# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_alb96(4) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 N8, 2 (C F3 O3 S)' _chemical_formula_sum 'C18 H18 F6 N8 O6 S2' _chemical_formula_weight 620.52 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _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' '-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 23.156(1) _cell_length_b 8.0465(3) _cell_length_c 26.901(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5012.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7209 _cell_measurement_theta_min 3.3950 _cell_measurement_theta_max 21.9622 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2364 _exptl_crystal_size_mid 0.1585 _exptl_crystal_size_min 0.0483 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 0.310 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) 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 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20946 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 22.01 _reflns_number_total 3069 _reflns_number_gt 2844 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0000P)^2^+42.5503P] 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 3069 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0918 _refine_ls_R_factor_gt 0.0870 _refine_ls_wR_factor_ref 0.1661 _refine_ls_wR_factor_gt 0.1640 _refine_ls_goodness_of_fit_ref 1.194 _refine_ls_restrained_S_all 1.194 _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 N1 N 0.2493(3) 0.0442(7) -0.0192(2) 0.0378(15) Uani 1 1 d . . . C1 C 0.3105(3) 0.0448(10) -0.0346(3) 0.049(2) Uani 1 1 d . . . H1A H 0.3249 0.1593 -0.0350 0.073 Uiso 1 1 calc R . . H1B H 0.3139 -0.0031 -0.0680 0.073 Uiso 1 1 calc R . . H1C H 0.3332 -0.0213 -0.0111 0.073 Uiso 1 1 calc R . . N2 N 0.2116(3) -0.0373(8) -0.0477(2) 0.0447(17) Uani 1 1 d . . . N3 N 0.1605(2) -0.0198(8) -0.0260(2) 0.0413(16) Uani 1 1 d . . . C2 C 0.2242(3) 0.1120(9) 0.0211(3) 0.0376(18) Uani 1 1 d . . . H2 H 0.2420 0.1744 0.0469 0.045 Uiso 1 1 calc R . . C3 C 0.1671(3) 0.0705(9) 0.0165(3) 0.0323(17) Uani 1 1 d . . . C4 C 0.1152(3) 0.1052(8) 0.0457(3) 0.0301(17) Uani 1 1 d . . . N4 N 0.1149(2) 0.0762(8) 0.0940(2) 0.0388(16) Uani 1 1 d . . . C5 C 0.1673(3) 0.0318(10) 0.1231(3) 0.044(2) Uani 1 1 d . . . H5A H 0.1883 0.1333 0.1320 0.065 Uiso 1 1 calc R . . H5B H 0.1923 -0.0400 0.1030 0.065 Uiso 1 1 calc R . . H5C H 0.1559 -0.0271 0.1534 0.065 Uiso 1 1 calc R . . N5 N 0.0675(3) 0.0871(7) 0.1237(2) 0.0396(16) Uani 1 1 d . . . C6 C 0.0642(3) 0.1679(8) 0.0228(3) 0.0299(17) Uani 1 1 d . . . C7 C 0.0627(3) 0.2209(8) -0.0272(3) 0.0320(17) Uani 1 1 d . . . H7 H 0.0960 0.2097 -0.0475 0.038 Uiso 1 1 calc R . . C8 C 0.0132(3) 0.2885(9) -0.0463(3) 0.0342(18) Uani 1 1 d . . . H8 H 0.0123 0.3227 -0.0800 0.041 Uiso 1 1 calc R . . C9 C -0.0362(3) 0.3081(9) -0.0166(3) 0.0351(18) Uani 1 1 d . . . H9 H -0.0704 0.3539 -0.0304 0.042 Uiso 1 1 calc R . . C10 C -0.0353(3) 0.2614(9) 0.0321(3) 0.0347(18) Uani 1 1 d . . . H10 H -0.0683 0.2787 0.0523 0.042 Uiso 1 1 calc R . . C11 C 0.0142(3) 0.1880(8) 0.0524(3) 0.0309(17) Uani 1 1 d . . . C12 C 0.0193(3) 0.1391(8) 0.1025(3) 0.0336(18) Uani 1 1 d . . . C13 C -0.0317(3) 0.1361(9) 0.1359(3) 0.0395(19) Uani 1 1 d . . . C14 C -0.0869(3) 0.0854(9) 0.1268(3) 0.039(2) Uani 1 1 d . . . H14 H -0.1019 0.0429 0.0966 0.047 Uiso 1 1 calc R . . N6 N -0.0307(3) 0.1852(9) 0.1839(2) 0.054(2) Uani 1 1 d . . . C15 C 0.0143(4) 0.2652(17) 0.2120(3) 0.095(4) Uani 1 1 d . . . H15A H 0.0496 0.1982 0.2102 0.142 Uiso 1 1 calc R . . H15B H 0.0022 0.2759 0.2467 0.142 Uiso 1 1 calc R . . H15C H 0.0218 0.3757 0.1981 0.142 Uiso 1 1 calc R . . C16 C -0.1766(4) 0.0750(10) 0.1789(4) 0.068(3) Uani 1 1 d . . . H16A H -0.1865 0.1134 0.2124 0.102 Uiso 1 1 calc R . . H16B H -0.1841 -0.0445 0.1763 0.102 Uiso 1 1 calc R . . H16C H -0.2003 0.1345 0.1545 0.102 Uiso 1 1 calc R . . N7 N -0.0831(3) 0.1661(9) 0.2050(3) 0.058(2) Uani 1 1 d . . . N8 N -0.1151(3) 0.1079(8) 0.1691(3) 0.053(2) Uani 1 1 d . . . O1 O 0.1505(2) 0.2224(7) 0.37509(18) 0.0470(14) Uani 1 1 d . . . O2 O 0.0917(2) -0.0218(7) 0.3620(2) 0.0546(16) Uani 1 1 d . . . O3 O 0.0704(3) 0.2368(8) 0.3185(3) 0.080(2) Uani 1 1 d . . . S1 S 0.11210(8) 0.1327(2) 0.34229(7) 0.0398(5) Uani 1 1 d . . . C17 C 0.1589(4) 0.0730(10) 0.2923(3) 0.051(2) Uani 1 1 d . . . F1 F 0.1983(2) -0.0350(6) 0.3069(2) 0.0801(18) Uani 1 1 d . . . F2 F 0.1873(3) 0.1998(6) 0.27260(19) 0.0826(19) Uani 1 1 d . . . F3 F 0.1298(3) -0.0005(6) 0.25549(18) 0.094(2) Uani 1 1 d . . . O4 O 0.0950(2) 0.4501(6) 0.1018(2) 0.0487(15) Uani 1 1 d . . . O5 O 0.1588(2) 0.6800(6) 0.08082(19) 0.0422(13) Uani 1 1 d . . . O6 O 0.1978(2) 0.4081(7) 0.0962(2) 0.0607(17) Uani 1 1 d . . . S2 S 0.15156(8) 0.5223(2) 0.10537(7) 0.0396(5) Uani 1 1 d . . . C18 C 0.1572(6) 0.5691(14) 0.1696(4) 0.082(3) Uani 1 1 d . . . F4 F 0.1170(4) 0.6776(8) 0.1838(2) 0.108(2) Uani 1 1 d . . . F5 F 0.2080(3) 0.6438(9) 0.1805(2) 0.112(3) Uani 1 1 d . . . F6 F 0.1527(3) 0.4364(8) 0.1985(2) 0.112(3) 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 N1 0.028(3) 0.030(3) 0.056(4) 0.011(3) 0.003(3) -0.002(3) C1 0.029(4) 0.046(5) 0.070(6) 0.012(5) 0.016(4) 0.002(4) N2 0.036(4) 0.037(4) 0.061(4) 0.006(3) 0.007(3) 0.009(3) N3 0.025(3) 0.038(4) 0.061(5) 0.009(4) 0.009(3) 0.003(3) C2 0.038(4) 0.037(4) 0.037(4) 0.010(4) 0.007(4) 0.007(4) C3 0.029(4) 0.031(4) 0.037(4) 0.010(4) 0.002(3) 0.008(3) C4 0.028(4) 0.021(4) 0.041(5) 0.001(3) 0.003(3) 0.005(3) N4 0.034(4) 0.040(4) 0.042(4) 0.015(3) 0.002(3) 0.011(3) C5 0.034(4) 0.040(5) 