# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_p1b _database_code_depnum_ccdc_archive 'CCDC 890678' #TrackingRef '0cdadipnicotinate3ampyrfinal2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H38 Cd2 N4 O16' _chemical_formula_weight 851.37 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9448(12) _cell_length_b 11.1929(17) _cell_length_c 18.000(3) _cell_angle_alpha 85.128(2) _cell_angle_beta 81.477(2) _cell_angle_gamma 85.234(2) _cell_volume 1573.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7411 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 25.01 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.797 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.430 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7910 _exptl_absorpt_correction_T_max 0.8702 _exptl_absorpt_process_details TWINABS _exptl_special_details ; Crystal was non-merohedrally twinned. Twin law was determined using CELL_NOW. Only reflections from the major twin component were used in the refinement. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5522 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5522 _reflns_number_gt 3915 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0523P)^2^+18.6023P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5522 _refine_ls_number_parameters 448 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.1685 _refine_ls_wR_factor_gt 0.1599 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.130 _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 Cd1 Cd 0.24719(8) 0.67367(6) 0.45164(4) 0.0201(2) Uani 1 1 d . . . Cd2 Cd 0.25495(9) 0.86364(7) 1.08230(4) 0.0260(2) Uani 1 1 d . . . O1 O 0.3443(9) 0.7999(8) 0.9542(4) 0.041(2) Uani 1 1 d . . . O1W O 1.0656(15) 0.4252(13) 0.9300(7) 0.099(4) Uani 1 1 d . . . O2 O 0.0743(10) 0.8250(10) 0.9944(4) 0.057(3) Uani 1 1 d . . . O2W O 0.6040(14) 0.5688(11) 1.0371(7) 0.088(4) Uani 1 1 d . . . O3 O 0.1684(9) 0.6721(6) 0.5896(4) 0.0294(16) Uani 1 1 d . . . O3W O 0.6665(12) 0.7371(10) 0.8872(6) 0.064(3) Uani 1 1 d D . . H3WA H 0.685(19) 0.798(7) 0.908(6) 0.077 Uiso 1 1 d D . . H3WB H 0.65(2) 0.677(7) 0.918(5) 0.077 Uiso 1 1 d D . . O4 O 0.4353(9) 0.6407(6) 0.5447(4) 0.0278(16) Uani 1 1 d . . . O4W O 0.8412(11) 0.5312(7) 0.8299(5) 0.042(2) Uani 1 1 d D . . H4WA H 0.865(16) 0.563(8) 0.785(2) 0.050 Uiso 1 1 d D . . H4WB H 0.837(16) 0.580(7) 0.864(4) 0.050 Uiso 1 1 d D . . O5 O -0.0429(8) 0.6566(6) 0.4493(4) 0.0222(15) Uani 1 1 d . . . O5W O 0.8713(10) 0.6124(7) 0.6819(4) 0.0354(18) Uani 1 1 d D . . H5WA H 0.811(11) 0.578(10) 0.655(4) 0.042 Uiso 1 1 d D . . H5WB H 0.961(8) 0.633(10) 0.653(4) 0.042 Uiso 1 1 d D . . O6 O 0.1025(8) 0.6888(7) 0.3361(4) 0.0319(17) Uani 1 1 d . . . O7 O 0.2556(8) 0.4674(6) 0.4441(4) 0.0242(15) Uani 1 1 d D . . H7A H 0.357(4) 0.437(8) 0.442(5) 0.029 Uiso 1 1 d D . . H7B H 0.195(9) 0.431(8) 0.481(4) 0.029 Uiso 1 1 d D . . O9 O -0.6074(8) 0.9339(7) 1.1893(4) 0.0309(17) Uani 1 1 d . . . O10 O -0.4574(8) 0.8857(7) 1.0814(4) 0.0313(17) Uani 1 1 d . . . O11 O 0.2279(9) 1.0682(7) 1.0439(4) 0.0305(17) Uani 1 1 d D . . H11A H 0.310(7) 1.076(10) 1.009(4) 0.037 Uiso 1 1 d D . . H11B H 0.134(6) 1.097(9) 1.031(5) 0.037 Uiso 1 1 d D . . O12 O 0.3300(11) 0.6714(7) 1.1257(5) 0.044(2) Uani 1 1 d D . . H12A H 0.412(11) 0.657(9) 1.091(5) 0.053 Uiso 1 1 d D . . H12B H 0.281(13) 0.609(6) 1.144(6) 0.053 Uiso 1 1 d D . . N1 N -0.5004(9) 0.6703(7) 0.3623(4) 0.0208(17) Uani 1 1 d . . . N2 N -0.0006(10) 0.8947(8) 1.1639(4) 0.0252(19) Uani 1 1 d . . . N3 N 0.2529(11) 0.8815(8) 0.4471(5) 0.029(2) Uani 1 1 d . . . N4 N 0.2793(14) 1.1264(9) 0.3013(5) 0.039(2) Uani 1 1 d D . . H4NA H 0.261(15) 1.206(2) 0.291(5) 0.047 Uiso 1 1 d D . . H4NB H 0.277(15) 1.095(8) 0.257(3) 0.047 Uiso 1 1 d D . . C1 C 0.2942(12) 0.7209(10) 0.8117(5) 0.029(2) Uani 1 1 d . . . H1A H 0.3597 0.6486 0.8310 0.034 Uiso 1 1 calc R . . H1B H 0.3720 0.7868 0.8006 0.034 Uiso 1 1 calc R . . C2 C 0.2302(12) 0.6945(10) 0.7395(5) 0.026(2) Uani 1 1 d . . . H2A H 0.1636 0.6225 0.7497 0.031 Uiso 1 1 calc R . . H2B H 0.1526 0.7630 0.7242 0.031 Uiso 1 1 calc R . . C3 C 0.1473(13) 0.7566(11) 0.8718(6) 0.035(3) Uani 1 1 d . . . H3A H 0.0762 0.8233 0.8497 0.042 Uiso 1 1 calc R . . H3B H 0.0756 0.6875 0.8848 0.042 Uiso 1 1 calc R . . C4 C 0.1946(13) 0.7950(10) 0.9433(6) 0.030(2) Uani 1 1 d . . . C5 C 0.3725(13) 0.6732(10) 0.6752(5) 0.029(2) Uani 1 1 d . . . H5A H 0.4466 0.7412 0.6697 0.035 Uiso 1 1 calc R . . H5B H 0.4424 0.5996 0.6891 0.035 Uiso 1 1 calc R . . C6 C -0.1914(11) 0.6617(9) 0.3440(5) 0.022(2) Uani 1 1 d . . . C7 C -0.0333(12) 0.6692(8) 0.3780(6) 0.021(2) Uani 1 1 d . . . C8 C 0.3195(13) 0.6597(9) 0.5999(5) 0.025(2) Uani 1 1 d . . . C9 C -0.3529(11) 0.6760(8) 0.3883(5) 0.019(2) Uani 1 1 d . . . H9 H -0.3568 0.6907 0.4398 0.023 Uiso 1 1 calc R . . C10 C -0.4946(12) 0.6515(10) 0.2890(6) 0.029(2) Uani 1 1 d . . . H10 H -0.5989 0.6466 0.2699 0.035 Uiso 1 1 calc R . . C11 C -0.3449(12) 0.6391(9) 0.2407(6) 0.025(2) Uani 1 1 d . . . H11 H -0.3459 0.6276 0.1891 0.030 Uiso 1 1 calc R . . C12 C -0.1900(13) 0.6436(9) 0.2687(6) 0.026(2) Uani 1 1 d . . . H12 H -0.0847 0.6342 0.2362 0.031 Uiso 1 1 calc R . . C13 C -0.1519(13) 0.8907(9) 1.1392(6) 0.028(2) Uani 1 1 d . . . H13 H -0.1527 0.8619 1.0911 0.034 Uiso 1 1 calc R . . C14 C -0.0038(12) 0.9333(10) 1.2319(5) 0.027(2) Uani 1 1 d . . . H14 H 0.1018 0.9362 1.2503 0.033 Uiso 1 1 calc R . . C15 C -0.1500(13) 0.9689(9) 1.2770(6) 0.028(2) Uani 1 1 d . . . H15 H -0.1457 0.9951 1.3255 0.034 Uiso 1 1 calc R . . C16 C -0.3044(12) 0.9261(9) 1.1800(5) 0.023(2) Uani 1 1 d . . . C17 C -0.3053(13) 0.9661(10) 1.2505(6) 0.030(2) Uani 1 1 d . . . H17 H -0.4093 0.9910 1.2802 0.036 Uiso 1 1 calc R . . C18 C -0.4683(12) 0.9163(9) 1.1483(6) 0.022(2) Uani 1 1 d . . . C19 C 0.218(2) 0.9428(11) 0.5092(7) 0.057(4) Uani 1 1 d . . . H19 H 0.2006 0.9003 0.5574 0.069 Uiso 1 1 calc R . . C20 C 0.2709(12) 0.9421(9) 0.3806(6) 0.025(2) Uani 1 1 d . . . H20 H 0.2942 0.8982 0.3369 0.030 Uiso 1 1 calc R . . C21 C 0.208(2) 1.0664(11) 0.5037(8) 0.068(5) Uani 1 1 d . . . H21 H 0.1872 1.1084 0.5482 0.081 Uiso 1 1 calc R . . C22 C 0.2268(17) 1.1295(11) 0.4351(7) 0.046(3) Uani 1 1 d . . . H22 H 0.2188 1.2149 0.4318 0.056 Uiso 1 1 calc R . . C23 C 0.2573(13) 1.0692(9) 0.3709(6) 0.028(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0156(4) 0.0209(4) 0.0243(4) -0.0027(3) -0.0029(3) -0.0034(3) Cd2 0.0171(4) 0.0362(5) 0.0257(4) -0.0061(3) -0.0024(3) -0.0058(3) O1 0.020(4) 0.070(6) 0.037(4) -0.017(4) -0.007(3) -0.008(4) O1W 0.065(8) 0.136(12) 0.095(9) 0.024(8) -0.022(6) -0.015(7) O2 0.030(5) 0.111(8) 0.034(5) -0.041(5) -0.002(4) -0.004(5) O2W 0.058(7) 0.091(9) 0.118(10) -0.052(7) -0.005(6) 0.003(6) O3 0.022(4) 0.036(4) 0.033(4) -0.006(3) -0.006(3) -0.006(3) O3W 0.031(5) 0.069(7) 0.099(8) -0.047(6) -0.009(5) -0.004(5) O4 0.026(4) 0.029(4) 0.028(4) -0.003(3) -0.004(3) 0.002(3) O4W 0.046(5) 0.032(5) 0.046(5) 0.002(4) -0.002(4) -0.007(4) O5 0.017(3) 0.017(4) 0.034(4) -0.003(3) -0.006(3) -0.002(3) O5W 0.031(4) 0.040(5) 0.038(4) -0.008(4) -0.003(3) -0.012(4) O6 0.013(4) 0.041(5) 0.040(4) 0.002(3) 0.002(3) -0.009(3) O7 0.015(3) 0.018(4) 0.039(4) -0.001(3) 0.000(3) 0.000(3) O9 0.018(4) 0.040(5) 0.036(4) -0.006(3) -0.006(3) -0.005(3) O10 0.018(4) 0.051(5) 0.026(4) -0.007(3) -0.002(3) -0.010(3) O11 0.021(4) 0.037(5) 0.031(4) -0.001(3) -0.001(3) 0.002(3) O12 0.037(5) 0.035(5) 0.056(6) 0.007(4) 0.005(4) -0.008(4) N1 0.014(4) 0.022(5) 0.028(4) -0.003(3) -0.003(3) -0.003(3) N2 0.017(4) 0.036(5) 0.020(4) 0.000(4) 0.006(3) -0.010(4) N3 0.030(5) 0.023(5) 0.036(5) -0.005(4) -0.004(4) -0.004(4) N4 0.057(7) 0.024(5) 0.036(6) -0.003(4) -0.005(5) -0.003(5) C1 0.020(5) 0.041(7) 0.025(5) -0.012(5) -0.001(4) -0.002(5) C2 0.021(5) 0.031(6) 0.029(5) -0.006(4) -0.007(4) -0.007(4) C3 0.019(5) 0.056(8) 0.033(6) -0.016(5) -0.005(4) -0.007(5) C4 0.022(6) 0.036(7) 0.032(6) -0.011(5) -0.003(5) -0.002(5) C5 0.032(6) 0.028(6) 0.028(6) -0.002(4) -0.004(4) 0.001(5) C6 0.011(5) 0.022(5) 0.031(6) -0.006(4) 0.004(4) 0.000(4) C7 0.018(5) 0.005(5) 0.039(6) -0.002(4) -0.002(4) 0.002(4) C8 0.025(6) 0.024(6) 0.027(5) -0.006(4) -0.002(4) -0.005(4) C9 0.011(5) 0.023(5) 0.024(5) -0.002(4) -0.006(4) -0.001(4) C10 0.016(5) 0.035(6) 0.037(6) -0.001(5) -0.010(4) 0.001(4) C11 0.025(5) 0.025(6) 0.026(5) -0.006(4) -0.002(4) -0.004(4) C12 0.022(5) 0.022(6) 0.032(6) -0.001(4) -0.001(4) 0.003(4) C13 0.025(6) 0.033(6) 0.027(6) -0.004(4) -0.004(4) -0.006(5) C14 0.017(5) 0.040(7) 0.024(5) 0.002(4) -0.001(4) -0.007(5) C15 0.027(6) 0.033(6) 0.026(5) -0.007(4) -0.004(4) -0.002(5) C16 0.018(5) 0.022(6) 0.029(5) 0.000(4) -0.004(4) -0.010(4) C17 0.018(5) 0.043(7) 0.027(6) -0.005(5) 0.007(4) -0.005(5) C18 0.015(5) 0.020(5) 0.030(6) 0.000(4) -0.002(4) -0.001(4) C19 