# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email George.Kostakis@kit.edu _publ_contact_author_name 'George Kostakis' _publ_author_name 'George Kostakis' data_kfk-224a _database_code_depnum_ccdc_archive 'CCDC 813335' #TrackingRef '- cif.cif' _audit_update_record ; 2011-02-16 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H10 N2 O6' _chemical_formula_weight 218.17 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 14.463(2) _cell_length_b 4.8155(7) _cell_length_c 14.291(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.922(11) _cell_angle_gamma 90.00 _cell_volume 887.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 1235 _cell_measurement_theta_min 3.19 _cell_measurement_theta_max 26.54 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9885 _exptl_absorpt_correction_T_max 0.9928 _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 2427 _diffrn_reflns_av_R_equivalents 0.0599 _diffrn_reflns_av_sigmaI/netI 0.0724 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 26.72 _reflns_number_total 931 _reflns_number_gt 533 _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^)+(0.0438P)^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 931 _refine_ls_number_parameters 84 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 0.898 _refine_ls_restrained_S_all 0.898 _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 O1 O 0.06666(14) 0.2176(4) 0.50358(13) 0.0482(5) Uani 1 1 d D . . H1 H 0.017(2) 0.238(6) 0.434(2) 0.058 Uiso 1 1 d D . . O2 O 0.15846(14) 0.5280(4) 0.46383(13) 0.0478(5) Uani 1 1 d . . . O3 O 0.41998(13) 0.2752(4) 0.80694(12) 0.0461(5) Uani 1 1 d . . . N1 N 0.31937(16) 0.5021(5) 0.65753(15) 0.0392(5) Uani 1 1 d D . . H1N H 0.320(2) 0.614(5) 0.6124(19) 0.047 Uiso 1 1 d D . . C1 C 0.14820(18) 0.3740(5) 0.52593(18) 0.0377(6) Uani 1 1 d . . . C2 C 0.22786(19) 0.3390(6) 0.63722(18) 0.0395(6) Uani 1 1 d D . . H21 H 0.198(2) 0.396(5) 0.6816(19) 0.047 Uiso 1 1 d D . . H22 H 0.246(2) 0.145(5) 0.6466(19) 0.047 Uiso 1 1 d D . . C3 C 0.41036(18) 0.4548(5) 0.74045(17) 0.0373(6) Uani 1 1 d . . . C4 C 0.5000 0.6335(8) 0.7500 0.0422(8) Uani 1 2 d S . . H41 H 0.517(2) 0.754(6) 0.8083(19) 0.051 Uiso 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 O1 0.0389(10) 0.0556(12) 0.0397(9) 0.0030(8) 0.0086(8) -0.0110(10) O2 0.0429(11) 0.0517(11) 0.0397(9) 0.0056(9) 0.0105(8) -0.0059(9) O3 0.0389(10) 0.0516(11) 0.0399(9) 0.0080(9) 0.0110(8) 0.0015(9) N1 0.0350(11) 0.0418(12) 0.0358(11) 0.0014(9) 0.0116(9) -0.0025(10) C1 0.0308(14) 0.0398(13) 0.0382(12) -0.0030(11) 0.0119(11) -0.0022(11) C2 0.0329(13) 0.0474(15) 0.0358(13) -0.0027(11) 0.0136(11) -0.0047(12) C3 0.0336(14) 0.0377(14) 0.0353(12) -0.0015(10) 0.0110(10) 0.0024(11) C4 0.0358(19) 0.040(2) 0.0437(19) 0.000 0.0117(17) 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 O1 C1 1.311(3) . ? O1 H1 0.93(3) . ? O2 C1 1.216(3) . ? O3 C3 1.245(3) . ? N1 C3 1.333(3) . ? N1 C2 1.451(3) . ? N1 H1N 0.85(2) . ? C1 C2 1.492(3) . ? C2 H21 0.96(2) . ? C2 H22 0.96(2) . ? C3 C4 1.510(3) . ? C4 C3 1.510(3) 2_656 ? C4 H41 0.95(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 C1 O1 H1 112.5(18) . . ? C3 N1 C2 122.0(2) . . ? C3 N1 H1N 115.8(19) . . ? C2 N1 H1N 121.5(19) . . ? O2 C1 O1 124.5(2) . . ? O2 C1 C2 123.8(2) . . ? O1 C1 C2 111.7(2) . . ? N1 C2 C1 110.3(2) . . ? N1 C2 H21 111.1(17) . . ? C1 C2 H21 108.2(17) . . ? N1 C2 H22 109.2(17) . . ? C1 C2 H22 106.7(15) . . ? H21 C2 H22 111(2) . . ? O3 C3 N1 121.4(2) . . ? O3 C3 C4 122.2(2) . . ? N1 C3 C4 116.4(2) . . ? C3 C4 C3 110.5(3) 2_656 . ? C3 C4 H41 113.4(17) 2_656 . ? C3 C4 