# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm loop_ _publ_author_name 'Brendan F Abrahams' 'Martin J Grannas' 'Laura J McCormick' 'Richard Robson' 'Peter J Thistlethwaite' _publ_contact_author_name 'Brendan F Abrahams' _publ_contact_author_address ; School of Chemistry University of Melbourne Parkville Victoria 3010 AUSTRALIA ; _publ_contact_author_email BFA@UNIMELB.EDU.AU _publ_section_title ; Linear Coordination Polymers from Aldaric Acids ; # Attachment 'lmd46d1.cif' data_lmd46d _database_code_depnum_ccdc_archive 'CCDC 763056' #TrackingRef 'lmd46d1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H46.50 N4 O23.25 Zn2' _chemical_formula_weight 989.97 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' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.9528(2) _cell_length_b 13.6506(2) _cell_length_c 26.0918(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3901.04(11) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 5881 _cell_measurement_theta_min 3.3946 _cell_measurement_theta_max 72.8017 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2148 _exptl_crystal_size_mid 0.1659 _exptl_crystal_size_min 0.1642 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2050 _exptl_absorpt_coefficient_mu 2.384 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.688 _exptl_absorpt_correction_T_max 0.756 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 16.0711 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10258 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 69.99 _reflns_number_total 6384 _reflns_number_gt 5502 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0863P)^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 _chemical_absolute_configuration rm _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(3) _refine_ls_number_reflns 6384 _refine_ls_number_parameters 557 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1304 _refine_ls_wR_factor_gt 0.1228 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1851(5) 0.6654(4) 0.0875(2) 0.0428(13) Uani 1 1 d . . . C2 C 0.1335(5) 0.7344(4) 0.04678(18) 0.0321(11) Uani 1 1 d . . . H2 H 0.0422 0.7324 0.0479 0.038 Uiso 1 1 calc R . . C3 C 0.1776(5) 0.7041(3) -0.00672(17) 0.0299(10) Uani 1 1 d . . . H3 H 0.1562 0.7584 -0.0308 0.036 Uiso 1 1 calc R . . C4 C 0.1241(4) 0.6095(4) -0.02900(18) 0.0295(11) Uani 1 1 d . . . H4 H 0.1516 0.5524 -0.0079 0.035 Uiso 1 1 calc R . . C5 C -0.0165(4) 0.6109(4) -0.03135(19) 0.0300(11) Uani 1 1 d . . . H5 H -0.0484 0.6197 0.0043 0.036 Uiso 1 1 calc R . . C6 C -0.0692(4) 0.5160(4) -0.0529(2) 0.0317(11) Uani 1 1 d . . . C7 C -0.2477(5) 0.3581(4) 0.07887(19) 0.0380(12) Uani 1 1 d . . . C8 C -0.3137(5) 0.2906(4) 0.04076(18) 0.0361(11) Uani 1 1 d . . . H8 H -0.2873 0.3076 0.0052 0.043 Uiso 1 1 calc R . . C9 C -0.4523(5) 0.3037(4) 0.04490(17) 0.0367(12) Uani 1 1 d . . . C10 C -0.5046(4) 0.3952(4) 0.01981(18) 0.0319(11) Uani 1 1 d . . . H10 H -0.4707 0.4544 0.0373 0.038 Uiso 1 1 calc R . . C11 C -0.4794(4) 0.4029(4) -0.03804(17) 0.0291(10) Uani 1 1 d . . . H11 H -0.3910 0.4172 -0.0438 0.035 Uiso 1 1 calc R . . C12 C -0.5561(4) 0.4879(4) -0.05789(18) 0.0279(10) Uani 1 1 d . . . C13 C 0.0567(5) 0.1657(4) 0.18648(19) 0.0352(11) Uani 1 1 d . . . H13 H 0.1029 0.1770 0.1562 0.042 Uiso 1 1 calc R . . C14 C 0.1182(5) 0.1563(4) 0.2332(2) 0.0420(13) Uani 1 1 d . . . H14 H 0.2048 0.1596 0.2347 0.050 Uiso 1 1 calc R . . C15 C 0.0508(6) 0.1423(4) 0.2767(2) 0.0454(14) Uani 1 1 d . . . H15 H 0.0902 0.1381 0.3090 0.055 Uiso 1 1 calc R . . C16 C -0.0743(6) 0.1342(4) 0.27345(19) 0.0379(12) Uani 1 1 d . . . H16 H -0.1219 0.1231 0.3033 0.045 Uiso 1 1 calc R . . C17 C -0.1297(5) 0.1425(3) 0.22559(17) 0.0300(10) Uani 1 1 d . . . C18 C -0.2625(5) 0.1269(3) 0.21779(17) 0.0296(11) Uani 1 1 d . . . C19 C -0.3448(6) 0.1090(4) 0.25736(19) 0.0388(12) Uani 1 1 d . . . H19 H -0.3177 0.1096 0.2919 0.047 Uiso 1 1 calc R . . C20 C -0.4655(5) 0.0905(4) 0.2464(2) 0.0432(14) Uani 1 1 d . . . H20 H -0.5223 0.0781 0.2731 0.052 Uiso 1 1 calc R . . C21 C -0.5030(5) 0.0903(4) 0.1950(2) 0.0428(14) Uani 1 1 d . . . H21 H -0.5855 0.0768 0.1862 0.051 Uiso 1 1 calc R . . C22 C -0.4191(5) 0.1098(4) 0.1580(2) 0.0357(12) Uani 1 1 d . . . H22 H -0.4446 0.1097 0.1232 0.043 Uiso 1 1 calc R . . C23 C 0.5285(5) 0.8280(4) 0.1862(2) 0.0413(12) Uani 1 1 d . . . H23 H 0.5700 0.8164 0.1548 0.050 Uiso 1 1 calc R . . C24 C 0.5944(6) 0.8269(4) 0.2312(2) 0.0455(13) Uani 1 1 d . . . H24 H 0.6799 0.8151 0.2308 0.055 Uiso 1 1 calc R . . C25 C 0.5341(6) 0.8433(5) 0.2772(2) 0.0513(15) Uani 1 1 d . . . H25 H 0.5777 0.8433 0.3087 0.062 Uiso 1 1 calc R . . C26 C 0.4098(6) 0.8595(4) 0.2765(2) 0.0465(14) Uani 1 1 d . . . H26 H 0.3668 0.8702 0.3076 0.056 Uiso 1 1 calc R . . C27 C 0.3474(6) 0.8603(4) 0.2298(2) 0.0401(12) Uani 1 1 d . . . C28 C 0.2160(5) 0.8783(4) 0.22451(19) 0.0364(12) Uani 1 1 d . . . C29 C 0.1370(6) 0.8871(4) 0.2666(2) 0.0430(14) Uani 1 1 d . . . H29 H 0.1681 0.8854 0.3006 0.052 Uiso 1 1 calc R . . C30 C 0.0131(6) 0.8984(4) 0.2580(2) 0.0458(15) Uani 1 1 d . . . H30 H -0.0414 0.9047 0.2861 0.055 Uiso 1 1 calc R . . C31 C -0.0310(6) 0.9003(4) 0.2086(2) 0.0446(14) Uani 1 1 d . . . H31 H -0.1159 0.9075 0.2022 0.053 Uiso 1 1 calc R . . C32 C 0.0508(5) 0.8914(4) 0.1687(2) 0.0400(13) Uani 1 1 d . . . H32 H 0.0206 0.8933 0.1346 0.048 Uiso 1 1 calc R . . N1 N -0.0638(4) 0.1594(3) 0.18296(14) 0.0313(9) Uani 1 1 d . . . N2 N -0.3008(4) 0.1294(3) 0.16859(15) 0.0291(9) Uani 1 1 d . . . N3 N 0.4088(4) 0.8448(3) 0.18516(17) 0.0402(10) Uani 1 1 d . . . N4 N 0.1715(4) 0.8803(3) 0.17595(16) 0.0377(10) Uani 1 1 d . . . O1A O 0.2634(3) 0.6995(3) 0.11813(14) 0.0413(8) Uani 1 1 d . . . O1B O 0.1467(5) 0.5799(3) 0.08735(16) 0.0619(13) Uani 1 1 d . . . O2 O 0.1739(3) 0.8309(3) 0.05685(13) 0.0345(8) Uani 1 1 d . . . H2A H 0.1166 0.8704 0.0515 0.052 Uiso 1 1 calc R . . O3 O 0.3064(3) 0.7003(3) -0.00362(14) 0.0404(9) Uani 1 1 d . . . H3A H 0.3313 0.6472 -0.0162 0.061 Uiso 1 1 calc R . . O4 O 0.1696(3) 0.5992(2) -0.08044(12) 0.0320(7) Uani 1 1 d . . . H4A H 0.2310 0.5623 -0.0804 0.048 Uiso 1 1 calc R . . O5 O -0.0570(3) 0.6934(2) -0.06201(13) 0.0327(8) Uani 1 1 d . . . O6A O -0.1449(3) 0.5198(3) -0.08987(13) 0.0347(8) Uani 1 1 d . . . O6B O -0.0368(4) 0.4383(3) -0.03188(15) 0.0412(9) Uani 1 1 d . . . O7A O -0.1846(3) 0.3205(2) 0.11386(13) 0.0377(8) Uani 1 1 d . . . O7B O -0.2645(4) 0.4483(3) 0.07283(16) 0.0473(10) Uani 1 1 d . . . O8 O -0.2829(3) 0.1913(3) 0.05100(13) 0.0390(9) Uani 1 1 d . . . H8A H -0.3448 0.1615 0.0618 0.059 Uiso 1 1 calc R . . O9 O -0.4815(4) 0.3047(3) 0.09878(12) 0.0494(11) Uani 1 1 d . . . H9 H -0.5372 0.3458 0.1043 0.074 Uiso 1 1 calc R . . O10 O -0.6345(3) 0.3940(4) 0.02593(14) 0.0518(11) Uani 1 1 d . . . H10A H -0.6535 0.4242 0.0528 0.078 Uiso 1 1 calc R . . O11 O -0.5125(4) 0.3173(3) -0.06529(12) 0.0377(8) Uani 1 1 d . . . O12A O -0.6427(3) 0.4695(2) -0.08796(12) 0.0297(7) Uani 1 1 d . . . O12B O -0.5301(3) 0.5715(3) -0.04193(16) 0.0418(9) Uani 1 1 d . . . Zn1 Zn -0.16770(5) 0.17235(4) 0.11533(2) 0.02746(16) Uani 1 1 d . . . Zn2 Zn 0.30408(6) 0.84825(5) 0.11824(3) 0.03478(18) Uani 1 1 d . . . O1W O 0.5874(4) 0.1454(3) 0.95223(15) 0.0489(10) Uani 1 1 d . . . O2W O 0.2977(4) 0.1938(3) 0.1026(2) 0.0681(14) Uani 1 1 d . . . O3W O -0.0977(5) 0.5869(3) 0.09607(18) 0.0615(13) Uani 1 1 d . . . O4W O 0.7670(5) 0.7378(3) 0.13406(16) 0.0718(15) Uani 1 1 d . . . O5W O 0.4110(8) 0.5176(6) 0.1209(3) 0.080 Uiso 0.711(12) 1 d P . . O6W O 0.623(4) 0.5652(14) 0.1420(12) 0.080 Uiso 0.46(3) 1 d P . . O7W O 0.1928(14) 0.3707(16) 0.1495(6) 0.080 Uiso 0.418(19) 1 d P . . O8W O 0.3423(12) 0.4758(9) 0.1169(5) 0.080 Uiso 0.479(12) 1 d P . . O10W O 0.567(3) 0.5593(12) 0.1287(8) 0.080 Uiso 0.39(3) 1 d P . . O11W O 0.662(2) 0.5771(14) 0.1590(11) 0.080 Uiso 0.39(4) 1 d P . . O9W O 0.1815(17) 0.4203(19) 0.1413(7) 0.080 Uiso 0.353(19) 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 C1 0.043(3) 0.049(3) 0.037(2) 0.008(2) -0.002(2) -0.012(3) C2 0.029(2) 0.035(3) 0.033(2) -0.001(2) 0.001(2) -0.005(2) C3 0.031(2) 0.026(2) 0.032(2) 0.0012(18) 0.001(2) 0.001(2) C4 0.022(2) 0.031(3) 0.035(2) 0.002(2) 0.000(2) 0.003(2) C5 0.028(3) 0.027(2) 0.034(2) 0.001(2) -0.002(2) 0.004(2) C6 0.024(2) 0.029(3) 0.042(3) 0.000(2) 0.000(2) 0.002(2) C7 0.039(3) 0.035(3) 0.039(3) 0.009(2) -0.006(2) -0.002(2) C8 0.040(3) 0.036(3) 0.032(2) 0.012(2) -0.006(2) -0.004(2) C9 0.041(3) 0.047(3) 0.022(2) 0.009(2) -0.004(2) -0.011(3) C10 0.025(2) 0.045(3) 0.026(2) -0.001(2) 0.0010(19) -0.004(2) C11 0.024(2) 0.037(3) 0.026(2) 0.0049(19) 0.0057(19) 0.004(2) C12 0.022(2) 0.030(3) 0.031(2) 0.004(2) 0.003(2) 0.006(2) C13 0.034(3) 0.035(3) 0.037(2) -0.007(2) -0.007(2) 0.002(2) C14 0.034(3) 0.039(3) 0.053(3) -0.012(3) -0.017(2) 0.007(3) C15 0.066(4) 0.037(3) 0.033(2) -0.006(2) -0.024(3) 0.004(3) C16 0.056(4) 0.030(3) 0.027(2) 0.001(2) -0.006(2) 0.008(3) C17 0.043(3) 0.021(2) 0.025(2) 0.0004(18) -0.003(2) 0.002(2) C18 0.041(3) 0.019(2) 0.028(2) 0.0048(18) 0.000(2) 0.006(2) C19 0.054(3) 0.027(2) 0.035(2) 0.002(2) 0.008(3) 0.006(3) C20 0.044(3) 0.029(3) 0.057(3) 0.009(3) 0.017(3) 0.000(3) C21 0.034(3) 0.030(3) 0.065(4) 0.003(3) -0.001(3) -0.007(2) C22 0.035(3) 0.022(2) 0.050(3) 0.006(2) -0.003(2) -0.005(2) C23 0.041(3) 0.037(3) 0.046(3) 0.002(2) -0.003(2) -0.015(3) C24 0.043(3) 0.035(3) 0.058(3) 0.006(3) -0.013(3) -0.004(3) C25 0.069(4) 0.039(3) 0.045(3) 0.004(3) -0.015(3) -0.009(3) C26 0.060(4) 0.036(3) 0.043(3) 0.003(2) -0.002(3) -0.019(3) C27 0.056(3) 0.024(2) 0.041(3) -0.003(2) 0.001(3) -0.010(3) C28 0.050(3) 0.021(2) 0.038(3) 0.000(2) 0.008(2) -0.012(2) C29 0.062(4) 0.029(3) 0.038(3) 0.002(2) 0.007(3) -0.007(3) C30 0.060(4) 0.030(3) 0.048(3) 0.006(2) 0.016(3) -0.002(3) C31 0.040(3) 0.031(3) 0.063(4) 0.006(3) 0.013(3) -0.002(3) C32 0.040(3) 0.034(3) 0.047(3) 0.001(2) 0.007(2) -0.015(3) N1 0.040(2) 0.027(2) 0.0267(18) -0.0038(16) -0.0067(17) 0.001(2) N2 0.032(2) 0.023(2) 0.0329(19) 0.0059(16) -0.0014(18) 0.0018(18) N3 0.043(2) 0.037(3) 0.041(2) 0.002(2) 0.003(2) -0.014(2) N4 