# 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_DG1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H20 Cd Cl2 N8 O4' _chemical_formula_weight 667.78 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' Cl Cl 0.1484 0.1585 '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 Tetragonal _symmetry_space_group_name_H-M P4/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' _cell_length_a 16.1284(2) _cell_length_b 16.1284(2) _cell_length_c 5.21340(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1356.14(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 27.6 _exptl_crystal_description Hexagonal _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 1.049 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8543 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20021 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0117 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.60 _reflns_number_total 1566 _reflns_number_gt 1505 _reflns_threshold_expression >2\s(I) __computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3v2 for windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.6544P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1566 _refine_ls_number_parameters 90 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0686 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 C1 C 0.24613(14) 0.05612(13) 0.7581(4) 0.0404(5) Uani 1 1 d . . . H1 H 0.2852 0.0755 0.6413 0.049 Uiso 1 1 calc R . . C2 C 0.22691(16) -0.02647(13) 0.7572(5) 0.0486(5) Uani 1 1 d . . . H2 H 0.2527 -0.0624 0.6425 0.058 Uiso 1 1 calc R . . C3 C 0.16867(18) -0.05581(14) 0.9290(5) 0.0490(6) Uani 1 1 d . . . H3 H 0.1550 -0.1118 0.9324 0.059 Uiso 1 1 calc R . . C4 C 0.13104(14) -0.00088(14) 1.0960(4) 0.0399(5) Uani 1 1 d . . . C5 C 0.15470(14) 0.08182(13) 1.0851(4) 0.0372(5) Uani 1 1 d . . . H5 H 0.1301 0.1191 1.1980 0.045 Uiso 1 1 calc R . . C6 C 0.06797(15) -0.02926(15) 1.2786(5) 0.0502(6) Uani 1 1 d . . . H6 H 0.0566 -0.0857 1.2904 0.060 Uiso 1 1 calc R . . N1 N 0.21108(11) 0.11017(11) 0.9200(3) 0.0346(4) Uani 1 1 d . . . N2 N 0.02871(14) 0.02037(14) 1.4198(4) 0.0519(5) Uani 1 1 d . . . O1 O 0.2707(3) -0.31634(17) 0.3433(6) 0.1250(13) Uani 1 1 d . . . Cl1 Cl 0.2500 0.2500 0.41877(18) 0.0400(2) Uani 1 4 d S . . Cl2 Cl 0.2500 -0.2500 0.5000 0.0456(2) Uani 1 4 d S . . Cd1 Cd 0.2500 0.2500 0.91827(5) 0.02554(11) Uani 1 4 d S . . 