# Electronic Supplementary Material (ESI) for Chemical Communications # 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 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C84 H54 Cu6 O33' _chemical_formula_weight 1972.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system tetragonal _space_group_IT_number 123 _space_group_name_H-M_alt 'P 4/m m m' _space_group_name_Hall '-P 4 2' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-y, x, z' '-x, -y, z' 'y, -x, z' 'x, -y, -z' '-x, y, -z' 'y, x, -z' '-y, -x, -z' '-x, -y, -z' 'y, -x, -z' 'x, y, -z' '-y, x, -z' '-x, y, z' 'x, -y, z' '-y, -x, z' 'y, x, z' _cell_length_a 30.2922(13) _cell_length_b 30.2922(13) _cell_length_c 29.597(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 27159(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6544 _cell_measurement_theta_min 3.6000 _cell_measurement_theta_max 39.7660 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 0.482 _exptl_crystal_F_000 3984 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_absorpt_coefficient_mu 0.743 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.53762 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_source ? _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean 10.5594 _diffrn_reflns_number 103205 _diffrn_reflns_av_unetI/netI 0.1116 _diffrn_reflns_av_R_equivalents 0.1763 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 4.128 _diffrn_reflns_theta_max 59.958 _diffrn_reflns_theta_full 67.684 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.818 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_Laue_measured_fraction_full 0.818 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_point_group_measured_fraction_full 0.818 _reflns_number_total 10997 _reflns_number_gt 3835 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; 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 -0.010 -0.005 -0.005 20799 6171 ' ' _platon_squeeze_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment geom _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 10997 _refine_ls_number_parameters 265 _refine_ls_number_restraints 59 _refine_ls_R_factor_all 0.2416 _refine_ls_R_factor_gt 0.1514 _refine_ls_wR_factor_ref 0.4281 _refine_ls_wR_factor_gt 0.3906 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.063 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.13000(4) 0.13000(4) 0.19565(6) 