four times, corresponding to non-metal positive residual densities of 2.46, 1.73, 1.66 and 1.63 eA-3. All of these peaks are located within 1.5 A of the metal centres. ; _vrf_PLAT972_1 ; PROBLEM: Large Calcd. Non-Metal Negative Residual Density -2.28 eA-3 RESPONSE: This alert appears twice, corresponding to non-metal positive residual densities of -2.28 and -2.07 eA-3. The larger hole is located between atoms O12 and La2. ; _vrf_PLAT975_1 ; PROBLEM: Positive Residual Density at 0.77A from O2W . 0.87 eA-3 RESPONSE: This alert arises twice, the other case is at 0.71A from O1W. These peaks are located toward the metal centres and, therefore, can not be assigned to H atoms. ; _vrf_PLAT976_1 ; PROBLEM: Negative Residual Density at 0.93A from O2 . -0.85 eA-3 RESPONSE: Because atom O2 is protonated this negative residual density could be related to a wrongly located H atom. However, the refined proton is directed toward the only acceptor atom in the neighbourhood, being this is a good indication that was correctly assigned. ; #============================================================================= _audit_creation_method 'SHELXL-97, manual editing plus enCIFer' _audit_creation_date '25 July 2013' #============================================================================= _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 F6 La2 O20 P6' _chemical_formula_sum 'C18 H22 F6 La2 O20 P6' _chemical_formula_weight 1136.00 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' 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' La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================= # CRYSTAL DATA #============================================================================= _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4435(4) _cell_length_b 11.7657(5) _cell_length_c 14.9918(7) _cell_angle_alpha 110.335(2) _cell_angle_beta 90.018(2) _cell_angle_gamma 93.142(2) _cell_volume 1559.23(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4633 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 24.13 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 3.135 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8849 _exptl_absorpt_correction_T_max 0.9693 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1997) ; #============================================================================= # EXPERIMENTAL DATA #============================================================================= _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Kappa CCD APEX II' _diffrn_measurement_method '\w / \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 44212 _diffrn_reflns_av_R_equivalents 0.0789 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5677 _reflns_number_gt 4152 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'APEX2 (Bruker, 2006)' _computing_data_reduction 'SAINT+ (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' #============================================================================= # REFINEMENT DATA #============================================================================= _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^)+(0.0493P)^2^+18.4761P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5677 _refine_ls_number_parameters 487 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 #============================================================================= # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS #============================================================================= 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 La1 La -0.31287(5) 0.98920(5) 0.84688(4) 0.01374(15) Uani 1 1 d D . . O1W O -0.5822(6) 0.9295(6) 0.8400(5) 0.0213(15) Uani 1 1 d D . . H1X H -0.614(9) 0.906(9) 0.892(4) 0.032 Uiso 1 1 d D . . H1Y H -0.646(8) 0.894(8) 0.787(4) 0.032 Uiso 1 1 d D . . La2 La 0.18889(5) 1.01564(5) 0.65512(4) 0.01366(15) Uani 1 1 d . . . O2W O -0.0728(6) 1.0734(6) 0.6626(5) 0.0215(15) Uani 1 1 d D . . H2X H -0.114(9) 1.085(9) 0.609(4) 0.032 Uiso 1 1 d D . . H2Y H -0.128(8) 1.109(9) 0.717(3) 0.032 Uiso 1 1 d D . . C1 C -0.0309(10) 1.3656(8) 0.6746(7) 0.016(2) Uani 1 1 d . . . C2 C 0.0347(10) 1.3671(8) 0.7573(7) 0.018(2) Uani 1 1 d . . . C3 C -0.0352(9) 1.3691(8) 0.8389(7) 0.0148(19) Uani 1 1 d . . . C4 C -0.1820(9) 1.3721(8) 0.8349(7) 0.016(2) Uani 1 1 d . . . C5 C -0.2582(10) 1.3661(8) 0.7540(7) 0.017(2) Uani 1 1 d . . . C6 C -0.1775(10) 1.3677(8) 0.6769(7) 0.017(2) Uani 1 1 d . . . C7 C 0.0480(10) 1.3571(9) 0.5851(7) 0.018(2) Uani 1 1 d . . . H7A H 0.1432 1.3988 0.6031 0.022 Uiso 1 1 calc R . . H7B H -0.0034 1.4006 0.5504 0.022 Uiso 1 1 calc R . . C8 C 0.0385(10) 1.3519(9) 0.9230(7) 0.019(2) Uani 1 1 d . . . H8A H -0.0144 1.3904 0.9818 0.023 Uiso 1 1 calc R . . H8B H 0.1357 1.3906 0.9316 0.023 Uiso 1 1 calc R . . C9 C -0.4157(10) 1.3391(8) 0.7464(7) 0.018(2) Uani 1 1 d . . . H9A H -0.4580 1.3715 0.7004 0.022 Uiso 1 1 calc R . . H9B H -0.4593 1.3770 0.8090 0.022 Uiso 1 1 calc R . . F1 F 0.1783(5) 1.3603(5) 0.7570(4) 0.0223(12) Uani 1 1 d . . . F2 F -0.2547(6) 1.3744(5) 0.9127(4) 0.0236(13) Uani 1 1 d . . . F3 F -0.2476(5) 1.3666(5) 0.5976(4) 0.0217(12) Uani 1 1 d . . . P1 P 0.0687(3) 1.2035(2) 0.50627(17) 0.0165(5) Uani 1 1 d . . . P2 P 0.0457(2) 1.1900(2) 0.90006(17) 0.0146(5) Uani 1 1 d . . . P3 P -0.4460(2) 1.1748(2) 0.70606(17) 0.0151(5) Uani 1 1 d . . . O1 O -0.0730(6) 1.1330(6) 0.4864(5) 0.0187(14) Uani 1 1 d . . . O2 O 0.1274(7) 1.2300(6) 0.4175(5) 0.0200(15) Uani 1 1 d . . . H2 H 0.1895 1.1811 0.3920 0.030 Uiso 1 1 calc R . . O3 O 0.1798(6) 1.1434(6) 0.5466(5) 0.0196(15) Uani 1 1 d . . . O4 O 0.1582(6) 1.1408(6) 0.8265(4) 0.0165(14) Uani 1 1 d . . . O5 O 0.0908(7) 1.1860(6) 1.0001(4) 0.0199(15) Uani 1 1 d . . . H5 H 0.1710 1.1574 0.9965 0.030 Uiso 1 1 calc R . . O6 O -0.1011(6) 1.1291(6) 0.8760(5) 0.0184(14) Uani 1 1 d . . . O7 O -0.3733(6) 1.1238(6) 0.6058(5) 0.0185(14) Uani 1 1 d . . . H7 H -0.4201 1.1417 0.5653 0.028 Uiso 1 1 calc R . . O8 O -0.3619(6) 1.1285(6) 0.7702(5) 0.0191(14) Uani 1 1 d . . . O9 O -0.6029(6) 1.1467(6) 0.6977(5) 0.0202(15) Uani 1 1 d . . . C10 C 0.4159(9) 0.6349(8) 0.6619(6) 0.0140(19) Uani 1 1 d . . . C11 C 0.2682(10) 0.6363(8) 0.6675(7) 0.016(2) Uani 1 1 d . . . C12 C 0.1941(9) 0.6397(8) 0.7464(7) 0.014(2) Uani 1 1 d . . . C13 C 0.2733(10) 0.6361(8) 0.8232(7) 0.017(2) Uani 1 1 d . . . C14 C 0.4209(9) 0.6330(8) 0.8251(7) 0.0150(19) Uani 1 1 d . . . C15 C 0.4860(9) 0.6332(8) 0.7411(6) 0.0134(19) Uani 1 1 d . . . C16 C 0.4909(9) 0.6541(8) 0.5793(7) 0.017(2) Uani 1 1 d . . . H16A H 0.4327 0.6159 0.5204 0.021 Uiso 1 1 calc R . . H16B H 0.5829 0.6155 0.5703 0.021 Uiso 1 1 calc R . . C17 C 0.0394(9) 0.6676(8) 0.7549(7) 0.017(2) Uani 1 1 d . . . H17A H -0.0072 0.6343 0.8004 0.020 Uiso 1 1 calc R . . H17B H -0.0098 0.6307 0.6922 0.020 Uiso 1 1 calc R . . C18 C 0.5011(10) 0.6404(9) 0.9128(7) 0.021(2) Uani 1 1 d . . . H18A H 0.5906 0.5990 0.8942 0.025 Uiso 1 1 calc R . . H18B H 0.4444 0.5964 0.9474 0.025 Uiso 1 1 calc R . . F4 F 0.1951(5) 0.6383(5) 0.5907(4) 0.0223(12) Uani 1 1 d . . . F5 F 0.2054(5) 0.6357(5) 0.9018(4) 0.0216(12) Uani 1 1 d . . . F6 F 0.6295(5) 0.6336(5) 0.7402(4) 0.0229(13) Uani 1 1 d . . . O10 O 0.6402(6) 0.8643(6) 0.6758(4) 0.0165(14) Uani 1 1 d . . . O11 O 0.5657(7) 0.8211(6) 0.5026(5) 0.0238(15) Uani 1 1 d . . . H11 H 0.6512 0.8463 0.5055 0.036 Uiso 1 1 calc R . . O12 O 0.3827(6) 0.8759(6) 0.6264(5) 0.0209(15) Uani 1 1 d . . . O13 O 0.1226(7) 0.8783(6) 0.7341(5) 0.0196(14) Uani 1 1 d . . . O14 O -0.1220(7) 0.8605(6) 0.8044(5) 0.0209(15) Uani 1 1 d . . . O15 O 0.1098(7) 0.8818(6) 0.8979(5) 0.0211(15) Uani 1 1 d . . . H15 H 0.0629 