0.115(13) 0.030(7) 0.025(6) -0.002(5) -0.003(7) -0.008(7) C20 0.014(5) 0.027(6) 0.033(6) -0.004(4) -0.004(4) -0.004(4) C21 0.133(15) 0.025(7) 0.045(8) -0.015(6) -0.007(8) -0.004(8) C22 0.069(9) 0.025(7) 0.043(7) 0.000(5) -0.004(6) 0.000(6) C23 0.021(5) 0.028(6) 0.036(6) -0.004(5) -0.005(4) -0.003(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O7 2.319(7) . ? Cd1 N3 2.325(9) . ? Cd1 O5 2.335(6) . ? Cd1 N1 2.377(8) 1_655 ? Cd1 O4 2.391(7) . ? Cd1 O3 2.468(7) . ? Cd1 O6 2.507(7) . ? Cd2 O12 2.288(8) . ? Cd2 O10 2.317(7) 1_655 ? Cd2 O11 2.337(8) . ? Cd2 N2 2.342(8) . ? Cd2 O2 2.375(8) . ? Cd2 O1 2.457(7) . ? Cd2 O9 2.559(7) 1_655 ? O1 C4 1.240(12) . ? O2 C4 1.270(12) . ? O3 C8 1.237(12) . ? O3W H3WA 0.85(2) . ? O3W H3WB 0.84(2) . ? O4 C8 1.270(12) . ? O4W H4WA 0.85(2) . ? O4W H4WB 0.84(2) . ? O5 C7 1.270(11) . ? O5W H5WA 0.85(2) . ? O5W H5WB 0.85(2) . ? O6 C7 1.245(11) . ? O7 H7A 0.85(2) . ? O7 H7B 0.85(2) . ? O9 C18 1.245(11) . ? O9 Cd2 2.559(7) 1_455 ? O10 C18 1.270(11) . ? O10 Cd2 2.317(7) 1_455 ? O11 H11A 0.85(2) . ? O11 H11B 0.84(2) . ? O12 H12A 0.85(2) . ? O12 H12B 0.85(2) . ? N1 C9 1.333(11) . ? N1 C10 1.348(12) . ? N1 Cd1 2.377(8) 1_455 ? N2 C14 1.329(13) . ? N2 C13 1.347(13) . ? N3 C20 1.320(13) . ? N3 C19 1.342(14) . ? N4 C23 1.353(13) . ? N4 H4NA 0.90(2) . ? N4 H4NB 0.89(2) . ? C1 C3 1.521(13) . ? C1 C2 1.524(13) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C5 1.513(14) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.498(14) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C8 1.499(14) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C12 1.386(14) . ? C6 C9 1.412(12) . ? C6 C7 1.488(13) . ? C9 H9 0.9500 . ? C10 C11 1.369(14) . ? C10 H10 0.9500 . ? C11 C12 1.404(14) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C16 1.368(14) . ? C13 H13 0.9500 . ? C14 C15 1.366(14) . ? C14 H14 0.9500 . ? C15 C17 1.390(14) . ? C15 H15 0.9500 . ? C16 C17 1.380(14) . ? C16 C18 1.513(13) . ? C17 H17 0.9500 . ? C19 C21 1.376(18) . ? C19 H19 0.9500 . ? C20 C23 1.415(14) . ? C20 H20 0.9500 . ? C21 C22 1.365(17) . ? C21 H21 0.9500 . ? C22 C23 1.367(15) . ? C22 H22 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Cd1 N3 174.3(3) . . ? O7 Cd1 O5 81.6(2) . . ? N3 Cd1 O5 100.3(3) . . ? O7 Cd1 N1 86.7(2) . 1_655 ? N3 Cd1 N1 88.2(3) . 1_655 ? O5 Cd1 N1 136.2(2) . 1_655 ? O7 Cd1 O4 89.0(2) . . ? N3 Cd1 O4 93.2(3) . . ? O5 Cd1 O4 135.8(2) . . ? N1 Cd1 O4 85.6(2) 1_655 . ? O7 Cd1 O3 96.7(2) . . ? N3 Cd1 O3 88.8(3) . . ? O5 Cd1 O3 85.3(2) . . ? N1 Cd1 O3 138.1(2) 1_655 . ? O4 Cd1 O3 52.9(2) . . ? O7 Cd1 O6 85.6(2) . . ? N3 Cd1 O6 91.2(3) . . ? O5 Cd1 O6 54.0(2) . . ? N1 Cd1 O6 83.2(2) 1_655 . ? O4 Cd1 O6 167.8(2) . . ? O3 Cd1 O6 138.6(2) . . ? O12 Cd2 O10 82.4(3) . 1_655 ? O12 Cd2 O11 169.1(3) . . ? O10 Cd2 O11 87.2(3) 1_655 . ? O12 Cd2 N2 98.4(3) . . ? O10 Cd2 N2 137.8(3) 1_655 . ? O11 Cd2 N2 87.4(3) . . ? O12 Cd2 O2 100.3(3) . . ? O10 Cd2 O2 137.2(3) 1_655 . ? O11 Cd2 O2 89.4(3) . . ? N2 Cd2 O2 84.5(3) . . ? O12 Cd2 O1 87.5(3) . . ? O10 Cd2 O1 84.6(2) 1_655 . ? O11 Cd2 O1 94.5(3) . . ? N2 Cd2 O1 137.5(3) . . ? O2 Cd2 O1 53.1(2) . . ? O12 Cd2 O9 87.0(3) . 1_655 ? O10 Cd2 O9 53.6(2) 1_655 1_655 ? O11 Cd2 O9 84.4(2) . 1_655 ? N2 Cd2 O9 84.3(2) . 1_655 ? O2 Cd2 O9 167.4(3) . 1_655 ? O1 Cd2 O9 138.2(2) . 1_655 ? C4 O1 Cd2 92.3(6) . . ? C4 O2 Cd2 95.5(6) . . ? C8 O3 Cd1 92.1(6) . . ? H3WA O3W H3WB 113(6) . . ? C8 O4 Cd1 94.9(6) . . ? H4WA O4W H4WB 114(5) . . ? C7 O5 Cd1 95.5(5) . . ? H5WA O5W H5WB 107(5) . . ? C7 O6 Cd1 88.1(6) . . ? Cd1 O7 H7A 110(7) . . ? Cd1 O7 H7B 114(7) . . ? H7A O7 H7B 108(5) . . ? C18 O9 Cd2 86.4(6) . 1_455 ? C18 O10 Cd2 97.1(5) . 1_455 ? Cd2 O11 H11A 103(7) . . ? Cd2 O11 H11B 118(8) . . ? H11A O11 H11B 113(5) . . ? Cd2 O12 H12A 97(8) . . ? Cd2 O12 H12B 138(8) . . ? H12A O12 H12B 112(5) . . ? C9 N1 C10 117.8(8) . . ? C9 N1 Cd1 117.3(6) . 1_455 ? C10 N1 Cd1 124.6(6) . 1_455 ? C14 N2 C13 117.0(8) . . ? C14 N2 Cd2 121.9(6) . . ? C13 N2 Cd2 120.5(6) . . ? C20 N3 C19 118.8(10) . . ? C20 N3 Cd1 118.5(7) . . ? C19 N3 Cd1 122.3(7) . . ? C23 N4 H4NA 125(6) . . ? C23 N4 H4NB 127(7) . . ? H4NA N4 H4NB 105(5) . . ? C3 C1 C2 111.4(8) . . ? C3 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? C3 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? C5 C2 C1 113.2(8) . . ? C5 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? C5 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C1 116.5(8) . . ? C4 C3 H3A 108.2 . . ? C1 C3 H3A 108.2 . . ? C4 C3 H3B 108.2 . . ? C1 C3 H3B 108.2 . . ? H3A C3 H3B 107.3 . . ? O1 C4 O2 119.0(9) . . ? O1 C4 C3 123.2(9) . . ? O2 C4 C3 117.8(9) . . ? C8 C5 C2 116.5(9) . . ? C8 C5 H5A 108.2 . . ? C2 C5 H5A 108.2 . . ? C8 C5 H5B 108.2 . . ? C2 C5 H5B 108.2 . . ? H5A C5 H5B 107.3 . . ? C12 C6 C9 116.7(9) . . ? C12 C6 C7 123.1(8) . . ? C9 C6 C7 120.2(8) . . ? O6 C7 O5 122.4(9) . . ? O6 C7 C6 119.3(9) . . ? O5 C7 C6 118.3(8) . . ? O3 C8 O4 119.5(9) . . ? O3 C8 C5 122.1(9) . . ? O4 C8 C5 118.3(9) . . ? N1 C9 C6 124.0(9) . . ? N1 C9 H9 118.0 . . ? C6 C9 H9 118.0 . . ? N1 C10 C11 122.9(9) . . ? N1 C10 H10 118.6 . . ? C11 C10 H10 118.6 . . ? C10 C11 C12 119.0(9) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C6 C12 C11 119.6(9) . . ? C6 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? N2 C13 C16 123.2(9) . . ? N2 C13 H13 118.4 . . ? C16 C13 H13 118.4 . . ? N2 C14 C15 123.8(9) . . ? N2 C14 H14 118.1 . . ? C15 C14 H14 118.1 . . ? C14 C15 C17 118.7(9) . . ? C14 C15 H15 120.7 . . ? C17 C15 H15 120.7 . . ? C13 C16 C17 119.0(9) . . ? C13 C16 C18 119.5(9) . . ? C17 C16 C18 121.5(9) . . ? C16 C17 C15 118.3(9) . . ? C16 C17 H17 120.9 . . ? C15 C17 H17 120.9 . . ? O9 C18 O10 122.7(9) . . ? O9 C18 C16 119.3(9) . . ? O10 C18 C16 118.0(8) . . ? N3 C19 C21 120.6(11) . . ? N3 C19 H19 119.7 . . ? C21 C19 H19 119.7 . . ? N3 C20 C23 123.4(10) . . ? N3 C20 H20 118.3 . . ? C23 C20 H20 118.3 . . ? C22 C21 C19 120.8(12) . . ? C22 C21 H21 119.6 . . ? C19 C21 H21 119.6 . . ? C21 C22 C23 119.7(11) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? N4 C23 C22 122.6(10) . . ? N4 C23 C20 120.7(10) . . ? C22 C23 C20 116.7(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 Cd2 O1 C4 103.5(7) . . . . ? O10 Cd2 O1 C4 -173.9(7) 1_655 . . . ? O11 Cd2 O1 C4 -87.2(7) . . . . ? N2 Cd2 O1 C4 3.9(9) . . . . ? O2 Cd2 O1 C4 -1.3(7) . . . . ? O9 Cd2 O1 C4 -173.8(6) 1_655 . . . ? O12 Cd2 O2 C4 -77.6(8) . . . . ? O10 Cd2 O2 C4 12.2(10) 1_655 . . . ? O11 Cd2 O2 C4 97.4(8) . . . . ? N2 Cd2 O2 C4 -175.2(8) . . . . ? O1 Cd2 O2 C4 1.3(7) . . . . ? O9 Cd2 O2 C4 157.6(11) 1_655 . . . ? O7 Cd1 O3 C8 88.0(6) . . . . ? N3 Cd1 O3 C8 -90.6(6) . . . . ? O5 Cd1 O3 C8 169.0(6) . . . . ? N1 Cd1 O3 C8 -4.6(8) 1_655 . . . ? O4 Cd1 O3 C8 4.4(6) . . . . ? O6 Cd1 O3 C8 179.0(6) . . . . ? O7 Cd1 O4 C8 -103.5(6) . . . . ? N3 Cd1 O4 C8 81.8(6) . . . . ? O5 Cd1 O4 C8 -26.6(7) . . . . ? N1 Cd1 O4 C8 169.7(6) 1_655 . . . ? O3 Cd1 O4 C8 -4.3(5) . . . . ? O6 Cd1 O4 C8 -167.1(10) . . . . ? O7 Cd1 O5 C7 -89.3(5) . . . . ? N3 Cd1 O5 C7 85.3(5) . . . . ? N1 Cd1 O5 C7 -13.0(7) 1_655 . . . ? O4 Cd1 O5 C7 -169.1(5) . . . . ? O3 Cd1 O5 C7 173.2(5) . . . . ? O6 Cd1 O5 C7 1.4(5) . . . . ? O7 Cd1 O6 C7 81.4(6) . . . . ? N3 Cd1 O6 C7 -103.3(6) . . . . ? O5 Cd1 O6 C7 -1.4(5) . . . . ? N1 Cd1 O6 C7 168.6(6) 1_655 . . . ? O4 Cd1 O6 C7 145.4(10) . . . . ? O3 Cd1 O6 C7 -13.8(7) . . . . ? O12 Cd2 N2 C14 85.9(8) . . . . ? O10 Cd2 N2 C14 -2.0(10) 1_655 . . . ? O11 Cd2 N2 C14 -84.9(8) . . . . ? O2 Cd2 N2 C14 -174.5(8) . . . . ? O1 Cd2 N2 C14 -178.7(7) . . . . ? O9 Cd2 N2 C14 -0.3(8) 1_655 . . . ? O12 Cd2 N2 C13 -103.8(8) . . . . ? O10 Cd2 N2 C13 168.3(7) 1_655 . . . ? O11 Cd2 N2 C13 85.5(8) . . . . ? O2 Cd2 N2 C13 -4.2(8) . . . . ? O1 Cd2 N2 C13 -8.3(10) . . . . ? O9 Cd2 N2 C13 170.1(8) 1_655 . . . ? O7 Cd1 N3 C20 22(3) . . . . ? O5 Cd1 N3 C20 -86.8(7) . . . . ? N1 Cd1 N3 C20 49.9(7) 1_655 . . . ? O4 Cd1 N3 C20 135.4(7) . . . . ? O3 Cd1 N3 C20 -171.9(7) . . . . ? O6 Cd1 N3 C20 -33.3(7) . . . . ? O7 Cd1 N3 C19 -166(2) . . . . ? O5 Cd1 N3 C19 84.9(10) . . . . ? N1 Cd1 N3 C19 -138.3(10) 1_655 . . . ? O4 Cd1 N3 C19 -52.8(10) . . . . ? O3 Cd1 N3 C19 -0.1(10) . . . . ? O6 Cd1 N3 C19 138.5(10) . . . . ? C3 C1 C2 C5 173.1(10) . . . . ? C2 C1 C3 C4 -174.9(10) . . . . ? Cd2 O1 C4 O2 2.3(12) . . . . ? Cd2 O1 C4 C3 -178.5(10) . . . . ? Cd2 O2 C4 O1 -2.3(12) . . . . ? Cd2 O2 C4 C3 178.3(9) . . . . ? C1 C3 C4 O1 0.9(17) . . . . ? C1 C3 C4 O2 -179.8(11) . . . . ? C1 C2 C5 C8 -173.7(9) . . . . ? Cd1 O6 C7 O5 2.5(9) . . . . ? Cd1 O6 C7 C6 -178.4(8) . . . . ? Cd1 O5 C7 O6 -2.7(9) . . . . ? Cd1 O5 C7 C6 178.2(7) . . . . ? C12 C6 C7 O6 17.7(14) . . . . ? C9 C6 C7 O6 -160.8(9) . . . . ? C12 C6 C7 O5 -163.2(9) . . . . ? C9 C6 C7 O5 18.4(13) . . . . ? Cd1 O3 C8 O4 -7.6(10) . . . . ? Cd1 