0.1129(8) Uani 1 2 d S T P . . Cu2 Cu 0.17510(4) 0.17510(4) 0.25716(6) 0.1155(8) Uani 1 2 d S T P . . Cu3 Cu 0.26058(8) 0.0000 0.0000 0.1136(9) Uani 1 4 d S T P . . Cu4 Cu 0.34824(8) 0.0000 0.0000 0.1122(9) Uani 1 4 d S T P . . O1 O 0.1876(2) 0.1241(2) 0.1654(2) 0.135(2) Uani 1 1 d . . . . . O2 O 0.2259(2) 0.1638(3) 0.2193(2) 0.150(3) Uani 1 1 d . . . . . O3 O 0.26617(17) 0.0448(2) 0.04503(19) 0.123(2) Uani 1 1 d . . . . . O4 O 0.34249(19) 0.0464(2) 0.04678(18) 0.122(2) Uani 1 1 d . . . . . O6 O 0.1433(2) 0.07966(19) 0.2342(2) 0.134(2) Uani 1 1 d . . . . . O7 O 0.1831(2) 0.1188(2) 0.2851(2) 0.137(2) Uani 1 1 d . . . . . O8 O 0.3377(4) 0.0000 0.5000 0.175(6) Uani 1 4 d S T P . . O9 O 0.2144(3) 0.2144(3) 0.3038(4) 0.190(4) Uiso 1 2 d S . P . . O10 O 0.0919(3) 0.0919(3) 0.1453(4) 0.193(4) Uiso 1 2 d S . P . . O11 O 0.4204(5) 0.0000 0.0000 0.179(5) Uiso 1 4 d S . P . . O12 O 0.1901(5) 0.0000 0.0000 0.169(5) Uiso 1 4 d S . P . . C1 C 0.2205(2) 0.1393(3) 0.1874(4) 0.106(3) Uani 1 1 d . . . . . C2 C 0.3026(3) 0.0531(3) 0.0573(2) 0.083(2) Uani 1 1 d . U . . . C3 C 0.2631(4) 0.1290(4) 0.1592(3) 0.134(4) Uani 1 1 d . . . . . C4 C 0.2645(3) 0.1005(3) 0.1182(4) 0.120(3) Uani 1 1 d . . . . . C5 C 0.3036(2) 0.0902(3) 0.0962(3) 0.100(3) Uani 1 1 d . . . . . C6 C 0.3427(4) 0.1088(4) 0.1132(4) 0.139(3) Uani 1 1 d . . . . . C7 C 0.3424(4) 0.1419(4) 0.1499(4) 0.145(4) Uani 1 1 d . . . . . C8 C 0.3024(4) 0.1482(4) 0.1705(4) 0.160(4) Uani 1 1 d . . . . . C9 C 0.3854(4) 0.1604(5) 0.1652(5) 0.215(6) Uiso 1 1 d D . . . . C12 C 0.4603(5) 0.2096(5) 0.1839(5) 0.223(6) Uiso 1 1 d D . . . . C15 C 0.1698(3) 0.0832(2) 0.2660(3) 0.089(2) Uani 1 1 d . . . . . C16 C 0.1686(4) 0.0000 0.2707(5) 0.120(5) Uani 1 2 d S T P . . C17 C 0.1822(3) 0.0379(3) 0.2890(3) 0.112(3) Uani 1 1 d . . . . . C18 C 0.2124(3) 0.0428(3) 0.3265(3) 0.123(3) Uani 1 1 d . . . . . C19 C 0.2264(5) 0.0000 0.3445(3) 0.136(5) Uani 1 2 d S T P . . C20 C 0.2587(4) 0.0000 0.3834(3) 0.109(4) Uiso 1 2 d DS . P . . C21 C 0.2510(4) -0.0316(4) 0.4188(5) 0.128(6) Uiso 0.5 1 d D . P . . C22 C 0.2784(5) -0.0311(4) 0.4568(4) 0.166(8) Uiso 0.5 1 d D . P . . C23 C 0.3124(4) 0.0000 0.4596(4) 0.137(5) Uiso 1 2 d DS . P . . C24 C 0.3196(5) 0.0296(4) 0.4255(6) 0.181(9) Uiso 0.5 1 d D . P . . C25 C 0.2930(5) 0.0297(4) 0.3880(4) 0.146(7) Uiso 0.5 1 d D . P . . C10A C 0.4268(7) 0.1399(5) 0.1668(6) 0.247(14) Uiso 0.5 1 d D . P A 1 C11A C 