0.8588 0.9368 0.032 Uiso 1 1 calc R . . O16 O 0.4106(6) 0.8639(6) 1.0116(4) 0.0183(14) Uani 1 1 d . . . O17 O 0.5970(7) 0.7670(6) 1.0814(5) 0.0197(15) Uani 1 1 d . . . H17 H 0.6763 0.8039 1.0997 0.030 Uiso 1 1 calc R . . O18 O 0.6601(6) 0.8556(6) 0.9525(5) 0.0191(14) Uani 1 1 d . . . P4 P 0.5206(2) 0.8158(2) 0.60201(17) 0.0138(5) Uani 1 1 d . . . P5 P 0.0314(3) 0.8314(2) 0.79673(17) 0.0157(5) Uani 1 1 d . . . P6 P 0.5426(3) 0.7940(2) 0.99183(18) 0.0175(5) 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 La1 0.0094(3) 0.0186(3) 0.0140(3) 0.0067(2) 0.0000(2) 0.0012(2) O1W 0.007(3) 0.036(4) 0.019(4) 0.008(3) -0.002(3) -0.005(3) La2 0.0097(3) 0.0184(3) 0.0141(3) 0.0073(2) -0.0006(2) 0.0004(2) O2W 0.005(3) 0.041(4) 0.019(4) 0.011(3) 0.001(3) 0.006(3) C1 0.019(5) 0.011(5) 0.020(5) 0.006(4) 0.002(4) 0.003(4) C2 0.016(5) 0.014(5) 0.022(5) 0.004(4) 0.001(4) 0.006(4) C3 0.012(5) 0.015(5) 0.018(5) 0.008(4) 0.003(4) -0.001(4) C4 0.016(5) 0.014(5) 0.020(5) 0.007(4) 0.003(4) 0.002(4) C5 0.017(5) 0.018(5) 0.015(5) 0.004(4) 0.002(4) 0.002(4) C6 0.019(5) 0.012(5) 0.015(5) 0.001(4) -0.003(4) -0.001(4) C7 0.015(5) 0.025(5) 0.016(5) 0.010(4) 0.000(4) -0.003(4) C8 0.017(5) 0.025(5) 0.016(5) 0.009(4) 0.000(4) -0.003(4) C9 0.017(5) 0.018(5) 0.026(5) 0.013(4) -0.002(4) 0.005(4) F1 0.012(3) 0.030(3) 0.027(3) 0.014(3) -0.001(2) 0.001(2) F2 0.020(3) 0.029(3) 0.024(3) 0.011(3) 0.006(2) 0.003(2) F3 0.017(3) 0.031(3) 0.022(3) 0.016(3) -0.004(2) -0.001(2) P1 0.0137(12) 0.0210(13) 0.0156(13) 0.0075(11) -0.0003(10) 0.0005(10) P2 0.0114(12) 0.0175(12) 0.0154(12) 0.0066(10) -0.0014(9) -0.0004(9) P3 0.0127(12) 0.0163(12) 0.0179(13) 0.0081(10) -0.0023(10) -0.0021(9) O1 0.014(3) 0.023(4) 0.019(4) 0.008(3) 0.000(3) 0.000(3) O2 0.019(4) 0.020(4) 0.021(4) 0.006(3) 0.001(3) 0.006(3) O3 0.014(3) 0.021(4) 0.024(4) 0.009(3) -0.002(3) 0.005(3) O4 0.013(3) 0.021(3) 0.014(3) 0.003(3) -0.002(3) 0.000(3) O5 0.014(3) 0.033(4) 0.018(4) 0.015(3) 0.002(3) 0.005(3) O6 0.009(3) 0.026(4) 0.021(4) 0.010(3) -0.002(3) -0.003(3) O7 0.016(3) 0.020(4) 0.020(4) 0.007(3) -0.004(3) -0.002(3) O8 0.016(3) 0.023(4) 0.022(4) 0.014(3) -0.005(3) -0.002(3) O9 0.010(3) 0.026(4) 0.026(4) 0.012(3) -0.002(3) 0.000(3) C10 0.014(5) 0.013(5) 0.013(5) 0.002(4) -0.001(4) 0.002(4) C11 0.023(5) 0.005(4) 0.016(5) 0.001(4) -0.002(4) -0.003(4) C12 0.010(4) 0.010(4) 0.022(5) 0.004(4) -0.005(4) -0.003(3) C13 0.024(5) 0.013(5) 0.015(5) 0.007(4) 0.000(4) 0.002(4) C14 0.016(5) 0.009(4) 0.018(5) 0.002(4) -0.008(4) -0.002(4) C15 0.011(4) 0.012(5) 0.017(5) 0.005(4) -0.001(4) -0.005(3) C16 0.012(5) 0.021(5) 0.014(5) -0.001(4) 0.000(4) 0.001(4) C17 0.013(5) 0.016(5) 0.020(5) 0.005(4) 0.000(4) -0.001(4) C18 0.020(5) 0.021(5) 0.025(6) 0.010(4) 0.004(4) 0.004(4) F4 0.016(3) 0.030(3) 0.021(3) 0.009(3) -0.003(2) 0.000(2) F5 0.016(3) 0.027(3) 0.025(3) 0.013(3) 0.005(2) 0.003(2) F6 0.013(3) 0.031(3) 0.027(3) 0.013(3) -0.002(2) 0.005(2) O10 0.013(3) 0.023(4) 0.012(3) 0.005(3) -0.001(3) 0.000(3) O11 0.017(4) 0.034(4) 0.020(4) 0.010(3) 0.001(3) 0.000(3) O12 0.009(3) 0.028(4) 0.028(4) 0.013(3) 0.001(3) 0.006(3) O13 0.020(3) 0.024(4) 0.018(4) 0.011(3) 0.006(3) 0.004(3) O14 0.017(3) 0.025(4) 0.023(4) 0.011(3) -0.003(3) 0.005(3) O15 0.017(3) 0.029(4) 0.021(4) 0.013(3) 0.005(3) 0.002(3) O16 0.015(3) 0.029(4) 0.010(3) 0.005(3) 0.002(3) 0.003(3) O17 0.013(3) 0.030(4) 0.019(4) 0.012(3) -0.007(3) -0.003(3) O18 0.015(3) 0.023(4) 0.019(4) 0.007(3) -0.002(3) -0.001(3) P4 0.0095(11) 0.0179(12) 0.0151(12) 0.0070(10) 0.0002(9) 0.0016(9) P5 0.0161(12) 0.0167(13) 0.0164(13) 0.0084(10) 0.0019(10) 0.0030(10) P6 0.0137(12) 0.0241(14) 0.0165(13) 0.0092(11) -0.0004(10) 0.0007(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. ; #============================================================================= # GEOMETRY #============================================================================= 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 La1 O14 2.361(6) . ? La1 O8 2.370(6) . ? La1 O16 2.443(6) 2_577 ? La1 O6 2.458(6) . ? La1 O10 2.499(6) 1_455 ? La1 O1W 2.593(6) . ? La1 O18 2.595(7) 1_455 ? O1W H1X 0.950(10) . ? O1W H1Y 0.950(10) . ? La2 O13 2.371(6) . ? La2 O9 2.374(6) 1_655 ? La2 O1 2.443(6) 2_576 ? La2 O12 2.465(6) . ? La2 O4 2.505(6) . ? La2 O3 2.575(7) . ? La2 O2W 2.591(6) . ? O2W H2X 0.948(10) . ? O2W H2Y 0.949(10) . ? C1 C2 1.380(13) . ? C1 C6 1.386(13) . ? C1 C7 1.511(13) . ? C2 F1 1.363(10) . ? C2 C3 1.385(13) . ? C3 C4 1.390(13) . ? C3 C8 1.518(13) . ? C4 F2 1.347(11) . ? C4 C5 1.388(13) . ? C5 C6 1.390(13) . ? C5 C9 1.499(13) . ? C6 F3 1.357(11) . ? C7 P1 1.804(10) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 P2 1.820(10) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 P3 1.819(9) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? P1 O1 1.508(7) . ? P1 O3 1.531(6) . ? P1 O2 1.563(7) . ? P2 O6 1.509(6) . ? P2 O4 1.517(7) . ? P2 O5 1.575(7) . ? P3 O9 1.497(7) . ? P3 O8 1.504(7) . ? P3 O7 1.584(7) . ? O1 La2 2.444(6) 2_576 ? O2 H2 0.8400 . ? O5 H5 0.8400 . ? O7 H7 0.8400 . ? O9 La2 2.374(6) 1_455 ? C10 C15 1.366(13) . ? C10 C11 1.398(13) . ? C10 C16 1.505(13) . ? C11 F4 1.350(11) . ? C11 C12 1.365(13) . ? C12 C13 1.387(13) . ? C12 C17 1.510(12) . ? C13 F5 1.342(11) . ? C13 C14 1.397(13) . ? C14 C15 1.401(13) . ? C14 C18 1.491(13) . ? C15 F6 1.355(10) . ? C16 P4 1.818(10) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 P5 1.813(9) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 P6 1.805(10) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? O10 P4 1.521(6) . ? O10 La1 2.499(6) 1_655 ? O11 P4 1.571(7) . ? O11 H11 0.8400 . ? O12 P4 1.501(6) . ? O13 P5 1.496(7) . ? O14 P5 1.503(7) . ? O15 P5 1.589(7) . ? O15 H15 0.8400 . ? O16 P6 1.504(7) . ? O16 La1 2.443(6) 2_577 ? O17 P6 1.576(7) . ? O17 H17 0.8400 . ? O18 P6 1.520(7) . ? O18 La1 2.595(7) 1_655 ? 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 O14 La1 O8 122.8(2) . . ? O14 La1 O16 139.4(2) . 2_577 ? O8 La1 O16 85.7(2) . 2_577 ? O14 La1 O6 75.7(2) . . ? O8 La1 O6 74.7(2) . . ? O16 La1 O6 86.7(2) 2_577 . ? O14 La1 O10 75.3(2) . 1_455 ? O8 La1 O10 74.1(2) . 1_455 ? O16 La1 O10 144.7(2) 2_577 1_455 ? O6 La1 O10 114.4(2) . 1_455 ? O14 La1 O1W 128.4(2) . . ? O8 La1 O1W 88.8(2) . . ? O16 La1 O1W 74.4(2) 2_577 . ? O6 La1 O1W 155.9(2) . . ? O10 La1 O1W 76.4(2) 1_455 . ? O14 La1 O18 75.5(2) . 1_455 ? O8 La1 O18 161.4(2) . 1_455 ? O16 La1 O18 80.6(2) 2_577 1_455 ? O6 La1 O18 116.8(2) . 1_455 ? O10 La1 O18 110.7(2) 1_455 1_455 ? O1W La1 O18 75.4(2) . 1_455 ? La1 O1W H1X 114(5) . . ? La1 O1W H1Y 131(5) . . ? H1X O1W H1Y 109.1(17) . . ? O13 La2 O9 122.4(2) . 1_655 ? O13 La2 O1 86.3(2) . 2_576 ? O9 La2 O1 139.3(2) 1_655 2_576 ? O13 La2 O12 74.7(2) . . ? O9 La2 O12 76.1(2) 1_655 . ? O1 La2 O12 86.3(2) 2_576 . ? O13 La2 O4 73.3(2) . . ? O9 La2 O4 75.3(2) 1_655 . ? O1 La2 O4 144.8(2) 2_576 . ? O12 La2 O4 114.3(2) . . ? O13 La2 O3 161.5(2) . . ? O9 La2 O3 75.8(2) 1_655 . ? O1 La2 O3 79.8(2) 2_576 . ? O12 La2 O3 116.1(2) . . ? O4 La2 O3 112.1(2) . . ? O13 La2 O2W 88.4(2) . . ? O9 La2 O2W 128.3(2) 1_655 . ? O1 La2 O2W 74.9(2) 2_576 . ? O12 La2 O2W 155.5(2) . . ? O4 La2 O2W 76.1(2) . . ? O3 La2 O2W 76.3(2) . . ? La2 O2W H2X 119(5) . . ? La2 O2W H2Y 129(5) . . ? H2X O2W H2Y 109.6(17) . . ? C2 C1 C6 115.5(9) . . ? C2 C1 C7 123.4(8) . . ? C6 C1 C7 121.0(8) . . ? F1 C2 C1 117.6(8) . . ? F1 C2 C3 117.6(8) . . ? C1 C2 C3 124.8(9) . . ? C2 C3 C4 115.6(8) . . ? C2 C3 C8 123.0(8) . . ? C4 C3 C8 120.9(8) . . ? F2 C4 C5 118.2(8) . . ? F2 C4 C3 117.7(8) . . ? C5 C4 C3 123.9(9) . . ? C4 C5 C6 115.6(8) . . ? C4 C5 C9 121.1(8) . . ? C6 C5 C9 122.5(8) . . ? F3 C6 C1 118.1(8) . . ? F3 C6 C5 117.6(8) . . ? C1 C6 C5 124.3(9) . . ? C1 C7 P1 113.9(7) . . ? C1 C7 H7A 108.8 . . ? P1 C7 H7A 108.8 . . ? C1 C7 H7B 108.8 . . ? P1 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C3 C8 P2 108.6(6) . . ? C3 C8 H8A 110.0 . . ? P2 C8 H8A 110.0 . . ? C3 C8 H8B 110.0 . . ? P2 C8 H8B 110.0 . . ? H8A C8 H8B 108.3 . . ? C5 C9 P3 107.1(6) . . ? C5 C9 H9A 110.3 . . ? P3 C9 H9A 110.3 . . ? C5 C9 H9B 110.3 . . ? P3 C9 H9B 110.3 . . ? H9A C9 H9B 108.5 . . ? O1 P1 O3 112.9(4) . . ? O1 P1 O2 112.7(4) . . ? O3 P1 O2 110.3(4) . . ? O1 P1 C7 110.2(4) . . ? O3 P1 C7 110.6(4) . . ? O2 P1 C7 99.4(4) . . ? O6 P2 O4 116.2(4) . . ? O6 P2 O5 107.5(4) . . ? O4 P2 O5 111.5(4) . . ? O6 P2 C8 109.7(4) . . ? O4 P2 C8 108.3(4) . . ? O5 P2 C8 102.8(4) . . ? O9 P3 O8 118.1(4) . . ? O9 P3 O7 111.5(4) . . ? O8 P3 O7 104.9(4) . . ? O9 P3 C9 107.6(4) . . ? O8 P3 C9 108.1(4) . . ? O7 P3 C9 106.1(4) . . ? P1 O1 La2 134.3(4) . 