# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_a1 _database_code_depnum_ccdc_archive 'CCDC 885608' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Cd N3 O4' _chemical_formula_weight 449.73 _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' Cd Cd -0.8075 1.2024 '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' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I41/a _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+3/4, x+1/4, z+1/4' '-x+1/2, -y, z+1/2' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-y+5/4, x+3/4, z+3/4' '-x+1, -y+1/2, z+1' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'y-3/4, -x-1/4, -z-1/4' 'x-1/2, y, -z-1/2' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' 'x, y+1/2, -z' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 22.425(5) _cell_length_b 22.425(5) _cell_length_c 15.091(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7589(6) _cell_formula_units_Z 16 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2508 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 19.63 _exptl_crystal_description cubic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3584 _exptl_absorpt_coefficient_mu 1.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8072 _exptl_absorpt_correction_T_max 0.8525 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 18433 _diffrn_reflns_av_R_equivalents 0.1354 _diffrn_reflns_av_sigmaI/netI 0.1106 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3429 _reflns_number_gt 1519 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. We have described as 114 restrains: DELU 0.01 C6 > C18. SIMU 0.01 C6 > C18. ; _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^)+(0.1169P)^2^+55.9605P] 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 3429 _refine_ls_number_parameters 225 _refine_ls_number_restraints 114 _refine_ls_R_factor_all 0.1800 _refine_ls_R_factor_gt 0.0780 _refine_ls_wR_factor_ref 0.2749 _refine_ls_wR_factor_gt 0.1814 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _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 0.24210(5) 0.17226(4) 0.80047(7) 0.0731(5) Uani 1 1 d . . . N1 N 0.1887(5) 0.1193(5) 0.7017(7) 0.071(3) Uani 1 1 d . . . N2 N 0.1352(4) 0.0588(5) 0.6152(7) 0.069(3) Uani 1 1 d . . . O1 O 0.2211(4) 0.2347(4) 0.6738(7) 0.086(3) Uani 1 1 d . . . O2 O 0.1931(5) 0.2324(5) 0.5350(7) 0.102(3) Uani 1 1 d . . . O3 O 0.1366(6) 0.1652(5) 0.4346(6) 0.103(4) Uani 1 1 d . . . H3 H 0.1513 0.1899 0.4681 0.124 Uiso 1 1 calc R . . O4 O 0.0936(5) 0.0785(5) 0.4460(6) 0.091(3) Uani 1 1 d . . . C1 C 0.2002(6) 0.2102(6) 0.6095(11) 0.073(4) Uani 1 1 d . . . C2 C 0.1784(6) 0.1477(6) 0.6228(9) 0.070(4) Uani 1 1 d . . . C3 C 0.1452(6) 0.1110(6) 0.5698(9) 0.069(3) Uani 1 1 d . . . C4 C 0.1236(8) 0.1170(7) 0.4790(12) 0.092(5) Uani 1 1 d . . . C5 C 0.1624(6) 0.0663(6) 0.6939(9) 0.075(4) Uani 1 1 d . . . C6 C 0.1639(8) 0.0191(8) 0.7640(10) 0.097(3) Uani 1 1 d U . . C7 C 0.2188(8) -0.0037(8) 0.7915(10) 0.100(3) Uani 1 1 d U . . H7A H 0.2543 0.0113 0.7689 0.120 Uiso 1 1 calc R . . C8 C 0.2189(10) -0.0479(8) 0.8514(11) 0.112(4) Uani 1 1 d U . . H8A H 0.2554 -0.0640 0.8685 0.135 Uiso 1 1 calc R . . C9 C 0.1688(10) -0.0703(9) 0.8880(13) 0.121(4) Uani 1 1 d U . . C10 C 0.1161(10) -0.0471(9) 0.8649(14) 0.125(4) Uani 1 1 d U . . C11 C 0.1095(9) -0.0050(8) 0.7986(12) 0.114(4) Uani 1 1 d U . . H11 H 0.0723 0.0068 0.7779 0.137 Uiso 1 1 calc R . . C12 C 0.1711(11) -0.1237(10) 0.9537(14) 0.149(7) Uani 1 1 d U . . H12A H 0.1315 -0.1329 0.9735 0.179 Uiso 1 1 calc R . . H12B H 0.1954 -0.1133 1.0037 0.179 Uiso 1 1 calc R . . H12C H 0.1879 -0.1578 0.9244 0.179 Uiso 1 1 calc R . . C13 C 0.0555(10) -0.0683(11) 0.8994(17) 0.159(7) Uani 1 1 d U . . H13A H 0.0511 -0.1102 0.8878 0.190 Uiso 1 1 calc R . . H13B H 0.0243 -0.0467 0.8700 0.190 Uiso 1 1 calc R . . H13C H 0.0532 -0.0613 0.9621 0.190 Uiso 1 1 calc R . . N3 N 0.1575(6) 0.1811(9) 0.8865(13) 0.192(6) Uani 1 1 d GU . . C14 C 0.1340(7) 0.2362(7) 0.9102(14) 0.203(6) Uani 1 1 d GU . . H14A H 0.1542 0.2711 0.8954 0.243 Uiso 1 1 calc R . . C15 C 0.0803(8) 0.2393(7) 0.9561(15) 0.208(6) Uani 1 1 d GU . . H15A H 0.0646 0.2761 0.9720 0.250 Uiso 1 1 calc R . . C16 C 0.0502(6) 0.1872(10) 0.9783(14) 0.209(6) Uani 1 1 d GU . . H16A H 0.0143 0.1892 1.0090 0.251 Uiso 1 1 calc R . . C17 C 0.0737(8) 0.1321(8) 0.9546(14) 0.206(6) Uani 1 1 d GU . . H17A H 0.0535 0.0973 0.9695 0.247 Uiso 1 1 calc R . . C18 C 0.1274(8) 0.1291(7) 0.9087(14) 0.199(6) Uani 1 1 d GU . . H18A H 0.1431 0.0922 0.8929 0.239 Uiso 1 1 calc R . . _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 0.0770(8) 0.0673(7) 0.0750(7) 0.0013(5) -0.0172(5) -0.0012(5) N1 0.077(7) 0.063(7) 0.074(7) 0.000(6) -0.011(6) -0.014(6) N2 0.055(6) 0.074(7) 0.078(7) -0.008(6) -0.010(5) -0.011(5) O1 0.099(7) 0.056(5) 0.105(7) 0.003(5) -0.041(6) -0.002(5) O2 0.125(9) 0.094(8) 0.088(7) 0.027(6) -0.021(6) -0.037(7) O3 0.157(11) 0.090(8) 0.062(6) 0.002(5) -0.027(6) -0.035(7) O4 0.118(8) 0.092(7) 0.063(6) 0.007(5) -0.010(5) -0.022(7) C1 0.068(9) 0.070(9) 0.081(10) -0.005(8) -0.017(8) -0.008(7) C2 0.066(8) 0.079(9) 0.065(8) 0.004(7) -0.013(7) -0.020(7) C3 0.071(8) 0.069(9) 0.069(9) 0.007(7) -0.009(7) 0.000(7) C4 0.100(12) 0.066(10) 0.110(13) -0.004(9) -0.012(10) -0.007(9) C5 0.072(9) 0.073(9) 0.079(9) 0.008(7) -0.004(8) -0.008(7) C6 0.105(8) 0.103(8) 0.081(7) 0.009(6) -0.020(6) -0.012(6) C7 0.113(7) 0.108(8) 0.080(7) 0.013(6) -0.017(6) -0.004(7) C8 0.129(8) 0.116(8) 0.092(8) 0.019(6) -0.018(7) 0.001(7) C9 0.140(8) 0.122(8) 0.101(8) 0.030(6) -0.018(7) -0.012(7) C10 0.132(8) 0.124(8) 0.118(8) 0.031(6) -0.008(7) -0.015(7) C11 0.117(7) 0.118(8) 0.107(8) 0.021(6) -0.016(7) -0.013(7) C12 0.176(15) 0.147(13) 0.125(13) 0.055(10) -0.025(11) -0.013(11) C13 0.150(10) 0.155(14) 0.171(15) 0.057(12) 0.009(12) -0.017(12) N3 0.111(9) 0.193(13) 0.273(15) -0.085(13) 0.035(10) -0.019(8) C14 0.124(10) 0.195(13) 0.288(15) -0.075(13) 0.043(10) -0.015(9) C15 0.130(10) 0.198(13) 0.296(15) -0.072(13) 0.053(11) -0.011(9) C16 0.131(10) 0.199(14) 0.297(15) -0.070(13) 0.055(11) -0.009(9) C17 0.130(10) 0.196(13) 0.290(15) -0.075(13) 0.050(10) -0.013(9) C18 0.123(10) 0.194(13) 0.282(15) -0.082(13) 0.042(10) -0.018(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. ; _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 N2 2.203(10) 8_444 ? Cd1 N1 2.250(10) . ? Cd1 O1 2.277(9) 13_556 ? Cd1 N3 2.308(12) . ? Cd1 O1 2.417(9) . ? Cd1 O4 2.524(10) 8_444 ? N1 C5 1.332(16) . ? N1 C2 1.371(16) . ? N2 C5 1.346(16) . ? N2 C3 1.374(16) . ? N2 Cd1 2.203(10) 6_444 ? O1 C1 1.209(15) . ? O1 Cd1 2.277(9) 13_556 ? O2 C1 1.239(16) . ? O3 C4 1.305(18) . ? O3 H3 0.8200 . ? O4 C4 1.201(17) . ? O4 Cd1 2.524(10) 6_444 ? C1 C2 1.497(18) . ? C2 C3 1.369(17) . ? C3 C4 1.46(2) . ? C5 C6 1.50(2) . ? C6 C7 1.40(2) . ? C6 C11 1.43(2) . ? C7 C8 1.34(2) . ? C7 H7A 0.9300 . ? C8 C9 1.35(3) . ? C8 H8A 0.9300 . ? C9 C10 1.34(3) . ? C9 C12 1.56(3) . ? C10 C11 1.38(2) . ? C10 C13 1.53(3) . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? N3 C14 1.3900 . ? N3 C18 1.3900 . ? C14 C15 1.3900 . ? C14 H14A 0.9300 . ? C15 C16 1.3900 . ? C15 H15A 0.9300 . ? C16 C17 1.3900 . ? C16 H16A 0.9300 . ? C17 C18 1.3900 . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? _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 N2 Cd1 N1 110.3(4) 8_444 . ? N2 Cd1 O1 102.3(4) 8_444 13_556 ? N1 Cd1 O1 142.1(4) . 13_556 ? N2 Cd1 N3 111.1(6) 8_444 . ? N1 Cd1 N3 88.9(5) . . ? O1 Cd1 N3 97.1(5) 13_556 . ? N2 Cd1 O1 145.3(4) 8_444 . ? N1 Cd1 O1 71.2(4) . . ? O1 Cd1 O1 71.0(4) 13_556 . ? N3 Cd1 O1 103.6(6) . . ? N2 Cd1 O4 70.9(4) 8_444 8_444 ? N1 Cd1 O4 85.4(4) . 8_444 ? O1 Cd1 O4 87.6(4) 13_556 8_444 ? N3 Cd1 O4 174.3(5) . 8_444 ? O1 Cd1 O4 74.8(4) . 8_444 ? C5 N1 C2 105.2(11) . . ? C5 N1 Cd1 139.9(9) . . ? C2 N1 Cd1 114.8(8) . . ? C5 N2 C3 105.1(10) . . ? C5 N2 Cd1 137.8(9) . 6_444 ? C3 N2 Cd1 116.9(9) . 6_444 ? C1 O1 Cd1 133.9(9) . 13_556 ? C1 O1 Cd1 116.5(9) . . ? Cd1 O1 Cd1 109.0(4) 13_556 . ? C4 O3 H3 109.5 . . ? C4 O4 Cd1 111.8(10) . 6_444 ? O1 C1 O2 126.4(13) . . ? O1 C1 C2 116.4(13) . . ? O2 C1 C2 117.1(12) . . ? C3 C2 N1 108.7(11) . . ? C3 C2 C1 131.5(13) . . ? N1 C2 C1 119.7(11) . . ? C2 C3 N2 108.0(11) . . ? C2 C3 C4 132.3(13) . . ? N2 C3 C4 119.5(13) . . ? O4 C4 O3 120.4(16) . . ? O4 C4 C3 120.6(15) . . ? O3 C4 C3 119.0(14) . . ? N1 C5 N2 113.0(12) . . ? N1 C5 C6 123.9(13) . . ? N2 C5 C6 123.1(13) . . ? C7 C6 C11 120.2(16) . . ? C7 C6 C5 119.3(15) . . ? C11 C6 C5 120.4(15) . . ? C8 C7 C6 118.3(18) . . ? C8 C7 H7A 120.9 . . ? C6 C7 H7A 120.9 . . ? C7 C8 C9 123(2) . . ? C7 C8 H8A 118.4 . . ? C9 C8 H8A 118.4 . . ? C10 C9 C8 119.0(19) . . ? C10 C9 C12 120(2) . . ? C8 C9 C12 121(2) . . ? C9 C10 C11 123(2) . . ? C9 C10 C13 125.1(19) . . ? C11 C10 C13 111(2) . . ? C10 C11 C6 115.5(18) . . ? C10 C11 H11 122.2 . . ? C6 C11 H11 122.2 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C14 N3 C18 120.0 . . ? C14 N3 Cd1 122.2(10) . . ? C18 N3 Cd1 117.6(10) . . ? C15 C14 N3 120.0 . . ? C15 C14 H14A 120.0 . . ? N3 C14 H14A 120.0 . . ? C14 C15 C16 120.0 . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C17 C16 C15 120.0 . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C18 C17 C16 120.0 . . ? C18 C17 H17A 120.0 . . ? C16 C17 H17A 120.0 . . ? C17 C18 N3 120.0 . . ? C17 C18 H18A 120.0 . . ? N3 C18 H18A 120.0 . . ? _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 N2 Cd1 N1 C5 42.2(16) 8_444 . . . ? O1 Cd1 N1 C5 -170.0(13) 13_556 . . . ? N3 Cd1 N1 C5 -69.9(16) . . . . ? O1 Cd1 N1 C5 -174.6(16) . . . . ? O4 Cd1 N1 C5 109.9(15) 8_444 . . . ? N2 Cd1 N1 C2 -137.3(9) 8_444 . . . ? O1 Cd1 N1 C2 10.5(13) 13_556 . . . ? N3 Cd1 N1 C2 110.6(11) . . . . ? O1 Cd1 N1 C2 5.8(9) . . . . ? O4 Cd1 N1 C2 -69.6(9) 8_444 . . . ? N2 Cd1 O1 C1 88.4(12) 8_444 . . . ? N1 Cd1 O1 C1 -10.3(10) . . . . ? O1 Cd1 O1 C1 172.7(13) 13_556 . . . ? N3 Cd1 O1 C1 -94.4(11) . . . . ? O4 Cd1 O1 C1 80.0(11) 8_444 . . . ? N2 Cd1 O1 Cd1 -84.3(7) 8_444 . . 