# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1L _database_code_depnum_ccdc_archive 'CCDC 916191' #TrackingRef '1-3-Revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N O4 ' _chemical_formula_sum 'C11 H13 N O4' _chemical_formula_weight 223.22 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.3335(6) _cell_length_b 5.8827(4) _cell_length_c 12.8465(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.790(7) _cell_angle_gamma 90.00 _cell_volume 546.14(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1198 _cell_measurement_theta_min 2.8129 _cell_measurement_theta_max 27.4586 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 236 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9596 _exptl_absorpt_correction_T_max 0.9897 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% ? _diffrn_reflns_number 2345 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1533 _reflns_number_gt 1153 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0230P)^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 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 0.4(14) _chemical_absolute_configuration syn _refine_ls_number_reflns 1533 _refine_ls_number_parameters 146 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0606 _refine_ls_wR_factor_gt 0.0585 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.011 _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 0.4448(3) 0.7885(3) 1.18122(15) 0.0640(6) Uani 1 1 d . . . H1A H 0.5175 0.8326 1.2329 0.096 Uiso 1 1 calc R . . O2 O 0.3415(3) 1.1399(3) 1.18019(14) 0.0650(7) Uani 1 1 d . . . O3 O 0.3117(3) 1.3705(3) 0.65172(13) 0.0419(5) Uani 1 1 d . . . O4 O 0.0456(2) 1.2182(3) 0.57245(13) 0.0480(5) Uani 1 1 d . . . N1 N 0.1436(3) 0.7916(3) 0.63157(14) 0.0314(5) Uani 1 1 d . . . H1B H 0.1996 0.6550 0.6386 0.038 Uiso 1 1 calc R . . H1C H 0.0830 0.8016 0.5646 0.038 Uiso 1 1 calc R . . C1 C 0.3515(3) 0.9623(5) 1.1357(2) 0.0378(7) Uani 1 1 d . . . C2 C 0.2619(3) 0.9159(4) 1.02586(19) 0.0295(6) Uani 1 1 d . . . C3 C 0.1521(3) 1.0806(4) 0.96953(19) 0.0348(7) Uani 1 1 d . . . H3A H 0.1345 1.2189 1.0015 0.042 Uiso 1 1 calc R . . C4 C 0.0686(3) 1.0425(4) 0.8668(2) 0.0372(7) Uani 1 1 d . . . H4A H -0.0040 1.1556 0.8300 0.045 Uiso 1 1 calc R . . C5 C 0.0913(3) 0.8377(4) 0.81778(18) 0.0309(7) Uani 1 1 d . . . C6 C 0.1999(3) 0.6704(5) 0.87415(18) 0.0359(6) Uani 1 1 d . . . H6A H 0.2161 0.5315 0.8423 0.043 Uiso 1 1 calc R . . C7 C 0.2839(3) 0.7094(5) 0.97756(18) 0.0357(6) Uani 1 1 d . . . H7A H 0.3558 0.5962 1.0149 0.043 Uiso 1 1 calc R . . C8 C 0.0028(3) 0.7983(5) 0.70409(18) 0.0385(7) Uani 1 1 d . . . H8A H -0.0644 0.6557 0.6989 0.046 Uiso 1 1 calc R . . H8B H -0.0854 0.9190 0.6817 0.046 Uiso 1 1 calc R . . C9 C 0.2067(4) 1.2052(5) 0.62104(17) 0.0305(6) Uani 1 1 d . . . C10 C 0.2901(3) 0.9705(4) 0.64736(18) 0.0279(6) Uani 1 1 d . . . H10A H 0.3510 0.9688 0.7214 0.034 Uiso 1 1 calc R . . C11 C 0.4325(4) 0.9158(4) 0.5776(2) 0.0545(9) Uani 1 1 d . . . H11A H 0.4844 0.7682 0.5956 0.082 Uiso 1 1 calc R . . H11B H 0.5291 1.0278 0.5884 0.082 Uiso 1 1 calc R . . H11C H 0.3739 0.9167 0.5048 0.082 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0873(16) 0.0389(12) 0.0502(13) -0.0011(11) -0.0327(11) 0.0029(13) O2 0.0753(14) 0.0623(17) 0.0507(13) -0.0216(13) -0.0087(11) 0.0299(14) O3 0.0552(12) 0.0201(10) 0.0444(12) -0.0044(9) -0.0089(9) -0.0035(10) O4 0.0566(11) 0.0340(13) 0.0441(10) 0.0079(9) -0.0179(9) 0.0020(11) N1 0.0470(12) 0.0209(12) 0.0228(11) -0.0014(9) -0.0042(9) 0.0037(11) C1 0.0352(16) 0.0418(18) 0.0356(17) -0.0030(17) 0.0039(13) 0.0020(17) C2 0.0286(14) 0.0277(18) 0.0328(14) -0.0003(13) 0.0070(12) 0.0010(14) C3 0.0389(16) 0.0274(16) 0.0396(17) -0.0019(13) 0.0108(14) 0.0069(14) C4 0.0387(17) 0.0358(18) 0.0364(17) 0.0071(13) 0.0043(13) 0.0111(14) C5 0.0293(15) 0.0357(17) 0.0288(15) 0.0061(14) 0.0075(12) -0.0039(14) C6 0.0409(14) 0.0275(16) 0.0396(15) -0.0010(14) 0.0076(12) 0.0041(15) C7 0.0368(15) 0.0343(18) 0.0352(15) 0.0066(15) 0.0035(12) 0.0059(15) C8 0.0345(15) 0.0402(17) 0.0392(16) 0.0038(13) 0.0022(13) -0.0045(14) C9 0.0473(16) 0.0243(16) 0.0177(12) 0.0045(12) -0.0001(11) 0.0063(17) C10 0.0343(14) 0.0199(14) 0.0282(14) -0.0024(12) 0.0012(12) 0.0000(14) C11 0.072(2) 0.036(2) 0.063(2) 0.0044(15) 0.0319(18) 0.0042(17) _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 H1A 0.8200 . ? O2 C1 1.199(3) . ? O3 C9 1.262(3) . ? O4 C9 1.241(3) . ? N1 C10 1.492(3) . ? N1 C8 1.504(3) . ? N1 H1B 0.9000 . ? N1 H1C 0.9000 . ? C1 C2 1.477(3) . ? C2 C3 1.383(3) . ? C2 C7 1.386(3) . ? C3 C4 1.375(3) . ? C3 H3A 0.9300 . ? C4 C5 1.382(3) . ? C4 H4A 0.9300 . ? C5 C6 1.390(3) . ? C5 C8 1.512(3) . ? C6 C7 1.385(3) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.524(3) . ? C10 C11 1.522(3) . ? C10 H10A 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1A 109.5 . . ? C10 N1 C8 116.82(18) . . ? C10 N1 H1B 108.1 . . ? C8 N1 H1B 108.1 . . ? C10 N1 H1C 108.1 . . ? C8 N1 H1C 108.1 . . ? H1B N1 H1C 107.3 . . ? O2 C1 O1 122.4(3) . . ? O2 C1 C2 124.3(3) . . ? O1 C1 C2 113.3(3) . . ? C3 C2 C7 118.8(2) . . ? C3 C2 C1 119.7(2) . . ? C7 C2 C1 121.5(2) . . ? C4 C3 C2 120.8(2) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C3 C4 C5 120.7(2) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C4 C5 C6 118.9(2) . . ? C4 C5 C8 120.6(2) . . ? C6 C5 C8 120.6(2) . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C6 C7 C2 120.5(2) . . ? C6 C7 H7A 119.7 . . ? C2 C7 H7A 119.7 . . ? N1 C8 C5 112.02(19) . . ? N1 C8 H8A 109.2 . . ? C5 C8 H8A 109.2 . . ? N1 C8 H8B 109.2 . . ? C5 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? O4 C9 O3 126.0(3) . . ? O4 C9 C10 118.6(2) . . ? O3 C9 C10 115.4(2) . . ? N1 C10 C11 108.73(19) . . ? N1 C10 C9 110.86(19) . . ? C11 C10 C9 110.52(19) . . ? N1 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 -2.7(4) . . . . ? O1 C1 C2 C3 177.2(2) . . . . ? O2 C1 C2 C7 177.7(3) . . . . ? O1 C1 C2 C7 -2.3(3) . . . . ? C7 C2 C3 C4 -1.1(3) . . . . ? C1 C2 C3 C4 179.4(2) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C3 C4 C5 C8 -178.6(2) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C8 C5 C6 C7 178.6(2) . . . . ? C5 C6 C7 C2 -0.4(3) . . . . ? C3 C2 C7 C6 1.0(3) . . . . ? C1 C2 C7 C6 -179.4(2) . . . . ? C10 N1 C8 C5 -44.6(3) . . . . ? C4 C5 C8 N1 109.3(3) . . . . ? C6 C5 C8 N1 -69.5(3) . . . . ? C8 N1 C10 C11 172.3(2) . . . . ? C8 N1 C10 C9 -66.0(2) . . . . ? O4 C9 C10 N1 -13.7(3) . . . . ? O3 C9 C10 N1 166.3(2) . . . . ? O4 C9 C10 C11 106.9(2) . . . . ? O3 C9 C10 C11 -73.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O3 0.82 1.78 2.593(2) 168.6 2_647 N1 H1B O3 0.90 1.86 2.759(3) 179.0 1_545 N1 H1C O4 0.90 1.92 2.783(3) 161.4 2_546 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.120 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.032 data_2L _database_code_depnum_ccdc_archive 'CCDC 916192' #TrackingRef '1-3-Revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 Cu N O5, H2 O' _chemical_formula_sum 'C11 H15 Cu N O6' _chemical_formula_weight 320.78 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 tetragonal _symmetry_space_group_name_H-M P4(3) _symmetry_space_group_name_Hall 'P 4cw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z+3/4' '-x, -y, z+1/2' 'y, -x, z+1/4' _cell_length_a 7.5402(2) _cell_length_b 7.5402(2) _cell_length_c 22.7232(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1291.92(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3596 _cell_measurement_theta_min 2.7009 _cell_measurement_theta_max 27.4835 _exptl_crystal_description prism _exptl_crystal_colour dark-blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 1.712 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5475 _exptl_absorpt_correction_T_max 0.6076 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% ? _diffrn_reflns_number 10145 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2847 _reflns_number_gt 2736 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0380P)^2^+0.6300P] 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 -0.004(16) _chemical_absolute_configuration rmad _refine_ls_number_reflns 2847 _refine_ls_number_parameters 173 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 0.34321(5) 0.19118(4) 0.102059(18) 0.03067(11) Uani 1 1 d . . . O1 O 0.3316(3) 0.0208(3) 0.03759(12) 0.0382(5) Uani 1 1 d . . . O2 O 0.6227(3) 0.0041(3) 0.05046(12) 0.0433(6) Uani 1 1 d . . . O3 O 0.3011(3) 0.3702(3) 0.16047(11) 0.0353(5) Uani 1 1 d . . . O4 O 0.2983(4) 0.6624(3) 0.17323(11) 0.0387(6) Uani 1 1 d . . . O5 O 0.2796(6) 0.0130(4) 0.15871(15) 0.0816(14) Uani 1 1 d . . . H5A H 0.2856 -0.0987 0.1632 0.098 Uiso 1 1 d R . . H5B H 0.2285 0.0407 0.1908 0.098 Uiso 1 1 d R . . O6 O -0.0299(4) 0.1160(5) 0.01442(16) 0.0621(8) Uani 1 1 d . . . H6C H -0.1148 0.0957 0.0381 0.093 Uiso 1 1 d R . . H6B H 0.0774 0.0881 0.0211 0.093 Uiso 1 1 d R . . N1 N 0.6048(3) -0.5822(3) -0.19928(12) 0.0261(5) Uani 1 1 d . . . H1A H 0.6264 -0.6221 -0.2364 0.031 Uiso 1 1 calc R . . C1 C 0.4877(5) -0.0267(4) 0.02104(16) 0.0336(7) Uani 1 1 d . . . C2 C 0.5014(5) -0.1261(4) -0.03554(16) 0.0318(7) Uani 1 1 d . . . C3 C 0.3551(5) -0.1701(4) -0.06931(17) 0.0357(7) Uani 1 1 d . . . H3A H 0.2421 -0.1402 -0.0562 0.043 Uiso 1 1 calc R . . C4 C 0.3749(4) -0.2583(4) -0.12235(16) 0.0347(7) Uani 1 1 d . . . H4A H 0.2748 -0.2890 -0.1439 0.042 Uiso 1 1 calc R . . C5 C 0.5423(4) -0.3016(4) -0.14391(16) 0.0293(6) Uani 1 1 d . . . C6 C 0.6891(4) -0.2581(5) -0.10935(17) 0.0371(8) Uani 1 1 d . . . H6A H 0.8022 -0.2875 -0.1224 0.044 Uiso 1 1 calc R . . C7 C 0.6693(5) -0.1724(5) -0.05622(18) 0.0379(8) Uani 1 1 d . . . H7A H 0.7690 -0.1451 -0.0339 0.045 Uiso 1 1 calc R . . C8 C 0.5679(4) -0.3870(4) -0.20285(15) 