2_576 ? P1 O2 H2 109.5 . . ? P1 O3 La2 138.2(4) . . ? P2 O4 La2 142.3(3) . . ? P2 O5 H5 109.5 . . ? P2 O6 La1 165.5(4) . . ? P3 O7 H7 109.5 . . ? P3 O8 La1 154.4(4) . . ? P3 O9 La2 154.3(4) . 1_455 ? C15 C10 C11 115.8(8) . . ? C15 C10 C16 122.9(8) . . ? C11 C10 C16 120.6(8) . . ? F4 C11 C12 118.2(8) . . ? F4 C11 C10 117.6(8) . . ? C12 C11 C10 124.2(8) . . ? C11 C12 C13 116.2(8) . . ? C11 C12 C17 121.1(8) . . ? C13 C12 C17 121.9(9) . . ? F5 C13 C12 118.7(8) . . ? F5 C13 C14 116.9(8) . . ? C12 C13 C14 124.4(9) . . ? C13 C14 C15 114.4(8) . . ? C13 C14 C18 121.8(8) . . ? C15 C14 C18 123.6(8) . . ? F6 C15 C10 118.3(8) . . ? F6 C15 C14 116.7(8) . . ? C10 C15 C14 125.0(8) . . ? C10 C16 P4 109.7(6) . . ? C10 C16 H16A 109.7 . . ? P4 C16 H16A 109.7 . . ? C10 C16 H16B 109.7 . . ? P4 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? C12 C17 P5 107.5(6) . . ? C12 C17 H17A 110.2 . . ? P5 C17 H17A 110.2 . . ? C12 C17 H17B 110.2 . . ? P5 C17 H17B 110.2 . . ? H17A C17 H17B 108.5 . . ? C14 C18 P6 113.5(7) . . ? C14 C18 H18A 108.9 . . ? P6 C18 H18A 108.9 . . ? C14 C18 H18B 108.9 . . ? P6 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? P4 O10 La1 142.0(4) . 1_655 ? P4 O11 H11 109.5 . . ? P4 O12 La2 165.3(4) . . ? P5 O13 La2 154.6(4) . . ? P5 O14 La1 155.2(4) . . ? P5 O15 H15 109.5 . . ? P6 O16 La1 134.5(4) . 2_577 ? P6 O17 H17 109.5 . . ? P6 O18 La1 138.9(4) . 1_655 ? O12 P4 O10 116.3(4) . . ? O12 P4 O11 107.6(4) . . ? O10 P4 O11 111.5(4) . . ? O12 P4 C16 109.3(4) . . ? O10 P4 C16 108.0(4) . . ? O11 P4 C16 103.4(4) . . ? O13 P5 O14 117.8(4) . . ? O13 P5 O15 104.8(4) . . ? O14 P5 O15 111.2(4) . . ? O13 P5 C17 107.8(4) . . ? O14 P5 C17 108.1(4) . . ? O15 P5 C17 106.5(4) . . ? O16 P6 O18 112.3(4) . . ? O16 P6 O17 112.3(4) . . ? O18 P6 O17 110.9(4) . . ? O16 P6 C18 110.1(4) . . ? O18 P6 C18 111.2(4) . . ? O17 P6 C18 99.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 F1 177.4(7) . . . . ? C7 C1 C2 F1 -0.2(13) . . . . ? C6 C1 C2 C3 0.8(14) . . . . ? C7 C1 C2 C3 -176.8(9) . . . . ? F1 C2 C3 C4 -177.9(7) . . . . ? C1 C2 C3 C4 -1.3(14) . . . . ? F1 C2 C3 C8 -6.0(13) . . . . ? C1 C2 C3 C8 170.7(9) . . . . ? C2 C3 C4 F2 -179.8(8) . . . . ? C8 C3 C4 F2 8.1(13) . . . . ? C2 C3 C4 C5 3.9(13) . . . . ? C8 C3 C4 C5 -168.3(9) . . . . ? F2 C4 C5 C6 178.1(8) . . . . ? C3 C4 C5 C6 -5.5(14) . . . . ? F2 C4 C5 C9 -11.6(13) . . . . ? C3 C4 C5 C9 164.8(8) . . . . ? C2 C1 C6 F3 179.9(8) . . . . ? C7 C1 C6 F3 -2.5(12) . . . . ? C2 C1 C6 C5 -2.7(13) . . . . ? C7 C1 C6 C5 174.9(9) . . . . ? C4 C5 C6 F3 -177.6(8) . . . . ? C9 C5 C6 F3 12.2(13) . . . . ? C4 C5 C6 C1 4.9(14) . . . . ? C9 C5 C6 C1 -165.2(8) . . . . ? C2 C1 C7 P1 89.2(10) . . . . ? C6 C1 C7 P1 -88.2(9) . . . . ? C2 C3 C8 P2 -84.2(10) . . . . ? C4 C3 C8 P2 87.4(9) . . . . ? C4 C5 C9 P3 -84.0(10) . . . . ? C6 C5 C9 P3 85.7(10) . . . . ? C1 C7 P1 O1 52.0(8) . . . . ? C1 C7 P1 O3 -73.6(7) . . . . ? C1 C7 P1 O2 170.5(7) . . . . ? C3 C8 P2 O6 -53.3(7) . . . . ? C3 C8 P2 O4 74.5(7) . . . . ? C3 C8 P2 O5 -167.5(6) . . . . ? C5 C9 P3 O9 -179.7(6) . . . . ? C5 C9 P3 O8 51.7(7) . . . . ? C5 C9 P3 O7 -60.3(7) . . . . ? O3 P1 O1 La2 -96.3(5) . . . 2_576 ? O2 P1 O1 La2 29.5(6) . . . 2_576 ? C7 P1 O1 La2 139.5(5) . . . 2_576 ? O1 P1 O3 La2 -33.5(7) . . . . ? O2 P1 O3 La2 -160.6(5) . . . . ? C7 P1 O3 La2 90.5(6) . . . . ? O13 La2 O3 P1 29.3(11) . . . . ? O9 La2 O3 P1 -141.7(6) 1_655 . . . ? O1 La2 O3 P1 71.1(6) 2_576 . . . ? O12 La2 O3 P1 151.8(5) . . . . ? O4 La2 O3 P1 -74.3(6) . . . . ? O2W La2 O3 P1 -5.7(5) . . . . ? O6 P2 O4 La2 17.9(8) . . . . ? O5 P2 O4 La2 141.5(6) . . . . ? C8 P2 O4 La2 -106.1(6) . . . . ? O13 La2 O4 P2 -75.6(6) . . . . ? O9 La2 O4 P2 153.4(6) 1_655 . . . ? O1 La2 O4 P2 -18.4(8) 2_576 . . . ? O12 La2 O4 P2 -139.6(6) . . . . ? O3 La2 O4 P2 85.7(6) . . . . ? O2W La2 O4 P2 16.9(6) . . . . ? O4 P2 O6 La1 74.9(17) . . . . ? O5 P2 O6 La1 -50.7(17) . . . . ? C8 P2 O6 La1 -161.8(15) . . . . ? O14 La1 O6 P2 -32.6(16) . . . . ? O8 La1 O6 P2 -163.0(17) . . . . ? O16 La1 O6 P2 110.5(16) 2_577 . . . ? O10 La1 O6 P2 -98.9(16) 1_455 . . . ? O1W La1 O6 P2 148.8(14) . . . . ? O18 La1 O6 P2 32.7(17) 1_455 . . . ? O9 P3 O8 La1 31.3(11) . . . . ? O7 P3 O8 La1 -93.5(10) . . . . ? C9 P3 O8 La1 153.6(9) . . . . ? O14 La1 O8 P3 108.7(9) . . . . ? O16 La1 O8 P3 -102.3(10) 2_577 . . . ? O6 La1 O8 P3 170.0(10) . . . . ? O10 La1 O8 P3 48.5(9) 1_455 . . . ? O1W La1 O8 P3 -27.8(10) . . . . ? O18 La1 O8 P3 -59.4(13) 1_455 . . . ? O8 P3 O9 La2 -64.7(10) . . . 1_455 ? O7 P3 O9 La2 56.8(10) . . . 1_455 ? C9 P3 O9 La2 172.7(9) . . . 1_455 ? C15 C10 C11 F4 179.8(7) . . . . ? C16 C10 C11 F4 9.0(12) . . . . ? C15 C10 C11 C12 2.0(13) . . . . ? C16 C10 C11 C12 -168.7(8) . . . . ? F4 C11 C12 C13 179.3(8) . . . . ? C10 C11 C12 C13 -3.0(13) . . . . ? F4 C11 C12 C17 -10.8(12) . . . . ? C10 C11 C12 C17 166.9(8) . . . . ? C11 C12 C13 F5 -178.2(8) . . . . ? C17 C12 C13 F5 12.0(13) . . . . ? C11 C12 C13 C14 2.0(13) . . . . ? C17 C12 C13 C14 -167.7(8) . . . . ? F5 C13 C14 C15 179.9(7) . . . . ? C12 C13 C14 C15 -0.3(13) . . . . ? F5 C13 C14 C18 -5.4(12) . . . . ? C12 C13 C14 C18 174.4(9) . . . . ? C11 C10 C15 F6 -179.0(7) . . . . ? C16 C10 C15 F6 -8.5(13) . . . . ? C11 C10 C15 C14 -0.1(13) . . . . ? C16 C10 C15 C14 170.5(8) . . . . ? C13 C14 C15 F6 178.3(7) . . . . ? C18 C14 C15 F6 3.7(13) . . . . ? C13 C14 C15 C10 -0.7(13) . . . . ? C18 C14 C15 C10 -175.3(9) . . . . ? C15 C10 C16 P4 -85.5(9) . . . . ? C11 C10 C16 P4 84.6(9) . . . . ? C11 C12 C17 P5 -83.3(9) . . . . ? C13 C12 C17 P5 86.0(9) . . . . ? C13 C14 C18 P6 -85.4(10) . . . . ? C15 C14 C18 P6 88.8(10) . . . . ? O13 La2 O12 P4 -163.9(17) . . . . ? O9 La2 O12 P4 -34.1(16) 1_655 . . . ? O1 La2 O12 P4 108.9(16) 2_576 . . . ? O4 La2 O12 P4 -100.6(16) . . . . ? O3 La2 O12 P4 32.2(17) . . . . ? O2W La2 O12 P4 148.3(14) . . . . ? O9 La2 O13 P5 111.6(9) 1_655 . . . ? O1 La2 O13 P5 -99.1(10) 2_576 . . . ? O12 La2 O13 P5 173.7(10) . . . . ? O4 La2 O13 P5 51.9(9) . . . . ? O3 La2 O13 P5 -58.0(13) . . . . ? O2W La2 O13 P5 -24.2(10) . . . . ? O8 La1 O14 P5 69.5(10) . . . . ? O16 La1 O14 P5 -58.5(11) 2_577 . . . ? O6 La1 O14 P5 8.7(9) . . . . ? O10 La1 O14 P5 129.1(10) 1_455 . . . ? O1W La1 O14 P5 -172.0(9) . . . . ? O18 La1 O14 P5 -114.4(10) 1_455 . . . ? La2 O12 P4 O10 77.2(17) . . . . ? La2 O12 P4 O11 -48.6(17) . . . . ? La2 O12 P4 C16 -160.3(16) . . . . ? La1 O10 P4 O12 17.0(8) 1_655 . . . ? La1 O10 P4 O11 140.7(6) 1_655 . . . ? La1 O10 P4 C16 -106.3(6) 1_655 . . . ? C10 C16 P4 O12 -53.1(7) . . . . ? C10 C16 P4 O10 74.3(7) . . . . ? C10 C16 P4 O11 -167.4(6) . . . . ? La2 O13 P5 O14 27.1(11) . . . . ? La2 O13 P5 O15 -97.2(10) . . . . ? La2 O13 P5 C17 149.6(9) . . . . ? La1 O14 P5 O13 -65.6(11) . . . . ? La1 O14 P5 O15 55.4(11) . . . . ? La1 O14 P5 C17 