0.4646(5) 0.1653(7) 0.1764(6) 0.186(9) Uiso 0.5 1 d D . P A 1 C13A C 0.4205(8) 0.2309(5) 0.1828(7) 0.250(15) Uiso 0.5 1 d D . P A 1 C14A C 0.3814(6) 0.2053(7) 0.1730(7) 0.236(13) Uiso 0.5 1 d D . P A 1 C10B C 0.4100(6) 0.1772(6) 0.1298(5) 0.195(10) Uiso 0.5 1 d D . P A 2 C13B C 0.4354(7) 0.1925(6) 0.2191(5) 0.234(13) Uiso 0.5 1 d D . P A 2 C14B C 0.3974(6) 0.1678(6) 0.2095(5) 0.156(7) Uiso 0.5 1 d D . P A 2 C11B C 0.4487(6) 0.2026(6) 0.1387(6) 0.253(15) Uiso 0.5 1 d D . P A 2 O5 O 0.5000 0.2161(7) 0.2078(6) 0.285(8) Uiso 1 2 d S . P A . 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 Cu1 0.1054(10) 0.1054(10) 0.1280(13) -0.0134(7) -0.0134(7) -0.0035(10) Cu2 0.1070(10) 0.1070(10) 0.1324(14) -0.0141(8) -0.0141(8) 0.0010(10) Cu3 0.0877(18) 0.130(2) 0.1235(18) 0.000 0.000 0.000 Cu4 0.0840(17) 0.137(2) 0.1157(17) 0.000 0.000 0.000 O1 0.148(6) 0.116(5) 0.141(5) -0.024(4) -0.014(4) -0.002(4) O2 0.121(6) 0.161(6) 0.170(6) -0.017(5) -0.064(5) -0.061(5) O3 0.039(3) 0.192(6) 0.139(4) 0.020(4) 0.001(3) 0.027(3) O4 0.073(4) 0.166(6) 0.127(4) 0.027(4) -0.005(3) -0.008(4) O6 0.146(5) 0.110(5) 0.145(5) -0.014(4) -0.008(4) -0.048(4) O7 0.153(6) 0.120(5) 0.139(5) -0.047(4) -0.020(4) -0.009(4) O8 0.108(10) 0.291(19) 0.125(9) 0.000 0.000 0.000 C1 0.009(4) 0.094(6) 0.215(10) -0.004(6) -0.027(5) -0.017(4) C2 0.060(4) 0.103(4) 0.087(4) -0.001(3) 0.004(3) 0.012(3) C3 0.097(8) 0.148(9) 0.156(8) -0.021(7) -0.046(7) -0.037(7) C4 0.082(7) 0.086(6) 0.194(9) -0.020(6) -0.022(6) -0.021(5) C5 0.016(4) 0.116(7) 0.167(7) 0.020(6) 0.001(5) 0.002(4) C6 0.111(9) 0.152(9) 0.153(8) -0.012(7) -0.008(6) 0.038(7) C7 0.104(9) 0.190(11) 0.141(8) -0.029(8) -0.016(7) -0.009(7) C8 0.115(10) 0.155(10) 0.211(11) -0.053(8) 0.029(9) 0.035(8) C15 0.106(6) 0.052(5) 0.108(6) -0.016(4) -0.033(5) -0.008(4) C16 0.132(11) 0.005(5) 0.223(14) 0.000 0.016(9) 0.000 C17 0.123(7) 0.102(7) 0.113(6) 0.027(6) 0.034(6) 0.056(6) C18 0.105(7) 0.148(9) 0.116(6) 0.045(6) -0.010(6) 0.030(6) C19 0.150(12) 0.193(16) 0.064(6) 0.000 -0.015(7) 0.000 _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 Cu1 O6 1.947(7) . ? Cu1 O6 1.947(7) 16 ? Cu1 O1 1.970(7) . ? Cu1 O1 1.970(7) 16 ? Cu1 O10 2.210(12) . ? Cu1 Cu2 2.655(2) . ? Cu2 O7 1.911(7) 16 ? Cu2 O7 1.911(7) . ? Cu2 O2 1.935(8) . ? Cu2 O2 1.935(8) 16 ? Cu2 O9 2.178(12) . ? Cu3 O3 1.910(7) . ? Cu3 O3 1.911(7) 5 ? Cu3 O3 1.911(7) 14 ? Cu3 O3 1.911(7) 11 ? Cu3 