# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Xiao-Jun Zhao' _publ_contact_author_email 'XIAOJUN ZHAO15@YAHOO.COM.CN' _publ_section_title ; Diverse mixed-ligand metal complexes with in situ generated 5-(pyrazinyl)tetrazolate chelating-bridging ligand: in situ synthesis, crystal structures, magnetic, and luminescent properties ; loop_ _publ_author_name 'Xiao-Jun Zhao' 'Yan Feng' 'Zhong-Yi Liu' 'Tian-Yu Liu' 'En-Cui Yang' # Attachment '1-9.cif' data_81129a _database_code_depnum_ccdc_archive 'CCDC 756331' #TrackingRef '1-9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 Co3 N12 O17' _chemical_formula_weight 883.32 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' Co Co 0.3494 0.9721 '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 8.2152(4) _cell_length_b 8.9387(4) _cell_length_c 12.3961(5) _cell_angle_alpha 109.8460(10) _cell_angle_beta 92.6510(10) _cell_angle_gamma 106.7250(10) _cell_volume 809.46(6) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3544 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 27.91 _exptl_crystal_description BLOCK _exptl_crystal_colour ORANGE _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.812 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 447 _exptl_absorpt_coefficient_mu 1.614 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6980 _exptl_absorpt_correction_T_max 0.7178 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 4127 _diffrn_reflns_av_R_equivalents 0.0107 _diffrn_reflns_av_sigmaI/netI 0.0205 _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 -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2823 _reflns_number_gt 2569 _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^)+(0.0306P)^2^+1.3841P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2823 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0743 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 Co1 Co 0.5000 0.5000 0.5000 0.01491(13) Uani 1 2 d S . . Co2 Co -0.03208(4) 0.94415(4) 0.82077(3) 0.01777(11) Uani 1 1 d . . . O1 O 0.3440(4) 0.3065(3) 0.7148(3) 0.0666(9) Uani 1 1 d . . . O2 O 0.5482(2) 0.4415(2) 0.64035(14) 0.0199(4) Uani 1 1 d . . . O3 O 0.2935(2) 0.2821(2) 0.42942(15) 0.0215(4) Uani 1 1 d . . . O4 O 0.1617(2) 0.0193(2) 0.31100(15) 0.0234(4) Uani 1 1 d . . . O5 O -0.2009(3) 0.7123(2) 0.80401(17) 0.0358(5) Uani 1 1 d . . . H5A H -0.2654 0.6411 0.7413 0.054 Uiso 1 1 d R . . H5B H -0.2217 0.6961 0.8663 0.054 Uiso 1 1 d R . . O6 O 0.1558(3) 1.1700(3) 0.84673(19) 0.0401(5) Uani 1 1 d . . . H6A H 0.2004 1.1843 0.7890 0.060 Uiso 1 1 d R . . H6B H 0.2198 1.2191 0.9128 0.060 Uiso 1 1 d R . . N1 N 0.1340(3) 0.9088(3) 0.94194(17) 0.0192(4) Uani 1 1 d . . . N2 N 0.1666(3) 0.9365(3) 1.05488(18) 0.0217(5) Uani 1 1 d . . . N3 N 0.2904(3) 0.8778(3) 1.0732(2) 0.0346(6) Uani 1 1 d . . . N4 N 0.3400(3) 0.8094(3) 0.9715(2) 0.0338(6) Uani 1 1 d . . . N5 N 0.1209(3) 0.8084(3) 0.70896(19) 0.0246(5) Uani 1 1 d . . . N6 N 0.3280(3) 0.6296(3) 0.59386(18) 0.0198(4) Uani 1 1 d . . . C1 C 0.2416(3) 0.8301(3) 0.8932(2) 0.0210(5) Uani 1 1 d . . . C2 C 0.2377(3) 0.7732(3) 0.7675(2) 0.0215(5) Uani 1 1 d . . . C3 C 0.1082(4) 0.7532(4) 0.5938(2) 0.0276(6) Uani 1 1 d . . . H3 H 0.0290 0.7760 0.5510 0.033 Uiso 1 1 calc R . . C4 C 0.2101(3) 0.6626(3) 0.5362(2) 0.0233(5) Uani 1 1 d . . . H4 H 0.1960 0.6239 0.4556 0.028 Uiso 1 1 calc R . . C5 C 0.3415(3) 0.6852(3) 0.7096(2) 0.0220(5) Uani 1 1 d . . . H5 H 0.4227 0.6645 0.7523 0.026 Uiso 1 1 calc R . . C6 C 0.4669(3) 0.1453(3) 0.5688(2) 0.0173(5) Uani 1 1 d . . . C7 C 0.3920(3) 0.0649(3) 0.4514(2) 0.0173(5) Uani 1 1 d . . . C8 C 0.5730(3) 0.0794(3) 0.6158(2) 0.0185(5) Uani 1 1 d . . . H8 H 0.6219 0.1328 0.6938 0.022 Uiso 1 1 calc R . . C9 C 0.4483(3) 0.3083(3) 0.6472(2) 0.0218(5) Uani 1 1 d . . . C10 C 0.2750(3) 0.1279(3) 0.3938(2) 0.0169(5) Uani 1 1 d . . . O7 O -0.0092(5) 0.3251(5) 0.6876(4) 0.1052(14) Uani 1 1 d . . . H7A H -0.0650 0.2323 0.6927 0.158 Uiso 1 1 d R . . H7B H 0.0980 0.3644 0.7139 0.158 Uiso 1 1 d R . . O8 O 0.4186(4) 0.3558(4) 0.0304(2) 0.0759(10) Uani 1 1 d . . . H8A H 0.4630 0.2775 0.0148 0.114 Uiso 1 1 d R . . H8B H 0.4875 0.4561 0.0578 0.114 Uiso 1 1 d R . . O9 O 0.9036(11) 0.5005(8) 0.8955(8) 0.101(2) Uani 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0178(2) 0.0154(2) 0.0136(2) 0.00507(18) 0.00420(17) 0.00852(18) Co2 0.01884(19) 0.0238(2) 0.01455(19) 0.00705(14) 0.00442(13) 0.01228(14) O1 0.102(2) 0.0414(14) 0.083(2) 0.0347(14) 0.0776(19) 0.0383(15) O2 0.0264(9) 0.0169(9) 0.0166(9) 0.0060(7) 0.0019(7) 0.0076(7) O3 0.0198(9) 0.0175(9) 0.0281(10) 0.0082(8) -0.0007(7) 0.0084(7) O4 0.0270(10) 0.0210(9) 0.0216(9) 0.0065(8) -0.0042(8) 0.0098(8) O5 0.0394(12) 0.0321(11) 0.0227(10) 0.0058(9) -0.0040(9) -0.0009(9) O6 0.0370(12) 0.0460(13) 0.0313(11) 0.0211(10) 0.0017(9) -0.0031(10) N1 0.0218(11) 0.0245(11) 0.0152(10) 0.0071(9) 0.0054(8) 0.0132(9) N2 0.0242(11) 0.0304(12) 0.0153(10) 0.0079(9) 0.0047(8) 0.0161(10) N3 0.0407(14) 0.0562(16) 0.0204(12) 0.0133(12) 0.0080(10) 0.0360(13) N4 0.0397(14) 0.0545(16) 0.0200(12) 0.0121(11) 0.0089(10) 0.0352(13) N5 0.0244(11) 0.0353(13) 0.0206(11) 0.0098(10) 0.0072(9) 0.0190(10) N6 0.0211(11) 0.0212(11) 0.0195(11) 0.0069(9) 0.0070(8) 0.0105(9) C1 0.0223(13) 0.0268(13) 0.0189(13) 0.0081(11) 0.0052(10) 0.0155(11) C2 0.0220(13) 0.0251(13) 0.0201(13) 0.0076(11) 0.0057(10) 0.0122(11) C3 0.0273(14) 0.0441(17) 0.0190(13) 0.0114(12) 0.0048(11) 0.0225(13) C4 0.0226(13) 0.0309(14) 0.0171(13) 0.0068(11) 0.0052(10) 0.0122(11) C5 0.0251(13) 0.0277(14) 0.0195(13) 0.0091(11) 0.0064(10) 0.0168(11) C6 0.0170(12) 0.0158(12) 0.0209(12) 0.0082(10) 0.0052(10) 0.0059(10) C7 0.0169(12) 0.0165(12) 0.0212(13) 0.0097(10) 0.0033(10) 0.0061(10) C8 0.0201(12) 0.0183(12) 0.0166(12) 0.0065(10) -0.0001(10) 0.0056(10) C9 0.0282(14) 0.0236(13) 0.0213(13) 0.0118(11) 0.0092(11) 0.0146(11) C10 0.0167(12) 0.0203(12) 0.0171(12) 0.0085(10) 0.0053(10) 0.0084(10) O7 0.071(2) 0.122(3) 0.136(3) 0.086(3) -0.014(2) 0.011(2) O8 0.077(2) 0.094(2) 0.0576(18) 0.0004(16) -0.0099(15) 0.0656(19) O9 0.123(6) 0.059(4) 0.126(7) 0.038(4) 0.029(5) 0.029(4) _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 Co1 O2 2.0321(16) . ? Co1 O2 2.0321(16) 2_666 ? Co1 O3 2.0594(17) . ? Co1 O3 2.0595(17) 2_666 ? Co1 N6 2.207(2) . ? Co1 N6 2.207(2) 2_666 ? Co2 O6 2.069(2) . ? Co2 O5 2.071(2) . ? Co2 O4 2.0762(17) 2_566 ? Co2 N2 2.110(2) 2_577 ? Co2 N1 2.145(2) . ? Co2 N5 2.207(2) . ? O1 C9 1.226(3) . ? O2 C9 1.269(3) . ? O3 C10 1.256(3) . ? O4 C10 1.256(3) . ? O4 Co2 2.0761(17) 2_566 ? O5 H5A 0.8499 . ? O5 H5B 0.8492 . ? O6 H6A 0.8501 . ? O6 H6B 0.8501 . ? N1 C1 1.327(3) . ? N1 N2 1.336(3) . ? N2 N3 1.315(3) . ? N2 Co2 2.110(2) 2_577 ? N3 N4 1.341(3) . ? N4 C1 1.328(3) . ? N5 C3 1.330(3) . ? N5 C2 1.346(3) . ? N6 C4 1.334(3) . ? N6 C5 1.336(3) . ? C1 C2 1.462(4) . ? C2 C5 1.385(4) . ? C3 C4 1.386(4) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C8 1.389(3) . ? C6 C7 1.401(3) . ? C6 C9 1.508(3) . ? C7 C8 1.395(3) 2_656 ? C7 C10 1.508(3) . ? C8 C7 1.395(3) 2_656 ? C8 H8 0.9300 . ? O7 H7A 0.8501 . ? O7 H7B 0.8504 . ? O8 H8A 0.8502 . ? O8 H8B 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Co1 O2 180.0 . 2_666 ? O2 Co1 O3 90.84(7) . . ? O2 Co1 O3 89.16(7) 2_666 . ? O2 Co1 O3 89.16(7) . 2_666 ? O2 Co1 O3 90.83(7) 2_666 2_666 ? O3 Co1 O3 180.0 . 2_666 ? O2 Co1 N6 88.33(7) . . ? O2 Co1 N6 91.67(7) 2_666 . ? O3 Co1 N6 89.45(7) . . ? O3 Co1 N6 90.55(7) 2_666 . ? O2 Co1 N6 91.67(7) . 2_666 ? O2 Co1 N6 88.33(7) 2_666 2_666 ? O3 Co1 N6 90.55(7) . 2_666 ? O3 Co1 N6 89.44(7) 2_666 2_666 ? N6 Co1 N6 180.0 . 2_666 ? O6 Co2 O5 173.97(9) . . ? O6 Co2 O4 87.59(8) . 2_566 ? O5 Co2 O4 98.11(8) . 2_566 ? O6 Co2 N2 92.02(9) . 2_577 ? O5 Co2 N2 89.78(9) . 2_577 ? O4 Co2 N2 91.96(8) 2_566 2_577 ? O6 Co2 N1 87.73(8) . . ? O5 Co2 N1 86.36(8) . . ? O4 Co2 N1 171.17(8) 2_566 . ? N2 Co2 N1 95.68(8) 2_577 . ? O6 Co2 N5 89.81(9) . . ? O5 Co2 N5 87.66(9) . . ? O4 Co2 N5 95.68(8) 2_566 . ? N2 Co2 N5 172.22(8) 2_577 . ? N1 Co2 N5 76.83(8) . . ? C9 O2 Co1 118.75(16) . . ? C10 O3 Co1 135.00(16) . . ? C10 O4 Co2 127.69(16) . 2_566 ? Co2 O5 H5A 124.6 . . ? Co2 O5 H5B 117.0 . . ? H5A O5 H5B 117.2 . . ? Co2 O6 H6A 118.7 . . ? Co2 O6 H6B 116.5 . . ? H6A O6 H6B 117.0 . . ? C1 N1 N2 105.0(2) . . ? C1 N1 Co2 113.82(16) . . ? N2 N1 Co2 141.20(16) . . ? N3 N2 N1 109.6(2) . . ? N3 N2 Co2 127.29(17) . 2_577 ? N1 N2 Co2 123.12(15) . 2_577 ? N2 N3 N4 108.8(2) . . ? C1 N4 N3 105.2(2) . . ? C3 N5 C2 117.2(2) . . ? C3 N5 Co2 128.90(18) . . ? C2 N5 Co2 113.88(17) . . ? C4 N6 C5 117.0(2) . . ? C4 N6 Co1 120.45(17) . . ? C5 N6 Co1 122.43(16) . . ? N1 C1 N4 111.5(2) . . ? N1 C1 C2 120.4(2) . . ? N4 C1 C2 128.1(2) . . ? N5 C2 C5 121.0(2) . . ? N5 C2 C1 115.1(2) . . ? C5 C2 C1 123.9(2) . . ? N5 C3 C4 121.6(2) . . ? N5 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? N6 C4 C3 121.5(2) . . ? N6 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? N6 C5 C2 121.7(2) . . ? N6 C5 H5 119.2 . . ? C2 C5 H5 119.2 . . ? C8 C6 C7 119.5(2) . . ? C8 C6 C9 116.8(2) . . ? C7 C6 C9 123.5(2) . . ? C8 C7 C6 119.0(2) 2_656 . ? C8 C7 C10 118.1(2) 2_656 . ? C6 C7 C10 122.8(2) . . ? C6 C8 C7 121.5(2) . 2_656 ? C6 C8 H8 119.3 . . ? C7 C8 H8 119.3 2_656 . ? O1 C9 O2 124.0(2) . . ? O1 C9 C6 119.7(2) . . ? O2 C9 C6 116.3(2) . . ? O4 C10 O3 123.5(2) . . ? O4 C10 C7 116.6(2) . . ? O3 C10 C7 119.9(2) . . ? H7A O7 H7B 117.0 . . ? H8A O8 H8B 117.