13_556 ? N1 Cd1 O1 Cd1 177.0(5) . . . 13_556 ? O1 Cd1 O1 Cd1 0.000(1) 13_556 . . 13_556 ? N3 Cd1 O1 Cd1 92.9(6) . . . 13_556 ? O4 Cd1 O1 Cd1 -92.7(5) 8_444 . . 13_556 ? Cd1 O1 C1 O2 0(2) 13_556 . . . ? Cd1 O1 C1 O2 -170.5(12) . . . . ? Cd1 O1 C1 C2 -177.4(9) 13_556 . . . ? Cd1 O1 C1 C2 12.2(16) . . . . ? C5 N1 C2 C3 1.0(16) . . . . ? Cd1 N1 C2 C3 -179.3(9) . . . . ? C5 N1 C2 C1 177.8(13) . . . . ? Cd1 N1 C2 C1 -2.5(16) . . . . ? O1 C1 C2 C3 169.0(15) . . . . ? O2 C1 C2 C3 -9(2) . . . . ? O1 C1 C2 N1 -7(2) . . . . ? O2 C1 C2 N1 175.4(13) . . . . ? N1 C2 C3 N2 -0.8(16) . . . . ? C1 C2 C3 N2 -177.2(14) . . . . ? N1 C2 C3 C4 -177.2(15) . . . . ? C1 C2 C3 C4 6(3) . . . . ? C5 N2 C3 C2 0.4(15) . . . . ? Cd1 N2 C3 C2 176.3(9) 6_444 . . . ? C5 N2 C3 C4 177.2(13) . . . . ? Cd1 N2 C3 C4 -6.8(17) 6_444 . . . ? Cd1 O4 C4 O3 179.9(12) 6_444 . . . ? Cd1 O4 C4 C3 -1.2(19) 6_444 . . . ? C2 C3 C4 O4 -178.7(15) . . . . ? N2 C3 C4 O4 5(2) . . . . ? C2 C3 C4 O3 0(3) . . . . ? N2 C3 C4 O3 -175.7(14) . . . . ? C2 N1 C5 N2 -0.8(16) . . . . ? Cd1 N1 C5 N2 179.7(10) . . . . ? C2 N1 C5 C6 178.0(14) . . . . ? Cd1 N1 C5 C6 -2(2) . . . . ? C3 N2 C5 N1 0.3(16) . . . . ? Cd1 N2 C5 N1 -174.3(9) 6_444 . . . ? C3 N2 C5 C6 -178.5(14) . . . . ? Cd1 N2 C5 C6 7(2) 6_444 . . . ? N1 C5 C6 C7 -60(2) . . . . ? N2 C5 C6 C7 118.6(17) . . . . ? N1 C5 C6 C11 123.8(17) . . . . ? N2 C5 C6 C11 -58(2) . . . . ? C11 C6 C7 C8 -1(3) . . . . ? C5 C6 C7 C8 -177.0(15) . . . . ? C6 C7 C8 C9 -2(3) . . . . ? C7 C8 C9 C10 -1(3) . . . . ? C7 C8 C9 C12 176.9(18) . . . . ? C8 C9 C10 C11 7(3) . . . . ? C12 C9 C10 C11 -171(2) . . . . ? C8 C9 C10 C13 179(2) . . . . ? C12 C9 C10 C13 1(4) . . . . ? C9 C10 C11 C6 -9(3) . . . . ? C13 C10 C11 C6 178.0(19) . . . . ? C7 C6 C11 C10 6(3) . . . . ? C5 C6 C11 C10 -178.2(16) . . . . ? N2 Cd1 N3 C14 126.7(10) 8_444 . . . ? N1 Cd1 N3 C14 -122.0(10) . . . . ? O1 Cd1 N3 C14 20.5(11) 13_556 . . . ? O1 Cd1 N3 C14 -51.6(11) . . . . ? O4 Cd1 N3 C14 -124(6) 8_444 . . . ? N2 Cd1 N3 C18 -58.4(10) 8_444 . . . ? N1 Cd1 N3 C18 53.0(10) . . . . ? O1 Cd1 N3 C18 -164.5(9) 13_556 . . . ? O1 Cd1 N3 C18 123.4(9) . . . . ? O4 Cd1 N3 C18 51(6) 8_444 . . . ? C18 N3 C14 C15 0.0 . . . . ? Cd1 N3 C14 C15 174.8(13) . . . . ? N3 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C17 0.0 . . . . ? C15 C16 C17 C18 0.0 . . . . ? C16 C17 C18 N3 0.0 . . . . ? C14 N3 C18 C17 0.0 . . . . ? Cd1 N3 C18 C17 -175.1(13) . . . . ? _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 O3 H3 O2 0.82 1.67 2.485(14) 169.0 . _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.918 _refine_diff_density_min -0.539 _refine_diff_density_rms 0.129 data_y _database_code_depnum_ccdc_archive 'CCDC 885609' #TrackingRef '- 2.cif' _audit_creation_date 2012-09-10 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'Sr, C13 H10 N2 O4, H2 O' _chemical_formula_sum 'C13 H12 N2 O5 Sr' _chemical_formula_weight 363.87 _chemical_melting_point ? 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' Sr Sr -1.5307 3.2498 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 16.346(3) _cell_length_b 6.6684(13) _cell_length_c 12.675(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.774(2) _cell_angle_gamma 90.00 _cell_volume 1308.1(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5164 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 27.51 _cell_measurement_theta_min 2.63 _exptl_absorpt_coefficient_mu 4.146 _exptl_absorpt_correction_T_max 0.3693 _exptl_absorpt_correction_T_min 0.3248 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.848 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 728 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_unetI/netI 0.0580 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 10903 _diffrn_reflns_theta_full 27.60 _diffrn_reflns_theta_max 27.60 _diffrn_reflns_theta_min 2.63 _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _reflns_number_gt 2393 _reflns_number_total 3032 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'SAINT v7.53A (Bruker, 2008)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 1.437 _refine_diff_density_min -1.267 _refine_diff_density_rms 0.189 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 3032 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0538 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1189P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1555 _refine_ls_wR_factor_ref 0.1671 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 Sr1 Sr 0.02400(3) 0.06811(5) 0.67965(3) 0.01775(19) Uani 1 1 d . . . O1 O 0.0895(2) 0.7201(4) 0.7250(3) 0.0229(7) Uani 1 1 d . . . O2 O 0.0259(2) 0.4365(4) 0.6483(3) 0.0197(7) Uani 1 1 d . . . O3 O 0.0737(2) 0.1357(5) 0.5138(3) 0.0279(8) Uani 1 1 d . . . O4 O 0.1005(2) 0.2148(5) 0.3596(2) 0.0211(7) Uani 1 1 d . . . O5 O 0.2048(3) 0.0838(5) 0.7456(3) 0.0312(9) Uani 1 1 d G . . H5A H 0.2210 0.2036 0.7408 0.047 Uiso 1 1 d G . . H5B H 0.2110 0.0567 0.8132 0.047 Uiso 1 1 d G . . N1 N 0.1911(3) 0.7306(5) 0.5914(3) 0.0216(9) Uani 1 1 d . . . H1 H 0.1985 0.8320 0.6354 0.026 Uiso 1 1 calc R . . N2 N 0.2047(3) 0.5309(6) 0.4598(3) 0.0200(8) Uani 1 1 d . . . C1 C 0.0819(3) 0.5715(6) 0.6595(4) 0.0176(9) Uani 1 1 d . . . C2 C 0.1397(3) 0.5665(6) 0.5909(4) 0.0186(10) Uani 1 1 d . . . C3 C 0.1491(3) 0.4422(6) 0.5076(4) 0.0203(10) Uani 1 1 d . . . C4 C 0.1050(3) 0.2520(6) 0.4587(3) 0.0165(9) Uani 1 1 d . . . C5 C 0.2278(3) 0.7045(7) 0.5108(4) 0.0212(9) Uani 1 1 d . . . C6 C 0.2875(3) 0.8491(7) 0.4854(4) 0.0232(10) Uani 1 1 d . . . C7 C 0.3213(4) 0.8077(8) 0.4005(4) 0.0323(12) Uani 1 1 d . . . H7 H 0.3086 0.6854 0.3636 0.039 Uiso 1 1 calc R . . C8 C 0.3735(4) 0.9429(8) 0.3689(5) 0.0330(13) Uani 1 1 d . . . C9 C 0.3916(4) 1.1290(9) 0.4227(5) 0.0336(12) Uani 1 1 d . . . C10 C 0.3589(4) 1.1679(8) 0.5080(5) 0.0364(13) Uani 1 1 d . . . H10 H 0.3716 1.2901 0.5451 0.044 Uiso 1 1 calc R . . C11 C 0.3078(4) 1.0316(8) 0.5404(5) 0.0332(13) Uani 1 1 d . . . H11 H 0.2871 1.0621 0.5988 0.040 Uiso 1 1 calc R . . C12 C 0.4087(5) 0.8883(11) 0.2760(6) 0.059(2) Uani 1 1 d . . . H12A H 0.3928 0.7529 0.2526 0.088 Uiso 1 1 calc R . . H12B H 0.4706 0.8998 0.3022 0.088 Uiso 1 1 calc R . . H12C H 0.3852 0.9776 0.2142 0.088 Uiso 1 1 calc R . . C13 C 0.4475(5) 1.2824(10) 0.3897(6) 0.0534(18) Uani 1 1 d . . . H13A H 0.4205 1.3203 0.3133 0.080 Uiso 1 1 calc R . . H13B H 0.5033 1.2253 0.3986 0.080 Uiso 1 1 calc R . . H13C H 0.4542 1.3987 0.4364 0.080 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 Sr1 0.0305(3) 0.0110(3) 0.0189(3) -0.00050(13) 0.0180(2) -0.00108(15) O1 0.038(2) 0.0136(15) 0.0251(16) -0.0030(12) 0.0214(16) -0.0021(14) O2 0.029(2) 0.0145(16) 0.0235(16) 0.0015(11) 0.0186(15) -0.0005(12) O3 0.052(3) 0.0162(15) 0.0270(17) -0.0023(13) 0.0280(18) -0.0091(16) O4 0.0265(19) 0.0220(16) 0.0178(15) -0.0032(12) 0.0115(14) -0.0046(14) O5 0.046(3) 0.031(2) 0.0239(18) -0.0006(13) 0.0216(18) 0.0000(17) N1 0.030(2) 0.0188(19) 0.0240(19) -0.0059(15) 0.0196(19) -0.0070(16) N2 0.023(2) 0.0204(19) 0.0220(19) -0.0015(14) 0.0154(18) -0.0033(16) C1 0.023(3) 0.016(2) 0.017(2) 0.0034(15) 0.0112(19) 0.0039(17) C2 0.028(3) 0.016(2) 0.016(2) 0.0013(15) 0.012(2) -0.0006(17) C3 0.030(3) 0.018(2) 0.020(2) 0.0014(16) 0.018(2) -0.0008(18) C4 0.024(3) 0.011(2) 0.019(2) 0.0008(15) 0.014(2) 0.0005(16) C5 0.024(3) 0.022(2) 0.024(2) -0.0008(18) 0.016(2) -0.001(2) C6 0.025(3) 0.023(2) 0.027(2) -0.0013(18) 0.016(2) -0.003(2) C7 0.044(3) 0.031(3) 0.034(3) -0.008(2) 0.028(3) -0.012(2) C8 0.032(3) 0.044(3) 0.030(3) -0.005(2) 0.021(3) -0.011(2) C9 0.032(3) 0.033(3) 0.041(3) 0.002(2) 0.020(3) -0.012(2) C10 0.044(4) 0.026(3) 0.048(3) -0.007(2) 0.028(3) -0.010(2) C11 0.047(4) 0.026(3) 0.040(3) -0.009(2) 0.032(3) -0.009(2) C12 0.068(5) 0.074(5) 0.056(4) -0.018(4) 0.051(4) -0.029(4) C13 0.060(5) 0.048(4) 0.064(4) 0.003(3) 0.036(4) -0.023(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 Sr1 Sr1 3.9767(7) 2_556 ? Sr1 O1 2.543(3) 1_545 ? Sr1 O1 2.716(3) 2_546 ? Sr1 O2 2.709(3) 2_546 ? Sr1 O2 2.490(3) . ? Sr1 O3 2.526(3) . ? Sr1 O3 2.809(3) 3_556 ? Sr1 O4 2.702(3) 3_556 ? Sr1 O4 2.651(3) 4_566 ? Sr1 O5 2.803(4) . ? Sr1 C1 3.070(4) 2_546 ? Sr1 C4 3.114(4) 3_556 ? O1 Sr1 2.716(3) 2_556 ? O1 Sr1 2.543(3) 1_565 ? O1 C1 1.272(5) . ? O2 Sr1 2.709(3) 2_556 ? O2 C1 1.259(5) . ? O3 Sr1 2.809(3) 3_556 ? O3 C4 1.258(5) . ? O4 Sr1 2.651(3) 4_565 ? O4 Sr1 2.702(3) 3_556 ? O4 C4 1.259(5) . ? O5 H5A 0.8500 . ? O5 H5B 0.8499 . ? N1 H1 0.8600 . ? N1 C2 1.377(5) . ? N1 C5 1.353(5) . ? N2 C3 1.378(6) . ? N2 C5 1.320(6) . ? C1 Sr1 3.070(4) 2_556 ? C1 C2 1.477(6) . ? C2 C3 1.388(6) . ? C3 C4 1.491(6) . ? C4 Sr1 3.114(4) 3_556 ? C5 C6 1.479(6) . ? C6 C7 1.387(6) . ? C6 C11 1.388(7) . ? C7 H7 0.9300 . ? C7 C8 1.386(7) . ? C8 C9 1.401(7) . ? C8 C12 1.513(8) . ? C9 C10 1.375(7) . ? C9 C13 1.518(7) . ? C10 H10 0.9300 . ? C10 C11 1.385(7) . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? 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 Sr1 Sr1 142.50(7) 1_545 2_556 ? O1 Sr1 Sr1 39.26(7) 2_546 2_556 ? O1 Sr1 O1 122.57(8) 1_545 2_546 ? O1 Sr1 O2 74.72(9) 1_545 2_546 ? O1 Sr1 O3 80.52(10) 1_545 3_556 ? O1 Sr1 O3 106.95(10) 2_546 3_556 ? O1 Sr1 O4 104.85(10) 1_545 4_566 ? O1 Sr1 O4 69.01(10) 1_545 3_556 ? O1 Sr1 O5 131.24(10) 2_546 . ? O1 Sr1 O5 68.89(11) 1_545 . ? O1 Sr1 C1 24.43(10) 2_546 2_546 ? O1 Sr1 C1 98.23(10) 1_545 2_546 ? O1 Sr1 C4 70.19(11) 1_545 3_556 ? O1 Sr1 C4 94.05(11) 2_546 3_556 ? O2 Sr1 Sr1 42.18(7) . 