O3 C8 C5 168.9(9) . . . . ? Cd1 O4 C8 O3 7.8(10) . . . . ? Cd1 O4 C8 C5 -168.8(8) . . . . ? C2 C5 C8 O3 4.1(15) . . . . ? C2 C5 C8 O4 -179.4(9) . . . . ? C10 N1 C9 C6 -1.1(14) . . . . ? Cd1 N1 C9 C6 172.7(7) 1_455 . . . ? C12 C6 C9 N1 1.7(14) . . . . ? C7 C6 C9 N1 -179.8(9) . . . . ? C9 N1 C10 C11 -0.4(15) . . . . ? Cd1 N1 C10 C11 -173.8(8) 1_455 . . . ? N1 C10 C11 C12 1.3(16) . . . . ? C9 C6 C12 C11 -0.7(14) . . . . ? C7 C6 C12 C11 -179.2(9) . . . . ? C10 C11 C12 C6 -0.7(15) . . . . ? C14 N2 C13 C16 1.3(15) . . . . ? Cd2 N2 C13 C16 -169.5(8) . . . . ? C13 N2 C14 C15 -0.4(15) . . . . ? Cd2 N2 C14 C15 170.3(8) . . . . ? N2 C14 C15 C17 -0.5(17) . . . . ? N2 C13 C16 C17 -1.2(16) . . . . ? N2 C13 C16 C18 -178.9(9) . . . . ? C13 C16 C17 C15 0.2(15) . . . . ? C18 C16 C17 C15 177.9(9) . . . . ? C14 C15 C17 C16 0.6(16) . . . . ? Cd2 O9 C18 O10 4.7(10) 1_455 . . . ? Cd2 O9 C18 C16 -172.5(8) 1_455 . . . ? Cd2 O10 C18 O9 -5.3(11) 1_455 . . . ? Cd2 O10 C18 C16 172.0(7) 1_455 . . . ? C13 C16 C18 O9 170.9(9) . . . . ? C17 C16 C18 O9 -6.8(15) . . . . ? C13 C16 C18 O10 -6.4(14) . . . . ? C17 C16 C18 O10 175.9(10) . . . . ? C20 N3 C19 C21 -2(2) . . . . ? Cd1 N3 C19 C21 -174.2(12) . . . . ? C19 N3 C20 C23 0.7(16) . . . . ? Cd1 N3 C20 C23 172.8(7) . . . . ? N3 C19 C21 C22 2(3) . . . . ? C19 C21 C22 C23 0(2) . . . . ? C21 C22 C23 N4 -179.2(13) . . . . ? C21 C22 C23 C20 -1.3(19) . . . . ? N3 C20 C23 N4 179.1(10) . . . . ? N3 C20 C23 C22 1.2(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3W H3WA O11 0.85(2) 2.00(4) 2.838(12) 170(15) 2_677 O3W H3WB O2W 0.84(2) 2.37(6) 3.157(18) 156(11) . O4W H4WA O5W 0.85(2) 1.89(3) 2.723(11) 166(11) . O4W H4WB O3W 0.84(2) 2.16(10) 2.784(13) 131(11) . O5W H5WA O7 0.85(2) 2.06(5) 2.852(10) 154(8) 2_666 O5W H5WB O3 0.85(2) 1.92(2) 2.773(10) 177(12) 1_655 O7 H7A O4 0.85(2) 1.83(3) 2.674(9) 170(8) 2_666 O7 H7B O5 0.85(2) 1.88(3) 2.728(9) 171(10) 2_566 O11 H11A O10 0.85(2) 1.89(3) 2.723(10) 167(9) 2_577 O11 H11B O2 0.84(2) 1.90(2) 2.747(11) 176(11) 2_577 O12 H12B O4W 0.85(2) 1.90(3) 2.741(11) 172(12) 2_667 O12 H12A O2W 0.85(2) 1.93(5) 2.733(13) 158(11) . N4 H4NA O5W 0.90(2) 2.27(5) 3.088(13) 152(10) 2_676 N4 H4NB O9 0.89(2) 2.32(6) 3.064(12) 141(9) 1_654 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 2.160 _refine_diff_density_min -0.854 _refine_diff_density_rms 0.177 data_p21 _database_code_depnum_ccdc_archive 'CCDC 890679' #TrackingRef 'cdadpnic3pnafinal1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H23 Cd N4 O8' _chemical_formula_weight 559.82 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' Cd Cd -0.8075 1.2024 '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(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9857(8) _cell_length_b 17.5783(17) _cell_length_c 16.1584(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.6140(10) _cell_angle_gamma 90.00 _cell_volume 2260.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9983 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 25.28 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1132 _exptl_absorpt_coefficient_mu 1.020 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8190 _exptl_absorpt_correction_T_max 0.8346 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17806 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.28 _reflns_number_total 4121 _reflns_number_gt 3525 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+4.1676P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4121 _refine_ls_number_parameters 322 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0703 _refine_ls_wR_factor_gt 0.0683 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.121 _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 Cd1 Cd 0.17913(3) 0.742665(14) 0.297984(17) 0.02306(9) Uani 1 1 d . . . O1 O 0.3756(5) 1.0182(2) 0.58277(19) 0.0647(10) Uani 1 1 d . . . O1W O 0.7004(4) 0.59666(17) 0.2950(2) 0.0485(8) Uani 1 1 d D . . H1WA H 0.763(5) 0.6334(19) 0.288(3) 0.058 Uiso 1 1 d D . . H1WB H 0.615(4) 0.611(2) 0.318(3) 0.058 Uiso 1 1 d D . . O2 O -0.1186(3) 0.74123(14) 0.28571(17) 0.0336(6) Uani 1 1 d . . . O2W O 0.0241(4) 1.00036(17) 0.3113(2) 0.0463(8) Uani 1 1 d D . . H2WA H 0.002(6) 0.9583(14) 0.288(3) 0.056 Uiso 1 1 d D . . H2WB H -0.043(5) 1.0316(19) 0.285(3) 0.056 Uiso 1 1 d D . . O3 O -0.0107(3) 0.85216(14) 0.25481(17) 0.0300(6) Uani 1 1 d . . . O3W O 0.9454(19) 0.5804(7) 0.4940(7) 0.095(4) Uani 0.50 1 d P A 1 O3W O 0.9077(18) 0.5615(7) 0.4480(6) 0.077(3) Uani 0.50 1 d P B 2 O5 O 0.1464(3) 0.62092(15) 0.35420(19) 0.0416(7) Uani 1 1 d . . . O6 O 0.4075(4) 0.65451(14) 0.34775(18) 0.0378(7) Uani 1 1 d . . . N1 N 0.1814(4) 0.79944(17) 0.4297(2) 0.0314(8) Uani 1 1 d . . . N2 N 0.2368(5) 1.0351(2) 0.4570(2) 0.0416(9) Uani 1 1 d D . . H2N H 0.172(5) 1.014(2) 0.414(2) 0.050 Uiso 1 1 d D . . N3 N -0.6014(4) 0.82685(16) 0.26638(19) 0.0251(7) Uani 1 1 d . . . N4 N 0.3254(4) 1.20783(18) 0.3420(2) 0.0319(8) Uani 1 1 d . . . C1 C 0.2207(5) 0.8734(2) 0.4376(2) 0.0341(10) Uani 1 1 d . . . H1 H 0.2370 0.9014 0.3887 0.041 Uiso 1 1 calc R . . C2 C 0.1540(6) 0.7621(3) 0.4991(3) 0.0508(12) Uani 1 1 d . . . H2 H 0.1219 0.7102 0.4952 0.061 Uiso 1 1 calc R . . C3 C 0.1703(8) 0.7957(3) 0.5758(3) 0.0710(18) Uani 1 1 d . . . H3 H 0.1504 0.7669 0.6238 0.085 Uiso 1 1 calc R . . C4 C 0.2149(7) 0.8702(3) 0.5837(3) 0.0620(15) Uani 1 1 d . . . H4 H 0.2293 0.8934 0.6369 0.074 Uiso 1 1 calc R . . C5 C 0.2389(6) 0.9114(2) 0.5131(3) 0.0403(11) Uani 1 1 d . . . C6 C 0.2896(6) 0.9928(3) 0.5223(3) 0.0480(12) Uani 1 1 d . . . C7 C -0.1330(5) 0.8101(2) 0.2649(2) 0.0258(8) Uani 1 1 d . . . C8 C -0.3064(4) 0.84266(19) 0.2517(2) 0.0223(8) Uani 1 1 d . . . C9 C -0.3366(5) 0.9152(2) 0.2190(2) 0.0296(9) Uani 1 1 d . . . H9 H -0.2467 0.9453 0.2020 0.035 Uiso 1 1 calc R . . C10 C -0.4994(5) 0.9426(2) 0.2115(3) 0.0343(10) Uani 1 1 d . . . H10 H -0.5227 0.9921 0.1902 0.041 Uiso 1 1 calc R . . C11 C -0.6258(5) 0.8974(2) 0.2350(3) 0.0336(9) Uani 1 1 d . . . H11 H -0.7372 0.9167 0.2290 0.040 Uiso 1 1 calc R . . C12 C -0.4431(4) 0.8018(2) 0.2748(2) 0.0247(8) Uani 1 1 d . . . H12 H -0.4231 0.7528 0.2983 0.030 Uiso 1 1 calc R . . C13 C 0.3000(5) 0.6074(2) 0.3667(2) 0.0273(9) Uani 1 1 d . . . C14 C 0.3575(5) 0.5313(2) 0.4043(2) 0.0312(9) Uani 1 1 d . . . H14A H 0.2574 0.5011 0.4159 0.037 Uiso 1 1 calc R . . H14B H 0.4185 0.5029 0.3632 0.037 Uiso 1 1 calc R . . C15 C 0.4698(5) 0.5390(2) 0.4834(2) 0.0324(9) Uani 1 1 d . . . H15A H 0.4077 0.5650 0.5258 0.039 Uiso 1 1 calc R . . H15B H 0.5683 0.5707 0.4728 0.039 Uiso 1 1 calc R . . C16 C 0.2860(6) 1.1133(2) 0.4440(3) 0.0394(10) Uani 1 1 d . . . C17 C 0.2892(5) 1.1370(2) 0.3642(3) 0.0339(10) Uani 1 1 d . . . H17 H 0.2641 1.1008 0.3213 0.041 Uiso 1 1 calc R . . C18 C 0.3260(7) 1.1649(3) 0.5065(3) 0.0575(14) Uani 1 1 d . . . H18 H 0.3261 1.1502 0.5631 0.069 Uiso 1 1 calc R . . C19 C 0.3645(6) 1.2585(3) 0.4023(3) 0.0489(12) Uani 1 1 d . . . H19 H 0.3917 1.3092 0.3879 0.059 Uiso 1 1 calc R . . C20 C 0.3661(7) 1.2383(3) 0.4852(3) 0.0661(16) Uani 1 1 d . . . H20 H 0.3946 1.2749 0.5273 0.079 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.01814(13) 0.02117(14) 0.02940(15) 0.00665(12) -0.00097(10) 0.00138(11) O1 0.086(3) 0.075(2) 0.0283(18) -0.0119(16) -0.0224(18) 0.006(2) O1W 0.045(2) 0.0343(17) 0.068(2) -0.0030(16) 0.0119(18) -0.0091(15) O2 0.0196(13) 0.0265(14) 0.0541(18) 0.0114(13) -0.0006(12) 0.0041(12) O2W 0.049(2) 0.0347(17) 0.051(2) -0.0081(15) -0.0216(16) 0.0053(15) O3 0.0165(14) 0.0304(14) 0.0427(17) 0.0037(12) 0.0014(12) -0.0010(11) O3W 0.117(11) 0.083(8) 0.092(9) 0.026(7) 0.060(9) 0.011(7) O3W 0.093(8) 0.079(7) 0.063(7) 0.003(6) 0.030(7) 0.004(5) O5 0.0285(16) 0.0325(15) 0.063(2) 0.0179(14) -0.0027(15) 0.0006(13) O6 0.0354(17) 0.0239(14) 0.0532(19) 0.0141(13) -0.0023(14) -0.0003(13) N1 0.039(2) 0.0260(17) 0.0297(19) 0.0068(14) 0.0048(16) 0.0052(15) N2 0.044(2) 0.049(2) 0.031(2) -0.0062(17) -0.0025(18) 0.0033(18) N3 0.0168(16) 0.0267(16) 0.0317(18) 0.0065(13) 0.0015(14) 0.0027(13) N4 0.0299(19) 0.0313(18) 0.0329(19) -0.0045(14) -0.0065(15) -0.0055(15) C1 0.043(3) 0.031(2) 0.029(2) 0.0056(17) 0.0062(19) 0.0027(19) C2 0.074(3) 0.038(2) 0.043(3) 0.012(2) 0.021(2) 0.013(2) C3 0.128(6) 0.051(3) 0.038(3) 0.017(2) 0.031(3) 0.026(3) C4 0.097(5) 0.060(3) 0.029(3) -0.001(2) 0.010(3) 0.024(3) C5 0.046(3) 0.038(2) 0.038(3) -0.0042(19) 0.006(2) 0.007(2) C6 0.054(3) 0.050(3) 0.040(3) -0.001(2) 0.005(2) 0.007(2) C7 0.023(2) 0.030(2) 0.024(2) -0.0004(16) -0.0015(16) 0.0003(17) C8 0.0186(19) 0.0247(18) 0.023(2) 0.0004(15) 0.0003(16) -0.0005(15) C9 0.022(2) 0.033(2) 0.034(2) 0.0064(17) 0.0000(17) -0.0036(17) C10 0.027(2) 0.029(2) 0.046(3) 0.0150(18) -0.0036(19) 0.0002(18) C11 0.024(2) 0.034(2) 0.042(2) 0.0092(18) -0.0008(19) 0.0074(18) C12 