H41 107.5(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 O1 H1 O3 0.93(3) 1.72(3) 2.646(2) 172(3) 8_455 N1 H1N O2 0.85(2) 2.13(3) 2.955(3) 164(2) 7_566 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.155 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.049 #============================================================================== data_kfk-36d _database_code_depnum_ccdc_archive 'CCDC 813336' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H12 Ca N2 O8' _chemical_formula_weight 292.27 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.7075(7) _cell_length_b 18.7331(15) _cell_length_c 8.3841(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.034(7) _cell_angle_gamma 90.00 _cell_volume 1169.11(17) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7690 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.15 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.574 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9038 _exptl_absorpt_correction_T_max 0.9774 _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 6547 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.68 _reflns_number_total 2471 _reflns_number_gt 2066 _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^)+(0.0383P)^2^+0.1413P] 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 2471 _refine_ls_number_parameters 175 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0654 _refine_ls_wR_factor_gt 0.0624 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ca1 Ca 0.76151(4) 0.024781(15) 0.53364(4) 0.02384(9) Uani 1 1 d . . . O1 O 0.93812(13) -0.00432(6) 0.31652(13) 0.0293(2) Uani 1 1 d . . . O2 O 0.64342(14) -0.00573(6) 0.22924(14) 0.0322(3) Uani 1 1 d . . . C1 C 0.79602(18) -0.02459(8) 0.21600(18) 0.0250(3) Uani 1 1 d . . . C2 C 0.8127(2) -0.07310(8) 0.0759(2) 0.0289(3) Uani 1 1 d . . . H2A H 0.8770 -0.0473 0.0054 0.035 Uiso 1 1 calc R . . H2B H 0.8855 -0.1153 0.1225 0.035 Uiso 1 1 calc R . . N1 N 0.63944(17) -0.09688(7) -0.02553(16) 0.0302(3) Uani 1 1 d . . . H1A H 0.5665 -0.0649 -0.0844 0.036 Uiso 1 1 calc R . . C3 C 0.5859(2) -0.16437(8) -0.03362(19) 0.0311(3) Uani 1 1 d . . . O3 O 0.68065(17) -0.21353(6) 0.04178(15) 0.0385(3) Uani 1 1 d . . . C4 C 0.3982(2) -0.17869(10) -0.1413(2) 0.0375(4) Uani 1 1 d . . . H4A H 0.4051 -0.2112 -0.2326 0.045 Uiso 1 1 calc R . . H4B H 0.3431 -0.1333 -0.1901 0.045 Uiso 1 1 calc R . . C5 C 0.2823(2) -0.21224(9) -0.0400(2) 0.0331(4) Uani 1 1 d . . . O4 O 0.2866(2) -0.19068(8) 0.09968(17) 0.0543(4) Uani 1 1 d . . . N2 N 0.17645(18) -0.26468(7) -0.11186(17) 0.0305(3) Uani 1 1 d . . . H2C H 0.1758 -0.2763 -0.2137 0.037 Uiso 1 1 calc R . . C6 C 0.0612(2) -0.30416(8) -0.0318(2) 0.0324(3) Uani 1 1 d . . . H6A H -0.0599 -0.3081 -0.1085 0.039 Uiso 1 1 calc R . . H6B H 0.0496 -0.2773 0.0666 0.039 Uiso 1 1 calc R . . C7 C 0.13132(19) -0.37862(8) 0.02124(18) 0.0262(3) Uani 1 1 d . . . O5 O 0.02513(13) -0.42306(6) 0.05663(13) 0.0296(2) Uani 1 1 d . . . O6 O 0.29022(15) -0.39434(6) 0.02681(17) 0.0392(3) Uani 1 1 d . . . O7 O 0.70256(16) 0.05272(7) 0.79441(15) 0.0332(3) Uani 1 1 d D . . H71 H 0.598(3) 0.0421(11) 0.793(3) 0.040 Uiso 1 1 d D . . H72 H 0.720(3) 0.0921(11) 0.827(2) 0.040 Uiso 1 1 d D . . O8 O 0.88755(16) 0.14006(6) 0.52351(18) 0.0372(3) Uani 1 1 d D . . H81 H 0.861(3) 0.1816(11) 0.504(3) 0.045 Uiso 1 1 d D . . H82 H 0.981(3) 0.1367(11) 0.506(3) 0.045 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 0.01792(14) 0.02350(15) 0.02898(15) -0.00287(12) 0.00410(10) 0.00093(11) O1 0.0205(5) 0.0319(6) 0.0323(6) -0.0038(4) 0.0012(4) -0.0009(4) O2 0.0206(5) 