2_556 ? O2 Sr1 Sr1 75.91(6) 2_546 2_556 ? O2 Sr1 O1 48.44(9) 2_546 2_546 ? O2 Sr1 O1 75.42(10) . 2_546 ? O2 Sr1 O1 155.55(11) . 1_545 ? O2 Sr1 O2 118.08(8) . 2_546 ? O2 Sr1 O3 70.55(11) . . ? O2 Sr1 O3 111.77(11) . 3_556 ? O2 Sr1 O3 108.19(10) 2_546 3_556 ? O2 Sr1 O4 134.98(11) . 3_556 ? O2 Sr1 O4 64.66(11) . 4_566 ? O2 Sr1 O5 86.82(11) . . ? O2 Sr1 O5 109.52(10) 2_546 . ? O2 Sr1 C1 24.14(10) 2_546 2_546 ? O2 Sr1 C1 97.90(10) . 2_546 ? O2 Sr1 C4 128.85(12) . 3_556 ? O2 Sr1 C4 84.62(10) 2_546 3_556 ? O3 Sr1 Sr1 131.18(8) 3_556 2_556 ? O3 Sr1 Sr1 112.72(8) . 2_556 ? O3 Sr1 O1 138.81(11) . 2_546 ? O3 Sr1 O1 97.25(10) . 1_545 ? O3 Sr1 O2 171.37(10) . 2_546 ? O3 Sr1 O3 66.71(12) . 3_556 ? O3 Sr1 O4 113.36(10) . 3_556 ? O3 Sr1 O4 115.43(10) . 4_566 ? O3 Sr1 O5 69.56(11) . . ? O3 Sr1 C1 162.23(12) . 2_546 ? O3 Sr1 C1 107.43(11) 3_556 2_546 ? O3 Sr1 C4 23.82(9) 3_556 3_556 ? O3 Sr1 C4 89.70(11) . 3_556 ? O4 Sr1 Sr1 114.98(7) 3_556 2_556 ? O4 Sr1 Sr1 42.51(7) 4_566 2_556 ? O4 Sr1 O1 76.14(9) 3_556 2_546 ? O4 Sr1 O1 67.29(10) 4_566 2_546 ? O4 Sr1 O2 61.16(9) 3_556 2_546 ? O4 Sr1 O2 70.44(9) 4_566 2_546 ? O4 Sr1 O3 173.58(10) 4_566 3_556 ? O4 Sr1 O3 47.03(8) 3_556 3_556 ? O4 Sr1 O4 131.21(5) 4_566 3_556 ? O4 Sr1 O5 137.80(10) 3_556 . ? O4 Sr1 O5 64.06(10) 4_566 . ? O4 Sr1 C1 64.83(10) 3_556 2_546 ? O4 Sr1 C1 68.63(11) 4_566 2_546 ? O4 Sr1 C4 154.87(10) 4_566 3_556 ? O4 Sr1 C4 23.66(9) 3_556 3_556 ? O5 Sr1 Sr1 100.16(7) . 2_556 ? O5 Sr1 O3 121.80(10) . 3_556 ? O5 Sr1 C1 124.60(11) . 2_546 ? O5 Sr1 C4 130.66(10) . 3_556 ? C1 Sr1 Sr1 57.40(7) 2_546 2_556 ? C1 Sr1 C4 87.38(11) 2_546 3_556 ? C4 Sr1 Sr1 129.16(8) 3_556 2_556 ? Sr1 O1 Sr1 98.22(11) 1_565 2_556 ? C1 O1 Sr1 128.2(3) . 1_565 ? C1 O1 Sr1 93.6(3) . 2_556 ? Sr1 O2 Sr1 99.70(10) . 2_556 ? C1 O2 Sr1 94.2(3) . 2_556 ? C1 O2 Sr1 137.2(3) . . ? Sr1 O3 Sr1 113.29(12) . 3_556 ? C4 O3 Sr1 91.8(3) . 3_556 ? C4 O3 Sr1 150.5(3) . . ? Sr1 O4 Sr1 95.97(11) 4_565 3_556 ? C4 O4 Sr1 127.6(3) . 4_565 ? C4 O4 Sr1 96.9(3) . 3_556 ? Sr1 O5 H5A 109.7 . . ? Sr1 O5 H5B 93.7 . . ? H5A O5 H5B 109.5 . . ? C2 N1 H1 125.9 . . ? C5 N1 H1 125.9 . . ? C5 N1 C2 108.2(4) . . ? C5 N2 C3 106.6(4) . . ? O1 C1 Sr1 62.0(2) . 2_556 ? O1 C1 C2 117.1(4) . . ? O2 C1 Sr1 61.6(2) . 2_556 ? O2 C1 O1 123.0(4) . . ? O2 C1 C2 119.8(4) . . ? C2 C1 Sr1 174.7(3) . 2_556 ? N1 C2 C1 118.9(3) . . ? N1 C2 C3 105.2(4) . . ? C3 C2 C1 135.2(4) . . ? N2 C3 C2 109.1(4) . . ? N2 C3 C4 118.7(4) . . ? C2 C3 C4 131.9(4) . . ? O3 C4 Sr1 64.4(2) . 3_556 ? O3 C4 O4 122.0(4) . . ? O3 C4 C3 121.4(4) . . ? O4 C4 Sr1 59.5(2) . 3_556 ? O4 C4 C3 116.6(4) . . ? C3 C4 Sr1 165.0(3) . 3_556 ? N1 C5 C6 124.4(4) . . ? N2 C5 N1 110.8(4) . . ? N2 C5 C6 124.7(4) . . ? C7 C6 C5 119.7(4) . . ? C7 C6 C11 118.3(4) . . ? C11 C6 C5 122.0(4) . . ? C6 C7 H7 119.0 . . ? C8 C7 C6 122.1(5) . . ? C8 C7 H7 119.0 . . ? C7 C8 C9 119.2(5) . . ? C7 C8 C12 119.5(5) . . ? C9 C8 C12 121.2(5) . . ? C8 C9 C13 121.0(5) . . ? C10 C9 C8 118.4(5) . . ? C10 C9 C13 120.7(5) . . ? C9 C10 H10 118.9 . . ? C9 C10 C11 122.3(5) . . ? C11 C10 H10 118.9 . . ? C6 C11 H11 120.1 . . ? C10 C11 C6 119.7(5) . . ? C10 C11 H11 120.1 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 O5 H5B N2 0.85 1.98 2.822(5) 169.6 4_566 N1 H1 O5 0.86 2.16 3.022(5) 174.7 1_565 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 Sr1 Sr1 O2 C1 107.1(5) 2_556 . . . ? Sr1 Sr1 O3 Sr1 -126.65(10) 2_556 . . 3_556 ? Sr1 Sr1 O3 C4 19.4(7) 2_556 . . . ? Sr1 O1 C1 Sr1 -103.4(3) 1_565 . . 2_556 ? Sr1 O1 C1 O2 8.9(5) 2_556 . . . ? Sr1 O1 C1 O2 -94.5(5) 1_565 . . . ? Sr1 O1 C1 C2 82.5(5) 1_565 . . . ? Sr1 O1 C1 C2 -174.1(3) 2_556 . . . ? Sr1 O2 C1 Sr1 -109.2(4) . . . 2_556 ? Sr1 O2 C1 O1 -118.0(4) . . . . ? Sr1 O2 C1 O1 -8.9(5) 2_556 . . . ? Sr1 O2 C1 C2 65.0(6) . . . . ? Sr1 O2 C1 C2 174.2(4) 2_556 . . . ? Sr1 O3 C4 Sr1 -149.1(7) . . . 3_556 ? Sr1 O3 C4 O4 -164.5(4) . . . . ? Sr1 O3 C4 O4 -15.4(5) 3_556 . . . ? Sr1 O3 C4 C3 164.2(4) 3_556 . . . ? Sr1 O3 C4 C3 15.1(10) . . . . ? Sr1 O4 C4 Sr1 103.0(3) 4_565 . . 3_556 ? Sr1 O4 C4 O3 119.2(4) 4_565 . . . ? Sr1 O4 C4 O3 16.2(5) 3_556 . . . ? Sr1 O4 C4 C3 -60.5(5) 4_565 . . . ? Sr1 O4 C4 C3 -163.5(4) 3_556 . . . ? Sr1 C1 C2 N1 -86(3) 2_556 . . . ? Sr1 C1 C2 C3 105(3) 2_556 . . . ? O1 Sr1 O2 Sr1 25.23(11) 2_546 . . 2_556 ? O1 Sr1 O2 Sr1 -115.3(2) 1_545 . . 2_556 ? O1 Sr1 O2 C1 -8.2(6) 1_545 . . . ? O1 Sr1 O2 C1 132.3(4) 2_546 . . . ? O1 Sr1 O3 Sr1 76.38(15) 1_545 . . 3_556 ? O1 Sr1 O3 Sr1 -89.43(18) 2_546 . . 3_556 ? O1 Sr1 O3 C4 -137.6(7) 1_545 . . . ? O1 Sr1 O3 C4 56.6(7) 2_546 . . . ? O1 C1 C2 N1 -7.2(6) . . . . ? O1 C1 C2 C3 -175.8(5) . . . . ? O2 Sr1 O2 Sr1 1.53(5) 2_546 . . 2_556 ? O2 Sr1 O2 C1 108.6(4) 2_546 . . . ? O2 Sr1 O3 Sr1 -125.46(17) . . . 3_556 ? O2 Sr1 O3 Sr1 55.2(8) 2_546 . . 3_556 ? O2 Sr1 O3 C4 -158.8(7) 2_546 . . . ? O2 Sr1 O3 C4 20.6(7) . . . . ? O2 C1 C2 N1 169.9(4) . . . . ? O2 C1 C2 C3 1.3(8) . . . . ? O3 Sr1 O2 Sr1 -178.36(15) . . . 2_556 ? O3 Sr1 O2 Sr1 127.97(11) 3_556 . . 2_556 ? O3 Sr1 O2 C1 -124.9(4) 3_556 . . . ? O3 Sr1 O2 C1 -71.2(4) . . . . ? O3 Sr1 O3 Sr1 0.0 3_556 . . 3_556 ? O3 Sr1 O3 C4 146.1(8) 3_556 . . . ? O4 Sr1 O2 Sr1 -46.21(11) 4_566 . . 2_556 ? O4 Sr1 O2 Sr1 77.65(16) 3_556 . . 2_556 ? O4 Sr1 O2 C1 -175.2(4) 3_556 . . . ? O4 Sr1 O2 C1 60.9(4) 4_566 . . . ? O4 Sr1 O3 Sr1 -173.35(11) 4_566 . . 3_556 ? O4 Sr1 O3 Sr1 6.16(17) 3_556 . . 3_556 ? O4 Sr1 O3 C4 -27.3(7) 4_566 . . . ? O4 Sr1 O3 C4 152.2(7) 3_556 . . . ? O5 Sr1 O2 Sr1 -108.93(12) . . . 2_556 ? O5 Sr1 O2 C1 -1.8(4) . . . . ? O5 Sr1 O3 Sr1 140.60(16) . . . 3_556 ? O5 Sr1 O3 C4 -73.3(7) . . . . ? N1 C2 C3 N2 0.0(5) . . . . ? N1 C2 C3 C4 -173.7(5) . . . . ? N1 C5 C6 C7 -179.8(5) . . . . ? N1 C5 C6 C11 -3.1(8) . . . . ? N2 C3 C4 Sr1 -91.5(12) . . . 3_556 ? N2 C3 C4 O3 159.9(5) . . . . ? N2 C3 C4 O4 -20.5(7) . . . . ? N2 C5 C6 C7 1.8(8) . . . . ? N2 C5 C6 C11 178.5(5) . . . . ? C1 Sr1 O2 Sr1 15.57(14) 2_546 . . 2_556 ? C1 Sr1 O2 C1 122.7(4) 2_546 . . . ? C1 Sr1 O3 Sr1 -74.1(4) 2_546 . . 3_556 ? C1 Sr1 O3 C4 72.0(8) 2_546 . . . ? C1 C2 C3 N2 169.6(5) . . . . ? C1 C2 C3 C4 -4.0(9) . . . . ? C2 N1 C5 N2 -1.4(6) . . . . ? C2 N1 C5 C6 180.0(5) . . . . ? C2 C3 C4 Sr1 81.6(12) . . . 3_556 ? C2 C3 C4 O3 -27.0(8) . . . . ? C2 C3 C4 O4 152.7(5) . . . . ? C3 N2 C5 N1 1.3(6) . . . . ? C3 N2 C5 C6 179.9(5) . . . . ? C4 Sr1 O2 Sr1 108.58(14) 3_556 . . 2_556 ? C4 Sr1 O2 C1 -144.3(4) 3_556 . . . ? C4 Sr1 O3 Sr1 6.39(14) 3_556 . . 3_556 ? C4 Sr1 O3 C4 152.4(6) 3_556 . . . ? C5 N1 C2 C1 -170.8(4) . . . . ? C5 N1 C2 C3 0.8(5) . . . . ? C5 N2 C3 C2 -0.8(6) . . . . ? C5 N2 C3 C4 173.8(4) . . . . ? C5 C6 C7 C8 176.2(5) . . . . ? C5 C6 C11 C10 -175.3(5) . . . . ? C6 C7 C8 C9 -1.2(9) . . . . ? C6 C7 C8 C12 179.7(6) . . . . ? C7 C6 C11 C10 1.5(9) . . . . ? C7 C8 C9 C10 2.1(9) . . . . ? C7 C8 C9 C13 -179.2(6) . . . . ? C8 C9 C10 C11 -1.3(10) . . . . ? C9 C10 C11 C6 -0.5(10) . . . . ? C11 C6 C7 C8 -0.6(9) . . . . ? C12 C8 C9 C10 -178.8(6) . . . . ? C12 C8 C9 C13 -0.2(10) . . . . ? C13 C9 C10 C11 -179.9(6) . . . . ? data_201110142_twin1_hklf4 _database_code_depnum_ccdc_archive 'CCDC 885610' #TrackingRef '- 3.cif' _audit_creation_date 2012-09-10 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '0.11(C234 H270 N36 O126 Zn27), 2(H2 O)' _chemical_formula_sum 'C26 H34 N4 O16 Zn3' _chemical_formula_weight 854.68 _chemical_melting_point ? _chemical_oxdiff_formula C20H20N4O4Zn1 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system trigonal _space_group_IT_number 148 _space_group_name_H-M_alt 'R -3' _space_group_name_Hall '-R 3' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-y, x-y, z' 3 '-x+y, -x, z' 4 'x+2/3, y+1/3, z+1/3' 5 '-y+2/3, x-y+1/3, z+1/3' 6 '-x+y+2/3, -x+1/3, z+1/3' 7 'x+1/3, y+2/3, z+2/3' 8 '-y+1/3, x-y+2/3, z+2/3' 9 '-x+y+1/3, -x+2/3, z+2/3' 10 '-x, -y, -z' 11 'y, -x+y, -z' 12 'x-y, x, -z' 13 '-x+2/3, -y+1/3, -z+1/3' 14 'y+2/3, -x+y+1/3, -z+1/3' 15 'x-y+2/3, x+1/3, -z+1/3' 16 '-x+1/3, -y+2/3, -z+2/3' 17 'y+1/3, -x+y+2/3, -z+2/3' 18 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 24.4118(16) _cell_length_b 24.4118(16) _cell_length_c 14.2677(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7363.5(9) _cell_formula_units_Z 9 _cell_measurement_reflns_used 2082 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 26.3114 _cell_measurement_theta_min 2.8781 _exptl_absorpt_coefficient_mu 2.261 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89173 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour cubic _exptl_crystal_density_diffrn 1.735 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description colorless _exptl_crystal_F_000 3924 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.21 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_unetI/netI 0.0612 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 6745 _diffrn_reflns_theta_full 26.50 _diffrn_reflns_theta_max 26.50 _diffrn_reflns_theta_min 2.89 _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean 16.2312 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -49.00 33.00 1.0000 28.8300 omega____ theta____ kappa____ phi______ frames - 19.8666 -57.0000 30.0000 82 #__ type_ start__ end____ width___ exp.time_ 2 omega 48.00 89.00 1.0000 28.8300 omega____ theta____ kappa____ phi______ frames - 19.8666 57.0000 -180.0000 41 #__ type_ start__ end____ width___ exp.time_ 3 omega 32.00 57.00 1.0000 28.8300 omega____ theta____ kappa____ phi______ frames - 19.8666 -178.0000 -90.0000 25 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0332920000 _diffrn_orient_matrix_UB_12 0.0138439000 _diffrn_orient_matrix_UB_13 -0.0031921000 _diffrn_orient_matrix_UB_21 -0.0033004000 _diffrn_orient_matrix_UB_22 -0.0136529000 _diffrn_orient_matrix_UB_23 -0.0450139000 _diffrn_orient_matrix_UB_31 0.0020402000 _diffrn_orient_matrix_UB_32 0.0273730000 _diffrn_orient_matrix_UB_33 -0.0208044000 loop_ _diffrn_oxdiff_twin_id _diffrn_oxdiff_twin_ratio _diffrn_oxdiff_twin_reflns_isolated _diffrn_oxdiff_twin_reflns_overlapped 1 0.5702 3231 3672 2 0.4298 3225 3672 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5205 _reflns_number_total 6745 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.457 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.093 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 6745 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0430 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0953 _refine_ls_wR_factor_ref 0.0992 _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. We have described as 10 restrains: DFIX 0.86 O7 H7b. DFIX 0.86 O6 H6a. DFIX 0.86 O6 H6b. DFIX 0.86 O5 H5a. DFIX 0.86 O5 H5b. DFIX 0.85 O8 H8b. DFIX 0.85 O8 H8a. DANG 1.38 H6b H6a. DANG 1.38 H5a H5b. DANG 1.38 H8b H8a. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C4 C 0.54543(14) 0.60237(14) 0.3481(2) 0.0185(7) Uani 1 1 d . . . C5 C 0.46364(15) 0.55748(14) 0.1318(2) 0.0186(7) Uani 1 1 d . . . C6 C 0.45319(14) 0.57458(15) 0.0379(2) 0.0236(8) Uani 1 1 d . . . C7 C 0.45930(15) 0.63331(16) 0.0218(2) 0.0289(9) Uani 1 1 d . . . H7 H 0.4726 0.6622 0.0709 0.043 Uiso 1 1 calc R . . C8 C 0.44668(16) 0.65084(17) -0.0630(3) 0.0344(9) Uani 1 1 d . . . C9 C 0.42751(16) 0.6083(2) -0.1377(3) 0.0382(10) Uani 1 1 d . . . C10 C 0.42199(18) 0.54947(19) -0.1237(3) 0.0420(10) Uani 1 1 d . . . H10 H 0.4095 0.5210 -0.1733 0.063 Uiso 1 1 calc R . . C11 C 0.43474(17) 0.53232(17) -0.0372(2) 0.0325(9) Uani 1 1 d . . . H11 H 0.4310 0.4928 -0.0293 0.049 Uiso 1 1 calc R . . C12 C 0.4527(2) 0.7153(2) -0.0744(3) 0.0601(14) Uani 1 1 d . . . H12A H 0.4119 0.7103 -0.0874 0.090 Uiso 1 1 calc R . . H12B H 0.4809 0.7373 -0.1254 0.090 Uiso 1 1 calc R . . H12C H 0.4692 0.7392 -0.0177 0.090 Uiso 1 1 calc R . . C13 C 0.4114(2) 0.6241(2) -0.2327(3) 0.0602(14) Uani 1 1 d . . . H13A H 0.3799 0.6364 -0.2254 0.090 Uiso 1 1 calc R . . H13B H 0.3952 0.5876 -0.2726 0.090 Uiso 1 1 calc R . . H13C H 0.4487 0.6582 -0.2603 0.090 Uiso 1 1 calc R . . N1 N 0.42402(12) 0.50235(11) 0.17462(18) 0.0176(6) Uani 1 1 d . . . N2 N 0.51057(11) 0.59744(11) 0.18872(18) 0.0180(6) Uani 1 1 d . . . O1 O 0.53904(12) 0.58166(10) 0.42939(17) 0.0418(7) Uani 1 1 d . . . O2 O 0.59086(10) 0.65678(9) 0.32713(15) 0.0214(5) Uani 1 1 d . . . O3 O 0.35912(10) 0.40944(10) 0.29505(15) 0.0235(5) Uani 1 1 d . . . O4 O 0.42316(11) 0.45538(11) 0.41329(16) 0.0338(6) Uani 1 1 d . . . O5 O 0.41999(12) 0.38744(13) 0.1161(2) 0.0588(9) Uani 1 1 d D . . H5A H 0.4085 0.3620 0.0670 0.088 Uiso 1 1 d RD . . H5B H 0.4433 0.3786 0.1533 0.088 Uiso 1 1 d RD . . O6 O 0.29076(13) 0.31064(11) 0.1578(2) 0.0452(7) Uani 1 1 d D . . H6A H 0.2850 0.2988 0.2159 0.068 Uiso 1 1 d RD . . H6B H 0.3311 0.3212 0.1450 0.068 Uiso 1 1 d RD . . C1 C 0.40860(14) 0.45546(14) 0.3297(2) 0.0207(8) Uani 1 1 d . . . O7 O 0.54740(13) 0.46393(14) 0.4124(2) 0.0590(9) Uani 1 1 d D . . H7A H 0.5833 0.4950 0.3924 0.089 Uiso 1 1 d R . . H7B H 0.5257 0.4349 0.3728 0.089 Uiso 1 1 d RD . . C2 C 0.44676(14) 0.50825(14) 0.2644(2) 0.0174(7) Uani 1 1 d . . . C3 C 0.50038(14) 0.56699(14) 0.2725(2) 0.0161(7) Uani 1 1 d . . . O8 O 0.5606(2) 0.6648(2) 0.6905(4) 0.0924(13) Uani 1 1 d D . . Zn1 Zn 0.345970(17) 0.414804(17) 0.14979(3) 0.01868(11) Uani 1 1 d . . . Zn2 Zn 0.5000 0.5000 0.5000 0.02875(16) Uani 1 2 d S . . H8A H 0.5758(19) 0.667(2) 0.6372(15) 0.043 Uiso 1 1 d D . . H8B H 0.5837(17) 0.6603(19) 0.728(2) 0.043 Uiso 1 1 d 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 C4 0.0189(18) 0.0167(18) 0.0177(18) 0.0013(15) -0.0022(15) 0.0072(15) C5 0.0219(17) 0.0193(18) 0.0124(17) 0.0020(14) -0.0019(15) 0.0088(15) C6 0.0167(17) 0.028(2) 0.0163(18) 0.0074(16) -0.0006(15) 0.0045(15) C7 0.0235(19) 0.031(2) 0.027(2) 0.0049(17) -0.0037(17) 0.0098(17) C8 0.024(2) 0.039(2) 0.036(2) 0.014(2) -0.0025(18) 0.0121(18) C9 0.024(2) 0.054(3) 0.026(2) 0.017(2) -0.0003(18) 0.012(2) C10 0.042(2) 0.053(3) 0.020(2) -0.002(2) -0.0083(19) 0.015(2) C11 0.037(2) 0.029(2) 0.022(2) 0.0037(17) -0.0030(18) 0.0086(18) C12 0.064(3) 0.063(3) 0.060(3) 0.024(3) -0.013(3) 0.037(3) C13 0.056(3) 0.096(4) 0.028(3) 0.021(3) -0.005(2) 0.038(3) N1 0.0171(14) 0.0152(14) 0.0158(14) 0.0008(12) -0.0010(12) 0.0046(12) N2 0.0187(14) 0.0168(14) 0.0135(14) 0.0034(12) -0.0003(12) 0.0052(12) O1 0.0506(17) 0.0250(14) 0.0202(15) 0.0117(12) -0.0153(13) -0.0033(12) O2 0.0219(12) 0.0181(12) 0.0166(12) 0.0006(10) -0.0036(11) 0.0043(10) O3 0.0220(12) 0.0174(12) 0.0186(13) 0.0020(11) -0.0069(11) 0.0004(10) O4 0.0282(14) 0.0313(14) 0.0171(13) 0.0085(12) -0.0095(12) -0.0037(11) O5 0.0518(19) 0.060(2) 0.075(2) -0.0307(19) -0.0114(17) 0.0353(17) O6 0.0584(18) 0.0302(15) 0.0382(17) 0.0078(14) -0.0037(15) 0.0157(14) C1 0.0180(18) 0.0191(18) 0.024(2) 0.0044(16) -0.0009(17) 0.0088(15) O7 0.0524(19) 0.058(2) 0.055(2) -0.0091(17) 0.0100(17) 0.0188(16) C2 0.0164(17) 0.0197(17) 0.0126(17) 0.0014(14) -0.0011(14) 0.0065(14) C3 0.0180(17) 0.0163(16) 0.0122(17) 0.0019(14) -0.0005(14) 0.0072(14) O8 0.083(3) 0.099(3) 0.114(4) -0.018(3) 0.007(3) 0.060(3) Zn1 0.0172(2) 0.0201(2) 0.0168(2) -0.00251(18) -0.00542(18) 0.00788(18) Zn2 0.0304(3) 0.0226(3) 0.0162(3) 0.0048(3) -0.0056(3) 0.0004(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 C4 O1 1.243(4) . ? C4 O2 1.269(3) . ? C4 C3 1.473(4) . ? C5 C6 1.463(4) . ? C5 N1 1.348(4) . ? C5 N2 1.344(4) . ? C6 C7 1.384(5) . ? C6 C11 1.397(5) . ? C7 H7 0.9300 . ? C7 C8 1.369(5) . ? C8 C9 1.395(5) . ? C8 C12 1.514(5) . ? C9 C10 1.388(5) . ? C9 C13 1.514(5) . ? C10 H10 0.9300 . ? C10 C11 1.387(5) . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? N1 C2 1.374(4) . ? N1 Zn1 2.062(2) . ? N2 C3 1.363(4) . ? N2 Zn1 2.069(2) 15 ? O1 Zn2 1.999(2) . ? O2 Zn1 2.106(2) 15 ? O3 C1 1.268(4) . ? O3 Zn1 2.111(2) . ? O4 C1 1.244(4) . ? O4 Zn2 2.048(2) . ? O5 H5A 0.8842 . ? O5 H5B 0.8805 . ? O5 Zn1 2.269(3) . ? O6 H6A 0.8657 . ? O6 H6B 0.9030 . ? O6 Zn1 2.206(2) . ? C1 C2 1.483(4) . ? O7 H7A 0.8718 . ? O7 H7B 0.8526 . ? O7 Zn2 2.167(3) . ? C2 C3 1.381(4) . ? O8 H8A 0.836(18) . ? O8 H8B 0.822(17) . ? Zn1 N2 2.069(2) 14_455 ? Zn1 O2 2.106(2) 14_455 ? Zn1 H6B 2.1275 . ? Zn2 O1 1.999(2) 10_666 ? Zn2 O4 2.048(2) 10_666 ? Zn2 O7 2.167(3) 10_666 ? 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 C4 O2 120.8(3) . . ? O1 C4 C3 122.7(3) . . ? O2 C4 C3 116.5(3) . . ? N1 C5 C6 124.0(3) . . ? N2 C5 C6 123.6(3) . . ? N2 C5 N1 112.1(3) . . ? C7 C6 C5 120.2(3) . . ? C7 C6 C11 117.7(3) . . ? C11 C6 C5 122.0(3) . . ? C6 C7 H7 118.5 . . ? C8 C7 C6 123.1(4) . . ? C8 C7 H7 118.5 . . ? C7 C8 C9 119.1(3) . . ? C7 C8 C12 120.0(4) . . ? C9 C8 C12 120.9(4) . . ? C8 C9 C13 121.8(4) . . ? C10 C9 C8 118.9(3) . . ? C10 C9 C13 119.3(4) . . ? C9 C10 H10 119.3 . . ? C11 C10 C9 121.3(4) . . ? C11 C10 H10 119.3 . . ? C6 C11 H11 120.1 . . ? C10 C11 C6 119.9(3) . . ? C10 C11 H11 120.1 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C5 N1 C2 105.5(2) . . ? C5 N1 Zn1 141.9(2) . . ? C2 N1 Zn1 112.6(2) . . ? C5 N2 C3 106.1(2) . . ? C5 N2 Zn1 140.5(2) . 15 ? C3 N2 Zn1 112.1(2) . 15 ? C4 O1 Zn2 140.9(2) . . ? C4 O2 Zn1 114.7(2) . 15 ? C1 O3 Zn1 115.8(2) . . ? C1 O4 Zn2 139.9(2) . . ? H5A O5 H5B 108.8 . . ? Zn1 O5 H5A 110.8 . . ? Zn1 O5 H5B 130.8 . . ? H6A O6 H6B 105.1 . . ? Zn1 O6 H6A 109.8 . . ? Zn1 O6 H6B 73.1 . . ? O3 C1 C2 115.5(3) . . ? O4 C1 O3 121.2(3) . . ? O4 C1 C2 123.3(3) . . ? H7A O7 H7B 116.3 . . ? Zn2 O7 H7A 110.1 . . ? Zn2 O7 H7B 118.9 . . ? N1 C2 C1 116.7(3) . . ? N1 C2 C3 108.1(3) . . ? C3 C2 C1 135.0(3) . . ? N2 C3 C4 116.3(3) . . ? N2 C3 C2 108.2(3) . . ? C2 C3 C4 135.5(3) . . ? H8A O8 H8B 107(3) . . ? N1 Zn1 N2 111.19(10) . 14_455 ? N1 Zn1 O2 112.13(9) . 14_455 ? N1 Zn1 O3 78.77(9) . . ? N1 Zn1 O5 83.24(10) . . ? N1 Zn1 O6 154.29(10) . . ? N1 Zn1 H6B 133.8 . . ? N2 Zn1 O2 78.66(9) 14_455 14_455 ? N2 Zn1 O3 102.74(10) 14_455 . ? N2 Zn1 O5 161.45(10) 14_455 . ? N2 Zn1 O6 91.29(10) 14_455 . ? N2 Zn1 H6B 114.6 14_455 . ? O2 Zn1 O3 167.93(8) 14_455 . ? O2 Zn1 O5 85.17(10) 14_455 . ? O2 Zn1 O6 83.62(9) 14_455 . ? O2 Zn1 H6B 83.5 14_455 . ? O3 Zn1 O5 91.22(10) . . ? O3 Zn1 O6 84.36(9) . . ? O3 Zn1 H6B 85.1 . . ? O5 Zn1 H6B 53.9 . . ? O6 Zn1 O5 77.83(10) . . ? O6 Zn1 H6B 24.0 . . ? O1 Zn2 O1 180.00(9) . 10_666 ? O1 Zn2 O4 85.46(9) 10_666 . ? O1 Zn2 O4 94.54(9) . . ? O1 Zn2 O4 85.46(9) . 10_666 ? O1 Zn2 O4 94.54(9) 10_666 10_666 ? O1 Zn2 O7 91.68(11) 10_666 10_666 ? O1 Zn2 O7 88.32(11) . 10_666 ? O1 Zn2 O7 91.68(11) . . ? O1 Zn2 O7 88.32(11) 10_666 . ? O4 Zn2 O4 180.0 10_666 . ? O4 Zn2 O7 88.21(11) 10_666 10_666 ? O4 Zn2 O7 91.79(11) . 10_666 ? O4 Zn2 O7 91.79(11) 10_666 . ? O4 Zn2 O7 88.21(11) . . ? O7 Zn2 O7 179.998(1) . 10_666 ? 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 O5 H5A O3 0.88 1.89 2.777(4) 179.8 9_554 O5 H5A O4 0.88 2.54 3.116(4) 123.2 9_554 O5 H5B O8 0.88 2.45 3.173(6) 139.8 10_666 O6 H6A O2 0.87 1.97 2.826(3) 170.3 18_545 O6 H6B O4 0.90 2.60 3.201(4) 124.6 9_554 O6 H6B O5 0.90 2.00 2.812(4) 149.5 . O7 H7A O8 0.87 1.97 2.836(5) 174.0 8_654 O7 H7B O8 0.85 2.46 3.270(6) 159.2 10_666 O8 H8A O6 0.836(18) 2.36(2) 3.172(5) 165(4) 17 O8 H8B O3 0.822(17) 2.71(3) 3.275(4) 128(3) 10_666 O8 H8B O5 0.822(17) 2.49(3) 3.173(6) 141(4) 10_666 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 C4 O1 Zn2 O1 -61(14) . . . 