# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Zaworotko, Michael' 'Perman, Jason' 'Wojtas, Lukasz' 'Cairns, Amy' 'Eddaoudi, Mohammed' _publ_contact_author_name 'Zaworotko, Michael' _publ_contact_author_email xtal@usf.edu _publ_section_title ; Cocrystal Controlled Solid-State Synthesis of a Rigid Tetracarboxylate Ligand that Pillars both Square Grid and Kagome Lattice Layers ; # Attachment '- 1.cif' data_me676 _database_code_depnum_ccdc_archive 'CCDC 789422' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H10 Cu2 N2 O14' _chemical_formula_weight 749.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Cu Cu 0.3201 1.2651 '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/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 32.461(12) _cell_length_b 18.024(6) _cell_length_c 19.748(7) _cell_angle_alpha 90.00 _cell_angle_beta 119.964(9) _cell_angle_gamma 90.00 _cell_volume 10010(6) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2244 _exptl_absorpt_coefficient_mu 0.672 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9672 _exptl_absorpt_correction_T_max 0.9801 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16510 _diffrn_reflns_av_R_equivalents 0.1855 _diffrn_reflns_av_sigmaI/netI 0.2432 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 20.99 _reflns_number_total 5453 _reflns_number_gt 2218 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART APEX (Bruker, 2000)' _computing_cell_refinement 'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'APEX2 (Bruker, 2010)' _publ_section_references ; Bruker AXS. (2009). SAINT Bruker AXS, Inc. Madison, Wisconsin, USA. Sheldrick, G. M. (2008). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _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^)+(0.0212P)^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 5453 _refine_ls_number_parameters 282 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1634 _refine_ls_R_factor_gt 0.0819 _refine_ls_wR_factor_ref 0.1568 _refine_ls_wR_factor_gt 0.1423 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.952 _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 O5 O 0.2620(2) 0.1296(4) -0.0004(4) 0.061(2) Uani 1 1 d . . . O7 O 0.1875(3) 0.1966(5) -0.0030(5) 0.072(2) Uani 1 1 d . . . O2 O 0.0454(2) 0.0747(4) 0.0965(3) 0.053(2) Uani 1 1 d . . . Cu1 Cu 0.00400(6) 0.0000 -0.06329(9) 0.0366(6) Uani 1 2 d S . . Cu2 Cu 0.27992(5) 0.28878(9) 0.06166(7) 0.0585(6) Uani 1 1 d . . . O1 O -0.0051(4) 0.0000 -0.1816(5) 0.073(3) Uani 1 2 d S . . O8 O 0.3280(2) 0.3584(5) 0.1600(4) 0.101(3) Uani 1 1 d . . . O3 O 0.0533(2) 0.0708(5) -0.0110(4) 0.066(3) Uani 1 1 d . . . O4 O 0.2382(3) 0.2623(4) 0.1008(4) 0.056(2) Uani 1 1 d . . . O6 O 0.3141(3) 0.1940(5) 0.1063(4) 0.065(3) Uani 1 1 d . . . C1 C 0.0672(4) 0.0999(7) 0.0614(8) 0.063(4) Uani 1 1 d . . . C2 C 0.1060(4) 0.1435(7) 0.0987(7) 0.055(3) Uani 1 1 d U . . C3 C 0.1300(3) 0.1652(6) 0.0618(5) 0.035(3) Uani 1 1 d . . . H3 H 0.1193 0.1504 0.0094 0.042 Uiso 1 1 calc R . . C4 C 0.1709(5) 0.2101(8) 0.1023(8) 0.076(4) Uani 1 1 d . . . C5 C 0.1976(6) 0.2270(9) 0.0664(9) 0.105(6) Uani 1 1 d . . . C6 C 0.1917(5) 0.2246(8) 0.1808(7) 0.091(5) Uani 1 1 d . . . H6 H 0.2207 0.2508 0.2097 0.109 Uiso 1 1 calc R . . C7 C 0.1655(5) 0.1966(7) 0.2140(6) 0.067(4) Uani 1 1 d . . . C8 C 0.1243(4) 0.1592(8) 0.1791(8) 0.098(5) Uani 1 1 d . . . H8 H 0.1084 0.1443 0.2064 0.118 Uiso 1 1 calc R . . C11 C 0.2232(4) 0.3058(9) 0.4079(8) 0.080(4) Uiso 1 1 d . . . C12 C 0.2382(4) 0.2468(7) 0.4599(5) 0.070(4) Uani 1 1 d . . . C13 C 0.2235(4) 0.1768(9) 0.4323(8) 0.081(4) Uiso 1 1 d . . . C14 C 0.2389(5) 0.3759(10) 0.4368(10) 0.152(7) Uiso 1 1 d . . . H14 H 0.2315 0.4168 0.4022 0.182 Uiso 1 1 calc R . . C15 C 0.2330(5) 0.1131(9) 0.4793(9) 0.127(6) Uiso 1 1 d . . . H15 H 0.2216 0.0655 0.4572 0.153 Uiso 1 1 calc R . . C16 C 0.3034(6) 0.0000 0.0717(10) 0.062(6) Uani 1 2 d S . . H16 H 0.2756 0.0000 0.0216 0.075 Uiso 1 2 calc SR . . C35 C 0.1947(5) 0.2855(11) 0.3201(9) 0.115(5) Uiso 1 1 d . . . C18 C 0.3626(5) 0.0651(9) 0.1859(8) 0.088(5) Uani 1 1 d . . . H18 H 0.3789 0.1093 0.2113 