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Co1 O2 C9 -162(4) 2_666 . . . ? O3 Co1 O2 C9 -2.15(18) . . . . ? O3 Co1 O2 C9 177.86(18) 2_666 . . . ? N6 Co1 O2 C9 87.28(18) . . . . ? N6 Co1 O2 C9 -92.72(18) 2_666 . . . ? O2 Co1 O3 C10 -63.4(2) . . . . ? O2 Co1 O3 C10 116.6(2) 2_666 . . . ? O3 Co1 O3 C10 59(15) 2_666 . . . ? N6 Co1 O3 C10 -151.7(2) . . . . ? N6 Co1 O3 C10 28.3(2) 2_666 . . . ? O6 Co2 N1 C1 -89.43(19) . . . . ? O5 Co2 N1 C1 89.35(19) . . . . ? O4 Co2 N1 C1 -31.5(6) 2_566 . . . ? N2 Co2 N1 C1 178.76(18) 2_577 . . . ? N5 Co2 N1 C1 0.91(18) . . . . ? O6 Co2 N1 N2 92.6(3) . . . . ? O5 Co2 N1 N2 -88.6(3) . . . . ? O4 Co2 N1 N2 150.5(4) 2_566 . . . ? N2 Co2 N1 N2 0.8(3) 2_577 . . . ? N5 Co2 N1 N2 -177.1(3) . . . . ? C1 N1 N2 N3 0.5(3) . . . . ? Co2 N1 N2 N3 178.6(2) . . . . ? C1 N1 N2 Co2 -179.01(17) . . . 2_577 ? Co2 N1 N2 Co2 -0.9(4) . . . 2_577 ? N1 N2 N3 N4 -0.4(3) . . . . ? Co2 N2 N3 N4 179.13(19) 2_577 . . . ? N2 N3 N4 C1 0.1(3) . . . . ? O6 Co2 N5 C3 -95.5(3) . . . . ? O5 Co2 N5 C3 89.9(3) . . . . ? O4 Co2 N5 C3 -8.0(3) 2_566 . . . ? N2 Co2 N5 C3 160.8(6) 2_577 . . . ? N1 Co2 N5 C3 176.8(3) . . . . ? O6 Co2 N5 C2 87.12(19) . . . . ? O5 Co2 N5 C2 -87.40(19) . . . . ? O4 Co2 N5 C2 174.67(19) 2_566 . . . ? N2 Co2 N5 C2 -16.5(7) 2_577 . . . ? N1 Co2 N5 C2 -0.59(18) . . . . ? O2 Co1 N6 C4 -161.1(2) . . . . ? O2 Co1 N6 C4 18.9(2) 2_666 . . . ? O3 Co1 N6 C4 -70.2(2) . . . . ? O3 Co1 N6 C4 109.8(2) 2_666 . . . ? N6 Co1 N6 C4 73(13) 2_666 . . . ? O2 Co1 N6 C5 22.2(2) . . . . ? O2 Co1 N6 C5 -157.8(2) 2_666 . . . ? O3 Co1 N6 C5 113.0(2) . . . . ? O3 Co1 N6 C5 -67.0(2) 2_666 . . . ? N6 Co1 N6 C5 -104(13) 2_666 . . . ? N2 N1 C1 N4 -0.5(3) . . . . ? Co2 N1 C1 N4 -179.20(19) . . . . ? N2 N1 C1 C2 177.6(2) . . . . ? Co2 N1 C1 C2 -1.1(3) . . . . ? N3 N4 C1 N1 0.3(3) . . . . ? N3 N4 C1 C2 -177.6(3) . . . . ? C3 N5 C2 C5 0.9(4) . . . . ? Co2 N5 C2 C5 178.6(2) . . . . ? C3 N5 C2 C1 -177.5(2) . . . . ? Co2 N5 C2 C1 0.2(3) . . . . ? N1 C1 C2 N5 0.6(4) . . . . ? N4 C1 C2 N5 178.3(3) . . . . ? N1 C1 C2 C5 -177.7(2) . . . . ? N4 C1 C2 C5 0.0(5) . . . . ? C2 N5 C3 C4 0.3(4) . . . . ? Co2 N5 C3 C4 -177.0(2) . . . . ? C5 N6 C4 C3 1.1(4) . . . . ? Co1 N6 C4 C3 -175.8(2) . . . . ? N5 C3 C4 N6 -1.4(4) . . . . ? C4 N6 C5 C2 0.1(4) . . . . ? Co1 N6 C5 C2 176.98(19) . . . . ? N5 C2 C5 N6 -1.2(4) . . . . ? C1 C2 C5 N6 177.1(2) . . . . ? C8 C6 C7 C8 -0.4(4) . . . 2_656 ? C9 C6 C7 C8 175.5(2) . . . 2_656 ? C8 C6 C7 C10 179.9(2) . . . . ? C9 C6 C7 C10 -4.2(4) . . . . ? C7 C6 C8 C7 0.4(4) . . . 2_656 ? C9 C6 C8 C7 -175.8(2) . . . 2_656 ? Co1 O2 C9 O1 -107.4(3) . . . . ? Co1 O2 C9 C6 74.6(2) . . . . ? C8 C6 C9 O1 -83.4(3) . . . . ? C7 C6 C9 O1 100.6(3) . . . . ? C8 C6 C9 O2 94.6(3) . . . . ? C7 C6 C9 O2 -81.4(3) . . . . ? Co2 O4 C10 O3 21.4(3) 2_566 . . . ? Co2 O4 C10 C7 -158.78(16) 2_566 . . . ? Co1 O3 C10 O4 -147.0(2) . . . . ? Co1 O3 C10 C7 33.3(3) . . . . ? C8 C7 C10 O4 29.8(3) 2_656 . . . ? C6 C7 C10 O4 -150.4(2) . . . . ? C8 C7 C10 O3 -150.4(2) 2_656 . . . ? C6 C7 C10 O3 29.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.447 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.066 #END data_90324b _database_code_depnum_ccdc_archive 'CCDC 756332' #TrackingRef '1-9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H9 Cu N6 O6' _chemical_formula_weight 372.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8365(10) _cell_length_b 8.2326(11) _cell_length_c 10.7944(15) _cell_angle_alpha 111.154(2) _cell_angle_beta 95.728(2) _cell_angle_gamma 94.674(2) _cell_volume 641.03(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2107 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.931 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 1.751 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7434 _exptl_absorpt_correction_T_max 0.8043 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 3195 _diffrn_reflns_av_R_equivalents 0.0111 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2235 _reflns_number_gt 1934 _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^)+(0.0285P)^2^+1.0776P] 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 2235 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Cu1 Cu 0.58265(5) 0.83661(5) 0.83242(4) 0.02951(14) Uani 1 1 d . . . O6 O 0.8227(5) 0.7398(10) 0.9722(5) 0.0523(14) Uani 0.765(12) 1 d P A 1 O6' O 0.836(2) 0.836(3) 1.0044(17) 0.0523(14) Uani 0.235(12) 1 d P A 2 O1 O 0.7108(3) 0.8447(3) 0.6904(2) 0.0307(5) Uani 1 1 d . A . O2 O 0.9814(3) 0.8035(3) 0.7516(2) 0.0318(5) Uani 1 1 d . A . O3 O 0.8366(3) 0.5474(3) 0.4541(2) 0.0308(5) Uani 1 1 d . . . O4 O 1.0208(3) 0.5423(3) 0.3065(2) 0.0332(5) Uani 1 1 d . . . H4' H 1.0100 0.4366 0.2911 0.050 Uiso 1 1 calc R . . O5 O 0.3430(3) 0.8726(3) 0.7053(2) 0.0411(6) Uani 1 1 d . A . H5A H 0.3660 0.9536 0.6759 0.062 Uiso 1 1 d R . . H5B H 0.2442 0.8641 0.7300 0.062 Uiso 1 1 d R . . N1 N 0.4280(3) 0.8081(3) 0.9621(2) 0.0292(6) Uani 1 1 d . A . N2 N 0.3537(3) 0.9044(3) 1.0670(3) 0.0322(6) Uani 1 1 d . . . N3 N 0.2475(4) 0.7981(4) 1.1000(3) 0.0412(7) Uani 1 1 d . A . N4 N 0.2501(4) 0.6321(4) 1.0170(3) 0.0392(7) Uani 1 1 d . . . N5 N 0.5211(3) 0.5679(3) 0.7530(3) 0.0288(6) Uani 1 1 d . A . N6 N 0.4250(4) 0.2090(3) 0.6815(3) 0.0360(6) Uani 1 1 d . . . C1 C 0.3622(4) 0.6439(4) 0.9348(3) 0.0282(7) Uani 1 1 d . A . C2 C 0.4169(4) 0.5050(4) 0.8228(3) 0.0275(7) Uani 1 1 d . . . C3 C 0.3711(4) 0.3278(4) 0.7871(3) 0.0331(7) Uani 1 1 d . A . H3 H 0.3003 0.2891 0.8377 0.040 Uiso 1 1 calc R . . C4 C 0.5247(4) 0.2724(5) 0.6124(4) 0.0380(8) Uani 1 1 d . A . H4 H 0.5633 0.1939 0.5377 0.046 Uiso 1 1 calc R . . C5 C 0.5734(4) 0.4507(4) 0.6470(3) 0.0325(7) Uani 1 1 d . . . H5 H 0.6433 0.4886 0.5955 0.039 Uiso 1 1 calc R A . C6 C 0.8702(4) 0.8469(3) 0.6821(3) 0.0233(6) Uani 1 1 d . . . C7 C 0.9318(4) 0.9211(4) 0.5829(3) 0.0216(6) Uani 1 1 d . A . C8 C 0.9749(4) 0.8179(4) 0.4581(3) 0.0226(6) Uani 1 1 d . . . C9 C 0.9372(4) 0.6229(4) 0.4085(3) 0.0241(6) Uani 1 1 d . A . C10 C 0.9566(4) 1.1021(4) 0.6231(3) 0.0240(6) Uani 1 1 d . . . H10 H 0.9272 1.1713 0.7055 0.029 Uiso 1 1 calc R A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0303(2) 0.0317(2) 0.0280(2) 0.01137(16) 0.01445(16) -0.00167(16) O6 0.0420(18) 0.066(4) 0.053(3) 0.027(3) 0.0099(17) 0.005(3) O6' 0.0420(18) 0.066(4) 0.053(3) 0.027(3) 0.0099(17) 0.005(3) O1 0.0293(12) 0.0355(12) 0.0296(11) 0.0136(10) 0.0134(9) -0.0006(9) O2 0.0366(13) 0.0316(12) 0.0330(12) 0.0179(10) 0.0078(10) 0.0056(10) O3 0.0332(12) 0.0245(11) 0.0381(12) 0.0139(10) 0.0141(10) 0.0006(9) O4 0.0483(14) 0.0212(11) 0.0339(12) 0.0102(10) 0.0200(10) 0.0081(10) O5 0.0310(13) 0.0446(14) 0.0559(15) 0.0289(12) 0.0059(11) 0.0020(10) N1 0.0281(14) 0.0347(14) 0.0246(13) 0.0106(11) 0.0095(11) -0.0013(11) N2 0.0300(15) 0.0392(15) 0.0262(14) 0.0101(12) 0.0126(11) -0.0023(12) N3 0.0410(17) 0.0427(17) 0.0350(16) 0.0086(13) 0.0179(13) -0.0106(13) N4 0.0408(17) 0.0399(16) 0.0337(15) 0.0100(13) 0.0164(13) -0.0083(13) N5 0.0259(14) 0.0344(14) 0.0302(14) 0.0160(12) 0.0084(11) 0.0026(11) N6 0.0379(16) 0.0314(15) 0.0405(16) 0.0156(13) 0.0059(13) 0.0035(12) C1 0.0270(16) 0.0359(17) 0.0234(15) 0.0140(13) 0.0049(13) -0.0015(13) C2 0.0234(15) 0.0366(17) 0.0261(15) 0.0171(13) 0.0028(12) -0.0004(13) C3 0.0323(18) 0.0386(19) 0.0325(17) 0.0192(15) 0.0046(14) -0.0016(14) C4 0.0370(19) 0.0403(19) 0.0398(19) 0.0160(16) 0.0122(15) 0.0079(15) C5 0.0305(17) 0.0372(18) 0.0353(18) 0.0176(15) 0.0125(14) 0.0064(14) C6 0.0309(17) 0.0161(14) 0.0208(14) 0.0034(11) 0.0104(13) -0.0002(12) C7 0.0192(14) 0.0244(15) 0.0239(15) 0.0112(12) 0.0070(12) 0.0023(11) C8 0.0234(15) 0.0199(14) 0.0260(15) 0.0093(12) 0.0074(12) 0.0028(12) C9 0.0249(15) 0.0256(15) 0.0229(15) 0.0100(12) 0.0045(12) 0.0042(12) C10 0.0266(15) 0.0237(15) 0.0231(15) 0.0081(12) 0.0105(12) 0.0047(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.932(2) . ? Cu1 N1 2.003(2) . ? Cu1 N2 2.005(3) 2_677 ? Cu1 N5 2.058(3) . ? Cu1 O5 2.316(2) . ? Cu1 O6' 2.578(16) . ? Cu1 O6 2.645(4) . ? O1 C6 1.261(4) . ? O2 C6 1.251(4) . ? O3 C9 1.211(3) . ? O4 C9 1.330(3) . ? O4 H4' 0.8200 . ? O5 H5A 0.8500 . ? O5 H5B 0.8497 . ? N1 C1 1.323(4) . ? N1 N2 1.345(3) . ? N2 N3 1.323(4) . ? N2 Cu1 2.005(3) 2_677 ? N3 N4 1.340(4) . ? N4 C1 1.332(4) . ? N5 C5 1.331(4) . ? N5 C2 1.356(4) . ? N6 C4 1.330(4) . ? N6 C3 1.339(4) . ? C1 C2 1.462(4) . ? C2 C3 1.373(4) . ? C3 H3 0.9300 . ? C4 C5 1.387(5) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.509(4) . ? C7 C10 1.384(4) . ? C7 C8 1.401(4) . ? C8 C10 1.394(4) 2_776 ? C8 C9 1.490(4) . ? C10 C8 1.394(4) 2_776 ? C10 H10 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 O1 Cu1 N1 173.06(10) . . ? O1 Cu1 N2 91.15(9) . 2_677 ? N1 Cu1 N2 94.11(10) . 2_677 ? O1 Cu1 N5 94.70(9) . . ? N1 Cu1 N5 80.44(10) . . ? N2 Cu1 N5 172.59(10) 2_677 . ? O1 Cu1 O5 86.52(9) . . ? N1 Cu1 O5 88.65(10) . . ? N2 Cu1 O5 93.33(10) 2_677 . ? N5 Cu1 O5 91.56(9) . . ? O1 Cu1 O6' 99.2(4) . . ? N1 Cu1 O6' 86.2(4) . . ? N2 Cu1 O6' 79.8(5) 2_677 . ? N5 Cu1 O6' 94.8(5) . . ? O5 Cu1 O6' 171.1(4) . . ? O1 Cu1 O6 98.61(11) . . ? N1 Cu1 O6 85.36(12) . . ? N2 Cu1 O6 95.88(18) 2_677 . ? N5 Cu1 O6 78.76(17) . . ? O5 Cu1 O6 169.34(16) . . ? O6' Cu1 O6 16.1(4) . . ? C6 O1 Cu1 131.0(2) . . ? C9 O4 H4' 109.5 . . ? Cu1 O5 H5A 111.5 . . ? Cu1 O5 H5B 119.1 . . ? H5A O5 H5B 117.1 . . ? C1 N1 N2 104.9(2) . . ? C1 N1 Cu1 114.1(2) . . ? N2 N1 Cu1 140.7(2) . . ? N3 N2 N1 108.9(2) . . ? N3 N2 Cu1 126.3(2) . 2_677 ? N1 N2 Cu1 124.38(19) . 