10_666 ? C4 O1 Zn2 O4 -35.3(4) . . . . ? C4 O1 Zn2 O4 144.7(4) . . . 10_666 ? C4 O1 Zn2 O7 -127.0(4) . . . 10_666 ? C4 O1 Zn2 O7 53.0(4) . . . . ? C5 C6 C7 C8 -176.2(3) . . . . ? C5 C6 C11 C10 176.4(3) . . . . ? C5 N1 C2 C1 175.4(3) . . . . ? C5 N1 C2 C3 -0.8(4) . . . . ? C5 N1 Zn1 N2 -76.9(4) . . . 14_455 ? C5 N1 Zn1 O2 9.1(4) . . . 14_455 ? C5 N1 Zn1 O3 -176.3(4) . . . . ? C5 N1 Zn1 O5 91.1(4) . . . . ? C5 N1 Zn1 O6 133.7(4) . . . . ? C5 N2 C3 C4 -178.5(3) . . . . ? C5 N2 C3 C2 0.1(3) . . . . ? C6 C5 N1 C2 -173.0(3) . . . . ? C6 C5 N1 Zn1 10.0(6) . . . . ? C6 C5 N2 C3 173.3(3) . . . . ? C6 C5 N2 Zn1 -21.4(5) . . . 15 ? C6 C7 C8 C9 -0.9(5) . . . . ? C6 C7 C8 C12 178.3(3) . . . . ? C7 C6 C11 C10 -1.3(5) . . . . ? C7 C8 C9 C10 -0.2(5) . . . . ? C7 C8 C9 C13 178.6(3) . . . . ? C8 C9 C10 C11 0.4(6) . . . . ? C9 C10 C11 C6 0.4(6) . . . . ? C11 C6 C7 C8 1.6(5) . . . . ? C12 C8 C9 C10 -179.3(4) . . . . ? C12 C8 C9 C13 -0.6(5) . . . . ? C13 C9 C10 C11 -178.4(4) . . . . ? N1 C5 C6 C7 132.0(3) . . . . ? N1 C5 C6 C11 -45.7(5) . . . . ? N1 C5 N2 C3 -0.7(4) . . . . ? N1 C5 N2 Zn1 164.7(2) . . . 15 ? N1 C2 C3 C4 178.7(3) . . . . ? N1 C2 C3 N2 0.4(4) . . . . ? N2 C5 C6 C7 -41.2(5) . . . . ? N2 C5 C6 C11 141.1(3) . . . . ? N2 C5 N1 C2 1.0(4) . . . . ? N2 C5 N1 Zn1 -176.1(2) . . . . ? O1 C4 O2 Zn1 174.6(3) . . . 15 ? O1 C4 C3 N2 175.1(3) . . . . ? O1 C4 C3 C2 -3.1(6) . . . . ? O2 C4 O1 Zn2 -156.4(3) . . . . ? O2 C4 C3 N2 -2.7(4) . . . . ? O2 C4 C3 C2 179.0(3) . . . . ? O3 C1 C2 N1 1.3(4) . . . . ? O3 C1 C2 C3 176.1(3) . . . . ? O4 C1 C2 N1 -178.6(3) . . . . ? O4 C1 C2 C3 -3.7(6) . . . . ? C1 O3 Zn1 N1 -6.5(2) . . . . ? C1 O3 Zn1 N2 -115.9(2) . . . 14_455 ? C1 O3 Zn1 O2 148.7(4) . . . 14_455 ? C1 O3 Zn1 O5 76.4(2) . . . . ? C1 O3 Zn1 O6 154.0(2) . . . . ? C1 O4 Zn2 O1 31.0(4) . . . . ? C1 O4 Zn2 O1 -149.0(4) . . . 10_666 ? C1 O4 Zn2 O4 -116.6(5) . . . 10_666 ? C1 O4 Zn2 O7 -60.5(4) . . . . ? C1 O4 Zn2 O7 119.5(4) . . . 10_666 ? C1 C2 C3 C4 3.6(6) . . . . ? C1 C2 C3 N2 -174.8(3) . . . . ? C2 N1 Zn1 N2 106.2(2) . . . 14_455 ? C2 N1 Zn1 O2 -167.8(2) . . . 14_455 ? C2 N1 Zn1 O3 6.7(2) . . . . ? C2 N1 Zn1 O5 -85.9(2) . . . . ? C2 N1 Zn1 O6 -43.2(4) . . . . ? C3 C4 O1 Zn2 25.8(6) . . . . ? C3 C4 O2 Zn1 -7.4(3) . . . 15 ? Zn1 N1 C2 C1 -6.6(4) . . . . ? Zn1 N1 C2 C3 177.20(19) . . . . ? Zn1 N2 C3 C4 11.4(3) 15 . . . ? Zn1 N2 C3 C2 -169.9(2) 15 . . . ? Zn1 O3 C1 O4 -175.4(3) . . . . ? Zn1 O3 C1 C2 4.8(4) . . . . ? Zn2 O4 C1 O3 161.9(2) . . . . ? Zn2 O4 C1 C2 -18.3(6) . . . . ? data_a2 _database_code_depnum_ccdc_archive 'CCDC 885611' #TrackingRef '- 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H34 Mn3 N4 O16' _chemical_formula_weight 823.39 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' Mn Mn 0.3368 0.7283 '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' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 25.043(7) _cell_length_b 25.043(7) _cell_length_c 14.612(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7936(5) _cell_formula_units_Z 9 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1014 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 18.91 _exptl_crystal_description CUBIC _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.551 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3789 _exptl_absorpt_coefficient_mu 1.132 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8222 _exptl_absorpt_correction_T_max 0.8397 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13700 _diffrn_reflns_av_R_equivalents 0.1421 _diffrn_reflns_av_sigmaI/netI 0.1421 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3294 _reflns_number_gt 1558 _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 'Bruker SHELXTL' _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. We have described as 24 restrains: ISOR 0.01 O5 > O8 ; _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^)+(0.1470P)^2^+16.0317P] 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 3294 _refine_ls_number_parameters 225 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1820 _refine_ls_R_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.2806 _refine_ls_wR_factor_gt 0.2223 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 1.000 _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 Mn1 Mn 0.25387(6) 0.26819(7) -0.02274(9) 0.0430(5) Uani 1 1 d . . . Mn2 Mn 0.3333 0.1667 -0.3333 0.0649(8) Uani 1 2 d S . . O1 O 0.3079(4) 0.0939(3) -0.2382(4) 0.075(2) Uani 1 1 d . . . O2 O 0.2870(3) 0.0310(3) -0.1234(4) 0.0529(18) Uani 1 1 d . . . O3 O 0.2693(3) 0.2544(3) -0.1648(4) 0.0491(17) Uani 1 1 d . . . O4 O 0.2789(4) 0.1942(3) -0.2648(4) 0.071(2) Uani 1 1 d . . . O5 O 0.3562(3) 0.3164(4) -0.0077(5) 0.074(2) Uani 1 1 d U . . H1W H 0.3751 0.3524 -0.0309 0.111 Uiso 1 1 d R . . H2W H 0.3805 0.3302 0.0378 0.111 Uiso 1 1 d R . . O6 O 0.2750(4) 0.3617(3) -0.0759(5) 0.076(2) Uani 1 1 d U . . H3W H 0.3025 0.3770 -0.1173 0.114 Uiso 1 1 d R . . H4W H 0.3033 0.3713 -0.0365 0.114 Uiso 1 1 d R . . O7 O 0.2538(5) 0.1064(5) -0.4228(8) 0.143(4) Uani 1 1 d U . . H5W H 0.2387 0.1252 -0.4459 0.214 Uiso 1 1 d R . . H6W H 0.2403 0.0720 -0.3956 0.214 Uiso 1 1 d R . . O8 O 0.2334(9) 0.2386(8) 0.4607(14) 0.266(9) Uani 1 1 d U . . H7W H 0.2502 0.2296 0.4175 0.399 Uiso 1 1 d R . . H8W H 0.2484 0.2570 0.5112 0.399 Uiso 1 1 d R . . N1 N 0.2436(4) 0.1758(3) -0.0270(4) 0.0437(19) Uani 1 1 d . . . N2 N 0.2557(4) 0.0932(4) -0.0089(5) 0.049(2) Uani 1 1 d . . . C1 C 0.2719(4) 0.2075(5) -0.1842(6) 0.050(2) Uani 1 1 d . . . C2 C 0.2647(4) 0.1650(4) -0.1078(5) 0.043(2) Uani 1 1 d . . . C3 C 0.2727(4) 0.1144(4) -0.0980(5) 0.047(2) Uani 1 1 d . . . C4 C 0.2907(4) 0.0787(4) -0.1581(6) 0.046(2) Uani 1 1 d . . . C5 C 0.2384(5) 0.1306(4) 0.0291(6) 0.047(2) Uani 1 1 d . . . C6 C 0.2109(5) 0.1204(5) 0.1213(6) 0.058(3) Uani 1 1 d . . . C7 C 0.2336(6) 0.1005(5) 0.1927(7) 0.072(3) Uani 1 1 d . . . H7 H 0.2675 0.0953 0.1842 0.086 Uiso 1 1 calc R . . C8 C 0.2038(8) 0.0886(5) 0.2777(7) 0.092(5) Uani 1 1 d . . . H8 H 0.2188 0.0758 0.3260 0.110 Uiso 1 1 calc R . . C9 C 0.1521(7) 0.0952(6) 0.2924(9) 0.092(5) Uani 1 1 d . . . C10 C 0.1294(6) 0.1161(5) 0.2204(9) 0.079(4) Uani 1 1 d . . . C11 C 0.1608(5) 0.1289(5) 0.1353(7) 0.063(3) Uani 1 1 d . . . H11 H 0.1473 0.1435 0.0872 0.075 Uiso 1 1 calc R . . C12 C 0.0732(7) 0.1228(7) 0.2269(12) 0.134(7) Uani 1 1 d . . . H12A H 0.0778 0.1495 0.2771 0.201 Uiso 1 1 calc R . . H12B H 0.0374 0.0831 0.2367 0.201 Uiso 1 1 calc R . . H12C H 0.0684 0.1402 0.1710 0.201 Uiso 1 1 calc R . . C13 C 0.1202(9) 0.0766(7) 0.3854(10) 0.143(7) Uani 1 1 d . . . H13A H 0.1465 0.0716 0.4282 0.215 Uiso 1 1 calc R . . H13B H 0.0820 0.0385 0.3796 0.215 Uiso 1 1 calc R . . H13C H 0.1122 0.1082 0.4069 0.215 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 Mn1 0.0525(10) 0.0544(10) 0.0250(7) -0.0040(6) 0.0018(6) 0.0288(8) Mn2 0.116(2) 0.0712(16) 0.0249(11) 0.0111(10) 0.0230(12) 0.0594(16) O1 0.148(7) 0.075(5) 0.028(4) 0.017(3) 0.035(4) 0.074(5) O2 0.089(5) 0.057(4) 0.028(3) 0.003(3) 0.006(3) 0.047(4) O3 0.077(5) 0.049(4) 0.032(4) 0.005(3) 0.010(3) 0.039(4) O4 0.133(7) 0.094(6) 0.024(3) 0.012(3) 0.026(4) 0.086(6) O5 0.060(4) 0.090(5) 0.052(4) -0.011(4) -0.008(3) 0.022(4) O6 0.088(5) 0.072(5) 0.067(5) 0.015(4) 0.014(4) 0.039(4) O7 0.142(7) 0.146(8) 0.114(7) -0.021(6) -0.003(6) 0.051(6) O8 0.265(12) 0.249(12) 0.261(13) -0.007(9) 0.000(9) 0.111(9) N1 0.065(5) 0.047(5) 0.023(4) -0.002(3) 0.003(4) 0.031(4) N2 0.070(6) 0.054(5) 0.028(4) 0.011(4) 0.008(4) 0.034(5) C1 0.065(7) 0.059(7) 0.032(5) 0.007(5) 0.000(5) 0.037(6) C2 0.067(7) 0.054(6) 0.020(4) 0.006(4) 0.007(4) 0.039(5) C3 0.062(6) 0.062(6) 0.019(4) 0.005(4) 0.007(4) 0.032(5) C4 0.068(7) 0.052(6) 0.025(5) -0.002(4) 0.006(4) 0.036(5) C5 0.070(7) 0.045(6) 0.030(5) 0.002(4) 0.006(5) 0.032(5) C6 0.079(8) 0.055(6) 0.032(6) 0.007(5) 0.013(5) 0.028(6) C7 0.116(10) 0.080(8) 0.034(6) 0.009(6) 0.016(6) 0.061(8) C8 0.180(15) 0.078(9) 0.025(6) 0.015(6) 0.016(7) 0.071(10) C9 0.152(14) 0.070(8) 0.072(9) 0.029(7) 0.065(9) 0.068(10) C10 0.105(10) 0.056(7) 0.071(8) 0.013(6) 0.038(7) 0.036(7) C11 0.086(8) 0.063(7) 0.050(6) 0.017(5) 0.030(6) 0.046(7) C12 0.130(14) 0.131(14) 0.146(16) 0.039(12) 0.087(12) 0.069(12) C13 0.23(2) 0.129(13) 0.089(11) 0.043(10) 0.101(13) 0.102(14) _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 Mn1 O3 2.170(6) . ? Mn1 O2 2.182(6) 12 ? Mn1 N2 2.200(8) 12 ? Mn1 N1 2.196(7) . ? Mn1 O5 2.232(7) . ? Mn1 O6 2.265(7) . ? Mn2 O4 2.068(6) 13_554 ? Mn2 O4 2.068(6) . ? Mn2 O1 2.121(6) . ? Mn2 O1 2.121(6) 13_554 ? Mn2 O7 2.225(11) 13_554 ? Mn2 O7 2.225(11) . ? O1 C4 1.240(10) . ? O2 C4 1.256(10) . ? O2 Mn1 2.182(6) 11 ? O3 C1 1.242(11) . ? O4 C1 1.260(10) . ? O5 H1W 0.8501 . ? O5 H2W 0.8501 . ? O6 H3W 0.8501 . ? O6 H4W 0.8501 . ? O7 H5W 0.8098 . ? O7 H6W 0.8499 . ? O8 H7W 0.8500 . ? O8 H8W 0.8501 . ? N1 C5 1.351(11) . ? N1 C2 1.375(10) . ? N2 C5 1.333(11) . ? N2 C3 1.389(10) . ? N2 Mn1 2.200(8) 11 ? C1 C2 1.490(12) . ? C2 C3 1.386(12) . ? C3 C4 1.476(12) . ? C5 C6 1.476(12) . ? C6 C11 1.390(14) . ? C6 C7 1.393(14) . ? C7 C8 1.402(15) . ? C7 H7 0.9300 . ? C8 C9 1.400(19) . ? C8 H8 0.9300 . ? C9 C10 1.414(18) . ? C9 C13 1.526(16) . ? C10 C11 1.420(14) . ? C10 C12 1.502(18) . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? 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 O3 Mn1 O2 169.6(2) . 12 ? O3 Mn1 N2 115.7(3) . 