# 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_compound_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H29 Cu2 N3 O10' _chemical_formula_weight 718.64 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' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.1849(4) _cell_length_b 17.0797(4) _cell_length_c 18.8731(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.172(2) _cell_angle_gamma 90.00 _cell_volume 4856.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.983 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 1.418 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8712 _exptl_absorpt_correction_T_max 0.9325 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9392 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.38 _diffrn_reflns_theta_max 73.10 _reflns_number_total 4707 _reflns_number_gt 4046 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1158P)^2^+0.1919P] 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 4707 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1560 _refine_ls_wR_factor_gt 0.1491 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 Cu1 Cu 0.466347(19) 0.438154(17) 0.527950(14) 0.03141(15) Uani 1 1 d . . . O3 O -0.01998(12) 0.89233(10) 0.43403(8) 0.0429(4) Uani 1 1 d . . . O2 O 0.35116(11) 0.48201(10) 0.48740(9) 0.0430(4) Uani 1 1 d . . . O1 O 0.41026(11) 0.58658(11) 0.43865(10) 0.0451(4) Uani 1 1 d . . . O4 O 0.03542(12) 0.99827(10) 0.38531(8) 0.0418(4) Uani 1 1 d . . . O5 O 0.41061(12) 0.33094(11) 0.56279(10) 0.0479(4) Uani 1 1 d . . . N1 N 0.0000 0.68140(16) 0.2500 0.0413(6) Uani 1 2 d S . . C9 C 0.00435(13) 0.80497(14) 0.31420(11) 0.0348(4) Uani 1 1 d . . . H9 H 0.0072 0.7778 0.3583 0.042 Uiso 1 1 calc R . . C8 C 0.0000 0.76216(18) 0.2500 0.0339(6) Uani 1 2 d S . . C10 C 0.00452(14) 0.88601(14) 0.31400(10) 0.0354(4) Uani 1 1 d . . . C11 C 0.0000 0.92797(19) 0.2500 0.0372(7) Uani 1 2 d S . . H11 H 0.0000 0.9836 0.2500 0.045 Uiso 1 2 calc SR . . C1 C 0.34657(15) 0.54384(14) 0.45008(11) 0.0385(5) Uani 1 1 d . . . C5 C 0.08916(15) 0.61305(14) 0.35009(13) 0.0432(5) Uani 1 1 d . . . C2 C 0.25629(17) 0.56764(13) 0.41647(14) 0.0410(5) Uani 1 1 d . . . C3 C 0.18022(18) 0.53126(15) 0.43448(15) 0.0495(6) Uani 1 1 d . . . H3 H 0.1850 0.4908 0.4693 0.059 Uiso 1 1 calc R . . C4 C 0.09681(19) 0.55415(16) 0.40146(17) 0.0529(7) Uani 1 1 d . . . H4 H 0.0450 0.5294 0.4141 0.063 Uiso 1 1 calc R . . C6 C 0.16490(16) 0.64951(16) 0.33304(14) 0.0471(6) Uani 1 1 d . . . H6 H 0.1601 0.6900 0.2983 0.056 Uiso 1 1 calc R . . C16 C -0.00207(16) 