0.024(2) 0.0232(18) 0.027(2) 0.0027(15) 0.0009(16) 0.0042(16) C13 0.033(2) 0.0225(19) 0.025(2) 0.0027(15) -0.0061(18) -0.0013(17) C14 0.034(2) 0.026(2) 0.033(2) 0.0096(16) -0.0074(18) 0.0000(17) C15 0.035(2) 0.024(2) 0.036(2) 0.0065(17) -0.0075(19) 0.0021(17) C16 0.040(3) 0.038(2) 0.040(3) 0.000(2) 0.002(2) 0.004(2) C17 0.034(2) 0.030(2) 0.037(2) -0.0057(18) 0.0014(19) 0.0016(18) C18 0.072(4) 0.064(3) 0.034(3) 0.006(2) -0.006(3) -0.011(3) C19 0.070(3) 0.039(2) 0.036(3) -0.009(2) -0.002(2) -0.017(2) C20 0.101(4) 0.059(3) 0.036(3) -0.015(2) -0.008(3) -0.025(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 Cd1 N4 2.340(3) 2_545 ? Cd1 O5 2.348(3) . ? Cd1 N1 2.349(3) . ? Cd1 O2 2.370(2) . ? Cd1 N3 2.380(3) 1_655 ? Cd1 O6 2.478(3) . ? Cd1 O3 2.514(2) . ? O1 C6 1.232(5) . ? O1W H1WA 0.830(19) . ? O1W H1WB 0.839(19) . ? O2 C7 1.259(4) . ? O2W H2WA 0.838(19) . ? O2W H2WB 0.854(19) . ? O3 C7 1.246(4) . ? O5 C13 1.250(4) . ? O6 C13 1.249(4) . ? N1 C2 1.332(5) . ? N1 C1 1.341(5) . ? N2 C6 1.331(6) . ? N2 C16 1.451(5) . ? N2 H2N 0.905(19) . ? N3 C12 1.335(4) . ? N3 C11 1.348(5) . ? N3 Cd1 2.380(3) 1_455 ? N4 C17 1.333(5) . ? N4 C19 1.338(5) . ? N4 Cd1 2.340(3) 2 ? C1 C5 1.389(6) . ? C1 H1 0.9500 . ? C2 C3 1.370(7) . ? C2 H2 0.9500 . ? C3 C4 1.360(7) . ? C3 H3 0.9500 . ? C4 C5 1.377(6) . ? C4 H4 0.9500 . ? C5 C6 1.491(6) . ? C7 C8 1.498(5) . ? C8 C12 1.383(5) . ? C8 C9 1.394(5) . ? C9 C10 1.382(5) . ? C9 H9 0.9500 . ? C10 C11 1.362(5) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.524(5) . ? C14 C15 1.507(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C15 1.536(7) 3_666 ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.358(6) . ? C16 C18 1.375(6) . ? C17 H17 0.9500 . ? C18 C20 1.380(7) . ? C18 H18 0.9500 . ? C19 C20 1.386(6) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? 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 N4 Cd1 O5 98.15(11) 2_545 . ? N4 Cd1 N1 170.02(11) 2_545 . ? O5 Cd1 N1 91.71(11) . . ? N4 Cd1 O2 88.79(10) 2_545 . ? O5 Cd1 O2 83.13(9) . . ? N1 Cd1 O2 90.85(11) . . ? N4 Cd1 N3 84.83(11) 2_545 1_655 ? O5 Cd1 N3 139.16(10) . 1_655 ? N1 Cd1 N3 88.75(11) . 1_655 ? O2 Cd1 N3 137.70(9) . 1_655 ? N4 Cd1 O6 95.96(10) 2_545 . ? O5 Cd1 O6 53.58(9) . . ? N1 Cd1 O6 91.14(10) . . ? O2 Cd1 O6 136.71(9) . . ? N3 Cd1 O6 85.58(9) 1_655 . ? N4 Cd1 O3 88.28(10) 2_545 . ? O5 Cd1 O3 136.21(9) . . ? N1 Cd1 O3 83.49(10) . . ? O2 Cd1 O3 53.60(8) . . ? N3 Cd1 O3 84.39(9) 1_655 . ? O6 Cd1 O3 168.72(8) . . ? H1WA O1W H1WB 110(4) . . ? C7 O2 Cd1 94.7(2) . . ? H2WA O2W H2WB 104(3) . . ? C7 O3 Cd1 88.3(2) . . ? C13 O5 Cd1 95.6(2) . . ? C13 O6 Cd1 89.5(2) . . ? C2 N1 C1 116.7(4) . . ? C2 N1 Cd1 124.3(3) . . ? C1 N1 Cd1 118.9(3) . . ? C6 N2 C16 124.9(4) . . ? C6 N2 H2N 120(3) . . ? C16 N2 H2N 115(3) . . ? C12 N3 C11 116.7(3) . . ? C12 N3 Cd1 118.7(2) . 1_455 ? C11 N3 Cd1 124.5(2) . 1_455 ? C17 N4 C19 117.9(4) . . ? C17 N4 Cd1 121.2(3) . 2 ? C19 N4 Cd1 120.9(3) . 2 ? N1 C1 C5 123.9(4) . . ? N1 C1 H1 118.1 . . ? C5 C1 H1 118.1 . . ? N1 C2 C3 122.7(4) . . ? N1 C2 H2 118.7 . . ? C3 C2 H2 118.7 . . ? C4 C3 C2 120.3(5) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 118.8(5) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C4 C5 C1 117.6(4) . . ? C4 C5 C6 118.5(4) . . ? C1 C5 C6 123.9(4) . . ? O1 C6 N2 123.2(5) . . ? O1 C6 C5 123.8(4) . . ? N2 C6 C5 113.0(4) . . ? O3 C7 O2 123.4(3) . . ? O3 C7 C8 118.7(3) . . ? O2 C7 C8 117.9(3) . . ? C12 C8 C9 117.5(3) . . ? C12 C8 C7 120.3(3) . . ? C9 C8 C7 122.2(3) . . ? C10 C9 C8 119.0(4) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C11 C10 C9 119.1(4) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? N3 C11 C10 123.6(4) . . ? N3 C11 H11 118.2 . . ? C10 C11 H11 118.2 . . ? N3 C12 C8 124.2(3) . . ? N3 C12 H12 117.9 . . ? C8 C12 H12 117.9 . . ? O6 C13 O5 121.3(3) . . ? O6 C13 C14 119.2(3) . . ? O5 C13 C14 119.5(3) . . ? C15 C14 C13 113.6(3) . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C14 C15 C15 111.4(4) . 3_666 ? C14 C15 H15A 109.3 . . ? C15 C15 H15A 109.3 3_666 . ? C14 C15 H15B 109.3 . . ? C15 C15 H15B 109.3 3_666 . ? H15A C15 H15B 108.0 . . ? C17 C16 C18 118.3(4) . . ? C17 C16 N2 117.0(4) . . ? C18 C16 N2 124.6(4) . . ? N4 C17 C16 124.3(4) . . ? N4 C17 H17 117.9 . . ? C16 C17 H17 117.9 . . ? C16 C18 C20 118.6(4) . . ? C16 C18 H18 120.7 . . ? C20 C18 H18 120.7 . . ? N4 C19 C20 121.2(4) . . ? N4 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C18 C20 C19 119.7(4) . . ? C18 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Cd1 O2 C7 -90.1(2) 2_545 . . . ? O5 Cd1 O2 C7 171.5(2) . . . . ? N1 Cd1 O2 C7 79.9(2) . . . . ? N3 Cd1 O2 C7 -9.2(3) 1_655 . . . ? O6 Cd1 O2 C7 172.5(2) . . . . ? O3 Cd1 O2 C7 -1.3(2) . . . . ? N4 Cd1 O3 C7 91.1(2) 2_545 . . . ? O5 Cd1 O3 C7 -8.9(3) . . . . ? N1 Cd1 O3 C7 -94.5(2) . . . . ? O2 Cd1 O3 C7 1.4(2) . . . . ? N3 Cd1 O3 C7 176.1(2) 1_655 . . . ? O6 Cd1 O3 C7 -156.5(4) . . . . ? N4 Cd1 O5 C13 91.8(2) 2_545 . . . ? N1 Cd1 O5 C13 -89.7(2) . . . . ? O2 Cd1 O5 C13 179.6(3) . . . . ? N3 Cd1 O5 C13 0.3(3) 1_655 . . . ? O6 Cd1 O5 C13 0.4(2) . . . . ? O3 Cd1 O5 C13 -172.1(2) . . . . ? N4 Cd1 O6 C13 -96.2(2) 2_545 . . . ? O5 Cd1 O6 C13 -0.4(2) . . . . ? N1 Cd1 O6 C13 90.9(2) . . . . ? O2 Cd1 O6 C13 -1.6(3) . . . . ? N3 Cd1 O6 C13 179.5(2) 1_655 . . . ? O3 Cd1 O6 C13 152.2(4) . . . . ? N4 Cd1 N1 C2 165.6(6) 2_545 . . . ? O5 Cd1 N1 C2 -5.3(4) . . . . ? O2 Cd1 N1 C2 77.8(4) . . . . ? N3 Cd1 N1 C2 -144.5(4) 1_655 . . . ? O6 Cd1 N1 C2 -58.9(4) . . . . ? O3 Cd1 N1 C2 131.0(4) . . . . ? N4 Cd1 N1 C1 -17.9(9) 2_545 . . . ? O5 Cd1 N1 C1 171.2(3) . . . . ? O2 Cd1 N1 C1 -105.7(3) . . . . ? N3 Cd1 N1 C1 32.0(3) 1_655 . . . ? O6 Cd1 N1 C1 117.6(3) . . . . ? O3 Cd1 N1 C1 -52.5(3) . . . . ? C2 N1 C1 C5 2.0(6) . . . . ? Cd1 N1 C1 C5 -174.7(3) . . . . ? C1 N1 C2 C3 -2.3(7) . . . . ? Cd1 N1 C2 C3 174.3(4) . . . . ? N1 C2 C3 C4 0.5(9) . . . . ? C2 C3 C4 C5 1.7(9) . . . . ? C3 C4 C5 C1 -1.9(8) . . . . ? C3 C4 C5 C6 -179.3(5) . . . . ? N1 C1 C5 C4 0.0(7) . . . . ? N1 C1 C5 C6 177.3(4) . . . . ? C16 N2 C6 O1 6.6(8) . . . . ? C16 N2 C6 C5 -171.5(4) . . . . ? C4 C5 C6 O1 31.0(7) . . . . ? C1 C5 C6 O1 -146.3(5) . . . . ? C4 C5 C6 N2 -150.9(5) . . . . ? C1 C5 C6 N2 31.7(7) . . . . ? Cd1 O3 C7 O2 -2.5(4) . . . . ? Cd1 O3 C7 C8 177.7(3) . . . . ? Cd1 O2 C7 O3 2.6(4) . . . . ? Cd1 O2 C7 C8 -177.5(3) . . . . ? O3 C7 C8 C12 -169.8(3) . . . . ? O2 C7 C8 C12 10.3(5) . . . . ? O3 C7 C8 C9 7.9(5) . . . . ? O2 C7 C8 C9 -171.9(4) . . . . ? C12 C8 C9 C10 0.2(6) . . . . ? C7 C8 C9 C10 -177.6(4) . . . . ? C8 C9 C10 C11 -1.1(6) . . . . ? C12 N3 C11 C10 0.7(6) . . . . ? Cd1 N3 C11 C10 -174.8(3) 1_455 . . . ? C9 C10 C11 N3 0.7(7) . . . . ? C11 N3 C12 C8 -1.7(6) . . . . ? Cd1 N3 C12 C8 174.1(3) 1_455 . . . ? C9 C8 C12 N3 1.2(6) . . . . ? C7 C8 C12 N3 179.1(3) . . . . ? Cd1 O6 C13 O5 0.7(4) . . . . ? Cd1 O6 C13 C14 179.6(3) . . . . ? Cd1 O5 C13 O6 -0.8(4) . . . . ? Cd1 O5 C13 C14 -179.6(3) . . . . ? O6 C13 C14 C15 58.3(5) . . . . ? O5 C13 C14 C15 -122.9(4) . . . . ? C13 C14 C15 C15 -177.5(4) . . . 3_666 ? C6 N2 C16 C17 150.4(4) . . . . ? C6 N2 C16 C18 -30.9(7) . . . . ? C19 N4 C17 C16 1.4(6) . . . . ? Cd1 N4 C17 C16 -178.5(3) 2 . . . ? C18 C16 C17 N4 -1.5(7) . . . . ? N2 C16 C17 N4 177.3(4) . . . . ? C17 C16 C18 C20 0.6(8) . . . . ? N2 C16 C18 C20 -178.1(5) . . . . ? C17 N4 C19 C20 -0.5(7) . . . . ? Cd1 N4 C19 C20 179.5(4) 2 . . . ? C16 C18 C20 C19 0.3(9) . . . . ? N4 C19 C20 C18 -0.3(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O2 0.830(19) 2.12(2) 2.933(4) 166(4) 1_655 O1W H1WB O6 0.839(19) 1.92(2) 2.748(4) 168(5) . O2W H2WA O3 0.838(19) 1.94(2) 2.767(4) 167(4) . O2W H2WB O1W 0.854(19) 2.07(2) 2.921(4) 171(4) 2 N2 H2N O2W 0.905(19) 1.98(2) 2.855(5) 163(4) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.639 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.081 data_twin5 _database_code_depnum_ccdc_archive 'CCDC 891129' #TrackingRef '0cdadipate3pinatwinfinal.cif' _audit_update_record ; 2012-08-30 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H38 Cd2 N6 O12' _chemical_formula_weight 947.50 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.506(7) _cell_length_b 10.573(9) _cell_length_c 20.792(18) _cell_angle_alpha 78.711(15) _cell_angle_beta 79.649(15) _cell_angle_gamma 88.877(15) _cell_volume 1804(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.744 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 1.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6153 _exptl_absorpt_correction_T_max 0.7916 _exptl_absorpt_process_details TWINABS _exptl_special_details ; Crystal was non-merohedrally twinned. The twin law was found using CELL NOW. Reflections for both twin components were used in the refinement. ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 34278 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_av_sigmaI/netI 0.0707 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.26 _reflns_number_total 10966 _reflns_number_gt 8143 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0972P)^2^+2.0608P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10966 _refine_ls_number_parameters 479 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1625 _refine_ls_wR_factor_gt 0.1487 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 Cd1 Cd 0.85128(6) 0.01841(5) 0.44035(2) 0.01604(15) Uani 1 1 d . . . Cd2 Cd 1.84190(6) 0.58868(5) -0.04524(2) 0.01612(15) Uani 1 1 d . . . O1 O 0.9045(6) 0.0732(5) 0.5449(3) 0.0317(14) Uani 1 1 d . . . O1W O 2.0391(7) 1.0178(6) -0.1372(3) 0.0521(18) Uani 1 1 d D . . H1WA H 1.992(9) 1.071(6) -0.164(4) 0.063 Uiso 1 1 d D . . H1WB H 1.974(8) 0.952(5) -0.125(4) 0.063 Uiso 1 1 d D . . O2 O 1.2837(6) 0.6107(5) 0.2722(3) 0.0324(13) Uani 1 1 d . . . O2W O 1.0366(9) 0.8013(7) 0.2454(3) 0.069(2) Uani 1 1 d D . . H2WA H 1.1086 0.7465 0.2532 0.083 Uiso 1 1 d RD . . H2WB H 1.017(10) 0.848(7) 0.275(3) 0.083 Uiso 1 1 d D . . O3 O 1.8052(6) 0.8221(5) -0.0828(2) 0.0245(12) Uani 1 1 d . . . O4 O 1.2769(7) 0.6105(5) 0.0438(3) 0.0350(15) Uani 1 1 d . . . O5 O 1.6554(6) 0.6834(4) -0.1114(2) 0.0211(11) Uani 1 1 d . . . O6 O 0.3340(6) -0.0554(5) 0.6347(2) 0.0221(12) Uani 1 1 d . . . O7 O 1.0719(6) 0.6273(5) -0.0039(3) 0.0297(13) Uani 1 1 d . . . O8 O 0.3560(8) -0.5310(6) 0.6561(3) 0.062(2) Uani 1 1 d . . . O9 O 0.6989(7) 0.1533(6) 0.5027(3) 0.0369(15) Uani 1 1 d . . . O10 O 0.1372(6) 0.0758(5) 0.6596(2) 0.0244(12) Uani 1 1 d . . . N1 N 1.7050(7) 0.6328(6) 0.0546(3) 0.0160(13) Uani 1 1 d . . . N2 N 1.3944(7) 0.4949(6) 0.1953(3) 0.0192(14) Uani 1 1 d . . . H2N H 1.3864 0.4215 0.1821 0.023 Uiso 1 1 calc R . . N3 N 1.0102(6) 0.1910(6) 0.3731(3) 0.0174(13) Uani 1 1 d . . . N4 N 0.7363(7) -0.1799(6) 0.4949(3) 0.0187(8) Uani 1 1 d . . . N5 N 0.4297(7) -0.3175(6) 0.6370(3) 0.0187(8) Uani 1 1 d . . . H5N H 0.4067 -0.2446 0.6507 0.022 Uiso 1 1 calc R . . N6 N 0.0246(7) -0.4121(6) 0.8558(3) 0.0187(8) Uani 1 1 d . . . C1 C 1.7454(9) 0.7403(7) 0.0725(3) 0.0210(16) Uani 1 1 d . . . H1 H 1.8269 0.7947 0.0436 0.025 Uiso 1 1 calc R . . C2 C 1.6742(9) 0.7762(7) 0.1311(4) 0.0277(18) Uani 1 1 d . . . H2 H 1.7073 0.8529 0.1425 0.033 Uiso 1 1 calc R . . C3 C 1.5524(10) 0.6976(7) 0.1734(3) 0.0272(19) Uani 1 1 d . . . H3 H 1.5001 0.7203 0.2138 0.033 Uiso 1 1 calc R . . C4 C 1.5104(8) 0.5867(7) 0.1550(3) 0.0170(16) Uani 1 1 d . . . C5 C 1.2957(8) 0.5102(7) 0.2519(3) 0.0179(16) Uani 1 1 d . . . C6 C 1.0928(9) 0.4120(8) 0.3489(4) 0.0258(18) Uani 1 1 d . . . H6 H 1.0849 0.4943 0.3609 0.031 Uiso 1 1 calc R . . C7 C 1.1978(8) 0.3928(7) 0.2909(3) 0.0169(16) Uani 1 1 d . . . C8 C 1.2074(9) 0.2725(7) 0.2761(3) 0.0253(18) Uani 1 1 d . . . H8 H 1.2781 0.2563 0.2378 0.030 Uiso 1 1 calc R . . C9 C 1.0021(9) 0.3088(7) 0.3877(4) 0.0233(18) Uani 1 1 d . . . H9 H 0.9307 0.3220 0.4264 0.028 Uiso 1 1 calc R . . C10 C 1.1118(9) 0.1740(8) 0.3181(4) 0.0279(19) Uani 1 1 d . . . H10 H 1.1187 0.0905 0.3075 0.033 Uiso 1 1 calc R . . C11 C 1.5884(8) 0.5557(7) 0.0947(3) 0.0150(15) Uani 1 1 d . . . H11 H 1.5584 0.4792 0.0820 0.018 Uiso 1 1 calc R . . C20 C 0.6197(8) -0.1940(7) 0.5484(3) 0.0188(16) Uani 1 1 d . . . H20 H 0.5830 -0.1197 0.5656 0.023 Uiso 1 1 calc R . . C21 C 0.5496(8) -0.3137(7) 0.5800(3) 0.0171(16) Uani 1 1 d . . . C22 C 0.6018(9) -0.4218(7) 0.5540(3) 0.0242(17) Uani 1 1 d . . . H22 H 0.5567 -0.5047 0.5741 0.029 Uiso 1 1 calc R . . C23 C 0.7882(9) -0.2823(7) 0.4689(4) 0.0237(18) Uani 1 1 d . . . H23 H 0.8704 -0.2718 0.4307 0.028 Uiso 1 1 calc R . . C24 C 0.7218(9) -0.4057(7) 0.4978(4) 0.0302(19) Uani 1 1 d . . . H24 H 0.7590 -0.4780 0.4789 0.036 Uiso 1 1 calc R . . C25 C 0.3462(9) -0.4261(8) 0.6726(4) 0.030(2) Uani 1 1 d . . . C31 C 1.6870(9) 0.7981(7) -0.1077(4) 0.0193(12) Uani 1 1 d . . . C32 C 1.5776(8) 0.9056(7) -0.1320(4) 0.0193(12) Uani 1 1 d . . . H32A H 1.5895 0.9195 -0.1812 0.023 Uiso 1 1 calc R . . H32B H 1.6075 0.9868 -0.1201 0.023 Uiso 1 1 calc R . . C33 C 1.4024(8) 0.8688(7) -0.0998(3) 0.0215(17) Uani 1 1 d . . . H33A H 1.3310 0.9272 -0.1241 0.026 Uiso 1 1 calc R . . H33B H 1.3805 0.7799 -0.1047 0.026 Uiso 1 1 calc R . . C34 C 1.3626(10) 0.8758(7) -0.0259(3) 0.0223(18) Uani 1 1 d . . . H34A H 1.4409 0.8249 -0.0020 0.027 Uiso 1 1 calc R . . H34B H 1.3715 0.9665 -0.0210 0.027 Uiso 1 1 calc R . . C35 C 1.1949(9) 0.8244(7) 0.0055(4) 0.0274(18) Uani 1 1 d . . . H35A H 1.1638 0.8498 0.0493 0.033 Uiso 1 1 calc R . . H35B H 1.1190 0.8641 -0.0233 0.033 Uiso 1 1 calc R . . C36 C 1.1825(8) 0.6790(7) 0.0149(3) 0.0174(16) Uani 1 1 d . . . C41 C 0.7867(8) 0.1441(7) 0.5461(3) 0.0198(17) Uani 1 1 d . . . C42 C 0.7467(8) 0.2223(7) 0.6002(4) 0.0238(18) Uani 1 1 d . . . H42A H 0.7710 0.3143 0.5804 0.029 Uiso 1 1 calc R . . H42B H 0.8159 0.1949 0.6338 0.029 Uiso 1 1 calc R . . C43 C 0.5705(10) 0.2085(7) 0.6354(4) 0.025(2) Uani 1 1 d . . . H43A H 0.5017 0.2064 0.6019 0.030 Uiso 1 1 calc R . . H43B H 0.5412 0.2849 0.6557 0.030 Uiso 1 1 calc R . . C44 C 0.5378(8) 0.0858(7) 0.6901(3) 0.0206(16) Uani 1 1 d . . . H44A H 0.5796 0.0100 0.6714 0.025 Uiso 1 1 calc R . . H44B H 0.5945 0.0929 0.7269 0.025 Uiso 1 1 calc R . . C45 C 0.3592(9) 0.0663(8) 0.7172(4) 0.0271(18) Uani 1 1 d . . . H45A H 0.3430 -0.0009 0.7584 0.032 Uiso 1 1 calc R . . H45B H 0.3140 0.1476 0.7289 0.032 Uiso 1 1 calc R . . C46 C 0.2715(9) 0.0263(7) 0.6669(3) 0.0190(16) Uani 1 1 d . . . C50 C 0.0360(8) -0.5157(8) 0.8272(4) 0.0237(18) Uani 1 1 d . . . H50 H -0.0303 -0.5888 0.8482 0.028 Uiso 1 1 calc R . . C51 C 0.1407(9) -0.5209(7) 0.7682(3) 0.0234(17) Uani 1 1 d . . . H51 H 0.1477 -0.5967 0.7498 0.028 Uiso 1 1 calc R . . C52 C 0.2353(8) -0.4120(7) 0.7368(3) 0.0192(16) Uani 1 1 d . . . C53 C 0.1138(8) -0.3071(8) 0.8250(4) 0.0206(17) Uani 1 1 d . . . H53 H 0.1029 -0.2320 0.8441 0.025 Uiso 1 1 calc R . . C54 C 0.2224(9) -0.3047(7) 0.7656(3) 0.0214(17) Uani 1 1 d . . . H54 H 0.2865 -0.2300 0.7454 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0123(3) 0.0219(3) 0.0120(3) -0.0006(2) 0.0003(2) -0.0011(2) Cd2 0.0113(3) 0.0218(3) 0.0127(3) 0.0015(2) -0.0003(2) -0.0020(2) O1 0.020(3) 0.044(4) 0.035(3) -0.015(3) -0.009(3) 0.017(3) O1W 0.038(4) 0.050(4) 0.058(4) 0.022(3) -0.016(3) -0.014(3) O2 0.035(3) 0.026(3) 0.031(3) -0.011(3) 0.011(3) -0.009(2) O2W 0.079(5) 0.094(6) 0.038(4) -0.021(4) -0.014(4) 0.051(4) O3 0.025(3) 0.020(3) 0.025(3) 0.007(2) -0.006(2) -0.009(2) O4 0.038(4) 0.018(3) 0.056(4) 0.002(3) -0.037(3) 0.000(3) O5 0.020(3) 0.019(3) 0.021(3) -0.001(2) 0.003(2) -0.004(2) O6 0.026(3) 0.024(3) 0.019(3) -0.003(2) -0.013(2) 0.002(2) O7 0.021(3) 0.026(3) 0.045(4) -0.005(3) -0.016(3) -0.001(2) O8 0.083(5) 0.024(3) 0.057(4) -0.011(3) 0.051(4) -0.003(3) O9 0.034(4) 0.058(4) 0.026(3) -0.021(3) -0.014(3) 0.020(3) O10 0.023(3) 0.030(3) 0.021(3) -0.006(2) -0.006(2) 0.005(2) N1 0.011(3) 0.022(3) 0.013(3) 0.001(2) -0.001(2) 0.000(2) N2 0.024(4) 0.015(3) 0.016(3) -0.006(2) 0.006(3) -0.008(3) N3 0.007(3) 0.028(4) 0.012(3) 0.008(3) -0.001(2) -0.005(2) N4 0.014(2) 0.024(2) 0.0141(18) -0.0032(16) 0.0056(15) -0.0004(16) N5 0.014(2) 0.024(2) 0.0141(18) -0.0032(16) 0.0056(15) -0.0004(16) N6 0.014(2) 0.024(2) 0.0141(18) -0.0032(16) 0.0056(15) -0.0004(16) C1 0.022(4) 0.019(4) 0.019(4) 0.001(3) -0.001(3) -0.004(3) C2 0.022(4) 0.030(4) 0.025(4) -0.003(3) 0.008(3) -0.005(3) C3 0.037(5) 0.032(4) 0.011(4) -0.002(3) -0.002(4) -0.012(4) C4 0.020(4) 0.020(4) 0.009(3) 0.002(3) 0.000(3) -0.009(3) C5 0.014(4) 0.022(4) 0.016(4) -0.002(3) -0.001(3) -0.004(3) C6 0.018(4) 0.033(5) 0.024(4) -0.005(4) 0.004(3) -0.008(3) C7 0.013(4) 0.026(4) 0.013(4) -0.001(3) -0.007(3) -0.007(3) C8 0.022(4) 0.035(5) 0.013(4) 0.001(3) 0.006(3) -0.003(3) C9 0.028(5) 0.016(4) 0.022(4) -0.006(3) 0.009(3) -0.006(3) C10 0.033(5) 0.031(5) 0.019(4) -0.009(3) 0.004(4) -0.003(4) C11 0.009(4) 0.023(4) 0.012(4) -0.005(3) 0.002(3) -0.002(3) C20 0.020(4) 0.020(4) 0.016(4) -0.002(3) -0.005(3) 0.001(3) C21 0.014(4) 0.024(4) 0.014(4) -0.004(3) -0.002(3) -0.004(3) C22 0.027(4) 0.020(4) 0.023(4) -0.001(3) 0.003(3) -0.011(3) C23 0.021(4) 0.028(4) 0.016(4) 0.002(3) 0.005(3) -0.004(3) C24 0.038(5) 0.028(4) 0.019(4) -0.005(3) 0.009(3) 0.005(4) C25 0.026(5) 0.034(5) 0.023(4) -0.003(4) 0.013(4) 0.004(4) C31 0.020(3) 0.015(3) 0.018(3) 0.008(2) -0.003(2) 0.002(2) C32 0.020(3) 0.015(3) 0.018(3) 0.008(2) -0.003(2) 0.002(2) C33 0.019(4) 0.017(4) 0.027(4) 0.006(3) -0.011(3) 0.004(3) C34 0.028(5) 0.017(4) 0.021(5) 0.000(3) -0.006(4) 0.000(3) C35 0.024(4) 0.027(4) 0.033(5) -0.008(4) -0.008(4) -0.001(3) C36 0.010(4) 0.027(4) 0.016(4) -0.010(3) 0.002(3) -0.001(3) C41 0.013(4) 0.030(4) 0.013(4) 0.001(3) 0.001(3) -0.003(3) C42 0.025(4) 