0.038(2) 0.035(2) 0.040(2) -0.0030(18) 0.006(2) -0.006(2) O1A 0.0409(19) 0.045(2) 0.0382(17) 0.0051(17) -0.0085(18) -0.0158(17) O1B 0.085(3) 0.047(2) 0.054(2) 0.0192(19) -0.024(2) -0.035(2) O2 0.0297(17) 0.0350(18) 0.0386(17) -0.0067(15) 0.0010(15) -0.0025(18) O3 0.0236(17) 0.047(2) 0.050(2) -0.0132(17) 0.0007(16) -0.0053(17) O4 0.0275(18) 0.0293(17) 0.0391(17) 0.0005(13) 0.0004(15) 0.0082(16) O5 0.0272(17) 0.0262(18) 0.0447(18) 0.0040(15) -0.0051(15) 0.0041(15) O6A 0.0254(17) 0.0336(19) 0.0451(19) -0.0033(15) -0.0078(16) 0.0047(16) O6B 0.043(2) 0.0274(19) 0.053(2) 0.0044(17) -0.0083(18) -0.0048(18) O7A 0.0458(19) 0.0293(16) 0.0382(17) 0.0013(16) -0.0170(18) -0.0042(16) O7B 0.048(2) 0.030(2) 0.064(2) 0.0096(18) -0.018(2) -0.0054(19) O8 0.045(2) 0.037(2) 0.0355(18) 0.0147(15) -0.0174(17) -0.0121(17) O9 0.068(3) 0.057(3) 0.0234(16) 0.0024(16) -0.0008(17) -0.018(2) O10 0.0295(19) 0.092(3) 0.0335(18) -0.011(2) 0.0089(16) -0.007(2) O11 0.046(2) 0.042(2) 0.0257(15) 0.0028(15) -0.0074(15) 0.0152(18) O12A 0.0280(18) 0.0241(16) 0.0370(16) 0.0018(14) -0.0007(15) 0.0065(15) O12B 0.0314(19) 0.0285(19) 0.066(2) -0.0065(18) -0.0061(19) 0.0107(17) Zn1 0.0307(3) 0.0288(3) 0.0229(3) 0.0044(2) -0.0051(3) -0.0041(3) Zn2 0.0290(3) 0.0385(4) 0.0368(3) -0.0015(3) 0.0027(3) -0.0092(3) O1W 0.053(2) 0.044(2) 0.050(2) 0.0002(18) -0.0047(19) 0.017(2) O2W 0.041(2) 0.052(3) 0.112(4) -0.020(3) -0.002(2) 0.002(2) O3W 0.068(3) 0.041(2) 0.075(3) -0.012(2) -0.005(2) -0.011(2) O4W 0.116(4) 0.057(3) 0.043(2) -0.003(2) -0.019(2) 0.037(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 C1 O1B 1.241(7) . ? C1 O1A 1.261(6) . ? C1 C2 1.529(7) . ? C2 O2 1.414(6) . ? C2 C3 1.535(6) . ? C3 O3 1.413(6) . ? C3 C4 1.532(7) . ? C4 O4 1.439(6) . ? C4 C5 1.541(7) . ? C5 O5 1.450(6) . ? C5 C6 1.526(7) . ? C6 O6B 1.246(6) . ? C6 O6A 1.272(6) . ? C7 O7A 1.255(6) . ? C7 O7B 1.255(6) . ? C7 C8 1.536(7) . ? C8 O8 1.422(6) . ? C8 C9 1.532(8) . ? C9 O9 1.442(6) . ? C9 C10 1.523(8) . ? C10 O10 1.431(6) . ? C10 C11 1.538(6) . ? C11 O11 1.415(6) . ? C11 C12 1.523(7) . ? C12 O12B 1.248(6) . ? C12 O12A 1.257(6) . ? C13 N1 1.326(7) . ? C13 C14 1.399(7) . ? C14 C15 1.367(8) . ? C15 C16 1.377(8) . ? C16 C17 1.393(6) . ? C17 N1 1.346(6) . ? C17 C18 1.484(7) . ? C18 N2 1.351(6) . ? C18 C19 1.392(7) . ? C19 C20 1.376(8) . ? C20 C21 1.403(9) . ? C21 C22 1.360(8) . ? C22 N2 1.351(7) . ? C23 N3 1.332(7) . ? C23 C24 1.379(8) . ? C24 C25 1.388(9) . ? C25 C26 1.380(9) . ? C26 C27 1.397(8) . ? C27 N3 1.361(7) . ? C27 C28 1.466(8) . ? C28 N4 1.358(7) . ? C28 C29 1.404(7) . ? C29 C30 1.384(9) . ? C30 C31 1.376(9) . ? C31 C32 1.379(8) . ? C32 N4 1.344(8) . ? N1 Zn1 2.107(4) . ? N2 Zn1 2.098(4) . ? N3 Zn2 2.089(5) . ? N4 Zn2 2.137(4) . ? O1A Zn2 2.079(4) . ? O5 Zn2 2.189(3) 4_465 ? O6A Zn2 2.026(4) 4_465 ? O7A Zn1 2.031(3) . ? O11 Zn1 2.148(4) 4_455 ? O12A Zn1 2.082(3) 4_455 ? Zn1 O12A 2.082(3) 4 ? Zn1 O11 2.148(4) 4 ? Zn2 O6A 2.026(4) 4_565 ? Zn2 O5 2.189(3) 4_565 ? O5W O8W 0.950(13) . ? O5W O10W 1.82(3) . ? O6W O11W 0.63(3) . ? O6W O10W 0.71(3) . ? O7W O9W 0.72(2) . ? O10W O11W 1.33(4) . ? 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 O1B C1 O1A 125.4(5) . . ? O1B C1 C2 116.9(5) . . ? O1A C1 C2 117.7(5) . . ? O2 C2 C1 109.2(4) . . ? O2 C2 C3 108.8(4) . . ? C1 C2 C3 110.5(4) . . ? O3 C3 C4 111.9(4) . . ? O3 C3 C2 105.8(4) . . ? C4 C3 C2 116.9(4) . . ? O4 C4 C3 107.7(4) . . ? O4 C4 C5 108.1(4) . . ? C3 C4 C5 112.7(4) . . ? O5 C5 C6 109.9(4) . . ? O5 C5 C4 109.7(4) . . ? C6 C5 C4 112.4(4) . . ? O6B C6 O6A 123.7(5) . . ? O6B C6 C5 116.9(4) . . ? O6A C6 C5 119.4(4) . . ? O7A C7 O7B 125.0(5) . . ? O7A C7 C8 119.0(5) . . ? O7B C7 C8 116.0(5) . . ? O8 C8 C9 109.5(4) . . ? O8 C8 C7 109.7(4) . . ? C9 C8 C7 110.6(5) . . ? O9 C9 C10 109.1(5) . . ? O9 C9 C8 106.9(4) . . ? C10 C9 C8 116.0(4) . . ? O10 C10 C9 108.5(5) . . ? O10 C10 C11 106.8(4) . . ? C9 C10 C11 114.2(4) . . ? O11 C11 C12 108.5(4) . . ? O11 C11 C10 113.0(4) . . ? C12 C11 C10 106.7(4) . . ? O12B C12 O12A 124.3(4) . . ? O12B C12 C11 117.3(4) . . ? O12A C12 C11 118.4(4) . . ? N1 C13 C14 122.3(5) . . ? C15 C14 C13 118.4(5) . . ? C14 C15 C16 119.9(5) . . ? C15 C16 C17 118.8(5) . . ? N1 C17 C16 121.4(5) . . ? N1 C17 C18 115.9(4) . . ? C16 C17 C18 122.6(5) . . ? N2 C18 C19 120.5(5) . . ? N2 C18 C17 115.6(4) . . ? C19 C18 C17 123.9(5) . . ? C20 C19 C18 120.0(5) . . ? C19 C20 C21 118.7(5) . . ? C22 C21 C20 118.8(5) . . ? N2 C22 C21 122.7(5) . . ? N3 C23 C24 122.3(6) . . ? C23 C24 C25 119.1(6) . . ? C26 C25 C24 118.9(5) . . ? C25 C26 C27 119.8(6) . . ? N3 C27 C26 120.2(6) . . ? N3 C27 C28 115.5(5) . . ? C26 C27 C28 124.3(5) . . ? N4 C28 C29 120.5(5) . . ? N4 C28 C27 116.3(5) . . ? C29 C28 C27 123.1(5) . . ? C30 C29 C28 119.1(5) . . ? C31 C30 C29 119.9(6) . . ? C30 C31 C32 118.5(6) . . ? N4 C32 C31 122.9(6) . . ? C13 N1 C17 119.2(4) . . ? C13 N1 Zn1 126.2(3) . . ? C17 N1 Zn1 114.6(3) . . ? C22 N2 C18 119.2(4) . . ? C22 N2 Zn1 125.8(3) . . ? C18 N2 Zn1 114.8(3) . . ? C23 N3 C27 119.7(5) . . ? C23 N3 Zn2 124.1(4) . . ? C27 N3 Zn2 116.1(4) . . ? C32 N4 C28 119.1(5) . . ? C32 N4 Zn2 126.3(4) . . ? C28 N4 Zn2 114.2(4) . . ? C1 O1A Zn2 120.5(4) . . ? C5 O5 Zn2 112.3(3) . 4_465 ? C6 O6A Zn2 119.6(3) . 4_465 ? C7 O7A Zn1 118.1(3) . . ? C11 O11 Zn1 117.0(3) . 4_455 ? C12 O12A Zn1 120.0(3) . 4_455 ? O7A Zn1 O12A 158.67(14) . 4 ? O7A Zn1 N2 103.14(15) . . ? O12A Zn1 N2 93.36(14) 4 . ? O7A Zn1 N1 98.55(15) . . ? O12A Zn1 N1 97.96(14) 4 . ? N2 Zn1 N1 78.30(16) . . ? O7A Zn1 O11 89.74(15) . 4 ? O12A Zn1 O11 75.43(14) 4 4 ? N2 Zn1 O11 166.16(15) . 4 ? N1 Zn1 O11 95.00(15) . 4 ? O6A Zn2 O1A 157.96(14) 4_565 . ? O6A Zn2 N3 100.02(16) 4_565 . ? O1A Zn2 N3 95.55(16) . . ? O6A Zn2 N4 105.26(16) 4_565 . ? O1A Zn2 N4 93.17(16) . . ? N3 Zn2 N4 77.80(18) . . ? O6A Zn2 O5 78.12(13) 4_565 4_565 ? O1A Zn2 O5 83.92(14) . 4_565 ? N3 Zn2 O5 99.95(16) . 4_565 ? N4 Zn2 O5 176.16(16) . 4_565 ? O8W O5W O10W 161.3(12) . . ? O11W O6W O10W 161(4) . . ? O6W O10W O11W 9(2) . . ? O6W O10W O5W 155(3) . . ? O11W O10W O5W 149.5(13) . . ? O6W O11W O10W 10(2) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 69.99 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.628 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.088 # Attachment 'lma331m1.cif' data_lma331m _database_code_depnum_ccdc_archive 'CCDC 763057' #TrackingRef 'lma331m1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H50 Cu2 N4 O25' _chemical_formula_weight 1017.84 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 Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.953(2) _cell_length_b 12.209(4) _cell_length_c 13.829(4) _cell_angle_alpha 111.295(6) _cell_angle_beta 97.980(5) _cell_angle_gamma 102.352(6) _cell_volume 1037.8(6) _cell_formula_units_Z 1 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2914 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 26.82 _exptl_crystal_description flat _exptl_crystal_colour blue _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 1.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.783541 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'Sheldrick, G. M. SAD ABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6354 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0566 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5223 _reflns_number_gt 4916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _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^)+(0.0831P)^2^+0.3085P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _chemical_absolute_configuration rm _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.030(16) _refine_ls_number_reflns 5223 _refine_ls_number_parameters 539 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1296 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 O3 O 0.5091(9) 0.4573(5) 0.4377(5) 0.0274(15) Uiso 0.712(10) 1 d P A 1 O1W O 0.5914(13) 0.5752(8) 0.6573(7) 0.056(2) Uiso 0.712(10) 1 d P A 1 O6B O 1.1031(12) 0.4285(7) 0.4480(6) 0.046(2) Uiso 0.712(10) 1 d P A 1 O3B O 0.629(2) 0.4936(13) 0.4291(11) 0.027(4) Uiso 0.288(10) 1 d P A 2 O2W O 0.457(3) 0.5220(18) 0.5946(16) 0.053(6) Uiso 0.288(10) 1 d P A 2 O6C O 1.030(2) 0.4727(14) 0.5107(13) 0.036(4) Uiso 0.288(10) 1 d P A 2 O3W O 0.9449(7) 0.2299(4) 0.1624(4) 0.0475(13) Uani 1 1 d . . . O4W O 0.3349(9) 0.1326(5) 0.9753(4) 0.0435(12) Uani 1 1 d . . . O5W O 0.4116(11) 0.7475(6) 0.7560(5) 0.060 Uiso 0.933(14) 1 d P . . O6W O 0.1154(11) 0.4798(6) 0.7690(5) 0.060 Uiso 0.905(14) 1 d P . . O7W O 0.7832(11) 0.7865(6) 0.9002(5) 0.060 Uiso 0.956(14) 1 d P . . O8W O 0.9437(12) 0.0428(7) 0.9790(6) 0.060 Uiso 0.847(14) 1 d P . . O9W O 0.0076(14) 0.6708(8) 0.7597(7) 0.060 Uiso 0.710(14) 1 d P . . O10W O 0.5459(16) 0.0034(9) 0.8372(8) 0.060 Uiso 0.661(14) 1 d P . . O11W O 0.400(3) -0.0268(18) 0.7876(15) 0.060 Uiso 0.344(14) 1 d P . . O12W O 0.795(3) 0.0871(19) 0.8266(16) 0.060 Uiso 0.315(14) 1 d P . . O13W O 0.875(4) 0.104(2) 0.932(2) 0.060 Uiso 0.254(14) 1 d P . . C1 C 0.4369(8) 0.4378(5) 0.2258(4) 0.0190(11) Uani 1 1 d . . . C2 C 0.4781(9) 0.3315(5) 0.2511(4) 0.0225(11) Uani 1 1 d . A . H2 H 0.3470 0.2766 0.2492 0.027 Uiso 1 1 calc R . . C3 C 0.6170(15) 0.3822(5) 0.3618(5) 0.047(2) Uani 1 1 d . . . C4 C 0.6411(11) 0.2779(6) 0.3959(5) 0.0333(14) Uani 1 1 d . A . H4 H 0.6884 0.2200 0.3386 0.040 Uiso 1 1 calc R . . C5 C 0.8056(15) 0.3241(7) 0.5018(5) 0.052(2) Uani 1 1 d . . . H5 H 0.7887 0.4006 0.5551 0.063 Uiso 1 1 calc R A . C6 C 1.0250(15) 0.3500(8) 0.4850(7) 0.068(3) Uani 1 1 d . A . C7 C 1.3600(10) 0.2300(6) 0.6843(5) 0.0305(13) Uani 1 1 d . A . C8 C 1.4833(10) 0.2821(6) 0.8011(5) 0.0307(13) Uani 1 1 d . . . H8 H 1.5736 0.2296 0.8057 0.037 Uiso 1 1 calc R . . C9 C 1.6180(11) 0.4114(6) 0.8274(6) 0.0383(16) Uani 1 1 d . . . H9 H 1.7300 0.4037 0.7895 0.046 Uiso 1 1 calc R . . C10 C 1.7135(11) 0.4860(6) 0.9495(6) 0.0416(18) Uani 1 1 d . . . H10 H 1.6036 0.5093 0.9849 0.050 Uiso 1 1 calc R . . C11 C 1.8220(9) 0.4240(6) 1.0088(5) 0.0284(13) Uani 1 1 d . . . H11 H 1.7272 0.3438 0.9974 0.034 Uiso 1 1 calc R . . C12 C 