0.105 Uiso 1 1 calc R . . C19 C 0.3748(8) 0.0000 0.2212(13) 0.102(8) Uani 1 2 d S . . C17 C 0.3228(4) 0.0655(8) 0.1065(8) 0.067(4) Uani 1 1 d . . . O100 O 0.1818(3) 0.3401(6) 0.2772(5) 0.114(3) Uiso 1 1 d . . . O101 O 0.1816(4) 0.0967(7) 0.3180(6) 0.141(4) Uiso 1 1 d . . . C31 C 0.1973(6) 0.1538(11) 0.3466(10) 0.124(6) Uiso 1 1 d . . . N32 N 0.1859(3) 0.2171(7) 0.2996(6) 0.085(3) Uiso 1 1 d . . . C33 C 0.3010(5) 0.1365(10) 0.0683(9) 0.081(5) Uani 1 1 d . . . C52 C 0.4379(8) 0.0250(14) 0.4366(13) 0.083(8) Uiso 0.50 1 d P . . C23 C 0.4820(5) 0.0000 0.4592(7) 0.047(4) Uiso 1 2 d S . . C57 C 0.5079(6) 0.0217(12) 0.5971(10) 0.044(6) Uiso 0.50 1 d P . . C55 C 0.4607(9) 0.0473(14) 0.5703(16) 0.123(11) Uiso 0.50 1 d P . . H55 H 0.4531 0.0608 0.6094 0.147 Uiso 0.50 1 calc PR . . C56 C 0.4230(12) 0.0550(17) 0.4899(18) 0.150(13) Uiso 0.50 1 d P . . H56 H 0.3928 0.0765 0.4740 0.180 Uiso 0.50 1 calc PR . . O52 O 0.3558(6) -0.0531(10) 0.3289(10) 0.124(7) Uiso 0.50 1 d P . . N105 N 0.4149(5) 0.0000 0.3045(7) 0.073(5) Uani 1 2 d S . . C51 C 0.4057(8) -0.0303(12) 0.3600(13) 0.072(8) Uiso 0.50 1 d P . . C58 C 0.4583(9) 0.021(2) 0.3188(14) 0.107(11) Uiso 0.50 1 d P . . O57 O 0.4714(8) 0.0534(13) 0.2743(13) 0.165(9) Uiso 0.50 1 d P . . 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 O5 0.053(5) 0.082(7) 0.047(5) 0.001(5) 0.024(4) -0.015(5) O7 0.086(6) 0.070(7) 0.078(6) -0.007(5) 0.054(5) -0.020(5) O2 0.029(4) 0.095(7) 0.039(5) -0.008(4) 0.019(4) -0.008(5) Cu1 0.0293(11) 0.0541(16) 0.0278(11) 0.000 0.0153(9) 0.000 Cu2 0.0528(9) 0.0919(14) 0.0289(8) -0.0155(9) 0.0189(7) -0.0344(10) O1 0.105(8) 0.097(10) 0.058(7) 0.000 0.073(7) 0.000 O8 0.074(6) 0.120(8) 0.085(6) -0.068(6) 0.022(5) -0.038(6) O3 0.044(5) 0.113(8) 0.040(5) -0.015(5) 0.019(4) -0.003(5) O4 0.073(5) 0.067(7) 0.041(5) -0.002(4) 0.037(4) -0.027(5) O6 0.062(5) 0.069(8) 0.055(5) 0.011(5) 0.023(4) -0.009(6) C1 0.046(9) 0.039(9) 0.105(12) 0.010(9) 0.037(9) -0.018(7) C2 0.055(7) 0.070(8) 0.048(6) -0.010(6) 0.032(6) -0.029(6) C3 0.031(6) 0.044(8) 0.027(6) -0.023(6) 0.012(5) -0.020(6) C4 0.081(11) 0.110(13) 0.074(10) -0.012(10) 0.066(9) -0.029(10) C5 0.106(14) 0.082(14) 0.087(13) -0.025(11) 0.018(11) 0.027(12) C6 0.114(12) 0.120(14) 0.053(10) -0.032(9) 0.052(9) -0.041(10) C7 0.074(9) 0.089(12) 0.034(7) -0.024(7) 0.025(7) -0.024(9) C8 0.061(9) 0.150(15) 0.077(11) -0.061(10) 0.030(8) -0.066(9) C12 0.105(11) 0.060(10) 0.057(9) -0.016(9) 0.050(9) -0.032(9) C16 0.055(13) 0.043(16) 0.069(14) 0.000 0.017(11) 0.000 C18 0.082(10) 0.113(17) 0.074(11) 0.031(10) 0.043(9) -0.006(11) C19 0.097(18) 0.14(3) 0.064(19) 0.000 0.038(15) 0.000 C17 0.058(10) 0.069(14) 0.082(12) 0.032(10) 0.041(9) 0.027(9) C33 0.052(10) 0.108(17) 0.089(13) -0.042(12) 0.040(10) -0.043(11) N105 0.037(9) 0.131(15) 0.048(10) 0.000 0.020(8) 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 O5 C33 1.320(13) . ? O5 Cu2 1.958(8) 7 ? O7 C5 1.354(15) . ? O7 Cu2 1.939(7) 7 ? O2 C1 1.296(12) . ? O2 Cu1 1.940(7) 5 ? Cu1 O3 1.898(7) . ? Cu1 O3 1.898(7) 6 ? Cu1 O2 1.940(7) 5 ? Cu1 O2 1.940(7) 2 ? Cu1 O1 2.204(8) . ? Cu1 Cu1 2.639(3) 5 ? Cu2 O4 1.925(7) . ? Cu2 O7 1.939(7) 7 ? Cu2 O5 1.958(8) 7 ? Cu2 O6 1.987(8) . ? Cu2 O8 2.180(7) . ? Cu2 Cu2 2.633(3) 7 ? O3 C1 1.370(13) . ? O4 C5 1.308(16) . ? O6 C33 1.225(14) . ? C1 C2 1.349(14) . ? C2 C3 1.363(13) . ? C2 C8 1.418(13) . ? C3 C4 1.413(14) . ? C3 H3 0.9500 . ? C4 C6 1.373(13) . ? C4 C5 1.400(18) . ? C6 C7 1.399(14) . ? C6 H6 0.9500 . ? C7 C8 1.342(13) . ? C7 N32 1.521(12) . ? C8 H8 0.9500 . ? C11 C14 1.376(18) . ? C11 C12 1.386(15) . ? C11 C35 1.548(16) . ? C12 C13 1.362(15) . ? C12 C12 1.378(18) 7_556 ? C13 C15 1.410(17) . ? C13 C31 1.524(17) . ? C14 C15 1.451(17) 7_556 ? C14 H14 0.9500 . ? C15 C14 1.451(17) 7_556 ? C15 H15 0.9500 . ? C16 C17 1.353(15) . ? C16 C17 1.353(15) 6 ? C16 H16 0.9500 . ? C35 O100 1.228(16) . ? C35 N32 1.285(17) . ? C18 C19 1.320(13) . ? C18 C17 1.451(17) . ? C18 H18 0.9500 . ? C19 C18 1.320(13) 6 ? C19 N105 1.50(2) . ? C17 C33 1.474(18) . ? O101 C31 1.161(17) . ? C31 N32 1.400(17) . ? C52 C52 0.90(5) 6 ? C52 C51 1.35(2) 6 ? C52 