171.9(9) . . . . ? C12 C17 P5 O13 51.0(7) . . . . ? C12 C17 P5 O14 179.4(6) . . . . ? C12 C17 P5 O15 -61.0(7) . . . . ? La1 O16 P6 O18 -96.6(5) 2_577 . . . ? La1 O16 P6 O17 29.3(7) 2_577 . . . ? La1 O16 P6 C18 138.9(5) 2_577 . . . ? La1 O18 P6 O16 -32.3(7) 1_655 . . . ? La1 O18 P6 O17 -158.9(5) 1_655 . . . ? La1 O18 P6 C18 91.6(6) 1_655 . . . ? C14 C18 P6 O16 51.5(8) . . . . ? C14 C18 P6 O18 -73.6(8) . . . . ? C14 C18 P6 O17 169.5(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1X O16 0.950(10) 2.04(4) 2.931(9) 155(8) 1_455 O1W H1X O15 0.950(10) 2.62(8) 3.114(9) 113(6) 1_455 O1W H1Y O12 0.950(10) 2.36(6) 3.054(10) 129(6) 1_455 O1W H1Y O13 0.950(10) 2.30(6) 3.132(9) 146(8) 1_455 O2W H2X O1 0.948(10) 2.13(5) 2.960(9) 146(8) . O2W H2X O7 0.948(10) 2.52(7) 3.109(8) 120(6) . O2W H2Y O6 0.949(10) 2.33(6) 3.049(9) 132(6) . O2W H2Y O8 0.949(10) 2.34(6) 3.154(9) 143(8) . O2 H2 O10 0.84 1.90 2.682(9) 153.7 2_676 O5 H5 O18 0.84 1.81 2.578(9) 152.1 2_677 O7 H7 O11 0.84 1.87 2.687(9) 164.0 2_576 O11 H11 O3 0.84 1.79 2.568(9) 152.5 2_676 O15 H15 O5 0.84 1.88 2.692(9) 161.4 2_577 O17 H17 O4 0.84 1.86 2.666(8) 158.9 2_677 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.163 _refine_diff_density_min -1.807 _refine_diff_density_rms 0.218 #============================================================================= # END #============================================================================= _database_code_depnum_ccdc_archive 'CCDC 952452' ####################################################################### # # 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_H6tftp # ======================================================================= # start Validation Reply Form _vrf_PLAT910_H6tftp ; PROBLEM: Missing # of FCF Reflections Below Th(Min) ..... 9 RESPONSE: Data completeness is 99.6% which is enough to guarantee a very good data refinement. ; # start Validation Reply Form # ======================================================================= #============================================================================= _audit_creation_method 'SHELXL-97, manual editing plus enCIFer' _audit_creation_date '25 July 2013' #============================================================================= _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H12 F3 O9 P3, 2(H2 O)' _chemical_formula_sum 'C9 H16 F3 O11 P3' _chemical_formula_weight 450.13 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' 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' #============================================================================= # CRYSTAL DATA #============================================================================= _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.7829(5) _cell_length_b 9.9524(5) _cell_length_c 17.0510(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.424(2) _cell_angle_gamma 90.00 _cell_volume 1632.74(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9795 _cell_measurement_theta_min 3.38 _cell_measurement_theta_max 33.85 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.455 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9475 _exptl_absorpt_correction_T_max 0.9776 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1997) ; #============================================================================= # EXPERIMENTAL DATA #============================================================================= _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Kappa CCD APEX II' _diffrn_measurement_method '\w / \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 68711 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 33.14 _reflns_number_total 6206 _reflns_number_gt 5139 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'APEX2 (Bruker, 2006)' _computing_data_reduction 'SAINT+ (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' #============================================================================= # REFINEMENT DATA #============================================================================= _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^)+(0.0496P)^2^+0.7191P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6206 _refine_ls_number_parameters 253 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 #============================================================================= # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS #============================================================================= 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 -0.13610(3) 0.67423(3) 0.187914(18) 0.01507(7) Uani 1 1 d . . . P2 P 0.39269(3) 0.34799(3) 0.126582(19) 0.01690(8) Uani 1 1 d . . . P3 P 0.27510(3) 0.93342(3) -0.019233(19) 0.01567(7) Uani 1 1 d . . . O1 O -0.16393(10) 0.75613(10) 0.11312(5) 0.01975(18) Uani 1 1 d . . . O2 O -0.11271(12) 0.52394(10) 0.16911(6) 0.0258(2) Uani 1 1 d . . . H2 H -0.1531 0.5064 0.1225 0.039 Uiso 1 1 calc R . . O3 O -0.25581(10) 0.67751(12) 0.23556(6) 0.0265(2) Uani 1 1 d . . . H3 H -0.2327 0.7253 0.2764 0.040 Uiso 1 1 calc R . . O4 O 0.25113(10) 0.29660(10) 0.13317(6) 0.02172(19) Uani 1 1 d . . . O5 O 0.50417(11) 0.23699(11) 0.14282(6) 0.0263(2) Uani 1 1 d . . . H5 H 0.5519 0.2375 0.1065 0.039 Uiso 1 1 calc R . . O6 O 0.39973(12) 0.40636(11) 0.04324(6) 0.0262(2) Uani 1 1 d . . . H6 H 0.3303 0.4556 0.0281 0.039 Uiso 1 1 calc R . . O7 O 0.32180(10) 0.80565(10) -0.05302(6) 0.02193(19) Uani 1 1 d . . . O8 O 0.33181(10) 1.05982(10) -0.05465(6) 0.0231(2) Uani 1 1 d . . . H8 H 0.2653 1.1101 -0.0742 0.035 Uiso 1 1 calc R . . O9 O 0.11477(10) 0.94808(11) -0.03453(6) 0.0233(2) Uani 1 1 d . . . H9 H 0.0786 0.8743 -0.0258 0.035 Uiso 1 1 calc R . . F1 F 0.20233(9) 0.50464(8) 0.26718(5) 0.02160(16) Uani 1 1 d . . . F2 F 0.49257(8) 0.70149(9) 0.10893(5) 0.02287(17) Uani 1 1 d . . . F3 F 0.10206(8) 0.93471(8) 0.15979(5) 0.02048(16) Uani 1 1 d . . . C1 C 0.14554(12) 0.71934(12) 0.21466(7) 0.0153(2) Uani 1 1 d . . . C2 C 0.23272(13) 0.60824(12) 0.22212(7) 0.0157(2) Uani 1 1 d . . . C3 C 0.35092(12) 0.59747(13) 0.18810(7) 0.0158(2) Uani 1 1 d . . . C4 C 0.37890(12) 0.70704(13) 0.14335(7) 0.0159(2) Uani 1 1 d . . . C5 C 0.29896(13) 0.82322(12) 0.13235(7) 0.0154(2) Uani 1 1 d . . . C6 C 0.18300(13) 0.82449(12) 0.16900(7) 0.0150(2) Uani 1 1 d . . . C7 C 0.01938(13) 0.72584(13) 0.25390(7) 0.0167(2) Uani 1 1 d . . . H7A H 0.0075 0.8190 0.2718 0.020 Uiso 1 1 calc R . . H7B H 0.0343 0.6672 0.3016 0.020 Uiso 1 1 calc R . . C8 C 0.44489(13) 0.47587(13) 0.20050(8) 0.0185(2) Uani 1 1 d . . . H8A H 0.4440 0.4379 0.2541 0.022 Uiso 1 1 calc R . . H8B H 0.5413 0.5040 0.1985 0.022 Uiso 1 1 calc R . . C9 C 0.33871(14) 0.94194(13) 0.08635(8) 0.0183(2) Uani 1 1 d . . . H9A H 0.4413 0.9489 0.0956 0.022 Uiso 1 1 calc R . . H9B H 0.3025 1.0248 0.1074 0.022 Uiso 1 1 calc R . . O1W O 0.79581(12) 0.42660(11) 0.02800(6) 0.0271(2) Uani 1 1 d D . . H1X H 0.7473(17) 0.3477(14) 0.0378(12) 0.041 Uiso 1 1 d D . . H1Y H 0.8770(14) 0.4034(19) 0.0081(12) 0.041 Uiso 1 1 d D . . O2W O 0.97281(11) 0.73218(12) 0.98878(6) 0.0273(2) Uani 1 1 d D . . H2X H 0.9016(16) 0.717(2) 0.9443(7) 0.041 Uiso 1 1 d D . . H2Y H 0.9297(18) 0.748(2) 1.0340(7) 0.041 Uiso 1 1 d 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 0.01777(14) 0.01326(14) 0.01473(14) -0.00024(10) 0.00443(11) 0.00015(10) P2 0.01831(15) 0.01557(15) 0.01804(15) 0.00248(11) 0.00653(11) 0.00272(11) P3 0.01430(14) 0.01430(15) 0.01948(15) 0.00362(11) 0.00592(11) 0.00235(10) O1 0.0223(4) 0.0181(4) 0.0192(4) 0.0041(3) 0.0047(3) 0.0036(3) O2 0.0410(6) 0.0147(4) 0.0190(4) -0.0019(4) -0.0015(4) 0.0030(4) O3 0.0207(5) 0.0375(6) 0.0231(5) -0.0070(4) 