0.63602(15) 0.31431(14) 0.0461(6) Uani 1 1 d . . . H16A H -0.0372 0.5879 0.3025 0.055 Uiso 1 1 calc R . . H16B H -0.0326 0.6668 0.3485 0.055 Uiso 1 1 calc R . . C7 C 0.24798(17) 0.62756(16) 0.36614(14) 0.0479(6) Uani 1 1 d . . . H7 H 0.2995 0.6536 0.3544 0.057 Uiso 1 1 calc R . . N2 N 0.2891(2) 0.2622(2) 0.59122(18) 0.0748(8) Uani 1 1 d . . . C13 C 0.3305(2) 0.3270(2) 0.57616(17) 0.0618(7) Uani 1 1 d . . . H13 H 0.2979 0.3746 0.5752 0.074 Uiso 1 1 calc R . . C14 C 0.1975(4) 0.2647(4) 0.6107(4) 0.1179(19) Uani 1 1 d . . . H14A H 0.1982 0.2494 0.6608 0.177 Uiso 1 1 calc R . . H14B H 0.1598 0.2285 0.5802 0.177 Uiso 1 1 calc R . . H14C H 0.1739 0.3180 0.6040 0.177 Uiso 1 1 calc R . . C15 C 0.3348(4) 0.1869(2) 0.5907(3) 0.1045(17) Uani 1 1 d . . . H15A H 0.3969 0.1956 0.5834 0.157 Uiso 1 1 calc R . . H15B H 0.3057 0.1543 0.5520 0.157 Uiso 1 1 calc R . . H15C H 0.3326 0.1603 0.6365 0.157 Uiso 1 1 calc R . . C12 C 0.00732(15) 0.92902(13) 0.38323(12) 0.0353(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 Cu1 0.0357(2) 0.0353(2) 0.0219(2) 0.00511(10) -0.00133(13) 0.00377(11) O3 0.0565(9) 0.0438(9) 0.0288(7) 0.0031(6) 0.0070(7) -0.0015(7) O2 0.0401(8) 0.0459(9) 0.0404(8) 0.0113(7) -0.0051(6) 0.0059(7) O1 0.0381(8) 0.0494(9) 0.0454(9) 0.0140(8) -0.0037(7) 0.0059(7) O4 0.0550(9) 0.0429(9) 0.0268(7) 0.0006(6) 0.0026(6) -0.0050(7) O5 0.0545(10) 0.0424(9) 0.0479(9) 0.0105(7) 0.0109(8) 0.0008(8) N1 0.0373(13) 0.0368(13) 0.0454(14) 0.000 -0.0122(11) 0.000 C9 0.0295(9) 0.0453(12) 0.0277(9) 0.0058(8) -0.0042(7) 0.0017(8) C8 0.0262(12) 0.0374(15) 0.0354(14) 0.000 -0.0064(10) 0.000 C10 0.0349(10) 0.0438(11) 0.0261(9) 0.0023(8) -0.0021(7) 0.0017(9) C11 0.0434(16) 0.0427(16) 0.0244(14) 0.000 -0.0008(12) 0.000 C1 0.0390(11) 0.0430(11) 0.0312(10) 0.0021(9) -0.0043(9) 0.0086(10) C5 0.0393(11) 0.0412(12) 0.0453(12) 0.0064(10) -0.0092(9) -0.0018(9) C2 0.0412(12) 0.0397(12) 0.0388(12) 0.0055(9) -0.0076(9) 0.0032(9) C3 0.0494(13) 0.0416(13) 0.0532(14) 0.0138(11) -0.0107(11) -0.0010(11) C4 0.0420(13) 0.0465(13) 0.0662(18) 0.0185(12) -0.0086(12) -0.0050(10) C6 0.0389(11) 0.0488(13) 0.0504(13) 0.0148(11) -0.0063(10) 0.0003(10) C16 0.0395(11) 0.0388(12) 0.0558(14) 0.0093(10) -0.0109(10) -0.0040(9) C7 0.0399(11) 0.0536(14) 0.0476(13) 0.0165(11) -0.0047(10) 0.0000(11) N2 0.0779(18) 0.0794(19) 0.0701(17) 0.0009(14) 0.0216(14) -0.0203(15) C13 0.0626(17) 0.0679(18) 0.0554(16) 0.0032(14) 0.0101(13) -0.0063(15) C14 0.097(3) 0.136(5) 0.130(5) 0.004(4) 0.050(3) -0.011(3) C15 0.160(5) 0.055(2) 0.106(3) 0.007(2) 