0.057(5) 0.018(4) 0.001(4) 0.008(4) N5 0.040(4) 0.033(4) 0.046(4) 0.018(3) 0.009(3) 0.012(3) C6 0.030(4) 0.019(4) 0.041(4) 0.006(3) 0.004(3) 0.001(3) C7 0.033(4) 0.027(4) 0.036(4) 0.011(3) 0.007(3) -0.003(3) C8 0.030(4) 0.035(4) 0.038(4) 0.014(4) -0.004(3) 0.001(3) C9 0.021(4) 0.040(4) 0.044(5) 0.010(4) -0.002(3) 0.000(3) C10 0.027(4) 0.036(4) 0.041(5) 0.010(4) 0.008(3) 0.000(3) C11 0.027(4) 0.026(4) 0.040(4) 0.011(3) 0.003(3) 0.000(3) C12 0.036(4) 0.023(4) 0.042(4) 0.017(3) 0.004(4) 0.004(3) C13 0.051(5) 0.030(4) 0.037(5) 0.020(4) 0.006(4) 0.011(4) C14 0.046(5) 0.026(4) 0.046(5) 0.013(4) 0.021(4) 0.007(4) N6 0.055(5) 0.071(5) 0.036(4) 0.023(4) 0.006(4) 0.027(4) C15 0.073(7) 0.168(13) 0.044(6) -0.002(7) -0.018(5) 0.046(8) C16 0.057(6) 0.036(5) 0.111(8) 0.029(5) 0.061(6) 0.018(4) N7 0.070(5) 0.064(5) 0.040(4) 0.025(4) 0.023(4) 0.033(4) N8 0.066(5) 0.040(4) 0.053(5) 0.027(4) 0.030(4) 0.019(4) O1 0.058(3) 0.048(3) 0.035(3) -0.013(3) -0.004(3) -0.017(3) O2 0.062(4) 0.041(3) 0.061(4) -0.018(3) 0.021(3) -0.024(3) O3 0.061(4) 0.061(4) 0.119(6) -0.022(4) -0.047(4) 0.028(4) S1 0.0369(11) 0.0421(12) 0.0405(11) -0.0100(10) -0.0021(9) -0.0004(10) C17 0.078(6) 0.027(4) 0.047(5) 0.005(4) 0.017(5) 0.013(5) F1 0.075(4) 0.044(3) 0.121(5) 0.017(3) 0.038(3) 0.021(3) F2 0.142(5) 0.037(3) 0.069(4) 0.010(3) 0.052(4) 0.002(3) F3 0.190(7) 0.054(3) 0.038(3) -0.017(3) -0.002(4) -0.014(4) O4 0.034(3) 0.043(3) 0.069(4) 0.024(3) -0.003(3) -0.004(3) O5 0.039(3) 0.035(3) 0.053(3) 0.014(3) 0.002(3) -0.001(2) O6 0.039(3) 0.045(3) 0.098(5) 0.024(3) 0.008(3) 0.010(3) S2 0.0355(11) 0.0382(11) 0.0451(12) 0.0160(10) -0.0015(9) 0.0002(9) C18 0.122(10) 0.062(7) 0.060(7) 0.021(6) -0.011(7) -0.025(7) F4 0.176(7) 0.078(5) 0.069(4) 0.004(4) 0.054(5) -0.016(5) F5 0.147(6) 0.110(5) 0.078(4) 0.023(4) -0.053(4) -0.049(5) F6 0.190(7) 0.090(5) 0.055(4) 0.042(3) -0.019(4) -0.026(5) _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 N1 N2 1.334(9) . ? N1 C2 1.346(9) . ? N1 C1 1.475(9) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? N2 N3 1.328(8) . ? N3 C3 1.364(9) . ? C2 C3 1.370(10) . ? C2 H2 0.9500 . ? C3 C4 1.461(9) . ? C4 N4 1.319(9) . ? C4 C6 1.426(9) . ? N4 N5 1.362(8) . ? N4 C5 1.487(9) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? N5 C12 1.320(9) . ? C6 C7 1.410(9) . ? C6 C11 1.414(9) . ? C7 C8 1.368(9) . ? C7 H7 0.9500 . ? C8 C9 1.405(10) . ? C8 H8 0.9500 . ? C9 C10 1.361(10) . ? C9 H9 0.9500 . ? C10 C11 1.401(9) . ? C10 H10 0.9500 . ? C11 C12 1.410(10) . ? C12 C13 1.482(10) . ? C13 N6 1.350(10) . ? C13 C14 1.363(11) . ? C14 N8 1.325(9) . ? C14 H14 0.9500 . ? N6 N7 1.349(9) . ? N6 C15 1.439(12) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 N8 1.473(10) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N7 N8 1.302(10) . ? O1 S1 1.446(5) . ? O2 S1 1.431(6) . ? O3 S1 1.429(6) . ? S1 C17 1.793(8) . ? C17 F1 1.321(9) . ? C17 F2 1.324(9) . ? C17 F3 1.335(10) . ? O4 S2 1.436(5) . ? O5 S2 1.440(5) . ? O6 S2 1.432(6) . ? S2 C18 1.774(11) . ? C18 F6 1.324(11) . ? C18 F4 1.332(13) . ? C18 F5 1.353(12) . ? 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 N2 N1 C2 112.3(6) . . ? N2 N1 C1 117.9(6) . . ? C2 N1 C1 129.8(7) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 N2 N1 106.2(6) . . ? N2 N3 C3 109.0(6) . . ? N1 C2 C3 104.2(7) . . ? N1 C2 H2 127.9 . . ? C3 C2 H2 127.9 . . ? N3 C3 C2 108.2(6) . . ? N3 C3 C4 117.4(6) . . ? C2 C3 C4 134.3(7) . . ? N4 C4 C6 119.0(6) . . ? N4 C4 C3 119.9(6) . . ? C6 C4 C3 121.1(6) . . ? C4 N4 N5 124.7(6) . . ? C4 N4 C5 123.8(6) . . ? N5 N4 C5 111.4(6) . . ? N4 C5 H5A 109.5 . . ? N4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C12 N5 N4 116.7(6) . . ? C7 C6 C11 118.9(6) . . ? C7 C6 C4 122.6(6) . . ? C11 C6 C4 118.3(6) . . ? C8 C7 C6 119.9(6) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.9(7) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C10 C9 C8 120.2(7) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.3(7) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C12 124.0(6) . . ? C10 C11 C6 119.8(6) . . ? C12 C11 C6 116.1(6) . . ? N5 C12 C11 124.8(6) . . ? N5 C12 C13 114.0(6) . . ? C11 C12 C13 121.1(6) . . ? N6 C13 C14 105.8(7) . . ? N6 C13 C12 124.1(7) . . ? C14 C13 C12 130.0(7) . . ? N8 C14 C13 105.6(8) . . ? N8 C14 H14 127.2 . . ? C13 C14 H14 127.2 . . ? N7 N6 C13 110.8(7) . . ? N7 N6 C15 118.8(7) . . ? C13 N6 C15 130.1(8) . . ? N6 C15 H15A 109.5 . . ? N6 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N6 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N8 C16 H16A 109.5 . . ? N8 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N8 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N8 N7 N6 104.0(6) . . ? N7 N8 C14 113.8(7) . . ? N7 N8 C16 118.9(7) . . ? C14 N8 C16 127.3(9) . . ? O3 S1 O2 116.9(4) . . ? O3 S1 O1 113.4(4) . . ? O2 S1 O1 114.3(3) . . ? O3 S1 C17 103.2(4) . . ? O2 S1 C17 104.1(3) . . ? O1 S1 C17 102.7(4) . . ? F1 C17 F2 106.4(7) . . ? F1 C17 F3 106.1(7) . . ? F2 C17 F3 107.2(7) . . ? F1 C17 S1 111.8(6) . . ? F2 C17 S1 113.2(5) . . ? F3 C17 S1 111.7(7) . . ? O6 S2 O4 114.2(3) . . ? O6 S2 O5 113.6(3) . . ? O4 S2 O5 115.6(3) . . ? O6 S2 C18 104.4(5) . . ? O4 S2 C18 102.6(5) . . ? O5 S2 C18 104.6(4) . . ? F6 C18 F4 107.9(10) . . ? F6 C18 F5 107.5(9) . . ? F4 C18 F5 104.8(9) . . ? F6 C18 S2 113.2(8) . . ? F4 C18 S2 111.5(8) . . ? F5 C18 S2 111.6(8) . . ? 