0.0398(6) 0.0350(6) -0.0054(5) 0.0054(4) 0.0021(4) C1 0.0221(6) 0.0240(7) 0.0276(7) 0.0018(6) 0.0043(5) -0.0001(6) C2 0.0251(7) 0.0282(8) 0.0327(8) -0.0030(6) 0.0063(6) -0.0029(6) N1 0.0307(7) 0.0265(6) 0.0298(7) 0.0007(5) 0.0017(5) -0.0041(5) C3 0.0374(8) 0.0299(8) 0.0264(7) -0.0012(6) 0.0089(6) -0.0070(7) O3 0.0452(7) 0.0279(6) 0.0407(7) 0.0034(5) 0.0079(5) -0.0027(5) C4 0.0427(9) 0.0384(9) 0.0283(8) 0.0007(7) 0.0038(7) -0.0164(7) C5 0.0371(8) 0.0285(8) 0.0326(9) -0.0009(6) 0.0069(7) -0.0053(6) O4 0.0811(10) 0.0485(8) 0.0390(7) -0.0156(6) 0.0258(7) -0.0251(7) N2 0.0333(7) 0.0274(7) 0.0309(7) -0.0007(5) 0.0086(5) -0.0054(5) C6 0.0277(8) 0.0282(8) 0.0434(9) 0.0020(7) 0.0128(7) -0.0001(6) C7 0.0235(7) 0.0253(7) 0.0293(7) -0.0025(6) 0.0059(6) -0.0027(6) O5 0.0245(5) 0.0284(6) 0.0352(6) 0.0033(4) 0.0065(4) -0.0066(4) O6 0.0245(6) 0.0286(6) 0.0664(8) 0.0033(5) 0.0152(5) 0.0015(4) O7 0.0287(6) 0.0351(6) 0.0365(6) -0.0057(5) 0.0095(5) -0.0045(5) O8 0.0265(6) 0.0245(6) 0.0634(8) 0.0030(5) 0.0166(6) 0.0022(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ca1 O5 2.3539(10) 2 ? Ca1 O1 2.3613(10) 3_756 ? Ca1 O8 2.3785(12) . ? Ca1 O7 2.4032(13) . ? Ca1 O6 2.4556(12) 4_656 ? Ca1 O2 2.5424(11) . ? Ca1 O1 2.5980(12) . ? Ca1 H82 2.74(2) . ? O1 C1 1.2551(17) . ? O1 Ca1 2.3613(10) 3_756 ? O2 C1 1.2602(18) . ? C1 C2 1.517(2) . ? C2 N1 1.4546(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? N1 C3 1.326(2) . ? N1 H1A 0.8800 . ? C3 O3 1.241(2) . ? C3 C4 1.517(2) . ? C4 C5 1.520(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O4 1.231(2) . ? C5 N2 1.319(2) . ? N2 C6 1.448(2) . ? N2 H2C 0.8800 . ? C6 C7 1.520(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O6 1.2487(19) . ? C7 O5 1.2558(18) . ? C7 Ca1 2.9088(15) 4 ? O5 Ca1 2.3539(10) 2_545 ? O5 Ca1 2.6776(11) 4 ? O6 Ca1 2.4557(12) 4 ? O7 H71 0.83(2) . ? O7 H72 0.79(2) . ? O8 H81 0.81(2) . ? O8 H82 0.78(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Ca1 O1 161.32(4) 2 3_756 ? O5 Ca1 O8 88.26(4) 2 . ? O1 Ca1 O8 79.23(4) 3_756 . ? O5 Ca1 O7 79.57(4) 2 . ? O1 Ca1 O7 86.67(4) 3_756 . ? O8 Ca1 O7 90.58(5) . . ? O5 Ca1 O6 119.23(4) 2 4_656 ? O1 Ca1 O6 76.65(4) 3_756 4_656 ? O8 Ca1 O6 149.60(4) . 4_656 ? O7 Ca1 O6 106.11(5) . 4_656 ? O5 Ca1 O2 73.07(4) 2 . ? O1 Ca1 O2 122.95(4) 3_756 . ? O8 Ca1 O2 102.21(5) . . ? O7 Ca1 O2 149.24(4) . . ? O6 Ca1 O2 76.34(4) 4_656 . ? O5 Ca1 O1 118.72(4) 2 . ? O1 Ca1 O1 73.69(4) 3_756 . ? O8 Ca1 O1 82.67(4) . . ? O7 Ca1 O1 160.08(4) . . ? O6 Ca1 O1 73.02(4) 4_656 . ? O2 Ca1 O1 50.63(3) . . ? O5 Ca1 H82 101.8(4) 2 . ? O1 Ca1 H82 68.1(4) 3_756 . ? O8 Ca1 H82 15.4(4) . . ? O7 Ca1 H82 100.2(5) . . ? O6 Ca1 H82 134.2(4) 4_656 . ? O2 Ca1 H82 98.9(4) . . ? O1 Ca1 H82 69.7(5) . . ? C1 O1 Ca1 150.76(10) . 3_756 ? C1 O1 Ca1 90.54(9) . . ? Ca1 O1 Ca1 106.31(4) 3_756 . ? C1 O2 Ca1 92.99(8) . . ? O1 C1 O2 121.86(14) . . ? O1 C1 C2 117.82(13) . . ? O2 C1 C2 120.31(12) . . ? O1 C1 Ca1 63.78(8) . . ? O2 C1 Ca1 61.25(8) . . ? C2 C1 Ca1 161.82(10) . . ? N1 C2 C1 112.75(12) . . ? N1 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N1 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C3 N1 C2 123.24(13) . . ? C3 N1 H1A 118.4 . . ? C2 N1 H1A 118.4 . . ? O3 C3 N1 123.17(15) . . ? O3 C3 C4 121.05(14) . . ? N1 C3 C4 115.78(14) . . ? C3 C4 C5 110.42(13) . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? O4 C5 N2 122.70(16) . . ? O4 C5 C4 121.41(15) . . ? N2 C5 C4 115.88(14) . . ? C5 N2 C6 123.35(14) . . ? C5 N2 H2C 118.3 . . ? C6 N2 H2C 118.3 . . ? N2 C6 C7 112.97(13) . . ? N2 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? N2 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? O6 C7 O5 121.86(14) . . ? O6 C7 C6 119.87(13) . . ? O5 C7 C6 118.26(13) . . ? O6 C7 Ca1 56.69(8) . 