2_677 ? N2 N3 N4 109.3(2) . . ? C1 N4 N3 104.6(3) . . ? C5 N5 C2 117.0(3) . . ? C5 N5 Cu1 129.0(2) . . ? C2 N5 Cu1 114.0(2) . . ? C4 N6 C3 116.1(3) . . ? N1 C1 N4 112.2(3) . . ? N1 C1 C2 118.4(3) . . ? N4 C1 C2 129.4(3) . . ? N5 C2 C3 121.3(3) . . ? N5 C2 C1 112.9(3) . . ? C3 C2 C1 125.9(3) . . ? N6 C3 C2 122.0(3) . . ? N6 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? N6 C4 C5 122.9(3) . . ? N6 C4 H4 118.6 . . ? C5 C4 H4 118.6 . . ? N5 C5 C4 120.7(3) . . ? N5 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? O2 C6 O1 127.0(3) . . ? O2 C6 C7 117.7(3) . . ? O1 C6 C7 115.3(3) . . ? C10 C7 C8 119.1(3) . . ? C10 C7 C6 117.0(2) . . ? C8 C7 C6 123.7(2) . . ? C10 C8 C7 119.9(3) 2_776 . ? C10 C8 C9 120.0(2) 2_776 . ? C7 C8 C9 119.9(3) . . ? O3 C9 O4 124.1(3) . . ? O3 C9 C8 123.1(3) . . ? O4 C9 C8 112.8(2) . . ? C7 C10 C8 120.9(3) . 2_776 ? C7 C10 H10 119.5 . . ? C8 C10 H10 119.5 2_776 . ? 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 Cu1 O1 C6 -140.1(8) . . . . ? N2 Cu1 O1 C6 80.6(3) 2_677 . . . ? N5 Cu1 O1 C6 -94.8(3) . . . . ? O5 Cu1 O1 C6 173.9(3) . . . . ? O6' Cu1 O1 C6 0.8(6) . . . . ? O6 Cu1 O1 C6 -15.5(3) . . . . ? O1 Cu1 N1 C1 44.3(10) . . . . ? N2 Cu1 N1 C1 -176.5(2) 2_677 . . . ? N5 Cu1 N1 C1 -1.5(2) . . . . ? O5 Cu1 N1 C1 90.3(2) . . . . ? O6' Cu1 N1 C1 -97.0(5) . . . . ? O6 Cu1 N1 C1 -80.9(3) . . . . ? O1 Cu1 N1 N2 -128.4(8) . . . . ? N2 Cu1 N1 N2 10.8(4) 2_677 . . . ? N5 Cu1 N1 N2 -174.3(3) . . . . ? O5 Cu1 N1 N2 -82.5(3) . . . . ? O6' Cu1 N1 N2 90.2(6) . . . . ? O6 Cu1 N1 N2 106.4(4) . . . . ? C1 N1 N2 N3 0.2(3) . . . . ? Cu1 N1 N2 N3 173.4(3) . . . . ? C1 N1 N2 Cu1 173.8(2) . . . 2_677 ? Cu1 N1 N2 Cu1 -13.1(5) . . . 2_677 ? N1 N2 N3 N4 -0.4(4) . . . . ? Cu1 N2 N3 N4 -173.8(2) 2_677 . . . ? N2 N3 N4 C1 0.5(4) . . . . ? O1 Cu1 N5 C5 5.8(3) . . . . ? N1 Cu1 N5 C5 -179.1(3) . . . . ? N2 Cu1 N5 C5 -136.2(7) 2_677 . . . ? O5 Cu1 N5 C5 92.5(3) . . . . ? O6' Cu1 N5 C5 -93.8(4) . . . . ? O6 Cu1 N5 C5 -92.0(3) . . . . ? O1 Cu1 N5 C2 -176.4(2) . . . . ? N1 Cu1 N5 C2 -1.4(2) . . . . ? N2 Cu1 N5 C2 41.6(9) 2_677 . . . ? O5 Cu1 N5 C2 -89.7(2) . . . . ? O6' Cu1 N5 C2 84.0(4) . . . . ? O6 Cu1 N5 C2 85.8(2) . . . . ? N2 N1 C1 N4 0.1(4) . . . . ? Cu1 N1 C1 N4 -175.2(2) . . . . ? N2 N1 C1 C2 179.4(3) . . . . ? Cu1 N1 C1 C2 4.1(4) . . . . ? N3 N4 C1 N1 -0.4(4) . . . . ? N3 N4 C1 C2 -179.5(3) . . . . ? C5 N5 C2 C3 1.5(4) . . . . ? Cu1 N5 C2 C3 -176.6(2) . . . . ? C5 N5 C2 C1 -178.2(3) . . . . ? Cu1 N5 C2 C1 3.7(3) . . . . ? N1 C1 C2 N5 -5.2(4) . . . . ? N4 C1 C2 N5 173.9(3) . . . . ? N1 C1 C2 C3 175.1(3) . . . . ? N4 C1 C2 C3 -5.8(5) . . . . ? C4 N6 C3 C2 -0.5(5) . . . . ? N5 C2 C3 N6 -0.6(5) . . . . ? C1 C2 C3 N6 179.0(3) . . . . ? C3 N6 C4 C5 0.9(5) . . . . ? C2 N5 C5 C4 -1.1(5) . . . . ? Cu1 N5 C5 C4 176.6(2) . . . . ? N6 C4 C5 N5 0.0(5) . . . . ? Cu1 O1 C6 O2 18.2(4) . . . . ? Cu1 O1 C6 C7 -157.73(19) . . . . ? O2 C6 C7 C10 -97.2(3) . . . . ? O1 C6 C7 C10 79.1(3) . . . . ? O2 C6 C7 C8 78.5(4) . . . . ? O1 C6 C7 C8 -105.1(3) . . . . ? C10 C7 C8 C10 0.6(5) . . . 2_776 ? C6 C7 C8 C10 -175.1(3) . . . 2_776 ? C10 C7 C8 C9 -175.5(3) . . . . ? C6 C7 C8 C9 8.8(4) . . . . ? C10 C8 C9 O3 -158.7(3) 2_776 . . . ? C7 C8 C9 O3 17.4(4) . . . . ? C10 C8 C9 O4 19.1(4) 2_776 . . . ? C7 C8 C9 O4 -164.9(3) . . . . ? C8 C7 C10 C8 -0.6(5) . . . 2_776 ? C6 C7 C10 C8 175.4(3) . . . 2_776 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.447 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.065 #END data_90430a _database_code_depnum_ccdc_archive 'CCDC 756333' #TrackingRef '1-9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H5 Cd N6 O3' _chemical_formula_weight 321.56 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.8768(5) _cell_length_b 13.1226(12) _cell_length_c 11.5664(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.7880(10) _cell_angle_gamma 90.00 _cell_volume 888.88(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4473 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 2.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 2.460 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5783 _exptl_absorpt_correction_T_max 0.6136 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 4389 _diffrn_reflns_av_R_equivalents 0.0142 _diffrn_reflns_av_sigmaI/netI 0.0134 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1556 _reflns_number_gt 1525 _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^)+(0.0202P)^2^+0.9227P] 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 1556 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0164 _refine_ls_R_factor_gt 0.0157 _refine_ls_wR_factor_ref 0.0400 _refine_ls_wR_factor_gt 0.0396 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.56817(3) 0.455348(12) 0.847191(13) 0.01795(7) Uani 1 1 d . . . N1 N 0.6897(3) 0.30000(15) 0.91634(17) 0.0225(4) Uani 1 1 d . . . O1 O 0.9646(3) 0.48847(13) 0.84915(13) 0.0233(4) Uani 1 1 d . . . O2 O 1.2801(3) 0.47717(13) 0.96941(14) 0.0231(4) Uani 1 1 d . . . O3W O 0.6388(3) 0.44017(13) 0.65401(15) 0.0312(4) Uani 1 1 d . . . H3A H 0.5496 0.4059 0.6072 0.047 Uiso 1 1 d R . . H3B H 0.7011 0.4925 0.6269 0.047 Uiso 1 1 d R . . N2 N 0.8814(4) 0.27335(16) 0.98161(18) 0.0280(5) Uani 1 1 d . . . N3 N 0.8872(4) 0.17406(16) 0.98878(18) 0.0278(5) Uani 1 1 d . . . N4 N 0.7011(4) 0.13293(15) 0.92992(18) 0.0270(5) Uani 1 1 d . . . N5 N 0.2885(3) 0.30051(15) 0.77341(16) 0.0220(4) Uani 1 1 d . . . N6 N 0.0632(3) 0.11789(15) 0.71779(17) 0.0240(4) Uani 1 1 d . . . C1 C 0.5852(4) 0.21301(18) 0.88680(19) 0.0204(5) Uani 1 1 d . . . C2 C 0.3686(4) 0.21077(18) 0.81388(19) 0.0199(5) Uani 1 1 d . . . C3 C 0.0919(4) 0.29764(19) 0.7066(2) 0.0259(5) Uani 1 1 d . . . H3 H 0.0271 0.3585 0.6789 0.031 Uiso 1 1 calc R . . C4 C -0.0184(4) 0.2069(2) 0.6776(2) 0.0264(5) Uani 1 1 d . . . H4 H -0.1526 0.2082 0.6288 0.032 Uiso 1 1 calc R . . C5 C 0.2551(4) 0.12042(18) 0.7878(2) 0.0241(5) Uani 1 1 d . . . H5 H 0.3139 0.0600 0.8198 0.029 Uiso 1 1 calc R . . C6 C 1.0685(4) 0.48996(17) 0.94653(19) 0.0182(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.01465(11) 0.01883(11) 0.01987(11) 0.00043(6) -0.00154(7) 0.00182(6) N1 0.0190(10) 0.0207(11) 0.0272(10) -0.0005(8) -0.0016(8) -0.0002(8) O1 0.0166(8) 0.0330(9) 0.0199(8) -0.0025(7) -0.0014(6) -0.0034(7) O2 0.0124(8) 0.0320(9) 0.0248(9) -0.0067(7) 0.0005(6) -0.0004(7) O3W 0.0401(11) 0.0298(9) 0.0229(9) -0.0013(7) -0.0026(8) -0.0138(8) N2 0.0229(11) 0.0299(12) 0.0302(11) 0.0021(9) -0.0039(9) 0.0009(9) N3 0.0287(11) 0.0280(11) 0.0260(11) 0.0014(9) -0.0027(9) 0.0053(9) N4 0.0305(11) 0.0211(11) 0.0284(11) -0.0005(9) -0.0037(9) 0.0029(9) N5 0.0224(10) 0.0208(10) 0.0230(10) -0.0013(8) 0.0026(8) 0.0011(8) N6 0.0222(10) 0.0247(11) 0.0251(10) -0.0026(8) 0.0021(8) -0.0028(8) C1 0.0201(12) 0.0213(12) 0.0202(11) -0.0019(9) 0.0032(9) 0.0007(9) C2 0.0207(11) 0.0206(12) 0.0189(11) -0.0020(9) 0.0045(9) 0.0013(9) C3 0.0257(13) 0.0241(13) 0.0278(12) -0.0008(10) 0.0016(10) 0.0068(10) C4 0.0210(12) 0.0319(14) 0.0259(12) -0.0035(11) -0.0004(9) 0.0022(10) C5 0.0250(12) 0.0205(12) 0.0267(12) -0.0009(10) 0.0012(10) -0.0009(10) C6 0.0143(11) 0.0167(11) 0.0232(12) -0.0026(9) -0.0004(9) -0.0022(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N1 2.283(2) . ? Cd1 O2 2.3121(16) 1_455 ? Cd1 O3W 2.3150(18) . ? Cd1 O1 2.3682(16) . ? Cd1 N6 2.369(2) 2_556 ? Cd1 O2 2.4007(16) 3_767 ? N1 C1 1.327(3) . ? N1 N2 1.349(3) . ? O1 C6 1.236(3) . ? O2 C6 1.261(3) . ? O2 Cd1 2.3121(16) 1_655 ? O2 Cd1 2.4006(16) 3_767 ? O3W H3A 0.8500 . ? O3W H3B 0.8500 . ? N2 N3 1.306(3) . ? N3 N4 1.352(3) . ? N4 C1 1.327(3) . ? N5 C3 1.336(3) . ? N5 C2 1.338(3) . ? N6 C4 1.332(3) . ? N6 C5 1.333(3) . ? N6 Cd1 2.369(2) 2_546 ? C1 C2 1.467(3) . ? C2 C5 1.381(3) . ? C3 C4 1.383(4) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C6 1.554(4) 3_767 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cd1 O2 96.89(7) . 1_455 ? N1 Cd1 O3W 100.68(7) . . ? O2 Cd1 O3W 143.14(6) 1_455 . ? N1 Cd1 O1 83.21(6) . . ? O2 Cd1 O1 137.85(6) 1_455 . ? O3W Cd1 O1 76.68(6) . . ? N1 Cd1 N6 177.86(7) . 2_556 ? O2 Cd1 N6 81.18(6) 1_455 2_556 ? O3W Cd1 N6 81.44(7) . 2_556 ? O1 Cd1 N6 97.59(7) . 2_556 ? N1 Cd1 O2 86.42(6) . 3_767 ? O2 Cd1 O2 69.57(6) 1_455 3_767 ? O3W Cd1 O2 143.26(6) . 3_767 ? O1 Cd1 O2 68.37(5) . 3_767 ? N6 Cd1 O2 92.03(6) 2_556 3_767 ? C1 N1 N2 105.55(19) . . ? C1 N1 Cd1 123.59(15) . . ? N2 N1 Cd1 130.53(15) . . ? C6 O1 Cd1 114.99(14) . . ? C6 O2 Cd1 130.38(14) . 1_655 ? C6 O2 Cd1 115.05(14) . 3_767 ? Cd1 O2 Cd1 110.43(6) 1_655 3_767 ? Cd1 O3W H3A 120.6 . . ? Cd1 O3W H3B 113.8 . . ? H3A O3W H3B 117.1 . . ? N3 N2 N1 108.1(2) . . ? N2 N3 N4 110.52(19) . . ? C1 N4 N3 103.98(19) . . ? C3 N5 C2 116.1(2) . . ? C4 N6 C5 116.9(2) . . ? C4 N6 Cd1 125.49(16) . 2_546 ? C5 N6 Cd1 116.87(16) . 2_546 ? N4 C1 N1 111.9(2) . . ? N4 C1 C2 126.4(2) . . ? N1 C1 C2 121.7(2) . . ? N5 C2 C5 122.0(2) . . ? N5 C2 C1 116.5(2) . . ? C5 C2 C1 121.5(2) . . ? N5 C3 C4 122.0(2) . . ? N5 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? N6 C4 C3 121.5(2) . . ? N6 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? N6 C5 C2 121.5(2) . . ? N6 C5 H5 119.2 . . ? C2 C5 H5 119.2 . . ? O1 C6 O2 126.4(2) . . ? O1 C6 C6 118.6(2) . 3_767 ? O2 C6 C6 115.0(2) . 