0.029(4) 0.019(4) -0.013(3) -0.001(3) -0.009(3) C43 0.016(4) 0.027(4) 0.031(6) -0.006(4) -0.002(4) 0.000(4) C44 0.021(4) 0.022(4) 0.019(4) -0.001(3) -0.007(3) 0.002(3) C45 0.030(4) 0.033(5) 0.018(4) -0.004(3) -0.004(3) -0.009(4) C46 0.018(4) 0.017(4) 0.016(4) 0.004(3) 0.006(3) -0.001(3) C50 0.011(4) 0.038(5) 0.018(4) 0.003(4) 0.001(3) -0.006(3) C51 0.029(5) 0.019(4) 0.018(4) 0.001(3) 0.001(3) -0.003(3) C52 0.017(4) 0.024(4) 0.012(4) 0.003(3) 0.002(3) 0.002(3) C53 0.022(4) 0.025(4) 0.017(4) -0.013(3) -0.001(3) 0.009(3) C54 0.023(4) 0.020(4) 0.017(4) 0.004(3) 0.001(3) -0.004(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 Cd1 O1 2.319(5) 2_756 ? Cd1 N4 2.322(6) . ? Cd1 O9 2.333(5) . ? Cd1 N3 2.352(6) . ? Cd1 O6 2.386(5) 2_656 ? Cd1 O10 2.461(5) 2_656 ? Cd1 O1 2.475(5) . ? Cd1 C46 2.748(8) 2_656 ? Cd1 C41 2.755(8) . ? Cd2 N1 2.317(6) . ? Cd2 O4 2.346(5) 2_865 ? Cd2 O7 2.346(5) 1_655 ? Cd2 N6 2.347(6) 1_764 ? Cd2 O5 2.365(5) . ? Cd2 O7 2.467(5) 2_865 ? Cd2 O3 2.470(5) . ? O1 C41 1.240(9) . ? O1 Cd1 2.319(5) 2_756 ? O1W H1WA 0.86(2) . ? O1W H1WB 0.87(2) . ? O2 C5 1.214(8) . ? O2W H2WA 0.8495 . ? O2W H2WB 0.86(2) . ? O3 C31 1.262(9) . ? O4 C36 1.230(8) . ? O4 Cd2 2.346(5) 2_865 ? O5 C31 1.267(8) . ? O6 C46 1.248(8) . ? O6 Cd1 2.386(5) 2_656 ? O7 C36 1.254(8) . ? O7 Cd2 2.346(5) 1_455 ? O7 Cd2 2.467(5) 2_865 ? O8 C25 1.220(10) . ? O9 C41 1.260(9) . ? O10 C46 1.269(8) . ? O10 Cd1 2.461(5) 2_656 ? N1 C1 1.333(9) . ? N1 C11 1.346(8) . ? N2 C5 1.354(9) . ? N2 C4 1.429(8) . ? N2 H2N 0.8800 . ? N3 C9 1.336(9) . ? N3 C10 1.344(9) . ? N4 C23 1.335(10) . ? N4 C20 1.338(8) . ? N5 C25 1.372(10) . ? N5 C21 1.413(8) . ? N5 H5N 0.8800 . ? N6 C53 1.341(10) . ? N6 C50 1.338(10) . ? N6 Cd2 2.347(6) 1_346 ? C1 C2 1.378(10) . ? C1 H1 0.9500 . ? C2 C3 1.399(10) . ? C2 H2 0.9500 . ? C3 C4 1.375(10) . ? C3 H3 0.9500 . ? C4 C11 1.404(9) . ? C5 C7 1.515(9) . ? C6 C9 1.379(10) . ? C6 C7 1.413(10) . ? C6 H6 0.9500 . ? C7 C8 1.363(10) . ? C8 C10 1.390(11) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C20 C21 1.397(9) . ? C20 H20 0.9500 . ? C21 C22 1.390(10) . ? C22 C24 1.391(10) . ? C22 H22 0.9500 . ? C23 C24 1.408(10) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C52 1.520(10) . ? C31 C32 1.521(9) . ? C32 C33 1.544(10) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.529(10) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.521(10) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.515(10) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C41 C42 1.509(10) . ? C42 C43 1.542(10) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.541(10) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C45 1.526(10) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C46 1.515(10) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 Cd1 2.748(8) 2_656 ? C50 C51 1.390(10) . ? C50 H50 0.9500 . ? C51 C52 1.398(10) . ? C51 H51 0.9500 . ? C52 C54 1.376(10) . ? C53 C54 1.399(10) . ? C53 H53 0.9500 . ? C54 H54 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cd1 N4 86.7(2) 2_756 . ? O1 Cd1 O9 128.14(19) 2_756 . ? N4 Cd1 O9 99.9(2) . . ? O1 Cd1 N3 83.8(2) 2_756 . ? N4 Cd1 N3 167.2(2) . . ? O9 Cd1 N3 92.7(2) . . ? O1 Cd1 O6 143.24(18) 2_756 2_656 ? N4 Cd1 O6 93.2(2) . 2_656 ? O9 Cd1 O6 88.12(18) . 2_656 ? N3 Cd1 O6 89.27(19) . 2_656 ? O1 Cd1 O10 89.46(18) 2_756 2_656 ? N4 Cd1 O10 83.3(2) . 2_656 ? O9 Cd1 O10 142.27(18) . 2_656 ? N3 Cd1 O10 88.0(2) . 2_656 ? O6 Cd1 O10 54.16(17) 2_656 2_656 ? O1 Cd1 O1 74.7(2) 2_756 . ? N4 Cd1 O1 92.7(2) . . ? O9 Cd1 O1 53.81(17) . . ? N3 Cd1 O1 93.0(2) . . ? O6 Cd1 O1 141.92(17) 2_656 . ? O10 Cd1 O1 163.85(16) 2_656 . ? O1 Cd1 C46 116.9(2) 2_756 2_656 ? N4 Cd1 C46 85.3(2) . 2_656 ? O9 Cd1 C46 114.9(2) . 2_656 ? N3 Cd1 C46 91.4(2) . 2_656 ? O6 Cd1 C46 26.96(18) 2_656 2_656 ? O10 Cd1 C46 27.48(18) 2_656 2_656 ? O1 Cd1 C46 168.01(18) . 2_656 ? O1 Cd1 C41 101.2(2) 2_756 . ? N4 Cd1 C41 97.8(2) . . ? O9 Cd1 C41 27.1(2) . . ? N3 Cd1 C41 92.5(2) . . ? O6 Cd1 C41 115.2(2) 2_656 . ? O10 Cd1 C41 169.36(19) 2_656 . ? O1 Cd1 C41 26.74(18) . . ? C46 Cd1 C41 141.9(2) 2_656 . ? N1 Cd2 O4 99.9(2) . 2_865 ? N1 Cd2 O7 84.8(2) . 1_655 ? O4 Cd2 O7 128.10(17) 2_865 1_655 ? N1 Cd2 N6 164.9(2) . 1_764 ? O4 Cd2 N6 94.7(2) 2_865 1_764 ? O7 Cd2 N6 83.4(2) 1_655 1_764 ? N1 Cd2 O5 96.28(19) . . ? O4 Cd2 O5 86.77(17) 2_865 . ? O7 Cd2 O5 144.55(17) 1_655 . ? N6 Cd2 O5 88.1(2) 1_764 . ? N1 Cd2 O7 95.1(2) . 2_865 ? O4 Cd2 O7 52.84(17) 2_865 2_865 ? O7 Cd2 O7 75.29(19) 1_655 2_865 ? N6 Cd2 O7 90.8(2) 1_764 2_865 ? O5 Cd2 O7 139.37(16) . 2_865 ? N1 Cd2 O3 81.8(2) . . ? O4 Cd2 O3 140.39(17) 2_865 . ? O7 Cd2 O3 91.51(17) 1_655 . ? N6 Cd2 O3 89.2(2) 1_764 . ? O5 Cd2 O3 53.92(16) . . ? O7 Cd2 O3 166.71(16) 2_865 . ? C41 O1 Cd1 163.5(5) . 2_756 ? C41 O1 Cd1 89.3(4) . . ? Cd1 O1 Cd1 105.3(2) 2_756 . ? H1WA O1W H1WB 103(4) . . ? H2WA O2W H2WB 111.9 . . ? C31 O3 Cd2 90.1(4) . . ? C36 O4 Cd2 97.1(4) . 2_865 ? C31 O5 Cd2 94.8(4) . . ? C46 O6 Cd1 92.9(4) . 2_656 ? C36 O7 Cd2 164.4(5) . 1_455 ? C36 O7 Cd2 90.6(4) . 2_865 ? Cd2 O7 Cd2 104.70(19) 1_455 2_865 ? C41 O9 Cd1 95.4(5) . . ? C46 O10 Cd1 89.0(4) . 2_656 ? C1 N1 C11 119.1(6) . . ? C1 N1 Cd2 117.5(5) . . ? C11 N1 Cd2 123.4(5) . . ? C5 N2 C4 126.1(6) . . ? C5 N2 H2N 116.9 . . ? C4 N2 H2N 116.9 . . ? C9 N3 C10 117.8(6) . . ? C9 N3 Cd1 121.6(5) . . ? C10 N3 Cd1 120.6(5) . . ? C23 N4 C20 120.0(7) . . ? C23 N4 Cd1 116.7(5) . . ? C20 N4 Cd1 123.2(5) . . ? C25 N5 C21 125.0(6) . . ? C25 N5 H5N 117.5 . . ? C21 N5 H5N 117.5 . . ? C53 N6 C50 118.6(7) . . ? C53 N6 Cd2 120.9(5) . 1_346 ? C50 N6 Cd2 120.4(5) . 1_346 ? N1 C1 C2 122.9(7) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 118.8(7) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 118.3(7) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C3 C4 C11 119.9(6) . . ? C3 C4 N2 123.8(6) . . ? C11 C4 N2 116.2(6) . . ? O2 C5 N2 123.6(7) . . ? O2 C5 C7 120.0(6) . . ? N2 C5 C7 116.4(6) . . ? C9 C6 C7 118.7(7) . . ? C9 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C8 C7 C6 118.7(7) . . ? C8 C7 C5 125.9(6) . . ? C6 C7 C5 115.3(6) . . ? C7 C8 C10 118.8(7) . . ? C7 C8 H8 120.6 . . ? C10 C8 H8 120.6 . . ? N3 C9 C6 122.8(7) . . ? N3 C9 H9 118.6 . . ? C6 C9 H9 118.6 . . ? N3 C10 C8 123.3(8) . . ? N3 C10 H10 118.4 . . ? C8 C10 H10 118.4 . . ? N1 C11 C4 120.9(6) . . ? N1 C11 H11 119.6 . . ? C4 C11 H11 119.6 . . ? N4 C20 C21 122.6(7) . . ? N4 C20 H20 118.7 . . ? C21 C20 H20 118.7 . . ? C22 C21 C20 118.5(6) . . ? C22 C21 N5 123.8(6) . . ? C20 C21 N5 117.7(6) . . ? C21 C22 C24 118.4(7) . . ? C21 C22 H22 120.8 . . ? C24 C22 H22 120.8 . . ? N4 C23 C24 120.5(7) . . ? N4 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C22 C24 C23 120.1(7) . . ? C22 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? O8 C25 N5 124.4(7) . . ? O8 C25 C52 119.2(7) . . ? N5 C25 C52 116.5(7) . . ? O3 C31 O5 120.3(6) . . ? O3 C31 C32 120.7(6) . . ? O5 C31 C32 119.0(7) . . ? C31 C32 C33 109.6(6) . . ? C31 C32 H32A 109.7 . . ? C33 C32 H32A 109.7 . . ? C31 C32 H32B 109.7 . . ? C33 C32 H32B 109.7 . . ? H32A C32 H32B 108.2 . . ? C34 C33 C32 113.7(6) . . ? C34 C33 H33A 108.8 . . ? C32 C33 H33A 108.8 . . ? C34 C33 H33B 108.8 . . ? C32 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? C35 C34 C33 111.6(6) . . ? C35 C34 H34A 109.3 . . ? C33 C34 H34A 109.3 . . ? C35 C34 H34B 109.3 . . ? C33 C34 H34B 109.3 . . ? H34A C34 H34B 108.0 . . ? C36 C35 C34 112.5(6) . . ? C36 C35 H35A 109.1 . . ? C34 C35 H35A 109.1 . . ? C36 C35 H35B 109.1 . . ? C34 C35 H35B 109.1 . . ? H35A C35 H35B 107.8 . . ? O4 C36 O7 119.4(7) . . ? O4 C36 C35 120.0(7) . . ? O7 C36 C35 120.5(7) . . ? O1 C41 O9 121.4(7) . . ? O1 C41 C42 119.9(7) . . ? O9 C41 C42 118.7(7) . . ? O1 C41 Cd1 64.0(4) . . ? O9 C41 Cd1 57.5(4) . . ? C42 C41 Cd1 175.2(5) . . ? C41 C42 C43 113.5(6) . . ? C41 C42 H42A 108.9 . . ? C43 C42 H42A 108.9 . . ? C41 C42 H42B 108.9 . . ? C43 C42 H42B 108.9 . . ? H42A C42 H42B 107.7 . . ? C42 C43 C44 112.7(7) . . ? C42 C43 H43A 109.1 . . ? C44 C43 H43A 109.1 . . ? C42 C43 H43B 109.1 . . ? C44 C43 H43B 109.1 . . ? H43A C43 H43B 107.8 . . ? C45 C44 C43 111.0(6) . . ? C45 C44 H44A 109.4 . . ? C43 C44 H44A 109.4 . . ? C45 C44 H44B 109.4 . . ? C43 C44 H44B 109.4 . . ? H44A C44 H44B 108.0 . . ? C46 C45 C44 111.6(6) . . ? C46 C45 H45A 109.3 . . ? C44 C45 H45A 109.3 . . ? C46 C45 H45B 109.3 . . ? C44 C45 H45B 109.3 . . ? H45A C45 H45B 108.0 . . ? O6 C46 O10 122.6(7) . . ? O6 C46 C45 118.4(7) . . ? O10 C46 C45 119.0(6) . . ? O6 C46 Cd1 60.1(4) . 2_656 ? O10 C46 Cd1 63.6(4) . 2_656 ? C45 C46 Cd1 170.2(5) . 2_656 ? N6 C50 C51 122.9(7) . . ? N6 C50 H50 118.6 . . ? C51 C50 H50 118.6 . . ? C50 C51 C52 118.3(7) . . ? C50 C51 H51 120.8 . . ? C52 C51 H51 120.8 . . ? C54 C52 C51 118.9(6) . . ? C54 C52 C25 126.3(7) . . ? C51 C52 C25 114.8(7) . . ? N6 C53 C54 121.9(7) . . ? N6 C53 H53 119.0 . . ? C54 C53 H53 119.0 . . ? C52 C54 C53 119.2(7) . . ? C52 C54 H54 120.4 . . ? C53 C54 H54 120.