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 C1 0.0425(11) 0.0355(10) 0.0433(11) -0.0027(9) 0.0067(9) -0.0001(8) C2 0.0543(13) 0.0338(10) 0.0577(14) -0.0087(10) 0.0043(11) 0.0029(9) C3 0.0563(14) 0.0269(10) 0.0638(16) 0.0006(9) -0.0029(11) -0.0065(9) C4 0.0408(11) 0.0332(10) 0.0456(12) 0.0070(8) -0.0012(9) -0.0083(8) C5 0.0397(11) 0.0307(10) 0.0413(12) 0.0000(8) 0.0061(8) -0.0055(8) C6 0.0518(13) 0.0382(11) 0.0607(15) 0.0125(11) 0.0043(12) -0.0161(10) N1 0.0381(9) 0.0273(8) 0.0385(9) -0.0007(6) 0.0062(7) -0.0043(7) N2 0.0471(12) 0.0461(11) 0.0626(14) 0.0158(9) 0.0112(9) -0.0145(9) O1 0.223(4) 0.0599(16) 0.0925(17) -0.0173(15) 0.026(2) 0.0253(19) Cl1 0.0489(4) 0.0489(4) 0.0223(4) 0.000 0.000 0.000 Cl2 0.0451(4) 0.0451(4) 0.0466(6) 0.000 0.000 0.000 Cd1 0.02444(12) 0.02444(12) 0.02774(16) 0.000 0.000 0.000 _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.339(3) . ? C1 C2 1.368(3) . ? C2 C3 1.382(4) . ? C3 C4 1.382(3) . ? C4 C5 1.389(3) . ? C4 C6 1.466(3) . ? C5 N1 1.333(3) . ? C6 N2 1.258(3) . ? N1 Cd1 2.3410(17) . ? N2 N2 1.410(4) 5_558 ? O1 Cl2 1.387(3) . ? Cl1 Cd1 2.6041(9) . ? Cl1 Cd1 2.6093(9) 1_554 ? Cl2 O1 1.387(3) 7_656 ? Cl2 O1 1.387(3) 2_545 ? Cl2 O1 1.387(3) 8_556 ? Cd1 N1 2.3410(17) 4 ? Cd1 N1 2.3410(17) 2 ? Cd1 N1 2.3410(17) 3 ? Cd1 Cl1 2.6093(9) 1_556 ? 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 N1 C1 C2 122.7(2) . . ? C1 C2 C3 119.0(2) . . ? C2 C3 C4 119.2(2) . . ? C3 C4 C5 118.0(2) . . ? C3 C4 C6 120.9(2) . . ? C5 C4 C6 121.1(2) . . ? N1 C5 C4 122.9(2) . . ? N2 C6 C4 122.0(2) . . ? C5 N1 C1 118.16(18) . . ? C5 N1 Cd1 121.06(14) . . ? C1 N1 Cd1 120.77(14) . . ? C6 N2 N2 112.4(3) . 5_558 ? Cd1 Cl1 Cd1 180.0 . 1_554 ? O1 Cl2 O1 110.30(15) 7_656 2_545 ? O1 Cl2 O1 110.30(15) 7_656 . ? O1 Cl2 O1 107.8(3) 2_545 . ? O1 Cl2 O1 107.8(3) 7_656 8_556 ? O1 Cl2 O1 110.30(15) 2_545 8_556 ? O1 Cl2 O1 110.30(15) . 8_556 ? N1 Cd1 N1 89.999(1) 4 . ? N1 Cd1 N1 89.999(1) 4 2 ? N1 Cd1 N1 179.55(8) . 2 ? N1 Cd1 N1 179.55(8) 4 3 ? N1 Cd1 N1 89.999(1) . 3 ? N1 Cd1 N1 89.999(1) 2 3 ? N1 Cd1 Cl1 90.23(4) 4 . ? N1 Cd1 Cl1 90.23(4) . . ? N1 Cd1 Cl1 90.23(4) 2 . ? N1 Cd1 Cl1 90.23(4) 3 . ? N1 Cd1 Cl1 89.77(4) 4 1_556 ? N1 Cd1 Cl1 89.77(4) . 1_556 ? N1 Cd1 Cl1 89.77(4) 2 1_556 ? N1 Cd1 Cl1 89.77(4) 3 1_556 ? Cl1 Cd1 Cl1 180.0 . 1_556 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.727 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 915228' ####################################################################### # # 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_DG2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H44 Cd Cl2 N16 O10' _chemical_formula_weight 1188.29 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6965(5) _cell_length_b 10.9917(5) _cell_length_c 11.8093(5) _cell_angle_alpha 99.715(2) _cell_angle_beta 98.778(2) _cell_angle_gamma 