O12 2.134(15) . ? Cu3 Cu4 2.655(3) . ? Cu4 O4 1.982(6) . ? Cu4 O4 1.982(6) 5 ? Cu4 O4 1.982(6) 14 ? Cu4 O4 1.982(6) 11 ? Cu4 O11 2.186(16) . ? O1 C1 1.276(9) . ? O2 C1 1.210(11) . ? O3 C2 1.189(9) . ? O4 C2 1.262(8) . ? O6 C15 1.241(8) . ? O7 C15 1.283(8) . ? O8 C23 1.420(12) 11_556 ? O8 C23 1.420(12) . ? C1 C3 1.567(13) . ? C2 C5 1.611(11) . ? C3 C8 1.369(14) . ? C3 C4 1.491(12) . ? C4 C5 1.386(11) . ? C5 C6 1.405(12) . ? C6 C7 1.477(13) . ? C7 C8 1.370(13) . ? C7 C9 1.489(14) . ? C9 C14B 1.379(13) . ? C9 C10B 1.383(14) . ? C9 C14A 1.385(15) . ? C9 C10A 1.399(15) . ? C12 C11A 1.366(14) . ? C12 C13A 1.370(15) . ? C12 C13B 1.386(14) . ? C12 C11B 1.399(15) . ? C12 O5 1.408(14) . ? C15 C17 1.576(10) . ? C16 C17 1.335(13) 14 ? C16 C17 1.335(13) . ? C17 C18 1.448(12) . ? C18 C19 1.464(9) . ? C19 C18 1.464(9) 14 ? C19 C20 1.514(15) . ? C20 C25 1.382(13) . ? C20 C25 1.382(13) 14 ? C20 C21 1.438(12) 14 ? C20 C21 1.438(12) . ? C21 C22 1.399(14) . ? C21 C25 1.568(18) 14 ? C21 C21 1.91(2) 14 ? C22 C23 1.397(13) . ? C22 C24 1.555(18) 14 ? C22 C22 1.88(2) 14 ? C23 C24 1.368(13) 14 ? C23 C24 1.368(13) . ? C23 C22 1.397(13) 14 ? C24 C25 1.371(14) . ? C24 C22 1.555(18) 14 ? C24 C24 1.79(2) 14 ? C25 C21 1.568(18) 14 ? C25 C25 1.80(2) 14 ? C10A C11A 1.409(15) . ? C13A C14A 1.444(15) . ? C10B C11B 1.426(15) . ? C13B C14B 1.405(15) . ? O5 C12 1.408(14) 13_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 O6 Cu1 O6 89.0(4) . 16 ? O6 Cu1 O1 90.7(3) . . ? O6 Cu1 O1 168.3(3) 16 . ? O6 Cu1 O1 168.3(3) . 16 ? O6 Cu1 O1 90.7(3) 16 16 ? O1 Cu1 O1 87.3(4) . 16 ? O6 Cu1 O10 95.4(3) . . ? O6 Cu1 O10 95.4(3) 16 . ? O1 Cu1 O10 96.3(3) . . ? O1 Cu1 O10 96.3(3) 16 . ? O6 Cu1 Cu2 83.9(2) . . ? O6 Cu1 Cu2 83.9(2) 16 . ? O1 Cu1 Cu2 84.38(19) . . ? O1 Cu1 Cu2 84.38(19) 16 . ? O10 Cu1 Cu2 179.1(3) . . ? O7 Cu2 O7 92.3(4) 16 . ? O7 Cu2 O2 169.5(3) 16 . ? O7 Cu2 O2 89.5(3) . . ? O7 Cu2 O2 89.5(3) 16 16 ? O7 Cu2 O2 169.5(3) . 16 ? O2 Cu2 O2 87.0(4) . 16 ? O7 Cu2 O9 98.3(3) 16 . ? O7 Cu2 O9 98.3(3) . . ? O2 Cu2 O9 91.6(3) . . ? O2 Cu2 O9 91.6(3) 16 . ? O7 Cu2 Cu1 84.46(19) 16 . ? O7 Cu2 Cu1 84.46(19) . . ? O2 Cu2 Cu1 85.45(19) . . ? O2 Cu2 Cu1 85.45(19) 16 . ? O9 Cu2 Cu1 176.0(3) . . ? O3 Cu3 O3 169.8(3) . 5 ? O3 Cu3 O3 90.6(3) . 14 ? O3 Cu3 O3 88.5(3) 5 14 ? O3 Cu3 O3 88.5(3) . 