12 ? O2 Mn1 N2 74.7(2) 12 12 ? O3 Mn1 N1 75.1(2) . . ? O2 Mn1 N1 103.4(3) 12 . ? N2 Mn1 N1 106.8(3) 12 . ? O3 Mn1 O5 86.2(3) . . ? O2 Mn1 O5 83.7(2) 12 . ? N2 Mn1 O5 152.7(3) 12 . ? N1 Mn1 O5 94.1(3) . . ? O3 Mn1 O6 82.4(2) . . ? O2 Mn1 O6 98.3(3) 12 . ? N2 Mn1 O6 84.7(3) 12 . ? N1 Mn1 O6 157.4(3) . . ? O5 Mn1 O6 82.1(3) . . ? O4 Mn2 O4 179.999(1) 13_554 . ? O4 Mn2 O1 89.7(3) 13_554 . ? O4 Mn2 O1 90.3(3) . . ? O4 Mn2 O1 90.3(3) 13_554 13_554 ? O4 Mn2 O1 89.7(3) . 13_554 ? O1 Mn2 O1 179.997(1) . 13_554 ? O4 Mn2 O7 89.7(4) 13_554 13_554 ? O4 Mn2 O7 90.3(4) . 13_554 ? O1 Mn2 O7 88.9(4) . 13_554 ? O1 Mn2 O7 91.1(4) 13_554 13_554 ? O4 Mn2 O7 90.3(4) 13_554 . ? O4 Mn2 O7 89.7(4) . . ? O1 Mn2 O7 91.1(4) . . ? O1 Mn2 O7 88.9(4) 13_554 . ? O7 Mn2 O7 179.997(1) 13_554 . ? C4 O1 Mn2 142.3(6) . . ? C4 O2 Mn1 118.9(5) . 11 ? C1 O3 Mn1 117.8(6) . . ? C1 O4 Mn2 138.0(7) . . ? Mn1 O5 H1W 114.5 . . ? Mn1 O5 H2W 133.8 . . ? H1W O5 H2W 88.6 . . ? Mn1 O6 H3W 115.3 . . ? Mn1 O6 H4W 77.8 . . ? H3W O6 H4W 89.0 . . ? Mn2 O7 H5W 111.7 . . ? Mn2 O7 H6W 100.4 . . ? H5W O7 H6W 135.9 . . ? H7W O8 H8W 130.2 . . ? C5 N1 C2 103.9(7) . . ? C5 N1 Mn1 141.0(6) . . ? C2 N1 Mn1 112.2(6) . . ? C5 N2 C3 105.6(7) . . ? C5 N2 Mn1 141.8(6) . 11 ? C3 N2 Mn1 112.6(6) . 11 ? O3 C1 O4 122.9(8) . . ? O3 C1 C2 117.4(8) . . ? O4 C1 C2 119.7(9) . . ? N1 C2 C3 109.8(7) . . ? N1 C2 C1 115.0(8) . . ? C3 C2 C1 135.2(8) . . ? C2 C3 N2 106.7(7) . . ? C2 C3 C4 136.1(8) . . ? N2 C3 C4 117.1(8) . . ? O1 C4 O2 121.5(8) . . ? O1 C4 C3 122.7(9) . . ? O2 C4 C3 115.8(8) . . ? N1 C5 N2 114.0(8) . . ? N1 C5 C6 122.7(8) . . ? N2 C5 C6 123.1(8) . . ? C11 C6 C7 120.3(9) . . ? C11 C6 C5 119.1(9) . . ? C7 C6 C5 120.5(10) . . ? C6 C7 C8 118.1(12) . . ? C6 C7 H7 120.9 . . ? C8 C7 H7 120.9 . . ? C9 C8 C7 122.4(12) . . ? C9 C8 H8 118.8 . . ? C7 C8 H8 118.8 . . ? C8 C9 C10 119.8(11) . . ? C8 C9 C13 118.3(14) . . ? C10 C9 C13 121.9(14) . . ? C9 C10 C11 117.0(12) . . ? C9 C10 C12 124.6(12) . . ? C11 C10 C12 118.3(13) . . ? C6 C11 C10 122.4(11) . . ? C6 C11 H11 118.8 . . ? C10 C11 H11 118.8 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Mn2 O1 C4 153.0(13) 13_554 . . . ? O4 Mn2 O1 C4 -27.0(13) . . . . ? O1 Mn2 O1 C4 -27(2) 13_554 . . . ? O7 Mn2 O1 C4 63.3(13) 13_554 . . . ? O7 Mn2 O1 C4 -116.7(13) . . . . ? O2 Mn1 O3 C1 76.1(16) 12 . . . ? N2 Mn1 O3 C1 -108.7(7) 12 . . . ? N1 Mn1 O3 C1 -6.9(7) . . . . ? O5 Mn1 O3 C1 88.4(7) . . . . ? O6 Mn1 O3 C1 171.0(7) . . . . ? O4 Mn2 O4 C1 -128(11) 13_554 . . . ? O1 Mn2 O4 C1 52.2(11) . . . . ? O1 Mn2 O4 C1 -127.8(11) 13_554 . . . ? O7 Mn2 O4 C1 -36.6(11) 13_554 . . . ? O7 Mn2 O4 C1 143.4(11) . . . . ? O3 Mn1 N1 C5 169.5(11) . . . . ? O2 Mn1 N1 C5 0.2(11) 12 . . . ? N2 Mn1 N1 C5 -77.6(10) 12 . . . ? O5 Mn1 N1 C5 84.6(10) . . . . ? O6 Mn1 N1 C5 163.9(9) . . . . ? O3 Mn1 N1 C2 13.0(6) . . . . ? O2 Mn1 N1 C2 -156.3(6) 12 . . . ? N2 Mn1 N1 C2 125.9(6) 12 . . . ? O5 Mn1 N1 C2 -71.9(6) . . . . ? O6 Mn1 N1 C2 7.4(11) . . . . ? Mn1 O3 C1 O4 177.9(8) . . . . ? Mn1 O3 C1 C2 -0.4(11) . . . . ? Mn2 O4 C1 O3 132.3(9) . . . . ? Mn2 O4 C1 C2 -49.5(15) . . . . ? C5 N1 C2 C3 -1.0(11) . . . . ? Mn1 N1 C2 C3 164.1(6) . . . . ? C5 N1 C2 C1 177.4(8) . . . . ? Mn1 N1 C2 C1 -17.5(10) . . . . ? O3 C1 C2 N1 12.5(13) . . . . ? O4 C1 C2 N1 -165.8(9) . . . . ? O3 C1 C2 C3 -169.6(11) . . . . ? O4 C1 C2 C3 12.0(18) . . . . ? N1 C2 C3 N2 0.3(11) . . . . ? C1 C2 C3 N2 -177.6(10) . . . . ? N1 C2 C3 C4 176.6(11) . . . . ? C1 C2 C3 C4 -1(2) . . . . ? C5 N2 C3 C2 0.5(11) . . . . ? Mn1 N2 C3 C2 -177.9(6) 11 . . . ? C5 N2 C3 C4 -176.6(9) . . . . ? Mn1 N2 C3 C4 5.0(11) 11 . . . ? Mn2 O1 C4 O2 -171.3(8) . . . . ? Mn2 O1 C4 C3 9.5(19) . . . . ? Mn1 O2 C4 O1 171.9(8) 11 . . . ? Mn1 O2 C4 C3 -8.8(11) 11 . . . ? C2 C3 C4 O1 5.5(19) . . . . ? N2 C3 C4 O1 -178.5(9) . . . . ? C2 C3 C4 O2 -173.7(11) . . . . ? N2 C3 C4 O2 2.3(13) . . . . ? C2 N1 C5 N2 1.4(11) . . . . ? Mn1 N1 C5 N2 -156.3(8) . . . . ? C2 N1 C5 C6 -173.6(9) . . . . ? Mn1 N1 C5 C6 28.7(16) . . . . ? C3 N2 C5 N1 -1.2(12) . . . . ? Mn1 N2 C5 N1 176.4(7) 11 . . . ? C3 N2 C5 C6 173.7(9) . . . . ? Mn1 N2 C5 C6 -8.7(18) 11 . . . ? N1 C5 C6 C11 37.1(15) . . . . ? N2 C5 C6 C11 -137.4(11) . . . . ? N1 C5 C6 C7 -145.1(10) . . . . ? N2 C5 C6 C7 40.4(15) . . . . ? C11 C6 C7 C8 1.0(17) . . . . ? C5 C6 C7 C8 -176.8(10) . . . . ? C6 C7 C8 C9 0.8(18) . . . . ? C7 C8 C9 C10 -2(2) . . . . ? C7 C8 C9 C13 175.7(12) . . . . ? C8 C9 C10 C11 0.6(19) . . . . ? C13 C9 C10 C11 -176.6(12) . . . . ? C8 C9 C10 C12 177.7(13) . . . . ? C13 C9 C10 C12 0(2) . . . . ? C7 C6 C11 C10 -2.0(17) . . . . ? C5 C6 C11 C10 175.8(10) . . . . ? C9 C10 C11 C6 1.2(18) . . . . ? C12 C10 C11 C6 -176.1(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 O5 H1W O1 0.85 2.37 3.219(10) 179.5 17_554 O6 H3W O2 0.85 1.91 2.757(9) 179.4 17_554 O5 H2W O3 0.85 2.03 2.849(9) 161.4 5 O5 H2W O4 0.85 2.30 2.963(9) 135.5 5 O6 H4W O5 0.85 2.37 2.953(11) 125.8 . O7 H6W O8 0.85 1.91 2.43(2) 118.6 11 O8 H7W O6 0.85 2.64 3.42(2) 154.6 5 O8 H8W O5 0.85 2.49 3.34(2) 179.2 9 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.328 _refine_diff_density_min -0.525 _refine_diff_density_rms 0.117 data_a3 _database_code_depnum_ccdc_archive 'CCDC 885612' #TrackingRef '- 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 Mg N2 O6' _chemical_formula_weight 318.57 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' Mg Mg 0.0486 0.0363 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.901(4) _cell_length_b 6.2170(12) _cell_length_c 12.443(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.566(2) _cell_angle_gamma 90.00 _cell_volume 1320.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2830 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.19 _exptl_crystal_description lumpish _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.603 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9622 _exptl_absorpt_correction_T_max 0.9670 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7313 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 27.24 _reflns_number_total 2918 _reflns_number_gt 2357 _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, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. We have described as 8 restrains: DANG 1.387 0.02 H6b H6a. DANG 1.387 0.02 H5b H5a . SADI 0.02 Mg1 H6a Mg1 H6b. SADI 0.02 Mg1 H5a Mg1 H5b. DFIX 0.85 0.01 O6 H6a O6 H6b. DFIX 0.85 0.01 O5 H5a O5 H5b. ; _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^)+(0.0692P)^2^+0.3098P] 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 2918 _refine_ls_number_parameters 213 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.059 _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 Mg1 Mg 0.90845(3) 1.29554(9) 0.59852(4) 0.01709(17) Uani 1 1 d D . . O2 O 0.91857(7) 1.27738(19) 0.43829(9) 0.0223(3) Uani 1 1 d . . . O1 O 0.90784(7) 0.9713(2) 0.60494(9) 0.0256(3) Uani 1 1 d . . . O3 O 0.89402(8) 1.2745(2) 0.75503(10) 0.0259(3) Uani 1 1 d . . . O5 O 0.78134(8) 1.3265(2) 0.52467(11) 0.0296(3) Uani 1 1 d D . . O4 O 0.89193(7) 1.62035(19) 0.59247(10) 0.0253(3) Uani 1 1 d . . . N2 N 0.78647(8) 0.6594(2) 0.37571(12) 0.0204(3) Uani 1 1 d . . . N1 N 0.79348(8) 0.9009(2) 0.24937(11) 0.0212(3) Uani 1 1 d . . . H1 H 0.7852 0.9634 0.1852 0.025 Uiso 1 1 calc R . . C1 C 0.88878(9) 1.1732(3) 0.34943(13) 0.0175(3) Uani 1 1 d . . . C4 C 0.88200(9) 0.8046(3) 0.54982(13) 0.0174(3) Uani 1 1 d . . . C5 C 0.76162(10) 0.7126(3) 0.26714(14) 0.0207(4) Uani 1 1 d . . . C2 C 0.84114(9) 0.9761(3) 0.35031(13) 0.0186(3) Uani 1 1 d . . . C11 C 0.67879(11) 0.6676(3) 0.06774(15) 0.0268(4) Uani 1 1 d . . . H11 H 0.6973 0.7994 0.0511 0.032 Uiso 1 1 calc R . . C3 C 0.83635(10) 0.8232(3) 0.42827(13) 0.0177(3) Uani 1 1 d . . . C8 C 0.62383(12) 0.2784(3) 0.11613(17) 0.0345(5) Uani 1 1 d . . . H8 H 0.6056 0.1463 0.1329 0.041 Uiso 1 1 calc R . . C6 C 0.70531(10) 0.5900(3) 0.17762(14) 0.0223(4) Uani 1 1 d . . . C10 C 0.62535(10) 0.5537(3) -0.01805(15) 0.0279(4) Uani 1 1 d . . . C12 C 0.59820(14) 0.6451(4) -0.13559(18) 0.0454(6) Uani 1 1 d . . . H12A H 0.6225 0.7825 -0.1366 0.068 Uiso 1 1 calc R . . H12B H 0.5423 0.6623 -0.1586 0.068 Uiso 1 1 calc R . . H12C H 0.6125 0.5490 -0.1865 0.068 Uiso 1 1 calc R . . C7 C 0.67699(11) 0.3926(3) 0.20117(16) 0.0296(4) Uani 1 1 d . . . H7 H 0.6937 0.3374 0.2740 0.036 Uiso 1 1 calc R . . C9 C 0.59702(11) 0.3562(3) 0.00656(16) 0.0296(4) Uani 1 1 d . . . C13 C 0.53924(14) 0.2266(4) -0.08439(19) 0.0472(6) Uani 1 1 d . . . H13A H 0.4895 0.2987 -0.1069 0.071 Uiso 1 1 calc R . . H13B H 0.5332 0.0865 -0.0557 0.071 Uiso 1 1 calc R . . H13C H 0.5584 0.2123 -0.1482 0.071 Uiso 1 1 calc R . . O6 O 1.02570(7) 1.3463(2) 0.66374(10) 0.0252(3) Uani 1 1 d D . . H5A H 0.7729(10) 1.420(3) 0.4716(14) 0.038 Uiso 1 1 d D . . H5B H 0.7581(10) 1.212(2) 0.5005(17) 0.038 Uiso 1 1 d D . . H6A H 1.0411(10) 1.457(2) 0.6359(15) 0.038 Uiso 1 1 d D . . H6B H 1.0447(10) 1.352(4) 0.7338(8) 0.038 Uiso 1 1 d 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 Mg1 0.0283(3) 0.0122(3) 0.0114(3) 0.00007(19) 0.0069(2) -0.0003(2) O2 0.0354(7) 0.0196(6) 0.0129(6) -0.0039(5) 0.0088(5) -0.0073(5) O1 0.0461(8) 0.0131(6) 0.0147(6) -0.0017(4) 0.0049(5) -0.0018(5) O3 0.0464(8) 0.0210(7) 0.0131(6) 0.0006(5) 0.0133(5) 0.0067(5) O5 0.0330(7) 0.0283(7) 0.0268(7) 0.0070(6) 0.0079(6) -0.0040(5) O4 0.0440(8) 0.0130(6) 0.0166(6) 0.0013(5) 0.0057(5) 0.0002(5) N2 0.0274(7) 0.0176(7) 0.0158(7) -0.0004(5) 0.0060(6) -0.0039(6) N1 0.0312(8) 0.0208(8) 0.0109(7) 0.0008(5) 0.0055(6) -0.0046(6) C1 0.0253(8) 0.0158(8) 0.0128(8) 0.0000(6) 0.0077(6) 0.0010(6) C4 0.0266(8) 0.0131(8) 0.0140(8) 0.0003(6) 0.0085(6) 0.0000(6) C5 0.0265(9) 0.0204(9) 0.0153(8) -0.0007(6) 