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 C2 N1 N2 N3 1.1(8) . . . . ? C1 N1 N2 N3 179.7(6) . . . . ? N1 N2 N3 C3 -1.0(8) . . . . ? N2 N1 C2 C3 -0.7(8) . . . . ? C1 N1 C2 C3 -179.1(7) . . . . ? N2 N3 C3 C2 0.6(8) . . . . ? N2 N3 C3 C4 179.3(6) . . . . ? N1 C2 C3 N3 0.1(8) . . . . ? N1 C2 C3 C4 -178.3(7) . . . . ? N3 C3 C4 N4 130.6(7) . . . . ? C2 C3 C4 N4 -51.1(12) . . . . ? N3 C3 C4 C6 -48.4(9) . . . . ? C2 C3 C4 C6 129.9(9) . . . . ? C6 C4 N4 N5 6.3(11) . . . . ? C3 C4 N4 N5 -172.7(6) . . . . ? C6 C4 N4 C5 -171.8(6) . . . . ? C3 C4 N4 C5 9.1(11) . . . . ? C4 N4 N5 C12 -3.7(10) . . . . ? C5 N4 N5 C12 174.6(6) . . . . ? N4 C4 C6 C7 172.2(7) . . . . ? C3 C4 C6 C7 -8.7(10) . . . . ? N4 C4 C6 C11 -3.3(10) . . . . ? C3 C4 C6 C11 175.7(6) . . . . ? C11 C6 C7 C8 -0.8(10) . . . . ? C4 C6 C7 C8 -176.4(7) . . . . ? C6 C7 C8 C9 0.8(11) . . . . ? C7 C8 C9 C10 0.8(11) . . . . ? C8 C9 C10 C11 -2.4(11) . . . . ? C9 C10 C11 C12 178.7(7) . . . . ? C9 C10 C11 C6 2.4(11) . . . . ? C7 C6 C11 C10 -0.8(10) . . . . ? C4 C6 C11 C10 175.0(6) . . . . ? C7 C6 C11 C12 -177.4(6) . . . . ? C4 C6 C11 C12 -1.6(10) . . . . ? N4 N5 C12 C11 -2.0(11) . . . . ? N4 N5 C12 C13 175.6(6) . . . . ? C10 C11 C12 N5 -172.0(7) . . . . ? C6 C11 C12 N5 4.4(11) . . . . ? C10 C11 C12 C13 10.5(11) . . . . ? C6 C11 C12 C13 -173.0(7) . . . . ? N5 C12 C13 N6 42.1(10) . . . . ? C11 C12 C13 N6 -140.2(7) . . . . ? N5 C12 C13 C14 -137.1(8) . . . . ? C11 C12 C13 C14 40.6(11) . . . . ? N6 C13 C14 N8 0.4(8) . . . . ? C12 C13 C14 N8 179.7(7) . . . . ? C14 C13 N6 N7 0.3(8) . . . . ? C12 C13 N6 N7 -179.1(6) . . . . ? C14 C13 N6 C15 -173.1(9) . . . . ? C12 C13 N6 C15 7.5(13) . . . . ? C13 N6 N7 N8 -0.9(8) . . . . ? C15 N6 N7 N8 173.4(8) . . . . ? N6 N7 N8 C14 1.2(9) . . . . ? N6 N7 N8 C16 -178.7(6) . . . . ? C13 C14 N8 N7 -1.0(9) . . . . ? C13 C14 N8 C16 178.9(7) . . . . ? O3 S1 C17 F1 -175.4(6) . . . . ? O2 S1 C17 F1 -52.8(7) . . . . ? O1 S1 C17 F1 66.6(7) . . . . ? O3 S1 C17 F2 64.5(8) . . . . ? O2 S1 C17 F2 -173.0(6) . . . . ? O1 S1 C17 F2 -53.6(7) . . . . ? O3 S1 C17 F3 -56.6(6) . . . . ? O2 S1 C17 F3 65.9(6) . . . . ? O1 S1 C17 F3 -174.7(5) . . . . ? O6 S2 C18 F6 -59.1(11) . . . . ? O4 S2 C18 F6 60.3(11) . . . . ? O5 S2 C18 F6 -178.7(9) . . . . ? O6 S2 C18 F4 179.1(7) . . . . ? O4 S2 C18 F4 -61.5(8) . . . . ? O5 S2 C18 F4 59.5(8) . . . . ? O6 S2 C18 F5 62.3(9) . . . . ? O4 S2 C18 F5 -178.3(8) . . . . ? O5 S2 C18 F5 -57.3(9) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 22.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.431 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.080 # start Validation Reply Form _vrf_THETM01_alb964 ; PROBLEM: ALERT: The value of sine(theta_max)/wavelength is less than 0.550 Calculated sin(theta_max)/wavelength = 0.5273 RESPONSE: Unfortunately no higher quality crystals could be obtained. The data to parameter ratio is still above 8 which is sufficient to rule out over-refinement. ; _database_code_depnum_ccdc_archive 'CCDC 948959' ####################################################################### # # 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_alb100(3) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 N8, C H Cl3, I' _chemical_formula_sum 'C16 H16 Cl3 I N8' _chemical_formula_weight 553.62 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 16.5447(6) _cell_length_b 6.8596(3) _cell_length_c 19.1037(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.175(4) _cell_angle_gamma 90.00 _cell_volume 2119.31(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5447 _cell_measurement_theta_min 3.3126 _cell_measurement_theta_max 24.0911 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.1849 _exptl_crystal_size_mid 0.1005 _exptl_crystal_size_min 0.0797 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.735 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 1.909 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.737 _exptl_absorpt_correction_T_max 0.866 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) 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 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15714 _diffrn_reflns_av_R_equivalents 0.0540 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 24.14 _reflns_number_total 3351 _reflns_number_gt 2791 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0197P)^2^+2.5839P] 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 3351 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0638 _refine_ls_wR_factor_gt 0.0578 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.001 _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 C1 C 0.3504(2) 1.3881(6) 0.5793(2) 0.0283(10) Uani 1 1 d . . . H1A H 0.3722 1.5155 0.5692 0.042 Uiso 1 1 calc R . . H1B H 0.3042 1.4064 0.6033 0.042 Uiso 1 1 calc R . . H1C H 0.3312 1.3174 0.5342 0.042 Uiso 1 1 calc R . . N1 N 0.41584(18) 1.2756(4) 0.62577(17) 0.0184(7) Uani 1 1 d . . . N2 N 0.40663(19) 1.2177(5) 0.69058(18) 0.0224(8) Uani 1 1 d . . . N3 N 0.47293(19) 1.1169(5) 0.71949(17) 0.0225(8) Uani 1 1 d . . . C2 C 0.4871(2) 1.2111(6) 0.6123(2) 0.0209(9) Uani 1 1 d . . . H2 H 0.5078 1.2308 0.5701 0.025 Uiso 1 1 calc R . . C3 C 0.5237(2) 1.1104(5) 0.67230(19) 0.0147(8) Uani 1 1 d . . . C4 C 0.6020(2) 1.0018(5) 0.68813(19) 0.0149(8) Uani 1 1 d . . . N4 N 0.60455(17) 0.8298(4) 0.65801(16) 0.0150(7) Uani 1 1 d . . . C5 C 0.5334(2) 0.7437(6) 0.6083(2) 0.0219(9) Uani 1 1 d . . . H5A H 0.4856 0.7402 0.6311 0.033 Uiso 1 1 calc R . . H5B H 0.5472 0.6108 0.5960 0.033 Uiso 1 1 calc R . . H5C H 0.5201 0.8227 0.5646 0.033 Uiso 1 1 calc R . . N5 N 0.67170(18) 0.7125(4) 0.66795(16) 0.0167(7) Uani 1 1 d . . . C6 C 0.6733(2) 1.0708(5) 0.73735(18) 0.0133(8) Uani 1 1 d . . . C7 C 0.6716(2) 1.2509(5) 