C23 1.35(2) . ? C52 C56 1.46(3) . ? C52 C51 1.67(2) . ? C23 C52 1.35(2) 6 ? C23 C57 1.363(17) 5_656 ? C23 C57 1.363(17) 2_656 ? C23 C23 1.44(2) 5_656 ? C57 C57 0.78(4) 6 ? C57 C23 1.363(17) 5_656 ? C57 C55 1.43(3) . ? C57 C58 1.46(2) 2_656 ? C57 C58 1.65(3) 5_656 ? C55 C56 1.45(3) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? O52 C51 1.48(2) . ? N105 C58 1.34(3) 6 ? N105 C58 1.34(3) . ? N105 C51 1.38(2) 6 ? N105 C51 1.38(2) . ? C51 C51 1.09(4) 6 ? C51 C52 1.35(2) 6 ? C58 C58 0.74(7) 6 ? C58 O57 1.29(3) . ? C58 C57 1.46(2) 2_656 ? C58 C57 1.65(3) 5_656 ? C58 O57 1.76(3) 6 ? O57 C58 1.76(3) 6 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C33 O5 Cu2 125.3(10) . 7 ? C5 O7 Cu2 128.4(10) . 7 ? C1 O2 Cu1 130.0(7) . 5 ? O3 Cu1 O3 84.4(5) . 6 ? O3 Cu1 O2 168.6(3) . 5 ? O3 Cu1 O2 92.7(3) 6 5 ? O3 Cu1 O2 92.7(3) . 2 ? O3 Cu1 O2 168.6(3) 6 2 ? O2 Cu1 O2 88.0(4) 5 2 ? O3 Cu1 O1 101.9(3) . . ? O3 Cu1 O1 101.9(3) 6 . ? O2 Cu1 O1 89.5(3) 5 . ? O2 Cu1 O1 89.5(3) 2 . ? O3 Cu1 Cu1 86.6(2) . 5 ? O3 Cu1 Cu1 86.6(2) 6 5 ? O2 Cu1 Cu1 82.20(19) 5 5 ? O2 Cu1 Cu1 82.20(19) 2 5 ? O1 Cu1 Cu1 168.4(3) . 5 ? O4 Cu2 O7 167.8(3) . 7 ? O4 Cu2 O5 91.3(3) . 7 ? O7 Cu2 O5 87.0(3) 7 7 ? O4 Cu2 O6 87.5(3) . . ? O7 Cu2 O6 91.8(3) 7 . ? O5 Cu2 O6 168.9(3) 7 . ? O4 Cu2 O8 96.8(3) . . ? O7 Cu2 O8 95.3(3) 7 . ? O5 Cu2 O8 94.9(3) 7 . ? O6 Cu2 O8 96.2(4) . . ? O4 Cu2 Cu2 84.1(2) . 7 ? O7 Cu2 Cu2 83.7(2) 7 7 ? O5 Cu2 Cu2 82.2(2) 7 7 ? O6 Cu2 Cu2 86.8(3) . 7 ? O8 Cu2 Cu2 176.9(3) . 7 ? C1 O3 Cu1 125.0(7) . . ? C5 O4 Cu2 129.8(10) . . ? C33 O6 Cu2 120.7(10) . . ? O2 C1 C2 121.5(13) . . ? O2 C1 O3 116.1(10) . . ? C2 C1 O3 121.7(12) . . ? C1 C2 C3 120.0(12) . . ? C1 C2 C8 118.8(12) . . ? C3 C2 C8 120.7(11) . . ? C2 C3 C4 119.2(10) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C6 C4 C5 116.9(13) . . ? C6 C4 C3 122.7(11) . . ? C5 C4 C3 118.8(13) . . ? O4 C5 O7 113.3(16) . . ? O4 C5 C4 124.1(14) . . ? O7 C5 C4 121.7(15) . . ? C4 C6 C7 113.0(12) . . ? C4 C6 H6 123.5 . . ? C7 C6 H6 123.5 . . ? C8 C7 C6 128.6(11) . . ? C8 C7 N32 117.4(12) . . ? C6 C7 N32 113.9(11) . . ? C7 C8 C2 115.2(12) . . ? C7 C8 H8 122.4 . . ? C2 C8 H8 122.4 . . ? C14 C11 C12 118.6(15) . . ? C14 C11 C35 124.8(16) . . ? C12 C11 C35 116.1(14) . . ? C13 C12 C12 114.8(16) . 7_556 ? C13 C12 C11 119.5(11) . . ? C12 C12 C11 125.1(16) 7_556 . ? C12 C13 C15 124.9(15) . . ? C12 C13 C31 125.9(14) . . ? C15 C13 C31 109.1(16) . . ? C11 C14 C15 119.2(17) . 7_556 ? C11 C14 H14 120.4 . . ? C15 C14 H14 120.4 7_556 . ? C13 C15 C14 116.6(16) . 7_556 ? C13 C15 H15 121.7 . . ? C14 C15 H15 121.7 7_556 . ? C17 C16 C17 121.6(19) . 6 ? C17 C16 H16 119.2 . . ? C17 C16 H16 119.2 6 . ? O100 C35 N32 127.3(16) . . ? O100 C35 C11 113.0(16) . . ? N32 C35 C11 119.7(15) . . ? C19 C18 C17 116.5(18) . . ? C19 C18 H18 121.7 . . ? C17 C18 H18 121.7 . . ? C18 C19 C18 125(2) 6 . ? C18 C19 N105 116.4(12) 6 . ? C18 C19 N105 116.4(12) . . ? C16 C17 C18 118.8(15) . . ? C16 C17 C33 120.9(14) . . ? C18 C17 C33 120.0(14) . . ? O101 C31 N32 119.5(17) . . ? O101 C31 C13 130.4(19) . . ? N32 C31 C13 109.3(16) . . ? C35 N32 C31 129.0(15) . . ? C35 N32 C7 119.3(13) . . ? C31 N32 C7 111.3(13) . . ? O6 C33 O5 124.8(17) . . ? O6 C33 C17 119.3(14) . . ? O5 C33 C17 114.5(14) . . ? C52 C52 C51 94.0(15) 6 6 ? C52 C52 C23 70.5(10) 6 . ? C51 C52 C23 120(2) 6 . ? C52 C52 C56 111.7(16) 6 . ? C51 C52 C56 116(2) 6 . ? C23 C52 C56 124(2) . . ? C23 C52 C51 100.3(17) . . ? C56 C52 C51 126(2) . . ? C51 C52 C56 113(2) 6 6 ? C23 C52 C56 94.7(17) . 6 ? C51 C52 C56 80.8(16) . 6 ? C52 C23 C57 106.5(14) 6 5_656 ? C52 C23 C57 118.4(15) . 5_656 ? C52 C23 C57 118.4(15) 6 2_656 ? C52 C23 C57 106.5(14) . 2_656 ? C52 C23 C23 120.2(18) 6 5_656 ? C52 C23 C23 120.2(18) . 5_656 ? C57 C23 C23 121.4(17) 5_656 5_656 ? C57 C23 C23 121.4(17) 2_656 5_656 ? C57 C57 C23 73.4(9) 6 5_656 ? C57 C57 C55 108.9(14) 6 . ? C23 C57 C55 116.3(18) 5_656 . ? C57 C57 C58 89.3(17) 6 2_656 ? C23 C57 C58 124.9(19) 5_656 2_656 ? C55 C57 C58 119(2) . 2_656 ? C57 C57 C58 62.5(13) 6 5_656 ? C23 C57 C58 112.2(16) 5_656 5_656 ? C55 C57 C58 125.0(19) . 