92.825(2) _cell_volume 1348.49(10) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour Yellow _exptl_crystal_size_max 1.0 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 0.575 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8732 _exptl_absorpt_correction_T_max 0.9745 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21757 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.64 _reflns_number_total 6189 _reflns_number_gt 5592 _reflns_threshold_expression >2\s(I) __computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3v2 for windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0961P)^2^+0.4247P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6189 _refine_ls_number_parameters 349 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1399 _refine_ls_wR_factor_gt 0.1352 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.041 _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 C1 C 1.2659(3) 0.0797(3) 0.9081(3) 0.0574(7) Uani 1 1 d . . . H1 H 1.3044 0.0662 0.9805 0.069 Uiso 1 1 calc R . . C2 C 1.3410(3) 0.1125(3) 0.8328(3) 0.0660(8) Uani 1 1 d . . . H2 H 1.4288 0.1198 0.8536 0.079 Uiso 1 1 calc R . . C3 C 1.2855(3) 0.1348(3) 0.7258(3) 0.0632(8) Uani 1 1 d . . . H3 H 1.3353 0.1571 0.6735 0.076 Uiso 1 1 calc R . . C4 C 1.1538(3) 0.1233(2) 0.6973(2) 0.0489(6) Uani 1 1 d . . . C5 C 1.0861(3) 0.0891(2) 0.7794(2) 0.0481(6) Uani 1 1 d . . . H5 H 0.9980 0.0819 0.7615 0.058 Uiso 1 1 calc R . . C6 C 1.0860(3) 0.1459(3) 0.5862(3) 0.0547(6) Uani 1 1 d . . . H6 H 1.1315 0.1578 0.5273 0.066 Uiso 1 1 calc R . . C7 C 0.8072(3) 0.2024(3) 0.4506(3) 0.0550(6) Uani 1 1 d . . . H7 H 0.7673 0.2103 0.5158 0.066 Uiso 1 1 calc R . . C8 C 0.7388(3) 0.2275(3) 0.3403(3) 0.0532(6) Uani 1 1 d . . . C9 C 0.6182(3) 0.2682(4) 0.3323(4) 0.0741(9) Uani 1 1 d . . . H9 H 0.5787 0.2816 0.3977 0.089 Uiso 1 1 calc R . . C10 C 0.5568(3) 0.2889(4) 0.2265(4) 0.0836(11) Uani 1 1 d . . . H10 H 0.4758 0.3170 0.2197 0.100 Uiso 1 1 calc R . . C11 C 0.6172(3) 0.2675(3) 0.1322(3) 0.0697(8) Uani 1 1 d . . . H11 H 0.5743 0.2787 0.0605 0.084 Uiso 1 1 calc R . . C12 C 0.7928(3) 0.2122(3) 0.2400(3) 0.0546(6) Uani 1 1 d . . . H12 H 0.8749 0.1870 0.2449 0.066 Uiso 1 1 calc R . . C13 C 1.2277(2) 0.0338(3) 1.2245(2) 0.0483(6) Uani 1 1 d . . . H13 H 1.2319 -0.0492 1.1936 0.058 Uiso 1 1 calc R . . C14 C 1.3071(2) 0.0845(3) 1.3284(2) 0.0448(5) Uani 1 1 d . . . C15 C 1.3021(2) 0.2077(3) 1.3734(3) 0.0518(6) Uani 1 1 d . . . H15 H 1.3535 0.2444 1.4428 0.062 Uiso 1 1 calc R . . C16 C 1.2192(3) 0.2758(3) 1.3132(3) 0.0616(7) Uani 1 1 d . . . H16 H 1.2150 0.3596 1.3411 0.074 Uiso 1 1 calc R . . C17 C 1.1432(3) 0.2193(3) 1.2123(3) 0.0582(7) Uani 1 1 d . . . H17 H 1.0873 0.2665 1.1734 0.070 Uiso 1 1 calc R . . C18 C 1.3919(2) 0.0032(3) 1.3848(2) 0.0494(6) Uani 1 1 d . . . H18 H 1.3933 -0.0791 1.3501 0.059 Uiso 1 1 calc R . . C19 C 0.9849(3) 0.4596(3) 0.6275(3) 0.0610(8) Uani 1 1 d . . . H19 H 0.8970 0.4462 0.6121 0.073 Uiso 1 1 calc R . . C20 C 1.0527(3) 0.4403(2) 0.7392(3) 0.0588(7) Uani 1 1 d . . . C21 C 0.9849(3) 0.3905(3) 0.8137(3) 0.0649(8) Uani 1 1 d . . . H21 H 0.8977 0.3739 0.7911 0.078 Uiso 1 1 calc R . . C22 C 1.2377(4) 0.4422(3) 0.8793(4) 0.0811(11) Uani 1 1 d . . . H22 H 1.3243 0.4603 0.9051 0.097 Uiso 1 1 calc R . . C23 C 1.1627(4) 0.3934(3) 0.9480(4) 0.0744(9) Uani 1 1 d . . . H23 H 1.2011 0.3794 1.0204 0.089 Uiso 1 1 calc R . . C24 C 1.1832(4) 0.4639(3) 0.7718(4) 0.0719(9) Uani 1 1 d . . . H24 H 1.2324 0.4936 0.7224 0.086 Uiso 1 1 calc R . . N1 N 1.1386(2) 0.0660(2) 0.8819(2) 0.0501(5) Uani 1 1 d . . . N2 N 0.9683(3) 0.1495(2) 0.5693(2) 0.0552(6) Uani 1 1 d . . . N3 N 0.9199(3) 0.1701(2) 0.4579(2) 0.0567(6) Uani 1 1 d . . . N4 N 0.7354(3) 0.2310(3) 0.1378(2) 0.0632(6) Uani 1 1 d . . . N5 N 1.1455(2) 0.0997(2) 1.1669(2) 0.0521(5) Uani 1 1 d . . . N6 N 1.4623(2) 0.0454(2) 1.4799(2) 0.0602(6) Uani 1 1 d . . . N7 N 1.0421(3) 0.4940(3) 0.5511(3) 0.0720(8) Uani 1 1 d . . . N8 N 1.0381(3) 0.3650(3) 0.9168(3) 0.0696(7) Uani 1 1 d . . . O1 O 0.5219(4) 0.6339(6) 0.3108(7) 0.198(3) Uani 1 1 d . . . O2 O 0.3773(12) 0.5264(7) 0.1790(8) 0.348(8) Uani 1 1 d . . . O1W O 1.09647(19) -0.1793(2) 1.01263(19) 0.0576(5) Uani 1 1 d D . . O3 O 0.3669(8) 0.7222(4) 0.2004(7) 0.221(3) Uani 1 1 d . . . O4 O 0.3228(6) 0.6061(17) 0.3118(12) 0.396(10) Uani 1 1 d . . . Cl1 Cl 0.40262(9) 0.62383(9) 0.24724(12) 0.0855(3) Uani 1 1 d . . . Cd1 Cd 1.0000 0.0000 1.0000 0.04770(12) Uani 1 2 d S . . H1WA H 1.1575 -0.2106 0.9644 0.061 Uiso 1 1 d D . . H1WB H 1.0421 -0.2456 1.0201 0.092 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 C1 0.0495(14) 0.0702(17) 0.0526(16) 0.0159(13) 0.0034(12) 0.0034(12) C2 0.0453(15) 0.086(2) 0.069(2) 0.0215(17) 0.0084(14) -0.0019(14) C3 0.0555(16) 0.0773(19) 0.0625(19) 0.0204(15) 0.0216(14) -0.0028(14) C4 0.0558(15) 0.0493(13) 0.0448(14) 0.0120(11) 0.0147(12) 0.0034(11) C5 0.0466(13) 0.0562(14) 0.0456(14) 0.0184(11) 0.0101(11) 0.0055(10) C6 0.0667(18) 0.0603(15) 0.0427(14) 0.0166(12) 0.0190(13) 0.0040(13) C7 0.0589(16) 0.0590(15) 0.0500(15) 0.0134(12) 0.0153(13) -0.0007(12) C8 0.0535(15) 0.0486(13) 0.0606(17) 0.0153(12) 0.0133(13) 0.0011(11) C9 0.0586(18) 0.091(2) 0.082(2) 0.028(2) 0.0259(17) 0.0111(16) C10 0.0505(17) 0.109(3) 0.103(3) 