0.7734(2) 0.0169(9) Uani 1 1 d . . . H7 H 0.6235 1.3305 0.7639 0.020 Uiso 1 1 calc R . . C8 C 0.7407(2) 1.3080(6) 0.8223(2) 0.0194(9) Uani 1 1 d . . . H8 H 0.7401 1.4269 0.8477 0.023 Uiso 1 1 calc R . . C9 C 0.8121(2) 1.1926(6) 0.8351(2) 0.0192(9) Uani 1 1 d . . . H9 H 0.8595 1.2358 0.8686 0.023 Uiso 1 1 calc R . . C10 C 0.8152(2) 1.0185(6) 0.80037(19) 0.0179(9) Uani 1 1 d . . . H10 H 0.8643 0.9425 0.8098 0.021 Uiso 1 1 calc R . . C11 C 0.7452(2) 0.9532(5) 0.75070(19) 0.0148(8) Uani 1 1 d . . . C12 C 0.7402(2) 0.7725(5) 0.71185(19) 0.0156(8) Uani 1 1 d . . . C13 C 0.8069(2) 0.6306(5) 0.71517(19) 0.0155(8) Uani 1 1 d . . . C14 C 0.8047(2) 0.4696(5) 0.6717(2) 0.0169(9) Uani 1 1 d . . . H14 H 0.7608 0.4296 0.6338 0.020 Uiso 1 1 calc R . . N6 N 0.88125(18) 0.6327(5) 0.76236(17) 0.0197(8) Uani 1 1 d . . . N7 N 0.92421(18) 0.4808(5) 0.74975(17) 0.0212(8) Uani 1 1 d . . . N8 N 0.87739(17) 0.3823(4) 0.69428(16) 0.0172(7) Uani 1 1 d . . . C15 C 0.9098(2) 0.2090(6) 0.6660(2) 0.0233(10) Uani 1 1 d . . . H15A H 0.8648 0.1414 0.6334 0.035 Uiso 1 1 calc R . . H15B H 0.9339 0.1220 0.7055 0.035 Uiso 1 1 calc R . . H15C H 0.9523 0.2468 0.6399 0.035 Uiso 1 1 calc R . . I I 0.321037(15) 0.89695(4) 0.476267(13) 0.02164(10) Uani 1 1 d . . . C16 C 0.8754(3) 0.7487(6) 0.5225(2) 0.0257(10) Uani 1 1 d . . . H16 H 0.8251 0.8189 0.5305 0.031 Uiso 1 1 calc R . . Cl1 Cl 0.95477(6) 0.77351(15) 0.60077(5) 0.0276(3) Uani 1 1 d . . . Cl2 Cl 0.85039(7) 0.50043(16) 0.50723(6) 0.0338(3) Uani 1 1 d . . . Cl3 Cl 0.90518(7) 0.85129(17) 0.44764(6) 0.0397(3) 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 C1 0.027(2) 0.025(2) 0.030(2) -0.006(2) 0.001(2) 0.0107(19) N1 0.0144(17) 0.0175(18) 0.0206(19) -0.0031(15) -0.0024(14) 0.0037(14) N2 0.0199(18) 0.0220(19) 0.026(2) 0.0021(16) 0.0065(15) 0.0019(15) N3 0.0201(17) 0.0261(19) 0.0239(19) 0.0026(16) 0.0103(15) 0.0052(15) C2 0.023(2) 0.023(2) 0.018(2) -0.0027(18) 0.0081(18) 0.0021(18) C3 0.0145(18) 0.0130(19) 0.016(2) -0.0022(17) 0.0023(17) -0.0026(16) C4 0.017(2) 0.013(2) 0.015(2) 0.0006(17) 0.0058(17) -0.0020(16) N4 0.0113(15) 0.0180(17) 0.0153(17) -0.0015(14) 0.0014(13) 0.0017(13) C5 0.017(2) 0.022(2) 0.022(2) -0.0044(18) -0.0045(18) -0.0006(17) N5 0.0148(16) 0.0162(17) 0.0180(17) -0.0016(14) 0.0012(14) 0.0013(13) C6 0.0153(19) 0.015(2) 0.0100(19) 0.0033(16) 0.0043(16) -0.0031(16) C7 0.018(2) 0.0129(19) 0.021(2) -0.0005(16) 0.0066(18) -0.0015(15) C8 0.025(2) 0.014(2) 0.020(2) -0.0027(17) 0.0062(19) -0.0032(17) C9 0.018(2) 0.021(2) 0.016(2) 0.0039(18) -0.0023(17) -0.0081(17) C10 0.020(2) 0.020(2) 0.014(2) 0.0044(17) 0.0018(17) 0.0000(17) C11 0.0179(19) 0.017(2) 0.0109(19) 0.0013(16) 0.0073(16) -0.0027(16) C12 0.018(2) 0.017(2) 0.014(2) 0.0034(16) 0.0065(17) -0.0024(16) C13 0.0140(19) 0.019(2) 0.014(2) 0.0009(17) 0.0044(16) -0.0006(16) C14 0.0134(19) 0.021(2) 0.016(2) 0.0039(17) 0.0035(17) 0.0016(16) N6 0.0166(16) 0.0209(19) 0.0202(18) -0.0001(15) 0.0011(14) 0.0013(14) N7 0.0175(17) 0.0238(19) 0.0203(18) -0.0026(15) -0.0009(15) 0.0030(15) N8 0.0136(16) 0.0199(18) 0.0174(17) 0.0005(14) 0.0016(14) 0.0012(14) C15 0.0147(19) 0.026(2) 0.028(2) -0.0010(19) 0.0006(18) 0.0076(17) I 0.02176(15) 0.02266(15) 0.01962(15) 0.00001(12) 0.00237(11) -0.00280(11) C16 0.029(2) 0.028(2) 0.021(2) 0.0006(19) 0.0078(19) 0.0023(19) Cl1 0.0231(5) 0.0335(6) 0.0245(6) -0.0026(5) 0.0011(4) -0.0025(4) Cl2 0.0478(7) 0.0278(6) 0.0228(6) -0.0015(5) 0.0004(5) -0.0063(5) Cl3 0.0433(7) 0.0467(7) 0.0310(6) 0.0145(5) 0.0122(5) -0.0026(5) _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 C1 N1 1.467(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? N1 C2 1.334(5) . ? N1 N2 1.339(4) . ? N2 N3 1.315(4) . ? N3 C3 1.357(5) . ? C2 C3 1.365(5) . ? C2 H2 0.9500 . ? C3 C4 1.470(5) . ? C4 N4 1.317(5) . ? C4 C6 1.425(5) . ? N4 N5 1.352(4) . ? N4 C5 1.471(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? N5 C12 1.326(4) . ? C6 C11 1.415(5) . ? C6 C7 1.418(5) . ? C7 C8 1.372(5) . ? C7 H7 0.9500 . ? C8 C9 1.399(5) . ? C8 H8 0.9500 . ? C9 C10 1.372(5) . ? C9 H9 0.9500 . ? C10 C11 1.406(5) . ? C10 H10 0.9500 . ? C11 C12 1.438(5) . ? C12 C13 1.462(5) . ? C13 N6 1.364(4) . ? C13 C14 1.378(5) . ? C14 N8 1.332(4) . ? C14 H14 0.9500 . ? N6 N7 1.312(4) . ? N7 N8 1.354(4) . ? N8 C15 1.454(5) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 Cl3 1.756(4) . ? C16 Cl2 1.762(4) . ? C16 Cl1 1.778(4) . ? C16 H16 1.0000 . ? 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 N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 N1 N2 110.9(3) . . ? C2 N1 C1 128.8(3) . . ? N2 N1 C1 120.2(3) . . ? N3 N2 N1 107.3(3) . . ? N2 N3 C3 108.5(3) . . ? N1 C2 C3 105.1(3) . . ? N1 C2 H2 127.5 . . ? C3 C2 H2 127.5 . . ? N3 C3 C2 108.3(3) . . ? N3 C3 C4 121.5(3) . . ? C2 C3 C4 130.2(4) . . ? N4 C4 C6 119.2(3) . . ? N4 C4 C3 118.2(3) . . ? C6 C4 C3 122.5(3) . . ? C4 N4 N5 124.9(3) . . ? C4 N4 C5 123.2(3) . . ? N5 N4 C5 111.9(3) . . ? N4 C5 H5A 109.5 . . ? N4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C12 N5 N4 118.2(3) . . ? C11 C6 C7 120.8(3) . . ? C11 C6 C4 118.4(3) . . ? C7 C6 C4 120.8(3) . . ? C8 C7 C6 118.7(3) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C7 C8 C9 120.5(4) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 121.6(3) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C9 C10 C11 119.6(3) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C6 118.8(3) . . ? C10 C11 C12 124.9(3) . . ? C6 C11 C12 116.4(3) . . ? N5 C12 C11 122.8(3) . . ? N5 C12 C13 111.0(3) . . ? C11 C12 C13 126.2(3) . . ? N6 C13 C14 108.2(3) . . ? N6 C13 C12 126.1(3) . . ? C14 C13 C12 125.7(3) . . ? N8 C14 C13 104.9(3) . . ? N8 C14 H14 127.5 . . ? C13 C14 H14 127.5 . . ? N7 N6 C13 108.6(3) . . ? N6 N7 N8 107.3(3) . . ? C14 N8 N7 111.0(3) . . ? C14 N8 C15 128.7(3) . . ? N7 N8 C15 120.3(3) . . ? N8 C15 H15A 109.5 . . ? N8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? Cl3 C16 Cl2 110.4(2) . . ? Cl3 C16 Cl1 111.2(2) . . ? Cl2 C16 Cl1 109.8(2) . . ? Cl3 C16 H16 108.5 . . ? Cl2 C16 H16 108.5 . . ? Cl1 C16 H16 108.5 . . ? 