0.048(3) -0.017(3) C12 0.0375(10) 0.0420(12) 0.0249(10) 0.0048(8) -0.0027(8) 0.0074(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9472(16) 5_666 ? Cu1 O4 1.9674(16) 7_566 ? Cu1 O2 1.9677(16) . ? Cu1 O3 1.9722(16) 3_545 ? Cu1 O5 2.1541(18) . ? Cu1 Cu1 2.6249(6) 5_666 ? O3 C12 1.258(3) . ? O3 Cu1 1.9722(16) 3_455 ? O2 C1 1.267(3) . ? O1 C1 1.252(3) . ? O1 Cu1 1.9472(16) 5_666 ? O4 C12 1.256(3) . ? O4 Cu1 1.9674(16) 7_566 ? O5 C13 1.274(4) . ? N1 C8 1.379(4) . ? N1 C16 1.444(3) 2 ? N1 C16 1.444(3) . ? C9 C10 1.384(3) . ? C9 C8 1.410(3) . ? C9 H9 0.9500 . ? C8 C9 1.410(3) 2 ? C10 C11 1.399(3) . ? C10 C12 1.495(3) . ? C11 C10 1.399(3) 2 ? C11 H11 0.9500 . ? C1 C2 1.493(3) . ? C5 C6 1.381(4) . ? C5 C4 1.392(4) . ? C5 C16 1.515(3) . ? C2 C3 1.391(4) . ? C2 C7 1.391(3) . ? C3 C4 1.396(4) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C6 C7 1.388(3) . ? C6 H6 0.9500 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C7 H7 0.9500 . ? N2 C13 1.322(4) . ? N2 C15 1.462(6) . ? N2 C14 1.483(6) . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 Cu1 O4 87.88(8) 5_666 7_566 ? O1 Cu1 O2 168.87(7) 5_666 . ? O4 Cu1 O2 90.56(7) 7_566 . ? O1 Cu1 O3 89.99(8) 5_666 3_545 ? O4 Cu1 O3 168.75(7) 7_566 3_545 ? O2 Cu1 O3 89.41(7) . 3_545 ? O1 Cu1 O5 96.64(7) 5_666 . ? O4 Cu1 O5 99.70(7) 7_566 . ? O2 Cu1 O5 94.49(7) . . ? O3 Cu1 O5 91.51(7) 3_545 . ? O1 Cu1 Cu1 84.11(6) 5_666 5_666 ? O4 Cu1 Cu1 86.37(5) 7_566 5_666 ? O2 Cu1 Cu1 84.79(5) . 5_666 ? O3 Cu1 Cu1 82.43(5) 3_545 5_666 ? O5 Cu1 Cu1 173.90(5) . 5_666 ? C12 O3 Cu1 124.67(15) . 3_455 ? C1 O2 Cu1 121.21(15) . . ? C1 O1 Cu1 123.41(15) . 5_666 ? C12 O4 Cu1 120.39(15) . 7_566 ? C13 O5 Cu1 121.7(2) . . ? C8 N1 C16 122.47(14) . 2 ? C8 N1 C16 122.47(14) . . ? C16 N1 C16 115.1(3) 2 . ? C10 C9 C8 121.08(19) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? N1 C8 C9 121.24(14) . . ? N1 C8 C9 121.24(14) . 2 ? C9 C8 C9 117.5(3) . 2 ? C9 C10 C11 121.0(2) . . ? C9 C10 C12 119.26(18) . . ? C11 C10 C12 119.7(2) . . ? C10 C11 C10 118.4(3) 2 . ? C10 C11 H11 120.8 2 . ? C10 C11 H11 120.8 . . ? O1 C1 O2 126.3(2) . . ? O1 C1 C2 117.1(2) . . ? O2 C1 C2 116.6(2) . . ? C6 C5 C4 119.3(2) . . ? C6 C5 C16 121.4(2) . . ? C4 C5 C16 119.3(2) . . ? C3 C2 C7 119.2(2) . . ? C3 C2 C1 121.4(2) . . ? C7 C2 C1 119.4(2) . . ? C2 C3 C4 120.1(2) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C5 C6 C7 120.7(2) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? N1 C16 C5 113.5(2) . . ? N1 C16 H16A 108.9 . . ? C5 C16 H16A 108.9 . . ? N1 C16 H16B 108.9 . . ? C5 