0.0309(6) Uani 1 1 d . . . H8A H 0.6658 -0.3293 -0.2228 0.037 Uiso 1 1 calc R . . H8B H 0.4620 -0.3684 -0.2263 0.037 Uiso 1 1 calc R . . C9 C 0.3067(4) 0.5296(4) 0.14098(15) 0.0282(6) Uani 1 1 d . . . C10 C 0.4493(4) -0.6808(4) -0.17583(15) 0.0277(6) Uani 1 1 d . . . H10A H 0.3402 -0.6162 -0.1853 0.033 Uiso 1 1 calc R . . C11 C 0.4410(5) -0.8655(5) -0.20227(18) 0.0428(8) Uani 1 1 d . . . H11A H 0.4335 -0.8567 -0.2443 0.064 Uiso 1 1 calc R . . H11B H 0.3384 -0.9263 -0.1875 0.064 Uiso 1 1 calc R . . H11C H 0.5459 -0.9302 -0.1917 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0441(2) 0.02321(16) 0.02470(19) -0.00164(15) 0.00475(17) 0.00038(14) O1 0.0471(13) 0.0317(11) 0.0358(15) -0.0073(10) 0.0056(11) -0.0003(10) O2 0.0506(14) 0.0449(13) 0.0343(15) -0.0104(12) -0.0048(12) 0.0002(11) O3 0.0585(15) 0.0248(10) 0.0226(12) 0.0015(9) 0.0050(11) -0.0005(10) O4 0.0595(15) 0.0267(10) 0.0299(14) -0.0051(9) 0.0015(11) 0.0035(10) O5 0.175(4) 0.0246(12) 0.045(2) 0.0017(12) 0.051(2) 0.0045(17) O6 0.0473(16) 0.082(2) 0.057(2) 0.0160(17) 0.0035(14) 0.0035(15) N1 0.0294(12) 0.0287(12) 0.0202(12) -0.0003(10) 0.0037(10) 0.0002(9) C1 0.0463(18) 0.0243(13) 0.0301(17) 0.0011(12) 0.0034(15) -0.0010(12) C2 0.0413(16) 0.0261(13) 0.0279(17) -0.0028(12) 0.0027(14) -0.0002(12) C3 0.0371(16) 0.0353(16) 0.035(2) -0.0055(13) 0.0058(14) 0.0032(13) C4 0.0361(16) 0.0335(15) 0.0344(18) -0.0074(13) -0.0042(14) 0.0001(13) C5 0.0367(14) 0.0263(12) 0.0249(16) -0.0023(13) 0.0027(14) -0.0010(11) C6 0.0322(16) 0.0451(19) 0.0340(19) -0.0121(15) 0.0016(14) 0.0001(14) C7 0.0394(17) 0.0463(18) 0.0279(19) -0.0089(15) -0.0022(14) -0.0009(14) C8 0.0409(16) 0.0285(14) 0.0233(16) 0.0001(12) -0.0012(13) 0.0010(12) C9 0.0343(15) 0.0280(14) 0.0222(16) -0.0009(12) 0.0008(12) -0.0013(12) C10 0.0255(13) 0.0305(14) 0.0270(17) 0.0018(13) -0.0020(12) -0.0017(11) C11 0.053(2) 0.0346(16) 0.040(2) -0.0025(15) -0.0030(18) -0.0099(15) _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 O3 1.919(2) . ? Cu1 O5 1.922(3) . ? Cu1 O1 1.950(3) . ? Cu1 N1 2.011(3) 4_665 ? O1 C1 1.287(4) . ? O2 C1 1.240(4) . ? O3 C9 1.282(4) . ? O4 C9 1.243(4) . ? O5 H5A 0.8499 . ? O5 H5B 0.8499 . ? O6 H6C 0.8499 . ? O6 H6B 0.8499 . ? N1 C10 1.487(4) . ? N1 C8 1.500(4) . ? N1 Cu1 2.011(3) 2_644 ? N1 H1A 0.9100 . ? C1 C2 1.491(5) . ? C2 C3 1.384(5) . ? C2 C7 1.395(5) . ? C3 C4 1.384(5) . ? C3 H3A 0.9300 . ? C4 C5 1.393(4) . ? C4 H4A 0.9300 . ? C5 C6 1.397(5) . ? C5 C8 1.498(5) . ? C6 C7 1.377(5) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.529(4) 4_665 ? C10 C11 1.518(4) . ? C10 C9 1.529(4) 2_644 ? C10 H10A 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu1 O5 89.26(12) . . ? O3 Cu1 O1 167.19(11) . . ? O5 Cu1 O1 91.81(11) . . ? O3 Cu1 N1 84.81(10) . 4_665 ? O5 Cu1 N1 173.38(14) . 4_665 ? O1 Cu1 N1 94.62(11) . 4_665 ? C1 O1 Cu1 111.2(2) . . ? C9 O3 Cu1 114.5(2) . . ? Cu1 O5 H5A 139.5 . . ? Cu1 O5 H5B 121.0 . . ? H5A O5 H5B 99.5 . . ? H6C O6 H6B 124.0 . . ? C10 N1 C8 111.3(2) . . ? C10 N1 Cu1 104.78(19) . 2_644 ? C8 N1 Cu1 116.60(19) . 2_644 ? C10 N1 H1A 107.9 . . ? C8 N1 H1A 107.9 . . ? Cu1 N1 H1A 107.9 2_644 . ? O2 C1 O1 122.8(3) . . ? O2 C1 C2 120.1(3) . . ? O1 C1 C2 117.1(3) . . ? C3 C2 C7 118.5(3) . . ? C3 C2 C1 122.9(3) . . ? C7 C2 C1 118.6(3) . . ? C4 C3 C2 120.8(3) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C3 C4 C5 121.1(3) . . ? C3 C4 H4A 119.4 . . ? C5 C4 H4A 119.4 . . ? C4 C5 C6 117.7(3) . . ? C4 C5 C8 122.1(3) . . ? C6 C5 C8 120.1(3) . . ? C7 C6 C5 121.2(3) . . ? C7 C6 H6A 119.4 . . ? C5 C6 H6A 119.4 . . ? C6 C7 C2 120.7(3) . . ? C6 C7 H7A 119.6 . . ? C2 C7 H7A 119.6 . . ? C5 C8 N1 113.4(3) . . ? C5 C8 H8A 108.9 . . ? N1 C8 H8A 108.9 . . ? C5 C8 H8B 108.9 . . ? N1 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? O4 C9 O3 123.4(3) . . ? O4 C9 C10 120.3(3) . 4_665 ? O3 C9 C10 116.3(3) . 4_665 ? N1 C10 C11 110.5(3) . . ? N1 C10 C9 107.7(3) . 2_644 ? C11 C10 C9 109.9(3) . 2_644 ? N1 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 2_644 . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Cu1 O1 C1 161.9(4) . . . . ? O5 Cu1 O1 C1 -103.5(3) . . . . ? N1 Cu1 O1 C1 74.9(2) 4_665 . . . ? O5 Cu1 O3 C9 -172.0(3) . . . . ? O1 Cu1 O3 C9 -77.1(5) . . . . ? N1 Cu1 O3 C9 11.0(2) 4_665 . . . ? Cu1 O1 C1 O2 13.8(4) . . . . ? Cu1 O1 C1 C2 -167.5(2) . . . . ? O2 C1 C2 C3 177.6(3) . . . . ? O1 C1 C2 C3 -1.1(5) . . . . ? O2 C1 C2 C7 -4.2(5) . . . . ? O1 C1 C2 C7 177.0(3) . . . . ? C7 C2 C3 C4 0.1(5) . . . . ? C1 C2 C3 C4 178.2(3) . . . . ? C2 C3 C4 C5 -1.4(5) . . . . ? C3 C4 C5 C6 1.9(5) . . . . ? C3 C4 C5 C8 -176.2(3) . . . . ? C4 C5 C6 C7 -1.1(5) . . . . ? C8 C5 C6 C7 177.1(3) . . . . ? C5 C6 C7 C2 -0.2(6) . . . . ? C3 C2 C7 C6 0.8(5) . . . . ? C1 C2 C7 C6 -177.5(3) . . . . ? C4 C5 C8 N1 -102.5(3) . . . . ? C6 C5 C8 N1 79.4(4) . . . . ? C10 N1 C8 C5 65.7(3) . . . . ? Cu1 N1 C8 C5 -54.4(3) 2_644 . . . ? Cu1 O3 C9 O4 -173.4(3) . . . . ? Cu1 O3 C9 C10 8.3(4) . . . 