0.0089(4) -0.0088(4) O4 0.0199(4) 0.0245(5) 0.0211(4) -0.0001(4) 0.0046(3) -0.0028(4) O5 0.0291(5) 0.0236(5) 0.0295(5) 0.0069(4) 0.0139(4) 0.0107(4) O6 0.0339(6) 0.0259(5) 0.0209(4) 0.0063(4) 0.0111(4) 0.0049(4) O7 0.0245(5) 0.0182(4) 0.0253(5) 0.0000(4) 0.0104(4) 0.0036(4) O8 0.0188(4) 0.0200(5) 0.0321(5) 0.0122(4) 0.0085(4) 0.0034(3) O9 0.0148(4) 0.0252(5) 0.0304(5) 0.0065(4) 0.0056(4) 0.0027(4) F1 0.0271(4) 0.0169(4) 0.0224(4) 0.0067(3) 0.0088(3) 0.0006(3) F2 0.0155(3) 0.0245(4) 0.0306(4) 0.0059(3) 0.0093(3) 0.0023(3) F3 0.0238(4) 0.0145(3) 0.0242(4) 0.0015(3) 0.0071(3) 0.0052(3) C1 0.0164(5) 0.0153(5) 0.0144(5) -0.0009(4) 0.0030(4) 0.0001(4) C2 0.0184(5) 0.0139(5) 0.0144(5) 0.0020(4) 0.0021(4) -0.0010(4) C3 0.0155(5) 0.0147(5) 0.0164(5) -0.0002(4) 0.0005(4) 0.0004(4) C4 0.0134(5) 0.0169(5) 0.0176(5) -0.0002(4) 0.0030(4) -0.0012(4) C5 0.0169(5) 0.0140(5) 0.0149(5) 0.0006(4) 0.0018(4) -0.0016(4) C6 0.0171(5) 0.0125(5) 0.0149(5) -0.0006(4) 0.0016(4) 0.0014(4) C7 0.0187(5) 0.0171(6) 0.0151(5) -0.0017(4) 0.0055(4) -0.0003(4) C8 0.0164(5) 0.0167(6) 0.0212(6) 0.0019(5) 0.0003(4) 0.0026(4) C9 0.0191(5) 0.0146(5) 0.0217(6) 0.0012(4) 0.0051(4) -0.0033(4) O1W 0.0356(6) 0.0209(5) 0.0242(5) -0.0017(4) 0.0038(4) -0.0012(4) O2W 0.0216(5) 0.0375(6) 0.0231(5) -0.0031(4) 0.0054(4) -0.0046(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. ; #============================================================================= # GEOMETRY #============================================================================= 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 O1 1.4964(10) . ? P1 O3 1.5417(10) . ? P1 O2 1.5553(10) . ? P1 C7 1.7956(13) . ? P2 O4 1.4994(10) . ? P2 O5 1.5418(10) . ? P2 O6 1.5482(10) . ? P2 C8 1.7989(14) . ? P3 O7 1.5010(10) . ? P3 O8 1.5416(10) . ? P3 O9 1.5496(10) . ? P3 C9 1.7972(14) . ? O2 H2 0.8400 . ? O3 H3 0.8400 . ? O5 H5 0.8400 . ? O6 H6 0.8400 . ? O8 H8 0.8400 . ? O9 H9 0.8400 . ? F1 C2 1.3508(14) . ? F2 C4 1.3492(13) . ? F3 C6 1.3453(14) . ? C1 C2 1.3882(17) . ? C1 C6 1.3925(17) . ? C1 C7 1.5080(16) . ? C2 C3 1.3884(16) . ? C3 C4 1.3863(17) . ? C3 C8 1.5114(17) . ? C4 C5 1.3894(17) . ? C5 C6 1.3907(16) . ? C5 C9 1.5077(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? O1W H1X 0.948(9) . ? O1W H1Y 0.947(9) . ? O2W H2X 0.944(9) . ? O2W H2Y 0.956(9) . ? 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 P1 O3 113.53(6) . . ? O1 P1 O2 111.04(6) . . ? O3 P1 O2 106.45(6) . . ? O1 P1 C7 112.40(6) . . ? O3 P1 C7 107.57(6) . . ? O2 P1 C7 105.35(6) . . ? O4 P2 O5 112.02(6) . . ? O4 P2 O6 113.07(6) . . ? O5 P2 O6 106.63(6) . . ? O4 P2 C8 109.75(6) . . ? O5 P2 C8 106.21(6) . . ? O6 P2 C8 108.88(6) . . ? O7 P3 O8 112.64(6) . . ? O7 P3 O9 112.60(6) . . ? O8 P3 O9 106.39(6) . . ? O7 P3 C9 110.50(6) . . ? O8 P3 C9 105.66(6) . . ? O9 P3 C9 108.70(6) . . ? P1 O2 H2 109.5 . . ? P1 O3 H3 109.5 . . ? P2 O5 H5 109.5 . . ? P2 O6 H6 109.5 . . ? P3 O8 H8 109.5 . . ? P3 O9 H9 109.5 . . ? C2 C1 C6 115.49(11) . . ? C2 C1 C7 122.15(11) . . ? C6 C1 C7 122.35(11) . . ? F1 C2 C1 117.73(10) . . ? F1 C2 C3 117.67(11) . . ? C1 C2 C3 124.58(11) . . ? C4 C3 C2 115.56(11) . . ? C4 C3 C8 122.09(11) . . ? C2 C3 C8 122.33(11) . . ? F2 C4 C3 117.87(11) . . ? F2 C4 C5 117.61(11) . . ? C3 C4 C5 124.51(11) . . ? C4 C5 C6 115.58(11) . . ? C4 C5 C9 122.05(11) . . ? C6 C5 C9 122.33(11) . . ? F3 C6 C5 117.76(10) . . ? F3 C6 C1 117.98(10) . . ? C5 C6 C1 124.26(11) . . ? C1 C7 P1 112.22(8) . . ? C1 C7 H7A 109.2 . . ? P1 C7 H7A 109.2 . . ? C1 C7 H7B 109.2 . . ? P1 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C3 C8 P2 112.34(9) . . ? C3 C8 H8A 109.1 . . ? P2 C8 H8A 109.1 . . ? C3 C8 H8B 109.1 . . ? P2 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C5 C9 P3 114.14(9) . . ? C5 C9 H9A 108.7 . . ? P3 C9 H9A 108.7 . . ? C5 C9 H9B 108.7 . . ? P3 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? H1X O1W H1Y 109.9(12) . . ? H2X O2W H2Y 107.7(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 F1 178.70(11) . . . . ? C7 C1 C2 F1 -0.90(18) . . . . ? C6 C1 C2 C3 0.37(19) . . . . ? C7 C1 C2 C3 -179.24(12) . . . . ? F1 C2 C3 C4 -179.10(11) . . . . ? C1 C2 C3 C4 -0.76(19) . . . . ? F1 C2 C3 C8 -0.47(18) . . . . ? C1 C2 C3 C8 177.86(12) . . . . ? C2 C3 C4 F2 -179.92(11) . . . . ? C8 C3 C4 F2 1.45(18) . . . . ? C2 C3 C4 C5 1.01(19) . . . . ? C8 C3 C4 C5 -177.62(12) . . . . ? F2 C4 C5 C6 -179.91(11) . . . . ? C3 C4 C5 C6 -0.84(19) . . . . ? F2 C4 C5 C9 -2.18(18) . . . . ? C3 C4 C5 C9 176.89(12) . . . . ? C4 C5 C6 F3 -179.76(11) . . . . ? C9 C5 C6 F3 2.51(18) . . . . ? C4 C5 C6 C1 0.39(18) . . . . ? C9 C5 C6 C1 -177.33(12) . . . . ? C2 C1 C6 F3 179.99(11) . . . . ? C7 C1 C6 F3 -0.41(18) . . . . ? C2 C1 C6 C5 -0.17(18) . . . . ? C7 C1 C6 C5 179.43(11) . . . . ? C2 C1 C7 P1 -94.75(13) . . . . ? C6 C1 C7 P1 85.67(13) . . . . ? O1 P1 C7 C1 -57.36(10) . . . . ? O3 P1 C7 C1 176.95(9) . . . . ? O2 P1 C7 C1 63.69(10) . . . . ? C4 C3 C8 P2 -92.07(13) . . . . ? C2 C3 C8 P2 89.39(13) . . . . ? O4 P2 C8 C3 -63.28(10) . . . . ? O5 P2 C8 C3 175.44(9) . . . . ? O6 P2 C8 C3 60.96(10) . . . . ? C4 C5 C9 P3 87.29(13) . . . . ? C6 C5 C9 P3 -95.14(13) . . . . ? O7 P3 C9 C5 -55.64(11) . . . . ? O8 P3 C9 C5 -177.75(9) . . . . ? O9 P3 C9 C5 68.40(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O1W 0.84 1.78 2.5979(14) 162.6 1_455 O3 H3 O4 0.84 1.74 2.5258(14) 155.9 2 O5 H5 O7 0.84 1.72 2.5233(13) 159.9 3_665 O6 H6 O1W 0.84 1.84 2.6567(16) 164.0 3_665 O8 H8 O1 0.84 1.72 2.5404(13) 164.8 3_575 O9 H9 O2W 0.84 1.80 2.6275(15) 169.9 1_454 O1W H1X O7 0.948(9) 1.708(10) 2.6506(15) 172.6(17) 3_665 O1W H1Y O2W 0.947(9) 1.988(14) 2.8173(16) 145.0(16) 3_766 O2W H2X O4 0.944(9) 1.812(10) 2.7490(14) 171.5(18) 3_666 O2W H2Y O1 0.956(9) 1.765(10) 2.7143(14) 171.5(19) 1_656 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.518 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.074 #============================================================================= # END #============================================================================= _database_code_depnum_ccdc_archive 'CCDC 952453' ####################################################################### # # 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_L1 # ======================================================================= # start Validation Reply Form _vrf_PLAT910_L1 ; PROBLEM: Missing # of FCF Reflections Below Th(Min) ..... 4 RESPONSE: Data completeness is 99.8% which is enough for guarantee a very good data refinement. ; # start Validation Reply Form # ======================================================================= # ======================================================================= _audit_creation_method 'SHELXL-97, manual editing plus enCIFer' _audit_creation_date '25 July 2013' # ======================================================================= _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H6 Cl3 F3' _chemical_formula_sum 'C9 H6 Cl3 F3' _chemical_formula_weight 277.49 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.1025(3) _cell_length_b 8.7996(3) _cell_length_c 14.9510(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1065.99(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9004 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 32.77 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.729 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.861 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8963 _exptl_absorpt_correction_T_max 0.9343 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1997) ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Kappa CCD APEX II' _diffrn_measurement_method '\w / \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 18734 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 33.08 _reflns_number_total 4042 _reflns_number_gt 3530 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'APEX2 (Bruker, 2006)' _computing_data_reduction 'SAINT+ (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' #============================================================================== # REFINEMENT DATA #============================================================================== _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^)+(0.0275P)^2^+0.3250P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(5) _refine_ls_number_reflns 4042 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0717 _refine_ls_wR_factor_gt 0.0671 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS #============================================================================== 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 Cl1 Cl 0.61830(5) 0.86012(5) -0.12565(3) 0.03440(10) Uani 1 1 d . . . Cl2 Cl 0.69379(6) 0.84703(5) 0.27713(3) 0.03576(10) Uani 1 1 d . . . Cl3 Cl 0.74646(6) 0.12318(4) 0.07473(4) 0.04097(11) Uani 1 1 d . . . C1 C 0.57999(17) 0.62777(16) -0.00599(9) 0.0196(2) Uani 1 1 d . . . C2 C 0.67966(19) 0.49916(17) -0.00722(9) 0.0203(3) Uani 1 1 d . . . C3 C 0.74922(18) 0.43214(15) 0.06806(10) 0.0212(3) Uani 1 1 d . . . C4 C 0.70792(18) 0.49944(16) 0.14901(9) 0.0204(3) Uani 1 1 d . . . C5 C 0.60793(17) 0.62671(16) 0.15767(9) 0.0198(2) Uani 1 1 d . . . C6 C 0.55008(17) 0.68830(15) 0.07811(9) 0.0187(2) Uani 1 1 d . . . C7 C 0.5069(2) 0.69386(18) -0.08908(10) 0.0257(3) Uani 1 1 d . . . H7A H 0.3904 0.7215 -0.0777 0.031 Uiso 1 1 calc R . . H7B H 0.5087 0.6165 -0.1371 0.031 Uiso 1 1 calc R . . C8 C 0.8607(2) 0.29714(18) 0.06259(12) 0.0290(3) Uani 1 1 d . . . H8A H 0.9452 0.3036 0.1103 0.035 Uiso 1 1 calc R . . H8B H 0.9183 0.2972 0.0042 0.035 Uiso 1 1 calc R . . C9 C 0.5608(2) 0.69076(18) 0.24676(10) 0.0259(3) Uani 1 1 d . . . H9A H 0.5685 0.6102 0.2928 0.031 Uiso 1 1 calc R . . H9B H 0.4449 0.7264 0.2446 0.031 Uiso 1 1 calc R . . F1 F 0.71212(13) 0.43512(11) -0.08736(6) 0.0301(2) Uani 1 1 d . . . F2 F 0.76957(12) 0.43678(10) 0.22429(6) 0.0297(2) Uani 1 1 d . . . F3 F 0.45852(11) 0.81606(10) 0.08308(6) 0.02672(19) 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 Cl1 0.03030(19) 0.02690(19) 0.0460(2) 0.01676(17) 0.00485(16) 0.00071(16) Cl2 0.0468(2) 0.02513(19) 0.03540(19) -0.00905(15) -0.00179(17) -0.00403(17) Cl3 0.0376(2) 0.01714(16) 0.0681(3) 0.00161(18) 0.0067(2) 0.00491(17) C1 0.0179(6) 0.0176(6) 0.0231(6) 0.0025(5) -0.0008(5) -0.0036(5) C2 0.0211(7) 0.0184(6) 0.0214(6) -0.0012(5) 0.0036(5) -0.0026(5) C3 0.0189(6) 0.0156(5) 0.0291(6) 0.0014(5) 0.0021(5) 0.0009(5) C4 0.0199(7) 0.0192(6) 0.0221(6) 0.0052(5) -0.0018(5) -0.0008(5) C5 0.0195(6) 0.0176(6) 0.0223(6) -0.0002(5) 0.0016(5) -0.0020(6) C6 0.0153(6) 0.0142(5) 0.0265(6) 0.0012(5) 0.0003(5) 0.0003(5) C7 0.0264(7) 0.0252(7) 0.0255(7) 0.0078(6) -0.0025(6) -0.0036(6) C8 0.0258(8) 0.0203(7) 0.0409(9) 0.0031(6) 0.0065(6) 0.0037(6) C9 0.0290(7) 0.0253(7) 0.0235(6) -0.0034(5) 0.0035(6) -0.0022(6) F1 0.0381(6) 0.0281(5) 0.0239(4) -0.0049(3) 0.0067(4) 0.0011(4) F2 0.0341(5) 0.0287(5) 0.0261(4) 0.0091(4) -0.0050(4) 0.0037(4) F3 0.0240(4) 0.0202(4) 0.0360(5) 0.0010(4) 0.0011(3) 0.0069(4) #============================================================================== # GEOMETRY #============================================================================== _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 Cl1 C7 1.8039(16) . ? Cl2 C9 1.8052(16) . ? Cl3 C8 1.7980(16) . ? C1 C6 1.3869(19) . ? C1 C2 1.390(2) . ? C1 C7 1.4939(19) . ? C2 F1 1.3500(16) . ? C2 C3 1.390(2) . ? C3 C4 1.388(2) . ? C3 C8 1.495(2) . ? C4 F2 1.3492(16) . ? C4 C5 1.388(2) . ? C5 C6 1.3887(19) . ? C5 C9 1.4960(19) . ? C6 F3 1.3490(16) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 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 C6 C1 C2 115.21(12) . . ? C6 C1 C7 122.35(13) . . ? C2 C1 C7 122.42(12) . . ? F1 C2 C3 117.55(13) . . ? F1 C2 C1 117.68(12) . . ? C3 C2 C1 124.76(13) . . ? C4 C3 C2 115.29(13) . . ? C4 C3 C8 122.17(13) . . ? C2 C3 C8 122.54(13) . . ? F2 C4 C5 117.90(12) . . ? F2 C4 C3 117.62(13) . . ? C5 C4 C3 124.48(12) . . ? C4 C5 C6 115.59(12) . . ? C4 C5 C9 122.42(12) . . ? C6 C5 C9 121.96(13) . . ? F3 C6 C1 117.78(12) . . ? F3 C6 C5 117.62(12) . . ? C1 C6 C5 124.59(13) . . ? C1 C7 Cl1 111.69(11) . . ? C1 C7 H7A 109.3 . . ? Cl1 C7 H7A 109.3 . . ? C1 C7 H7B 109.3 . . ? Cl1 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C3 C8 Cl3 111.11(11) . . ? C3 C8 H8A 109.4 . . ? Cl3 C8 H8A 109.4 . . ? C3 C8 H8B 109.4 . . ? Cl3 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C5 C9 Cl2 111.00(11) . . ? C5 C9 H9A 109.4 . . ? Cl2 C9 H9A 109.4 . . ? C5 C9 H9B 109.4 . . ? Cl2 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 F1 179.69(12) . . . . ? C7 C1 C2 F1 1.1(2) . . . . ? C6 C1 C2 C3 -0.7(2) . . . . ? C7 C1 C2 C3 -179.28(14) . . . . ? F1 C2 C3 C4 -178.07(13) . . . . ? C1 C2 C3 C4 2.3(2) . . . . ? F1 C2 C3 C8 1.9(2) . . . . ? C1 C2 C3 C8 -177.67(14) . . . . ? C2 C3 C4 F2 178.69(13) . . . . ? C8 C3 C4 F2 -1.3(2) . . . . ? C2 C3 C4 C5 -1.4(2) . . . . ? C8 C3 C4 C5 178.57(14) . . . . ? F2 C4 C5 C6 178.92(12) . . . . ? C3 C4 C5 C6 -1.0(2) . . . . ? F2 C4 C5 C9 -3.0(2) . . . . ? C3 C4 C5 C9 177.13(14) . . . . ? C2 C1 C6 F3 177.89(12) . . . . ? C7 C1 C6 F3 -3.5(2) . . . . ? C2 C1 C6 C5 -2.0(2) . . . . ? C7 C1 C6 C5 176.53(14) . . . . ? C4 C5 C6 F3 -177.11(12) . . . . ? C9 C5 C6 F3 4.8(2) . . . . ? C4 C5 C6 C1 2.8(2) . . . . ? C9 C5 C6 C1 -175.28(14) . . . . ? C6 C1 C7 Cl1 79.21(16) . . . . ? C2 C1 C7 Cl1 -102.33(15) . . . . ? C4 C3 C8 Cl3 87.05(16) . . . . ? C2 C3 C8 Cl3 -92.96(16) . . . . ? C4 C5 C9 Cl2 97.10(15) . . . . ? C6 C5 C9 Cl2 -84.93(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 33.08 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.500 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.056 #============================================================================== # END #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 952454' ####################################################################### # # 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_L2 #============================================================================ # start Validation Reply Form # ALERT LEVEL A _vrf_PLAT241_L2 ; PROBLEM: Check High Ueq as Compared to Neighbors for C18 RESPONSE: The ethyl groups are affected by strong thermal motion, which activates some alerts. C18 is an atom particularly affected by this motion which also activates alerts _vrf_PLAT213, _vrf_PLAT242 and _vrf_PLAT360. The thermal motion of the ethyl group also contributes to a large Ueq(max)/Ueq(min) for C and Uiso(max)/Uiso(min) for H, further explaining the alerts _vrf_PLAT220 and _vrf_PLAT222. ; # ALERT LEVEL B _vrf_PLAT220_L2 ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 6.5 Ratio RESPONSE: Please see our response to _vrf_PLAT241. ; _vrf_PLAT910_L2 ; PROBLEM: Missing # of FCF Reflections Below Th(Min) ..... 15 RESPONSE: Data completeness is 98.6% which is enough to guarantee a very good data refinement. ; # ALERT LEVEL C _vrf_PLAT213_L2 ; PROBLEM: Atom C18 has ADP max/min Ratio ..... 3.1 prola RESPONSE: Please see our response to _vrf_PLAT241. ; _vrf_PLAT222_L2 ; PROBLEM: Large Non-Solvent H Uiso(max)/Uiso(min) .. 5.8 Ratio RESPONSE: Please see our response to _vrf_PLAT241. ; _vrf_PLAT242_L2 ; PROBLEM: Check Low Ueq as Compared to Neighbors for O7 RESPONSE: Please see our response to _vrf_PLAT241. ; _vrf_PLAT360_L2 ; PROBLEM: Short C(sp3)-C(sp3) Bond C18 - C19 ... 