4 ? O5 C7 Ca1 66.88(8) . 4 ? C6 C7 Ca1 165.34(11) . 4 ? C7 O5 Ca1 144.50(10) . 2_545 ? C7 O5 Ca1 87.57(9) . 4 ? Ca1 O5 Ca1 106.31(4) 2_545 4 ? C7 O6 Ca1 98.17(9) . 4 ? Ca1 O7 H71 110.5(14) . . ? Ca1 O7 H72 118.0(15) . . ? H71 O7 H72 108(2) . . ? Ca1 O8 H81 142.8(15) . . ? Ca1 O8 H82 110.0(16) . . ? H81 O8 H82 104(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 H1A O2 0.88 2.20 3.0713(17) 172.7 3_655 N2 H2C O3 0.88 2.07 2.9410(19) 170.9 4 O7 H71 O2 0.83(2) 1.95(2) 2.7661(16) 172(2) 3_656 O7 H72 O4 0.79(2) 1.95(2) 2.7269(19) 169(2) 3_656 O8 H81 O3 0.81(2) 2.01(2) 2.8195(17) 175(2) 2_655 O8 H82 O6 0.78(2) 1.94(2) 2.7028(17) 167(2) 2_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.194 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.041 #============================================================================== data_kfk-57b _database_code_depnum_ccdc_archive 'CCDC 813337' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H64 Ca4 Cu4 N8 O46' _chemical_formula_weight 1663.35 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' 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.6989(9) _cell_length_b 19.186(2) _cell_length_c 22.557(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.501(11) _cell_angle_gamma 90.00 _cell_volume 2880.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 11234 _cell_measurement_theta_min 1.39 _cell_measurement_theta_max 27.09 _exptl_crystal_description needle _exptl_crystal_colour pink _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.918 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1704 _exptl_absorpt_coefficient_mu 1.937 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7219 _exptl_absorpt_correction_T_max 0.9442 _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 19609 _diffrn_reflns_av_R_equivalents 0.0886 _diffrn_reflns_av_sigmaI/netI 0.1073 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 26.78 _reflns_number_total 6125 _reflns_number_gt 3770 _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^)+(0.0448P)^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 6125 _refine_ls_number_parameters 461 _refine_ls_number_restraints 65 _refine_ls_R_factor_all 0.1098 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.951 _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 Cu1 Cu 0.07561(11) 0.73187(3) 0.10118(3) 0.02385(17) Uani 1 1 d . . . Cu2 Cu 0.35285(12) 0.32763(3) 0.35975(3) 0.02599(18) Uani 1 1 d . . . Ca1 Ca 0.05561(18) 0.58737(5) -0.04765(5) 0.0241(3) Uani 1 1 d . . . Ca2 Ca 0.21109(19) 0.55045(5) 0.33012(5) 0.0269(3) Uani 1 1 d . . . N1 N 0.1143(7) 0.8156(2) 0.14709(18) 0.0225(10) Uani 1 1 d . . . N2 N 0.0717(7) 0.6692(2) 0.16625(18) 0.0232(10) Uani 1 1 d . . . N3 N 0.3691(7) 0.2987(2) 0.27947(19) 0.0235(10) Uani 1 1 d . . . N4 N 0.3992(7) 0.2381(2) 0.39595(19) 0.0255(10) Uani 1 1 d . . . O1 O 0.0877(6) 0.79068(18) 0.03287(16) 0.0291(9) Uani 1 1 d . . . O2 O 0.1091(7) 0.9019(2) 0.00609(18) 0.0393(11) Uani 1 1 d . . . O3 O 0.1575(6) 0.87901(18) 0.23376(16) 0.0289(9) Uani 1 1 d . . . O4 O 0.1452(7) 0.63646(18) 0.26243(16) 0.0308(10) Uani 1 1 d . . . O5 O 0.0326(6) 0.64795(18) 0.05053(16) 0.0263(9) Uani 1 1 d . . . O6 O -0.0081(7) 0.53450(18) 0.05481(16) 0.0310(10) Uani 1 1 d . . . O7 O 0.3112(7) 0.42073(19) 0.32621(16) 0.0301(9) Uani 1 1 d . . . O8 O 0.3154(7) 0.48098(19) 0.24376(17) 0.0347(10) Uani 1 1 d . . . O9 O 0.3701(6) 0.21931(19) 