# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? #TrackingRef '- 1.cif' _publ_contact_author ; Wang Jinglin Institute of Molecular Science, Chemical Biology and Molecular Engineering Laboratory of Education Ministry, Shanxi University Taiyuan, Shanxi 030006 China ; _publ_contact_author_email 200812801003@mail.sxu.cn _publ_contact_author_fax '0086 351 701 6358' _publ_contact_author_phone '0086 351 701 6358' _publ_section_title ; Synthesis, characterization and Properties of Metal complexes with (E)-1-methyl-4-nitro-N'-(pyridin-2-ylmethylene)-1H-pyrrole-2-carbohydrazide ; _publ_contact_author_name 'Wang, Jinglin' _publ_author_name 'Binsheng Yang' data_090721c _database_code_depnum_ccdc_archive 'CCDC 773660' #=================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N5 O4' _chemical_formula_weight 291.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' _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 7.2750(8) _cell_length_b 7.5246(6) _cell_length_c 13.6360(13) _cell_angle_alpha 100.5400(10) _cell_angle_beta 99.3280(10) _cell_angle_gamma 108.548(2) _cell_volume 676.03(11) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1393 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 27.992 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9478 _exptl_absorpt_correction_T_max 0.9571 _exptl_absorpt_process_details sadabs _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 3513 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2333 _reflns_number_gt 1611 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0544P)^2^+0.1156P] 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 SHELXL _refine_ls_extinction_coef 0.020(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2333 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 N1 N 0.7926(2) 0.5096(2) 0.54237(11) 0.0394(4) Uani 1 1 d . . . N2 N 0.6849(2) 0.4777(2) 0.44452(11) 0.0389(4) Uani 1 1 d . . . H2 H 0.7005 0.5701 0.4140 0.047 Uiso 1 1 calc R . . N3 N 1.1578(2) 0.9092(2) 0.72834(13) 0.0466(5) Uani 1 1 d . . . N4 N 0.3084(2) 0.1006(2) 0.23107(12) 0.0410(4) Uani 1 1 d . . . N5 N 0.2768(3) 0.3989(3) 0.05997(13) 0.0507(5) Uani 1 1 d . . . O1 O 0.5270(2) 0.1613(2) 0.43682(11) 0.0598(5) Uani 1 1 d . . . O2 O 0.1537(2) 0.2927(2) -0.01905(11) 0.0676(5) Uani 1 1 d . . . O3 O 0.3589(3) 0.5741(2) 0.07203(12) 0.0740(6) Uani 1 1 d . . . O4 O 0.7067(3) 0.8375(2) 0.39916(12) 0.0677(5) Uani 1 1 d . . . H4A H 0.7483 0.9137 0.3620 0.081 Uiso 1 1 d R . . H4B H 0.6380 0.8790 0.4359 0.081 Uiso 1 1 d R . . C1 C 0.9168(3) 0.6804(3) 0.58358(14) 0.0412(5) Uani 1 1 d . . . H1 H 0.9318 0.7758 0.5476 0.049 Uiso 1 1 calc R . . C2 C 1.0360(3) 0.7251(3) 0.68844(14) 0.0376(5) Uani 1 1 d . . . C3 C 1.0214(3) 0.5853(3) 0.74296(15) 0.0458(5) Uani 1 1 d . . . H3 H 0.9359 0.4582 0.7131 0.055 Uiso 1 1 calc R . . C4 C 1.1342(3) 0.6358(3) 0.84153(16) 0.0537(6) Uani 1 1 d . . . H4 H 1.1276 0.5433 0.8790 0.064 Uiso 1 1 calc R . . C5 C 1.2566(3) 0.8249(4) 0.88379(16) 0.0547(6) Uani 1 1 d . . . H5 H 1.3329 0.8637 0.9509 0.066 Uiso 1 1 calc R . . C6 C 1.2643(3) 0.9558(3) 0.82515(16) 0.0547(6) Uani 1 1 d . . . H6 H 1.3481 1.0838 0.8542 0.066 Uiso 1 1 calc R . . C7 C 0.5532(3) 0.2969(3) 0.39703(15) 0.0383(5) Uani 1 1 d . . . C8 C 0.4458(3) 0.2776(3) 0.29188(14) 0.0364(5) Uani 1 1 d . . . C9 C 0.4553(3) 0.4125(3) 0.23666(14) 0.0390(5) Uani 1 1 d . . . H9 H 0.5341 0.5433 0.2582 0.047 Uiso 1 1 calc R . . C10 C 0.3231(3) 0.3152(3) 0.14115(14) 0.0395(5) Uani 1 1 d . . . C11 C 0.2350(3) 0.1248(3) 0.13993(15) 0.0436(5) Uani 1 1 d . . . H11 H 0.1408 0.0291 0.0855 0.052 Uiso 1 1 calc R . . C12 C 0.2432(4) -0.0861(3) 0.25767(19) 0.0615(7) Uani 1 1 d . . . H12A H 0.1400 -0.1800 0.2019 0.092 Uiso 1 1 calc R . . H12B H 0.1926 -0.0721 0.3183 0.092 Uiso 1 1 calc R . . H12C H 0.3543 -0.1283 0.2702 0.092 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 N1 0.0422(10) 0.0429(10) 0.0303(9) 0.0082(8) 0.0019(7) 0.0151(8) N2 0.0431(9) 0.0382(9) 0.0291(9) 0.0094(7) -0.0016(7) 0.0108(8) N3 0.0472(10) 0.0411(10) 0.0413(10) 0.0061(8) 0.0021(8) 0.0085(8) N4 0.0411(9) 0.0348(9) 0.0397(10) 0.0073(8) 0.0017(8) 0.0089(7) N5 0.0543(11) 0.0489(11) 0.0362(10) 0.0085(9) -0.0035(9) 0.0100(9) O1 0.0801(11) 0.0420(9) 0.0465(9) 0.0164(7) -0.0007(8) 0.0122(8) O2 0.0747(11) 0.0623(10) 0.0397(9) 0.0071(8) -0.0175(8) 0.0081(9) O3 0.0948(13) 0.0486(10) 0.0548(11) 0.0185(8) -0.0117(9) 0.0054(9) O4 0.0955(13) 0.0505(10) 0.0633(11) 0.0248(8) 0.0178(9) 0.0290(9) C1 0.0447(12) 0.0416(12) 0.0349(11) 0.0127(9) 0.0044(9) 0.0129(10) C2 0.0355(11) 0.0424(11) 0.0317(10) 0.0072(9) 0.0043(8) 0.0124(9) C3 0.0470(12) 0.0448(12) 0.0393(12) 0.0127(10) 0.0018(9) 0.0107(10) C4 0.0529(14) 0.0662(15) 0.0429(13) 0.0220(12) 0.0043(10) 0.0215(12) C5 0.0457(13) 0.0792(17) 0.0324(12) 0.0079(12) -0.0002(10) 0.0210(13) C6 0.0467(13) 0.0543(14) 0.0429(13) -0.0037(11) -0.0013(10) 0.0061(11) C7 0.0428(11) 0.0374(11) 0.0347(11) 0.0098(9) 0.0072(9) 0.0149(9) C8 0.0346(11) 0.0352(10) 0.0338(11) 0.0035(9) 0.0035(8) 0.0103(9) C9 0.0386(11) 0.0350(10) 0.0351(11) 0.0045(9) 0.0019(9) 0.0078(9) C10 0.0396(11) 0.0415(11) 0.0319(11) 0.0076(9) 0.0009(9) 0.0117(9) C11 0.0393(11) 0.0435(12) 0.0372(12) 0.0018(9) -0.0026(9) 0.0106(9) C12 0.0663(16) 0.0358(12) 0.0638(15) 0.0126(11) -0.0047(12) 0.0034(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.271(2) . ? N1 N2 1.370(2) . ? N2 C7 1.355(2) . ? N2 H2 0.8600 . ? N3 C2 1.337(2) . ? N3 C6 1.339(3) . ? N4 C11 1.339(2) . ? N4 C8 1.393(2) . ? N4 C12 1.465(2) . ? N5 O3 1.228(2) . ? N5 O2 1.232(2) . ? N5 C10 1.416(3) . ? O1 C7 1.218(2) . ? O4 H4A 0.8500 . ? O4 H4B 0.8499 . ? C1 C2 1.465(3) . ? C1 H1 0.9300 . ? C2 C3 1.382(3) . ? C3 C4 1.372(3) . ? C3 H3 0.9300 . ? C4 C5 1.370(3) . ? C4 H4 0.9300 . ? C5 C6 1.371(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.475(3) . ? C8 C9 1.361(3) . ? C9 C10 1.398(2) . ? C9 H9 0.9300 . ? C10 C11 1.366(3) . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 N1 N2 116.30(16) . . ? C7 N2 N1 118.27(16) . . ? C7 N2 H2 120.9 . . ? N1 N2 H2 120.9 . . ? C2 N3 C6 117.35(17) . . ? C11 N4 C8 108.94(16) . . ? C11 N4 C12 122.70(17) . . ? C8 N4 C12 128.34(16) . . ? O3 N5 O2 123.07(18) . . ? O3 N5 C10 118.61(17) . . ? O2 N5 C10 118.31(17) . . ? H4A O4 H4B 110.6 . . ? N1 C1 C2 119.21(18) . . ? N1 C1 H1 120.4 . . ? C2 C1 H1 120.4 . . ? N3 C2 C3 122.20(17) . . ? N3 C2 C1 115.96(17) . . ? C3 C2 C1 121.84(18) . . ? C4 C3 C2 119.4(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 118.8(2) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 118.7(2) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? N3 C6 C5 123.5(2) . . ? N3 C6 H6 118.2 . . ? C5 C6 H6 118.2 . . ? O1 C7 N2 123.22(18) . . ? O1 C7 C8 122.76(18) . . ? N2 C7 C8 114.01(16) . . ? C9 C8 N4 108.01(15) . . ? C9 C8 C7 130.37(17) . . ? N4 C8 C7 121.62(16) . . ? C8 C9 C10 106.36(17) . . ? C8 C9 H9 126.8 . . ? C10 C9 H9 126.8 . . ? C11 C10 C9 108.87(17) . . ? C11 C10 N5 124.56(18) . . ? C9 C10 N5 126.48(18) . . ? N4 C11 C10 107.82(17) . . ? N4 C11 H11 126.1 . . ? C10 C11 H11 126.1 . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C1 N1 N2 C7 178.91(18) . . . . ? N2 N1 C1 C2 179.55(17) . . . . ? C6 N3 C2 C3 -1.3(3) . . . . ? C6 N3 C2 C1 178.09(19) . . . . ? N1 C1 C2 N3 -177.48(18) . . . . ? N1 C1 C2 C3 1.9(3) . . . . ? N3 C2 C3 C4 0.4(3) . . . . ? C1 C2 C3 C4 -179.0(2) . . . . ? C2 C3 C4 C5 0.9(3) . . . . ? C3 C4 C5 C6 -1.2(3) . . . . ? C2 N3 C6 C5 1.0(3) . . . . ? C4 C5 C6 N3 0.3(4) . . . . ? N1 N2 C7 O1 -0.5(3) . . . . ? N1 N2 C7 C8 -179.70(16) . . . . ? C11 N4 C8 C9 0.3(2) . . . . ? C12 N4 C8 C9 -178.2(2) . . . . ? C11 N4 C8 C7 -179.65(18) . . . . ? C12 N4 C8 C7 1.8(3) . . . . ? O1 C7 C8 C9 179.3(2) . . . . ? N2 C7 C8 C9 -1.5(3) . . . . ? O1 C7 C8 N4 -0.8(3) . . . . ? N2 C7 C8 N4 178.41(17) . . . . ? N4 C8 C9 C10 -0.4(2) . . . . ? C7 C8 C9 C10 179.5(2) . . . . ? C8 C9 C10 C11 0.4(2) . . . . ? C8 C9 C10 N5 177.0(2) . . . . ? O3 N5 C10 C11 176.4(2) . . . . ? O2 N5 C10 C11 -2.6(3) . . . . ? O3 N5 C10 C9 0.2(3) . . . . ? O2 N5 C10 C9 -178.8(2) . . . . ? C8 N4 C11 C10 0.0(2) . . . . ? C12 N4 C11 C10 178.6(2) . . . . ? C9 C10 C11 N4 -0.2(2) . . . . ? N5 C10 C11 N4 -176.93(19) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.153 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.036 data_090720g _database_code_depnum_ccdc_archive 'CCDC 773661' #=================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 Cd Cl2 N5 O3' _chemical_formula_weight 456.56 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' O O 0.0106 0.0060 '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' 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 7.3001(10) _cell_length_b 9.2759(12) _cell_length_c 11.6302(15) _cell_angle_alpha 83.1550(10) _cell_angle_beta 87.769(2) _cell_angle_gamma 88.654(2) _cell_volume 781.19(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2473 _cell_measurement_theta_min 2.662 _cell_measurement_theta_max 28.213 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.941 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 1.760 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5394 _exptl_absorpt_correction_T_max 0.7423 _exptl_absorpt_process_details sadabs _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 '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 4056 _diffrn_reflns_av_R_equivalents 0.0127 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2722 _reflns_number_gt 2316 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0257P)^2^+0.6750P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2722 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0641 _refine_ls_wR_factor_gt 0.0579 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 Cd1 Cd 0.24877(4) 0.42105(3) 0.49383(2) 0.03196(10) Uani 1 1 d . . . Cl1 Cl -0.04354(12) 0.47092(9) 0.35728(7) 0.0347(2) Uani 1 1 d . . . Cl2 Cl 0.43842(12) 0.62048(9) 0.37492(7) 0.0351(2) Uani 1 1 d . . . N1 N 0.1891(4) 0.1825(3) 0.5684(2) 0.0315(7) Uani 1 1 d . . . N2 N 0.3752(4) 0.2540(3) 0.3667(2) 0.0307(6) Uani 1 1 d . . . N3 N 0.4713(4) 0.3110(3) 0.2701(2) 0.0395(8) Uani 1 1 d . . . H3 H 0.4970 0.4014 0.2677 0.047 Uiso 1 1 calc R . . N4 N 0.6939(4) 0.3156(3) -0.0184(2) 0.0391(7) Uani 1 1 d . . . N5 N 0.8472(4) 0.6823(4) -0.0302(3) 0.0466(8) Uani 1 1 d . . . O1 O 0.5048(4) 0.1187(3) 0.1652(2) 0.0513(7) Uani 1 1 d . . . O2 O 0.9140(4) 0.7153(3) -0.1278(3) 0.0642(9) Uani 1 1 d . . . O3 O 0.8387(5) 0.7650(3) 0.0448(3) 0.0646(9) Uani 1 1 d . . . C1 C 0.1098(6) 0.1460(4) 0.6724(3) 0.0419(9) Uani 1 1 d . . . H1 H 0.0726 0.2196 0.7163 0.050 Uiso 1 1 calc R . . C2 C 0.0804(6) 0.0043(4) 0.7181(3) 0.0441(10) Uani 1 1 d . . . H2 H 0.0248 -0.0175 0.7912 0.053 Uiso 1 1 calc R . . C3 C 0.1349(5) -0.1034(4) 0.6532(3) 0.0389(9) Uani 1 1 d . . . H3A H 0.1160 -0.2001 0.6818 0.047 Uiso 1 1 calc R . . C4 C 0.2177(5) -0.0686(4) 0.5456(3) 0.0350(8) Uani 1 1 d . . . H4 H 0.2541 -0.1412 0.5004 0.042 Uiso 1 1 calc R . . C5 C 0.2459(4) 0.0753(3) 0.5056(3) 0.0287(7) Uani 1 1 d . . . C6 C 0.3410(5) 0.1198(4) 0.3928(3) 0.0328(8) Uani 1 1 d . . . H6 H 0.3747 0.0521 0.3426 0.039 Uiso 1 1 calc R . . C7 C 0.5336(5) 0.2452(4) 0.1755(3) 0.0356(8) Uani 1 1 d . . . C8 C 0.6357(5) 0.3482(4) 0.0918(3) 0.0355(8) Uani 1 1 d . . . C9 C 0.6865(5) 0.4874(4) 0.1018(3) 0.0366(8) Uani 1 1 d . . . H9 H 0.6662 0.5374 0.1660 0.044 Uiso 1 1 calc R . . C10 C 0.7746(5) 0.5395(4) -0.0032(3) 0.0370(9) Uani 1 1 d . . . C11 C 0.7766(5) 0.4322(4) -0.0753(3) 0.0425(9) Uani 1 1 d . . . H11 H 0.8266 0.4392 -0.1505 0.051 Uiso 1 1 calc R . . C12 C 0.6710(7) 0.1779(5) -0.0674(4) 0.0582(12) Uani 1 1 d . . . H12A H 0.7135 0.1887 -0.1471 0.087 Uiso 1 1 calc R . . H12B H 0.5437 0.1532 -0.0625 0.087 Uiso 1 1 calc R . . H12C H 0.7408 0.1022 -0.0245 0.087 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 0.03362(16) 0.02707(15) 0.03468(16) -0.00410(10) 0.00866(11) -0.00388(10) Cl1 0.0383(5) 0.0367(5) 0.0303(5) -0.0101(4) 0.0017(4) 0.0025(4) Cl2 0.0387(5) 0.0309(4) 0.0343(5) 0.0012(4) 0.0027(4) -0.0071(4) N1 0.0346(17) 0.0241(14) 0.0352(16) -0.0021(12) 0.0035(13) -0.0050(13) N2 0.0313(17) 0.0327(16) 0.0278(15) -0.0036(12) 0.0044(12) -0.0028(13) N3 0.050(2) 0.0343(17) 0.0342(17) -0.0067(13) 0.0173(14) -0.0072(15) N4 0.0356(18) 0.054(2) 0.0276(16) -0.0061(14) 0.0055(13) 0.0050(15) N5 0.0344(19) 0.057(2) 0.045(2) 0.0063(18) 0.0049(15) 0.0018(16) O1 0.064(2) 0.0474(17) 0.0449(17) -0.0171(13) 0.0075(14) -0.0073(14) O2 0.066(2) 0.070(2) 0.0498(18) 0.0136(15) 0.0189(16) -0.0038(17) O3 0.075(2) 0.0572(19) 0.061(2) -0.0069(16) 0.0092(17) -0.0124(17) C1 0.055(3) 0.033(2) 0.037(2) -0.0038(16) 0.0102(18) -0.0060(18) C2 0.054(3) 0.039(2) 0.036(2) 0.0041(17) 0.0043(18) -0.0066(19) C3 0.039(2) 0.0250(18) 0.050(2) 0.0085(17) -0.0064(18) -0.0073(16) C4 0.033(2) 0.0270(18) 0.046(2) -0.0066(16) -0.0057(16) -0.0006(15) C5 0.0224(17) 0.0300(17) 0.0333(18) -0.0014(14) -0.0021(14) -0.0020(14) C6 0.031(2) 0.033(2) 0.035(2) -0.0089(15) 0.0018(15) -0.0028(15) C7 0.029(2) 0.049(2) 0.0292(19) -0.0067(17) 0.0010(15) 0.0020(17) C8 0.030(2) 0.050(2) 0.0270(19) -0.0075(16) 0.0021(15) 0.0049(17) C9 0.029(2) 0.052(2) 0.0287(19) -0.0055(16) 0.0033(15) -0.0018(17) C10 0.025(2) 0.049(2) 0.034(2) 0.0033(17) 0.0021(15) 0.0013(17) C11 0.034(2) 0.061(3) 0.031(2) -0.0008(19) 0.0061(16) 0.0093(19) C12 0.073(3) 0.065(3) 0.038(2) -0.020(2) 0.014(2) 0.001(2) _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 N1 2.323(3) . ? Cd1 N2 2.410(3) . ? Cd1 Cl1 2.5276(9) 2_566 ? Cd1 Cl2 2.5715(9) . ? Cd1 Cl1 2.7077(10) . ? Cd1 Cl2 2.7899(10) 2_666 ? Cl1 Cd1 2.5276(9) 2_566 ? Cl2 Cd1 2.7899(10) 2_666 ? N1 C1 1.331(4) . ? N1 C5 1.351(4) . ? N2 C6 1.274(4) . ? N2 N3 1.360(4) . ? N3 C7 1.377(4) . ? N3 H3 0.8600 . ? N4 C11 1.342(5) . ? N4 C8 1.399(4) . ? N4 C12 1.475(5) . ? N5 O2 1.226(4) . ? N5 O3 1.227(4) . ? N5 C10 1.433(5) . ? O1 C7 1.218(4) . ? C1 C2 1.376(5) . ? C1 H1 0.9300 . ? C2 C3 1.365(5) . ? C2 H2 0.9300 . ? C3 C4 1.375(5) . ? C3 H3A 0.9300 . ? C4 C5 1.378(4) . ? C4 H4 0.9300 . ? C5 C6 1.478(5) . ? C6 H6 0.9300 . ? C7 C8 1.473(5) . ? C8 C9 1.371(5) . ? C9 C10 1.397(5) . ? C9 H9 0.9300 . ? C10 C11 1.374(5) . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 N1 Cd1 N2 69.09(9) . . ? N1 Cd1 Cl1 94.19(7) . 2_566 ? N2 Cd1 Cl1 161.19(7) . 2_566 ? N1 Cd1 Cl2 153.80(8) . . ? N2 Cd1 Cl2 87.72(7) . . ? Cl1 Cd1 Cl2 110.32(3) 2_566 . ? N1 Cd1 Cl1 98.63(7) . . ? N2 Cd1 Cl1 89.77(7) . . ? Cl1 Cd1 Cl1 84.14(3) 2_566 . ? Cl2 Cd1 Cl1 93.10(3) . . ? N1 Cd1 Cl2 84.01(7) . 2_666 ? N2 Cd1 Cl2 89.43(7) . 2_666 ? Cl1 Cd1 Cl2 97.57(3) 2_566 2_666 ? Cl2 Cd1 Cl2 83.73(3) . 2_666 ? Cl1 Cd1 Cl2 176.76(3) . 2_666 ? Cd1 Cl1 Cd1 95.86(3) 2_566 . ? Cd1 Cl2 Cd1 96.27(3) . 2_666 ? C1 N1 C5 118.4(3) . . ? C1 N1 Cd1 123.1(2) . . ? C5 N1 Cd1 118.4(2) . . ? C6 N2 N3 125.0(3) . . ? C6 N2 Cd1 117.5(2) . . ? N3 N2 Cd1 117.4(2) . . ? N2 N3 C7 129.4(3) . . ? N2 N3 H3 115.3 . . ? C7 N3 H3 115.3 . . ? C11 N4 C8 108.7(3) . . ? C11 N4 C12 124.1(3) . . ? C8 N4 C12 127.2(3) . . ? O2 N5 O3 123.5(4) . . ? O2 N5 C10 117.8(4) . . ? O3 N5 C10 118.7(3) . . ? N1 C1 C2 123.0(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 118.3(4) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C3 C4 C5 119.1(3) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? N1 C5 C4 121.4(3) . . ? N1 C5 C6 116.8(3) . . ? C4 C5 C6 121.8(3) . . ? N2 C6 C5 117.8(3) . . ? N2 C6 H6 121.1 . . ? C5 C6 H6 121.1 . . ? O1 C7 N3 123.0(3) . . ? O1 C7 C8 126.2(3) . . ? N3 C7 C8 110.8(3) . . ? C9 C8 N4 107.9(3) . . ? C9 C8 C7 129.3(3) . . ? N4 C8 C7 122.8(3) . . ? C8 C9 C10 106.6(3) . . ? C8 C9 H9 126.7 . . ? C10 C9 H9 126.7 . . ? C11 C10 C9 108.6(3) . . ? C11 C10 N5 126.5(3) . . ? C9 C10 N5 124.9(4) . . ? N4 C11 C10 108.2(3) . . ? N4 C11 H11 125.9 . . ? C10 C11 H11 125.9 . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 N1 Cd1 Cl1 Cd1 93.37(7) . . . 2_566 ? N2 Cd1 Cl1 Cd1 162.17(7) . . . 2_566 ? Cl1 Cd1 Cl1 Cd1 0.0 2_566 . . 2_566 ? Cl2 Cd1 Cl1 Cd1 -110.12(3) . . . 2_566 ? Cl2 Cd1 Cl1 Cd1 -122.0(5) 2_666 . . 2_566 ? N1 Cd1 Cl2 Cd1 -62.54(17) . . . 2_666 ? N2 Cd1 Cl2 Cd1 -89.68(7) . . . 2_666 ? Cl1 Cd1 Cl2 Cd1 95.77(3) 2_566 . . 2_666 ? Cl1 Cd1 Cl2 Cd1 -179.33(3) . . . 2_666 ? Cl2 Cd1 Cl2 Cd1 0.0 2_666 . . 2_666 ? N2 Cd1 N1 C1 174.5(3) . . . . ? Cl1 Cd1 N1 C1 -14.4(3) 2_566 . . . ? Cl2 Cd1 N1 C1 145.3(2) . . . . ? Cl1 Cd1 N1 C1 -99.1(3) . . . . ? Cl2 Cd1 N1 C1 82.8(3) 2_666 . . . ? N2 Cd1 N1 C5 -2.1(2) . . . . ? Cl1 Cd1 N1 C5 169.0(2) 2_566 . . . ? Cl2 Cd1 N1 C5 -31.3(3) . . . . ? Cl1 Cd1 N1 C5 84.3(2) . . . . ? Cl2 Cd1 N1 C5 -93.8(2) 2_666 . . . ? N1 Cd1 N2 C6 5.1(2) . . . . ? Cl1 Cd1 N2 C6 -23.4(4) 2_566 . . . ? Cl2 Cd1 N2 C6 172.6(2) . . . . ? Cl1 Cd1 N2 C6 -94.3(2) . . . . ? Cl2 Cd1 N2 C6 88.9(2) 2_666 . . . ? N1 Cd1 N2 N3 -177.6(3) . . . . ? Cl1 Cd1 N2 N3 153.90(19) 2_566 . . . ? Cl2 Cd1 N2 N3 -10.1(2) . . . . ? Cl1 Cd1 N2 N3 83.1(2) . . . . ? Cl2 Cd1 N2 N3 -93.8(2) 2_666 . . . ? C6 N2 N3 C7 8.0(6) . . . . ? Cd1 N2 N3 C7 -169.2(3) . . . . ? C5 N1 C1 C2 -1.1(6) . . . . ? Cd1 N1 C1 C2 -177.7(3) . . . . ? N1 C1 C2 C3 -0.2(6) . . . . ? C1 C2 C3 C4 0.4(6) . . . . ? C2 C3 C4 C5 0.6(5) . . . . ? C1 N1 C5 C4 2.1(5) . . . . ? Cd1 N1 C5 C4 178.9(2) . . . . ? C1 N1 C5 C6 -177.2(3) . . . . ? Cd1 N1 C5 C6 -0.5(4) . . . . ? C3 C4 C5 N1 -1.9(5) . . . . ? C3 C4 C5 C6 177.4(3) . . . . ? N3 N2 C6 C5 175.7(3) . . . . ? Cd1 N2 C6 C5 -7.2(4) . . . . ? N1 C5 C6 N2 5.2(5) . . . . ? C4 C5 C6 N2 -174.2(3) . . . . ? N2 N3 C7 O1 1.6(6) . . . . ? N2 N3 C7 C8 -178.7(3) . . . . ? C11 N4 C8 C9 -0.7(4) . . . . ? C12 N4 C8 C9 179.4(4) . . . . ? C11 N4 C8 C7 177.8(3) . . . . ? C12 N4 C8 C7 -2.1(6) . . . . ? O1 C7 C8 C9 -173.9(4) . . . . ? N3 C7 C8 C9 6.4(5) . . . . ? O1 C7 C8 N4 8.0(6) . . . . ? N3 C7 C8 N4 -171.7(3) . . . . ? N4 C8 C9 C10 0.5(4) . . . . ? C7 C8 C9 C10 -177.9(3) . . . . ? C8 C9 C10 C11 -0.1(4) . . . . ? C8 C9 C10 N5 179.0(3) . . . . ? O2 N5 C10 C11 2.1(6) . . . . ? O3 N5 C10 C11 -178.3(4) . . . . ? O2 N5 C10 C9 -176.8(3) . . . . ? O3 N5 C10 C9 2.8(5) . . . . ? C8 N4 C11 C10 0.6(4) . . . . ? C12 N4 C11 C10 -179.5(4) . . . . ? C9 C10 C11 N4 -0.4(4) . . . . ? N5 C10 C11 N4 -179.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.723 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.077 data_100402e _database_code_depnum_ccdc_archive 'CCDC 773662' #=================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 Cl2 Hg N6 O4' _chemical_formula_weight 617.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Hg Hg -2.3894 9.2266 '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 11.9014(12) _cell_length_b 11.9685(13) _cell_length_c 15.4255(16) _cell_angle_alpha 90.4130(10) _cell_angle_beta 93.2980(10) _cell_angle_gamma 108.853(2) _cell_volume 2075.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2717 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 21.573 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.978 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 7.708 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1363 _exptl_absorpt_correction_T_max 0.2702 _exptl_absorpt_process_details sadabs _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 10775 _diffrn_reflns_av_R_equivalents 0.0749 _diffrn_reflns_av_sigmaI/netI 0.1244 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.02 _reflns_number_total 7140 _reflns_number_gt 3951 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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^)+(0.1606P)^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_number_reflns 7140 _refine_ls_number_parameters 511 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1549 _refine_ls_R_factor_gt 0.0945 _refine_ls_wR_factor_ref 0.2730 _refine_ls_wR_factor_gt 0.2360 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 Hg1 Hg 0.47882(8) 0.29775(8) 0.04430(6) 0.0574(3) Uani 1 1 d . . . Hg2 Hg 0.68927(8) 0.52230(8) 0.55038(6) 0.0589(3) Uani 1 1 d . . . Cl1 Cl 0.2914(5) 0.1646(5) -0.0009(4) 0.0730(17) Uani 1 1 d . . . Cl2 Cl 0.5945(6) 0.4857(5) 0.0995(4) 0.0676(16) Uani 1 1 d . . . Cl3 Cl 0.8279(6) 0.7085(6) 0.5267(5) 0.0780(18) Uani 1 1 d . . . Cl4 Cl 0.5048(6) 0.4001(6) 0.5943(4) 0.0765(18) Uani 1 1 d . . . N1 N 0.5070(17) 0.1753(16) 0.3903(11) 0.055(5) Uani 1 1 d . . . N2 N 0.711(2) 0.0859(18) 0.5167(12) 0.066(5) Uani 1 1 d . . . N3 N 0.6135(15) 0.1447(15) 0.1749(10) 0.048(4) Uani 1 1 d . . . H3 H 0.6673 0.1145 0.1919 0.058 Uiso 1 1 calc R . . N4 N 0.5971(15) 0.1662(15) 0.0885(10) 0.047(4) Uani 1 1 d . . . N5 N 0.5745(14) 0.2294(15) -0.0776(10) 0.046(4) Uani 1 1 d . . . N6 N 0.8098(17) 0.4930(16) 0.8972(11) 0.057(5) Uani 1 1 d . . . N7 N 0.9264(18) 0.2981(18) 1.0167(12) 0.062(5) Uani 1 1 d . . . N8 N 0.8557(15) 0.3960(15) 0.6811(10) 0.050(4) Uani 1 1 d . . . H8 H 0.8927 0.3476 0.6963 0.059 Uiso 1 1 calc R . . N9 N 0.8280(15) 0.4131(15) 0.5952(10) 0.048(4) Uani 1 1 d . . . N10 N 0.7548(17) 0.4293(16) 0.4286(10) 0.052(4) Uani 1 1 d . . . N11 N 0.158(3) 0.204(2) 0.704(2) 0.098(8) Uani 1 1 d . . . N12 N 0.007(2) 0.075(2) 0.2036(16) 0.082(7) Uani 1 1 d . . . O1 O 0.6873(18) 0.0921(18) 0.5916(11) 0.093(6) Uani 1 1 d . . . O2 O 0.7973(19) 0.0608(18) 0.4973(11) 0.088(6) Uani 1 1 d . . . O3 O 0.4665(14) 0.2109(13) 0.2084(9) 0.060(4) Uani 1 1 d . . . O4 O 0.9214(16) 0.3210(16) 1.0940(9) 0.076(5) Uani 1 1 d . . . O5 O 0.9680(19) 0.2205(18) 0.9910(12) 0.089(6) Uani 1 1 d . . . O6 O 0.7699(15) 0.5317(14) 0.7189(9) 0.064(4) Uani 1 1 d . . . O7 O -0.008(2) 0.247(2) 0.7080(14) 0.104(7) Uani 1 1 d . . . O8 O -0.1817(19) 0.082(2) 0.2120(14) 0.093(6) Uani 1 1 d . . . C1 C 0.545(2) 0.1712(19) 0.2324(13) 0.052(5) Uani 1 1 d . . . C2 C 0.570(2) 0.1499(19) 0.3202(13) 0.054(5) Uani 1 1 d . . . C3 C 0.655(2) 0.1130(19) 0.3606(13) 0.056(6) Uani 1 1 d . . . H3A H 0.7135 0.0925 0.3333 0.067 Uiso 1 1 calc R . . C4 C 0.640(2) 0.111(2) 0.4523(14) 0.058(6) Uani 1 1 d . . . C5 C 0.552(2) 0.1538(19) 0.4638(14) 0.056(6) Uani 1 1 d . . . H5 H 0.5262 0.1666 0.5176 0.068 Uiso 1 1 calc R . . C6 C 0.407(2) 0.214(2) 0.3801(16) 0.077(7) Uani 1 1 d . . . H6A H 0.3779 0.2215 0.4360 0.115 Uiso 1 1 calc R . . H6B H 0.3452 0.1580 0.3444 0.115 Uiso 1 1 calc R . . H6C H 0.4290 0.2895 0.3530 0.115 Uiso 1 1 calc R . . C7 C 0.6422(18) 0.1225(18) 0.0313(12) 0.046(5) Uani 1 1 d . . . H7 H 0.6877 0.0747 0.0466 0.055 Uiso 1 1 calc R . . C8 C 0.6223(18) 0.1476(18) -0.0599(12) 0.046(5) Uani 1 1 d . . . C9 C 0.6568(18) 0.0872(18) -0.1234(13) 0.049(5) Uani 1 1 d . . . H9 H 0.6922 0.0302 -0.1097 0.059 Uiso 1 1 calc R . . C10 C 0.637(2) 0.114(2) -0.2098(14) 0.055(6) Uani 1 1 d . . . H10 H 0.6600 0.0758 -0.2544 0.067 Uiso 1 1 calc R . . C11 C 0.584(2) 0.196(2) -0.2289(14) 0.056(6) Uani 1 1 d . . . H11 H 0.5678 0.2127 -0.2861 0.067 Uiso 1 1 calc R . . C12 C 0.5564(19) 0.2522(19) -0.1616(13) 0.052(5) Uani 1 1 d . . . H12 H 0.5224 0.3107 -0.1740 0.063 Uiso 1 1 calc R . . C13 C 0.821(2) 0.4601(19) 0.7396(13) 0.050(5) Uani 1 1 d . . . C14 C 0.8434(19) 0.4358(19) 0.8308(13) 0.051(5) Uani 1 1 d . . . C15 C 0.8940(19) 0.3570(19) 0.8655(12) 0.049(5) Uani 1 1 d . . . H15 H 0.9266 0.3085 0.8354 0.059 Uiso 1 1 calc R . . C16 C 0.887(2) 0.365(2) 0.9561(14) 0.057(6) Uani 1 1 d . . . C17 C 0.839(2) 0.447(2) 0.9731(14) 0.057(6) Uani 1 1 d . . . H17 H 0.8270 0.4698 1.0285 0.068 Uiso 1 1 calc R . . C18 C 0.760(2) 0.588(2) 0.8930(14) 0.061(6) Uani 1 1 d . . . H18A H 0.6824 0.5609 0.8641 0.091 Uiso 1 1 calc R . . H18B H 0.8108 0.6520 0.8613 