11 ? O3 Cu3 O3 90.6(3) 5 11 ? O3 Cu3 O3 169.8(3) 14 11 ? O3 Cu3 O12 95.09(17) . . ? O3 Cu3 O12 95.08(17) 5 . ? O3 Cu3 O12 95.08(17) 14 . ? O3 Cu3 O12 95.08(17) 11 . ? O3 Cu3 Cu4 84.91(17) . . ? O3 Cu3 Cu4 84.92(17) 5 . ? O3 Cu3 Cu4 84.92(17) 14 . ? O3 Cu3 Cu4 84.92(17) 11 . ? O12 Cu3 Cu4 180.0 . . ? O4 Cu4 O4 169.9(4) . 5 ? O4 Cu4 O4 90.5(3) . 14 ? O4 Cu4 O4 88.7(3) 5 14 ? O4 Cu4 O4 88.7(3) . 11 ? O4 Cu4 O4 90.5(3) 5 11 ? O4 Cu4 O4 169.9(4) 14 11 ? O4 Cu4 O11 95.05(18) . . ? O4 Cu4 O11 95.05(18) 5 . ? O4 Cu4 O11 95.05(18) 14 . ? O4 Cu4 O11 95.05(18) 11 . ? O4 Cu4 Cu3 84.95(18) . . ? O4 Cu4 Cu3 84.95(18) 5 . ? O4 Cu4 Cu3 84.95(18) 14 . ? O4 Cu4 Cu3 84.95(18) 11 . ? O11 Cu4 Cu3 180.0 . . ? C1 O1 Cu1 115.3(6) . . ? C1 O2 Cu2 116.9(5) . . ? C2 O3 Cu3 116.4(5) . . ? C2 O4 Cu4 111.7(5) . . ? C15 O6 Cu1 120.7(5) . . ? C15 O7 Cu2 121.2(5) . . ? C23 O8 C23 114.6(14) 11_556 . ? O2 C1 O1 136.4(9) . . ? O2 C1 C3 115.2(7) . . ? O1 C1 C3 107.3(10) . . ? O3 C2 O4 141.2(8) . . ? O3 C2 C5 112.5(7) . . ? O4 C2 C5 105.6(7) . . ? C8 C3 C4 114.8(10) . . ? C8 C3 C1 120.1(9) . . ? C4 C3 C1 125.0(8) . . ? C5 C4 C3 122.5(8) . . ? C4 C5 C6 117.6(9) . . ? C4 C5 C2 118.4(7) . . ? C6 C5 C2 123.5(8) . . ? C5 C6 C7 122.0(9) . . ? C8 C7 C6 115.4(10) . . ? C8 C7 C9 125.8(12) . . ? C6 C7 C9 118.3(11) . . ? C3 C8 C7 127.0(11) . . ? C14B C9 C10B 121.4(9) . . ? C14A C9 C10A 120.6(9) . . ? C14B C9 C7 125.4(12) . . ? C10B C9 C7 112.3(12) . . ? C14A C9 C7 110.2(13) . . ? C10A C9 C7 128.7(13) . . ? C11A C12 C13A 122.9(10) . . ? C13B C12 C11B 121.6(10) . . ? C11A C12 O5 97.9(16) . . ? C13A C12 O5 134.3(16) . . ? C13B C12 O5 98.0(13) . . ? C11B C12 O5 135.7(14) . . ? O6 C15 O7 127.7(7) . . ? O6 C15 C17 113.9(7) . . ? O7 C15 C17 117.8(8) . . ? C17 C16 C17 118.9(13) 14 . ? C16 C17 C18 126.4(9) . . ? C16 C17 C15 120.1(9) . . ? C18 C17 C15 113.1(9) . . ? C17 C18 C19 111.8(9) . . ? C18 C19 C18 124.7(11) 14 . ? C18 C19 C20 117.6(6) 14 . ? C18 C19 C20 117.6(6) . . ? C25 C20 C25 81.4(10) . 14 ? C25 C20 C21 67.5(8) . 14 ? C25 C20 C21 119.0(8) 14 14 ? C25 C20 C21 119.0(8) . . ? C25 C20 C21 67.5(8) 14 . ? C21 C20 C21 83.4(9) 14 . ? C25 C20 C19 124.2(8) . . ? C25 C20 C19 124.2(8) 14 . ? C21 C20 C19 116.7(8) 14 . ? C21 C20 C19 116.7(8) . . ? C22 C21 C20 118.8(9) . . ? C22 C21 C25 89.1(7) . 14 ? C20 C21 C25 54.5(7) . 14 ? C22 C21 C21 89.4(5) . 14 ? C20 C21 C21 48.3(4) . 14 ? C25 C21 C21 88.0(5) 14 14 ? C23 C22 C21 119.5(9) . . ? C23 C22 C24 54.9(8) . 14 ? C21 C22 C24 89.9(7) . 14 ? C23 C22 C22 47.7(5) . 