# 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_1 _database_code_depnum_ccdc_archive 'CCDC 886200' #TrackingRef 'All.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 N2 O6' _chemical_formula_weight 280.24 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 6.4778(14) _cell_length_b 7.3896(11) _cell_length_c 26.049(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.345(16) _cell_angle_gamma 90.00 _cell_volume 1241.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3358 _cell_measurement_theta_min 1.57 _cell_measurement_theta_max 27.30 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9584 _exptl_absorpt_correction_T_max 0.9783 _exptl_absorpt_process_details 'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate ( 34 cm diameter )' _diffrn_detector_type STOE _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 4153 _diffrn_reflns_av_R_equivalents 0.0716 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.73 _reflns_number_total 1301 _reflns_number_gt 1027 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1301 _refine_ls_number_parameters 98 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0970 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.29808(18) 0.80465(18) 0.37316(5) 0.0405(3) Uani 1 1 d D . . H1N H 0.369(3) 0.707(2) 0.3647(8) 0.049 Uiso 1 1 d D . . O1 O 0.05725(19) 0.82732(17) 0.45310(5) 0.0551(3) Uani 1 1 d D . . H1 H -0.024(3) 0.869(3) 0.4704(9) 0.066 Uiso 1 1 d D . . O2 O 0.22797(17) 1.07004(15) 0.48424(5) 0.0540(3) Uani 1 1 d . . . O3 O 0.07594(16) 1.02751(15) 0.34905(4) 0.0502(3) Uani 1 1 d . . . C1 C 0.2079(2) 0.94058(19) 0.45464(6) 0.0407(3) Uani 1 1 d . . . C2 C 0.3736(2) 0.9042(2) 0.41861(6) 0.0421(4) Uani 1 1 d . . . H2A H 0.4310 1.0212 0.4080 0.051 Uiso 1 1 calc R . . H2B H 0.4877 0.8352 0.4374 0.051 Uiso 1 1 calc R . . C3 C 0.1490(2) 0.8773(2) 0.34067(6) 0.0404(4) Uani 1 1 d . . . C4 C 0.0749(2) 0.7701(2) 0.29422(5) 0.0392(3) Uani 1 1 d . . . C5 C 0.0765(2) 0.5809(2) 0.29392(6) 0.0403(4) Uani 1 1 d . . . H5A H 0.1299 0.5160 0.3237 0.048 Uiso 1 1 calc R . . C6 C 0.0000 0.4890(3) 0.2500 0.0415(5) Uani 1 2 d S . . H6A H 0.0000 0.3604 0.2500 0.050 Uiso 1 2 calc SR . . C7 C 0.0000 0.8619(3) 0.2500 0.0394(5) Uani 1 2 d S . . H7A H 0.0000 0.9905 0.2500 0.047 Uiso 1 2 calc SR . . 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 N1 0.0445(6) 0.0417(7) 0.0352(7) -0.0039(5) 0.0041(5) 0.0065(5) O1 0.0575(7) 0.0604(7) 0.0498(7) -0.0129(5) 0.0179(5) -0.0136(6) O2 0.0625(7) 0.0500(6) 0.0516(7) -0.0147(5) 0.0168(6) -0.0076(5) O3 0.0520(6) 0.0476(6) 0.0502(7) -0.0090(5) 0.0012(5) 0.0125(5) C1 0.0476(7) 0.0408(8) 0.0335(7) -0.0005(6) 0.0034(6) -0.0001(6) C2 0.0435(7) 0.0450(8) 0.0379(8) -0.0041(6) 0.0039(6) 0.0013(6) C3 0.0407(7) 0.0427(7) 0.0389(8) 0.0008(6) 0.0094(6) 0.0047(6) C4 0.0357(7) 0.0446(8) 0.0381(8) -0.0014(6) 0.0078(6) 0.0024(6) C5 0.0400(7) 0.0429(8) 0.0385(8) 0.0030(6) 0.0071(6) 0.0026(6) C6 0.0422(10) 0.0390(10) 0.0444(12) 0.000 0.0090(8) 0.000 C7 0.0389(9) 0.0399(10) 0.0402(11) 0.000 0.0076(8) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.336(2) . ? N1 C2 1.440(2) . ? N1 H1N 0.892(17) . ? O1 C1 1.2834(18) . ? O1 H1 0.79(2) . ? O2 C1 1.2280(18) . ? O3 C3 1.2342(18) . ? C1 C2 1.514(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.488(2) . ? C4 C7 1.3851(18) . ? C4 C5 1.398(2) . ? C5 C6 1.3821(18) . ? C5 H5A 0.9500 . ? C6 C5 1.3822(18) 2 ? C6 H6A 0.9500 . ? C7 C4 1.3851(18) 2 ? C7 H7A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C2 119.04(13) . . ? C3 N1 H1N 121.8(13) . . ? C2 N1 H1N 118.1(12) . . ? C1 O1 H1 105.9(16) . . ? O2 C1 O1 124.28(14) . . ? O2 C1 C2 119.19(13) . . ? O1 C1 C2 116.48(13) . . ? N1 C2 C1 113.22(12) . . ? N1 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? N1 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? O3 C3 N1 121.05(14) . . ? O3 C3 C4 121.51(13) . . ? N1 C3 C4 117.44(13) . . ? C7 C4 C5 119.18(14) . . ? C7 C4 C3 118.49(14) . . ? C5 C4 C3 122.33(13) . . ? C6 C5 C4 119.60(15) . . ? C6 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? C5 C6 C5 121.11(19) . 2 ? C5 C6 H6A 119.4 . . ? C5 C6 H6A 119.4 2 . ? C4 C7 C4 121.32(19) . 2 ? C4 C7 H7A 119.3 . . ? C4 C7 H7A 119.3 2 . ? 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 H1N O3 0.892(17) 1.957(18) 2.8352(17) 167.9(15) 3_545 O1 H1 O2 0.79(2) 1.91(2) 2.6860(17) 170(2) 5_576 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.159 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.049 data_2 _database_code_depnum_ccdc_archive 'CCDC 886201' #TrackingRef 'All.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H64 Mg2 N4 O35' _chemical_formula_weight 1017.41 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2573(10) _cell_length_b 12.1847(16) _cell_length_c 14.7493(18) _cell_angle_alpha 106.389(10) _cell_angle_beta 102.151(9) _cell_angle_gamma 100.772(9) _cell_volume 1180.3(3) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9049 _cell_measurement_theta_min 1.50 _cell_measurement_theta_max 26.11 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.158 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9324 _exptl_absorpt_correction_T_max 0.9616 _exptl_absorpt_process_details 'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate ( 34 cm diameter )' _diffrn_detector_type STOE _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 7070 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.61 _reflns_number_total 4356 _reflns_number_gt 3703 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+0.5922P] 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 4356 _refine_ls_number_parameters 353 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.050 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mg1 Mg 0.36682(9) 0.21137(5) 0.22372(4) 0.02242(17) Uani 1 1 d . . . O1 O 1.0699(2) -0.13641(14) 0.05123(11) 0.0341(4) Uani 1 1 d . . . O2 O 1.1820(2) -0.13261(13) 0.20451(10) 0.0297(3) Uani 1 1 d . . . O3 O 0.7701(2) -0.03238(12) 0.20881(10) 0.0265(3) Uani 1 1 d . . . O4 O 0.7983(2) 0.27609(12) 0.50678(10) 0.0266(3) Uani 1 1 d . . . O5 O 1.1627(2) 0.40534(12) 0.71691(11) 0.0282(3) Uani 1 1 d . . . O6 O 1.0335(2) 0.55961(12) 0.73616(11) 0.0297(3) Uani 1 1 d . . . O7 O 0.4560(2) 0.06643(13) 0.23928(11) 0.0290(3) Uani 1 1 d D . . H72 H 0.560(4) 0.050(2) 0.228(2) 0.043 Uiso 1 1 d D . . H71 H 0.374(4) 0.000(2) 0.227(2) 0.043 Uiso 1 1 d D . . O8 O 0.2226(2) 0.10795(14) 0.07923(11) 0.0312(3) Uani 1 1 d D . . H82 H 0.139(4) 0.127(3) 0.045(2) 0.047 Uiso 1 1 d D . . H81 H 0.189(4) 0.039(2) 0.071(2) 0.047 Uiso 1 1 d D . . O9 O 0.6104(2) 0.26201(14) 0.17955(12) 0.0327(3) Uani 1 1 d D . . H92 H 0.708(4) 0.321(2) 0.206(2) 0.049 Uiso 1 1 d D . . H91 H 0.608(4) 0.226(3) 0.121(2) 0.049 Uiso 1 1 d D . . O10 O 0.2633(2) 0.34859(13) 0.19936(12) 0.0316(3) Uani 1 1 d D . . H101 H 0.168(4) 0.376(3) 0.220(2) 0.047 Uiso 1 1 d D . . H102 H 0.330(4) 0.402(2) 0.180(2) 0.047 Uiso 1 1 d D . . O11 O 0.1255(2) 0.15568(14) 0.26975(12) 0.0321(3) Uani 1 1 d D . . H112 H 0.099(4) 0.206(3) 0.315(2) 0.048 Uiso 1 1 d D . . H111 H 0.027(4) 0.102(2) 0.241(2) 0.048 Uiso 1 1 d D . . O12 O 0.5079(2) 0.31230(13) 0.36737(11) 0.0297(3) Uani 1 1 d D . . H122 H 0.534(4) 0.386(2) 0.384(2) 0.045 Uiso 1 1 d D . . H121 H 0.586(4) 0.295(3) 0.409(2) 0.045 Uiso 1 1 d D . . O13 O 0.6191(3) 0.54989(14) 0.41658(13) 0.0372(4) Uani 1 1 d D . . H131 H 0.685(5) 0.560(3) 0.378(2) 0.056 Uiso 1 1 d D . . H132 H 0.705(4) 0.585(3) 0.475(2) 0.056 Uiso 1 1 d D . . O14 O 0.9363(2) 0.66394(14) 0.59123(12) 0.0348(4) Uani 1 1 d D . . H141 H 0.969(5) 0.622(3) 0.627(2) 0.052 Uiso 1 1 d D . . H142 H 1.028(4) 0.683(3) 0.564(2) 0.052 Uiso 1 1 d D . . O15 O 0.5068(3) 0.50547(19) 0.86552(16) 0.0536(5) Uani 1 1 d D . . H151 H 0.407(5) 0.463(3) 0.813(2) 0.080 Uiso 1 1 d D . . H152 H 0.485(6) 0.522(3) 0.922(2) 0.080 Uiso 1 1 d D . . O16 O 0.3574(3) 0.6151(2) 0.01711(18) 0.0691(6) Uani 1 1 d D . . H161 H 0.2476 0.5915 0.0308 0.104 Uiso 1 1 d RD . . H162 H 0.4448 0.6602 0.0728 0.104 Uiso 1 1 d RD . . O17 O 0.4172(3) 0.84499(19) 0.01757(14) 0.0583(5) Uani 1 1 d D . . H171 H 0.5060 0.9088 0.0500 0.087 Uiso 1 1 d RD . . H172 H 0.3127 0.8537 0.0324 0.087 Uiso 1 1 d