0.091 Uiso 1 1 calc R . . H18C H 0.7552 0.6160 0.9507 0.091 Uiso 1 1 calc R . . C19 C 0.8741(19) 0.3690(19) 0.5379(12) 0.050(5) Uani 1 1 d . . . H19 H 0.9244 0.3260 0.5533 0.060 Uiso 1 1 calc R . . C20 C 0.8458(19) 0.3878(18) 0.4454(12) 0.048(5) Uani 1 1 d . . . C21 C 0.9086(19) 0.3560(19) 0.3825(13) 0.051(5) Uani 1 1 d . . . H21 H 0.9675 0.3229 0.3977 0.061 Uiso 1 1 calc R . . C22 C 0.882(2) 0.3742(19) 0.2968(13) 0.057(6) Uani 1 1 d . . . H22 H 0.9256 0.3575 0.2530 0.069 Uiso 1 1 calc R . . C23 C 0.789(2) 0.419(2) 0.2775(14) 0.059(6) Uani 1 1 d . . . H23 H 0.7673 0.4307 0.2202 0.071 Uiso 1 1 calc R . . C24 C 0.729(2) 0.4449(19) 0.3437(13) 0.055(5) Uani 1 1 d . . . H24 H 0.6679 0.4750 0.3298 0.066 Uiso 1 1 calc R . . C25 C 0.057(3) 0.206(3) 0.675(2) 0.099(10) Uani 1 1 d . . . H25 H 0.0297 0.1693 0.6213 0.119 Uiso 1 1 calc R . . C26 C 0.241(3) 0.159(3) 0.664(2) 0.117(12) Uani 1 1 d . . . H26A H 0.2088 0.1271 0.6075 0.176 Uiso 1 1 calc R . . H26B H 0.2549 0.0988 0.6994 0.176 Uiso 1 1 calc R . . H26C H 0.3143 0.2223 0.6592 0.176 Uiso 1 1 calc R . . C27 C 0.190(4) 0.268(4) 0.784(3) 0.138(14) Uani 1 1 d . . . H27A H 0.1669 0.3374 0.7816 0.207 Uiso 1 1 calc R . . H27B H 0.2748 0.2902 0.7963 0.207 Uiso 1 1 calc R . . H27C H 0.1506 0.2189 0.8299 0.207 Uiso 1 1 calc R . . C28 C -0.118(3) 0.054(3) 0.181(3) 0.102(10) Uani 1 1 d . . . H28 H -0.1475 0.0073 0.1308 0.122 Uiso 1 1 calc R . . C29 C 0.071(3) 0.022(3) 0.154(2) 0.121(12) Uani 1 1 d . . . H29A H 0.1551 0.0616 0.1652 0.182 Uiso 1 1 calc R . . H29B H 0.0501 0.0262 0.0934 0.182 Uiso 1 1 calc R . . H29C H 0.0530 -0.0597 0.1691 0.182 Uiso 1 1 calc R . . C30 C 0.029(4) 0.131(4) 0.284(3) 0.145(15) Uani 1 1 d . . . H30A H -0.0292 0.1695 0.2925 0.218 Uiso 1 1 calc R . . H30B H 0.1071 0.1894 0.2877 0.218 Uiso 1 1 calc R . . H30C H 0.0249 0.0745 0.3285 0.218 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 Hg1 0.0521(6) 0.0619(6) 0.0618(6) -0.0082(4) 0.0000(4) 0.0243(5) Hg2 0.0558(6) 0.0657(6) 0.0634(6) 0.0090(4) 0.0088(4) 0.0301(5) Cl1 0.055(4) 0.061(4) 0.099(5) -0.013(3) 0.003(3) 0.015(3) Cl2 0.073(4) 0.061(4) 0.070(4) -0.011(3) -0.014(3) 0.026(3) Cl3 0.051(4) 0.077(4) 0.106(5) 0.007(4) 0.012(3) 0.020(3) Cl4 0.061(4) 0.088(5) 0.082(4) 0.023(3) 0.020(3) 0.022(3) N1 0.062(12) 0.062(12) 0.048(11) -0.001(9) 0.009(9) 0.027(10) N2 0.077(15) 0.075(14) 0.045(12) -0.005(10) 0.004(11) 0.023(12) N3 0.054(11) 0.056(11) 0.038(9) -0.004(8) 0.005(8) 0.024(9) N4 0.048(10) 0.057(11) 0.040(9) -0.001(8) -0.001(8) 0.021(9) N5 0.037(9) 0.057(11) 0.044(10) -0.002(8) 0.002(7) 0.014(8) N6 0.060(12) 0.070(12) 0.046(10) -0.002(9) 0.005(9) 0.027(10) N7 0.064(13) 0.068(13) 0.053(12) 0.006(10) 0.004(10) 0.022(11) N8 0.056(11) 0.062(11) 0.039(9) -0.005(8) 0.004(8) 0.030(9) N9 0.054(11) 0.057(11) 0.040(9) -0.001(8) 0.003(8) 0.028(9) N10 0.061(12) 0.059(11) 0.041(9) 0.007(8) 0.002(8) 0.025(10) N11 0.11(2) 0.098(19) 0.12(2) 0.028(16) 0.026(18) 0.068(18) N12 0.077(16) 0.097(18) 0.094(17) 0.007(14) 0.011(13) 0.055(14) O1 0.112(16) 0.109(15) 0.044(10) -0.007(9) -0.005(10) 0.018(13) O2 0.091(15) 0.120(16) 0.062(11) 0.001(10) 0.003(10) 0.048(13) O3 0.061(10) 0.071(10) 0.054(9) 0.000(7) 0.006(8) 0.029(9) O4 0.091(13) 0.098(13) 0.033(8) 0.001(8) 0.016(8) 0.023(11) O5 0.104(16) 0.100(15) 0.074(12) 0.016(10) -0.003(11) 0.050(13) O6 0.071(11) 0.076(11) 0.055(9) 0.000(8) 0.002(8) 0.037(9) O7 0.117(18) 0.130(18) 0.103(15) 0.013(13) 0.012(13) 0.093(17) O8 0.077(14) 0.114(17) 0.106(16) 0.021(12) 0.028(12) 0.053(13) C1 0.056(14) 0.061(14) 0.043(12) 0.000(10) 0.006(10) 0.024(12) C2 0.059(14) 0.057(13) 0.047(12) 0.003(10) 0.007(10) 0.021(11) C3 0.063(15) 0.061(14) 0.044(12) 0.001(10) -0.001(11) 0.024(12) C4 0.065(15) 0.066(15) 0.043(12) 0.004(10) 0.000(11) 0.022(13) C5 0.064(15) 0.061(14) 0.043(12) -0.003(10) 0.009(11) 0.017(12) C6 0.072(18) 0.10(2) 0.066(16) -0.009(14) 0.006(13) 0.034(16) C7 0.046(12) 0.053(12) 0.041(11) -0.003(9) 0.000(9) 0.021(10) C8 0.044(12) 0.052(12) 0.042(11) -0.006(9) -0.005(9) 0.016(10) C9 0.052(13) 0.049(12) 0.046(12) -0.006(9) 0.008(9) 0.015(10) C10 0.053(13) 0.063(15) 0.045(12) -0.004(10) 0.009(10) 0.012(12) C11 0.054(14) 0.064(15) 0.042(12) -0.006(11) 0.002(10) 0.008(12) C12 0.052(13) 0.055(13) 0.049(12) 0.004(10) 0.000(10) 0.018(11) C13 0.053(13) 0.061(14) 0.046(12) 0.001(10) 0.004(10) 0.031(12) C14 0.054(13) 0.061(13) 0.043(11) -0.010(10) 0.001(10) 0.027(11) C15 0.055(13) 0.060(13) 0.042(11) -0.006(10) 0.005(10) 0.032(11) C16 0.057(14) 0.068(15) 0.047(12) 0.006(11) 0.002(10) 0.023(12) C17 0.056(14) 0.068(15) 0.046(12) -0.001(11) 0.002(10) 0.021(12) C18 0.065(15) 0.071(15) 0.062(14) -0.009(12) 0.007(11) 0.044(13) C19 0.055(13) 0.062(14) 0.040(11) 0.001(10) 0.003(10) 0.028(11) C20 0.055(13) 0.058(13) 0.038(11) 0.002(9) 0.006(10) 0.028(11) C21 0.055(13) 0.063(14) 0.044(11) -0.004(10) -0.002(10) 0.033(11) C22 0.059(14) 0.066(15) 0.046(13) 0.000(10) 0.008(10) 0.017(12) C23 0.067(16) 0.064(15) 0.046(12) 0.003(10) 0.002(11) 0.019(12) C24 0.059(14) 0.063(14) 0.044(12) 0.006(10) 0.004(10) 0.023(12) C25 0.11(3) 0.10(2) 0.12(3) 0.016(19) 0.01(2) 0.08(2) C26 0.12(3) 0.12(3) 0.13(3) 0.04(2) 0.02(2) 0.06(3) C27 0.14(4) 0.12(3) 0.15(4) 0.00(3) 0.00(3) 0.05(3) C28 0.10(3) 0.09(2) 0.12(3) 0.02(2) 0.01(2) 0.05(2) C29 0.11(3) 0.12(3) 0.14(3) 0.01(2) 0.05(2) 0.05(2) C30 0.13(4) 0.13(4) 0.17(4) 0.01(3) 0.03(3) 0.04(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 Hg1 Cl1 2.347(6) . ? Hg1 Cl2 2.348(6) . ? Hg1 N4 2.502(16) . ? Hg1 N5 2.515(16) . ? Hg1 O3 2.738(15) . ? Hg2 Cl3 2.350(7) . ? Hg2 Cl4 2.351(6) . ? Hg2 N10 2.465(17) . ? Hg2 N9 2.488(16) . ? Hg2 O6 2.708(15) . ? N1 C5 1.29(3) . ? N1 C6 1.42(3) . ? N1 C2 1.43(3) . ? N2 O2 1.21(3) . ? N2 O1 1.21(2) . ? N2 C4 1.36(3) . ? N3 C1 1.34(2) . ? N3 N4 1.37(2) . ? N3 H3 0.8600 . ? N4 C7 1.25(2) . ? N5 C8 1.31(2) . ? N5 C12 1.35(2) . ? N6 C17 1.37(3) . ? N6 C14 1.38(2) . ? N6 C18 1.44(3) . ? N7 O4 1.23(2) . ? N7 O5 1.26(2) . ? N7 C16 1.39(3) . ? N8 C13 1.35(2) . ? N8 N9 1.38(2) . ? N8 H8 0.8600 . ? N9 C19 1.26(2) . ? N10 C20 1.34(3) . ? N10 C24 1.36(2) . ? N11 C25 1.27(4) . ? N11 C27 1.42(4) . ? N11 C26 1.42(4) . ? N12 C30 1.38(4) . ? N12 C29 1.40(4) . ? N12 C28 1.45(4) . ? O3 C1 1.22(2) . ? O6 C13 1.23(2) . ? O7 C25 1.17(3) . ? O8 C28 1.06(3) . ? C1 C2 1.41(3) . ? C2 C3 1.36(3) . ? C3 C4 1.43(3) . ? C3 H3A 0.9300 . ? C4 C5 1.33(3) . ? C5 H5 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.46(3) . ? C7 H7 0.9300 . ? C8 C9 1.37(3) . ? C9 C10 1.40(3) . ? C9 H9 0.9300 . ? C10 C11 1.34(3) . ? C10 H10 0.9300 . ? C11 C12 1.35(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.46(3) . ? C14 C15 1.37(3) . ? C15 C16 1.41(3) . ? C15 H15 0.9300 . ? C16 C17 1.31(3) . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.48(3) . ? C19 H19 0.9300 . ? C20 C21 1.38(3) . ? C21 C22 1.37(3) . ? C21 H21 0.9300 . ? C22 C23 1.40(3) . ? C22 H22 0.9300 . ? C23 C24 1.36(3) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 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 Cl1 Hg1 Cl2 149.2(2) . . ? Cl1 Hg1 N4 103.5(4) . . ? Cl2 Hg1 N4 104.5(4) . . ? Cl1 Hg1 N5 91.4(4) . . ? Cl2 Hg1 N5 111.9(4) . . ? N4 Hg1 N5 65.1(5) . . ? Cl1 Hg1 O3 92.4(4) . . ? Cl2 Hg1 O3 90.4(4) . . ? N4 Hg1 O3 60.3(5) . . ? N5 Hg1 O3 124.6(5) . . ? Cl3 Hg2 Cl4 152.3(2) . . ? Cl3 Hg2 N10 92.5(5) . . ? Cl4 Hg2 N10 110.8(5) . . ? Cl3 Hg2 N9 99.6(4) . . ? Cl4 Hg2 N9 103.4(4) . . ? N10 Hg2 N9 65.9(5) . . ? Cl3 Hg2 O6 91.2(4) . . ? Cl4 Hg2 O6 86.9(4) . . ? N10 Hg2 O6 126.1(5) . . ? N9 Hg2 O6 60.5(5) . . ? C5 N1 C6 124.6(19) . . ? C5 N1 C2 110.6(18) . . ? C6 N1 C2 124.7(19) . . ? O2 N2 O1 122(2) . . ? O2 N2 C4 119(2) . . ? O1 N2 C4 119(2) . . ? C1 N3 N4 119.4(17) . . ? C1 N3 H3 120.3 . . ? N4 N3 H3 120.3 . . ? C7 N4 N3 121.0(17) . . ? C7 N4 Hg1 119.2(13) . . ? N3 N4 Hg1 119.8(12) . . ? C8 N5 C12 118.1(17) . . ? C8 N5 Hg1 116.8(13) . . ? C12 N5 Hg1 123.5(14) . . ? C17 N6 C14 106.4(18) . . ? C17 N6 C18 124.4(18) . . ? C14 N6 C18 129.1(18) . . ? O4 N7 O5 123(2) . . ? O4 N7 C16 117(2) . . ? O5 N7 C16 119.5(19) . . ? C13 N8 N9 115.6(16) . . ? C13 N8 H8 122.2 . . ? N9 N8 H8 122.2 . . ? C19 N9 N8 117.8(16) . . ? C19 N9 Hg2 119.6(13) . . ? N8 N9 Hg2 122.7(11) . . ? C20 N10 C24 115.8(18) . . ? C20 N10 Hg2 117.5(12) . . ? C24 N10 Hg2 124.2(14) . . ? C25 N11 C27 109(3) . . ? C25 N11 C26 130(3) . . ? C27 N11 C26 120(3) . . ? C30 N12 C29 134(3) . . ? C30 N12 C28 105(3) . . ? C29 N12 C28 120(3) . . ? C1 O3 Hg1 116.0(13) . . ? C13 O6 Hg2 116.0(13) . . ? O3 C1 N3 120.6(19) . . ? O3 C1 C2 123(2) . . ? N3 C1 C2 116(2) . . ? C3 C2 C1 133(2) . . ? C3 C2 N1 103.7(18) . . ? C1 C2 N1 124(2) . . ? C2 C3 C4 109(2) . . ? C2 C3 H3A 125.6 . . ? C4 C3 H3A 125.6 . . ? C5 C4 N2 126(2) . . ? C5 C4 C3 106(2) . . ? N2 C4 C3 128(2) . . ? N1 C5 C4 111(2) . . ? N1 C5 H5 124.6 . . ? C4 C5 H5 124.6 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N4 C7 C8 119.2(19) . . ? N4 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? N5 C8 C9 122.3(19) . . ? N5 C8 C7 118.3(18) . . ? C9 C8 C7 119.4(19) . . ? C8 C9 C10 118(2) . . ? C8 C9 H9 121.2 . . ? C10 C9 H9 121.2 . . ? C11 C10 C9 121(2) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 117(2) . . ? C10 C11 H11 121.5 . . ? C12 C11 H11 121.5 . . ? N5 C12 C11 124(2) . . ? N5 C12 H12 117.9 . . ? C11 C12 H12 117.9 . . ? O6 C13 N8 123.0(19) . . ? O6 C13 C14 121.6(18) . . ? N8 C13 C14 115.4(18) . . ? C15 C14 N6 108.9(18) . . ? C15 C14 C13 129.6(18) . . ? N6 C14 C13 121.4(19) . . ? C14 C15 C16 105.9(18) . . ? C14 C15 H15 127.0 . . ? C16 C15 H15 127.0 . . ? C17 C16 N7 126(2) . . ? C17 C16 C15 108(2) . . ? N7 C16 C15 125(2) . . ? C16 C17 N6 110(2) . . ? C16 C17 H17 124.9 . . ? N6 C17 H17 124.9 . . ? N6 C18 H18A 109.5 . . ? N6 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N6 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N9 C19 C20 118.2(19) . . ? N9 C19 H19 120.9 . . ? C20 C19 H19 120.9 . . ? N10 C20 C21 124.4(18) . . ? N10 C20 C19 116.5(17) . . ? C21 C20 C19 119.0(18) . . ? C22 C21 C20 118.7(19) . . ? C22 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? C21 C22 C23 118(2) . . ? C21 C22 H22 121.0 . . ? C23 C22 H22 121.0 . . ? C24 C23 C22 119(2) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? N10 C24 C23 124(2) . . ? N10 C24 H24 118.1 . . ? C23 C24 H24 118.1 . . ? O7 C25 N11 129(4) . . ? O7 C25 H25 115.5 . . ? N11 C25 H25 115.5 . . ? N11 C26 H26A 109.5 . . ? N11 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N11 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N11 C27 H27A 109.5 . . ? N11 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N11 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O8 C28 N12 131(4) . . ? O8 C28 H28 114.6 . . ? N12 C28 H28 114.6 . . ? N12 C29 H29A 109.5 . . ? N12 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N12 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N12 C30 H30A 109.5 . . ? N12 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N12 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 C1 N3 N4 C7 -166.0(19) . . . . ? C1 N3 N4 Hg1 15(2) . . . . ? Cl1 Hg1 N4 C7 81.2(15) . . . . ? Cl2 Hg1 N4 C7 -111.9(15) . . . . ? N5 Hg1 N4 C7 -4.1(14) . . . . ? O3 Hg1 N4 C7 166.1(17) . . . . ? Cl1 Hg1 N4 N3 -100.0(13) . . . . ? Cl2 Hg1 N4 N3 66.9(13) . . . . ? N5 Hg1 N4 N3 174.7(15) . . . . ? O3 Hg1 N4 N3 -15.1(12) . . . . ? Cl1 Hg1 N5 C8 -94.7(14) . . . . ? Cl2 Hg1 N5 C8 105.9(14) . . . . ? N4 Hg1 N5 C8 9.6(13) . . . . ? O3 Hg1 N5 C8 -0.8(16) . . . . ? Cl1 Hg1 N5 C12 70.2(15) . . . . ? Cl2 Hg1 N5 C12 -89.2(15) . . . . ? N4 Hg1 N5 C12 174.5(17) . . . . ? O3 Hg1 N5 C12 164.1(14) . . . . ? C13 N8 N9 C19 170(2) . . . . ? C13 N8 N9 Hg2 -12(2) . . . . ? Cl3 Hg2 N9 C19 -83.4(16) . . . . ? Cl4 Hg2 N9 C19 112.1(16) . . . . ? N10 Hg2 N9 C19 5.0(16) . . . . ? O6 Hg2 N9 C19 -169.3(18) . . . . ? Cl3 Hg2 N9 N8 98.0(14) . . . . ? Cl4 Hg2 N9 N8 -66.5(14) . . . . ? N10 Hg2 N9 N8 -173.6(16) . . . . ? O6 Hg2 N9 N8 12.1(13) . . . . ? Cl3 Hg2 N10 C20 87.4(15) . . . . ? Cl4 Hg2 N10 C20 -107.9(15) . . . . ? N9 Hg2 N10 C20 -12.0(14) . . . . ? O6 Hg2 N10 C20 -5.9(18) . . . . ? Cl3 Hg2 N10 C24 -73.9(17) . . . . ? Cl4 Hg2 N10 C24 90.9(17) . . . . ? N9 Hg2 N10 C24 -173.3(19) . . . . ? O6 Hg2 N10 C24 -167.2(15) . . . . ? Cl1 Hg1 O3 C1 120.6(15) . . . . ? Cl2 Hg1 O3 C1 -90.1(15) . . . . ? N4 Hg1 O3 C1 16.4(15) . . . . ? N5 Hg1 O3 C1 27.2(17) . . . . ? Cl3 Hg2 O6 C13 -112.6(16) . . . . ? Cl4 Hg2 O6 C13 95.0(16) . . . . ? N10 Hg2 O6 C13 -18.7(18) . . . . ? N9 Hg2 O6 C13 -12.3(15) . . . . ? Hg1 O3 C1 N3 -16(3) . . . . ? Hg1 O3 C1 C2 164.0(17) . . . . ? N4 N3 C1 O3 2(3) . . . . ? N4 N3 C1 C2 -178.2(18) . . . . ? O3 C1 C2 C3 -176(2) . . . . ? N3 C1 C2 C3 4(4) . . . . ? O3 C1 C2 N1 -2(4) . . . . ? N3 C1 C2 N1 178.6(19) . . . . ? C5 N1 C2 C3 -1(2) . . . . ? C6 N1 C2 C3 -178(2) . . . . ? C5 N1 C2 C1 -176(2) . . . . ? C6 N1 C2 C1 6(3) . . . . ? C1 C2 C3 C4 178(2) . . . . ? N1 C2 C3 C4 3(2) . . . . ? O2 N2 C4 C5 -171(2) . . . . ? O1 N2 C4 C5 7(4) . . . . ? O2 N2 C4 C3 -1(4) . . . . ? O1 N2 C4 C3 177(2) . . . . ? C2 C3 C4 C5 -4(3) . . . . ? C2 C3 C4 N2 -176(2) . . . . ? C6 N1 C5 C4 176(2) . . . . ? C2 N1 C5 C4 -2(3) . . . . ? N2 C4 C5 N1 176(2) . . . . ? C3 C4 C5 N1 4(3) . . . . ? N3 N4 C7 C8 179.9(17) . . . . ? Hg1 N4 C7 C8 -1(2) . . . . ? C12 N5 C8 C9 2(3) . . . . ? Hg1 N5 C8 C9 167.3(15) . . . . ? C12 N5 C8 C7 180.0(17) . . . . ? Hg1 N5 C8 C7 -14(2) . . . . ? N4 C7 C8 N5 11(3) . . . . ? N4 C7 C8 C9 -171(2) . . . . ? N5 C8 C9 C10 -1(3) . . . . ? C7 C8 C9 C10 -179.6(18) . . . . ? C8 C9 C10 C11 -1(3) . . . . ? C9 C10 C11 C12 2(3) . . . . ? C8 N5 C12 C11 0(3) . . . . ? Hg1 N5 C12 C11 -164.6(17) . . . . ? C10 C11 C12 N5 -2(3) . . . . ? Hg2 O6 C13 N8 12(3) . . . . ? Hg2 O6 C13 C14 -165.1(16) . . . . ? N9 N8 C13 O6 -2(3) . . . . ? N9 N8 C13 C14 176.1(17) . . . . ? C17 N6 C14 C15 -1(3) . . . . ? C18 N6 C14 C15 175(2) . . . . ? C17 N6 C14 C13 178(2) . . . . ? C18 N6 C14 C13 -6(4) . . . . ? O6 C13 C14 C15 177(2) . . . . ? N8 C13 C14 C15 0(4) . . . . ? O6 C13 C14 N6 -1(3) . . . . ? N8 C13 C14 N6 -178(2) . . . . ? N6 C14 C15 C16 2(3) . . . . ? C13 C14 C15 C16 -176(2) . . . . ? O4 N7 C16 C17 -3(4) . . . . ? O5 N7 C16 C17 179(2) . . . . ? O4 N7 C16 C15 175(2) . . . . ? O5 N7 C16 C15 -3(4) . . . . ? C14 C15 C16 C17 -3(3) . . . . ? C14 C15 C16 N7 179(2) . . . . ? N7 C16 C17 N6 -180(2) . . . . ? C15 C16 C17 N6 2(3) . . . . ? C14 N6 C17 C16 -1(3) . . . . ? C18 N6 C17 C16 -177(2) . . . . ? N8 N9 C19 C20 -179.5(17) . . . . ? Hg2 N9 C19 C20 2(3) . . . . ? C24 N10 C20 C21 -3(3) . . . . ? Hg2 N10 C20 C21 -166.0(17) . . . . ? C24 N10 C20 C19 -179.4(18) . . . . ? Hg2 N10 C20 C19 18(2) . . . . ? N9 C19 C20 N10 -13(3) . . . . ? N9 C19 C20 C21 170(2) . . . . ? N10 C20 C21 C22 4(3) . . . . ? C19 C20 C21 C22 -180(2) . . . . ? C20 C21 C22 C23 -3(3) . . . . ? C21 C22 C23 C24 1(3) . . . . ? C20 N10 C24 C23 1(3) . . . . ? Hg2 N10 C24 C23 162.8(17) . . . . ? C22 C23 C24 N10 -1(3) . . . . ? C27 N11 C25 O7 -3(5) . . . . ? C26 N11 C25 O7 -177(3) . . . . ? C30 N12 C28 O8 7(5) . . . . ? C29 N12 C28 O8 176(4) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 3.828 _refine_diff_density_min -3.221 _refine_diff_density_rms 0.279 data_091103a _database_code_depnum_ccdc_archive 'CCDC 773663' #=================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 Cl2 N5 O3 Zn' _chemical_formula_weight 409.53 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5944(8) _cell_length_b 12.6407(13) _cell_length_c 16.4624(16) _cell_angle_alpha 90.00 _cell_angle_beta 93.9700(10) _cell_angle_gamma 90.00 _cell_volume 1576.