3_767 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Cd1 N1 C1 79.60(18) 1_455 . . . ? O3W Cd1 N1 C1 -67.85(19) . . . . ? O1 Cd1 N1 C1 -142.87(19) . . . . ? N6 Cd1 N1 C1 105.0(18) 2_556 . . . ? O2 Cd1 N1 C1 148.51(18) 3_767 . . . ? O2 Cd1 N1 N2 -107.9(2) 1_455 . . . ? O3W Cd1 N1 N2 104.6(2) . . . . ? O1 Cd1 N1 N2 29.62(19) . . . . ? N6 Cd1 N1 N2 -82.5(18) 2_556 . . . ? O2 Cd1 N1 N2 -39.0(2) 3_767 . . . ? N1 Cd1 O1 C6 -65.61(17) . . . . ? O2 Cd1 O1 C6 27.2(2) 1_455 . . . ? O3W Cd1 O1 C6 -168.32(17) . . . . ? N6 Cd1 O1 C6 112.39(17) 2_556 . . . ? O2 Cd1 O1 C6 23.22(16) 3_767 . . . ? C1 N1 N2 N3 0.3(3) . . . . ? Cd1 N1 N2 N3 -173.20(16) . . . . ? N1 N2 N3 N4 -0.4(3) . . . . ? N2 N3 N4 C1 0.4(3) . . . . ? N3 N4 C1 N1 -0.2(3) . . . . ? N3 N4 C1 C2 179.2(2) . . . . ? N2 N1 C1 N4 -0.1(3) . . . . ? Cd1 N1 C1 N4 174.01(15) . . . . ? N2 N1 C1 C2 -179.5(2) . . . . ? Cd1 N1 C1 C2 -5.4(3) . . . . ? C3 N5 C2 C5 0.3(3) . . . . ? C3 N5 C2 C1 179.7(2) . . . . ? N4 C1 C2 N5 -175.7(2) . . . . ? N1 C1 C2 N5 3.6(3) . . . . ? N4 C1 C2 C5 3.7(4) . . . . ? N1 C1 C2 C5 -177.0(2) . . . . ? C2 N5 C3 C4 -2.3(3) . . . . ? C5 N6 C4 C3 0.4(3) . . . . ? Cd1 N6 C4 C3 -169.27(17) 2_546 . . . ? N5 C3 C4 N6 2.0(4) . . . . ? C4 N6 C5 C2 -2.4(3) . . . . ? Cd1 N6 C5 C2 168.19(17) 2_546 . . . ? N5 C2 C5 N6 2.1(4) . . . . ? C1 C2 C5 N6 -177.2(2) . . . . ? Cd1 O1 C6 O2 158.56(19) . . . . ? Cd1 O1 C6 C6 -21.9(3) . . . 3_767 ? Cd1 O2 C6 O1 4.0(4) 1_655 . . . ? Cd1 O2 C6 O1 158.55(19) 3_767 . . . ? Cd1 O2 C6 C6 -175.61(17) 1_655 . . 3_767 ? Cd1 O2 C6 C6 -21.0(3) 3_767 . . 3_767 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.264 _refine_diff_density_min -0.525 _refine_diff_density_rms 0.081 #END data_90601a _database_code_depnum_ccdc_archive 'CCDC 756334' #TrackingRef '1-9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 Cl2 Hg2 N12' _chemical_formula_weight 766.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.1407(6) _cell_length_b 6.9435(2) _cell_length_c 30.3299(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3399.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9951 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description strip _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.995 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2752 _exptl_absorpt_coefficient_mu 18.383 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1202 _exptl_absorpt_correction_T_max 0.1691 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 16098 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2958 _reflns_number_gt 2692 _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^)+(0.0538P)^2^+15.9637P] 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 2958 _refine_ls_number_parameters 235 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.055 _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 0.413318(17) 0.16567(5) 0.098263(10) 0.02904(13) Uani 1 1 d . . . Hg2 Hg 0.356327(17) -0.07477(5) 0.353499(10) 0.03050(13) Uani 1 1 d . . . Cl2 Cl 0.22109(14) -0.1619(3) 0.36480(11) 0.0576(7) Uani 1 1 d . . . Cl1 Cl 0.55308(12) 0.0865(3) 0.10355(8) 0.0410(5) Uani 1 1 d . . . N1 N 0.2984(4) 0.2796(10) 0.0760(2) 0.0272(14) Uani 1 1 d . . . N2 N 0.2265(4) 0.2815(10) 0.0978(2) 0.0333(16) Uani 1 1 d . . . N3 N 0.1689(4) 0.3382(10) 0.0694(2) 0.0338(16) Uani 1 1 d . . . N4 N 0.2024(4) 0.3667(10) 0.0289(2) 0.0312(15) Uani 1 1 d . . . N5 N 0.4214(4) 0.2659(11) 0.0113(2) 0.0301(15) Uani 1 1 d . . . N6 N 0.3940(4) 0.4313(10) -0.0711(2) 0.0329(16) Uani 1 1 d . . . N7 N 0.4728(3) -0.0140(10) 0.3250(2) 0.0300(14) Uani 1 1 d . . . N8 N 0.5477(4) -0.0097(11) 0.3451(2) 0.0325(15) Uani 1 1 d U . . N9 N 0.6027(4) 0.0306(11) 0.3150(2) 0.0343(16) Uani 1 1 d . . . N10 N 0.5669(4) 0.0505(11) 0.2753(2) 0.0348(16) Uani 1 1 d . . . N11 N 0.3433(4) 0.0146(12) 0.2642(2) 0.0351(16) Uani 1 1 d . . . N12 N 0.3770(4) 0.0628(10) 0.1751(2) 0.0327(16) Uani 1 1 d . . . C1 C 0.2825(4) 0.3302(10) 0.0344(3) 0.0263(16) Uani 1 1 d . . . C2 C 0.3472(4) 0.3383(11) 0.0005(3) 0.0255(16) Uani 1 1 d . . . C3 C 0.4803(5) 0.2724(12) -0.0189(3) 0.0336(18) Uani 1 1 d . . . H3 H 0.5317 0.2182 -0.0128 0.040 Uiso 1 1 calc R . . C4 C 0.4673(5) 0.3575(12) -0.0592(3) 0.0346(19) Uani 1 1 d . . . H4 H 0.5111 0.3640 -0.0790 0.042 Uiso 1 1 calc R . . C5 C 0.3339(5) 0.4214(11) -0.0404(3) 0.0303(17) Uani 1 1 d . . . H5 H 0.2819 0.4717 -0.0469 0.036 Uiso 1 1 calc R . . C6 C 0.4215(4) 0.0309(11) 0.2487(3) 0.0239(16) Uani 1 1 d . . . C7 C 0.2835(5) 0.0274(14) 0.2342(3) 0.038(2) Uani 1 1 d . . . H7 H 0.2287 0.0196 0.2435 0.046 Uiso 1 1 calc R . . C8 C 0.2994(5) 0.0516(13) 0.1901(3) 0.038(2) Uani 1 1 d . . . H8 H 0.2554 0.0604 0.1703 0.045 Uiso 1 1 calc R . . C9 C 0.4375(5) 0.0525(12) 0.2055(3) 0.0305(18) Uani 1 1 d . . . H9 H 0.4923 0.0607 0.1963 0.037 Uiso 1 1 calc R . . C10 C 0.4873(4) 0.0241(11) 0.2824(2) 0.0258(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Hg1 0.02074(18) 0.0481(2) 0.0183(2) 0.00320(12) -0.00364(10) 0.00243(12) Hg2 0.02083(19) 0.0490(2) 0.0217(2) -0.00066(13) 0.00523(10) -0.00290(12) Cl2 0.0321(12) 0.0425(12) 0.098(2) -0.0063(13) 0.0241(13) -0.0079(10) Cl1 0.0211(10) 0.0515(12) 0.0503(14) -0.0128(10) -0.0070(8) 0.0052(9) N1 0.025(3) 0.043(4) 0.014(3) 0.002(3) 0.004(2) 0.002(3) N2 0.024(3) 0.044(4) 0.032(4) 0.006(3) 0.007(3) 0.006(3) N3 0.028(3) 0.052(4) 0.021(4) 0.011(3) 0.001(3) 0.003(3) N4 0.030(3) 0.046(4) 0.017(4) 0.001(3) -0.004(3) 0.010(3) N5 0.022(3) 0.047(4) 0.021(4) -0.002(3) -0.001(2) 0.004(3) N6 0.035(4) 0.040(4) 0.024(4) 0.006(3) 0.005(3) 0.000(3) N7 0.016(3) 0.051(4) 0.023(4) 0.003(3) -0.005(2) 0.002(3) N8 0.028(3) 0.055(3) 0.015(3) 0.002(3) -0.006(2) -0.002(3) N9 0.024(3) 0.060(5) 0.019(4) 0.006(3) 0.002(3) -0.007(3) N10 0.022(3) 0.059(5) 0.024(4) 0.004(3) -0.001(3) -0.008(3) N11 0.025(3) 0.061(5) 0.019(4) 0.003(3) 0.003(3) -0.004(3) N12 0.028(3) 0.058(4) 0.011(4) 0.012(3) -0.002(3) -0.002(3) C1 0.022(4) 0.033(4) 0.024(4) 0.001(3) 0.001(3) 0.006(3) C2 0.028(4) 0.038(4) 0.011(4) 0.000(3) -0.001(3) 0.001(3) C3 0.030(4) 0.046(5) 0.025(5) -0.003(4) 0.003(3) -0.003(4) C4 0.030(4) 0.043(5) 0.031(5) -0.004(4) 0.007(3) -0.007(4) C5 0.033(4) 0.037(4) 0.020(4) -0.002(3) -0.001(3) 0.003(3) C6 0.021(4) 0.032(4) 0.019(4) 0.003(3) -0.002(3) -0.001(3) C7 0.018(4) 0.071(6) 0.026(5) 0.007(4) 0.002(3) -0.003(4) C8 0.027(4) 0.056(5) 0.031(5) 0.009(4) -0.007(3) -0.007(4) C9 0.024(4) 0.045(5) 0.023(5) 0.006(3) 0.000(3) -0.004(3) C10 0.030(4) 0.036(4) 0.012(4) 0.002(3) 0.003(3) -0.001(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 N1 2.126(6) . ? Hg1 Cl1 2.3274(19) . ? Hg1 N12 2.507(7) . ? Hg2 N7 2.111(6) . ? Hg2 Cl2 2.291(2) . ? Hg2 N6 2.568(7) 7_566 ? N1 N2 1.336(9) . ? N1 C1 1.336(10) . ? N2 N3 1.329(9) . ? N3 N4 1.357(9) . ? N4 C1 1.329(10) . ? N5 C3 1.323(10) . ? N5 C2 1.338(9) . ? N6 C4 1.338(11) . ? N6 C5 1.346(11) . ? N6 Hg2 2.568(7) 7_565 ? N7 C10 1.340(10) . ? N7 N8 1.354(8) . ? N8 N9 1.305(9) . ? N9 N10 1.343(10) . ? N10 C10 1.316(10) . ? N11 C7 1.329(10) . ? N11 C6 1.352(9) . ? N12 C8 1.335(11) . ? N12 C9 1.345(10) . ? C1 C2 1.465(10) . ? C2 C5 1.386(12) . ? C3 C4 1.374(12) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C9 1.343(11) . ? C6 C10 1.474(10) . ? C7 C8 1.374(12) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 H9 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 N1 Hg1 Cl1 162.78(17) . . ? N1 Hg1 N12 101.4(2) . . ? Cl1 Hg1 N12 95.47(16) . . ? N7 Hg2 Cl2 164.2(2) . . ? N7 Hg2 N6 94.3(2) . 7_566 ? Cl2 Hg2 N6 101.23(17) . 7_566 ? N2 N1 C1 107.4(6) . . ? N2 N1 Hg1 127.2(5) . . ? C1 N1 Hg1 124.4(5) . . ? N3 N2 N1 106.9(6) . . ? N2 N3 N4 110.6(6) . . ? C1 N4 N3 104.3(6) . . ? C3 N5 C2 117.4(7) . . ? C4 N6 C5 115.5(7) . . ? C4 N6 Hg2 126.7(5) . 7_565 ? C5 N6 Hg2 117.7(5) . 7_565 ? C10 N7 N8 105.9(6) . . ? C10 N7 Hg2 126.1(5) . . ? N8 N7 Hg2 128.0(5) . . ? N9 N8 N7 107.3(6) . . ? N8 N9 N10 110.9(6) . . ? C10 N10 N9 105.0(6) . . ? C7 N11 C6 115.8(7) . . ? C8 N12 C9 116.4(7) . . ? C8 N12 Hg1 123.5(5) . . ? C9 N12 Hg1 118.9(5) . . ? N4 C1 N1 110.8(7) . . ? N4 C1 C2 126.8(7) . . ? N1 C1 C2 122.4(6) . . ? N5 C2 C5 121.0(7) . . ? N5 C2 C1 116.8(7) . . ? C5 C2 C1 122.2(7) . . ? N5 C3 C4 121.4(8) . . ? N5 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? N6 C4 C3 122.7(8) . . ? N6 C4 H4 118.7 . . ? C3 C4 H4 118.7 . . ? N6 C5 C2 121.9(7) . . ? N6 C5 H5 119.0 . . ? C2 C5 H5 119.0 . . ? C9 C6 N11 121.8(7) . . ? C9 C6 C10 122.8(7) . . ? N11 C6 C10 115.4(7) . . ? N11 C7 C8 122.6(7) . . ? N11 C7 H7 118.7 . . ? C8 C7 H7 118.7 . . ? N12 C8 C7 120.9(7) . . ? N12 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C6 C9 N12 122.4(7) . . ? C6 C9 H9 118.8 . . ? N12 C9 H9 118.8 . . ? N10 C10 N7 110.9(6) . . ? N10 C10 C6 125.8(7) . . ? N7 C10 C6 123.3(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl1 Hg1 N1 N2 -171.2(5) . . . . ? N12 Hg1 N1 N2 -3.5(7) . . . . ? Cl1 Hg1 N1 C1 21.8(11) . . . . ? N12 Hg1 N1 C1 -170.5(6) . . . . ? C1 N1 N2 N3 -1.7(9) . . . . ? Hg1 N1 N2 N3 -170.5(5) . . . . ? N1 N2 N3 N4 2.1(9) . . . . ? N2 N3 N4 C1 -1.7(9) . . . . ? Cl2 Hg2 N7 C10 21.3(12) . . . . ? N6 Hg2 N7 C10 -149.9(7) 7_566 . . . ? Cl2 Hg2 N7 N8 -156.9(5) . . . . ? N6 Hg2 N7 N8 31.9(7) 7_566 . . . ? C10 N7 N8 N9 0.4(9) . . . . ? Hg2 N7 N8 N9 178.9(6) . . . . ? N7 N8 N9 N10 -0.9(10) . . . . ? N8 N9 N10 C10 1.1(10) . . . . ? N1 Hg1 N12 C8 12.5(7) . . . . ? Cl1 Hg1 N12 C8 -171.1(7) . . . . ? N1 Hg1 N12 C9 -154.6(6) . . . . ? Cl1 Hg1 N12 C9 21.8(6) . . . . ? N3 N4 C1 N1 0.6(9) . . . . ? N3 N4 C1 C2 179.5(7) . . . . ? N2 N1 C1 N4 0.7(9) . . . . ? Hg1 N1 C1 N4 169.9(5) . . . . ? N2 N1 C1 C2 -178.3(7) . . . . ? Hg1 N1 C1 C2 -9.1(10) . . . . ? C3 N5 C2 C5 -1.7(11) . . . . ? C3 N5 C2 C1 -180.0(7) . . . . ? N4 C1 C2 N5 -169.3(8) . . . . ? N1 C1 C2 N5 9.5(11) . . . . ? N4 