5_656 ? C23 C57 C55 94.5(14) 5_656 6 ? C58 C57 C55 111.3(19) 2_656 6 ? C58 C57 C55 91.0(17) 5_656 6 ? C57 C55 C56 127(3) . . ? C57 C55 H55 116.6 . . ? C56 C55 H55 116.6 . . ? C55 C56 C52 111(3) . . ? C55 C56 H56 124.6 . . ? C52 C56 H56 124.6 . . ? C58 N105 C51 124.1(19) 6 6 ? C58 N105 C51 110.0(17) . 6 ? C58 N105 C51 110.0(17) 6 . ? C58 N105 C51 124.1(19) . . ? C58 N105 C19 118.4(16) 6 . ? C58 N105 C19 118.4(16) . . ? C51 N105 C19 117.0(15) 6 . ? C51 N105 C19 117.0(15) . . ? C51 C51 C52 86.0(15) 6 6 ? C51 C51 N105 66.8(9) 6 . ? C52 C51 N105 121(2) 6 . ? C51 C51 O52 106.2(11) 6 . ? C52 C51 O52 124(2) 6 . ? N105 C51 O52 114.1(19) . . ? N105 C51 C52 101.5(16) . . ? O52 C51 C52 126.9(18) . . ? C58 C58 O57 117.1(19) 6 . ? C58 C58 N105 73.9(15) 6 . ? O57 C58 N105 130(2) . . ? C58 C58 C57 90.7(17) 6 2_656 ? O57 C58 C57 117(3) . 2_656 ? N105 C58 C57 111(2) . 2_656 ? C58 C58 C57 62.5(13) 6 5_656 ? O57 C58 C57 128(2) . 5_656 ? N105 C58 C57 101(2) . 5_656 ? O57 C58 O57 76(2) . 6 ? N105 C58 O57 100(2) . 6 ? C57 C58 O57 110(2) 2_656 6 ? C57 C58 O57 87.0(18) 5_656 6 ? 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 0.188 -0.003 -0.003 2435 756 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 20.99 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.699 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.075 # Attachment '- 2a.cif' data_me840 _database_code_depnum_ccdc_archive 'CCDC 789423' #TrackingRef '- 2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H28 Cu2 N4 O14' _chemical_formula_weight 891.72 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 orthorhombic _symmetry_space_group_name_H-M Imma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z' '-x, y+1/2, -z' 'x, -y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1, z+1/2' '-x+1/2, y+1, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z' 'x, -y-1/2, z' '-x, y, z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y, -z+1/2' 'x+1/2, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 15.2248(3) _cell_length_b 36.4392(7) _cell_length_c 10.3036(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5716.23(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2295 _cell_measurement_theta_min 4.45 _cell_measurement_theta_max 64.4 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.036 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1816 _exptl_absorpt_coefficient_mu 1.352 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8766 _exptl_absorpt_correction_T_max 0.8766 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEXII CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12420 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 65.69 _reflns_number_total 2594 _reflns_number_gt 2170 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'APEX2 (Bruker, 2010)' _publ_section_references ; Bruker AXS. (2010). APEX2 Bruker AXS, Inc. Madison, Wisconsin, USA. Bruker AXS. (2009). SAINT Bruker AXS, Inc. Madison, Wisconsin, USA. Sheldrick, G. M. (2008). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _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^)+(0.0705P)^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 2594 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.0000 0.474731(10) 0.09328(4) 0.02224(16) Uani 1 2 d S . . O1 O 0.08887(10) 0.44875(4) -0.00660(15) 0.0358(4) Uani 1 1 d . . . O2 O 0.09227(9) 0.50740(4) 0.15961(15) 0.0341(4) Uani 1 1 d . . . O3 O 0.1506(2) 0.34679(5) -0.4110(3) 0.0990(10) Uani 1 1 d . . . C1 C 0.11725(13) 0.46310(5) -0.1085(2) 0.0281(4) Uani 1 1 d . . . C2 C 0.2500 0.46143(7) -0.2500 0.0285(6) Uani 1 2 d S . . H2 H 0.2500 0.4875 -0.2500 0.034 Uiso 1 2 calc SR . . C3 C 0.18739(13) 0.44268(5) -0.1802(2) 0.0297(5) Uani 1 1 d . . . C4 C 0.18865(14) 0.40432(5) -0.1766(2) 0.0346(5) Uani 1 1 d . . . H4 H 0.1479 0.3912 -0.1245 0.042 Uiso 1 1 calc R . . C5 C 0.2500 0.38600(8) -0.2500 0.0373(7) Uani 1 2 d S . . N1 N 0.2500 0.34610(6) -0.2500 0.0397(7) Uani 1 2 d S . . C6 C 0.1956(2) 0.32898(7) -0.3391(3) 0.0578(7) Uani 1 1 d . . . C7 C 0.1954(2) 0.28809(7) -0.3372(3) 0.0558(7) Uani 1 1 d . . . C8 C 