RD . . N1 N 0.8048(2) -0.21070(15) 0.21291(12) 0.0242(3) Uani 1 1 d D . . H1N H 0.818(4) -0.255(2) 0.2459(18) 0.036 Uiso 1 1 d D . . N2 N 0.8008(2) 0.24531(14) 0.64961(12) 0.0238(3) Uani 1 1 d D . . H2N H 0.809(4) 0.205(2) 0.6846(19) 0.036 Uiso 1 1 d D . . C1 C 1.0498(3) -0.16324(17) 0.12605(14) 0.0253(4) Uani 1 1 d . . . C2 C 0.8494(3) -0.23807(17) 0.11902(14) 0.0262(4) Uani 1 1 d . . . H2A H 0.7477 -0.2239 0.0706 0.031 Uiso 1 1 calc R . . H2B H 0.8463 -0.3231 0.0949 0.031 Uiso 1 1 calc R . . C3 C 0.7752(3) -0.10563(17) 0.25378(14) 0.0227(4) Uani 1 1 d . . . C4 C 0.7524(3) -0.07644(17) 0.35561(14) 0.0219(4) Uani 1 1 d . . . C5 C 0.7818(3) 0.04218(17) 0.40924(14) 0.0221(4) Uani 1 1 d . . . H5 H 0.8116 0.1007 0.3796 0.027 Uiso 1 1 calc R . . C6 C 0.7686(3) 0.07702(17) 0.50524(14) 0.0218(4) Uani 1 1 d . . . C7 C 0.7271(3) -0.00942(17) 0.54900(14) 0.0245(4) Uani 1 1 d . . . H7 H 0.7204 0.0133 0.6151 0.029 Uiso 1 1 calc R . . C8 C 0.6960(3) -0.12798(17) 0.49569(15) 0.0256(4) Uani 1 1 d . . . H8 H 0.6668 -0.1864 0.5254 0.031 Uiso 1 1 calc R . . C9 C 0.7069(3) -0.16228(17) 0.39935(14) 0.0242(4) Uani 1 1 d . . . H9 H 0.6836 -0.2439 0.3631 0.029 Uiso 1 1 calc R . . C10 C 0.7916(3) 0.20625(17) 0.55470(14) 0.0222(4) Uani 1 1 d . . . C11 C 0.8185(3) 0.36953(17) 0.69849(15) 0.0258(4) Uani 1 1 d . . . H11A H 0.7875 0.3786 0.7620 0.031 Uiso 1 1 calc R . . H11B H 0.7208 0.3954 0.6574 0.031 Uiso 1 1 calc R . . C12 C 1.0214(3) 0.45082(17) 0.71807(14) 0.0241(4) Uani 1 1 d . . . O18 O 0.9668(11) 0.5062(7) 0.9436(5) 0.116(2) Uiso 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mg1 0.0202(3) 0.0227(3) 0.0239(3) 0.0082(3) 0.0052(3) 0.0047(3) O1 0.0296(8) 0.0481(9) 0.0270(7) 0.0173(7) 0.0083(6) 0.0081(7) O2 0.0266(7) 0.0347(8) 0.0262(7) 0.0147(6) 0.0035(6) 0.0017(6) O3 0.0300(7) 0.0262(7) 0.0282(7) 0.0134(6) 0.0108(6) 0.0093(6) O4 0.0311(7) 0.0250(7) 0.0265(7) 0.0125(6) 0.0081(6) 0.0078(6) O5 0.0258(7) 0.0249(7) 0.0357(8) 0.0111(6) 0.0095(6) 0.0084(6) O6 0.0295(7) 0.0210(7) 0.0384(8) 0.0099(6) 0.0094(6) 0.0063(6) O7 0.0221(7) 0.0260(7) 0.0394(8) 0.0134(6) 0.0063(6) 0.0066(6) O8 0.0314(8) 0.0269(8) 0.0290(8) 0.0087(6) -0.0012(6) 0.0049(6) O9 0.0277(8) 0.0343(8) 0.0314(8) 0.0063(7) 0.0117(6) 0.0002(6) O10 0.0305(8) 0.0296(8) 0.0428(9) 0.0180(7) 0.0153(7) 0.0120(6) O11 0.0268(8) 0.0287(8) 0.0379(8) 0.0069(7) 0.0137(7) 0.0018(6) O12 0.0328(8) 0.0252(7) 0.0265(7) 0.0078(6) 0.0014(6) 0.0058(6) O13 0.0413(9) 0.0311(8) 0.0353(8) 0.0096(7) 0.0095(7) 0.0038(7) O14 0.0362(9) 0.0369(9) 0.0368(8) 0.0167(7) 0.0151(7) 0.0104(7) O15 0.0438(11) 0.0547(12) 0.0571(12) 0.0316(10) 0.0002(9) -0.0035(9) O16 0.0552(13) 0.0810(16) 0.0739(14) 0.0372(13) 0.0101(11) 0.0158(11) O17 0.0385(10) 0.0765(14) 0.0467(11) -0.0011(10) 0.0184(8) 0.0106(9) N1 0.0262(8) 0.0226(8) 0.0270(8) 0.0101(7) 0.0101(7) 0.0078(7) N2 0.0265(8) 0.0205(8) 0.0235(8) 0.0085(6) 0.0058(7) 0.0039(6) C1 0.0269(10) 0.0274(10) 0.0246(10) 0.0095(8) 0.0090(8) 0.0104(8) C2 0.0258(10) 0.0258(10) 0.0247(9) 0.0057(8) 0.0073(8) 0.0054(8) C3 0.0165(8) 0.0242(9) 0.0257(9) 0.0082(8) 0.0048(7) 0.0034(7) C4 0.0163(8) 0.0243(9) 0.0258(9) 0.0099(8) 0.0055(7) 0.0052(7) C5 0.0192(9) 0.0230(9) 0.0251(9) 0.0112(8) 0.0048(7) 0.0044(7) C6 0.0166(9) 0.0239(9) 0.0239(9) 0.0090(7) 0.0030(7) 0.0045(7) C7 0.0227(9) 0.0291(10) 0.0229(9) 0.0106(8) 0.0065(7) 0.0063(8) C8 0.0242(10) 0.0247(10) 0.0301(10) 0.0137(8) 0.0073(8) 0.0049(8) C9 0.0221(9) 0.0216(9) 0.0296(10) 0.0085(8) 0.0085(8) 0.0060(7) C10 0.0166(8) 0.0243(9) 0.0243(9) 0.0092(8) 0.0030(7) 0.0032(7) C11 0.0252(10) 0.0235(10) 0.0274(10) 0.0066(8) 0.0074(8) 0.0061(8) C12 0.0266(10) 0.0241(10) 0.0207(9) 0.0075(7) 0.0061(7) 0.0056(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mg1 O10 2.0454(16) . ? Mg1 O7 2.0453(15) . ? Mg1 O12 2.0483(16) . ? Mg1 O9 2.0578(16) . ? Mg1 O8 2.0684(16) . ? Mg1 O11 2.0744(16) . ? O1 C1 1.265(2) . ? O2 C1 1.247(2) . ? O3 C3 1.255(2) . ? O4 C10 1.251(2) . ? O5 C12 1.255(2) . ? O6 C12 1.258(2) . ? O7 H72 0.85(3) . ? O7 H71 0.86(2) . ? O8 H82 0.82(3) . ? O8 H81 0.80(3) . ? O9 H92 0.84(3) . ? O9 H91 0.84(3) . ? O10 H101 0.90(3) . ? O10 H102 0.88(3) . ? O11 H112 0.85(3) . ? O11 H111 0.82(3) . ? O12 H122 0.83(3) . ? O12 H121 0.85(3) . ? O13 H131 0.83(3) . ? O13 H132 0.88(3) . ? O14 H141 0.86(3) . ? O14 H142 0.87(3) . ? O15 H151 0.89(3) . ? O15 H152 0.85(3) . ? O16 H161 0.8799 . ? O16 H162 0.8800 . ? O17 H171 0.8500 . ? O17 H172 0.8495 . ? N1 C3 1.330(3) . ? N1 C2 1.450(3) . ? N1 H1N 0.83(2) . ? N2 C10 1.328(3) . ? N2 C11 1.449(2) . ? N2 H2N 0.80(2) . ? C1 C2 1.531(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.495(3) . ? C4 C5 1.389(3) . ? C4 C9 1.400(3) . ? C5 C6 1.388(3) . ? C5 H5 0.9500 . ? C6 C7 1.401(3) . ? C6 C10 1.497(3) . ? C7 C8 1.385(3) . ? C7 H7 0.9500 . ? C8 C9 1.387(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C11 C12 1.532(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? O18 O18 1.689(15) 2_767 ? 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 O10 Mg1 O7 176.01(7) . . ? O10 Mg1 O12 91.15(7) . . ? O7 Mg1 O12 92.68(7) . . ? O10 Mg1 O9 91.73(7) . . ? O7 Mg1 O9 89.29(7) . . ? O12 Mg1 O9 91.72(7) . . ? O10 Mg1 O8 89.23(7) . . ? O7 Mg1 O8 86.93(7) . . ? O12 Mg1 O8 179.32(7) . . ? O9 Mg1 O8 88.84(7) . . ? O10 Mg1 O11 90.35(7) . . ? O7 Mg1 O11 88.66(7) . . ? O12 Mg1 O11 88.01(7) . . ? O9 Mg1 O11 177.91(7) . . ? O8 Mg1 O11 91.42(7) . . ? Mg1 O7 H72 125.3(19) . . ? Mg1 O7 H71 121.6(19) . . ? H72 O7 H71 106(3) . . ? Mg1 O8 H82 122(2) . . ? Mg1 O8 H81 114(2) . . ? H82 O8 H81 110(3) . . ? Mg1 O9 H92 132(2) . . ? Mg1 O9 H91 117(2) . . ? H92 O9 H91 111(3) . . ? Mg1 O10 H101 127.6(18) . . ? Mg1 O10 H102 121.9(19) . . ? H101 O10 H102 109(3) . . ? Mg1 O11 H112 118(2) . . ? Mg1 O11 H111 130(2) . . ? H112 O11 H111 108(3) . . ? Mg1 O12 H122 119(2) . . ? Mg1 O12 H121 128(2) . . ? H122 O12 H121 108(3) . . ? H131 O13 H132 103(3) . . ? H141 O14 H142 110(3) . . ? H151 O15 H152 117(4) . . ? H161 O16 H162 107.7 . . ? H171 O17 H172 107.7 . . ? C3 N1 C2 120.14(16) . . ? C3 N1 H1N 119.1(18) . . ? C2 N1 H1N 119.8(18) . . ? C10 N2 C11 120.11(16) . . ? C10 N2 H2N 123.9(19) . . ? C11 N2 H2N 115.7(19) . . ? O2 C1 O1 124.26(19) . . ? O2 C1 C2 118.35(17) . . ? O1 C1 C2 117.39(17) . . ? N1 C2 C1 112.27(16) . . ? N1 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? N1 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? O3 C3 N1 120.94(18) . . ? O3 C3 C4 120.97(17) . . ? N1 C3 C4 118.07(16) . . ? C5 C4 C9 119.07(17) . . ? C5 C4 C3 117.71(16) . . ? C9 C4 C3 123.21(17) . . ? C6 C5 C4 121.31(17) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 119.13(18) . . ? C5 C6 C10 117.16(16) . . ? C7 C6 C10 123.66(17) . . ? C8 C7 C6 119.87(18) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.68(17) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C4 119.92(18) . . ? C8 C9 H9 120.0 . . ? C4 C9 H9 120.0 . . ? O4 C10 N2 120.45(17) . . ? O4 C10 C6 120.40(17) . . ? N2 C10 C6 119.13(16) . . ? N2 C11 C12 113.92(16) . . ? N2 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? N2 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? O5 C12 O6 124.91(18) . . ? O5 C12 C11 118.32(17) . . ? O6 C12 C11 116.76(17) . . ? 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 O7 H72 O3 0.85(3) 2.00(3) 2.828(2) 164(3) . O7 H71 O2 0.86(2) 1.82(3) 2.677(2) 174(3) 1_455 O8 H82 O1 0.82(3) 1.89(3) 2.694(2) 168(3) 2_655 O8 H81 O1 0.80(3) 2.06(3) 2.854(2) 173(3) 1_455 O9 H92 O6 0.84(3) 1.99(3) 2.823(2) 170(3) 2_766 O9 H91 O17 0.84(3) 1.94(3) 2.777(2) 173(3) 2_665 O10 H101 O6 0.90(3) 1.92(3) 2.821(2) 178(3) 2_666 O10 H102 O15 0.88(3) 1.84(3) 2.717(2) 170(3) 2_666 O11 H112 O14 0.85(3) 1.88(3) 2.729(2) 170(3) 2_666 O11 H111 O3 0.82(3) 2.10(3) 2.892(2) 163(3) 1_455 O12 H122 O13 0.83(3) 1.86(3) 2.693(2) 173(3) . O12 H121 O4 0.85(3) 1.97(3) 2.811(2) 171(3) . O13 H131 O5 0.83(3) 2.04(3) 2.877(2) 176(3) 2_766 O13 H132 O14 0.88(3) 1.99(3) 2.855(2) 169(3) . O14 H141 O6 0.86(3) 1.97(3) 2.814(2) 165(3) . O14 H142 O4 0.87(3) 1.88(3) 2.753(2) 173(3) 2_766 O15 H151 O5 0.89(3) 1.89(3) 2.753(2) 164(4) 1_455 O15 H152 O16 0.85(3) 2.04(3) 2.799(4) 148(4) 1_556 O16 H161 O18 0.88 1.95 2.795(8) 161.8 2_666 O16 H161 O18 0.88 2.06 2.732(8) 132.6 1_454 O17 H171 O3 0.85 2.51 3.146(2) 131.9 1_565 O17 H172 O1 0.85 1.86 2.707(2) 174.0 1_465 N1 H1N O5 0.83(2) 2.08(2) 2.871(2) 161(3) 2_756 N2 H2N O2 0.80(2) 2.07(2) 2.855(2) 168(3) 2_756 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.743 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.056 data_3 _database_code_depnum_ccdc_archive 'CCDC 886202' #TrackingRef 'All.