0.0103(8) 0.4012(5) -0.0329(5) 0.0251(12) Uani 1 1 d . . . C13 C 0.3137(11) 0.7316(8) 0.0505(6) 0.0357(16) Uani 1 1 d . . . H13 H 0.2827 0.6566 -0.0106 0.043 Uiso 1 1 calc R B 1 C14 C 0.3690(12) 0.8386(8) 0.0377(7) 0.044(2) Uani 1 1 d . D . H14 H 0.3740 0.8379 -0.0308 0.053 Uiso 1 1 calc R . . C15 C 0.4182(11) 0.9493(7) 0.1274(7) 0.043(2) Uani 1 1 d . . . H15 H 0.4576 1.0255 0.1212 0.052 Uiso 1 1 calc R D . C16 C 0.4082(10) 0.9457(7) 0.2259(7) 0.0407(18) Uani 1 1 d . D . H16 H 0.4400 1.0197 0.2881 0.049 Uiso 1 1 calc R . . C17 C 0.3516(9) 0.8332(6) 0.2329(6) 0.0274(14) Uani 1 1 d . . . C18 C 0.3358(9) 0.8199(6) 0.3333(6) 0.0280(14) Uani 1 1 d . D . C19 C 0.3798(10) 0.9166(6) 0.4328(6) 0.0351(17) Uani 1 1 d . . . H19 H 0.4238 0.9990 0.4401 0.042 Uiso 1 1 calc R D . C20 C 0.3591(11) 0.8916(6) 0.5200(6) 0.0346(16) Uani 1 1 d . D . H20 H 0.3920 0.9568 0.5888 0.042 Uiso 1 1 calc R . . C21 C 0.2894(11) 0.7699(7) 0.5082(6) 0.0363(16) Uani 1 1 d . . . H21 H 0.2702 0.7512 0.5677 0.044 Uiso 1 1 calc R D . C22 C 0.2485(10) 0.6762(6) 0.4053(5) 0.0304(15) Uani 1 1 d . D . H22 H 0.2044 0.5930 0.3957 0.037 Uiso 1 1 calc R C 1 C23 C 0.9611(18) 0.0306(12) 0.2893(10) 0.022(3) Uiso 0.598(17) 1 d P A 1 H23 H 1.0169 0.1114 0.2949 0.027 Uiso 0.598(17) 1 calc PR A 1 C24 C 0.9087(19) -0.0642(13) 0.1925(10) 0.031(3) Uiso 0.598(17) 1 d P A 1 H24 H 0.9197 -0.0495 0.1303 0.038 Uiso 0.598(17) 1 calc PR A 1 C25 C 0.839(2) -0.1830(13) 0.1843(14) 0.033(3) Uiso 0.598(17) 1 d P A 1 H25 H 0.8052 -0.2506 0.1169 0.040 Uiso 0.598(17) 1 calc PR A 1 C26 C 0.8195(18) -0.2010(11) 0.2715(11) 0.028(3) Uiso 0.598(17) 1 d P A 1 H26 H 0.7709 -0.2823 0.2663 0.033 Uiso 0.598(17) 1 calc PR A 1 C27 C 0.8699(18) -0.1012(11) 0.3726(12) 0.025(3) Uiso 0.598(17) 1 d P A 1 C28 C 0.8595(18) -0.1143(11) 0.4721(12) 0.026(3) Uiso 0.598(17) 1 d P A 1 C29 C 0.788(2) -0.2290(12) 0.4726(14) 0.035(3) Uiso 0.598(17) 1 d P A 1 H29 H 0.7387 -0.3030 0.4099 0.042 Uiso 0.598(17) 1 calc PR A 1 C30 C 0.796(3) -0.2235(19) 0.5792(16) 0.053(4) Uiso 0.598(17) 1 d P A 1 H30 H 0.7557 -0.2978 0.5884 0.063 Uiso 0.598(17) 1 calc PR A 1 C31 C 0.858(3) -0.1163(17) 0.6660(17) 0.056(5) Uiso 0.598(17) 1 d P A 1 H31 H 0.8613 -0.1171 0.7346 0.068 Uiso 0.598(17) 1 calc PR A 1 C32 C 0.920(2) -0.0013(15) 0.6575(14) 0.040(3) Uiso 0.598(17) 1 d P A 1 H32 H 0.9536 0.0763 0.7160 0.048 Uiso 0.598(17) 1 calc PR A 1 N1 N 0.3006(8) 0.7267(5) 0.1451(5) 0.0278(12) Uani 1 1 d . D 1 N2 N 0.2703(8) 0.7018(5) 0.3212(4) 0.0220(11) Uani 1 1 d . D 1 N3 N 0.9356(16) 0.0131(10) 0.3799(9) 0.022(3) Uiso 0.598(17) 1 d P A 1 N4B N 0.925(2) -0.0205(13) 0.5315(12) 0.037(3) Uiso 0.598(17) 1 d P A 1 O1A O 0.2554(6) 0.4458(4) 0.2218(3) 0.0238(8) Uani 1 1 d . D . O1B O 0.5738(6) 0.5098(4) 0.2116(3) 0.0270(9) Uani 1 1 d . . . O2 O 0.5737(7) 0.2623(4) 0.1770(3) 0.0309(10) Uani 1 1 d . . . H2A H 0.4995 0.2340 0.1150 0.046 Uiso 1 1 calc R A . O4 O 0.4517(8) 0.2112(5) 0.3996(4) 0.0451(13) Uani 1 1 d . . . O5 O 0.7800(9) 0.2313(6) 0.5423(4) 0.0499(14) Uani 1 1 d . A . H5A H 0.6622 0.2149 0.5516 0.075 Uiso 1 1 calc R . . O6A O 1.1260(9) 0.2793(5) 0.4899(4) 0.0447(13) Uani 1 1 d . . . O7A O 1.1733(7) 0.2262(5) 0.6741(4) 0.0372(11) Uani 1 1 d . . . O7B O 1.4379(8) 0.1908(5) 0.6103(4) 0.0421(12) Uani 1 1 d . . . O8 O 1.3614(6) 0.2847(4) 0.8771(3) 0.0317(9) Uani 1 1 d . . . H8A H 1.2462 0.2878 0.8525 0.047 Uiso 1 1 calc R . . O9 O 1.5072(9) 0.4835(5) 0.7939(5) 0.0630(17) Uani 1 1 d . . . O10 O 1.8531(9) 0.5946(5) 0.9598(5) 0.0594(17) Uani 1 1 d . . . O11 O 1.8864(6) 0.5006(4) 1.1209(3) 0.0334(10) Uani 1 1 d . . . O12A O 0.1849(6) 0.4660(4) 0.0265(3) 0.0253(9) Uani 1 1 d . D . O12B O -0.0173(7) 0.3217(4) -0.1236(3) 0.0368(11) Uani 1 1 d . . . Cu1 Cu 0.22322(7) 0.57652(5) 0.17341(4) 0.01996(17) Uani 1 1 d . . . Cu2 Cu 1.02660(9) 0.14235(6) 0.52521(5) 0.0302(2) Uani 1 1 d . A . N3A N 0.956(3) 0.0299(16) 0.3589(15) 0.028(4) Uiso 0.402(17) 1 d P A 2 C24B C 0.932(3) -0.023(2) 0.1759(17) 0.040(5) Uiso 0.402(17) 1 d P A 2 H24B H 0.9457 -0.0016 0.1169 0.048 Uiso 0.402(17) 1 calc PR A 2 C28B C 0.868(3) -0.1159(16) 0.432(2) 0.030(4) Uiso 0.402(17) 1 d P A 2 C26B C 0.833(3) -0.1849(17) 0.235(2) 0.030(4) Uiso 0.402(17) 1 d P A 2 H26B H 0.7819 -0.2694 0.2204 0.036 Uiso 0.402(17) 1 calc PR A 2 C27B C 0.884(3) -0.0913(16) 0.3413(17) 0.028(4) Uiso 0.402(17) 1 d P A 2 C29B C 0.789(5) -0.236(3) 0.423(3) 0.070(8) Uiso 0.402(17) 1 d P A 2 H29B H 0.7370 -0.3050 0.3566 0.084 Uiso 0.402(17) 1 calc PR A 2 C23B C 0.980(3) 0.069(2) 0.2840(16) 0.034(5) Uiso 0.402(17) 1 d P A 2 H23B H 1.0286 0.1537 0.2999 0.041 Uiso 0.402(17) 1 calc PR A 2 C25B C 0.859(3) -0.149(2) 0.1634(16) 0.036(5) Uiso 0.402(17) 1 d P A 2 H25B H 0.8293 -0.2103 0.0929 0.043 Uiso 0.402(17) 1 calc PR A 2 C30B C 0.792(4) -0.246(2) 0.519(3) 0.054(6) Uiso 0.402(17) 1 d P A 2 H30B H 0.7480 -0.3274 0.5150 0.065 Uiso 0.402(17) 1 calc PR A 2 C32B C 0.919(3) -0.037(2) 0.6140(19) 0.036(5) Uiso 0.402(17) 1 d P A 2 H32B H 0.9912 0.0236 0.6829 0.043 Uiso 0.402(17) 1 calc PR A 2 C31B C 0.849(3) -0.155(2) 0.620(2) 0.043(5) Uiso 0.402(17) 1 d P A 2 H31B H 0.8442 -0.1665 0.6837 0.051 Uiso 0.402(17) 1 calc PR A 2 N4 N 0.916(2) -0.0011(13) 0.5654(14) 0.016(3) Uiso 0.402(17) 1 d P A 2 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 O3W 0.024(2) 0.036(3) 0.064(3) 0.006(2) 0.006(2) 0.001(2) O4W 0.059(3) 0.039(3) 0.026(2) 0.008(2) 0.005(2) 0.014(2) C1 0.023(3) 0.013(2) 0.012(2) -0.001(2) -0.002(2) 0.003(2) C2 0.024(3) 0.022(3) 0.021(3) 0.007(2) 0.004(2) 0.009(2) C3 0.091(6) 0.019(4) 0.019(3) -0.002(3) -0.009(3) 0.025(4) C4 0.046(4) 0.029(3) 0.021(3) 0.006(2) -0.002(3) 0.019(3) C5 0.089(7) 0.040(4) 0.023(3) 0.002(3) -0.009(4) 0.042(4) C6 0.071(6) 0.050(5) 0.052(5) 0.034(4) -0.043(4) -0.029(4) C7 0.028(3) 0.023(3) 0.033(3) 0.004(3) 0.001(3) 0.011(2) C8 0.028(3) 0.025(3) 0.031(3) 0.006(3) -0.002(3) 0.008(2) C9 0.031(4) 0.030(3) 0.049(4) 0.018(3) -0.006(3) 0.006(3) C10 0.035(4) 0.026(3) 0.041(4) -0.005(3) -0.014(3) 0.012(3) C11 0.020(3) 0.032(3) 0.024(3) 0.001(3) 0.002(2) 0.009(2) C12 0.018(3) 0.029(3) 0.030(3) 0.013(3) 0.003(2) 0.010(2) C13 0.031(4) 0.050(4) 0.026(3) 0.020(3) 0.002(3) 0.005(3) C14 0.039(4) 0.058(5) 0.049(5) 0.042(4) 0.007(3) 0.006(4) C15 0.033(4) 0.049(4) 0.072(6) 0.052(4) 0.017(4) 0.009(3) C16 0.021(3) 0.033(3) 0.075(5) 0.031(4) 0.009(3) 0.007(3) C17 0.016(3) 0.031(3) 0.040(4) 0.020(3) 0.006(3) 0.008(2) C18 0.016(3) 0.026(3) 0.042(4) 0.011(3) 0.006(3) 0.011(2) C19 0.018(3) 0.026(3) 0.048(4) 0.003(3) -0.002(3) 0.008(2) C20 0.027(3) 0.030(3) 0.036(4) 0.001(3) 0.001(3) 0.012(3) C21 0.038(4) 0.047(4) 0.028(3) 0.014(3) 0.011(3) 0.021(3) C22 0.027(3) 0.031(3) 0.031(3) 0.011(3) 0.004(3) 0.009(3) N1 0.017(3) 0.039(3) 0.033(3) 0.022(3) 0.004(2) 0.006(2) N2 0.015(2) 0.026(3) 0.022(3) 0.008(2) 0.003(2) 0.006(2) O1A 0.023(2) 0.027(2) 0.027(2) 0.0153(17) 0.0069(17) 0.0111(17) O1B 0.025(2) 0.028(2) 0.027(2) 0.0104(17) 0.0060(17) 0.0058(16) O2 0.030(2) 0.032(2) 0.027(2) 0.0045(19) 0.0051(18) 0.0173(19) O4 0.056(3) 0.069(4) 0.035(2) 0.031(3) 0.022(2) 0.041(3) O5 0.056(3) 0.085(4) 0.041(3) 0.042(3) 0.024(3) 0.048(3) O6A 0.051(3) 0.038(3) 0.033(3) 0.018(2) -0.005(2) -0.008(2) O7A 0.026(2) 0.057(3) 0.028(2) 0.019(2) -0.0009(19) 0.012(2) O7B 0.037(3) 0.045(3) 0.037(3) 0.004(2) 0.009(2) 0.018(2) O8 0.023(2) 0.040(2) 0.034(2) 0.015(2) 0.0080(18) 0.0139(19) O9 0.058(4) 0.036(3) 0.081(4) 0.027(3) -0.025(3) 0.006(3) O10 0.042(3) 0.039(3) 0.084(4) 0.029(3) -0.023(3) 0.001(2) O11 0.019(2) 0.044(3) 0.028(2) 0.0040(19) 0.0063(17) 0.0078(18) O12A 0.018(2) 0.032(2) 0.023(2) 0.0079(17) 0.0062(17) 0.0069(17) O12B 0.029(2) 0.042(3) 0.028(2) 0.000(2) 0.0052(19) 0.013(2) Cu1 0.0173(3) 0.0201(3) 0.0227(3) 0.0096(3) 0.0032(3) 0.0052(2) Cu2 0.0211(4) 0.0342(4) 0.0264(4) 0.0074(3) -0.0011(3) 0.0033(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 O3 C3 1.523(9) . ? O6B C6 1.299(11) . ? O3B C3 1.317(15) . ? O6C C6 1.399(19) . ? O8W O13W 1.28(3) . ? O10W O11W 1.05(2) . ? O12W O13W 1.41(3) . ? C1 O1B 1.240(7) . ? C1 O1A 1.281(7) . ? C1 C2 1.533(7) . ? C2 O2 1.417(7) . ? C2 C3 1.518(8) . ? C3 C4 1.543(9) . ? C4 O4 1.410(9) . ? C4 C5 1.558(9) . ? C5 O5 1.426(10) . ? C5 C6 1.558(15) . ? C6 O6A 1.237(12) . ? C7 O7B 1.217(8) . ? C7 O7A 1.275(8) . ? C7 C8 1.543(9) . ? C8 O8 1.436(8) . ? C8 C9 1.535(9) . ? C9 O9 1.439(8) . ? C9 C10 1.560(10) . ? C10 O10 1.412(10) . ? C10 C11 1.529(9) . ? C11 O11 1.433(7) . ? C11 C12 1.541(8) 1_756 ? C12 O12B 1.233(7) . ? C12 O12A 1.271(7) . ? C12 C11 1.541(8) 1_354 ? C13 N1 1.347(9) . ? C13 C14 1.362(11) . ? C14 C15 1.396(13) . ? C15 C16 1.390(12) . ? C16 C17 1.387(10) . ? C17 N1 1.352(9) . ? C17 C18 1.472(10) . ? C18 N2 1.356(9) . ? C18 C19 1.388(9) . ? C19 C20 1.366(11) . ? C20 C21 1.400(11) . ? C21 C22 1.407(10) . ? C22 N2 1.328(9) . ? C23 C24 1.351(18) . ? C23 N3 1.373(17) . ? C24 C25 1.38(2) . ? C25 C26 1.32(2) . ? C26 C27 1.417(17) . ? C27 N3 1.334(18) . ? C27 C28 1.451(18) . ? C28 N4B 1.088(18) . ? C28 C29 1.39(2) . ? C29 C30 1.44(2) . ? C30 C31 1.35(3) . ? C31 C32 1.43(2) . ? C32 N4B 1.68(2) . ? N1 Cu1 1.990(6) . ? N2 Cu1 1.988(5) . ? N3 Cu2 1.961(10) . ? N4B Cu2 2.000(13) . ? O1A Cu1 1.983(4) . ? O6A Cu2 1.925(5) . ? O7A Cu2 1.941(4) . ? O11 Cu1 2.232(4) 1_756 ? O12A Cu1 1.930(4) . ? Cu1 O11 2.232(4) 1_354 ? Cu2 N4 2.053(15) . ? Cu2 N3A 2.125(18) . ? N3A C23B 1.30(3) . ? N3A C27B 1.37(3) . ? C24B C23B 1.44(3) . ? C24B C25B 1.45(3) . ? C28B C27B 1.41(3) . ? C28B C29B 1.41(4) . ? C28B N4 1.80(3) . ? C26B C25B 1.24(3) . ? C26B C27B 1.43(3) . ? C29B C30B 1.37(4) . ? C30B C31B 1.37(4) . ? C32B N4 0.92(2) . ? C32B C31B 1.45(3) . ? 