1.38 Ang. RESPONSE: Please see our response to _vrf_PLAT241. ; _vrf_PLAT911_L2 ; PROBLEM: Missing # FCF Refl Between THmin & STh/L= 0.600 10 RESPONSE: Data completeness is 98.6% which is enough to guarantee a very good data refinement. ; # end Validation Reply Form #============================================================================ # ======================================================================= _audit_creation_method 'SHELXL-97, manual editing plus enCIFer' _audit_creation_date '25 July 2013' # ======================================================================= _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H36 F3 O9 P3' _chemical_formula_sum 'C21 H36 F3 O9 P3' _chemical_formula_weight 582.41 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' 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' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3141(6) _cell_length_b 10.5339(6) _cell_length_c 15.0122(10) _cell_angle_alpha 69.566(3) _cell_angle_beta 71.856(3) _cell_angle_gamma 69.669(3) _cell_volume 1399.25(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4765 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 29.04 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_T_max 0.9945 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1997) ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Kappa CCD APEX II' _diffrn_measurement_method '\w / \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 24478 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0772 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 29.13 _reflns_number_total 7427 _reflns_number_gt 4665 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'APEX2 (Bruker, 2006)' _computing_data_reduction 'SAINT+ (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' #============================================================================== # REFINEMENT DATA #============================================================================== _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^)+(0.0559P)^2^+0.3264P] 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 7427 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1017 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 P1 P 0.34847(6) 0.95800(6) 0.14860(5) 0.02279(15) Uani 1 1 d . . . P2 P 0.17043(6) 0.46056(6) 0.09391(5) 0.02286(15) Uani 1 1 d . . . P3 P -0.25549(7) 0.89832(8) 0.35205(5) 0.03068(17) Uani 1 1 d . . . F1 F 0.28762(13) 0.79171(13) -0.00929(10) 0.0252(3) Uani 1 1 d . . . F2 F -0.16192(13) 0.72597(13) 0.15131(10) 0.0271(3) Uani 1 1 d . . . F3 F -0.03759(13) 1.10248(12) 0.16749(10) 0.0257(3) Uani 1 1 d . . . O1 O 0.46991(17) 1.01580(18) 0.12224(13) 0.0315(4) Uani 1 1 d . . . O2 O 0.38833(17) 0.79237(17) 0.17520(13) 0.0324(4) Uani 1 1 d . . . O3 O 0.23347(17) 0.98842(19) 0.24133(12) 0.0306(4) Uani 1 1 d . . . O4 O 0.18509(17) 0.35430(16) 0.04648(13) 0.0296(4) Uani 1 1 d . . . O5 O 0.31080(17) 0.47262(17) 0.10612(13) 0.0304(4) Uani 1 1 d . . . O6 O 0.07683(17) 0.43949(16) 0.20067(12) 0.0283(4) Uani 1 1 d . . . O7 O -0.1467(2) 0.7480(2) 0.36924(14) 0.0460(5) Uani 1 1 d . . . O8 O -0.4030(2) 0.8656(2) 0.39186(14) 0.0470(5) Uani 1 1 d . . . O9 O -0.2332(2) 0.9933(2) 0.39329(15) 0.0545(6) Uani 1 1 d . . . C1 C 0.2437(2) 1.0235(2) 0.05890(17) 0.0198(5) Uani 1 1 d . . . H1A H 0.1960 1.1244 0.0533 0.024 Uiso 1 1 calc R . . H1B H 0.3069 1.0154 -0.0050 0.024 Uiso 1 1 calc R . . C2 C 0.0957(2) 0.6347(2) 0.02574(18) 0.0231(5) Uani 1 1 d . . . H2A H 0.1613 0.6546 -0.0384 0.028 Uiso 1 1 calc R . . H2B H 0.0062 0.6360 0.0136 0.028 Uiso 1 1 calc R . . C3 C -0.2504(2) 0.9617(2) 0.22391(17) 0.0226(5) Uani 1 1 d . . . H3A H -0.3175 0.9275 0.2093 0.027 Uiso 1 1 calc R . . H3B H -0.2820 1.0658 0.2056 0.027 Uiso 1 1 calc R . . C4 C 0.1334(2) 0.9465(2) 0.08210(16) 0.0181(5) Uani 1 1 d . . . C5 C 0.1600(2) 0.8302(2) 0.04969(16) 0.0179(4) Uani 1 1 d . . . C6 C 0.0647(2) 0.7528(2) 0.06997(16) 0.0180(5) Uani 1 1 d . . . C7 C -0.0645(2) 0.7981(2) 0.12877(16) 0.0188(5) Uani 1 1 d . . . C8 C -0.1045(2) 0.9150(2) 0.16322(16) 0.0182(5) Uani 1 1 d . . . C9 C -0.0015(2) 0.9853(2) 0.13744(16) 0.0184(5) Uani 1 1 d . . . C10 C 0.5202(3) 0.7117(3) 0.1266(2) 0.0437(7) Uani 1 1 d . . . H10A H 0.5019 0.6814 0.0773 0.052 Uiso 1 1 calc R . . H10B H 0.5871 0.7708 0.0930 0.052 Uiso 1 1 calc R . . C11 C 0.5811(4) 0.5902(4) 0.1981(3) 0.0853(14) Uani 1 1 d . . . H11A H 0.6065 0.6210 0.2434 0.128 Uiso 1 1 calc R . . H11B H 0.6661 0.5316 0.1652 0.128 Uiso 1 1 calc R . . H11C H 0.5119 0.5356 0.2342 0.128 Uiso 1 1 calc R . . C12 C 0.2719(3) 0.9410(3) 0.3352(2) 0.0449(7) Uani 1 1 d . . . H12A H 0.3602 0.9643 0.3282 0.054 Uiso 1 1 calc R . . H12B H 0.2880 0.8378 0.3609 0.054 Uiso 1 1 calc R . . C13 C 0.1559(4) 1.0115(5) 0.4019(3) 0.0724(12) Uani 1 1 d . . . H13A H 0.1458 1.1129 0.3786 0.109 Uiso 1 1 calc R . . H13B H 0.1767 0.9754 0.4670 0.109 Uiso 1 1 calc R . . H13C H 0.0676 0.9931 0.4048 0.109 Uiso 1 1 calc R . . C14 C 0.4208(3) 0.3466(3) 0.1384(2) 0.0394(7) Uani 1 1 d . . . H14A H 0.5142 0.3671 0.1119 0.047 Uiso 1 1 calc R . . H14B H 0.4225 0.2709 0.1130 0.047 Uiso 1 1 calc R . . C15 C 0.3949(3) 0.2978(4) 0.2474(3) 0.0597(9) Uani 1 1 d . . . H15A H 0.3757 0.3776 0.2732 0.090 Uiso 1 1 calc R . . H15B H 0.4788 0.2256 0.2671 0.090 Uiso 1 1 calc R . . H15C H 0.3133 0.2582 0.2730 0.090 Uiso 1 1 calc R . . C16 C -0.0355(3) 0.3713(3) 0.2294(2) 0.0414(7) Uani 1 1 d . . . H16A H 0.0051 0.2712 0.2296 0.050 Uiso 1 1 calc R . . H16B H -0.0989 0.4172 0.1828 0.050 Uiso 1 1 calc R . . C17 C -0.1168(3) 0.3826(4) 0.3288(2) 0.0569(9) Uani 1 1 d . . . H17A H -0.0526 0.3403 0.3740 0.085 Uiso 1 1 calc R . . H17B H -0.1906 0.3331 0.3505 0.085 Uiso 1 1 calc R . . H17C H -0.1607 0.4819 0.3273 0.085 Uiso 1 1 calc R . . C18 C -0.0128(5) 0.7293(6) 0.3917(4) 0.116(2) Uani 1 1 d . . . H18A H 0.0099 0.8210 0.3672 0.139 Uiso 1 1 calc R . . H18B H -0.0238 0.6991 0.4633 0.139 Uiso 1 1 calc R . . C19 C 0.0993(4) 0.6319(4) 0.3521(3) 0.0724(11) Uani 1 1 d . . . H19A H 0.0801 0.5395 0.3787 0.109 Uiso 1 1 calc R . . H19B H 0.1862 0.6267 0.3684 0.109 Uiso 1 1 calc R . . H19C H 0.1109 0.6607 0.2812 0.109 Uiso 1 1 calc R . . C20 C -0.4501(4) 0.8039(4) 0.4955(2) 0.0639(10) Uani 1 1 d . . . H20A H -0.5414 0.8657 0.5211 0.077 Uiso 1 1 calc R . . H20B H -0.3797 0.7954 0.5309 0.077 Uiso 1 1 calc R . . C21 C -0.4674(5) 0.6639(4) 0.5115(3) 0.0872(14) Uani 1 1 d . . . H21A H -0.5302 0.6715 0.4714 0.131 Uiso 1 1 calc R . . H21B H -0.5087 0.6272 0.5803 0.131 Uiso 1 1 calc R . . H21C H -0.3747 0.5999 0.4933 0.131 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 0.0173(3) 0.0304(3) 0.0226(3) -0.0091(3) -0.0020(3) -0.0087(2) P2 0.0213(3) 0.0208(3) 0.0312(4) -0.0129(3) -0.0065(3) -0.0048(2) P3 0.0237(3) 0.0470(4) 0.0225(4) -0.0139(3) 0.0002(3) -0.0108(3) F1 0.0209(7) 0.0283(7) 0.0269(8) -0.0147(6) 0.0036(6) -0.0077(5) F2 0.0224(7) 0.0278(7) 0.0365(8) -0.0095(6) -0.0039(6) -0.0146(6) F3 0.0245(7) 0.0221(6) 0.0345(8) -0.0162(6) -0.0025(6) -0.0058(5) O1 0.0209(9) 0.0439(10) 0.0345(11) -0.0141(8) -0.0031(8) -0.0133(8) O2 0.0277(9) 0.0299(9) 0.0316(11) -0.0022(8) -0.0049(8) -0.0056(7) O3 0.0214(9) 0.0514(11) 0.0220(9) -0.0164(8) -0.0031(7) -0.0082(8) O4 0.0307(9) 0.0225(8) 0.0417(11) -0.0186(8) -0.0090(8) -0.0035(7) O5 0.0236(9) 0.0302(9) 0.0429(11) -0.0160(8) -0.0104(8) -0.0048(7) O6 0.0299(9) 0.0269(8) 0.0315(10) -0.0108(7) -0.0053(8) -0.0099(7) O7 0.0445(12) 0.0492(12) 0.0319(12) -0.0016(9) -0.0097(10) -0.0059(10) O8 0.0332(11) 0.0789(15) 0.0266(11) -0.0101(10) 0.0048(9) -0.0267(10) O9 0.0588(14) 0.0799(16) 