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Ca N2 O8' _chemical_formula_weight 354.33 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' Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 6.6529(11) _cell_length_b 25.696(6) _cell_length_c 8.8244(14) _cell_angle_alpha 90.00 _cell_angle_beta 105.668(12) _cell_angle_gamma 90.00 _cell_volume 1452.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 1370 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 23.26 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.478 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9449 _exptl_absorpt_correction_T_max 0.9765 _exptl_absorpt_process_details 'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate ( 34 cm diameter )' _diffrn_detector_type STOE _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 3404 _diffrn_reflns_av_R_equivalents 0.1602 _diffrn_reflns_av_sigmaI/netI 0.1968 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.61 _reflns_number_total 1375 _reflns_number_gt 571 _reflns_threshold_expression >2\s(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0207P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1375 _refine_ls_number_parameters 114 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1677 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.933 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ca1 Ca 0.0000 0.20507(6) 0.5000 0.0377(5) Uani 1 2 d S . . O1 O 0.2522(5) 0.23614(14) 0.3464(4) 0.0439(10) Uani 1 1 d . . . O2 O 0.0211(5) 0.17709(14) 0.2351(4) 0.0449(10) Uani 1 1 d . . . O3 O 0.3968(5) 0.09268(13) 0.2585(5) 0.0451(10) Uani 1 1 d . . . N1 N 0.2634(6) 0.14087(17) 0.0437(5) 0.0388(11) Uani 1 1 d . . . H1A H 0.2003 0.1422 -0.0577 0.047 Uiso 1 1 calc R . . C1 C 0.1869(7) 0.2006(2) 0.2452(6) 0.0381(13) Uani 1 1 d . . . C2 C 0.3204(9) 0.1888(2) 0.1344(6) 0.0418(14) Uani 1 1 d . . . H2A H 0.3094 0.2183 0.0603 0.050 Uiso 1 1 calc R . . H2B H 0.4681 0.1863 0.1967 0.050 Uiso 1 1 calc R . . C3 C 0.3084(7) 0.0952(2) 0.1165(7) 0.0391(13) Uani 1 1 d . . . C4 C 0.2583(7) 0.0476(2) 0.0180(6) 0.0363(12) Uani 1 1 d . . . C5 C 0.2939(9) 0.0000 0.0997(9) 0.0359(18) Uani 1 2 d S . . H5 H 0.3426 0.0000 0.2113 0.043 Uiso 1 2 calc SR . . C7 C 0.1849(7) 0.0473(2) -0.1440(7) 0.0418(14) Uani 1 1 d . . . H7A H 0.1566 0.0793 -0.1998 0.050 Uiso 1 1 calc R . . C8 C 0.1518(11) 0.0000 -0.2266(9) 0.044(2) Uani 1 2 d S . . H8 H 0.1070 0.0000 -0.3384 0.053 Uiso 1 2 calc SR . . O4 O 0.2456(6) 0.13246(16) 0.5371(5) 0.0530(11) Uani 1 1 d D . . H41 H 0.270(9) 0.139(2) 0.448(5) 0.064 Uiso 1 1 d D . . H42 H 0.365(7) 0.126(2) 0.618(5) 0.064 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 Ca1 0.0281(8) 0.0455(10) 0.0359(10) 0.000 0.0023(7) 0.000 O1 0.041(2) 0.047(2) 0.042(2) -0.009(2) 0.0071(17) -0.0041(18) O2 0.033(2) 0.058(3) 0.041(2) -0.001(2) 0.0047(16) 0.0014(19) O3 0.041(2) 0.048(2) 0.038(2) 0.001(2) -0.0021(18) -0.0025(19) N1 0.036(2) 0.041(3) 0.035(3) 0.000(2) 0.003(2) 0.004(2) C1 0.027(3) 0.045(3) 0.038(3) 0.005(3) 0.003(2) 0.003(3) C2 0.048(3) 0.039(3) 0.037(3) 0.004(3) 0.011(3) -0.005(3) C3 0.025(3) 0.048(4) 0.039(4) 0.000(3) -0.001(2) 0.001(3) C4 0.027(2) 0.044(3) 0.033(3) 0.002(3) -0.001(2) -0.001(2) C5 0.020(3) 0.050(5) 0.034(5) 0.000 0.001(3) 0.000 C7 0.028(3) 0.049(3) 0.043(4) 0.001(3) 0.000(2) -0.002(3) C8 0.032(4) 0.055(6) 0.041(5) 0.000 0.005(4) 0.000 O4 0.042(2) 0.069(3) 0.041(3) 0.007(2) 0.000(2) 0.012(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 2.373(4) 7_556 ? Ca1 O1 2.373(4) 8_455 ? Ca1 O4 2.443(4) 2_556 ? Ca1 O4 2.443(4) . ? Ca1 O2 2.486(4) . ? Ca1 O2 2.486(4) 2_556 ? Ca1 O1 2.553(3) . ? Ca1 O1 2.553(3) 2_556 ? Ca1 C1 2.850(5) . ? Ca1 C1 2.850(5) 2_556 ? Ca1 H41 2.60(6) . ? O1 C1 1.269(6) . ? O1 Ca1 2.373(4) 7_556 ? O2 C1 1.240(6) . ? O3 C3 1.234(6) . ? N1 C3 1.333(6) . ? N1 C2 1.462(6) . ? N1 H1A 0.8800 . ? C1 C2 1.519(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.485(7) . ? C4 C7 1.380(7) . ? C4 C5 1.407(6) . ? C5 C4 1.407(6) 6 ? C5 H5 0.9500 . ? C7 C8 1.404(6) . ? C7 H7A 0.9500 . ? C8 C7 1.404(6) 6 ? C8 H8 0.9500 . ? O4 H41 0.86(3) . ? O4 H42 0.92(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ca1 O1 100.91(18) 7_556 8_455 ? O1 Ca1 O4 154.04(13) 7_556 2_556 ? O1 Ca1 O4 94.21(12) 8_455 2_556 ? O1 Ca1 O4 94.21(12) 7_556 . ? O1 Ca1 O4 154.04(13) 8_455 . ? O4 Ca1 O4 80.4(2) 2_556 . ? O1 Ca1 O2 120.95(12) 7_556 . ? O1 Ca1 O2 81.60(12) 8_455 . ? O4 Ca1 O2 81.89(13) 2_556 . ? O4 Ca1 O2 72.51(13) . . ? O1 Ca1 O2 81.60(12) 7_556 2_556 ? O1 Ca1 O2 120.95(12) 8_455 2_556 ? O4 Ca1 O2 72.51(13) 2_556 2_556 ? O4 Ca1 O2 81.89(13) . 2_556 ? O2 Ca1 O2 146.38(18) . 2_556 ? O1 Ca1 O1 69.47(14) 7_556 . ? O1 Ca1 O1 87.28(10) 8_455 . ? O4 Ca1 O1 132.79(13) 2_556 . ? O4 Ca1 O1 78.36(13) . . ? O2 Ca1 O1 51.61(12) . . ? O2 Ca1 O1 143.32(12) 2_556 . ? O1 Ca1 O1 87.28(10) 7_556 2_556 ? O1 Ca1 O1 69.47(14) 8_455 2_556 ? O4 Ca1 O1 78.36(13) 2_556 2_556 ? O4 Ca1 O1 132.79(13) . 2_556 ? O2 Ca1 O1 143.32(12) . 2_556 ? O2 Ca1 O1 51.61(12) 2_556 2_556 ? O1 Ca1 O1 143.55(18) . 2_556 ? O1 Ca1 C1 95.30(15) 7_556 . ? O1 Ca1 C1 87.64(13) 8_455 . ? O4 Ca1 C1 106.39(15) 2_556 . ? O4 Ca1 C1 69.91(14) . . ? O2 Ca1 C1 25.72(12) . . ? O2 Ca1 C1 151.37(14) 2_556 . ? O1 Ca1 C1 26.43(12) . . ? O1 Ca1 C1 157.02(14) 2_556 . ? O1 Ca1 C1 87.64(13) 7_556 2_556 ? O1 Ca1 C1 95.30(15) 8_455 2_556 ? O4 Ca1 C1 69.91(14) 2_556 2_556 ? O4 Ca1 C1 106.39(15) . 2_556 ? O2 Ca1 C1 151.37(14) . 2_556 ? O2 Ca1 C1 25.72(12) 2_556 2_556 ? O1 Ca1 C1 157.02(14) . 2_556 ? O1 Ca1 C1 26.43(12) 2_556 2_556 ? C1 Ca1 C1 175.4(2) . 2_556 ? O1 Ca1 H41 96.2(13) 7_556 . ? O1 Ca1 H41 136.2(9) 8_455 . ? O4 Ca1 H41 87.1(12) 2_556 . ? O4 Ca1 H41 19.4(8) . . ? O2 Ca1 H41 55.1(10) . . ? O2 Ca1 H41 101.2(9) 2_556 . ? O1 Ca1 H41 61.6(10) . . ? O1 Ca1 H41 151.9(9) 2_556 . ? C1 Ca1 H41 50.6(9) . . ? C1 Ca1 H41 125.7(9) 2_556 . ? C1 O1 Ca1 155.9(3) . 7_556 ? C1 O1 Ca1 90.0(3) . . ? Ca1 O1 Ca1 110.53(14) 7_556 . ? C1 O2 Ca1 93.8(3) . . ? C3 N1 C2 119.1(4) . . ? C3 N1 H1A 120.4 . . ? C2 N1 H1A 120.4 . . ? O2 C1 O1 122.0(5) . . ? O2 C1 C2 121.3(5) . . ? O1 C1 C2 116.6(4) . . ? O2 C1 Ca1 60.5(3) . . ? O1 C1 Ca1 63.6(3) . . ? C2 C1 Ca1 166.3(4) . . ? N1 C2 C1 114.2(4) . . ? N1 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? N1 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? O3 C3 N1 121.3(5) . . ? O3 C3 C4 121.4(5) . . ? N1 C3 C4 117.2(5) . . ? C7 C4 C5 119.3(6) . . ? C7 C4 C3 124.8(6) . . ? C5 C4 C3 115.8(5) . . ? C4 C5 C4 120.7(7) 6 . ? C4 C5 H5 119.6 6 . ? C4 C5 H5 119.6 . . ? C4 C7 C8 120.3(6) . . ? C4 C7 H7A 119.9 . . ? C8 C7 H7A 119.9 . . ? C7 C8 C7 120.0(8) . 6 ? C7 C8 H8 120.0 . . ? C7 C8 H8 120.0 6 . ? Ca1 O4 H41 91(4) . . ? Ca1 O4 H42 129(4) . . ? H41 O4 H42 114(6) . . ? 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 Ca1 O1 C1 167.1(4) 7_556 . . . ? O1 Ca1 O1 C1 -90.2(2) 8_455 . . . ? O4 Ca1 O1 C1 3.0(3) 2_556 . . . ? O4 Ca1 O1 C1 68.1(3) . . . . ? O2 Ca1 O1 C1 -8.7(3) . . . . ? O2 Ca1 O1 C1 126.9(3) 2_556 . . . ? O1 Ca1 O1 C1 -139.2(3) 2_556 . . . ? C1 Ca1 O1 C1 172.7(4) 2_556 . . . ? O1 Ca1 O1 Ca1 0.0 7_556 . . 7_556 ? O1 Ca1 O1 Ca1 102.7(2) 8_455 . . 7_556 ? O4 Ca1 O1 Ca1 -164.07(16) 2_556 . . 7_556 ? O4 Ca1 O1 Ca1 -99.04(15) . . . 7_556 ? O2 Ca1 O1 Ca1 -175.8(2) . . . 7_556 ? O2 Ca1 O1 Ca1 -40.2(3) 2_556 . . 7_556 ? O1 Ca1 O1 Ca1 53.67(11) 2_556 . . 7_556 ? C1 Ca1 O1 Ca1 -167.1(4) . . . 7_556 ? C1 Ca1 O1 Ca1 5.6(4) 2_556 . . 