0.0065(7) -0.0025(7) C2 0.0268(8) 0.0171(8) 0.0126(8) -0.0016(6) 0.0068(6) -0.0014(6) C11 0.0316(10) 0.0271(10) 0.0203(9) -0.0002(7) 0.0057(7) -0.0061(7) C3 0.0258(8) 0.0134(8) 0.0144(8) -0.0014(6) 0.0069(6) 0.0001(6) C8 0.0422(11) 0.0286(11) 0.0309(11) -0.0031(8) 0.0081(9) -0.0136(8) C6 0.0263(9) 0.0233(9) 0.0168(8) -0.0033(7) 0.0059(7) -0.0032(7) C10 0.0284(9) 0.0347(11) 0.0186(9) -0.0031(8) 0.0039(7) -0.0019(8) C12 0.0548(14) 0.0551(15) 0.0191(10) 0.0014(10) 0.0002(9) -0.0106(11) C7 0.0395(11) 0.0278(10) 0.0195(9) 0.0012(7) 0.0059(8) -0.0088(8) C9 0.0302(10) 0.0343(11) 0.0236(10) -0.0093(8) 0.0070(8) -0.0073(8) C13 0.0478(13) 0.0549(15) 0.0342(12) -0.0148(11) 0.0053(10) -0.0219(11) O6 0.0302(7) 0.0263(7) 0.0179(6) -0.0019(5) 0.0053(5) -0.0029(5) _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 Mg1 O1 2.0174(14) . ? Mg1 O6 2.0335(14) . ? Mg1 O4 2.0390(14) . ? Mg1 O3 2.0446(13) . ? Mg1 O2 2.0589(13) . ? Mg1 O5 2.1903(15) . ? O2 C1 1.2532(19) . ? O1 C4 1.252(2) . ? O3 C1 1.249(2) 4_586 ? O5 H5A 0.859(9) . ? O5 H5B 0.834(9) . ? O4 C4 1.253(2) 1_565 ? N2 C5 1.330(2) . ? N2 C3 1.382(2) . ? N1 C5 1.349(2) . ? N1 C2 1.370(2) . ? N1 H1 0.8600 . ? C1 O3 1.249(2) 4_585 ? C1 C2 1.495(2) . ? C4 O4 1.253(2) 1_545 ? C4 C3 1.491(2) . ? C5 C6 1.470(2) . ? C2 C3 1.379(2) . ? C11 C10 1.393(2) . ? C11 C6 1.391(2) . ? C11 H11 0.9300 . ? C8 C7 1.386(3) . ? C8 C9 1.389(3) . ? C8 H8 0.9300 . ? C6 C7 1.392(3) . ? C10 C9 1.397(3) . ? C10 C12 1.506(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C7 H7 0.9300 . ? C9 C13 1.514(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? O6 H6A 0.855(9) . ? O6 H6B 0.836(9) . ? 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 Mg1 O6 99.01(6) . . ? O1 Mg1 O4 171.31(6) . . ? O6 Mg1 O4 88.96(6) . . ? O1 Mg1 O3 83.95(5) . . ? O6 Mg1 O3 92.40(6) . . ? O4 Mg1 O3 92.29(5) . . ? O1 Mg1 O2 89.24(5) . . ? O6 Mg1 O2 90.75(5) . . ? O4 Mg1 O2 94.17(5) . . ? O3 Mg1 O2 172.87(6) . . ? O1 Mg1 O5 94.99(6) . . ? O6 Mg1 O5 166.00(6) . . ? O4 Mg1 O5 77.10(5) . . ? O3 Mg1 O5 89.50(6) . . ? O2 Mg1 O5 88.99(5) . . ? C1 O2 Mg1 138.10(11) . . ? C4 O1 Mg1 144.19(11) . . ? C1 O3 Mg1 161.06(12) 4_586 . ? Mg1 O5 H5A 107.6(12) . . ? Mg1 O5 H5B 114.8(13) . . ? H5A O5 H5B 110.5(17) . . ? C4 O4 Mg1 157.22(11) 1_565 . ? C5 N2 C3 105.51(14) . . ? C5 N1 C2 108.84(14) . . ? C5 N1 H1 125.6 . . ? C2 N1 H1 125.6 . . ? O3 C1 O2 124.22(16) 4_585 . ? O3 C1 C2 115.16(14) 4_585 . ? O2 C1 C2 120.60(14) . . ? O1 C4 O4 122.91(15) . 1_545 ? O1 C4 C3 119.38(14) . . ? O4 C4 C3 117.70(14) 1_545 . ? N2 C5 N1 110.72(15) . . ? N2 C5 C6 125.68(16) . . ? N1 C5 C6 123.57(15) . . ? N1 C2 C3 104.83(14) . . ? N1 C2 C1 118.15(14) . . ? C3 C2 C1 136.62(15) . . ? C10 C11 C6 121.91(18) . . ? C10 C11 H11 119.0 . . ? C6 C11 H11 119.0 . . ? C2 C3 N2 110.09(14) . . ? C2 C3 C4 129.46(15) . . ? N2 C3 C4 120.07(14) . . ? C7 C8 C9 121.70(19) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C11 C6 C7 118.34(16) . . ? C11 C6 C5 121.16(16) . . ? C7 C6 C5 120.50(16) . . ? C11 C10 C9 119.31(17) . . ? C11 C10 C12 119.87(18) . . ? C9 C10 C12 120.81(17) . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C7 C6 120.02(18) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C8 C9 C10 118.71(17) . . ? C8 C9 C13 120.27(19) . . ? C10 C9 C13 121.01(18) . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? Mg1 O6 H6A 112.5(12) . . ? Mg1 O6 H6B 118.0(13) . . ? H6A O6 H6B 107.9(18) . . ? 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 Mg1 O2 C1 44.35(17) . . . . ? O6 Mg1 O2 C1 143.35(17) . . . . ? O4 Mg1 O2 C1 -127.64(17) . . . . ? O3 Mg1 O2 C1 27.2(5) . . . . ? O5 Mg1 O2 C1 -50.65(17) . . . . ? O6 Mg1 O1 C4 -132.0(2) . . . . ? O4 Mg1 O1 C4 71.9(4) . . . . ? O3 Mg1 O1 C4 136.6(2) . . . . ? O2 Mg1 O1 C4 -41.3(2) . . . . ? O5 Mg1 O1 C4 47.6(2) . . . . ? O1 Mg1 O3 C1 172.0(4) . . . 4_586 ? O6 Mg1 O3 C1 73.2(4) . . . 4_586 ? O4 Mg1 O3 C1 -15.9(4) . . . 4_586 ? O2 Mg1 O3 C1 -170.7(4) . . . 4_586 ? O5 Mg1 O3 C1 -92.9(4) . . . 4_586 ? O1 Mg1 O4 C4 -107.4(4) . . . 1_565 ? O6 Mg1 O4 C4 96.1(3) . . . 1_565 ? O3 Mg1 O4 C4 -171.5(3) . . . 1_565 ? O2 Mg1 O4 C4 5.4(3) . . . 1_565 ? O5 Mg1 O4 C4 -82.6(3) . . . 1_565 ? Mg1 O2 C1 O3 164.15(13) . . . 4_585 ? Mg1 O2 C1 C2 -13.8(3) . . . . ? Mg1 O1 C4 O4 -173.76(13) . . . 1_545 ? Mg1 O1 C4 C3 5.4(3) . . . . ? C3 N2 C5 N1 0.06(19) . . . . ? C3 N2 C5 C6 -178.10(16) . . . . ? C2 N1 C5 N2 -0.3(2) . . . . ? C2 N1 C5 C6 177.93(16) . . . . ? C5 N1 C2 C3 0.37(19) . . . . ? C5 N1 C2 C1 174.29(14) . . . . ? O3 C1 C2 N1 -15.0(2) 4_585 . . . ? O2 C1 C2 N1 163.19(15) . . . . ? O3 C1 C2 C3 156.46(19) 4_585 . . . ? O2 C1 C2 C3 -25.4(3) . . . . ? N1 C2 C3 N2 -0.34(19) . . . . ? C1 C2 C3 N2 -172.53(18) . . . . ? N1 C2 C3 C4 172.49(16) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C5 N2 C3 C2 0.19(19) . . . . ? C5 N2 C3 C4 -173.42(15) . . . . ? O1 C4 C3 C2 29.1(3) . . . . ? O4 C4 C3 C2 -151.72(17) 1_545 . . . ? O1 C4 C3 N2 -158.73(16) . . . . ? O4 C4 C3 N2 20.5(2) 1_545 . . . ? C10 C11 C6 C7 -0.1(3) . . . . ? C10 C11 C6 C5 -179.89(17) . . . . ? N2 C5 C6 C11 175.31(18) . . . . ? N1 C5 C6 C11 -2.6(3) . . . . ? N2 C5 C6 C7 -4.5(3) . . . . ? N1 C5 C6 C7 177.56(17) . . . . ? C6 C11 C10 C9 0.3(3) . . . . ? C6 C11 C10 C12 179.76(19) . . . . ? C9 C8 C7 C6 -0.4(3) . . . . ? C11 C6 C7 C8 0.1(3) . . . . ? C5 C6 C7 C8 179.93(18) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C7 C8 C9 C13 179.7(2) . . . . ? C11 C10 C9 C8 -0.6(3) . . . . ? C12 C10 C9 C8 179.9(2) . . . . ? C11 C10 C9 C13 -179.63(19) . . . . ? C12 C10 C9 C13 1.0(3) . . . . ? 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 N1 H1 O5 0.86 2.37 3.221(2) 170.1 4_585 N1 H1 O4 0.86 2.57 3.0020(19) 112.5 4_585 O5 H5A N2 0.859(9) 1.967(11) 2.798(2) 162.5(17) 1_565 O6 H6A O2 0.855(9) 2.120(9) 2.9740(18) 177(2) 3_786 O6 H6B O4 0.836(9) 2.561(15) 3.2635(18) 142(2) 2_746 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.24 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.519 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.069 data_20110582 _database_code_depnum_ccdc_archive 'CCDC 885613' #TrackingRef '- 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 Ca N2 O6' _chemical_formula_weight 334.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ca Ca 0.3641 1.2855 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.4040(10) _cell_length_b 6.8778(2) _cell_length_c 12.9582(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.484(6) _cell_angle_gamma 90.00 _cell_volume 1401.91(12) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1594 _cell_measurement_theta_min 3.5541 _cell_measurement_theta_max 66.9625 _exptl_crystal_description PRISMATIC _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 4.179 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.3225 _exptl_absorpt_correction_T_max 0.4886 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5221 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 5.63 _diffrn_reflns_theta_max 67.07 _reflns_number_total 2504 _reflns_number_gt 2070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT v7.53A (Bruker, 2008)' _computing_cell_refinement 'SAINT v7.53A (Bruker, 2008)' _computing_data_reduction 'SAINT v7.53A (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (Sheldrick, 1997)' _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^)+(0.0572P)^2^+0.0357P] 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 2504 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Ca1 Ca 0.06425(3) 1.34126(7) 0.73866(4) 0.02345(17) Uani 1 1 d . . . O1 O 0.12996(13) 1.3009(3) 0.59868(15) 0.0327(5) Uani 1 1 d . . . O2 O 0.11156(13) 1.2364(3) 0.42598(14) 0.0360(5) Uani 1 1 d . . . O3 O 0.05617(12) 1.0010(3) 0.70584(16) 0.0302(4) Uani 1 1 d . . . O4 O 0.07720(12) 0.6838(3) 0.72166(16) 0.0317(5) Uani 1 1 d . . . O5 O 0.22528(13) 1.4056(3) 0.80586(16) 0.0394(5) Uani 1 1 d . . . H1W H 0.2530 1.2996 0.8182 0.059 Uiso 1 1 d R . . H2W H 0.2313 1.4459 0.8696 0.047 Uiso 1 1 d R . . O6 O -0.04649(13) 1.3900(3) 0.57700(16) 0.0397(5) Uani 1 1 d . . . H3W H -0.0829 1.4804 0.5706 0.060 Uiso 1 1 d R . . H4W H -0.0223 1.3840 0.5272 0.060 Uiso 1 1 d R . . N1 N 0.22158(14) 0.9120(3) 0.49818(17) 0.0267(5) Uani 1 1 d . . . N2 N 0.20203(14) 0.6977(3) 0.61511(18) 0.0277(5) Uani 1 1 d . . . H2 H 0.2058 0.5914 0.6512 0.033 Uiso 1 1 calc R . . C1 C 0.13280(17) 1.1902(4) 0.5233(2) 0.0243(6) Uani 1 1 d . . . C2 C 0.16842(17) 0.9903(4) 0.5520(2) 0.0240(5) Uani 1 1 d . . . C3 C 0.15509(17) 0.8582(4) 0.6257(2) 0.0243(5) Uani 1 1 d . . . C4 C 0.09301(16) 0.8481(4) 0.6898(2) 0.0238(5) Uani 1 1 d . . . C5 C 0.24107(17) 0.7350(4) 0.5387(2) 0.0274(6) Uani 1 1 d . . . C6 C 0.3219(2) 0.6416(4) 0.4124(2) 0.0380(7) Uani 1 1 d . . . H6A H 0.3026 0.7558 0.3750 0.046 Uiso 1 1 calc R . . C7 C 0.29705(18) 0.5985(4) 0.5042(2) 0.0296(6) Uani 1 1 d . . . C8 C 0.32631(19) 0.4283(4) 0.5594(2) 0.0370(7) Uani 1 1 d . . . H8 H 0.3110 0.3967 0.6212 0.044 Uiso 1 1 calc R . . C9 C 0.3784(2) 0.3059(5) 0.5220(3) 0.0441(8) Uani 1 1 d . . . H9 H 0.3971 0.1912 0.5593 0.053 Uiso 1 1 calc R . . C10 C 0.4039(2) 0.3477(5) 0.4306(3) 0.0397(7) Uani 1 1 d . . . C11 C 0.3747(2) 0.5185(5) 0.3750(2) 0.0389(7) Uani 1 1 d . . . C12 C 0.4599(3) 0.2075(6) 0.3917(3) 0.0622(11) Uani 1 1 d . . . H12C H 0.5176 0.2525 0.4142 0.093 Uiso 1 1 calc R . . H12A H 0.4409 0.2000 0.3146 0.093 Uiso 1 1 calc R . . H12B H 0.4566 0.0810 0.4217 0.093 Uiso 1 1 calc R . . C13 C 0.3999(3) 0.5753(7) 0.2757(3) 0.0690(13) Uani 1 1 d . . . H13B H 0.3824 0.7067 0.2563 0.103 Uiso 1 1 calc R . . H13A H 0.3727 0.4899 0.2175 0.103 Uiso 1 1 calc R . . H13C H 0.4605 