0.20419(16) 0.0309(9) Uani 1 1 d . . . O10 O 0.4635(7) 0.12203(19) 0.39772(17) 0.0324(10) Uani 1 1 d . . . O11 O 0.3551(7) 0.36211(19) 0.44021(17) 0.0334(10) Uani 1 1 d . . . O12 O 0.3933(7) 0.3283(2) 0.53512(17) 0.0405(11) Uani 1 1 d . . . O13 O -0.2861(7) 0.6020(2) -0.07827(19) 0.0346(10) Uani 1 1 d D . . H131 H -0.353(9) 0.570(2) -0.101(2) 0.041 Uiso 1 1 d D . . H132 H -0.349(9) 0.6405(19) -0.090(3) 0.041 Uiso 1 1 d D . . O14 O 0.1522(7) 0.5792(2) -0.14518(17) 0.0326(10) Uani 1 1 d D . . H141 H 0.261(7) 0.556(3) -0.145(2) 0.039 Uiso 1 1 d D . . H142 H 0.132(9) 0.598(3) -0.1808(19) 0.039 Uiso 1 1 d D . . O15 O 0.1146(7) 0.70627(19) -0.06934(18) 0.0327(10) Uani 1 1 d D . . H151 H 0.229(7) 0.713(3) -0.083(2) 0.039 Uiso 1 1 d D . . H152 H 0.110(9) 0.735(3) -0.041(2) 0.039 Uiso 1 1 d D . . O16 O 0.3903(7) 0.5705(2) -0.00433(18) 0.0352(10) Uani 1 1 d D . . H161 H 0.437(9) 0.590(3) 0.0298(17) 0.042 Uiso 1 1 d D . . H162 H 0.487(8) 0.575(3) -0.026(2) 0.042 Uiso 1 1 d D . . O17 O 0.5515(8) 0.5921(2) 0.3445(2) 0.0498(13) Uani 1 1 d D . . H171 H 0.581(14) 0.595(4) 0.3800(16) 0.075 Uiso 1 1 d D . . H172 H 0.562(13) 0.631(3) 0.327(3) 0.075 Uiso 1 1 d D . . O18 O -0.1200(7) 0.5131(2) 0.2991(2) 0.0379(11) Uani 1 1 d D . . H181 H -0.151(9) 0.4689(19) 0.292(3) 0.045 Uiso 1 1 d D . . H182 H -0.208(9) 0.527(3) 0.322(3) 0.045 Uiso 1 1 d D . . O19 O 0.2738(9) 0.5067(2) 0.42902(19) 0.0470(13) Uani 1 1 d D . . H191 H 0.226(10) 0.526(3) 0.460(2) 0.056 Uiso 1 1 d D . . H192 H 0.319(11) 0.467(2) 0.444(3) 0.056 Uiso 1 1 d D . . O20 O 0.0589(8) 0.6329(2) 0.38841(19) 0.0467(13) Uani 1 1 d D . . H201 H 0.023(11) 0.630(3) 0.4240(19) 0.056 Uiso 1 1 d D . . H202 H 0.010(11) 0.672(3) 0.375(3) 0.056 Uiso 1 1 d D . . C1 C 0.1074(10) 0.8566(3) 0.0451(2) 0.0278(13) Uani 1 1 d . . . C2 C 0.1307(10) 0.8772(3) 0.1103(2) 0.0275(13) Uani 1 1 d . . . H2A H 0.2631 0.8995 0.1209 0.033 Uiso 1 1 calc R . . H2B H 0.0250 0.9111 0.1176 0.033 Uiso 1 1 calc R . . C3 C 0.1321(9) 0.8216(3) 0.2057(2) 0.0234(12) Uani 1 1 d . . . C4 C 0.1287(9) 0.7575(2) 0.2449(2) 0.0222(12) Uani 1 1 d . . . H4A H 0.0138 0.7640 0.2684 0.027 Uiso 1 1 calc R . . H4B H 0.2514 0.7602 0.2737 0.027 Uiso 1 1 calc R . . C5 C 0.1160(9) 0.6827(3) 0.2230(2) 0.0228(12) Uani 1 1 d . . . C6 C 0.0483(10) 0.5960(3) 0.1478(2) 0.0264(13) Uani 1 1 d . . . H6A H -0.0699 0.5756 0.1640 0.032 Uiso 1 1 calc R . . H6B H 0.1688 0.5691 0.1638 0.032 Uiso 1 1 calc R . . C7 C 0.0214(9) 0.5914(3) 0.0812(2) 0.0258(12) Uani 1 1 d . . . C8 C 0.3255(9) 0.4239(3) 0.2696(2) 0.0258(12) Uani 1 1 d . . . C9 C 0.3529(9) 0.3565(3) 0.2367(2) 0.0258(13) Uani 1 1 d . . . H9A H 0.2369 0.3489 0.2062 0.031 Uiso 1 1 calc R . . H9B H 0.4760 0.3591 0.2164 0.031 Uiso 1 1 calc R . . C10 C 0.3757(9) 0.2341(3) 0.2591(2) 0.0248(12) Uani 1 1 d . . . C11 C 0.4004(9) 0.1732(3) 0.3020(2) 0.0276(13) Uani 1 1 d . . . H11A H 0.2832 0.1425 0.2911 0.033 Uiso 1 1 calc R . . H11B H 0.5196 0.1471 0.2918 0.033 Uiso 1 1 calc R . . C12 C 0.4229(9) 0.1786(3) 0.3691(2) 0.0255(12) Uani 1 1 d . . . C13 C 0.4180(9) 0.2409(3) 0.4610(2) 0.0270(13) Uani 1 1 d . . . H13A H 0.5528 0.2242 0.4775 0.032 Uiso 1 1 calc R . . H13B H 0.3163 0.2101 0.4760 0.032 Uiso 1 1 calc R . . C14 C 0.3875(9) 0.3155(3) 0.4811(2) 0.0286(13) Uani 1 1 d . . . O21 O 0.4970(7) 0.2799(2) 0.10678(18) 0.0340(10) Uani 1 1 d D . . H211 H 0.464(10) 0.264(3) 0.1413(16) 0.041 Uiso 1 1 d D . . H212 H 0.457(10) 0.246(3) 0.0823(19) 0.041 Uiso 1 1 d D . . O22 O 0.4935(7) -0.00497(19) 0.35508(18) 0.0307(9) Uani 1 1 d D . . H221 H 0.484(10) 0.038(2) 0.364(2) 0.037 Uiso 1 1 d D . . H222 