7_556 ? O1 Ca1 O2 C1 4.4(3) 7_556 . . . ? O1 Ca1 O2 C1 102.2(3) 8_455 . . . ? O4 Ca1 O2 C1 -162.3(3) 2_556 . . . ? O4 Ca1 O2 C1 -79.9(3) . . . . ? O2 Ca1 O2 C1 -122.0(3) 2_556 . . . ? O1 Ca1 O2 C1 9.0(3) . . . . ? O1 Ca1 O2 C1 139.8(3) 2_556 . . . ? C1 Ca1 O2 C1 -172.2(4) 2_556 . . . ? Ca1 O2 C1 O1 -16.9(5) . . . . ? Ca1 O2 C1 C2 164.2(4) . . . . ? Ca1 O1 C1 O2 165.5(5) 7_556 . . . ? Ca1 O1 C1 O2 16.4(5) . . . . ? Ca1 O1 C1 C2 -15.5(11) 7_556 . . . ? Ca1 O1 C1 C2 -164.7(4) . . . . ? Ca1 O1 C1 Ca1 149.2(8) 7_556 . . . ? O1 Ca1 C1 O2 -176.2(3) 7_556 . . . ? O1 Ca1 C1 O2 -75.4(3) 8_455 . . . ? O4 Ca1 C1 O2 18.3(3) 2_556 . . . ? O4 Ca1 C1 O2 91.3(3) . . . . ? O2 Ca1 C1 O2 101.7(4) 2_556 . . . ? O1 Ca1 C1 O2 -164.1(5) . . . . ? O1 Ca1 C1 O2 -80.7(5) 2_556 . . . ? C1 Ca1 C1 O2 54.3(3) 2_556 . . . ? O1 Ca1 C1 O1 -12.1(3) 7_556 . . . ? O1 Ca1 C1 O1 88.6(2) 8_455 . . . ? O4 Ca1 C1 O1 -177.7(3) 2_556 . . . ? O4 Ca1 C1 O1 -104.7(3) . . . . ? O2 Ca1 C1 O1 164.1(5) . . . . ? O2 Ca1 C1 O1 -94.3(4) 2_556 . . . ? O1 Ca1 C1 O1 83.4(5) 2_556 . . . ? C1 Ca1 C1 O1 -141.6(3) 2_556 . . . ? O1 Ca1 C1 C2 82.3(16) 7_556 . . . ? O1 Ca1 C1 C2 -177.0(16) 8_455 . . . ? O4 Ca1 C1 C2 -83.3(16) 2_556 . . . ? O4 Ca1 C1 C2 -10.3(16) . . . . ? O2 Ca1 C1 C2 -101.5(17) . . . . ? O2 Ca1 C1 C2 0.1(18) 2_556 . . . ? O1 Ca1 C1 C2 94.4(16) . . . . ? O1 Ca1 C1 C2 177.8(14) 2_556 . . . ? C1 Ca1 C1 C2 -47.2(16) 2_556 . . . ? C3 N1 C2 C1 -72.4(6) . . . . ? O2 C1 C2 N1 -13.4(7) . . . . ? O1 C1 C2 N1 167.7(4) . . . . ? Ca1 C1 C2 N1 80.1(17) . . . . ? C2 N1 C3 O3 0.0(7) . . . . ? C2 N1 C3 C4 -176.7(4) . . . . ? O3 C3 C4 C7 -171.1(5) . . . . ? N1 C3 C4 C7 5.5(7) . . . . ? O3 C3 C4 C5 7.6(7) . . . . ? N1 C3 C4 C5 -175.7(5) . . . . ? C7 C4 C5 C4 0.9(9) . . . 6 ? C3 C4 C5 C4 -178.0(4) . . . 6 ? C5 C4 C7 C8 -1.8(8) . . . . ? C3 C4 C7 C8 176.9(5) . . . . ? C4 C7 C8 C7 2.7(10) . . . 6 ? 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 H1A O2 0.88 2.04 2.826(6) 147.3 2 O4 H41 O3 0.86(3) 2.39(5) 3.072(5) 137(5) . O4 H41 O2 0.86(3) 2.36(6) 2.915(5) 123(5) . O4 H42 O3 0.92(4) 1.88(4) 2.764(5) 160(5) 2_656 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.341 _refine_diff_density_min -0.652 _refine_diff_density_rms 0.087 # start Validation Reply Form _vrf_RINTA01_3 ; PROBLEM: The value of Rint is greater than 0.12 RESPONSE: The crystal is very weakly diffracting. Several efforts to collect data at lower temperatures didn't improve the quality of the data. ; data_4 _database_code_depnum_ccdc_archive 'CCDC 886203' #TrackingRef 'All.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 N2 O11 Sr' _chemical_formula_weight 455.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 15.246(3) _cell_length_b 6.8008(9) _cell_length_c 8.0856(13) _cell_angle_alpha 90.00 _cell_angle_beta 92.234(14) _cell_angle_gamma 90.00 _cell_volume 837.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 2220 _cell_measurement_theta_min 1.33 _cell_measurement_theta_max 25.25 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.807 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 3.282 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.4942 _exptl_absorpt_correction_T_max 0.8799 _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_absorpt_correction_T_ave 0.6871 _exptl_crystal_size_rad 0.0300 _diffrn_ambient_temperature 180(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 '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate ( 34 cm diameter )' _diffrn_detector_type STOE _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 4170 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0795 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 25.67 _reflns_number_total 4170 _reflns_number_gt 2822 _reflns_threshold_expression >2\s(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4182 _refine_ls_number_parameters 124 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1666 _refine_ls_wR_factor_gt 0.1558 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _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 Sr1 Sr 0.5000 0.49293(10) 0.2500 0.02816(19) Uani 1 2 d S . . N1 N 0.2010(2) 0.8453(6) 0.0277(6) 0.0365(10) Uani 1 1 d D . . H1N H 0.1987 0.9743 0.0355 0.044 Uiso 1 1 calc RD . . O1 O 0.3378(2) 0.6567(5) 0.2046(5) 0.0400(8) Uani 1 1 d . . . O2 O 0.41702(19) 0.6331(5) -0.0175(4) 0.0342(7) Uani 1 1 d . . . O3 O 0.1376(2) 0.5575(5) 0.0948(5) 0.0437(10) Uani 1 1 d . . . O4 O 0.4109(2) 0.1902(5) 0.0931(5) 0.0388(8) Uani 1 1 d D . . H41 H 0.3578 0.2249 0.0671 0.047 Uiso 1 1 d RD . . H42 H 0.4350 0.1668 0.0085 0.047 Uiso 1 1 d RD . . O5 O 0.5000 0.8837(7) 0.2500 0.0527(15) Uani 1 2 d SD . . O6 O 0.2432(2) 0.2619(5) -0.0210(5) 0.0362(8) Uani 1 1 d D . . H61 H 0.2603 0.2813 -0.1145 0.043 Uiso 1 1 d RD . . H62 H 0.2128 0.3521 0.0236 0.043 Uiso 1 1 d RD . . C1 C 0.3460(3) 0.6783(6) 0.0524(7) 0.0325(11) Uani 1 1 d . . . C2 C 0.2729(3) 0.7585(7) -0.0604(7) 0.0335(12) Uani 1 1 d . . . H2A H 0.2975 0.8594 -0.1337 0.040 Uiso 1 1 calc R . . H2B H 0.2494 0.6506 -0.1313 0.040 Uiso 1 1 calc R . . C3 C 0.1386(3) 0.7409(7) 0.0970(6) 0.0341(11) Uani 1 1 d . . . C4 C 0.0672(3) 0.8569(7) 0.1762(7) 0.0348(11) Uani 1 1 d . . . C5 C 0.0000 0.7567(10) 0.2500 0.0361(17) Uani 1 2 d S . . H5 H 0.0000 0.6170 0.2500 0.054 Uiso 1 2 calc SR . . C6 C 0.0672(3) 1.0611(7) 0.1788(8) 0.0397(13) Uani 1 1 d . . . H6A H 0.1137 1.1315 0.1312 0.048 Uiso 1 1 calc R . . C7 C 0.0000 1.1624(11) 0.2500 0.045(2) Uani 1 2 d S . . H7 H 0.0000 1.3021 0.2500 0.068 Uiso 1 2 calc SR . . H51 H 0.461(3) 0.969(7) 0.215(7) 0.054 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 Sr1 0.0315(3) 0.0270(3) 0.0264(3) 0.000 0.0062(2) 0.000 N1 0.033(2) 0.0297(19) 0.047(3) 0.0056(19) 0.0111(18) 0.0039(16) O1 0.0346(17) 0.053(2) 0.033(2) 0.0017(17) 0.0075(15) 0.0060(15) O2 0.0323(16) 0.0418(17) 0.0292(19) -0.0012(15) 0.0097(14) 0.0047(13) O3 0.0427(18) 0.0328(18) 0.057(3) -0.0002(15) 0.0139(17) 0.0014(13) O4 0.0354(16) 0.0387(18) 0.042(2) -0.0002(16) 0.0042(15) 0.0024(14) O5 0.057(3) 0.029(3) 0.071(4) 0.000 -0.017(3) 0.000 O6 0.0389(18) 0.0342(17) 0.036(2) 0.0013(16) 0.0115(16) 0.0045(14) C1 0.033(2) 0.027(2) 0.038(3) -0.002(2) 0.006(2) -0.0010(18) C2 0.031(2) 0.032(2) 0.038(3) 0.004(2) 0.011(2) 0.0039(19) C3 0.036(2) 0.034(2) 0.032(3) 0.001(2) 0.003(2) 0.0008(19) C4 0.032(2) 0.034(2) 0.039(3) 0.000(2) 0.002(2) 0.001(2) C5 0.033(3) 0.031(3) 0.044(5) 0.000 0.008(3) 0.000 C6 0.036(3) 0.033(2) 0.052(4) 0.002(2) 0.014(2) -0.0016(19) C7 0.054(4) 0.028(3) 0.055(6) 0.000 0.018(4) 0.000 _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 2.460(3) 3_665 ? Sr1 O2 2.460(3) 4_566 ? Sr1 O2 2.641(4) 2_655 ? Sr1 O2 2.641(4) . ? Sr1 O5 2.658(5) . ? Sr1 O1 2.724(3) 2_655 ? Sr1 O1 2.724(3) . ? Sr1 O4 2.749(3) . ? Sr1 O4 2.749(3) 2_655 ? Sr1 C1 3.059(5) 2_655 ? Sr1 C1 3.059(5) . ? N1 C3 1.328(6) . ? N1 C2 1.455(6) . ? N1 H1N 0.8800 . ? O1 C1 1.251(6) . ? O2 C1 1.278(6) . ? O2 Sr1 2.460(3) 3_665 ? O3 C3 1.248(6) . ? O4 H41 0.8623 . ? O4 H42 0.8049 . ? O5 H51 0.87(3) . ? O6 H61 0.8203 . ? O6 H62 0.8566 . ? C1 C2 1.515(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.507(7) . ? C4 C5 1.385(6) . ? C4 C6 1.389(7) . ? C5 C4 1.385(6) 2 ? C5 H5 0.9500 . ? C6 C7 1.379(6) . ? C6 H6A 0.9500 . ? C7 C6 1.379(6) 2 ? C7 H7 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Sr1 O2 139.23(16) 3_665 4_566 ? O2 Sr1 O2 120.48(12) 3_665 2_655 ? O2 Sr1 O2 75.18(11) 4_566 2_655 ? O2 Sr1 O2 75.18(11) 3_665 . ? O2 Sr1 O2 120.48(12) 4_566 . ? O2 Sr1 O2 137.69(15) 2_655 . ? O2 Sr1 O5 110.39(8) 3_665 . ? O2 Sr1 O5 110.39(8) 4_566 . ? O2 Sr1 O5 68.84(7) 2_655 . ? O2 Sr1 O5 68.84(7) . . ? O2 Sr1 O1 75.76(11) 3_665 2_655 ? O2 Sr1 O1 122.06(11) 4_566 2_655 ? O2 Sr1 O1 48.61(10) 2_655 2_655 ? O2 Sr1 O1 111.48(11) . 2_655 ? O5 Sr1 O1 65.87(8) . 2_655 ? O2 Sr1 O1 122.06(11) 3_665 . ? O2 Sr1 O1 75.76(11) 4_566 . ? O2 Sr1 O1 111.48(11) 2_655 . ? O2 Sr1 O1 48.61(10) . . ? O5 Sr1 O1 65.87(8) . . ? O1 Sr1 O1 131.74(16) 2_655 . ? O2 Sr1 O4 69.27(11) 3_665 . ? O2 Sr1 O4 80.33(11) 4_566 . ? O2 Sr1 O4 149.37(11) 2_655 . ? O2 Sr1 O4 71.35(10) . . ? O5 Sr1 O4 138.50(7) . . ? O1 Sr1 O4 142.92(11) 2_655 . ? O1 Sr1 O4 79.31(11) . . ? O2 Sr1 O4 80.33(11) 3_665 2_655 ? O2 Sr1 O4 69.27(11) 4_566 2_655 ? O2 Sr1 O4 71.35(10) 2_655 2_655 ? O2 Sr1 O4 149.37(11) . 2_655 ? O5 Sr1 O4 138.50(7) . 2_655 ? O1 Sr1 O4 79.31(11) 2_655 2_655 ? O1 Sr1 O4 142.92(11) . 2_655 ? O4 Sr1 O4 83.00(14) . 2_655 ? O2 Sr1 C1 97.78(12) 3_665 2_655 ? O2 Sr1 C1 98.72(13) 4_566 2_655 ? O2 Sr1 C1 24.54(12) 2_655 2_655 ? O2 Sr1 C1 127.75(12) . 