0.1424(3) 0.26930(8) -0.4189(4) 0.0909(14) Uani 1 1 d . . . H8 H 0.1049 0.2823 -0.4766 0.109 Uiso 1 1 calc R . . C9 C 0.2500 0.26941(8) -0.2500 0.0413(8) Uani 1 2 d S . . O11 O 0.0000 0.43927(6) 0.2543(2) 0.0440(6) Uani 1 2 d S . . N11 N 0.0146(14) 0.43603(14) 0.4673(4) 0.070(5) Uani 0.50 1 d P A -1 C11 C -0.0286(3) 0.43730(12) 0.3590(5) 0.0406(12) Uani 0.50 1 d P A -1 C12 C -0.0231(11) 0.4291(3) 0.5976(6) 0.120(7) Uani 0.50 1 d P A -1 H12A H -0.0791 0.4422 0.6059 0.180 Uiso 0.50 1 calc PR A -1 H12B H 0.0178 0.4379 0.6642 0.180 Uiso 0.50 1 calc PR A -1 H12C H -0.0329 0.4028 0.6089 0.180 Uiso 0.50 1 calc PR A -1 C13 C 0.1101(6) 0.4415(3) 0.4632(10) 0.117(4) Uani 0.50 1 d P A -1 H13A H 0.1392 0.4178 0.4503 0.175 Uiso 0.50 1 calc PR A -1 H13B H 0.1298 0.4523 0.5452 0.175 Uiso 0.50 1 calc PR A -1 H13C H 0.1250 0.4580 0.3914 0.175 Uiso 0.50 1 calc PR A -1 C14 C -0.1297(4) 0.4333(2) 0.3572(8) 0.080(2) Uani 0.50 1 d P A -1 H14A H -0.1567 0.4569 0.3794 0.120 Uiso 0.50 1 calc PR A -1 H14B H -0.1476 0.4147 0.4207 0.120 Uiso 0.50 1 calc PR A -1 H14C H -0.1489 0.4258 0.2704 0.120 Uiso 0.50 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0212(2) 0.0203(2) 0.0253(2) 0.00153(15) 0.000 0.000 O1 0.0385(8) 0.0292(7) 0.0396(9) 0.0038(6) 0.0145(7) 0.0065(6) O2 0.0319(7) 0.0293(8) 0.0410(9) 0.0027(6) -0.0109(6) -0.0075(6) O3 0.140(2) 0.0282(10) 0.129(2) 0.0059(11) -0.070(2) -0.0003(13) C1 0.0254(10) 0.0205(9) 0.0385(12) -0.0021(8) 0.0035(9) -0.0042(8) C2 0.0288(14) 0.0196(13) 0.0372(16) 0.000 0.0020(12) 0.000 C3 0.0303(10) 0.0228(10) 0.0359(12) -0.0007(8) 0.0063(9) 0.0001(8) C4 0.0377(12) 0.0227(10) 0.0435(13) 0.0022(9) 0.0112(10) -0.0033(8) C5 0.0449(17) 0.0193(14) 0.0477(19) 0.000 0.0128(15) 0.000 N1 0.0501(16) 0.0198(12) 0.0493(17) 0.000 0.0152(13) 0.000 C6 0.0759(19) 0.0250(12) 0.0725(19) 0.0008(12) -0.0062(16) 0.0012(12) C7 0.0739(18) 0.0254(12) 0.0682(18) 0.0003(12) -0.0034(15) -0.0017(12) C8 0.123(3) 0.0281(15) 0.122(3) -0.0002(16) -0.058(3) 0.0033(17) C9 0.053(2) 0.0225(15) 0.048(2) 0.000 0.0145(16) 0.000 O11 0.0707(16) 0.0334(12) 0.0280(13) 0.0091(9) 0.000 0.000 N11 0.086(15) 0.092(3) 0.033(2) 0.0056(18) -0.009(3) -0.025(6) C11 0.049(3) 0.033(2) 0.039(3) 0.0064(18) 0.0077(19) -0.0019(16) C12 0.17(2) 0.145(7) 0.044(3) -0.003(4) 0.027(6) -0.062(10) C13 0.092(7) 0.155(9) 0.102(7) 0.042(7) -0.045(6) -0.064(6) C14 0.052(4) 0.102(5) 0.085(5) 0.040(4) 0.014(4) 0.000(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 O1 1.9458(14) 12 ? Cu1 O1 1.9458(14) . ? Cu1 O2 1.9641(14) . ? Cu1 O2 1.9641(14) 12 ? Cu1 O11 2.103(2) . ? Cu1 Cu1 2.6620(7) 9_565 ? O1 C1 1.250(3) . ? O2 C1 1.256(3) 4_565 ? O3 C6 1.200(4) . ? C1 O2 1.256(3) 4_565 ? C1 C3 1.496(3) . ? C2 C3 1.376(2) 7_544 ? C2 C3 1.376(2) . ? C2 H2 0.9500 . ? C3 C4 1.399(3) . ? C4 C5 1.375(3) . ? C4 H4 0.9500 . ? C5 C4 1.375(3) 7_544 ? C5 N1 1.454(4) . ? N1 C6 1.385(3) . ? N1 C6 1.385(3) 7_544 ? C6 C7 1.490(3) . ? C7 C8 1.352(4) . ? C7 C9 1.401(3) . ? C8 C8 1.407(6) 11_565 ? C8 H8 0.9500 . ? C9 C7 1.401(3) 7_544 ? C9 C9 1.415(6) 13_554 ? O11 C11 1.165(5) 12 ? O11 C11 1.165(5) . ? N11 C11 1.295(13) . ? N11 C13 1.47(2) . ? N11 C12 1.482(13) . ? C11 C14 1.547(8) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 O1 88.11(10) 12 . ? O1 Cu1 O2 167.50(6) 12 . ? O1 Cu1 O2 88.95(7) . . ? O1 Cu1 O2 88.95(7) 12 12 ? O1 Cu1 O2 167.50(6) . 12 ? O2 Cu1 O2 91.33(9) . 12 ? O1 Cu1 O11 96.79(6) 12 . ? O1 Cu1 O11 96.79(6) . . ? O2 Cu1 O11 95.61(6) . . ? O2 Cu1 O11 95.61(6) 12 . ? O1 Cu1 Cu1 87.41(5) 12 9_565 ? O1 Cu1 Cu1 87.41(5) . 9_565 ? O2 Cu1 Cu1 80.33(4) . 9_565 ? O2 Cu1 Cu1 80.33(4) 12 9_565 ? O11 Cu1 Cu1 174.14(7) . 9_565 ? C1 O1 Cu1 118.75(13) . . ? C1 O2 Cu1 126.13(14) 4_565 . ? O1 C1 O2 127.25(19) . 4_565 ? O1 C1 C3 116.95(17) . . ? O2 C1 C3 115.78(18) 4_565 . ? C3 C2 C3 120.5(2) 7_544 . ? C3 C2 H2 119.8 7_544 . ? C3 C2 H2 119.8 . . ? C2 C3 C4 120.05(19) . . ? C2 C3 C1 120.37(18) . . ? C4 C3 C1 119.58(18) . . ? C5 C4 C3 118.70(19) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C4 121.9(3) . 7_544 ? C4 C5 N1 119.05(13) . . ? C4 C5 N1 119.05(13) 7_544 . ? C6 N1 C6 126.4(3) . 