H 0.554(9) -0.008(3) 0.325(2) 0.037 Uiso 1 1 d D . . O23 O 0.728(3) 0.5384(9) 0.4418(8) 0.265(7) Uiso 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 Cu1 0.0308(4) 0.0192(3) 0.0216(3) -0.0004(3) 0.0030(3) 0.0001(3) Cu2 0.0326(4) 0.0205(3) 0.0253(3) 0.0027(3) 0.0050(3) 0.0034(3) Ca1 0.0266(7) 0.0206(5) 0.0250(5) -0.0011(4) 0.0028(5) -0.0011(5) Ca2 0.0310(7) 0.0216(5) 0.0284(6) 0.0031(4) 0.0048(5) 0.0019(5) N1 0.027(3) 0.019(2) 0.022(2) 0.0012(17) 0.003(2) -0.0031(19) N2 0.030(3) 0.018(2) 0.022(2) -0.0008(18) 0.005(2) 0.000(2) N3 0.027(3) 0.015(2) 0.028(2) 0.0060(18) 0.002(2) 0.0047(19) N4 0.029(3) 0.022(2) 0.024(2) -0.0007(19) 0.001(2) 0.003(2) O1 0.041(3) 0.0232(19) 0.0239(19) -0.0002(15) 0.0057(18) 0.0014(18) O2 0.056(3) 0.029(2) 0.033(2) 0.0054(18) 0.010(2) -0.005(2) O3 0.042(3) 0.0177(17) 0.026(2) -0.0038(15) -0.0006(18) -0.0010(17) O4 0.047(3) 0.0249(19) 0.0199(19) 0.0055(16) 0.0027(18) 0.0020(19) O5 0.034(3) 0.0224(18) 0.0236(19) 0.0001(15) 0.0062(17) -0.0008(17) O6 0.045(3) 0.0194(18) 0.029(2) -0.0049(16) 0.0064(19) -0.0040(18) O7 0.043(3) 0.0222(19) 0.026(2) 0.0026(16) 0.0063(18) 0.0032(18) O8 0.052(3) 0.025(2) 0.030(2) 0.0060(17) 0.015(2) 0.0120(19) O9 0.042(3) 0.026(2) 0.026(2) 0.0018(16) 0.0058(18) 0.0028(18) O10 0.044(3) 0.0259(19) 0.026(2) 0.0023(16) -0.0013(19) 0.0068(19) O11 0.046(3) 0.0240(19) 0.030(2) 0.0032(17) 0.006(2) 0.0071(19) O12 0.071(4) 0.026(2) 0.025(2) -0.0010(17) 0.007(2) 0.012(2) O13 0.029(3) 0.031(2) 0.042(3) -0.0037(19) -0.001(2) 0.0010(19) O14 0.037(3) 0.037(2) 0.025(2) 0.0044(18) 0.0075(19) 0.009(2) O15 0.041(3) 0.027(2) 0.032(2) -0.0005(17) 0.009(2) -0.0014(19) O16 0.030(3) 0.045(2) 0.031(2) -0.0052(19) 0.0051(19) -0.002(2) O17 0.034(3) 0.041(3) 0.074(3) 0.024(3) 0.002(3) 0.004(2) O18 0.032(3) 0.028(2) 0.054(3) -0.001(2) 0.008(2) -0.0032(19) O19 0.085(4) 0.026(2) 0.030(2) 0.0033(18) 0.006(2) 0.009(2) O20 0.084(4) 0.027(2) 0.031(2) 0.0011(19) 0.013(2) 0.013(2) C1 0.030(4) 0.024(3) 0.030(3) 0.001(2) 0.005(3) 0.001(3) C2 0.035(4) 0.024(3) 0.024(3) 0.001(2) 0.004(3) -0.004(2) C3 0.024(3) 0.017(2) 0.029(3) -0.003(2) 0.005(2) -0.001(2) C4 0.028(3) 0.018(2) 0.020(3) 0.003(2) 0.001(2) -0.001(2) C5 0.022(3) 0.021(3) 0.025(3) 0.000(2) 0.002(2) 0.000(2) C6 0.034(4) 0.020(3) 0.026(3) -0.002(2) 0.006(3) -0.001(2) C7 0.021(3) 0.029(3) 0.028(3) -0.001(2) 0.005(2) -0.001(2) C8 0.027(3) 0.024(3) 0.028(3) 0.007(2) 0.009(2) 0.005(2) C9 0.032(4) 0.022(2) 0.024(3) 0.001(2) 0.006(3) 0.002(2) C10 0.021(3) 0.029(3) 0.024(3) 0.003(2) 0.005(2) -0.002(2) C11 0.030(4) 0.023(3) 0.030(3) -0.001(2) 0.004(3) 0.001(3) C12 0.023(3) 0.024(3) 0.030(3) 0.003(2) 0.005(2) 0.001(2) C13 0.027(3) 0.033(3) 0.021(3) 0.003(2) 0.003(2) 0.003(3) C14 0.029(4) 0.029(3) 0.028(3) 0.004(2) 0.004(3) 0.001(3) O21 0.045(3) 0.028(2) 0.030(2) 0.0008(17) 0.006(2) -0.005(2) O22 0.034(3) 0.0233(19) 0.036(2) -0.0033(17) 0.009(2) 0.0016(18) _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 N2 1.899(4) . ? Cu1 N1 1.913(4) . ? Cu1 O1 1.919(4) . ? Cu1 O5 1.976(3) . ? Cu2 N3 1.909(4) . ? Cu2 N4 1.912(4) . ? Cu2 O11 1.930(4) . ? Cu2 O7 1.948(4) . ? Ca1 O13 2.332(5) . ? Ca1 O6 2.363(4) 3_565 ? Ca1 O16 2.364(5) . ? Ca1 O14 2.368(4) . ? Ca1 O15 2.376(4) . ? Ca1 O5 2.521(4) . ? Ca1 O6 2.603(4) . ? Ca1 H141 2.79(5) . ? Ca2 O4 2.258(4) . ? Ca2 O18 2.360(5) . ? Ca2 O20 2.361(4) . ? Ca2 O19 2.376(4) . ? Ca2 O17 2.404(5) . ? Ca2 O8 2.524(4) . ? Ca2 O7 2.582(4) . ? Ca2 H171 2.74(8) . ? N1 C3 1.319(7) . ? N1 C2 1.455(6) . ? N2 C5 1.306(6) . ? N2 C6 1.470(6) . ? N3 C10 1.324(7) . ? N3 C9 1.466(6) . ? N4 C12 1.310(7) . ? N4 