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 O8W O13W O12W 137(2) . . ? O1B C1 O1A 124.1(5) . . ? O1B C1 C2 120.6(5) . . ? O1A C1 C2 115.3(5) . . ? O2 C2 C3 108.1(5) . . ? O2 C2 C1 111.6(5) . . ? C3 C2 C1 109.4(4) . . ? O3B C3 C2 118.3(8) . . ? O3B C3 O3 36.1(7) . . ? C2 C3 O3 105.9(6) . . ? O3B C3 C4 123.9(8) . . ? C2 C3 C4 111.0(5) . . ? O3 C3 C4 106.9(6) . . ? O4 C4 C3 110.4(6) . . ? O4 C4 C5 112.8(6) . . ? C3 C4 C5 112.6(6) . . ? O5 C5 C6 107.3(6) . . ? O5 C5 C4 108.6(7) . . ? C6 C5 C4 112.5(7) . . ? O6A C6 O6B 114.4(10) . . ? O6A C6 O6C 145.2(10) . . ? O6B C6 O6C 47.6(8) . . ? O6A C6 C5 119.4(7) . . ? O6B C6 C5 125.1(9) . . ? O6C C6 C5 89.1(10) . . ? O7B C7 O7A 124.5(6) . . ? O7B C7 C8 120.8(6) . . ? O7A C7 C8 114.6(6) . . ? O8 C8 C9 110.7(5) . . ? O8 C8 C7 114.1(5) . . ? C9 C8 C7 107.6(6) . . ? O9 C9 C8 112.1(5) . . ? O9 C9 C10 106.3(6) . . ? C8 C9 C10 112.8(6) . . ? O10 C10 C11 108.7(5) . . ? O10 C10 C9 106.2(7) . . ? C11 C10 C9 117.4(5) . . ? O11 C11 C10 110.2(5) . . ? O11 C11 C12 108.4(5) . 1_756 ? C10 C11 C12 110.3(6) . 1_756 ? O12B C12 O12A 123.4(5) . . ? O12B C12 C11 117.8(5) . 1_354 ? O12A C12 C11 118.8(5) . 1_354 ? N1 C13 C14 123.5(8) . . ? C13 C14 C15 118.6(7) . . ? C16 C15 C14 118.6(7) . . ? C17 C16 C15 119.6(8) . . ? N1 C17 C16 121.3(7) . . ? N1 C17 C18 115.1(6) . . ? C16 C17 C18 123.6(7) . . ? N2 C18 C19 121.2(7) . . ? N2 C18 C17 113.8(6) . . ? C19 C18 C17 125.0(6) . . ? C20 C19 C18 119.1(7) . . ? C19 C20 C21 120.1(6) . . ? C20 C21 C22 117.9(7) . . ? N2 C22 C21 121.4(7) . . ? C24 C23 N3 121.7(13) . . ? C23 C24 C25 119.6(14) . . ? C26 C25 C24 119.1(13) . . ? C25 C26 C27 121.1(13) . . ? N3 C27 C26 119.5(14) . . ? N3 C27 C28 116.3(11) . . ? C26 C27 C28 124.1(12) . . ? N4B C28 C29 136.6(18) . . ? N4B C28 C27 102.6(14) . . ? C29 C28 C27 120.7(13) . . ? C28 C29 C30 112.5(14) . . ? C31 C30 C29 122.0(18) . . ? C30 C31 C32 121.7(18) . . ? C31 C32 N4B 111.6(14) . . ? C13 N1 C17 118.4(6) . . ? C13 N1 Cu1 127.0(5) . . ? C17 N1 Cu1 114.5(5) . . ? C22 N2 C18 120.2(6) . . ? C22 N2 Cu1 124.5(5) . . ? C18 N2 Cu1 115.2(5) . . ? C27 N3 C23 118.8(11) . . ? C27 N3 Cu2 115.8(10) . . ? C23 N3 Cu2 124.7(9) . . ? C28 N4B C32 114.9(14) . . ? C28 N4B Cu2 134.6(14) . . ? C32 N4B Cu2 110.1(10) . . ? C1 O1A Cu1 109.5(4) . . ? C6 O6A Cu2 122.1(6) . . ? C7 O7A Cu2 111.1(4) . . ? C11 O11 Cu1 111.4(3) . 1_756 ? C12 O12A Cu1 122.2(4) . . ? O12A Cu1 O1A 90.80(18) . . ? O12A Cu1 N2 175.3(2) . . ? O1A Cu1 N2 93.5(2) . . ? O12A Cu1 N1 93.9(2) . . ? O1A Cu1 N1 158.89(19) . . ? N2 Cu1 N1 81.3(2) . . ? O12A Cu1 O11 78.03(17) . 1_354 ? O1A Cu1 O11 93.11(18) . 1_354 ? N2 Cu1 O11 103.66(19) . 1_354 ? N1 Cu1 O11 108.0(2) . 1_354 ? O6A Cu2 O7A 94.6(2) . . ? O6A Cu2 N3 98.3(4) . . ? O7A Cu2 N3 157.8(3) . . ? O6A Cu2 N4B 168.3(5) . . ? O7A Cu2 N4B 95.1(4) . . ? N3 Cu2 N4B 70.5(6) . . ? O6A Cu2 N4 178.5(5) . . ? O7A Cu2 N4 84.8(5) . . ? N3 Cu2 N4 82.7(6) . . ? N4B Cu2 N4 13.0(5) . . ? O6A Cu2 N3A 87.1(6) . . ? O7A Cu2 N3A 160.4(5) . . ? N3 Cu2 N3A 11.3(6) . . ? N4B Cu2 N3A 81.6(8) . . ? N4 Cu2 N3A 93.9(8) . . ? C23B N3A C27B 124(2) . . ? C23B N3A Cu2 125.6(15) . . ? C27B N3A Cu2 110.1(15) . . ? C23B C24B C25B 115(2) . . ? C27B C28B C29B 121(2) . . ? C27B C28B N4 124.9(14) . . ? C29B C28B N4 113(2) . . ? C25B C26B C27B 115.9(19) . . ? N3A C27B C28B 116.3(16) . . ? N3A C27B C26B 120(2) . . ? C28B C27B C26B 123.5(18) . . ? C30B C29B C28B 115(3) . . ? N3A C23B C24B 117(2) . . ? C26B C25B C24B 127(2) . . ? C31B C30B C29B 129(3) . . ? N4 C32B C31B 141(3) . . ? C30B C31B C32B 110(2) . . ? C32B N4 C28B 110.2(19) . . ? C32B N4 Cu2 150(2) . . ? C28B N4 Cu2 94.2(11) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.690 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.099 # Attachment 'lmd59o1.cif' data_lmd59o _database_code_depnum_ccdc_archive 'CCDC 763058' #TrackingRef 'lmd59o1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 N2 O10 Zn' _chemical_formula_weight 489.73 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' Zn Zn -1.5491 0.6778 '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 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' _cell_length_a 8.0660(2) _cell_length_b 25.1855(6) _cell_length_c 9.8493(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.551(3) _cell_angle_gamma 90.00 _cell_volume 1873.51(9) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3461 _cell_measurement_theta_min 3.5049 _cell_measurement_theta_max 72.4186 _exptl_crystal_description 'pentagonal plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1718 _exptl_crystal_size_mid 0.1265 _exptl_crystal_size_min 0.0193 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.736 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 2.414 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.770 _exptl_absorpt_correction_T_max 0.955 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 16.0711 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3882 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 72.51 _reflns_number_total 2495 _reflns_number_gt 2398 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0749P)^2^+8.4071P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _chemical_absolute_configuration rm _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.11(5) _refine_ls_number_reflns 2495 _refine_ls_number_parameters 207 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1346 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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 C1 C 0.6055(8) 0.1936(3) 0.7691(7) 0.0215(14) Uani 1 1 d . . . C2 C 0.4285(7) 0.1667(3) 0.6882(6) 0.0169(12) Uani 1 1 d . . . H2 H 0.4512 0.1299 0.6608 0.020 Uiso 1 1 calc R . . C3 C 0.3200(7) 0.1636(3) 0.7886(6) 0.0207(12) Uani 1 1 d . . . H3 H 0.3755 0.1364 0.8650 0.025 Uiso 1 1 calc R . . C4 C 0.1256(7) 0.1476(3) 0.7083(6) 0.0237(13) Uani 1 1 d . . . H4 H 0.1197 0.1200 0.6337 0.028 Uiso 1 1 calc R . . C5 C 0.0342(8) 0.1267(3) 0.8114(7) 0.0224(14) Uani 1 1 d . . . H5 H -0.0051 0.1580 0.8547 0.027 Uiso 1 1 calc R . . C6 C -0.1300(8) 0.0933(3) 0.7310(7) 0.0218(13) Uani 1 1 d . . . C10 C 0.2471(8) 0.3184(3) 0.6188(6) 0.0247(15) Uani 1 1 d . . . H10 H 0.2048 0.2850 0.6374 0.030 Uiso 1 1 calc R . . C11 C 0.1795(8) 0.3637(3) 0.6565(7) 0.0297(16) Uani 1 1 d . . . H11 H 0.0936 0.3613 0.7020 0.036 Uiso 1 1 calc R . . C12 C 0.2357(9) 0.4125(3) 0.6284(7) 0.0355(17) Uani 1 1 d . . . H12 H 0.1866 0.4440 0.6514 0.043 Uiso 1 1 calc R . . C13 C 0.3687(8) 0.4152(2) 0.5642(6) 0.0250(13) Uani 1 1 d . . . C14 C 0.4333(8) 0.3663(2) 0.5333(5) 0.0193(13) Uani 1 1 d . . . C15 C 0.44012(18) 0.46412(4) 0.53145(14) 0.0308(15) Uani 1 1 d . . . H15 H 0.3999 0.4970 0.5557 0.037 Uiso 1 1 calc R . . N2 N -0.14694(18) -0.02551(4) 1.06518(14) 0.018(2) Uiso 0.50 1 d PR A 1 C16 C -0.27335(18) -0.02176(4) 1.13096(14) 0.036(3) Uiso 0.50 1 d PR A 1 H16 H -0.3133 0.0121 1.1489 0.043 Uiso 0.50 1 calc PR B 1 C17 C -0.34135(18) -0.06755(4) 1.17045(14) 0.031(3) Uiso 0.50 1 d PR A 1 H17 H -0.4277 -0.0650 1.2154 0.037 Uiso 0.50 1 calc PR C 1 C18 C -0.28294(18) -0.11710(4) 1.14415(14) 0.027(3) Uiso 0.50 1 d PR A 1 H18 H -0.3294 -0.1484 1.1711 0.032 Uiso 0.50 1 calc PR D 1 C19 C -0.15654(18) -0.12086(4) 1.07838(14) 0.025(3) Uiso 0.50 1 d PR A 1 C20 C -0.08854(18) -0.07507(4) 1.03889(14) 0.015(2) Uiso 0.50 1 d PR . 1 C21B C -0.09301(18) -0.17217(4) 1.04807(14) 0.028(3) Uiso 0.50 1 d PR . 1 H21B H -0.1369 -0.2044 1.0723 0.034 Uiso 0.50 1 calc PR E 1 N1 N 0.37056(18) 0.31944(4) 0.55663(14) 0.0201(11) Uani 1 1 d R . . O1A O 0.64922(18) 0.23358(4) 0.71115(14) 0.0221(9) Uani 1 1 d R . . O1B O 0.69895(18) 0.17484(4) 0.88811(14) 0.0248(10) Uani 1 1 d R . . O2 O 0.33830(18) 0.19644(4) 0.55835(14) 0.0213(9) Uani 1 1 d R . . H2A H 0.2750 0.1758 0.4939 0.032 Uiso 1 1 calc R . . O3 O 0.32865(18) 0.21405(4) 0.85813(14) 0.0248(9) Uani 1 1 d R . . H3A H 0.3237 0.2095 0.9411 0.037 Uiso 1 1 calc R . . O4 O 0.02450(18) 0.19290(4) 0.63997(14) 0.0238(8) Uani 1 1 d R . . O5 O 0.14789(18) 0.09534(4) 0.92717(14) 0.0219(9) Uani 1 1 d R . . H5A H 0.2270 0.1147 0.9836 0.033 Uiso 1 1 calc R . . O6A O -0.16444(18) 0.05346(4) 0.79445(14) 0.0229(9) Uani 1 1 d R A . O6B O -0.22443(18) 0.10633(4) 0.60218(14) 0.0292(10) Uani 1 1 d R . . Zn1 Zn 0.50000(18) 0.25327(4) 0.50000(14) 0.0177(3) Uani 1 2 d SR . . Zn2 Zn 0.00000(18) 0.03647(4) 1.00000(14) 0.0252(3) Uani 1 2 d SR . . N3 N -0.11060(18) -0.02940(4) 1.04614(14) 0.028(2) Uiso 0.50 1 d PR A 2 C22 C -0.04732(18) -0.07750(4) 1.01500(14) 0.022(3) Uiso 0.50 1 d PR . 2 C23 C -0.10924(18) -0.12497(4) 1.05129(14) 0.032(3) Uiso 0.50 1 d PRD . 2 C24 C -0.23444(18) -0.12435(4) 1.11872(14) 0.024(3) Uiso 0.50 1 d PR A 2 H24 H -0.2768 -0.1568 1.1435 0.028 Uiso 0.50 1 calc PR F 2 C25 C -0.29772(18) -0.07625(4) 1.14986(14) 0.027(3) Uiso 0.50 1 d PR A 2 H25 H -0.3833 -0.0758 1.1959 0.033 Uiso 0.50 1 calc PR G 2 C26 C -0.23580(18) -0.02877(4) 1.11358(14) 0.015(2) Uiso 0.50 1 d PR A 2 H26 H -0.2791 0.0041 1.1349 0.018 Uiso 0.50 1 calc PR H 2 C27 C -0.03413(18) -0.17171(4) 1.01910(14) 0.022(3) Uiso 0.50 1 d PRD . 