4_665 ? C8 N1 C10 C11 148.5(3) . . . . ? Cu1 N1 C10 C11 -84.6(3) 2_644 . . . ? C8 N1 C10 C9 -91.5(3) . . . 2_644 ? Cu1 N1 C10 C9 35.4(3) 2_644 . . 2_644 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5A O4 0.85 1.82 2.668(4) 179.7 1_545 O5 H5B O6 0.85 1.88 2.703(5) 163.3 4 O6 H6C O2 0.85 2.11 2.871(4) 148.0 1_455 O6 H6B O1 0.85 2.02 2.867(4) 179.6 . N1 H1A O4 0.91 2.15 3.048(4) 168.0 3_654 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.269 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.060 data_2D _database_code_depnum_ccdc_archive 'CCDC 916193' #TrackingRef '1-3-Revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 Cu N O5, H2 O' _chemical_formula_sum 'C11 H15 Cu N O6' _chemical_formula_weight 320.78 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 tetragonal _symmetry_space_group_name_H-M P4(1) _symmetry_space_group_name_Hall 'P 4w' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z+1/4' '-x, -y, z+1/2' 'y, -x, z+3/4' _cell_length_a 7.53850(1) _cell_length_b 7.53850(1) _cell_length_c 22.7308(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1291.77(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1475 _cell_measurement_theta_min 2.6828 _cell_measurement_theta_max 28.9464 _exptl_crystal_description prism _exptl_crystal_colour dark-blue _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 1.713 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4927 _exptl_absorpt_correction_T_max 0.6640 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% ? _diffrn_reflns_number 2891 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 26.43 _reflns_number_total 1851 _reflns_number_gt 1752 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0320P)^2^+0.2000P] 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 0.009(16) _chemical_absolute_configuration rmad _refine_ls_number_reflns 1851 _refine_ls_number_parameters 173 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0649 _refine_ls_wR_factor_gt 0.0632 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.003 _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 0.80916(5) 0.65734(6) 0.171310(18) 0.02214(12) Uani 1 1 d . . . O1 O 0.9799(3) 0.6683(3) 0.10701(12) 0.0286(6) Uani 1 1 d . . . O2 O 0.9961(4) 0.3776(4) 0.11991(11) 0.0327(7) Uani 1 1 d . . . O3 O 0.6296(3) 0.6997(3) 0.22976(11) 0.0263(6) Uani 1 1 d . . . O4 O 0.3379(3) 0.7028(4) 0.24212(12) 0.0303(6) Uani 1 1 d . . . O5 O 0.9872(4) 0.7225(6) 0.22784(15) 0.0709(14) Uani 1 1 d . . . H5A H 1.0991 0.7168 0.2322 0.106 Uiso 1 1 d R . . H5B H 0.9394 0.7720 0.2575 0.106 Uiso 1 1 d R . . O6 O 0.9706(4) 0.8823(4) 0.33389(15) 0.0525(9) Uani 1 1 d . . . H6B H 1.0778 0.9108 0.3406 0.079 Uiso 1 1 d R . . H6C H 0.8720 0.9310 0.3421 0.079 Uiso 1 1 d R . . N1 N 0.6047(4) 0.5830(4) 0.11968(13) 0.0176(6) Uani 1 1 d . . . H1A H 0.6262 0.6228 0.0826 0.021 Uiso 1 1 calc R . . C1 C 1.0271(4) 0.5120(5) 0.09037(17) 0.0225(8) Uani 1 1 d . . . C2 C 0.5019(5) 0.1264(4) 0.28346(16) 0.0214(8) Uani 1 1 d . . . C3 C 0.3552(5) 0.1710(5) 0.25003(18) 0.0264(8) Uani 1 1 d . . . H3A H 0.2422 0.1420 0.2633 0.032 Uiso 1 1 calc R . . C4 C 0.3756(5) 0.2584(5) 0.19700(18) 0.0265(8) Uani 1 1 d . . . H4A H 0.2755 0.2889 0.1754 0.032 Uiso 1 1 calc R . . C5 C 0.5429(5) 0.3018(4) 0.17526(19) 0.0220(7) Uani 1 1 d . . . C6 C 0.6896(5) 0.2583(5) 0.21007(18) 0.0284(9) Uani 1 1 d . . . H6A H 0.8029 0.2874 0.1971 0.034 Uiso 1 1 calc R . . C7 C 0.6689(5) 0.1730(5) 0.26314(19) 0.0296(9) Uani 1 1 d . . . H7A H 0.7683 0.1463 0.2857 0.036 Uiso 1 1 calc R . . C8 C 0.5676(5) 0.3876(4) 0.11643(16) 0.0225(8) Uani 1 1 d . . . H8A H 0.4613 0.3691 0.0932 0.027 Uiso 1 1 calc R . . H8B H 0.6651 0.3298 0.0963 0.027 Uiso 1 1 calc R . . C9 C 0.4710(5) 0.6935(5) 0.21054(17) 0.0197(8) Uani 1 1 d . . . C10 C 0.4497(5) 0.6819(5) 0.14351(17) 0.0193(8) Uani 1 1 d . . . H10A H 0.3405 0.6173 0.1342 0.023 Uiso 1 1 calc R . . C11 C 0.4414(6) 0.8654(5) 0.11656(18) 0.0349(10) Uani 1 1 d . . . H11A H 0.4296 0.8554 0.0746 0.052 Uiso 1 1 calc R . . H11B H 0.5481 0.9290 0.1258 0.052 Uiso 1 1 calc R . . H11C H 0.3411 0.9282 0.1322 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0153(2) 0.0353(3) 0.01588(19) -0.0047(2) 0.0015(2) 0.00100(18) O1 0.0251(14) 0.0373(15) 0.0234(14) -0.0048(13) 0.0088(12) -0.0008(12) O2 0.0331(15) 0.0388(15) 0.0261(15) 0.0050(14) 0.0102(13) 0.0006(12) O3 0.0175(12) 0.0466(16) 0.0149(13) -0.0064(13) -0.0008(11) 0.0003(11) O4 0.0216(13) 0.0497(17) 0.0197(14) -0.0048(14) 0.0044(12) 0.0001(12) O5 0.0142(14) 0.159(4) 0.039(2) -0.050(3) 0.0005(14) 0.0041(19) O6 0.0385(17) 0.071(2) 0.048(2) -0.0141(19) 0.0010(16) -0.0013(16) N1 0.0230(14) 0.0190(14) 0.0107(13) 0.0010(12) 0.0021(13) -0.0028(11) C1 0.0119(16) 0.038(2) 0.0175(18) -0.0064(18) 