14 ? C21 C22 C22 90.6(5) . 14 ? C24 C22 C22 88.4(6) 14 14 ? C24 C23 C24 82.0(10) 14 . ? C24 C23 C22 68.4(9) 14 . ? C24 C23 C22 121.0(9) . . ? C24 C23 C22 121.0(9) 14 14 ? C24 C23 C22 68.4(9) . 14 ? C22 C23 C22 84.7(10) . 14 ? C24 C23 O8 122.3(9) 14 . ? C24 C23 O8 122.3(9) . . ? C22 C23 O8 116.6(9) . . ? C22 C23 O8 116.6(9) 14 . ? C23 C24 C25 120.3(10) . . ? C23 C24 C22 56.7(8) . 14 ? C25 C24 C22 90.6(8) . 14 ? C23 C24 C24 49.0(5) . 14 ? C25 C24 C24 90.2(6) . 14 ? C22 C24 C24 91.6(6) 14 14 ? C24 C25 C20 121.3(9) . . ? C24 C25 C21 90.4(7) . 14 ? C20 C25 C21 57.9(7) . 14 ? C24 C25 C25 89.8(6) . 14 ? C20 C25 C25 49.3(5) . 14 ? C21 C25 C25 92.0(5) 14 14 ? C9 C10A C11A 119.5(10) . . ? C12 C11A C10A 119.5(10) . . ? C12 C13A C14A 118.3(10) . . ? C9 C14A C13A 119.3(10) . . ? C9 C10B C11B 120.0(10) . . ? C12 C13B C14B 119.7(10) . . ? C9 C14B C13B 119.5(10) . . ? C12 C11B C10B 117.7(10) . . ? C12 O5 C12 117(2) 13_655 . ? _refine_diff_density_max 0.855 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.083 _shelxl_version_number 2013-2 _shelx_res_file ; REM CF solution in P4/mmm REM R1 = 0.3805 for 3856 Fo > 4sig(Fo) and 0.5034 for all 10997 data REM 205 parameters refined using 0 restraints REM Highest difference peak 1.873, deepest hole -1.488, 1-sigma level 0.204 REM The information below was added by Olex2. REM REM R1 = 0.3805 for 3856 Fo > 4sig(Fo) and n/a for all 103205 data REM n/a parameters refined using n/a restraints REM Highest difference peak 1.87, deepest hole -1.49 REM Mean Shift 0.128, Max Shift 1.797. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = n/a REM R1_gt = 0.3805 REM wR_ref = 0.7605 REM GOOF = 2.369 REM Shift_max = 1.797 REM Shift_mean = 0.128 REM Reflections_all = 103205 REM Reflections_gt = 3856 REM Parameters = n/a REM Hole = 1.87 REM Peak = -1.49 REM Flack = n/a REM CF solution in P4/mmm REM R1 = 0.3413 for 3856 Fo > 4sig(Fo) and 0.4674 for all 10997 data REM 265 parameters refined using 53 restraints REM Highest difference peak 3.120, deepest hole -0.909, 1-sigma level 0.199 REM CF solution in P4/mmm REM R1 = 0.1452 for 3835 Fo > 4sig(Fo) and 0.2356 for all 10997 data REM 265 parameters refined using 53 restraints REM Highest difference peak 0.817, deepest hole -0.557, 1-sigma level 0.078 TITL CF solution in P4/mmm CELL 1.54184 30.2922 30.2922 29.5968 90.000 90.000 90.000 ZERR 4.0000 0.0013 0.0013 0.0025 0.000 0.000 