2_655 ? O5 Sr1 C1 65.67(8) . 2_655 ? O1 Sr1 C1 24.09(12) 2_655 2_655 ? O1 Sr1 C1 125.17(11) . 2_655 ? O4 Sr1 C1 154.78(11) . 2_655 ? O4 Sr1 C1 73.29(11) 2_655 2_655 ? O2 Sr1 C1 98.72(13) 3_665 . ? O2 Sr1 C1 97.78(12) 4_566 . ? O2 Sr1 C1 127.75(12) 2_655 . ? O2 Sr1 C1 24.54(12) . . ? O5 Sr1 C1 65.67(8) . . ? O1 Sr1 C1 125.17(11) 2_655 . ? O1 Sr1 C1 24.09(12) . . ? O4 Sr1 C1 73.29(11) . . ? O4 Sr1 C1 154.78(11) 2_655 . ? C1 Sr1 C1 131.33(17) 2_655 . ? C3 N1 C2 123.7(4) . . ? C3 N1 H1N 118.2 . . ? C2 N1 H1N 118.2 . . ? C1 O1 Sr1 93.2(3) . . ? C1 O2 Sr1 153.1(3) . 3_665 ? C1 O2 Sr1 96.4(3) . . ? Sr1 O2 Sr1 104.82(11) 3_665 . ? Sr1 O4 H41 110.5 . . ? Sr1 O4 H42 107.9 . . ? H41 O4 H42 107.5 . . ? Sr1 O5 H51 132(4) . . ? H61 O6 H62 118.0 . . ? O1 C1 O2 121.8(4) . . ? O1 C1 C2 122.3(4) . . ? O2 C1 C2 115.9(5) . . ? O1 C1 Sr1 62.8(2) . . ? O2 C1 Sr1 59.1(3) . . ? C2 C1 Sr1 174.2(3) . . ? N1 C2 C1 113.7(4) . . ? N1 C2 H2A 108.8 . . ? C1 C2 H2A 108.8 . . ? N1 C2 H2B 108.8 . . ? C1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? O3 C3 N1 122.5(5) . . ? O3 C3 C4 121.4(4) . . ? N1 C3 C4 116.1(4) . . ? C5 C4 C6 119.0(5) . . ? C5 C4 C3 118.9(4) . . ? C6 C4 C3 122.1(5) . . ? C4 C5 C4 121.0(6) 2 . ? C4 C5 H5 119.5 2 . ? C4 C5 H5 119.5 . . ? C7 C6 C4 120.4(5) . . ? C7 C6 H6A 119.8 . . ? C4 C6 H6A 119.8 . . ? C6 C7 C6 120.1(7) . 2 ? C6 C7 H7 120.0 . . ? C6 C7 H7 120.0 2 . ? 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 O4 H41 O6 0.86 1.88 2.728(5) 168.8 . O4 H42 O5 0.80 2.37 3.176(4) 175.9 3_665 O5 H51 O4 0.87(3) 1.94(4) 2.768(5) 159(6) 1_565 O6 H61 O1 0.82 1.96 2.749(5) 160.8 4_565 O6 H62 O3 0.86 1.91 2.762(5) 172.4 . N1 H1N O6 0.88 2.13 2.935(5) 152.6 1_565 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.682 _refine_diff_density_min -0.876 _refine_diff_density_rms 0.105 # start Validation Reply Form _vrf_PLAT021_4 ; PROBLEM: Ratio Unique / Expected Reflections too High ... 2.616 RESPONSE: The higher number of reflections comes from the twin refinement method. The reflections will not be merged during refinement because the equivalent reflections are not equal due to the twinning of the crystal. A great number of reflections are affected by 2 different twin components. So the SHELXL program sets the MERG method from 2 (merge equivalent reflections) to 0 (do nothing). The Platon program can not recognise it because the cif file has no informations about twinning. ; data_5 _database_code_depnum_ccdc_archive 'CCDC 886204' #TrackingRef 'All.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 Mn N2 O12' _chemical_formula_weight 437.22 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 6.9305(12) _cell_length_b 7.8963(13) _cell_length_c 30.874(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.20(3) _cell_angle_gamma 90.00 _cell_volume 1689.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 4905 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 26.93 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.719 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 0.852 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8828 _exptl_absorpt_correction_T_max 0.9350 _exptl_absorpt_process_details 'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate ( 34 cm diameter )' _diffrn_detector_type STOE _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 5075 _diffrn_reflns_av_R_equivalents 0.1016 _diffrn_reflns_av_sigmaI/netI 0.1128 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 25.63 _reflns_number_total 2951 _reflns_number_gt 2010 _reflns_threshold_expression >2\s(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.1179P)^2^+2.6319P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.11(8) _refine_ls_number_reflns 2951 _refine_ls_number_parameters 232 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.1146 _refine_ls_R_factor_gt 0.0829 _refine_ls_wR_factor_ref 0.2445 _refine_ls_wR_factor_gt 0.2256 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.320 _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 0.9449(2) 0.7680(2) 0.88468(9) 0.0347(5) Uani 1 1 d . . . C1 C 1.2164(17) 0.7581(19) 0.9660(4) 0.036(3) Uani 1 1 d . . . C2 C 1.2814(19) 0.6440(18) 1.0033(5) 0.040(3) Uani 1 1 d . . . H2A H 1.1682 0.5798 1.0140 0.048 Uiso 1 1 calc R . . H2B H 1.3756 0.5609 0.9920 0.048 Uiso 1 1 calc R . . C3 C 1.2630(19) 0.8225(17) 1.0674(5) 0.037(3) Uani 1 1 d . . . C4 C 1.3810(10) 0.9126(12) 1.1025(3) 0.035(3) Uani 1 1 d G . . C5 C 1.5816(10) 0.9124(12) 1.1027(3) 0.037(3) Uani 1 1 d G . . H5A H 1.6505 0.8529 1.0808 0.045 Uiso 1 1 calc R . . C6 C 1.6814(7) 0.9994(13) 1.1348(3) 0.042(3) Uani 1 1 d G . . H6A H 1.8185 0.9993 1.1349 0.051 Uiso 1 1 calc R . . C7 C 1.5807(10) 1.0864(12) 1.1667(3) 0.039(4) Uani 1 1 d G . . H7A H 1.6489 1.1459 1.1886 0.047 Uiso 1 1 calc R . . C8 C 1.3801(10) 1.0866(12) 1.1665(3) 0.035(3) Uani 1 1 d G . . C9 C 1.2803(7) 0.9996(13) 1.1344(3) 0.041(3) Uani 1 1 d G . . H9A H 1.1432 0.9997 1.1343 0.049 Uiso 1 1 calc R . . C10 C 1.2634(18) 1.1762(17) 1.2017(5) 0.040(4) Uani 1 1 d . . . C11 C 1.280(2) 1.3540(18) 1.2660(5) 0.043(3) Uani 1 1 d . . . H11A H 1.1656 1.4168 1.2553 0.052 Uiso 1 1 calc R . . H11B H 1.3723 1.4385 1.2773 0.052 Uiso 1 1 calc R . . C12 C 1.2155(17) 1.242(2) 1.3035(4) 0.044(4) Uani 1 1 d . . . N1 N 1.3679(15) 0.7322(16) 1.0395(4) 0.043(3) Uani 1 1 d . . . H1A H 1.4937 0.7261 1.0432 0.051 Uiso 1 1 calc R . . N2 N 1.3662(14) 1.2710(16) 1.2305(4) 0.041(3) Uani 1 1 d . . . H2C H 1.4916 1.2808 1.2268 0.049 Uiso 1 1 calc R . . O1 O 1.2517(14) 0.9104(13) 0.9663(3) 0.047(2) Uani 1 1 d . . . O2 O 1.1341(15) 0.6792(14) 0.9347(4) 0.051(3) Uani 1 1 d . . . O3 O 1.0889(13) 0.8369(12) 1.0647(4) 0.045(2) Uani 1 1 d . . . O4 O 1.0886(13) 1.1634(12) 1.2045(4) 0.044(2) Uani 1 1 d . . . O5 O 1.2482(15) 1.0866(12) 1.3028(3) 0.047(3) Uani 1 1 d . . . O6 O 1.1347(14) 1.3161(13) 1.3345(4) 0.045(3) Uani 1 1 d . . . O7 O 0.9690(17) 1.0413(11) 0.8851(5) 0.050(2) Uani 1 1 d D . . H72 H 0.8939 1.1185 0.8840 0.060 Uiso 1 1 d RD . . H71 H 1.0221 1.0522 0.8607 0.060 Uiso 1 1 d RD . . O8 O 0.8786(13) 0.4970(11) 0.8846(3) 0.036(2) Uani 1 1 d D . . H81 H 0.7800 0.4737 0.9066 0.054 Uiso 1 1 d RD . . H82 H 0.8301 0.4640 0.8560 0.054 Uiso 1 1 d RD . . O9 O 0.7089(15) 0.8109(14) 0.8363(4) 0.048(3) Uani 1 1 d D . . H91 H 0.6785 0.7037 0.8218 0.072 Uiso 1 1 d RD . . H92 H 0.7517 0.8939 0.8147 0.072 Uiso 1 1 d RD . . O10 O 0.7108(16) 0.8117(13) 0.9327(4) 0.049(3) Uani 1 1 d D . . H101 H 0.5966 0.8561 0.9177 0.073 Uiso 1 1 d RD . . H102 H 0.6783 0.7043 0.9468 0.073 Uiso 1 1 d RD . . O11 O 0.7830(13) 0.6970(13) 0.7536(3) 0.044(2) Uani 1 1 d . . . O12 O 0.7826(13) 0.7011(14) 1.0155(3) 0.046(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0223(8) 0.0271(10) 0.0546(11) -0.0012(13) -0.0042(7) 0.0053(10) C1 0.025(6) 0.047(9) 0.036(7) -0.004(7) -0.004(5) 0.014(6) C2 0.025(7) 0.047(8) 0.048(9) -0.008(7) -0.005(6) 0.010(6) C3 0.031(8) 0.032(7) 0.046(8) -0.001(6) -0.002(6) -0.005(5) C4 0.018(6) 0.036(8) 0.053(9) -0.001(6) -0.005(5) -0.001(5) C5 0.011(6) 0.056(10) 0.045(8) -0.004(7) 0.008(5) 0.005(5) C6 0.014(5) 0.058(9) 0.055(7) 0.000(8) -0.005(5) -0.004(6) C7 0.025(7) 0.041(9) 0.052(9) -0.001(7) -0.012(6) -0.010(6) C8 0.011(6) 0.041(8) 0.051(8) -0.006(6) 0.000(5) 0.009(5) C9 0.006(5) 0.052(8) 0.066(9) -0.004(7) -0.003(6) 0.001(5) C10 0.017(7) 0.030(7) 0.073(11) 0.006(6) 0.010(6) -0.001(5) C11 0.044(9) 0.040(8) 0.046(9) -0.005(7) -0.004(7) -0.009(6) C12 0.019(6) 0.075(12) 0.038(7) 0.004(8) -0.005(5) -0.019(7) N1 0.024(6) 0.057(8) 0.047(7) -0.006(6) -0.007(5) -0.005(5) N2 0.020(5) 0.055(8) 0.049(6) -0.004(6) -0.003(5) -0.012(5) O1 0.047(6) 0.038(6) 0.056(6) -0.001(5) -0.007(5) -0.008(5) O2 0.047(7) 0.049(7) 0.057(7) -0.007(5) -0.024(5) 0.012(5) O3 0.025(5) 0.042(6) 0.068(7) -0.003(5) -0.005(5) -0.006(4) O4 0.024(5) 0.041(5) 0.067(7) -0.005(5) -0.002(4) -0.001(4) O5 0.056(6) 0.026(6) 0.060(7) 0.002(5) -0.001(5) 0.010(4) O6 0.039(6) 0.044(6) 0.053(7) -0.008(5) 0.014(5) -0.010(4) O7 0.027(5) 0.036(5) 0.088(7) -0.007(7) 0.007(5) 0.004(5) O8 0.024(4) 0.036(5) 0.049(5) -0.001(4) -0.002(4) -0.007(3) O9 0.041(6) 0.042(6) 