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 C2 N1 N2 N3 0.8(4) . . . . ? C1 N1 N2 N3 178.5(3) . . . . ? N1 N2 N3 C3 -0.5(4) . . . . ? N2 N1 C2 C3 -0.7(4) . . . . ? C1 N1 C2 C3 -178.2(4) . . . . ? N2 N3 C3 C2 0.0(4) . . . . ? N2 N3 C3 C4 -177.8(3) . . . . ? N1 C2 C3 N3 0.4(4) . . . . ? N1 C2 C3 C4 178.0(4) . . . . ? N3 C3 C4 N4 101.8(4) . . . . ? C2 C3 C4 N4 -75.4(5) . . . . ? N3 C3 C4 C6 -74.8(5) . . . . ? C2 C3 C4 C6 107.9(5) . . . . ? C6 C4 N4 N5 -2.6(5) . . . . ? C3 C4 N4 N5 -179.4(3) . . . . ? C6 C4 N4 C5 178.1(3) . . . . ? C3 C4 N4 C5 1.3(5) . . . . ? C4 N4 N5 C12 0.8(5) . . . . ? C5 N4 N5 C12 -179.8(3) . . . . ? N4 C4 C6 C11 1.5(5) . . . . ? C3 C4 C6 C11 178.2(3) . . . . ? N4 C4 C6 C7 -176.9(3) . . . . ? C3 C4 C6 C7 -0.3(5) . . . . ? C11 C6 C7 C8 -0.8(5) . . . . ? C4 C6 C7 C8 177.6(3) . . . . ? C6 C7 C8 C9 1.4(6) . . . . ? C7 C8 C9 C10 -1.0(6) . . . . ? C8 C9 C10 C11 -0.1(6) . . . . ? C9 C10 C11 C6 0.6(5) . . . . ? C9 C10 C11 C12 -178.9(4) . . . . ? C7 C6 C11 C10 -0.2(5) . . . . ? C4 C6 C11 C10 -178.6(3) . . . . ? C7 C6 C11 C12 179.4(3) . . . . ? C4 C6 C11 C12 1.0(5) . . . . ? N4 N5 C12 C11 1.9(5) . . . . ? N4 N5 C12 C13 -178.8(3) . . . . ? C10 C11 C12 N5 176.8(3) . . . . ? C6 C11 C12 N5 -2.8(5) . . . . ? C10 C11 C12 C13 -2.3(6) . . . . ? C6 C11 C12 C13 178.1(3) . . . . ? N5 C12 C13 N6 -170.0(3) . . . . ? C11 C12 C13 N6 9.2(6) . . . . ? N5 C12 C13 C14 8.9(5) . . . . ? C11 C12 C13 C14 -171.9(4) . . . . ? N6 C13 C14 N8 -0.1(4) . . . . ? C12 C13 C14 N8 -179.2(3) . . . . ? C14 C13 N6 N7 -0.1(4) . . . . ? C12 C13 N6 N7 179.0(4) . . . . ? C13 N6 N7 N8 0.3(4) . . . . ? C13 C14 N8 N7 0.3(4) . . . . ? C13 C14 N8 C15 -177.7(4) . . . . ? N6 N7 N8 C14 -0.4(4) . . . . ? N6 N7 N8 C15 177.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.14 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.789 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 948960' ####################################################################### # # 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_alb114sqz(5) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H34 Cl N14 Ru2, 3 (F6 P), 2 (C3 H6 O)' _chemical_formula_sum 'C50 H46 Cl F18 N14 O2 P3 Ru2' _chemical_formula_weight 1547.51 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/m' _symmetry_space_group_name_Hall '-P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 11.8427(5) _cell_length_b 21.0984(7) _cell_length_c 12.933(1) _cell_angle_alpha 90.00 _cell_angle_beta 103.303(6) _cell_angle_gamma 90.00 _cell_volume 3144.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4181 _cell_measurement_theta_min 3.3716 _cell_measurement_theta_max 24.1020 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.2620 _exptl_crystal_size_mid 0.1305 _exptl_crystal_size_min 0.0335 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 0.703 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.915 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) 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 ; The PLATON "squeeze" procedure was used to treat regions of diffuse solvent(s) which could not be modelled in terms of atomic sites. The number of electrons thus located, 69 per unit cell, is included in the formula, formula weight, calculated density, \m and F(000). This residual electron density was assigned to two molecules of acetone per unit cell. Two acetones would give 68 e^-^. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14563 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0635 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 24.15 _reflns_number_total 5106 _reflns_number_gt 3837 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0701P)^2^+1.1102P] 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 5106 _refine_ls_number_parameters 423 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1204 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 Ru Ru 0.40116(3) 0.163339(16) 0.14911(3) 0.02075(16) Uani 1 1 d . . . Cl Cl 0.49322(13) 0.2500 0.08236(15) 0.0263(4) Uani 1 2 d S . . N1 N 0.3165(3) 0.09697(17) 0.2108(3) 0.0223(9) Uani 1 1 d . . . N2 N 0.3241(3) 0.03440(17) 0.2120(3) 0.0268(10) Uani 1 1 d . . . N3 N 0.2417(4) 0.01506(18) 0.2619(4) 0.0301(10) Uani 1 1 d . . . C1 C 0.2236(5) -0.0529(2) 0.2744(5) 0.0352(14) Uani 1 1 d . . . H1A H 0.2811 -0.0688 0.3359 0.053 Uiso 1 1 calc R . . H1B H 0.2321 -0.0753 0.2102 0.053 Uiso 1 1 calc R . . H1C H 0.1454 -0.0600 0.2854 0.053 Uiso 1 1 calc R . . C2 C 0.1845(5) 0.0634(2) 0.2922(5) 0.0351(14) Uani 1 1 d . . . H2 H 0.1223 0.0611 0.3272 0.042 Uiso 1 1 calc R . . C3 C 0.2338(4) 0.1172(2) 0.2624(4) 0.0256(12) Uani 1 1 d . . . C4 C 0.2236(4) 0.1856(2) 0.2725(4) 0.0280(12) Uani 1 1 d . . . N4 N 0.2924(3) 0.21736(17) 0.2207(3) 0.0237(9) Uani 1 1 d . . . C5 C 0.1557(5) 0.2168(2) 0.3360(5) 0.0416(15) Uani 1 1 d . . . C6 C 0.0961(6) 0.1843(3) 0.4014(6) 0.061(2) Uani 1 1 d . . . H6 H 0.0959 0.1393 0.4023 0.073 Uiso 1 1 calc R . . C7 C 0.0383(7) 0.2174(3) 0.4641(7) 0.080(3) Uani 1 1 d . . . H7 H -0.0023 0.1951 0.5082 0.096 Uiso 1 