0.5654 0.2901 0.103 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 Ca1 0.0377(3) 0.0139(3) 0.0218(3) 0.00030(19) 0.0135(2) 0.00136(19) O1 0.0594(13) 0.0172(9) 0.0290(10) -0.0017(8) 0.0246(9) 0.0005(9) O2 0.0579(13) 0.0279(11) 0.0231(10) 0.0025(8) 0.0131(9) 0.0107(9) O3 0.0427(11) 0.0153(10) 0.0407(11) -0.0008(8) 0.0247(9) 0.0019(8) O4 0.0452(12) 0.0142(9) 0.0429(11) 0.0017(8) 0.0245(9) -0.0001(8) O5 0.0488(13) 0.0400(12) 0.0310(10) -0.0028(9) 0.0138(9) 0.0031(10) O6 0.0505(13) 0.0357(12) 0.0305(10) -0.0012(9) 0.0076(9) 0.0093(10) N1 0.0359(12) 0.0220(11) 0.0270(11) 0.0001(9) 0.0164(10) 0.0026(9) N2 0.0368(13) 0.0184(11) 0.0324(12) 0.0049(9) 0.0171(10) 0.0052(9) C1 0.0326(14) 0.0178(13) 0.0255(13) -0.0010(10) 0.0133(11) -0.0015(10) C2 0.0337(14) 0.0181(13) 0.0223(12) -0.0009(10) 0.0115(10) 0.0019(10) C3 0.0313(14) 0.0178(12) 0.0259(13) -0.0015(10) 0.0114(11) -0.0004(10) C4 0.0339(14) 0.0146(12) 0.0253(12) 0.0001(10) 0.0122(10) 0.0012(10) C5 0.0345(14) 0.0224(13) 0.0289(13) 0.0002(11) 0.0148(11) 0.0017(11) C6 0.0487(18) 0.0308(15) 0.0401(16) 0.0057(13) 0.0218(14) 0.0108(13) C7 0.0348(15) 0.0255(14) 0.0322(14) -0.0028(12) 0.0154(12) 0.0012(11) C8 0.0459(17) 0.0315(16) 0.0404(16) 0.0050(13) 0.0234(14) 0.0064(13) C9 0.056(2) 0.0312(17) 0.0514(19) 0.0084(15) 0.0248(16) 0.0158(15) C10 0.0414(17) 0.0394(18) 0.0423(17) -0.0073(14) 0.0181(14) 0.0078(14) C11 0.0435(17) 0.0453(19) 0.0339(15) -0.0004(14) 0.0207(13) 0.0084(14) C12 0.071(3) 0.063(3) 0.064(2) 0.000(2) 0.038(2) 0.028(2) C13 0.091(3) 0.082(3) 0.050(2) 0.020(2) 0.046(2) 0.035(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 Ca1 O1 2.3746(18) . ? Ca1 O3 2.3755(18) . ? Ca1 O6 2.375(2) . ? Ca1 O4 2.3810(18) 1_565 ? Ca1 O2 2.3897(19) 4_586 ? Ca1 O3 2.5363(18) 2_556 ? Ca1 O5 2.574(2) . ? Ca1 O4 2.7384(19) 2_556 ? Ca1 C4 2.979(3) 2_556 ? Ca1 Ca1 4.0875(6) 2_546 ? Ca1 Ca1 4.0875(6) 2_556 ? Ca1 H4W 2.7210 . ? O1 C1 1.250(3) . ? O2 C1 1.251(3) . ? O2 Ca1 2.3897(19) 4_585 ? O3 C4 1.259(3) . ? O3 Ca1 2.5363(18) 2_546 ? O4 C4 1.255(3) . ? O4 Ca1 2.3810(18) 1_545 ? O4 Ca1 2.7384(19) 2_546 ? O5 H1W 0.8499 . ? O5 H2W 0.8500 . ? O6 H3W 0.8499 . ? O6 H4W 0.8501 . ? N1 C5 1.328(3) . ? N1 C2 1.372(3) . ? N2 C5 1.348(3) . ? N2 C3 1.375(3) . ? N2 H2 0.8600 . ? C1 C2 1.499(3) . ? C2 C3 1.380(4) . ? C3 C4 1.487(3) . ? C4 Ca1 2.979(3) 2_546 ? C5 C7 1.469(4) . ? C6 C11 1.394(4) . ? C6 C7 1.394(4) . ? C6 H6A 0.9300 . ? C7 C8 1.385(4) . ? C8 C9 1.381(4) . ? C8 H8 0.9300 . ? C9 C10 1.393(4) . ? C9 H9 0.9300 . ? C10 C11 1.390(4) . ? C10 C12 1.514(4) . ? C11 C13 1.511(4) . ? C12 H12C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C13 H13B 0.9600 . ? C13 H13A 0.9600 . ? C13 H13C 0.9600 . ? 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 Ca1 O3 76.25(6) . . ? O1 Ca1 O6 75.06(7) . . ? O3 Ca1 O6 89.49(7) . . ? O1 Ca1 O4 88.48(7) . 1_565 ? O3 Ca1 O4 163.74(7) . 1_565 ? O6 Ca1 O4 81.08(7) . 1_565 ? O1 Ca1 O2 131.51(7) . 4_586 ? O3 Ca1 O2 86.97(7) . 4_586 ? O6 Ca1 O2 150.94(8) . 4_586 ? O4 Ca1 O2 107.66(7) 1_565 4_586 ? O1 Ca1 O3 145.71(7) . 2_556 ? O3 Ca1 O3 117.98(5) . 2_556 ? O6 Ca1 O3 74.14(7) . 2_556 ? O4 Ca1 O3 72.22(6) 1_565 2_556 ? O2 Ca1 O3 82.15(7) 4_586 2_556 ? O1 Ca1 O5 68.52(7) . . ? O3 Ca1 O5 103.29(7) . . ? O6 Ca1 O5 136.78(7) . . ? O4 Ca1 O5 75.60(7) 1_565 . ? O2 Ca1 O5 71.85(7) 4_586 . ? O3 Ca1 O5 129.54(7) 2_556 . ? O1 Ca1 O4 133.60(7) . 2_556 ? O3 Ca1 O4 68.70(6) . 2_556 ? O6 Ca1 O4 75.20(7) . 2_556 ? O4 Ca1 O4 120.75(5) 1_565 2_556 ? O2 Ca1 O4 76.65(7) 4_586 2_556 ? O3 Ca1 O4 49.35(6) 2_556 2_556 ? O5 Ca1 O4 147.93(6) . 2_556 ? O1 Ca1 C4 149.36(7) . 2_556 ? O3 Ca1 C4 93.55(7) . 2_556 ? O6 Ca1 C4 76.06(7) . 2_556 ? O4 Ca1 C4 96.95(7) 1_565 2_556 ? O2 Ca1 C4 75.39(7) 4_586 2_556 ? O3 Ca1 C4 24.77(6) 2_556 2_556 ? O5 Ca1 C4 142.02(7) . 2_556 ? O4 Ca1 C4 24.91(6) 2_556 2_556 ? O1 Ca1 Ca1 108.15(5) . 2_546 ? O3 Ca1 Ca1 34.95(4) . 2_546 ? O6 Ca1 Ca1 84.32(6) . 2_546 ? O4 Ca1 Ca1 154.20(5) 1_565 2_546 ? O2 Ca1 Ca1 76.37(5) 4_586 2_546 ? O3 Ca1 Ca1 83.40(4) 2_556 2_546 ? O5 Ca1 Ca1 128.39(5) . 2_546 ? O4 Ca1 Ca1 34.10(4) 2_556 2_546 ? C4 Ca1 Ca1 58.74(5) 2_556 2_546 ? O1 Ca1 Ca1 120.56(5) . 2_556 ? O3 Ca1 Ca1 146.93(5) . 2_556 ? O6 Ca1 Ca1 70.35(5) . 2_556 ? O4 Ca1 Ca1 40.15(5) 1_565 2_556 ? O2 Ca1 Ca1 98.08(5) 4_586 2_556 ? O3 Ca1 Ca1 32.45(4) 2_556 2_556 ? O5 Ca1 Ca1 109.37(5) . 2_556 ? O4 Ca1 Ca1 80.65(4) 2_556 2_556 ? C4 Ca1 Ca1 56.94(5) 2_556 2_556 ? Ca1 Ca1 Ca1 114.56(2) 2_546 2_556 ? O1 Ca1 H4W 57.5 . . ? O3 Ca1 H4W 86.5 . . ? O6 Ca1 H4W 17.6 . . ? O4 Ca1 H4W 80.5 1_565 . ? O2 Ca1 H4W 166.8 4_586 . ? O3 Ca1 H4W 90.8 2_556 . ? O5 Ca1 H4W 120.9 . . ? O4 Ca1 H4W 90.2 2_556 . ? C4 Ca1 H4W 93.5 2_556 . ? Ca1 Ca1 H4W 91.8 2_546 . ? Ca1 Ca1 H4W 81.3 2_556 . ? C1 O1 Ca1 142.56(18) . . ? C1 O2 Ca1 152.22(18) . 4_585 ? C4 O3 Ca1 147.92(17) . . ? C4 O3 Ca1 97.69(15) . 2_546 ? Ca1 O3 Ca1 112.61(7) . 2_546 ? C4 O4 Ca1 162.42(17) . 1_545 ? C4 O4 Ca1 88.33(15) . 2_546 ? Ca1 O4 Ca1 105.75(7) 1_545 2_546 ? Ca1 O5 H1W 111.0 . . ? Ca1 O5 H2W 102.1 . . ? H1W O5 H2W 100.8 . . ? Ca1 O6 H3W 122.0 . . ? Ca1 O6 H4W 104.9 . . ? H3W O6 H4W 115.4 . . ? C5 N1 C2 106.0(2) . . ? C5 N2 C3 108.5(2) . . ? C5 N2 H2 125.8 . . ? C3 N2 H2 125.8 . . ? O1 C1 O2 124.9(2) . . ? O1 C1 C2 117.6(2) . . ? O2 C1 C2 117.5(2) . . ? N1 C2 C3 110.0(2) . . ? N1 C2 C1 119.5(2) . . ? C3 C2 C1 130.5(2) . . ? N2 C3 C2 104.9(2) . . ? N2 C3 C4 120.7(2) . . ? C2 C3 C4 133.2(2) . . ? O4 C4 O3 123.0(2) . . ? O4 C4 C3 117.6(2) . . ? O3 C4 C3 119.3(2) . . ? O4 C4 Ca1 66.76(14) . 2_546 ? O3 C4 Ca1 57.54(13) . 2_546 ? C3 C4 Ca1 164.86(18) . 2_546 ? N1 C5 N2 110.7(2) . . ? N1 C5 C7 124.5(2) . . ? N2 C5 C7 124.8(2) . . ? C11 C6 C7 121.9(3) . . ? C11 C6 H6A 119.1 . . ? C7 C6 H6A 119.1 . . ? C8 C7 C6 118.6(3) . . ? C8 C7 C5 122.5(3) . . ? C6 C7 C5 118.9(3) . . ? C9 C8 C7 119.5(3) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 122.5(3) . . ? C8 C9 H9 118.8 . . ? C10 C9 H9 118.8 . . ? C11 C10 C9 118.2(3) . . ? C11 C10 C12 121.2(3) . . ? C9 C10 C12 120.6(3) . . ? C10 C11 C6 119.3(3) . . ? C10 C11 C13 121.6(3) . . ? C6 C11 C13 119.1(3) . . ? C10 C12 H12C 109.5 . . ? C10 C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C13 H13B 109.5 . . ? C11 C13 H13A 109.5 . . ? H13B C13 H13A 109.5 . . ? C11 C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Ca1 O1 C1 24.1(3) . . . . ? O6 Ca1 O1 C1 -69.1(3) . . . . ? O4 Ca1 O1 C1 -150.2(3) 1_565 . . . ? O2 Ca1 O1 C1 97.3(3) 4_586 . . . ? O3 Ca1 O1 C1 -95.8(3) 2_556 . . . ? O5 Ca1 O1 C1 134.7(3) . . . . ? O4 Ca1 O1 C1 -17.3(3) 2_556 . . . ? C4 Ca1 O1 C1 -49.1(4) 2_556 . . . ? Ca1 Ca1 O1 C1 9.7(3) 2_546 . . . ? Ca1 Ca1 O1 C1 -124.9(3) 2_556 . . . ? O1 Ca1 O3 C4 44.9(3) . . . . ? O6 Ca1 O3 C4 119.6(3) . . . . ? O4 Ca1 O3 C4 65.4(5) 1_565 . . . ? O2 Ca1 O3 C4 -89.2(3) 4_586 . . . ? O3 Ca1 O3 C4 -168.7(4) 2_556 . . . ? O5 Ca1 O3 C4 -18.7(3) . . . . ? O4 Ca1 O3 C4 -166.1(4) 2_556 . . . ? C4 Ca1 O3 C4 -164.4(3) 2_556 . . . ? Ca1 Ca1 O3 C4 -159.6(4) 2_546 . . . ? Ca1 Ca1 O3 C4 170.6(3) 2_556 . . . ? O1 Ca1 O3 Ca1 -155.52(10) . . . 2_546 ? O6 Ca1 O3 Ca1 -80.79(9) . . . 2_546 ? O4 Ca1 O3 Ca1 -135.0(2) 1_565 . . 2_546 ? O2 Ca1 O3 Ca1 70.35(9) 4_586 . . 2_546 ? O3 Ca1 O3 Ca1 -9.10(5) 2_556 . . 2_546 ? O5 Ca1 O3 Ca1 140.91(8) . . . 2_546 ? O4 Ca1 O3 Ca1 -6.49(7) 2_556 . . 2_546 ? C4 Ca1 O3 Ca1 -4.79(9) 2_556 . . 2_546 ? Ca1 Ca1 O3 Ca1 -29.82(14) 2_556 . . 2_546 ? Ca1 O1 C1 O2 117.4(3) . . . . ? Ca1 O1 C1 C2 -65.8(4) . . . . ? Ca1 O2 C1 O1 -156.6(3) 4_585 . . . ? Ca1 O2 C1 C2 26.6(5) 4_585 . . . ? C5 N1 C2 C3 -0.4(3) . . . . ? C5 N1 C2 C1 -178.6(2) . . . . ? O1 C1 C2 N1 -138.6(3) . . . . ? O2 C1 C2 N1 38.4(4) . . . . ? O1 C1 C2 C3 43.6(4) . . . . ? O2 C1 C2 C3 -139.4(3) . . . . ? C5 N2 C3 C2 0.1(3) . . . . ? C5 N2 C3 C4 169.1(2) . . . . ? N1 C2 C3 N2 0.2(3) . . . . ? C1 C2 C3 N2 178.2(3) . . . . ? N1 C2 C3 C4 -166.7(3) . . . . ? C1 C2 C3 C4 11.2(5) . . . . ? Ca1 O4 C4 O3 156.8(5) 1_545 . . . ? Ca1 O4 C4 O3 13.0(3) 2_546 . . . ? Ca1 O4 C4 C3 -20.1(8) 1_545 . . . ? Ca1 O4 C4 C3 -163.9(2) 2_546 . . . ? Ca1 O4 C4 Ca1 143.8(6) 1_545 . . 2_546 ? Ca1 O3 C4 O4 146.9(2) . . . . ? Ca1 O3 C4 O4 -14.1(3) 2_546 . . . ? Ca1 O3 C4 C3 -36.2(5) . . . . ? Ca1 O3 C4 C3 162.7(2) 2_546 . . . ? Ca1 O3 C4 Ca1 161.1(4) . . . 2_546 ? N2 C3 C4 O4 -9.0(4) . . . . ? C2 C3 C4 O4 156.3(3) . . . . ? N2 C3 C4 O3 174.0(2) . . . . ? C2 C3 C4 O3 -20.7(5) . . . . ? N2 C3 C4 Ca1 -112.2(6) . . . 2_546 ? C2 C3 C4 Ca1 53.1(8) . . . 2_546 ? C2 N1 C5 N2 0.5(3) . . . . ? C2 N1 C5 C7 -179.9(3) . . . . ? C3 N2 C5 N1 -0.4(3) . . . . ? C3 N2 C5 C7 -180.0(3) . . . . ? C11 C6 C7 C8 0.2(5) . . . . ? C11 C6 C7 C5 -179.9(3) . . . . ? N1 C5 C7 C8 169.6(3) . . . . ? N2 C5 C7 C8 -10.8(4) . . . . ? N1 C5 C7 C6 -10.3(4) . . . . ? N2 C5 C7 C6 169.3(3) . . . . ? C6 C7 C8 C9 -0.5(5) . . . . ? C5 C7 C8 C9 179.6(3) . . . . ? C7 C8 C9 C10 0.8(5) . . . . ? C8 C9 C10 C11 -0.7(5) . . . . ? C8 C9 C10 C12 -179.0(3) . . . . ? C9 C10 C11 C6 0.3(5) . . . . ? C12 C10 C11 C6 178.7(3) . . . . ? C9 C10 C11 C13 179.6(4) . . . . ? C12 C10 C11 C13 -2.1(5) . . . . ? C7 C6 C11 C10 -0.1(5) . . . . ? C7 C6 C11 C13 -179.3(3) . . . . ? 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 O5 H2W N1 0.85 1.98 2.806(3) 164.8 4_586 N2 H2 O1 0.86 2.35 2.958(3) 127.9 1_545 N2 H2 O5 0.86 2.32 3.123(3) 155.2 1_545 O6 H3W O1 0.85 2.59 3.132(3) 122.7 3_586 O6 H3W O2 0.85 2.01 2.779(3) 150.5 3_586 O6 H4W O6 0.85 2.53 3.214(4) 138.8 3_586 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 67.07 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.605 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.066