0.000 LATT 1 SYMM -Y, X, Z SYMM -X, -Y, Z SYMM Y, -X, Z SYMM X, -Y, -Z SYMM -X, Y, -Z SYMM Y, X, -Z SYMM -Y, -X, -Z SFAC C H O CU UNIT 336 216 132 24 MERG 2 FMAP 2 GRID PLAN 5 TEMP -173 BOND $H DFIX 1.39 0.02 C20 C21 C21 C22 C22 C23 C23 C24 C24 C25 C25 C20 DFIX 2.40 0.02 C20 C22 C21 C23 C22 C24 C23 C25 C24 C20 C25 C21 DFIX 2.80 0.02 C20 C23 C21 C24 C22 C25 FLAT 0.01 C20 C21 C22 C23 C24 C25 DFIX 1.39 0.02 C9 C10A C10A C11A C11A C12 C12 C13A C13A C14A C14A C9 DFIX 2.40 0.02 C9 C11A C10A C12 C11A C13A C12 C14A C13A C9 C14A C10A DFIX 2.80 0.02 C9 C12 C10A C13A C11A C14A DFIX 1.39 0.02 C9 C10B C10B C11B C11B C12 C12 C13B C13B C14B C14B C9 DFIX 2.40 0.02 C9 C11B C10B C12 C11B C13B C12 C14B C13B C9 C14B C10B DFIX 2.80 0.02 C10B C13B C11B C14B FLAT 0.01 C9 C10A C11A C12 C13A C14A FLAT 0.01 C9 C10B C11B C12 C13B C14B ISOR 0.005 C2 L.S. 20 ACTA WGHT 0.200000 FVAR 6.92390 CU1 4 0.129999 0.129999 0.195652 10.50000 0.10542 0.10542 = 0.12796 -0.01338 -0.01338 -0.00345 CU2 4 0.175101 0.175101 0.257164 10.50000 0.10705 0.10705 = 0.13240 -0.01412 -0.01412 0.00100 CU3 4 0.260582 0.000000 0.000000 10.25000 0.08770 0.12962 = 0.12352 0.00000 0.00000 0.00000 CU4 4 0.348244 0.000000 0.000000 10.25000 0.08400 0.13687 = 0.11568 0.00000 0.00000 0.00000 O1 3 0.187635 0.124133 0.165401 11.00000 0.14817 0.11648 = 0.14068 -0.02352 -0.01363 -0.00158 O2 3 0.225918 0.163756 0.219286 11.00000 0.12117 0.16053 = 0.16958 -0.01714 -0.06364 -0.06150 O3 3 0.266172 0.044845 0.045026 11.00000 0.03906 0.19190 = 0.13859 0.01970 0.00136 0.02709 O4 3 0.342487 0.046437 0.046783 11.00000 0.07298 0.16572 = 0.12707 0.02687 -0.00463 -0.00808 O6 3 0.143343 0.079662 0.234192 11.00000 0.14592 0.10962 = 0.14518 -0.01357 -0.00828 -0.04775 O7 3 0.183142 0.118816 0.285136 11.00000 0.15251 0.12001 = 0.13926 -0.04654 -0.02005 -0.00928 O8 3 0.337739 0.000000 0.500000 10.25000 0.10806 0.29115 = 0.12479 0.00000 0.00000 0.00000 O9 3 0.214446 0.214446 0.303766 10.50000 0.19022 O10 3 0.091875 0.091875 0.145329 10.50000 0.19342 O11 3 0.420402 0.000000 0.000000 10.25000 0.17857 O12 3 0.190126 0.000000 0.000000 10.25000 0.16863 C1 1 0.220520 0.139310 0.187422 11.00000 0.00942 0.09370 = 0.21460 -0.00389 -0.02693 -0.01694 C2 1 0.302648 0.053103 0.057257 11.00000 0.05985 0.10346 = 0.08682 -0.00115 0.00371 0.01181 C3 1 0.263058 0.128995 0.159223 11.00000 0.09727 0.14770 = 0.15605 -0.02095 -0.04594 -0.03710 C4 1 