1 calc R . . N5 N 0.2974(3) 0.14879(17) -0.0011(3) 0.0243(10) Uani 1 1 d . . . C8 C 0.1857(4) 0.1667(2) -0.0403(5) 0.0289(13) Uani 1 1 d . . . H8 H 0.1480 0.1911 0.0036 0.035 Uiso 1 1 calc R . . C9 C 0.1250(5) 0.1511(2) -0.1402(5) 0.0370(14) Uani 1 1 d . . . H9 H 0.0468 0.1647 -0.1643 0.044 Uiso 1 1 calc R . . C10 C 0.1766(5) 0.1159(3) -0.2058(5) 0.0419(15) Uani 1 1 d . . . H10 H 0.1354 0.1050 -0.2755 0.050 Uiso 1 1 calc R . . C11 C 0.2914(5) 0.0967(2) -0.1670(5) 0.0379(14) Uani 1 1 d . . . H11 H 0.3291 0.0719 -0.2104 0.045 Uiso 1 1 calc R . . C12 C 0.3502(4) 0.1137(2) -0.0660(5) 0.0294(13) Uani 1 1 d . . . C13 C 0.4707(4) 0.0944(2) -0.0170(4) 0.0269(12) Uani 1 1 d . . . N6 N 0.5038(3) 0.10976(17) 0.0864(4) 0.0230(10) Uani 1 1 d . . . C14 C 0.5460(4) 0.0619(2) -0.0664(5) 0.0331(13) Uani 1 1 d . . . H14 H 0.5228 0.0499 -0.1390 0.040 Uiso 1 1 calc R . . C15 C 0.6560(5) 0.0475(2) -0.0063(5) 0.0382(15) Uani 1 1 d . . . H15 H 0.7090 0.0257 -0.0388 0.046 Uiso 1 1 calc R . . C16 C 0.6897(4) 0.0640(2) 0.0984(5) 0.0360(15) Uani 1 1 d . . . H16 H 0.7651 0.0536 0.1387 0.043 Uiso 1 1 calc R . . C17 C 0.6109(4) 0.0966(2) 0.1454(5) 0.0290(13) Uani 1 1 d . . . C18 C 0.6304(4) 0.1195(2) 0.2545(5) 0.0309(13) Uani 1 1 d . . . N7 N 0.5406(3) 0.15324(18) 0.2778(4) 0.0262(10) Uani 1 1 d . . . C19 C 0.7300(5) 0.1082(3) 0.3325(6) 0.0454(16) Uani 1 1 d . . . H19 H 0.7923 0.0853 0.3154 0.054 Uiso 1 1 calc R . . C20 C 0.7397(5) 0.1298(3) 0.4347(6) 0.0500(17) Uani 1 1 d . . . H20 H 0.8088 0.1228 0.4877 0.060 Uiso 1 1 calc R . . C21 C 0.6465(6) 0.1621(3) 0.4589(5) 0.0455(16) Uani 1 1 d . . . H21 H 0.6497 0.1766 0.5290 0.055 Uiso 1 1 calc R . . C22 C 0.5488(5) 0.1726(2) 0.3780(5) 0.0381(14) Uani 1 1 d . . . H22 H 0.4849 0.1945 0.3944 0.046 Uiso 1 1 calc R . . P1 P 0.0000 0.0000 0.5000 0.0301(5) Uani 1 2 d S . . F1 F 0.1344(3) 0.00936(17) 0.5039(3) 0.0544(10) Uani 1 1 d . . . F2 F -0.0337(3) 0.02717(19) 0.3820(3) 0.0580(11) Uani 1 1 d . . . F3 F -0.0056(3) 0.06929(17) 0.5450(4) 0.0714(12) Uani 1 1 d . . . P2 P 0.0000 0.0000 0.0000 0.0349(5) Uani 1 2 d S . . F4 F 0.1169(2) 0.04017(15) 0.0386(3) 0.0453(9) Uani 1 1 d . . . F5 F -0.0700(3) 0.06337(15) -0.0404(3) 0.0523(10) Uani 1 1 d . . . F6 F -0.0285(3) 0.00907(16) 0.1149(3) 0.0479(9) Uani 1 1 d . . . P3 P 0.7730(3) 0.2500 0.7614(3) 0.0421(10) Uani 0.710(6) 2 d SP . 1 F7 F 0.8889(9) 0.2500 0.8532(10) 0.063(3) Uani 0.710(6) 2 d SP . 1 F8 F 0.6579(6) 0.2500 0.6687(6) 0.054(2) Uani 0.710(6) 2 d SP . 1 F9 F 0.8273(6) 0.1944(2) 0.6992(5) 0.0500(16) Uani 0.710(6) 1 d P . 1 F10 F 0.7198(5) 0.1968(2) 0.8233(5) 0.0621(17) Uani 0.710(6) 1 d P . 1 P4 P 0.8598(7) 0.2500 0.6882(8) 0.050(3) Uani 0.290(6) 2 d SP . 2 F11 F 0.8204(14) 0.2500 0.5607(14) 0.052(5) Uiso 0.290(6) 2 d SP . 2 F12 F 0.769(2) 0.2027(14) 0.696(3) 0.139(12) Uiso 0.290(6) 1 d P . 2 F13 F 0.905(3) 0.2500 0.812(2) 0.066(10) Uiso 0.290(6) 2 d SP . 2 F14 F 0.933(3) 0.1953(18) 0.670(3) 0.222(14) Uiso 0.290(6) 1 d P . 2 O1 O 1.0351(5) 0.2500 0.0985(5) 0.0501(16) Uani 1 2 d S . . C23 C 0.9339(7) 0.2500 0.0981(8) 0.045(2) Uani 1 2 d S . . C24 C 0.8684(7) 0.1904(4) 0.0974(8) 0.088(3) Uani 1 1 d . . . H24A H 0.8054 0.1886 0.0333 0.132 Uiso 1 1 calc R . . H24B H 0.8356 0.1887 0.1604 0.132 Uiso 1 1 calc R . . H24C H 0.9205 0.1542 0.0981 0.132 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 Ru 0.0218(2) 0.0112(2) 0.0351(3) -0.00030(17) 0.01844(18) 0.00059(15) Cl 0.0261(8) 0.0144(8) 0.0447(12) 0.000 0.0214(8) 0.000 N1 0.023(2) 0.015(2) 0.033(3) -0.0016(18) 0.0149(19) -0.0006(16) N2 0.032(2) 0.014(2) 0.039(3) 0.0030(19) 0.016(2) -0.0039(17) N3 0.042(2) 0.013(2) 0.043(3) 0.0001(19) 0.027(2) -0.0045(18) C1 0.050(3) 0.012(2) 0.051(4) 0.008(2) 0.028(3) 0.002(2) C2 0.049(3) 0.016(3) 0.052(4) -0.001(3) 0.035(3) -0.002(2) C3 0.032(3) 0.014(2) 0.036(3) 0.002(2) 0.020(2) 0.000(2) C4 0.034(3) 0.011(2) 0.045(4) -0.002(2) 0.022(3) -0.001(2) N4 0.028(2) 0.0101(17) 0.038(3) 0.0035(19) 0.017(2) 0.0043(17) C5 0.050(3) 0.017(2) 0.075(5) 0.000(3) 0.050(3) -0.001(2) C6 0.087(5) 0.018(3) 0.104(6) 0.000(3) 0.080(5) -0.003(3) C7 0.115(6) 0.031(3) 0.135(7) -0.001(4) 0.113(6) 0.001(4) N5 0.024(2) 0.016(2) 0.039(3) 0.0031(19) 0.020(2) -0.0043(16) C8 0.022(2) 0.019(3) 0.049(4) 0.003(2) 0.014(3) 0.001(2) C9 0.034(3) 0.027(3) 0.050(4) 0.006(3) 0.010(3) -0.002(2) C10 0.049(3) 0.032(3) 0.043(4) 0.000(3) 0.008(3) -0.008(3) C11 0.048(3) 0.026(3) 0.048(4) -0.005(3) 0.028(3) -0.003(3) C12 0.037(3) 0.016(2) 0.041(4) 0.001(2) 0.022(3) -0.003(2) C13 0.033(3) 0.022(3) 0.034(4) -0.002(2) 0.025(3) -0.001(2) N6 0.023(2) 0.0125(19) 0.039(3) 0.0038(19) 0.018(2) 0.0045(16) C14 0.038(3) 0.026(3) 0.041(4) -0.008(3) 0.020(3) -0.001(2) C15 0.038(3) 0.021(3) 0.066(5) -0.010(3) 0.033(3) -0.004(2) C16 0.024(3) 0.019(3) 0.069(5) -0.008(3) 0.020(3) 0.001(2) C17 0.030(3) 0.014(2) 0.052(4) 0.002(2) 0.026(3) -0.002(2) C18 0.024(3) 0.021(3) 0.052(4) 0.002(3) 0.017(3) 0.001(2) N7 0.032(2) 0.017(2) 0.030(3) -0.0002(19) 0.008(2) -0.0004(17) C19 0.040(3) 0.035(3) 0.062(5) 0.007(3) 0.013(3) 0.011(3) C20 0.054(4) 0.038(3) 0.053(5) 0.009(3) 0.001(3) 0.010(3) C21 0.068(4) 0.030(3) 0.033(4) 0.000(3) 0.002(3) -0.003(3) C22 0.052(3) 0.018(3) 0.049(4) 0.005(3) 0.023(3) -0.002(2) P1 0.0274(9) 0.0244(10) 0.0456(14) 0.0083(9) 0.0226(9) 0.0027(8) F1 0.0320(16) 0.064(2) 0.072(3) 0.030(2) 0.0218(17) 0.0004(16) F2 0.0366(17) 0.086(3) 0.059(2) 0.039(2) 0.0281(17) 0.0158(18) F3 0.062(2) 0.040(2) 0.102(3) -0.020(2) -0.001(2) 0.0205(18) P2 0.0246(9) 0.0274(10) 0.0559(15) 0.0035(10) 0.0162(10) -0.0008(8) F4 0.0321(16) 