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2288 _cell_measurement_theta_min 2.689 _cell_measurement_theta_max 24.937 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 1.917 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7121 _exptl_absorpt_correction_T_max 0.8464 _exptl_absorpt_process_details sadabs _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 8088 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2771 _reflns_number_gt 1927 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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^)+(0.0416P)^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_number_reflns 2771 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0767 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _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 Zn1 Zn 0.03308(6) 0.79934(3) 0.11183(2) 0.04731(16) Uani 1 1 d . . . Cl1 Cl 0.12941(13) 0.67625(7) 0.19891(5) 0.0557(3) Uani 1 1 d . . . Cl2 Cl -0.21008(14) 0.89453(8) 0.14254(6) 0.0621(3) Uani 1 1 d . . . N1 N 0.2274(3) 0.9653(2) 0.02156(18) 0.0446(7) Uani 1 1 d . . . H1 H 0.2570 1.0039 -0.0183 0.054 Uiso 1 1 calc R . . N2 N 0.1324(3) 0.8747(2) 0.01015(18) 0.0401(7) Uani 1 1 d . . . N3 N 0.4161(4) 1.1333(2) 0.18919(18) 0.0475(8) Uani 1 1 d . . . N4 N 0.5836(4) 1.3316(2) 0.0593(2) 0.0516(8) Uani 1 1 d . . . N5 N -0.0594(3) 0.7038(2) 0.00936(16) 0.0381(7) Uani 1 1 d . . . O1 O 0.2301(3) 0.9325(2) 0.15636(15) 0.0612(7) Uani 1 1 d . . . O2 O 0.6428(4) 1.4029(2) 0.10328(18) 0.0704(8) Uani 1 1 d . . . O3 O 0.5835(4) 1.3326(2) -0.01485(18) 0.0703(8) Uani 1 1 d . . . C1 C 0.2726(4) 0.9904(3) 0.1013(2) 0.0429(9) Uani 1 1 d . . . C2 C 0.3705(4) 1.0893(3) 0.1124(2) 0.0397(8) Uani 1 1 d . . . C3 C 0.4281(4) 1.1565(3) 0.0546(2) 0.0416(8) Uani 1 1 d . . . H3 H 0.4164 1.1471 -0.0015 0.050 Uiso 1 1 calc R . . C4 C 0.5077(4) 1.2414(3) 0.0964(2) 0.0418(8) Uani 1 1 d . . . C5 C 0.4990(5) 1.2257(3) 0.1786(2) 0.0499(10) Uani 1 1 d . . . H5 H 0.5426 1.2711 0.2197 0.060 Uiso 1 1 calc R . . C6 C 0.3846(6) 1.0887(4) 0.2693(2) 0.0768(14) Uani 1 1 d . . . H6A H 0.4333 1.1350 0.3113 0.115 Uiso 1 1 calc R . . H6B H 0.4400 1.0206 0.2750 0.115 Uiso 1 1 calc R . . H6C H 0.2599 1.0813 0.2741 0.115 Uiso 1 1 calc R . . C7 C 0.0870(4) 0.8387(3) -0.0606(2) 0.0423(8) Uani 1 1 d . . . H7 H 0.1169 0.8732 -0.1076 0.051 Uiso 1 1 calc R . . C8 C -0.0145(4) 0.7403(2) -0.0637(2) 0.0373(8) Uani 1 1 d . . . C9 C -0.0587(5) 0.6868(3) -0.1353(2) 0.0480(9) Uani 1 1 d . . . H9 H -0.0283 0.7140 -0.1849 0.058 Uiso 1 1 calc R . . C10 C -0.1489(5) 0.5920(3) -0.1320(2) 0.0529(10) Uani 1 1 d . . . H10 H -0.1785 0.5541 -0.1794 0.064 Uiso 1 1 calc R . . C11 C -0.1938(5) 0.5548(3) -0.0593(2) 0.0483(9) Uani 1 1 d . . . H11 H -0.2549 0.4914 -0.0561 0.058 Uiso 1 1 calc R . . C12 C -0.1472(5) 0.6126(3) 0.0105(2) 0.0472(9) Uani 1 1 d . . . H12 H -0.1787 0.5866 0.0603 0.057 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 Zn1 0.0595(3) 0.0422(3) 0.0401(3) 0.0038(2) 0.00242(19) -0.0023(2) Cl1 0.0788(7) 0.0439(6) 0.0435(5) 0.0021(4) -0.0020(5) 0.0066(5) Cl2 0.0767(7) 0.0575(6) 0.0521(6) -0.0002(5) 0.0042(5) 0.0098(5) N1 0.0513(18) 0.0335(17) 0.0499(18) 0.0034(15) 0.0090(15) -0.0088(14) N2 0.0425(17) 0.0286(16) 0.0495(19) -0.0011(14) 0.0045(14) -0.0015(13) N3 0.0504(19) 0.0457(19) 0.0455(18) 0.0051(15) -0.0038(14) -0.0071(15) N4 0.0442(19) 0.0418(19) 0.069(2) 0.0070(18) 0.0030(17) -0.0044(15) N5 0.0441(17) 0.0333(16) 0.0368(16) 0.0031(13) 0.0018(12) -0.0020(14) O1 0.0774(19) 0.0549(17) 0.0508(16) 0.0101(14) 0.0010(14) -0.0257(15) O2 0.080(2) 0.0475(17) 0.083(2) -0.0088(16) 0.0023(16) -0.0232(16) O3 0.089(2) 0.0586(18) 0.065(2) 0.0108(16) 0.0136(16) -0.0226(16) C1 0.039(2) 0.036(2) 0.053(2) 0.0032(19) 0.0027(17) -0.0026(17) C2 0.0362(19) 0.037(2) 0.046(2) 0.0038(17) 0.0008(15) 0.0016(16) C3 0.040(2) 0.041(2) 0.044(2) -0.0017(18) 0.0037(16) 0.0005(17) C4 0.038(2) 0.036(2) 0.050(2) 0.0038(17) 0.0010(17) -0.0036(17) C5 0.051(2) 0.043(2) 0.054(2) -0.0014(19) -0.0105(18) -0.0063(18) C6 0.102(4) 0.081(3) 0.046(2) 0.014(2) -0.006(2) -0.027(3) C7 0.046(2) 0.038(2) 0.044(2) 0.0027(18) 0.0114(17) -0.0011(17) C8 0.042(2) 0.0296(18) 0.040(2) 0.0040(16) 0.0040(15) 0.0002(16) C9 0.063(2) 0.044(2) 0.037(2) 0.0021(17) 0.0078(17) -0.001(2) C10 0.069(3) 0.039(2) 0.050(2) -0.0047(19) 0.000(2) -0.002(2) C11 0.056(2) 0.033(2) 0.055(2) -0.0001(19) -0.0036(19) -0.0066(17) C12 0.054(2) 0.042(2) 0.046(2) 0.0108(18) 0.0065(18) -0.0016(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 2.110(3) . ? Zn1 N5 2.153(3) . ? Zn1 Cl1 2.2059(10) . ? Zn1 Cl2 2.2897(11) . ? Zn1 O1 2.336(2) . ? N1 N2 1.359(3) . ? N1 C1 1.371(4) . ? N1 H1 0.8600 . ? N2 C7 1.275(4) . ? N3 C5 1.344(4) . ? N3 C2 1.403(4) . ? N3 C6 1.470(4) . ? N4 O3 1.221(4) . ? N4 O2 1.222(4) . ? N4 C4 1.433(4) . ? N5 C12 1.332(4) . ? N5 C8 1.354(4) . ? O1 C1 1.226(4) . ? C1 C2 1.459(5) . ? C2 C3 1.369(5) . ? C3 C4 1.391(5) . ? C3 H3 0.9300 . ? C4 C5 1.374(5) . ? C5 H5 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.463(4) . ? C7 H7 0.9300 . ? C8 C9 1.379(4) . ? C9 C10 1.384(5) . ? C9 H9 0.9300 . ? C10 C11 1.351(5) . ? C10 H10 0.9300 . ? C11 C12 1.386(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Zn1 N5 75.35(10) . . ? N2 Zn1 Cl1 135.51(8) . . ? N5 Zn1 Cl1 100.89(8) . . ? N2 Zn1 Cl2 106.00(8) . . ? N5 Zn1 Cl2 104.09(8) . . ? Cl1 Zn1 Cl2 117.61(4) . . ? N2 Zn1 O1 70.56(10) . . ? N5 Zn1 O1 144.83(10) . . ? Cl1 Zn1 O1 97.34(7) . . ? Cl2 Zn1 O1 93.50(8) . . ? N2 N1 C1 115.0(3) . . ? N2 N1 H1 122.5 . . ? C1 N1 H1 122.5 . . ? C7 N2 N1 122.3(3) . . ? C7 N2 Zn1 118.3(2) . . ? N1 N2 Zn1 119.1(2) . . ? C5 N3 C2 108.4(3) . . ? C5 N3 C6 123.8(3) . . ? C2 N3 C6 127.7(3) . . ? O3 N4 O2 124.0(3) . . ? O3 N4 C4 117.5(3) . . ? O2 N4 C4 118.5(3) . . ? C12 N5 C8 117.6(3) . . ? C12 N5 Zn1 127.7(2) . . ? C8 N5 Zn1 114.6(2) . . ? C1 O1 Zn1 113.2(2) . . ? O1 C1 N1 120.5(3) . . ? O1 C1 C2 125.3(3) . . ? N1 C1 C2 114.2(3) . . ? C3 C2 N3 108.0(3) . . ? C3 C2 C1 129.0(3) . . ? N3 C2 C1 123.0(3) . . ? C2 C3 C4 106.5(3) . . ? C2 C3 H3 126.7 . . ? C4 C3 H3 126.7 . . ? C5 C4 C3 109.1(3) . . ? C5 C4 N4 125.7(3) . . ? C3 C4 N4 125.3(3) . . ? N3 C5 C4 108.0(3) . . ? N3 C5 H5 126.0 . . ? C4 C5 H5 126.0 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C8 116.4(3) . . ? N2 C7 H7 121.8 . . ? C8 C7 H7 121.8 . . ? N5 C8 C9 122.0(3) . . ? N5 C8 C7 115.0(3) . . ? C9 C8 C7 123.0(3) . . ? C8 C9 C10 118.9(3) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 119.5(4) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 119.0(3) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? N5 C12 C11 123.0(3) . . ? N5 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? 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 C1 N1 N2 C7 -177.0(3) . . . . ? C1 N1 N2 Zn1 9.6(3) . . . . ? N5 Zn1 N2 C7 4.8(2) . . . . ? Cl1 Zn1 N2 C7 95.5(3) . . . . ? Cl2 Zn1 N2 C7 -95.9(2) . . . . ? O1 Zn1 N2 C7 176.0(3) . . . . ? N5 Zn1 N2 N1 178.5(2) . . . . ? Cl1 Zn1 N2 N1 -90.8(2) . . . . ? Cl2 Zn1 N2 N1 77.7(2) . . . . ? O1 Zn1 N2 N1 -10.3(2) . . . . ? N2 Zn1 N5 C12 175.0(3) . . . . ? Cl1 Zn1 N5 C12 40.5(3) . . . . ? Cl2 Zn1 N5 C12 -81.8(3) . . . . ? O1 Zn1 N5 C12 160.5(3) . . . . ? N2 Zn1 N5 C8 -1.9(2) . . . . ? Cl1 Zn1 N5 C8 -136.4(2) . . . . ? Cl2 Zn1 N5 C8 101.3(2) . . . . ? O1 Zn1 N5 C8 -16.5(3) . . . . ? N2 Zn1 O1 C1 10.6(2) . . . . ? N5 Zn1 O1 C1 25.5(4) . . . . ? Cl1 Zn1 O1 C1 146.4(3) . . . . ? Cl2 Zn1 O1 C1 -95.2(3) . . . . ? Zn1 O1 C1 N1 -9.7(4) . . . . ? Zn1 O1 C1 C2 169.8(3) . . . . ? N2 N1 C1 O1 1.1(5) . . . . ? N2 N1 C1 C2 -178.4(3) . . . . ? C5 N3 C2 C3 0.4(4) . . . . ? C6 N3 C2 C3 -178.7(4) . . . . ? C5 N3 C2 C1 -177.6(3) . . . . ? C6 N3 C2 C1 3.3(6) . . . . ? O1 C1 C2 C3 177.5(4) . . . . ? N1 C1 C2 C3 -3.0(5) . . . . ? O1 C1 C2 N3 -4.9(6) . . . . ? N1 C1 C2 N3 174.6(3) . . . . ? N3 C2 C3 C4 -0.4(4) . . . . ? C1 C2 C3 C4 