0.045(2) 0.0154(19) 0.0160(18) C11 0.0604(18) 0.076(2) 0.074(2) 0.0274(17) 0.0003(16) 0.0060(15) C12 0.0572(15) 0.0570(15) 0.0519(16) 0.0131(12) 0.0101(12) 0.0127(12) C13 0.0401(12) 0.0638(15) 0.0403(13) 0.0172(11) -0.0042(10) 0.0035(11) C14 0.0351(11) 0.0620(15) 0.0386(12) 0.0182(11) 0.0002(9) 0.0028(10) C15 0.0397(13) 0.0652(16) 0.0490(15) 0.0107(12) 0.0029(11) 0.0029(11) C16 0.0535(16) 0.0613(16) 0.070(2) 0.0143(15) 0.0058(14) 0.0110(13) C17 0.0449(14) 0.0729(18) 0.0620(18) 0.0295(15) 0.0028(12) 0.0134(12) C18 0.0432(13) 0.0597(14) 0.0419(13) 0.0120(11) -0.0068(10) 0.0037(11) C19 0.0593(16) 0.0446(13) 0.079(2) 0.0182(14) 0.0018(15) 0.0033(12) C20 0.0636(17) 0.0390(12) 0.073(2) 0.0135(12) 0.0054(14) 0.0038(11) C21 0.0602(17) 0.0575(16) 0.078(2) 0.0119(15) 0.0141(16) 0.0100(13) C22 0.070(2) 0.074(2) 0.095(3) 0.033(2) -0.014(2) -0.0149(17) C23 0.087(2) 0.0610(18) 0.072(2) 0.0180(16) 0.0001(19) -0.0005(16) C24 0.071(2) 0.0617(17) 0.083(2) 0.0281(17) 0.0001(17) -0.0109(15) N1 0.0482(12) 0.0619(13) 0.0446(12) 0.0187(10) 0.0101(9) 0.0070(10) N2 0.0678(15) 0.0597(13) 0.0406(12) 0.0139(10) 0.0109(11) 0.0048(11) N3 0.0718(16) 0.0585(13) 0.0431(12) 0.0156(10) 0.0114(11) 0.0088(11) N4 0.0694(16) 0.0686(15) 0.0546(15) 0.0187(12) 0.0082(12) 0.0159(12) N5 0.0416(11) 0.0720(15) 0.0459(12) 0.0265(11) -0.0019(9) 0.0073(10) N6 0.0607(14) 0.0623(14) 0.0504(13) 0.0116(11) -0.0173(11) 0.0101(11) N7 0.0647(16) 0.0677(16) 0.084(2) 0.0344(15) -0.0066(14) -0.0045(13) N8 0.0776(19) 0.0625(15) 0.0722(19) 0.0155(13) 0.0187(15) 0.0069(13) O1 0.094(3) 0.211(6) 0.276(8) 0.068(5) -0.020(4) -0.053(3) O2 0.482(16) 0.156(5) 0.280(10) -0.085(6) -0.243(11) 0.146(7) O1W 0.0520(10) 0.0715(12) 0.0578(12) 0.0302(10) 0.0113(9) 0.0164(9) O3 0.295(9) 0.096(3) 0.261(8) 0.062(4) -0.023(7) 0.001(4) O4 0.107(5) 0.72(3) 0.465(18) 0.374(19) 0.079(8) 0.026(9) Cl1 0.0585(5) 0.0695(5) 0.1251(9) 0.0055(5) 0.0199(5) -0.0034(4) Cd1 0.03732(15) 0.0726(2) 0.03784(16) 0.02759(12) 0.00005(10) 0.00717(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.344(4) . ? C1 C2 1.365(5) . ? C2 C3 1.378(5) . ? C3 C4 1.392(4) . ? C4 C5 1.384(4) . ? C4 C6 1.465(4) . ? C5 N1 1.325(4) . ? C6 N2 1.248(4) . ? C7 N3 1.269(4) . ? C7 C8 1.469(4) . ? C8 C9 1.381(4) . ? C8 C12 1.384(4) . ? C9 C10 1.380(6) . ? C10 C11 1.363(6) . ? C11 N4 1.341(4) . ? C12 N4 1.322(4) . ? C13 N5 1.345(3) . ? C13 C14 1.394(4) . ? C14 C15 1.376(4) . ? C14 C18 1.470(4) . ? C15 C16 1.380(4) . ? C16 C17 1.368(5) . ? C17 N5 1.336(4) . ? C18 N6 1.255(3) . ? C19 N7 1.262(5) . ? C19 C20 1.459(5) . ? C20 C21 1.385(5) . ? C20 C24 1.390(5) . ? C21 N8 1.344(5) . ? C22 C23 1.376(6) . ? C22 C24 1.378(5) . ? C23 N8 1.334(5) . ? N1 Cd1 2.353(2) . ? N2 N3 1.397(3) . ? N5 Cd1 2.382(2) . ? N6 N6 1.412(5) 2_858 ? N7 N7 1.421(6) 2_766 ? O1 Cl1 1.367(5) . ? O2 Cl1 1.217(6) . ? O1W Cd1 2.286(2) . ? O3 Cl1 1.341(6) . ? O4 Cl1 1.257(9) . ? Cd1 O1W 2.286(2) 2_757 ? Cd1 N1 2.353(2) 2_757 ? Cd1 N5 2.382(2) 2_757 ? 