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C6 C7 C2 120.4(2) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? C13 N2 C15 119.8(3) . . ? C13 N2 C14 121.0(4) . . ? C15 N2 C14 119.2(4) . . ? O5 C13 N2 125.3(3) . . ? O5 C13 H13 117.3 . . ? N2 C13 H13 117.3 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O4 C12 O3 126.0(2) . . ? O4 C12 C10 117.5(2) . . ? O3 C12 C10 116.4(2) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 73.10 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.773 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.078 # 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 -0.002 0.131 0.232 2316 664 ' ' _platon_squeeze_details ? _database_code_depnum_ccdc_archive 'CCDC 943580' ####################################################################### # # 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_compound_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H19 Cu2 N O10' _chemical_formula_weight 608.48 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' N N 0.0311 0.0180 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6325(9) _cell_length_b 10.7258(8) _cell_length_c 18.3532(14) _cell_angle_alpha 76.671(6) _cell_angle_beta 86.717(6) _cell_angle_gamma 74.278(7) _cell_volume 1960.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.031 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 1.665 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8783 _exptl_absorpt_correction_T_max 0.9675 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13873 _diffrn_reflns_av_R_equivalents 0.1120 _diffrn_reflns_av_sigmaI/netI 0.0953 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.32 _diffrn_reflns_theta_max 67.31 _reflns_number_total 6984 _reflns_number_gt 3979 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1353P)^2^+0.0000P] 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 6984 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1269 _refine_ls_R_factor_gt 0.0903 _refine_ls_wR_factor_ref 0.2342 _refine_ls_wR_factor_gt 0.2137 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _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 Cu1 Cu 0.92931(8) 0.10292(9) 0.02452(5) 0.0488(3) Uani 1 1 d . . . Cu2 Cu 1.09021(8) -1.08455(9) 0.54611(5) 0.0498(3) Uani 1 1 d . . . O8 O 1.8245(4) -0.0212(4) 0.0696(3) 0.0623(12) Uani 1 1 d . . . C1 C 1.1257(6) -0.0816(7) 0.1209(3) 0.0470(15) Uani 1 1 d . . . O7 O 1.9409(4) -0.1934(4) 0.0242(3) 0.0587(12) Uani 1 1 d . . . O5 O 1.1989(5) -0.9588(5) 0.5183(3) 0.0660(12) Uani 1 1 d . . . O6 O 1.0426(5) -0.8166(5) 