7_544 ? C6 N1 C5 116.78(14) . . ? C6 N1 C5 116.78(14) 7_544 . ? O3 C6 N1 120.5(2) . . ? O3 C6 C7 123.2(3) . . ? N1 C6 C7 116.3(2) . . ? C8 C7 C9 120.5(2) . . ? C8 C7 C6 120.0(3) . . ? C9 C7 C6 119.6(2) . . ? C7 C8 C8 120.43(17) . 11_565 ? C7 C8 H8 119.8 . . ? C8 C8 H8 119.8 11_565 . ? C7 C9 C7 121.8(3) 7_544 . ? C7 C9 C9 119.08(15) 7_544 13_554 ? C7 C9 C9 119.08(15) . 13_554 ? C11 O11 Cu1 140.2(3) 12 . ? C11 O11 Cu1 140.2(3) . . ? C11 N11 C13 118.2(10) . . ? C11 N11 C12 126.2(17) . . ? C13 N11 C12 115.6(11) . . ? O11 C11 N11 127.6(10) . . ? O11 C11 C14 111.5(5) . . ? N11 C11 C14 120.7(9) . . ? N11 C12 H12A 109.5 . . ? N11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N11 C13 H13A 109.5 . . ? N11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 -0.016 0.250 0.250 1106 309 ' ' 2 -0.023 0.750 -0.250 1106 309 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 65.69 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.271 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.052 # Attachment '- 2b.cif' data_pj289e _database_code_depnum_ccdc_archive 'CCDC 789424' #TrackingRef '- 2b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H28 Cu2 N4 O12' _chemical_formula_weight 931.78 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Imma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z' '-x, y+1/2, -z' 'x, -y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1, z+1/2' '-x+1/2, y+1, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z' 'x, -y-1/2, z' '-x, y, z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y, -z+1/2' 'x+1/2, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 14.981(2) _cell_length_b 36.371(5) _cell_length_c 10.922(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5951.1(16) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 6212 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.3 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.040 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1896 _exptl_absorpt_coefficient_mu 0.763 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9276 _exptl_absorpt_correction_T_max 0.9276 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15247 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.47 _reflns_number_total 2922 _reflns_number_gt 2488 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART APEX (Bruker, 2010)' _computing_cell_refinement 'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'APEX2 (Bruker, 2010)' _publ_section_references ; Bruker AXS. (2009). SAINT Bruker AXS, Inc. Madison, Wisconsin, USA. Sheldrick, G. M. (2008). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _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^)+(0.0904P)^2^+0.7804P] 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 2922 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 1.0000 0.473733(9) 0.08590(3) 0.01812(17) Uani 1 2 d S . . N1 N 0.7500 0.34650(7) -0.2500 0.0302(6) Uani 1 2 d S . . O1 O 0.90614(11) 0.49402(4) -0.15409(15) 0.0302(4) Uani 1 1 d . . . O2 O 0.91021(11) 0.44887(4) -0.01447(15) 0.0309(4) Uani 1 1 d . . . O3 O 0.6362(2) 0.34674(6) -0.1161(3) 0.0992(12) Uani 1 1 d . . . C1 C 0.88184(16) 0.46370(7) -0.1108(2) 0.0250(5) Uani 1 1 d . . . C2 C 0.81278(14) 0.44327(6) -0.1814(2) 0.0251(5) Uani 1 1 d . . . C3 C 0.81138(16) 0.40494(6) -0.1792(2) 0.0292(5) Uani 1 1 d . . . H3 H 0.8523 0.3917 -0.1294 0.035 Uiso 1 1 calc R . . C4 C 0.7500 0.38643(8) -0.2500 0.0279(7) Uani 1 2 d S . . C5 C 0.7500 0.46214(9) -0.2500 0.0272(7) Uani 1 2 d S . . H5 H 0.7500 0.4883 -0.2500 0.033 Uiso 1 2 calc SR . . C6 C 0.6881(2) 0.32928(7) -0.1760(3) 0.0491(8) Uani 1 1 d . . . C7 C 0.6894(2) 0.28826(7) -0.1758(3) 0.0471(7) Uani 1 1 d . . . C8 C 0.6337(3) 0.26934(9) -0.1015(5) 0.108(2) Uani 1 1 d . . . H8 H 0.5943 0.2823 -0.0488 0.130 Uiso 1 1 calc R . . C9 C 0.7500 0.26957(9) -0.2500 0.0300(8) Uani 1 2 d S . . N21 N 1.0000 0.43559(8) 0.2363(2) 0.0262(6) Uani 1 2 d S . . C23 C 1.0000 0.38756(18) 0.4281(5) 0.0800(19) Uani 1 2 d S . . H23 H 1.0000 0.3709 0.4950 0.096 Uiso 1 2 d SR A . C21 C 0.9866(5) 