2 H27 H -0.0697 -0.2049 1.0460 0.027 Uiso 0.50 1 calc PR I 2 O1W O 0.9910(6) 0.27133(18) 0.8492(6) 0.0369(11) Uani 1 1 d . . . O3W O 0.4529(19) 0.0288(6) 0.6547(16) 0.068(4) Uiso 0.50 1 d P . . O2W O 0.5000 0.0346(13) 0.5000 0.057(7) Uiso 0.30 2 d SP . . O4W O 0.494(3) 0.0173(9) 0.749(2) 0.068(5) Uiso 0.35 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 C1 0.014(2) 0.030(3) 0.024(3) 0.011(3) 0.011(2) 0.009(3) C2 0.018(3) 0.016(3) 0.016(3) 0.000(2) 0.005(2) 0.001(2) C3 0.017(3) 0.026(3) 0.021(3) 0.004(2) 0.008(2) 0.004(2) C4 0.014(2) 0.033(4) 0.024(3) 0.003(3) 0.007(2) -0.002(2) C5 0.024(3) 0.021(3) 0.028(3) 0.008(3) 0.016(2) 0.009(3) C6 0.022(3) 0.023(3) 0.028(3) -0.008(3) 0.018(2) -0.003(3) C10 0.025(3) 0.032(4) 0.023(3) 0.006(2) 0.014(2) 0.002(2) C11 0.023(3) 0.043(4) 0.029(3) -0.003(3) 0.015(2) 0.003(3) C12 0.030(3) 0.042(4) 0.032(3) -0.004(3) 0.008(3) 0.016(3) C13 0.027(3) 0.023(3) 0.016(3) -0.001(2) -0.003(2) 0.005(2) C14 0.029(3) 0.018(3) 0.012(2) -0.001(2) 0.007(2) 0.001(2) C15 0.040(3) 0.016(3) 0.030(3) -0.005(2) 0.004(3) 0.010(3) N1 0.020(2) 0.023(3) 0.020(2) 0.0057(19) 0.0104(18) 0.0030(19) O1A 0.0145(17) 0.030(3) 0.021(2) 0.0012(19) 0.0054(15) -0.0020(18) O1B 0.0186(18) 0.037(3) 0.018(2) 0.001(2) 0.0059(15) 0.0054(19) O2 0.0124(17) 0.030(3) 0.019(2) 0.0007(19) 0.0019(15) -0.0023(18) O3 0.0270(19) 0.027(2) 0.0225(18) -0.0017(17) 0.0117(15) -0.0004(17) O4 0.0183(17) 0.025(2) 0.030(2) 0.0072(17) 0.0105(15) 0.0038(17) O5 0.026(2) 0.021(2) 0.021(2) 0.0044(19) 0.0114(17) -0.0012(19) O6A 0.031(2) 0.020(2) 0.021(2) 0.0001(19) 0.0137(18) -0.0029(19) O6B 0.0207(19) 0.035(3) 0.029(2) 0.009(2) 0.0048(17) 0.000(2) Zn1 0.0142(5) 0.0214(6) 0.0178(5) 0.000 0.0059(4) 0.000 Zn2 0.0428(7) 0.0129(6) 0.0248(6) 0.000 0.0180(5) 0.000 O1W 0.027(2) 0.022(2) 0.064(3) -0.008(2) 0.018(2) -0.0011(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1B 1.243(6) . ? C1 O1A 1.266(7) . ? C1 C2 1.528(8) . ? C2 O2 1.439(6) . ? C2 C3 1.536(7) . ? C3 O3 1.433(6) . ? C3 C4 1.541(7) . ? C4 O4 1.426(6) . ? C4 C5 1.543(8) . ? C5 O5 1.425(6) . ? C5 C6 1.533(9) . ? C6 O6A 1.264(7) . ? C6 O6B 1.272(7) . ? C10 N1 1.339(6) . ? C10 C11 1.371(9) . ? C11 C12 1.370(11) . ? C12 C13 1.426(10) . ? C13 C14 1.412(8) . ? C13 C15 1.443(7) . ? C14 N1 1.335(6) . ? C14 C14 1.443(12) 2_656 ? C15 C15 1.318(3) 2_656 ? N2 C16 1.3900 . ? N2 C20 1.3901 . ? N2 Zn2 2.1881 . ? C16 C17 1.3900 . ? C17 C18 1.3900 . ? C18 C19 1.3899 . ? C19 C20 1.3900 . ? C19 C21B 1.4590 . ? C20 C20 1.843(3) 2_557 ? C21B C21B 2.036(3) 2_557 ? N1 Zn1 2.1419 . ? O1A Zn1 2.0645 . ? O6A Zn2 2.0386 . ? Zn1 O1A 2.065(2) 2_656 ? Zn1 N1 2.1419(18) 2_656 ? Zn1 O2 2.146(2) 2_656 ? Zn2 N3 2.0097(16) 2_557 ? Zn2 N3 2.0097 . ? Zn2 O6A 2.039(2) 2_557 ? Zn2 O5 2.176(2) 2_557 ? Zn2 N2 2.188(2) 2_557 ? N3 C22 1.3900 . ? N3 C26 1.3900 . ? C22 C22 0.910(3) 2_557 ? C22 C23 1.3900 . ? C22 C23 2.007(2) 2_557 ? C23 C24 1.3900 . ? C23 C27 1.4100 . ? C23 C27 1.941(2) 2_557 ? C23 C22 2.007(2) 2_557 ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? C27 C27 0.768(3) 2_557 ? C27 C23 1.941(2) 2_557 ? O3W O4W 0.91(2) . ? O3W O2W 1.702(15) . ? O2W O3W 1.702(15) 2_656 ? 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 O1B C1 O1A 123.7(5) . . ? O1B C1 C2 118.0(5) . . ? O1A C1 C2 118.3(5) . . ? O2 C2 C1 108.7(5) . . ? O2 C2 C3 111.9(4) . . ? C1 C2 C3 109.0(5) . . ? O3 C3 C2 108.6(4) . . ? O3 C3 C4 110.3(5) . . ? C2 C3 C4 112.9(4) . . ? O4 C4 C3 110.1(5) . . ? O4 C4 C5 104.9(4) . . ? C3 C4 C5 112.8(5) . . ? O5 C5 C6 107.8(5) . . ? O5 C5 C4 113.2(4) . . ? C6 C5 C4 111.9(5) . . ? O6A C6 O6B 122.6(5) . . ? O6A C6 C5 118.7(5) . . ? O6B C6 C5 118.7(5) . . ? N1 C10 C11 122.6(6) . . ? C12 C11 C10 120.0(6) . . ? C11 C12 C13 119.1(6) . . ? C14 C13 C12 116.4(6) . . ? C14 C13 C15 119.4(6) . . ? C12 C13 C15 124.2(5) . . ? N1 C14 C13 122.9(5) . . ? N1 C14 C14 117.8(3) . 2_656 ? C13 C14 C14 119.2(4) . 2_656 ? C15 C15 C13 121.4(3) 2_656 . ? C16 N2 C20 120.0 . . ? C16 N2 Zn2 130.5 . . ? C20 N2 Zn2 109.4 . . ? N2 C16 C17 120.0 . . ? C16 C17 C18 120.0 . . ? C19 C18 C17 120.0 . . ? C18 C19 C20 120.0 . . ? C18 C19 C21B 121.6 . . ? C20 C19 C21B 118.4 . . ? C19 C20 N2 120.0 . . ? C19 C20 C20 123.8 . 2_557 ? N2 C20 C20 116.1 . 2_557 ? C19 C21B C21B 117.7 . 2_557 ? C14 N1 C10 118.9(4) . . ? C14 N1 Zn1 113.2(3) . . ? C10 N1 Zn1 127.8(3) . . ? C1 O1A Zn1 119.3(3) . . ? C6 O6A Zn2 118.6(3) . . ? O1A Zn1 O1A 152.2 2_656 . ? O1A Zn1 N1 106.50(5) 2_656 . ? O1A Zn1 N1 95.1 . . ? O1A Zn1 N1 95.14(10) 2_656 2_656 ? O1A Zn1 N1 106.50(7) . 2_656 ? N1 Zn1 N1 77.82(6) . 2_656 ? O1A Zn1 O2 76.37(8) 2_656 2_656 ? O1A Zn1 O2 85.15(7) . 2_656 ? N1 Zn1 O2 170.48(5) . 2_656 ? N1 Zn1 O2 92.96(11) 2_656 2_656 ? N3 Zn2 N3 68.73(7) 2_557 . ? N3 Zn2 O6A 102.25(10) 2_557 2_557 ? N3 Zn2 O6A 97.7 . 2_557 ? N3 Zn2 O6A 97.72(7) 2_557 . ? N3 Zn2 O6A 102.2 . . ? O6A Zn2 O6A 155.8 2_557 . ? N3 Zn2 O5 167.17(12) 2_557 2_557 ? N3 Zn2 O5 98.61(5) . 2_557 ? O6A Zn2 O5 76.73(8) 2_557 2_557 ? O6A Zn2 O5 86.76(7) . 2_557 ? N3 Zn2 N2 10.1 2_557 2_557 ? N3 Zn2 N2 78.85(5) . 2_557 ? O6A Zn2 N2 102.15(10) 2_557 2_557 ? O6A Zn2 N2 95.10(7) . 2_557 ? O5 Zn2 N2 177.11(11) 2_557 2_557 ? N3 Zn2 N2 78.85(7) 2_557 . ? N3 Zn2 N2 10.1 . . ? O6A Zn2 N2 95.10(6) 2_557 . ? O6A Zn2 N2 102.2 . . ? O5 Zn2 N2 88.47(5) 2_557 . ? N2 Zn2 N2 88.98(5) 2_557 . ? C22 N3 C26 120.0 . . ? C22 N3 Zn2 116.3 . . ? C26 N3 Zn2 123.6 . . ? C22 C22 C23 120.1 2_557 . ? C22 C22 N3 119.1 2_557 . ? C23 C22 N3 120.0 . . ? C22 C22 C23 36.80(5) 2_557 2_557 ? C23 C22 C23 84.0 . 2_557 ? N3 C22 C23 155.9 . 2_557 ? C24 C23 C22 120.0 . . ? C24 C23 C27 124.0 . . ? C22 C23 C27 116.0 . . ? C24 C23 C27 143.28(5) . 2_557 ? C22 C23 C27 96.71(5) . 2_557 ? C27 C23 C27 19.33(5) . 2_557 ? C24 C23 C22 142.58(5) . 2_557 ? C22 C23 C22 23.1 . 2_557 ? C27 C23 C22 93.2 . 2_557 ? C27 C23 C22 73.94(10) 2_557 2_557 ? C25 C24 C23 120.0 . . ? C24 C25 C26 120.0 . . ? C25 C26 N3 120.0 . . ? C27 C27 C23 123.3 2_557 . ? C27 C27 C23 37.41(5) 2_557 2_557 ? C23 C27 C23 86.04(5) . 2_557 ? O4W O3W O2W 145(2) . . ? O3W O2W O3W 170(2) . 2_656 ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 72.51 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 1.104 _refine_diff_density_min -0.693 _refine_diff_density_rms 0.119 # Attachment 'lmd59t1.cif' data_lmd59t _database_code_depnum_ccdc_archive 'CCDC 763059' #TrackingRef 'lmd59t1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20.50 Mn N2 O10.25' _chemical_formula_weight 483.80 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' Mn Mn -0.5299 2.8052 '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 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' _cell_length_a 8.09180(10) _cell_length_b 25.5718(3) _cell_length_c 9.95990(10) _cell_angle_alpha 90.00 _cell_angle_beta 111.096(2) _cell_angle_gamma 90.00 _cell_volume 1922.80(4) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3172 _cell_measurement_theta_min 3.4494 _cell_measurement_theta_max 72.8528 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.1021 _exptl_crystal_size_mid 0.0606 _exptl_crystal_size_min 0.0249 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 998 _exptl_absorpt_coefficient_mu 6.177 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.644 _exptl_absorpt_correction_T_max 0.863 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 16.0711 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4512 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 73.01 _reflns_number_total 2697 _reflns_number_gt 2397 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1186P)^2^+14.4460P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _chemical_absolute_configuration rm _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.009(13) _refine_ls_number_reflns 2697 _refine_ls_number_parameters 206 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0761 _refine_ls_wR_factor_ref 0.2098 _refine_ls_wR_factor_gt 0.2025 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 C1 C 0.6049(11) 0.1914(4) 0.7724(8) 0.0213(17) Uani 1 1 d . . . C2 C 0.4246(10) 0.1663(3) 0.6890(8) 0.0209(16) Uani 1 1 d . . . H2 H 0.4449 0.1299 0.6618 0.025 Uiso 1 1 calc R . . C3 C 0.3169(10) 0.1635(3) 0.7897(8) 0.0217(15) Uani 1 1 d . . . H3 H 0.3725 0.1366 0.8655 0.026 Uiso 1 1 calc R . . C4 C 0.1222(10) 0.1477(3) 0.7078(8) 0.0220(15) Uani 1 1 d . . . H4 H 0.1166 0.1208 0.6334 0.026 Uiso 1 1 calc R . . C5 C 0.0313(11) 0.1265(3) 0.8087(8) 0.0202(16) Uani 1 1 d . . . H5 H -0.0095 0.1571 0.8509 0.024 Uiso 1 1 calc R . . C6 C -0.1335(12) 0.0939(3) 0.7235(9) 0.0223(17) Uani 1 1 d . . . C10 C 0.2533(11) 0.3234(3) 0.6217(8) 0.0238(17) Uani 1 1 d . . . H10 H 0.2109 0.2916 0.6463 0.029 Uiso 1 1 calc R . . C11 C 0.1844(12) 0.3692(4) 0.6587(9) 0.034(2) Uani 1 1 d . . . H11 H 0.0999 0.3673 0.7045 0.041 Uiso 1 1 calc R . . C12 C 0.2412(13) 0.4172(4) 0.6276(10) 0.036(2) Uani 1 1 d . . . H12 H 0.1938 0.4487 0.6495 0.043 Uiso 1 1 calc R . . C13 C 0.3695(12) 0.4188(3) 0.5634(8) 0.030(2) Uani 1 1 d . . . C14 C 0.4334(11) 0.3703(3) 0.5331(7) 0.0206(16) Uani 1 1 d . . . C15 C 0.4379(2) 0.46344(5) 0.53238(18) 0.038(2) Uani 1 1 d . . . H15 H 0.3988 0.4960 0.5561 0.045 Uiso 1 1 calc R . . N2 N -0.1485(2) -0.02620(5) 1.06601(18) 0.049(5) Uiso 0.50 1 d PR A 1 C16 C -0.2749(2) -0.02244(5) 1.13179(18) 0.056(6) Uiso 0.50 1 d PR A 1 H16 H -0.3146 0.0109 1.1497 0.067 Uiso 0.50 1 d PR B 1 C17 C -0.3429(2) -0.06823(5) 1.17129(18) 0.041(5) Uiso 0.50 1 d PR A 1 H17 H -0.4285 -0.0657 1.2159 0.049 Uiso 0.50 1 d PR C 1 C18 C -0.2845(2) -0.11778(5) 1.14498(18) 0.029(4) Uiso 0.50 1 d PR A 1 H18 H -0.3307 -0.1486 1.1717 0.035 Uiso 0.50 1 d PR D 1 C19 C -0.1581(2) -0.12154(5) 1.07920(18) 0.023(3) Uiso 0.50 1 d PR A 1 C21B C -0.0946(2) -0.17284(5) 1.04889(18) 0.048(5) Uiso 0.50 1 d PR A 1 C20 C -0.0901(2) -0.07575(5) 1.03970(18) 0.024(3) Uiso 0.50 1 d PR . 1 N1 N 0.3690(2) 0.31876(5) 0.55746(18) 0.0181(14) Uani 1 1 d R . . O1A O 0.6477(2) 0.23290(5) 0.71198(18) 0.0208(12) Uani 1 1 d R . . O1B O 0.6974(2) 0.17416(5) 0.88894(18) 0.0258(13) Uani 1 1 d R . . O2 O 0.3367(2) 0.19576(5) 0.55917(18) 0.0290(14) Uani 1 1 d R . . O3 O 0.3271(2) 0.21337(5) 0.85896(18) 0.0255(12) Uani 1 1 d R . . H3A H 0.3222 0.2090 0.9410 0.038 Uiso 1 1 calc R . . O4 O 0.0229(2) 0.19222(5) 0.64080(18) 0.0245(11) Uani 1 1 d R . . O5 O 0.1463(2) 0.09465(5) 0.92800(18) 0.0205(12) Uani 1 1 d R . . H5A H 0.2268 0.1135 0.9839 0.031 Uiso 1 1 calc R . . O6A O -0.1660(2) 0.05277(5) 0.79527(18) 0.0343(15) Uani 1 1 d R . . O6B O -0.2260(2) 0.10565(5) 0.60301(18) 0.0354(15) Uani 1 1 d R . . Mn1 Mn 0.5000(2) 0.25259(5) 0.50000(18) 0.0176(4) Uani 1 2 d SR . . Mn2 Mn 0.0000(2) 0.03578(5) 1.00000(18) 0.0308(5) Uani 1 2 d SR . . N3 N -0.1122(2) -0.03008(5) 1.04697(18) 0.031(3) Uiso 0.50 1 d PR A 2 C22 C -0.0489(2) -0.07818(5) 1.01582(18) 0.021(3) Uiso 0.50 1 d PR . 2 C23 C -0.1108(2) -0.12566(5) 1.05211(18) 0.024(3) Uiso 0.50 1 d PR . 2 C24 C -0.2360(2) -0.12503(5) 1.11954(18) 0.023(3) Uiso 0.50 1 d PR A 2 H24 H -0.2780 -0.1570 1.1442 0.027 Uiso 0.50 1 calc PR E 2 C25 C -0.2993(2) -0.07693(5) 1.15069(18) 0.026(4) Uiso 0.50 1 d PR A 2 H25 H -0.3841 -0.0765 1.1964 0.031 Uiso 0.50 1 calc PR F 2 C26 C -0.2374(2) -0.02946(5) 1.11440(18) 0.015(3) Uiso 0.50 1 d PR A 2 H26 H -0.2803 0.0029 1.1356 0.018 Uiso 0.50 1 calc PR G 2 C27 C -0.0357(2) -0.17240(5) 1.01993(18) 0.029(4) Uiso 0.50 1 d PR . 