0.4401(3) 0.0714(14) Uani 1 1 d . . . O3 O 1.1583(5) -0.1563(5) 0.4588(3) 0.0649(12) Uani 1 1 d . . . O1 O 1.1629(4) -0.1508(5) 0.0722(3) 0.0607(12) Uani 1 1 d . . . N9 N 1.4614(5) -0.4169(5) 0.2930(3) 0.0631(15) Uani 1 1 d . . . C7 C 1.3504(6) -0.3124(6) 0.2816(4) 0.0574(17) Uani 1 1 d . . . C15 C 1.8488(6) -0.1370(6) 0.0627(3) 0.0514(15) Uani 1 1 d . . . O10 O 0.8112(5) 0.2685(6) 0.0658(4) 0.093(2) Uani 1 1 d . . . C14 C 1.2959(7) -0.2490(6) 0.2093(4) 0.0603(18) Uani 1 1 d . . . H14 H 1.3351 -0.2819 0.1673 0.072 Uiso 1 1 calc R . . C2 C 1.1885(6) -0.1418(6) 0.1985(4) 0.0585(17) Uani 1 1 d . . . C24 C 1.6965(7) -0.1844(7) 0.1661(4) 0.065(2) Uani 1 1 d . . . H24 H 1.7013 -0.1060 0.1803 0.078 Uiso 1 1 calc R . . C4 C 1.1741(6) -0.1539(6) 0.3286(3) 0.0544(16) Uani 1 1 d . . . C6 C 1.2828(7) -0.2626(7) 0.3412(4) 0.0618(18) Uani 1 1 d . . . H6 H 1.3120 -0.3041 0.3911 0.074 Uiso 1 1 calc R . . C10 C 1.6105(6) -0.3767(6) 0.1858(4) 0.0563(16) Uani 1 1 d . . . C13 C 1.7664(6) -0.2222(6) 0.1062(4) 0.0571(17) Uani 1 1 d . . . C12 C 1.7570(7) -0.3336(7) 0.0855(4) 0.075(2) Uani 1 1 d . . . H12 H 1.8036 -0.3585 0.0431 0.090 Uiso 1 1 calc R . . C16 C 1.4917(7) -0.5037(7) 0.3655(4) 0.0661(19) Uani 1 1 d . . . H16A H 1.4857 -0.4486 0.4027 0.079 Uiso 1 1 calc R . . H16B H 1.5834 -0.5576 0.3653 0.079 Uiso 1 1 calc R . . C23 C 1.1555(7) -0.8540(7) 0.4700(4) 0.0576(16) Uani 1 1 d . . . C11 C 1.6796(7) -0.4112(7) 0.1261(4) 0.0633(18) Uani 1 1 d . . . H11 H 1.6755 -0.4895 0.1115 0.076 Uiso 1 1 calc R . . C9 C 1.6179(7) -0.2621(7) 0.2062(4) 0.067(2) Uani 1 1 d . . . H9 H 1.5693 -0.2362 0.2478 0.080 Uiso 1 1 calc R . . C8 C 1.5300(7) -0.4652(7) 0.2299(4) 0.067(2) Uani 1 1 d . . . H8A H 1.4653 -0.4735 0.1959 0.080 Uiso 1 1 calc R . . H8B H 1.5885 -0.5550 0.2488 0.080 Uiso 1 1 calc R . . C17 C 1.4045(7) -0.5978(7) 0.3912(4) 0.0641(18) Uani 1 1 d . . . C18 C 1.2956(7) -0.5872(8) 0.3522(5) 0.075(2) Uani 1 1 d . . . H18 H 1.2746 -0.5215 0.3069 0.090 Uiso 1 1 calc R . . C22 C 1.2452(7) -0.7670(7) 0.4429(4) 0.0593(17) Uani 1 1 d . . . C3 C 1.1260(8) -0.0947(7) 0.2596(4) 0.066(2) Uani 1 1 d . . . H3 H 1.0503 -0.0215 0.2524 0.080 Uiso 1 1 calc R . . C20 C 1.2143(8) -0.6703(7) 0.3771(5) 0.074(2) Uani 1 1 d . . . H20 H 1.1383 -0.6609 0.3494 0.089 Uiso 1 1 calc R . . C19 C 1.4386(9) -0.6981(11) 0.4554(5) 0.096(3) Uani 1 1 d . . . H19 H 1.5164 -0.7088 0.4819 0.115 Uiso 1 1 calc R . . C21 C 1.3595(10) -0.7828(10) 0.4812(5) 0.090(3) Uani 1 1 d . . . H21 H 1.3835 -0.8516 0.5250 0.108 Uiso 1 1 calc R . . O2 O 1.0428(5) 0.0255(5) 