0.0402(18) 0.066(3) 0.0050(17) 0.0158(16) -0.0111(14) F5 0.0402(17) 0.0331(18) 0.086(3) 0.0125(18) 0.0196(18) 0.0072(14) F6 0.0401(17) 0.055(2) 0.056(2) -0.0007(18) 0.0263(17) -0.0055(16) P3 0.056(2) 0.0171(15) 0.047(2) 0.000 0.0000(16) 0.000 F7 0.061(6) 0.056(6) 0.063(8) 0.000 -0.002(6) 0.000 F8 0.056(4) 0.045(4) 0.053(5) 0.000 -0.003(4) 0.000 F9 0.054(3) 0.021(3) 0.072(4) -0.005(2) 0.008(3) 0.003(3) F10 0.076(4) 0.039(3) 0.069(4) 0.009(3) 0.012(3) -0.002(3) P4 0.037(4) 0.055(7) 0.060(6) 0.000 0.018(4) 0.000 O1 0.039(3) 0.047(4) 0.073(5) 0.000 0.030(3) 0.000 C23 0.049(5) 0.027(4) 0.070(7) 0.000 0.036(5) 0.000 C24 0.080(5) 0.057(5) 0.139(9) -0.009(5) 0.052(6) -0.029(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 Ru N6 1.966(4) . ? Ru N1 1.993(4) . ? Ru N7 2.068(4) . ? Ru N5 2.068(4) . ? Ru N4 2.089(4) . ? Ru Cl 2.3896(10) . ? Cl Ru 2.3896(10) 4_565 ? N1 N2 1.323(5) . ? N1 C3 1.374(6) . ? N2 N3 1.350(5) . ? N3 C2 1.333(6) . ? N3 C1 1.464(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.371(7) . ? C2 H2 0.9500 . ? C3 C4 1.457(6) . ? C4 N4 1.346(6) . ? C4 C5 1.434(7) . ? N4 N4 1.377(7) 4_565 ? C5 C6 1.399(8) . ? C5 C5 1.401(10) 4_565 ? C6 C7 1.368(8) . ? C6 H6 0.9500 . ? C7 C7 1.375(12) 4_565 ? C7 H7 0.9500 . ? N5 C8 1.358(6) . ? N5 C12 1.373(6) . ? C8 C9 1.366(8) . ? C8 H8 0.9500 . ? C9 C10 1.372(8) . ? C9 H9 0.9500 . ? C10 C11 1.397(8) . ? C10 H10 0.9500 . ? C11 C12 1.379(8) . ? C11 H11 0.9500 . ? C12 C13 1.480(7) . ? C13 N6 1.344(7) . ? C13 C14 1.390(7) . ? N6 C17 1.350(6) . ? C14 C15 1.389(8) . ? C14 H14 0.9500 . ? C15 C16 1.366(8) . ? C15 H15 0.9500 . ? C16 C17 1.405(7) . ? C16 H16 0.9500 . ? C17 C18 1.460(8) . ? C18 N7 1.370(6) . ? C18 C19 1.385(8) . ? N7 C22 1.342(7) . ? C19 C20 1.377(9) . ? C19 H19 0.9500 . ? C20 C21 1.393(9) . ? C20 H20 0.9500 . ? C21 C22 1.387(9) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? P1 F3 1.580(3) 3_556 ? P1 F3 1.580(3) . ? P1 F2 1.593(3) . ? P1 F2 1.593(3) 3_556 ? P1 F1 1.594(3) 3_556 ? P1 F1 1.594(3) . ? P2 F5 1.596(3) 3 ? P2 F5 1.597(3) . ? P2 F4 1.602(3) 3 ? P2 F4 1.602(3) . ? P2 F6 1.609(3) 3 ? P2 F6 1.609(3) . ? P3 F10 1.590(6) . ? P3 F10 1.590(6) 4_565 ? P3 F7 1.594(11) . ? P3 F8 1.595(8) . ? P3 F9 1.636(6) 4_565 ? P3 F9 1.636(6) . ? P4 F12 1.48(3) . ? P4 F12 1.48(3) 4_565 ? P4 F14 1.50(4) . ? P4 F14 1.50(4) 4_565 ? P4 F13 1.57(3) . ? P4 F11 1.61(2) . ? O1 C23 1.197(9) . ? C23 C24 1.477(8) . ? C23 C24 1.477(8) 4_565 ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 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 N6 Ru N1 100.19(15) . . ? N6 Ru N7 79.51(17) . . ? N1 Ru N7 89.30(16) . . ? N6 Ru N5 79.47(16) . . ? N1 Ru N5 91.53(15) . . ? N7 Ru N5 158.77(16) . . ? N6 Ru N4 177.57(15) . . ? N1 Ru N4 77.73(14) . . ? N7 Ru N4 99.15(16) . . ? N5 Ru N4 101.75(15) . . ? N6 Ru Cl 85.08(11) . . ? N1 Ru Cl 174.72(11) . . ? N7 Ru Cl 91.34(12) . . ? N5 Ru Cl 89.78(11) . . ? N4 Ru Cl 97.00(10) . . ? Ru Cl Ru 99.84(6) . 4_565 ? N2 N1 C3 111.0(4) . . ? N2 N1 Ru 131.8(3) . . ? C3 N1 Ru 117.2(3) . . ? N1 N2 N3 104.6(3) . . ? C2 N3 N2 112.4(4) . . ? C2 N3 C1 128.3(4) . . ? N2 N3 C1 119.3(4) . . ? N3 C1 H1A 109.5 . . ? N3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 C3 105.8(4) . . ? N3 C2 H2 127.1 . . ? C3 C2 H2 127.1 . . ? C2 C3 N1 106.1(4) . . ? C2 C3 C4 138.2(4) . . ? N1 C3 C4 115.7(4) . . ? N4 C4 C5 122.7(4) . . ? N4 C4 C3 112.1(4) . . ? C5 C4 C3 125.1(4) . . ? C4 N4 N4 119.8(2) . 4_565 ? C4 N4 Ru 117.0(3) . . ? N4 N4 Ru 123.06(10) 4_565 . ? C6 C5 C5 119.3(3) . 4_565 ? C6 C5 C4 123.3(5) . . ? C5 C5 C4 117.3(3) 4_565 . ? C7 C6 C5 120.0(5) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C7 120.7(3) . 4_565 ? C6 C7 H7 119.6 . . ? C7 C7 H7 119.6 4_565 . ? C8 N5 C12 117.6(5) . . ? C8 N5 Ru 128.8(4) . . ? C12 N5 Ru 113.5(3) . . ? N5 C8 C9 122.8(5) . . ? N5 C8 H8 118.6 . . ? C9 C8 H8 118.6 . . ? C8 C9 C10 120.2(5) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C11 118.1(6) . . ? C9 C10 H10 121.0 . . ? C11 C10 H10 121.0 . . ? C12 C11 C10 120.1(5) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? N5 C12 C11 121.2(5) . . ? N5 C12 C13 114.6(5) . . ? C11 C12 C13 124.1(5) . . ? N6 C13 C14 120.3(5) . . ? N6 C13 C12 113.0(4) . . ? C14 C13 C12 126.6(5) . . ? C13 N6 C17 122.2(4) . . ? C13 N6 Ru 118.9(3) . . ? C17 N6 Ru 118.3(4) . . ? C15 C14 C13 118.0(5) . . ? C15 C14 H14 121.0 . . ? C13 C14 H14 121.0 . . ? C16 C15 C14 121.4(5) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 118.8(5) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? N6 C17 C16 119.2(5) . . ? N6 C17 C18 113.4(4) . . ? C16 C17 C18 127.4(5) . . ? N7 C18 C19 120.3(5) . . ? N7 C18 C17 115.2(5) . . ? C19 C18 C17 124.5(5) . . ? C22 N7 C18 118.9(5) . . ? C22 N7 Ru 127.8(4) . . ? C18 N7 Ru 113.2(4) . . ? C20 C19 C18 120.7(5) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 118.8(6) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C22 C21 C20 118.4(6) . . ? C22 C21 H21 120.8 . . ? C20 C21 H21 120.8 . . ? N7 C22 C21 122.8(5) . . ? N7 C22 H22 118.6 . . ? C21 C22 H22 118.6 . . ? F3 P1 F3 179.998(1) 3_556 . ? F3 P1 F2 90.2(2) 3_556 . ? F3 P1 F2 89.8(2) . . ? F3 P1 F2 89.8(2) 3_556 3_556 ? F3 P1 F2 90.2(2) . 3_556 ? F2 P1 F2 180.0(3) . 3_556 ? F3 P1 F1 89.98(19) 3_556 3_556 ? F3 P1 F1 90.02(19) . 3_556 ? F2 P1 F1 89.22(17) . 3_556 ? F2 P1 F1 90.78(17) 3_556 3_556 ? F3 P1 F1 90.02(19) 3_556 . ? F3 P1 F1 89.98(19) . . ? F2 P1 F1 90.78(17) . . ? F2 P1 F1 89.22(17) 3_556 . ? F1 P1 F1 180.0 3_556 . ? F5 P2 F5 179.996(2) 3 . ? F5 P2 F4 90.33(16) 3 3 ? F5 P2 F4 89.68(16) . 