0.44679(13) 0.3485(4) 0.0410(14) Uiso 0.50 1 d P A -1 H21 H 0.9770 0.4723 0.3615 0.049 Uiso 0.50 1 calc PR A -1 C22 C 0.9855(5) 0.42426(14) 0.4480(5) 0.0481(15) Uiso 0.50 1 d P A -1 C24 C 1.0179(5) 0.37442(18) 0.3126(6) 0.065(2) Uiso 0.50 1 d P A -1 C25 C 1.0157(4) 0.39969(14) 0.2174(4) 0.0477(15) Uiso 0.50 1 d P A -1 H25 H 1.0255 0.3913 0.1361 0.057 Uiso 0.50 1 calc PR A -1 C26 C 0.9725(6) 0.4382(3) 0.5765(7) 0.090(3) Uiso 0.50 1 d P A -1 H26A H 1.0089 0.4602 0.5890 0.135 Uiso 0.50 1 calc PR A -1 H26B H 0.9906 0.4191 0.6349 0.135 Uiso 0.50 1 calc PR A -1 H26C H 0.9094 0.4442 0.5893 0.135 Uiso 0.50 1 calc PR A -1 C27 C 1.0316(6) 0.3332(2) 0.2839(8) 0.105(3) Uiso 0.50 1 d P A -1 H27A H 1.0941 0.3288 0.2619 0.157 Uiso 0.50 1 calc PR A -1 H27B H 0.9931 0.3261 0.2154 0.157 Uiso 0.50 1 calc PR A -1 H27C H 1.0163 0.3186 0.3562 0.157 Uiso 0.50 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0187(2) 0.0151(2) 0.0205(2) 0.00101(14) 0.000 0.000 N1 0.0363(15) 0.0138(13) 0.0404(16) 0.000 -0.0063(13) 0.000 O1 0.0326(9) 0.0234(9) 0.0346(9) 0.0023(7) -0.0112(7) -0.0073(7) O2 0.0361(9) 0.0237(8) 0.0330(9) 0.0040(7) -0.0141(7) -0.0065(7) O3 0.124(3) 0.0222(11) 0.151(3) -0.0040(14) 0.089(2) 0.0073(14) C1 0.0228(11) 0.0200(11) 0.0323(12) -0.0028(10) -0.0024(10) 0.0018(10) C2 0.0256(12) 0.0200(11) 0.0297(12) -0.0015(10) -0.0053(10) 0.0014(9) C3 0.0341(13) 0.0201(12) 0.0334(12) -0.0004(10) -0.0122(10) 0.0036(10) C4 0.0337(17) 0.0119(15) 0.0379(18) 0.000 -0.0044(15) 0.000 C5 0.0301(17) 0.0177(16) 0.0338(17) 0.000 -0.0046(14) 0.000 C6 0.0601(19) 0.0205(14) 0.0665(19) -0.0047(13) 0.0163(16) 0.0027(13) C7 0.0553(18) 0.0175(13) 0.0686(19) -0.0045(13) 0.0177(15) 0.0016(12) C8 0.138(4) 0.0254(18) 0.161(5) 0.002(2) 0.106(4) 0.003(2) C9 0.0358(18) 0.0186(17) 0.0356(17) 0.000 -0.0069(15) 0.000 N21 0.0324(15) 0.0215(14) 0.0247(14) 0.0065(12) 0.000 0.000 C23 0.112(5) 0.079(4) 0.049(3) 0.038(3) 0.000 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 O2 1.9568(15) . ? Cu1 O2 1.9568(15) 12_755 ? Cu1 O1 1.9767(15) 9_765 ? Cu1 O1 1.9767(15) 4_565 ? Cu1 N21 2.150(3) . ? Cu1 Cu1 2.6780(7) 9_765 ? N1 C6 1.380(3) . ? N1 C6 1.380(3) 7_644 ? N1 C4 1.453(4) . ? O1 C1 1.254(3) . ? O1 Cu1 1.9767(15) 9_765 ? O2 C1 1.257(3) . ? O3 C6 1.198(4) . ? C1 C2 1.489(3) . ? C2 C5 1.384(3) . ? C2 C3 1.395(3) . ? C3 C4 1.377(3) . ? C3 H3 0.9500 . ? C4 C3 1.377(3) 7_644 ? C5 C2 1.385(3) 7_644 ? C5 H5 0.9500 . ? C6 C7 1.492(4) . ? C7 C8 1.351(4) . ? C7 C9 1.394(3) . ? C8 C8 1.407(7) 11_565 ? C8 H8 0.9500 . ? C9 C7 1.394(3) 7_644 ? C9 C9 1.424(6) 13_654 ? N21 C21 1.307(5) 12_755 ? N21 C21 1.307(5) . ? N21 C25 1.342(6) . ? N21 C25 1.342(6) 12_755 ? C23 C22 1.370(8) 12_755 ? C23 C22 1.370(8) . ? C23 C24 1.375(8) . ? C23 C24 1.375(8) 12_755 ? C23 H23 0.9493 . ? C21 C22 1.361(7) . ? C21 H21 0.9500 . ? C22 C26 1.504(9) . ? C24 C25 1.388(8) . ? C24 C27 1.545(10) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 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 O2 Cu1 O2 86.85(10) . 12_755 ? O2 Cu1 O1 166.98(7) . 9_765 ? O2 Cu1 O1 89.79(7) 12_755 9_765 ? O2 Cu1 O1 89.79(7) . 4_565 ? O2 Cu1 O1 166.98(7) 12_755 4_565 ? O1 Cu1 O1 90.69(10) 9_765 4_565 ? O2 Cu1 N21 97.45(7) . . ? O2 Cu1 N21 97.45(7) 12_755 . ? O1 Cu1 N21 95.45(7) 9_765 . ? O1 Cu1 N21 95.45(7) 4_565 . ? O2 Cu1 Cu1 86.40(5) . 9_765 ? O2 Cu1 Cu1 86.40(5) 12_755 9_765 ? O1 Cu1 Cu1 80.83(5) 9_765 9_765 ? O1 Cu1 Cu1 80.83(5) 4_565 9_765 ? N21 Cu1 Cu1 174.67(8) . 9_765 ? C6 N1 C6 126.0(3) . 7_644 ? C6 N1 C4 116.98(15) . . ? C6 N1 C4 116.98(15) 7_644 . ? C1 O1 Cu1 125.90(15) . 9_765 ? C1 O2 Cu1 120.21(15) . . ? O1 C1 O2 126.5(2) . . ? O1 C1 C2 116.5(2) . . ? O2 C1 C2 117.0(2) . . ? C5 C2 C3 119.6(2) . . ? C5 C2 C1 120.3(2) . . ? C3 C2 C1 120.0(2) . . ? C4 C3 C2 119.3(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C3 121.5(3) 7_644 . ? C3 C4 N1 119.26(15) 7_644 . ? C3 C4 N1 119.26(15) . . ? C2 C5 C2 120.6(3) . 7_644 ? C2 C5 H5 119.7 . . ? C2 C5 H5 119.7 7_644 . ? O3 C6 N1 121.0(3) . . ? O3 C6 C7 122.5(3) . . ? N1 C6 C7 116.5(2) . . ? C8 C7 C9 120.2(3) . . ? C8 C7 C6 120.2(3) . . ? C9 C7 C6 119.6(3) . . ? C7 C8 C8 120.62(19) . 