0.0035(15) -0.0016(15) C2 0.034(2) 0.0147(16) 0.0156(17) -0.0013(14) 0.0014(17) 0.0000(15) C3 0.0263(19) 0.0256(19) 0.028(2) 0.0057(17) 0.0051(17) -0.0040(16) C4 0.0226(18) 0.0259(19) 0.031(2) 0.0046(17) -0.0057(17) -0.0006(15) C5 0.0309(17) 0.0157(15) 0.0193(17) 0.0002(17) 0.001(2) -0.0011(14) C6 0.0220(19) 0.039(2) 0.025(2) 0.0100(19) 0.0030(17) 0.0002(17) C7 0.0261(19) 0.037(2) 0.025(2) 0.0085(19) -0.0019(17) 0.0004(17) C8 0.0300(19) 0.0219(18) 0.0155(17) 0.0005(16) 0.0003(16) 0.0000(15) C9 0.0176(18) 0.0264(19) 0.0152(18) -0.0026(16) -0.0014(16) -0.0011(15) C10 0.0177(17) 0.0234(18) 0.0169(18) -0.0021(16) -0.0031(16) -0.0004(14) C11 0.044(2) 0.028(2) 0.033(2) 0.0015(19) -0.002(2) 0.0091(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 O5 1.922(3) . ? Cu1 O3 1.923(2) . ? Cu1 O1 1.949(3) . ? Cu1 N1 2.017(3) . ? O1 C1 1.288(5) . ? O2 C1 1.238(5) . ? O3 C9 1.274(4) . ? O4 C9 1.235(4) . ? O5 H5A 0.8500 . ? O5 H5B 0.8500 . ? O6 H6B 0.8500 . ? O6 H6C 0.8499 . ? N1 C10 1.488(4) . ? N1 C8 1.501(4) . ? N1 H1A 0.9100 . ? C1 C2 1.498(5) 4_664 ? C2 C3 1.383(5) . ? C2 C7 1.387(5) . ? C2 C1 1.498(5) 2_645 ? C3 C4 1.382(5) . ? C3 H3A 0.9300 . ? C4 C5 1.393(5) . ? C4 H4A 0.9300 . ? C5 C6 1.399(5) . ? C5 C8 1.497(5) . ? C6 C7 1.376(6) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.535(5) . ? C10 C11 1.515(5) . ? C10 H10A 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cu1 O3 89.27(12) . . ? O5 Cu1 O1 91.68(12) . . ? O3 Cu1 O1 167.31(11) . . ? O5 Cu1 N1 173.63(14) . . ? O3 Cu1 N1 84.85(11) . . ? O1 Cu1 N1 94.59(11) . . ? C1 O1 Cu1 111.3(2) . . ? C9 O3 Cu1 114.7(2) . . ? Cu1 O5 H5A 139.3 . . ? Cu1 O5 H5B 110.2 . . ? H5A O5 H5B 110.5 . . ? H6B O6 H6C 133.1 . . ? C10 N1 C8 111.3(3) . . ? C10 N1 Cu1 104.4(2) . . ? C8 N1 Cu1 116.4(2) . . ? C10 N1 H1A 108.2 . . ? C8 N1 H1A 108.2 . . ? Cu1 N1 H1A 108.2 . . ? O2 C1 O1 122.5(3) . . ? O2 C1 C2 120.4(3) . 4_664 ? O1 C1 C2 117.1(3) . 4_664 ? C3 C2 C7 118.8(4) . . ? C3 C2 C1 122.7(3) . 2_645 ? C7 C2 C1 118.5(3) . 2_645 ? C4 C3 C2 120.4(4) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 121.5(4) . . ? C3 C4 H4A 119.3 . . ? C5 C4 H4A 119.3 . . ? C4 C5 C6 117.4(4) . . ? C4 C5 C8 122.0(3) . . ? C6 C5 C8 120.6(3) . . ? C7 C6 C5 121.1(4) . . ? C7 C6 H6A 119.5 . . ? C5 C6 H6A 119.5 . . ? C6 C7 C2 120.9(4) . . ? C6 C7 H7A 119.6 . . ? C2 C7 H7A 119.6 . . ? C5 C8 N1 113.8(3) . . ? C5 C8 H8A 108.8 . . ? N1 C8 H8A 108.8 . . ? C5 C8 H8B 108.8 . . ? N1 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? O4 C9 O3 124.1(3) . . ? O4 C9 C10 119.7(3) . . ? O3 C9 C10 116.2(3) . . ? N1 C10 C11 110.1(3) . . ? N1 C10 C9 107.9(3) . . ? C11 C10 C9 110.7(3) . . ? N1 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Cu1 O1 C1 104.1(3) . . . . ? O3 Cu1 O1 C1 -161.8(4) . . . . ? N1 Cu1 O1 C1 -74.8(3) . . . . ? O5 Cu1 O3 C9 171.9(3) . . . . ? O1 Cu1 O3 C9 77.5(6) . . . . ? N1 Cu1 O3 C9 -10.6(3) . . . . ? O5 Cu1 N1 C10 49.0(15) . . . . ? O3 Cu1 N1 C10 26.3(2) . . . . ? O1 Cu1 N1 C10 -141.0(2) . . . . ? O5 Cu1 N1 C8 -74.1(15) . . . . ? O3 Cu1 N1 C8 -96.8(2) . . . . ? O1 Cu1 N1 C8 95.9(2) . . . . ? Cu1 O1 C1 O2 -14.1(4) . . . . ? Cu1 O1 C1 C2 167.2(2) . . . 4_664 ? C7 C2 C3 C4 0.8(6) . . . . ? C1 C2 C3 C4 -178.2(3) 2_645 . . . ? C2 C3 C4 C5 0.9(6) . . . . ? C3 C4 C5 C6 -1.9(6) . . . . ? C3 C4 C5 C8 176.6(3) . . . . ? C4 C5 C6 C7 1.2(6) . . . . ? C8 C5 C6 C7 -177.4(4) . . . . ? C5 C6 C7 C2 0.5(6) . . . . ? C3 C2 C7 C6 -1.6(6) . . . . ? C1 C2 C7 C6 177.5(4) 2_645 . . . ? C4 C5 C8 N1 102.5(4) . . . . ? C6 C5 C8 N1 -79.0(4) . . . . ? C10 N1 C8 C5 -65.6(4) . . . . ? Cu1 N1 C8 C5 53.8(4) . . . . ? Cu1 O3 C9 O4 173.8(3) . . . . ? Cu1 O3 C9 C10 -8.9(4) . . . . ? C8 N1 C10 C11 -148.2(3) . . . . ? Cu1 N1 C10 C11 85.4(3) . . . . ? C8 N1 C10 C9 90.8(3) . . . . ? Cu1 N1 C10 C9 -35.5(3) . . . . ? O4 C9 C10 N1 -151.3(3) . . . . ? O3 C9 C10 N1 31.3(4) . . . . ? O4 C9 C10 C11 88.2(4) . . . . ? O3 C9 C10 C11 -89.2(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 O5 H5A O4 0.85 1.82 2.668(4) 179.4 1_655 O5 H5B O6 0.85 1.94 2.698(5) 147.7 . O6 H6B O1 0.85 2.02 2.868(4) 179.6 2_755 O6 H6C O2 0.85 2.04 2.881(4) 167.6 2_655 N1 H1A O4 0.91 2.16 3.051(4) 167.7 4_564 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.323 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.062 data_3L _database_code_depnum_ccdc_archive 'CCDC 916194' #TrackingRef '1-3-Revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H28 Cd N2 O10, H2 O' _chemical_formula_sum 'C22 H30 Cd N2 O11' _chemical_formula_weight 610.88 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 P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.8266(2) _cell_length_b 17.2093(7) _cell_length_c 23.5764(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2364.05(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1941 _cell_measurement_theta_min 2.5147 _cell_measurement_theta_max 28.9765 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.990 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8556 _exptl_absorpt_correction_T_max 0.9805 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% ? _diffrn_reflns_number 7207 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 26.65 _reflns_number_total 4174 _reflns_number_gt 3283 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0340P)^2^+0.6000P] 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 -0.04(3) _chemical_absolute_configuration rmad _refine_ls_number_reflns 4174 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0763 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.75647(7) 0.08838(2) 0.847728(14) 0.02401(10) Uani 1 1 d . . . O1 O 1.0737(6) 0.1340(2) 0.89762(16) 0.0309(10) Uani 1 1 d . . . O2 O 0.8455(7) 0.0662(3) 0.95267(17) 0.0433(12) Uani 1 1 d . . . O3 O 2.1782(6) 0.2073(2) 1.21283(16) 0.0347(10) Uani 1 1 d . . . O4 O 2.0586(6) 0.2950(2) 1.14944(17) 0.0329(9) Uani 1 1 d . . . O5 O 0.9445(7) 0.1156(3) 0.76569(16) 0.0419(12) Uani 1 1 d . . . O6 O 0.6195(7) 0.0595(3) 0.74183(18) 0.0564(17) Uani 1 1 d . . . O7 O 1.5243(6) 0.1990(3) 0.48790(17) 0.0352(10) Uani 1 1 d . . . O8 O 1.6671(6) 0.1483(2) 0.40867(17) 0.0349(10) Uani 1 1 d . . . O9 O 0.4177(6) 0.0289(2) 0.86435(17) 0.0378(11) Uani 1 1 d . . . H9A H 0.3140 0.0607 0.8746 0.057 Uiso 1 1 d R . . H9B H 0.3784 0.0054 0.8342 0.057 Uiso 1 1 d R . . O10 O 0.9035(7) -0.0327(2) 0.83618(17) 0.0448(12) Uani 1 1 d . . . H10B H 0.8803 -0.0698 0.8593 0.067 Uiso 1 1 d R . . H10C H 1.0134 -0.0388 0.8129 0.067 Uiso 1 1 d R . . O11 O 0.7276(9) 0.4466(3) 0.74179(19) 0.0610(14) Uani 1 1 d . . . H11D H 0.7141 0.4010 0.7552 0.091 Uiso 1 1 d R . . H11E H 0.6037 0.4683 0.7524 0.091 Uiso 1 1 d R . . N1 N 1.6162(6) 0.2292(3) 1.16474(18) 0.0217(11) Uani 1 1 d . . . H1A H 1.4717 0.2307 1.1782 0.026 Uiso 1 1 calc R . . H1B H 1.6314 0.2687 1.1399 0.026 Uiso 1 1 calc R . . N2 N 1.0940(7) 0.1538(3) 0.46378(19) 0.0230(11) Uani 1 1 d . . . H2A H 1.1175 0.1933 0.4881 0.028 Uiso 1 1 calc R . . H2B H 0.9504 0.1583 0.4501 0.028 Uiso 1 1 calc R . . C1 C 1.0205(9) 0.1058(3) 0.9459(2) 0.0233(13) Uani 1 1 d . . . C2 C 1.1830(8) 0.1213(3) 0.9944(2) 0.0219(12) Uani 1 1 d . . . C3 C 1.3881(9) 0.1601(4) 0.9865(3) 0.0290(14) Uani 1 1 d . . . H3A H 1.4271 0.1784 0.9506 0.035 Uiso 1 1 calc R . . C4 C 1.5362(9) 0.1720(4) 1.0317(3) 0.0334(15) Uani 1 1 d . . . H4A H 1.6734 0.1985 1.0260 0.040 Uiso 1 1 calc R . . C5 C 1.4819(9) 0.1447(3) 1.0854(2) 0.0275(13) Uani 1 1 d . . . C6 C 1.2781(10) 0.1052(3) 1.0930(2) 0.0314(13) Uani 1 1 d . . . H6A H 1.2405 0.0861 1.1287 0.038 Uiso 1 1 calc R . . C7 C 1.1303(9) 0.0939(4) 1.0484(2) 0.0276(12) Uani 1 1 d . . . H7A H 0.9930 0.0676 1.0544 0.033 Uiso 1 1 calc R . . C8 C 1.6488(10) 0.1550(3) 1.1338(3) 0.0372(16) Uani 1 1 d . . . H8A H 1.6305 0.1121 1.1602 0.045 Uiso 1 1 calc R . . H8B H 1.8041 0.1530 1.1191 0.045 Uiso 1 1 calc R . . C9 C 2.0286(8) 0.2476(3) 1.1894(2) 0.0234(13) Uani 1 1 d . . . C10 C 1.7780(9) 0.2425(3) 1.2129(2) 0.0244(12) Uani 1 1 d . . . H10A H 1.7413 0.2937 1.2287 0.029 Uiso 1 1 calc R . . C11 C 1.7376(13) 0.1843(4) 1.2594(2) 0.0441(15) Uani 1 1 d . . . H11A H 1.5775 0.1835 1.2690 0.066 Uiso 1 1 calc R . . H11B H 1.8255 0.1987 1.2922 0.066 Uiso 1 1 calc R . . H11C H 1.7842 0.1337 1.2468 0.066 Uiso 1 1 calc R . . C12 C 0.8101(9) 0.0870(4) 0.7299(2) 0.0318(14) Uani 1 1 d . . . C13 C 0.8890(9) 0.0854(4) 0.6688(2) 0.0259(12) Uani 1 1 d . . . C14 C 1.1020(9) 0.1144(4) 0.6535(3) 0.0335(14) Uani 1 1 d . . . H14A H 1.1993 0.1340 0.6813 0.040 Uiso 1 1 calc R . . C15 C 1.1726(9) 0.1145(3) 0.5970(2) 0.0311(14) Uani 1 1 d . . . H15A H 1.3148 0.1351 0.5873 0.037 Uiso 1 1 calc R . . C16 C 1.0317(9) 0.0841(3) 0.5556(2) 0.0253(12) Uani 1 1 d . . . C17 C 0.8181(9) 0.0562(4) 0.5704(2) 0.0325(15) Uani 1 1 d . . . H17A H 0.7200 0.0374 0.5425 0.039 Uiso 1 1 calc R . . C18 C 0.7488(12) 0.0560(3) 0.6266(2) 0.0306(11) Uani 1 1 d . . . H18A H 0.6058 0.0357 0.6361 0.037 Uiso 1 1 calc R . . C19 C 1.1138(10) 0.0791(3) 0.4950(2) 0.0288(13) Uani 1 1 d . . . H19A H 1.2731 0.0626 0.4949 0.035 Uiso 1 1 calc R . . H19B H 1.0251 0.0397 0.4753 0.035 Uiso 1 1 calc R . . C20 C 1.5037(9) 0.1695(3) 0.4404(2) 0.0218(12) Uani 1 1 d . . . C21 C 1.2599(11) 0.1604(3) 0.41601(18) 0.0239(10) Uani 1 1 d . . . H21A H 1.2529 0.1131 0.3929 0.029 Uiso 1 1 calc R . . C22 C 1.2021(9) 0.2292(4) 0.3799(2) 0.0389(16) Uani 1 1 d . . . H22A H 1.0438 0.2265 0.3688 0.058 Uiso 1 1 calc R . . H22B H 1.2975 0.2292 0.3467 0.058 Uiso 1 1 calc R . . H22C H 1.2279 0.2761 0.4011 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02173(16) 0.02665(17) 0.02367(17) 0.00281(19) -0.0009(2) -0.0007(3) O1 0.033(2) 0.036(2) 0.024(2) 0.006(2) -0.0069(18) -0.002(2) O2 0.031(2) 0.069(3) 0.030(2) -0.002(2) -0.0012(17) -0.024(2) O3 