C13 1.459(7) . ? O1 C1 1.297(6) . ? O2 C1 1.239(6) . ? O3 C3 1.272(6) . ? O4 C5 1.256(6) . ? O5 C7 1.293(6) . ? O6 C7 1.249(6) . ? O6 Ca1 2.363(4) 3_565 ? O7 C8 1.293(6) . ? O8 C8 1.238(6) . ? O9 C10 1.268(6) . ? O10 C12 1.275(6) . ? O11 C14 1.286(6) . ? O12 C14 1.238(6) . ? O13 H131 0.88(3) . ? O13 H132 0.88(3) . ? O14 H141 0.85(3) . ? O14 H142 0.88(3) . ? O15 H151 0.87(3) . ? O15 H152 0.86(3) . ? O16 H161 0.88(3) . ? O16 H162 0.86(3) . ? O17 H171 0.80(4) . ? O17 H172 0.85(4) . ? O18 H181 0.88(3) . ? O18 H182 0.87(3) . ? O19 H191 0.89(3) . ? O19 H192 0.87(3) . ? O20 H201 0.87(3) . ? O20 H202 0.86(3) . ? C1 C2 1.513(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.517(7) . ? C4 C5 1.518(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C6 C7 1.494(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C8 C9 1.512(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.515(7) . ? C11 C12 1.509(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C13 C14 1.523(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? O21 H211 0.89(3) . ? O21 H212 0.88(3) . ? O22 H221 0.86(3) . ? O22 H222 0.84(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 N2 Cu1 N1 97.23(18) . . ? N2 Cu1 O1 176.41(17) . . ? N1 Cu1 O1 85.73(17) . . ? N2 Cu1 O5 85.26(16) . . ? N1 Cu1 O5 177.44(17) . . ? O1 Cu1 O5 91.80(15) . . ? N3 Cu2 N4 96.90(18) . . ? N3 Cu2 O11 175.2(2) . . ? N4 Cu2 O11 85.58(17) . . ? N3 Cu2 O7 85.35(16) . . ? N4 Cu2 O7 177.42(19) . . ? O11 Cu2 O7 92.09(16) . . ? O13 Ca1 O6 88.77(15) . 3_565 ? O13 Ca1 O16 172.76(15) . . ? O6 Ca1 O16 90.40(15) 3_565 . ? O13 Ca1 O14 95.45(16) . . ? O6 Ca1 O14 85.38(14) 3_565 . ? O16 Ca1 O14 91.65(16) . . ? O13 Ca1 O15 90.23(16) . . ? O6 Ca1 O15 163.84(14) 3_565 . ? O16 Ca1 O15 92.56(16) . . ? O14 Ca1 O15 78.65(14) . . ? O13 Ca1 O5 92.82(14) . . ? O6 Ca1 O5 119.67(13) 3_565 . ? O16 Ca1 O5 81.35(14) . . ? O14 Ca1 O5 153.80(14) . . ? O15 Ca1 O5 76.49(13) . . ? O13 Ca1 O6 93.20(15) . . ? O6 Ca1 O6 68.94(14) 3_565 . ? O16 Ca1 O6 79.79(14) . . ? O14 Ca1 O6 152.69(13) . . ? O15 Ca1 O6 127.22(13) . . ? O5 Ca1 O6 50.75(11) . . ? O13 Ca1 H141 110.4(10) . . ? O6 Ca1 H141 79.0(13) 3_565 . ? O16 Ca1 H141 76.5(10) . . ? O14 Ca1 H141 16.6(8) . . ? O15 Ca1 H141 86.2(12) . . ? O5 Ca1 H141 151.2(13) . . ? O6 Ca1 H141 139.7(9) . . ? O4 Ca2 O18 85.19(16) . . ? O4 Ca2 O20 79.83(15) . . ? O18 Ca2 O20 85.31(18) . . ? O4 Ca2 O19 153.32(15) . . ? O18 Ca2 O19 103.39(18) . . ? O20 Ca2 O19 75.84(16) . . ? O4 Ca2 O17 87.58(16) . . ? O18 Ca2 O17 170.48(17) . . ? O20 Ca2 O17 99.51(19) . . ? O19 Ca2 O17 85.80(19) . . ? O4 Ca2 O8 85.07(13) . . ? O18 Ca2 O8 86.76(16) . . ? O20 Ca2 O8 163.46(15) . . ? O19 Ca2 O8 120.21(15) . . ? O17 Ca2 O8 86.46(17) . . ? O4 Ca2 O7 135.49(13) . . ? O18 Ca2 O7 86.33(15) . . ? O20 Ca2 O7 142.66(14) . . ? O19 Ca2 O7 70.88(13) . . ? O17 Ca2 O7 94.54(15) . . ? O8 Ca2 O7 50.85(12) . . ? O4 Ca2 H171 98.6(12) . . ? O18 Ca2 H171 173.0(12) . . ? O20 Ca2 H171 89.5(17) . . ? O19 Ca2 H171 70.7(10) . . ? O17 Ca2 H171 16.4(11) . . ? O8 Ca2 H171 99.5(16) . . ? O7 Ca2 H171 95.0(17) . . ? C3 N1 C2 119.8(4) . . ? C3 N1 Cu1 127.4(3) . . ? C2 N1 Cu1 112.8(3) . . ? C5 N2 C6 118.2(4) . . ? C5 N2 Cu1 127.6(4) . . ? C6 N2 Cu1 113.3(3) . . ? C10 N3 C9 118.9(4) . . ? C10 N3 Cu2 127.5(3) . . ? C9 N3 Cu2 113.3(3) . . ? C12 N4 C13 119.7(4) . . ? C12 N4 Cu2 127.5(4) . . ? C13 N4 Cu2 112.8(3) . . ? C1 O1 Cu1 114.5(3) . . ? C5 O4 Ca2 176.6(4) . . ? C7 O5 Cu1 112.8(3) . . ? C7 O5 Ca1 95.5(3) . . ? Cu1 O5 Ca1 149.76(18) . . ? C7 O6 Ca1 155.6(4) . 