C1 C2 C5 12.4(13) . . . . ? N1 C1 C2 C5 -168.8(7) . . . . ? C2 N5 C3 C4 2.7(12) . . . . ? C5 N6 C4 C3 1.6(12) . . . . ? Hg2 N6 C4 C3 -175.7(6) 7_565 . . . ? N5 C3 C4 N6 -2.8(13) . . . . ? C4 N6 C5 C2 -0.6(11) . . . . ? Hg2 N6 C5 C2 177.0(6) 7_565 . . . ? N5 C2 C5 N6 0.7(12) . . . . ? C1 C2 C5 N6 178.9(7) . . . . ? C7 N11 C6 C9 -2.0(12) . . . . ? C7 N11 C6 C10 177.7(8) . . . . ? C6 N11 C7 C8 1.3(14) . . . . ? C9 N12 C8 C7 -1.2(13) . . . . ? Hg1 N12 C8 C7 -168.5(7) . . . . ? N11 C7 C8 N12 0.3(15) . . . . ? N11 C6 C9 N12 1.2(13) . . . . ? C10 C6 C9 N12 -178.5(7) . . . . ? C8 N12 C9 C6 0.5(12) . . . . ? Hg1 N12 C9 C6 168.4(6) . . . . ? N9 N10 C10 N7 -0.8(9) . . . . ? N9 N10 C10 C6 -179.8(8) . . . . ? N8 N7 C10 N10 0.3(9) . . . . ? Hg2 N7 C10 N10 -178.3(6) . . . . ? N8 N7 C10 C6 179.3(7) . . . . ? Hg2 N7 C10 C6 0.7(11) . . . . ? C9 C6 C10 N10 4.8(13) . . . . ? N11 C6 C10 N10 -174.9(8) . . . . ? C9 C6 C10 N7 -174.0(8) . . . . ? N11 C6 C10 N7 6.2(11) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.955 _refine_diff_density_min -1.740 _refine_diff_density_rms 0.218 #END data_90801b _database_code_depnum_ccdc_archive 'CCDC 756335' #TrackingRef '1-9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H7 Cd Cl N6 O2' _chemical_formula_weight 331.02 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 Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3629(3) _cell_length_b 13.9028(6) _cell_length_c 11.8372(4) _cell_angle_alpha 90.00 _cell_angle_beta 123.425(2) _cell_angle_gamma 90.00 _cell_volume 1011.31(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5115 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 2.414 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6067 _exptl_absorpt_correction_T_max 0.6439 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 4916 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1757 _reflns_number_gt 1726 _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^)+(0.0000P)^2^+7.8149P] 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 1757 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 0.72237(6) 0.04559(3) 0.43314(4) 0.03112(14) Uani 1 1 d . . . Cl1 Cl 0.9289(3) -0.00212(14) 0.3225(2) 0.0614(5) Uani 1 1 d . . . O1 O 0.4127(6) 0.0853(3) 0.2170(4) 0.0377(9) Uani 1 1 d . . . H1A H 0.3509 0.0344 0.1721 0.057 Uiso 1 1 d R . . H1B H 0.4460 0.1274 0.1793 0.057 Uiso 1 1 d R . . N1 N 0.5515(7) 0.1216(3) 0.5293(4) 0.0262(9) Uani 1 1 d . . . N2 N 0.4349(7) 0.1009(3) 0.5814(4) 0.0284(9) Uani 1 1 d . . . N3 N 0.3872(7) 0.1804(3) 0.6198(5) 0.0320(10) Uani 1 1 d . . . N4 N 0.4719(7) 0.2555(3) 0.5923(5) 0.0305(10) Uani 1 1 d . . . N5 N 0.7833(7) 0.2152(3) 0.4417(4) 0.0263(9) Uani 1 1 d . . . N6 N 0.7897(9) 0.4145(3) 0.4320(6) 0.0446(13) Uani 1 1 d . . . C1 C 0.5703(8) 0.2169(3) 0.5370(5) 0.0259(11) Uani 1 1 d . . . C2 C 0.6841(8) 0.2694(4) 0.4861(5) 0.0276(11) Uani 1 1 d . . . C3 C 0.8920(9) 0.2612(4) 0.3972(6) 0.0341(12) Uani 1 1 d . . . H3 H 0.9672 0.2259 0.3687 0.041 Uiso 1 1 calc R . . C4 C 0.8940(9) 0.3603(4) 0.3930(6) 0.0414(14) Uani 1 1 d . . . H4 H 0.9710 0.3903 0.3616 0.050 Uiso 1 1 calc R . . C5 C 0.6864(10) 0.3686(4) 0.4800(6) 0.0398(14) Uani 1 1 d . . . H5 H 0.6141 0.4043 0.5101 0.048 Uiso 1 1 calc R . . O2 O 0.1489(9) 0.2615(4) 0.7507(5) 0.0703(15) Uani 1 1 d . . . H2A H 0.2371 0.3044 0.7580 0.106 Uiso 1 1 d R . . H2B H 0.2038 0.2107 0.7974 0.106 Uiso 1 1 d 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 0.0335(2) 0.0212(2) 0.0472(3) 0.00132(17) 0.0276(2) 0.00272(16) Cl1 0.0561(10) 0.0655(11) 0.0750(12) 0.0100(10) 0.0440(10) 0.0174(9) O1 0.049(2) 0.0283(19) 0.036(2) 0.0014(17) 0.0236(19) -0.0078(17) N1 0.030(2) 0.019(2) 0.032(2) -0.0005(17) 0.019(2) 0.0006(17) N2 0.034(2) 0.025(2) 0.033(2) -0.0005(19) 0.023(2) -0.0002(18) N3 0.039(3) 0.024(2) 0.041(3) -0.001(2) 0.028(2) 0.0009(19) N4 0.039(2) 0.023(2) 0.036(3) -0.0020(19) 0.025(2) 0.0020(19) N5 0.027(2) 0.028(2) 0.028(2) 0.0010(18) 0.0173(19) -0.0016(18) N6 0.048(3) 0.029(3) 0.058(3) 0.005(2) 0.030(3) -0.004(2) C1 0.026(2) 0.021(2) 0.027(3) -0.001(2) 0.013(2) 0.002(2) C2 0.027(3) 0.027(3) 0.027(3) 0.002(2) 0.014(2) 0.002(2) C3 0.031(3) 0.039(3) 0.033(3) 0.003(2) 0.018(2) -0.001(2) C4 0.038(3) 0.041(3) 0.047(4) 0.009(3) 0.024(3) -0.008(3) C5 0.048(3) 0.027(3) 0.050(4) 0.002(3) 0.031(3) 0.001(3) O2 0.063(3) 0.096(4) 0.062(3) -0.007(3) 0.041(3) -0.013(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N2 2.302(4) 3_656 ? Cd1 N1 2.361(4) . ? Cd1 O1 2.371(4) . ? Cd1 N5 2.392(4) . ? Cd1 Cl1 2.5812(18) . ? Cd1 Cl1 2.672(2) 3_756 ? Cl1 Cd1 2.672(2) 3_756 ? O1 H1A 0.8500 . ? O1 H1B 0.8500 . ? N1 C1 1.330(6) . ? N1 N2 1.335(6) . ? N2 N3 1.314(6) . ? N2 Cd1 2.302(4) 3_656 ? N3 N4 1.344(6) . ? N4 C1 1.327(7) . ? N5 C3 1.339(7) . ? N5 C2 1.341(7) . ? N6 C4 1.327(8) . ? N6 C5 1.335(8) . ? C1 C2 1.468(7) . ? C2 C5 1.382(7) . ? C3 C4 1.379(8) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? O2 H2A 0.8505 . ? O2 H2B 0.8501 . ? 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 Cd1 N1 92.98(14) 3_656 . ? N2 Cd1 O1 88.86(14) 3_656 . ? N1 Cd1 O1 88.01(14) . . ? N2 Cd1 N5 161.85(14) 3_656 . ? N1 Cd1 N5 71.10(14) . . ? O1 Cd1 N5 82.10(13) . . ? N2 Cd1 Cl1 98.48(11) 3_656 . ? N1 Cd1 Cl1 168.29(11) . . ? O1 Cd1 Cl1 89.85(11) . . ? N5 Cd1 Cl1 97.21(11) . . ? N2 Cd1 Cl1 91.42(12) 3_656 3_756 ? N1 Cd1 Cl1 91.64(11) . 3_756 ? O1 Cd1 Cl1 179.57(11) . 3_756 ? N5 Cd1 Cl1 97.54(11) . 3_756 ? Cl1 Cd1 Cl1 90.44(6) . 3_756 ? Cd1 Cl1 Cd1 89.56(6) . 3_756 ? Cd1 O1 H1A 110.3 . . ? Cd1 O1 H1B 110.0 . . ? H1A O1 H1B 117.1 . . ? C1 N1 N2 104.6(4) . . ? C1 N1 Cd1 114.6(3) . . ? N2 N1 Cd1 140.9(3) . . ? N3 N2 N1 110.0(4) . . ? N3 N2 Cd1 123.4(3) . 3_656 ? N1 N2 Cd1 125.5(3) . 3_656 ? N2 N3 N4 108.7(4) . . ? C1 N4 N3 104.9(4) . . ? C3 N5 C2 117.3(5) . . ? C3 N5 Cd1 126.4(4) . . ? C2 N5 Cd1 116.1(3) . . ? C4 N6 C5 116.8(5) . . ? N4 C1 N1 111.8(5) . . ? N4 C1 C2 126.3(5) . . ? N1 C1 C2 121.9(5) . . ? N5 C2 C5 121.0(5) . . ? N5 C2 C1 116.1(4) . . ? C5 C2 C1 122.9(5) . . ? N5 C3 C4 120.8(5) . . ? N5 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? N6 C4 C3 122.3(5) . . ? N6 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? N6 C5 C2 121.6(6) . . ? N6 C5 H5 119.2 . . ? C2 C5 H5 119.2 . . ? H2A O2 H2B 117.0 . . ? 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 N2 Cd1 Cl1 Cd1 -91.50(12) 3_656 . . 3_756 ? N1 Cd1 Cl1 Cd1 100.3(5) . . . 3_756 ? O1 Cd1 Cl1 Cd1 179.68(10) . . . 3_756 ? N5 Cd1 Cl1 Cd1 97.66(11) . . . 3_756 ? Cl1 Cd1 Cl1 Cd1 0.0 3_756 . . 3_756 ? N2 Cd1 N1 C1 -169.8(4) 3_656 . . . ? O1 Cd1 N1 C1 -81.0(4) . . . . ? N5 Cd1 N1 C1 1.3(3) . . . . ? Cl1 Cd1 N1 C1 -1.5(8) . . . . ? Cl1 Cd1 N1 C1 98.7(4) 3_756 . . . ? N2 Cd1 N1 N2 9.9(6) 3_656 . . . ? O1 Cd1 N1 N2 98.6(5) . . . . ? N5 Cd1 N1 N2 -179.0(5) . . . . ? Cl1 Cd1 N1 N2 178.2(4) . . . . ? Cl1 Cd1 N1 N2 -81.6(5) 3_756 . . . ? C1 N1 N2 N3 -0.5(6) . . . . ? Cd1 N1 N2 N3 179.8(4) . . . . ? C1 N1 N2 Cd1 167.5(3) . . . 3_656 ? Cd1 N1 N2 Cd1 -12.2(7) . . . 3_656 ? N1 N2 N3 N4 0.4(6) . . . . ? Cd1 N2 N3 N4 -168.0(3) 3_656 . . . ? N2 N3 N4 C1 -0.1(6) . . . . ? N2 Cd1 N5 C3 -148.9(5) 3_656 . . . ? N1 Cd1 N5 C3 -178.7(5) . . . . ? O1 Cd1 N5 C3 -88.1(4) . . . . ? Cl1 Cd1 N5 C3 0.7(4) . . . . ? Cl1 Cd1 N5 C3 92.1(4) 3_756 . . . ? N2 Cd1 N5 C2 25.7(7) 3_656 . . . ? N1 Cd1 N5 C2 -4.1(3) . . . . ? O1 Cd1 N5 C2 86.5(4) . . . . ? Cl1 Cd1 N5 C2 175.3(3) . . . . ? Cl1 Cd1 N5 C2 -93.3(4) 3_756 . . . ? N3 N4 C1 N1 -0.2(6) . . . . ? N3 N4 C1 C2 178.5(5) . . . . ? N2 N1 C1 N4 0.5(6) . . . . ? Cd1 N1 C1 N4 -179.8(3) . . . . ? N2 N1 C1 C2 -178.3(4) . . . . ? Cd1 N1 C1 C2 1.4(6) . . . . ? C3 N5 C2 C5 2.9(8) . . . . ? Cd1 N5 C2 C5 -172.2(4) . . . . ? C3 N5 C2 C1 -178.7(4) . . . . ? Cd1 N5 C2 C1 6.2(6) . . . . ? N4 C1 C2 N5 176.1(5) . . . . ? N1 C1 C2 N5 -5.3(7) . . . . ? N4 C1 C2 C5 -5.6(9) . . . . ? N1 C1 C2 C5 173.1(5) . . . . ? C2 N5 C3 C4 -2.4(8) . . . . ? Cd1 N5 C3 C4 172.2(4) . . . . ? C5 N6 C4 C3 1.9(9) . . . . ? N5 C3 C4 N6 -0.1(9) . . . . ? C4 N6 C5 C2 -1.3(9) . . . . ? N5 C2 C5 N6 -1.1(9) . . . . ? C1 C2 C5 N6 -179.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.926 _refine_diff_density_min -0.778 _refine_diff_density_rms 0.098 #END #END data_90812b _database_code_depnum_ccdc_archive 'CCDC 756336' #TrackingRef '1-9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H5 Hg0.50 N6 O' _chemical_formula_weight 265.45 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' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.5940(9) _cell_length_b 12.643(2) _cell_length_c 11.2431(16) _cell_angle_alpha 90.00 _cell_angle_beta 106.662(7) _cell_angle_gamma 90.00 _cell_volume 761.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2753 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.97 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 10.