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 N1 C1 C2 122.8(3) . . ? C1 C2 C3 119.4(3) . . ? C2 C3 C4 118.9(3) . . ? C5 C4 C3 117.2(3) . . ? C5 C4 C6 119.8(3) . . ? C3 C4 C6 123.0(3) . . ? N1 C5 C4 124.3(3) . . ? N2 C6 C4 121.1(3) . . ? N3 C7 C8 120.8(3) . . ? C9 C8 C12 117.1(3) . . ? C9 C8 C7 121.5(3) . . ? C12 C8 C7 121.4(3) . . ? C10 C9 C8 119.5(3) . . ? C11 C10 C9 118.7(3) . . ? N4 C11 C10 123.2(4) . . ? N4 C12 C8 124.3(3) . . ? N5 C13 C14 122.9(3) . . ? C15 C14 C13 118.6(2) . . ? C15 C14 C18 123.2(2) . . ? C13 C14 C18 118.2(2) . . ? C14 C15 C16 118.5(3) . . ? C17 C16 C15 119.7(3) . . ? N5 C17 C16 123.2(3) . . ? N6 C18 C14 119.7(3) . . ? N7 C19 C20 122.0(3) . . ? C21 C20 C24 118.5(3) . . ? C21 C20 C19 118.5(3) . . ? C24 C20 C19 122.9(3) . . ? N8 C21 C20 123.6(3) . . ? C23 C22 C24 119.3(4) . . ? N8 C23 C22 123.7(4) . . ? C22 C24 C20 118.2(4) . . ? C5 N1 C1 117.3(2) . . ? C5 N1 Cd1 116.73(17) . . ? C1 N1 Cd1 125.9(2) . . ? C6 N2 N3 113.2(2) . . ? C7 N3 N2 112.4(3) . . ? C12 N4 C11 117.2(3) . . ? C17 N5 C13 117.2(2) . . ? C17 N5 Cd1 122.38(18) . . ? C13 N5 Cd1 120.24(19) . . ? C18 N6 N6 111.7(3) . 2_858 ? C19 N7 N7 112.5(4) . 2_766 ? C23 N8 C21 116.6(3) . . ? O2 Cl1 O4 96.9(9) . . ? O2 Cl1 O3 113.0(5) . . ? O4 Cl1 O3 105.5(7) . . ? O2 Cl1 O1 113.4(5) . . ? O4 Cl1 O1 109.1(6) . . ? O3 Cl1 O1 116.7(4) . . ? O1W Cd1 O1W 180.000(1) . 2_757 ? O1W Cd1 N1 93.15(8) . . ? O1W Cd1 N1 86.85(8) 2_757 . ? O1W Cd1 N1 86.85(8) . 2_757 ? O1W Cd1 N1 93.15(8) 2_757 2_757 ? N1 Cd1 N1 180.000(1) . 2_757 ? O1W Cd1 N5 88.77(8) . . ? O1W Cd1 N5 91.23(8) 2_757 . ? N1 Cd1 N5 88.76(8) . . ? N1 Cd1 N5 91.24(8) 2_757 . ? O1W Cd1 N5 91.23(8) . 2_757 ? O1W Cd1 N5 88.77(8) 2_757 2_757 ? N1 Cd1 N5 91.24(8) . 2_757 ? N1 Cd1 N5 88.76(8) 2_757 2_757 ? N5 Cd1 N5 180.000(1) . 2_757 ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.64 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.948 _refine_diff_density_min -0.749 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 915229' ####################################################################### # # 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_DG3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 Cd N4 O8' _chemical_formula_weight 510.78 