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cd1 O1 C41 172.3(6) 2_756 . . . ? N4 Cd1 O1 C41 -101.9(5) . . . . ? O9 Cd1 O1 C41 -1.6(4) . . . . ? N3 Cd1 O1 C41 89.5(4) . . . . ? O6 Cd1 O1 C41 -3.1(6) 2_656 . . . ? O10 Cd1 O1 C41 -177.1(6) 2_656 . . . ? C46 Cd1 O1 C41 -21.8(11) 2_656 . . . ? O1 Cd1 O1 Cd1 0.0 2_756 . . 2_756 ? N4 Cd1 O1 Cd1 85.8(2) . . . 2_756 ? O9 Cd1 O1 Cd1 -173.8(3) . . . 2_756 ? N3 Cd1 O1 Cd1 -82.7(2) . . . 2_756 ? O6 Cd1 O1 Cd1 -175.41(19) 2_656 . . 2_756 ? O10 Cd1 O1 Cd1 10.7(8) 2_656 . . 2_756 ? C46 Cd1 O1 Cd1 165.9(8) 2_656 . . 2_756 ? C41 Cd1 O1 Cd1 -172.3(6) . . . 2_756 ? N1 Cd2 O3 C31 -98.8(4) . . . . ? O4 Cd2 O3 C31 -3.1(5) 2_865 . . . ? O7 Cd2 O3 C31 176.7(4) 1_655 . . . ? N6 Cd2 O3 C31 93.3(4) 1_764 . . . ? O5 Cd2 O3 C31 5.1(4) . . . . ? O7 Cd2 O3 C31 -176.5(7) 2_865 . . . ? N1 Cd2 O5 C31 70.0(4) . . . . ? O4 Cd2 O5 C31 169.6(4) 2_865 . . . ? O7 Cd2 O5 C31 -19.8(5) 1_655 . . . ? N6 Cd2 O5 C31 -95.6(4) 1_764 . . . ? O7 Cd2 O5 C31 175.4(4) 2_865 . . . ? O3 Cd2 O5 C31 -5.1(4) . . . . ? O1 Cd1 O9 C41 -6.0(6) 2_756 . . . ? N4 Cd1 O9 C41 87.6(5) . . . . ? N3 Cd1 O9 C41 -90.2(5) . . . . ? O6 Cd1 O9 C41 -179.4(5) 2_656 . . . ? O10 Cd1 O9 C41 179.5(4) 2_656 . . . ? O1 Cd1 O9 C41 1.6(4) . . . . ? C46 Cd1 O9 C41 177.0(4) 2_656 . . . ? O4 Cd2 N1 C1 177.8(5) 2_865 . . . ? O7 Cd2 N1 C1 50.0(5) 1_655 . . . ? N6 Cd2 N1 C1 11.7(11) 1_764 . . . ? O5 Cd2 N1 C1 -94.4(5) . . . . ? O7 Cd2 N1 C1 124.7(5) 2_865 . . . ? O3 Cd2 N1 C1 -42.3(5) . . . . ? O4 Cd2 N1 C11 -2.1(6) 2_865 . . . ? O7 Cd2 N1 C11 -129.9(6) 1_655 . . . ? N6 Cd2 N1 C11 -168.2(7) 1_764 . . . ? O5 Cd2 N1 C11 85.7(5) . . . . ? O7 Cd2 N1 C11 -55.2(6) 2_865 . . . ? O3 Cd2 N1 C11 137.8(6) . . . . ? O1 Cd1 N3 C9 -118.5(6) 2_756 . . . ? N4 Cd1 N3 C9 -160.9(9) . . . . ? O9 Cd1 N3 C9 9.6(6) . . . . ? O6 Cd1 N3 C9 97.7(6) 2_656 . . . ? O10 Cd1 N3 C9 151.8(6) 2_656 . . . ? O1 Cd1 N3 C9 -44.3(6) . . . . ? C46 Cd1 N3 C9 124.5(6) 2_656 . . . ? C41 Cd1 N3 C9 -17.5(6) . . . . ? O1 Cd1 N3 C10 62.0(6) 2_756 . . . ? N4 Cd1 N3 C10 19.6(13) . . . . ? O9 Cd1 N3 C10 -169.9(6) . . . . ? O6 Cd1 N3 C10 -81.8(6) 2_656 . . . ? O10 Cd1 N3 C10 -27.7(6) 2_656 . . . ? O1 Cd1 N3 C10 136.2(6) . . . . ? C46 Cd1 N3 C10 -55.0(6) 2_656 . . . ? C41 Cd1 N3 C10 163.0(6) . . . . ? O1 Cd1 N4 C23 -56.4(6) 2_756 . . . ? O9 Cd1 N4 C23 175.4(5) . . . . ? N3 Cd1 N4 C23 -14.2(13) . . . . ? O6 Cd1 N4 C23 86.8(6) 2_656 . . . ? O10 Cd1 N4 C23 33.4(5) 2_656 . . . ? O1 Cd1 N4 C23 -130.9(6) . . . . ? C46 Cd1 N4 C23 61.0(6) 2_656 . . . ? C41 Cd1 N4 C23 -157.3(5) . . . . ? O1 Cd1 N4 C20 125.9(6) 2_756 . . . ? O9 Cd1 N4 C20 -2.2(6) . . . . ? N3 Cd1 N4 C20 168.1(7) . . . . ? O6 Cd1 N4 C20 -90.9(6) 2_656 . . . ? O10 Cd1 N4 C20 -144.2(6) 2_656 . . . ? O1 Cd1 N4 C20 51.5(6) . . . . ? C46 Cd1 N4 C20 -116.7(6) 2_656 . . . ? C41 Cd1 N4 C20 25.1(6) . . . . ? C11 N1 C1 C2 0.8(11) . . . . ? Cd2 N1 C1 C2 -179.1(6) . . . . ? N1 C1 C2 C3 -1.0(12) . . . . ? C1 C2 C3 C4 0.8(12) . . . . ? C2 C3 C4 C11 -0.6(11) . . . . ? C2 C3 C4 N2 176.5(7) . . . . ? C5 N2 C4 C3 9.2(12) . . . . ? C5 N2 C4 C11 -173.7(7) . . . . ? C4 N2 C5 O2 7.2(12) . . . . ? C4 N2 C5 C7 -172.4(7) . . . . ? C9 C6 C7 C8 -1.1(11) . . . . ? C9 C6 C7 C5 -178.7(7) . . . . ? O2 C5 C7 C8 -175.5(7) . . . . ? N2 C5 C7 C8 4.1(11) . . . . ? O2 C5 C7 C6 1.9(10) . . . . ? N2 C5 C7 C6 -178.5(7) . . . . ? C6 C7 C8 C10 1.0(11) . . . . ? C5 C7 C8 C10 178.3(7) . . . . ? C10 N3 C9 C6 0.0(11) . . . . ? Cd1 N3 C9 C6 -179.5(6) . . . . ? C7 C6 C9 N3 0.6(12) . . . . ? C9 N3 C10 C8 -0.2(12) . . . . ? Cd1 N3 C10 C8 179.3(6) . . . . ? C7 C8 C10 N3 -0.3(12) . . . . ? C1 N1 C11 C4 -0.5(10) . . . . ? Cd2 N1 C11 C4 179.4(5) . . . . ? C3 C4 C11 N1 0.4(11) . . . . ? N2 C4 C11 N1 -176.9(7) . . . . ? C23 N4 C20 C21 1.2(11) . . . . ? Cd1 N4 C20 C21 178.8(5) . . . . ? N4 C20 C21 C22 -1.1(10) . . . . ? N4 C20 C21 N5 178.7(7) . . . . ? C25 N5 C21 C22 -2.1(12) . . . . ? C25 N5 C21 C20 178.1(7) . . . . ? C20 C21 C22 C24 0.2(11) . . . . ? N5 C21 C22 C24 -179.5(7) . . . . ? C20 N4 C23 C24 -0.5(11) . . . . ? Cd1 N4 C23 C24 -178.3(6) . . . . ? C21 C22 C24 C23 0.4(12) . . . . ? N4 C23 C24 C22 -0.3(12) . . . . ? C21 N5 C25 O8 -6.4(13) . . . . ? C21 N5 C25 C52 173.4(7) . . . . ? Cd2 O3 C31 O5 -9.0(7) . . . . ? Cd2 O3 C31 C32 169.3(6) . . . . ? Cd2 O5 C31 O3 9.4(7) . . . . ? Cd2 O5 C31 C32 -168.8(6) . . . . ? O3 C31 C32 C33 -127.2(7) . . . . ? O5 C31 C32 C33 51.1(9) . . . . ? C31 C32 C33 C34 72.8(8) . . . . ? C32 C33 C34 C35 -173.6(6) . . . . ? C33 C34 C35 C36 72.6(8) . . . . ? Cd2 O4 C36 O7 -2.2(7) 2_865 . . . ? Cd2 O4 C36 C35 174.6(6) 2_865 . . . ? Cd2 O7 C36 O4 171.4(14) 1_455 . . . ? Cd2 O7 C36 O4 2.0(7) 2_865 . . . ? Cd2 O7 C36 C35 -5(2) 1_455 . . . ? Cd2 O7 C36 C35 -174.7(6) 2_865 . . . ? C34 C35 C36 O4 52.0(10) . . . . ? C34 C35 C36 O7 -131.3(7) . . . . ? Cd1 O1 C41 O9 155.6(14) 2_756 . . . ? Cd1 O1 C41 O9 2.8(7) . . . . ? Cd1 O1 C41 C42 -24(2) 2_756 . . . ? Cd1 O1 C41 C42 -176.9(6) . . . . ? Cd1 O1 C41 Cd1 152.8(18) 2_756 . . . ? Cd1 O9 C41 O1 -2.9(8) . . . . ? Cd1 O9 C41 C42 176.7(6) . . . . ? O1 Cd1 C41 O1 -7.6(5) 2_756 . . . ? N4 Cd1 C41 O1 80.6(5) . . . . ? O9 Cd1 C41 O1 177.2(7) . . . . ? N3 Cd1 C41 O1 -91.8(4) . . . . ? O6 Cd1 C41 O1 177.9(4) 2_656 . . . ? O10 Cd1 C41 O1 175.6(8) 2_656 . . . ? C46 Cd1 C41 O1 172.8(4) 2_656 . . . ? O1 Cd1 C41 O9 175.2(5) 2_756 . . . ? N4 Cd1 C41 O9 -96.6(5) . . . . ? N3 Cd1 C41 O9 91.0(5) . . . . ? O6 Cd1 C41 O9 0.6(5) 2_656 . . . ? O10 Cd1 C41 O9 -1.6(13) 2_656 . . . ? O1 Cd1 C41 O9 -177.2(7) . . . . ? C46 Cd1 C41 O9 -4.4(6) 2_656 . . . ? O1 Cd1 C41 C42 138(6) 2_756 . . . ? N4 Cd1 C41 C42 -134(6) . . . . ? O9 Cd1 C41 C42 -37(6) . . . . ? N3 Cd1 C41 C42 54(6) . . . . ? O6 Cd1 C41 C42 -37(6) 2_656 . . . ? O10 Cd1 C41 C42 -39(7) 2_656 . . . ? O1 Cd1 C41 C42 145(6) . . . . ? C46 Cd1 C41 C42 -42(6) 2_656 . . . ? O1 C41 C42 C43 -130.1(7) . . . . ? O9 C41 C42 C43 50.2(10) . . . . ? Cd1 C41 C42 C43 86(6) . . . . ? C41 C42 C43 C44 81.7(8) . . . . ? C42 C43 C44 C45 -172.4(6) . . . . ? C43 C44 C45 C46 71.4(8) . . . . ? Cd1 O6 C46 O10 11.9(7) 2_656 . . . ? Cd1 O6 C46 C45 -168.9(6) 2_656 . . . ? Cd1 O10 C46 O6 -11.5(7) 2_656 . . . ? Cd1 O10 C46 C45 169.3(6) 2_656 . . . ? C44 C45 C46 O6 42.5(9) . . . . ? C44 C45 C46 O10 -138.3(7) . . . . ? C44 C45 C46 Cd1 -36(3) . . . 2_656 ? C53 N6 C50 C51 2.5(11) . . . . ? Cd2 N6 C50 C51 179.2(6) 1_346 . . . ? N6 C50 C51 C52 -1.5(11) . . . . ? C50 C51 C52 C54 0.6(11) . . . . ? C50 C51 C52 C25 -180.0(7) . . . . ? O8 C25 C52 C54 173.2(8) . . . . ? N5 C25 C52 C54 -6.7(12) . . . . ? O8 C25 C52 C51 -6.2(12) . . . . ? N5 C25 C52 C51 174.0(7) . . . . ? C50 N6 C53 C54 -2.6(11) . . . . ? Cd2 N6 C53 C54 -179.4(5) 1_346 . . . ? C51 C52 C54 C53 -0.8(11) . . . . ? C25 C52 C54 C53 179.9(7) . . . . ? N6 C53 C54 C52 1.8(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N O5 0.88 2.09 2.892(8) 151.4 2_865 N5 H5N O6 0.88 2.06 2.867(8) 151.3 . O1W H1WA O2W 0.86(2) 2.00(4) 2.815(8) 159(8) 2_875 O1W H1WB O3 0.87(2) 1.97(3) 2.820(8) 168(9) . O2W H2WA O2 0.85 2.08 2.933(8) 179.5 . O2W H2WB O10 0.86(2) 1.99(5) 2.766(8) 150(9) 2_666 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.630 _refine_diff_density_min -1.113 _refine_diff_density_rms 0.175 data_p1b _database_code_depnum_ccdc_archive 'CCDC 898728' #TrackingRef '0cdadipate4pnafinal.cif' _audit_update_record ; 2012-07-16 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H34 Cd N6 O10' _chemical_formula_weight 727.01 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6991(7) _cell_length_b 9.5878(12) _cell_length_c 14.1723(18) _cell_angle_alpha 74.2130(10) _cell_angle_beta 89.7140(10) _cell_angle_gamma 84.8810(10) _cell_volume 742.07(16) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8440 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 25.36 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.804 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8603 _exptl_absorpt_correction_T_max 0.9189 _exptl_absorpt_process_details SADABS _exptl_special_details ? _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11888 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.39 _reflns_number_total 2716 _reflns_number_gt 2563 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0168P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2716 _refine_ls_number_parameters 220 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0473 _refine_ls_wR_factor_gt 0.0467 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 Cd1 Cd 0.0000 0.0000 0.0000 0.01732(8) Uani 1 2 d S . . O1 O 0.6461(2) -0.54906(15) 0.41473(10) 0.0243(3) Uani 1 1 d . . . O1W O 