11_565 ? C7 C8 H8 119.7 . . ? C8 C8 H8 119.7 11_565 . ? C7 C9 C7 121.6(3) 7_644 . ? C7 C9 C9 119.18(16) 7_644 13_654 ? C7 C9 C9 119.18(16) . 13_654 ? C21 N21 C25 114.9(4) 12_755 . ? C21 N21 C25 118.3(4) . . ? C21 N21 C25 118.3(4) 12_755 12_755 ? C21 N21 C25 114.9(4) . 12_755 ? C21 N21 Cu1 121.0(3) 12_755 . ? C21 N21 Cu1 121.0(3) . . ? C25 N21 Cu1 120.7(3) . . ? C25 N21 Cu1 120.7(3) 12_755 . ? C22 C23 C24 117.0(5) 12_755 . ? C22 C23 C24 121.0(5) . . ? C22 C23 C24 121.0(5) 12_755 12_755 ? C22 C23 C24 117.0(5) . 12_755 ? C22 C23 H23 119.9 12_755 . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.0 . . ? C24 C23 H23 119.0 12_755 . ? N21 C21 C22 124.3(4) . . ? N21 C21 H21 117.9 . . ? C22 C21 H21 117.9 . . ? C21 C22 C23 117.2(5) . . ? C21 C22 C26 123.0(5) . . ? C23 C22 C26 119.8(6) . . ? C23 C24 C25 116.9(6) . . ? C23 C24 C27 123.3(6) . . ? C25 C24 C27 119.6(6) . . ? N21 C25 C24 122.2(5) . . ? N21 C25 H25 118.9 . . ? C24 C25 H25 118.9 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 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 O2 Cu1 O2 C1 -89.30(18) 12_755 . . . ? O1 Cu1 O2 C1 -14.0(4) 9_765 . . . ? O1 Cu1 O2 C1 78.12(18) 4_565 . . . ? N21 Cu1 O2 C1 173.59(18) . . . . ? Cu1 Cu1 O2 C1 -2.71(17) 9_765 . . . ? Cu1 O1 C1 O2 2.6(4) 9_765 . . . ? Cu1 O1 C1 C2 -177.04(14) 9_765 . . . ? Cu1 O2 C1 O1 1.0(3) . . . . ? Cu1 O2 C1 C2 -179.28(15) . . . . ? O1 C1 C2 C5 -30.2(3) . . . . ? O2 C1 C2 C5 150.1(2) . . . . ? O1 C1 C2 C3 149.4(2) . . . . ? O2 C1 C2 C3 -30.3(3) . . . . ? C5 C2 C3 C4 3.0(3) . . . . ? C1 C2 C3 C4 -176.64(19) . . . . ? C2 C3 C4 C3 -1.50(16) . . . 7_644 ? C2 C3 C4 N1 178.50(16) . . . . ? C6 N1 C4 C3 -81.1(2) . . . 7_644 ? C6 N1 C4 C3 98.9(2) 7_644 . . 7_644 ? C6 N1 C4 C3 98.9(2) . . . . ? C6 N1 C4 C3 -81.1(2) 7_644 . . . ? C3 C2 C5 C2 -1.50(16) . . . 7_644 ? C1 C2 C5 C2 178.1(2) . . . 7_644 ? C6 N1 C6 O3 -179.0(4) 7_644 . . . ? C4 N1 C6 O3 1.0(4) . . . . ? C6 N1 C6 C7 0.6(2) 7_644 . . . ? C4 N1 C6 C7 -179.4(2) . . . . ? O3 C6 C7 C8 -3.4(6) . . . . ? N1 C6 C7 C8 176.9(4) . . . . ? O3 C6 C7 C9 178.4(3) . . . . ? N1 C6 C7 C9 -1.3(4) . . . . ? C9 C7 C8 C8 -2.5(5) . . . 11_565 ? C6 C7 C8 C8 179.3(2) . . . 11_565 ? C8 C7 C9 C7 -177.5(4) . . . 7_644 ? C6 C7 C9 C7 0.7(2) . . . 7_644 ? C8 C7 C9 C9 2.5(4) . . . 13_654 ? C6 C7 C9 C9 -179.3(2) . . . 13_654 ? O2 Cu1 N21 C21 -146.4(4) . . . 12_755 ? O2 Cu1 N21 C21 125.8(4) 12_755 . . 12_755 ? O1 Cu1 N21 C21 35.3(4) 9_765 . . 12_755 ? O1 Cu1 N21 C21 -55.9(4) 4_565 . . 12_755 ? O2 Cu1 N21 C21 -125.8(4) . . . . ? O2 Cu1 N21 C21 146.4(4) 12_755 . . . ? O1 Cu1 N21 C21 55.9(4) 9_765 . . . ? O1 Cu1 N21 C21 -35.3(4) 4_565 . . . ? O2 Cu1 N21 C25 55.6(3) . . . . ? O2 Cu1 N21 C25 -32.2(3) 12_755 . . . ? O1 Cu1 N21 C25 -122.7(3) 9_765 . . . ? O1 Cu1 N21 C25 146.1(3) 4_565 . . . ? O2 Cu1 N21 C25 32.2(3) . . . 12_755 ? O2 Cu1 N21 C25 -55.6(3) 12_755 . . 12_755 ? O1 Cu1 N21 C25 -146.1(3) 9_765 . . 12_755 ? O1 Cu1 N21 C25 122.7(3) 4_565 . . 12_755 ? C21 N21 C21 C22 -84.8(7) 12_755 . . . ? C25 N21 C21 C22 -1.5(8) . . . . ? C25 N21 C21 C22 20.7(8) 12_755 . . . ? Cu1 N21 C21 C22 179.9(5) . . . . ? N21 C21 C22 C23 0.4(10) . . . . ? N21 C21 C22 C26 178.2(7) . . . . ? C22 C23 C22 C21 84.4(6) 12_755 . . . ? C24 C23 C22 C21 2.2(8) . . . . ? C24 C23 C22 C21 -23.2(8) 12_755 . . . ? C22 C23 C22 C26 -93.4(7) 12_755 . . . ? C24 C23 C22 C26 -175.7(7) . . . . ? C24 C23 C22 C26 158.9(7) 12_755 . . . ? C22 C23 C24 C25 -23.9(8) 12_755 . . . ? C22 C23 C24 C25 -3.4(9) . . . . ? C24 C23 C24 C25 82.6(6) 12_755 . . . ? C22 C23 C24 C27 161.8(7) 12_755 . . . ? C22 C23 C24 C27 -177.8(7) . . . . ? C24 C23 C24 C27 -91.8(7) 12_755 . . . ? C21 N21 C25 C24 19.5(8) 12_755 . . . ? C21 N21 C25 C24 0.0(8) . . . . ? C25 N21 C25 C24 -85.3(6) 12_755 . . . ? Cu1 N21 C25 C24 178.7(5) . . . . ? C23 C24 C25 N21 2.4(10) . . . . ? C27 C24 C25 N21 176.9(6) . . . . ? 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 0.188 -0.003 -0.003 2435 756 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.580 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.073