3_565 ? C7 O6 Ca1 92.8(3) . . ? Ca1 O6 Ca1 111.06(14) 3_565 . ? C8 O7 Cu2 113.8(3) . . ? C8 O7 Ca2 92.1(3) . . ? Cu2 O7 Ca2 153.79(19) . . ? C8 O8 Ca2 96.2(3) . . ? C14 O11 Cu2 114.8(3) . . ? Ca1 O13 H131 120(4) . . ? Ca1 O13 H132 128(4) . . ? H131 O13 H132 102(4) . . ? Ca1 O14 H141 111(4) . . ? Ca1 O14 H142 142(4) . . ? H141 O14 H142 105(4) . . ? Ca1 O15 H151 113(4) . . ? Ca1 O15 H152 117(4) . . ? H151 O15 H152 106(4) . . ? Ca1 O16 H161 122(4) . . ? Ca1 O16 H162 120(4) . . ? H161 O16 H162 104(4) . . ? Ca2 O17 H171 106(7) . . ? Ca2 O17 H172 111(6) . . ? H171 O17 H172 112(5) . . ? Ca2 O18 H181 122(4) . . ? Ca2 O18 H182 114(4) . . ? H181 O18 H182 104(4) . . ? Ca2 O19 H191 124(4) . . ? Ca2 O19 H192 134(4) . . ? H191 O19 H192 101(4) . . ? Ca2 O20 H201 131(4) . . ? Ca2 O20 H202 123(4) . . ? H201 O20 H202 106(4) . . ? O2 C1 O1 122.8(5) . . ? O2 C1 C2 119.9(5) . . ? O1 C1 C2 117.3(5) . . ? N1 C2 C1 109.7(4) . . ? N1 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? N1 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? O3 C3 N1 124.5(5) . . ? O3 C3 C4 114.9(4) . . ? N1 C3 C4 120.5(4) . . ? C3 C4 C5 125.5(4) . . ? C3 C4 H4A 105.9 . . ? C5 C4 H4A 105.9 . . ? C3 C4 H4B 105.9 . . ? C5 C4 H4B 105.9 . . ? H4A C4 H4B 106.3 . . ? O4 C5 N2 123.7(5) . . ? O4 C5 C4 116.0(4) . . ? N2 C5 C4 120.3(5) . . ? N2 C6 C7 109.7(4) . . ? N2 C6 H6A 109.7 . . ? C7 C6 H6A 109.7 . . ? N2 C6 H6B 109.7 . . ? C7 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? O6 C7 O5 119.6(5) . . ? O6 C7 C6 121.6(5) . . ? O5 C7 C6 118.7(5) . . ? O6 C7 Ca1 62.1(3) . . ? O5 C7 Ca1 58.5(3) . . ? C6 C7 Ca1 168.5(4) . . ? O8 C8 O7 120.1(5) . . ? O8 C8 C9 121.9(5) . . ? O7 C8 C9 118.1(4) . . ? O8 C8 Ca2 58.9(3) . . ? O7 C8 Ca2 61.7(3) . . ? C9 C8 Ca2 171.9(4) . . ? N3 C9 C8 109.2(4) . . ? N3 C9 H9A 109.8 . . ? C8 C9 H9A 109.8 . . ? N3 C9 H9B 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? O9 C10 N3 123.4(5) . . ? O9 C10 C11 116.0(5) . . ? N3 C10 C11 120.5(5) . . ? C12 C11 C10 125.4(5) . . ? C12 C11 H11A 106.0 . . ? C10 C11 H11A 106.0 . . ? C12 C11 H11B 106.0 . . ? C10 C11 H11B 106.0 . . ? H11A C11 H11B 106.3 . . ? O10 C12 N4 122.5(5) . . ? O10 C12 C11 116.1(5) . . ? N4 C12 C11 121.3(5) . . ? N4 C13 C14 109.6(4) . . ? N4 C13 H13A 109.8 . . ? C14 C13 H13A 109.8 . . ? N4 C13 H13B 109.8 . . ? C14 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? O12 C14 O11 123.5(5) . . ? O12 C14 C13 119.3(5) . . ? O11 C14 C13 117.2(5) . . ? H211 O21 H212 102(4) . . ? H221 O22 H222 108(4) . . ? 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 O13 H131 O22 0.88(3) 1.84(4) 2.721(6) 176(6) 4_465 O13 H132 O21 0.88(3) 1.84(4) 2.709(6) 173(6) 3_565 O14 H141 O22 0.85(3) 1.84(3) 2.693(6) 179(6) 4_565 O14 H142 O3 0.88(3) 2.00(4) 2.850(5) 162(5) 4_575 O15 H151 O21 0.87(3) 1.97(4) 2.838(6) 173(6) 3_665 O15 H152 O1 0.86(3) 1.99(3) 2.840(5) 171(6) . O16 H161 O10 0.88(3) 1.80(3) 2.681(6) 175(6) 2_655 O16 H162 O13 0.86(3) 2.09(4) 2.944(6) 171(6) 1_655 O17 H172 O9 0.85(4) 1.91(4) 2.751(6) 170(8) 2_655 O18 H181 O3 0.88(3) 1.82(3) 2.681(5) 164(6) 2_545 O18 H182 O17 0.87(3) 2.14(4) 2.950(7) 155(6) 1_455 O19 H191 O2 0.89(3) 1.94(4) 2.784(6) 158(6) 4_576 O19 H191 O23 0.89(3) 2.52(6) 3.041(18) 118(5) 3_666 O19 H192 O11 0.87(3) 2.03(4) 2.833(6) 152(6) . O19 H191 O23 0.89(3) 2.52(6) 3.041(18) 118(5) 3_666 O20 H201 O2 0.87(3) 1.97(4) 2.721(6) 144(6) 4_576 O21 H211 O9 0.89(3) 1.82(4) 2.707(5) 170(5) . O22 H221 O10 0.86(3) 1.79(3) 2.636(5) 169(5) . O22 H222 O8 0.84(3) 1.87(3) 2.707(5) 177(5) 2_645 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.851 _refine_diff_density_min -0.647 _refine_diff_density_rms 0.105