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2363 _exptl_absorpt_correction_T_max 0.3115 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 3739 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1333 _reflns_number_gt 1053 _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^)+(0.0608P)^2^+0.5408P] 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 1333 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Hg1 Hg 0.5000 0.5000 0.5000 0.04199(18) Uani 1 2 d S . . O1 O 0.1779(8) 0.5721(4) 0.3097(4) 0.0861(16) Uani 1 1 d . . . H1A H 0.2139 0.6140 0.2582 0.129 Uiso 1 1 d R . . H1B H 0.0375 0.5410 0.2862 0.129 Uiso 1 1 d R . . N1 N 0.6356(8) 0.4016(3) 0.3858(4) 0.0403(10) Uani 1 1 d . . . N2 N 0.7834(9) 0.4263(4) 0.3142(4) 0.0542(12) Uani 1 1 d . . . N3 N 0.8257(9) 0.3403(4) 0.2612(4) 0.0555(12) Uani 1 1 d . . . N4 N 0.7123(8) 0.2578(3) 0.2983(4) 0.0423(10) Uani 1 1 d . . . N5 N 0.3336(7) 0.2997(3) 0.5075(4) 0.0356(9) Uani 1 1 d . . . N6 N 0.2531(9) 0.0823(3) 0.4786(5) 0.0574(13) Uani 1 1 d . . . C1 C 0.5954(9) 0.2981(3) 0.3747(4) 0.0317(10) Uani 1 1 d . . . C2 C 0.4396(8) 0.2410(3) 0.4375(4) 0.0308(10) Uani 1 1 d . . . C3 C 0.1882(10) 0.2472(4) 0.5625(5) 0.0466(13) Uani 1 1 d . . . H3 H 0.1115 0.2844 0.6128 0.056 Uiso 1 1 calc R . . C4 C 0.1475(10) 0.1413(4) 0.5479(6) 0.0527(14) Uani 1 1 d . . . H4 H 0.0422 0.1090 0.5876 0.063 Uiso 1 1 calc R . . C5 C 0.4010(10) 0.1333(4) 0.4237(6) 0.0487(14) Uani 1 1 d . . . H5 H 0.4802 0.0954 0.3749 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Hg1 0.0604(3) 0.0285(3) 0.0414(3) -0.00190(10) 0.02141(18) 0.00408(10) O1 0.073(3) 0.078(3) 0.084(4) 0.042(3) -0.014(3) -0.025(3) N1 0.057(3) 0.031(2) 0.040(2) 0.0018(18) 0.026(2) -0.0012(18) N2 0.073(3) 0.046(2) 0.056(3) 0.008(2) 0.038(3) -0.003(2) N3 0.072(3) 0.058(3) 0.049(3) -0.003(2) 0.038(3) -0.004(3) N4 0.054(2) 0.042(2) 0.037(2) -0.008(2) 0.023(2) 0.000(2) N5 0.040(2) 0.037(2) 0.031(2) -0.0051(18) 0.0116(19) 0.0001(17) N6 0.064(3) 0.043(3) 0.076(4) 0.000(3) 0.039(3) -0.008(2) C1 0.040(3) 0.030(2) 0.026(2) -0.0021(19) 0.011(2) 0.001(2) C2 0.034(2) 0.032(2) 0.027(3) -0.004(2) 0.0082(19) -0.001(2) C3 0.047(3) 0.059(3) 0.039(3) -0.006(3) 0.021(2) -0.005(3) C4 0.050(3) 0.056(3) 0.061(4) 0.004(3) 0.029(3) -0.008(3) C5 0.056(3) 0.034(3) 0.067(4) -0.009(3) 0.034(3) -0.006(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 Hg1 N1 2.080(4) 3_666 ? Hg1 N1 2.080(4) . ? Hg1 O1 2.539(4) 3_666 ? Hg1 O1 2.539(4) . ? O1 H1A 0.8502 . ? O1 H1B 0.8500 . ? N1 C1 1.328(6) . ? N1 N2 1.346(5) . ? N2 N3 1.295(6) . ? N3 N4 1.347(6) . ? N4 C1 1.321(5) . ? N5 C3 1.330(6) . ? N5 C2 1.338(5) . ? N6 C5 1.332(6) . ? N6 C4 1.333(7) . ? C1 C2 1.460(6) . ? C2 C5 1.381(7) . ? C3 C4 1.360(7) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5 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 N1 Hg1 N1 179.999(1) 3_666 . ? N1 Hg1 O1 89.49(17) 3_666 3_666 ? N1 Hg1 O1 90.51(17) . 3_666 ? N1 Hg1 O1 90.51(17) 3_666 . ? N1 Hg1 O1 89.49(17) . . ? O1 Hg1 O1 180.000(1) 3_666 . ? Hg1 O1 H1A 123.2 . . ? Hg1 O1 H1B 117.7 . . ? H1A O1 H1B 117.0 . . ? C1 N1 N2 106.8(4) . . ? C1 N1 Hg1 124.4(3) . . ? N2 N1 Hg1 128.7(3) . . ? N3 N2 N1 107.8(4) . . ? N2 N3 N4 110.0(4) . . ? C1 N4 N3 105.6(4) . . ? C3 N5 C2 115.5(4) . . ? C5 N6 C4 116.0(5) . . ? N4 C1 N1 109.8(4) . . ? N4 C1 C2 126.8(4) . . ? N1 C1 C2 123.4(4) . . ? N5 C2 C5 122.1(4) . . ? N5 C2 C1 115.9(4) . . ? C5 C2 C1 122.0(4) . . ? N5 C3 C4 122.6(5) . . ? N5 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? N6 C4 C3 122.3(5) . . ? N6 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? N6 C5 C2 121.5(5) . . ? N6 C5 H5 119.2 . . ? C2 C5 H5 119.2 . . ? 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 Hg1 N1 C1 -16(8) 3_666 . . . ? O1 Hg1 N1 C1 74.5(4) 3_666 . . . ? O1 Hg1 N1 C1 -105.5(4) . . . . ? N1 Hg1 N1 N2 167(8) 3_666 . . . ? O1 Hg1 N1 N2 -102.8(4) 3_666 . . . ? O1 Hg1 N1 N2 77.2(4) . . . . ? C1 N1 N2 N3 0.9(6) . . . . ? Hg1 N1 N2 N3 178.6(4) . . . . ? N1 N2 N3 N4 -1.3(6) . . . . ? N2 N3 N4 C1 1.1(6) . . . . ? N3 N4 C1 N1 -0.5(6) . . . . ? N3 N4 C1 C2 178.3(5) . . . . ? N2 N1 C1 N4 -0.3(6) . . . . ? Hg1 N1 C1 N4 -178.1(3) . . . . ? N2 N1 C1 C2 -179.1(4) . . . . ? Hg1 N1 C1 C2 3.1(7) . . . . ? C3 N5 C2 C5 -0.2(7) . . . . ? C3 N5 C2 C1 178.8(4) . . . . ? N4 C1 C2 N5 -177.9(5) . . . . ? N1 C1 C2 N5 0.8(7) . . . . ? N4 C1 C2 C5 1.2(8) . . . . ? N1 C1 C2 C5 179.8(5) . . . . ? C2 N5 C3 C4 -0.6(8) . . . . ? C5 N6 C4 C3 -0.3(9) . . . . ? N5 C3 C4 N6 0.9(9) . . . . ? C4 N6 C5 C2 -0.6(8) . . . . ? N5 C2 C5 N6 0.8(9) . . . . ? C1 C2 C5 N6 -178.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.712 _refine_diff_density_min -1.999 _refine_diff_density_rms 0.208 #END data_90814b _database_code_depnum_ccdc_archive 'CCDC 756337' #TrackingRef '1-9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H7 Br Cd N6 O2' _chemical_formula_weight 375.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.4195(11) _cell_length_b 13.9422(19) _cell_length_c 9.9089(14) _cell_angle_alpha 90.00 _cell_angle_beta 95.093(2) _cell_angle_gamma 90.00 _cell_volume 1021.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4420 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 27.92 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 2.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 6.043 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.3499 _exptl_absorpt_correction_T_max 0.4093 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 4950 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1760 _reflns_number_gt 1670 _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^)+(0.0334P)^2^+13.9276P] 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 1760 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 Br1 Br 0.38624(13) 0.50092(7) -0.18930(10) 0.0520(3) Uani 1 1 d . . . Cd1 Cd 0.28527(7) 0.54631(3) 0.06864(6) 0.02732(19) Uani 1 1 d . . . O1 O 0.1907(7) 0.5863(4) 0.2841(5) 0.0348(12) Uani 1 1 d . . . H1A H 0.1724 0.5471 0.3471 0.052 Uiso 1 1 d R . . H1B H 0.2739 0.6237 0.3168 0.052 Uiso 1 1 d R . . N1 N 0.0198(7) 0.6215(4) -0.0273(6) 0.0236(12) Uani 1 1 d . . . N2 N -0.1463(7) 0.6005(4) -0.0806(6) 0.0265(12) Uani 1 1 d . . . N3 N -0.2327(8) 0.6806(4) -0.1190(6) 0.0292(13) Uani 1 1 d . . . N4 N -0.1232(8) 0.7544(4) -0.0919(6) 0.0276(13) Uani 1 1 d . . . N5 N 0.3364(8) 0.7158(4) 0.0587(6) 0.0247(12) Uani 1 1 d . . . N6 N 0.3502(10) 0.9145(5) 0.0691(7) 0.0392(16) Uani 1 1 d . . . C1 C 0.0303(9) 0.7168(5) -0.0358(7) 0.0232(14) Uani 1 1 d . . . C2 C 0.1938(10) 0.7692(5) 0.0159(7) 0.0252(14) Uani 1 1 d . . . C3 C 0.4891(10) 0.7615(6) 0.1024(8) 0.0321(16) Uani 1 1 d . . . H3 H 0.5919 0.7262 0.1308 0.039 Uiso 1 1 calc R . . C4 C 0.4960(11) 0.8602(6) 0.1059(8) 0.0378(18) Uani 1 1 d . . . H4 H 0.6047 0.8902 0.1347 0.045 Uiso 1 1 calc R . . C5 C 0.2014(11) 0.8684(5) 0.0233(8) 0.0362(17) Uani 1 1 d . . . H5 H 0.0985 0.9036 -0.0048 0.043 Uiso 1 1 calc R . . O2 O 0.3924(10) 0.7623(6) 0.7504(8) 0.0638(19) Uani 1 1 d . . . H2A H 0.4803 0.7316 0.7907 0.096 Uiso 1 1 d R . . H2B H 0.4180 0.8120 0.7061 0.096 Uiso 1 1 d 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 Br1 0.0414(5) 0.0580(6) 0.0554(6) -0.0055(4) -0.0026(4) 0.0115(4) Cd1 0.0224(3) 0.0174(3) 0.0415(3) -0.0010(2) -0.0007(2) 0.00199(19) O1 0.045(3) 0.026(3) 0.033(3) 0.000(2) -0.001(2) -0.006(2) N1 0.024(3) 0.017(3) 0.028(3) -0.001(2) -0.001(2) 0.001(2) N2 0.021(3) 0.023(3) 0.035(3) 0.002(3) -0.002(2) -0.001(2) N3 0.026(3) 0.020(3) 0.041(3) 0.002(3) -0.002(3) 0.001(2) N4 0.029(3) 0.020(3) 0.033(3) 0.003(2) -0.003(3) 0.004(2) N5 0.023(3) 0.021(3) 0.029(3) 0.001(2) 0.000(2) -0.001(2) N6 0.045(4) 0.025(3) 0.047(4) -0.005(3) 0.003(3) -0.009(3) C1 0.028(4) 0.019(3) 0.023(3) 0.000(3) 0.003(3) 0.002(3) C2 0.030(4) 0.019(3) 0.027(3) -0.002(3) 0.005(3) -0.002(3) C3 0.031(4) 0.032(4) 0.033(4) -0.006(3) 0.002(3) -0.005(3) C4 0.034(4) 0.038(4) 0.041(4) -0.008(4) 0.003(3) -0.015(3) C5 0.039(4) 0.023(4) 0.045(5) 0.001(3) 0.000(4) -0.001(3) O2 0.055(4) 0.076(5) 0.059(4) 0.012(4) -0.001(3) -0.003(4) _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 Br1 Cd1 2.6992(11) 3_665 ? Br1 Cd1 2.7990(12) . ? Cd1 N2 2.300(6) 3_565 ? Cd1 N1 2.356(5) . ? Cd1 O1 2.372(5) . ? Cd1 N5 2.396(6) . ? Cd1 Br1 2.6992(11) 3_665 ? O1 H1A 0.8500 . ? O1 H1B 0.8503 . ? N1 N2 1.329(8) . ? N1 C1 1.334(8) . ? N2 N3 1.327(8) . ? N2 Cd1 2.300(6) 3_565 ? N3 N4 1.323(8) . ? N4 C1 1.330(9) . ? N5 C2 1.332(9) . ? N5 C3 1.338(9) . ? N6 C5 1.322(11) . ? N6 C4 1.344(11) . ? C1 C2 1.468(10) . ? C2 C5 1.385(10) . ? C3 C4 1.377(11) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? O2 H2A 0.8501 . ? O2 H2B 0.8500 . ? 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 Cd1 Br1 Cd1 87.42(3) 3_665 . ? N2 Cd1 N1 93.11(19) 3_565 . ? N2 Cd1 O1 89.6(2) 3_565 . ? N1 Cd1 O1 87.44(19) . . ? N2 Cd1 N5 162.4(2) 3_565 . ? N1 Cd1 N5 70.99(19) . . ? O1 Cd1 N5 82.29(19) . . ? N2 Cd1 Br1 98.72(14) 3_565 3_665 ? N1 Cd1 Br1 167.68(14) . 3_665 ? O1 Cd1 Br1 89.21(13) . 3_665 ? N5 Cd1 Br1 96.82(14) . 3_665 ? N2 Cd1 Br1 90.19(15) 3_565 . ? N1 Cd1 Br1 90.80(14) . . ? O1 Cd1 Br1 178.21(13) . . ? N5 Cd1 Br1 97.42(14) . . ? Br1 Cd1 Br1 92.58(3) 3_665 . ? Cd1 O1 H1A 126.1 . . ? Cd1 O1 H1B 103.0 . . ? H1A O1 H1B 105.8 . . ? N2 N1 C1 104.6(5) . . ? N2 N1 Cd1 140.7(4) . . ? C1 N1 Cd1 114.6(4) . . ? N3 N2 N1 109.6(5) . . ? N3 N2 Cd1 123.8(4) . 3_565 ? N1 N2 Cd1 125.5(4) . 3_565 ? N4 N3 N2 108.9(5) . . ? N3 N4 C1 105.5(6) . . ? C2 N5 C3 117.5(6) . . ? C2 N5 Cd1 116.1(4) . . ? C3 N5 Cd1 126.1(5) . . ? C5 N6 C4 116.5(7) . . ? N4 C1 N1 111.4(6) . . ? N4 C1 C2 127.0(6) . . ? N1 C1 C2 121.6(6) . . ? N5 C2 C5 120.9(7) . . ? N5 C2 C1 116.2(6) . . ? C5 C2 C1 122.9(7) . . ? N5 C3 C4 120.8(7) . . ? N5 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? N6 C4 C3 121.9(7) . . ? N6 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? N6 C5 C2 122.2(8) . . ? N6 C5 H5 118.9 . . ? C2 C5 H5 118.9 . . ? H2A O2 H2B 117.1 . . ? 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 Cd1 Br1 Cd1 N2 -98.74(14) 3_665 . . 