0.1131(2) 0.0607(12) Uani 1 1 d . . . O9 O 1.2161(5) -1.2318(5) 0.6308(3) 0.0801(15) Uani 1 1 d . . . O4 O 1.0029(5) -0.0152(5) 0.3810(2) 0.0698(14) Uani 1 1 d . . . C5 C 1.1058(7) -0.1053(7) 0.3959(4) 0.0567(16) 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 Cu1 0.0522(5) 0.0516(5) 0.0574(5) -0.0286(4) 0.0361(4) -0.0319(4) Cu2 0.0576(5) 0.0455(5) 0.0543(5) -0.0165(4) 0.0276(4) -0.0280(4) O8 0.072(3) 0.054(3) 0.076(3) -0.024(2) 0.043(2) -0.043(2) C1 0.061(3) 0.070(4) 0.034(3) -0.030(3) 0.026(2) -0.046(3) O7 0.059(2) 0.056(3) 0.075(3) -0.026(2) 0.034(2) -0.037(2) O5 0.070(3) 0.065(3) 0.071(3) -0.005(2) 0.015(2) -0.043(2) O6 0.077(3) 0.055(3) 0.091(4) -0.013(2) 0.037(3) -0.044(3) O3 0.064(3) 0.069(3) 0.069(3) -0.031(3) 0.024(2) -0.021(2) O1 0.064(3) 0.063(3) 0.069(3) -0.036(2) 0.034(2) -0.030(2) N9 0.064(3) 0.054(3) 0.079(4) -0.016(3) 0.041(3) -0.035(3) C7 0.064(4) 0.052(4) 0.066(4) -0.019(3) 0.041(3) -0.036(3) C15 0.053(3) 0.046(4) 0.058(3) -0.013(3) 0.024(3) -0.021(3) O10 0.080(3) 0.078(4) 0.151(6) -0.083(4) 0.056(4) -0.035(3) C14 0.072(4) 0.056(4) 0.071(4) -0.028(3) 0.046(3) -0.044(3) C2 0.063(4) 0.047(4) 0.076(4) -0.025(3) 0.038(3) -0.029(3) C24 0.075(4) 0.061(4) 0.081(4) -0.034(4) 0.047(4) -0.047(4) C4 0.061(4) 0.053(4) 0.055(4) -0.020(3) 0.034(3) -0.026(3) C6 0.071(4) 0.066(4) 0.062(4) -0.018(3) 0.036(3) -0.044(4) C10 0.057(3) 0.051(4) 0.069(4) -0.022(3) 0.032(3) -0.028(3) C13 0.047(3) 0.055(4) 0.082(4) -0.026(3) 0.040(3) -0.034(3) C12 0.075(5) 0.072(5) 0.093(5) -0.034(4) 0.059(4) -0.042(4) C16 0.064(4) 0.057(4) 0.082(5) -0.011(3) 0.029(4) -0.034(3) C23 0.071(4) 0.056(4) 0.052(3) -0.009(3) 0.019(3) -0.034(3) C11 0.069(4) 0.053(4) 0.082(5) -0.031(3) 0.035(3) -0.035(3) C9 0.080(5) 0.060(4) 0.068(4) -0.019(3) 0.046(4) -0.036(4) C8 0.065(4) 0.053(4) 0.089(5) -0.020(4) 0.041(4) -0.033(3) C17 0.080(5) 0.061(4) 0.054(4) -0.011(3) 0.029(3) -0.030(4) C18 0.063(4) 0.070(5) 0.099(6) -0.012(4) 0.018(4) -0.036(4) C22 0.066(4) 0.054(4) 0.067(4) -0.018(3) 0.032(3) -0.035(3) C3 0.085(5) 0.052(4) 0.076(5) -0.026(3) 0.048(4) -0.040(4) C20 0.069(4) 0.062(5) 0.095(5) -0.006(4) 0.025(4) -0.035(4) C19 0.096(6) 0.135(8) 0.086(6) -0.020(6) 0.005(5) -0.086(6) C21 0.114(7) 0.100(7) 0.077(5) -0.003(5) 0.008(5) -0.077(6) O2 0.077(3) 0.057(3) 0.059(3) -0.025(2) 0.028(2) -0.031(3) O9 0.074(3) 0.059(3) 0.097(4) 0.001(3) -0.008(3) -0.015(3) O4 0.101(4) 0.065(3) 0.048(2) -0.029(2) 0.034(2) -0.023(3) C5 0.071(4) 0.048(4) 0.054(4) -0.014(3) 0.023(3) -0.024(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. ; 