0.061(7) -0.003(5) -0.010(5) 0.008(4) O10 0.049(6) 0.033(6) 0.064(7) 0.012(5) 0.003(5) 0.013(4) O11 0.030(5) 0.046(6) 0.055(6) 0.002(4) -0.001(4) 0.001(4) O12 0.028(5) 0.054(6) 0.055(6) 0.004(5) -0.006(4) -0.006(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O6 2.140(10) 2_574 ? Mn1 O2 2.144(10) . ? Mn1 O7 2.165(9) . ? Mn1 O8 2.188(9) . ? Mn1 O10 2.224(12) . ? Mn1 O9 2.241(11) . ? C1 O1 1.228(18) . ? C1 O2 1.285(18) . ? C1 C2 1.53(2) . ? C2 N1 1.445(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O3 1.215(16) . ? C3 N1 1.334(19) . ? C3 C4 1.532(15) . ? C4 C5 1.3900 . ? C4 C9 1.3900 . ? C5 C6 1.3900 . ? C5 H5A 0.9500 . ? C6 C7 1.3900 . ? C6 H6A 0.9500 . ? C7 C8 1.3900 . ? C7 H7A 0.9500 . ? C8 C9 1.3900 . ? C8 C10 1.529(16) . ? C9 H9A 0.9500 . ? C10 O4 1.219(16) . ? C10 N2 1.36(2) . ? C11 N2 1.410(18) . ? C11 C12 1.53(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O5 1.25(2) . ? C12 O6 1.253(19) . ? N1 H1A 0.8800 . ? N2 H2C 0.8800 . ? O6 Mn1 2.140(10) 2_575 ? O7 H72 0.8024 . ? O7 H71 0.8431 . ? O8 H81 0.9801 . ? O8 H82 0.9799 . ? O9 H91 0.9801 . ? O9 H92 0.9800 . ? O10 H101 0.9800 . ? O10 H102 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 Mn1 O2 92.5(4) 2_574 . ? O6 Mn1 O7 105.4(5) 2_574 . ? O2 Mn1 O7 105.9(5) . . ? O6 Mn1 O8 79.9(4) 2_574 . ? O2 Mn1 O8 79.0(4) . . ? O7 Mn1 O8 172.3(4) . . ? O6 Mn1 O10 168.4(5) 2_574 . ? O2 Mn1 O10 91.0(5) . . ? O7 Mn1 O10 84.1(5) . . ? O8 Mn1 O10 90.0(4) . . ? O6 Mn1 O9 90.7(4) 2_574 . ? O2 Mn1 O9 167.5(5) . . ? O7 Mn1 O9 84.8(5) . . ? O8 Mn1 O9 89.7(4) . . ? O10 Mn1 O9 83.6(4) . . ? O1 C1 O2 124.6(13) . . ? O1 C1 C2 120.9(12) . . ? O2 C1 C2 114.3(13) . . ? N1 C2 C1 114.8(12) . . ? N1 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? N1 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? O3 C3 N1 123.1(13) . . ? O3 C3 C4 122.4(12) . . ? N1 C3 C4 114.5(11) . . ? C5 C4 C9 120.0 . . ? C5 C4 C3 122.4(7) . . ? C9 C4 C3 117.6(7) . . ? C4 C5 C6 120.0 . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C7 C6 C5 120.0 . . ? C7 C6 H6A 120.0 . . ? C5 C6 H6A 120.0 . . ? C6 C7 C8 120.0 . . ? C6 C7 H7A 120.0 . . ? C8 C7 H7A 120.0 . . ? C9 C8 C7 120.0 . . ? C9 C8 C10 118.2(7) . . ? C7 C8 C10 121.8(7) . . ? C8 C9 C4 120.0 . . ? C8 C9 H9A 120.0 . . ? C4 C9 H9A 120.0 . . ? O4 C10 N2 121.3(13) . . ? O4 C10 C8 122.5(13) . . ? N2 C10 C8 116.2(10) . . ? N2 C11 C12 116.3(13) . . ? N2 C11 H11A 108.2 . . ? C12 C11 H11A 108.2 . . ? N2 C11 H11B 108.2 . . ? C12 C11 H11B 108.2 . . ? H11A C11 H11B 107.4 . . ? O5 C12 O6 123.9(14) . . ? O5 C12 C11 120.3(13) . . ? O6 C12 C11 115.8(15) . . ? C3 N1 C2 122.0(12) . . ? C3 N1 H1A 119.0 . . ? C2 N1 H1A 119.0 . . ? C10 N2 C11 122.7(11) . . ? C10 N2 H2C 118.7 . . ? C11 N2 H2C 118.7 . . ? C1 O2 Mn1 131.0(10) . . ? C12 O6 Mn1 132.9(10) . 2_575 ? Mn1 O7 H72 135.0 . . ? Mn1 O7 H71 97.5 . . ? H72 O7 H71 99.6 . . ? Mn1 O8 H81 109.2 . . ? Mn1 O8 H82 109.4 . . ? H81 O8 H82 109.5 . . ? Mn1 O9 H91 109.3 . . ? Mn1 O9 H92 109.5 . . ? H91 O9 H92 109.5 . . ? Mn1 O10 H101 109.4 . . ? Mn1 O10 H102 109.3 . . ? H101 O10 H102 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 N1 H1A O12 0.88 2.19 2.978(15) 149.4 1_655 N2 H2C O11 0.88 2.19 2.986(14) 150.4 2_675 O7 H72 O6 0.80 2.41 3.013(17) 132.2 4_474 O7 H72 O2 0.80 2.43 2.986(17) 127.0 3_455 O7 H71 O9 0.84 2.53 3.094(17) 124.9 3 O8 H81 O1 0.98 1.92 2.757(14) 141.6 3_445 O8 H81 O7 0.98 2.32 2.861(14) 114.1 3_445 O8 H82 O5 0.98 1.78 2.763(14) 177.0 4_464 O9 H91 O11 0.98 2.23 2.754(16) 112.4 . O9 H92 O6 0.98 2.50 2.990(15) 110.4 4_474 O10 H102 O12 0.98 2.24 2.747(16) 110.9 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.881 _refine_diff_density_min -0.815 _refine_diff_density_rms 0.122 # start Validation Reply Form _vrf_PLAT113_5 ; PROBLEM: Type_2 Report New space-group suggested by ADDSYM RESPONSE: Upon completion of the refinement, PLATON (Spek,1991) and IUCR's CheckCIF were used to verify the correctness of the structure and a new space group, Ama2, was suggested by both programs. Refinement in this space group was proved impossible. ; _vrf_PLAT112_5 ; PROBLEM: Type_2 Test for additional symmetry [0, 1] RESPONSE: Upon completion of the refinement, PLATON (Spek,1991) and IUCR's CheckCIF were used to verify the correctness of the structure and a new space group, Ama2, was suggested by both programs. Refinement in this space group was proved impossible. ; data_8 _database_code_depnum_ccdc_archive 'CCDC 886205' #TrackingRef 'All.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 Cu N2 O11' _chemical_formula_weight 431.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 15.211(3) _cell_length_b 6.8469(14) _cell_length_c 8.1434(16) _cell_angle_alpha 90.00 _cell_angle_beta 92.16(3) _cell_angle_gamma 90.00 _cell_volume 847.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 2867 _cell_measurement_theta_min 1.34 _cell_measurement_theta_max 24.07 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.692 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 446 _exptl_absorpt_coefficient_mu 1.352 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.7553 _exptl_absorpt_correction_T_max 0.8996 _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_absorpt_correction_T_ave 0.8275 _exptl_crystal_size_rad 0.0500 _diffrn_ambient_temperature 180(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 '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate ( 34 cm diameter )' _diffrn_detector_type STOE _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 4578 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1048 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 25.61 _reflns_number_total 4578 _reflns_number_gt 2593 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4578 _refine_ls_number_parameters 125 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1200 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.2099 _refine_ls_wR_factor_gt 0.1803 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.059 _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 Cu1 Cu 0.5000 0.0000 1.0000 0.0346(3) Uani 1 2 d S . . C1 C 0.3442(3) 0.2532(7) 0.9962(8) 0.0380(12) Uani 1 1 d . . . C2 C 0.2719(3) 0.3359(7) 1.0991(7) 0.0368(12) Uani 1 1 d . . . H2A H 0.2476 0.2292 1.1658 0.044 Uiso 1 1 calc R . . H2B H 0.2980 0.4339 1.1759 0.044 Uiso 1 1 calc R . . C3 C 0.1386(3) 0.3220(7) 0.9228(7) 0.0381(12) Uani 1 1 d . . . C4 C 0.0684(4) 0.4333(7) 0.8327(7) 0.0369(13) Uani 1 1 d . . . C5 C 0.0662(4) 0.6386(8) 0.8314(8) 0.0445(14) Uani 1 1 d . . . H5 H 0.1113 0.7106 0.8878 0.053 Uiso 1 1 calc R . . C6 C 0.0000 0.3382(11) 0.7500 0.042(2) Uani 1 2 d S . . H6 H 0.0000 0.1995 0.7500 0.050 Uiso 1 2 calc SR . . C7 C 0.0000 0.7338(11) 0.7500 0.051(2) Uani 1 2 d S . . H7 H 0.0000 0.8725 0.7500 0.061 Uiso 1 2 calc SR . . N1 N 0.2002(3) 0.4270(6) 1.0039(6) 0.0392(11) Uani 1 1 d D . . H1N H 0.211(4) 0.570(5) 1.006(7) 0.047 Uiso 1 1 d D . . O1 O 0.4063(2) 0.1699(5) 1.0820(4) 0.0379(8) Uani 1 1 d . . . O2 O 0.3410(2) 0.2666(5) 0.8446(5) 0.0453(9) Uani 1 1 d . . . O3 O 0.1403(3) 0.1399(5) 0.9212(5) 0.0484(10) Uani 1 1 d . . . O4 O 0.5000 -0.1556(7) 1.2500 0.0420(12) Uani 1 2 d SD . . H41 H 0.4529 -0.2202 1.2609 0.050 Uiso 1 1 d RD . . O5 O 0.5892(2) 0.1914(5) 1.0848(5) 0.0399(8) Uani 1 1 d D . . H51 H 0.5859 0.1832 1.1884 0.048 Uiso 1 1 d RD . . H52 H 0.6393 0.2367 1.0614 0.048 Uiso 1 1 d RD . . O6 O 0.2443(2) 0.8381(5) 0.0466(5) 0.0429(9) Uani 1 1 d D . . H61 H 0.2059 0.9215 0.0144 0.051 Uiso 1 1 d RD . . H62 H 0.2619 0.8644 0.1444 0.051 Uiso 1 1 d RD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0266(4) 0.0386(4) 0.0385(5) -0.0005(5) 0.0001(3) 0.0015(5) C1 0.029(3) 0.036(3) 0.049(4) 0.004(3) 0.006(3) -0.002(2) C2 0.031(3) 0.039(3) 0.041(3) -0.002(2) -0.002(2) 0.003(2) C3 0.029(3) 0.041(3) 0.045(3) -0.004(2) 0.001(2) 0.001(2) C4 0.028(3) 0.040(3) 0.043(3) -0.005(2) 0.001(2) -0.001(2) C5 0.036(3) 0.040(3) 0.057(4) 0.000(3) -0.006(3) -0.001(3) C6 0.035(4) 0.035(4) 0.057(6) 0.000 -0.002(4) 0.000 C7 0.041(4) 0.027(4) 0.083(7) 0.000 -0.011(5) 0.000 N1 0.030(2) 0.039(2) 0.048(3) 0.0004(19) -0.003(2) 0.0063(18) O1 0.0318(18) 0.0425(18) 0.039(2) -0.0044(16) -0.0026(16) 0.0025(15) O2 0.035(2) 0.060(2) 0.040(3) 0.0067(19) 0.0035(18) 0.0072(17) O3 0.045(2) 0.038(2) 0.062(3) -0.0017(18) -0.008(2) 0.0021(17) O4 0.033(3) 0.050(3) 0.043(3) 0.000 0.000(2) 0.000 O5 0.0330(18) 0.051(2) 0.035(2) 0.0023(16) -0.0031(16) -0.0002(16) O6 0.040(2) 0.0439(19) 0.045(2) 0.0040(17) -0.0029(18) 0.0004(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.975(3) . ? Cu1 O1 1.975(3) 3_657 ? Cu1 O5 1.991(4) . ? Cu1 O5 1.991(4) 3_657 ? Cu1 O4 2.298(2) . ? Cu1 O4 2.298(2) 3_657 ? C1 O2 1.237(7) . ? C1 O1 1.287(6) . ? C1 C2 1.517(7) . ? C2 N1 1.455(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O3 1.247(6) . ? C3 N1 1.336(7) . ? C3 C4 1.483(8) . ? C4 C6 1.381(6) . ? C4 C5 1.406(8) . ? C5 C7 1.351(6) . ? C5 H5 0.9500 . ? C6 C4 1.381(6) 2_556 ? C6 H6 0.9500 . ? C7 C5 1.351(6) 2_556 ? C7 H7 0.9500 . ? N1 H1N 0.99(3) . ? O4 Cu1 2.298(2) 2_657 ? O4 H41 0.8500 . ? O5 H51 0.8495 . ? O5 H52 0.8505 . ? O6 H61 0.8510 . ? O6 H62 0.8495 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 180.0 . 