3_565 ? Cd1 Br1 Cd1 N1 168.15(14) 3_665 . . . ? Cd1 Br1 Cd1 O1 178(100) 3_665 . . . ? Cd1 Br1 Cd1 N5 97.22(14) 3_665 . . . ? Cd1 Br1 Cd1 Br1 0.0 3_665 . . 3_665 ? N2 Cd1 N1 N2 -10.2(8) 3_565 . . . ? O1 Cd1 N1 N2 -99.6(7) . . . . ? N5 Cd1 N1 N2 177.6(7) . . . . ? Br1 Cd1 N1 N2 -174.0(4) 3_665 . . . ? Br1 Cd1 N1 N2 80.1(7) . . . . ? N2 Cd1 N1 C1 170.9(5) 3_565 . . . ? O1 Cd1 N1 C1 81.5(5) . . . . ? N5 Cd1 N1 C1 -1.3(5) . . . . ? Br1 Cd1 N1 C1 7.1(10) 3_665 . . . ? Br1 Cd1 N1 C1 -98.8(5) . . . . ? C1 N1 N2 N3 -0.3(7) . . . . ? Cd1 N1 N2 N3 -179.3(5) . . . . ? C1 N1 N2 Cd1 -168.5(5) . . . 3_565 ? Cd1 N1 N2 Cd1 12.5(10) . . . 3_565 ? N1 N2 N3 N4 0.4(8) . . . . ? Cd1 N2 N3 N4 168.8(4) 3_565 . . . ? N2 N3 N4 C1 -0.3(8) . . . . ? N2 Cd1 N5 C2 -21.8(10) 3_565 . . . ? N1 Cd1 N5 C2 4.8(5) . . . . ? O1 Cd1 N5 C2 -85.1(5) . . . . ? Br1 Cd1 N5 C2 -173.4(5) 3_665 . . . ? Br1 Cd1 N5 C2 93.1(5) . . . . ? N2 Cd1 N5 C3 152.3(7) 3_565 . . . ? N1 Cd1 N5 C3 178.9(6) . . . . ? O1 Cd1 N5 C3 88.9(6) . . . . ? Br1 Cd1 N5 C3 0.7(6) 3_665 . . . ? Br1 Cd1 N5 C3 -92.8(6) . . . . ? N3 N4 C1 N1 0.1(8) . . . . ? N3 N4 C1 C2 -178.2(7) . . . . ? N2 N1 C1 N4 0.2(8) . . . . ? Cd1 N1 C1 N4 179.4(4) . . . . ? N2 N1 C1 C2 178.6(6) . . . . ? Cd1 N1 C1 C2 -2.2(8) . . . . ? C3 N5 C2 C5 -3.3(10) . . . . ? Cd1 N5 C2 C5 171.3(6) . . . . ? C3 N5 C2 C1 177.9(6) . . . . ? Cd1 N5 C2 C1 -7.5(8) . . . . ? N4 C1 C2 N5 -175.2(7) . . . . ? N1 C1 C2 N5 6.7(10) . . . . ? N4 C1 C2 C5 6.1(11) . . . . ? N1 C1 C2 C5 -172.1(7) . . . . ? C2 N5 C3 C4 1.6(11) . . . . ? Cd1 N5 C3 C4 -172.4(6) . . . . ? C5 N6 C4 C3 -2.9(12) . . . . ? N5 C3 C4 N6 1.6(12) . . . . ? C4 N6 C5 C2 1.2(12) . . . . ? N5 C2 C5 N6 1.9(12) . . . . ? C1 C2 C5 N6 -179.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.112 _refine_diff_density_min -1.292 _refine_diff_density_rms 0.152 #END data_90825b _database_code_depnum_ccdc_archive 'CCDC 756338' #TrackingRef '1-9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H5 Cd I N6 O' _chemical_formula_weight 404.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.276(2) _cell_length_b 10.159(3) _cell_length_c 16.055(5) _cell_angle_alpha 90.00 _cell_angle_beta 112.545(11) _cell_angle_gamma 90.00 _cell_volume 1096.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5315 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description BLOCK _exptl_crystal_colour PALE-YELLOW _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 2.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 4.788 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.4189 _exptl_absorpt_correction_T_max 0.4966 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 5364 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1935 _reflns_number_gt 1834 _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^)+(0.0219P)^2^+1.2674P] 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 0.0053(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1935 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0221 _refine_ls_R_factor_gt 0.0202 _refine_ls_wR_factor_ref 0.0533 _refine_ls_wR_factor_gt 0.0525 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.23510(3) 0.05119(2) 0.145152(15) 0.02295(11) Uani 1 1 d . . . I1 I 0.61537(3) 0.03955(3) 0.280131(16) 0.03734(11) Uani 1 1 d . . . O1 O 0.2852(3) 0.2456(3) 0.07630(18) 0.0382(6) Uani 1 1 d . . . N1 N -0.1051(3) 0.1060(3) 0.05014(17) 0.0231(6) Uani 1 1 d . . . N2 N -0.2491(4) 0.0776(3) -0.03010(17) 0.0258(6) Uani 1 1 d . . . N3 N -0.4129(4) 0.1388(3) -0.03911(19) 0.0351(7) Uani 1 1 d . . . N4 N -0.3808(4) 0.2109(3) 0.03456(18) 0.0335(7) Uani 1 1 d . . . N5 N 0.0947(4) 0.1971(3) 0.22502(17) 0.0262(6) Uani 1 1 d . . . N6 N -0.0832(4) 0.3807(3) 0.29822(17) 0.0275(6) Uani 1 1 d . . . C1 C -0.1907(4) 0.1885(3) 0.0876(2) 0.0231(7) Uani 1 1 d . . . C2 C -0.0884(4) 0.2437(3) 0.1780(2) 0.0243(7) Uani 1 1 d . . . C3 C 0.1852(5) 0.2413(4) 0.3084(2) 0.0337(8) Uani 1 1 d . . . H3 H 0.3124 0.2111 0.3429 0.040 Uiso 1 1 calc R . . C4 C 0.0963(5) 0.3306(4) 0.3455(2) 0.0340(8) Uani 1 1 d . . . H4 H 0.1631 0.3568 0.4050 0.041 Uiso 1 1 calc R . . C5 C -0.1739(4) 0.3369(3) 0.2143(2) 0.0268(7) Uani 1 1 d . . . H5 H -0.2987 0.3702 0.1791 0.032 Uiso 1 1 calc R . . H1B H 0.2892 0.3171 0.1046 0.040 Uiso 1 1 d R . . H1A H 0.3781 0.2330 0.0573 0.040 Uiso 1 1 d 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 0.01981(14) 0.02732(16) 0.02100(15) -0.00134(9) 0.00702(10) 0.00119(9) I1 0.02333(14) 0.04320(18) 0.03799(17) 0.00507(10) 0.00340(11) -0.00184(9) O1 0.0352(13) 0.0354(14) 0.0500(15) -0.0004(12) 0.0230(12) 0.0001(11) N1 0.0194(12) 0.0277(15) 0.0197(13) -0.0013(11) 0.0048(10) 0.0005(11) N2 0.0219(13) 0.0329(15) 0.0207(14) -0.0013(12) 0.0059(11) 0.0035(12) N3 0.0255(14) 0.0483(19) 0.0260(15) -0.0077(14) 0.0039(12) 0.0095(14) N4 0.0225(13) 0.0476(18) 0.0245(15) -0.0091(13) 0.0025(12) 0.0094(13) N5 0.0196(13) 0.0305(15) 0.0252(14) -0.0031(12) 0.0050(11) 0.0016(11) N6 0.0254(13) 0.0302(15) 0.0247(14) -0.0039(12) 0.0073(11) 0.0014(12) C1 0.0197(14) 0.0280(17) 0.0205(16) -0.0015(13) 0.0064(12) 0.0015(13) C2 0.0207(15) 0.0279(17) 0.0236(16) -0.0024(14) 0.0080(12) -0.0028(13) C3 0.0242(16) 0.039(2) 0.0304(19) -0.0091(16) 0.0017(14) 0.0062(15) C4 0.0302(17) 0.039(2) 0.0253(17) -0.0080(15) 0.0019(14) 0.0052(15) C5 0.0194(14) 0.0340(18) 0.0242(17) -0.0050(15) 0.0051(12) 0.0037(14) _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 N2 2.298(3) 3 ? Cd1 O1 2.359(3) . ? Cd1 N6 2.412(3) 2_545 ? Cd1 N1 2.423(2) . ? Cd1 N5 2.427(3) . ? Cd1 I1 2.7871(8) . ? O1 H1B 0.8514 . ? O1 H1A 0.8508 . ? N1 C1 1.318(4) . ? N1 N2 1.344(3) . ? N2 N3 1.302(4) . ? N2 Cd1 2.298(3) 3 ? N3 N4 1.334(4) . ? N4 C1 1.337(4) . ? N5 C3 1.323(4) . ? N5 C2 1.341(4) . ? N6 C5 1.328(4) . ? N6 C4 1.335(4) . ? N6 Cd1 2.412(3) 2 ? C1 C2 1.466(4) . ? C2 C5 1.379(4) . ? C3 C4 1.375(5) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5 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 Cd1 O1 92.16(10) 3 . ? N2 Cd1 N6 93.55(10) 3 2_545 ? O1 Cd1 N6 162.42(9) . 2_545 ? N2 Cd1 N1 88.53(9) 3 . ? O1 Cd1 N1 79.43(9) . . ? N6 Cd1 N1 84.11(9) 2_545 . ? N2 Cd1 N5 158.45(9) 3 . ? O1 Cd1 N5 84.73(9) . . ? N6 Cd1 N5 83.86(10) 2_545 . ? N1 Cd1 N5 69.93(9) . . ? N2 Cd1 I1 105.31(7) 3 . ? O1 Cd1 I1 96.55(6) . . ? N6 Cd1 I1 97.94(6) 2_545 . ? N1 Cd1 I1 165.79(6) . . ? N5 Cd1 I1 96.23(6) . . ? Cd1 O1 H1B 116.4 . . ? Cd1 O1 H1A 109.2 . . ? H1B O1 H1A 116.8 . . ? C1 N1 N2 104.0(2) . . ? C1 N1 Cd1 113.98(19) . . ? N2 N1 Cd1 141.9(2) . . ? N3 N2 N1 110.4(3) . . ? N3 N2 Cd1 120.23(19) . 3 ? N1 N2 Cd1 129.37(19) . 3 ? N2 N3 N4 108.8(2) . . ? N3 N4 C1 104.9(3) . . ? C3 N5 C2 116.8(3) . . ? C3 N5 Cd1 126.5(2) . . ? C2 N5 Cd1 116.6(2) . . ? C5 N6 C4 116.5(3) . . ? C5 N6 Cd1 120.1(2) . 2 ? C4 N6 Cd1 123.3(2) . 2 ? N1 C1 N4 111.9(3) . . ? N1 C1 C2 123.1(3) . . ? N4 C1 C2 125.0(3) . . ? N5 C2 C5 121.1(3) . . ? N5 C2 C1 116.1(3) . . ? C5 C2 C1 122.8(3) . . ? N5 C3 C4 121.9(3) . . ? N5 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? N6 C4 C3 121.7(3) . . ? N6 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? N6 C5 C2 121.9(3) . . ? N6 C5 H5 119.0 . . ? C2 C5 H5 119.0 . . ? 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 N2 Cd1 N1 C1 -178.7(2) 3 . . . ? O1 Cd1 N1 C1 -86.3(2) . . . . ? N6 Cd1 N1 C1 87.6(2) 2_545 . . . ? N5 Cd1 N1 C1 2.0(2) . . . . ? I1 Cd1 N1 C1 -11.6(4) . . . . ? N2 Cd1 N1 N2 5.0(4) 3 . . . ? O1 Cd1 N1 N2 97.5(3) . . . . ? N6 Cd1 N1 N2 -88.7(3) 2_545 . . . ? N5 Cd1 N1 N2 -174.3(4) . . . . ? I1 Cd1 N1 N2 172.2(2) . . . . ? C1 N1 N2 N3 -0.9(4) . . . . ? Cd1 N1 N2 N3 175.6(3) . . . . ? C1 N1 N2 Cd1 177.0(2) . . . 3 ? Cd1 N1 N2 Cd1 -6.5(5) . . . 3 ? N1 N2 N3 N4 0.9(4) . . . . ? Cd1 N2 N3 N4 -177.3(2) 3 . . . ? N2 N3 N4 C1 -0.4(4) . . . . ? N2 Cd1 N5 C3 177.5(3) 3 . . . ? O1 Cd1 N5 C3 -99.9(3) . . . . ? N6 Cd1 N5 C3 93.5(3) 2_545 . . . ? N1 Cd1 N5 C3 179.4(3) . . . . ? I1 Cd1 N5 C3 -3.9(3) . . . . ? N2 Cd1 N5 C2 -6.8(4) 3 . . . ? O1 Cd1 N5 C2 75.7(2) . . . . ? N6 Cd1 N5 C2 -90.9(2) 2_545 . . . ? N1 Cd1 N5 C2 -4.9(2) . . . . ? I1 Cd1 N5 C2 171.7(2) . . . . ? N2 N1 C1 N4 0.6(4) . . . . ? Cd1 N1 C1 N4 -177.0(2) . . . . ? N2 N1 C1 C2 178.6(3) . . . . ? Cd1 N1 C1 C2 0.9(4) . . . . ? N3 N4 C1 N1 -0.1(4) . . . . ? N3 N4 C1 C2 -178.0(3) . . . . ? C3 N5 C2 C5 2.3(5) . . . . ? Cd1 N5 C2 C5 -173.8(2) . . . . ? C3 N5 C2 C1 -176.8(3) . . . . ? Cd1 N5 C2 C1 7.1(4) . . . . ? N1 C1 C2 N5 -5.6(5) . . . . ? N4 C1 C2 N5 172.1(3) . . . . ? N1 C1 C2 C5 175.3(3) . . . . ? N4 C1 C2 C5 -7.0(5) . . . . ? C2 N5 C3 C4 0.1(5) . . . . ? Cd1 N5 C3 C4 175.8(3) . . . . ? C5 N6 C4 C3 1.8(5) . . . . ? Cd1 N6 C4 C3 -174.6(3) 2 . . . ? N5 C3 C4 N6 -2.3(6) . . . . ? C4 N6 C5 C2 0.6(5) . . . . ? Cd1 N6 C5 C2 177.1(2) 2 . . . ? N5 C2 C5 N6 -2.8(5) . . . . ? C1 C2 C5 N6 176.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.603 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.094 #END data_90907b _database_code_depnum_ccdc_archive 'CCDC 756339' #TrackingRef '1-9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Hg1.50 N15 O2' _chemical_formula_weight 673.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.2819(6) _cell_length_b 17.4904(16) _cell_length_c 14.8161(10) _cell_angle_alpha 90.00 _cell_angle_beta 115.224(3) _cell_angle_gamma 90.00 _cell_volume 1707.