0.0421(13) -0.0351(12) -0.0058(11) -0.0248(12) C1 0.0204(11) 0.0201(10) 0.0206(12) -0.0078(9) -0.0009(10) -0.0084(9) C2 0.0244(12) 0.0239(11) 0.0275(14) -0.0127(10) -0.0058(10) -0.0081(9) C3 0.0167(11) 0.0262(12) 0.0236(13) -0.0084(10) -0.0020(10) -0.0044(9) C4 0.0189(11) 0.0194(10) 0.0163(12) -0.0031(9) -0.0035(9) -0.0076(9) C5 0.0148(11) 0.0212(10) 0.0157(11) -0.0086(9) 0.0013(9) -0.0029(8) C6 0.0209(11) 0.0171(10) 0.0179(12) -0.0034(9) -0.0077(10) -0.0055(9) C7 0.0180(11) 0.0197(10) 0.0214(12) -0.0028(9) -0.0062(10) -0.0094(9) C8 0.0168(11) 0.0206(10) 0.0166(12) -0.0049(9) -0.0032(9) -0.0045(8) C9 0.0240(12) 0.0164(10) 0.0177(12) -0.0077(9) -0.0049(10) -0.0054(9) C10 0.0355(16) 0.0405(16) 0.0442(19) -0.0141(14) -0.0110(14) 0.0075(13) C11 0.047(2) 0.050(2) 0.113(4) 0.018(2) -0.011(2) -0.0055(17) C12 0.0401(17) 0.075(2) 0.0227(16) -0.0123(15) -0.0085(13) -0.0184(15) C13 0.053(2) 0.139(4) 0.037(2) -0.047(2) 0.0001(17) -0.024(2) C14 0.0241(14) 0.0414(15) 0.056(2) -0.0250(14) -0.0154(14) 0.0048(11) C15 0.0428(19) 0.063(2) 0.057(2) -0.0071(18) -0.0210(18) 0.0040(16) C16 0.0353(15) 0.0522(17) 0.0443(18) -0.0146(14) -0.0017(14) -0.0254(13) C17 0.0473(19) 0.074(2) 0.047(2) -0.0169(17) 0.0065(16) -0.0280(17) C18 0.085(3) 0.144(4) 0.134(5) -0.087(4) -0.085(3) 0.055(3) C19 0.042(2) 0.100(3) 0.083(3) -0.037(2) -0.016(2) -0.013(2) C20 0.059(2) 0.097(3) 0.0275(18) -0.0109(18) 0.0124(16) -0.038(2) C21 0.101(3) 0.094(3) 0.056(3) 0.017(2) -0.016(2) -0.052(3) _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. ; #============================================================================== # GEOMETRY #============================================================================== 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 O1 1.4659(16) . ? P1 O3 1.5705(18) . ? P1 O2 1.5779(17) . ? P1 C1 1.788(2) . ? P2 O4 1.4678(16) . ? P2 O5 1.5669(16) . ? P2 O6 1.5769(18) . ? P2 C2 1.790(2) . ? P3 O9 1.455(2) . ? P3 O8 1.5643(19) . ? P3 O7 1.579(2) . ? P3 C3 1.793(2) . ? F1 C5 1.355(2) . ? F2 C7 1.356(2) . ? F3 C9 1.353(2) . ? O2 C10 1.455(3) . ? O3 C12 1.453(3) . ? O5 C14 1.460(3) . ? O6 C16 1.447(3) . ? O7 C18 1.454(4) . ? O8 C20 1.457(4) . ? C1 C4 1.507(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C6 1.503(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.511(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.382(3) . ? C4 C9 1.383(3) . ? C5 C6 1.386(3) . ? C6 C7 1.379(3) . ? C7 C8 1.383(3) . ? C8 C9 1.385(3) . ? C10 C11 1.444(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.463(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.499(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.489(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.384(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.475(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 P1 O3 116.08(10) . . ? O1 P1 O2 114.16(10) . . ? O3 P1 O2 101.61(10) . . ? O1 P1 C1 114.88(10) . . ? O3 P1 C1 101.56(10) . . ? O2 P1 C1 106.94(10) . . ? O4 P2 O5 116.49(9) . . ? O4 P2 O6 114.41(9) . . ? O5 P2 O6 103.14(10) . . ? O4 P2 C2 111.86(10) . . ? O5 P2 C2 102.68(9) . . ? O6 P2 C2 107.10(10) . . ? O9 P3 O8 116.00(12) . . ? O9 P3 O7 113.63(12) . . ? O8 P3 O7 103.56(11) . . ? O9 P3 C3 114.79(12) . . ? O8 P3 C3 100.82(10) . . ? O7 P3 C3 106.59(11) . . ? C10 O2 P1 121.68(16) . . ? C12 O3 P1 120.20(16) . . ? C14 O5 P2 120.63(15) . . ? C16 O6 P2 120.47(16) . . ? C18 O7 P3 119.7(2) . . ? C20 O8 P3 120.1(2) . . ? C4 C1 P1 113.14(15) . . ? C4 C1 H1A 109.0 . . ? P1 C1 H1A 109.0 . . ? C4 C1 H1B 109.0 . . ? P1 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C6 C2 P2 117.33(16) . . ? C6 C2 H2A 108.0 . . ? P2 C2 H2A 108.0 . . ? C6 C2 H2B 108.0 . . ? P2 C2 H2B 108.0 . . ? H2A C2 H2B 107.2 . . ? C8 C3 P3 112.68(16) . . ? C8 C3 H3A 109.1 . . ? P3 C3 H3A 109.1 . . ? C8 C3 H3B 109.1 . . ? P3 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C9 114.68(18) . . ? C5 C4 C1 122.15(19) . . ? C9 C4 C1 123.17(19) . . ? F1 C5 C4 117.45(17) . . ? F1 C5 C6 117.32(18) . . ? C4 C5 C6 125.2(2) . . ? C7 C6 C5 114.98(19) . . ? C7 C6 C2 122.27(18) . . ? C5 C6 C2 122.6(2) . . ? F2 C7 C6 117.59(18) . . ? F2 C7 C8 117.41(19) . . ? C6 C7 C8 124.94(18) . . ? C7 C8 C9 115.03(19) . . ? C7 C8 C3 121.94(18) . . ? C9 C8 C3 123.03(19) . . ? F3 C9 C4 117.98(17) . . ? F3 C9 C8 116.91(19) . . ? C4 C9 C8 125.10(19) . . ? C11 C10 O2 109.1(3) . . ? C11 C10 H10A 109.9 . . ? O2 C10 H10A 109.9 . . ? C11 C10 H10B 109.9 . . ? O2 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O3 C12 C13 108.3(2) . . ? O3 C12 H12A 110.0 . . ? C13 C12 H12A 110.0 . . ? O3 C12 H12B 110.0 . . ? C13 C12 H12B 110.0 . . ? H12A C12 H12B 108.4 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O5 C14 C15 111.1(2) . . ? O5 C14 H14A 109.4 . . ? C15 C14 H14A 109.4 . . ? O5 C14 H14B 109.4 . . ? C15 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O6 C16 C17 108.6(2) . . ? O6 C16 H16A 110.0 . . ? C17 C16 H16A 110.0 . . ? O6 C16 H16B 110.0 . . ? C17 C16 H16B 110.0 . . ? H16A C16 H16B 108.4 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 O7 113.9(3) . . ? C19 C18 H18A 108.8 . . ? O7 C18 H18A 108.8 . . ? C19 C18 H18B 108.8 . . ? O7 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O8 C20 C21 109.8(3) . . ? O8 C20 H20A 109.7 . . ? C21 C20 H20A 109.7 . . ? O8 C20 H20B 109.7 . . ? C21 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 P1 O2 C10 -34.7(2) . . . . ? O3 P1 O2 C10 -160.40(19) . . . . ? C1 P1 O2 C10 93.6(2) . . . . ? O1 P1 O3 C12 -59.4(2) . . . . ? O2 P1 O3 C12 65.0(2) . . . . ? C1 P1 O3 C12 175.24(19) . . . . ? O4 P2 O5 C14 -43.4(2) . . . . ? O6 P2 O5 C14 82.81(19) . . . . ? C2 P2 O5 C14 -165.97(19) . . . . ? O4 P2 O6 C16 -28.5(2) . . . . ? O5 P2 O6 C16 -155.97(18) . . . . ? C2 P2 O6 C16 96.11(19) . . . . ? O9 P3 O7 C18 -20.5(3) . . . . ? O8 P3 O7 C18 -147.2(3) . . . . ? C3 P3 O7 C18 107.0(3) . . . . ? O9 P3 O8 C20 -58.2(3) . . . . ? O7 P3 O8 C20 67.0(3) . . . . ? C3 P3 O8 C20 177.2(2) . . . . ? O1 P1 C1 C4 171.59(15) . . . . ? O3 P1 C1 C4 -62.29(17) . . . . ? O2 P1 C1 C4 43.79(18) . . . . ? O4 P2 C2 C6 175.51(16) . . . . ? O5 P2 C2 C6 -58.84(19) . . . . ? O6 P2 C2 C6 49.40(19) . . . . ? O9 P3 C3 C8 92.23(18) . . . . ? O8 P3 C3 C8 -142.33(16) . . . . ? O7 P3 C3 C8 -34.51(18) . . . . ? P1 C1 C4 C5 -90.9(2) . . . . ? P1 C1 C4 C9 88.8(2) . . . . ? C9 C4 C5 F1 176.50(19) . . . . ? C1 C4 C5 F1 -3.8(3) . . . . ? C9 C4 C5 C6 -1.1(3) . . . . ? C1 C4 C5 C6 178.6(2) . . . . ? F1 C5 C6 C7 -178.80(18) . . . . ? C4 C5 C6 C7 -1.2(3) . . . . ? F1 C5 C6 C2 -2.9(3) . . . . ? C4 C5 C6 C2 174.7(2) . . . . ? P2 C2 C6 C7 -90.7(2) . . . . ? P2 C2 C6 C5 93.6(2) . . . . ? C5 C6 C7 F2 -179.80(18) . . . . ? C2 C6 C7 F2 4.2(3) . . . . ? C5 C6 C7 C8 3.0(3) . . . . ? C2 C6 C7 C8 -172.9(2) . . . . ? F2 C7 C8 C9 -179.50(18) . . . . ? C6 C7 C8 C9 -2.3(3) . . . . ? F2 C7 C8 C3 0.2(3) . . . . ? C6 C7 C8 C3 177.3(2) . . . . ? P3 C3 C8 C7 96.3(2) . . . . ? P3 C3 C8 C9 -84.1(2) . . . . ? C5 C4 C9 F3 -176.67(19) . . . . ? C1 C4 C9 F3 3.7(3) . . . . ? C5 C4 C9 C8 1.9(3) . . . . ? C1 C4 C9 C8 -177.7(2) . . . . ? C7 C8 C9 F3 178.27(19) . . . . ? C3 C8 C9 F3 -1.4(3) . . . . ? C7 C8 C9 C4 -0.3(3) . . . . ? C3 C8 C9 C4 180.0(2) . . . . ? P1 O2 C10 C11 137.4(3) . . . . ? P1 O3 C12 C13 166.5(2) . . . . ? P2 O5 C14 C15 -87.2(3) . . . . ? P2 O6 C16 C17 -172.8(2) . . . . ? P3 O7 C18 C19 -144.6(4) . . . . ? P3 O8 C20 C21 -116.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.529 _refine_diff_density_min -0.608 _refine_diff_density_rms 0.068 #============================================================================== # END #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 952455'