0.0176(18) 0.045(2) 0.042(2) 0.012(2) -0.0035(16) 0.0038(18) O4 0.035(2) 0.035(2) 0.028(2) 0.007(2) -0.002(2) -0.010(2) O5 0.054(3) 0.050(3) 0.021(2) -0.001(2) 0.007(2) -0.013(3) O6 0.040(2) 0.096(5) 0.033(3) 0.014(3) 0.007(2) -0.016(3) O7 0.029(2) 0.042(3) 0.035(2) -0.015(2) -0.0072(19) -0.003(2) O8 0.0218(18) 0.044(3) 0.039(2) -0.011(2) 0.0037(17) -0.0019(19) O9 0.028(2) 0.046(3) 0.040(3) -0.003(2) 0.0047(18) -0.005(2) O10 0.061(3) 0.033(2) 0.041(3) 0.005(2) 0.018(2) 0.015(2) O11 0.057(3) 0.044(2) 0.082(3) 0.013(3) 0.035(3) 0.009(3) N1 0.017(2) 0.023(2) 0.026(3) 0.003(2) -0.0020(19) 0.004(2) N2 0.020(2) 0.023(3) 0.026(3) -0.004(2) 0.000(2) 0.004(2) C1 0.023(3) 0.027(3) 0.020(3) -0.003(3) -0.002(2) 0.006(3) C2 0.018(3) 0.024(3) 0.024(3) 0.000(3) -0.001(2) 0.002(2) C3 0.025(3) 0.032(4) 0.030(3) 0.003(3) 0.003(3) -0.001(3) C4 0.024(3) 0.033(4) 0.043(4) 0.000(3) -0.002(3) -0.007(3) C5 0.030(3) 0.027(3) 0.025(3) -0.001(3) -0.012(3) 0.004(3) C6 0.038(3) 0.032(3) 0.024(3) 0.002(2) -0.006(3) -0.003(4) C7 0.025(2) 0.031(3) 0.028(3) -0.004(3) 0.000(2) -0.008(3) C8 0.038(3) 0.033(3) 0.040(4) -0.009(3) -0.016(3) 0.008(3) C9 0.018(2) 0.024(3) 0.028(3) -0.006(3) 0.000(2) -0.005(3) C10 0.017(3) 0.033(3) 0.023(2) -0.009(2) -0.003(3) -0.003(3) C11 0.027(3) 0.075(4) 0.030(3) 0.015(3) -0.006(4) 0.001(5) C12 0.037(4) 0.031(3) 0.028(3) 0.014(3) -0.001(2) 0.000(3) C13 0.030(3) 0.024(3) 0.024(3) 0.007(3) 0.000(2) 0.004(3) C14 0.026(3) 0.047(4) 0.028(3) -0.012(4) -0.005(3) -0.005(3) C15 0.024(3) 0.038(3) 0.031(3) 0.004(3) 0.003(2) -0.007(3) C16 0.033(3) 0.019(3) 0.024(3) 0.004(3) 0.000(2) 0.000(3) C17 0.036(3) 0.037(3) 0.025(3) 0.005(3) -0.009(2) -0.008(3) C18 0.028(2) 0.035(3) 0.028(3) 0.005(2) 0.003(4) -0.005(4) C19 0.038(3) 0.020(3) 0.028(3) 0.002(3) 0.004(2) 0.002(3) C20 0.023(3) 0.015(3) 0.027(3) 0.000(3) -0.005(3) -0.002(3) C21 0.022(2) 0.032(3) 0.017(2) -0.005(2) 0.001(3) -0.005(4) C22 0.032(4) 0.054(4) 0.031(3) 0.006(3) 0.001(3) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O9 2.258(4) . ? Cd1 O10 2.269(4) . ? Cd1 O5 2.272(4) . ? Cd1 O4 2.315(4) 3_357 ? Cd1 O1 2.327(4) . ? Cd1 O2 2.556(4) . ? Cd1 O6 2.668(5) . ? O1 C1 1.276(6) . ? O2 C1 1.236(6) . ? O3 C9 1.244(6) . ? O4 C9 1.258(6) . ? O4 Cd1 2.315(4) 3_657 ? O5 C12 1.252(7) . ? O6 C12 1.239(7) . ? O7 C20 1.234(6) . ? O8 C20 1.265(6) . ? O9 H9A 0.8500 . ? O9 H9B 0.8500 . ? O10 H10B 0.8501 . ? O10 H10C 0.8500 . ? O11 H11D 0.8501 . ? O11 H11E 0.8500 . ? N1 C8 1.484(7) . ? N1 C10 1.494(6) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N2 C19 1.487(7) . ? N2 C21 1.489(6) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? C1 C2 1.508(7) . ? C2 C3 1.382(7) . ? C2 C7 1.392(7) . ? C3 C4 1.386(8) . ? C3 H3A 0.9300 . ? C4 C5 1.386(8) . ? C4 H4A 0.9300 . ? C5 C6 1.380(8) . ? C5 C8 1.511(7) . ? C6 C7 1.373(7) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.565(7) . ? C10 C11 1.502(7) . ? C10 H10A 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.513(7) . ? C13 C18 1.384(7) . ? C13 C14 1.386(7) . ? C14 C15 1.393(8) . ? C14 H14A 0.9300 . ? C15 C16 1.379(7) . ? C15 H15A 0.9300 . ? C16 C17 1.379(7) . ? C16 C19 1.508(7) . ? C17 C18 1.385(7) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.541(8) . ? C21 C22 1.497(7) . ? C21 H21A 0.9800 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 Cd1 O10 86.26(15) . . ? O9 Cd1 O5 131.52(15) . . ? O10 Cd1 O5 84.55(16) . . ? O9 Cd1 O4 87.27(14) . 3_357 ? O10 Cd1 O4 170.84(15) . 3_357 ? O5 Cd1 O4 94.94(16) . 3_357 ? O9 Cd1 O1 139.42(14) . . ? O10 Cd1 O1 94.03(15) . . ? O5 Cd1 O1 88.73(15) . . ? O4 Cd1 O1 95.10(14) 3_357 . ? O9 Cd1 O2 86.67(13) . . ? O10 Cd1 O2 84.41(15) . . ? O5 Cd1 O2 139.19(14) . . ? O4 Cd1 O2 101.67(14) 3_357 . ? O1 Cd1 O2 53.12(13) . . ? O9 Cd1 O6 79.43(14) . . ? O10 Cd1 O6 80.18(16) . . ? O5 Cd1 O6 52.11(15) . . ? O4 Cd1 O6 92.27(16) 3_357 . ? O1 Cd1 O6 140.66(14) . . ? O2 Cd1 O6 159.82(17) . . ? C1 O1 Cd1 97.5(3) . . ? C1 O2 Cd1 87.8(3) . . ? C9 O4 Cd1 127.6(3) . 3_657 ? C12 O5 Cd1 101.0(3) . . ? C12 O6 Cd1 82.7(4) . . ? Cd1 O9 H9A 112.2 . . ? Cd1 O9 H9B 107.8 . . ? H9A O9 H9B 110.7 . . ? Cd1 O10 H10B 123.6 . . ? Cd1 O10 H10C 118.4 . . ? H10B O10 H10C 116.2 . . ? H11D O11 H11E 102.5 . . ? C8 N1 C10 115.1(4) . . ? C8 N1 H1A 108.5 . . ? C10 N1 H1A 108.5 . . ? C8 N1 H1B 108.5 . . ? C10 N1 H1B 108.5 . . ? H1A N1 H1B 107.5 . . ? C19 N2 C21 113.0(4) . . ? C19 N2 H2A 109.0 . . ? C21 N2 H2A 109.0 . . ? C19 N2 H2B 109.0 . . ? C21 N2 H2B 109.0 . . ? H2A N2 H2B 107.8 . . ? O2 C1 O1 121.6(5) . . ? O2 C1 C2 121.2(5) . . ? O1 C1 C2 117.2(5) . . ? C3 C2 C7 118.6(5) . . ? C3 C2 C1 121.7(5) . . ? C7 C2 C1 119.7(5) . . ? C2 C3 C4 120.4(5) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 120.7(5) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C6 C5 C4 118.9(5) . . ? C6 C5 C8 120.8(5) . . ? C4 C5 C8 120.3(5) . . ? C7 C6 C5 120.6(5) . . ? C7 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C6 C7 C2 120.9(5) . . ? C6 C7 H7A 119.5 . . ? C2 C7 H7A 119.5 . . ? N1 C8 C5 112.9(5) . . ? N1 C8 H8A 109.0 . . ? C5 C8 H8A 109.0 . . ? N1 C8 H8B 109.0 . . ? C5 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? O3 C9 O4 126.7(5) . . ? O3 C9 C10 117.7(5) . . ? O4 C9 C10 115.6(5) . . ? N1 C10 C11 110.8(5) . . ? N1 C10 C9 109.1(4) . . ? C11 C10 C9 116.3(5) . . ? N1 C10 H10A 106.7 . . ? C11 C10 H10A 106.7 . . ? C9 C10 H10A 106.