0.0164(3) 0.21118(17) 0.34297(11) 0.0279(4) Uani 1 1 d D . . H1WA H -0.012(4) 0.229(2) 0.2833(11) 0.033 Uiso 1 1 d D . . H1WB H 0.108(3) 0.136(2) 0.3612(15) 0.033 Uiso 1 1 d D . . O2 O -0.0317(2) 0.24847(16) 0.13604(10) 0.0291(4) Uani 1 1 d . . . O3 O 0.2326(2) 0.15720(14) 0.04800(9) 0.0203(3) Uani 1 1 d . . . O4 O 0.3048(2) -0.06169(16) -0.09248(11) 0.0237(3) Uani 1 1 d D . . H4A H 0.236(3) -0.125(2) -0.1104(15) 0.028 Uiso 1 1 d D . . H4B H 0.437(3) -0.099(2) -0.0713(14) 0.028 Uiso 1 1 d D . . N1 N 0.1073(3) -0.18842(18) 0.13692(11) 0.0185(4) Uani 1 1 d . . . N2 N 0.2614(3) -0.55821(19) 0.37166(12) 0.0222(4) Uani 1 1 d D . . H2N H 0.160(3) -0.620(2) 0.3747(15) 0.027 Uiso 1 1 d D . . N3 N 0.6324(3) -0.96856(19) 0.60562(12) 0.0254(4) Uani 1 1 d . . . C1 C 0.6319(4) -0.8460(2) 0.53224(14) 0.0218(5) Uani 1 1 d . . . H1 H 0.7708 -0.8286 0.4952 0.026 Uiso 1 1 calc R . . C2 C 0.4344(4) -0.9888(2) 0.65653(15) 0.0274(5) Uani 1 1 d . . . H2 H 0.4315 -1.0749 0.7090 0.033 Uiso 1 1 calc R . . C3 C 0.2349(4) -0.8934(2) 0.63804(15) 0.0260(5) Uani 1 1 d . . . H3 H 0.0990 -0.9130 0.6768 0.031 Uiso 1 1 calc R . . C4 C 0.3097(3) -0.2065(2) 0.18792(14) 0.0206(5) Uani 1 1 d . . . H4 H 0.4164 -0.1336 0.1688 0.025 Uiso 1 1 calc R . . C5 C 0.4400(3) -0.7439(2) 0.50774(13) 0.0187(5) Uani 1 1 d . . . C6 C 0.0060(3) -0.4124(2) 0.24391(13) 0.0200(5) Uani 1 1 d . . . H6 H -0.1062 -0.4820 0.2623 0.024 Uiso 1 1 calc R . . C7 C 0.4632(4) -0.6078(2) 0.42709(13) 0.0196(5) Uani 1 1 d . . . C8 C 0.2365(4) -0.7682(2) 0.56174(14) 0.0226(5) Uani 1 1 d . . . H8 H 0.1012 -0.7002 0.5465 0.027 Uiso 1 1 calc R . . C9 C 0.2198(3) -0.4326(2) 0.29520(13) 0.0187(5) Uani 1 1 d . . . C10 C 0.3727(4) -0.3245(2) 0.26646(14) 0.0210(5) Uani 1 1 d . . . H10 H 0.5184 -0.3318 0.3005 0.025 Uiso 1 1 calc R . . C11 C -0.0406(3) -0.2916(2) 0.16704(14) 0.0198(5) Uani 1 1 d . . . H11 H -0.1870 -0.2801 0.1328 0.024 Uiso 1 1 calc R . . C12 C 0.1605(3) 0.2496(2) 0.09317(14) 0.0200(5) Uani 1 1 d . . . C13 C 0.3194(4) 0.3672(2) 0.09522(15) 0.0253(5) Uani 1 1 d . . . H13A H 0.4502 0.3241 0.1428 0.030 Uiso 1 1 calc R . . H13B H 0.2282 0.4429 0.1194 0.030 Uiso 1 1 calc R . . C14 C 0.4239(3) 0.4401(2) -0.00308(14) 0.0230(5) Uani 1 1 d . . . H14A H 0.5204 0.3657 -0.0267 0.028 Uiso 1 1 calc R . . H14B H 0.2943 0.4820 -0.0515 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.01600(12) 0.01615(13) 0.01804(12) -0.00138(9) 0.00077(8) -0.00234(9) O1 0.0209(8) 0.0225(9) 0.0261(8) 0.0000(6) 0.0016(6) -0.0038(7) O1W 0.0318(9) 0.0230(9) 0.0275(8) -0.0050(7) -0.0004(7) -0.0008(7) O2 0.0211(8) 0.0377(10) 0.0332(9) -0.0161(7) 0.0065(7) -0.0077(7) O3 0.0186(8) 0.0168(8) 0.0266(8) -0.0076(6) 0.0002(6) -0.0024(6) O4 0.0164(8) 0.0252(9) 0.0298(8) -0.0079(7) 0.0027(7) -0.0023(7) N1 0.0164(9) 0.0176(10) 0.0195(9) -0.0021(7) 0.0005(7) -0.0006(7) N2 0.0231(10) 0.0173(10) 0.0223(9) 0.0031(8) -0.0037(8) -0.0073(8) N3 0.0288(10) 0.0218(11) 0.0224(9) -0.0010(8) -0.0039(8) -0.0006(8) C1 0.0225(12) 0.0231(13) 0.0189(11) -0.0035(9) -0.0017(9) -0.0031(10) C2 0.0376(14) 0.0198(12) 0.0211(11) 0.0025(9) -0.0042(10) -0.0073(11) C3 0.0268(12) 0.0283(13) 0.0221(11) -0.0038(10) 0.0034(9) -0.0085(10) C4 0.0208(11) 0.0183(12) 0.0219(11) -0.0030(9) 0.0013(9) -0.0055(9) C5 0.0228(11) 0.0167(11) 0.0160(10) -0.0026(8) -0.0021(8) -0.0043(9) C6 0.0175(11) 0.0198(12) 0.0207(11) -0.0011(9) 0.0031(9) -0.0049(9) C7 0.0232(12) 0.0193(12) 0.0168(10) -0.0056(9) 0.0010(9) -0.0019(10) C8 0.0213(11) 0.0234(12) 0.0237(11) -0.0076(9) -0.0016(9) -0.0022(10) C9 0.0223(11) 0.0173(11) 0.0157(10) -0.0034(8) 0.0013(8) -0.0008(9) C10 0.0193(11) 0.0209(12) 0.0214(11) -0.0028(9) -0.0033(9) -0.0038(9) C11 0.0165(11) 0.0217(12) 0.0203(11) -0.0046(9) -0.0002(8) -0.0014(9) C12 0.0210(12) 0.0191(12) 0.0177(10) -0.0016(9) -0.0034(9) -0.0010(9) C13 0.0251(12) 0.0246(13) 0.0305(12) -0.0131(10) 0.0041(10) -0.0083(10) C14 0.0236(12) 0.0180(13) 0.0280(12) -0.0071(10) -0.0015(9) -0.0027(9) _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 Cd1 O4 2.3022(14) 2 ? Cd1 O4 2.3022(14) . ? Cd1 N1 2.3045(15) 2 ? Cd1 N1 2.3045(15) . ? Cd1 O3 2.3269(13) 2 ? Cd1 O3 2.3269(13) . ? O1 C7 1.218(2) . ? O1W H1WA 0.830(15) . ? O1W H1WB 0.834(15) . ? O2 C12 1.249(2) . ? O3 C12 1.267(2) . ? O4 H4A 0.845(15) . ? O4 H4B 0.827(15) . ? N1 C11 1.337(2) . ? N1 C4 1.337(2) . ? N2 C7 1.369(2) . ? N2 C9 1.386(2) . ? N2 H2N 0.859(15) . ? N3 C2 1.337(3) . ? N3 C1 1.340(2) . ? C1 C5 1.380(3) . ? C1 H1 0.9500 . ? C2 C3 1.373(3) . ? C2 H2 0.9500 . ? C3 C8 1.380(3) . ? C3 H3 0.9500 . ? C4 C10 1.376(3) . ? C4 H4 0.9500 . ? C5 C8 1.388(3) . ? C5 C7 1.498(3) . ? C6 C11 1.364(3) . ? C6 C9 1.393(3) . ? C6 H6 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.389(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.514(3) . ? C13 C14 1.523(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C14 1.521(4) 2_665 ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 O4 Cd1 O4 180.0 2 . ? O4 Cd1 N1 94.10(5) 2 2 ? O4 Cd1 N1 85.90(5) . 2 ? O4 Cd1 N1 85.89(5) 2 . ? O4 Cd1 N1 94.11(5) . . ? N1 Cd1 N1 180.0 2 . ? O4 Cd1 O3 89.64(5) 2 2 ? O4 Cd1 O3 90.36(5) . 2 ? N1 Cd1 O3 92.64(5) 2 2 ? N1 Cd1 O3 87.36(5) . 2 ? O4 Cd1 O3 90.36(5) 2 . ? O4 Cd1 O3 89.64(5) . . ? N1 Cd1 O3 87.36(5) 2 . ? N1 Cd1 O3 92.64(5) . . ? O3 Cd1 O3 180.0 2 . ? H1WA O1W H1WB 109(2) . . ? C12 O3 Cd1 125.35(12) . . ? Cd1 O4 H4A 95.7(14) . . ? Cd1 O4 H4B 125.7(15) . . ? H4A O4 H4B 108(2) . . ? C11 N1 C4 116.46(16) . . ? C11 N1 Cd1 117.93(12) . . ? C4 N1 Cd1 125.58(13) . . ? C7 N2 C9 128.14(17) . . ? C7 N2 H2N 116.3(14) . . ? C9 N2 H2N 113.9(14) . . ? C2 N3 C1 116.59(18) . . ? N3 C1 C5 123.40(19) . . ? N3 C1 H1 118.3 . . ? C5 C1 H1 118.3 . . ? N3 C2 C3 124.31(19) . . ? N3 C2 H2 117.8 . . ? C3 C2 H2 117.8 . . ? C2 C3 C8 118.39(19) . . ? C2 C3 H3 120.8 . . ? C8 C3 H3 120.8 . . ? N1 C4 C10 123.88(19) . . ? N1 C4 H4 118.1 . . ? C10 C4 H4 118.1 . . ? C1 C5 C8 118.66(18) . . ? C1 C5 C7 118.71(18) . . ? C8 C5 C7 122.56(18) . . ? C11 C6 C9 119.32(19) . . ? C11 C6 H6 120.3 . . ? C9 C6 H6 120.3 . . ? O1 C7 N2 124.88(18) . . ? O1 C7 C5 121.63(18) . . ? N2 C7 C5 113.48(17) . . ? C3 C8 C5 118.64(19) . . ? C3 C8 H8 120.7 . . ? C5 C8 H8 120.7 . . ? N2 C9 C10 125.30(18) . . ? N2 C9 C6 117.34(18) . . ? C10 C9 C6 117.36(18) . . ? C4 C10 C9 118.96(18) . . ? C4 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? N1 C11 C6 123.98(18) . . ? N1 C11 H11 118.0 . . ? C6 C11 H11 118.0 . . ? O2 C12 O3 123.89(19) . . ? O2 C12 C13 118.70(18) . . ? O3 C12 C13 117.40(17) . . ? C12 C13 C14 115.00(17) . . ? C12 C13 H13A 108.5 . . ? C14 C13 H13A 108.5 . . ? C12 C13 H13B 108.5 . . ? C14 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C14 C14 C13 112.5(2) 2_665 . ? C14 C14 H14A 109.1 2_665 . ? C13 C14 H14A 109.1 . . ? C14 C14 H14B 109.1 2_665 . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Cd1 O3 C12 -10.52(15) 2 . . . ? O4 Cd1 O3 C12 169.48(15) . . . . ? N1 Cd1 O3 C12 83.57(15) 2 . . . ? N1 Cd1 O3 C12 -96.43(15) . . . . ? O3 Cd1 O3 C12 -3(36) 2 . . . ? O4 Cd1 N1 C11 64.90(14) 2 . . . ? O4 Cd1 N1 C11 -115.10(14) . . . . ? N1 Cd1 N1 C11 81(11) 2 . . . ? O3 Cd1 N1 C11 -24.93(14) 2 . . . ? O3 Cd1 N1 C11 155.07(14) . . . . ? O4 Cd1 N1 C4 -117.26(16) 2 . . . ? O4 Cd1 N1 C4 62.74(16) . . . . ? N1 Cd1 N1 C4 -101(11) 2 . . . ? O3 Cd1 N1 C4 152.91(16) 2 . . . ? O3 Cd1 N1 C4 -27.09(16) . . . . ? C2 N3 C1 C5 -0.5(3) . . . . ? C1 N3 C2 C3 0.2(3) . . . . ? N3 C2 C3 C8 0.3(3) . . . . ? C11 N1 C4 C10 1.3(3) . . . . ? Cd1 N1 C4 C10 -176.59(15) . . . . ? N3 C1 C5 C8 0.2(3) . . . . ? N3 C1 C5 C7 177.36(18) . . . . ? C9 N2 C7 O1 -2.8(4) . . . . ? C9 N2 C7 C5 176.58(19) . . . . ? C1 C5 C7 O1 -36.0(3) . . . . ? C8 C5 C7 O1 141.1(2) . . . . ? C1 C5 C7 N2 144.68(19) . . . . ? C8 C5 C7 N2 -38.3(3) . . . . ? C2 C3 C8 C5 -0.6(3) . . . . ? C1 C5 C8 C3 0.3(3) . . . . ? C7 C5 C8 C3 -176.72(19) . . . . ? C7 N2 C9 C10 -6.7(3) . . . . ? C7 N2 C9 C6 174.23(19) . . . . ? C11 C6 C9 N2 -178.87(18) . . . . ? C11 C6 C9 C10 2.0(3) . . . . ? N1 C4 C10 C9 0.4(3) . . . . ? N2 C9 C10 C4 178.93(19) . . . . ? C6 C9 C10 C4 -2.0(3) . . . . ? C4 N1 C11 C6 -1.3(3) . . . . ? Cd1 N1 C11 C6 176.73(15) . . . . ? C9 C6 C11 N1 -0.3(3) . . . . ? Cd1 O3 C12 O2 15.7(3) . . . . ? Cd1 O3 C12 C13 -164.67(12) . . . . ? O2 C12 C13 C14 -134.48(19) . . . . ? O3 C12 C13 C14 45.9(3) . . . . ? C12 C13 C14 C14 178.4(2) . . . 2_665 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O2 0.830(15) 2.047(16) 2.868(2) 170(2) . O1W H1WB N3 0.834(15) 2.038(15) 2.865(2) 172(2) 2_646 O4 H4A O2 0.845(15) 1.836(15) 2.668(2) 168(2) 2 O4 H4B O3 0.827(15) 1.918(15) 2.7312(19) 168(2) 2_655 N2 H2N O1W 0.859(15) 2.029(17) 2.837(2) 156(2) 1_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.381 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.059