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 O7 1.957(4) 2_855 ? Cu1 O2 1.961(5) . ? Cu1 O1 1.970(5) 2_755 ? Cu1 O8 1.972(4) 1_455 ? Cu1 O10 2.146(4) . ? Cu1 Cu1 2.6282(15) 2_755 ? Cu2 O3 1.953(4) 1_545 ? Cu2 O6 1.957(4) 2_736 ? Cu2 O4 1.961(4) 2_746 ? Cu2 O5 1.969(4) . ? Cu2 O9 2.159(5) . ? Cu2 Cu2 2.628(2) 2_736 ? O8 C15 1.232(7) . ? O8 Cu1 1.972(4) 1_655 ? C1 O2 1.228(8) . ? C1 O1 1.271(6) . ? C1 C2 1.530(10) . ? O7 C15 1.273(7) . ? O7 Cu1 1.957(4) 2_855 ? O5 C23 1.252(8) . ? O6 C23 1.271(9) . ? O6 Cu2 1.957(4) 2_736 ? O3 C5 1.249(8) . ? O3 Cu2 1.953(4) 1_565 ? O1 Cu1 1.970(5) 2_755 ? N9 C7 1.377(9) . ? N9 C16 1.434(9) . ? N9 C8 1.454(8) . ? C7 C6 1.403(8) . ? C7 C14 1.421(10) . ? C15 C13 1.502(7) . ? C14 C2 1.369(10) . ? C14 H14 0.9500 . ? C2 C3 1.397(8) . ? C24 C13 1.369(8) . ? C24 C9 1.400(8) . ? C24 H24 0.9500 . ? C4 C3 1.340(10) . ? C4 C6 1.387(10) . ? C4 C5 1.522(8) . ? C6 H6 0.9500 . ? C10 C11 1.351(8) . ? C10 C9 1.389(9) . ? C10 C8 1.515(7) . ? C13 C12 1.363(9) . ? C12 C11 1.392(8) . ? C12 H12 0.9500 . ? C16 C17 1.530(8) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C23 C22 1.497(8) . ? C11 H11 0.9500 . ? C9 H9 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C17 C18 1.360(11) . ? C17 C19 1.391(12) . ? C18 C20 1.391(9) . ? C18 H18 0.9500 . ? C22 C20 1.387(11) . ? C22 C21 1.389(11) . ? C3 H3 0.9500 . ? C20 H20 0.9500 . ? C19 C21 1.388(10) . ? C19 H19 0.9500 . ? C21 H21 0.9500 . ? O4 C5 1.243(9) . ? O4 Cu2 1.961(4) 2_746 ? 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 O7 Cu1 O2 89.78(19) 2_855 . ? O7 Cu1 O1 88.92(19) 2_855 2_755 ? O2 Cu1 O1 168.59(18) . 2_755 ? O7 Cu1 O8 168.23(18) 2_855 1_455 ? O2 Cu1 O8 86.8(2) . 1_455 ? O1 Cu1 O8 92.2(2) 2_755 1_455 ? O7 Cu1 O10 95.81(18) 2_855 . ? O2 Cu1 O10 96.0(2) . . ? O1 Cu1 O10 95.4(2) 2_755 . ? O8 Cu1 O10 95.75(19) 1_455 . ? O7 Cu1 Cu1 85.40(13) 2_855 2_755 ? O2 Cu1 Cu1 83.91(14) . 2_755 ? O1 Cu1 Cu1 84.69(13) 2_755 2_755 ? O8 Cu1 Cu1 83.03(13) 1_455 2_755 ? O10 Cu1 Cu1 178.78(15) . 2_755 ? O3 Cu2 O6 90.6(2) 1_545 2_736 ? O3 Cu2 O4 168.3(2) 1_545 2_746 ? O6 Cu2 O4 88.6(2) 2_736 2_746 ? O3 Cu2 O5 88.4(2) 1_545 . ? O6 Cu2 O5 168.7(2) 2_736 . ? O4 Cu2 O5 90.1(2) 2_746 . ? O3 Cu2 O9 98.8(2) 1_545 . ? O6 Cu2 O9 92.4(2) 2_736 . ? O4 Cu2 O9 92.9(2) 2_746 . ? O5 Cu2 O9 98.8(2) . . ? O3 Cu2 Cu2 85.31(16) 1_545 2_736 ? O6 Cu2 Cu2 80.56(18) 2_736 2_736 ? O4 Cu2 Cu2 83.05(17) 2_746 2_736 ? O5 Cu2 Cu2 88.17(16) . 2_736 ? O9 Cu2 Cu2 171.95(15) . 2_736 ? C15 O8 Cu1 124.2(3) . 