2 H27 H -0.0711 -0.2050 1.0465 0.035 Uiso 0.50 1 calc PR H 2 O1W O 0.9894(8) 0.2696(2) 0.8497(7) 0.0343(14) Uani 1 1 d . . . O2W O -0.556(2) 0.0286(6) 0.6539(16) 0.047(3) Uiso 0.50 1 d P . . O3W O -0.5000 0.0376(8) 0.5000 0.043(4) Uiso 0.50 2 d SP . . O4W O -0.498(3) 0.0107(9) 0.760(2) 0.079(6) 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 C1 0.022(4) 0.026(4) 0.022(4) 0.005(3) 0.015(3) 0.009(3) C2 0.021(4) 0.022(4) 0.020(4) 0.002(3) 0.008(3) 0.008(3) C3 0.027(4) 0.024(4) 0.020(3) 0.002(3) 0.016(3) 0.008(3) C4 0.022(4) 0.025(4) 0.024(4) 0.007(3) 0.014(3) 0.005(3) C5 0.027(4) 0.013(3) 0.024(4) 0.005(3) 0.014(3) 0.001(3) C6 0.030(4) 0.017(4) 0.027(4) -0.003(3) 0.019(3) -0.002(3) C10 0.024(4) 0.024(4) 0.023(4) -0.002(3) 0.008(3) 0.010(3) C11 0.032(4) 0.040(5) 0.032(4) -0.013(4) 0.013(3) 0.014(4) C12 0.046(5) 0.024(4) 0.030(4) -0.011(3) 0.005(4) 0.018(4) C13 0.039(4) 0.026(4) 0.014(4) -0.005(3) -0.003(3) 0.008(4) C14 0.030(4) 0.016(3) 0.011(3) -0.001(2) 0.001(3) 0.004(3) C15 0.053(6) 0.020(4) 0.026(4) -0.010(3) -0.003(4) 0.006(4) N1 0.025(3) 0.021(3) 0.009(3) 0.001(2) 0.007(2) 0.011(3) O1A 0.023(3) 0.026(3) 0.015(2) 0.001(2) 0.008(2) -0.006(2) O1B 0.019(2) 0.041(3) 0.018(3) 0.007(2) 0.009(2) 0.008(2) O2 0.015(2) 0.052(4) 0.023(3) 0.002(3) 0.010(2) -0.002(3) O3 0.029(3) 0.033(3) 0.018(2) 0.001(2) 0.013(2) 0.006(2) O4 0.022(2) 0.024(3) 0.030(3) 0.009(2) 0.012(2) 0.005(2) O5 0.038(3) 0.009(2) 0.019(3) 0.004(2) 0.015(2) -0.001(2) O6A 0.046(4) 0.025(3) 0.039(4) -0.007(3) 0.024(3) 0.001(3) O6B 0.025(3) 0.038(4) 0.041(4) 0.012(3) 0.008(3) 0.002(3) Mn1 0.0183(8) 0.0206(9) 0.0159(8) 0.000 0.0083(6) 0.000 Mn2 0.0640(14) 0.0131(8) 0.0264(10) 0.000 0.0296(10) 0.000 O1W 0.031(3) 0.030(3) 0.045(3) -0.007(3) 0.017(3) 0.001(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 C1 O1B 1.216(8) . ? C1 O1A 1.325(9) . ? C1 C2 1.536(11) . ? C2 O2 1.444(8) . ? C2 C3 1.549(10) . ? C3 O3 1.438(8) . ? C3 C4 1.545(10) . ? C4 O4 1.414(8) . ? C4 C5 1.541(10) . ? C5 O5 1.464(8) . ? C5 C6 1.542(11) . ? C6 O6B 1.202(9) . ? C6 O6A 1.349(9) . ? C10 N1 1.316(8) . ? C10 C11 1.402(12) . ? C11 C12 1.384(15) . ? C12 C13 1.402(15) . ? C13 C15 1.351(10) . ? C13 C14 1.420(11) . ? C14 C14 1.452(17) 2_656 ? C14 N1 1.468(8) . ? C15 C15 1.376(4) 2_656 ? N2 C16 1.4025 . ? N2 C20 1.4096 . ? N2 Mn2 2.2265 . ? C16 C17 1.4088 . ? C17 C18 1.4095 . ? C18 C19 1.4025 . ? C19 C20 1.4088 . ? C19 C21B 1.4793 . ? C20 C20 1.893(4) 2_557 ? N1 Mn1 2.1798 . ? O1A Mn1 2.0791 . ? Mn1 O1A 2.079(3) 2_656 ? Mn1 N1 2.180(2) 2_656 ? Mn1 O2 2.183(3) 2_656 ? Mn2 O6A 2.044(3) 2_557 ? Mn2 N3 2.046(2) 2_557 ? Mn2 N3 2.0458 . ? Mn2 O5 2.189(3) 2_557 ? Mn2 N2 2.226(3) 2_557 ? N3 C26 1.4027 . ? N3 C22 1.4091 . ? C22 C22 0.951(4) 2_557 ? C22 C23 1.4092 . ? C23 C24 1.4027 . ? C23 C27 1.4286 . ? C23 C27 1.990(3) 2_557 ? C24 C25 1.4091 . ? C25 C26 1.4092 . ? C27 C27 0.810(4) 2_557 ? C27 C23 1.990(3) 2_557 ? O2W O4W 1.09(2) . ? O2W O3W 1.763(15) . ? O3W O2W 1.763(15) 2_456 ? 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 O1B C1 O1A 123.6(7) . . ? O1B C1 C2 120.1(7) . . ? O1A C1 C2 116.3(6) . . ? O2 C2 C1 109.3(6) . . ? O2 C2 C3 113.2(6) . . ? C1 C2 C3 108.4(6) . . ? O3 C3 C4 110.9(6) . . ? O3 C3 C2 108.7(6) . . ? C4 C3 C2 112.0(6) . . ? O4 C4 C5 105.6(6) . . ? O4 C4 C3 109.7(6) . . ? C5 C4 C3 112.5(6) . . ? O5 C5 C4 114.3(6) . . ? O5 C5 C6 108.5(6) . . ? C4 C5 C6 110.7(7) . . ? O6B C6 O6A 123.7(7) . . ? O6B C6 C5 121.2(7) . . ? O6A C6 C5 115.1(7) . . ? N1 C10 C11 128.6(8) . . ? C12 C11 C10 119.0(9) . . ? C11 C12 C13 119.3(8) . . ? C15 C13 C12 124.1(7) . . ? C15 C13 C14 118.6(8) . . ? C12 C13 C14 117.2(8) . . ? C13 C14 C14 118.9(5) . 2_656 ? C13 C14 N1 124.9(7) . . ? C14 C14 N1 116.2(3) 2_656 . ? C13 C15 C15 122.4(4) . 2_656 ? C16 N2 C20 119.9 . . ? C16 N2 Mn2 130.6 . . ? C20 N2 Mn2 109.4 . . ? N2 C16 C17 119.8 . . ? C16 C17 C18 120.3 . . ? C19 C18 C17 119.9 . . ? C18 C19 C20 119.8 . . ? C18 C19 C21B 121.4 . . ? C20 C19 C21B 118.7 . . ? C19 C20 N2 120.3 . . ? C19 C20 C20 123.6 . 2_557 ? N2 C20 C20 116.0 . 2_557 ? C10 N1 C14 110.8(5) . . ? C10 N1 Mn1 134.2(4) . . ? C14 N1 Mn1 114.7(3) . . ? C1 O1A Mn1 120.4(4) . . ? O1A Mn1 O1A 152.0 . 2_656 ? O1A Mn1 N1 94.4 . . ? O1A Mn1 N1 107.37(7) 2_656 . ? O1A Mn1 N1 107.37(9) . 2_656 ? O1A Mn1 N1 94.44(13) 2_656 2_656 ? N1 Mn1 N1 78.15(8) . 2_656 ? O1A Mn1 O2 86.02(9) . 2_656 ? O1A Mn1 O2 75.35(10) 2_656 2_656 ? N1 Mn1 O2 170.56(7) . 2_656 ? N1 Mn1 O2 92.70(14) 2_656 2_656 ? O6A Mn2 N3 102.52(13) 2_557 2_557 ? O6A Mn2 N3 97.66(6) 2_557 . ? N3 Mn2 N3 69.16(9) 2_557 . ? O6A Mn2 O5 76.46(10) 2_557 2_557 ? N3 Mn2 O5 167.88(16) 2_557 2_557 ? N3 Mn2 O5 98.89(7) . 2_557 ? O6A Mn2 N2 102.42(13) 2_557 2_557 ? N3 Mn2 N2 10.1 2_557 2_557 ? N3 Mn2 N2 79.19(7) . 2_557 ? O5 Mn2 N2 177.67(15) 2_557 2_557 ? O6A Mn2 N2 95.02(8) 2_557 . ? N3 Mn2 N2 79.19(9) 2_557 . ? N3 Mn2 N2 10.1 . . ? O5 Mn2 N2 88.84(7) 2_557 . ? N2 Mn2 N2 89.23(7) 2_557 . ? C26 N3 C22 119.8 . . ? C26 N3 Mn2 123.8 . . ? C22 N3 Mn2 116.2 . . ? C22 C22 N3 119.0 2_557 . ? C22 C22 C23 120.0 2_557 . ? N3 C22 C23 120.3 . . ? C24 C23 C22 119.8 . . ? C24 C23 C27 123.8 . . ? C22 C23 C27 116.4 . . ? C24 C23 C27 143.72(7) . 2_557 ? C22 C23 C27 96.43(7) . 2_557 ? C27 C23 C27 19.94(7) . 2_557 ? C23 C24 C25 119.8 . . ? C24 C25 C26 120.3 . . ? N3 C26 C25 119.8 . . ? C27 C27 C23 123.1 2_557 . ? C27 C27 C23 36.97(7) 2_557 2_557 ? C23 C27 C23 86.29(7) . 2_557 ? O4W O2W O3W 137.7(18) . . ? O2W O3W O2W 165.1(18) 2_456 . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 73.01 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 1.557 _refine_diff_density_min -1.263 _refine_diff_density_rms 0.133 # Attachment 'lmd65b1.cif' data_lmd65b _database_code_depnum_ccdc_archive 'CCDC 763060' #TrackingRef 'lmd65b1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 Co N2 O10' _chemical_formula_weight 483.29 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' Co Co -2.3653 3.6143 '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 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' _cell_length_a 8.0565(4) _cell_length_b 25.1374(8) _cell_length_c 9.8567(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.482(5) _cell_angle_gamma 90.00 _cell_volume 1869.98(13) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2281 _cell_measurement_theta_min 5.1095 _cell_measurement_theta_max 72.4823 _exptl_crystal_description plate _exptl_crystal_colour pink _exptl_crystal_size_max 0.2192 _exptl_crystal_size_mid 0.1483 _exptl_crystal_size_min 0.0633 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.717 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 996 _exptl_absorpt_coefficient_mu 7.790 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.303 _exptl_absorpt_correction_T_max 0.657 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 16.0711 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4814 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.95 _diffrn_reflns_theta_max 72.71 _reflns_number_total 2858 _reflns_number_gt 2160 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0918P)^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 _chemical_absolute_configuration rm _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.002(9) _refine_ls_number_reflns 2858 _refine_ls_number_parameters 206 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1497 _refine_ls_wR_factor_gt 0.1395 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6065(10) 0.1937(3) 0.7702(7) 0.0290(16) Uani 1 1 d . . . C2 C 0.4285(9) 0.1671(3) 0.6887(7) 0.0242(14) Uani 1 1 d . . . H2 H 0.4510 0.1301 0.6617 0.029 Uiso 1 1 calc R . . C3 C 0.3190(9) 0.1640(3) 0.7900(6) 0.0284(14) Uani 1 1 d . . . H3 H 0.3746 0.1368 0.8666 0.034 Uiso 1 1 calc R . . C4 C 0.1261(9) 0.1478(2) 0.7093(7) 0.0270(13) Uani 1 1 d . . . H4 H 0.1218 0.1202 0.6350 0.032 Uiso 1 1 calc R . . C5 C 0.0329(9) 0.1267(3) 0.8100(7) 0.0285(16) Uani 1 1 d . . . H5 H -0.0074 0.1580 0.8528 0.034 Uiso 1 1 calc R . . C6 C -0.1291(10) 0.0931(2) 0.7308(8) 0.0266(15) Uani 1 1 d . . . C10 C 0.2483(10) 0.3172(3) 0.6187(7) 0.0337(17) Uani 1 1 d . . . H10 H 0.2073 0.2835 0.6375 0.040 Uiso 1 1 calc R . . C11 C 0.1788(10) 0.3639(3) 0.6570(7) 0.0394(18) Uani 1 1 d . . . H11 H 0.0919 0.3620 0.7016 0.047 Uiso 1 1 calc R . . C12 C 0.2387(11) 0.4118(3) 0.6287(7) 0.0390(18) Uani 1 1 d . . . H12 H 0.1919 0.4437 0.6528 0.047 Uiso 1 1 calc R . . C13 C 0.3684(10) 0.4146(3) 0.5644(6) 0.0310(16) Uani 1 1 d . . . C14 C 0.4343(10) 0.3658(2) 0.5319(6) 0.0296(16) Uani 1 1 d . . . C15 C 0.4397(2) 0.46425(4) 0.53144(15) 0.0356(17) Uani 1 1 d . . . H15 H 0.3990 0.4971 0.5555 0.043 Uiso 1 1 calc R . . N2 N -0.1467(2) -0.02538(4) 1.06506(15) 0.0135(19) Uiso 0.50 1 d PR A 1 C16 C -0.2731(2) -0.02162(4) 1.13084(15) 0.040(4) Uiso 0.50 1 d PR A 1 H16 H -0.3122 0.0116 1.1484 0.048 Uiso 0.50 1 d PR B 1 C17 C -0.3411(2) -0.06742(4) 1.17033(15) 0.040(4) Uiso 0.50 1 d PR A 1 H17 H -0.4275 -0.0648 1.2153 0.048 Uiso 0.50 1 calc PR C 1 C18 C -0.2827(2) -0.11697(4) 1.14403(15) 0.032(3) Uiso 0.50 1 d PR A 1 H18 H -0.3292 -0.1483 1.1710 0.038 Uiso 0.50 1 calc PR D 1 C19 C -0.1562(2) -0.12073(4) 1.07826(15) 0.029(3) Uiso 0.50 1 d PR A 1 C20 C -0.0882(2) -0.07493(4) 1.03877(15) 0.018(2) Uiso 0.50 1 d PR . 1 C21B C -0.0927(2) -0.17203(4) 1.04795(15) 0.040(4) Uiso 0.50 1 d PR . 1 H21B H -0.1366 -0.2044 1.0723 0.048 Uiso 0.50 1 calc PR E 1 N1 N 0.3709(2) 0.31958(4) 0.55651(15) 0.0289(13) Uani 1 1 d R . . O1A O 0.6495(2) 0.23372(4) 0.71103(15) 0.0294(11) Uani 1 1 d R . . O1B O 0.6992(2) 0.17498(4) 0.88799(15) 0.0319(11) Uani 1 1 d R . . O2 O 0.3386(2) 0.19658(4) 0.55823(15) 0.0251(10) Uani 1 1 d R . . O3 O 0.3289(2) 0.21418(4) 0.85801(15) 0.0304(10) Uani 1 1 d R . . H3A H 0.3241 0.2099 0.9411 0.046 Uiso 1 1 calc R . . O4 O 0.0248(2) 0.19303(4) 0.63985(15) 0.0315(10) Uani 1 1 d R . . O5 O 0.1482(2) 0.09547(4) 0.92705(15) 0.0285(10) Uani 1 1 d R . . H5A H 0.1917 0.1148 1.0005 0.043 Uiso 1 1 calc R . . O6A O -0.1641(2) 0.05359(4) 0.79433(15) 0.0318(11) Uani 1 1 d R A . O6B O -0.2241(2) 0.10647(4) 0.60207(15) 0.0357(12) Uani 1 1 d R . . Co1 Co 0.5000(2) 0.25340(4) 0.50000(15) 0.0235(4) Uani 1 2 d SR . . Co2 Co 0.0000(2) 0.03660(4) 1.00000(15) 0.0293(4) Uani 1 2 d SR . . N3 N -0.1103(2) -0.02927(4) 1.04603(15) 0.030(3) Uiso 0.50 1 d PR A 2 C22 C -0.0470(2) -0.07737(4) 1.01488(15) 0.027(3) Uiso 0.50 1 d PR . 