177.5(3) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C2 C3 C4 N4 -178.7(3) . . . . ? O3 N4 C4 C5 178.8(4) . . . . ? O2 N4 C4 C5 -1.8(5) . . . . ? O3 N4 C4 C3 -2.4(5) . . . . ? O2 N4 C4 C3 177.0(3) . . . . ? C2 N3 C5 C4 -0.2(4) . . . . ? C6 N3 C5 C4 178.9(4) . . . . ? C3 C4 C5 N3 0.0(4) . . . . ? N4 C4 C5 N3 179.0(3) . . . . ? N1 N2 C7 C8 179.8(3) . . . . ? Zn1 N2 C7 C8 -6.7(4) . . . . ? C12 N5 C8 C9 0.7(5) . . . . ? Zn1 N5 C8 C9 178.0(3) . . . . ? C12 N5 C8 C7 -177.9(3) . . . . ? Zn1 N5 C8 C7 -0.7(4) . . . . ? N2 C7 C8 N5 4.8(5) . . . . ? N2 C7 C8 C9 -173.8(3) . . . . ? N5 C8 C9 C10 -1.1(5) . . . . ? C7 C8 C9 C10 177.4(3) . . . . ? C8 C9 C10 C11 0.9(6) . . . . ? C9 C10 C11 C12 -0.3(6) . . . . ? C8 N5 C12 C11 -0.1(5) . . . . ? Zn1 N5 C12 C11 -176.9(2) . . . . ? C10 C11 C12 N5 -0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.466 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.064 # Attachment '- 5.cif' data_101107b _database_code_depnum_ccdc_archive 'CCDC 823232' #TrackingRef '- 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 K N6 O6' _chemical_formula_weight 374.37 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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8049(12) _cell_length_b 10.0800(10) _cell_length_c 13.9721(15) _cell_angle_alpha 90.00 _cell_angle_beta 105.1080(10) _cell_angle_gamma 90.00 _cell_volume 1605.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1384 _cell_measurement_theta_min 2.547 _cell_measurement_theta_max 21.515 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8704 _exptl_absorpt_correction_T_max 0.9152 _exptl_absorpt_process_details sadabs _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 7781 _diffrn_reflns_av_R_equivalents 0.0814 _diffrn_reflns_av_sigmaI/netI 0.0953 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2815 _reflns_number_gt 1440 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0776P)^2^+2.1510P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2815 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1382 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.2036 _refine_ls_wR_factor_gt 0.1482 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 K1 K 0.75339(10) 0.70570(13) 0.61067(10) 0.0531(4) Uani 1 1 d . . . N1 N 0.4621(4) 0.5837(4) 0.6208(3) 0.0450(11) Uani 1 1 d . . . H1 H 0.4076 0.5375 0.6353 0.054 Uiso 1 1 calc R A . N2 N 0.5707(4) 0.5290(5) 0.6241(3) 0.0446(11) Uani 1 1 d . A . N3 N 0.3055(4) 0.9016(4) 0.5939(3) 0.0449(11) Uani 1 1 d . A . N4 N 0.0211(4) 0.7771(5) 0.5898(3) 0.0497(12) Uani 1 1 d . . . N5 N 0.7918(4) 0.4234(4) 0.6487(3) 0.0482(12) Uani 1 1 d . A . N6 N 0.7402(5) 0.8306(6) 0.8331(4) 0.0533(13) Uani 1 1 d . . . O1 O 0.5201(3) 0.7823(4) 0.5723(3) 0.0604(11) Uani 1 1 d . A . O2 O -0.0421(3) 0.8738(4) 0.5915(3) 0.0665(12) Uani 1 1 d . . . O3 O -0.0142(3) 0.6621(5) 0.5877(3) 0.0702(13) Uani 1 1 d . . . O4 O 0.805(3) 0.738(3) 0.825(2) 0.073(5) Uani 0.70(12) 1 d P A 1 O5 O 0.686(5) 0.905(2) 0.7631(10) 0.078(8) Uani 0.70(12) 1 d P A 1 O4' O 0.749(12) 0.908(4) 0.769(4) 0.073(18) Uani 0.30(12) 1 d P A 2 O5' O 0.767(10) 0.716(7) 0.816(5) 0.076(13) Uani 0.30(12) 1 d P A 2 O6 O 0.7108(4) 0.8521(5) 0.9106(3) 0.0811(14) Uani 1 1 d . . . C1 C 0.4447(5) 0.7146(6) 0.5934(4) 0.0441(14) Uani 1 1 d . A . C2 C 0.3279(4) 0.7654(5) 0.5946(4) 0.0388(12) Uani 1 1 d . . . C3 C 0.2246(4) 0.6994(5) 0.5920(4) 0.0408(13) Uani 1 1 d . A . H3 H 0.2129 0.6081 0.5909 0.049 Uiso 1 1 calc R . . C4 C 0.1408(4) 0.7986(5) 0.5913(4) 0.0395(12) Uani 1 1 d . . . C5 C 0.1925(5) 0.9216(5) 0.5935(4) 0.0450(14) Uani 1 1 d . A . H5 H 0.1561 1.0032 0.5944 0.054 Uiso 1 1 calc R . . C6 C 0.3907(5) 1.0103(6) 0.5969(5) 0.0677(19) Uani 1 1 d . . . H6A H 0.4096 1.0156 0.5343 0.102 Uiso 1 1 calc R A . H6B H 0.4608 0.9929 0.6484 0.102 Uiso 1 1 calc R . . H6C H 0.3569 1.0927 0.6101 0.102 Uiso 1 1 calc R . . C7 C 0.5853(4) 0.4057(6) 0.6429(4) 0.0429(13) Uani 1 1 d . . . H7 H 0.5232 0.3549 0.6521 0.052 Uiso 1 1 calc R A . C8 C 0.7003(5) 0.3428(5) 0.6501(4) 0.0409(13) Uani 1 1 d . A . C9 C 0.7110(5) 0.2061(6) 0.6586(4) 0.0482(14) Uani 1 1 d . . . H9 H 0.6465 0.1543 0.6606 0.058 Uiso 1 1 calc R A . C10 C 0.8188(5) 0.1470(6) 0.6641(4) 0.0541(15) Uani 1 1 d . A . H10 H 0.8279 0.0554 0.6694 0.065 Uiso 1 1 calc R . . C11 C 0.9113(5) 0.2275(6) 0.6613(4) 0.0552(16) Uani 1 1 d . . . H11 H 0.9847 0.1913 0.6646 0.066 Uiso 1 1 calc R A . C12 C 0.8943(5) 0.3625(6) 0.6537(4) 0.0515(15) Uani 1 1 d . A . H12 H 0.9584 0.4153 0.6520 0.062 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 K1 0.0342(8) 0.0645(9) 0.0651(9) -0.0011(7) 0.0211(6) -0.0009(6) N1 0.027(3) 0.049(3) 0.063(3) 0.012(2) 0.021(2) 0.005(2) N2 0.029(3) 0.052(3) 0.056(3) 0.005(2) 0.016(2) 0.007(2) N3 0.037(3) 0.046(3) 0.057(3) 0.005(2) 0.021(2) -0.001(2) N4 0.033(3) 0.060(3) 0.059(3) 0.013(3) 0.018(2) 0.010(3) N5 0.031(3) 0.059(3) 0.056(3) 0.003(2) 0.015(2) 0.006(2) N6 0.048(4) 0.053(4) 0.065(4) -0.003(3) 0.025(3) -0.004(3) O1 0.034(2) 0.060(3) 0.097(3) 0.012(2) 0.035(2) 0.0021(19) O2 0.039(3) 0.074(3) 0.091(3) 0.005(2) 0.026(2) 0.017(2) O3 0.036(2) 0.068(3) 0.108(4) 0.007(3) 0.022(2) -0.004(2) O4 0.042(11) 0.073(10) 0.111(8) -0.022(8) 0.032(8) 0.010(7) O5 0.07(2) 0.083(6) 0.086(6) 0.018(5) 0.021(7) 0.015(8) O4' 0.07(5) 0.074(13) 0.083(15) 0.012(10) 0.036(19) -0.012(16) O5' 0.06(3) 0.069(19) 0.097(19) 0.010(15) 0.02(2) 0.00(2) O6 0.078(3) 0.106(4) 0.069(3) -0.011(3) 0.036(3) 0.005(3) C1 0.033(3) 0.052(4) 0.050(3) 0.003(3) 0.016(3) 0.002(3) C2 0.031(3) 0.048(3) 0.043(3) 0.003(2) 0.019(2) 0.003(2) C3 0.032(3) 0.046(3) 0.047(3) 0.002(2) 0.015(2) 0.003(2) C4 0.026(3) 0.052(3) 0.044(3) 0.007(3) 0.014(2) 0.004(2) C5 0.036(3) 0.046(3) 0.055(4) 0.004(3) 0.016(3) 0.012(3) C6 0.065(4) 0.048(4) 0.102(5) 0.002(3) 0.044(4) -0.002(3) C7 0.030(3) 0.053(4) 0.048(3) -0.001(3) 0.014(2) 0.002(3) C8 0.037(3) 0.050(3) 0.038(3) 0.001(2) 0.013(2) 0.009(3) C9 0.039(3) 0.057(4) 0.050(3) 0.002(3) 0.014(3) 0.002(3) C10 0.056(4) 0.055(4) 0.053(4) -0.001(3) 0.017(3) 0.013(3) C11 0.044(4) 0.068(4) 0.056(4) 0.005(3) 0.018(3) 0.024(3) C12 0.036(3) 0.065(4) 0.056(4) 0.003(3) 0.016(3) 0.002(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 K1 O6 2.771(5) 4_575 ? K1 O1 2.775(4) . ? K1 O5' 2.83(6) . ? K1 N2 2.840(5) . ? K1 O3 2.878(4) 1_655 ? K1 N5 2.909(5) . ? K1 O4 2.91(3) . ? K1 O2 3.018(4) 1_655 ? K1 O4' 3.02(4) . ? K1 O5 3.17(2) . ? K1 N4 3.328(5) 1_655 ? N1 C1 1.374(7) . ? N1 N2 1.385(5) . ? N1 H1 0.8600 . ? N2 C7 1.273(6) . ? N3 C5 1.348(6) . ? N3 C2 1.398(6) . ? N3 C6 1.480(7) . ? N4 O3 1.229(6) . ? N4 O2 1.233(6) . ? N4 C4 1.424(7) . ? N4 K1 3.328(5) 1_455 ? N5 C12 1.342(7) . ? N5 C8 1.356(7) . ? N6 O4' 1.21(3) . ? N6 O4 1.23(3) . ? N6 O5' 1.24(6) . ? N6 O6 1.239(6) . ? N6 O5 1.262(15) . ? O1 C1 1.217(6) . ? O2 K1 3.018(4) 1_455 ? O3 K1 2.878(4) 1_455 ? O6 K1 2.771(5) 4_576 ? C1 C2 1.475(7) . ? C2 C3 1.382(7) . ? C3 C4 1.405(7) . ? C3 H3 0.9300 . ? C4 C5 1.378(7) . ? C5 H5 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.478(7) . ? C7 H7 0.9300 . ? C8 C9 1.385(7) . ? C9 C10 1.389(8) . ? C9 H9 0.9300 . ? C10 C11 1.369(8) . ? C10 H10 0.9300 . ? C11 C12 1.376(8) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 K1 O1 87.33(14) 4_575 . ? O6 K1 O5' 168(2) 4_575 . ? O1 K1 O5' 89(2) . . ? O6 K1 N2 89.64(14) 4_575 . ? O1 K1 N2 56.97(12) . . ? O5' K1 N2 79(2) . . ? O6 K1 O3 77.47(14) 4_575 1_655 ? O1 K1 O3 161.44(14) . 1_655 ? O5' K1 O3 108(2) . 1_655 ? N2 K1 O3 132.37(13) . 1_655 ? O6 K1 N5 87.55(14) 4_575 . ? O1 K1 N5 114.03(13) . . ? O5' K1 N5 83.5(13) . . ? N2 K1 N5 57.27(13) . . ? O3 K1 N5 76.31(13) 1_655 . ? O6 K1 O4 174.1(6) 4_575 . ? O1 K1 O4 95.7(6) . . ? O5' K1 O4 9.6(18) . . ? N2 K1 O4 87.8(8) . . ? O3 K1 O4 100.4(6) 1_655 . ? N5 K1 O4 86.6(6) . . ? O6 K1 O2 88.15(13) 4_575 1_655 ? O1 K1 O2 127.09(12) . 