0.264531 0.100460 0.118194 11.00000 0.08182 0.08579 = 0.19379 -0.01985 -0.02216 -0.02123 C5 1 0.303637 0.090241 0.096223 11.00000 0.01631 0.11618 = 0.16654 0.01989 0.00056 0.00205 C6 1 0.342733 0.108844 0.113223 11.00000 0.11060 0.15219 = 0.15284 -0.01172 -0.00797 0.03815 C7 1 0.342420 0.141906 0.149895 11.00000 0.10380 0.18976 = 0.14072 -0.02864 -0.01601 -0.00933 C8 1 0.302429 0.148235 0.170544 11.00000 0.11467 0.15453 = 0.21099 -0.05286 0.02919 0.03530 C9 1 0.385420 0.160442 0.165203 11.00000 0.21501 C12 1 0.460342 0.209600 0.183887 11.00000 0.22336 C15 1 0.169774 0.083230 0.266003 11.00000 0.10602 0.05209 = 0.10791 -0.01592 -0.03342 -0.00766 C16 1 0.168609 0.000000 0.270683 10.50000 0.13218 0.00495 = 0.22273 0.00000 0.01596 0.00000 C17 1 0.182156 0.037949 0.288958 11.00000 0.12268 0.10188 = 0.11272 0.02745 0.03427 0.05560 C18 1 0.212433 0.042816 0.326508 11.00000 0.10542 0.14800 = 0.11607 0.04484 -0.01015 0.03030 C19 1 0.226379 0.000000 0.344472 10.50000 0.14999 0.19342 = 0.06363 0.00000 -0.01493 0.00000 C20 1 0.258727 0.000000 0.383448 10.50000 0.10945 C21 1 0.250966 -0.031569 0.418836 10.50000 0.12812 C22 1 0.278427 -0.031063 0.456827 10.50000 0.16621 C23 1 0.312419 0.000000 0.459618 10.50000 0.13715 C24 1 0.319616 0.029617 0.425517 10.50000 0.18126 C25 1 0.293018 0.029736 0.388026 10.50000 0.14592 PART 1 C10A 1 0.426760 0.139917 0.166805 10.50000 0.24701 C11A 1 0.464601 0.165296 0.176421 10.50000 0.18564 C13A 1 0.420488 0.230923 0.182844 10.50000 0.24993 C14A 1 0.381422 0.205328 0.173041 10.50000 0.23619 PART 2 C10B 1 0.410036 0.177169 0.129788 10.50000 0.19501 C13B 1 0.435447 0.192539 0.219078 10.50000 0.23371 C14B 1 0.397358 0.167781 0.209540 10.50000 0.15646 C11B 1 0.448726 0.202553 0.138699 10.50000 0.25295 PART 0 O5 3 0.500000 0.216078 0.207776 10.50000 0.28478 HKLF 4 REM CF solution in P4/mmm REM R1 = 0.1514 for 3835 Fo > 4sig(Fo) and 0.2416 for all 10997 data REM 265 parameters refined using 59 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.855, deepest hole -0.587, 1-sigma level 0.083 Q1 1 0.5000 0.2445 0.1886 10.50000 0.05 0.86 Q2 1 0.3049 0.0000 0.0000 10.25000 0.05 0.63 Q3 1 0.3926 0.0000 0.0000 10.25000 0.05 0.59 Q4 1 0.4137 -0.0261 0.0000 10.50000 0.05 0.58 Q5 1 0.1734 0.1734 0.2449 10.50000 0.05 0.55 ; _shelx_res_checksum 26246 _shelx_hkl_file ; ; _shelx_hkl_checksum 87512 _database_code_depnum_ccdc_archive 'CCDC 963684'