2 C23 C -0.1089(2) -0.12484(4) 1.05118(15) 0.030(3) Uiso 0.50 1 d PR . 2 C24 C -0.2341(2) -0.12421(4) 1.11861(15) 0.034(3) Uiso 0.50 1 d PR A 2 H24 H -0.2765 -0.1567 1.1434 0.041 Uiso 0.50 1 calc PR F 2 C25 C -0.2974(2) -0.07612(4) 1.14974(15) 0.029(3) Uiso 0.50 1 d PR A 2 H25 H -0.3831 -0.0757 1.1959 0.034 Uiso 0.50 1 calc PR G 2 C26 C -0.2355(2) -0.02864(4) 1.11346(15) 0.017(3) Uiso 0.50 1 d PR A 2 H26 H -0.2788 0.0043 1.1348 0.021 Uiso 0.50 1 calc PR H 2 C27 C -0.0338(2) -0.17158(4) 1.01898(15) 0.025(3) Uiso 0.50 1 d PR . 2 H27 H -0.0693 -0.2048 1.0460 0.030 Uiso 0.50 1 calc PR I 2 O1W O 0.9909(7) 0.27180(19) 0.8496(6) 0.0463(13) Uani 1 1 d . . . O3W O 0.455(2) 0.0289(6) 0.6497(16) 0.071(4) Uiso 0.50 1 d P . . O2W O 0.5000 0.0333(11) 0.5000 0.052(6) Uiso 0.30 2 d SP . . O4W O 0.492(3) 0.0189(8) 0.746(2) 0.065(5) Uiso 0.35 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 C1 0.030(4) 0.038(4) 0.022(4) 0.007(3) 0.013(3) 0.008(3) C2 0.024(3) 0.024(3) 0.025(3) 0.004(3) 0.009(3) 0.003(3) C3 0.032(3) 0.033(4) 0.024(3) 0.000(3) 0.015(3) 0.007(3) C4 0.029(3) 0.027(3) 0.029(3) -0.001(3) 0.015(3) -0.003(3) C5 0.033(4) 0.030(4) 0.024(3) 0.003(3) 0.013(3) 0.006(3) C6 0.034(4) 0.018(3) 0.033(4) 0.000(3) 0.018(3) 0.002(3) C10 0.037(4) 0.039(4) 0.032(4) -0.007(3) 0.020(3) 0.001(3) C11 0.033(4) 0.056(5) 0.032(4) -0.009(3) 0.015(3) 0.006(3) C12 0.044(4) 0.032(4) 0.035(4) -0.006(3) 0.007(3) 0.010(3) C13 0.041(4) 0.026(3) 0.017(3) -0.001(2) 0.000(3) 0.007(3) C14 0.043(4) 0.030(4) 0.012(3) 0.001(2) 0.004(3) 0.001(3) C15 0.047(4) 0.020(3) 0.034(4) -0.004(3) 0.007(3) 0.008(3) N1 0.031(3) 0.040(3) 0.018(3) 0.003(2) 0.011(2) 0.009(2) O1A 0.027(2) 0.034(3) 0.027(3) 0.000(2) 0.009(2) -0.001(2) O1B 0.030(2) 0.043(3) 0.024(2) 0.004(2) 0.010(2) 0.007(2) O2 0.029(2) 0.030(2) 0.019(2) 0.0057(18) 0.0117(19) -0.006(2) O3 0.040(3) 0.032(2) 0.023(2) 0.0011(18) 0.0146(19) 0.0064(19) O4 0.033(2) 0.030(2) 0.032(2) 0.0093(18) 0.012(2) 0.0039(19) O5 0.039(3) 0.026(2) 0.021(2) 0.0035(19) 0.013(2) 0.003(2) O6A 0.047(3) 0.024(3) 0.026(3) 0.003(2) 0.016(2) -0.002(2) O6B 0.033(3) 0.042(3) 0.031(3) 0.010(2) 0.010(2) -0.006(2) Co1 0.0251(8) 0.0269(8) 0.0218(8) 0.000 0.0122(7) 0.000 Co2 0.0498(11) 0.0175(8) 0.0246(9) 0.000 0.0182(8) 0.000 O1W 0.041(3) 0.027(3) 0.072(4) -0.007(2) 0.020(3) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1B 1.233(7) . ? C1 O1A 1.270(7) . ? C1 C2 1.531(10) . ? C2 O2 1.441(7) . ? C2 C3 1.549(8) . ? C3 O3 1.417(7) . ? C3 C4 1.533(9) . ? C4 O4 1.428(6) . ? C4 C5 1.533(8) . ? C5 O5 1.435(7) . ? C5 C6 1.520(10) . ? C6 O6A 1.259(7) . ? C6 O6B 1.276(8) . ? C10 N1 1.334(7) . ? C10 C11 1.407(9) . ? C11 C12 1.364(11) . ? C12 C13 1.401(11) . ? C13 C14 1.417(9) . ? C13 C15 1.457(7) . ? C14 N1 1.325(7) . ? C14 C14 1.408(14) 2_656 ? C15 C15 1.322(3) 2_656 ? N2 C20 1.3876 . ? N2 C16 1.3887 . ? N2 Co2 2.1829 . ? C16 C17 1.3878 . ? C17 C18 1.3876 . ? C18 C19 1.3886 . ? C19 C20 1.3878 . ? C19 C21B 1.4565 . ? C20 C20 1.835(3) 2_557 ? C21B C21B 2.028(3) 2_557 ? N1 Co1 2.1367 . ? O1A Co1 2.0662 . ? O6A Co2 2.0408 . ? Co1 O1A 2.066(3) 2_656 ? Co1 N1 2.137(2) 2_656 ? Co1 O2 2.141(2) 2_656 ? Co2 N3 2.0048(18) 2_557 ? Co2 N3 2.0048 . ? Co2 O6A 2.041(3) 2_557 ? Co2 O5 2.175(2) 2_557 ? Co2 N2 2.183(2) 2_557 ? N3 C22 1.3877 . ? N3 C26 1.3888 . ? C22 C22 0.903(3) 2_557 ? C22 C23 1.3877 . ? C22 C23 2.000(2) 2_557 ? C23 C24 1.3888 . ? C23 C27 1.4077 . ? C23 C27 1.934(2) 2_557 ? C23 C22 2.000(2) 2_557 ? C24 C25 1.3876 . ? C25 C26 1.3878 . ? C27 C27 0.762(3) 2_557 ? C27 C23 1.934(2) 2_557 ? O3W O4W 0.92(2) . ? O3W O2W 1.642(15) . ? O2W O3W 1.642(15) 2_656 ? 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 O1B C1 O1A 124.2(6) . . ? O1B C1 C2 118.4(6) . . ? O1A C1 C2 117.4(6) . . ? O2 C2 C1 109.3(5) . . ? O2 C2 C3 112.3(5) . . ? C1 C2 C3 108.9(5) . . ? O3 C3 C4 111.2(5) . . ? O3 C3 C2 108.0(5) . . ? C4 C3 C2 112.4(5) . . ? O4 C4 C3 110.0(5) . . ? O4 C4 C5 105.0(5) . . ? C3 C4 C5 113.1(5) . . ? O5 C5 C6 107.9(5) . . ? O5 C5 C4 112.6(5) . . ? C6 C5 C4 112.7(6) . . ? O6A C6 O6B 122.7(6) . . ? O6A C6 C5 119.0(6) . . ? O6B C6 C5 118.3(5) . . ? N1 C10 C11 120.8(6) . . ? C12 C11 C10 118.7(7) . . ? C11 C12 C13 120.7(6) . . ? C12 C13 C14 117.2(6) . . ? C12 C13 C15 123.9(6) . . ? C14 C13 C15 118.9(6) . . ? N1 C14 C14 118.7(3) . 2_656 ? N1 C14 C13 121.3(6) . . ? C14 C14 C13 120.0(4) 2_656 . ? C15 C15 C13 121.1(3) 2_656 . ? C20 N2 C16 120.0 . . ? C20 N2 Co2 109.4 . . ? C16 N2 Co2 130.5 . . ? C17 C16 N2 120.0 . . ? C18 C17 C16 119.9 . . ? C17 C18 C19 120.0 . . ? C20 C19 C18 120.0 . . ? C20 C19 C21B 118.4 . . ? C18 C19 C21B 121.6 . . ? N2 C20 C19 119.9 . . ? N2 C20 C20 116.1 . 2_557 ? C19 C20 C20 123.8 . 2_557 ? C19 C21B C21B 117.7 . 2_557 ? C14 N1 C10 121.3(4) . . ? C14 N1 Co1 112.4(3) . . ? C10 N1 Co1 126.2(3) . . ? C1 O1A Co1 119.7(3) . . ? C6 O6A Co2 118.6(4) . . ? O1A Co1 O1A 152.3 2_656 . ? O1A Co1 N1 95.14(10) 2_656 2_656 ? O1A Co1 N1 106.46(7) . 2_656 ? O1A Co1 N1 106.46(6) 2_656 . ? O1A Co1 N1 95.1 . . ? N1 Co1 N1 77.75(6) 2_656 . ? O1A Co1 O2 76.42(8) 2_656 2_656 ? O1A Co1 O2 85.14(7) . 2_656 ? N1 Co1 O2 93.02(12) 2_656 2_656 ? N1 Co1 O2 170.47(6) . 2_656 ? N3 Co2 N3 68.64(7) 2_557 . ? N3 Co2 O6A 97.62(8) 2_557 . ? N3 Co2 O6A 102.3 . . ? N3 Co2 O6A 102.31(11) 2_557 2_557 ? N3 Co2 O6A 97.61(5) . 2_557 ? O6A Co2 O6A 155.8 . 2_557 ? N3 Co2 O5 167.05(13) 2_557 2_557 ? N3 Co2 O5 98.57(6) . 2_557 ? O6A Co2 O5 86.91(7) . 2_557 ? O6A Co2 O5 76.65(8) 2_557 2_557 ? N3 Co2 N2 10.2 2_557 2_557 ? N3 Co2 N2 78.78(6) . 2_557 ? O6A Co2 N2 94.98(7) . 2_557 ? O6A Co2 N2 102.24(11) 2_557 2_557 ? O5 Co2 N2 177.01(12) 2_557 2_557 ? N3 Co2 N2 78.78(7) 2_557 . ? N3 Co2 N2 10.2 . . ? O6A Co2 N2 102.2 . . ? O6A Co2 N2 94.98(6) 2_557 . ? O5 Co2 N2 88.42(6) 2_557 . ? N2 Co2 N2 88.92(6) 2_557 . ? C22 N3 C26 120.0 . . ? C22 N3 Co2 116.3 . . ? C26 N3 Co2 123.5 . . ? C22 C22 N3 119.1 2_557 . ? C22 C22 C23 120.1 2_557 . ? N3 C22 C23 119.9 . . ? C22 C22 C23 36.88(5) 2_557 2_557 ? N3 C22 C23 155.96(5) . 2_557 ? C23 C22 C23 83.93(5) . 2_557 ? C22 C23 C24 120.0 . . ? C22 C23 C27 116.0 . . ? C24 C23 C27 124.0 . . ? C22 C23 C27 96.77(6) . 2_557 ? C24 C23 C27 143.20(6) . 2_557 ? C27 C23 C27 19.22(6) . 2_557 ? C22 C23 C22 22.99(5) . 2_557 ? C24 C23 C22 142.50(5) . 2_557 ? C27 C23 C22 93.21(5) . 2_557 ? C27 C23 C22 74.09(11) 2_557 2_557 ? C25 C24 C23 120.0 . . ? C24 C25 C26 120.0 . . ? C25 C26 N3 120.0 . . ? C27 C27 C23 123.3 2_557 . ? C27 C27 C23 37.49(6) 2_557 2_557 ? C23 C27 C23 85.98(6) . 2_557 ? O4W O3W O2W 148(2) . . ? O3W O2W O3W 172(2) 2_656 . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 72.71 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.043 _refine_diff_density_min -0.913 _refine_diff_density_rms 0.094 # Attachment 'lmd72fabs1.cif' data_lmd72fabs _database_code_depnum_ccdc_archive 'CCDC 763061' #TrackingRef 'lmd72fabs1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Cd0.50 N O5' _chemical_formula_weight 268.38 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' Cd Cd 0.1185 4.6533 '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 7.9270(19) _cell_length_b 25.929(5) _cell_length_c 10.234(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.7850(10) _cell_angle_gamma 90.00 _cell_volume 1939.4(7) _cell_formula_units_Z 8 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1097 _cell_measurement_theta_min 4.6813 _cell_measurement_theta_max 72.8152 _exptl_crystal_description leaf-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2991 _exptl_crystal_size_mid 0.0670 _exptl_crystal_size_min 0.0316 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.838 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 9.594 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.258 _exptl_absorpt_correction_T_max 0.753 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 16.0711 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3400 _diffrn_reflns_av_R_equivalents 0.0834 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 5.80 _diffrn_reflns_theta_max 64.86 _reflns_number_total 1554 _reflns_number_gt 1259 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1409P)^2^+81.5946P] 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 1554 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1281 _refine_ls_R_factor_gt 0.1158 _refine_ls_wR_factor_ref 0.3022 _refine_ls_wR_factor_gt 0.2911 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 O2W O 0.457(4) 0.1337(11) 0.354(3) 0.098(11) Uiso 0.58(4) 1 d P . . O1W O 0.504(4) 0.1172(12) 0.476(3) 0.071(12) Uiso 0.42(4) 1 d P . . O3 O 0.261(4) 0.1803(9) 0.491(3) 0.035(9) Uiso 0.34(3) 1 d P A 1 H3 H 0.1874 0.1579 0.4974 0.052 Uiso 0.34(3) 1 calc PR A 1 O3B O 0.1869(19) 0.1875(5) 0.4055(17) 0.035(5) Uiso 0.66(3) 1 d P A 2 H3B H 0.1453 0.1897 0.3168 0.052 Uiso 0.66(3) 1 calc PR A 2 C1 C -0.1266(17) 0.1984(5) 0.4683(15) 0.035(3) Uani 1 1 d . . . C2 C 0.0479(16) 0.2289(5) 0.5504(13) 0.031(3) Uani 1 1 d . A . C3 C 0.1642(18) 0.2349(5) 0.4630(15) 0.038(3) Uani 1 1 d . . . H3A H 0.0954 0.2438 0.3610 0.045 Uiso 1 1 calc R A 1 N1A N -0.142(3) 0.0640(5) 0.791(2) 0.030(5) Uiso 0.50 1 d PG B 1 C4A C -0.072(3) 0.0186(7) 0.759(2) 0.047(9) Uiso 0.50 1 d PG . 1 C5A C -0.124(3) -0.0287(6) 0.796(2) 0.039(7) Uiso 0.50 1 d PG . 1 C6A C -0.246(3) -0.0306(6) 0.864(3) 0.053(8) Uiso 0.50 1 d PG B 1 H6A H -0.2810 -0.0629 0.8887 0.064 Uiso 0.50 1 calc PR B 1 C7A C -0.315(3) 0.0148(8) 0.896(2) 0.053(7) Uiso 0.50 1 d PG B 1 H7A H -0.3975 0.0135 0.9422 0.063 Uiso 0.50 1 calc PR B 1 C8A C -0.263(2) 0.0621(6) 0.859(2) 0.028(5) Uiso 0.50 1 d PG B 1 H8A H -0.3100 0.0932 0.8808 0.034 Uiso 0.50 1 calc PR B 1 C9A C -0.037(4) -0.0735(10) 0.767(3) 0.040(7) Uiso 0.50 1 d P . 1 H9A H -0.0703 -0.1061 0.7924 0.047 Uiso 0.50 1 calc PR . 