1_655 ? O2 C1 O1 127.1(6) . . ? O2 C1 C2 117.0(5) . . ? O1 C1 C2 115.8(6) . . ? C15 O7 Cu1 121.1(4) . 2_855 ? C23 O5 Cu2 118.2(4) . . ? C23 O6 Cu2 127.3(4) . 2_736 ? C5 O3 Cu2 120.9(4) . 1_565 ? C1 O1 Cu1 120.7(5) . 2_755 ? C7 N9 C16 120.8(5) . . ? C7 N9 C8 120.5(6) . . ? C16 N9 C8 116.4(6) . . ? N9 C7 C6 121.9(7) . . ? N9 C7 C14 122.5(6) . . ? C6 C7 C14 115.6(6) . . ? O8 C15 O7 126.1(5) . . ? O8 C15 C13 117.5(5) . . ? O7 C15 C13 116.4(5) . . ? C2 C14 C7 121.8(6) . . ? C2 C14 H14 119.1 . . ? C7 C14 H14 119.1 . . ? C14 C2 C3 120.2(7) . . ? C14 C2 C1 120.8(6) . . ? C3 C2 C1 118.6(6) . . ? C13 C24 C9 119.5(6) . . ? C13 C24 H24 120.3 . . ? C9 C24 H24 120.3 . . ? C3 C4 C6 121.9(6) . . ? C3 C4 C5 119.8(6) . . ? C6 C4 C5 118.3(6) . . ? C4 C6 C7 121.2(7) . . ? C4 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C11 C10 C9 118.8(5) . . ? C11 C10 C8 119.6(6) . . ? C9 C10 C8 121.6(5) . . ? C12 C13 C24 119.7(5) . . ? C12 C13 C15 121.2(5) . . ? C24 C13 C15 119.0(5) . . ? C13 C12 C11 120.6(6) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? N9 C16 C17 115.4(6) . . ? N9 C16 H16A 108.4 . . ? C17 C16 H16A 108.4 . . ? N9 C16 H16B 108.4 . . ? C17 C16 H16B 108.4 . . ? H16A C16 H16B 107.5 . . ? O5 C23 O6 125.6(6) . . ? O5 C23 C22 117.6(7) . . ? O6 C23 C22 116.7(6) . . ? C10 C11 C12 120.9(6) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C10 C9 C24 120.5(5) . . ? C10 C9 H9 119.7 . . ? C24 C9 H9 119.7 . . ? N9 C8 C10 113.9(5) . . ? N9 C8 H8A 108.8 . . ? C10 C8 H8A 108.8 . . ? N9 C8 H8B 108.8 . . ? C10 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C18 C17 C19 119.1(7) . . ? C18 C17 C16 121.8(7) . . ? C19 C17 C16 119.1(7) . . ? C17 C18 C20 121.5(8) . . ? C17 C18 H18 119.2 . . ? C20 C18 H18 119.2 . . ? C20 C22 C21 119.5(6) . . ? C20 C22 C23 118.9(7) . . ? C21 C22 C23 121.6(7) . . ? C4 C3 C2 119.1(7) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C22 C20 C18 119.4(8) . . ? C22 C20 H20 120.3 . . ? C18 C20 H20 120.3 . . ? C21 C19 C17 120.4(8) . . ? C21 C19 H19 119.8 . . ? C17 C19 H19 119.8 . . ? C19 C21 C22 119.9(8) . . ? C19 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C1 O2 Cu1 123.0(4) . . ? C5 O4 Cu2 123.3(4) . 2_746 ? O4 C5 O3 127.1(6) . . ? O4 C5 C4 114.8(6) . . ? O3 C5 C4 118.1(6) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 67.31 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.813 _refine_diff_density_min -0.648 _refine_diff_density_rms 0.102 # 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 0.057 0.382 0.138 993 356 ' ' _platon_squeeze_details ? _database_code_depnum_ccdc_archive 'CCDC 943581'