3_657 ? O1 Cu1 O5 89.20(14) . . ? O1 Cu1 O5 90.80(14) 3_657 . ? O1 Cu1 O5 90.79(14) . 3_657 ? O1 Cu1 O5 89.20(14) 3_657 3_657 ? O5 Cu1 O5 180.0 . 3_657 ? O1 Cu1 O4 87.11(13) . . ? O1 Cu1 O4 92.89(13) 3_657 . ? O5 Cu1 O4 91.19(14) . . ? O5 Cu1 O4 88.81(14) 3_657 . ? O1 Cu1 O4 92.89(13) . 3_657 ? O1 Cu1 O4 87.11(13) 3_657 3_657 ? O5 Cu1 O4 88.81(14) . 3_657 ? O5 Cu1 O4 91.19(13) 3_657 3_657 ? O4 Cu1 O4 180.0 . 3_657 ? O2 C1 O1 125.1(5) . . ? O2 C1 C2 121.5(5) . . ? O1 C1 C2 113.4(5) . . ? N1 C2 C1 114.2(5) . . ? N1 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? N1 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? O3 C3 N1 121.9(5) . . ? O3 C3 C4 121.6(5) . . ? N1 C3 C4 116.5(4) . . ? C6 C4 C5 116.7(6) . . ? C6 C4 C3 120.9(5) . . ? C5 C4 C3 122.3(5) . . ? C7 C5 C4 120.2(6) . . ? C7 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C4 C6 C4 123.7(7) . 2_556 ? C4 C6 H6 118.1 . . ? C4 C6 H6 118.1 2_556 . ? C5 C7 C5 122.3(7) . 2_556 ? C5 C7 H7 118.8 . . ? C5 C7 H7 118.8 2_556 . ? C3 N1 C2 122.1(4) . . ? C3 N1 H1N 131(4) . . ? C2 N1 H1N 107(4) . . ? C1 O1 Cu1 127.0(4) . . ? Cu1 O4 Cu1 124.7(2) 2_657 . ? Cu1 O4 H41 96.9 2_657 . ? Cu1 O4 H41 111.2 . . ? Cu1 O5 H51 103.6 . . ? Cu1 O5 H52 140.1 . . ? H51 O5 H52 109.5 . . ? H61 O6 H62 109.6 . . ? 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 H1N O6 0.99(3) 1.93(4) 2.912(6) 169(5) 1_556 O4 H41 O2 0.85 1.88 2.676(4) 154.5 4_556 O5 H51 O1 0.85 1.87 2.716(5) 172.8 2_657 O5 H52 O6 0.85 2.07 2.794(5) 142.4 3_666 O6 H61 O3 0.85 1.94 2.773(5) 167.5 1_564 O6 H62 O2 0.85 2.18 2.881(6) 139.3 4_565 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.363 _refine_diff_density_min -0.781 _refine_diff_density_rms 0.112 # start Validation Reply Form _vrf_PLAT021_l8cut2 ; PROBLEM: Ratio Unique / Expected Reflections too High ... 2.880 RESPONSE: The higher number of reflections comes from the twin refinement method. The reflections will not be merged during refinement because the equivalent reflections are not equal due to the twinning of the crystal. A great number of reflections are affected by 2 different twin components. So the SHELXL program sets the MERG method from 2 (merge equivalent reflections) to 0 (do nothing). The Platon program can not recognise it because the cif file has no informations about twinning. ; data_9 _database_code_depnum_ccdc_archive 'CCDC 886206' #TrackingRef 'All.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 N2 O11 Zn' _chemical_formula_weight 433.67 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M C2221 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.8874(7) _cell_length_b 7.6896(8) _cell_length_c 29.879(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1582.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 2426 _cell_measurement_theta_min 1.36 _cell_measurement_theta_max 25.16 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.820 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.620 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6422 _exptl_absorpt_correction_T_max 0.9091 _exptl_absorpt_process_details 'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate ( 34 cm diameter )' _diffrn_detector_type STOE _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 2949 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.97 _diffrn_reflns_theta_max 26.67 _reflns_number_total 1589 _reflns_number_gt 1488 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0289P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.002(13) _refine_ls_number_reflns 1589 _refine_ls_number_parameters 138 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0247 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0514 _refine_ls_wR_factor_gt 0.0510 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.023 _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 Zn1 Zn 0.0000 0.82540(4) 0.2500 0.02562(10) Uani 1 2 d S . . O1 O 0.1163(2) 0.6694(2) 0.20432(5) 0.0273(3) Uani 1 1 d . . . O2 O 0.2257(3) 0.9161(2) 0.17507(6) 0.0369(4) Uani 1 1 d . . . O3 O 0.0966(2) 0.8337(2) 0.07173(5) 0.0319(4) Uani 1 1 d . . . O4 O -0.2662(2) 0.8287(2) 0.21058(5) 0.0286(3) Uani 1 1 d D . . H41 H -0.319(4) 0.920(4) 0.2055(10) 0.034 Uiso 1 1 d D . . H42 H -0.248(4) 0.813(4) 0.1840(9) 0.034 Uiso 1 1 d D . . O5 O 0.0000 1.0833(3) 0.2500 0.0316(4) Uani 1 2 d SD . . H51 H -0.071(4) 1.158(4) 0.2625(8) 0.038 Uiso 1 1 d D . . O6 O 0.2933(3) 1.2071(2) 0.12496(6) 0.0298(4) Uani 1 1 d D . . H61 H 0.289(4) 1.103(4) 0.1305(10) 0.036 Uiso 1 1 d D . . H62 H 0.395(4) 1.223(4) 0.1110(9) 0.036 Uiso 1 1 d D . . C1 C 0.2072(3) 0.7571(3) 0.17416(8) 0.0260(5) Uani 1 1 d . . . C2 C 0.2913(4) 0.6457(3) 0.13706(7) 0.0285(5) Uani 1 1 d . . . H2A H 0.3894 0.5667 0.1502 0.034 Uiso 1 1 calc R . . H2B H 0.1861 0.5726 0.1245 0.034 Uiso 1 1 calc R . . C3 C 0.2756(3) 0.8271(3) 0.07024(7) 0.0263(4) Uani 1 1 d . . . C4 C 0.3905(4) 0.9155(4) 0.03411(9) 0.0251(5) Uani 1 1 d . . . C5 C 0.5922(4) 0.9132(4) 0.03326(10) 0.0295(6) Uani 1 1 d . . . H5A H 0.6618 0.8517 0.0557 0.035 Uiso 1 1 calc R . . C6 C 0.6919(6) 1.0000 0.0000 0.0302(8) Uani 1 2 d S . . H6A H 0.8299 1.0000 0.0000 0.036 Uiso 1 2 calc SR . . C7 C 0.2906(6) 1.0000 0.0000 0.0264(8) Uani 1 2 d S . . H7A H 0.1527 1.0000 0.0000 0.032 Uiso 1 2 calc SR . . N1 N 0.3802(3) 0.7407(3) 0.10109(6) 0.0298(4) Uani 1 1 d D . . H1N H 0.509(4) 0.739(3) 0.0995(8) 0.036 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 Zn1 0.02663(17) 0.02549(16) 0.02475(15) 0.000 0.0010(2) 0.000 O1 0.0289(8) 0.0291(8) 0.0238(7) 0.0021(7) 0.0014(6) 0.0018(8) O2 0.0492(11) 0.0273(9) 0.0343(10) 0.0006(8) 0.0039(8) -0.0016(8) O3 0.0254(8) 0.0378(9) 0.0324(8) 0.0076(8) 0.0024(6) -0.0001(8) O4 0.0322(9) 0.0273(8) 0.0263(8) 0.0008(8) 0.0001(6) 0.0021(8) O5 0.0283(11) 0.0222(10) 0.0443(12) 0.000 0.0063(16) 0.000 O6 0.0298(8) 0.0296(10) 0.0300(8) 0.0029(7) 0.0023(7) 0.0011(7) C1 0.0239(11) 0.0300(11) 0.0240(11) 0.0026(10) 0.0006(9) 0.0014(10) C2 0.0300(11) 0.0291(13) 0.0264(11) 0.0039(10) 0.0011(9) 0.0027(11) C3 0.0286(11) 0.0265(10) 0.0239(9) -0.0007(10) 0.0011(8) 0.0011(11) C4 0.0261(13) 0.0266(14) 0.0226(12) -0.0016(11) -0.0003(10) -0.0009(12) C5 0.0305(14) 0.0304(15) 0.0277(13) 0.0045(12) -0.0030(11) 0.0012(13) C6 0.0223(17) 0.037(2) 0.0316(19) 0.0028(16) 0.000 0.000 C7 0.0245(17) 0.0298(19) 0.0250(17) 0.0009(15) 0.000 0.000 N1 0.0269(10) 0.0366(11) 0.0259(9) 0.0063(8) 0.0029(8) 0.0032(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O5 1.983(2) . ? Zn1 O1 1.9856(16) . ? Zn1 O1 1.9857(16) 3 ? Zn1 O4 2.1792(16) 3 ? Zn1 O4 2.1793(16) . ? Zn1 O2 2.8135(18) 3 ? Zn1 O2 2.8135(18) . ? O1 C1 1.288(3) . ? O2 C1 1.229(3) . ? O3 C3 1.235(3) . ? O4 H41 0.81(3) . ? O4 H42 0.81(3) . ? O5 H51 0.84(2) . ? O6 H61 0.82(3) . ? O6 H62 0.83(3) . ? C1 C2 1.516(3) . ? C2 N1 1.437(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N1 1.345(3) . ? C3 C4 1.501(3) . ? C4 C5 1.390(3) . ? C4 C7 1.391(3) . ? C5 C6 1.380(4) . ? C5 H5A 0.9500 . ? C6 C5 1.380(4) 4_575 ? C6 H6A 0.9500 . ? C7 C4 1.391(3) 4_575 ? C7 H7A 0.9500 . ? N1 H1N 0.89(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Zn1 O1 127.16(5) . . ? O5 Zn1 O1 127.15(5) . 