1_655 ? O5' K1 O2 103(2) . 1_655 ? N2 K1 O2 175.24(13) . 1_655 ? O3 K1 O2 42.95(12) 1_655 1_655 ? N5 K1 O2 118.39(12) . 1_655 ? O4 K1 O2 94.0(8) . 1_655 ? O6 K1 O4' 148.1(14) 4_575 . ? O1 K1 O4' 75(3) . . ? O5' K1 O4' 40.4(13) . . ? N2 K1 O4' 102.5(17) . . ? O3 K1 O4' 113(3) 1_655 . ? N5 K1 O4' 123.9(10) . . ? O4 K1 O4' 37.8(13) . . ? O2 K1 O4' 81.6(18) 1_655 . ? O6 K1 O5 143.0(4) 4_575 . ? O1 K1 O5 62.9(9) . . ? O5' K1 O5 41.8(13) . . ? N2 K1 O5 91.4(11) . . ? O3 K1 O5 125.7(11) 1_655 . ? N5 K1 O5 123.4(5) . . ? O4 K1 O5 42.4(6) . . ? O2 K1 O5 92.9(11) 1_655 . ? O4' K1 O5 13.1(15) . . ? O6 K1 N4 83.32(13) 4_575 1_655 ? O1 K1 N4 147.19(13) . 1_655 ? O5' K1 N4 106(2) . 1_655 ? N2 K1 N4 153.65(13) . 1_655 ? O3 K1 N4 21.30(11) 1_655 1_655 ? N5 K1 N4 96.96(13) . 1_655 ? O4 K1 N4 96.7(8) . 1_655 ? O2 K1 N4 21.70(11) 1_655 1_655 ? O4' K1 N4 97(2) . 1_655 ? O5 K1 N4 109.3(11) . 1_655 ? C1 N1 N2 117.5(4) . . ? C1 N1 H1 121.3 . . ? N2 N1 H1 121.3 . . ? C7 N2 N1 118.0(4) . . ? C7 N2 K1 124.2(3) . . ? N1 N2 K1 117.4(3) . . ? C5 N3 C2 109.4(4) . . ? C5 N3 C6 123.6(5) . . ? C2 N3 C6 126.9(4) . . ? O3 N4 O2 122.9(5) . . ? O3 N4 C4 118.3(5) . . ? O2 N4 C4 118.9(5) . . ? O3 N4 K1 58.3(3) . 1_455 ? O2 N4 K1 64.9(3) . 1_455 ? C4 N4 K1 173.2(3) . 1_455 ? C12 N5 C8 115.9(5) . . ? C12 N5 K1 123.5(4) . . ? C8 N5 K1 120.1(3) . . ? O4' N6 O4 104(4) . . ? O4' N6 O5' 112(3) . . ? O4 N6 O5' 23(4) . . ? O4' N6 O6 129(3) . . ? O4 N6 O6 122.5(14) . . ? O5' N6 O6 119(3) . . ? O4' N6 O5 34(4) . . ? O4 N6 O5 125.0(19) . . ? O5' N6 O5 120(3) . . ? O6 N6 O5 112.0(18) . . ? C1 O1 K1 123.3(3) . . ? N4 O2 K1 93.4(3) . 1_455 ? N4 O3 K1 100.4(3) . 1_455 ? N6 O4 K1 102.2(16) . . ? N6 O5 K1 89.1(11) . . ? N6 O4' K1 97(2) . . ? N6 O5' K1 106(3) . . ? N6 O6 K1 145.7(4) . 4_576 ? O1 C1 N1 122.7(5) . . ? O1 C1 C2 123.5(5) . . ? N1 C1 C2 113.7(5) . . ? C3 C2 N3 108.0(4) . . ? C3 C2 C1 130.9(5) . . ? N3 C2 C1 121.1(5) . . ? C2 C3 C4 105.8(5) . . ? C2 C3 H3 127.1 . . ? C4 C3 H3 127.1 . . ? C5 C4 C3 109.5(5) . . ? C5 C4 N4 124.7(5) . . ? C3 C4 N4 125.8(5) . . ? N3 C5 C4 107.3(4) . . ? N3 C5 H5 126.4 . . ? C4 C5 H5 126.4 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C8 120.4(5) . . ? N2 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? N5 C8 C9 122.8(5) . . ? N5 C8 C7 117.6(5) . . ? C9 C8 C7 119.6(5) . . ? C8 C9 C10 119.6(5) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 118.0(6) . . ? C11 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? C10 C11 C12 119.1(5) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? N5 C12 C11 124.6(5) . . ? N5 C12 H12 117.7 . . ? C11 C12 H12 117.7 . . ? 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 C1 N1 N2 C7 -175.4(5) . . . . ? C1 N1 N2 K1 11.5(5) . . . . ? O6 K1 N2 C7 89.0(4) 4_575 . . . ? O1 K1 N2 C7 176.1(5) . . . . ? O5' K1 N2 C7 -87.9(16) . . . . ? O3 K1 N2 C7 16.4(5) 1_655 . . . ? N5 K1 N2 C7 1.7(4) . . . . ? O4 K1 N2 C7 -85.7(6) . . . . ? O2 K1 N2 C7 26.7(17) 1_655 . . . ? O4' K1 N2 C7 -121(2) . . . . ? O5 K1 N2 C7 -127.9(6) . . . . ? N4 K1 N2 C7 15.0(6) 1_655 . . . ? O6 K1 N2 N1 -98.4(3) 4_575 . . . ? O1 K1 N2 N1 -11.3(3) . . . . ? O5' K1 N2 N1 84.7(16) . . . . ? O3 K1 N2 N1 -171.0(3) 1_655 . . . ? N5 K1 N2 N1 174.3(4) . . . . ? O4 K1 N2 N1 86.9(6) . . . . ? O2 K1 N2 N1 -160.7(14) 1_655 . . . ? O4' K1 N2 N1 52(2) . . . . ? O5 K1 N2 N1 44.7(5) . . . . ? N4 K1 N2 N1 -172.4(3) 1_655 . . . ? O6 K1 N5 C12 83.4(4) 4_575 . . . ? O1 K1 N5 C12 169.4(4) . . . . ? O5' K1 N5 C12 -105(2) . . . . ? N2 K1 N5 C12 174.6(5) . . . . ? O3 K1 N5 C12 5.8(4) 1_655 . . . ? O4 K1 N5 C12 -95.8(8) . . . . ? O2 K1 N5 C12 -3.1(4) 1_655 . . . ? O4' K1 N5 C12 -102(3) . . . . ? O5 K1 N5 C12 -118.2(13) . . . . ? N4 K1 N5 C12 0.5(4) 1_655 . . . ? O6 K1 N5 C8 -88.3(4) 4_575 . . . ? O1 K1 N5 C8 -2.4(4) . . . . ? O5' K1 N5 C8 83(2) . . . . ? N2 K1 N5 C8 2.8(3) . . . . ? O3 K1 N5 C8 -166.0(4) 1_655 . . . ? O4 K1 N5 C8 92.4(8) . . . . ? O2 K1 N5 C8 -174.9(3) 1_655 . . . ? O4' K1 N5 C8 86(3) . . . . ? O5 K1 N5 C8 70.0(13) . . . . ? N4 K1 N5 C8 -171.3(4) 1_655 . . . ? O6 K1 O1 C1 103.9(5) 4_575 . . . ? O5' K1 O1 C1 -64.6(17) . . . . ? N2 K1 O1 C1 12.6(4) . . . . ? O3 K1 O1 C1 138.7(5) 1_655 . . . ? N5 K1 O1 C1 17.7(5) . . . . ? O4 K1 O1 C1 -71.1(9) . . . . ? O2 K1 O1 C1 -170.5(4) 1_655 . . . ? O4' K1 O1 C1 -103.2(7) . . . . ? O5 K1 O1 C1 -98.9(9) . . . . ? N4 K1 O1 C1 177.2(4) 1_655 . . . ? O3 N4 O2 K1 5.7(5) . . . 1_455 ? C4 N4 O2 K1 -173.6(4) . . . 1_455 ? O2 N4 O3 K1 -6.0(6) . . . 1_455 ? C4 N4 O3 K1 173.2(4) . . . 1_455 ? O4' N6 O4 K1 -42(3) . . . . ? O5' N6 O4 K1 72(10) . . . . ? O6 N6 O4 K1 159.4(6) . . . . ? O5 N6 O4 K1 -12.6(16) . . . . ? O6 K1 O4 N6 -153(5) 4_575 . . . ? O1 K1 O4 N6 -32(2) . . . . ? O5' K1 O4 N6 -75(10) . . . . ? N2 K1 O4 N6 -88(2) . . . . ? O3 K1 O4 N6 139(2) 1_655 . . . ? N5 K1 O4 N6 -146(2) . . . . ? O2 K1 O4 N6 96(2) 1_655 . . . ? O4' K1 O4 N6 25(3) . . . . ? O5 K1 O4 N6 6.0(9) . . . . ? N4 K1 O4 N6 118(2) 1_655 . . . ? O4' N6 O5 K1 71(3) . . . . ? O4 N6 O5 K1 11.3(15) . . . . ? O5' N6 O5 K1 -15(4) . . . . ? O6 N6 O5 K1 -161.5(5) . . . . ? O6 K1 O5 N6 170.7(14) 4_575 . . . ? O1 K1 O5 N6 131(3) . . . . ? O5' K1 O5 N6 9(2) . . . . ? N2 K1 O5 N6 79(3) . . . . ? O3 K1 O5 N6 -69(3) 1_655 . . . ? N5 K1 O5 N6 29(4) . . . . ? O4 K1 O5 N6 -5.8(8) . . . . ? O2 K1 O5 N6 -99(3) 1_655 . . . ? O4' K1 O5 N6 -68(4) . . . . ? N4 K1 O5 N6 -84(3) 1_655 . . . ? O4 N6 O4' K1 40(3) . . . . ? O5' N6 O4' K1 17(2) . . . . ? O6 N6 O4' K1 -163.9(16) . . . . ? O5 N6 O4' K1 -94(4) . . . . ? O6 K1 O4' N6 154(3) 4_575 . . . ? O1 K1 O4' N6 95(7) . . . . ? O5' K1 O4' N6 -10.7(16) . . . . ? N2 K1 O4' N6 44(7) . . . . ? O3 K1 O4' N6 -103(7) 1_655 . . . ? N5 K1 O4' N6 -14(9) . . . . ? O4 K1 O4' N6 -25(3) . . . . ? O2 K1 O4' N6 -133(7) 1_655 . . . ? O5 K1 O4' N6 78(4) . . . . ? N4 K1 O4' N6 -118(7) 1_655 . . . ? O4' N6 O5' K1 -19(3) . . . . ? O4 N6 O5' K1 -92(10) . . . . ? O6 N6 O5' K1 161.9(13) . . . . ? O5 N6 O5' K1 18(4) . . . . ? O6 K1 O5' N6 -129(5) 4_575 . . . ? O1 K1 O5' N6 -58(6) . . . . ? N2 K1 O5' N6 -114(7) . . . . ? O3 K1 O5' N6 114(6) 1_655 . . . ? N5 K1 O5' N6 -172(7) . . . . ? O4 K1 O5' N6 79(10) . . . . ? O2 K1 O5' N6 70(7) 1_655 . . . ? O4' K1 O5' N6 10.8(15) . . . . ? O5 K1 O5' N6 -9(2) . . . . ? N4 K1 O5' N6 92(6) 1_655 . . . ? O4' N6 O6 K1 -139(8) . . . 4_576 ? O4 N6 O6 K1 13(3) . . . 4_576 ? O5' N6 O6 K1 39(6) . . . 4_576 ? O5 N6 O6 K1 -174(3) . . . 4_576 ? K1 O1 C1 N1 -12.8(7) . . . . ? K1 O1 C1 C2 165.6(4) . . . . ? N2 N1 C1 O1 0.1(8) . . . . ? N2 N1 C1 C2 -178.4(4) . . . . ? C5 N3 C2 C3 1.5(6) . . . . ? C6 N3 C2 C3 179.4(5) . . . . ? C5 N3 C2 C1 178.9(5) . . . . ? C6 N3 C2 C1 -3.2(8) . . . . ? O1 C1 C2 C3 161.7(6) . . . . ? N1 C1 C2 C3 -19.8(8) . . . . ? O1 C1 C2 N3 -15.1(8) . . . . ? N1 C1 C2 N3 163.4(5) . . . . ? N3 C2 C3 C4 -0.9(6) . . . . ? C1 C2 C3 C4 -178.0(5) . . . . ? C2 C3 C4 C5 0.0(6) . . . . ? C2 C3 C4 N4 -179.4(5) . . . . ? O3 N4 C4 C5 179.9(5) . . . . ? O2 N4 C4 C5 -0.9(8) . . . . ? K1 N4 C4 C5 -122(3) 1_455 . . . ? O3 N4 C4 C3 -0.8(8) . . . . ? O2 N4 C4 C3 178.4(5) . . . . ? K1 N4 C4 C3 57(3) 1_455 . . . ? C2 N3 C5 C4 -1.5(6) . . . . ? C6 N3 C5 C4 -179.4(5) . . . . ? C3 C4 C5 N3 0.9(6) . . . . ? N4 C4 C5 N3 -179.7(5) . . . . ? N1 N2 C7 C8 -178.3(4) . . . . ? K1 N2 C7 C8 -5.7(7) . . . . ? C12 N5 C8 C9 1.4(7) . . . . ? K1 N5 C8 C9 173.8(4) . . . . ? C12 N5 C8 C7 -178.9(4) . . . . ? K1 N5 C8 C7 -6.5(6) . . . . ? N2 C7 C8 N5 8.2(7) . . . . ? N2 C7 C8 C9 -172.2(5) . . . . ? N5 C8 C9 C10 -1.2(8) . . . . ? C7 C8 C9 C10 179.1(5) . . . . ? C8 C9 C10 C11 0.3(8) . . . . ? C9 C10 C11 C12 0.2(8) . . . . ? C8 N5 C12 C11 -0.8(8) . . . . ? K1 N5 C12 C11 -172.9(4) . . . . ? C10 C11 C12 N5 0.0(9) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.667 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.075