3 ? F5 P2 F4 89.68(16) 3 . ? F5 P2 F4 90.32(16) . . ? F4 P2 F4 180.0 3 . ? F5 P2 F6 89.96(18) 3 3 ? F5 P2 F6 90.04(18) . 3 ? F4 P2 F6 89.96(16) 3 3 ? F4 P2 F6 90.04(16) . 3 ? F5 P2 F6 90.04(18) 3 . ? F5 P2 F6 89.96(18) . . ? F4 P2 F6 90.04(16) 3 . ? F4 P2 F6 89.96(16) . . ? F6 P2 F6 180.0 3 . ? F10 P3 F10 89.7(4) . 4_565 ? F10 P3 F7 89.9(4) . . ? F10 P3 F7 89.9(4) 4_565 . ? F10 P3 F8 90.5(3) . . ? F10 P3 F8 90.5(3) 4_565 . ? F7 P3 F8 179.4(6) . . ? F10 P3 F9 179.0(3) . 4_565 ? F10 P3 F9 89.3(3) 4_565 4_565 ? F7 P3 F9 89.9(4) . 4_565 ? F8 P3 F9 89.7(3) . 4_565 ? F10 P3 F9 89.3(3) . . ? F10 P3 F9 179.0(3) 4_565 . ? F7 P3 F9 89.9(4) . . ? F8 P3 F9 89.7(3) . . ? F9 P3 F9 91.6(4) 4_565 . ? F12 P4 F12 85(2) . 4_565 ? F12 P4 F14 86.9(16) . . ? F12 P4 F14 170(2) 4_565 . ? F12 P4 F14 170(2) . 4_565 ? F12 P4 F14 86.9(16) 4_565 4_565 ? F14 P4 F14 101(3) . 4_565 ? F12 P4 F13 90.7(15) . . ? F12 P4 F13 90.7(15) 4_565 . ? F14 P4 F13 94.9(16) . . ? F14 P4 F13 94.9(16) 4_565 . ? F12 P4 F11 91.4(14) . . ? F12 P4 F11 91.4(14) 4_565 . ? F14 P4 F11 83.3(15) . . ? F14 P4 F11 83.3(15) 4_565 . ? F13 P4 F11 177.2(13) . . ? O1 C23 C24 121.6(4) . . ? O1 C23 C24 121.6(4) . 4_565 ? C24 C23 C24 116.8(8) . 4_565 ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 N6 Ru Cl Ru -176.95(14) . . . 4_565 ? N7 Ru Cl Ru -97.60(12) . . . 4_565 ? N5 Ru Cl Ru 103.60(12) . . . 4_565 ? N4 Ru Cl Ru 1.79(13) . . . 4_565 ? N6 Ru N1 N2 0.3(5) . . . . ? N7 Ru N1 N2 -78.9(4) . . . . ? N5 Ru N1 N2 79.9(4) . . . . ? N4 Ru N1 N2 -178.4(5) . . . . ? N6 Ru N1 C3 -179.6(4) . . . . ? N7 Ru N1 C3 101.2(4) . . . . ? N5 Ru N1 C3 -100.0(4) . . . . ? N4 Ru N1 C3 1.7(4) . . . . ? C3 N1 N2 N3 2.2(5) . . . . ? Ru N1 N2 N3 -177.7(3) . . . . ? N1 N2 N3 C2 -0.6(6) . . . . ? N1 N2 N3 C1 178.2(5) . . . . ? N2 N3 C2 C3 -1.3(7) . . . . ? C1 N3 C2 C3 -179.9(5) . . . . ? N3 C2 C3 N1 2.6(6) . . . . ? N3 C2 C3 C4 -176.0(6) . . . . ? N2 N1 C3 C2 -3.1(6) . . . . ? Ru N1 C3 C2 176.9(4) . . . . ? N2 N1 C3 C4 175.9(4) . . . . ? Ru N1 C3 C4 -4.2(6) . . . . ? C2 C3 C4 N4 -176.5(7) . . . . ? N1 C3 C4 N4 5.0(7) . . . . ? C2 C3 C4 C5 7.9(11) . . . . ? N1 C3 C4 C5 -170.6(5) . . . . ? C5 C4 N4 N4 -5.1(7) . . . 4_565 ? C3 C4 N4 N4 179.1(3) . . . 4_565 ? C5 C4 N4 Ru 172.1(4) . . . . ? C3 C4 N4 Ru -3.7(6) . . . . ? N1 Ru N4 C4 1.3(4) . . . . ? N7 Ru N4 C4 -86.0(4) . . . . ? N5 Ru N4 C4 90.3(4) . . . . ? Cl Ru N4 C4 -178.5(4) . . . . ? N1 Ru N4 N4 178.39(16) . . . 4_565 ? N7 Ru N4 N4 91.12(13) . . . 4_565 ? N5 Ru N4 N4 -92.61(13) . . . 4_565 ? Cl Ru N4 N4 -1.37(10) . . . 4_565 ? N4 C4 C5 C6 -171.2(6) . . . . ? C3 C4 C5 C6 4.0(10) . . . . ? N4 C4 C5 C5 5.0(6) . . . 4_565 ? C3 C4 C5 C5 -179.8(4) . . . 4_565 ? C5 C5 C6 C7 0.3(9) 4_565 . . . ? C4 C5 C6 C7 176.4(7) . . . . ? C5 C6 C7 C7 -0.3(10) . . . 4_565 ? N6 Ru N5 C8 174.5(4) . . . . ? N1 Ru N5 C8 74.4(4) . . . . ? N7 Ru N5 C8 166.4(4) . . . . ? N4 Ru N5 C8 -3.3(4) . . . . ? Cl Ru N5 C8 -100.4(4) . . . . ? N6 Ru N5 C12 -2.3(3) . . . . ? N1 Ru N5 C12 -102.4(3) . . . . ? N7 Ru N5 C12 -10.4(6) . . . . ? N4 Ru N5 C12 179.8(3) . . . . ? Cl Ru N5 C12 82.7(3) . . . . ? C12 N5 C8 C9 0.2(7) . . . . ? Ru N5 C8 C9 -176.5(4) . . . . ? N5 C8 C9 C10 0.0(8) . . . . ? C8 C9 C10 C11 0.3(8) . . . . ? C9 C10 C11 C12 -0.7(8) . . . . ? C8 N5 C12 C11 -0.6(7) . . . . ? Ru N5 C12 C11 176.6(4) . . . . ? C8 N5 C12 C13 -178.4(4) . . . . ? Ru N5 C12 C13 -1.2(5) . . . . ? C10 C11 C12 N5 0.8(8) . . . . ? C10 C11 C12 C13 178.5(5) . . . . ? N5 C12 C13 N6 5.9(6) . . . . ? C11 C12 C13 N6 -171.9(4) . . . . ? N5 C12 C13 C14 -176.1(4) . . . . ? C11 C12 C13 C14 6.1(8) . . . . ? C14 C13 N6 C17 2.3(7) . . . . ? C12 C13 N6 C17 -179.6(4) . . . . ? C14 C13 N6 Ru 173.7(4) . . . . ? C12 C13 N6 Ru -8.2(5) . . . . ? N1 Ru N6 C13 95.7(3) . . . . ? N7 Ru N6 C13 -176.9(4) . . . . ? N5 Ru N6 C13 6.0(3) . . . . ? Cl Ru N6 C13 -84.7(3) . . . . ? N1 Ru N6 C17 -92.6(3) . . . . ? N7 Ru N6 C17 -5.3(3) . . . . ? N5 Ru N6 C17 177.7(3) . . . . ? Cl Ru N6 C17 87.0(3) . . . . ? N6 C13 C14 C15 -1.5(7) . . . . ? C12 C13 C14 C15 -179.4(5) . . . . ? C13 C14 C15 C16 0.6(8) . . . . ? C14 C15 C16 C17 -0.4(8) . . . . ? C13 N6 C17 C16 -2.1(7) . . . . ? Ru N6 C17 C16 -173.4(3) . . . . ? C13 N6 C17 C18 177.7(4) . . . . ? Ru N6 C17 C18 6.3(5) . . . . ? C15 C16 C17 N6 1.1(7) . . . . ? C15 C16 C17 C18 -178.6(5) . . . . ? N6 C17 C18 N7 -3.4(6) . . . . ? C16 C17 C18 N7 176.3(5) . . . . ? N6 C17 C18 C19 175.3(5) . . . . ? C16 C17 C18 C19 -5.0(8) . . . . ? C19 C18 N7 C22 -2.8(7) . . . . ? C17 C18 N7 C22 175.9(4) . . . . ? C19 C18 N7 Ru -179.5(4) . . . . ? C17 C18 N7 Ru -0.8(5) . . . . ? N6 Ru N7 C22 -173.3(4) . . . . ? N1 Ru N7 C22 -72.8(4) . . . . ? N5 Ru N7 C22 -165.2(4) . . . . ? N4 Ru N7 C22 4.7(4) . . . . ? Cl Ru N7 C22 102.0(4) . . . . ? N6 Ru N7 C18 3.1(3) . . . . ? N1 Ru N7 C18 103.6(3) . . . . ? N5 Ru N7 C18 11.2(6) . . . . ? N4 Ru N7 C18 -179.0(3) . . . . ? Cl Ru N7 C18 -81.7(3) . . . . ? N7 C18 C19 C20 0.9(8) . . . . ? C17 C18 C19 C20 -177.8(5) . . . . ? C18 C19 C20 C21 1.4(9) . . . . ? C19 C20 C21 C22 -1.7(9) . . . . ? C18 N7 C22 C21 2.5(7) . . . . ? Ru N7 C22 C21 178.7(4) . . . . ? C20 C21 C22 N7 -0.3(8) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 24.15 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.028 _refine_diff_density_min -0.523 _refine_diff_density_rms 0.103 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.240 0.500 528 69 '2 (C3 H6 O)' _platon_squeeze_details ; PLATON: A.L. Spek, J. Appl. Cryst. 36 (2003), 7-13 PLATON version from 20.02.2011 ; _database_code_depnum_ccdc_archive 'CCDC 948961'