3 ? O1 Zn1 O1 105.69(10) . 3 ? O5 Zn1 O4 89.33(5) . 3 ? O1 Zn1 O4 92.25(6) . 3 ? O1 Zn1 O4 88.57(6) 3 3 ? O5 Zn1 O4 89.33(5) . . ? O1 Zn1 O4 88.57(6) . . ? O1 Zn1 O4 92.25(6) 3 . ? O4 Zn1 O4 178.65(10) 3 . ? O5 Zn1 O2 75.65(4) . 3 ? O1 Zn1 O2 156.86(6) . 3 ? O1 Zn1 O2 51.66(6) 3 3 ? O4 Zn1 O2 91.83(6) 3 3 ? O4 Zn1 O2 87.84(6) . 3 ? O5 Zn1 O2 75.65(4) . . ? O1 Zn1 O2 51.67(6) . . ? O1 Zn1 O2 156.86(6) 3 . ? O4 Zn1 O2 87.84(6) 3 . ? O4 Zn1 O2 91.82(6) . . ? O2 Zn1 O2 151.31(7) 3 . ? C1 O1 Zn1 111.16(16) . . ? C1 O2 Zn1 73.38(14) . . ? Zn1 O4 H41 120(2) . . ? Zn1 O4 H42 113.4(18) . . ? H41 O4 H42 91(3) . . ? Zn1 O5 H51 132.8(19) . . ? H61 O6 H62 106(3) . . ? O2 C1 O1 123.7(2) . . ? O2 C1 C2 122.6(2) . . ? O1 C1 C2 113.7(2) . . ? N1 C2 C1 115.0(2) . . ? N1 C2 H2A 108.5 . . ? C1 C2 H2A 108.5 . . ? N1 C2 H2B 108.5 . . ? C1 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? O3 C3 N1 122.0(2) . . ? O3 C3 C4 122.2(2) . . ? N1 C3 C4 115.7(2) . . ? C5 C4 C7 119.1(3) . . ? C5 C4 C3 122.3(3) . . ? C7 C4 C3 118.6(3) . . ? C6 C5 C4 120.3(3) . . ? C6 C5 H5A 119.8 . . ? C4 C5 H5A 119.8 . . ? C5 C6 C5 120.3(4) 4_575 . ? C5 C6 H6A 119.9 4_575 . ? C5 C6 H6A 119.9 . . ? C4 C7 C4 120.7(4) . 4_575 ? C4 C7 H7A 119.6 . . ? C4 C7 H7A 119.6 4_575 . ? C3 N1 C2 122.4(2) . . ? C3 N1 H1N 120.3(17) . . ? C2 N1 H1N 117.3(17) . . ? 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 O4 H41 O1 0.81(3) 1.97(3) 2.748(3) 163(3) 5_455 O4 H42 O6 0.81(3) 1.97(3) 2.754(2) 164(3) 5_445 O5 H51 O4 0.84(2) 1.91(2) 2.746(2) 179(3) 7_455 O6 H61 O2 0.82(3) 2.01(3) 2.733(3) 148(3) . O6 H62 O3 0.83(3) 2.00(3) 2.800(3) 161(3) 5 N1 H1N O6 0.89(3) 2.12(3) 2.945(3) 155(2) 5_545 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.208 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.048 data_10 _database_code_depnum_ccdc_archive 'CCDC 886207' #TrackingRef 'All.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 Cd N2 O11' _chemical_formula_weight 480.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M C2221 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.9402(7) _cell_length_b 7.9330(7) _cell_length_c 29.988(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1651.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 2656 _cell_measurement_theta_min 1.36 _cell_measurement_theta_max 24.93 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.934 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.388 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7883 _exptl_absorpt_correction_T_max 0.9596 _exptl_absorpt_process_details 'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate ( 34 cm diameter )' _diffrn_detector_type STOE _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 3396 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 25.59 _reflns_number_total 1545 _reflns_number_gt 1351 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0258P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(4) _refine_ls_number_reflns 1545 _refine_ls_number_parameters 138 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0590 _refine_ls_wR_factor_gt 0.0575 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.0000 0.33773(5) 0.2500 0.03451(13) Uani 1 2 d S . . O1 O 0.1080(4) 0.1501(4) 0.29951(10) 0.0378(7) Uani 1 1 d . . . O2 O 0.2079(5) 0.3974(4) 0.32606(12) 0.0425(9) Uani 1 1 d . . . O3 O 0.0925(4) 0.3261(5) 0.43027(10) 0.0397(7) Uani 1 1 d . . . O4 O -0.2768(4) 0.3326(5) 0.29408(10) 0.0367(7) Uani 1 1 d D . . H41 H -0.342(8) 0.425(5) 0.2972(18) 0.044 Uiso 1 1 d D . . H42 H -0.249(8) 0.319(8) 0.3204(12) 0.044 Uiso 1 1 d D . . O5 O 0.0000 0.6115(5) 0.2500 0.0467(10) Uani 1 2 d SD . . H51 H 0.066(7) 0.677(6) 0.2676(14) 0.056 Uiso 1 1 d D . . O6 O -0.2167(6) 0.1922(4) 0.37725(12) 0.0388(9) Uani 1 1 d D . . H61 H -0.111(6) 0.222(6) 0.3873(17) 0.047 Uiso 1 1 d D . . H62 H -0.218(8) 0.089(4) 0.373(2) 0.047 Uiso 1 1 d D . . C1 C 0.1977(7) 0.2414(6) 0.32865(16) 0.0351(11) Uani 1 1 d . . . C2 C 0.2872(8) 0.1412(7) 0.36596(16) 0.0368(12) Uani 1 1 d . . . H2A H 0.1864 0.0690 0.3794 0.044 Uiso 1 1 calc R . . H2B H 0.3863 0.0658 0.3531 0.044 Uiso 1 1 calc R . . C3 C 0.2705(6) 0.3228(6) 0.43148(15) 0.0352(9) Uani 1 1 d . . . C4 C 0.3830(9) 0.4120(7) 0.4670(2) 0.0329(15) Uani 1 1 d . . . C5 C 0.5814(10) 0.4119(8) 0.4672(2) 0.0351(15) Uani 1 1 d . . . H5A H 0.6506 0.3517 0.4450 0.042 Uiso 1 1 calc R . . C6 C 0.6794(15) 0.5000 0.5000 0.040(2) Uani 1 2 d S . . H6A H 0.8163 0.5000 0.5000 0.048 Uiso 1 2 calc SR . . C7 C 0.2811(14) 0.5000 0.5000 0.032(2) Uani 1 2 d S . . H7A H 0.1442 0.5000 0.5000 0.038 Uiso 1 2 calc SR . . N1 N 0.3753(6) 0.2393(5) 0.40093(13) 0.0380(9) Uani 1 1 d D . . H1N H 0.513(5) 0.229(5) 0.4049(15) 0.046 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 Cd1 0.0354(2) 0.03267(18) 0.0355(2) 0.000 -0.0009(4) 0.000 O1 0.0421(17) 0.0383(15) 0.0331(15) -0.0037(16) -0.0043(14) 0.0017(16) O2 0.046(2) 0.0348(16) 0.047(2) 0.0034(15) -0.0011(18) -0.0018(16) O3 0.0331(16) 0.0447(16) 0.0414(17) -0.0043(16) -0.0010(13) -0.0008(16) O4 0.0395(18) 0.0345(14) 0.0359(16) -0.0001(18) -0.0048(14) 0.0046(17) O5 0.041(2) 0.041(2) 0.058(3) 0.000 -0.017(5) 0.000 O6 0.040(2) 0.036(2) 0.0406(19) -0.0033(15) -0.0033(17) 0.0016(16) C1 0.034(3) 0.036(2) 0.036(3) -0.001(2) 0.001(2) 0.004(2) C2 0.043(3) 0.036(3) 0.032(3) -0.007(2) -0.002(2) 0.000(2) C3 0.032(2) 0.035(2) 0.039(2) -0.003(2) -0.0012(19) 0.001(2) C4 0.031(3) 0.034(3) 0.034(3) 0.004(3) 0.004(3) 0.001(2) C5 0.033(3) 0.038(3) 0.035(3) -0.008(3) 0.006(2) 0.000(2) C6 0.023(4) 0.048(4) 0.048(5) 0.002(4) 0.000 0.000 C7 0.027(5) 0.039(4) 0.030(4) -0.006(3) 0.000 0.000 N1 0.036(2) 0.0421(19) 0.036(2) -0.0094(17) -0.002(2) 0.0022(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O5 2.172(4) . ? Cd1 O1 2.232(3) . ? Cd1 O1 2.232(3) 3 ? Cd1 O4 2.333(3) . ? Cd1 O4 2.333(3) 3 ? Cd1 O2 2.740(4) . ? Cd1 O2 2.740(4) 3 ? O1 C1 1.294(6) . ? O2 C1 1.242(5) . ? O3 C3 1.236(5) . ? O4 H41 0.87(3) . ? O4 H42 0.82(3) . ? O5 H51 0.87(3) . ? O6 H61 0.83(3) . ? O6 H62 0.82(3) . ? C1 C2 1.507(7) . ? C2 N1 1.442(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N1 1.344(6) . ? C3 C4 1.499(8) . ? C4 C5 1.377(7) . ? C4 C7 1.402(7) . ? C5 C6 1.384(9) . ? C5 H5A 0.9500 . ? C6 C5 1.384(9) 4_566 ? C6 H6A 0.9500 . ? C7 C4 1.402(8) 4_566 ? C7 H7A 0.9500 . ? N1 H1N 0.96(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cd1 O1 131.83(9) . . ? O5 Cd1 O1 131.83(8) . 3 ? O1 Cd1 O1 96.35(17) . 3 ? O5 Cd1 O4 91.00(9) . . ? O1 Cd1 O4 83.57(11) . . ? O1 Cd1 O4 95.09(12) 3 . ? O5 Cd1 O4 91.00(9) . 3 ? O1 Cd1 O4 95.09(12) . 3 ? O1 Cd1 O4 83.57(11) 3 3 ? O4 Cd1 O4 178.00(19) . 3 ? O5 Cd1 O2 80.06(7) . . ? O1 Cd1 O2 52.02(11) . . ? O1 Cd1 O2 147.75(10) 3 . ? O4 Cd1 O2 88.00(11) . . ? O4 Cd1 O2 92.35(11) 3 . ? O5 Cd1 O2 80.06(7) . 3 ? O1 Cd1 O2 147.75(11) . 3 ? O1 Cd1 O2 52.02(11) 3 3 ? O4 Cd1 O2 92.35(11) . 3 ? O4 Cd1 O2 88.00(11) 3 3 ? O2 Cd1 O2 160.12(14) . 3 ? C1 O1 Cd1 103.7(3) . . ? C1 O2 Cd1 81.4(3) . . ? Cd1 O4 H41 118(4) . . ? Cd1 O4 H42 111(4) . . ? H41 O4 H42 97(6) . . ? Cd1 O5 H51 127(3) . . ? H61 O6 H62 110(6) . . ? O2 C1 O1 122.9(5) . . ? O2 C1 C2 123.3(5) . . ? O1 C1 C2 113.9(4) . . ? N1 C2 C1 115.5(4) . . ? N1 C2 H2A 108.4 . . ? C1 C2 H2A 108.4 . . ? N1 C2 H2B 108.4 . . ? C1 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? O3 C3 N1 122.1(4) . . ? O3 C3 C4 122.1(4) . . ? N1 C3 C4 115.8(4) . . ? C5 C4 C7 120.1(7) . . ? C5 C4 C3 121.6(7) . . ? C7 C4 C3 118.3(6) . . ? C4 C5 C6 119.6(8) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C5 C6 C5 121.1(10) 4_566 . ? C5 C6 H6A 119.4 4_566 . ? C5 C6 H6A 119.4 . . ? C4 C7 C4 119.4(9) 4_566 . ? C4 C7 H7A 120.3 4_566 . ? C4 C7 H7A 120.3 . . ? C3 N1 C2 122.2(4) . . ? C3 N1 H1N 120(3) . . ? C2 N1 H1N 117(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 O4 H41 O1 0.87(3) 1.82(4) 2.648(5) 159(6) 5_455 O4 H42 O6 0.82(3) 1.99(4) 2.763(5) 156(6) . O5 H51 O4 0.87(3) 1.83(3) 2.687(4) 168(5) 5 O6 H61 O3 0.83(3) 2.08(4) 2.874(5) 160(5) . O6 H62 O2 0.82(3) 2.14(5) 2.847(5) 143(6) 5_445 N1 H1N O6 0.96(4) 2.07(4) 2.943(6) 149(4) 1_655 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.586 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.069