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.47630(10) _cell_length_b 8.37070(10) _cell_length_c 9.01210(10) _cell_angle_alpha 93.2460(10) _cell_angle_beta 113.2910(10) _cell_angle_gamma 105.2300(10) _cell_volume 491.575(10) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 200 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 258 _exptl_absorpt_coefficient_mu 1.163 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8234 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8278 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.60 _reflns_number_total 2274 _reflns_number_gt 2258 _reflns_threshold_expression >2\s(I) __computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3v2 for windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0283P)^2^+0.0752P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2274 _refine_ls_number_parameters 152 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0180 _refine_ls_R_factor_gt 0.0178 _refine_ls_wR_factor_ref 0.0477 _refine_ls_wR_factor_gt 0.0476 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.108 _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 C1 C 0.7225(3) -0.1524(2) 0.6068(2) 0.0364(4) Uani 1 1 d . . . H1 H 0.6855 -0.2508 0.6454 0.044 Uiso 1 1 calc R . . C2 C 0.6317(3) -0.1538(2) 0.4408(2) 0.0406(4) Uani 1 1 d . . . H2 H 0.5352 -0.2512 0.3692 0.049 Uiso 1 1 calc R . . C3 C 0.6854(3) -0.0089(2) 0.3817(2) 0.0372(4) Uani 1 1 d . . . H3 H 0.6273 -0.0074 0.2697 0.045 Uiso 1 1 calc R . . C4 C 0.8277(2) 0.1347(2) 0.49261(19) 0.0296(3) Uani 1 1 d . . . C5 C 0.9128(2) 0.1248(2) 0.65821(19) 0.0291(3) Uani 1 1 d . . . H5 H 1.0097 0.2205 0.7325 0.035 Uiso 1 1 calc R . . C6 C 0.8877(3) 0.2929(2) 0.4371(2) 0.0332(3) Uani 1 1 d . . . H6 H 0.8618 0.2917 0.3272 0.040 Uiso 1 1 calc R . . C7 C 0.6050(2) -0.27730(18) 0.95974(18) 0.0243(3) Uani 1 1 d . . . C8 C 0.4600(2) -0.45397(19) 0.92935(19) 0.0274(3) Uani 1 1 d . . . H8A H 0.4426 -0.5175 0.8286 0.033 Uiso 1 1 calc R . . H8B H 0.3269 -0.4471 0.9155 0.033 Uiso 1 1 calc R . . Cd1 Cd 1.0000 0.0000 1.0000 0.02716(6) Uani 1 2 d S . . N1 N 0.8624(2) -0.01510(17) 0.71582(16) 0.0303(3) Uani 1 1 d . . . N2 N 0.9747(3) 0.43156(18) 0.53778(18) 0.0387(3) Uani 1 1 d . . . O1 O 0.77674(17) -0.26574(14) 0.95918(16) 0.0334(3) Uani 1 1 d . . . O2 O 0.5532(2) -0.15466(17) 0.9852(2) 0.0526(4) Uani 1 1 d . . . O1W O 1.17857(19) -0.19066(18) 0.98797(19) 0.0413(3) Uani 1 1 d D . . O2W O 0.8092(2) -0.55503(18) 0.8098(2) 0.0470(3) Uani 1 1 d GD . . H1WA H 1.174(4) -0.267(3) 1.059(3) 0.075(9) Uiso 1 1 d D . . H1WB H 1.307(3) -0.159(3) 0.992(3) 0.058(7) Uiso 1 1 d D . . H2WA H 0.812(4) -0.459(3) 