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O6 C12 O5 123.9(6) . . ? O6 C12 C13 118.7(5) . . ? O5 C12 C13 117.3(5) . . ? C18 C13 C14 118.3(5) . . ? C18 C13 C12 120.8(5) . . ? C14 C13 C12 120.9(5) . . ? C13 C14 C15 120.9(5) . . ? C13 C14 H14A 119.6 . . ? C15 C14 H14A 119.6 . . ? C16 C15 C14 120.1(5) . . ? C16 C15 H15A 120.0 . . ? C14 C15 H15A 120.0 . . ? C17 C16 C15 119.3(5) . . ? C17 C16 C19 120.4(5) . . ? C15 C16 C19 120.2(5) . . ? C16 C17 C18 120.4(5) . . ? C16 C17 H17A 119.8 . . ? C18 C17 H17A 119.8 . . ? C13 C18 C17 121.0(6) . . ? C13 C18 H18A 119.5 . . ? C17 C18 H18A 119.5 . . ? N2 C19 C16 113.2(5) . . ? N2 C19 H19A 108.9 . . ? C16 C19 H19A 108.9 . . ? N2 C19 H19B 108.9 . . ? C16 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? O7 C20 O8 125.6(5) . . ? O7 C20 C21 118.0(5) . . ? O8 C20 C21 116.3(5) . . ? N2 C21 C22 110.2(5) . . ? N2 C21 C20 108.9(4) . . ? C22 C21 C20 109.9(5) . . ? N2 C21 H21A 109.3 . . ? C22 C21 H21A 109.3 . . ? C20 C21 H21A 109.3 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O9 Cd1 O1 C1 8.2(4) . . . . ? O10 Cd1 O1 C1 -80.8(3) . . . . ? O5 Cd1 O1 C1 -165.2(3) . . . . ? O4 Cd1 O1 C1 99.9(3) 3_357 . . . ? O2 Cd1 O1 C1 -0.8(3) . . . . ? O6 Cd1 O1 C1 -160.2(3) . . . . ? O9 Cd1 O2 C1 -173.3(3) . . . . ? O10 Cd1 O2 C1 100.2(3) . . . . ? O5 Cd1 O2 C1 25.2(5) . . . . ? O4 Cd1 O2 C1 -86.8(3) 3_357 . . . ? O1 Cd1 O2 C1 0.8(3) . . . . ? O6 Cd1 O2 C1 140.4(4) . . . . ? O9 Cd1 O5 C12 -1.2(5) . . . . ? O10 Cd1 O5 C12 78.9(4) . . . . ? O4 Cd1 O5 C12 -91.9(4) 3_357 . . . ? O1 Cd1 O5 C12 173.1(4) . . . . ? O2 Cd1 O5 C12 153.8(4) . . . . ? O6 Cd1 O5 C12 -2.9(4) . . . . ? O9 Cd1 O6 C12 -175.9(4) . . . . ? O10 Cd1 O6 C12 -87.9(4) . . . . ? O5 Cd1 O6 C12 2.9(4) . . . . ? O4 Cd1 O6 C12 97.4(4) 3_357 . . . ? O1 Cd1 O6 C12 -3.5(5) . . . . ? O2 Cd1 O6 C12 -128.6(4) . . . . ? Cd1 O2 C1 O1 -1.5(5) . . . . ? Cd1 O2 C1 C2 179.9(5) . . . . ? Cd1 O1 C1 O2 1.6(6) . . . . ? Cd1 O1 C1 C2 -179.7(4) . . . . ? O2 C1 C2 C3 174.7(5) . . . . ? O1 C1 C2 C3 -3.9(8) . . . . ? O2 C1 C2 C7 -3.2(8) . . . . ? O1 C1 C2 C7 178.2(5) . . . . ? C7 C2 C3 C4 -0.6(9) . . . . ? C1 C2 C3 C4 -178.6(5) . . . . ? C2 C3 C4 C5 0.4(9) . . . . ? C3 C4 C5 C6 0.3(9) . . . . ? C3 C4 C5 C8 177.4(5) . . . . ? C4 C5 C6 C7 -0.8(9) . . . . ? C8 C5 C6 C7 -177.9(5) . . . . ? C5 C6 C7 C2 0.6(9) . . . . ? C3 C2 C7 C6 0.1(9) . . . . ? C1 C2 C7 C6 178.1(5) . . . . ? C10 N1 C8 C5 -179.7(5) . . . . ? C6 C5 C8 N1 -93.6(7) . . . . ? C4 C5 C8 N1 89.3(7) . . . . ? Cd1 O4 C9 O3 -67.6(7) 3_657 . . . ? Cd1 O4 C9 C10 109.6(4) 3_657 . . . ? C8 N1 C10 C11 -65.9(6) . . . . ? C8 N1 C10 C9 63.3(6) . . . . ? O3 C9 C10 N1 -130.5(5) . . . . ? O4 C9 C10 N1 52.0(6) . . . . ? O3 C9 C10 C11 -4.3(7) . . . . ? O4 C9 C10 C11 178.2(5) . . . . ? Cd1 O6 C12 O5 -4.9(7) . . . . ? Cd1 O6 C12 C13 174.2(5) . . . . ? Cd1 O5 C12 O6 5.9(8) . . . . ? Cd1 O5 C12 C13 -173.3(4) . . . . ? O6 C12 C13 C18 1.9(9) . . . . ? O5 C12 C13 C18 -178.8(6) . . . . ? O6 C12 C13 C14 -179.0(6) . . . . ? O5 C12 C13 C14 0.2(9) . . . . ? C18 C13 C14 C15 0.5(9) . . . . ? C12 C13 C14 C15 -178.5(5) . . . . ? C13 C14 C15 C16 -1.3(9) . . . . ? C14 C15 C16 C17 2.1(9) . . . . ? C14 C15 C16 C19 -175.7(5) . . . . ? C15 C16 C17 C18 -2.3(9) . . . . ? C19 C16 C17 C18 175.6(5) . . . . ? C14 C13 C18 C17 -0.7(9) . . . . ? C12 C13 C18 C17 178.4(6) . . . . ? C16 C17 C18 C13 1.6(9) . . . . ? C21 N2 C19 C16 154.5(5) . . . . ? C17 C16 C19 N2 101.5(6) . . . . ? C15 C16 C19 N2 -80.7(7) . . . . ? C19 N2 C21 C22 169.3(4) . . . . ? C19 N2 C21 C20 -70.2(5) . . . . ? O7 C20 C21 N2 -27.1(7) . . . . ? O8 C20 C21 N2 155.4(5) . . . . ? O7 C20 C21 C22 93.7(6) . . . . ? O8 C20 C21 C22 -83.9(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 O9 H9A O1 0.85 1.96 2.811(6) 179.6 1_455 O9 H9B O11 0.85 2.15 2.997(6) 178.9 4_646 O10 H10B O8 0.85 1.80 2.655(6) 179.5 2_755 O10 H10C O11 0.85 2.00 2.850(6) 179.8 4_746 O11 H11D O3 0.85 2.02 2.870(6) 179.3 3_357 O11 H11E O6 0.85 2.04 2.831(7) 153.7 4_656 N1 H1A O3 0.90 1.94 2.818(5) 165.6 1_455 N1 H1B O1 0.90 1.92 2.786(6) 159.7 3_557 N2 H2A O7 0.90 2.01 2.808(6) 146.5 3_456 N2 H2B O8 0.90 1.93 2.808(6) 166.1 1_455 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.65 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.446 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.101