1 C9B C -0.095(6) -0.0687(15) 0.794(4) 0.062(9) Uiso 0.50 1 d P . 2 H9B H -0.1520 -0.0995 0.8064 0.075 Uiso 0.50 1 calc PR . 2 N1B N -0.112(3) 0.0705(6) 0.827(2) 0.040(7) Uiso 0.50 1 d PG B 2 C4B C -0.061(3) 0.0219(7) 0.798(2) 0.027(6) Uiso 0.50 1 d PG . 2 C5B C -0.135(3) -0.0220(6) 0.834(3) 0.050(8) Uiso 0.50 1 d PG B 2 C6B C -0.260(3) -0.0172(8) 0.897(3) 0.059(9) Uiso 0.50 1 d PG B 2 H6B H -0.3110 -0.0472 0.9214 0.071 Uiso 0.50 1 calc PR B 2 C7B C -0.311(3) 0.0314(10) 0.926(3) 0.089(13) Uiso 0.50 1 d PG B 2 H7B H -0.3968 0.0347 0.9700 0.106 Uiso 0.50 1 calc PR B 2 C8B C -0.237(3) 0.0752(7) 0.891(3) 0.053(8) Uiso 0.50 1 d PG B 2 H8B H -0.2717 0.1085 0.9110 0.064 Uiso 0.50 1 calc PR B 2 O1A O -0.1695(13) 0.1612(4) 0.5259(10) 0.044(2) Uani 1 1 d . B . O1B O -0.2242(15) 0.2157(4) 0.3470(12) 0.056(3) Uani 1 1 d . . . O2 O 0.1473(13) 0.2036(4) 0.6802(11) 0.052(3) Uani 1 1 d . . . H2 H 0.1719 0.2247 0.7473 0.077 Uiso 1 1 calc R A . Cd1 Cd 0.0000 0.13807(5) 0.7500 0.0651(8) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(7) 0.037(7) 0.052(8) -0.011(5) 0.038(7) -0.006(5) C2 0.032(6) 0.037(6) 0.041(7) 0.002(5) 0.032(6) -0.002(5) C3 0.042(7) 0.038(6) 0.056(8) -0.006(5) 0.043(7) -0.011(5) O1A 0.049(5) 0.047(5) 0.059(6) 0.003(4) 0.047(5) -0.007(4) O1B 0.050(6) 0.079(7) 0.058(7) -0.007(5) 0.040(6) -0.008(5) O2 0.036(5) 0.082(7) 0.054(6) 0.013(5) 0.035(5) -0.018(5) Cd1 0.1353(18) 0.0211(8) 0.0780(13) 0.000 0.0842(13) 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 O2W O1W 1.24(4) . ? O3 C3 1.58(3) . ? O3B C3 1.403(18) . ? C1 O1A 1.245(15) . ? C1 O1B 1.264(17) . ? C1 C2 1.531(17) . ? C2 O2 1.415(16) . ? C2 C3 1.521(16) . ? C3 C3 1.50(3) 7_556 ? N1A C4A 1.3900 . ? N1A C8A 1.3900 . ? N1A Cd1 2.342(13) . ? C4A C4A 1.23(3) 2_556 ? C4A C5A 1.3900 . ? C5A C6A 1.3900 . ? C5A C9A 1.44(3) . ? C5A C9A 2.01(3) 2_556 ? C6A C7A 1.3900 . ? C7A C8A 1.3900 . ? C9A C9A 0.79(6) 2_556 ? C9A C5A 2.01(3) 2_556 ? C9B C5B 1.35(4) . ? C9B C9B 2.03(9) 2_556 ? N1B C4B 1.3900 . ? N1B C8B 1.3900 . ? N1B Cd1 2.241(14) . ? C4B C5B 1.3900 . ? C4B C4B 1.63(3) 2_556 ? C5B C6B 1.3900 . ? C6B C7B 1.3900 . ? C7B C8B 1.3900 . ? O1A Cd1 2.244(10) . ? Cd1 N1B 2.241(14) 2_556 ? Cd1 O1A 2.244(10) 2_556 ? Cd1 O2 2.325(9) 2_556 ? Cd1 N1A 2.342(13) 2_556 ? 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 O1A C1 O1B 124.4(12) . . ? O1A C1 C2 119.6(12) . . ? O1B C1 C2 115.8(11) . . ? O2 C2 C3 110.8(10) . . ? O2 C2 C1 109.4(10) . . ? C3 C2 C1 110.8(10) . . ? O3B C3 C3 115.6(14) . 7_556 ? O3B C3 C2 111.3(11) . . ? C3 C3 C2 113.2(14) 7_556 . ? O3B C3 O3 33.0(10) . . ? C3 C3 O3 95.6(16) 7_556 . ? C2 C3 O3 99.3(13) . . ? C4A N1A C8A 120.0 . . ? C4A N1A Cd1 113.1(8) . . ? C8A N1A Cd1 126.2(8) . . ? C4A C4A N1A 120.7(6) 2_556 . ? C4A C4A C5A 115.5(8) 2_556 . ? N1A C4A C5A 120.0 . . ? C6A C5A C4A 120.0 . . ? C6A C5A C9A 123.6(17) . . ? C4A C5A C9A 116.2(17) . . ? C6A C5A C9A 142.2(12) . 2_556 ? C4A C5A C9A 97.7(12) . 2_556 ? C9A C5A C9A 18.6(14) . 2_556 ? C5A C6A C7A 120.0 . . ? C6A C7A C8A 120.0 . . ? C7A C8A N1A 120.0 . . ? C9A C9A C5A 126.0(14) 2_556 . ? C9A C9A C5A 35.5(13) 2_556 2_556 ? C5A C9A C5A 91(2) . 2_556 ? C5B C9B C9B 116(2) . 2_556 ? C4B N1B C8B 120.0 . . ? C4B N1B Cd1 116.6(10) . . ? C8B N1B Cd1 123.3(10) . . ? C5B C4B N1B 120.0 . . ? C5B C4B C4B 124.5(4) . 2_556 ? N1B C4B C4B 114.74(18) . 2_556 ? C9B C5B C4B 119(2) . . ? C9B C5B C6B 121(2) . . ? C4B C5B C6B 120.0 . . ? C7B C6B C5B 120.0 . . ? C6B C7B C8B 120.0 . . ? C7B C8B N1B 120.0 . . ? C1 O1A Cd1 121.7(9) . . ? N1B Cd1 N1B 77.1(9) 2_556 . ? N1B Cd1 O1A 114.1(6) 2_556 2_556 ? N1B Cd1 O1A 90.6(6) . 2_556 ? N1B Cd1 O1A 90.6(6) 2_556 . ? N1B Cd1 O1A 114.1(6) . . ? O1A Cd1 O1A 149.0(5) 2_556 . ? N1B Cd1 O2 173.6(6) 2_556 2_556 ? N1B Cd1 O2 98.5(6) . 2_556 ? O1A Cd1 O2 70.4(3) 2_556 2_556 ? O1A Cd1 O2 86.9(4) . 2_556 ? N1B Cd1 N1A 72.8(5) 2_556 . ? N1B Cd1 N1A 9.5(7) . . ? O1A Cd1 N1A 100.1(6) 2_556 . ? O1A Cd1 N1A 105.2(6) . . ? O2 Cd1 N1A 102.2(5) 2_556 . ? N1B Cd1 N1A 9.5(7) 2_556 2_556 ? N1B Cd1 N1A 72.8(5) . 2_556 ? O1A Cd1 N1A 105.2(6) 2_556 2_556 ? O1A Cd1 N1A 100.1(6) . 2_556 ? O2 Cd1 N1A 170.5(5) 2_556 2_556 ? N1A Cd1 N1A 69.9(8) . 2_556 ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 64.86 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 2.582 _refine_diff_density_min -1.964 _refine_diff_density_rms 0.211 # Attachment 'lme1f1.cif' data_lme1f _database_code_depnum_ccdc_archive 'CCDC 763062' #TrackingRef 'lme1f1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 Cu N2 O11' _chemical_formula_weight 505.92 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 Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 9.7117(3) _cell_length_b 10.2821(2) _cell_length_c 10.9564(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.107(4) _cell_angle_gamma 90.00 _cell_volume 1006.30(5) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2758 _cell_measurement_theta_min 4.2869 _cell_measurement_theta_max 73.2549 _exptl_crystal_description rod _exptl_crystal_colour blue _exptl_crystal_size_max 0.2868 _exptl_crystal_size_mid 0.0679 _exptl_crystal_size_min 0.0594 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 2.145 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.707 _exptl_absorpt_correction_T_max 0.885 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 16.0711 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3809 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.30 _diffrn_reflns_theta_max 69.96 _reflns_number_total 1803 _reflns_number_gt 1573 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0456P)^2^+3.4251P] 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 1803 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1376 _refine_ls_wR_factor_gt 0.1340 _refine_ls_goodness_of_fit_ref 1.216 _refine_ls_restrained_S_all 1.216 _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 O1W O 0.5000 0.7243(4) 0.2500 0.0207(9) Uani 1 2 d S . . O2W O -0.4617(4) 0.3662(3) 0.0030(4) 0.0401(9) Uani 1 1 d . . . C1 C 0.2101(4) -0.0254(4) 0.2318(4) 0.0137(8) Uani 1 1 d . . . C2 C -0.2891(4) -0.0064(4) 0.1175(4) 0.0138(8) Uani 1 1 d . . . H2 H -0.2672 -0.0836 0.0726 0.017 Uiso 1 1 calc R . . C3 C -0.4591(4) 0.0035(4) 0.0752(4) 0.0135(8) Uani 1 1 d . . . H3 H -0.4928 -0.0711 0.1152 0.016 Uiso 1 1 calc R . . C4 C 0.1826(5) 0.3044(5) 0.1227(5) 0.0280(10) Uani 1 1 d . . . H4 H 0.2122 0.2221 0.1019 0.034 Uiso 1 1 calc R . . C5 C 0.2380(5) 0.4169(5) 0.0868(5) 0.0360(12) Uani 1 1 d . . . H5 H 0.3051 0.4108 0.0431 0.043 Uiso 1 1 calc R . . C6 C 0.1952(5) 0.5358(5) 0.1150(5) 0.0379(12) Uani 1 1 d . . . H6 H 0.2303 0.6130 0.0890 0.046 Uiso 1 1 calc R . . C7 C 0.0988(5) 0.5433(5) 0.1826(5) 0.0300(10) Uani 1 1 d . . . C8 C 0.0499(4) 0.4259(4) 0.2157(4) 0.0208(9) Uani 1 1 d . . . C9 C 0.0469(6) 0.6626(5) 0.2177(6) 0.0406(13) Uani 1 1 d . . . H9 H 0.0789 0.7431 0.1953 0.049 Uiso 1 1 calc R . . N1 N 0.0895(4) 0.3087(3) 0.1852(3) 0.0199(7) Uani 1 1 d . . . O1A O 0.0891(3) 0.0323(3) 0.1692(3) 0.0206(6) Uani 1 1 d . . . O1B O 0.2688(3) -0.1029(3) 0.1775(3) 0.0163(6) Uani 1 1 d . . . O2 O -0.2305(3) 0.1054(3) 0.0800(3) 0.0156(6) Uani 1 1 d . . . H2A H -0.2275 0.0931 0.0053 0.023 Uiso 1 1 calc R . . O3 O -0.4971(3) 0.1217(3) 0.1229(3) 0.0171(6) Uani 1 1 d . . . Cu1 Cu 0.0000 0.15973(8) 0.2500 0.0155(3) Uani 1 2 d S . . 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 O1W 0.024(2) 0.014(2) 0.024(2) 0.000 0.0093(17) 0.000 O2W 0.054(2) 0.037(2) 0.039(2) -0.0068(16) 0.0292(18) 0.0033(17) C1 0.0153(17) 0.0142(19) 0.0119(18) 0.0011(15) 0.0057(15) -0.0024(15) C2 0.0152(18) 0.0135(19) 0.0133(19) 0.0014(15) 0.0062(16) 0.0008(14) C3 0.0144(17) 0.0120(18) 0.014(2) -0.0004(15) 0.0052(15) 0.0002(14) C4 0.023(2) 0.035(3) 0.029(2) 0.004(2) 0.0127(19) -0.0002(19) C5 0.027(2) 0.048(3) 0.037(3) 0.009(2) 0.016(2) -0.007(2) C6 0.031(2) 0.041(3) 0.039(3) 0.010(2) 0.010(2) -0.015(2) C7 0.026(2) 0.024(2) 0.032(3) 0.007(2) 0.002(2) -0.0060(18) C8 0.0177(19) 0.016(2) 0.024(2) 0.0013(18) 0.0033(18) -0.0006(16) C9 0.041(3) 0.018(2) 0.050(3) 0.004(2) 0.004(2) -0.004(2) N1 0.0167(16) 0.0237(19) 0.0200(18) 0.0034(15) 0.0079(14) -0.0005(14) O1A 0.0170(13) 0.0259(16) 0.0145(14) -0.0032(12) 0.0013(11) 0.0057(12) O1B 0.0180(13) 0.0173(14) 0.0131(14) -0.0015(11) 0.0055(11) 0.0017(11) O2 0.0159(12) 0.0203(14) 0.0104(13) 0.0008(11) 0.0049(11) -0.0024(11) O3 0.0170(13) 0.0192(14) 0.0153(14) -0.0032(11) 0.0066(12) 0.0018(11) Cu1 0.0155(4) 0.0155(4) 0.0161(4) 0.000 0.0068(3) 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 C1 O1A 1.253(5) . ? C1 O1B 1.257(4) . ? C1 C2 1.536(5) 2 ? C2 O2 1.413(4) . ? C2 C3 1.533(5) . ? C2 C1 1.536(5) 2 ? C3 O3 1.428(4) . ? C3 C3 1.525(7) 3_455 ? C4 N1 1.332(5) . ? C4 C5 1.397(6) . ? C5 C6 1.365(8) . ? C6 C7 1.406(7) . ? C7 C8 1.396(6) . ? C7 C9 1.435(7) . ? C8 N1 1.346(5) . ? C8 C8 1.441(8) 2 ? C9 C9 1.355(11) 2 ? N1 Cu1 2.023(3) . ? O1A Cu1 1.962(3) . ? Cu1 O1A 1.962(3) 2 ? Cu1 N1 2.023(3) 2 ? Cu1 O2 2.350(3) 2 ? 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 O1A C1 O1B 123.0(4) . . ? O1A C1 C2 119.5(3) . 2 ? O1B C1 C2 117.5(3) . 2 ? O2 C2 C3 111.5(3) . . ? O2 C2 C1 109.2(3) . 2 ? C3 C2 C1 111.0(3) . 2 ? O3 C3 C3 109.6(4) . 3_455 ? O3 C3 C2 110.4(3) . . ? C3 C3 C2 111.5(4) 3_455 . ? N1 C4 C5 122.1(5) . . ? C6 C5 C4 119.5(4) . . ? C5 C6 C7 119.6(4) . . ? C8 C7 C6 117.0(4) . . ? C8 C7 C9 118.6(4) . . ? C6 C7 C9 124.4(4) . . ? N1 C8 C7 123.4(4) . . ? N1 C8 C8 116.5(2) . 2 ? C7 C8 C8 120.1(3) . 2 ? C9 C9 C7 121.3(3) 2 . ? C4 N1 C8 118.4(4) . . ? C4 N1 Cu1 128.8(3) . . ? C8 N1 Cu1 112.8(3) . . ? C1 O1A Cu1 123.7(3) . . ? O1A Cu1 O1A 96.20(18) 2 . ? O1A Cu1 N1 172.09(13) 2 . ? O1A Cu1 N1 91.21(13) . . ? O1A Cu1 N1 91.21(13) 2 2 ? O1A Cu1 N1 172.09(13) . 2 ? N1 Cu1 N1 81.5(2) . 2 ? O1A Cu1 O2 86.30(10) 2 2 ? O1A Cu1 O2 75.35(10) . 2 ? N1 Cu1 O2 92.94(11) . 2 ? N1 Cu1 O2 107.99(11) 2 2 ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 69.96 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.658 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.096