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6305 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 27.91 _exptl_crystal_description BLUE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 2.619 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_absorpt_coefficient_mu 13.539 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.1546 _exptl_absorpt_correction_T_max 0.1943 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 8423 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2965 _reflns_number_gt 2639 _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^)+(0.0346P)^2^+2.1424P] 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 2965 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0734 _refine_ls_wR_factor_gt 0.0710 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.14068(3) 0.801424(12) 0.139296(15) 0.03295(11) Uani 1 1 d . . . Hg2 Hg 0.0000 1.0000 0.0000 0.03969(12) Uani 1 2 d S . . O1 O 0.4293(9) 0.8906(3) 0.1318(5) 0.086(2) Uani 1 1 d . . . H1B H 0.5374 0.8709 0.1334 0.128 Uiso 1 1 d R . . H1A H 0.4012 0.9358 0.1094 0.128 Uiso 1 1 d R . . N1 N 0.0313(7) 0.7992(2) -0.0160(4) 0.0295(11) Uani 1 1 d . . . N2 N 0.0512(8) 0.8553(3) -0.0738(4) 0.0409(13) Uani 1 1 d . . . N3 N -0.0347(9) 0.8323(3) -0.1647(4) 0.0454(13) Uani 1 1 d . . . N4 N -0.1095(8) 0.7606(3) -0.1693(4) 0.0390(12) Uani 1 1 d . . . N5 N -0.0596(7) 0.6680(3) 0.0582(4) 0.0333(11) Uani 1 1 d . . . N6 N -0.2585(10) 0.5470(4) -0.0643(5) 0.0599(17) Uani 1 1 d . . . N7 N 0.2684(8) 0.8080(3) 0.2925(4) 0.0361(12) Uani 1 1 d . . . N8 N 0.2469(8) 0.8645(3) 0.3495(4) 0.0384(12) Uani 1 1 d . . . N9 N 0.3485(8) 0.8465(3) 0.4431(4) 0.0384(12) Uani 1 1 d . . . N10 N 0.4392(7) 0.7768(3) 0.4494(4) 0.0335(11) Uani 1 1 d . . . N11 N 0.3951(7) 0.6792(3) 0.2253(4) 0.0337(11) Uani 1 1 d . . . N12 N 0.6087(8) 0.5633(3) 0.3555(4) 0.0452(13) Uani 1 1 d . . . N13 N -0.0126(10) 0.9409(3) 0.1148(4) 0.0481(14) Uani 1 1 d . . . N14 N -0.0914(8) 0.9701(3) 0.1634(4) 0.0381(12) Uani 1 1 d . . . N15 N -0.1575(11) 0.9931(4) 0.2156(6) 0.0676(19) Uani 1 1 d . . . C1 C -0.0646(8) 0.7416(3) -0.0759(4) 0.0308(12) Uani 1 1 d . . . C2 C -0.1133(8) 0.6702(3) -0.0389(5) 0.0326(13) Uani 1 1 d . . . C3 C -0.1075(10) 0.6052(4) 0.0943(5) 0.0467(16) Uani 1 1 d . . . H3 H -0.0737 0.6018 0.1622 0.056 Uiso 1 1 calc R . . C4 C -0.2071(12) 0.5446(4) 0.0321(6) 0.0541(18) Uani 1 1 d . . . H4 H -0.2382 0.5013 0.0593 0.065 Uiso 1 1 calc R . . C5 C -0.2094(11) 0.6102(4) -0.0997(5) 0.0491(17) Uani 1 1 d . . . H5 H -0.2415 0.6135 -0.1674 0.059 Uiso 1 1 calc R . . C6 C 0.3871(8) 0.7552(3) 0.3579(4) 0.0283(12) Uani 1 1 d . . . C7 C 0.4461(8) 0.6840(3) 0.3240(4) 0.0292(12) Uani 1 1 d . . . C8 C 0.4503(9) 0.6162(4) 0.1933(5) 0.0399(15) Uani 1 1 d . . . H8 H 0.4150 0.6101 0.1255 0.048 Uiso 1 1 calc R . . C9 C 0.5596(10) 0.5595(3) 0.2594(5) 0.0406(15) Uani 1 1 d . . . H9 H 0.6002 0.5170 0.2349 0.049 Uiso 1 1 calc R . . C10 C 0.5508(9) 0.6262(3) 0.3882(5) 0.0377(14) Uani 1 1 d . . . H10 H 0.5821 0.6308 0.4557 0.045 Uiso 1 1 calc R . . O2 O 0.7351(8) 0.7976(3) 0.1335(4) 0.0566(13) Uani 1 1 d . . . H2A H 0.7681 0.7786 0.1911 0.085 Uiso 1 1 d R . . H2B H 0.6682 0.7693 0.0836 0.085 Uiso 1 1 d 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 0.03934(16) 0.03127(14) 0.01876(15) -0.00012(8) 0.00330(11) 0.00041(9) Hg2 0.0614(2) 0.02639(17) 0.0329(2) 0.00229(13) 0.02162(18) -0.00246(14) O1 0.065(4) 0.060(3) 0.138(7) -0.027(4) 0.049(4) -0.016(3) N1 0.034(3) 0.028(2) 0.023(3) 0.005(2) 0.008(2) 0.0059(19) N2 0.055(3) 0.038(3) 0.031(3) 0.004(2) 0.020(3) 0.012(2) N3 0.058(4) 0.050(3) 0.029(3) 0.006(3) 0.019(3) 0.017(3) N4 0.039(3) 0.050(3) 0.020(3) -0.002(2) 0.005(2) 0.009(2) N5 0.029(3) 0.038(3) 0.022(3) -0.002(2) 0.000(2) -0.001(2) N6 0.066(4) 0.051(3) 0.050(4) -0.015(3) 0.013(3) -0.018(3) N7 0.037(3) 0.031(2) 0.032(3) 0.002(2) 0.006(2) 0.000(2) N8 0.045(3) 0.033(2) 0.028(3) -0.009(2) 0.007(2) 0.000(2) N9 0.046(3) 0.041(3) 0.022(3) -0.004(2) 0.008(2) 0.000(2) N10 0.033(3) 0.040(3) 0.020(3) -0.007(2) 0.004(2) 0.000(2) N11 0.031(3) 0.035(2) 0.025(3) -0.005(2) 0.002(2) 0.002(2) N12 0.046(3) 0.044(3) 0.040(3) 0.004(3) 0.014(3) 0.014(2) N13 0.080(4) 0.033(3) 0.045(4) 0.013(2) 0.040(3) 0.014(3) N14 0.041(3) 0.034(3) 0.034(3) 0.000(2) 0.011(3) -0.005(2) N15 0.075(5) 0.072(4) 0.074(5) -0.001(4) 0.050(4) 0.000(4) C1 0.024(3) 0.036(3) 0.026(3) 0.000(3) 0.004(2) 0.012(2) C2 0.019(3) 0.038(3) 0.037(4) -0.005(3) 0.009(2) 0.006(2) C3 0.052(4) 0.047(4) 0.032(4) 0.005(3) 0.009(3) -0.006(3) C4 0.059(5) 0.045(4) 0.053(5) -0.002(3) 0.019(4) -0.008(3) C5 0.055(4) 0.047(4) 0.038(4) -0.009(3) 0.014(3) -0.006(3) C6 0.022(3) 0.034(3) 0.018(3) 0.003(2) 0.000(2) -0.004(2) C7 0.022(3) 0.035(3) 0.024(3) -0.002(2) 0.003(2) -0.002(2) C8 0.035(3) 0.052(4) 0.024(3) -0.007(3) 0.004(3) 0.002(3) C9 0.044(4) 0.035(3) 0.040(4) -0.007(3) 0.015(3) 0.002(3) C10 0.042(4) 0.042(3) 0.023(3) 0.002(3) 0.008(3) 0.005(3) O2 0.069(3) 0.052(3) 0.047(3) -0.005(2) 0.023(3) -0.008(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 Hg1 N7 2.057(5) . ? Hg1 N1 2.090(5) . ? Hg1 N13 2.642(5) . ? Hg1 O1 2.657(6) . ? Hg2 N13 2.026(5) 3_575 ? Hg2 N13 2.026(5) . ? O1 H1B 0.8502 . ? O1 H1A 0.8489 . ? N1 C1 1.327(7) . ? N1 N2 1.351(7) . ? N2 N3 1.285(8) . ? N3 N4 1.357(8) . ? N4 C1 1.322(8) . ? N5 C2 1.321(8) . ? N5 C3 1.332(8) . ? N6 C4 1.314(10) . ? N6 C5 1.335(9) . ? N7 C6 1.350(7) . ? N7 N8 1.352(7) . ? N8 N9 1.303(7) . ? N9 N10 1.372(7) . ? N10 C6 1.297(7) . ? N11 C8 1.328(8) . ? N11 C7 1.350(8) . ? N12 C9 1.313(8) . ? N12 C10 1.341(8) . ? N13 N14 1.208(8) . ? N14 N15 1.144(9) . ? C1 C2 1.468(8) . ? C2 C5 1.366(9) . ? C3 C4 1.390(10) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.474(8) . ? C7 C10 1.375(8) . ? C8 C9 1.383(9) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? O2 H2A 0.8499 . ? O2 H2B 0.8489 . ? 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 N7 Hg1 N1 175.47(19) . . ? N7 Hg1 N13 93.79(18) . . ? N1 Hg1 N13 85.74(17) . . ? N7 Hg1 O1 91.1(2) . . ? N1 Hg1 O1 84.4(2) . . ? N13 Hg1 O1 75.41(19) . . ? N13 Hg2 N13 179.999(2) 3_575 . ? Hg1 O1 H1B 120.1 . . ? Hg1 O1 H1A 120.1 . . ? H1B O1 H1A 116.9 . . ? C1 N1 N2 107.2(5) . . ? C1 N1 Hg1 126.6(4) . . ? N2 N1 Hg1 126.2(4) . . ? N3 N2 N1 107.5(5) . . ? N2 N3 N4 110.4(5) . . ? C1 N4 N3 105.3(5) . . ? C2 N5 C3 117.0(5) . . ? C4 N6 C5 117.0(6) . . ? C6 N7 N8 105.1(5) . . ? C6 N7 Hg1 127.2(4) . . ? N8 N7 Hg1 127.7(4) . . ? N9 N8 N7 108.9(5) . . ? N8 N9 N10 109.0(5) . . ? C6 N10 N9 105.6(5) . . ? C8 N11 C7 117.0(5) . . ? C9 N12 C10 116.7(5) . . ? N14 N13 Hg2 119.1(4) . . ? N14 N13 Hg1 126.1(4) . . ? Hg2 N13 Hg1 114.7(2) . . ? N15 N14 N13 174.0(7) . . ? N4 C1 N1 109.6(5) . . ? N4 C1 C2 127.9(5) . . ? N1 C1 C2 122.5(5) . . ? N5 C2 C5 121.8(6) . . ? N5 C2 C1 115.2(5) . . ? C5 C2 C1 123.0(6) . . ? N5 C3 C4 121.0(7) . . ? N5 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? N6 C4 C3 121.5(7) . . ? N6 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? N6 C5 C2 121.6(7) . . ? N6 C5 H5 119.2 . . ? C2 C5 H5 119.2 . . ? N10 C6 N7 111.4(5) . . ? N10 C6 C7 127.1(5) . . ? N7 C6 C7 121.5(5) . . ? N11 C7 C10 121.2(5) . . ? N11 C7 C6 115.9(5) . . ? C10 C7 C6 122.8(5) . . ? N11 C8 C9 120.8(6) . . ? N11 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? N12 C9 C8 122.8(6) . . ? N12 C9 H9 118.6 . . ? C8 C9 H9 118.6 . . ? N12 C10 C7 121.4(6) . . ? N12 C10 H10 119.3 . . ? C7 C10 H10 119.3 . . ? H2A O2 H2B 117.2 . . ? 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 N7 Hg1 N1 C1 139(2) . . . . ? N13 Hg1 N1 C1 -136.6(5) . . . . ? O1 Hg1 N1 C1 147.7(5) . . . . ? N7 Hg1 N1 N2 -38(2) . . . . ? N13 Hg1 N1 N2 45.8(5) . . . . ? O1 Hg1 N1 N2 -29.9(4) . . . . ? C1 N1 N2 N3 1.6(6) . . . . ? Hg1 N1 N2 N3 179.6(4) . . . . ? N1 N2 N3 N4 -1.1(6) . . . . ? N2 N3 N4 C1 0.3(6) . . . . ? N1 Hg1 N7 C6 -92(2) . . . . ? N13 Hg1 N7 C6 -175.8(5) . . . . ? O1 Hg1 N7 C6 -100.4(5) . . . . ? N1 Hg1 N7 N8 90(2) . . . . ? N13 Hg1 N7 N8 6.5(5) . . . . ? O1 Hg1 N7 N8 81.9(5) . . . . ? C6 N7 N8 N9 0.5(6) . . . . ? Hg1 N7 N8 N9 178.7(4) . . . . ? N7 N8 N9 N10 -0.2(7) . . . . ? N8 N9 N10 C6 -0.2(6) . . . . ? N13 Hg2 N13 N14 35(3) 3_575 . . . ? N13 Hg2 N13 Hg1 -147(3) 3_575 . . . ? N7 Hg1 N13 N14 -40.5(6) . . . . ? N1 Hg1 N13 N14 144.0(6) . . . . ? O1 Hg1 N13 N14 -130.6(6) . . . . ? N7 Hg1 N13 Hg2 141.5(3) . . . . ? N1 Hg1 N13 Hg2 -33.9(3) . . . . ? O1 Hg1 N13 Hg2 51.4(3) . . . . ? Hg2 N13 N14 N15 -163(7) . . . . ? Hg1 N13 N14 N15 19(7) . . . . ? N3 N4 C1 N1 0.8(6) . . . . ? N3 N4 C1 C2 179.1(5) . . . . ? N2 N1 C1 N4 -1.5(6) . . . . ? Hg1 N1 C1 N4 -179.5(4) . . . . ? N2 N1 C1 C2 -179.9(5) . . . . ? Hg1 N1 C1 C2 2.1(7) . . . . ? C3 N5 C2 C5 -1.5(8) . . . . ? C3 N5 C2 C1 177.7(5) . . . . ? N4 C1 C2 N5 -176.4(5) . . . . ? N1 C1 C2 N5 1.7(7) . . . . ? N4 C1 C2 C5 2.8(9) . . . . ? N1 C1 C2 C5 -179.1(6) . . . . ? C2 N5 C3 C4 0.8(9) . . . . ? C5 N6 C4 C3 0.4(11) . . . . ? N5 C3 C4 N6 -0.3(11) . . . . ? C4 N6 C5 C2 -1.1(11) . . . . ? N5 C2 C5 N6 1.7(10) . . . . ? C1 C2 C5 N6 -177.5(6) . . . . ? N9 N10 C6 N7 0.6(6) . . . . ? N9 N10 C6 C7 179.7(5) . . . . ? N8 N7 C6 N10 -0.7(6) . . . . ? Hg1 N7 C6 N10 -178.8(4) . . . . ? N8 N7 C6 C7 -179.8(5) . . . . ? Hg1 N7 C6 C7 2.0(8) . . . . ? C8 N11 C7 C10 0.1(8) . . . . ? C8 N11 C7 C6 178.7(5) . . . . ? N10 C6 C7 N11 -171.4(6) . . . . ? N7 C6 C7 N11 7.6(8) . . . . ? N10 C6 C7 C10 7.2(9) . . . . ? N7 C6 C7 C10 -173.8(6) . . . . ? C7 N11 C8 C9 -1.6(9) . . . . ? C10 N12 C9 C8 -1.3(10) . . . . ? N11 C8 C9 N12 2.3(10) . . . . ? C9 N12 C10 C7 -0.3(9) . . . . ? N11 C7 C10 N12 0.9(9) . . . . ? C6 C7 C10 N12 -177.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.114 _refine_diff_density_min -1.840 _refine_diff_density_rms 0.146