0.862(3) 0.067(8) Uiso 1 1 d D . . H2WB H 0.887(4) -0.531(4) 0.754(3) 0.078(9) 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 C1 0.0443(9) 0.0238(8) 0.0371(9) 0.0050(7) 0.0182(7) 0.0033(7) C2 0.0446(9) 0.0289(9) 0.0345(9) -0.0042(7) 0.0112(7) 0.0003(7) C3 0.0445(9) 0.0358(9) 0.0245(8) 0.0018(7) 0.0098(7) 0.0102(8) C4 0.0353(8) 0.0274(8) 0.0263(7) 0.0067(6) 0.0131(6) 0.0099(6) C5 0.0343(8) 0.0231(8) 0.0254(7) 0.0046(6) 0.0099(6) 0.0059(6) C6 0.0437(9) 0.0320(9) 0.0242(7) 0.0107(6) 0.0138(6) 0.0119(7) C7 0.0257(7) 0.0201(7) 0.0259(7) 0.0066(5) 0.0114(5) 0.0041(6) C8 0.0233(6) 0.0203(7) 0.0336(8) 0.0068(6) 0.0099(6) 0.0021(6) Cd1 0.03686(10) 0.01628(9) 0.02442(9) 0.00589(6) 0.01208(6) 0.00318(6) N1 0.0370(7) 0.0234(7) 0.0271(7) 0.0060(5) 0.0122(5) 0.0056(6) N2 0.0579(9) 0.0286(8) 0.0280(7) 0.0121(6) 0.0180(7) 0.0099(7) O1 0.0268(5) 0.0237(6) 0.0509(7) 0.0075(5) 0.0204(5) 0.0034(5) O2 0.0495(8) 0.0230(6) 0.0986(12) 0.0079(7) 0.0462(8) 0.0093(6) O1W 0.0321(6) 0.0399(7) 0.0608(9) 0.0128(6) 0.0276(6) 0.0118(6) O2W 0.0534(8) 0.0325(7) 0.0574(9) 0.0023(6) 0.0304(7) 0.0077(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.344(2) . ? C1 C2 1.374(3) . ? C2 C3 1.379(3) . ? C3 C4 1.388(2) . ? C4 C5 1.389(2) . ? C4 C6 1.464(2) . ? C5 N1 1.333(2) . ? C6 N2 1.269(2) . ? C7 O2 1.228(2) . ? C7 O1 1.2644(19) . ? C7 C8 1.521(2) . ? C8 C8 1.525(3) 2_647 ? Cd1 O1 2.3110(11) . ? Cd1 O1 2.3110(11) 2_757 ? Cd1 N1 2.3334(13) 2_757 ? Cd1 N1 2.3334(13) . ? Cd1 O1W 2.3570(13) . ? Cd1 O1W 2.3570(13) 2_757 ? N2 N2 1.409(3) 2_766 ? 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 N1 C1 C2 122.95(16) . . ? C1 C2 C3 119.18(16) . . ? C2 C3 C4 118.71(16) . . ? C3 C4 C5 118.34(15) . . ? C3 C4 C6 121.08(15) . . ? C5 C4 C6 120.58(15) . . ? N1 C5 C4 123.17(15) . . ? N2 C6 C4 120.55(15) . . ? O2 C7 O1 123.34(14) . . ? O2 C7 C8 119.79(14) . . ? O1 C7 C8 116.87(13) . . ? C7 C8 C8 111.78(15) . 2_647 ? O1 Cd1 O1 180.00(4) . 2_757 ? O1 Cd1 N1 91.26(5) . 2_757 ? O1 Cd1 N1 88.74(5) 2_757 2_757 ? O1 Cd1 N1 88.74(5) . . ? O1 Cd1 N1 91.26(5) 2_757 . ? N1 Cd1 N1 180.0 2_757 . ? O1 Cd1 O1W 73.82(4) . . ? O1 Cd1 O1W 106.18(4) 2_757 . ? N1 Cd1 O1W 87.86(5) 2_757 . ? N1 Cd1 O1W 92.14(5) . . ? O1 Cd1 O1W 106.18(4) . 2_757 ? O1 Cd1 O1W 73.82(4) 2_757 2_757 ? N1 Cd1 O1W 92.14(5) 2_757 2_757 ? N1 Cd1 O1W 87.86(5) . 2_757 ? O1W Cd1 O1W 180.000(1) . 2_757 ? C5 N1 C1 117.64(14) . . ? C5 N1 Cd1 118.00(10) . . ? C1 N1 Cd1 124.13(11) . . ? C6 N2 N2 112.10(17) . 2_766 ? C7 O1 Cd1 118.17(10) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.336 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 915230'